Double date

Let me start by saying this is a true story. It's kinda long

So my best friend and I had plans to go out one night. She called me earlier in the day to tell me she was going to hang out with this guy she was interested in and that he had a friend that could also come over.
I really wasn't interested in a blind date, especially if its only purpose is to justify my friend from ditching me for the night. I told her that i really didn't want to have some guy i wasn't into trying to grope me and fuck me all night because i will be stranded with nowhere to go because we where going to borrow here parents minivan for the night.
She assured me that he was a nice guy and he was supposedly a virgin. I reluctantly agreed. she came and picked me up and we where all going to meet up at her soon to be bf's house. when we arrived both the guys where sitting on the porch. i said right off the bat as soon as i seen my date "Don" that I wasn't interested to her before we ever got out of the car. He was a bigger guy, not really fat , he looked built and strong but also overweight. he looked kinda dirty in a punk rock sort of way.
They decided that she would drive and her date would ride in the passenger seat while Don and I rode in the back. there was very little dialog from him, unless he was talking to John, "her date". he would sneak a peek of me now and again but for the most part it seemed like he was driving to a funeral. First we went to dinner and he held the door open for me and pulled my chair out for me, I was actually charmed. He seemed really shy, and to top it off my friend and her date couldn't keep there hands off each other. at one point I tought she was jerking him off under the table. So I started small talk to try and get some kind of dialog out of him because as soon as my gf and her date started kissing and flirting with each other he became mute. I got him to start talking but it was painfully obvious he was terrified of me, but he was actually really sweet.
He offered to pay for my meal but i declined.

