Boyfriend Overnight - Saturday 13th June 2026

I visited my new 'girlfriend' again on Saturday 13th June 2026, and stayed overnight alongside her in bed.

My new girlfriend's name is Francesca Elise, who is a crossdresser like me but needed her visitor to be in male mode to be able to kiss and cuddle him and to be penetrated by him.

I arrived at 14:00 on Saturday 13^th June and Francesca was not ready because she had underestimated the time taken to do a thorough multiple enemas internal cleaning in preparation for my visit. So I setup my laptop in the lounge, attached the XXX hard drive, and started to play the many XXX Trans videos on a random loop in VLC.

When Francesca came into the room, she looked gorgeous, wearing a wig, makeup, earrings, a long black and white flowing dress, black hold-up stockings and high heel shoes, plus Calvin Klein Eternity perfume. I got up to greet her, kissed her and held her hand as we sat on the sofa in front of the laptop. Then we started kissing and Francesca stroked my cock through my clothing; I took off my shorts and resumed kissing her, and she now had full access to my cock; we French kissed deeply and for a prolonged period; I started to fondle Francesca’s semi-erect clit through her dress, then pulled her dress up and fondled her clit through her panties; Francesca suggested that I might do a little more to her now erect clit, the inference being felatio (cunnilingus) and I got off the sofa, kneeling between her spread legs stocking-clad legs; I pulled her clit out from her panties and started to lick and suck it, spending time pleasuring it for her as Francesca watched the XXX video and enjoyed my attention to her clit; I could taste her precum in my mouth; I said that I wanted to fuck Francesca, and she got into ‘the position’ on all fours in front of me; I tried to enter her but Francesca’s cunt entrance was incredibly tight as she was a virgin; so we moved to the bedroom intending to have sex on her bed; Francesca covered the bed with a sheet and put pillows below the sheet to raise her butt; then she lay face down, butt raised, with her legs spread; I tried several times to enter her and still found her cunt too tight; so I went back into the lounge to fetch the three strap-on dildos that I had put into my ‘toys bag’; I put on the smallest strap-on dildo, applied lubricant to it and pushed more lubricant into Francesca’s cunt; then I got into position between her legs and slowly inserted the dildo into her cunt; after a moment her entrance widened and I progressively inserted the dildo until it was eventually penetrating Francesca to the hilt; now I could fuck her, gently moving back and forth, pulling the dildo almost out and then pushing it deep inside her again; Francesca was now being truly fucked as I started to increase the speed of my thrusting; it was a perfect scenario, Francesca face down legs spread on the bed, myself above her and between her legs and my strap-on ‘cock’ rapidly thrusting into her to the hilt; exactly what Francesca had been anticipating, the only difference being the dildo being used instead of my cock, which had now become fully erect; so I withdrew the strap-on dildo and swopped it for my erect cock, easing my cock into Francesca’s cunt and fucking her; a wonderful feeling and fulfilling for both of us. I returned to the lounge and sat on the sofa while Francesca changed her outfit; Francesca returned to the lounge wearing a pink dress, stockings and pink trainers, and more CK Eternity perfume; she looked and smelt wonderful; we sat watching the XXX video, the video we were watching was a Petra TV Training video and Petra was being severely and repeatedly fucked by a man in many positions; Francesca was calm and relaxed, having just been fucked on the bed; she pulled my cock out from my briefs and started to masturbate it; all this time we were watching Petra being dominated and rapidly fucked to the hilt by the man; then Francesca started to suck my cock, and she performed felatio on me which felt wonderful; Francesca asked me about the wigs I had brought and we got them out of the box to look at them; Francesca left the room, returned wearing one of the wigs and she looked fantastic in it; we continued to French kiss, each fondling the other; I pulled her clit out and pleasured it; I was now wearing a black nightie, black panties and black hold-up stockings; Francesca accepted this, her ‘boyfriend’ now clothed in female attire, and we kissed deeply as each of us pleasured the other with our hands, her clit fully erect and my cock inside my panties also erect; we kissed like this for a long time, enjoying the post-coital moment; I asked Francesca is she would fuck me and she said “Yes”, so I moved to ‘the position’, all fours on the floor; Francesca, knelt behind me and entered me, starting to slowly fuck me with her erect clit, as I knelt on all fours with my head on the sofa; it felt wonderful, feeling her large clit penetrating me and thrusting to the hilt inside me, the pleasure was enormous; I suggested that Francesca use a strap-on dildo to fuck me, as I had used to fuck her, and Francesca put on the strap-on, inserted the dildo into me and was now fucking me very deep to the hilt; it was momentarily uncomfortable as the dildo spread my ‘sissy cunt lips’ and also uncomfortable because of this second dildo was longer than that I had used to fuck Francesca; but after a while, with her rhythmically thrusting the dildo into me, I got more and more aroused; Francesca was pleasuring her ‘boyfriend’ by ‘pegging’ him with a long thick strap-on dildo; all I could do was kneel on all fours and take her thrusting, feeling more and more aroused with each thrust and getting closer and closer to orgasm; my ‘sissy cunt lips’ were tightening around the dildo