Thanks for all the great response! And for sharing your similar growing up stories with me.
This is a brief one, but entirely true. I have relived it more than a few times. : )
Pt. 4 "I did a stupid thing"
After my three first encounters pretty close together, I was actually feeling a lot of guilt. I turned 17 around this time, and felt like maybe I was getting off track with my sexual adventures, and I had better cool it. I had some real worries that maybe I wasn't quite normal. Plus, I was afraid someone would find out.
I went a couple of months without any sexual contact, but I have to admit it was a struggle when I was with some of my buddies swimming, and doing things like that.
Anyway, I had picked up som magazines with stories and pictures, and when my folks weren't around I would get it out and jerk off to it and fantasize about the stories. I had also picked up a film, and when no one was home I watched it. It was a young farm guy getting fucked doggy style by two buddies who took turns. It really turned me on, and it looked pretty easy. I started thinking about anal activities- it was scary, but pretty hot.
Finally, I ventured back to the bookstore. I was there a little while when a guy came in who looked like a jock-tanned, swimmer kind of body, with blonde curly hair. Compared to the guys I had seen so far, this one was genuinely hot. He took notice of me, and flashed a smile, then walked on back to the magazines. He wasn't in the gay section. He was looking at totally straight stuff, and so at first I figured he was off limits.
I pretended to look at the movie titles, but several times I looked up again to see him looking in my direction. We made eye contact, and he smiled again. I was getting dizzy.
He nodded his head toward the back door and headed that way, so I followed. When we got outside, he flashed me a smile (beautiful white teeth- must have had braces when he was a kid) and said, "How you doing?' "Pretty good," I responded nervously. "What are you doing tonight?" he asked. "Not much- just out messing around, I guess," hoping I answered it right. "Do you have a place? My girlfriend's gone this week, but I have a couple of roomates that share my apartment." "Uh, no, I live at home with my family," I answered, feeling dissappointed. "Hmmm. Well, I think the guys are gone for most of the evening, so let's go by my place and we'll see if anyone's there. It should be ok," he assured me. "Just follow me." He pointed to a nice, fairly new black car on the street parking. "Um. I'm around back in a lot, if you can pull around there, I'll follow you," I answered. "I live close to here," he said.
About the time I reached my car, he had pulled up behind me, and so I followed him to the northside of the town to an off campus apartment complex.
"We're down in the basement. I'll go first to see if anyone is there," he said with a nod, as I followed behind.
I noticed bicyles in the entrance as we headed down the interior stairs. I admired his curly, blond hair as we went down the stairs. Much nicer than my strawlike hair.
He opened the door and announced, "We're fine, nobody home. I think they're probably gone for the night. Can I get you something to drink? A beer, or coke or something?"
"Yeah, a coke sounds ok. Thanks!" I said as I looked around what was a typical jocks apartment.
There was a bed that looked like it doubled for a couch, not too far from the kitchenette. I sat down on the edge, waiting on my new friend to fix the drinks.
"Hey, dude, just wanted to let you know that I have a girlfriend, she's just out of town right now." He paused, then went on, "Sometimes when she's gone I like to try some different stuff. Every now and then, I like to find a guy to hook up with. Is that ok?"
"Uh, yeah, sounds like a good plan." I stuttered.
"I'm not gay or anything. I just like a little variety." He walked around and handed me my coke, and stood a few feet away looking me over as he paused. "You know what I mean? How about you?"
"Yeah," I replied nervously, not use to a lot of talk about sex. "That's the way I am, except I haven't really seen a lot of action. I have only been with a couple of other guys. I'm pretty new to this. Mainly just girls for me, too."
"Do you like to be fucked? Cause that's mainly what I like to do with a boy. I like to find one that wants it up the ass," he smiled.
Oh boy- now I was really in for it. I had been fantasizing about this whole anal thing, but I wasn't really expecting it tonight. And it scared me to think of having a part of a guys anatomy inside of my body. But if I was ever going to experiment with it, this guy was really, really hot. Plus, I felt like I had obligated myself by coming over to his apartment. It would not be cool to back down.
