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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.

This is the second part of my previous story. I will write about how I had rough Cross dresser Sex with him.

This is my sex confession of a time when I was 15 years old. I was a teenager but quite the virgin. I never had any girlfriends and like any normal teenager I was obsessed with breasts. Any grown woman that I would cross, I would automatically get drawn to her boobs. I would try to imagine how they would feel against my hands. I wanted to touch and explore the female body and suck on milky boobs for pleasure. One day my wish was granted.

Do you often orgasm before your women? You probably have, most of the time. There could be two reasons for that. Either you are suffering from premature ejaculation or your woman is the kind who takes longer to orgasm. We will discuss about how to cope up with Women’s orgasm time but first thing first, let’s talk about premature ejaculation.

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.

BJ and I were going strong. If you haven’t read the previous story yet, read the part-1. We were attracted to each other, were intimate and pined for each other when away. Then slowly things started to get hotter and we just couldn’t get enough. There was no opportunity we left to touch each other, to fondle or even kiss each other. We kissed behind closed door elevators, within ATM kiosks and even behind bushes if we got a chance. And then just one day on the fly, we decided to do it. Have first sex and lose our virginity.

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 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.

That night was burned into my brain. I had broken up with my boyfriend, my dom, but I couldn’t get him out of my mind. His pleasuring skills still tormenting me day and night. It had been only a week and here I was rethinking going back to him. One of these days I was remembering one kinky night we had where we did it and it was so memorable. I had orgasmed so hard and he had seemed so proud to give that to me.

My wife Alana and I had been living in a new neighborhood for a few months. We were great friends with our neighbors – another married couple. We would often meet socially and invite each other for gatherings. I did desire my wife sexually, but on occasion, I would often think of Arrow, my neighbor’s wife. Jordan, Arrow’s husband, was a great guy and one day he asked me something – did I fancy his wife? After a bit of distracting talk, when he didn’t let up, I accepted that I did. Then suggested we can try exchanging wives for a night.

I never believed in online dating. Although, I had been single form quite some time now. So, a friend nagged and tricked me in to registering on one of the sites. I did not use it for almost 8 days. However, it was the weekend and I had no plans. So, I thought of checking the dating site if there’s something interesting. I found out quite some good options and thought that connecting with them is not going to cause me any harm. Little did I know that I was going to experience something crazy and it ended up having the best sex but was dramatic at the end.

When I turned 18, I was moving out to California for college. As my stay wasn’t figured yet, my mom invited my dad to our home and proposed the idea of me living with him and his wife for a few months. My dad and his wife were very happy to hear that and came all the way to Toronto to pick me up. I was never close to my dad, but I always remembered my first experience of sex with my stepmother.

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.

In my family, women are always covered in a Burkha. It is believed that covering up a woman’s body keeps them safe from evil eye be it from their own father or even their husband’s ninth wife. Like in the western world, when I was a kid, we were never exposed to a woman’s body, apart from their eyes or their feet. Clean beautiful feet with mehendi design or alta dye stain, often made me wonder about what lied under it. Destiny had something else defined for me and I sharing my story of fetish seduction on my wedding night.

The stock market today had given me a lot of profit, I was on the way to my apartment. I will have to wait for 10 full stations. I took a seat and started scrolling my phone, I had a lousy weekend ahead of me, many people had sent messages asking about my weekend plans. Two stations had passed and I was starting to feel sleepy, I gazed around me and found a cute guy staring at me. He had a huge book in his hand and a bag-pack, most likely a college student I thought. As soon as he noticed me looking at him, he turned away. The next station arrived and he stood up, it was a bummer, I thought he was leaving but instead he offered his seat to an old lady. How humble of him, didn’t know generations like these still existed. I noticed his broad shoulders and sleek back, when the seat next to me got empty I gently tapped on his shoulders and asked him to sit next to me. He got all shy but took the seat, “hey” I said, “hii”, he replied he had brown eyes and matching brown his frizzy hair which fell on his eyes. Until then, I had no idea that things are going to get hot and he will become my subway gay partner.

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.

We had a huge garden which had been walled on all sides. But because it was so big, we had difficulty in maintaining it. Dad would be away on business a lot and I had school. My stepmother tried to manage it but it wasn’t easy work. She often nagged me about it and it irritated me and one day I just gave it back to her.

I have been into cross dressing for a while now and have kept it a secret from my wife. She likes to play and is a dominatrix. Usually, we go into dom and sub mode where I worship her cunt with my tongue as she flogs my ass. I like getting dominated by my wife. But tonight, she saw me, in my female form. I was at a local club, which she doesn’t frequent, with my gang and we were all dressed up as pretty women. I was wearing her glitziest dress and had a full face of makeup with a wig. Yet she recognized me. Now I am going home and I am not sure what awaits me.

My name is Aryan and I was posted in Chickmanglur, an area with a lot of hills and coffee plantations. I was sent there for handling the production work. I was given a guesthouse to stay and a house-help, a man named Hari, who helped me with basic things I needed. His wife used to prepare food and do cleaning stuff for me. His wife, Rekha, was a very beautiful and desirable woman. I am going to share my story of how I came closer to her and had sex with the wife of caretaker of my guest house.

Andy knew me like no one else. My likes dislikes he knew everything. No wonder I was smitten with him. We were dating and going strong now for 6 months. Our sex life was explosive and we couldn’t get enough of one another. However, he hadn’t touched me anally. He hadn’t gone there and fucked my ass. So I decided to surprise him. I wanted him to claim me in every way. I was planning for a session so he can claim my anal hole and fill me up.

Alyssa is my sexy servant. Not literally but I like to dominate her sexually. It isn’t BDSM – our relationship, but just that we like role play where she is at my mercy and I can do all kinds of things with her during playtime. But that time I invited a common friend Walter to enjoy playtime with us.

Jace and I had been dating for some time and had even indulged in sex. However, when it came to anal sex I was a virgin. As Jason likes to call it “this ass is mine”. Truly it probably is, as he is the only one who has been there.

I am a lonely man in his forties. I love to travel, dine and explore new places by myself. But I often wish for a partner. I got divorced early, so the little chance of being with someone was also ruined in my memory. So, each morning I would go to work, do my mundane bank job and visit my nearest LGBT bar. I am sharing my memory of sex with a Shemale and how I found pleasure in it.

I had a different sexual relationship with my husband Jan. He liked being the cuckolded husband and it added spice to our sex life. We had experimented with many kinks and one was when I had tied him up put him inside the slotted cupboard. From there he watched me getting fucked by a bouncer that we had found at a nightclub. He came just by watching us and I had a lot of fun getting rammed by a big black dick. That was a fun night.

I am Neila. I will share my story of how I my boss had BDSM Sex with Domestic Servant who worked with her. I was 19 years old when I signed up a job for a domestic servant. When I reached the place, it was an empty room. All it had mirrored walls and in the middle was a metallic table. I had no idea what to expect. I signed up because the pay offered was good and they were offering food and lodging. I had to pay for my student’s debt. While I was deep in my thought, I jumped up from my place when I heard someone walking in. It was a middle-aged woman. She looked sexy in her leather cat suit. She was carrying a cardboard box and a riding crop. Her long thick hair was neatly tied in a high ponytail and her heels made a clicking sound when she walked.