Straight Virgin Loses a bet and his Anal Virginity
Introduction:
Hi, so this is the story of the hottest and most life changing sexual experience I’ve ever had. If you not into bisexuality this isn’t your thing and you should leave. Otherwise enjoy!
This tale takes place about 13 years ago when I was in school. At this age I was fairly awkward and unaware of how attractive I was. Years of a passion for rock climbing and puberty had recently changed my body from that of dorky awkward boy to that of a fairly attractive teen. Spending 3-4 days a week at the local indoor rock climbing gym along with normal PE activities and running and lifting had given me a very Lynn strong body. I had a toned 6-pack, VERY large and toned forearms for my size (135 lbs) along with a strong back and a decent tan that I got from doing yardwork shirtless for spending money. I was also fairly hairless, except my pubes which I had just started shaving because I preferred the feel of bare skin while masturbating my ignorantly large 8-inch cock. Which I did constantly.
Ever since I was young I always had an uncommonly high sex drive. So much so that I was caught masturbating in class more then once. This is one of those things that led to my misconception of how attractive I was. Getting caught playing with myself in class had turned me into a social outcast throughout most of my school experience, and in my head no one that’s that socially shunned could be a cool hot guy. Along with a misconception of my attractiveness, I was also misled about the size of my cock. This was because with the exception of the cocks I’d seen in porn magazines, the only cock I had seen before was the occasional glimpse at my brothers when we both had to pee at the same time. As a result, I had no idea what a normal size cock looked like, and since I didn’t have high self-esteem I assumed I must be on the smaller side of average. I was soon to learn that wasn’t so.
I haven’t finished this section of the story yet, honestly it’s a boring part of the story that only really sets up the continuity. Eventually I will and I’ll post the revised version. Until then though the next paragraph cuts to a party that I ended up at by accident with 8 people from my high school. Bibi, my ex-girlfriend who was openly gay. Lyn, the Czechoslovakian foreign exchange student that was rumored to be bisexual and have a “European attitude towards sex.” Missy, my friend from elementary school who Bibi dated for years before she dated me. This mixed with the fact that Missy had a thing for me made her have a lot of animosity for me. Kat, a very hippie friend of mine who smoked a LOT of weed and would get insatiably horny when she did. Sadly, she wasn’t attractive to me, but I did like how intelligent she was. Mathew, a quiet timid blonde boy from my school. I had recently learned that he was gay, in the closet, and apparently attracted to me. Ty, a fashionable tall black gay guy from my school. I didn’t know him well, but like Mathew apparently he was ALSO attracted to me. Ty, Micah’s current boy toy who I knew nothing about other than he was timid, curly haired, blonde, and skinny. And last but not least, Micah. The most openly gay teen from my high school. He had short brunette hair, a skinny fit body, and was VERY opinionated. He got off on bringing out the homophobia in straight people.
Cut to the party. Were all in Kat’s room, passing around 2 pipes of weed and fairly stoned.
After taking another toke of weed from the communal pipe, I noticed Ty, Mathew, Micah, Ash, Bibi, and Lyn were missing. I heard girls giggling in the closet and saw bodies moving under the bedsheets. That’s when my obliviously stoned brain put two and two together… this wasn’t a normal party, it was a bisexual orgy!! The giggling in the closet was my lesbian x-girlfriend, Bibi, making her moves on the Czech foreign exchange student, Lyn. And the movement under the covers was surely Ty and Mathew! I couldn’t believe what I was in the middle of!! This was the start of a teen bisexual orgy with 8 other people in the room! Then a crazy thought occurred to me, Bibi was my ex. From both her and her ex Missy I had heard that Micah was VERY attracted to me and Mathew and Ty were also. Ontop of that I knew that Missy and Kat were attracted to me, because they had both admitted as much when we were high months prior, and I had a suspicion that Lyn also thought I was attractive because she would flirt with me in English Lit class a lot. Where was this leading?
At that moment Micah and Ash walked back into the room smiling and blushing. Micah had an erection clearly visible through his tight jeans. He must have noticed it caught my eye, because he turned to me, grabbed his dick through his jeans, and said “Do you like this? Big isn’t it? I bet it’s the biggest you’ve ever seen.”
This wasn’t the first time Micah had fucked with me like this. He legit believed that there was no such thing as “straight people”, just people who haven’t come out of the closet yet. He also got off on flaunting his homosexuality in front of any straight male in our high school to get a rise out of them. When he got said rise he would call them things like “homophobic breeders!” He especially liked to toy with me, as he currently was, because he thought I was “clearly closeted” and had admitted to my ex that he “wanted to fuck me.” Not to mention I’m sure he fantasized about turning my straight cock. This made me detest him, even though part of me was VERY attracted to him. He was right to some extent, even though I thought he was an asshole, I was attracted to him! But I also was attracted to women slightly more and still am. So I wasn’t “gay” like he thought, I was bi. And even then some part of me knew that.
So when he flaunted his cock in front of me I got the great idea of challenging him to a size comparison. Whoever had a bigger cock had to do whatever the other one wanted. For me that was for him to leave me alone and stop hitting on me, for him that was probably to finally get the chance to turn me like I guessed he wanted to. He acted apprehensive, but agreed on the stipulation that we were “hard when we compared.”
I said “Obviously, but who will get me hard?” Knowing full well that Ash would be his fluffer.
Micah smiled at me and said “I can do that.”
I told him to “Fuck off.”
That’s when Missy, who had been watching this whole thing play out stepped in and said “I’ll do it, but you can’t tell anyone at school about this!”Being fairly attracted to Missy, I said “Ditto” and agreed.
