I’ll call myself Will for this story.
About 17 years ago when I was in high school and barely 18, I had an odd group of friends. The bulk of us were the weird anime kids who played in band. I liked anime but not like THEM. I became part of that group because I was on the swim team and another guy who I got along great (I’ll call him Bill) with kind of invited me to hang out with them. This group was about 8 women, 2 other guys, and me. The high ratio of women to men is because most guys avoided this group and went for BFS to bulk up and join the football team.
This was also a VERY small rural town that was super religious. The Fellowship of Christian Athletes was the largest group or clique at the school. I was not religious at all, so the venn diagram of my friend groups was super weird and complicated, and I’m sure a handful of them only hung out with me to convert me. Especially since I dealt with my intense awkwardness via drugs and alcohol.
This was also before I hit my growth spurt. I was about 5’7″ at this time, but since I swam two to three hours every day I was toned. Just not bulky. Genuinely wish I had this physique again even if it meant losing the 5″ of height I eventually gained. I was also packing heat, if you catch my drift. My dick is a tad over 8″ hard and thick as hell, but as mentioned in another post (and if I find an old picture before I had it fixed I’ll post it) I had a botched circumcision that made me super self conscious about it.
What that means is that anyone not on the swim team who only ever saw me with clothes and hoodies on all thought I was just a gangly guy with long hair who smoked weed and swam a lot. Even that close group of friends thought I was just another weeb who was out of shape like them. They weren’t super wrong because I didn’t have strength. Swimming comes from endurance, form, and shape, so anytime we had to lift something big I clearly wasn’t standing out.
At one point one of our friends (I’ll call her Jill) said she was moving and we were all gonna have a party at her place. It wasn’t gonna be a rager, but it wasn’t gonna be alcohol free either. Her parents knew and intentionally left for the night so their daughter could have a good time. I didn’t bring drugs because I’m fairly sure I was the only one in that group that did them, but I brought a ton of alcohol.
The party started with a bunch of people, maybe twenty, and all just doing nerd shit like MtG and watching Harry Potter. Eventually the number of people dies down until it’s pretty much just our close group, minus one guy and a few girls. If I remember it’s like 5 girls, Bill, and me and I had a crush on all but one of them (Who I’ll call Lill). Since it’s just the close group, a few gifts come out at this point. Some heartfelt things like a signed copy of a book and whatnot. But also a few gag gifts like dildos and hentai novels.
We’re all pretty buzzed and like most horny, drunk, high schoolers, Truth or Dare comes up.
It starts out tame enough, asking if people had crushes and whatnot. It was pretty clear that most of these girls were interested in Bill. He was also swim team and showed off his body every chance he got, so everyone knew he was in shape. He also had a reputation (for better or worse) as a bit of a player at this time, as he lost his virginity in 8th grade and took several women’s V-Card over the next 2 or 3 years. We actually stopped being friends a few years later because of this but that’s another story.
But all these tipsy horny girls kept focusing on him, getting him to show his abs or making out with him. I went mostly ignored which was fine, until one girl dared me to take my shirt off. In hindsight I suspect it was in an effort to mock me in comparison to him, and thus getting me to leave. But when I took off my shirt, a lot of “oh damn!” happened because now people saw that I was TONED. AS. FUCK.
At this point everything shifted tonally. Bill and I kept our shirts off and dares were now with the girls trying to show off. A few times flashing boobs, one girl streaked to the mailbox and back. Eventually Bill and I lost our pants and underwear. He sat there comfortable in the nude and he had an okay, uncircumcised dick. But I was self conscious, so I was covering myself with one of my shoes (yeah gross I get it). The girls giggled at my timidness mistaking my self doubt about dick SHAPE for self doubt about dick SIZE. A few of them goaded me saying it must be small if someone built like me felt bad about it. They weren’t being mean and I knew that at the time, they just wanted me to show them. So I said someone would have to use a dare if they wanted to see it.
Unbeknownst to me up until that evening, Jill had a crush on me. So she didn’t hesitate to use her dare.
“Okay, I dare you to remove everything and put it on full display.”
So, to my dismay, I pulled the shoe off and widened my legs so there was nothing preventing view of it. Now all attention was on me, but not in a good way. Yeah I’m big when hard, but I was flaccid and that botched circumcision is VERY noticeable. Everyone zoomed in and began asking questions about it. Was I born that way? Does it hurt? Has anyone ever made fun of it? I answered all of them, but then got one I hadn’t anticipated.
“Can it even get hard? I mean like…. if the skin is attached like that wouldn’t it hurt if it started to stretch?”
