Date: Sat, 12 Jun 1999 03:59:44 PDT
From: Jeremy kinkaide <jkinkaide@hotmail.com>
Subject: Sister's Underwear
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.