High School Archives — Page 519 of 805 — NSFW story

Spanking a [F] college swimmer by [m]e

During my freshman year of college I visited a friend from high school who swam for her college which was located near where I went to school. That night, I went with my friend to a party at the swim team house, which was a three story building nicknamed “the castle,” by the swim team and both members of the women’s and men’s swim teams lived there. The party was slow at first, then it got more fun as more people arrived. My friend introduced me to her teammates, including a senior on the team named Laura. Laura was a white woman with brown hair, about 5’5 or so with average sized boobs and had what I’ll call a “swimmers booty,” that I noticed when she turned around for a minute. She was wearing tight jeans and her ass looked so nice. A long story short we hit it off right away and start flirting with each other, eventually sneaking away to a secluded part of the swim house to make out. After making out for a little while Laura invited me back to her room, not too far away. Read more »

We finally had another Redditor join us! [MFF]

This one will be kinda short. Per our last post, we were looking for another girl ideally to join my BF & I. We almost “settled” for another couple (still wanna do another foursome) but we were lucky enough to find a unicorn!

Since my BF (James) last shared me with another guy, we agreed to try something a little different. We wanted to find a girl to join BUT I was going to mostly watch (essentially a cuckqueen situation). It ended up being tougher than expected, but we finally found someone (but did not give the ok for us to share her username, since she wanted to be as discreet as possible). The main reason for her discretion was two things: She didn’t want anyone, especially her friends in her sorority, to know about her “experimenting” with a couple/girl (did not find out about this until after our threesome). Some details though: She was 20, curly-ish brown hair and skinny with small boobs (typical sorority girl who looks like she just graduated high school). She claimed to be “100% straight” and was really only interested in the dick, but, said she would be ok with me watching and possibly some touching. Read more »

[MF] Flirting with friend leads to deepthroat and possibly more

This all happened a few years ago we were both 21 at the time, 24 now. Recent events have brought this all back to mind. Me and Abby had been good friends through high school. We remained friends after and ended up attending the same college.

Abby is hot, she is skinny and her hips stick out from her thin frame. She has tiny but perky tits and a nice heart shaped ass. Her hair was dyed dark red at the time.

We had never hooked up before but she would tell me about her hookups and I would tell her about mine.

Then things escalated. I was on a road trip for a week. Long drives were getting dull so I was texting Abby quite a bit and things started to get sexual. Our conversations would get sexual but always just general talk but never personal like this. She asked if my dick had a curve to it, it does and she says girls must like that. She asks about the best blowjob I have ever had. She asks if I like puffy nipples because hers are puffy and it makes her self conscious sometimes. Things keep heating up and she ends it with a “goodnight, I’m surprised you have never got to have the Abby experience ;) talk to you later.” Read more »

[M]e and the married Canadian mil[f] I met in Vegas

My best friend Dan and I went on our annual guy’s trip to Vegas. As usual Dan was pressing hard to meet someone to have a 1-2 day fling with, but I was mostly along for the ride. Ready for some serious wingman duty, drinking and naps by the pool.

On our second night there, around 10pm (after some serious pregaming), we hit the bars and just had drinks and talked to people. After a few hours, Dan met someone, a cute latina girl named Jackie and they were chatting it up pretty seriously. So I did what any good wingman would do, I said I needed to use the restroom and I just never came back.

I walked down the strip to another hotel, and another bar, and kept up the drinking, but with a party of one. I keep myself pretty entertained and am good at talking to strangers once I have a few drinks in me, so it’s not sooo bad. This threesome (two girls and a guy) start talking with me as they were waiting for their drinks at the bar. Once the drinks arrived one of the women motions to a booth and says I should come drink with them. I’m more than happy to oblige. The women are fairly conservatively dressed and in their mid to late 30s. The guy seems a little out of place as he’s dressed up to go clubbing and maybe 10 years younger than all of us. Read more »

Jane [FM] [ANAL]

Jane was a horny woman. She had been since she first noticed the nice feelings when she rubbed her privates against her pillow at a young age. Since that night, she had sought after that sensation with a passion. She fucked her first boyfriend at fifteen, loving every inch of his throbbing cock filling her up and satisfying her like nothing else. She tried anal when she was eighteen and was hooked instantly. The orgasms she experienced when simultaneously probing her tight asshole with a hairbrush and pounding her pussy with her dildo were cosmic. Since that day (she had cum seven times in an hour), she had sought something more.