as I got near to cumming, which did not happen but the feeling was wonderful; Francesca changed her attire into a grey pleated skirt, and she looked fantastic; I suggested that we might go back to the bedroom to perform 69 felatio on each other; I got on the bed upside down, with my head to the bottom of the bed, and Francesca lay beside me in the normal position; we lay on our sides to give access to cock and clit, and we started pleasuring each other with our mouths; it felt wonderful, being pleasured with felatio, feeling lips and tongue on my cock as I sucked and licked Francesca’s clit; then Francesca asked me to use my teeth on her clit as part of pleasuring her; I was surprised but I did as requested, gently pressing my teeth onto her clit and I moved my mouth up and down,  sucking, and licking her at the same time, also masturbating her with my hand gripping the shaft of her clit; Francesca got more and more aroused, thrusting upwards as she lay on the bed completely ignoring my cock and focussed on receiving pleasure; she thrust deep into my mouth as I bit her, so deep that I was repeatedly gagging as her very erect clit hit the back of my throat and threatened to go further down my windpipe; Francesca obviously enjoyed the feeling of me biting her, as well as my constant licking and sucking; then I started to taste her precum in my mouth, savouring it as I moved my flickering tongue over the tip of her clit; I had not tasted cum for a very long time, for decades, and it tasted divine; Francesca did not spurt into my mouth, she simply ‘leaked’ cum as she trust upwards and I sucked and licked her; it was obvious that Francesca would not actually cum but she had really enjoyed the moment; I asked Francesca if she could use her teeth on my cock as she performed felatio, because no-one male or female had ever dragged their pressing teeth up and down my cock; Francesca did as requested and started to give me felatio, with her lips, mouth, tongue and teeth; it felt amazing and I was writhing in pleasure, trying desperately not to cum in Francesca’s mouth (which she had requested on my first visit to her home); clearly Francesca did not like or had never really tasted cum, and was reluctant to receive it in her mouth; so I told her that she had been leaking pre-cum into my mouth while she thrust her clit deep into it, and while I sucked, licked and bit her clit; I told Francesca that pre-cum tasted slightly salty and that I actually liked the taste, also telling her that cum itself was salty; after Francesca had performed her wonderful biting version of felatio on my cock, she asked me if I was hungry for food and I said “Yes”, so while Francesca changed into yet another costume, I changed into male attire, took the laptop and XXX hard disk down to the kitchen and set it up on the table still playing XXX videos; Francesca had put the pink dress on again with a wig, and she looked wonderful as she came downstairs and entered the kitchen area; we chatted as she prepared dinner for us; a salad and a very tasty fish; we ate and chatted, drank wine and chatted, ate some more and chatted, all an easy ‘get to know you more' conversation, occasionally interrupted by us watching a particularly interesting XXX video now showing on the laptop; we chatted endlessly and pleasantly for hours, finishing off the original Rosé wine and then a bottle of white wine, then cold beer; because I was stopping the night this time, there was no need to worry about alcohol or time, which moved to after midnight and on to beyond two o’clock in the morning when we finally got up from the table and cleared the plates into the kitchen area; then we sat on one of the sofas, cuddled and kissed, started to fondle each other and became aroused again; rather than start sucking cocks and clits in the den, Francesca suggested that we move up to the bedroom and onto her bed; I put the laptop and XXX hard disk away, packed the toys in their large bag, prepared my items for leaving early in the morning, took my toiletries into the main bathroom and put on my nightie and panties; Francesca joined me in the bedroom and went into the ensuite to take off her makeup; then she got into bed with me and we started kissing again, me with both my arms around her; she started to rub my cock through my panties, then slid my cock out so that she could grip it with her hand and masturbate it; I moved one hand down to her clit and did the same thing; then I changed position and started sucking her clit, biting is as instructed earlier, sucking and licking it; Francesca almost immediately started thrusting her very erect clit deep into my mouth, causing me to gag again but this time I could control the gagging; Francesca’s salty precum started to leak onto my flapping eager tongue and she continued to leak precum until she started to thrust in earnest into my recipient mouth; Francesca came in my mouth, not copiously but obviously given the deepest thrusts were held against my throat; I could feel her salty cum, not a lot of it but enough to know that she was satisfied; I asked her to resume sucking and biting my cock, which she did, and that’s how our afternoon and evening ended, with a very satisfied Francesca and me also being very satisfied (but not cumming in her mouth); my cum and associated orgasm would have to wait until I returned home in the morning; it must already have been 3 am and I had asked for a 7:30 am alarm, so we did not get much sleep but we slept side by side, my arm around her after briefly fondling her clit through her panties; when the alarm did sound, even though I needed to go to receive a home delivery, I couldn’t resist sucking and licking Francesca’s clit again for a final time on this visit, biting it gently as I gripped and masturbated it with my hand.

