tagTransgender & CrossdressersJessica Loses Her Virginity

Jessica Loses Her Virginity


This is a true story.

My name is Jessica and I've been a cross-dresser pretty much all my life. I still remember my first time with a guy.

During college I'd often get dressed up and call these phone dating lines that are free for girls. The guys had to pay but the girls didn't. I've always had a knack for speaking like a girl so I'd call and pretend to be a girl. On these lines I'd either talk dirty to these guys and have phone sex with them or tell them dirty slutty stories of my female self. Both ways were a means to get off and pretend to be a girl for me.

However, sometimes I guess either I wasn't convincing enough or I gave it away on purpose, the guy would know I'm a CD. The reaction ranged to people calling me a freak to others who were even more turned on and wanted to meet me. With that came my first means to meet guys.

The first time I gathered enough nerve and drank enough vodka to finally agree to have a guy come over to my apartment to meet me. I was just out of college and was living in a pretty gay friendly city so wasn't too worried about meeting a phony bad guy.

I'm about 5'11" and weighed about 165lbs. I wasn't super skinny but since I was tall enough I wore a size 10 and looked like your average tall sorority girl at the time. I had this wig with auburn straight hair that kinda looked like Jennifer Aniston's hairstyle. And I followed the natural make up scheme because i didn't want to look drag.

I brought out a matching pair of black sheer Victoria secret string bra and thong, and a pair of sheer thigh-high's. Inside my bra was a pair of silicon bra inserts that I also bought at Vicky's. With the "enhancers" I was around a 36C, 32 waist, with a cute little bubble butt. With my height and proportions I thought I kinda looked like Jessica Biel. I put on a light blue sweater tank top and a sheer black blouse and slid on a black pleaded miniskirt. I looked so good. I looked like someone I'd totally want to fuck her brains out.

About 30 minutes later it finally came time to go out and meet what potentially could be my first fuck as a girl. I was so nervous that only another shot of vodka calmed me down. I finally gathered up enough nerves to walk out into the parking lot when my mystery date's car pull up.

He was tall and skinny with dark hair and artsy glasses. He walked right up to me and came close and kissed me. I've never kissed a guy before then and my heart fluttered. We immediately embraced some more and I flirtatiously grabbed his hand and lead him back towards my place.

Once we got there he kept kissing me and told me how pretty I was. As we're making out I found my hand, almost as if it had a mind of its own, creeping towards his jeans. He was already hard and I stroked his cock from the outside of his jeans.

I wasted no time and quickly knelt in front of him and started unbuckling his belt and unbuttoning his jeans. I finally pulled his cock out and it was the first time I had a close and personal look at someone else's cock. It was long, smooth, and not too thick. As if by instinct I opened my mouth, stuck my tongue out and started licking his cock like a lollipop. It was such a weird sensation and feel in my mouth. It was like nothing else I've ever tasted.

I was so turned on knowing that I was finally doing what a girl does. I started really getting into it and started bobbing my head up and down his cock and slurping at it as if I was starving. I licked and sucked and jerked him and eventually I started to taste a familiar taste....it was his precum. I had tasted my own precum before and knew what it tasted like. Being so turned on and this guy being so cute and nice I was determined to have him be my first fuck.

In between slurps I asked him if he wanted to fuck me. And he nodded yes with enthusiasm. I got up, danced over to my purse and grabbed a condom, went back on my knees and rolled the condom on his cock with my lips. From seeing how other girls did it to me, I've always wanted to do that.

After making sure he's all set, I slicked his cock with lube and turned around reaching behind me to put some lube on my virgin asshole. I knelt on my hands and knees on the couch and lifted my ass up in the air, waiting for him to do me.

He lifted up skirt and moved my black v-string thong aside and started slowly easing himself in. It took a little bit of "hit and miss" but even that was turning me on. He was rubbing the tip of his cock up and down my hole.

Then it happened. I felt his nice mushroom shaped tip slowly parting my ass. With a small "pop" his head was in. I've practiced with smaller dildos before, but never the real thing. I was so excited but I knew I needed to breath and relax. As soon as his head was in, she started slowly pushing his full length into me. He was so gentle, telling me to relax and stroking my back. He had such a nice cock for my first. It wasn't too thick and it was nice and long. He slowly glided into my ass. And when I felt his full length into me as his pelvis bumped into my tush, I finally felt like a woman!!