Then we went to go see a movie. I already knew where this was going. as soon as we got to the theater he asked if i liked popcorn, i said if you want to buy some ill eat some. as soon as we sat in our seats the 2hour tonsil boxing started between my gf and her date. at one point i swallowed a piece of popcorn wrong and started to choke a little bit. Don offered me some of his drink. he pulled the top off of the cup so i didn't have to drink from his straw. i thought it was sweet but kinda weird. i laughed and whispered in his ear, What do you think i have coodies? he smiled and said no. about 5 mins later he put his hand on my leg. i could tell it took every ounce of confidence he ever had. so to reassure him i put my hand on his thigh, we wound up holding hands for the rest of the movie and i couldnt help but think"no wonder he's a virgin". I was also getting kind of hot watching my gf and her date going at it. I mean it looked like they where rounding third base in the theater.
We left the theater and where on out way back to johns house, his parents where out and no one was home. the plus side was Don was actually warming up and talking to me now. I have to admit although he's not really my type i was kinda starting to like him, he was so charming and sweet. he opened every door for me, and the shyness was kind of charming. when we got to johns house he immediately offered to make us some drinks from his dads liquor cabinet. after a few drinks John and my gf went back to it, they where going at it strong and it was making it uncomfortable for Don and I. John was obviously fingering her out and she started to moan, It turned me on so much i wanted to join right then and there. I didn't really want to but i made the decision that Don and i should leave them to do there thing. I asked him if he wanted to go for a walk. we went around the block and talked a bit, i asked him if he had a gf. he obviously said no, he said he didnt really date too many girls. I asked him if he was gay and he laughed and said yea im gay, in a sarcastic way. we where almost back to Johns house when we saw his parents pull in the driveway. neither one of us wanted to go back in, i texted my gf to see what was going on and tell her that his parents where home, she texted me back that they was kinda busy and to take her moms minivan if i wanted.
I decided i was walking anymore because i was wearing heals,and i really didn't want to go in to get her keys. so we decided to just chill in the van. we got in the van and sat in the back seat. not really having anything to talk about i asked again why he didn't date too many girls, he replied that none of the girls he likes like him. I asked how id he know? he said well, i asked them. I said you asked all of them? he said well no. i said then how do you know. he said i dont know. then I asked him what he thought about me. He kinda stuttered and said your beautiful. Now it might have been from the fact that I was already hot from watching my best friend and his best friend practically fuck in front of us, or the fact that i knew they where inside the house fucking at that moment leaving us with nowhere to go but sit outside thinking about them fucking, or maybe the fact that he was really sweet and charming. but i asked him if he wanted to kiss me. without thinking twice he leaned towards me and kissed me long and deep, we started making out in the backseat of the van. he started grabbing my breast and trying to slip his hand under my shirt. i got on top of him and straddled him and he reached around and was squeezing my ass. it felt like he had an iron pipe in his pants and i couldn't help but to start grinding on it. this really got him going and i thought for sure he was going to cum in his pants. I was wearing a skirt and he was trying to feel my pussy under my skirt from behind. i undid his belt and unbuttoned his pants,his eyes got really big. i told him in a sexy kinda joking voice ill show you mine if you show me yours. I expected him to pull out his cock but he took it a step further and kicked off his shoes and pulled his pants and underwear completely off. I was kind of shocked. i could see his heart beating through his cock. it was throbbing and pulsating. i decided to tease him and i pulled my skirt up and grinded his cock with my panties on. I was so wet that my panties where soaked through. i pulled them off and grinded his cock between my bare ass cheeks as we locked our lips together. my juices where running all on the top of his cock and i wanted to rub my clit on his cock. i attempted to reposition so his cock would slide down my wet pussy and i could rub my clit with his cock. what i didnt plan on was my pussy being so wet slippery that when i repositioned his cock slipped inside me. his eyes got really big and he moaned really loud. in as much time as it took for me to realize that his cock was in me I also realized that he was cumming inside me. at first i was pissed but before i could do anything about it he grabbed me by the back of the head and kissed me. then he wrapped his arms around me and just held me I never got off of him and we just sat there kissing with his cock still inside of me,until he got hard again. we started again only this time we fucked bareback until both of us came together. he came inside me again, it turned me on sooo much to have him cum in me. after awile he decided he wanted to lick my pussy, i have never been so turned on in my life that he was eating his own cum out of my pussy. everything down there was so wet and slippery that he tried to put hiis finger in me and i honestly think he was trying for my pussy but is went in my ass instead, i jumped and said thats m ass. he quickly pulled it out and apologized, it actually felt kinda good so i told him it was ok and he could do it if he wanted to. he ate my pussy and fingered my ass and i never thought that i would have liked it as much as i did. I got on top of him and said your turn, i put his cock in my mouth and eventually worked up the guts to put my finger in his ass. it really turned me on, i got back on top of him and whispered in his ear "do you want to fuck my ass". he said ohh yea baby. i tried to straddle him and kind of lower myself on his cock but it wasnt working so i decided to bend over and let him do some work for a change. as he put his cock in my ass it hurt at first and i was wondering if i could go through with it but after a few mins if felt better and better. i reached down and started rubbing my clit before i knew it i had the most powerful orgasm of my life. that was my first time doing any anal play and i loved it. After we where done we got dressed and just sat in the back of the van talking, my gf eventually came out and he went in to johns house and we went back to her house. I never thought that i would have had sex with Don, let alone the best sex I ever had, but i thought i was going to show him a thing or two about sex and it turned out i learned more about my own sexuality that night than i will probably ever learn again. We hung out a few times after that but it fizzled out quickly and we just stopped talking but i will never forget that night.






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Categories: AnalFirst TimeTaboo
Posted by gurl1990
4 years ago    Views: 2,197
Comments (9)
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3 years ago
real nice story
skelly
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4 years ago
wow that was a great story
TheDarkSa...
retired
4 years ago
real nice story
humths
retired
4 years ago
well written and I see your into the same taboo's as me. LoL
4 years ago
good story. know how he felt. took me ages to do the same. girl led the way. best yet.
like it.
4 years ago
Great story, all the better for the reality factor, well done
4 years ago
Well if im not wet like da hoover dam............;)
4 years ago
Well, there's this thing called a "Paragraph..."
4 years ago
That's story got me hard!