Subject: High School Regrets (MF, M+F+, oral)
By: Kelly <pghkelly@yahoo.com>
Diary Date: July 13, 2007
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!!!WARNING!!!!
This file is a work of fiction containing sexually explicit material which may
include depictions of underage, nonconsensual and unprotected sex as well as
incest and adultery. It is not intended to implicate any person or action by
them or me, nor advocate such practices. If you can't separate fantasy from
reality, get professional help - FAST!
The material is distributed as "For Adults Only" and possession by a minor is
strictly forbidden. If you are not legally empowered to be in possession of
this material, do not read it and delete it immediately.
This work is copyrighted to the author ©2010. It may be posted to non-commercial
"free" sites, or in the "free" area of commercial sites so long as no changes
are made AND the author information is retained.
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Summary:
If you’re like me, it’s probably more the things you DIDN’T do in high school
that you regret more than anything you did. Even then, it’s not really WHAT I
didn’t do so much as WHO I didn’t do. Although we can’t go back in time and do
things over, sometimes you get another chance at it later in life. The question
was, what would I do when such an opportunity arose?
Table of Contents
Chapter 1 – High School Class Slut
Chapter 2 – Nancy Puts Her Plan Into Action
Chapter 1 – High School Class Slut
==================================
While I was in high school I would imagine that if you asked most people who the
smartest kid was, who the richest kid was, who was the class clown, etc. that
you would have gotten pretty consistent answers. We all knew who those kids
were when we were in school. Many of us had label that may not have been listed
in the yearbook but were well-known by everyone. For instance, there was
nothing listed next to my picture but I’m pretty confident that most people
still remember me as the class slut. Every class has one and I worked hard for
my position (no pun intended).
Actually, being THE class slut isn’t as easy as you might think. First, there’s
a lot of competition from other slutty girls, all of whom would scratch your
eyes out given half the chance. Then there’s the pressure from people always
having such high expectations of you, especially the guys. It seemed like every
day some new guy would hit on me, expecting me to at the very least suck his
dick on demand if not more.
Contrary to popular belief, being a class slut takes a of work. It’s more than
just spreading your legs for every guy tat asks, any girl could do that. In
fact, when I look back at it I really didn't fuck all that many guys while I was
in high school compared to some girls I knew - only about a dozen by the time I
graduated. When you consider I’d been having sex throughout all four years,
that’s not exactly a lot of guys. OK, more than most girls but nothing for the
record books. Just because a girl had fucked more than me didn’t confer on her
the same “status” I enjoyed in high school.
It’s all in the intangibles – your attitude, clothes, makeup, hair, and
especially the way you act when you’re around people. My class had its share of
girls that fucked just about every guy in school they could lure into bed with
but that just earned them the reputation for being whores, not sluts. It’s a
fine line!
Based on what people have told me and asked me, apparently most people thought
that as the class slut I could get laid by just about anybody I wanted, any time
I wanted it. Unfortunately, that’s wasn’t exactly true. Of course there was
always some horny boy wanting to get in my panties (that’s only a figure of
speech).
Then there were those boys who were so ridiculously shy that I could’ve
literally hog-tied and dragged into my bedroom, stripped right in front of them
and they STILL wouldn't have done anything because they were so unsure of
themselves. There were also a few diehards that genuinely believed that sex
before marriage was wrong and I respected their beliefs. Some guys had
girlfriends they wouldn't cheat on. I know, that sounds ridiculous that they
would not take advantage of what was available to them but those kind of guys
are actually out there.
Two boys stand out in my mind from my high school years that I never was able to
add to my “sexual history”. First and foremost on my list was Todd who worked
in the chemistry lab. Many a day Robin, my lab partner, and I would tease him
mercilessly as he spied on us from behind the curtains in door to the supply
room at the back of the classroom. We knew he was jerking off back there even
though we never could catch him in that act. Maybe it was the way he would look
at us and try to hide his erection that endeared me to him but try as I might, I
was never able to get him to even talk to me because he was so shy. Something
about the fact that I knew he masturbated about me in class (and probably at
home as well), together with his insane shyness, made me want to be his first.
The second boy was totally different from Todd. Whereas Todd was ridiculously
shy, Rich was the class hunk. My only problem was that he was “in love” with
one of the hottest cheerleaders and refused to date any other girls.
Personally, I don’t think he was just being true to her so much as scare she
would dump him if he cheated on her. I’d done everything I could to let him
know I was “available” but he wouldn't even give me the time of day, especially
if the bitch was around. The more he turned me down, the more determined I was
that I was going to get him one way or another. Well, it never happened, one of
the few times in my life that I really wanted a guy and he turned me down.