It was time to get up, my bags were almost packed earlier, so it was just a matter of packing my toiletries and putting on male attire, leaving without having a shower because I could do that at home; we kissed at the door in the hallway and I left my fully cross-dressed Francesca inside the doorway as I said “Bye for now” and walked to my car.

I eagerly await my next ‘boyfriend’ visit to Francesca my girlfriend, because on my next visit we will take our relationship further; I have instructed Francesca to train and expand the capacity of her ‘clit lips’ with an anal plug that I had left behind; also for Francesca to install an under mattress restraint system in her bedroom, ready for me to immediately restrain her, at a time of my choosing on my next visit; Francesca would be face down on her bed with her spread legs and arms held by the wrist and ankle cuffs of the under mattress restraint system; then, while Francesca is helpless, I will tease her sissy cunt with a lubricated finger, insert a range of objects into her, penetrate her with plugs, dildos and other toys, then fuck her lubricated cunt first with a strap-on and subsequently with my erect cock; I will then proceed to fuck Francesca deeply and increasingly more rapid until I cum inside her, spurting my cum into her helpless sissy cunt; after that Francesca will need punishing, for being a naughty girl, and I will use my hand, a whip, a paddle and a riding crop on Francesca’s butt until it is showing red marks (not blood); I will probably want to lubricate her cunt again and fuck her to completion again, which will take some time for my second cum. I have requested weekly overnight visits, on Fridays/Saturdays (moved occasionally to Saturdays/Sundays if necessary).

Until the next visit….

x

Boyfriend

I have become the boyfriend of my new friend in Spain. He, like myself, is a crossdresser and he ('she' when 'dressed') has been thinking for some time about having a boyfriend. We have met twice now. The first time was as two crossdressers in my home where we kissed and fondled each other, sucked cocks and my friend then fucked me with 'her' cock, which was a wonderful experience. The second time was at my friend's home, so 'she' could have time to put 'her' clothes and make-up on before I 'the boyfriend' arrived. We kissed and I helped attach 'her' rear suspenders to 'her' stockings, which was very arousing for me. We had a wonderful evening, kissing and caressing, fondling and sucking cocks while watching XXX trans videos and pictures, the latter played while we enjoyed dinner together.

I am looking forward to returning to my friend's house, for more of the same and to extend our exploration of each other to include rimming, anal play and anal teasing, toys, lovemaking with my cock inside 'her', while we are in the house, on the bed and in the bed for a sleepover, so we can kiss and cuddle at night.

