[M]y first time fucking another man… (M/M)

Originally posted this in /r/bigonewildstories about a year ago… Cross posting from /r/gaystoriesgonewild … got a few DM's that it might be liked here…

So this isn't about my first time with a guy (I'll maybe do another story later on that)… but definitely my favourite. So I was at home (living alone)… about 25 years old (7 years ago or so) and felt the need for some cock. So I'm on the gay.com chat rooms seeing what's what.

As usual a bunch of guys message me.. usually older, out of shape guys (no my thing) but this one guy.. lets call him Steve (since I can't remember his name) messages me. He's a bit older.. like 28-29.. good looking (for the pics anyway).. about 5'11".. 190lbs and about 7 " cut. (I'm about the same) We get to chatting and decide we should meet up.

So Steve comes over to my place.. even better than the pictures! We hang out for a bit.. have a few beers to loosen the mood. After 20 minutes or so of random chit chat I decided to make my move and start unbuckling his pants. He's rock hard and his cock is perfect! Normally I'm a little hesitant but it (and him) looked so good that I had my mouth around it in no time. I've never enjoyed sucking cock so much! After about 5 minutes we decide we should turn it up a notch.

Molly, Jacob, and Camden – Summertime Blues 2 [FF][MF][oral]

Click on my username to see the previous story posts featuring these three. There will be more to come.


Early Saturday morning Molly and Jacob were dressed in grungy sweats and ready to move into their new apartment. Molly could still detect the faint aroma of Zoe's personal scent as she moved around the dining room packing the last few items in boxes. It kept a smile on her face and her thoughts away from Camden.

Jacob had just headed out with a large box when their father, Justin, appeared looking uncomfortable. "You're getting an early start," he observed.

"Hey Dad," Molly said as she taped the box closed she was working on. "You gonna miss us?" She knew he was worried about the empty nest, but there seemed to be something else bothering him. "You okay?"

"Camden stopped by last night," he said with a carefully neutral expression.

The official cover story had been that Camden and Jacob had been dating. No one had questioned Molly always hanging around her best friend and brother. Even though Camden insisted she wanted to be open about her relationship with Molly as well, they had never found the right time to come out.

Oh John! [anal, Gay, Best Friends] First Post

This is how I remember the events that evening. We had too much drinks and started to talk about sex. Me, John and 4 or 5 other guys talked for what seemed a long time. I made some stories up but admitted I was a virgin. John surprised me by saying the same and Paul too. That made me happy – I wasn't the only one.

I kept listening to those guys barging about banging some girls imagining me instead – those small shorts showing off hot hairy muscled legs, those strong arms… all that time I was hiding my bonner.

Eventually we went to bed. We were enjoying holidays at Paul’s beach house – no parents allowed. Three rooms – a large one for Paul, Richard was sleeping on the living room, Joshua (?) and Matt were sharing a bed and me and John another one. Old friends, old habits.

John brought some bears to the bedroom – “hey wanna talk some more?”

“Sure!” I was fucking drunk to say no.

Let me introduce you to John (or just skip this part if you’re horny).

Molly, Jacob, and Camden – Summertime Blues 1 [MF][FF][oral]

Click on my username to see the previous story posts featuring these three. There will be more to come.


When the charter bus from Camp Wikinoki finally pulled into the school parking lot, Molly looked at her twin brother Jacob who was licking his lips. He had a spray of colorful wild flowers in his fist. She knew they each loved Camden in their own way, so the six weeks she'd spent away as a senior camp counselor had been hard on them both.

"Why am I so nervous?" Jacob whispered.

"Six weeks of pent up sexual frustration?" Molly whispered back with a raised eyebrow. When he blushed she asked, "Don't tell me you cheated? Her instructions were very specific when she left."

"It would have been easier if you hadn't spent the whole time out at our pool in that black bikini. I swear you outgrew it in eighth grade." He gave her a dirty look.

