So the thought of crossdressing was the logical next step, and I began collecting feminine items to wear, most bought off eBay or via the internet. I already had several chastity items and dildos to play with while looking at and watching porn; now I wanted to wear women's clothing and shoes during my private home sessions. I also started carefully experimenting with self-bondage and purchased a number of bondage items, including ice locks to keep me bound and helpless until the ice melted.
I started to make contact with other crossdressers and bisexuals on the internet, mainly via Craigs List but also through other websites. Initially, it was just emails and chat but I knew that eventually it would lead to discreet encounters in hotels or their homes.
This was a big step, to move from mere communication to actually meeting someone for mutual crossdressing, bisexual oral sex, bondage and BDSM and full penetrative sex. It took a while for me to commit to this activity but eventually I decided to make some tentative steps towards meeting.
The first thing that I noticed was that many of my contacts were unreliable, cancelling at the last minute or just not appearing as promised. I was not the only one a little nervous at such encounters.
Then I started to make contact with a man who liked sucking cocks and we arranged to meet in a hotel, sharing the cost of the room. He was very amenable and friendly, easy to talk to and became a trusted friend over the many encounters that we had. He would not let me touch his cock, even though I was desperate to do so, and he would not fuck me which I so wanted him to do. However, he would suck my cock for hours in the hotel room, with me writhing on the bed in ecstasy. He knew how to control my arousal, bringing me repeatedly to the brink of orgasm, then pressing my cock with his fingers to stop me cumming, then sucking me slowly again and bringing me close to orgasm before holding back and calming me down. He could keep me on the edge for hours before he finally allowed me to cum in his mouth as he gulped down my semen and sucked me dry. Then he would continue to suck me gently as my passion subsided, rubbing my groin, balls and cock as I slowly came back to earth. He was extremely good at fellatio oral sex and much better than any woman who has sucked my cock. After a while, when I had rested, he would start to gently sucking my cock again; taking his time to build up my arousal, sucking me gently but earnestly. We both knew that the second time would take much longer for me to cum and that he would have me writhing for hours in passion close to agony. He sucked my cock harder and deeper in his moist mouth, caressing me with his tongue and stroking my torso, nipples, legs and my balls with his hands. My stocking clad legs would be wrapped around him, my hands pressing on his head, my cock thrust into his mouth and my sissy cunt desperate for him to fuck me, only to be disappointed that he kept his own cock to himself. After what seemed like two or three hours for this second orgasm, with him continually edging me and then denying me release, he would start to suck harder and deeper, his hands and fingers would begin to caress me more fervently as we both started to gasp and pant; then I would almost without warning explode into his mouth, crying out with passion and pulling his head deep onto my cock as he sucked me dry and caressed my cock with his tongue. An absolutely wonderful experience with him every time we met; with me fully crossdressed, wearing women's clothing, wig, makeup, lipstick, bra, panties, stockings and shoes. We had a very strong and bonded relationship that lasted for a long time before we were unable to meet again. I miss him and miss his wonderful oral technique.
I was now comfortable in an encounter with another man, whether he was also crossdressing or in normal male clothing. Some of the men I met were only OK for one meet but many were more long term, with multiple meets over two or three years; the latter was my preference, as it built up trust and understanding with the other man. My own preference was to either meet in an equal relationship with another crossdresser or to meet with a normally dressed man who would dominate me. The first type could involve me being the 'top' or 'bottom', or even 'switching', dependent on the bisexual nature of the other crossdressed man. I was happy to suck and fuck, or suck and be fucked, preparing myself beforehand for either eventuality. This preparation involved my not eating solids for 48 hours beforehand, taking laxative tablets to clear my system, giving myself multiple enemas in the days before and on the day of the meet. As well as my crossdressing clothing, wigs, make up, lipstick, lingerie, stockings and shoes; I also took wet wipes, towels, an enema shower attachment, dildos and toys, cock cages, restraints and other BDSM items, a laptop to watch porn videos and a camera.
I would arrive at the hotel 30 minutes before the meet; giving me time to get changed, apply make up and lipstick, have a final enema, then lubricate my sissy cunt in anticipation of being fucked; then put my stockings and shoes on; finally my blonde wig. I would power up the laptop and start playing continuous porn videos, lay out the various dildos and toys, also the BDSM items; attach the long restraints to the bed legs and arrange the wrist and ankle restraints ready for use. I had a metal leg spreader, gags and blindfolds, plus a cane switch, whip with multiple tails, leather belts and a wide rubber paddle to be beaten with; I also had a leather 'gimp' mask, which could be put over my head, then laces were pulled tight at the back and the multiple straps on the sides were tightened around my head, over my ears and around my neck to fully enclose and isolate me, then a very efficient blindfold could be fitted with press-studs and a choice of gags (ball, dildo or large dildo) strapped onto the gimp mask to complete the job of disorientating and isolating me from sound and light in the room; in this state I was very vulnerable but it was a supreme way of being dominated. My meet would either want me to use the items on them or would want to use them on me. I was happy with both choices, particularly if the other person wanted to be the dominant partner. After preparing myself and the room for the encounter, I would text the room number to my meet who would be waiting in the hotel car park, and I usually had a few minutes before they arrived to freshen my lipstick and spray some perfume onto my lower back, wrists and neck. There would be a discreet knock on the door and I would open it while standing out of sight; my meet would enter and I would attach a Do Not Disturb sign to the door before closing it; we would usually kiss at this point and my meet would start to fondle my butt, before we moved further in the room to the bed. My meet would lay on the bed with me and we would kiss and caress each other, at first just face, neck and torso followed by more intimate exploring and cock touching through clothes; my meet would then remove their socks, shoes, top and trousers; then dependent on if they were a crossdresser or not, we would progress to the next steps; exploring each other and deliberately arousing the other person's cock and if my meet was a dominant man I would let him explore me with his hands and fingers while I sucked his hardening cock; if my meet was a crossdresser then we would suck each other's cock in turn and caress stocking clad legs before moving into a 69 position for mutual simultaneous cock sucking. For a first meet it would not be long before we were fucking each other or I was being fucked hard by a dominant; it would seem to my meet that was the reason we were there and the event needed to be consummated and completed as soon as possible; for second and subsequent meets the fucking would be part of a progression to more and more intimacy and exploration, slowly raising arousal to the point where it became necessary to fuck. Condoms got in the way at this point but they were part of the process, as was sufficient lubrication of the recipient of the ready and willing cock. On all meets the second round of intimacy was better than the first; less urgent, more relaxed, cocks still ready to get hard but less likely to cum too early and much more likely to give a profound, prolonged fucking before cumming; so with all meets I encouraged them to stay after the first fuck, rest for a while then start again with slow oral and a steady build up to a wonderful second long lasting fuck and more expansive orgasms; creating memories of the meet for both of us to savour afterwards.