Chapter 2 – Nancy Puts Her Plan Into Action
===========================================
After high school I went to college about of state and other than during summer
and various holiday breaks, I didn’t see much of the hometown and I had no idea
what happened to either guy. With time, memories fade and I hadn’t really even
thought about either of them in ages until I played Truth or Dare with my
friends and Nancy mentioned that one of her secrets in high school had been he
desire to fuck Todd. You can imagine the shocked look on my face we I learned
that we both had wanted the same nerd to fuck us.
After our “Truth or Dare” get-together, the next time I had lunch with Nancy we
discussed her answer about Todd. Of course, neither us had wanted him as a
boyfriend and would have dropped him like a hot rock after the first time, but
each of us felt the same way – that he was the “fish” we both had let get away.
Guys aren’t the only ones that occasionally look to add a notch in their belt.
A couple a days later, Nancy called me and asked if I wanted to go out the
following Friday night with her to see a movie. There were several we hadn’t
seen yet and since I had nothing planned I figured why not and accepted. Nancy
was the quietest in our infamous little foursome that dated back to when we were
all in preschool. As one of her closest friends, I knew that “innocent and
naïve” Nancy could get just as horny and naughty as the rest of us, she just
didn’t express it publicly to the degree the rest of us did. She was always
more the follower than the leader, willing to go along with about anything but
hardly ever initiating anything herself.
Friday night came along before I knew it and I got myself ready to go. I
figured we would go to the movie and then probably grab something to eat
afterwards, maybe at a local Eat ’N Park restaurant or TGI Friday. It was just
going to be the two of us and while we may have gotten a bit carried away the
previous week at my house, I had no expectations whatsoever that anything would
happen like that again between just the two of us. We were good friends and I
enjoyed being with her, trading stories and gossip. When I went out with my
cousin Kristi or best friend Beth, I never knew what was going to happen; but
with Nancy, it was a pretty safe bet we would have a pleasant, rather uneventful
evening out.
With that in mind, I decided to stick with a simple pair of tight, low cut jeans
and my favorite pink tank top. Even if I was with Nancy, I was STILL out in
public so why not look good? You never know, maybe some hot guy would walk by
while we were having dessert! The tank top was a bit too small for me but I
liked the way it clung to me as if it was painted on. Without a bra, my nipples
poked through as if nothing was there and you could even make out the full
outline of the entire areola.
Nancy had volunteered to drive so I waited on the couch in the living room,
watching out the picture window. It wasn't long before I heard a car
approaching, the noisy brick street in front of our house amplifying the sound
of the tires. Soon her little red Saturn appeared and pulled up to the curb.
Nancy didn't bother get out of the car but instead just beeped her horn quickly
a couple of times to let me know she was there.
Since my parents were out for the night, I turned off the lights, grabbed my
purse, and locked the front door behind me. I jumped in the front seat and
Nancy immediately took off almost before I had the door closed, not even
bothering to say hello. She seemed to be nervous but at the same time she had
this mischievous smile on her face that she always got whenever she was trying
to hide something, a habit which just made her attempted deception all the more
obvious.
“Well, hello to you too girl!” I huffed, trying to put on my seatbelt as she
took the turn onto the main road sharp that I was thrown against the door,
“Ummmm, is there something I should know about?”
“You could say that,” she replied with an air of mystery. It wasn't like Nancy
to be so mysterious so what was she up to anyway?
“And are you gonna tell me or what?”
“Well, if you’d paid the least bit of attention when you got in the car, you
would’ve noticed.”
Now what the heck was she talking about? The hair seemed to stand up on the
back of my neck suddenly and I looked over my shoulder to the back seat. It was
then that I noticed for the first time that we weren’t alone. Holy crap, there
was a guy in the back seat! I turned to Nancy with my mouth wide open. What
the heck? My expression couldn't have been hard for her to read.
“What’s the matter Kelly, don’t tell me that you don’t know who that is!”
I looked back again where he was sitting with his hands on the seat next to him,
a grin on his face but so far not saying a word. He looked to be tall and while
not skinny, he wasn't overweight by any means. He had thick blonde hair that
he’d let grow over his ears, which seemed to stick out from his head a little
more than necessary. One thing that immediately caught my eye was that he had
the most piercing blue eyes. It was like they could shine in the dark they were
so bright and when he looked at me, it was like he was seeing into my soul. He
was dressed casually, jeans and a polo shirt. Overall, he was your typical
decent looking guy you might find anywhere and walk by without noticing. Why
she thought I would know him was beyond me.
