Ride share turns into rough sex and my first anal

Several years ago, when I was in my late teens, I put out an ad on craigslist to get a ride from Chicago to Atlanta to see some f****y. Several people answered the ad and one of the rides pulled through. His name was John and he picked me up at four a.m. so we could get an early start and by 7 a.m. we were throughly discussing our sexual exploits. He was in graduate school working towards his doctorate's in criminal justice and being, in his early thirties, had had many exciting sexual experiences.
Although I was so young, I had had my fair share as well. We found out that we were both very interested in rough sex. I had only had one sexual experience where the guy was in control and demanding and it turned me on very much so I was eager to further explore this avenue of my sexuality. I told him all about this former lover of mine who had surprised me by being controlling in the bedroom and how much it turned me on. I went into intimate detail about how he held my head down on his cock the first time I sucked his dick and how this made my pussy throb with anticipation and make it so wet that I came almost the instant he started thrusting his fingers inside of me. He told me about his ex-girlfriend who loved it when he pulled her hair while he fucked her doggy style and how much he loved to hear her scream and moan while he pounded her into the bed, wall, whatever. He went into intimate detail about anal sex and how much he loved to bang a girl in her ass. I admitted to fingering my ass and how much I wanted to try anal. My pussy was getting wet by all this sharing. He adjusted his growing erection and said that our conversation was very hot and making him hard as a rock.
I reached over and began rubbing his hard cock while his hand went to my breasts and he began playing with them.
"take your tits out" he said. He had heavily tinted windows so I did just as he asked. i lifted my shirt and pulled my tits out the top of their bra. He groped them, squeezed them, and played with my nipples as I rubbed his crotch harder and harder. I took his cock out of his pants and through the hole in his boxers. I gripped his head in my hand and rubbed it up and down. It wasn't too big or too small, just a normal size and very soft. I couldn't wait to put it on my lips.
His hand went down to my crotch which was very wet. I opened the front of my jeans and slid them down over my hips. He fondled and played with my pussy lips through my panties, sliding them over my soaking pussy. Both of our hands moved faster and faster over each other's genitals and the sexual tension built. Eventually he couldn't take it anymore and he pulled over to a remote area. He put his hand on the back of my head and pushed my face onto his dick, rubbing it all over my face while his other hand once again played roughly with my tits.
"fuck baby, you're so hot. suck my cock"
I obeyed and sucked the tip of his sexy cock, putting more and more of it into my mouth while I rubbed the shaft up and down. i got into a nice rhythmn, anticipating him exploding in my mouth, when he insisted I no longer use my hands. I bobbed up and down on his erection, my tits bouncing on the consol between our seats. his hands occasionally went to the back of my head, pressing his cock further down my throat. He lifted his hips to fit more into my mouth and moaned with pleasure. once he got really turned on, he began calling me names. telling me what a dirty slut i was, how glad he was that he gave me a ride, that he was going to cum down my throat, all kinds of nasty stuff. Finally, he pumped his shaft a few times and announced that he was cumming. "Swallow all of it," he insisted and began to jizz down my throat. I sucked and sucked until he was finished.
By this time we were almost to Atlanta so we got back onto the highway and I leaned back, fingering my pussy and rubbing my clit to climax.
He dropped me off at the train which I was going to take to an outer part of Atlanta and we agreed we'd meet back there in one week. Both of us were looking forward to the ride back.
We exchanged sexy texts throughout the week and were both glad to leave our relative's houses to get back to Chicago.
On the ride back we got stuck in traffic right outside of Chicago so once again I gave him head and listened to him talk dirty. He fingered me to climax and also watched me play with my pussy and use a dildo on myself while he drove. We were both very tired from the drive and our vacation so he just dropped me off at my apartment once we got back from Chicago.
Two weeks later we met up again for drinks and i figured it would be a wild night. Just in case, I had done all the proper cleaning and was anticipation the night anxiously. I was even a little nervous when we met for drinks.
We were sitting in a dark bar and after exchanging the usual nicities, he reached over to fondle my breast.
"I've been thinking about you all week. That was an incredibly hot trip we took. I haven't been blown like that in years. Are you ready to take this to the next level? because once we get back to your place, there's no going back."
A jolt of nervousness serged through me but I was definitely interested in going to the next level.
