Wayout2: Where Fun and Terror meet over a glass of Red wine and a Fondled Bottom

On Saturday night, as part of an uber-session with the sublime Cindy at BWBG which I’ll talk about at length in the next couple of posts, I went back to the Wayout Club in London. I spent a good three hours dressed identically to the picture at the top of this blog post surrounded by admirers, T-Gurls and a surprisingly large amount of transexual prostitutes. It was…….. eye-opening.

I have a good imagination. I’m not even going to be modest about it. As such I had built up a picture in my head about how the evening would go. I’ve been to the Wayout once before but this was different – the first time I used a friend as a safety shield, which was a good and a bad thing. Good in that I had an arm to lean on, bad in that I couldn’t not be ‘him’. Being with someone who has known me for thirty-odd years meant that I couldn’t be Sarah, I defaulted to ‘him’ and got very drunk. It was fun but I’ve always felt that it would be nice to go to the Wayout with no strings tying me to ‘him’ at all. I could finally be ‘me’, completely, and see where she took me.

Of course, it was nothing like that. It was humorous but it also highlighted some of the problems that I think I’ll always have.


But first, a brief overview of what happened.

I spent all day in a nine hour session with Cindy, the second nine hour session in two days. To say I ached would be a vast understatement, my hips felt detached, my ankles were sore, my feet had stopped feeling like feet the day before and my back hurt a little bit from carrying that little bit of additional weight up front. I *love* these sessions, but boy, they do take it out of a girl.

We were going with Cindy’s lovely partner, Vicky, and two other T-Girls who were showing up for a makeover just before we went out. The first T-Girl was an experienced girl who had spent a year working every Saturday as a barmaid in Paris, which was instantly impressive and a little humbling. She wore a bodycon dress and a pair of thigh-high boots to die for. The second was a lovely T-Girl from America who, having retired, wanted to discover herself. She’d never been out so she had a level of fear/excitement that I could understand.

Me, I was terrified again. All the ideas and wonderful fantasies kind of slide into the background as the time got closer and it dawned on me that I’d be going out into the dark night of London with nothing between me and whatever lay out there but a blue lace bodycon dress and a very tight corset. In stockings and four inch heels.

It got closer to the time that we’d head out and I took to pacing, shoes off of course. Heels are wonderfully sexy, and I think they’re essential for the look, but as a full-time bloke my legs and feet suffer a little after wearing heels for an hour. The anxiety was rising and I found myself asking whether I should, err, bail.

Before I got the chance to embrace my cowardice the time came to go out and suddenly I found myself squeezed into the back of Vicky’s cab with two other T-Girls and Cindy, speeding off across Tower Bridge towards the venue of the Wayout.

I watched the city flow by, letting myself down by turning my face away from the taxi’s windows whenever we stopped to avoid making eye contact with any Muggle in their car parked next to us.

A bit of small talk, surprisingly normal for three men but odd when the men are dressed in sexy club gear, and we arrived outside the club. I stepped out of the taxi, wobbling on the pavement before I caught my balance, and I was there again. Out of the safety of the cab I felt vulnerable, a feeling I’m not used to. So I pulled my legs together as I think women do, and starting tottering towards the club, the terror driving my pace as fast as it could, that wonderful clicking sound of my heels ignored in my haste to try and get somewhere safe.

Like the first time I went I almost stumbled over the step, forgetting how odd women’s shoes are, and almost tumbled gracelessly into the packed club.


Now, in a lot of my fantasies I swan into wherever I choose to go as Sarah, wide smile and sexy walk, find a seat, take in the atmosphere and get serious thrills from the idea of being the woman I’d like to be. In reality, it doesn’t quite work like that. For a start, regardless of how hot I was dressed (and, to give Cindy credit, I think I was kinda hot) all I could see was some strands of blonde hair that I kept trying to eat or sweep out of my eyes. I had a smile, but that was to counter the terror within that kept reminding me that my comfortable usual shield to the outside world of t’shirt, hoodie and jeans was piled in a nicely folded stack a mile or so away while I was stood, dress to mid-thigh, feeling the cool air from outside the club circulating around my bare, shaved legs beneath a thin layer of nude stocking, wobbling around a little on an uneven floor in serious fuck-me heels. I tried standing in a feminine way, putting weight on one leg and letting the hip push out, and that felt nice. Hand on my hip clutching a purse, other hand wrapped, shaking slightly, around a glass of red wine, I watched the club while trying to make my 6ft2in *before* heels frame as small as possible.

