The first time I had gay sex
I was from a small Mid-western town. Going to college was the first real experience of my life. Sure I had a girl friend back home and we were fucking every chance we got. And when I was younger, my buddies and I use to jack off together. But nothing compared to my pledging.
I went to the same college as my father and his father before him. I was told that I would pledge the same frat. It wasn't a choice. I never thought of myself as a frat boy. I was rather skinny and I wasn't very good at sports. But it was "tradition."
So I went to the party when I received the invitation. I listened to the talk. I had already read the pledge book and had memorized the rules because of my dad. I was invited back. And I went through the motions.
Once hell week came, life changed. I was use to having my own room and now I had to share an attic with 24 other guys. Most of them were jocks. I found myself starting to stare at their well-formed chest and legs.
On the first night, we were all stripped and shaved from head to toe. We had to shave the body of the brother standing next to us. This was the first time I had ever actually touched another guy's penis. As I shaved him, he became aroused. And I did as well as the next guy shaved me. I must admit, we looked so funny standing there with no cloths and no hair, even our eyebrows were gone. We were instructed that we were to keep ourselves clean-shaven for the week. Most of the guys had some color to their skin and tan lines showed very clearly. I on the other hand was very white all over.
We were then escorted to the attic to find five double sized beds for 25 guys. Sleeping was next to impossible. 25 naked guys had to sleep in five beds. We put four across and one lying crosswise at the foot of the bed. I was stuck in the middle. It was impossible to sleep. When I did actually doze off that first night, I woke to find my penis at its full 8 inches getting to know the dick next to him who was also at full attention, standing around 6.5". I was basically lying with my shoulder on the guy next to me, who was flat on his back. Our dicks were rubbing together. His hand was also on my ass.
I attempted to pull off of him and put some space between our hard cocks. As I was concentrating on the dick rubbing my dick, I didn't pay attention to the guy on the other side of me. As I attempted to push back, I quickly came to the realization that the guy on that side of me was laying so that his front right shoulder was on my back and his head was nuzzled between my shoulder and neck. As I pushed my ass back, it was greeted by stiff dick at my ass crack. I was in an impossible situation and could not move, which made it all the harder to attempt to go back to sleep.
The next day we were assigned our big brothers. I was assigned to Drew. He was a junior and a baseball star. Being one of the brothers with the most seniority, he had his own bedroom on the second floor.
The first day, he gave me my daily chores list, which included laundry and cleaning his room. And then he started the interview. He drilled me on the rules and the pledge book. He seemed frustrated that I knew the answers.
So he was asking me why I was pledging. I told him my father and his father was both brothers. His face lit up.
"So you have to make it or you will upset the family?" Drew asked.
"Yeah, I guess so." I answered.
"Basically, you have to have my endorsement for you to get in. I am the only thing that is in your way. Being a legacy, nothing else matters but my approval." He laid back on his bed, smiled and said, "I have you by the balls. This is going to be a fucking great time. I now own your ass."
He readjusted himself and said, "Fuck the formality shit. Get over here and suck my dick."
"Fuck you. I'm not a fag!" I said.
"I don't give a damn what you are or aren't. What I know is that you have to please me or you're out. I can only imagine how ashamed your father will be. I bet he has talked to you for years about being in this frat. So you can either do what I tell you, or you can go call him and tell him that you didn't make it."
I knew he was right. My father talked about me joining the fraternity since I was old enough to understand. He had always wanted a jock for a son. But I was much more interested in computers and video games. I stood there thinking things over.
"Well, what's it going to be? Are you going to suck my dick or get you ass thrown out?"
I didn't move. My head was spinning. I was being forced to make a decision I did not want to make.
"Decide now before I decide to throw your ass out." He demanded. Before I realized what I was doing, I walked over to him and kneeled in front of him. My hand, while shaking reached for the fly on his jeans. I opened it and unzipped his pants. I tugged them down and then went for the waste band of his boxers.
As I pulled his boxers down, his 7" erect penis popped out. I grabbed it in one hand and slowly jacked him while I finished removing his boxers. I then licked the large mushroom head of his dick. He was oozing pr-cum. As I licked down the shaft, he was saying things like, "Oh yah, that's it." And "go ahead and suck it."
He had a very pungent smell. I was not sure I was going to be able to take it. When I licked my way to the base of his cock, I lifted my head, opened my mouth and took the head of his cock into my mouth. It was a very distinctive man taste, nothing like my girlfriend.
