Tag: Prostate

[MM] My first encounter with another guy

This happened almost six years ago, back when Craigslist personals was still a thing. I had always wondered what it would be like to be with a guy, and I started watching gay/bi porn to see if it was actually a turn on. It was.

I found myself jerking it to the thought of getting a blowjob from a guy and one day after smoking a shit ton of weed for courage and just enough “fuck it”, I replied to a post on the m4m personals. The poster simply wanted to come over and service a cock, that’s all. Sounded perfect to me and while I waited for him to arrive my heart was pounding and my cock was hard as rock in anticipation.

The guy arrived about fifteen minutes later and I let him inside. I was super stoned and nervous but super excited, and since I had answered the door only wearing tight boxer briefs he could see my excited state as well. I sat on the couch and he got down between my legs and massaged my cock and balls through my boxers and asked if it was my first time with another guy. I said yes and he smiled and slowly pulled down my boxers. Read more »

First time sharing my ex-girlfriend [MFM]

My ex-girlfriend Nina and I had a very interesting relationship. When we first met, all we did was have sex. Multiple times a day, anything you can imagine. She loved playing in public places, giving me blowjobs while I drove, jerking me off in restaurants and movie theaters, you name it. Our sex life remained vibrant and only expanded with time. A little about each of us, I’m your typical white male, tall dark and handsome as I have been told. Never received any complaints about the size of my package, most women especially admired my girth. Nina was black, slightly shorter than me with suckable size breasts and nipples and an ass that would fit perfectly in your hands. She was a mother from a previous relationship so her vagina was stretched out from the childbirth. She was very much into being stuffed so we would often play with dildos and double penetrate her pussy when having sex. Read more »

Amazing miniature college orgy over fall break with Kylie. [Group]

(Long, but totally worth it!)

In my first two years of college, my roommate Jay and I both would both have sex with our friend with benefits, Kylie. Regularly, almost weekly, we would have a threesome with her. In fact, I lost my virginity to Kylie when we first did the deed. Though it sounds crazy, I could have not have first had sex in a better environment, as Jay is one of my best friends. My nerves were calmed in a very supportive environment. They both kind of guided me through it, every step of the way. It was incredibly hot to basically take turns with her and communicate with her on such an intimate level. In hindsight, it was fairly reckless to not wear condoms, but she was on very good birth control (an insert in her arm) and we were very upfront with our sexual history. During all of our erotic activities with her, we never used condoms and it really upped the pleasure level. Anyway, because of this, we made an agreement to be exclusive sexual partners with only her. This only changed a few times, when we brought more people we trusted into the mix. Read more »

Amazing miniature college orgy over fall break. [Group]

(Long, but worth it, I swear!)

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In my first two years of college, my roommate Jay and I both would both have sex with our friend with benefits, Kylie. Regularly, almost weekly, we would have a threesome with her. In fact, I lost my virginity to Kylie when we first did the deed. Though it sounds crazy, I could have not have first had sex in a better environment, as Jay is one of my best friends. My nerves were calmed in a very supportive environment. They both kind of guided me through it, every step of the way. It was incredibly hot to basically take turns with her and communicate with her on such an intimate level. In hindsight, it was fairly reckless to not wear condoms, but she was on very good birth control (an insert in her arm) and we were very upfront with our sexual history. During all of our erotic activities with her, we never used condoms and it really upped the pleasure level. Anyway, because of this, we made an agreement to be exclusive sexual partners with only her. This only changed a few times, when we brought more people we trusted into the mix. Read more »

Hot and quick sex with Kylie in the back of my car. [MF]

It was mid-August in 2011. I just got back to college for my second year, Saturday before my first week of classes. From my previous stories, you will know about my awesome and ravenous sexual relationship with this girl named Kylie. My dorm-mate and great friend Jay and I would have many threesomes with her, as friends with major benefits. I’d say we both had sex sessions with her together at least two dozen times in our dorm room. We are talking multiple-round, vigorous, sweaty, messy and raw smash fests. Don’t worry though, we were exclusive with her and she is on good birth control. It was an extra risk not to wear condoms, but we really loved the extra closeness and sensitivity it provided us, as well as give us all great orgasms. Between the two of us guys, we probably dropped more than a hundred loads inside of her before summer break. What can I say? We were just super horny and needed to relieve some stress of studying. None of this was romantic with her in nature, though we generally got extremely close as friends and genuinely cared for each other. That tends to happen when you have a regular bang buddy. Read more »

How to get Bi, Part 4 [MM]

[Part 1 here](https://www.reddit.com/r/gonewildstories/comments/b8n551/how_to_get_bi_mm_mmf)

[Part 2 here](https://www.reddit.com/r/gonewildstories/comments/b8tfjz/how_to_get_bi_part_2_mm_mf)

[Part 3 here](https://www.reddit.com/r/gonewildstories/comments/b8xry4/how_to_get_bi_part_3_mm)

Our first time. This is pretty heavy stuff, so be warned. Part 5 will be more so.

