Hello, I had such a great response to my last story, I figured I would give it another shot. This is also very true, and probably one of my best experiences ever. I hope you enjoy it, but only if you are legally allowed to read sexually explicit material. Otherwise, please leave now. Thank you.
Sister's Underwear
I'll never forget him, he was about 5'8 and around 135lbs, and was the most adorable thing I'd ever seen. His name was also Jeremy, Jeremy Tinkey to be exact, and he was about the hottest kid I had have ever seen in my life. He moved to my school midway through my sophomore year and I immediately knew that I had to get to know him. I found out that he was a year younger than me, so at the time he was only 15 years old. I was 16 and had just recently got my license.
I almost wet myself when I found out that he was in my gym class. I kept trying to figure out a way to talk to him. I was finally able to talk to him when we became friends with one of my close friends. Once I got to know more about him I found him even more attractive than before. He was so forward about everything, nothing seemed to embarrass him or make him nervous. Everything about him was beautiful. The way he talked, the way he smelled, the look of his slightly curly black hair, the boyish young look of his face, and his body, especially that ass of his. It was sooooo perfect.
Eventually we talked a lot and before the school year was over he wrote his number on my hand and said that I had better call him over the summer. As you can imagine, I never wanted to wash that hand again. It took me almost a week to muster up the nerve to call. You know, even though we had talked in school and stuff, the first time you call someone has a totally different nervousness about it.
When I finally called him we decided that we should do something together. You see, he had become a huge ladies man at our school, but I knew that there was something about him. He went through a lot of girls in a short period of time.
We finally decided that he would spend the night at my house after a school dance one night, and then we would go out the next night. (I loved being able to drive!) That night my parents were not at home and my sister was away at volleyball camp. So we just rented a movie and called our girlfriends when we got home, they were also having a sleepover with a couple of their friends. (Yes I had a girlfriend, she was really nice, but it was mostly a social pressure thing, nothing sexual.)
I was done talking and he was talking to his girl. I heard him laughing really hard, so I asked him what was so funny. "They're measuring their boobs!" He chuckled.
"What?" I said.
"They're measuring their boobs man, to see whose are bigger." He laughed even harder. I loved his laugh.
"Oh my God, I think we should hang up and let them have their fun dude." I said.
The next thing he said was the last thing I expected, but turned out to be the best thing that could happen. "No man, the want us to measure our peckers to see whose is bigger."
"What !?" I said with half a smile on my face. I was very shocked.
"Yeah, man let's do it. Do you have a ruler, or a tape measure or something?" He said. (I told you he was very forward, but I loved it.)
I couldn't believe it he was actually gonna measure his pecker right in front of me. When I came back with a ruler it got even better.
"To prove that we're not lying, I told them that we would measure each others." He pulled his shorts down to reveal what, to this day, is probably the most beautiful pecker I have ever seen. It was 4 inches soft, cut, and definitely the smoothest cock I have ever seen or felt. It was just like silk against my fingers.
"Are you serious?" I said. Still not believing that this was happening.
"Yeah man, just go ahead, it's no big deal."
How was I going to do this without popping a huge boner? I had about half of one just thinking about it, and knowing him, he would insist on measuring mine too. So how would I explain it?
"O.K. if you insist." I said. I figured what the hell. After all, when would I get this chance again?
He told the girls to hold on and I sat down on my bed next to him and leaned over and lifted his dick up by the head, of course I had an instant boner. I put the ruler right next to his dick and rested it in the little tuft of black pubic hair just over the top of his dick. It was just over 4 inches long, but I pretended that I couldn't read the ruler right so I had to bend down and get a closer look. I tugged on the end of his cock just a little, like I was trying to get a better measurement. I felt his dick start to get slightly hard and he immediately told me to hurry up. Before he could do anything though he had a boner. From what I saw it was awesome, but he quickly nudged me aside and pulled up his shorts.
"What are you doing?" I said.
"Shut up!" He said. I could tell he was embarrassed, his cute little face was so red. I couldn't believe it; I had actually embarrassed him.