Slowly I started to take more of his stiff dick in my mouth. I took about 4" in my mouth before I started to pull up. I was only really using my lips, trying to make sure that I did not hit is dick with my teeth. I continued to go up and down on his dick, taking only about 4".
"Use your tongue, suck it hard. Make me feel good." He said. I started to wiggle my tongue on the shaft of his hard dick as I raised and lowered my head. Once and awhile, I would keep just the head of his dick in my mouth and swirled my tongue around it. >From his moaning, I was assuming that he enjoyed my new found techniques.
At one point as I was going up and down on his dick, he grabbed the back of my head and forced the full length of his dick down my throat. I gagged as he did this. None-the-less, he held my head with my nose buried in his pubs until I stopped gagging and relaxed my throat. Next he used his hands to guide my head up and down the full 7". He forced my head much faster than I was going. He made comments like, "this is how I like it" or "take it all you faggot."
Eventually, he dropped one of his hands and used the other hand to more or less encourage me to keep up the pace. And I did. Once I learned how to open my throat and I was not gagging any more, I was receiving a sensation that I had never had before. My head was swimming in the thoughts that I may actually be enjoying myself as I sucked on his cock. Found myself moving a hand inside my shorts and stroking my dick as I sucked his dick.
He began to tense. I thought he was getting close to shooting, so I attempted to remove his dick from my mouth. Drew had other ideas and he again grabbed my head and forced his dick all the way down my throat and held me there. I felt his dick throbbing in my mouth and then I felt his cum being forced down my throat. I had no choice other than to swallow or I would have choked. He shot a good three spurts down my throat before he loosened the grip on my head. As I raised my head up some, he continued to shoot his load in my mouth and I tasted the salty male juices. I just kept sucking his dick until he was soft again.
Without thinking, I pushed my shorts down and started to stroke my rock hard 8" cock leaning back on my heels. Drew said, "I don't want to see that. You're here for my pleasure not yours. But by that wood there, I would say you enjoyed yourself."
I didn't respond and only slowed the speed of my stroking. He added, "If you're going to jerk off, go to the attic with the rest of the fags. I want you back here after your last class tomorrow. Now get the fuck out of here."
I pulled up my shorts knowing that I couldn't jack off in the attic and I am sure Drew knew it as well. I headed up there still as hard as could be. I took my time getting there hoping my woody would subside. We were not allowed to sleep in clothing. It was one of our "bonding" events. It was nearing 11:00 and we had to be in bed by 11:00, unless a brother accompanied us.
I took my time undressing, hoping to be fully deflated by the time I got to my boxers. By the time I dropped them, I was for the most part soft. And none of the guys noticed anything, or at least they didn't say anything. I climbed into my bed with my four bedmates. Once I had naked skin on both sides of me, my dick sprang back to life. I slept on my stomach to try to hide my large boner.
By morning, I was still hard and the guys on each side of me were using my shoulders as their pillow and both were rubbing their hard dicks on my sides. I noticed as all the guys got up that morning that they all were sporting morning woodys. I was also rather proud that through my quick observations, I had one of the, if not the largest dick in the room.
This particular day was one of my most busy days. I wanted to get away somewhere and jack so badly. I was hard most of the day. But I never got the chance I desperately wanted. After my last class, I headed to Drew's room.
He wasn't there yet so I went about doing my chores that he assigned to me, hard the whole time. I was finishing up when he arrived. He entered the room and walked around with a shit-eating grin on his face. He acted as if he was inspecting my cleaning, but his eyes never left me. He sat in the recliner and said, "Strip."
"What?" I responded.
"You heard me take off all of your clothes." He demanded. I turned my back to him and I did, after which he said, "Now come over here and take my clothes off." He stood and I turned towards him, exposing my very stiff pole. As I went to him, he snickered at the sight of my hard cock. I undid his belt and pants, pulling them down. I helped him out of his shoes then pulled his pants off. Next I hooked my fingers in the sides on his boxers, pulling them down in one smooth movement.
Drew grabbed the back of my head and forced his crotch in my face. "You like sucking my cock don't you?" I didn't respond. "I want you to say you like sucking my cock." I still said nothing. He pushed me back, causing me to fall back. "Just look at your dick and tell me you don't like sucking my dick. Now say it!"
I quietly said, "I like sucking your dick."
"What I can't hear you. Say it like a man. You are a man aren't you?"
Slightly loader, I said, "I like sucking your cock."
"That's better." He said as he sat in the recliner. "Well get over here and do what you love." I kneeled between his legs and took his semi hard dick in my mouth. As I sucked his dick to life, I started to stroke my own hard dick. Once Drew noticed my jerking, he said, "What in the hell are you doing?" I stopped sucking his dick and responded, "What you told me to."
