- Transgender & Crossdressers
- How I Became a Whore
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Totally true story. I hope you enjoy!
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So I had always had this fantasy of selling my body for a man's sexual pleasure. To me there is something validating about the fact me dressed in woman's clothes, lingerie, and acting girly could be attractive and sexy enough for a man that he would be willing to pay me to suck his cock and let him slide it inside my boy pussy and cum. Well this happened years ago when Yahoo still had public chat rooms catering to different adult tastes. I used to hang out in the cd-tv and gay rooms and meet all kinds of interesting people. One night I was bored hanging out in the cd-tv rooms and started chatting with a guy who was staying in a hotel close by on business. We cammed and he apparently liked what he saw because he invited me to come over to his room. I shared with him my desire to play out my whore fantasy and he said simply "ok..how much?" I said twenty bucks. He said done...but I get to fuck you. Who am I to argue? Of course I told him he had to use a condom to which he replied he had a dozen!
Well I was already dressed to play in bra, panties, garter belt and stockings. He was staying in a nicer hotel where you had to walk in through the lobby so I decided to go downplayed unisex for my outer clothes. I put on some tight women's jeans, high heeled leather boots, cute top and a denim fake fur trimmed jacket. I did not wear a wig, just did my short boy cut hair in kind of a butch woman style and put on some light makeup. Put a couple of condoms and some cherry red lipstick in my pocket and off I went. I really liked the look: kind of unisex...but really all woman's clothes. From a distance I looked like a butch classy call girl.
Well I got to his hotel and walked in the lobby. It was quite late, and even though I tried to downplay my clothing with nothing too outrageous, it was obvious I did not belong there. The lady behind the front desk asked if she could help me and I just replied "I am here to see one of your guests" and kept walking. I think she knew I was a hooker, but was too shocked to stop me. My heart was beating like crazy at that point. I was a whore. Going to a stranger's hotel room to earn $20 for letting him fuck me. And I had been called out by a woman.
After what seemed like a mile long walk I knocked on his door. He opened the door fully naked with a nice thick, but not too thick, 6.5 in cock halfway erect. He smiled at me and just said "Sexy....I cannot wait for you to earn your money!" I asked him to lay on the bed and put the $20 on the nightstand. I took off my outer clothes and was soon standing with my back to him in my lingerie putting on my lipstick. I could hear him playing with his cock and sure enough when I turned around he was hard as a rock.
I walked over to the night stand and took the $20 and put it inside my bra and unwrapped a condom. Then I rubbed my self down his body to his wonderful cock and started licking it before I took it inside my mouth. I have been told I am a pretty good cocksucker, and I guess he thought so as well. After a few minutes he said "Damn sexy you are going to make me cum, and I want to cum inside your sweet little ass." So I took the condom and put it in my mouth and put it on him just like a real hooker. Oh wait a minute I guess I am a real hooker now since I have his $20 in my bra and am putting a condom on his cock like a pro.
He started to get up and I told him to just lay there and let me do the work. Luckily I had been playing with my toys and was ready for him so I sat on top of him, facing away towards a mirror reverse cowboy style and slid my panties aside. I grabbed his cock and guided it to my waiting hole and slowly sat down on him. Slowly...letting my self get used to him inside me. Then I looked up and watched myself in the mirror: money in my bra, cock up my ass, and my cock showing hard in my panties. So I got the pace going and pulled my cock out and wanked myself while I worked on his cock with my ass. Pretty soon he started breathing real heavy and grabbed my hips and started thrusting hard. I wanked harder and shot loads of cum over my stocking covered legs and the hotel bedspread.
Once we had both cum I just stared at the sexy whore smiling back at me in the mirror and I slowly got up, pulled his condom off and cleaned him up with my mouth. As I was getting dressed he said "That was so hot I think you deserve a tip." With that he took out another twenty and shoved it down my panties feeling my cock as he did.