Jane had had a long string of lovers, each more exciting than the last. There was Peter, who was mild mannered, but hung like a horse (gods, that had felt good sinking into her asshole). Then there was Justin, who took every opportunity he could to eat Jane’s pussy and ass like a five-course meal. Then there had been Thomas, who dominated her life in every way for six months when she was twenty-two. She had been forced to walk around the house naked, ready to be used at his desire. She enjoyed the sex, as she often did, but after a while found the submission to be tiresome, so she broke it off. After him had been Ben, who liked nothing more than to fuck her in the most daring and public places. He was a bartender by trade and had fucked her behind the bar in his pub not once, not twice, but eight times. It had been exhilarating, but there was still something she was searching for. Read more »

My first time sucking dick [MM]

When I was younger, I was very fluid with my sexuality. I had long hair and was mistaken for a girl more than once, but it didn’t bother me. A few times, I even had men come up and flirt with me, only to realize I was a boy and back off. I was into girls, but would find myself sometimes fantasizing about having sex with another guy. I didn’t know where those fantasies came from and just chalked them up to being a horny teen, as I never had any opportunity to fulfill them in high school.

That changed when I got to college. My freshman year, I became friends with a guy named David. We hung out a lot, especially when it came to the summer semester after our freshman year when we were both taking classes and found things were really slow with not as many students on campus and not much to do. One night, we were hanging out and drinking and decided to go swimming naked in David’s apartment complex pool. Read more »

[MF] My years of lusting after my hot, crazy friend finally went my way.

This was years ago in the Midwest. I’m pushing 40 now but I still think about this night like once a week. I’ll call her Ann. I would’ve been 25 at the time. She was 26. I’ve known her since high school, she was my best friend’s sister. Total party girl, very hot. Very slim frame, probably 5’7”, brunette, C cup tits that looked unbelievable on her slender body, nice little ass, eyes that could just flatten a guy. Her tits were so perfect, I’d later find out. Perky with tiny pink nipples. She always wore a bra one size too small to keep them perky. I don’t know if that actually works, but it seemed to for her. We weren’t college-types, just working class people who happened to be pretty good looking. She was a 9, I was maybe an 8 at best.

And she was wild – nightclub bartender, a little crazy, big drinker, which always led to excitement, sometimes good, sometimes bad. Sometimes we’d laugh for hours and briefly make out, sometimes she’d start a fight with someone. You never knew what you’d get that night. Total smokeshow though, sultry. Her entire vibe would be like a white Rihanna. Read more »

Jailbird Part I [MMM][Drugs]

Alright so, they got me. When we went to trial, they had all my emails. Every single letter, spelled it all out. I was never too good at covering my tracks. Either way, I was sentences to 24 months for insider trading. Boo freaking hoo. A year and a half wasn’t going to be the end of the world. I honestly didn’t care about myself. What I was worried about was my wife and kid. I hid my money well so they were provided for but it must have sucked to go to school and have kids mock you for your dad being in jail. I was worried about him. But little I could do when I was in here. I hoped he wouldn’t be too mad at me when I got out.

I was sentences to a minimum security prison with time served. So all I had to do was survive 15 more months. Don’t let the “minimum security” fool you. It was still jail. The food was shit, inmates fought in the shower, and every once in a while a couple guys got thrown into solitary for getting caught doing something they weren’t supposed to. I think the only way that it was really “minimum security” was in how easy it was to get drugs in. Read more »