As Ash pulled Micah’s pants down slowly I noticed he had a huge grin on his face that made me nervous. He wasn’t wearing underwear and the first thing I noticed was his upper pubic area. It was shaved uncommonly smooth, possibly even waxed knowing Micah. Next I saw his shaft, as his tight jeans slid down they revealed the shaft of his cock. The further down they slid the more shaft they exposed, it just kept going. That’s when I started to get a sinking feeling as inch after inch of Micah’s already half-hard shaft was exposed. Finally, after what seemed like ages, his head slipped out and I saw all of his enormous cock! I couldn’t believe what I was seeing, he must have been 7 inches long already and he wasn’t even hard! I knew I was fucked, possibly literally.
Ash grabbed Micah’s shaft and started moving his hand up and down. Then he took Micah’s cock into his mouth and deepthroated it until it disappeared inside his esophagus before pulling it back out, glistening with saliva. He kept this up as Micah looked me over like a piece of meat he was eager to bite into. At that moment I started to feel myself get hard. The thought of that giant cock was making my mouth water, but why? I was caught like a deer in the headlights not even realizing how much I was staring at his now rock hard cock. IT MUST HAVE BEEN 9” LONG!!
My gaze was finally broken by Missy, who had pulled my pants and breifs down and had just slid her hand around my already hardening shaft. She spat on it before sliding her hand up and down. I was already harder than I’ve ever been at this point, but she still slid her mouth over my head and started working it slowly, getting me as hard as possible to gove me a fighting chance. To this day I don’t know if she did that to hide the fact that in front of everyone else in the room I was getting turned on by Micah getting a blowjob from Ash, to help me get a leg up by making sure I was as hard as possible, or simply because she had just wanted to suck my cock, but I suspect it was a bit of all three.
After Missy blew me for a while I looked up to notice that Micah had his cock out of Ash’s mouth, rigidly sticking nearly straight out with a slight curve, and was waiting for me. His cock seemed to twitch with anticipation. I tapped Missy on the head and she pulled my engorged 8” cock out of her mouth. It was at that moment that I realized that she and the 8 other people in the room were all watching to see how this played out. I thought “This is so crazy!” But I had taken this to far to stop.
I tried to hide what I was thinking and act confident, but my nervousness must have been obvious because Micah looked me right in the eye and asked “You like what you see? I hope you do, because I’m going to make you worship my cock all night!”
I pulled myself together and responded “We all know you like what YOU see. Don’t get too excited yet.” I thought that was clever, little did I know I was just digging the hole deeper.
The moment was up. It was time to compare despite the fact that the winner was obvious. Micah must have known I was too nervous to make the first move, so he walked up to me and before I could react he grabbed my cock and held it up against his, arranging them so his was on top of mine, foreshadowing what was to come. With our members pulled together, mine pulsing with nervousness, his with anticipation, he slid his down mine until his head touched my lower stomach. But there was a little over a solid inch of space between my head and his balls. The winner was clear, but regardless he said out loud for everyone to hear.
“You lost. Now take off your shirt and get on your knees! Your gonna start by sucking my cock”
Shaking with nervousness, I responded “But…. You…… in front of everyone?”
And he replied, “This could’ve been private, but you dug this hole for yourself. Now your my slave for the night and you’ll do as your told!”
I looked around and the 8 other people in the room were anxiously watching, a few of them had visible erections. I looked back at him and then at his massive cock, still hard as ever. At that moment I accepted my fate. He won fair and square. I was going to be Micah’s boy toy until sunrise.
I took off my shirt, now completely naked and exposed, and got down on my knees as I was told. I was shaking so hard; this wasn’t supposed to play out this way!! As I thought about what Micah might do to me he grabbed the back of my head and guided my mouth onto his massive cock.
My mouth stretched open as his head slid past my moist shaking lips. Then he kept pushing as his shaft slid down my throat until his head hit the back of my throat. I never told anyone this, but I have almost no gag reflex. This came in handy as he pushed harder and forced all of his 9 inches down my throat until his balls rested on my chin. I remember the scent of his balls was intoxicating. He then told me to look up at him and said “I knew you were a good little cock sucker!”
Then he pulled his cock out to the tip fast and pushed it back down my throat even faster. My face started turning red and he said “breathe through your nose! This isn’t stopping anytime soon!”
He was right, his repeated this for a good 10 minutes. Shoving his cock down my throat faster and faster. His balls slapping against my chin over and over as my throat became sore. He then pulled his cock out of my mouth, dripping with my saliva, and pulled me up to my feet.
As I stood up he turned me around and shoved me against the wall face first. Then he grabbed my legs and pulled them open before pushing down on my back until my face pressed against the wall. Then he got down on his knees behind me and took a big wiff of my ass before shoving his face into my ass crack.
I felt his hands grasp my asscheeks and spread them open, then something wet and warm started probing around my asshole!! IT WAS HIS TOUNGE!! I couldn’t believe it; this was all happening so fast. And the crazy part is………I was liking it. No, I was loving it. Just then I gasped as his tongue slipped inside my tight virgin asshole!! My cock twitched and hardened even MORE as he drove his tongue in and out of my ass!! I gasped with the intense pleasure.
Micah noticed and pulled his tongue out to say “your liking this aren’t you you little slur?”
I responded “No, I’m straight Micah!”
To which he said “sure you are slut!! No straight guy sucks cock that well” before shoving his tongue back into my now slick asshole.
At this moment moaning from the bed caught my attention. I looked around and noticed Bibi had dawned a strapon and had Lyn bent over the bed, pounding her pussy while Lyn watched Ty drive his huge black cock into Mathews asshole while Mathew had his face buried in a pillow. Then on the floor I noticed Kat had her face buried in Missy’s vagina, making her shake with pleasure!! Everyone else had clearly followed our lead after I lost the bet. This was it, the orgy was happening and I was part of it. We were a writhing mass of bodies!!
Part 2 to come soon!!