The first time I was fucked without a condom was during a follow up meet with a dominant man. On the first meet, he had beaten me with the cane, leaving long weals on my sissy bottom; he had also restrained me and fingered my sissy cunt with his hands in lubricated latex gloves; he played with my toys, inserting them into me and sliding them to full extent inside me; then he had put on a condom and fucked me hard as I knelt on the bed, forcing me to lie face down while he continued to fuck me hard and fast before he came inside me in the condom. I really enjoyed it and we agreed to meet again soon. The second time we met he was even more dominant, whipping my sissy bottom as I moaned close to crying on the bed; he then made me put on the wrist and ankle restraints, locking my wrists together behind my back; then he locked my ankles to the spreader bar and took photographs of me lying helpless on the bed. He got on top of me and started to kiss me, while his hands explored my body, stocking clad spread legs, my panties and my throbbing sissy cock clit. He got off me, smiled at me and then pushed the metal leg spreader high in the air over my head and shoulders, leaving my vulnerable sissy cunt with only my panties covering his target. I was helpless as he got on top of me again, this time with his hard cock directed towards my (lubricated) sissy cunt; he moved my panties to one side and slowly eased his large cock into my sissy cunt; little by little he moved back and forth, allowing me to get used to the size of his cock; deeper and deeper he went into me as he looked down on his helpless sissy girlfriend while I looked up at him; I had not seen him put on a condom and I suspected he was about to fuck me bareback but I did not complain; the look on his face and my helpless state meant that any complaint would have been ignored, even punished afterwards. Having prepared me with whip and restraints, he was going to have his wicked way with me regardless of what I said. His large swollen cock thrust deeper into me, then he would withdraw his cock completely and enter my now gaping sissy cunt again; he did this repeatedly for many minutes, teasing me with his cock until I was gasping and writhing under him; he still kept pressure on the metal leg restraints, holding my legs high in the air over my shoulders while I lay on my back with my hands restrained behind and under me; he looked down and smiled into my face, as he began fucking me more quickly, deeper and deeper, faster and faster, his big hard cock filling me and demanding my attention; my own cock clit was now also swollen and hard in my panties, probably dripping pre-cum with the increasing excitement. We were both breathing hard now and his thrusts were becoming more meaningful; no more entering and then leaving my sissy cunt to tease me; now his cock was firmly and permanently inside me, fucking me hard, deep and fast. His eyes closed as I looked up at him, his breathing got more rapid; his whole body was becoming nearer to me as he lowered himself, my legs now almost touching my shoulders, with my high heeled shoes poised high up somewhere near the bedroom wall. His face was close to mine, he leaned even further down and he kissed my lips as he fucked me very hard and fast, smudging my lipstick on his lips and cheeks; and I knew that he was close to cumming inside me. It seemed as if time stood still and I can remember every detail of those final moments; with me totally helpless lying on the bed, him on top of me fucking me hard and very deep; the metal leg spreader between us but still allowing him to kiss me; as we both rose to the highest passion I could remember. Then it happened; after teasing me and fucking me for so long; after he had deliberately looked down at me while he entered me with his bare cock; after earlier forcing me to suck and deep throat his cock, then him whipping me in preparation, including taking photographs, before this final act of bareback domination; he let out a long, long groan and thrust hard and deepest into me, holding his cock there while I could feel him in spasm; his warm spurting cum filling my sissy cunt as we looked at each other. He waited in that position for some moments, looking at me, before he kissed me and started to withdraw; he wiped his cock on a towel and lay down next to me; while I lay in wonder at what had just happened, the best fuck of my life. We both rested, with me still in restraints and having to lie twisted n the bed because of my wrists locked together behind my back. We lay there for some time, drifting in and out of sleep, before he unlocked me and allowed me to stretch my arms and legs. It had been a wonderful long meet and we went on to have many more encounters. He was always dominant and most times he would restrain and punish me with a cane, whip or paddle; leaving some marks on my sissy bottom for several days but they would be hidden by clothing. I would wear perfume and red finger and toe nail varnish for him; as well as fully crossdressing, with wig, make up, lipstick, lingerie, bras and panties, dresses, blouses and skirts, nighties, suspender belts and stockings, or hold up stockings, with different types and colours of high heel shoes, sandals or boots.We had many hours in the hotel, with an early check-in at 12:00 noon and late nights or overnight stays, so there was time for everything. Sometimes we would have a drink of wine and watch porn videos on the laptop, lying on the bed touching and teasing each other; other times he would tie me to the bed face up or face down, while he teased and explored me; we got used to quickly fitting the bed leg long restraints and my lockable wrist and ankle restraints, or the leg spreader; I also had ropes and other types of restraint, so that he could put me in any position he choose, gag me with a ball or dildo gag, blindfold me; even hogtie me. When he had me so restrained he would occasionally experiment with breath play, holding my mouth closed and pinching my nose, so I could not breathe; all in trust and none of it dangerous, but it was still arousing for both of us. He would tape my mouth, pinch my nose to stop me breathing, then caress and play with my sissy cock clit, making me hard as I struggled for breath. He would reward me afterwards by him playing for minutes with my little cock, as I lay restrained getting my breath back, but he would never let me cum only to drip and dribble pre-cum which he loved to slide over the head of my sissy cock clit. He liked to restrain me spread eagled, face up or face down, so he had access to all of my helpless body. On occasion he would restrain me spread eagle sideways on the bed, with my head halfway down one side of the bed. In these spread eagle positions, even with my head at the top or bottom of the bed, he would force me to suck his cock, making me deep throat him almost to gagging, fucking my willing mouth and throat sometimes until he came spurting down my throat; he would also put on latex gloves, lubricate my sissy cunt and explore me with his fingers, massaging my prostate gland, widening my already gaping hole with more and more fingers until he would worm and rotate his lubricated complete hand inside me, then forming a fist which he would fuck me with like a huge dildo inside me, his thick wrist sliding in and out of gaping my sissy cunt, while I (still restrained) bucked and squirmed in a mix of pain and pleasure, particularly when he opened and closed his fist inside me to tease me (he only fucked me with his left fist, because his right hand was too big for me to endure); on other occasions he would force my large flexible dildos into me and fuck me with them like a real cock, while teasing my own sissy cock clit with a vibrator; sometimes at the end of all this preparation, when my sissy cunt was most enlarged and gaping, he would insert a large metal expanding 'bomb' (see photos) into me, covered with a condom instead of the supplied rubber band (to stop the metal nipping my skin), he would open up this metal butt plug inside me and lock it on the outside, so I was permanently and helplessly 'filled' with this metal expanded uncomfortable spreader until he decided to unlock and remove it carefully from my sissy cunt. I have two of these expanding metal butt plugs, one push-pull to expand and the other screw to expand, both similar diameters closed or expanded, and both lockable for permanence; there is no way that they can be removed from my sissy cunt without unlocking, so they are another way of me feeling helpless, this time with an internal restraint. If I was lying face down in a spread eagle position, he could eventually decide to tease me with his large swollen cock; repeatedly entering and exiting my sissy cunt, taking photos of my gaping hole or of his cock partially or fully inside me; he would then take his time to fuck me for many minutes, exploring my sissy cunt with his big cock; when he was finally ready, he would fuck me harder, faster and deeper, making me moan with pleasure; if I was face down, he would grab my head and pull it towards him to arch my back, his hand over my mouth and partially covering my nose to restrict my breathing; he would fuck me long and hard until he was ready to fill me with his cum, spurting deep inside me (we never used a condom after that first forced bareback occasion); I could feel him throbbing and pulsing deep inside me, while my little sissy cock clit was rock hard reflecting my own passion. When we stayed overnight in the hotel, I would change into a nightie and panties for him, with hold up stockings for him to stroke; we would sleep for a while, then he would get horny in the middle of the night, touching and exploring me, feeling my sissy cock clit, rubbing his hardening cock against my sissy cunt; then I would lubricate myself with an inserted applicator and lay in the spoon position for him to slowly insert his now hard cock into my sissy cunt; it felt wonderful as the bulbous head of cock opened me up and passed inside my sphincter muscles, free to move deeper inside me; he would fuck me like this for a long time, both of us enjoying the feeling of closeness as we lay in the spoon position, his hand touching and manipulating my erect sissy cock clit and using my pre-cum to slide his hand up and down my enlarged sissy cock clit; sometimes he would cum in me like this, usually gently with a groan and final deep thrust; on other occasions he would move on top of me, forcing me to lay face down under the duvet, and he would fuck me hard and deep for the final minutes before thrusting faster and faster, building up to a more dominant orgasm, jetting his hot sperm into me as I lay under him, often with his hand covering my mouth to stop me crying out. I loved sleeping and fucking overnight, because it was a different relationship, sleeping or just laying under the duvet with arms around each other, with plenty of time to explore each other in the dark and for multiple fucks before the morning. My dominant male had a wonderful, long and thick cock with a big bulbous head which stretched me every time he entered my willing sissy cunt; he also repeatedly complimented me on my clean, tight sissy cunt; so we both enjoyed fucking and could not get enough of each other, even overnight. I would suck his cock to waken him, feeling it growing in my warm moist mouth; then he would groan and put his hand on my head, moving into a more accessible position for me to deep throat him and bob my head up and down, using my tongue to lick the sides of his now hard cock; then he would make me lie face down and he would forceable enter my (already lubricated) sissy cunt and he would fuck my brains out for waking him up; wonderful feeling of being so dominated in response to just a little gentle sucking of his cock. We had many, many meets and wonderful encounters, always in hotels, including him organising group meets where I was the central entertainment to be fucked multiple times by multiple men; sucking each of them in turn in a spit roast while I was being fucked by an already prepared cock. He was a great organiser, encouraging each of us to participate to the fullest; photographing me in a spit roast (with a cock both in my mouth and sissy cunt), sometimes with two cocks in my mouth or sissy cunt at the same time, often with me being restrained and punished in between penetrations, or with my pleasuring any one of them who was ready to be sucked or to fuck me. He organised meets with other crossdressers, as well as with normal clad men, so I could be a 'top', 'bottom' or 'switch' with another crossdresser while he watched and took photos; or I could be the only sissy crossdresser in the room, dominated by all the men who he invited to fuck me. We had a wonderful relationship that I wished would continue today but sadly it ended when he moved away. I miss him and his dominance.
