Losing my Cherry

Although l have been secretly cross dressing for years I have never took it beyond the confines of my bedroom or hotel room. Well I have been really wanting to take this to the next level. So as I was traveling on business this past week I answered an ad on Craigslist for a massage in my hotel room from a male masseur I made the appointment and waited with anticipation for my masseur to arrive. At promptly 8:00 there was a knock on the door and when I answered there was Chris a very handsome young man, I invited him in and he promptly set up his table..
As he was setting up his table and supplies I put on some soothing music as well as lighting some candles. Chris and I made some small talk and he let me know he was ready if I was ready. I was dressed in my boxers which I dropped to the floor and laid face down on his table and he put hot wash cloths on my feet which felt heavenly. He then proceeded to massage my back. Even tough he was dressed in a tight tank top and running shorts. He looked so nice but I invited him to get more comfortable which he gladly obliged. He had the most beautiful penis, and since I was new at this I was a bit nervous being alone in a hotel Rommel with a naked man. Many thoughts were going through my mind but I quickly calmed down as his hands started caressing my shoulders. As he worked his way around the table I felt his now erect penis brushing against my body. I gently reached out a and brushed my hand against his penis and oh my god it was so thick and erect. I waited for a reaction but Chris kept massaging and allowing me to stroke his penis.
He asked me to my back and he proceeded to give me a "happy ending" with his strong hands and as the pre cum was starting to ooze out of my penis he lowered himself down and took me into his mouth and he completed my massage and it was a glorious happy ending. However, I didn't want the night to end so I asked if he wanted something out of the mini bar and he helped himself. I stepped in the bathroom and let him know that I would be right back. I was nervous and my heart was pounding inside my chest hoping my plan would work. For the first time i was dressing and going to be stepping into a room with another person in it. I had my black nightie, I slipped my mesh black thong over my penis which was already getting a little tingly from my happy ending. I then rolled up my black thigh high stockings on my legs then slipped on my black pumps. Took one look in the mirror and said to my self "whet the hell"! I stepped out of the bath ronin and presented myself to Chris and waited. To my surprise he asked me to sit next to him and have a drink. He was still undressed and his penis was quickly becoming erect again. His cock was a thick 8 to 9 inches and I wrapped my hand around it and I could feel it pulsing. He was very comfortable as I grabbed some of his massage oil and oiled up his penis and started to stroke his penis paying close attention to the head and balls. After some time using my hands I went to my knees in front of him I parted his legs and placed that huge erect penis in my mouth. Oh it was so smooth and I flicked the head with my tongue and I tasted the sweet pre cum and I just started thrusting feeling his penis hitting the back of my throat holding back a gag reflex. Chris started thrusting his hips up and down going with my rhythm and I started hearing him breathe heavier and heavier and there was a little more pre cum and he tensed up and I sped up and pow just like that I felt this warm gooey substance on the back of my throat and in my mouth and like a good little girl I swallowed every drop. What a rush I can't wait to suck my next dick now that I lost my cherry.
95% (23/1)
 
Posted by mikkas72
5 months ago    Views: 4,044
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5 months ago
HOT blowjob and hot story!
5 months ago
Wow great story! And yes I'd love to be you too!
5 months ago
Great story! Wish I was there! I still fantasize about having a hard cock erupt in my mouth!
5 months ago
wow gurl I want to be you
Jay