Fair warning, this is not a short story, but it’s pretty sexy, pretty funny, and 100% the truth (minus a few name changes). Hopefully you enjoy it!
This all started back when I was in college… I dated a chick named Sara for a summer when I was 22, she was 19. She had gone to HS in the town that I went to college and was home for
The summer. she went to school about 3 hours from me so it was just a summer thing, we had no interest in a long distance relationship. She was a soccer player, 5’5”, about 125 lbs, small boobs (which I didn’t mind at all, I’m an ass man), but everything else about her was perfect. Ass, legs, stomach, smile, eyes, bubbly personality with just enough sass to keep me in line. She really was the total package and I was proud to have her on my arm all summer. Long story short, we broke up at the end of the summer with no hard feelings, no intentions of getting back together and ended up hooking up a few times when she was back home from school. Remember Sara, she’s important later…
Fast forward a year and a half… me and my roommates used to run off to border towns in Texas about once a month. We were about three hours from the US/Mexico border and we could grab a room at the motel 6 for like $50 and then go across the border and get trashed in Mexico for next to nothing. It wasn’t as dangerous then and there was just something cool about crossing the border.
This time, two of my roomies were bringing their gfs, my friend Chris was bringing this chick he was trying to hook up with, Kelsey, who lived about two hours from us. Kelsey was bringing a friend, Jenn, who was single. This was perfect because I was the only single guy in the group so I felt like if we meshed at all, I had a decent chance of at least fooling around with her. I had never met Jenn before but Chris and Kelsey assured me that she was pretty good looking.
Let me stop right there and say that I think I’m a fairly attractive guy. 6’ 185lbs with short brown hair and I was actually pretty toned at that point in my life. So I hoped she’d be at least mildly interested since we were going with a bunch of couples and we would kind of get paired together.
We had been at the motel for an hour or so pregaming when the girls showed up. They undersold how attractive Jenn was… tall, maybe 5’9”, with beautiful brunette hair that ran about halfway down her back. She had a small but round ass, long muscular legs and tits that we’re average in size but looked to be very perky. She also had these big full lips and some dark brown eyes, that even when we first met, seemed to be wanting something. Kelsey introduced us and we hit it off quickly. We piled into two cabs, and headed across the border.
Jenn and I were incredibly flirty right from the get go, she was very touchy and I, fueled by copious amounts of Dos Equis and tequila, was getting more and more bold and suggestive with my comments. We headed out to the dance floor for some dirty dancing, and boy could she dance. I was trying my best to conceal a growing erection from her grinding all over me, but she could feel it and turned around, visibly proud of herself.
Her: “I can’t believe I made you hard!”
Me (laughing): “why not? You knew what you were doing”
Her: “well because you know… you are the way you… are”
Me (confused as I’ve ever been in my life): “what the hell are you talking about?!”
At this point I looked over at my friends and they were all laughing hysterically and pointing at us. As soon as she started showing serious interest in me, they had convinced her that I was gay. What are friends for? Bunch of assholes… lol but it had actually worked in my favor! She seemed to want what she couldn’t have, and now all of a sudden, it was available to her and she was all about it.
After assuring her that I was 100% straight, we kept grinding on each other and started making out. We all went back to our hotel rooms at about 4 am and instead of getting to have sex, we passed out drunk. Opportunity missed, and now I had blue balls. The next morning we went home, Jenn and Kelsey did too and I thought I might never get another shot at it. Turns out the same thing happened to Chris and Kelsey. They passed out before getting to do anything at all too.
The next weekend, me and Chris decided after a few beers and round of texts with Jenn and Kelsey that we were going to their town right now to spend the night. Everyone was very clear about what was going to happen when we got there, which was a few rounds of drinking games and then fuck each other’s brains out. We left our house about 10:00 pm and got to their place about midnight. We had a few beers before we left so we decided it would be a good idea to take some caffeine pills (hardcore I know) on our way so we wouldn’t fall asleep. This was a TERRIBLE idea. All it did was give me multiple rounds of the worst diarrhea I’ve ever had. I definitely wasn’t getting laid and I cock blocked Chris by accident too. Kind of difficult for them to get into it when they could hear me making all kinds of ridiculous sounds in the bathroom. We left at about 3:00 and got home about 5 am, after a completely wasted trip. My stomach was killing me, my butthole was on fire and my balls were blue yet again. I was my own worst enemy.
