Connecting with an old crush [MF]

I had a huge crush on a girl when I was in high school. She got a bit of a reputation by the time we graduated (make of that what you will) and we ran in different circles. We lost touch in college except for being connected on social media. All I knew she got married, had a couple of kids and got divorced.

When I was working at a beach bar I saw her in person for the first time since high school. When you go to the town I was in it was usually to “cut loose”. We started talking and pretty soon I was ready to go on my break.

Her reputation may have been justified, we ended up going to the employees bathroom. She sat down, and took out my cock and started eagerly sucking. I’ve always heard “sloppy blow job” and seen them in porn but had never had truly sloppy head. She told me to tell her when I was getting close, which I did and she slowed her pace. She did that two more times before letting me unload in her mouth. After swallowing, she up, gave me a hug and told me to text her since she’s be around all weekend.

First time for everything [MF]

As a bartender at a kind-of-dirty beach down you get a lot of interest from horny people. Doesn’t matter how good looking you are or aren’t, you just get some magical gravitas. One night this group of women came in and one who was way out of my league opened the tab. She was gorgeous; part Hawaiian, maybe 5’8”-5’9”, long legs, toned abs, well shaped ass and easily c cups. Every time she came up for drinks for the table she would stay longer and longer before. I went for it and gave her my number on a napkin (I had a stash of napkins with my number on it behind the bar I would hand to women with their drinks it was shockingly effective), thinking nothing would come of it.

She texted me right when she got back to her friends and we would flirt and text all night. Eventually she asked how far away I lived since their group has ten women in two hotel rooms. At the end of the night she went to my place, we barely got through the door and her bikini was off. She pushed me against the wall and took my cock in her mouth for a couple of minutes before just saying “fuck me”.

Late night viewing party [MF]

There were two women who lived across the courtyard from me in my apartment. They were both hot, both were trainers…and sold weed. I hadn’t smoked before and my experience was limited but the stuff was apparently really, really good at the price they sold it for. One woman was blonde, toned, perky tits and a firm ass. The other was half Korean, also toned, slightly bigger tits and rounder ass.

One night I was sitting on my balcony after work so close to 3:30. I left my lights out and enjoyed the peace and quiet when their lights turned on. The blonde was in a robe and the other wearing nothing but a garter and midthighs. They opened the door and three hulking dudes walked in with four duffel bags. They sat down the bags and pulled out bricks of weed and the woman in the robe handed over cash.

The woman in midthighs took one guy to the couch and started sucking his cock. The blonde took another guy into her room and fucked him while the third guy counted the money. Over the next hour both women sucked and fucked all three guys. A couple of weeks later the same thing happened. Guess we were getting subsidized weed all the while

Not sure which of us was getting used [MF]

See “Sister Peeper” for backstory

My friend Cate worked at the adjoining bar and we’d walk home together most nights. Despite living together, she and her sister had an passive aggressive relationship that could be openly antagonistic. Rhea seemed to have her life more together and guys gravitated to her more. Cate was pretty enough, not gorgeous or anything; full face, big tits, thick thighs, athletic with a dark complexion and blue eyes.

One day the power went out so she and I were sitting on her balcony smoking, her in a bikini and me in shorts. I asked where yRhea was when I noticed her room door closed despite the heat and Cate said she was staying with a guy. That was fine, we were just there to “fill our biological needs” as she put it. I listened to Cate complain about Rhea, which wasn’t uncommon when it was just us, we talked about how fun it would be to live on the beach like this forever and other usual high convos.

Sister Peeper [MF]

This is the opening of a sort of mini series…I guess?

I had about four months between getting out of the Army and starting business school. After a pretty rough break up I took a friend up on a offer to take the sublease of his apartment in a beach town since he was moving. Through sheer luck he introduced me to an owner of a bar in the town and I told him my situation and asked if I could work there, which he obliged. That launched the four most fun months I could have had.

I worked there from April through mid August, so spring break through summer break. It wasn’t a classy beach town, more known for partying and “what happens here stays here.” I couldn’t have gotten more lucky in my setup.

Coincidentally my brother’s girlfriend had a friend (we’ll call her Rhea) who lived in the same building. Initially she was an innocent connection but quickly became a consistent hook up buddy. We knew it was a terminal relationship so would just have sex and enjoy ourselves. She was tall, a runner, with the best ass I’ve ever seen and bigger tits than I expected, she wasn’t beautiful but cute enough. By far the hottest thing about her was her motto in bed could’ve been “we can try if you want.”