I had some lovely chats with the American T-Girl, Ellie, who was in the same boat as me, just dealing with it *way* better. For a start she was stunning, and stunning in a small framed, feminine looking way, while I hulked over her like her court-assigned Amazon bodyguard. And as we chatted it became apparent that, although I felt myself to be terrified and in a minority of one, we felt the same way.

There’s something about taking on the woman’s role that is immensely shocking for a man. You’re used to a level of independence, of power, in and of being someone with external genitalia. I’ve never been, nor never will be, a sexist, but I’ve been very unaware at how hostile and unfriendly a lot of environments are for a woman out looking to have a fun evening, and this time, for the first time, I felt it.

It was hard to find somewhere to look. Everywhere I looked there were girls who looked *way* better than me, and occasionally I’d lock eyes with them, and get a smile, and I’d go terribly shy. Or worse still I’d make eye contact with an admirer.

And that’s when it struck me at how very, very far I was out of my depth. I’d gone for a sexy club look and was about to reap some of the ‘benefits’, and I was nowhere near to be prepared for the next couple of hours.

Firstly, the groping. It’s a busy club, so finding a place to stand was tricky and we ended up stood next to the dance floor but almost in the passageway to the toilets at the back of the club. I had a chat with Elie, and a chat with Gina, the other T-Girl that had came along, and then I got fondled for the first of a number of times.

It’s hard to describe the reaction you get. I’m a bloke 99.9% of the time and I have space issues – I like my personal space, I would never touch a woman without her consent. Not here though. My tight rear-end was easy game.

The first grope was from a middle-aged admirer who had obviously been on his way to the gents but decided that standing behind the 6ft++ leggy blonde in the too-short lace dress was a nice place to take a breather. To give him his due it wasn’t an aggressive grope but rather the firm placing of his hand on my bottom and a slow rub, circular at first and then drawn out to the top of my thigh. I seriously thought I had pins and needles until I turned and he drew his hand back, winked at me and then carried on to the toilet.

Now, there’s a lot of T-fantasies where that is a wonderful thing that leads on to whatever. But in this case, right then and there, it felt creepy as hell. I genuinely felt a little violated and it just became apparent that the ‘but she was dressed like she was asking for it’ defence of many a scumbag is reprehensible.

I was trying to find words to explain to my comrades-in-skirts as to what had happened when bam, it happened again. This time a gentle hand placed on one side of my derriere drawn across to the other side.

A bit of explanation at this point – I had two butt padded undies on, on top of my own Y-fronts. Yeah, it spoils the illusion a bit, but I’d been doing 18 hours of posing in underwear that passed as ‘cheese-wire-for-the-groin’ and I needed to keep my abused and partially crushed dangly bits as gently contained as possible, so for me to feel a hand across my bum meant that there was a bit of pressure going on.

I spun on the spot and instead of an admirer it was one of the most beautiful T-Girls I had ever seen and, flashing me a smile that made my knees wobble, she headed off to the toilet as well.


With a kind of ‘two strikes and you’re out’ approach I decided I needed to get out of the firing line and luckily a booth had opened up, so we all headed over and sat down, me with somewhat of a sigh of relief, constrained as it was by the awfully tight corset that was keeping my figure somewhere near an hourglass while moving my internal organs around.

I had a chance for another wonderful chat with Elie and was gladdened to hear that like me she was stunned by the difference in feeling you get when you attend a club as a girl.

You need confidence. Tonnes and tonnes of confidence, and mine was ebbing towards zero. Granted, I’d done 18 hours of posing with minimal sleep, had drunk about a bottle of red by now and the idea of being behind closed doors was stronger than ever, but I started to warm up a little to the situation. I was sat down, which was a blessing, I was crushed into the seat between Elie and Cindy and, without sounding like an odd beast myself, the feeling of stocking on stocking was nice in a soul-warming way, and I could watch the club without being an active member of the grope/fondle floorshow.

At some point Cindy and Vicky stepped out and it was just myself and Elie, and, approaching closing time, the admirers started to descend.

The first guy I felt sorry for. If I had had a modicum more confidence I would have engaged with him, he was pleasant, very polite (he complemented myself and Elie as ‘very beautiful ladies’), but my urge to communicate was non-existent and after a couple of half-hearted attempts to engage in conversation he drifted away, leaving myself and Elie to sigh in relief and raise eyebrows at each other.