She glared back. "Who kept walking around naked every morning?"

"Who cares? We made it," he sighed. "And there she is."

Molly's smile faded when she saw Camden's downcast eyes.

Mutual Masturbation Story [m m, mastrubation, porn mag, mutual masturbation] not gay

[This is a real story of an experience from my time in Jr. High. All though I did in face masturbate with another male, he touched me and I touched him. I do not think that I'm gay, nor was I trying to be gay. There was no kissing, we weren't dating, he wasn't a boyfriend and we never did it to be gay. It was two male adolescences experimenting.]

I think it was in eight grade when I lived in Glendale UT, my friend Hamilton Porter or Ham as he was always called told me about him and another friend masturbating together in a tree house. He said the friend has stolen a nudie mag from the store and they had gone up to the tree house to look at it.

Ham was a shorter and fatter kid in my grade. He was often picked on because of his glasses. His mom was a strict lady that today I think had some kind of sick views.

i [F]inally [F]ucked my best friend, my love

So 9 months ago I met this girl at a gay bar in my hometown. I usually dont go for the girls in my hometown, I live in LA usually and my town is full of a bunch of baby mama lesbians. But this girl was immediately different, i kind of fell in love right then and there. She is hispanic (me too) crazy fit body with perky c cups, beautiful big brown eyes, luscious lips (like as big as angelina jolies–no joke), and could easily be a model or actress. Shes also incredibly smart and works in the oil field as a welder. YEAH like the girl in flashdance.

I was done, i was madly in love. We liked all the same books, had the same philosophers, and it wasnt long before me, her best friend, and i were all three best friends.

it was complicated tho bc we had started out dating but she soon made it clear she only wanted to be friends. i thought we had gotten along great, had passionate hookups (no sex) and great conversations…but her best friend let me know she had a lot of baggage from exes who had used her. So i agreed to just be her friend even tho it was killing me inside.

My first time and it was amazing (M/M)

Throughout high school I was very anti-gay and was a total asshole to everyone whom I considered gay. My senior year, I came to my senses and realized that they're people too. Well, my senior year I became friends with a boy who is openly gay. We chatted at school and lunch. Things extended to texting after school and hanging out. He never made a move on me or anything but I developed a small crush for him. At the time, I just thought he was a good friend. Well after graduation, we started flirting which moved to sexting. He sent me picture of his cock, which is very beautiful, and some pictures of himself posing. I sent a few back. After a couple of weeks, he asked if I wanted to fool around. I said sure.

We were at his house, sitting on the couch. He rubbed my leg and gave me a smile. My heart skipped a beat. He started rubbing my leg. As he did this, my body was sending me chills and getting me hard. He rubbed my cock through the outside of my shorts and half way through I got spooked and told him to stop. A few weeks later, I moved 500 miles south. Didn't talk for a year.

My roommate and I had a threesome with a lawyer this weekend… He is in an open marriage.

We went to go visit my roommates family in Houston this weekend and while we were there, we decided to go out Friday night. I'm 18 and she's 21. I lost my fake, the only clubs that would allow 18+ there, were 2 gay clubs. My roommate happens to be bi and she was looking to meet a girl anyways. We had a lot of fun and I wanted my roommate to have a good time. We met a group of guys who were mostly gay.. One of them though had a ring on his finger and my roomie whispered in my ear that he was married. However, we kept talking and he was extremely nice/funny. We left the club where we met them and he walked us out and gave us his phone number in case we needed anything, he lived in the neighborhood. My roomie and I ended up at another club but shortly after we got bored and called the lawyer, told him we were coming over, and 10 min later we arrived at his place. While making conversation at his place we learned that his wife is an opera singer and he has a daughter. His wife often leaves town for several months due to her career and for that they have a "don't ask don't tell" policy. That made us feel better about wanting to hookup with a married man. BTW I had never done this before. My roommate who is bi started kissing me and since I was a bit drunk I went along with all that happened. I told the lawyer to have sex with my roommate and he kept kissing me while they did that.. Then my roommate and the lawyer took turns eating me out.. I was totally scared to eat my roommate out but I did it anyway.. And it wasn't too bad. I did it for like 10 seconds because I had no idea what I was doing but she didn't care that much. Until this point I still hadn't had actual sex with the lawyer, but I did make him cum by giving him a blow job. After the lawyer finished having sex with my roommate, she passed out on the couch (this all took place in the living room) The lawyer and I cuddled under a blanket and started watching American horror story while suddenly I got really horny again… I was determined this time, that I was going to fuck him. And he picked me up and we did it on his (and his wife's) bed. the next day he bought us dinner and we repeated the night again. Just FYI I've only had sex with 4 people, 2 of whom I had a long term relationships with.. This was a brand new experience but the sex was great and I'm really proud of myself for letting my guard down a little bit, you could say it was a crazy wild weekend.