I was the real contest winner [MF]

When I (34M) was a senior in college (then 22) I was president of my fraternity. The fall semester was always time for pledging and when the Greek organizations got their new members. Late in the semester a cute freshman girl started talking to me at a house party. This wasn’t unusual, sorority girls where I went to school were very attractive (in my opinion) and most just wanted to thank me for hosting the party. So I was used to cute girls approaching just to say a quick hello and thanks even though I didn’t really have to do much as host.

This one girl in particular was very friendly and much more flirtatious than I was used to, especially since the party had just started. Eventually she asked if I wanted to go somewhere more private. At the time I thought fraternity president only had three benefits: resume builder, free room and more importantly a private room. I said sure and we went to my room, but I left the door open, assuming she just wanted to thank me or ask about my “little brother” (Greek-speak for your mentee) who’s a really good looking guy. She closed the door and told me about a contest she and another pledge were having. They were tallying how many fraternity presidents they could give a blow job before initiation at the end of the semester. Finally being fraternity president had some actual benefit. I sheepishly said ok (though my heart was about to explode) and she asked me to get undressed lay on my bed.

Revenge and relief [MF]

I dated a woman about a year in my mid-20s. We were serious, or so I thought, and I got along with her and her best friend who had been her roommate since their freshman year of college (approximately seven years). Her roommate and I became really good friends. She (and my gf on her behalf) would complain regularly about the fact she couldn’t find a good guy to date and would even talk about how long it would be between getting laid. I’d try to set her up with guys and “scratch” her itch but it never seemed to work out. Admittedly I found her dating mentality kind of weird; she wouldn’t really have much sex but would complain about not having sex even when she was dating a guy. I’m sure there was more to explore behind that so I hope she found whatever she was looking for.

My friend and I got a little closer one afternoon [MF]

My friend (34F) is gay and as such, we’ve never had any kind of mutual attraction. She and I (34M) hand out, our girlfriends are very close, nothing abnormal, a completely platonic relationship. One thing about my friend is she has an incredible body, easily one of the best I’ve ever seen. She’s tall, with long legs and perfect proportions. The only time I’ve ever had an issue around her is a few times around a pool when she’s in a bathing suit, and that’s only because I have to adjust myself if I start getting hard and make sure my glances on her cleavage aren’t too long. Nothing could ever happen, even if there’s a natural response from my cock.

A couple of years ago, several friends of ours got a house a few miles from the beach. One afternoon my friend and I had to work later than everyone else so they went to beach at noon. My friend finished up a couple of hours later, slightly earlier than I did. She said she would go to the pool and came back downstairs in a nearly-translucent white bikini that looked almost pained on her full tits and hugged her round ass. She clearly didn’t notice my stare (probably mouth agape) as she walked to the pool. For the first time since knowing her, I walked to my room and masturbated to her.

Still scared of my little sister [MF]…& [MF] again

In retrospect this may have been better as a multi-parter. Also I tell this story as often as possible…it’s easily the most sexually magnetic I’ve ever been. Since nothing like it happened again, I’m pretty proud of it. I wish there was a place on my resume or LinkedIn for it.

When my younger sister (by two years) first started working in NYC she had two roommates…because it’s NYC and absurdly expensive. My sister and her roommates worked in finance and tended to go out all the time. After my first deployment I (then 25) went to visit her for a long weekend. Both of my sister’s roommates were attractive, one a gregarious, beautiful Indian woman (let’s call her Div) and the other was a reserved, kind of mousy Jewish girl (let’s call her Hannah). And yeah, I know, it sounds like a stereotypical set up for an NYC apartment of young women who work in finance. I flirted with both of her roommates, but my sister used to get mad at me in college for hooking up with her sorority sisters, so I knew her unwritten rules.

My gf once rubbed my cum all over her chest in front of her family [MF]

The first time I (then 29) met my whole gf’s family (then 26) was at a beach house. Everyone was there: her grandparents, all of her aunts and uncles, cousins, siblings, nieces and nephews, everyone. We were staying in a house and she wasn’t very comfortable with me staying in the same room with her, which I completely understood. There was zero privacy in the house and you couldn’t be in a bathroom two minutes without a disturbance.
On day three of this trip though we were both getting pretty pent up. When the whole family was at the beach we snuck up to the house using some excuse. My gf took off her bathing suit and I went down on her until she came then she returned the favor. Since I hadn’t cum in three days she said that she wanted me to cum on her chest, which I did. I don’t remember the last time I went that long without cumming so forgot how much there could be. Her tits were absolutely covered. I helped her wipe up and we went back outside.
When we got there, her aunt told her she missed some sunscreen and motioned to her chest. My gf quickly spread across her chest…and that’s how my gf rubbed my cum on her tits in front of her family.