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I'm a 65 year old bisexual male who loves to cross-dress. I've been doing this now for seven years. Wearing women's clothing just feels so good to me. When I get up in the morning, I can't wait to get my entire body shaved completely smooth, put on makeup and do my nails. Next comes my thong, corset, push-up bra, hip and butt pads, garter belt and nylons. Since I've been taking phytoestrogen supplements the whole time, my boobs have grown to fit snugly into a 42C bra. My boobs are really nice. Guys go crazy for them. I began using breast forms to augment my appearance, but I don't need them anymore to get a nice effect. I really love my boobs and fondle them as often as possible. Next comes a silky slip to drape over my torso, followed by a sexy dress with its hemline falling just above my knees. The neckline of my dress must plunge low enough to expose my cleavage. My legs have received many compliments on their shape, so I always wear a fashionable pair of heels to bolster their appearance. Earrings, necklace, bracelet and a nice wig complete the look.
My wardrobe is extensive. I have dozens of dresses, skirts, blouses, shoes. outerwear and accessories. Wigs of all shades and lengths are available to me as well. No matter how much I have, I can't resist the urge to buy more. Its definitely an obsession. When I'm fully dressed and see myself in the mirror, I nearly come to climax. OMG, how I wish I could be a woman. I'm so jealous of those who are.
Being bisexual, I crave having sex other men. As a younger man, it was relatively easy to hook up for same sex experiences. However, as I aged, it became harder to arrange such trysts. Becoming a crossdresser definitely increased my chances for success. I discovered that many men love "chicks with dicks". It opened up a whole new world for me. As soon as I began appearing in drag, I became much more desirable. My date requests grew immensely. I could pick and choose which ones to accept.
One thing I've always fantasized about was being a prostitute. How lucky women are that they can do this. I could never understand why more ladies don't participate in that occupation. I fantasized about it so much, I decided to try my luck as a crossdressing escort. Websites for escort service advertising are all over the internet. I offered my services on as many of them as I could. I really didn't know if I'd get any responses. To my surprise, the replies were overwhelming.
It was so easy to find men who wanted to have sex with me. There were several women as well. I've lost count of how many men I've sold my body to, but it has to be at least several hundred. Age range also surprised me. The youngest man I did told me he was 18, and I'm not sure if he really was . He looked no more than 16 and didn't have a car. I asked to see his ID, but he declined to show me anything. I probably shouldn't have had sex with him, but the opportunity was too irresistible. The oldest guy was in his 70's and the rest were part of every age group in between.
So far, I've made tens of thousands of dollars over the years as a part-time prostitute. I know its not the right thing to do, but I just can't stop. I've tried to quit many times. I love the work so much the idea of quitting is to depressing. I can't keep doing this forever. What am I going to do?
I had sex with an escort. I can't tell this to anyone in real life. I feel shame but I don't regret it. I think I might do it again soon.
When I was 19, in order to pay my way through college I started working as an Escort. Men (and sometimes women) would pay me to have sex with them. It was good money, and the alternative was dropping out. After finishing college, I quit and met this really nice guy. We've been dating for a while now, and he has no idea about my past. Recently, I met his father and recognized him immediately: He was one of my regulars. I was so freaked out, and now I'm afraid my boyfriend will find out. It was before i ever met him, but I don't know what he'd do if he found out.
I’ve always fantasized about transexuals but don’t really act on it often. The last one I met was an escort I found online. Her ad said with condom.
She was really feminine and beautiful. We talked a bit when she showed up at my place. We then moved to the bedroom and played around. She first tried to top me with a condom but I was too tight. It hurt quite a bit since I had not done this in a long time. We just laid there for me to recover and talked more. She told me she fantasized about Asian guys but never been with one before.
After some time, I went down on her for a bit. She then pulled me up and forward toward her. I thought she was going to suck me off, but she just positioned her dick and pushed in bareback. I was shocked and really turned on. I had never done that before. She then just fucked me raw in all kinds of positions and praising how tight and sweet my ass was.