"Don't be embarrassed man, hell I have a boner already and you haven't even touched it." I said, trying to comfort him. "I'll tell you what, let's just measure each others boners to see whose is bigger." I couldn't believe how forward I was being. I guess it's easier when the other person is embarrassed like that.
He looked at me kind of strangely at first. I knew he was either going to punch me (even though I was bigger than he was) or agree.
"Fine, but you're going first this time." He said, kind of angrily, but I could see a smile form at the corners of his lips.
I knew he was back to normal, because he took the front of my shorts and just yanked them down. My boxers went right down with them. So there I stood bare-ass naked with a 6 inch boner. I sat down on the bed and Jeremy sat down next to me. He did the same as I did and grabbed my boner by the head. I thought I was going to cum right then, but I closed my eyes and did the best I could to restrain myself. I felt the ruler next to my cock and I felt his hot breath when he leaned closer to read the measurement, it seemed to take him a while.
"O.K. your turn now." He said excitedly. It was finally done, I didn't think I could restrain myself any more from telling him how much I wanted him.
"All right, let's do it." I was calmer this time. He just stood there for a moment before I realized that he wanted me to take his shorts down like he did mine. "Oh, sorry." I said as I grabbed for his shorts. I gave them a yank and Jeremy stood there I his dark blue, bikini briefs. I could see the outline of his large boner clearly through them. I then slid down the bikinis to reveal the boner that I had caught just a glimpse of before. Man was it ever awesome. If he only knew how badly I wanted to take it in my mouth right there, he probably would've never spoken to me again.
He sat down on the bed next to me and I again leaned over to take the measurement, how I ever resisted taking that beautiful thing in my mouth I'll never know. I finally got the measurement and it was 7.5 inches!! This young kid was bigger than I was!! I was a little embarrassed and excited all at the same time. Of course, I took my time again and right before I was done I felt his hand on the back of my head, but he quickly pulled it away. That had me very curious.
"You little asshole, you're bigger than me." I said.
"No way! Really?" He said, trying to act surprised.
He then pulled up his pants and got back on the phone. I could hear him bragging to the girls as I left the room. I really didn't care what they thought, I just had to get out of there before I lost control and did or said something I would regret.
We went to bed shortly after he got off of the phone. I was going to sleep in my sister's vacant bed, because it was a huge king size water bed, that was extremely comfortable, and you could fit like 8 people into it, but he wanted us to both sleep in my room. So we both got in my bed that night and began to talk. We talked about our girlfriends, and baseball, and even jacking off. He told me about a time when he shot his load all the way onto his face! He was proud of that. I wanted, so badly to tell him how many times I had fantasized about him while I jacked off, but I just couldn't. I knew it would ruin what I did have with him
When we woke up the next day I found that my parents left us money to get food, because they were both off to work. Once again we were alone, so what would we do? We ended up playing living room football. Whoever had the ball would start from the dining room and had four downs to get into the "end-zone" which was actually my couch. I didn't much care about who won, but more about how I tackled him, and how we ended up. All he was wearing was a pair of cut-off sweats, and he was beautiful. We were both shirtless, so that left many opportunities to rub my body on his, without looking conspicuous. On occasion I would "accidentally" grab his crotch, or when he would run into me I would fall backwards and take him with me so his crotch would be right in my face. On a couple of occasions he would just lay there for a minute and I loved it.
We were both rather hot and sweaty so after an hour or so we stopped. He wanted to see the rest of my house so I took him on the grand tour. The last room we came to was my sister's. As soon as he saw the bed he had to try it out.
"This is the biggest bed I've ever seen in my life! Why didn't we sleep here last night?" He said.
"I wanted to, but you wanted us to sleep in my room so we could talk about you splooging all over yourself!" I said, laughing. I ran over and jumped on the bed too.
"Screw you man, you're just jealous because I wasn't splooging on you!" He replied.
Boy if he only knew how true that was. I still had the Nerf football we were playing with, so I threw it at him. We wrestled around for a while, and eventually he jumped off of the bed and started looking around the room. I had a little trouble getting up since I had a big boner from wrestling with him.