I am happy to be the boyfriend, dressed in male clothing but I do hope for shared oral, 69, even pegging using a strap-on and hopefully after I have fucked 'her', 'she' will then reciprocate and fuck me.

Versatile

I have not had the opportunity yet in Spain but in the UK I was versatile during XXX meets with other males and/or crossdressers. There is the idea of being a 'Top' and being a 'Bottom', where the Top is normally the one to penetrate the Bottom; but this separation doesn't hold up in many situations where the XXX session is prolonged. The first time that I was penetrated by a penis (having already pleasured myself for many years with a variety of dildos, vibrators, and other suitable objects), it was during a XXX meet in Leeds (UK); we were both wearing stockings and lingerie and he (she) had a wonderful, beautiful long cock that I could only stare at as I sat on the sofa as he (she) dropped her jeans directly in front of me; it was natural for me to immediately touch and suck her cock; she lay on the sofa and I spent many minutes just pleasuring her with my lips, mouth and tongue being careful not to over arouse her, just keeping her on the edge for long moments before pausing, relaxing then starting again; it meant that she did not cum on the sofa and when I was not sucking her cock, just holding and masturbating it, we kissed for a long time, fondling and cuddling each other; she asked me if I wanted to join her in the bedroom upstairs; when we entered the bedroom she asked me if I knew how to give myself an enema and offered to show me the best way to do it, guiding me into the bathroom where there was an enema attachment on the flexible shower hose; she inserted the attachment inside herself and slowly opened up the tap, warning me to keep the water pressure low when it was my turn and just let it flow inside me until I felt full, then stop pause for a moment and release into the toilet before repeating the process until the ejected water was clean; then use the enema attachment at least five more times checking each time for a clean release of ejected water, plus one additional enema which she said I should hold inside me, walk around for a few moments and then release, again checking for a clean ejection; she did the whole process while I watched, then I did the same while she watched; we then dried ourselves with a towel and returned to the bedroom; what happened next was that she asked me to fuck her because she liked to feel a penis thrusting inside her; she got on the bed on all fours, spreading her legs while I put a condom on; I then lubricated her sissy cunt, pleasuring and exploring her with my fingers for a few moments while I positioned myself behind her and between her legs; I lubricated my erect cock and very slowly, pressed gently against her opening, encouraging her to widen her sissy cunt for me as I carefully increased the pressure, easing off or pausing for a moment to allow her to adjust to the cock widening her sissy cunt lips; I took my time and she was moaning with pleasure, then there was a plop and the head of my cock passed beyond her sissy sphincter; after that it was easier to enter her but I still did it slowly, backing up a little, pushing forward beyond the previous depth and eventually I was inside her to the hilt; at that point she was used to my cock in her cunt and I could start gently fucking her, almost pulling out, then thrusting my cock back in again; I increased speed over a period of time and she was moaning constantly as she rocked back and forth on her elbows with her head on the pillow; I fucked her rapidly now, with my hand underneath her gripping her cock, manipulating her erect sissy clit as I fucked her at speed; at no point was I totally forceful, although I could do so if requested, on this occasion I could tell that she wanted me to 'love' her and treat her with respect; as I came inside her she was releasing long low moans of pleasure; then I carefully withdrew my cock from her sated sissy cunt and I removed the condom now swollen with my cum. We cuddled for a while on the bed, kissing and talking, as she told me how much she had enjoyed it. Then 'she' fucked me with her cock also in a condom and she took my anal virginity.

So I had kissed, cuddled, and talked to her, fondled, licked and sucked her, felt her cock growing in my mouth; I had entered her sissy cunt and fucked her gently, then increasingly more rapidly as she moaned with pleasure and I came inside her; then she did the same for me.

That's why the title of this blog entry is "Versatile", because a 'Top' is not always a Top and a "Bottom" is not always a Bottom, even during the same XXX session. I discovered that I enjoyed pleasuring and fucking her, and then we switched. The bottom line (if you excuse the pun), is that I am very happy with both and if my XXX crossdressing partner wants me to fuck her, then I am very happy to oblige.