"I never told you that you could jerk off. While you are in my room do don't get to jerk off. You are here for my pleasure and you will not gratify yourself in front of me. You can cum up in the attic or in the shower. But not here."
"Why did you have me strip then?" I asked.
"To torment you," he said with a huge grin. "Now take your hands off of your dick and get sucking mine."
I did as he said. In an attempt not to stroke my dick, I massaged his balls with one hand and used the other hand to rub his chest. As I sucked his dick, I followed the same routine as last night, however I took the full length of his cock down my throat from the get go. I started to sense his dick tensing. I was thinking that I was about to be done and able to go to the bathroom to jack my own dick. But Drew, once again had other ideas.
Before he went over the edge, he had me stop sucking his dick. He said, "Lick my balls." So I started to lick his balls as if they were a lollie-pop. Soon I just naturally took one testicle in my mouth and gently sucked on it. I then switch to the other and soon had both of them in my mouth with my tongue massaging them.
As Drew spread his legs further apart, I started to lick the area behind his ball sac. From his moaning, I knew that he was enjoying himself. He had soon placed his hands on my head and was rubbing my head. He then began to push my head lower. The more I resisted the more force he used. Before I knew it, I was licking his ass. Next he said, "Tongue my hole."
I guess I was naive, because I didn't know what he was talking about. I reluctantly licked his hole. I feared the taste, but quickly realized that it did not taste as bad as I imagined. I continued to lick his rosebud. Drew attempted to push force my head further in to his groin.
"Push your tongue in my hole. Eat out my ass you faggot." At Drew's direction, I attempted to push my tongue in to his ass. As my tongue started to open his ass, he moaned, "Yah, that's it. Go deeper." I tried to comply with his request, forcing my tongue in as deep as I could. Soon I had a loose hair on my tongue so I raised a finger to help get it off. In my attempt, I accidentally, ok maybe on purpose, pushed my finger into his hole up to the first knuckle. I at first feared he was going to be pissed, but he just moaned louder.
I continued to lick around my finger and slowly pushed it in to the second knuckle. I paused, waiting for him to react. I continued to push my finger in his ass as far as I could. His moaning only increased. I was licking around my finger and then started to slowly fuck him with my finger. At this point, he grabbed my ears and raised my mouth back to his cock. I continued to finger fuck him as I sucked on his dick. Within a minute he was shooting a huge load down my throat. His ass muscles clamped down hard on my finger.
I slowly pulled my finger from his ass as his dick went soft in my mouth. I was so damn horny and my dick was so hard that it hurt. I resisted stroking my self, but I kept touching my dick and balls.
"Its time for you to go help set up dinner. I want your ass back here at 8:30." Drew instructed. I threw my clothes on and headed out the door. I could hear all of my pledge brothers already downstairs so headed down, hoping I wasn't too late. More importantly, I was hoping no one would notice the boner was sporting in my pants.
Each day at 6:30, we have mandatory study time for two hours in the down stairs study room. By the time dinner was cleaned up, it was exactly 6:30. I was aching so bad for some relief. My dick seems to have been hard for nearly 24 hours. But I did not get the break I badly needed.
At 8:30 I ran up to Drew's room. When I got there, he again had me strip. He then had me kneels and then he blind folded me and had me put my hands behind my back, so I could not touch myself. As he did this he was lecturing me about following orders to the fullest. I did not hear him or notice his moving behind me where suddenly I felt cold steel on my wrist. He had handcuffed my arms. "This will make to stop touching your dick." He said half laughing. He then ordered me to open my mouth wide, saying wider.
Drew pushed his hard dick in my mouth saying, "Suck it good faggot." A few minutes later, he pulled his dick from my mouth and pulled me by my ear to get me to follow him. When we stopped, he had me sit on the floor. He then had me turn some and told be to lean back. I quickly realized that I was leaning against his bed. He pushed my head back till I was facing the ceiling. He instructed me to open my mouth and wait.
As I waited for him, I could hear him fumbling around. I figured he was undressing. Next he basically sat on my face, say "eat out that ass you nasty faggot."
As I tried to drive my tongue as deep as I could in his ass, my neck quickly became sore, with much of his weight pressing on it. I was so glad when his cell phone rang and he jumped up to get it. It gave me the break I needed.