"I guess I'll have to tell the truth. I haven't really done anything like that, cause this is all pretty new to me....but I have thought about it a lot.
I just don't really know how to do it," I honestly replied.
"Don't worry about that. I can help you through it. But I'll warn you, some guys think the first time is great, and sometimes it's pretty tough for a guy whose a virgin. You have to really trust the guy on the other end. Do you think you can do that, because I don't want you to do something that you don't want to? But I'd sure like to be the first to break you in." He reached down and started rubbing my shoulder.
"Yeah, that's cool. I mean, no, I want to do it, and I think your really hot. You'll just have to help me," I said, feeling almost queezy with fear and anticipation. I really felt like a girl who was about to have her cherry popped by the Prom King. I was actually going to have this guy hook into my body with his cock. Wow!
He tugged on my shirt, until he pulled it off and told me to stand up. With my chin cupped in his hand, he looked at me, then put his lips on mine. I had only kissed a guy one other time, but this was awesome. He opened his lips and I felt a warm, wet tongue licking my lips. I parted them slightly, and his tongue went in.
"Mmmm, you taste good. Mmmm." He kissed my neck and shoulder then hugged me. "Be honest with me, you look like your still just in high school. How old are you?"
"17," I answered truthfully, hoping it wouldn't matter.
"That's even better." He reached in and began another warm, wet kiss, then licked my neck. "Get the rest of your clothes off and lay down on the bed," he ordered.
I obeyed, watching him the whole time, as he pulled off his shirt and shoes, then unbuckled his blue jeans. I was getting hotter by the minute. He was tanned, with light blond hair around his body. He had long slender feet and toes and a beautiful ass.
When he finally reached his undershorts, I could tell he had a boner underneath. He walked in the kitchen and shouted back, "I don't have any lube, so I'll have to find something." He walked back in with a can of Crisco. "Guess this'll have to do!"
He pulled his short off and I about fainted. His cock looked like a long pepperoni stick. I mean, it looked huge to me, compared to my 5 incher. He took a generous handful of Crisco and started lubricating it.
Man, I was trying fast to think of a way out of this. There was NO way that thing would fit inside my body! No possible way. I couldn't even imagine a girl taking that inside of her.
"Turn over on your stomach and let me see your ass," he ordered, almost roughly. I complied, and he put two pillows underneath me, so my butt was in the air.
He spread my cheeks aside, and started probing with his finger covered in Crisco.
"Man your tight. I can barely get past your hole. You were telling the truth- you are a virgin. But we'll fix that in a minute. Don't worry, we're gonna fix that tonight!"
I felt like I was shaking with fear, but there was still a fascination with what was about to happen.
"Push on my finger- like you gotta go to the bathroom," he instructed. I tried, but it seemed like the harder I tried, the tighter it got. He slapped me lightly, then order a little harsher, "C'mon, you gotta push. It'll go in a lot easier that way."
He pushed his finger until I could sense the tip of it break through. He wiggled it around. "That's better. Just keep pushing until I get it all the way in."
It hurt. It hurt a lot. And as it slid in, I suddenly felt like I needed to go to the bathroom. "I think maybe I should go to the bathroom," I almost whimpered.
"Nah, that's how it feels. It's just my finger, you'll get used to that feeling." He kept pushing, until I felt his knuckle on my ass cheeks. "Yeah, that's about as far as I can go."
I felt a really weird feeling. I knew he had hit something inside there that was sending shockwaves through my body.
"Relax for a few minutes, while it opens up." He massaged my back and buttocks. "This is gonna be so good. I've never felt a guy this tight. I've never had a girl this tight, even when it was her first time."
I shuddered. After a few minutes, he started to withdraw his finger, and a feeling of relief swept over me. It was like I was taking a dump, and finally had emptied myself. He rubbed my ass cheeks a little longer and asked, "Ready?"
"I guess so..." I responded weakly.
"Just remember and push. It will make it easier," he said as I felt him move up to his knees and get in position. Oh boy, I felt like the roller coaster that is creeping toward the top of the hill getting ready to roll. Or like the girl in the front seat with her guy, after the football game.
