lostindebauchery, Author at NSFW story

Getting sucked off by a crossdressing teacher in my car [MT] [M30, T35]

So, let me describe Nikki. She is a thirty-something crossdresser – about 6 feet tall, slim, smooth and with quite a feminine face. She wears her hair fairly short, but it can be teased into a girly style and on both occasions we have met she has used a hairband to achieve that look. Nikki is a drama teacher and is just as confident as an actor-type would seem, but when it comes to sex she is shy as they come.

I first met Nikki not long before Craigslist casual encounters closed down, I think around 18 months ago. I had replied to her ad, and we arranged to meet for some light fun in a car park about 15 minutes from my house. That first time, Nikki was wearing jeans and a t-shirt, but underneath she showed off her sexy white lingerie, with mismatching black stockings. Nothing sexual happened on that first meet, but we sat and chatted for about an hour, mainly about Nikki’s gender dysphoria and her wish that she had transitioned as a teen. Nikki was somewhat sexually experienced with women, having been married for 5 years in her 20s, but following the breakdown of her marriage, the urge to crossdress and the desire to fuck men returned with a vengeance. Read more »

Meeting a high-class escort for a nylon footjob [MF] [M30, F22]

I was staying in London for 2 nights last week. The first night I was out with friends, while the second I planned to relax in the hotel. Unfortunately for me, on day 2 I attended a meeting with a client, and one of his colleagues attended. She was absolutely drop dead gorgeous. A sleek, fitted black suit, black patent heels, and grey opaque tights. My eyes were falling to her legs far too regularly. I thought she must have noticed. Her face was a pretty sight – she couldn’t have been older than 25 – but her legs were the real draw for me. I sat in the meeting fantasising about fucking her feet in those tights.

After the meeting, I went to another meeting, but still couldn’t get her out of my head. The tights were matte grey, and beautifully accentuated her toned legs. She had really slim thighs and small, slim feet. Her blonde hair was perfectly set and her smile was infectious. It had been a long time from a girl had such an immediate effect on me. I knew I had no chance – her boss is one of my biggest clients, and, well…how does one approach a woman and say, “will you please give me a footjob?” It’s just not the done thing. Read more »

Getting sucked by a “straight” crossdresser [MT] [M30, T26]

I’d been talking to Stefi on Kik for a few weeks. Lots of pictures had been exchanged, my favourite being her doggystyle on a single bed looking back cheekily at the camera, albeit with most of her face blurred. Stefi is 27, with a postdoctoral role at a London university. She’s staying in dorms over the summer and was glad to find out the floor she’s living on is empty. She invited me over to be “serviced”. The rules were very clear – I wasn’t to touch her, nor was I to try to initiate anal sex. She was going to suck me to completion and I was to leave. A classic suck and go.

Stefi assured me at least twice that she is straight. Personally, I think there’s only so straight someone can be if they’re meeting up with a man to suck his cock, but I wasn’t going to complain. This girl is hot. Smooth all over, dark almost Mediterranean tanned skin, a bright blue wig, and in every picture wearing an assortment of invariably black lingerie. She told me she’s been meeting up with men for nearly 10 years and is only interested in fulfilling her fantasy of swallowing a load. I, for all intents and purposes, am just to be an enabler for her fetish, a role I was happy to undertake. Read more »

Taking the virginity of an athletic crossdressing student [MT] [M30,T19]

I haven’t been able to share a good story for quite a well. There haven’t been any to share. I was travelling on business almost constantly from August until the end of the 2017. During that time, I had sex with two women, but neither story is overly exciting. I do have a great experience from New Year but I’ll save that for another time. Instead, this is an experience that happened only just last weekend written up while it’s fresh in my mind and not embellished in any way.