I was definitely caught off guard and just muttered out something along the lines of “of course! It just looks fucking weird, that’s all. You’ll understand when you see it.” This made me tense up because of how forward that was, which wasn’t my intent/
Now the game shifted again. It was no longer a tug of war for attention between Bill and Myself. It was a carnival game for the girls, and we were the prize. Each new dare was for them to get somewhat more daring with our dicks. Bill and I didn’t even really receive any new dares as a result, and mostly sat there having fun. Over what I guess was about 15 minutes, dares ranged from getting their faces close to our dicks, to holding them for a few seconds, and finally to stroking them for 30 seconds. They were mostly all still wearing clothes. I think they all still had their panties and 3 of them still had bras on. These were the first times anyone other than myself and doctors had ever touched my dick, and I’ll tell you it was difficult to not become TOO excited by every single touch.
Bill’s dick was above average at maybe 6.5″ or 7″ and had average thickness. But he had the advantage because he was uncut (scandalous in our Christian town) and therefore extra naughty. I won the size and thickness category and it received some nice high praise, but the shape detracted from overall attraction. Now that the girls knew what each tool looked like, they could decide for themselves which one was the best fit for their job.
Now they had to compete for us. Dares were for them to completely show themselves off, even spreading their pussies open. A few times they had to get on their hands and knees and show off their form for doggystyle. Lill had great form. She arched her back and had her face down. Of all of them she was the only one who shaved, too. So even though I wasn’t super attracted to her, since she had hygiene problems and a garbage personality, I wanted to fuck the shit out of her. I wanted to bury my mouth into her pussy and just go to town. But of course, after each dare they’d put their panties back on and sit in their position.
Needless to say, Bill and I were rock hard and ready to attack at the drop of a hat. Finally we started getting dares again. The first was for Bill.
“I dare you to lick Lill’s pussy for 30 seconds.”
And he did. No hesitation. She lay down in the middle and pulled her panties off in that crazy sexy way where it reveals the gem at the last second before going up her legs. Then she lowered them and before even being on the ground Bill was on her. There was no time keeper, just an estimated amount. But I don’t think anyone even bothered estimating. We just sat and watched this happen and I found myself stroking my dick until Bill stopped on his own. At this point the girls saw I was stroking and it was open season for them.
Bill used his dare on Jill. “I dare you to suck off Will for a minute.”
So she crawled over to me, still with panties and bra, and took me into her mouth. This was it. This was the first time I had been inside another person in any way. Never had any sexual contact before tonight and I barely ever even made out with people before.
She didn’t need a minute.
I lay back and instinctively grabbed her head and just held her hair. I didn’t push her head or anything, I just held it like she was the bull and I was just trying not to fly off. Thirty seconds later I had to warn her to stop. I said I was gonna cum soon.
The rest of the girls laughed at that measly amount of time, an even Jill giggled. But she backed off. A few more dares and whatnot later, and someone dared Lill to give me a blowjob now. I preemptively warned her I wouldn’t last long and she said that was fine. She gestured for me to sit on the couch behind everyone and got between my legs. As I looked at her I really just did not find her attractive at all. I do feel bad about that because I think she had a crush on me too, but I could never have reciprocated those feelings. I just wanted to use her. I needed to cum and she seemed willing.
She took me into her mouth and everyone watched. Once again, maybe thirty seconds later I told her I was about to cum. She didn’t slow down and just kept her pace. As I felt it build, I grabbed her hair and told her it’s coming, and she gripped my thighs and sped up. I started cumming so hard into her mouth I was getting dizzy. After a few seconds she stopped bobbing her hear and just held her mouth on the tip of my dick. When I stopped, she pulled away and turned to everyone. She spit my cum into her hand and said “Only losers quit at the finish line.” Before smearing it on another girl’s face.
Being my first time, I don’t think that anything anyone could have done could have gotten me hard again. The combination of post-nut clarity realizing my first blowjob was in front of several people at a party, mixed with the intensity of my orgasm, completely spent all my energy.
So I sat there and watched the game turn into Bill just doing what he could to make them cum. He either fucked them while they played with themselves, or ate them out to completion. When he wasn’t with a girl, the dildo was in use. Very unhygienic and I would absolutely not advocate for that as an adult, but holy shit was it hot watching a girl cum on a dildo, then pull it out and watch another girl use it.
Once everyone was spent and post-orgasm clarity kicked in for everyone, someone put a movie on and we all watched it together on the couch or floor until we fell asleep. Jill left a few days later, Lill continued to have a bad personality, and Bill would go on to be a douchebag who would hit on girls by asking if he could take their virginity. Word got out around school that I had a large but weird dick, and that led to some other interesting situations that I’ll post about later.
Source: reddit.com/r/gonewildstories/comments/v0qkbd/my_first_sexual_encounter_a_blowjob_was_at_a