I met other crossdressers, either in hotels or in their homes. One did not like any form of anal, 'top' or 'bottom' but loved to give and receive oral; he was happy for me to suck his cock and for him to suck mine; I would crossdress with stockings but he preferred tights, so it was a different experience for me to feel and tease a large firm cock inside nylon tights, then to seek it out with my hands, lips, tongue and mouth to give him pleasure; he loved me giving him deep throat and, when the time was right, he loved to cum deep inside my mouth with his hot juicy sperm jetting down my open waiting throat; he had long dark natural hair, so he did not need a wig; he was very good at giving oral, often in a 69 position, licking and exploring my cock with his tongue, not deep throat but deep as far as was possible in his mouth; and he also liked the taste and feel of fresh cum in his mouth, rolling it around on his tongue to savour it; I met him several times, loved the size of his cock and I really savoured the high volumes of hot tasty sperm he would jet into my mouth and down my throat, interestingly he said that he loved my cock, which was just the right size for him to suck and enjoy, he also enjoyed receiving my cum into his warm mouth and he eagerly drank my initial cum before continuing to suck me for long minutes to drain me of all my remaining cum; he took some photos of me before one of our sessions, which I have included in this blog. There were others I met in hotels, not normally overnight (although I did several overnights once I got to know someone); the hotels were normally part of motorway service stations, so the access was easy and discreet; one hotel was in a big city centre but the guy was drunk when he arrived, so it was not a success; most of the hotels offered a quick check-out facility with just a key drop-off; none of them raised any issue with our meets and if they suspected anything they were most discreet. I went to a conference in another region once and arranged to meet a local crossdresser in my hotel in the evening; we got on very well, chatting and talking, then moved onto being more and more intimate; eventually to full oral and penetration; I enjoyed my time with him, which was very educational; he taught me a lot, not just about sexual technique but about myself. On another occasion, I booked a long All Inclusive holiday for a month in the Canaries and got in touch with several normal males or crossdressers (a mix of locals and holidaymakers like myself), who came to my hotel room in both the afternoons and evenings; I obtained extra door keys for them, which allowed them to enter my room at a given agreed time without having to wait in the corridor; they would find me fully crossdressed with wig and make up, plus high heel shoes; I would be waiting for them, self restrained and unable to escape, face down spread eagled on the bed with my stocking clad legs wide apart, my sissy cunt available but hidden by my dress, with lubricant visible nearby and porn videos playing on my laptop for them to watch while they fucked me (by agreement without a condom, so they could cum freely and fully into my sissy cunt). Usually, they could not resist closing the door quickly behind them, complete with Do Not Disturb sign (in English and Spanish), immediately getting on the bed behind me and teasing both my sissy cock clit and sissy cunt; they would undress and make me suck their cocks, although they would already be erect, hard and visibly ready; then they would mount the bed behind me and mount the sissy beneath them by inserting their prepared bare cocks into my sissy cunt; I would expand my sphincter muscles to accept them inside me, feeling their cock slide beyond my sphincter and move deeper inside me; they would usually slide in as far at their cock would go, before withdrawing and starting to fuck me with a regular rhythm. I would be completely helpless beneath them, accepting their cock inside my sissy cunt and enjoying them fucking me as hard and deep as they wished; feeling them increase their rhythm in intensity before their breathing increased and they groaned, while spurting their cum deep inside me from their bare cocks. I was able to wear permanent red toe nail varnish for them, which they appreciated, as well as my normal wig, makeup, perfume and lipstick; I had taken an extra large baggage case, containing many crossdressing items, including wig and high heel shoes, plus BDSM and bondage gear; these were all much appreciated by my visitors, who fucked me repeatedly (most often while I was restrained) during my long stay in the hotel; I always met them individually, for discretion and because they had different tastes in how they wished to use me; one of them had a particularly large long thick cock and huge balls, which was wonderful when he was fucking me, feeling him stretching me inside with his balls bashing regularly against me and then literally flooding my sissy cunt when he came strongly inside me; he was also a 'repeater' in that he had huge stamina and seemingly endless desire to fuck me many times in long overnight sessions. Not all but some of the men I met in the Canaries hotel were also into BDSM, so I was not only restrained during sessions but also smacked and whipped before being 'punished' for being a 'dirty sissy' by a strong firm bareback fuck. I really enjoyed that holiday, which was based on mutual trust; for those who entered my room with a key and discovered me helplessly bound and restrained to the bed in self bondage. it was obvious that they should release me from the restraints after they had fucked me; all of them did this and all of them returned for another session, which meant a nice relaxing holiday for me with at least one daily fuck to add to the enjoyment. Back in the UK, I travelled to a group session in a man's house; there were four of us, all crossdressers; and we had the equivalent of an orgy, fucking and sucking in chains on the bed, changing positions and partners, cumming inside someone and then feeling someone else cumming inside me, receiving multiple dumps of cum down my throat and cumming down someone else's throat; we were there for a long time and were exhausted afterwards. I had many 'triples' with either crossdressers or dominant males, which would involve a spit roast (cock in mouth and sissy cunt) for all the crossdressers at the meet, plus lots of photos taken by the 'spare' as a pair would perform on the bed; there was also endless opportunity and encouragement for smacking, whipping and caning of the subservient member of the group, usually my bottom being the one punished. There was one occasion when I met a young man (in his early 20s) in his house and we went upstairs to the bedroom; I had arrived wearing my crossdressing clothes under my normal male outdoor clothes, so all I had to do was strip off the outer layers and put on some high heels; he was already wearing stockings and suspenders; as he lay down on the bed I noticed that his cock was enormous, the biggest I have ever seen in my life (before and since) and it was wonderful for me to explore this magnificent beast with my hands, mouth and tongue; the only problem was that we both wanted to be 'bottom', that is we both wanted to be fucked; so I ended up being the 'top' and fucking him with my small cock, when what I actually wanted was for him to put his enormous cock inside me and fuck my brains out; such a waste of such a wonderful huge cock. I went discreetly every week to the house of another man, whose wife was at work on those days and who wanted me to behave and dress like his wife, using her style of makeup, lipstick and perfume; he bought me clothes to wear and high heel shoes, laying the items out on the bed for me to put on; then he would compliment me on my clothes while stroking my body and legs; he used 'poppers' to get high but I declined to join him in taking drugs; he was not interested in using restraints but he did regularly pin me to the bed, sofa or floor with his strong arms and hands while he had his wicked way with me; his cock was enormous, very thick and long with a large bulbous head; it was difficult but not impossible for me to give him oral; his cock was so big I had to relearn how to fit it into my mouth, to suck him and eventually give him deep throat without gagging; then he would take his prepared cock out of my mouth and fuck me on a sofa in the dining room, on the carpet or sofa in the lounge, or upstairs in the bedroom on the marital bed; he could fuck for a long time, had enormous stamina, and made me squeal and moan as he pounded me with no mercy; my little sissy cock clit would be hard and dripping in my panties as he fucked me with his length, thrusting deep inside me; he would fuck me easily like this, in different positions, for up to an hour before he finally started to fuck me in earnest and his breathing got faster, until he let out a long satisfied groan and spurted his cum inside me from his bare cock (he did not like to use condoms, because he was treating me as his wife); he would remain deep inside me for a few moments, then he would slowly withdraw his long cock before thanking me and sitting or laying down down for a rest; I just lay in the position he left me in, remembering all that had happened with a satisfied smile; we got on very well and I went to his house many times, always for a wonderful long and memorable fuck. Elsewhere, there were a couple of occasions when the area, house or the person I was meeting did not meet my standards; if that happened then I was polite but firm in not continuing the meet. However, the vast majority of encounters were a success for all concerned.When I had purchased my ESTIM items, I searched for and found other like-minded crossdressers also interested in ESTIM; this was a different kind of meet in that the focus was on the ESTIM rather than oral or anal sex. I travelled south to one such person and met him a number of times in his very nice ground floor apartment; he also liked to crossdress, so the first thing we did was put on our lingerie, stockings and high heels (not make up or lipstick, although I did use perfume for him to savour during our sessions); then we would suck each other's cocks to gain arousal before I would ask him to lay down face up on the bed and I would attach ESTIM items (a mix of silicon rubber loops around his balls and at the base of his cock, thick press stud cock permanent silicon loops of different diameters on his cock, ESTIM sticky pads in his groin, near his prostate and over his anus); when I had fitted these, I asked him to just lay back, relax and enjoy the experience, as I connected all the cables to the ESTIM controllers and slowly turned them on; this in turn turned him on as the electro pulses surged through his cock, tickled his balls and stimulated his prostate and anus; his cock bounced up and down to the rhythm of the electro pulses, his breathing becoming faster as the stimulation increased; I did everything slowly and carefully, so as not to torment or torture his cock (unlike my dominants with me, who delighted in turning up the controllers rapidly to a high level to make me squirm in my restraints); he loved the feeling of ESTIM when applied to him by another person and would close his eyes as his arousal grew; then suddenly his cock would start to throb and leak fluid, pre-cum dribbling from the eye of his cock as I watched it (I could not touch it because of the ESTIM); not long afterwards he would cum strongly as he moaned to himself, spurting streams of cum over his belly and legs; I slowly reduced the ESTIM level to bring him down from his high and then turned off the ESTIM controllers completely; at this point I could clean up his cum by licking it off his body and legs, then sucking his semi hard cock to drain the last drops of warm precious cum; he liked this, allowing me to tease his anus with my fingers as I sucked him; we only fucked twice, although he had a large cock that I enjoyed inside me (he did not want me to fuck him), because he was more interested in receiving the ESTIM; but in every ESTIM session we started and finished with oral, including 69 which he preferred, and he would suck my cum out of me after I had cum in his mouth at the end of our XXX sessions. We had a number of meets over one summer, even though it was a long way for me to travel; in the end I decided that I preferred being restrained and fucked, rather than giving ESTIM to another passive person, and I liked ESTIM being used on me while I was helpless to resist.
