amatuer crossdressing prostituteSo it started out by just a regular day. Work was really becoming a drag, and it was only 11:00 am, and my mind started wandering about what I was going to do when work was over for the day. I stopped at the mall on my lunch break and when I was done at the food court I decided to stroll through Dillard’s on the way back to the parking lot. I couldn’t help but pass through their lingerie section and noticed the cutest little bra and panty set. It was kind of a purplish flower ensemble that I pictured would look good underneath my black mini skirt. I hadn’t dressed in quite some time, so yeah I was daydreaming again and feeling the urge to dress again soon. Approaching the exit doors I passed by the makeup counter and seen an attractive female getting all dolled up by their onsite beautician. I thought that maybe someday I should come in here and ask one of them to do my make up just to see the look on their faces. Well I finally made it out of there and back to work. While sitting in my cubicle my mind kept telling myself that it sure would be fun to get that panty and bra from Dillard’s and play dress up tonight. I pictured myself posing and walking through my apartment and maybe taking a few new pictures. Well work finally ended and I was headed home. As I drove by the mall again, and maybe looking forward to a dull evening alone, I spontaneously flipped a U-turn and went into Dillard’s to check out the lingerie again. I went straight to the lingerie section and found the purple bra and panty set in my size. I said screw it I’ll face the embarrassment and went to the counter to check out. I threw in a pair of sweats and a pack of t-shirts as to not look totally weird to the clerk. My luck it was an older lady who didn’t even look at me much less notice I was a guy. Back at home to unwind from work. I took a warm bubble bath and shaved my legs. I couldn’t wait to break out my dress up totes and doll myself up. I sat in front of my mirror and put my make up on. I decided on a smokey blue look for my eye shadow and “paint the town” red lip stick ought to do the trick. I put on my 34DD silicone breast forms under my new bra and slip on the matching panties. I then put on my black mini skirt, black stiletto heels with matching fishnet stockings and finally my dark wig and blue blouse and of course my 5” hoop earrings. I have to admit it was a nice look. After posing for a bit and taking pics with my webcam I was getting pretty horny. I started watching crossdresser porn videos and came across one called transvestite prostitute. I didn’t watch all of it but the intro made me want to try something I never had before. After all it was still early in the evening. With the thoughts still in my head, and the pent up sexual frustration, I logged into an online sexual encounter site and placed an ad. I titled it, “amateur transvestite hooker looking for motel fun tonight.” A little role play is always fun. nevşehir escort I added a pic of myself and within a half hour I received 5 replies. The first four guys that responded were either fat or ugly and had a weird looking penis or just came off sounding creepy and demanding. Nothing really attracted me and their replies just weren’t appealing enough. Maybe it’s just my CD ego being very picky and selective as usual. The last reply wasn’t bad. A mid 30’s married man who included a pic of himself and his cock. He was very handsome and said he his wife and k**s were away for a couple of days visiting his mother in law. His cock wasn’t that bad looking at all either. Had to be at least 7” cut nice and neatly trimmed. That got me even more excited. I paced in my kitchen nervous wondering if I should really reply back and go through with it. Every click of my heels in the kitchen and every passing glance of me through the living room mirror kept me thinking about his cock. So I went for it I replied back to him and he told me to meet him at the Holiday Inn across town. He said he’d text me when he’d get there to tell me what room he was in. I decided to get into my car and drive around town for a bit. I feel somewhat anonymous at night. I stopped by a gas station and pumped some gas into my car. I couldn’t help noticing a couple of young good looking college guys watching me and checking me out. I overheard one tell the other, “look at her, she’s hot bending over like that”. I felt a little more relaxed and couldn’t wait for later. After getting back into my car I received a text from him. He said he was in room 115 and that the only entrance was on the inside down from the front desk. Well here go the nerves again. While driving over to the motel I sat in the parking lot thinking how I’m going to manage to get passed the clerk. I mean what are they going to think of a guy dressed like a girl walking in there. I’m sure they’d stare. But then I looked at myself again in my rear view mirror. I looked at least semi passable enough. So I grabbed my purse, sprayed on some quick spritzes of perfume and headed inside. Lucky for me the female front desk clerk was checking in an older couple. Although my heels clicked all through the lobby, they really didn’t pay much attention to me. I glanced back when entering the hallway and noticed the old man checking out my ass…..lol. I made it to the door of room 115. I was really feeling like a “wanna- be” hooker after shaking my ass down the hallway on my way to meet my “John”. I wasn’t quite sure what I was going to say or do. But was really getting excited at what I was doing and the path so far. It’s like something else inside me took over. I knocked quietly and heard him walk to the door from the other side. He opened the door and smiled. He looked pleased at what he saw as did I. he was a very handsome dark haired fellow dressed in jeans and a T-shirt. He had some nice strong escort nevşehir arms and a muscled chest that showed through the tight t-shirt he was wearing. He