He was looking through my sister's closet and we laughed at some of the things she had. Old "Teen Beat" magazines, (J/O material for me!) and her old Chippendale calendars. He went to her dresser and was looking through. He pulled out a pair of her laced, lingerie, type of underwear and held them up in front of himself.
"How do they look, are they me?" He said and laughed.
"I don't know I can't really tell, try them on." I said jokingly.
"O.K., but don't look." He responded teasingly, knowing that I was going to.
I couldn't believe it he actually pulled down his shorts like he was actually going to do it.
"Are you really gonna do it?" I laughed.
"Yeah." He said with a little squeak in his voice and a laugh.
All I could do was giggle as he turned his back to me and pulled down his underwear. When I saw that ass I thought that I was going to explode. It was so beautiful and smooth that my dick almost jumped out of pants right there. I swallowed deeply and just enjoyed the show.
"No peeking now." He reminded me, still knowing that I was watching.
He finally got them on and turned around. At first he stood sideways, giving me the side profile and it was amazing. I could tell that he had half a boner, by the tent that had formed in the lacy underwear. All I could think was that it was a good thing I brought that Nerf football with me so I had something to cover up my boner. He didn't care he was just enjoying wearing my sister's underwear. The next thing, however, would shock me and excite me all at the same time.
Jeremy turned around and dove onto the bed, right on top of me! He acted like he was humping me and making moaning sounds like sex, but laughing at the same time. After the initial shock I figured I should play along. I went to grab him by the ass, but my hands slipped under the panties and I grabbed his bare ass, but he just kept going. So I went through the motions of dry humping too. HE did this for like 5 minutes! I was so happy, but all I could think was that he had to feel my boner. So how could I tell if he had one? I decided to try and slip my hand down there to try and make "incidental" contact.
I finally worked my hand into position and realized that he did have a boner! I kept my hand there to see if he would say anything, but he didn't! That's when I decided that it was time to just go for it. In one swift motion I slid my right hand down the lace panties and grabbed his boner. He went on humping for another few seconds, but would eventually stop. I thought it was all over. He rolled over to my side and just laid there for a minute.
"Have you ever given a blow job?" He asked in a way, in which I couldn't tell whether or not he was joking. He was so good at that.
"No, I don't know how." I responded to try and see where this was going, still holding a foam football over my groin.
"Can I show you?" He asked, looking me directly in the eyes. The smile on his face still looked like it may be a joke.
"Sure, go ahead." I figured, what the hell, why not. I still couldn't believe I was lying next to him while he was wearing my sister's underwear and had a big, beautiful boner.
He leaned over and I just thought, "Oh my God he's gonna do it!" The next thing I knew he grabbed the football, held it straight up in the air and started licking the tip of the ball.
"The first thing you have to do is lick the tip of it like this." He said as he circled the very tip of the ball with his tongue and the bottom of it rested on the boner concealed only by my shorts.
He then proceeded to describe the steps to giving a blowjob one by one, while demonstrating them on the football that was resting on my boner. The way he was describing it was so awesome that I just melted. It was like he was trying to be seductive and that he knew how it was affecting me, so he was trying to tease me, or something.
When he was finished he tossed the football off of the bed, revealing the clear fact that I had enjoyed every minute of it. I saw that he had a huge boner as well, because the panties couldn't contain it. The head of his pecker was sticking out the top of the panties.
He rolled over beside me and we both laid silent for a minute. I propped up on one arm and looked at him, he was so beautiful. He looked at me with about a half smile, almost like he wasn't sure whether he should actually be enjoying this or not.
"Is it my turn to give it a try?" I asked very softly, trying to keep the mood.
"Sure, why not." He responded.
"Should I get the football, or do you think I'm ready for the real thing?" I asked.
"I think you can handle the real thing, after all you've had a good teacher." He said and left out that little giggle that I loved so much.
It felt like a huge weight had been lifted off of my shoulders. I didn't need to hold back, or restrain myself any longer; it was time to let it all out. I leaned over and gave him such a big kiss on the lips, it was like heaven.