Chris found the plug that Melody gave me in the shower. I had used it like I normally did, but fucked up and left it there when I was done and had washed it.

I had told him once that Melody was suuupeerr into anal, which he somewhat knew since he dp’d her with me with his fingers (part 1). I told him it was Melody’s, and that I was cleaning it up because she was visiting (a lie).

Chris called me out.

“No way, man, it was in the shower! It’s either yours our theirs [our suitemates], and I think you’re the only one that has showered today!”

He gave me shit until I finally confessed. I told him Melody and I had experimented, and I liked it. She had given it to me, and I still used it. End of story.

Not end of story. Read more »

How to get Bi, Part 3 [MM]

[Part 1 here](https://www.reddit.com/r/gonewildstories/comments/b8n551/how_to_get_bi_mm_mmf)

[Part 2 here](https://www.reddit.com/r/gonewildstories/comments/b8tfjz/how_to_get_bi_part_2_mm_mf)

I kept the plug. Melody and I used it together, but I really used it to explore myself. The typical solo session went like this: I’d get in the shower, clean up, and open myself up with a few fingers before sliding it in to the hilt. Back then, I used it maybe 20% of the time I jacked off.

I like to feel stretched and full – I wasn’t used to the feeling of being fucked then, but in general I love pressure on my prostate. The plug is a reaaaalllyyy good size. It takes a while to get it in, but once it’s there, it doesn’t go anywhere. I have explosive orgasms with it. Melody loved it when I wore it with her because after edging for a few hours, my orgasms were enormous, and she loved cum.

After a long, crazy summer, Chris and I packed our things up and moved away to school. We both decided to go to a pretty big regional university, which was really the only option for us and our chosen fields of study. We decided not to go “blind” and agreed to room with eachother. We moved in without much fanfare – met our two suitemates, and set a big jar of community condoms in our shared bathroom. Getting laid is a #1 priority for guys that age :) Read more »

[MM&MF] [Oral] [Anal] [Prostate] [Gay] [Bi] [Swallow] [Creampie] Rigged From The Start Pt 2

I take my position on my knees in front of you. You’re naked, your hands on the chair arms. Cock limp, yet engorged as blood begins pumping.

Your wife kisses us both on the head and leaves us to play, sitting across the room watching. ‘I’m going to give you your first prostate orgasm today.’ I take my thumb and let it slowly trace up your leg and along your cock as I’m speaking. ‘You’ve gotta want it.’ I say looking in your eyes.

You take my hand in yours and and bring it to your lips. Kissing each of my finger tips. ‘I want you.’ I moan and kiss you pulling your ass over the edge of the seat so your back is in the chair. I set to work preparing your hole. Lifting your rear up so I can fully taste you. My tongue opening you up and making you grind your ass on my face. Read more »

[MM brief F] [Anal] [Oral] [Bi] [Gay] [Cheating] [Passion] [Breeding] ‘Rigged From The Start’

When you first met your wife’s gay friend you had no idea how bad you’d eventually want me. The way I bend over showing my ass when I know you’re looking. The obvious semi hanging in my pants as you walk by most days. The way I shudder when we get close.

Finally one day your wife steps out for a bit and before you realize what’s happening I’m on my knees in front of you. My hands on your thighs. You tense up at first, but one look at the fire in my eyes and you’re already unzipping your fly. Letting your meaty married cock peek out. I lean forward kissing the head and letting my tongue take you into my mouth. Your cock is still soft, but I have it hard in no time. I feel it get bigger as I move my tongue along the underside, taking care to massage your balls through your pants.

Before long you’re so engorged it aches. When you can’t take it anymore you grab either side of my head and pump a massive load of hot cum into my mouth. Flowing over my lips onto your balls. I clean up every drop before standing up. Read more »

[MM] Staright mate from work fucks me with my dildo

Thanks for all the feedback and messages about [part 1](https://www.reddit.com/r/gonewildstories/comments/azz8ex/mm_my_straight_mate_from_work_becomes_curious/) of my adventures with my straight mate from work. I thought I’d share the second of our encounters.

After our first session I was a little worried that Jack my loose interest and I’d lose a friend, however it wasn’t long till he messaged saying how much he enjoyed himself and has been playing with himself thinking about it. We start to pretty regularly send each other pics and videos of each other naked, jerking off and fingering ourselves. It surprised me that as a straight guy he was really into anal (perhaps I should be less stereotypical about my straight mates!) and would often finger himself when he jerked off. Now he was single and had already made a big step in experimenting he decided to buy himself a dildo to really give anal a go.

We soon started to swap videos of us using our respective toys (if you ask nicely and have something to share in return I might show you some of mine) and talk quickly turned to us using our toys on each other when we next meet up. Read more »