“Oh come on Kelly, I can’t believe you don’t recognize him,” Nancy teased me,
“Maybe I should’ve had him wear his lab coat with his hard cock poking out of
it.”
The poor guy grimaced at that one, as if her last comment had caused him
physical pain but he was a good sport and kept silent. Lab coat? Erection? What
the heck was she talking about?
“God Almighty Kelly, you’re suppose to be the smart one but you can be so blind
sometimes. Really girl, don’t you remember who we talked about the other day….
the guy we both wished we’d done back in high school?”
No, it couldn't be! Todd? Geeky and skinny little dork Todd? Where was the
acne, the horrible black rimmed glasses, the ever-present pocket protector? No
crew cut? How did he grow up so much since high school that I didn't even
recognize him?
“You’ve GOT to be kidding... Todd?” I said to him, staring at him like he was
the latest exhibit at the zoo.
“Yeah, it’s me and...,” he started to say, the grin broadening on his face but
Nancy cut him off before he could finish.
“Well, after we talked the other day it hit me…. why not see if Todd was still
around? So I called up some people who called some other people and it didn’t
take long to find him. Did you know that he still lives around here, just on
the North Side now?”
I looked back at Nancy, still unsure exactly what was going on. Had aliens
abducted my friend and replaced her with this replica? The Nancy I’d known all
these years would never have done such a thing.
“OK, like so I called him told him about what we talked about and then asked if
he wanted to join us tonight.”
“You told him about THAT?” I asked, feeling a little funny inside now. This was
getting to be WAY too weird for me.
“Hey Todd, why don’t you be a good boy and tell Kelly what I asked you about,”
Nancy called back to Todd as she drove on. It was then I noticed we weren’t
heading to the theater but instead were going almost exactly OPPOSITE the way I
would have expected.
Todd’s face reddened a bit as he seemed to be working up the courage to speak.
Well, at least he still had some of the old shyness about him.
“Nancy told me about your game last week and asked if I had wanted to do either
of you back then.”
“And then what did you tell me?” Nancy pressed on.
“Well heck, EVERY guy in school wanted to,” he said, swallowing hard, “It wasn’t
just me.”
“And do you still want to?” Nancy pushed him more.
“I guess,” he stammered, “Are you really serious about this?”
Nancy slapped her hand onto my leg sharply and asked, “What do you say Kelly,
are we serious?”
Sheesh, what COULD I say at that moment. Talk about your night’s plans taking a
sudden detour. First off, I still couldn't believe Nancy had done such a thing.
Second, how had she convinced him to do this in the first place? Finally, I was
still trying to get my head around the fact that this guy in the back seat was
really the same dork I knew back in high school!
“OK, what’s going on Nancy?” I finally managed to get out. “Why is he here, for
real I mean?”
“Well, after we talked about him the other day I couldn't get him out of my head
so that’s why I tried to find him,” she explained, “I just figured we could go
back to my place and get to know each other a little better, if you know what I
mean. Sure beats a movie, don’t you think?”
Well, that all made sense based on the direction we were heading. At the speed
she was driving, we would be at her house in a few minutes provided we didn’t
get pulled over in the meantime. That didn't leave a lot of time to say yea or
nay to the whole idea. Of course my first instinct was to say yes. After all,
it wasn't like he was still that stupid dork at school so why not take advantage
of an opportunity to get laid? Besides, it had been a while since I’d been
fucked so this was like a dream cum true! On the other hand, the whole thing
seemed rather manipulative. What was REALLY happening? What was I missing
here?
Before I could say anything more, Nancy pulled into a parking space in front of
her apartment building. I’d been to her place several times, but it was always
just to visit, never anything like what I thought she had in mind now. For that
matter, Nancy and I had NEVER done anything together like what I starting to
suspect she was plotting. Boy, you think you know someone like the back of your
hand and then she pulls something like this on you!
We got out and quickly went up the wooden stairs to her apartment. Todd fell in
behind and didn’t say a word but I had a feeling I knew where his eyes were
focused as Nancy and I made our way up the stairs right in front of him – at
least I knew where his eyes had BETTER be. Nancy unlocked the door and we both
followed her inside. The first thing I noticed was the place was empty, even
though I knew she shared it with another girl. What exactly Nancy’s
relationship was with her was a subject of controversy among the rest of her
friends as she steadfastly refuse to even discuss it. Whether she was doing
that to tease us or hide something I hadn’t quite figured out yet Nancy must
have noticed me looking around for her.
