You know, before now I’ve never actually gone over, in detail my sexual history with anyone!
I’d like to go over girls I’ve had sex with, it turns me on sharing details and I’ve never actually sat down and gone over it all with anyone before! I’d love to hear your stories in response, I always like some interaction. Feel free to ask questions and comments about my experiences!
I’m trying to keep it realistic, I don’t like huge lists of bragadocoious, unrealistic sexploits and this is not supposed to be one of them. We aren’t all porn stars here.
That being said, I was in a fraternity and on the football team so I did have plenty of encounters. There’s stereotyping for a reason haha. And for the record I measure 6in long by 6in girth, for some girls that’s nothing for other’s it can be a bit much!
Kira –
The first girl I ever had sex with, she was a year+ older than me, which in highschool was a big deal! She was my female best friend’s, best friend. She had a reputation for getting around but actually talking with her she is the nicest girl who is just truly interested in life.
I first had sex with her at my family’s Christmas Party. Most of the other guests had left, the wine was mostly gone, and she led me up to my room. She laid me down on my own bed and gently kissed my neck, taking the initiative to undress me. We had made out a few times before at house parties but this time was different. She went slower and she was more hands on, she rode on top of me until I came.
Stayed friends with her for years after we hooked up, still on good terms with her. Her body was thin but not skinny, smaller tits but she knew how to fuck and deepthroat. Forever ruined blowjobs for me cause of how good she was. Dated her for awhile after I lost my virginity to her but she got bored and dumped me. Cute little butt, could use her hips like crazy, learned a lot from her about how to go down on a girl among other things
Bailey-
She was bold and actually asked me out first, we went to a high school dance together junior year, made out there and then later hooked up every summer and winter break freshman and sophomore year in college. She was so fun. Always dancing and partying, she’s a bit bigger and hit my kink of being with thick girls. Redhead who is now a successful professional person. We used to sneak down to golf courses at night to make out and hook up.
We were never together and never had a bad breakup or falling out either. She was bigger than average, great butt, small tits and nice thighs/legs. Super inexperienced but so was I. She always struggled to fit me in her mouth and pussy but it was fun trying in the dark under the stars as teens nonetheless.
We would typically sneak some of our parents wine or vodka down to the Golf course after dark and lay on the green just talking and kissing until I would get on top of her and awkwardly thrust inside her. We got better as time went on, it was more fun than kinky.
Nicolette-
My prom date senior year. She was a bitch not gonna lie. Always craved attention and I was pretty sure she was just using me to make her on-again off-again boyfriend jealous. I didn’t care. I fell under her spell. We only hooked up twice but made out all summer before college. I got pretty upset at her and we had a falling out before college started.
She had full, big D cup tits, super thin and she was fun to fuck cause she was so tiny! My dick looked huge inside her, she also really struggle to fit me inside her and also refused to give head but always wanted me to go down on her.
I would just rub my head in and out of her till I came all over the outside of her sweet little pussy. She got so mad lol she didn’t ever want me to cum on her. She would usually have me penetrate her for a few minutes then finish her off by eating her out.We always went to the beach and got coffee and burritos together afterwards
Ashley-
Alright well I’ve written thousands of words about this one. She was my best friend’s girlfriend and we all had several threesomes together. She was into cum play and some light bi stuff. Most experienced girl I might have ever been with. Came from a broken home and used us to get her sexual frustration out. She was two years younger than us.
We kinda “dated” as a threesome for some time our senior year of highschool. Easily took my size and my friends length, the best sex I had for almost a decade. She was short, curvy, dark haired but not too eye catching. Perfectly hot though once you knew her. She was super slutty, but only for certain guys. No one else had any idea, she was so innocent to everyone else. I can link to previous stories about her, not enough room here! Learned damn near everything from her
Tracy- Her and I were both from the same area but didn’t meet until college. We were in the dorms together and she was so cool! Another super tiny girl, barely 5 feet tall thin as a rail. Used to be as cheerleader, I was a football player. Turned out she cheered at a game I played where I performed really well at against her school.
We would go out to college parties and get drunk and hook up back in our dorm rooms. I always wanted more, I coulda seen myself being her boyfriend but she was in love with a guy from home.