Which was another fantasy crumbled. I love the idea of embracing my feminine persona, letting her run wild, but I was like a rabbit in the headlights. And the sad thing was my form of defence seemed to be to try and drag ‘him’ back to the surface. I kept the pose, let my head tilt to the left in what I thought was a sexy way, pushed the hair from my eyes gently with the ends of my long red fingertips, and talked like a bricklayer after five pints.

Not because I wanted to show any masculinity. The fear of being where I was, dressed as I was, was having a reaction that afterwards I was quite saddened by.

Being out is a wonderful chance to experience the highs *and* lows of being a woman int he 21st century. The clothes are restrictive, at least in different ways to the usual male attire. The shoes make every step a delicious battle with gravity. The smell of perfume on your skin is like no other drug. Yet I was too afraid in myself to really embrace it.

I had a great time, granted. There’s lots of moments I will treasure until the day I die – meeting Vicky Lee, the proprietor and organiser of the Wayout club, was lovely. She was so friendly even though she must have to talk to so many terrified people, I just wanted to hug her. And should have, but the terror stopped me. Sharing a look with Elie as she was grabbed by another T-Girl who wanted to gush over her outfit. Meeting a girl called Zoey who had a wonderfully kinky way of getting past people who were sat on the sofa next to us (she sidled over the lap of a very attractive TV and stopped to rub her bum on the girl’s lap which left the TV and her date looking stunned). Using the Ladies (although the same conversation about blow job techniques seemed to be going on which was mildly off-putting while I was fighting through the bottom of the corset and my two thick sets of bum-padding to get at my undies so I could pee sitting down in the cubicle which I had locked as quickly as was humanly possible).

But there were other moments. A young admirer at the end of the night who wouldn’t take no for an answer from me or Elie and was determined that one of us would go home with him. That wasn’t fun, partly because I was trying to work out how I could disable him without killing him (having nails on means that it is very possible you can break a hyoid bone in the throat when you punch them there – subtle tip girls, the throat is a good place to incapacitate someone but if you shatter the hyoid bone you better be ready to give them a combat-trach, or cricothyroidotomy (go look it up, 🙂 ) so they can breath through the swelling. Too much info?). Luckily Elie was very firm and we got rescued by the ever watchful Vicky and Cindy, but for a moment again I saw a side of late night trysts in the T-community that has a dark edge.

All in all I feel a little disappointed in myself, but not at all surprised. It’s been two nights since I did it and I’ve been over what I would have done differently if I’d had any balls (so to speak). I would have talked to the nice admirer rather than shun him at the table (although in my defence 30 years of heavy metal concerts has made it so any conversation in a night club has to be repeated three times). I would have danced with Gina when she asked me if I’d like to go to the dance floor with her (although I *think* she may have been after more than a dance, but given my level of terror and complete life-time absence of any form of gaydar who knows what was going on). I would have *relaxed* more.

One thing that myself and Elie said which rang so, so true was this – if they made it mandatory as part of sex education in schools that for one day and one night every male student has to dress completely in the clothes of the opposite gender and spend that time in situations such as a night club, a city street, shopping, travelling on public transport, going out for food, then the attitudes of people would be so utterly different. Until you’ve tried it and experienced the sexual inequality of some of these situations you can’t understand or start to change.

It may be an unwanted but unavoidable part of the whole scene – men who want to be women being around men who perhaps want to offset some level of homosexuality by forcing a woman’s role onto the man they now fancy because he looks like a smoking hot girl, which makes the behaviour so intense and polarised. Some T-Girls want to be treated like sluts. But some of us don’t.

Maybe there’s a need for another type of club, somewhere where people can get together and just be romantic. I think I’d love to go to a club where I could sit and sip a nice glass of something while talking (at a volume I could bloody hear) with an admirer. Understand the psyche, but more importantly understand what it is that draws me to want to be a woman in the company of men. Not a sexual thing, but a role thing, the final casting off of the unwanted shackles of genetic binary choice and the ability to embrace a deeper, more visceral need to experience life through a softer, more wonderful and warmer perspective.

But anyway, I made it back to the cab. And the first thing I did in the back was take off my fuck-me heels, rest my corset-bound body into the seat, and not stop smiling for the next two hours.

Go figure.

Stay beautiful and true to yourself, and don’t let the behaviours of others hide your light.