“Yeah, Julie’s out with her guy tonight… probably won’t see until tomorrow if I
know her.”
Was that suppose to be a hint that Julie wasn’t a lesbian or did it mean she was
bi? Nancy didn’t bother to elaborate as she headed for the refrigerator and
called back to us, “Beer anyone?”
I breathed a sigh of relief when Todd refused as I hate the taste of beer and
even more so, what it does to the flavor of a guy’s cum. As much as I normally
LOVE to eat as much cum as I can get, there is an unpleasant aftertaste when the
guy has been drinking too much beer that I’ve never cared for. Nancy knew
better than to expect me to drink any so she wound up bringing out a few Diet
Cokes.
“So tell me Todd, what do you think?” Nancy asked, a naughty grin on her face.
Todd looked bewildered, sort of like a little lost puppy. Apparently Nancy
really hadn’t told him a lot and I was getting the impression her call to him
had put him in an awkward position where he couldn't refuse her request to meet
us without seeming rude. I had a sneaky suspicion that until the past few
minutes he really hadn’t believed that anything was going to actually happen and
probably was prepared for it to turn out to be some kind of practical joke.
“Ummmm.. what do you mean?” he said, his voice sounding a little strained as his
eyes moved between the two of us girls.
“Oh Todd,” Nancy said seductively, shaking her head slowly, “You know what I
mean. Kelly and me... do you still want us?”
This was an interested side of Nancy, one I hadn’t seen before. To openly taunt
and tease a guy wasn't her usually M.O. and I wondered if she was doing it more
for my benefit than his.
“Yeah right, like you’re REALLY serious,” he said, sounding a little annoyed now
if anything, “I should have never gone along with this.”
He started looking around as if he was waiting for the cameras to emerge and
someone to yell “surprise!” Well, there was one way to demonstrate our intent
(well, at least what was already Nancy’s intent which was now becoming mine as
well). If for me it was like some kind of dream and the reality of the
situation hadn’t quite sunk in yet, I could only imagine what was going through
poor Todd’s head! At times like this a person just responds automatically and
with my past experiences, I was undoubtedly much better equipped to handle the
situation than he was. But first I had a couple of issues to clear up that had
been bugging me for years while I had the opportunity.
“So tell me Todd, did you masturbate when you peeked though the lab door window
blinds at Robin and me in Chemistry class?” I asked. Of course we both had been
convinced at the time that he did but there had never been an “official”
confirmation.
“Ummmm,” Todd looked decidedly embarrassed but managed to answer, “I guess so.”
“Ha, I KNEW it!” Nancy cried out, hearing the answer, “I TOLD you he was doing
it.”
“Hey, don’t blame me... it was your fault,” he tried to explain, “I mean,
wearing those short skirt outfits and showing off your legs and ass all the
time. Damn, what did you EXPECT a guy to do?”
“Well... we expected you to do exactly what you did,” I replied with a smile.
“So if you did THAT, then why did you avoid me all the time whenever I tried to
get close to you?”
“I don’t know,” he stammered, “I mean, look at the reputation you had. I
figured you were just teasing me and having fun at my expense like the other
girls did. I knew you never would have gone out with someone like me.”
I was starting to realize that while Todd had matured into a good looking guy,
he was still a little on the insecure side. Well, I knew I could fix that!
“Do you know what I would have done if you had asked me out, Todd?” I asked in a
low, seductive voice, deliberately licking my lips just enough for him to
notice.
“Ahhhhhh, I’m not sure,” he said, hesitating before he answered.
“You said I had a reputation. So what do you think I would have done?”
Todd’s face was flushed now and I knew I was getting awfully close to crossing
the line in terms of teasing him versus embarrassing him. I’m sure there were
enough guys telling their friends about me that there was no doubt he knew
exactly what I liked to do on a first date. Judging from the growing bulge in
his pants, he was probably thinking about that reputation right now.
“Well then, since I didn't get to show you back then, would you like me to show
you now?” I asked with a wink towards Nancy who was grinning from ear to ear,
obviously pleased with herself for setting up this little encounter.
Without waiting for Todd to respond, I stood up and quickly stepped up in front
of him where he was seated on the center cushion of the couch. Reaching to my
waist with my arms crossed, I grabbed my tank top with both hands and with one
swift motion, lifted it up and over my head, dropping it to the couch beside
him. For a few moments I just stood there in front of him, wearing just my
jeans and shoes with my now bare breasts on display for him.
