Free Erotic Stories

Afternoon with a Transgendered Escort, Bi-sexual, I had an afternoon with a transgendered escort

In my case, I am a bisexual male who enjoys the company of other males in a male-female configuration (I have also shared my ex-wife with another bi male). I also enjoy cd/tg types on a one on one basis, but the scenario that I was looking for was impossible to find. I used to use Craigslist to find cd/tg types of lovers, but it was awful. I tried through sites like SLS and AFF to find the same, but again, nothing. So I decided to have a "boutique" type of experience, and yes, this meant paying for the experience that I wanted to have.

I'm not going to go deep about my search, except for telling you that I found what I was looking for. I just had to pay for it. And yet, it was a mind blowing sexual experience. I found Sheila through YouTube, and reached out. Sheila was a sex worker in a major city in the US, and when I was in town for work, she told me that I should reach out. We'd emailed back in forth, then text back and forth then I would call from my phone when I was a few blocks away from her place. She told me that the experience I wanted to enjoy was something that she could provide, and as I had paid a deposit for a three-hour session, we would have plenty of time.

I asked Sheila for a fashion show, and then I wanted to seduce her, and I wanted us to be able to go for a few hours. I wanted to taste her. I wanted us to kiss. And I wanted to top her at least a couple of times. Plus, I wanted to be able to pick exactly what she would wear.

As promised, I called Sheila from a few blocks away. She gave me her address, then buzzed me in once I hit her front door. She gave me a hug and peck on the cheek once I entered her loft. She wore a business suit with a skirt, stockings, and heels. She offered me a glass of wine, and I accepted. We sat across from each other, and I told her how beautiful she looked. I asked if I could touch her stockings, and if I could touch her a bit, and she agreed. I'm super tactile, and touching her stocking-covered legs was such a thrill.

Then she reminded me that we had limited time, and an hour had already passed. She started the fashion show, and I was thrilled. I got to touch and admire for about 45 minutes. But then she changed into the look that I requested. I wanted to see a dark wig with an Asian keyhole dress, tight, with thigh highs, and the highest of heels. It took her another half hour to get ready, but when she appeared in the room, it was game on.

I stood up and came over to her. We started making out. Hands groped all over each others bodies. I forced her dress up and pulled down her tight gaffe. Her immense member nearly smacked me in the face. She was practically pouring pre-cum out of her clitty. I could not believe how hot this all was. And I couldn't believe that I was there, in the moment. I took her in my mouth, and I jerked her off with my hand. Her talk was filthy, yet encouraging. Eventually she stopped me and told me that she was getting too close. She bent over the couch, and said that I could take her bareback if I wanted. Yes, I wanted to. But then again, she's a sex worker. So unless we met up a few times in the future, I would sheath up. So I did.

She told me that she wanted me. I guess that she prepped ahead of time, because I didn't need to force my way in. It just worked, and while she was super tight, there was zero resistance. I took her doggy on the couch, and kept thinking of different things so that I wouldn't cum so fast. Because I wanted to. I wanted the relief. But then again, I'd paid for it, so I wanted to get my money's worth.

I think that it was 15 minutes or so before Sheila asked me to stop, and she disrobed in front of me. She asked me what she should leave on, and I told her thigh highs and heels. She completely undressed me, taking my condom off to suck me off, then she put a new condom on me before grabbing me by the hand and pulling me towards her bed. She asked how I wanted her, and I told her to get on top. I told her to ride me gently. I wanted a nice, slow fuck. Sure enough, we had massive eye contact, and her slapping her ass down on my thighs was sexy as hell. I pinched her eraser nipples, and I tugged at her clitty. She ended up shooting a load on my chest after 15 minutes or so, and I shot heavily into the condom a couple of seconds after that.

I ended up falling asleep on the bed, and to my surprise, she woke me up and asked me to stay a few more hours... but it was on her. Amazing. Yeah, we still used a condom, and we fucked a few more times, but after 3-4 more meet ups over 18 months, I went bare with her, and it was beyond comprehension in its amazingness.