Author: crick5885

She thought I was gay, and then she took my ass.

If you’ve read about the relationship I had with my friend Brad during high school you might remember Steph.

Here’s a link to that story: https://www.reddit.com/r/gaystoriesgonewild/comments/k8wy6p/hooking_up_with_the_gay_kid_at_a_house_party/?utm_medium=android_app&utm_source=share

She found out about us and continued letting us fuck at her house for the rest of our senior year, including one time where she watched us.

Well after high school Brad went to another college far away, but Steph and I attended the same school closer to home. In high school we hadn’t been very close, but college forced us to become friends. We were basically the only other people we knew and that led to us relying on one another. We ate dinner almost every night at the dining hall together to start with and eventually started hanging out in her single dorm room since she didn’t have a roommate.

We would cuddle on her bed and watch movies but somehow nothing happened for a while between us. She treated me almost like a brother which was unfortunate because I was incredibly turned on by her athletic, petite body.

During this time I was still seeing Brad fairly regularly during breaks from school, Steph knew about it and loved hearing about me and him messing around. Read more »

Brad and I return to Steph’s (mmf)

Part 4: https://www.reddit.com/r/gaystoriesgonewild/comments/k95r5e/back_in_the_locker_room_with_the_gay_kid/?utm_medium=android_app&utm_source=share

After a while Brad and I settled into a neat routine. We both had siblings, who would’ve known something was up if we were hanging out behind closed doors all day, so we kept on doing what we had been doing. Meeting up in random places to pleasure each other.

The locker room at school was the most common place, but basketball season ended and I had to move all my stuff out of the locker room. Brad was still running track though, which kept him at school later than me.

We still found ways to be together but it was never ideal. The best we could usually do was the back seat of my small dodge neon. Being 6’1 and Brad just a little shorter, it wasn’t ideal for the hardcore flip fucking we had been trying to pull off, which is where Steph re-enters our story.

I got a message from Brad on Friday while I was at school. Short version of it was, Steph’s parents were getting divorced, her dad moved out to live with another woman and her mom was going to be gone all weekend. She wanted Brad to stay over. Brad, of course viewed this as a ticket to ride my cock all weekend, and who was I to tell him no. Read more »

Hot for teacher 18m and older woman

While I’m pretty sure she hated me when she first had me, we eventually got very close. She was always having after school things, like SAT preps or just helping with homework, and I got into the habit of attending most of these things (it didn’t hurt that I was missing football and basketball practice). I can’t explain it, but we just became good friends. I was a popular kid but she became one of the few people I could ever confide in.

During my senior year we went on a field trip to a college a few hours away. On the way back it was dark and she was the chaperone. Another teacher sat in the front and Tina sat in the back. I sat in the seat across from her. The bus wasn’t close to being full but there was quite a few kids and eventually some of the kids started to play never have I ever. Tina and I were just talking as they did, but eventually we started to play along quietly so the kids didn’t know she was doing it. Most of the things were harmless little things to start. Read more »

Forbidden relationship (male+older female)

After college I took a job as a one-on-one for a local school. Basically I worked with an autistic kid who’s mom happened to be a teacher at the school.

Karen was the kid’s mom. I think she was hesitant about working with my son initially but eventually I won her over. I was always down to stay late to help the kid or just talk with her. Eventually we start to have lunches together and she opened up more to me about her struggles with her own husband.

Now I don’t know when I became attracted to Karen. I really didn’t pay her any mind the first time we met but at some point she became one of my top jack off fantasies. She was probably around 50 and a blonde. She’s one of those heavier girls who has her weight spread perfectly between her ass and her tits.

So after about a year of work the sexual tension between us started to bubble up. There must’ve been a dozen times where we had these weird moments of silence when we were standing just a little too close together. Read more »

A fun time at the sex club (bi) (mmf)

So the wife and I went to a local establishment for a swingers night. It’s the first time we’ve dabbled in swinging since we moved back to our home town which definitely added to our nerves.

We got there though and things went off without a hitch. We are both bisexual and ended up talking with two other bisexual couples. The guys were both handsome and talking openly about how they’d been looking forward to getting dick all week. The night went on and everyone was getting slightly drunker. More people began to have sex around us when we retreated to a comfy L-shaped couch in the corner. We all hung out, watching the fun go on around us for about an hour until our three girls all got up to go to the bathroom and look around the club.

The other two guys took this as their opportunity to get to business. They started talking about who was going to suck who’s dick first. I suggested whoever’s dick was largest should get head from the two smaller guys. Read more »

The bartender (trans+ male)

Back before the pandemic ruined every one’s social life, an old friend of mine opened a bar where I live.

The first time I went I meant Chrissy, who just started her first day as a bartender. She was gorgeous, and being a cocky flirt we hit it off and I spent the better part of 3 hours chatting with her.

I definitely thought she was into me, so I left her my number but she never messaged me so I figured she was just being a friendly bartender. So no harm, no foul, I kept going to the bar, we would flirt but it’d never go anywhere, but I basically developed a school boy crush on her which always kept me coming back.

Well one night I go in, and I’m surprised to see this guy I know, Matt, in at the bar. Matt is gay, and went to the same high school and college as me. What no one knows is that Matt became my personal cock sucker throughout all of college and I even fucked him a few times. Read more »

Meeting the principal (mm)

So I’m a lean handsome 28 year old who shouldn’t have any trouble exploring my bi side, unfortunately I live in the middle of nowhere so even my most desperate times on Grindr don’t offer up much.

Which brings us to the story of how i met my boss on Grindr. Now I knew my boss was gay but he’s also married and I just never imagined him cheating. He’s a real tall twink with a bit of a nerdy vibe.

So anyways I’m at work on one of those staff development days with no students around. Mostly the day was to finish up grades before report cards came out but I was ahead of the curve and had nothing to do really. So I downloaded Grindr.

Almost immediately I get a message. Its a pic of a huge photogenic tool. It’s cut and perfectly shaved. Just mouth watering.

So of course I return the favor and send my own cock pic. My cock is slightly smaller than the monster this guy had but still 7 inches cut. Read more »