Tag: High School

[M] My wildest night ever

I am a 53 years old [M], single now. When i was a 22 years old, I was single and just looking to hookup. I had a girlfriend in high school and got laid daily. After she broke up with me and ran off with an older dude, i kind of went of the rails and started juggling a few different girls leading up to this infamous night.

Colleen was my FWB hookup. She was about my age. We would get together every Thursday because her mom worked late. I lived on the north shore of Long Island and she lived way east, about 45 minutes to an hour away. Her mom worked near where i lived. I would get home from work, take a shower and head out to her house. Colleen was a redhead, blue eyes, medium build, big tits and LOVED giving head. Read more »

[MF] Giving her first orgasm

I was 22 and heading in to my senior year of college. I spent the summer working at the beach, enjoying it all.

One of the cashiers from my store was throwing a party one Thursday night, before her parents came down on Friday. She was very cute, but too young for me, being only 17. But, I had nothing to do, and she begged me to buy beer.

My friends and I showed-up with some beer, hung-out for an hour or two. A friend of the cashier was super cute, and chatting me up. She had turned 18 last week, and you could tell she was trying to act “older”. Her make-up was a little heavy, and was dressed in a revealing v-neck and cut-off jean shorts. If she didn’t seem so young & cute, it could have come off as a whorish outfit. We made plans to meet-up that weekend, and my friends and I went to the bar.

As we were getting out after last call, the friend texted me to come back to the party. Most of the “kids” had fallen asleep or paired off, but she had been drinking Red Bull all night. Read more »

All my Firsts [MF] [Virgins] [Long]

This is going to be a little tame, but hopefully some of you will enjoy it all the same.

I started dating my girlfriend in February a couple years ago. For a senior in high school, I was shockingly inexperienced. Holding hands was a big deal for me! It’s not that I had any moral hangups, I was just nervous and shy to a fault. As a result, the physicality in our relationship developed at a snail’s pace, but that meant I got to savor every milestone.

Our first kiss came more than a month after we started dating. We were sitting together at a mutual friend’s house and somehow one of us worked up the nerve to ask. We kissed once, then kissed again for longer. Her lips were wonderfully soft. While the kiss was far from passionate, there was an intimacy in the gentleness. That night, she texted me and said it was the most “comfortable” kiss she’d ever had. See, I wasn’t her first boyfriend. Her ex, however was quite terrible in bed (as well as being terrible in a lot of other ways). That simple complement gave a sorely needed boost to my self-confidence. Read more »

[FMM] Me, my girl, and my best friend [long] [bi] [dp]

Since my first story got some love, here goes round number 2!

This one takes place right after I graduated high school. Me and my gf at the time we’re talking about maybe having our first threesome. She was gorgeous. Maybe the most beautiful I have ever laid my eyes on, even to this day(don’t tell my fiancée lol).

Kaitlyn was 5′, 110lbs, with the best c cups I have ever seen in my life, the softest skin, the smoothest, tightest ass, and best pussy I’ve ever had. Big blue eyes that looked right into your soul, and a smile that made my world stop.

My best friend Ryan, is about 5′ 6″ but was a wrestler so he was 165 without an ounce of fat on him, 6″ but thick as hell, and was bi like me and my girl. Read more »

[MF] The night I jumped out of a window!

It all started my senior year in High school. I met Mandy doing an after school work program that us students went to work at different places of business and we were paid to do so. Twice a month we would go to a class during the evening to meet up and go over what we were doing at work and if we were learning anything new. That’s where I met Mandy.

Mandy and I hit it off very well. We were constantly flirting during class and I began taking her home after class. We began fooling around before we got to Mandy’s house. This lasted for the duration of the classes. We never got the chance to have sex because her parents were very strict! So she would have to be home in an acceptable amount of time from class.

After our work program was over we kept in touch but never met up for quite sometime. Until I get a text message from Mandy saying that she had the house to herself and that I should go there as soon as possible. I ended up going right after I got out of graduation practice. Read more »

[FM] Lyft Driving slut parties with pilots

Hey y’all,

With summer coming and the kids asking about some cool camps they could attend I decided I better make some extra money. So last weekend I arranged a couple of sleep overs for the kids at their friends and turned on my Lyft app to make some much needed cash.