I have already talked in an earlier entry (22/02/2014) on this Blog, about the first time I was sucked by a man and then in another entry (03/03/2015) the first time I fucked and was fucked by a man (luckily he had a huge, long, beautiful cock); I have copied those same words below, so they are part of this narrative.
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Blog Entry (22/02/2014)
Bisexual Stockings Meet and Cock Sucking
I met a guy recently in a local hotel who had answered my request
online for a bisexual experience. He sent me a text when I arrived at
the hotel, giving me the room number and after knocking on the door I
was soon in the hotel bedroom with him. After a few moments chatting to
get to know each other he asked me if I wanted to continue with this XXX
meeting and I said "Yes".
I put on a pair of stockings, panties and high heel shoes and lay on the bed awaiting him. It was a strange experience, lying with my legs apart feeling him rubbing my stocking-clad legs as he knelt at the base of the bed. He moved up the bed and removed my high heel shoes, then my panties, nuzzling my semi-hard cock with his lips. Then he started sucking and licking my cock expertly, while his hands stroked my widespread, straining legs. He was so good that I was soon squirming and yearning for him to let me touch and suck his own cock. I wanted to make him hard and lubricate his bare cock so that he could push it slowly into my anus and fuck me. As he continued to suck my cock I got closer and closer to orgasm, opening up my legs and self for him to explore but he refrained from touching my anus and would not let me near his cock. He seemed content just to give me pleasure, taking his pleasure from having my cock in his mouth. I so wanted him to fuck me, I was desperate for his cock to enter me and for him to take his pleasure from fucking me hard and fast but it was not to be. After some time, I realised that it was not going to happen and I became fully focussed on his tongue and my cock. I felt myself slowly rising to orgasm and at the moment of release he took my cock out of his mouth, pumping me with his hand so that I came on my chest, spurting my cum up to my nipples while he finished me off rapidly with his hand. Then he put my cock back into his mouth and sucked out my remaining cum while I squirmed in pleasure.
If he had wanted to fuck me I would have let him and I remain an anal virgin who is longing for that experience, with a man who wants to take me in many positions and fill me with his cum after a long XXX session.
Hopefully, I will have more bisexual experiences in future.
----I put on a pair of stockings, panties and high heel shoes and lay on the bed awaiting him. It was a strange experience, lying with my legs apart feeling him rubbing my stocking-clad legs as he knelt at the base of the bed. He moved up the bed and removed my high heel shoes, then my panties, nuzzling my semi-hard cock with his lips. Then he started sucking and licking my cock expertly, while his hands stroked my widespread, straining legs. He was so good that I was soon squirming and yearning for him to let me touch and suck his own cock. I wanted to make him hard and lubricate his bare cock so that he could push it slowly into my anus and fuck me. As he continued to suck my cock I got closer and closer to orgasm, opening up my legs and self for him to explore but he refrained from touching my anus and would not let me near his cock. He seemed content just to give me pleasure, taking his pleasure from having my cock in his mouth. I so wanted him to fuck me, I was desperate for his cock to enter me and for him to take his pleasure from fucking me hard and fast but it was not to be. After some time, I realised that it was not going to happen and I became fully focussed on his tongue and my cock. I felt myself slowly rising to orgasm and at the moment of release he took my cock out of his mouth, pumping me with his hand so that I came on my chest, spurting my cum up to my nipples while he finished me off rapidly with his hand. Then he put my cock back into his mouth and sucked out my remaining cum while I squirmed in pleasure.
If he had wanted to fuck me I would have let him and I remain an anal virgin who is longing for that experience, with a man who wants to take me in many positions and fill me with his cum after a long XXX session.
Hopefully, I will have more bisexual experiences in future.
Blog Entry (03/03/2015)
My First Time
I have finally fulfilled a long dream of enjoying a man while we both wore stockings and knickers. He answered an advert I put on Craigslist which read as follows:
Stockings Loving Male - m4m - 50 (Leeds)
Age : 50
Body : curvy
Height : 5'8" (172cm)
Status : divorced
Likes : Non Smoker
"Stockings loving clean and healthy male seeking same for hotel fun in Leeds (UK) area; including wearing stockings, heels, lingerie, etc. Love to explore light BDSM, cock-sucking, mutual touching, safe anal play and full safe anal with right man."
He got in touch and we arranged to meet at his home. I arrived carrying a few items in a bag that we made use of later in the bedroom. Initially, we chatted in the lounge about general things, then gradually the conversation got more sexual and we talked about us wearing stockings. He removed his jeans and revealed lovely stocking-clad legs. He also revealed that he was wearing peep-through men's lace knickers and his long cock was hanging through a long way down one leg. I could hardly take my eyes off his cock as we continued to chat. He moved nearer and got close enough for me to touch his cock. I reached out and put my fingers around it and immediately began sucking him. It was wonderful, feeling a cock becoming more and more aroused in my hand and mouth. He became quite hard and moved to lay back on the sofa with his legs apart, while I continued to give him head with my mouth and stroke his balls with my fingers. He started to pant and I got very aroused myself. So much so that I started to deep throat him while watched, slowly lowering my head over him and taking his long cock deeper into my mouth until it was pushing down and then inside my throat. I managed not to gag and slowly moved my head back and forth so that he had a lingering experience of warmth and motion in my mouth. I also flicked my tongue rapidly over the head of his cock while he was just inside my mouth. Then I moved down on him again in full deep throat and started to slowly bob my head up and down, giving him repeated deep throat fucking and only moving my head up again when I started to gag and needed air. He was gasping now and I could taste his pre-cum as I licked the head of his cock, so I slowed down a little and concentrated on stroking his balls with my fingers and licking the side of his cock with my tongue. I asked him if it was OK and he said that it was very relaxing. I looked at his cock, it had changed colour and was vividly redder than before with the veins prominent all over. He was definitely very aroused. When he had calmed down a little, I started to deep throat him again but as I moved my head very slowly back up again I put my thumb and fingers around his cock at the base and followed my mouth up his cock with my tightly gripped hand, all the while now sucking strongly on his cock; effectively 'control wanking' him while fucking him gently with my throat. He loved this and started squirming on the sofa. I repeated this four or five times but always slowly so that he did not come. Then I took his cock out of my mouth and just stroked it while we talked about sex.
