Wednesday, 11 March 2026

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.

Monday, 2 March 2026

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.


Wednesday, 25 February 2026

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.