then asked me to come in. while entering the one bed room I quickly scanned around making sure he was the only one there. You never could be too careful. After feeling safe enough I walked over as girlie as I could and sat down in one of the motel room chairs sexily crossing my legs. I knew he was checking me out the whole time. He told me that he’s always had an attraction to crossdressers and fantasized about a meet someday but his wife was the jealous kind. He said that he rarely has time to himself much less watching tranny porn. He said when he found out his wife and k**s would be gone the weekend he said he was going to take full advantage. After commenting on how good and sexy he found me he started asking about price. I then told him that my ad stated amateur prostitute and told him I’ve never done this before either. We both laughed a little and felt more relaxed. I asked him, in a joking way, if he was a cop. Having worked around plenty for so many years I could smell the bacon a mile away and knew by the way he acted and looked that he was far from one. But from further incrimination I told him I wasn’t going to discuss “how much” with him. I told him that I’ll only accept tips or donations for my companionship. He could tip me whatever he feels like and to not hand it to me directly after our time together. I then asked him what he wanted to do and it was then that he told me to stand up. He then stood in front of me and put both hands on my hips. He was just a little taller than me and I was close enough to smell his after shave. I put both my hand around his hard strong arms. He leaned over to give me a kiss on the lips but I instinctively turned away. For some reason when dressed I have no desire to lip kiss men or top with one either. Now with other CD/TV/TS that’s a different story. I guess I feel more comfortable playing the submissive bottom type with straight men. He then started caressing my ass and ran his hands down my legs. I could see he was nervous and shaking and it was probably his first time with a CD. He told me how sexy my legs were and really liked the fishnet, heels and mini skirt look. He also said I had great looking boobs. We both had a good chuckle again after I told him, “They are fake you know”. Since he couldn’t kiss me on the lips he put his head down and began to kiss my neck. I have to admit his warm breath on my neck was such a turn on and I could feel my erection beginning to grow. I got even hotter when he put both his hands and squeezed my ass. It was then that I felt he was just as excited. I felt his boner press up against my stomach. He then told me he wasn’t sure what to do next. He admitted his nervousness and asked me if I had any ideas. Without hesitation I knelt down in front of him. I reached up and unzipped nevşehir escort bayan his pants pulling them down to the floor. I could see his big hard bulge in his boxer briefs which I then slowly pulled down. It was then that I put one hand on the back of his right leg and used the other hand to reach up and grab his long hard shaft. I rubbed it and stroked it enough to see and feel it get hard. He was more like 7 ½ “than 7”. But it looked so hot and I couldn’t wait to put it in my mouth. I asked him, “is this what you want?” as I slowly licked the head of his cock. He said, “Yes baby, it’s one of the things”. Him calling me “baby” was such a turn on too. I then slowly engulfed his gorgeous rod in my mouth. It tasted just as good as it looked. After sucking his cock for a few minutes and rubbing the back of his legs and ass his heavy breathing told me he was ready to cum. But before he did I pushed him away and told him to sit on the edge of the bed. I then turned around with my ass facing toward him and pretended to give him a lap dance. I slowly pulled down my mini skirt exposing my pantied ass in front of him. I asked him if he liked what he saw and he told me that my panties looked so hot on my round ass. I laughed and told him, “Thanks, I just got them today”. I then asked if he liked his blow job and if he wanted more. He said, “yes babe, I want to fuck you, if you’d let me” I then pushed his back against the bed, pulled off my panties and got on top of him. I reached under his shirt and massaged his manly chest. I pressed my ass on top of his big hard cock and rubbed my ass pussy up and down on his erection. I then reached over and grabbed the bottle of lube I had in my purse. I placed a good size amount on his hard cock and rubbed the rest on my boi pussy. I then mounted his cock slowly and felt his hardness all the way in as I sat on him. I leaned forward to hold both his shoulders as I rode his fine rod. First slow then fast until I we found a medium pace. I loved the way he moaned. “Oh yes, fuck me baby, you feel so good” after another few minutes he told me he was going to cum. I then got off of him and had him stand up again. I knelt down in front of him again and told him to cum on my face. As he was stroking his big hard cock in front of me I began to play with my cock. That turned him on even more. He started jacking it faster telling me, “that’s it babe, play with your clit” I then told him, “C’mon you could do it cum on my face honey” he then let out a loud moan and sprayed his hot juice all over my mouth and cheeks. To his surprise I put his cock in my mouth and cleaned the rest of his cum off his gorgeous cock. I then told him I had to go and went to the bathroom to straighten up. Before I left the room he told me what a wonderful time he had and that it was just what he wanted for his first time. He also said he couldn’t wait to do it again sometime. I left with him saying to check my purse when in get home. I left the room strutting through the hallway and lobby just completely beside myself. I actually pulled it off.When I got back home I checked my purse and found $120 and his phone number. I guess I’ll be shopping at Victoria’s Secret from now on.