Former employee needs a friend (PART 1)

I recently left a job after training one of my employees to replace me. Needed a change of scene and I wanted to promote Shawna, one of my employees, to manager. I liked her spirit and was proud of how she well she had done at the company. I guess I just liked her as a person and wanted to see her succeed – kinda corny but true. We had a fun relationship in the shop – we both had the same sense of humor, both learned from each other and we both found each other interesting. She was one of the few people I could talk to comfortably about most things. I never brought up inappropriate subjects seriously, only ever as a punchline to startle someone and make her laugh. She had been going out with a guy she had met at school before she graduated and they seemed like they were okay together, but I always felt like it was one sided. Whenever we hung out, she seemed like she was making all the effort to talk, have fun, even just come up with ideas of what to do like what to cook or what movie to go see. He wasn't a jerk, just seemingly uninterested.

Jake’s Magic Remote, Part XI – Misdirection

Jake and Sarah were reading in the living room when the doorbell rang. Petra answered, knowing it would be Katie arriving, and welcomed her in.
“Did you eat, Kat? We already did, but there’s some snacks if you want. Oh, you remember my parents.”
Katie came around the corner with Petra and smiled. She was wearing a white tee and a tight pair of jeans, and Jake could swear that she’d grown a cup size since he’d seen her last, although that might just be the work of a really impressive feat of bramanship. Her hazel eyes, strikingly incongruous with her dark skin and hair, locked on Jake as she spoke. “Of course I do. Hi, Mrs. Stevens. Hi Mr. Stevens. Thank you for having me.”
Petra’s eyes widened a little as she tried not to laugh at Katie’s accidental double-entendre. Then again, the way the girl was eye-fucking Jake, he wasn’t so sure it was accidental. He smiled as Sarah greeted her, then replied. “Hey, good to see you again. What have you two got planned?”
Katie shrugged. “A little studying, maybe a board game… you know, whatever comes up. Girl stuff.”
“Well, you two have fun then,” Jake replied.
“Oh, we will. Thanks again.”
As they left, Katie whispered something to Petra that sent them both into a giggling fit. Sarah watched them and frowned.
“I’m starting to regret this,” she said quietly.
Jake scoffed. “They’re just kids. What’s the worry?”
“Clearly, you were never a teenage girl.”
“Well, I thought about it, but I just enjoy having a dong too much.”
Sarah grumbled. “Look, just… check in on them, alright? Don’t let them get up to mischief.”
“You don’t want to do that yourself?”
Sarah shook her head. “I haven’t been sleeping well. I’m taking a pill tonight.”
“Suit yourself. Our daughter’s virtue is safe in my hands.”
Jake meant it, too. Just not in the way that his wife intended. Still, he was a little worried about her behavior. She’d been more withdrawn lately, more surly, and generally avoided spending time with her husband or daughter. Which was just as well, given that her husband was fucking her daughter, but still, it kind of hurt to see the person you fell in love with pull away.