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Hello friends, my name is Ricky and this is the story of how I became a paid cross dresser two years back. It was during the Christmas holidays when I was in need of some money. I called my friend Kris and asked for his help. Though he agreed, he asked a favour in return. When I met him, he told me that his job was in danger and that the only way to save is by pleasing my boss. He told that his boss was a bisexual who had a thing for cross dresser. I used to dress like a girl at times but never showed it to anyone. Kris came to know about it when he once caught me in a floral maxi dress, masturbating myself. That small incident changed my life and I became centre of attraction for rich gay men.

I had been planning a trip to Japan for a good while. I had saved money, booked tickets and made bookings at hotels. But maybe it wasn’t in my destiny because at that time, the covid pandemic struck and everything was put on hold. I had booked my stay such that I had an opportunity to court some local ladies. I had a thing for Asian women and I was super attracted to them. I have many kinks but wanted to satisfy my fetish desires with them.

I watched her moving through the room. Her gaze was fixed on the couple on the platform. I could tell she was feeling horny, by the way her legs moved, as if she was trying to rub something down there. Her body stiffened every time, the man penetrated his playmate with the whip handle. I knew what she was feeling and the atmosphere in the sex club was getting hotter.

I was at my friend’s bachelor party in Vegas and was going to experience something different. We were hitting up several clubs and in one I met Irina. I saw her dancing over the bar. Great body and amazing tits. I looked up and smiled when she caught my eye. She smiled as well and came down towards me. I am well built and was 27 when this incident happened.

It was 12 am at night and I just couldn’t get my eyes to close. I was thinking about Shari, how hot she looked tonight while setting up for dinner. She was employed with me and I was attracted to my maid. I couldn’t explain it, but it was there. She had come to me a year ago seeking employment. She studied during the night and worked for me during the day.

I was feeling horny today but that doesn’t mean I should think of fucking my stepmom. Cassie my usual was out of town and in this sweltering heat, my chances of finding a new girl to bang were almost zero. Anyway, I was still hoping that some girl would walk in through the door as I waited in the ice cream parlour. It was hot outside. Then the door opened and in came my stepmother.

My wife Shana and I wanted to experiment a bit to spice up our sex life.  So, I had been learning a little of rope tying techniques as we both dabbled in BDSM role play. We were also planning on adding a little bit of role play to stimulate each other as acting like strangers just make things naughtier. The date was set and I was to come in as the handyman to fix the sink.

I have been exploring my sexuality for a while now and while I cannot confirm that I am a straight man, I am still not sure which category I fall into. But a trans person is living right next to my apartment – Benny and I feel like doing dirty things with him. I mean like he dresses so well and rocks a full face of makeup with a slight beard. He does have generous boobs and I have thoughts of my trans neighbor, every time.

It was typical lazy afternoon and I was lounging on my couch trying to jack myself off. I was fantasising about my neighbour, but I didn’t know if he was into fucking shemales. I was a shemale, with a great set of boobs and a dick. And then the bell rang.

Carla, my girlfriend and me were looking at options to move in together. We had just started dating, but my family knew that I was a lesbian, a long while back. Carla was new in my life and it felt like I was dating for the first time. Yes, when she arrived, I felt butterflies in my stomach. I loved what she could make me feel and I knew there was a special connection that makes me horny with my Lesbian girlfriend.

I was dating Jana for two years now and I wanted to give her a surprise for valentine’s day. Last year, she had given me a lacy lingerie set and I surprised her with some jewellery. But this year I was out of ideas and didn’t want to copy her last year’s idea. I was thinking about what to do for her to make her feel good. I was thinking of doing something spicy that would mean a gift a both of us. So, I came up with a plan of rubbing my lover’s tits to pleasure her.

I was meeting a group of guy friends at a bar. It was a renowned gay bar where drag shows were held on Tuesdays. So I went there, a woman. I was bisexual and enjoyed dallying with both sexes. I was enjoying the show, singing along when I went to get a drink at the bar. Max was serving drinks and the first thing I noticed about her was that she had heavy eye jewellery. Piercings and heavy makeup made her eyes pop even more. I didn’t know I would end up sleeping with the Waitress I met there.

I was dating Julianna for a while now. She was all of 21 and I knew she was it for me. I also knew that she hadn’t had a boyfriend before me. I had proposed her that Christmas and we were engaged to marry. It was a beautiful summer day and I had asked to take her on a picnic just to spend some time together – unsupervised. I hadn’t intended it, but we ended up making love under the open skies that day and devouring my virgin fiance.

Chad was an asshole! He had been cheating on me for months and I had turned a blind eye to all the warnings that my friends and even his friends gave me. I believed that he really loved me, as much as I loved him. But the one thing, I learnt was that men are never to be trusted. They will use you and then throw you away. Will not show you the respect you deserve. In my string of failed relationships, each one of them had used me for their own benefit. And in the end, it was a “sorry” that I got. For all that pain, for all that I did for them – sorry – one word as a return gift. But I had had enough and I was going to get back through revenge sex.