9 thoughts on “Wayout2: Where Fun and Terror meet over a glass of Red wine and a Fondled Bottom

  1. Yet another great blog post hun. X
    And with a lot of insight brought on by your experiences of the events as they unfolded. I really enjoy reading your posts. 🙂
    They resonate with me quite a lot and I will say that from what you’ve written here today I would have caved in and ran as fast as my heels would take if I had been there.
    Take care hun.

    Liked by 1 person

  2. What and adventure, sadly my clubbing days have long since passed but if you ever find that other kind of club where you can sit and sip a nice glass of something while talking (at a volume you can bloody hear) be sure to let me know… Louise x

    Liked by 1 person

  3. You are so brave to write about your experiences, much less live them! You open your vulnerable self and I admire you for that. I’m an male admirer from the USA–and I experienced something similar to your terror with my first recent date with a TG woman–out to dinner in a well-known, busy downtown establishment. No hiding. I was so nervous in the time leading up to the date–but the date itself was amazing! But then, the fear afterwards about “what it all means…” Still sorting that one out. Now, what you experienced was so much more intense, and it gives me some perspective on my own life and direction. So, thank you for that. And, I must tell you that your observations as “a woman in a man’s world” are compelling and support what many of my female friends have told me for years. As Louis CK says…”Men are women’s greatest enemy..”

    Here’s to more adventures for us both!

    Liked by 1 person

  4. Hi Sarah,

    Just reading this 18 months after the event and working my way through your blog posts in date order. I have to say I really dont think I would have the bottle to attend a club as you did, I also have the hearing problem you mentioned which makes it near impossible to carry on a meaningful conversation which I find very frustrating even in a drab situation. I must say you looked wonderful in that gorgeous outfit, even if some of the underpinnings were less than sexy! I am very much enjoying reading your blog pages though its going to take a while to catch up. I find your musings very thought provoking, I often wonder why I do so enjoy dressing and particularly taking photos which give me such great pleasure. Thank you for sharing your thoughts and experiences.

    Margaret xx

    Liked by 1 person

  5. Like Margret, above, I’m also a little late with my comments. I think the choice of that particular club was to give you and your friends at least a little more anonymity (in spite of the unwanted PDA)
    and more of a comfort zone for your new experience. As for myself, I’ve never been able to tolerate the noise and awful music. The crowd is enough reason to head for the door, if you can find it. But you have the keyword; Romance. No matter who, isn’t that what were all looking for?

    Liked by 1 person

  6. Hi Sarah. Your blue lace dress is to die for! You look absolutely stunning in it. I find it hard to believe that there were T-girls or even real girls there who were more beautiful than you. Re a club where you can actually talk to each other – many years ago, I used to frequent the Tv/Ts Group in French Place, Shoreditch. It was wonderful and I made so many good friends there. Stay safe and happy, Sylvia xxx


  7. Hi Sarah,

    Lara-Lilly has been on a whirlwind/hurricane introduction to trans/crossdresser (I know you dislike this word) life in the last seven weeks . The only two things she is desperate to do are :-

    1) further the daytime walk into maybe venturing into a cafe or coffee shop with Cindy
    2) to venture out to a club

    Now Lara-Lilly was really confident about the latter until reading this blog entry! Now she is a little scared 😱 , it’s a good job COVID has still kept the clubs shut ! Sounds like you were at an auction and you were one of the lots up for grabs (literally) but didn’t want to be sold . I don’t recall my man days clubbing being like this ? Yes admittedly I talked to the girls and of course male hormones were rampant but cmon guys respect the girls ffs ……most of the times I was unsuccessful but I went to clubs more for the music and drink ! To meet a nice young lady was a bonus . My mrs was actually the one that stalked me week after week in the club ……she was the sex pest not me 😂…..sometimes I would talk to her and sometimes I would blatantly ignore her (kept her interested) .

    I am still very interested in experiencing a night out ,I still need to see it for myself if that makes sense? I sort of still want to believe that there are respectful young men like me there , just out for a polite but enjoyable evening.

    I wonder if your experience would be different in let’s say a conventional nightclub ? Do you think that cis women at conventional clubs really get the same treatment as you did at the way out club? Or do you think your treatment was over the top in comparison ?

    Lara-Lilly x

    Liked by 1 person

    1. I think cis girls get the same treatment, but with t-girls and admirers it’s much more focussed. I think for some of the nightclubs it’s an expectation that everyone is there to get laid….


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