She started officially dating him and we had to end things although we made out once after that :) we’re still tight, we comment and like each other’s social media posts. Loved being a freshman in college with her she was awesome! She was fun in bed cause I could pick her up and throw her around. She liked it kinda rough and fast and could actually fit me completely inside her no problem. I loved holding her in the air while she worked herself against my cock. We hooked up on and off for about a semester
Sarah-
She was such a nice girl, probably from a religious home and super conservative. We would talk alot and I made her laugh like crazy. That’s the common theme with every single one of these girls, they loved my sense of humor even if I wasn’t the most fit or outgoing guy. I do have nice arms and shoulders though :)
I was probably her only one night stand lol. Also a doormate, me her and Tracy were all on the same floor and hung out with the same groups of people. We were just friends after hooking up. She was just as unexperienced as Bailey, but in college! I couldn’t cum. Super cute pale blonde, kinda tall but very plain. Legs were her best feature. She seemed to have fun but really needed a boyfriend to open her up
Lauren-
My first fraternity hookup, she was at a Halloween party we had and her and I hit it off while super drunk. We danced, laughed and drunkenly sloppily made out. Typical college stranger hookup, sloppy awkward and funny to look back on. I don’t remember every detail but she wasn’t that cute lol. Last hookup of fresham college year
Jessica-
She went to a nearby college and found herself at our frat party. We got drunk and started talking politics, she was entirely pro Obama while I thought Romney had merits too. (Spoiler i ended up voting for Obama) we both hated Bush.
We had a deep talks that ended with us making out, once even disrobing and having sex in the open on campus at night. We did this twice, again on New Years Eve my Sophomore year too. That story is unreal and I can never tell it in detail in a way that seems realistic. We fucked in and against every building we found, in the elevator, the stairwell you name it. Borderline blacked out drunk the entire time. This is my go-to “crazy sex story”
We Facebook chatted a few times but barely saw each other after that. Different schools and all. When we did though, it was hot. She was a cute blonde, average body in every regard. That’s a common theme too, most these girls are cute to average, I’m not slaying stunners here haha, just girls I actually have a connection too.
Erika-
She and I held the same titles in our Greek organizations sophomore year. We both coordinated parties essentially. We planned several events together and after the first successful one, she was my guaranteed hook up at any Greek event. Also a tiny girl, she was short and feisty with curly dark hair. Great hips for someone so short.
Most enthusiastic girl in bed I’ve had. She craved me, first girl to shower my dick with compliments, there’s pictures of me on her laptop and phone somewhere still haha. I was the biggest she’d had, supposedly! She showed my pics to two of her friends, one later gave me a blowjob.
First girl that seemed to really love being stretched by my thickness instead of it being slightly uncomfortable or challenging. She would get laid pretty often and tell me about the guys she fucked as she was fucking me. I went crazy for that, it was hot knowing how many other men wanted her. Probably the “craziest” girl I ever stuck my dick in, totally worth it for her pussy. Loved her being on top of me. We would hook up maybe 3-4 times a month
Lauren2-
Erika’s friend who saw pics of my cock before ever hooking up with me. We actually didn’t have sex, she just sucked me off in the fraternity bathroom lol. Kinda trashy but incredibly hot in the moment. She’s on the list cause I was the second guy she sucked off that night in that bathroom and I found that so bold. So fucking sexy. I never minded having sex with a girl who just had/was fucking other guys
Kayla-
Summer between sophomore and junior years I lived in the fraternity house over the summer. We would have much smaller parties with students who lived locally. She was a theater major who was good friends with a guy in the Frat. She kept getting around and he never got with her, but I didn’t feel the slightest bit bad when she picked me out on a slow night after we day partied.
She had a deceptively sexy body under her bohemian hippy type clothes and she knew how to use her hips. Brunette, pale but kinda pretty with her freckles. We just had sex once and we actually got interrupted by drunk guys banging on the door yelling at us! Not an ideal ending, details are hazy, this is the girl I knew the least amount about before having sex with, never really talked to her after either.
Kayla2-
She was a bad ass mommy in every sense… except for actually having a kid. Latina, curvy, huge saggy mom tits, kinda overweight, bossy, demanding and opinionated.
We had philosophy class together and always were on the opposite sides of arguments and debates. We’d be the annoying people in class arguing with each other over philosophy questions haha, little did I know we were actually building sexual tension. She had a long term boyfriend but she discovered he was cheating. She showed up to my room with no bra and massive cleavage that night. Her natural tits were just unreal.
She drained me. She took out all her anger on me and milked my dick for all its worth. We got drunk at a party an she took my hand and lead me to my own room. She roughly rode my dick while on top of me, her ass slapping loudly, I was afraid she’d break me as I lay under her!