His cock was now pressing the outside of my hole. "C'mon, you gotta push out...he pushed so hard against me, that it mashed into the pillows, "C'mon, push back at me- HARDER," he commanded.
I was so scared, that I literally thought I was going to die. But I also felt like I had to obey his orders, so I pushed back, and felt something give. There was a feeling like the tearing of fabric and I knew that he had entered my body.
"Oh yeah. I'm in now. Are you ready to get laid? Huh? Keep pushing," he moaned.
I kept the pressure as he pressed inch by inch. By now I was clutching a pillow to my face, with part of it in my mouth. I was trembling, and feeling like my body was being split in half. I felt like surely my insides were being torn up. And yet I couldn't tell him to stop. In a weird way, it was so erotic, and I wanted to endure this.
He pushed deeper and deeper, until I thought it would press through my intestines and stomach. After what seemed like an eternity, he reached his limit and his hips were pressed into my butt cheeks he stopped and laid down on my back.
Wow. I wandered what happened now. He lay panting on me with his pole completely thrust inside of me. "You ok?" He gasped.
"Yeah, I think so. It really hurts," I said with tears in my eyes.
"It'll get better. Hang in there dude," he said, as I felt him begin to pull out.
If going in was harder, pulling out was harder. It was not coming out, and I thought, 'he's going to get stuck inside me.' I had this crazy thought- I don't want him to pull it out, it hurts too much. But he can't leave it where its at!
As he continued pulling, it lifted me off of the pillow, before my clutching rectum began to let go. I wandered if m insides were being pulled out with it. It sure felt like it.
After a long time, it finally broke free and came out- and as I felt relief that this was over, he rammed the entire sausage all the way in as hard as he could go. I yelped through the pillow in my mouth and felt pushed into the bed. Then, with no warning he jerked back out. By now he was grunting and groaning as I clutched the sides of the bed.
Back in- then jerked out, then in....I felt swimmy headed. There was more feelings of tearing as he shoved as hard and deep as he could go.
"You like it? Huh? I knew you would?" He whispered hoarsely in my ear, without waiting for a response, then started the battering ram again.
I thought, he'll cum in a minute- but it went on and on and on. I felt like a pony giving a ride as he adjusted up to get a different entrance, then collapsed on my back in quick jabs.
"You're still tight. Really tight. Tighter than any girl I've ever fucked," he gasped.
Finally, without cumming, he start to wear himself down, and slowed to longer slower strokes. I was laying, almost not moving at all. Eventually he seemed to notice me.
"Hey, dude, are you ok? Do you like it?" He asked, finally aware of me.
I thought fast. If I encouraged him too much, he would start again. But I didn't want to sound stupid so I blurted out (sounding stupid anyway), "I'd like to suck you. Can I suck you?"
He paused, then said, "Yeah, sure, if that's what you want." He pulled out slowly, then leaned back against the wall the bed sat against,and spread his legs. "Help yourself."
I very carefully moved around, feeling like I had a huge hole on my backside. I took a hold of his feet, then buried my head on his long cock. I could smell a musky smell that I knew came from me, and there was a small trace of Crisco left on his pubic hair and balls. I was determined to finish him off, so I lay on my belly between his legs and begin to lick and suck.
While I did, he tousled my hair, then reached back and rrubbed my back and butt cheeks. I felt his legs wrap around me.
"Good job, boy. Good. You love cock, don't you." He started thrusting in my face, then pushed me off as he started shooting on his stomach, hand and bed. It was only inches from my face, and I could smell it (but I was scared to eat it).
We both lay there for a few minutes, then he said, "My roomies are going to be back." I knew he thought I better go before he got caught.
"Yeah, I gotta go," I said as I got dressed.
"Hey, I work at the JC Penneys store in the Mall. Men's department. Stop by and see me." He was still sitting on the bed in the nude, with cum drying as he watched me dress.
"Yeah, I'd like that. I'll do it." But after I slipped out alone in the dark night, I didn't know if I could get the courage to see him at the mall. It was weird.