We moved up to the bedroom and I carried my bag up with me. In it I had a towel, two bottles of Super Slik anal lubricant, two lubricant applicators (to squirt the lube directly inside my anus) and a number of Extra Safe condoms. I took these items out of the bag and it would have been obvious to him that I was ready for full anal sex if he wished it. We lay the large towel on the bed above the duvet and I took off my outer clothes. Underneath I was wearing tight G-string panties and black Fiore 20 denier hold-up stockings. We lay on the bed side by side and I resumed sucking his cock while he lay relaxed with eyes closed. We were both getting very aroused. I let my fingers stray down to his anus and started to tease his hole with them, occasionally easing one finger inside him just a little. I stopped when he said "Naughty", at which he got up and asked me to follow him to the bathroom. He showed me how to give myself an enema with the shower hose (with the shower head removed) by turning the shower on and setting the water nicely warm (but not too hot), then holding the shower hose tightly against my anus and allowing the water to flow up inside me until I felt full. Then to remove the hose and sit on the toilet, evacuating the water and other material out of my anus. We did this twice each, then we both filled ourselves with water again and held it in for at least five minutes while walking around and talking. Finally we both evacuated ourselves and cleaned up, before returning to the bedroom. I have used this enema technique ever since but with five enemas each time before the final 'held inside' enema and now with a shower enema attachment (complete with On/Off tap) to screw onto the shower hose.
He lay on the towel and I started giving his now flaccid cock some very strong sucking, getting him nice and hard again. I pumped some of the Super Slik lubricant onto one of my hands and, while I continued to suck him, I slowly teased his anus with my fingers and then fully inserted my right index finger right into him. He raised his bottom briefly off the towel, pushing his cock deep into my mouth, while I pushed my finger firmly all the way into him. I moved my body between his legs and began a continual process of finger fucking him and deep throating his cock. After a few minutes of this he folded back his stocking-clad legs, making it obvious that he wanted me to fuck him. To confirm this, I moved up and teased his lubricated anus with the tip of my cock. He did not resist, so I leaned over to the bedside table to get a condom and put it onto my cock. Then I pumped some Super Slik lubricant onto the palm of my hand and rubbed it onto my very hard condom-covered cock. When ready, I resumed teasing both his cock and anus, while he lay there on his back with his knees folded up near his face. Then I raised myself up above him and presented my 'anal virgin' cock to his anus. We both helped to ease my cock into him, myself being very gentle so as not to hurt him. Gradually my cock got further and further, deeper and deeper into him as I lay on him with my arms and shoulders pushing his stocking-clad legs back into an anvil love-making position. My cock was deep now, inside him to the hilt, and I began fucking him, slowly at first, then ever more quickly as we both got extremely, pantingly aroused. He urged me to fuck him harder and I did not need any encouragement to fuck him as fast and as deep as I could. For at least five minutes (I can last a long time when in a condom), I fucked him at full pace, before climaxing gruntingly to an 'anal virgin' bisexual orgasm. I pumped my cum into him, held safely inside the condom, before looking at him in awe at what had just happened. My first time I had worn stockings and panties with a man; the first time that I had sucked a cock; the first time I had deep throated a cock rather than a dildo; the first time I had stroked a man's balls; the first time I had teased a man's anus; the first time I had pushed a lubricated finger into a man and teased his gripping anal muscles; the first time I had put on a condom for a man; the first time I had fucked a man; the first time that I had cum inside a man. He knew it and could see the look on my face.
I took off the condom and we talked for a while, then we both went to the bathroom to clean up. I got back to the bedroom first and filled an applicator twice with Super Slik lubricant, pumping it up into my 'anal virgin arse'. Then I lay face down on the towel until he returned to the bedroom, presenting my widespread stocking-clad legs and bare butt to him. I asked him if he would fuck me and he said "Yes". Then he masturbated himself hard with lubricant, put on a condom, rubbed lubricant onto the condom and rubbed more lubricant onto and into my anus. He got onto the towel behind me, kneeling between my legs. He pushed my legs wider, then pushed a finger into me to check if I was lubed up OK. I knew what was coming next and I braced myself both emotionally and physically for my first anal fucking by a man (I have used dildos and vibrators in the past). He could not get his cock easily into me, so he moved up closer to me and spread my legs further. I could feel his cock pushing on my anal sphincter muscles, feel it trying to enter my most intimate and deepest parts, feel it trying to take my anal virginity. He got into the entrance but then withdrew his cock. He asked me to kneel up and to put my shoulders back down on the towel, presenting myself before him and offering myself to him, allowing him to take my vulnerable virginity. Now he moved very close to my butt and I knew the time had come. His cock was now entering me with a considered urgency, slowly at first as he passed beyond my tight sissy cunt entrance, pausing to allowed me to get used to the size of him, then withdrawing a little, then entering me further. I helped him by pushing back with my anal muscles, opening myself and my sphincter up for him. He repeated the entering and withdrawal over and over again, getting deeper and deeper into me each time, until I suddenly realised that the whole of his long and large cock was inside me. We both paused while I got used to the idea of being fucked by a man. Then he gradually but not fully withdrew and started to slowly fuck me from behind while holding my butt and stroking my stocking-clad legs. I pushed back into him each time he drove his cock into me. I was becoming more and more aroused internally and externally, panting now with each of his thrusts. He was also panting and, although I could not see him, I knew that he was enjoying fucking me. He was driving his huge cock hard and deep into my sissy cunt, pushing me forward each time before I could regain balance. He was also fucking me at an increasing pace, so fast that he could not have fucked me any faster or deeper. It was exhausting for both of us but it was also extremely enjoyable. I could feel the grip of his hands on my bottom tighten and knew that he was about to cum. He was about to cum inside my 'virginal anus'. With a final flurry of very fast and very deep multiple thrusts of his pulsing cock, he came noisily inside me, pushing his cock in all the way as he jetted semen into my now no longer virginal 'sissy' pussy. I was ecstatic; it had happened. Not only had I taken a man but I had also been taken by one. The first time a man had teased my anus; the first time I had lain with my butt in the air in anticipation for a man; the first time I had felt a man lubricating my anus and exploring me with his fingers; the first time I had felt a (very large) cock trying to take me; the first time I had eased my anal muscles apart to help a cock enter me; the first time I had felt a cock disappear inside me slowly and fully; the first time I had felt a cock begin to fuck me; the first time I had felt a man grip my bottom as he enjoyed me; the first time I had felt a man fuck me hard, deep and very fast as if I was a women; the first time I had felt the anticipation of a man about to cum inside me; the first time I felt a man shudder and pulse inside me as he exploded in orgasm; the first time that I felt a sated cock withdraw from me; the first time that I had fully understood me.
He got off the bed and removed the full condom, putting it on the floor for later disposal. I was still very aroused, so I asked him if he would play with my arse for a while. He put on latex gloves, lubricated them, then inserted several fingers into me, pushing hard and deep, widening my anal entrance to the point that it nearly but not quite hurt. I started to pant and loved his attention, so he thrust his fingers even deeper and widened my anus beyond the pain barrier. I was extremely excited but could only take a few seconds of this glorious abuse before I moved up the bed away from his fingers and he realised that I could take no more. However, it had been superb and memorable.
We relaxed and chatted for a few moments, looking at his extensive 'clothes' collection of stockings, panties and lingerie. Then we both realised it was time for me to go and I dressed reluctantly before heading for the door. We had not kissed and had not embraced, perhaps leaving this for another time.
This was the most memorable experience that I have ever had in over fifty years of life; hence, my sharing this with you at length. I hope that you have enjoyed reading it on my Blog and I hope that you will encourage others to read it.
I am now, thankfully, no longer an 'anal virgin'.
----
That 'first time' changed my life, in that it confirmed to myself that I was a bisexual and showed me that I could also enjoy it. I was no longer a sissy 'virgin' and will remember that first time forever.