"You don't know how long I've been waiting for that I said." I said.
"Me too." He responded and flashed that cute little smile at me.
I worked my way down, kissing his neck and chest, licking his sweet little nipples, and kissing that sweet stomach of his, I felt like I was floating. I pulled down the lace panties and did as he had shown me before. I softly kissed the head first, which, as I said before, was so smooth. I then worked my tongue in a circular motion around the very tip as he had done to the football. I thought that he was going to jump straight through the ceiling, I guess he really liked that. I ran my tongue down his dick and licked his balls, which were just perfect.
Then came the moment of truth, I took his pecker into my mouth and tried, as he told me, to get it as far in as I could. I knew that there was no way I would get 7.5 inches all the way in, but I tried really hard, and he really seemed to be loving it, as he let out many moans of satisfaction. I worked slowly up and down and grabbing tightly onto his ass at the same time. I then began to speed up, as well as began to stroke the base of he dick at the same time.
As I began to feel his dick swelling, I heard him moan, "jack it off, please jack it off."
I pulled his wonderful cock out of my mouth and began jacking it rapidly. I could feel him begin to clench, and he grabbed my free hand and squeezed. Finally he exploded, with cum flying everywhere. The first shot landed up between his eyes, from there on he hit his throat, his chest, and finally it just began rolling over my fingers that I didn't want to remove from his cock.
I began rubbing his cum all over him. I rubbed it on his stomach and chest, and licked it from his throat and face. He had a huge smile on his face and I gave him a big kiss. We laid there for a minute and caught our breath.
"Are you going to do mine for real now, or are you just going to tease me?" I asked, still sporting a huge boner.
"Sure, I'll give you another lesson." He said, with that cute smile that could charm the devil himself.
He rolled over and pulled down my shorts, revealing the boner that he had just measured the night before. He looked up at me as he licked the head of my hard cock. I was surprised that I hadn't jizzed already, but I was in such total ecstasy, I guess there's no other way to describe it. I'll never forget the look on his face as he looked up at me and took my cock into his mouth. I felt like I had lost my breath, almost as if I were going to faint, but I didn't.
It only took a few minutes before I felt my cock begin to swell. I warned Jeremy ahead of time that I was going to cum, so he pulled it out and begin jacking me off. Just when I thought that I couldn't take anymore I exploded all over the place. The first shot went all the way to my neck and the rest was all over my chest and stomach. Jeremy licked it off of my neck and rubbed the rest all over his balls and his cock.
We laid there and relaxed for what seemed like forever, but I never wanted it to end. Eventually we decided to get a shower. We got in together, so it wasn't that bad. We scrubbed each other down after we had gotten all sweated up and cummed on during this wonderful day.
We got out of the shower and dried each other off. I still couldn't believe that any of this was happening. I was waiting to wake up to an empty bed full of cum, but it never happened. As we were drying Jeremy said something that just put a great cap on this day.
"What would happen if I shave my pubes?"
"Nothing, it's hair, it will grow back." I said.
"Really?" He said, like he thought he would remain bald down there forever.
"Yeah, I'll do it for you if you want me too." I said.
"I guess so." He said, still a little unsure.
"C'mon, sit down and trust me."
He sat down on the toilet as I got out the shaving cream and lathered him up. I coated him all around his balls, and the wonderful black tuft above his cock. He got excited about me lathering him up and got a boner.
As I began to shave him he seemed to get even more excited. I had to pull his, now fully-grown cock, forward in order to shave just above it. When I was finally done, I toweled him off and admired his, now bare, but just as beautiful crotch. I slowly began jacking him off and before I knew it he was cumming everywhere again. I licked some of it off of him and toweled off the rest. I gave him a long kiss and told him how glad I was that we were together.
He then said the first thing that I ever felt I could tell was serious; "I'm glad too."
This would be the start of many more memorable moments between Jeremy, myself, and others.
If you liked this story go ahead and respond to jkinkaide@hotmail.com. I plan to post other stories soon. I hope you liked it. If so, you can see my other story "cock-holder", in the nifty archive, gay/high school section.