He answered the cell phone and I tried to stretch my neck muscles. As I was rolling my head and he was talking on his cell phone, Drew grabbed my head and forced his dick in my mouth. As I sucked his dick, I heard him his side of the conversation: "Nothing, baby." "Thinking about you." "What do you mean you're not coming over tonight? Are you going to leave me without a little somtin, somtin?" "No baby, I understand, I will see you tomorrow." I heard the phone be flipped closed and he said, "Besides, who need her when I have an expert cocksucker right here." And with that he fucked my face with vengeance. Once I sense his dick about to shoot, he pulled out and told me to lick his balls.
Next, he had me lay on the floor and he did pushups with is dick entering deep in my throat with every downward thrust. Next he sat again on face. Though it was better than on the bed, it was still painful since my hands were cuffed behind my back. The other thing was that I could not see what he was doing since I was blind folded.
Eventually he stood me up and pushed me forward. I ran in to his desk. He instructed to stay bent over the desk. I felt something cold rubbing on my ass. Before I could figure it out, he smacked my ass with a wooden paddle. He proceeded to hit me another 25 time. My ass was on fire. When he stopped beating my ass, he began to softly rub my ass as if he was saying he was sorry.
I was dizzy from the mixed sensations I was getting. As my head was swimming, I did not notice Drew's presence. I was lost in my own thought.
I was quickly reeled back to reality as Drew forced his full 7" in my ass. The pain was too much and I started to scream. Drew covered my mouth and said, "You will greatly regret bringing any attention to what is going on in here." He then pulled out of me as tears were rolling down my face.
He had gotten something, moved in front of me and told me, "Open your mouth." I did as I was told and he shoved his jock strap in my mouth. It was obvious from the taste that it had not been washed in long time.
"I'm not ready to share you yet. That should help keep you quiet."
Drew then repositioned himself behind me and again shoved his dick up my ass. In one thrust, he buried his seven inches in me.
This time my screams were muzzled by his dirty jock in my mouth. The pain was intense. He made several hard thrust and then he paused for a minute with his dick deep inside of me. He then slowly began to fuck my sore ass. As he went on, the pain began to subside. Before long, it was actually feeling good. As Drew continued to thrust into my ass, my own hard dick was being jammed into the edge of the desk.
After about 20 minutes or so, Drew withdrew from me and lay on the bed. He then told me to find my way to the bed and climb on top of him. He laughed as I ran into things. I was still blindfolded and my hands were cuffed. Once I got to the bed, he helped me to straddle him. He pushed me back slightly and I could feel his hands under my groin. He apparently was lining his dick up with my ass.
He pushed up into and then instructed me to sit back. As I did, he lowered his ass back to the bed and said, "You have to do the work now."
I understood what he wanted. I started to slowly rise up till his dick was barely in and then I sat back down. I did this for awhile. I soon began to notice as I grind down on him harder, I was getting more pleasure. I guessed that his dick had begun hitting my prostate. Soon I was bobbing up and down on him like there was no tomorrow.
Without my dick being touched, or without warning, I erupted all over Drew.
"Son of a bitch," he yelled. "Get off me." I climbed off of him. He reached up and roughly pulled off my blindfold. I saw that I had shot my load from his bellybutton to his cheek.
"Well, what are you waiting for?" he asked. I of course could not answer with a jock in my mouth. "Spit that jock out and lick up your mess."
I did as he instructed. I had never tasted my own cum before. I started at his bellybutton and worked my way up. By the time I was licking his neck and chin, I was already hard again, a fact that did not escape Drew.
"You really like this shit don't you?" I just continued to lick off my cum and didn't answer him. When I had finished, he stood up and took off the hand cuffs. I was so glad he did because my fingers were beginning to tingle. "Get on your hands and knees like a dog," he ordered.
He reentered me and fucked me hard with long fast strokes. He kept an incredible pace. In about 10 minutes he was dumping his load deep inside of me. I could actually feel his spurts going deep inside of me. He collapsed on top of me, causing me to fall flat on the floor. He did not move for about 10 minutes. I could feel his stiff dick softening inside of me. Once he popped out of me he got up wrapped a towel around his waist and said, "You only have two minutes to get to the attic."
I grabbed my shorts and slid them on. That was when I realized how sore my ass was from the beating it took. I ran out the door, leaving my shoes, shirt and boxers there.
I got upstairs and all of the pledges were there and ready for bed. I slipped my shorts off and the room went almost dead silent as they saw my ass. Some whispered to each other. Seeing this, I said, "I didn't do some of my chores and Drew took the paddle to my ass." I didn't bother to address the issue of why I was only wearing shorts.
