My night of first times!!!

I was sitting in the bar with my friends when she walked in. Black short dress, low cut neckline. I can see the garter straps holding her stockings. I think that is what caught my attention first. I had seen garters and stockings in movies but never in real life and her legs looked great. I couldn't keep my eye off her all night. I had to seem like a stalker with my eye's, I wasn't paying much attention to the conversation at the table with my friends she was lust at first sight. I had to make a restroom trip and when I walked out she was standing there. My heart skipped a beat and my stomach creeped up to my throat when she said hi. I had a high school k**s reaction when I look back on it, kind of makes me smile and giggle. I managed to say hi back, when she walked close to me and asked if I liked what I saw. I don't think I said anything just nodded my head yes. I remember her saying something about how cute it was that the cat had my tongue. She then walked in the restroom and I returned to my friends. When returned to the bar my attention was back to her. All evening she was center of attention playing darts and pool and flirting with all the guys. As the evening was coming to an end I used the restroom one more time and again she was waiting outside when I walked out. She asked if I had a ride home, I did ride with my friends but I said no. She asked if she could take me home, after a big gulp I said sure. As we walked out my friends saw me with her and I wave my hand for them to go ahead. She had a little pick up truck, I climbed in the passenger side. When she climbed in she pulled her dress up a few inches and I couldn't take my eyes off the garter straps and her long legs. She giggled and said how sweet i was that I couldn't take my eyes off her. I told her I didn't mean to stare but I couldn't help myself, Then she asked if I wanted to go somewhere and see more. My jaw hit my lap, and I could manage to talk I said of course. She drove a little bit then turned off onto a dirt road that headed back into a wooded area. She pulled up into a small openning and placed the truck in park. Then she turned to me grabbed me by my head and started kissing me very deeply. Her one hand slid down to my chest stopping to squeeze my nipple. Soft and lightly at first then she gave it a hard squeeze. I moaned into her soft mouth as we continued to kiss. Her hand then trailed down to my lap where she found my already erect cock. Now she moaned as she squeezed it. She broke our kiss and said that we need to free him from these cloths. I fumbled with my belt and she unbuttoned my levi's and we both pulled my jeans and underware to my knees. She placed her hand on my erections and slowly stroked me as we kissed again. Now Thinking back this only lasted a few minutes but at the time it felt like it lasted for hours. But she broke our kiss and lowered her head into my lap, she kissed the tip and licked around the head then my cock disappeared into her mouth. She went down then up and back down nice and slow. Then the pace picked up slowly, her hand grabbing my balls and she rolled then in her hand as she quickened her pace. All of a sudden my eye's rolled back as I told her I was cuming, she never slowed down and I shot my load in her mouth. She just kept sucking to get every drop out, one last squeeze on my balls and I was spent. Gave her everything I had, then with out warning and for my first time she gave me a big sum kiss. I couldn't believe what I was doing, it was so hot and i tasted so good from her mouth. I grabbed her head and licked the inside of her mouth trying to get all of me back. While doing so I got so worked up my cock was erect again, she pulled it and said she was glad I wasn't done. I told her I was far from done and that I wanted to go down on her. She said she was glad to hear me say that. She pulled up her dress and I pulled down her panties...... Again my jaw hit the floor at what I saw..... She had a penis I couldn't believe what I was seeing. I looked up at her and didn't know what to say. Then she broke the silence, she said what did you change your mind. Now all I think of was the best job I had just gotten and she was beautiful. Amazing eye's that just screamed fuck me. Next thing I knew I had her cock in my mouth. Sucking her head in until her half limp cock was all the way in and my nose was hitting her bare pubic area. This was also the first time I saw a shaved cock, I was very turned on by her shaved cock in the middle of those garter straps. I just sucked her cock in my mouth until she was nice and hard. Then I place my hand on the shaft and stroked it while I licked and sucked and lick her cock head. She then stopped me and said lets get out. When I meet her on the other side she had her dress and panties off. there she stood nice smallish breast, garter and stocking, high heels and a rock hard boner. I nearly passed out at that sight. It was the sexy thing my eye's had ever seen and my heartbeat would have proved that. She turned around and bent over while saying that she wanted me in her asspussy. When i walked up I bent down and started licking her, she was surprised when she felt my tougne. She looked back put her hand on the back of my head and said that i was such a dirty little boy. She tasted so good and again this was another first for me, first time I had lick an asshole and I was glad she tasted so good. After a few minutes I stood up placed my cock at her openning and pushed forward just a little. When I stopped she pushed back and I watched as my cock disappeared in her asspussy until it was gone. She pulled back until just the head was in and looked back and said its ok baby take it. I grabbed her hips and moved in, not fast but a nice paced until I slammed her cheeks. Then my pace quickened and started fucking her good as my cock went in and came out. next thing I knew I was about to cum again, I heard her say not to cum in her ass so I pulled out and shot my second load on her back. She stood up turned around kissed me and said that she wanted to do the samething to me. I told her I didn't know and that it would hurt. She smiled and asked if my asspussy still had its cherry and I said ya. Her cock went from half limp to rock hard. She grabbed my head and lowered me to her cock, I was sucking her again while she begged to let her have my cherry. Next thing I knew I stopped sucking turned around and bent over. She popped her cock head in my ass and I jumped, It hurt like hell and burned. She said she was sorry and that she would go easy so I bent over again and she eased her tip in again. This time the pain wasn't as bad, she worked her cock in little at a time, almost like a rocking motion slowly in and out. Then I felt a pop and all pain was gone and all i felt was pleasure, a plwasure i never felted before. Then she grabbed my hips and buried her cock inside me and all i could do was moan. She sarted to pound my ass and my cock was getting hard again so i started to stroke it while getting my ass fucked. Then she told me she was cuming and i spun around taking her cock in my mouth and swallowed her load. Again my first time.

We had more sex after that, I dont remember how times I came but it was the greast night of my life.

This is just not a story but very true. This night happened 20 years ago and I'll never forget it. This is also the first time I've ever told it. I've never had a real cock in my ass again nor had one explode in my mouth. My wife takes her strap on to me from time to time but not the same. I have often thought about stepping out on my marriage to repeat this but it must be a shemale again. I'm obsessed with t gurls as they are now called. Who knows maybe i'll never have that feeling again. It feels good writing this story kind of getting that feeling just thinking bak to a night to remember...

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Categories: Shemales
Posted by Trudru
3 years ago    Views: 1,977
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3 years ago
3 years ago
3 years ago
Lucky guy!
3 years ago
Now that was some experience thats what happens on first time with a t gurl thanks for the story.
3 years ago
Nice story.
3 years ago
thanks for sharing your great story!