Chatting About Crossdressing

Yesterday, I enjoyed chatting about crossdressing with another person, while we sat next to each other. It was wonderful and so refreshing to be able to talk, admiring 'her' clothes and make-up while exploring our thoughts and each other. It was arousing and fulfilling, kissing and fondling, feeling her arousal growing in my hand as we kissed on the sofa. I moved my head down and sought that arousal with my tongue and lips, sucking on 'her' beautiful cock, licking it and feeling it grow hard in my mouth.

We moved to the bedroom and, with me on all fours on the bed, that large cock slowly entered me, stretching my sphincter. A little painful at first, because of the size of the bulbous tip of 'her' long thick cock, then beyond the entry a slow penetration to the hilt. The repeated withdrawal and subsequent inwards thrusting had me gasping in pleasure, as my sissy cunt was filled again and again with 'her' beautiful, long and thick cock. Literally 'fulfilling'. My sissy clit was weeping precum into my panties. my stocking clad legs were spread in submission, my breasts, shoulders and head resting on the bed, with my butt raised and sissy cunt gaping. The pleasurable feelings continued as I was pounded by 'her' cock and our coitus bound us together.

Afterwards, as we lay on the bed watching XXX videos of similar actions, I sucked and licked 'her' cock in prolonged felatio, alternating between gripping 'her' cock tight and releasing it so that I could lick along it's length, then flicking my tongue over the head, pleasuring it with my moist lips, taking as much of 'her' long thick cock in my mouth as I could and sucking it while using my hand to twist or pull along it's length. There is a similar amount of pleasure in oral sex before and after penetration, feeling a cock grow erect in a mouth and subsequently thrusting inside a sissy cunt, then relaxing afterwards with that same cock given an oral gift of thanks.

What was so wonderful about yesterday was that, after two crossdressers had enjoyed each other, the chatting continued in a natural way until we parted.

Nice memories.

Conversations about Crossdressing

I wear ladies clothes every day now at home, comfortable in crossdressing while doing normal daily tasks. The choice of clothing varies but normally includes panties, tights, leggings, padded under bra (with silicon inserts), strappy camisole, sports bra, padded long camisole, long sleeved top and a ladies sweater, plus wedge heeled open-toe sandals This keeps me warm in the winter months, and allows for me to wear a skirt if I wish, or I can change from sweater into full flowing long dress. On occasion, if I wish, I can also wear a bra and stockings (hold-ups or with suspenders), perfume, lipstick, mascara and make-up.

What I am hoping for is someone for me to talk to openly about crossdressing, who is on the same wavelength and with whom I can just chat about crossdressing as if it is a normal topic of conversation. 

The ability to express my thoughts to a person while I am cross-dressed would be wonderful.

Nights Out and Conversations about Crossdressing

Recently, I went to a nearby LGBTQ+ friendly bar (marked as a Gay Bar in Google Maps). I have actually been there four times now but on the first two occasions I was too early and there was only access to the ground floor bar, whereas arriving later towards 11pm or midnight gives access to the lower bar where the shows are on. On both occasions when I have been in the lower bar, the evening did not really get started until midnight and the clubbing atmosphere continues into the early hours and until 4am in the morning.

I went to this gay bar in male visible clothing but underneath I was wearing female panties, tights, and a camisole; which became part of the conversation with an openly gay guy who kept buying me drinks.

Nothing happened, and I left the bar while the gay guy was dancing with the TS singer on the stage.

Quite an experience for me, because as a closet crossdresser I was finally able to talk freely and openly, face to face with another person about crossdressing.

Cross-dressing

 I started cross-dressing as a child, wearing borrowed clothes and tights. I found it arousing and enjoyed it. At the same time, I also experimented with self-bondage, while 'dressed', which I still do today.

My journey through life, being a willing cuckold, watching my partner enjoy another man, included the desire to clean her up afterwards, licking and sucking his copious, salty cum from her now gaping vagina. Initially, I was allowed to push my tiny cock into her and also cum inside her, but then that too was denied. She started seeing him without me and I only got to know about their meetings afterwards, when Jayne would tease me as I cleaned her up with my tongue. That meant my desire to suck his cock, before he fucked her and later clean their coital fluids from his cock, was unfulfilled because I was no longer present to watch them and we did not progress that far.