I climbed into bed. I have to admit I was a bit pissed off at Drew. First of all he didn't have to beat me. Second of all, I was pissed at the way he fucked me. Although I began to enjoy it, he shouldn't have done it. It is one thing to blow a guy, but it is something else to have him fuck your ass. I was both pissed off and turned on at the same time. This of course made sleeping even more difficult than sharing a bed with four others.
When I woke in the morning, I found that I was sleeping half on the guy next to me with my hard dick wedged in his ass cheeks. My arm was over his shoulder and my leg was between his legs. The guy on the other side of me was sleeping half on me. His hard dick was pushing on my ass opening. His arm was over my shoulder and his head was nuzzled in the back of my neck. His leg was also between my legs. As a result, my legs were spread far apart leaving room for the two bed mate's legs to be between them.
I started to move some in hope to see the clock. It was only 4:30. My moving however stirred the guy on my back. Not enough to wake him, but enough for him to start rubbing his dick between my ass crack. As he gently rubbed his 6 inch dick on my ass, I returned to thoughts about Drew. I guess I drifted back to sleep. I woke as the dick in my ass crack entered my hole. This caused me to push forward, parting the way of the rosebud my dickhead was kissing. This of course woke him.
The guy behind me must have been dreaming, because he continued to try to go deeper in me. Much to my surprise, the ass I entered pushed back allowing me in. He continued to slowly rock on my hard dick, taking more and more of my very hard 8" and he began to very softly moan. His movements caused me to move up and down on the dick that was entering my sore asshole.
Both guys moved very slowly and quietly. I was sure that the one behind me was no longer sleeping. They seemed to move deliberately as not to wake the other two guys in the bed. Because of the direction I was laying, I could not see the fourth guy, the guy behind the guy fucking my ass. All movement stopped as the guy at the foot of the bed began to move. At first we didn't know if he woke or if he was just turning over. As we heard his snoring start back up, we knew it was safe.
We could only go at a very slow pace and we could not move too much, so I push down on the shoulder of the guy I was fucking so that more of my dick would be in his ass instead of the few inches currently there. He took the offer and scooted down so that my full 8" were buried in his ass. He then resumed his slow and deliberate rocking of his ass. I reached over him and took his stiff dick in my hand and slow massaged it.
Meanwhile the guy behind me scooted up in the bed so that his full six inches were buried in my ass. He also began to lick and nibble at my ear and neck. His one free hand was slowly rubbing my side. Suddenly, I felt another hand on my side and it wasn't from the guy I was fucking.
I raised my head and turn back trying to figure out who's it was. That is when the hand raised up and gave me a slight wave. In the dim lit room, I could see it belonged to the fourth guy, who was apparently fucking the guy fucking me.
Here we were, four guys engaged in sex in a double size bed with a fifth person sleeping at our feet in a room filled with 20 other guys. This was risky behavior, making it that much hotter.
After about 30 minutes of this slow fuck and me stroking the first guy, he erupted in my hand, which triggered me to erupt in his ass. This then led to the dick in my ass shooting his load deep in me.
I did not remove my dick from his ass, nor did the dick in my ass exit. We fell asleep like that. I woke a minute or two before the alarm went off with my morning woody buried deep in his ass. The dick behind me had slipped out sometime in the hours we slept. I gently started to fuck his ass until he woke and the alarm went off. I quickly pulled out before anyone noticed my dick in his ass.
Later that day in my Chem Lab, Rob, the guy who fucked me, came up to me and asked if I had any free time. I told him that my next period was free and he asked if we could talk then. I agreed and we decided to meet back at his apartment, only a block off of campus.
When I arrived at the address he gave me, Rob answered the door wearing only a towel.
"Heading for a shower?" I asked.
"Hey, yah, eventually," he said rather sheepishly. "I guess I wanted to ask you about, well, we didn't know you were gay. We all assumed that you were just shy but not gay."
"Well, I'm not gay, or at least I don't know if I am. This week was the first time I have ever done anything with a guy before," I replied. "Who is all of us?"
Almost no cue, the other two guys from last nights fucking session came out of the bedroom. They did not bother to put any clothing on.
Rob then explained that he current roommate was not going to return next year. So he was looking for roommates. Although only two lived there now, he thought it would be much more affordable to have three roommates. The apartment was very large, a huge living room and kitchen. The problem was that there was only one very large bedroom.
I told him I would think about it. Rob then began to rub my chest and unbutton my shirt. He was quickly joined by the others.
After an afternoon of the four of us fucking each other I said yes to the offer.