First Crossdressing Experiences - Old Man In Hotel free porn video

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As a young teenager, I remember getting a bit of a cheap thrill whenever I found some knickers or ladies underwear where we played as k**s, usually under bridges and tips etc. But it wasn't until I was in my early 20's, when I realised that there was anything other than peeing to be done in a public toilet. I discovered a large public toilet with very small holes in the adjoining wooden walls - this certainly opened my eyes. I was (and am) straight, but seeing guys playing with their cocks for all to see was such a thrill. First day I just watched one guy playing with himself. After a day or two I had seen several, and then it happened, some guy in suspenders and stockings wanking himself off - I was amazed, thrilled, super horny, I still remember it to this day.

Within a few days I was in there, wearing my girlfriends gear, just sitting there with my cock pointing upwards between my stockings and suspender belt - getting lots of messages slipped under the walls to me. That was enough for me for a long time, I was happy to wank myself off in undies whenever I could.

By the time I was in my mid twenties I had a good job that involved a lot of travel and hotels. My thrill by that time was to leave my hotel late in the evening, and go out running in some super tight lycra dance shorts in the dark. It gave me a monster hard on. I loved the occasional car going past and knowing they couldn't miss my bulge in the headlights.

Eventually I had my first real contact with another man. I was in a hotel near the M5, and I had a few drinks with dinner and got chatting to some other suited guys in the bar. It was just a few words here and there watching football. By the time it got towards midnight, it was just myself and an older stocky guy with a moustache and slightly posh accent. His name was Derek. We chatted away a bit more and he was asking if I was married and this and that, and he got round to talking about the time spent away by guys in hotels. He started talking about dirty magazines he found under beds in hotels rooms ( the internet was in its infancy at this point), and jokingly asked me if I wanted to borrow some. I had had a good few drinks by then, and said "too right". He told me to drink up and we went back to his room. The mini bar was soon opened and he was sort of joking about putting a porn movie on. I said I was uncomfortable with that - and I was. I wasn't really up for what I was beginning to suspect was a gay encounter. Anyway, he got a huge stash of Magazines out - 80's glamour mags, my favourites, Razzle, Escort etc, loads of nice undies on show. We both agreed they were great, and I was starting to feel horny as he poured me another drink. Then he threw down another few mags - German I think they were, a lot of the pics in black and white, and he told me these were his favourites. My eyes nearly popped out when I looked. Typically lots of huge breasts in leather etc, but then....... several pages of men in ladies underwear, suspenders, heels stockings girdles etc and lots of big hard cocks. Derek asked me if I liked that, and I said I did. I was so thrilled and horny and shaking, I'll never forget it.


He told me to enjoy, and he would be back in a sec and he disappeared into the toilet. When he was in the loo, I could help but give myself a quick feel through my trousers. My heart was hammering in my chest. I heard Derek come back out of the loo as I sat facing slight away on the bed looking at the mag. I could sense him a couple of feet away and hear his breathing, so I very quickly glanced up and caught a bit of reflection in the mirror. Good god, he was standing there in big white knickers and some tan stockings. My face flushed red hot. He walked right up to the edge of the bed and I could see his cock stiff through the fabric. It wasn't very big, but look like it was rock hard.....................I'll never forget the next ten minutes. 

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I have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This is a story about my favorite slave I have ever trained. I had been anticipating the arrival of my new toy all week, and he was moments away. My new slave, eager to be trained under my heels. The first time I saw him I had brief fantasies of my hands and mouth exploring every inch of his petite and...

3 years ago
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Forced Crossdressing Stories

All of these stories share a central theme of Crossdressing. Rather than add yet another story for one of my ideas, new ones will now go here. I'm making the call, out loud, for additional authors to add their own threads and work with me. I would love anyone interested in any of these stories or my previous ones to add their own threads. If writing isn't your thing but you have ideas, send me a message. I'd love to hear of anything you come up with.

Transsexual
4 years ago
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Crossdressing for sex

The act of crossdressing for sex is incredibly arousing. It gets me in the mood for the debauchery to come and allows me to come Brooke the cock loving whore. Even having been dressing for over twenty years, I still look forward to it. Adding to the experience I like to dress while my lover waits in another room. I want them to sit there thinking about what I am doing, what I’m putting on, what I will look like when I enter the room. I want their imagination to flow, and I want their cock...