It opened up a huge range of encounters that I have enjoyed since. In particular, I discovered that I enjoy sucking a cock, preparing it for action, feeling it grow in my mouth from a semi-erect state to full pulsing erection; I am very good at deep throat, which is a great skill to learn, and I enjoy allowing a flaccid or an erect cock to enter and slide down my throat to full extent, as deep as it will go; I enjoy being mouth fucked and eventually being the recipient of warm spurting fresh salty cum, flooding my mouth and forcing me to swallow to avoid an overflow; I enjoy suckling and encouraging the last few drops of cum from a satisfied cock now becoming flaccid again; most of all I enjoy doing this oral worship when I am fully restrained and totally helpless to do otherwise, tied to a chair or bent over a small table, tied spread eagle face up or down on a bed with my head halfway down the bed side or at the bottom, wearing my gimp mask and disorientated while on my knees being roughly face fucked and sometimes simultaneously anally fucked up my eager sissy cunt; all these wonderful scenarios of restraint and forced oral sex I have experienced and enjoyed. Similarly, I enjoy being tied or otherwise restrained bent over a chair or table or restrained face down on a bed, with a ball or dildo gag in my mouth or a pair of my panties stuffed inside in my mouth and my lips held firmly together by a covering of tape, my helpless sissy bottom exposed in the air ready to receive my punishment for being a brazen sissy, smacked by a hand, whipped by a multi-tail leather whip, paddled by a firm rubber paddle, caned by a teacher's bamboo cane; all of these leaving their own different marks on my now red skin, either finger and hand marks, spread weals from the whip, round bruises from the paddle or long red weals from the cane, sometimes just breaking the skin, displaying bloody red lines and all of them painful to the point of crying. I enjoy being left after punishment to ponder my position and to feel the warmth of freshly smacked, whipped, paddled or caned flesh; photographed both before and after being punished; touched and soothed in my lingering pain; contemplating the combined state of passion, arousal and pain. In the same restrained and helpless positions around a bedroom or house, dependent on the ingenuity of my dominant partner; I thoroughly enjoy the feeling of being taken without even a request for consent, a cock entering my sissy cunt while I am helplessly restrained, gagged and unable to stop this hard cock from widening my sissy cunt entrance enough to disappear inside me to the hilt; sometimes it is a little painful at first but that pain changes to passionate acceptance as the penetration proceeds; the large bulbous cock pushing past my entrance and then being free to explore inside my sissy cunt, to play with and tease me deep inside, to seek full entry and depth, to be withdrawn completely and my gaping sissy cunt photographed before the dominant cock is thrust once more deep inside me, rampant and completely dominant; then the increasing rhythm and deepening thrusts, increased urgency and more obvious passion, faster and faster, deeper and deeper, taking me without consent while I am fully restrained before such a bare cock explodes deep inside me and floods my sissy cunt with hot juicy fresh cum; I enjoy all of this even more if I am forced to wear my gimp mask to disorientate me, as well as my being helplessly restrained. Then there are the long moments where my dominant partner restrains me; spread eagled or hog tied on a bed, or tied to a chair or table, sometimes with a large plug or an anal hook in my sissy cunt, while he caresses me, talks to me and takes photographs or videos of his helplessly restrained sissy crossdresser; nothing I can do in my tight restraints but wait until the next stage of punishment or passion; all of it enjoyable by both my dominant and myself. I have a 'pair' of leather arm binders, in which both my arms can be inserted and secured behind my back; these arm binders have restraining straps that fit over my shoulders and around my neck, ensuring that there is no possibility of me escaping from the arm restraints and no way to use my hands which are hidden behind my back enclosed together in a single mono leather glove at the end of the arm binders; attached to this mono glove is a large steel ring which can be used with other BDSM items, such as attached to an anal hook or to a rope attached to the ceiling, high up a wall or over a door, to make me stand uncomfortably in high heels on my toes in a 'strapado' position, with my arms stretched up behind me in the arm binders and my head forced down to accommodate the painful position; this is one of the most extreme BDSM positions and my dominants love it because of the pain it causes me. While I have been restrained spread eagle lying face up on the bed, I have had my small, inadequate, sissy cock clit teased for hours; made erect then forced to become flaccid again; sucked and licked; gripped firmly and wanked; covered and rubbed with an irritant like toothpaste, massaged painfully while in such hot agony; lubricated and masturbated slowly; edged repeatedly but never allowed to cum, always on the brink but not allowed to go over; close but always so far away; wonderfully teased for long, endless moments of yearning without release; then tormented with electro stimulation in the same restraints after I made the decision to buy ESTIM items, which were pounced on by my dominant males for teasing my cock while they had a rest from abusing my sissy cunt with their rampant but now flaccid cocks; ESTIM in the hands of a dominant male and carried out on the sissy cock clit of a restrained gagged crossdresser, is a real eye opener and eye waterer; because I am helpless and fully restrained in the position of choice for my dominant, the ESTIM seems to take the dominant male to another level of aggression, they delight in my groaning and squirming caused by the simple turn of an ESTIM controller dial; they won't let me cum, turning the dials up high to torment me but then back down again before I can get any relief by cumming; if we have the whole day or night, a dominant male can spend hours using ESTIM on me while watching my face twisted in a combination of pain and passion; always with a pair of panties pushed in my mouth and taped over or a solid gag (rubber ball or penis dildo) tightly locked onto my head to avoid any overheard screaming; eventually my dominants might take pity on me and leave the ESTIM at a high enough level to stimulate me but not too high to torture me, allowing me to become more aroused to the point of cumming all over myself while they watched and laughed; but not all my dominants would allow me to cum, only to dribble pre-cum to show my arousal; these dominants wanted total control of my sissy cock clit, which included what flowed from it and when; such dominants only used ESTIM for teasing, torment and torture, never for my pleasure but all of it for their pleasure and amusement. Including the ESTIM, I have such fabulous, long lasting memories of my encounters and the best are while I was restrained and totally helpless to change the immediate future; dominated by an ingenious man and his big cock; punished without remorse; almost raped without any consent; fucked to spurting conclusion by bare cocks with no permission given; spread and exposed, explored by fingers, hands, fists, dildos and vibrators; fucked by multiple cocks in long group sessions; brought to the dripping stage of pre-cum from my sissy cock clit but not allowed release. This is what I eventually craved for most and looked forward to in my encounters, although I was happy if my meet was another crossdresser rather than a dominant male..
My life has changed now but I have many fond crossdressing and bisexual memories of sucking, fucking, being sucked and fucked, savouring the taste of warm fresh cum, being restrained and punished, being happy dressing up in stockings and lingerie with high heels, putting on make up, lipstick and perfume, and being appreciated by all my admirers who would usually show that appreciation by fucking me hard and filling me with their hot juicy cum.
I have sucked and been fucked by many different shapes and sizes of cock, particularly evident in the group sessions where I could do a comparison in the same room. All cocks are enjoyable regardless of size, circumcised or with foreskin, as long as they are clean; all my encounters with males and other crossdressers were very respectful in that we had washed our cocks or sissy clits before the meet. I am lucky in that many of the cocks I enjoyed were huge, making it initially difficult to fit them into my mouth and to deep throat them; the thought of being fucked by such a big cock as I kissed, licked and sucked it, used to arouse me to distraction and make my sissy cock clit drip with pre-cum; then when it was time, I used to squirt lubricant into myself with an applicator and wait with anticipation while my male partner worked his large hard cock into me, slowly opening up my sphincter muscles to pass his bulbous head inside, then sliding deeper inside my sissy cunt eventually to full extent, filling me up and pausing before withdrawing then thrusting deep, repeatedly and more frequently inside my willing sissy cunt, then that final deepest thrust and groan before cumming inside me with juicy spurts of fresh flowing cum in volumes that would eventually dribble from me down my legs afterwards. Similarly, if I was with a crossdresser who preferred to be the 'bottom', then we would suck each other's cocks for many minutes, singly and/or in a 69 position, tasting and playing with the other's pre-cum, deep throating (perhaps just me doing it, if my partner could not deep throat) and getting each other in a fully aroused state ready for penetration; I would ask the other 'bottom' crossdresser to kneel on the bed with a towel under them, while I put on a condom and squirted lubricant into them with an applicator; I would also rub lubricant onto my condom covered cock, before moving into position behind them; often the other crossdresser would tell me that this was their first time being fucked by a real cock (they had used dildos on themselves), so I was actually taking their anal virginity just as I had lost my virginity to a wonderful large cock earlier in my encounters; with this in mind I would be very gentle and careful to expand their sissy cunt slowly, rather than just thrust painfully inside them, taking my time while they adjusted to my cock; it was always the early moments that were important, gaining access beyond the sphincter muscles, waiting for the muscles to relax enough to move a few millimetres further inside while being aware of any indication that the other crossdresser was uncomfortable or in pain, asking them if they were still OK and if it was OK to proceed; eventually there would be a silent plop as my cock head moved beyond the now gaping sphincter muscles gaining access deeper inside (I was aware of this significant moment from being fucked myself probably hundreds, maybe thousands, of times by large bulbous cocks); now we could both relax and I could begin to slowly work my cock back and forth, fucking in a slow rhythm that would be comfortable for my crossdressing 'bottom' partner, who would at this time be moaning beneath me, possibly wanking their own cock to get better satisfaction from the occasion; if my 'bottom' crossdresser partner did not play with their own cock, I found that I could reach around and under them to touch, grasp and wank their cock for them, sometimes gently but also occasionally forcefully to make them grunt in discomfort; because I was in a condom I found that I could maintain an erection and sustain it for a long time while fucking another man's sissy cunt; I could easily control myself and could fuck at a good pace for a long time to give full enjoyment to the recipient; only when we were both obviously ready would I let myself go, fucking 'her' much harder, deeper and faster until we both came in a final moment of joined passion; then I would pause for a moment while we savoured our arousal and emotions, before slowly withdrawing my cock while holding onto the filled condom which I would remove and tie up ready for disposal; them I would cuddle my crossdressing partner as they went over and processed their memories (possibly of losing their anal virginity) and I also reminded myself of how much I enjoyed being a 'top' and fucking someone else, as well as my enjoying being a 'bottom' on other occasions; I am a true 'switch', happy being either a 'top' or 'bottom' or both on an encounter. Very versatile, although my preference is definitely to be the submissive 'bottom' and my preference is to be the recipient of multiple hard and dominant fucks, even better if I am also restrained and helpless at the time.