I received a message last Monday afternoon on a fetish social network from someone listed as a man. “Jay” he called himself. I make it clear on my profile that I’m only interested in messages from crossdressers and transsexuals, but before I deleted the message (which I hadn’t even read at this point) I clicked through onto his page. There were no pictures of his face, but I could see that he was very well built and kept himself in good shape. He was 19 and looking for women and couples. This piqued my interest as I wondered why he would be messaging me when we have such incompatible interests. I went through to his message and read it. Read more »

Mutual sucking with a straight, virgin crossdresser [MT] [M29,T20]

A couple of weeks ago I was browsing a fetish social network and saw there was a new user in my area. A crossdresser calling herself Lara, 20 years old, slim, 5’9”. There were two pictures, one of her ass in a black thong, showing a nice muscular ass, not hugely feminine, but more androgynous. There was a second photo or her crotch from the front, in black satin panties with a slight bulge and just the smallest hint of her cock head. She said she had no experience with guys and was looking to try everything from kissing to anal, but lived with her parents so couldn’t host.

I messaged her right away and we began chatting. Over the course of the coming days I found she was “straight” – or as straight as you can be when she’s telling me she wants a man to fuck her in the ass while dressed in her sisters clothes. We chatted back and forth for a bit and built up a good rapport. Eventually I suggested we meet last Friday night. She was kind of cagey about meeting, but did agree that we would meet at a car park close to my home and chat, before going to my house after if she was comfortable. Read more »

My first nylon footjob [M18,F18] [MF] [Fetish]

Today I’ll be taking a trip down memory lane. Back to late 2004 or early 2005. I definitely remember it being the winter just prior to me finishing school. It’s a story that for me has a tinge of sadness; it’s about a girl called Jenna. She was I suppose what one might call a childhood sweetheart. We were never in a formal relationship, but we might as well have been. We held hands, kissed in public and both of us had a lot of first experiences with one another. For all intents and purposes we were boyfriend and girlfriend. It’s a bit of a cliché, but after we finished school she moved away to university, I moved away to university and we drifted apart.

You see the thing about Jenna was that she was by far the prettiest girl at her school. By a long stretch. Every guy fancied her. 5’4”, naturally blonde hair, big brown eyes, flawless milky white skin, 32D tits, a super slim waistline and she was a dancer. I don’t know why, but she would never actually commit to me. Read more »

Mutual handjobs with my new crossdresser friend [M29, T19] [MT]

Well, it’s been a while since I shared a story. Unfortunately since the summer I’ve had a lack of interesting stories, particularly about crossdresser encounters. But this experience was so hot it would be a shame to keep it to myself.

Way back in August I noticed a new profile had come up on a well known scene website. The profile gave very little away, but what I could see was one photo of a crossdresser wearing only black panties and black stockings bent over from behind. The photo was black and white and deliberately didn’t give much away. The girl called herself Poppy and was aged 19. As I said, this profile was pretty much bare. Usually I don’t bother with profiles like this, as from experience they are usually the flakiest people, but this girl was so smooth and slim that I had to introduce myself. Read more »

The time I (accidentally) kept a crossdresser in chastity for over 50 days [M27, T23]

This story took place in June, July and August 2015. It was between myself and a crossdresser I’ve been meeting for a few years. She’s called Kyla – and I might as well shout out to her as she’ll be reading this story. If you have any questions for her, post below and I’ll try my best to get an answer. Kyla is 23 in this story and crossdresses only part time, really as an outlet. We’ve had a few deep meaningful conversations over the years and I’ve learnt that Kyla would transition but for the good things she’s got going in her life. She lives as a male, has a good job, a good family and good prospects. She doesn’t want to rock the boat too much.

I don’t think I could really say I “live” in the UK. I’m usually travelling with work so only spend perhaps ten days per month in England, and sometimes that time is in London hotels as I stopover. I do have a nice house though that I enjoy returning to when I’ve got time. When I return home I also enjoy getting Kyla to come over for a good, lengthy, overnight session. She’ll come already dolled up, will bring an overnight bag and we’ll eat, fuck and sleep until the next morning. Read more »

Getting sucked off by a good Catholic girl in a changing room [M27, F28]

As I’ve mentioned in previous stories, I travel a lot for work. I rarely ever find myself in the United States, but when I do it’s usually a good experience because on my downtime from work I can meet up with old friends and contacts. In July 2015 I found myself on a four-day trip to New York City. I was going to meet a few paper pushers, just to make sure what we needed to happen went smoothly. What this meant is that my actual work commitments were unusually minimal. I’ve only been to New York a couple of times, and don’t know the city all that well aside from the well-known sights of Manhattan, so took a look on Facebook to see who I knew in the area. Read more »