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.