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In high school, I was a geek with my horn rimmed glasses. Wearing Baja style sweatshirts, often with sweat pants, I wasn't going to win any fashion awards. Definitely was not part of the "in crowd," guess the nerd group that was on the far fringes, as the jocks got all the attention. This was fine for me. At 6 feet with blonde hair and blue eyes, I was so skinny. Women wanted a guy who was accomplished and built, with Athletics beating academics every time. Yet that was fine for me, as I was gay. My freshman year I had given regular blowjobs to my friend Mark, and I really enjoyed it when he jerked me off for my work. While he wasn't as into it as I was, now as a sophomore, I missed my Buddy. So desired his fire red pubic hair and pretty pinkish white cock, that easily was eight inches in length. Why did he have to come from a military family? He was now deployed in Japan, and occasionally we would write letters to each other. Due to his dads job in the army, all I knew was they were engaging the Soviets in the Cold War. Scary times although far simpler. Sophomore year was going decent, and my first quarter grades would be all A's. Due to my acumen, I volunteered to be a tutor, which counted for graduation service hours. Here's where I met Milo and Evan, two juniors who'd be at my house quite regularly after school. Mrs Johnson our advisory teacher, had me working with them on chemistry classes. Milo and Evan both cared, and weren't by any means stupid. It was just that the math formulas, for whatever reason didn't compute. Pardon the pun, and both were student athletes. Milo was the team quarterback, and 6'2 and built, he was a handsome looking guy. His brown hair and dark eyes, and by his last name, it was obvious he was of Italian descent. Very friendly and outgoing, even though a jock, everyone found him affable. He had earlier in the year, stopped a bully from harassing a fellow nerd.
Evan was a wide receiver. He wasn't tall, but wow was he fast. I'll never forget the first game I saw him, as he blazed past all of the defenders. At 5'6 and not bulky, I heard parents in the stands, concerned about his welfare. Yet as the season went on, even after a big hit, it was obvious that he was durable. The guy caught passes from Milo, including a one handed one on a Hail Mary to win a game against the despised Stansfield Ravens. What a joy that was, and it was the only sport I followed or understood. Theater was my sport, and designing sets was my specialty. A lot of hours went into this, but it was a labor of love. Our high school had always been known for our drama productions, and next year I was going to try out for speaking roles. My parents and older sister were encouraging, and they said it would help my self confidence.
So far I was on the high school newspaper. It definitely was a nerd indicator. Yet some of my articles, that subtly hit away at school administrators, was loved by some in the student body. Milo and Evan brought this up in our chemistry tutoring sessions. Athletes read? Actually I was impressed, that I slung some lead at Mr Woodward. No one liked him, probably even his assistant principals, but I was thrilled that both of these football studs had caught on to my handiwork. Evans mischievous grin made me laugh. Milo who usually was more stoic, gave me a high five. Our study of mathematics went well, and I felt confident that their gpa would improve. Mrs Johnson thought the same, and sure enough in the next couple weeks, they were doing above expectations.
It was nice to have some credibility with Evan and Milo. Now they actually said "hi" to me in the hallways, and a pretty girl named Carrie beamed at me afterwards. Yet I didn't know what to make of this. I had kissed a girl "spin the bottle " in fifth grade, and also of course really only knew how to give blowjobs like I did my freshman year. Mark's sperm in my mouth let me know I had that down, although quite often I'd look at Carrie's ample chest. Yet the more I jerked off at home or in a bathroom stall, the more I thought about guys. I always came thinking about giving or having yet still haven't received a blowjob, thought about it and watched my cock shoot out globs of white sperm.
It was incredible almost being 16. Sure I had my learners permit, and driving my moms station wagon with her. Mostly she closed her eyes. Yet I was hormonal and confused. What would I do next year for prom? Would anyone accept my invitation? If I asked Carrie, would she laugh at me? Humiliate me publicly? That was a genuine and real fear, and I did want a thousand plus other students finding out. Yet I had dreams like everyone else, and put most of my passion into academics, the student newspaper, and also being a member of Model UN. This was such a terrific experience, and I was at every meeting. All of the international scenarios were fun, and teacher Mr Wilson made it even more believable. Before teaching he was a diplomat. Having served in multiple countries, he made our model UN the best in the county.
As I walked to history class, Evan was by the door. He said "would you like to party at Milo's house this Saturday?" Wow. I was floored. How to respond when I had never been to a party. "Ummm yes." Without even reasoning the reasons "no," that day after school was going to be my first drinking and social event. I went home immediately, and lied to my parents, that I was going to Adam's house. His family was gone the whole weekend, and my folks never checked up on my stories. Soon I'd be with the football team, cheerleaders, and so many more. Maybe after a few drinks I'd loosen up with Carrie, who Evan assured me "will be there."
How should I dress? The Baja wasn't going to cut it. I settled on my 32" Levi jeans, and a Eddie Bauer sweatshirt. Showing up to the address provided, Milo greeted me at the door. Lots of football players, jocks, and indeed cheerleaders. A year ago, I would have been intimidated, but there was Evan giving me a Bud Light. Someone out back was smoking weed, and Evan asked me, "you want to try it?" "Yeah, why not?" A little while later the beer and marijuana calmed me down more. Most people had left, but Milo said "let's go to my room, I've got some ecstasy." Totally comfortable it seemed the right thing to do, and sure enough everything became warmer. Saw streaks and it didn't hit me at the time, but would soon enough.
