Jenny is a Gen X trans crossdresser from the UK with an obsession with red satin and lycra, and a sizzlingly honest take on Public Play and Partner Play. Her answers to my Crossdresser Survey were vivid, brave and brilliantly honest, and I had to share them. What follows is her story, edited into a Q and A so you can read her in her own words.
Meet Jenny
Q – Jenny, tell us a bit about yourself.
Jenny – I find myself as female to be a very sexy concept. I find myself as female to be sexy and attractive. I find validation in being seen/treated as female. And amusingly, I find enjoyment in the artifice and care needed to change to a passable female presentation.
Q – If we went out together tonight, all dolled up, what would the perfect evening look like?
Jenny – I find being seen as female validating and sexually arousing. I find other trans women to be sexually attractive, the more feminine the better.
Q – Your style — what is it about your colours and fabrics that fires you up?
Jenny – I like tight bright clothing, to show off my curves and make me feel sexy.
Q – And your favourite fantasy clothing — paint us a picture.
Jenny – I have a specialist silicone breastplate, with four breasts on it. I love the feeling of having breasts, the weight, the jiggle, the soft bulk of them, and it makes me feel more feminine than I would with two… I have a fair bit of xenophilia, and I think I look sexier with four breasts…. I look at myself in the mirror and it’s not just woman, it’s woman+.
Various items of clothing, but this one piece stands out :)
Crossdressing origins: early experiences and first sexual memories
Q – Do you remember your first orgasm while dressed as a girl?
Jenny – In a boring way, it was while masturbating while dressed. Felt pretty good, but nothing special.
Q – And the first time you had any sexual contact with someone while dressed?
Jenny – It was at a club (Candygirls, London), with another trans woman, and I was fondling her new breasts in admiration. I sank down to stroke her gorgeous satin clad thighs, moved across to kiss them, and found myself with her cock in my mouth… which was more than I was planning, so I backed off and let her other admirers have a go. It felt good at the time, then a bit much.
Out in the world: Jenny’s public dressing
Q – Do you crossdress in public? Do you wish you could, more often?
Jenny – Not too often but I do on occasion
Q – Tell us about your most intense encounter while dressed.
Jenny – I met a handsome man in a sex club, who was interested in having sex with me. Having got some practise, I ended up riding him reverse cowboy, with him fucking my (fake) pussy. As he did so, he also finger-fucked my ass….. it was in a side room with the door open, and likely there were some people watching as I was double-penetrated and fucked like a slutty busty woman…. It felt amazingly validating and sexy. :D
My partner isn’t interested in me while dressed up, and doesn’t care to know the details. So she doesn’t know.
Q – Shopping. Does going clothes shopping with another girl excite you?
Jenny – Get you excited
Jenny’s fantasies: body swaps, deepest desires and dress-up dreams
Q – Your most vivid or exciting crossdressing fantasy?
Jenny – Actually, I wrote these up during lockdown, and they still stand :)
Plan A (entirely viable)
I want to get glammed and femmed up, I want to walk dark streets on the way to a club attracting glances from passers by at my looks and figure. I want to strut into a club and turn heads from admirers and other t-girls. I want to have a few drinks and get my femme voice right. I want to take to the dancefloor, waggling my wide hips and deep cleavage, running my hands over my curvaceous body and lip-synching, if not singing along, as I dance and strut and lose my boy self in the music. I want to spend the evening thinking of myself as abundantly female, confirmed by how I look and act and how people react to me. I want to rest and chat and flirt with other t-girls, maybe having a little cuddle and a stroke. I want to trick people into thinking I’m most of the way through transition. I want admiring glances from men and women and perhaps the occasional fondle…
Plan X (pushing things)
I want the above, in somewhere more towards sex club than dance club. I want a sexier outfit that allows my perky nipples to show and my breasts to jiggle. I want to be fondled and lusted after. I want to cuddle a cute t-girl and feel our breasts pushed together. I want to go to a dark room or similar and feel hands stroking me, squeezing my breasts and my bum. I want to feel hot cock pressed against me. I want someone to run their hands under my clothes and find my new (fake) pussy. I want to put on a show for a sexy t-girl and kiss her deeply, before retiring to a private room. I want to straddle on top of them, stroking their breasts and cock, before lowering my pussy onto it. I want to be fucked in my (fake) pussy and if that doesn’t make them cum, to suck them off (with condom) until they cum in my mouth. I want to finish a night out feeling well fucked and appreciated.