Well I finished getting dressed and walked out through the lobby where the same lady was behind the desk. My hair was kind of messed up and my lipstick and makeup were a mess. She looked at me and frowned as I walked by, but I just smiled. I was now a whore, $40 richer, and had just had a good fuck. What girl wouldn't be happy...
- COMMENTS
Anonymous2 months agoI want to have my fantasy come true to git a pimp and have him send this cross dressing slut out to make him money selling my mouth and ass to lots of men or a large gang bang would be great I have a large dildo up in me and going to try for two fucking my self love cock and loads of cum to swallow tonight it will have to be my cum down my throat if I bend up I can git the tip of my own cock in my mouth.and swallow my load
Anonymousalmost 2 years agoomg, I love your story, I have fantasized about doing this too. I admire you, I dont see anything wrong with with being compensated, after all you are providing a service to other men whose spouse wont provide. Enjoy and stay safe. Adrian, CD
Anonymousover 8 years agoI enjoyed reading your story very much.
Sincerely,
Josie of Augusta, Georgia
email> Josie.karaoke@yahoo.com
Anonymousabout 10 years agoI dress, always a black wig, tight black skirt,,nice blouse, pantyhose, flat shoes. I sit in the medium size hotel lobbies, there are 3 that I frequent, my fetish is to get picked up and get paid for sex.The only other place I dress is at home. I am 46, just passable, I usually get there about 9.30. Guys are coming in after eating, drinking. Last night, I was sitting drinking coffee, I saw a guy looking at me, I smiled at him, he looked down, he looked back up, I smiled again and uncrossed my legs, he got up, went to the bar and then moved towards me, looking for some company, I smiled again, could be, he asked the usual questions, when I told him I lived in the town and I worked here, he hesitated so I said if you have a room, $50 buys my company. He said , who could resist a lovely lady like you and took my hand and I stood up. We went to the lift, his hand went under my skirt, I opened my legs a little, his hand touched my bottom, my cock grew, his other hand went up the front of my skirt, brushed my cock then placed his hands on it. I touched the front of his pants, his cock was already hard. We reached the floor, as the lift opened, I lifted the back of my skirt, his hand groped me as we reached his door. As soon as we were in, I took my skirt off as he dropped his trousers, I went straight to his cock, which was very thick, licking and then taking it in my mouth, he pulled back, I want to fuck you, I stood, that's o.k, as I put a condom on him,, lay down,i lowered my pantyhose, I put some lube on my hand and straddled him, rubbing my hand up his cock then holding it, I had no trouble positioning him as he was rock hard then worked his cock into me, my hole opening as his thick cock split me, I sat right down on him and waited, my cock standing out, then I moved up and down, then he grabbed my hips, fuck you feel good as he pushed up into me, oh, oh, your going to make me cumm and as he fucked me my cumm shot onto his chest in big spurts, I felt his cock spasm and I knew he was cumming into me, I moved up and down faster, milking him, making sure he was emptied until we stopped moving. I moved off, then knelt beside him, took the condom off, and cleaned him with my tongue and mouth. He lay there as I went into the bathroom and cleaned myself and came back out and dressed, he handed me $70 and said, hope I see you next time I am in town. I went home, satisfied.
Anonymousover 12 years agoI loved your story -- I make love to men because I love to be touched and appreciated as a female and sucking cock and getting fucked in my assy is just a bonus ever since I can remember. However, my Collage years at UCSD could not be paid off without all the gentlemen that appreciate me. They enjoyed my company as well as I enjoyed theirs while they gladly and generously paid for my time with them. I was neither a prostitute nor a Whore but greatly appreciated and enjoyed in all aspects and forms and I was compensated financially. The man that I frequented wanted to pay to demonstrate their superiority of being able to take care of lady and empowered me to be that appreciated lady. I don't take money for sex and I don’t fuck but it makes me feel hot that my guys are making love to me because they finds me sexy, lavish, and attractively dressed lady that fulfills their desire, needs and fantasy, and my collage mate has not been complaining since graduation either.