"Excellent because I'm gonna pound you so hard your legs will be sore for week." My pussy throbbed. He continued to whisper dirty nothings in my ear, telling me all the things he wanted to do to me and how it was going to feel and how he couldn't wait to see me covered in his cum. After several drinks we went back to my place and as promised, it was on.
He pulled me to him and his hands went to my ass, he lifted my skirt and squeezed my cheeks, pulling my belly to his erect penis. I moaned as his lips went to my neck and he lightly bit me. Before I knew it, his hands were all over me and half my clothes were off. He pushed me to my knees and took out his cock, his hand guiding my head, urging me to put it in my mouth. again, he told me not to use my hands and i obeyed, letting him thrust his cock down my throat further and further with each thrust. it felt amazing, my pussy was soaking wet and my nipples were at erect attention, waiting to be fondled and squeezed.
Hours passed and we did every position we were unable to achieve in his car. He ate my pussy for atleast 20 minutes and I had cum atleast 2 or 3 times before he put his dick inside of me. Finally, he mounted me and eased his cock inside of me.
"Fuck, you're so tight." He moaned. He grunted with each thrust into my soaking pussy and pulled my hair to make me scream louder while his other hand mauled my breast. He told me how good my pussy felt and that I was his whore.
He turned me over and pushed me to my knees, inserting his cock into my pussy doggy style. This is where he stuck his first finger into my tight ass. I moaned with pleasure and begged him to finger my ass while he fucked me. He obliged and began thrusting his finger into my sweet hole, adding another finger a little while later. I screamed into the pillow while he fucked me harder and harder. He got up and got the dildo and oil I had set on the night stand and squeezed out some oil onto my asshole. I gasped at the coldness of it and tensed up a bit.
"Relax, baby" he said, as he put the dildo at the entrance of my asshole. He slowly pushed it into me. I had used my dildo in my ass several times before so the sensation wasn't new and I greatly enjoyed the mixture of pleasure and pain. He got past the sphincter and pushed it in further, lubing it up mmore as he slid it in and out of my hole, further each time. I was quiet at first and later began to moan deeply. He pumped his cock, enjoying playing with me. He started to push it in and out faster and faster. I could tell it was really turning him on and he aching to get his cock balls deep into my ass.
Without a word, he took the dildo out my ass and positioned himself behind me. I was unsure if he was going to stick it back into my pussy or deep into my ass and the anticipation made me very hot. I felt him put the tip of his head at the opening of my ass. Him not telling me where he was going to stick it really turned me on and I pushed back.
"You want it in your ass?"
"Yes" I moaned
"Tell me."
"I want your cock in my ass. Please stick your cock in my ass."
He pushed the head inside of me and it felt way better and more painful than the dildo. It was thicker than the dildo and I really enjoyed the sensation of his skin on mine.
Slowly, slowly he fed my ass his cock, taking his time and lubing it up very well. I played with my pussy and moaned each time he stuck more of it into me. He began to pick up the pace and within a few minutes I was cumming again. He got faster and faster and eventually stopped so that he wouldn't cum so soon.
The night continued well into the morning and he stuck his cock in all my holes many times. He spanked me, fucked me against the wall, on the floor, from behind while on my dresser, held my hands down and pounded me into the mattress, held my hands behind my back while I gave him head, and did me in every known position. It was quite an amazing night.
We had sex like this four or five times and eventually stopped seeing one another because he was in a relationship but it was inccredibly hot and I have yet to meet a man who could fuck me like this on a regular basis.
100% (61/0)
Categories: Anal
Posted by sweetsimone
3 years ago    Views: 2,709
Comments (17)
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1 year ago
Ooops - gonna have to wank my old cock - horny story
1 year ago
very very hot story :) I take road trips all the time maybe we can repeat this story :)
1 year ago
Loved reading about your experience
2 years ago
very good
3 years ago
hell of a story
3 years ago
I'm glad you liked my story. Unlike most of my others, this one actually happened and was extremely hot!
3 years ago
mmmmm very sexy
3 years ago
Wow that was a HOT story. Great piece of erotic writing :)
3 years ago
Excellent!!! Loved It!!!
3 years ago
Oh my, Simone, you create a very sensuous word picture. Quite stimulating.
3 years ago
Fuckin awesome
3 years ago
You sure do know how to write an erotic story :)
3 years ago
great story
3 years ago
Good read, Thanks.
3 years ago
hot hot hot great story!!
3 years ago
Very good
3 years ago
Fine blend of exciting and believable.