Two weeks later was NYE and as usual, we were hosting a party. It was about 11:00 and things were really getting going when I looked up and Jenn was walking right towards me! I had no idea she would be there, but Chris and Kelsey were right behind her laughing. They wanted to surprise me, and it worked because I was blown away.
I was already several drinks in and I was determined not to make the same mistake for a third time. I was going to need to pace myself… Jenn ran up and kissed me and gave me this look that told me that pacing myself wasn’t going to be necessary. She wanted it now.
There were probably about 30-40 people at this party but if it wasn’t going to stop her, it damn sure wasn’t going to stop me. I grabbed her by the hand and we took off to my room. Clothes came off quickly and she went straight to her knees and started working on my zipper. I was already rock hard when she worked me free. She was impressed with my size (I’m not a pornstar but I’m not small, pics in the profile if you don’t believe me or are really that interested. Lol). She immediately took me into her mouth as far as she could, no teasing, and started working up and down my shaft ferociously. I had to slow her down to avoid instantly blowing my load.
I pulled her up and we moved onto the bed where she laid back and took her pants off over her red heels to reveal a black thong, it was my turn to go to my knees. After gently rubbing her over the panties I could feel how wet she was… I pulled her thong off with my teeth and buried my face into her waiting lips. She tasted amazing…
I stood up and looked at her and asked her what she wanted.
“You, inside of me, now”
I didn’t need to be told twice, and picked her legs up over my shoulders and slid it in raw. (Probably not smart, but it no one got an std or got pregnant so quit judging me! Lol). I started pumping away and rubbing her clit with my thumb and she had a massive orgasm, the biggest I had experienced, which was obviously a major turn on. She was also still wearing those red heels which was incredibly hot.
She told me she wanted to get on top, and I’m a gentleman so I said sure. She grabbed my Cowboy hat off my dresser, put it on, climbed on top and started grinding away. My God was it sexy… I was doing everything I could to concentrate on not cumming and then the craziest thing happened, the bedroom door opened.
Standing in the doorway was Sara and her friend Ashley with stunned looks on their faces. I didn’t even know she was in town, usually she’d let me know and more often then not, we’d end up hooking up.
Here I was, lights on, on top of the sheets, balls deep into Jenn who was riding my cock in red heels with my cowboy hat on like she was in the damn rodeo.
They stood there shocked and watched for a sec and then giggled and shut the door and ran off. For a fleeting moment, I thought they were just going to watch and the more I play it back in my mind, the hotter that is…
It was admittedly weird but I shrugged it off and kept going. Sara and I had obviously slept together several times but weren’t together so I didn’t think it was a big deal. I wasn’t going to let it fuck up my night.
Jenn and I went right back after it, not missing a beat. We switched positions again, she liked me standing up with her on the edge of the bed. I wanted to make her cum at least one more time. It didn’t take long before she was gushing again. I wanted to fuck her all night but I was only going to be able to hold on for so much longer… I asked her where she wanted it and she seductively looked up at me and opened her mouth. I took my cue, pulled out and shot several ropes of hot cum onto her tongue and face.
We cleaned up and went back out to the party, where it was no mystery what we had just done. We didn’t care… we basically had a month long tease that led up to this. Sara and Ashley had bailed to go to another party and I didn’t blame them. Jenn stayed the night, we had sex again in the morning and then she left. We texted a few times, but we both got what we were looking for and that was that. Haven’t seen her since…
So if you stuck around, the best part of the story is here: Two years later, Sara and I ran into each other and started dating. Two years after that, we got married. Eight years after that, we’re still happily married! The story is now funny to us and we tell it every now and then. I always end it with she knew she was going to marry me when she saw me in action. She liked the night moves!??.
Source: reddit.com/r/gonewildstories/comments/ecw8bq/the_hilarious_sequence_of_events_that_led_to_the
Nice!
Sure miss the good ole days of leaving Stephenville, TX and driving to Acuna to party!
That’s a great story man! Have any stories of you fucking Sara (when married or before)? Keep up the excellent work man!
That’s was some good shit, funny and hot as fuck
Very funny, enjoyed your story a lot!
Yes! Always down for a good story that mixes humor with sexytimes!
Your wife is sexy ?
Ohhh yeah!!! Id love to hear how you and sara reunited.
Way to go for sliding into Jenn raw in the heat of passion.