So I have progressed from tentatively asking my female partner if she would like to fuck another man; to the pleasant surprise when she eventually said "Yes"; to seeking and finding possible partners for her on the internet, shortlisting them for her to 'chat' to while she used a vibrator on herself; to her selecting the men she wanted to meet in person; to me buying her many items of lingerie and types of stockings, even a gold 'cuckoldress' anklet; to me doing the final arrangements and booking a suitable hotel; to us eating a meal with this possible 'Bull' in the hotel, while they sat opposite me at the table and he was touching and teasing her clit making her squirm in front of me; to use retiring to our room and me watching them standing in the room, kissing and caressing each other; to me watching them and taking photos while he slid his hand up her skirt to fondle her clit; to her taking off his shirt and him removing her top, exposing her new basque, then removing her skirt to reveal her stockings; to her removing his trousers and looking with obvious desire at his hardening cock inside his pants; to them moving to the bed and my partner laying down presenting him with her spread legs for him to kneel beside the bed, stroke her legs and groin and begin a long oral exploration of her wet cunt and clit; to them both getting on the bed and my partner making me a real Cuckold by exposing then worshipping his big cock with her hands, lips, tongue and mouth; all while I watched in awe and took photos of this escalating situation (I the Cuckold, could not have stopped them at this point, even if I had tried; because they had gone beyond the point of initial intimacy and they would have refused to stop); so I remained quietly in the room invisible, as they were both focussed only on the other person, completely ignoring my presence in the room, moving from single oral to the 69 position, to him forcing her to suck his cock; he was becoming more dominant and she was enjoying his dominance; he moved her to a normal laying position on the bed, with her head on the pillows and her legs spread wide ready for him, inviting him, welcoming his next move; he got on top of her, elbows on either side supporting him, kissed her firmly and passionately, while teasing her clit with his big hard cock; she was gasping and submissive as he moved his cock to the entrance to her cunt, not entering her but teasing her while they kissed, while I took photos of his cock head at her entrance; then I watched as he subtly changed position, arching his back, pointing his long big fat cock directly at her now wet and willing entrance, pushing it firmly beyond her cunt lips while I watched it disappear inside her; he still kissed her and she kissed him back fervently, welcoming his advances with her arms initially wrapped around him before he took hold of her wrists and held them firmly either side of her head; now he was totally dominant, his cock paused unmoving an inch inside her, his body over her, his head directly above hers looking down at her, his hands pinning her to the bed with her wrists held firmly and pushed down into the mattress; from that position, I watched and listened in awe as he slowly inserted his cock into her fully submissive cunt, deeper and deeper until the full length of his long wide cock had stretched her and filled her to full depth, touching her womb and totally dominating her; while she was unable (and unwilling) to stop him, probably pleasantly surprised by his transition from polite man at the dinner table to dominant alpha male in the bedroom; I watched as he withdrew just a little and then thrust his cock hard back into her, making her gasp; then he withdrew a little more and did the same, thrusting back into her deep and penetrating her to the full; he did this repeatedly, withdrawing further each time, before thrusting hard back into her to full extent, bruising her womb lips; eventually he withdrew his cock completely from my partner's cunt, teased her cunt lips for a moment, before positioning himself and violently thrusting back deep inside her, forcing her to accept anything he did to her; he now started to fuck her, slowly at first then with increasing pace, as she lay below him and I watched; he kissed her briefly before he began fucking her with long firm strokes, full length from entrance to womb; he was getting faster and faster, while she was coming in multiple orgasms below him on the bed, my partner crying out her in passion as he fucked her while I watched; he got faster and faster, always fucking her to full extent and depth, very skilfully prolonging her orgasms; I watched in almost reverence as he brought her again and again to long lasting orgasm with his seemingly everlasting cock (she had completely lost is by now, shaking her head from side to side as she came); his stamina and strength was amazing, matching the size of his dominant cock, while I 'the Cuckold' could only watch and try not to breathe; then, after Jayne had succumbed fully beneath him, her bucking repeatedly in sobbing orgasms, with me subservient and helpless beside them, her Bull decided it was time to finish her off; he fucked her unbelievably hard, deep and fast while she came repeatedly beneath him, he totally dominated her pinning her firmly to the bed with her wrists held tightly by his strong hands, he fucked her now with real purpose and I knew he would cum inside her shortly, his bare cock would spurt his fresh sperm deep into her at the very entrance to her womb; I watched as they had a final joint climax, both gasping as he held his cock deep inside her and was obviously shooting his load into her on the first time they had met; while I watched and took photos of this momentous event. He was not finished, and after only a short while he made her suck his cock hard again; I watched as she willingly allowed him to force his cock inside her mouth and she sucked it from soft to hard, caressing and worshipping it, preparing his cock for what must be another longer coital joining together of Jayne and her Bull; he was extraordinary not just in the size and thickness of his cock but also is his stamina and dominance, and we were about to see how resourceful and ingenious he could be with different ideas of how to fuck a woman and in many different sexual positions; he began by pushing Jayne to a standing position facing the full length wall mirror, with him behind her looking at her reflection in the mirror; he pushed her head down, so she presented her butt to him, then he inserted his cock into her cunt from behind while standing on his toes to get the right height with her high heels; when he was inside her he pulled her head back so Jayne was looking at him in the mirror while he fucked her slowly at first then much quicker as she pushed back onto his cock; they fucked in this position for some time, looking at each other in the mirror, while I watched and took photos; then her Bull moved Jayne to sit on the armchair with her legs wide apart and he sucked and licked her clit until she came in a wet orgasm, spurting liquid into his face while they laughed; he moved her and this time he sat on the desk chair while she sat on his still erect cock, and I watched as Jayne fucked herself to orgasm by bouncing up and down above him as he steadied her with his hands; I realised that he had not cum a second time yet, amazing control, and her Bull now moved Jayne back to the bed to present herself on all fours to him while I quietly took more photos; he got on the bed behind Jayne and her Bull now forced his cock into her in the doggy position, while pulling back on her hair to make her gasp in surprise; he took no prisoners as he fucked Jayne hard and deep in that doggy position, which she was clearly enjoying by cumming once again on his wonderful cock; we discovered later that this is her Bull's favourite coital position and Jayne has been fucked many times by him like this since; it is also his favourite position to finally cum inside her, pulling her back onto him by grasping her shoulders, while he fucks her rapidly to full depth bouncing his cock repeatedly against her womb lips (she has told me he bruises her like this but she would not stop him doing it); on this first occasion he fucked Jayne at length like this, while she knelt in receipt of his cock and I watched in amazement at his stamina and control; finally he would fuck her harder and harder, until he pulled her back towards him and held her there while he came inside her yet again filling her with another big load of his active sperm while the Cuckold watched with my small erect cock clit hidden in my trousers. They lay in each other's arms on the bed to recover while I sat on the desk chair and mulled over what had just happened; it was obvious that they got on with each other very well, also that they were compatible sexually with his stamina and Jayne high libido; he had given her twenty or thirty multiple orgasms at a conservative estimate in only their first XXX session; he had fucked her bareback after asking her permission (not mine) and he had shot his sperm into her willing cunt; with only a short recovery time, he had then fucked her around the bedroom while I moved out of their way; then her Bull had fucked Jayne on the bed, cumming inside her again while she knelt before him; now they were in each other's arms completely ignoring my presence in the room; my conclusion as I sat at the desk looking at them, pondering the present and future, was that I had lost Jayne completely in only one session with her Bull; that she had found a sole mate and I had lost one; that Jayne would want to fuck her Bull many times in the future regardless of what I said; all this came true. I had become a subservient Cuckold in just one night, Jayne found she enjoyed being a Cuckoldress and her Bull liked to dominate both of us. This was the story of our lives from then on, initially with me the Cuckold being present at our meets with her Bull; with me having sloppy seconds afterwards by pushing my little cock into her when her Bull had gone or if Jayne was too tired, she would allow me to lick her clean, sucking fresh globs