I came so hard so fast and she sunk her teeth into me and then gently stroked my chest while keeping my cock inside her, wiggling her hips and pussy, dirty talking me until I got hard again. I fucked my still warm creampie, or rather she did as she rode me hard and fast again. She made me cum inside her a second time. Still never taking me out of her pussy, my dick dripping with my own cum, she would alternately cuddle me and played rough until I got hard a third time. She furiously rode my dick again until I was limp and sore and covered in my own cum from three creampies.
We got dressed and headed back to the party, an hour having passed with us “missing”. After several beers and some dancing she pulled me back into bed and rode me again, same position,s name result.
This repeated once more, partying then sex until we collapsed from exhaustion. That was the single best night I’ve ever had in bed. The next morning and weekend were dissapointing but damn I still get off to that memory! Only my current girlfriend has made me cum as many times in one day as Kayla 2
Willy-
She was a bigger girl too, we met in Geography class and instantly hit it off with similar music tastes. She also loved my thick dick and we would get so drunk and stoned together.
I felt like an adult fucking her, we had our own apartments and would cook dinner, go to parties come home together. She loved laying on her back on the edge of the bed with me standing and forcefully fucking her, holding her legs and thighs. I could never cum inside her which always killed the vibe for me.
She actually had a somewhat serious boyfriend back at home who she would visit on the weekends and fuck, returning to class and me on the weekdays for casual sex and convrsation. I loved being her side piece, it was hot knowing some days she at separate times had sex with us both.
We would smoke weed and listen to rap all night whole fucking. Despite how chill she was she was super below average in looks and in bed. Never gave any effort. We hooked up for months though
Amanda-
Really tight friend, was never attracted to her initially until one night she pulled me into her bathroom at an apartment party and dropped to her knees. The only girl who’s ever wordlessly made a move on me. It worked cause we were friends and knew each other already.
I had started dating (non exclusively) my current girlfriend and Amanada knew it was about to get serious. Between mouthfuls of my cock she said she always wanted me and knew this was her last chance for awhile. I knew from a good friend that she gave super-head, turned out to be true! One of only two girls (along with Kira, see took me this long to equal her oral skills!) ever to easily be able to give me head and swallow my entire shaft. Deepthroat Queen!
She gagged and spit on my cock like a porn video, only time that’s ever happened. She led my by the hand in front of the whole house party to her room where we briefly fucked. I barely lasted, her head skills were too much. She’s gotta let guys get inside her pussy before showing off her head skills unless she doesn’t mind guys lasting like 3 mins!
Kinda tall, curly black hair Latina with a solidly cute body but avoidable face. Super great freind, loved hanging out with her. That was our one and only hook up. It’s hot cause she used to sleep with and give head to my good friend, and now we talk about how amazing she was!
Jamie-
Current girlfriend and will be my wife! I struggle to explain how I landed her other that maybe she was tired of douche bags and frat bros. Yes I’m in a fraternity but I don’t fit the stereotype. We had long talks about her family and really got to know each other before sharing a tender first kiss.
She is kinda tall and models as a hobby. She’s been on local TV and in print ads for bikinis. She’s very pale with long legs and full, perky tits. Full C cups that stand on thier own. Hands down the best body I’ve ever been with. Her hip to waist ratio is just stupidly sexy. I knew I had to wife her immediately. Plus… she was a virgin!!
She’d blown a few and made out with tons of guys but I was her first penetration. She is clinically tight. As in her gynecologist has stated she’s the tightest pussy she’s examined at her age. In very professional medical terms of course. The downside is that it was a STRUGGLE to get my dick inside her. Step by step we would get my head in, then a little more, little more etc.
She’s bi, and open to swinging once she’s mentally more comfortable taking a dick other than mine. Although her blowjobs are still lacking the sex itself is amazing and her enthusiasm is par none. Plus she lets me do basically whatever I want with her ;)
She’s thin enough I can pick her up and toss her about, but she had these curves that just enthrall me when she bends and poses for me. I’ve also started eating my cum out of her pussy after I finish in her, damn I recommend that!! Loves showing off and posing while fucking, loves being on top of me
–Some names may (definitely) have been changed!–
Source: reddit.com/r/gonewildstories/comments/7jofy7/mf_sharing_stories_of_the_girls_ive_been_with_26m