My ex-wife (5'5", 125lbs, blonde, blue-eyed, 38 D boobs from a boob job) and I went to the Bahamas. We heard about a popular nightclub and decided to go. She loves to dress sexy, especially on vacation. She wore a white spaghetti strap bodycon dress that came down just a few inches below her butt. The dress and some sparkly five-inch-high heels, her 3K wedding ring with matching earrings was all she had on. No panties or...

Accidental Escort Part 3 Okay, this part is embarrassing. Tom had been texting with updates about our next date and bringing one or two of his along. His friend John, readily agreed after seeing the pictures and videos. Tom texted me, asking if it was okay to give John my number. Of course, I said yes. A few minutes later, John texted me. John: Hi Robin. I’m looking forward to seeing you in person Friday night. Those pics...

After Tom left that first night, he texted me when he got home. He asked if I was free next weekend, saying he could not wait to see me again. I told him I could be available Friday night at the same time. The whole week I was worried about how I was going to handle taking his big cock in me. Most of the guys I had been with before were five to six inches. I have a regular guy I see two to three times a month, who is abou...

It started innocently enough. I was all dressed up one Friday night, waiting for a date that canceled on me. Disappointed, I decided to chat online with other crossdressers and transvestites. One person I talk to often asked me if I had ever pursued my fantasy of becoming an escort. I explained that I had never found a suitable website to sign up on. After our conversation, I reconsidered and found a TS/CD escort site tha...

I forgot the cable guy was coming. I was completely dressed. Nails, make-up, etc. I was wearing a thin pink top and very short blue jean shorts. They had slits on the side, and my panties could be seen. I had my size D boobs with erect nipples in a pink lacy bra. The thin top made my nipples stand out. My long brown hair was pulled over and down my left shoulder. I planned to spend the whole Saturday dressed up until my d...

Before the night I met Cory, I had only been with three average-sized white guys. Cory and I had been chatting online for a couple of months and late one Friday night he asked if he could come over. We decided I would come out to his car in my driveway. Unbelievably, I didn't know he was a black man until I got in his car. It just never came up in our chats. He was very handsome and about 20 years younger than me. He was...

After our first night together, Shane (my twenty-three-year-old roommate) and I spent every Saturday night together for three weeks. It was on the fourth Saturday, and things got a little different. I was expecting him around midnight, so I started getting ready at 7 pm. He had seen me in my three best outfits already, I wanted something different and to look as sexy as I could. After doing a lot of shopping, I found a gr...

I had been chatting off and on with a local man for a few months. A couple of weeks ago he asked me if I would be interested in being a server for his next poker party and he would pay me $200.00 plus tips. I got really excited at the thought of doing it. I told him that I had a few thousand questions first! Lol! First, how many guys would be there? Four, he responded. Second, do all of them know that I am CD? He said tha...

I had a four-bedroom house, just me. I knew him from a local bar. He needed a place to stay for the summer, so I rented him a room. I did not do it just for him, however. He was always pulling these hot-looking babes and we ended up having a few parties with all these babes around. Loved it! I also got laid a few times. I had been dressing for about a year before he moved in, mostly every weekend. One night around 2 am, I...