all throughout high school we would mess with my buddy and talk about how hot his mom was. She was THE hot mom in our town, and had gotten a divorce from my buddies dad a couple years before. Im talking fit body, kept herself looking nice, nice ass, nice big perky boobs, the works. Hell my dad even commented on how hot she was once, my mom didn’t find it amusing. lol. But anyway we would always hang out at his house, for obvious reasons. She was super nice to all of us and pretty much let us do what we wanted. One day when I was over i was joking about how i wanted to bang her to my buddy and she walked in, I got super embarrased and didnt know what to do. She pretended like she didn’t hear and went on her way. My buddy and I kept hanging out after highschool and throughout college.
One day after class I went over to see if he was home and his mom answered the door and said he had gone to work. As I was about to leave she said he would be home soon and I could wait inside, so I went in because i figured she was just gonna let me wait for him. Well…. I was wrong on that in the best way possible. She was wearing some tight blue jeans and a tight white tshirt. We sit down on the couch and she sits next to me and said, “Can i ask you something.” i said ok cuz this was nothing out of the ordinary. and she asked me if i thought she was sexy!!! I kinda didn’t know what to do, but eventually I said yes. She kinda smiled and said good. she left and went upstairs and at this point im sweating like a dog. nervous and flustered. she comes back down and I asked her when my friend would be home and she said he had just gone to work and wouldn’t be home for a while, and it was at this point that she said she thought i was hot and that she wanted to fuck me! Im freaking out internally at this point. ive dreamed of fucking her for so long and she is basically throwing it at me. I almost didn’t do it but thankfully I did. She started blowing me and I didn’t think I would last very long. She gives fucking fantastic head. Im a well hung guy, about 9″ and she deep throated me all the way down. she too off her pants and started riding me. Her pussy and body were so good. At this point in my life I had only slept with like 2 other girls, so she was the best I had had at the time. (still top 5) she told me to cum in her and you bet your ass I did! I filled her up like a beach ball lol.
Tag: High School
[MF] Want your first blowjob now? yes please!
In my previous story I mentioned how Jessica my long time friend was the my first sexual experience and blowjob. We never became what I would have liked but It’s an experience that shaped our relationship and my personal confidence.
Jessica and I became close in high school and we would practically hangout everyday during and after school. Jessica has a light olive completion, a beautiful thick butt with matching hips and very small breasts. This story took place in the summer after senior year, both eighteen years old. Jessica has always been a sexual person which is what I loved about her. We would talk for hours of who we though was hot and who we’d like to fuck. I always would get turned on by our conversations and wish we had a fuck buddy relationship or more. When she would make comments of how horny she was getting I’d always joke I could help her out! This of course was always ignored with a joke by her.
In grad school I unexpectedly hooked up with my former ‘boss’ [MF] [LONG]
When I was twenty-four, in February of my final semester at grad school, I was reeling from chaos in my personal life—to keep an already long story from getting even longer, let’s just say I’d fallen in love with my coworker, roommate, and best friend, who ended up sleeping with our other coworker and lying about it. The first time just so happened to be the same night we’d all gotten plastered together on the Upper West Side and she told me she’d been ‘mortified’ when he asked her out, because they were just friends. They didn’t have the same kind of relationship we did, she said. *Yikes.* The next morning I did not react well, to say the least. The following two months only made things worse. By February we were at the tensest moment of what became a year-long, painful disintegration of our friendship.
A Fun Night with a High School Crush [MF]
Sabrine walked into the room wearing nothing but a green robe. My heart stopped in my chest. I had to think back for a second.
Somehow, my chance meeting with her in the street resulted in an invitation for a cup of coffee together, a lovely conversation that led me to her apartment, and has now led me here -looking up at her looking down at me, with those beautiful seductive eyes.
Sabrine has always been the hottest girl I’ve ever known. Her body is unbelievably perfect; big perky breasts rested on a tender chest, long pale legs held up a glorious rounded ass. I had spent many days of high school trying not to stare at her, mostly unsuccessfully, and many long nights fantasizing about my hands on her body… and hers on mine.
There were two opportunities in the last years of high school for us to have hooked up, both of which I somehow managed to screw up. The first was at a party where her friend was trying to suggest to me that she wanted to, but it went over my head. The second was when a large group of people were all hanging out at my friends house, and me and her somehow ended up cuddling in a bed together. There were two other people also in the bed, so nothing could really happen, and we all ended up leaving before there would have been a chance for either of us to make a move.
[M] The time I [F]ucked the milf next door
Let me start off with some background info. When I was in high school, a new family moved in next-door. I immediately found myself attracted to the mom of the family, Zoey. She was around 5’ 10”, with a very curvy figure. She had C-cup tits that were unbelievably perky. Her hair was brown and shoulder length and her eyes were bright green. Now, as hot as this woman was, her husband was very much the opposite. He was very chubby with a red face, glasses, and a balding head. I, for the life of me, could not figure out how they were together. I felt like Ben Wyatt reacting to Jerry and Gayle from Parks and Rec.