I was a student by day and a firefighter by night. I had joined the team two years ago and was trying to get a college degree by attending classes at night. I often used to silently masturbate when I would go to the library, as I was alone in the evenings, at the almost closing time and it would take the edge off a bit. During one of these times, I saw the local librarian and oh she was hot. Perky tits, tight ass and a low cut blouse. Wow. She would probably feature in my fantasies for a while.

I live in Florida with my girlfriend of 2 years. We are very happy together. She works at a travel agency which often gives her the opportunity of travelling around the world. When she travels, she ensures that I am taken care off. She would often cook for me, or keep my clothes ironed, or even dry clean my shoes. The latest addition to her ‘care for Simon’ routine is hiring a maid. So, she hired Tressa. The story is about my romantic session with her and how I got the best blowjob I got from my maid.

I met Lisa in college and then we also had some steamy webcam sex. But that’s not the end. It was because she wanted to relax sexually and didn’t want the hassle of dating a guy. I wanted her. Oh, I so wanted her. But she kept denying me. And now we are stuck together on a plane. Right next to each other, in economy. Why, you ask? Because we are on a freaking college trip or an educational trip if you prefer. That was it. I had some sexy moments up in the air itself.

Cheating can be defined as an accident, unintentional or maybe intentional act. It depends on person to person and maybe situations are different for everyone. We can’t say until we go through the same condition and become the game changer.

The newest trend in the dating industry is not a new app but a whole new experience of dating someone. It is called a girlfriend experience. As the name suggests, you can now hire a beautiful girl for a day to walk around the city hand in hand or just cosy up in bed all afternoon. These girls are highly trained escorts. Unlike the traditional understanding of an escort, these girls go beyond just sleeping with you to deliver utmost pleasure in their time. You are literally like friends with benefits, who do not shy away from lending an ear when you are in need. Toronto being one of the most craziest cities of Canada has also the need of some softcore romantic life instead of just sex and there comes the need of girlfriend experience escort in Toronto.

I was a part of our college football team and had practice that afternoon. I arrived at the locker room to change and saw this skinny older guy. He was wearing spectacles and talking to coach. That was the first time I saw Laurent. Later I found out that he was a visiting Maths professor. He taught at the university. We slowly became friends, even though we were from opposite spectrum. I was a jock and he was more interested in theorems. Everything seems so good so far right? It went way too far from just studies and I ended up having sex with my maths professor.

I am Sagar, a 24-year aged man, or woman you might say. I started loving the clothes of the woman since my teenage and I like turning into a woman. I always use to wear women’s nightwear while sleeping and even during the day I used to wear a bra and panty under my men’s wear. It used to give me immense pleasure. One day, I went to watch a late night movie. Beside me, a handsome man was sitting. After half an hour or so, I felt his hands caressing my thighs. I was a little confused but I was enjoying his touch. So, I let it be. His caress deepened and my erection was getting stronger with each stroke. Slowly his hands touched my hard cock and I sucked in my breath.

Hi, my name is Sam and I am a 26-year-old, slim physic cross dresser. I am a fashion designer and have a thing for female clothing. Not only I love designing female clothes but I also enjoy dressing as a girl. Coming to my story, this incident took place some years back when I was around 20 years old and had cross dresser romance session with my real Aunt. With fair and curvy physic, I can look more girly than a girl with my cross dressed attire.

This happened four years back when I joined a new office. I was 26 years old at that time with fresh mind and body but inclined toward lesbian sex. My boss cum manager there was Betty. She was a 52-year-old lady with a little chubby body and a figure of 38D-38-36. She was a very strict lady, and I have often seen her shouting at other colleagues. But she was a little soft in the approach towards me. During my initial days at the office, I had only a few interactions with her, but after a couple of months, we started to talk more and she often dropped me at my house. She led a happy family life with her husband who works in the Government sector and two sons working in MNC’s.

I had a maid working for me for a year now and often I had caught her masturbating. She didn’t know yet, but when she thought I was away, I would secretly watch her as she cleaned my bedroom. And one day when I caught her masturbating on my bed, I gave her a good pounding – in her pussy with my cock. Now she would sometimes shamelessly walk around only in an apron, showing me her cunt. So, one day I brought James, my friend, over to watch my juicy maid.

This is my own story which is little long but read it completely, you will enjoy if you like real gay erotica. This incident happened a few months ago, in September. I met this guy on a flight while coming back from Chicago. I had gone there for some office work. The flight was late in the night, and it was delayed by almost an hour. I was tired, and I tried to take a small nap while I was on the flight. Unfortunately, the nap lasted for only 20 minutes or so, and I woke up due to turbulence. I opened my eyes and glanced over. A middle-aged guy was sitting next to me and was reading something on his mobile. Unable to sleep again, I just started looking outside the window. There wasn’t much to see because of the night and dark rain clouds. I peeked at his mobile screen and tried to see what he was so engrossed about. It seemed like an e-book and I tried to read a few lines to figure out what kind of book it was.