Plan XXX (screw normality)
I want a sex club, with play in the lounge area. I want an outfit of tights, corset, netsleeves, and bra/panty set: lingerie and little more. I want to walk through there, swinging my hips, to feel hands on my thighs and butt. I want to lean against a wall in some grope room or glory holes or whatever, for hands to take my wide hips, to run caresses up and down my legs, to caress my breasts and tweak my nipple, to probe my lubricated holes…I want a sexy T-girl to press herself up against me, her hot cock against my thigh, calling me a sexy sissy slut as she squeezes my breasts before siezing me by the hair and dragging me in for a deep kiss…. I want another figure to grab me around my corsetted waist, holding me tight while fingers probe my ass. I want the t-girl to push herself onto me, our breasts squashed together as she slides her cock into my (fake) pussy, while from behind, the fingers are replaced by a slim cock, sliding between my bum cheeks and into my ass, fucking me from front and back. And then after being thoroughly fucked, I wander through the tables to find a pussy or indeed a friendly cock, and while I’m applying my tongue to that I get penetrated from behind by another, staggering as I get spit-roasted, moaning as my hands and tongue work frantically and my breasts sway beneath me…
Q – If you could body swap with anyone in the world for 24 hours, who and why?
Jenny – Nobody in particular comes to mind, but I’d like a female body, blonde, causascian, and breasts at D cup. Basically, my female self. To take out for a social trip and a wild night :D
Q – And if a fairy godmother made you the object of someone’s deepest desire for 24 hours?
Jenny – I… have no idea. :o
Q – If you could spend an evening playfully dressing up with anyone, who would it be?
Jenny – A trans girl I think a trans girl would understand and appreciate the effort and the artifice more, and maybe even find it sexier.
Reflections from Jenny: advice to her younger self
Q – If you could go back in time and offer your younger femme self some advice, what would it be?
Jenny – I’d say to myself at university: go for it. Start on the hormones, apply for the gender flipping paperwork, and go for it. Try going to the LGBT clubs, don’t be afraid to be shot down, and don’t think you’ll lose friends over it. Don’t worry about family opinions, get started now, because by the time you’ve got financial stability and your own house, you’ll have gone the [wife and family] route and be unwilling to jeopardise that. Also, I’ve seen the 20th century, and the sooner you get through transition the better.
Q – Is there a question I should have asked?
Jenny – A question would be: Why do you crossdress to the degree (not frequency) that you do?
I think of there being a spectrum of gender-bending activity, from the shy private cross-dresser to the full physical transition, and I sometimes wonder why people are at the point on that that they are.
My answer would be that occasionally I want to experience life as a female, but I can’t do so permanently for social reasons. So cross-dressing to the extent that I can pass (“femulation”) is my best way to taste that other POV….
Thank you so much for taking the time, Jenny. Honesty is everything to me, and you delivered it in spades.
If reading this stirred anything for you, gurls, you know what to do. Drop your thoughts in the comments. And if you haven’t filled out the survey yet, what are you waiting for?
Jenny xx
I live for all things feminine—stockings, heels, scarlet nails, and above all, the intoxicating touch of another woman. A translesbian muse and unapologetic hedonist, I share my most divine and wicked misadventures in words and now as a podcaster too. All gurls welcome. You are gorgeous. Just like me. xxx
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