Jerking Off with My Best Friend in the Early 2000s [MM]

Growing up, my best friend was Don. We were smart, did martial arts, and were a great comedy duo, so in high school we ended up working our way through all of the women in our friend circle. We’d share tips with each other to help the other one score better. “Rachel likes a firm tongue on her clit and 3 fingers in her pussy” or “Kristen likes to have her hair pulled and be pounded like a jackhammer,” or “Laura has daddy issues, order her around like she’s a useless slut and she won’t stop cumming.” We’d talk about sex late into the night, and it would always make us super horny. But we grew up in a conservative town, so even that level of open communication was a little taboo. Now I realize that Don is probably bi and ashamed about it, but I’m secure in my straightness and have never been too hung up on labels anyway. I like what I like. By our senior year though, we broke through some of that bullshit and had some great times.

For anyone reading this who grew up always having internet, parts of this story might sound quaint. But there was indeed a time when we couldn’t access porn 24/7. It was a dark time, but we managed with what we had. We both had the internet by the time we were in high school, but my parents had monitoring software on my computer, so no internet porn at my house. But Don’s family computer was clear. We just had to wait until everyone was asleep since the computer was in the living room. Once the coast was clear, we would spend hours searching for pictures and videos of hot women. Our favorites were bikini and fake nude shots of Sarah Michelle Gellar, Jessica Alba, and Kristen Kreuk. After a while we moved on to porn videos, but it was rare because internet was so slow back then. We would stare in silence, occasionally commenting on how hot the women were. This was fun but frustrating. I’d always end up jerking off in his bathroom. One time I came out of the bathroom earlier than usual and watched Don cleaning cum off his cock. I was pleased to know that he was doing the same thing, even if we didn’t address it.

One of our favorite things to do at my house was watch the E! Channel, because they would always show the Girls Gone Wild ads, and feature shows about hot women in bikinis dancing at night clubs. My room was tiny, so Don would have the bed and I would be on the floor in front of the TV. One night we were talking about how we had both banged Ginny, and were comparing notes. It was summer so we were both down to our boxer shorts, and I was rock hard and knew he was too. However, we were strategically positioned to stop the other one from seeing. I realized that this was crazy: Two best friends who were eskimo brothers a half-dozen times over shouldn’t have to pretend like they’re not horny when they talk about sex with tits bobbing in the background! So as we watched the hot sluts on the screen, I laid back, put my hands behind my head, and stopped hiding my boner. I let it stand straight up under my shorts, knowing I was in line of sight with the TV. We kept talking, and when I glanced over I saw that he had laid back too and was also flying at full mast. From then on, when one of us would get hard, the other could always clearly see.

One day Don told me he had a huge surprise, and that our next sleepover would be amazing. A few days later, we got off the bus and practically ran to my room and locked the door: From his backpack, Don pulled out SIX Penthouse magazines. His older brother had owned them, but his girlfriend threatened to dump him if she caught him with porn, so they were passed along to us! Glorious Day. We read them all cover-to-cover. Every hot story, every great centerfold. And this was back when Penthouse had hardcore content, so we were in heaven. Aria Giovanni, Sunny Leone, and Tera Patrick all right there for us to ogle. Don sat on the bed, I sat in my computer chair. Both in boxers, both fully erect as we flipped through the pages admiring the sights. By probably the 2nd hour of reading porno mags, I couldn’t take it any more. I started absentmindedly grabbing my cock over my boxers. It felt so good. I knew Don might call me names or something for playing with myself in front of him, but there was only one way to find out. So I starting slowly stroking over my underwear. Penthouse in one hand, cock in the other, best friend 3 feet away as the good lord intended. After about 30 seconds Don says, “Enjoying the magazines, eh bud?” I said, “Yeah man, you can too if you want.” He shrugged, and we both stroked our cocks through our boxers. After a few minutes of that, Don reached into his boxers and started jerking himself off properly. I was so turned on, but we were still being modest by leaving our boxers on. After a few minutes of stroking together, Don suddenly jumped up and went to the bathroom without saying anything. I knew what was happening, so I finished myself off into a towel and threw it in the hamper. Don came back about 10 minutes later with a soft cock, visibly more relaxed. We shot the shit the rest of the night.

This went on for weeks. We’d talk about girls and read porno mags, jerk off under our boxers then finish in separate rooms. It was a blast. But things changed when a friend of ours got hold of a few porn VHS tapes. He made copies and sold them for $20 a piece. Don and I pooled our money and bought 3. One was a space parody starring Stormy Daniels. One was about an Asian prostitute recounting her sexual escapades starring Kia, and an all anal video starring Leanni Lei. They’re pretty bad by today’s standards, but it was the first time we’d been able to watch full length porn. We were in heaven. We were sitting side by side on the edge of the bed in just our boxers again (we wouldn’t discover the magic of boxer-briefs for a few more years. Ah the 2000s), our cocks straining against the fabric. We had been stroking under our boxers for a couple minutes when I noticed we were both absolutely soaking through the fly with pre-cum. So I said, “Hey do you mind if I take my boxers off?” He thought about it for a second…looked down at his cock….looked over at my cock…and said, “I don’t know, isn’t that gay?” I said, “I don’t think so. We’re getting off to hot women, not dudes.” He thought about it for another second. He was hesitant, but I could tell he really wanted to jerk with me. He just needed permission. “Think of it like this,” I said. “If you were at home right now, watching this porno, what would you be doing?” He chuckled. “I’d be naked, jerking off with hand lotion.” I laughed myself. “Exactly. I’d do the same if you weren’t here. So the way I see it, we’d be stroking our cocks to the same exact pornstars at the same exact time if we were alone. So what’s the difference if we do it together?” He started nodding and said “I should tell you…every time we watch porn here, I cum in your bathroom.” “I know bud!” I said. “I do the same at your house. So we’re probably shooting a load at the same time, only we’re 30 feet apart instead of 3. So why not just do it here where it’s more comfortable?”

He started stroking himself again. “Fuck it” he said, and pulled his boxers off. I did the same, and he fixed his eyes on the TV as he started stroking. I took a good look at what he was packing: a solid long cock (almost the exact same length as mine, oddly enough) but I was thicker. We stroked side-by-side for a few more minutes, when I asked “Hey, you mentioned you like using hand lotion. Want some of mine?” “Fuck yes I do,” he said, looking away from the screen for the first time and glancing quickly at my package. I grabbed the lotion, used it on myself, and handed it to him. With both groaned in satisfaction as a super hot, super slutty asian girl in high heels was taking it doggy-style. I laid back as I was getting close. “Fuck dude, I’m going to cum” I said. He nodded and leaned back too, ready to do the same. We both finished within a few seconds of each other, cum covering our hands and bellies. I handed him a towel, and we cleaned ourselves off. “What’d you think?” I asked after we had cleaned up. He laughed. “Much better this way. For sure.” This became our weekly tradition. We’d get home from school, hang out, and once everyone went to sleep we’d watch porn and jerk off together. Good times.

We shared a dorm at college the next year, and things got even better.

Source: reddit.com/r/gonewildstories/comments/fvjk87/jerking_off_with_my_best_friend_in_the_early