Milo, Evan, and I were all of a sudden only wearing underwear. We all were drinking water bottles. On the bed we all sat, and right before my eyes, Milo and Evan kissed. Was I hallucinating? They did it again, and I looked down and saw they were both erect. I was hard too. Soon I felt hands on my crotch. There was no resistance, as Milo said, "Usually Evan and I have sex, tonight it's your turn." Sweat was coming down my forehead. Did they really just say that? Then I felt their hands in my underwear, jumping up in the air. "It's ok." That's all I remember, as soon my 6" penis was being shared orally between the guys.
Your first blowjob is always the best. It's a final frontier for many, and I know lots of straight, gay, and bi couples who find this the most enjoyable. Oh wow my fingers and toes curled, as I couldn't ward off either of the guys. They were taking turns. It was an eye opening experience, and resistance wasn't going to happen. I soon felt them slurping up my balls too. No wonder Mark loved it when I sucked him off. This was mind bending state of consciousness, that I simply couldn't believe how good it felt. They went all the way down my penis, which was wet from their saliva, and soon enough my hands took their underwear off.
Evan and Milo had nicely scaped black pubic hair, and although Evan was smaller in size, it appeared he had a stallion pedigree. I had never seen such a big penis, in life as I peered at others, or when Mark was my guy that I sucked. What a huge unit, must have been 9 inches and thick. Definitely turned on, as was Milo who came in at around 6 or 7, but not quite the same girth. They both kissed as I massaged their private parts, and soon I bounced their genitals together. Hearing their moaning I just decided to go for it.
First Milo and I licked his shaft. So pulsating. His cut penis flew into my hot lips quickly, and I was bobbing up and down on him. Seeing him smile, and Evan touching his chest, I was literally losing it. I turned my mouth to Evan, who played with Milo's balls, and my lips sank on the elephant like trunk. Oh yes precum was already there. As I went up and down on him, releasing saliva to slide down his male organ, I couldn't wait for their cum in my mouth. Two guys blown to completion was so damn hot and horny. I was still rock hard, and soon I rubbed my crotch with these guys. It was like time itself had stopped. Evan and Milo continued to kiss. I asked them for some too. Oh yes their mouth's were on mine, our lips and tongues together for the trifecta. The room seemed to get smaller, and Milo brought out a bottle. "Ready to get fucked Terry?" Oh. It was lube.
I shook a bit. Hesitancy was adding stress to an already tense room. Finally Milo just gauged by my body language, as I felt his wet finger probing me. Mostly it felt like pressure inside me, but soon I was anticipating and enjoying the feeling this made. Silence and the room seemed to spin, as Milo was behind me. "Hold on and push down Terry." I did and was greeted by substantial pain. Thankfully Milo caught on to this, and went in and out slower. It felt different, and with time I started to enjoy it. Evan was feeling up his penis, so I gave him a hand. His moans and that of Milo made me stir crazy. I was getting fucked in the ass. My virginity was now over.
Before I knew it Evans monster was by my ass, yet the first thing was his long and strong tongue. An eye opening moment in my sexuality, as now I knew I was gay. It felt so amazing to have Evan in my ass now, and I could hear the lube, my hole, and his Dick meeting in one jurisdiction. Milo sat in front of me, and I attacked his cock. I wanted him to be satisfied. As I got plowed from behind, I licked Milo's penis and balls. The heater went on with a racket, but Evan was tearing me up inside. Finally I had to give him in a little smile.Evan at first wanted to keep tagging me, but was content enough, to know that sometimes even the most gay need a mind trick that can be used.
As I got my insides pummeled, I loved looking at Milo's eyes as I took his musky cock in my lips. Seeing him close his eyes. Watching him bite his mouth down. To feel him shudder as I also did getting porked. Evan was really making me feel him inside me, and soon I felt his hot load as he screamed some sort of wild animal like call to my being his bitch. As he recovered and watched his usual getting sucked, I couldn't help myself. "Do me too Milo." He grinned like a Cheshire Cat, like the one in Alice in Wonderland. I felt my hole played with and soon the surge of anticipation and relief. He was finger fucking me. The feeling was surreal, and just before I came, Evans mouth gobbled up my penis. Oh wow. Just full walking on the moon, as I cream filled his mouth with the biggest explosion of my lifetime.
Soon Milo was in me. He took me from behind. Despite not being as endowed, I couldn't help but gasp. His hands were so strong. Soon he was pumping in and out of me. It was too much yet I wanted him. The desire to make my new high status friends was my duty, and I took all I could despite the aching. Then Milo switched me to my back, taking me from the edge of the bed. I watched him probing me, as him and Evan kissed, also as his balls were gently massaged. Seeing this was amazing and sure enough, the visuals overtook us all, as Milo bred me really hard. The smell of sex, sweat and DNA permeated the room.
The next morning I woke up sore. Evan and Milo were polite, and made sure I was alright. They actually were quite understanding for the jock crowd. Later that day as I kind of walked, I knew that Milo and Evan were going to fuck me again. Smiling at the dinner table, my parents and sister wondered what I was beaming about. Of course I couldn't tell them the truth. "Yes mom and dad, and Bonnie my ass was fucked last night." That wasn't going to work. Instead it was "I feel that my social skills are improving at school." As my dad passed the side dishes, I got a bit hot and bothered thinking of the guys. Soon I'd have another chance, and now that I lost my virginity, all bets were off.