3 years ago
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An Introduction To Crossdressing The Finale

Reliving our evening’s events had Jackie and Chandra pretty worked up. “You girls seem to be getting a little excited," I stated. "Are you ready for some more fun?” Simultaneously they both grunted, “Yes we are!” I leaned across the table to find them both holding the others cock and slowly working each other into a frenzy. “You should probably save some of that for back at the hotel, before you run dry,” I said. But that didn’t seem to deter their enthusiasm, until Susan walked up. “I’m done...

Crossdressing
3 years ago
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An Introduction to Crossdressing Pt 6

After Steven leaves me at the table with Jackie and his new friend Chandra, I start to fill them in on the details. I tell them, “It’s really Jackie’s fault that I got fucked so good; since he was being so aggressive with his dance partner, I got jealous and grabbed Steven’s ass.” Then I continued with, “This led to Steven grabbing mine beneath my skirt, and then stroking my cock and balls under my panties.” Jackie interrupted with, “Forget about the dance floor, tell us what happened in the...

Crossdressing
4 years ago
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An Introduction to Crossdressing Pt 4

In Part 3, Jackie and I had our way with each other for the first time and then headed to the shower to ‘clean up’. As I was removing my feminine attributes - the wig, makeup and lingerie - it occurred to me that even without those items I still felt rather girly. Previously whenever I would change out of my lingerie back into my man clothes, my attitude would change as well. Maybe my attitude hadn’t changed this time since I had dressed all the way and given myself completely as a woman....

Crossdressing
2 years ago
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Bookstore Crossdressing

It was at an adult book store in the north part of Denver. I had just gotten a nice pair of stockings with the latex band to keep them up and I had a hot pair of heels that brought out the tramp in me. I always entered the store with the heels tucked in my jacket, so they weren’t that noticeable. Once I was inside a booth, the heels came out the clothes came off and the slut came out. The hallway was empty where the booths were so I ducked into the booth that had a video of a luscious...

Crossdressing
3 years ago
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Married Crossdressing Fun Ch 3

“Mikki?” Caz asked. “Yeah, babe?” “I’ve been thinking...” “Always a dangerous thing,” I said, cheekily. “Yeah, whatever. Seriously, I’ve been thinking about what happens next.” “What do you mean, what happens next?” “Well, you are really beautiful but I was thinking of stepping it up a notch.” My wife Caz is the most beautiful woman I know. I love her with all my heart. She is sexually voracious. We played a little game a while ago. She saw how turned on I got when she treated me like a bitch...

Crossdressing
2 years ago
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Married Crossdressing Fun Ch 2

Caz and I had been living in our new home for about two months. Our life was wonderful. We loved each other more deeply every day. Caz enjoyed her new job and she was really good at it. She was a beautiful, sexy woman and in the field of international finance surrounded by mainly middle-aged men, she had the advantage and wasn’t ashamed to use it to further her cause. Her company was making record profits and she had already had a pay rise. She was also in line to get a huge bonus at the end of...

Crossdressing
4 years ago
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Married Crossdressing Fun Ch 1

I was lying on our marital bed blindfolded, with my hands cuffed to the bedhead, wearing a pair of sheer black knickers. I was waiting for my beautiful wife to come home from her date with Antwan, her big black lover. I thought back to how this all began. Caz and I met when we were both studying at the State University. I was doing an MBA having completed my degree in Business. She was finishing her degree in International Finance. She was the most beautiful woman I had seen and I thought I had...

Crossdressing
2 years ago
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An Introduction to Crossdressing Pt 3

As I was following Jackie to the hotel I couldn’t stop looking in the rear view mirror at what was a complete transformation in my mind. I kept doing that thing where you look away and then back hoping to catch your reflection not keeping up with you because you are sure it is not you. It is probably a good thing that there were not very many cars on the road since I wasn’t paying any attention to it while I was admiring myself. I did see Jackie’s turn signal and brake lights just in time to...

Crossdressing
2 years ago
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An Introduction to Crossdressing Pt 2

So as Jacky was going through his story about how we ended up in this shop, I started to look around. I found that my initial belief that the shop was just a hair dresser was completely wrong. The shop was split in two, long ways, with the left side having about four stations for regular hair work, two stations for nails and a couple of closed rooms for massages, waxing and tanning. The right side had several racks of all sorts of women’s clothes including lingerie, dresses, shoes, wigs and...

Crossdressing

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