of his cum from her, savouring and enjoying the salty taste of her Bull's cum, rolling his cum around on my tongue before I swallowed it; she would have known then that I was bisexual but we never talked about it. After a while, I discovered by accident that Jayne had started to meet her Bull without me and our relationship changed yet again; she refused to stop seeing him and I reluctantly acquiesced to her will, only getting the one compromise that she would still allow me to lick and suck her clean when she returned home; after my discovery of their ongoing activity, Jayne agreed to tell me when she was meeting her Bull and I even continued to buy lingerie for her to dress up for him; I used to find this lingerie, her panties and her stockings freshly washed and drying in the airing cupboard after her meets, which would confirm to me without asking that her Bull had fucked Jayne that day; the other discreet confirmation signal that we had was that of Jayne putting a second slice of lemon in my G&T if she had met her Bull while I was at work; later this progressed to Jayne staying overnight with her Bull in his home or in hotels, while I stayed at home with my cock locked in a chastity cage; finally Jayne invited her Bull to fuck her in our home and bedroom, while I was at work or away on a trip, treating her Bull to white wedding lingerie, basque and panties, and white stockings as if this was their wedding night exploring each other, sucking and fucking all evening and overnight in our bed; they began living on these occasions as married partners, Jayne preparing meals and wine, her Bull being loving and attentive during and after the meal, then they would make love in the lounge before retiring to the bedroom to continue their loving close relationship by more fellatio, cunnilingus, 69 oral, playing for hours with toys, vibrators and dildos, before Jayne would encourage her Bull to fuck her in our bed as if it was their first time together. Jayne stopped telling me beforehand that she was meeting her Bull and became reluctant to tell me afterwards unless I specifically asked (she never lied and always told the truth to me, but I had to ask); they became very close friends and were in daily loving communication and Jayne used to glow when she described their time together, telling me the amazing things that they had done and how her Bull could bring her to multiple orgasms with his very mobile tongue and large cock; how they fucked in many different positions and how her Bull could cum many times in one session, each fuck longer than the last as he prolonged his control. Jayne was truly smitten by her Bull, loving his dominant nature in the bedroom but his polite and respectful nature at other times; Jayne started to tease me about my lack of stamina, my cumming too early, my inability to bring her to satisfy her and how she struggled to have an orgasm with me, in sharp contrast to the easy multiple orgasms Jayne had with her Bull; then Jayne also told me my cock was very small and not suitable to fuck her with, refusing to let me fuck her, making me resort to dildos and vibrators to satisfy her; there was just one concession that Jayne allowed to help me deal with everything, if I wore a large hollow strap-on pink penis-shaped dildo with my little cock constrained inside the dildo itself, Jayne would allow me to fuck her with this on our bed and would even dress up for me in used lingerie (only her Bull got to see the lingerie new and first time worn), with stockings and high heels; she would force me to use a vibrator on her first, then to give her clit and cunt cunnilingus to prepare her, then make me insert other large flexible coloured dildos into her and fuck her to orgasm with them, even making me use a triple method on her of a smooth metal vibrator inside her anus, a dildo in her cunt and a vibrator on her clit; all this before finally allowing me the concession to enter her with my cock inside the hollow strap on dildo and for me to fuck her like this until she came (I could never cum inside the hollow dildo); it was very humiliating for me but at least it was one way of me being emotionally close to Jayne and to give her pleasure when she was not with her Bull; I got nothing sexually out of it except that of the subservient Cuckold doing the bidding of his Mistress and Cuckoldress. This was how our relationship progressed, with Jayne becoming more confident, dominant and aggressive with me (while in contrast she loved being submissive to her dominant Bull); Jayne would make me sleep in separate rooms if she returned from her Bull in pain from his constant and long fucking sessions; she discovered and then used my chastity cages against me, locking me in a cage while she teased me verbally for hours with stories of what her Bull did to her and how he satisfied her so much she wanted to be with him every day; she locked me in a chastity cage and drove off to meet her Bull with me remaining locked up and helpless at home, often leaving me in a chastity cage overnight; then we progressed to my being locked up for more than a day at the weekend, then the whole weekend; once Jayne went straight to work after staying overnight with her Bull, leaving me locked in my chastity cage with no choice but for me to go to work and endure the fear of being discovered in a chastity cage by my work colleagues. Jayne became a different person and I became less and less of a man on her eyes; this is how we went forward in our relationship, with Jayne calling all the shots and enjoying her Bull's large and energetic cock whenever she chose, in his house, a hotel or in our own bedroom at home; Jayne also made all decisions about whether she stayed overnight with her Bull and I noticed this became more frequent, in fact everything was more frequent, their meets, overnights, his visits to our home and their daily contact. I realised that I had lost Jayne, even my being a subservient and accepting Cuckold was not enough; my allowing her to lock up and control my cock for hours or days did not satisfy her; my cock and everything about me was not good enough any more, when compared with her Bull; maybe if we had talked about my being bisexual Jayne might have shown me some sympathy and even empathy, allowing me to crossdress openly with her, she may even have helped me to apply my make up and given me tips on correct female dressing and applying nail varnish; she may even have fucked me with a special 'gay' strap on dildo, as long as I was clean and ready to be impaled; Jayne was of a character that such changed sexual activity might have been OK with her in our new relationship, with me becoming even more subservient and Jayne becoming the only person with a decent cock in our house (if her Bull was not visiting). With hindsight, I regret not asking Jayne to fuck me and my not talking to her about my bisexual and crossdressing desires; also about my not asking her to tie me up and whip me or ask Jayne to tie me to a bed or chair and leave me in restraints for hours, possibly for a whole night. These are the regrets of an ex-Cuckold, no longer in that relationship, who watched as his Cuckoldress got emotionally and physically closer and closer to her Bull, a dominant man who satisfied Jayne every time they met and who could bring her to multiple orgasms many times during their XXX sessions. He was and remains a better man than than me in every department and I have accepted that fact; he dominated me just as much as he dominates Jayne. Another regret I have is that I never asked to suck his cock in front of them after their first fuck in a session, it would have been a pleasure for me to suck his flaccid cock back to erection, it would have been wonderful for me to raise his arousal and prepare him to fuck Jayne a second time while I watched. I should have asked Jayne and her Bull if I could suck her Bull's cock and lick it clean after they had fucked. This is a real regret but I have sucked and been fucked by many equally large cocks since Jayne and I parted; she remained firmly with her Bull and I went on a crossdressing bisexual adventure on my own. Both Jayne and myself (her ex- Cuckold) are now in different places, which many would have predicted at the start of our journey years ago as she first accepted another man to insert his cock into her while I watched; she found she enjoyed being with her Bull more than her being with me, so the inevitable happened and we eventually parted; Jayne remaining loyal to her Bull and myself leaving for pastures new.
If you are a cuckold now (as I was with Jayne and her Bull), and you are having bisexual thoughts or tendencies, including crossdressing; then this story of my crossdressing bisexual encounters may also be your future. Don't be shy; literally grasp it in both hands and enjoy it.
DavidP
Ex-Cuckold, Bisexual Crossdresser.
Photos below of Jayne's first time with her Bull, them undressing each other, giving oral him fucking her bareback in different positions and her Bull cumming inside Jayne while I (her Cuckold) watched.
I can still remember everything as if it was yesterday; the way Jayne accepted her Bull immediately and was so comfortable with him; how they kissed and undressed each other as if I was not in the room; how Jayne had an orgasm while just lying on the bed with her Bull's head between her legs and his tongue on her clit; then she willingly allowed her Bull to tease her with his cock poised at the entrance to her now wet and ready cunt; I watched and can still see in my mind, how his cock slowly disappeared inside Jayne (my partner) while she first wrapped her arms around him as they kissed in coital union; then her Bull pinned Jayne to the bed by firmly grasping her wrists on either side of her head as he fucked her, giving her multiple orgasms before they both came simultaneously as he filled her cunt with his cum. All this while I watched, and then followed by her Bull fucking Jayne in many positions all over the room and on the bed, before he came again when fucking her from behind as she knelt on the bed to receive him. Amazing first time meet, never to be forgotten.
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