Sensing that I've finally relaxed enough so he couldn't hurt me, he started to pump back and forth, in and out. It was the most incredible feeling ever. I started to moan and snapping my head back and forth as well.

I sigh and moan saying out loud, "oh my god you're inside me,"

"I can't I'm being fucked by a stranger...."

"I've just met you and I'm letting you fuck my brains out, I'm so slutty..."

Talking dirty like a little slut definitely turned him on because now he's working up a rhythm pumping his cock in and out of my ass. He started fucking me so hard and deep that with each pump he was bumping my ass cheek so hard with his pelvis that it almost hurt. He placed both hands on my ass and squeezed it as he kept fucking me harder and harder.

The action was getting too rough for the couch so I moved down to the floor and resumed the position by getting on my elbows and knees.

He got back behind me and with me whining, "get back inside me," he quickly pushed his cock back into my ass.

This time was much easier as he slid right in with no problem whatsoever. He reached one hand up to cradle my breasts while the other was on my neck as he whispered to me how hot I was and how much he loved fucking my ass.

I was beyond turned on at this point and moaning so hard that I'm sure my neighbor knew someone was getting fucked in here. Finally he was fucking me so hard and I knew he was about to cum.

He had a condom on but I didn't want to take the risk of him cumming inside me, plus I wanted to do what all slutty girls did on a one night stand with a stranger.

I yelled out, "oh my god please I want you to cum on my face!!" and that pushed him over the edge.

He yelled back, "oh yes Jessica I'm cumming..."

With that I quickly spun around opened my mouth and with him knowing what I wanted, he ripped off his condom just in time to spray my face with my first hot spurt of creamy white cum.

His must have been totally turned on and plus the fact that we must have fucked for an hour because he kept cumming. Spurt after spurt his seed splashed against my face, and into my opened waiting mouth.

I felt hot thick streams of cum hitting my tongue and the back of my throat. It tasted kinda sweet, kinda salty, and kinda bitter. But it was the consistency that was odd. Kinda gooey and slid around in my mouth and down my throat like warm oysters. Even with my eyes closed I could smell his load as it dripped down my face, across my lips and down my chin...onto my cleavage and eventually down my lap.

Unable to resist, I wrapped my cum covered lips around his cum dripping cock again just to suck off all that I might have missed. I put my hand on his cock again just to jerk and gently squeeze any a little bit out and finally finishing with the tip of my tongue licking the tip of his cock for that last drop. Then we both collapsed onto each other.

As nice as it was it is always awkward afterward. He was really sweet and held me while caressing my arms and neck while telling me how beautiful I am and how sexy I was during the whole thing.

I felt like a well fucked girl and a total slut lying there with a strange man and his cum all over my face and down my throat.

I got up to light a cigarette and went to the bathroom to both look at myself and also to clean up. Even though I've just finished getting fucked, I was instantly turned on again when I saw myself in the mirror. What I saw wasn't me, it was a hot, gorgeous slut with a face full of cum who just got her brains fucked out.

Pearly white globs of semen was still around my lips and chin. I couldn't help it and licked my lips around my mouth just to taste it one more time. I could have gone right back out there and have him fuck me all over again.

But I didn't.

Reality slowly seeped in and along with that, guilt.

Kind of in disbelief of what I've just done, I quickly cleaned off my face and went back into the living room, gave him a quick hug and a kiss and told him that I'll call him again. He left and I never did. Thinking back I should have called him because he was such a sweetheart and he was really gentle to me for my first. I've been a quite a few since then and although all were nice, there's nothing like a girl's first. Til this day I still can't remember his name.

But I will never forget his cock!

*please let me know if you like this story! I'm always looking for new friends to share stories with!

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byDCJessicaCD© 11 comments/ 108398 views/ 28 favorites

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by Anonymous

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by Bo_likes_go05/02/19


Very sexy story I always loved taking a naughty cute girls virgin ass and making her moan on my throbbing hard cock

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