I was so worried but also extremely turned on at the same time. I came riding her. After I recovered, she asked me to fuck her raw and creampie her. I hesitated but gave into my desires. It was wonderful and worrisome at the same time. She told me she was only 21 and not to worry. I hope she’s right.
six months ago, I was away from home for three days. I was attending a family funeral. usually my wife of ten years would have accompanied me, but on this ocaision, she was unwell. finding myself alone in a five star hotel room, my pinch faced shrew of a wife, three hundred miles away, I picked up my phone and browsed the local escorts. I had built in a contingency of a thousand, in my budget for this trip. that would get me a very nice escort indeed.
I browsed for a while, pausing on the 18 year old blonde who still had her actual school uniform and the two girls that offered the ultimate lesbian fantasy for men.
then, from somewhere deep in my subconcious, a long held fantasy materialised. transsexuals.
I typed transsexual escorts into my search engine and I was amazed at the number listed locally to me. I browsed through them until I found one that fitted my fantasy completely. TSNicole. she was tall, slim, blonde, pert natural breasts and a nice feminine bottom . she was perfect!
200 an hour or 1000 for a night. right on my budget. I rang the number for the agency and gave them my details. they sent me an email confirming the booking with a receipt for the payment.
when my phone vibrated again half an hour later, it was a text from the escort, saying she was in the hotel reception. I texted her back that I would see her soon then.
five minutes later, she knocked on my room door.
when I opened it I was astonished. she was absolutely stunning. you would never guess she was a once a man. I took her coat and handed her a glass of champagne. I had ordered a " james bond " as I called it, from room service. champagne, caviar and some smoked salmon nibbles in case she was hungry. we had a nice " getting to know you " chat . she was intelligent and well educated. she was studying to become a social worker.
I won't demean her, or my memory of that night by detailing our intimacy. it is enough to say that we made love several times during the time we spent together and I was left extremely satisfied.
I do not consider my liason in any way homosexual. she was a woman in every way, with the exclusion of her very small penis..
I'm hoping my work will take me near that hotel again soon.
I cheated on my girlfriend with a sexy hot smoking escort. She also peed on me. It was so hot I would do it again but I feel bad.
I was in my late 20's, and in Florida for a few weeks working. After a few nights, I called an escort service and Marie came to my hotel room. She was dressed nicely, wore nice clothes, and had a nice body. She was about 35, 5ft. 6in tall, really nice figure, great legs which is my favorite. She was good looking and though this usually isn't appealing to me had 34DD boobs with nice pink areolae and nipples. Once naked as we talked she opened up that she had supposedly "just started" being a hooker. I figured she couldn't have too much experience as she was giving the entire GFE for the standard price. Then I asked her if she did anal and she told me yes, and didn't charge extra. I was very gentle and she remarked how her ex used to be really brutal when he did it to her, usually in the shower using soap as a lube. I had been fucking her pussy bareback (another reason I figured she might be new) for a long time, so didn't need to lube up, I just slipped in. She let me cum in her twice once in her puss and once in her butt, all for the same price.
All along she kept saying how she would like to see me "personally" if I'd like. I didn't answer and as she was dressed to leave I pulled up her skirt, pulled her panties down and bent her over the desk. While I shoved my finger up her butthole I told her to write down her personal phone number. She did and we started going out. Since we'd already fucked it was a sure thing that we'd have sex every time I wanted. She had an 8year old daughter and a 10 year old son. She and I went nude in front of the children, they accepted it as their mom and dad had always been nude around them Marie told me. Marie started sucking me in the living room while we were all watching television.
I started getting off on fucking her in front of the kids, I never touched them and wouldn't but knowing they were seeing me fuck their mother in her mouth, pussy and asshole was really great. Marie and I started fucking in public, which was really great, I liked that a lot. I left Florida a couple of weeks after my work was done, rather than immediately after. I spent those last two weeks at her house instead of a hotel. I still think back to her rolling over and telling the kids as she was coming while ramming my cock up her poop chute that I "wasn't hurting mommy" rather she said "he's making mommy's bottom and her pee pee, feel really good".
All that and my first natural blonde cunt too. Best $150 I ever spent.
I am a prostitute and I run an entire 'escorting' business. I didn't need the money; I'd been a self-harmer and suicidal for years so I did it out of self hatred, and now I have a business so I can't really get out of it. The most disgusting parts about this are:
1) I have a girlfriend and she doesn't know anything about my business or the people I've slept with
2) I aren't actually 18 yet, unknown by my clients...
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