The next phase on my long journey, was to meet other like-minded males, either also cross-dressers or later with dominant males who liked to fuck a compliant 'sissy cunt'. With other cross-dressers I could be a 'top', 'bottom' or 'switch' dependent on my meet partner(s) but, because of my small cock, I preferred to be a 'bottom' and for my 'sissy clit' to be sometimes locked up in a cock cage. Other men, cross-dressers or dominant, have sucked my cock and I have sucked theirs; I enjoyed giving and receiving fellatio, 69 and other oral positions; I could do deep throat, with a cock pushed all the way down without me gagging. I also craved to be helpless during these meets, and punished for allowing others to explore me, because now I was also being fucked in my 'sissy cunt'. To be 'dressed', tied up, bound, gagged and totally helpless while an erect cock pounded inside me and exploded into a condom or filled me up, was a wonderful experience. Then to be smacked, caned, whipped afterwards was both painful and fulfilling to my subservient mind. I remember the first time I was fucked bareback, by a man I had met several times before; on this occasion I had my hands bound together behind my back, while I lay face up on the hotel bed wearing a blond wig and makeup; my ankles were also cuffed and locked to a leg spreader, which he raised over my head to give him access while he pushed his throbbing cock slowly into me; I knew that he had not put a condom on this time but I was totally helpless to stop him as his long, thick cock took me inch by inch; when he was fully inside me, balls deep, the look in his eyes was of triumph and almost manic; he was taking me bareback whether I liked it or not, and I liked it; he took his time, gently fucking me, then gradually increased speed until eventually he was rapidly taking me as I lay helpless beneath him; he came deep inside me, spurting his cum into my  'sissy cunt' as I lay there wearing a bra, panties (pushed aside), suspender belt and stockings, high stiletto heals, the blonde wig, mascara, makeup and lipstick; I was fulfilled and on all our subsequent meets he fucked my 'sissy cunt' bareback many times. Another dominant male, with a enormous cock, liked me to come to his home and get 'dressed' in his bedroom and ensuite while he remained downstairs in the lounge, waiting in anticipation; he used to buy new clothes and shoes for me, laying them out on the bed for me to look at and put on; then I would go into the bathroom to put on my mascara, eye shadow, makeup, lipstick and perfume, also spraying the latter inside my panties for him to enjoy when rimming me and teasing my 'sissy clit'; sometimes I would wear a cock cage and then he would tease my swollen balls; he liked to hear me clip-clopping down the stairs in new high heeled shoes, touch me and stroke my stockings, kiss me and fondle my breasts, rub and squeeze my cock and balls; I used to suck his already erect cock while he sat on the sofa with his legs spread for me, so I could get nearer, on my knees before him, hovering my mouth over his throbbing cock and blowing on it, then licking and sucking it while he encouraged and sometimes forced me to do it with his hand on the back of my wig; we fucked in many different positions, with me sat on him in cowboy or reverse cowboy, him mounting me in rear entry while I was resting my elbows on the sofa, or on all fours or pushed flat onto the carpet, missionary when he would kiss me while I had my legs raised and spread for him; each time he would be gentle at first because his cock was huge, thick and long, allowing me to get used to him again on each visit; he would offer me poppers and he would take them himself; we would use lubricant and I would inject myself with lube beforehand; he never used a condom because he wanted to enjoy spurting into me, which he did on multiple occasions during each visit; after each climax we would rest a little while, then I would suck his cock and when he was erect he would enter me again, in a different position; we never used bondage but he was very dominant, smacking me and telling me that I was a dirty sissy, before, during or after sex; and I used to crave his cock and his dominant nature, enjoying the tremendous feeling of him spreading my 'sissy cunt lips', then entering me, and thrusting his cock deep inside me, then finally I could feel his wonderful cock exploding into my 'sissy cunt'; I miss his cock and I miss the clothes and shoes he used to buy me.

I gave all my cross-dressing items away when I left the UK and settled in Spain, but have now started to buy female items for me to wear. What I miss is the opportunity to meet other like-minded males, either cross-dressers or dominant. This is the next step on my journey, to share a cross-dressing life, to talk and chat with others while cross-dressed and, maybe to also have a sexual experience with them. The first step is writing this, in the hope that someone reading it will contact me.

The next part of my journey has begun.