tagTranssexuals & CrossdressersHow I Became a Whore

How I Became a Whore

bycutemorri©

Totally true story. I hope you enjoy!

*

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...

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by Anonymous04/04/14

I 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.Themore...

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