I started by picking up a bunch of riders going to the Sounders game. They were a rowdy bunch and invited me to the game but I told them my story of needing to work and was rewarded with a nice tip. They did invite me to a post game celebration but as you’ll see I got side-tracked. I then headed over to SeaTac and was able to quickly find three rides in a row to and from the airport. The night was going really well. Then however around 10PM it really slowed down. Read more »

Sissy fantasy to nightmare [blkmail, Msub, huml]

Hi, this my first ever attempt at writing so please let me know what you think! I really appreciate it, hope you enjoy it. I just wrote about what turned me on.

Part One

Sunlight drifted gently through the hotel room as I woke up and rolled over to feel the warmth of Rosie next to me.

“Morning sleepy head”, she greeted me with a smile “no time to waste if you’re getting ready for the stag”.

It was just 3 days until our wedding and the pre-ceremony traditions were happening today.

Rosie rolled out of bed and I watched her seductively walk to the bathroom for a hot shower. She was dressed in an ivory silk chemise and boyshorts trimmed with lace. Her taste in lingerie was impeccable and some thing I loved (and indulged) about her.

We’d met 2 years earlier during a leaving party for someone at work. She’d been getting a drink at the bar next to me, we’d started talking after she accidentally got my drinks order and before we knew it were making out on the dance floor before heading to her house. It had been a whirlwind romance. Read more »

Sissy fantasy to nightmare [SM] [humil] [Crossdresser] [Forced]

Hi, this my first ever attempt at writing so please let me know what you think! I really appreciate it, hope you enjoy it. I just wrote about what turned me on.

Part One

Sunlight drifted gently through the hotel room as I woke up and rolled over to feel the warmth of Rosie next to me.

“Morning sleepy head”, she greeted me with a smile “no time to waste if you’re getting ready for the stag”.

It was just 3 days until our wedding and the pre-ceremony traditions were happening today.

Rosie rolled out of bed and I watched her seductively walk to the bathroom for a hot shower. She was dressed in an ivory silk chemise and boyshorts trimmed with lace. Her taste in lingerie was impeccable and some thing I loved (and indulged) about her.

We’d met 2 years earlier during a leaving party for someone at work. She’d been getting a drink at the bar next to me, we’d started talking after she accidentally got my drinks order and before we knew it were making out on the dance floor before heading to her house. It had been a whirlwind romance. Read more »

Fiancée doesn’t know [M]y secrets [true] [long]

Hey Reddit I’m a 23 year old engaged male. Been with my s.o. For 3 years and engaged for the past year. I’ve known her for about 6 years and I love her with all my heart. She is great in every way I just have an extremely active sex drive and I am very open minded. She is a bit more vanilla and scheduled in the bedroom. I am into a lot of things (I.e. Gay , lesbian, trans, cds, bi, femdom, just to name a few) I will watch porn when I feel the urge and she never knows. Recently I have been doing what I can to find a physical way to fill that urge. Don’t get me wrong the sex with her is great just not often. She said she would be open to try things with another girl but she can’t find one that she “likes” so to speak. Personally I think she doesn’t really wanna try it. But that’s not why I am here. On occasion a “friend” of mine will come over and when she trots off to go to sleep I’ll hang out with my friend. Every time is different than the last. Either he will just start sucking my cock right away or he will pull his out and play with it till I start sucking him. We have done this for years even before she and I started dating. His mouth feels wonderful as it wraps around my hard dick. He performs like a champ. Deepthroating me before moving to my balls and taint as he strokes my shaft. He can damn near make me cum in 5 minutes. I love his hot wet mouth. And he loves mine. His cock while a bit shorter than mine is so thick. I’ve taken the curved rod down my throats countless times and licked his balls while his head throbbed on my tonsils. It was fun at first then it became even better. I sucked him to climax one day within minutes and I swallowed every drop. I felt like such a whore and I loved it. I went to the bathroom while he cleaned himself and spit on my hand. I lathered my middle finger up with it and pressed it into my virgin asshole while I jerked myself. When I came I ate every drop of it off of my hand. I’ve came on his cock and sucked my seed right off of it till he came for me. He has taken my load on his chest, his face and down his throats as well. One time I got him to slide it up and down my asscrack till he exploded and I let his warm sperm drop down onto my hole while I knelt by him and came on his spent cock. Fucking has never crossed our minds and that is fine by me. I’m happy fucking his face or frotting. Read more »