Anyways, she was incredibly hot, and she quickly turned into my ultimate fantasy. Every time she mowed the lawn in her short shorts and tight tank top, I found a reason to go outside. Over the years, I would even purposely do things in my yard shirtless if I knew she was outside. I thought I had caught her watching me once or twice but convinced myself I was imagining it. I never had the courage to do anything other than that or some mild flirting when we bumped into each other. I didn’t think anything would ever actually happen in my wildest dreams.
Brittany’s New Puppy: Beginnings [f] [bst]
Brittany awoke not with a bang, but with a whimper. Softly groaning to herself, she slowly slid open her eyes, rolling over onto her back to stare up the ceiling.
Light streamed through the window, causing her half closed eyes to squint even further. With a great force of will, Brittany forced herself to roll her head and open her eyes just enough to acknowledge the time. 9:53.
She sighed, knowing that with this new found information her body wouldn’t allow her to rest for long. Though it was a Saturday, Brittany’s mind couldn’t justify wasting the day lounging in bed. She was a doer, and the furthest thing from complacent.
Sitting up slightly so her head was just barely resting on her pillow, Brittany noticed that the house was unusually quiet. Her still groggy head spun for a few seconds before remembering that her sister was receiving an award for a writing competition, taking both proud parents along with her. At 19 Brittany had just begun her college experience, and wasn’t overly concerned with winning any awards. She was content to simply stay afloat.
Trusting Me to Take Her Virginity [MF]
“Paul, I want you to be the one to take my virginity. This has gone on too long, I just want to have sex one time before we leave college.”
How do you respond to something like that?
“Yes please”? Sounds a little too lecherous.
“Okay, alright”? Not serious enough, she’s trusting me with something really important to her here, I can’t just wave it off.
I just took a sip of my coffee and looked over at Maddy. Of course I wanted to be the one to take her virginity. She was one of my best friends, and I’d had to hear far more than I cared to hear about her boy troubles over the past few years. I wouldn’t mind if that was behind me.
Maddy was one of the first people I met in college and she’d become one of my best friends. When I first met her, she was quite shy, someone clearly trying to discover herself in college. Like me, she hadn’t had much success with the other sex in high school, and she came to college with this idea that she was going to find “Mr. Perfect,” and he was going to sweep her off her feet and she’d be happy ever after.
[FM] Fucking The Beast at the Gym [Hotwife]
We’re a little bashful to share this story – a lot of people like to judge on these sorts of things – but to be honest, this is a story I like to jerk off to, so maybe you will too. From here on out, my wife will be telling the story.
**The Set Up (A little long for this one)**
Normally, when we play we do it out of town..good to keep it separate. Most of our experiences have been threesomes or swaps together on vacation or on business out of town. But I had a guilty pleasure near by. There was a guy at my gym I really wanted to fuck.
During one of horny, dirt talk, truth sessions, I told my husband this, and he agreed that it was ok.
The girl who wouldn’t touch me in high school [MF]
I couldn’t believe it when I saw her at the one bar in our hometown, with a group of her friends, some of whom I recognized, some of whom I didn’t. The girl who tortured me for the entire four years of high school. She always flirted with me, we studied together all the time, it was to the point where my mom assumed we were dating. But we weren’t, we very much weren’t, and it was a bit of a shock to my mom that I had to invite someone else to prom.
In high school, Kendall was the perfect girl – beautiful, rich, and smart. She was in all the AP classes with me, that’s how we came to study together. Me, I was a nerd, to my core. I may not have looked like one, per se, but I was, no doubt about it. I read history books for fun, I devoured baseball statistics like I was Bill James. She wanted my help for her homework, and I was naive enough to think she wanted to hang out with me otherwise.
Weekend Trip with an Old Friend [MF] [cum] [anal] [oral] [mast] [creampie] [squirt] [facefuck] [pee]
Jenna and Phil had known each other since childhood. The sexual tension was INSANE, but other than one time when they made out in 9th grade, they never touched each other. Perhaps because they were too scared of the powerful attraction they shared.
But we all know how life is and things happen. Relationships change. Life interrupts. Next thing we know, we’re finishing college, looking for a job, moving, dating, settling down, getting married, etc. etc.
Predictably, these life altering events happened to Jenna. As a result, her friendship with Phil faded and faded until they barely spoke until Jenna’s husband asked for a divorce. She was stunned. The news came out of nowhere. She called up her girlfriends, but they weren’t as supportive as she’d wanted.
Then, it occurred to her. She needed Phil. She needed her old friend. She dug up his number and gave him a call. They spoke for hours. Phil had also gone through a rough breakup recently and the two friends found themselves picking up just where they left off.
“Let’s go away this weekend,” he said. “We can rent a house on AirBNB or something.”