“So what do you think, Todd, worth the wait?” I asked him as I cupped my boobs
and bounced them a little in my hands..
The way his jaw dropped and his eyes zeroed in on my boobs like a laser told me
more than anything he might have said if he had found his voice. I loved the
way it made me feel when guys like Todd stared at my body. It made me feel sexy
and good about myself.
Moving up closer to him, I leaned over him and put my hands on his shoulders so
that my boobs hung down in front of his face. At barely a 34C, it wasn’t like
they swung like pendulums or anything but he was getting a pretty good eyeful of
what I had.
“You know, you CAN touch them if you want to,” I whispered softly to him, “I
don’t mind.”
Todd hesitated and then reached out and put one hand on each of my boobs. At
first he just planted his hands against them with his palms flat. Then his
fingers slowly curled, just slightly at first and then more as he started to
squeeze my boobs.
“Well, do they feel good?” I asked.
Todd just nodded and then squeezed them some more, letting my hard nipples poke
out between his fingers as he did. I looked over at Nancy, who was watching our
every move, and motioned with my head for her to join in. After all, it had
been her idea to do all this in the first place so why should she be relegated
to spectator status? Nancy took a deep breath and moved in besides me, dropping
her blouse and bra along the way.
“Here Todd, why don’t you try Nancy’s now,” I said as she moved up tight against
me. She felt so warm and soft and for a moment I recalled being with her not so
long ago at my house with our friends, Her boobs were more like a 36D – or
bigger and they hung down a lot more than mine but at the same time, it gave him
a lot more to grab onto.
“Mmmmm,” Nancy purred as he massaged her hefty boobs, “Suck on them.”
For a moment I almost bent over to grab her boobs between my lips but then I
realized she was talking to Todd. He dropped his head and took one of her
nipples in his mouth and began to gently suck on it. As Todd seemed to be happy
sucking on her larger boobs, I decided to stop messing around and get down to
business.
I dropped to my knees on the carpeting in front of him where I pushed his legs
apart and then reached in to unzip his jeans. His belt was a pain to undo but I
figured it out and unbuttoned his jeans. Pulling the jeans apart in the
middle, I reached in under the elastic band of his Jockey underwear (it would
have been a lot easier if he’d worn boxers, or better yet, none at all) and
finally found the head of his dick. Not surprisingly, he was already erect and
I released his cock from the containment of his underwear and it popped out,
evidently happy to have been freed from its cotton prison.
“You know Todd, I bet this is what you wanted me to do when you spied on us in
Chemistry class,” I said as I grabbed his dick in my hand.
Todd took a couple of seconds away from sucking on Nancy’s incredible boobs to
answer saying, “Oh my god, you have no idea how much.”
“So have you had a girl suck your dick yet, Todd?” I asked him, stroking his
dick with my hand slowly. Based on my experience, I placed him at about six
inches but he was nice and thick, more so than average for his size.
“I’ve had a couple of girls in college who did it,” he admitted before Nancy
pulled his head back to her chest which shut him up.
I couldn't help but feel a little disappointed. It would’ve been hot to give
him his first BJ but then again, he WAS 23 and it was a bit much to expect any
boy that age not to have had his dick sucked at least once. But still, you
can’t blame me for wishing he hadn’t.
Keeping his mouth on Nancy’s nipple, Todd helped me pull his pants down and off
his ass until they were gathered at his ankles. That was good enough for me, at
least for the moment. I took a long look at his dick and wondered how many
times had he masturbated and then squirted cum out of it dreaming of me doing
what I was about to do now.
Lowering my head to his crotch, I took just the top of his dick in my mouth and
then let my tongue tease him, poking it into the tip of his dick and then
running it around the smooth skin of his engorged cock head. As I breathed in
deeply, I noticed that he smelled especially good, a little musky and sweaty but
then it WAS hot outside and who could blame him for having a little body odor to
him?
Taking my mouth off of him, I let my tongue run down the length of his smooth
dick and then back up again until I was circling the swollen head once again.
Mmmmm, he tasted pretty damn good too! Finally I went down on him, taking his
entire dick in my mouth until it pushed down my throat slightly and my kips met
the hairy base of his cock. Holding it there for a few seconds, I slowly lifted
myself off of him, twisting my head back and forth as I did as my tongue worked
around it to stimulate him even more.
“Mmmmm, you have a great cock Todd,” I murmured to him, looking up at him where
he still had Nancy’s large nipple deep in his mouth.
“Nancy, you have GOT to try this bad boy out for yourself,” I invited her.
Nancy pulled back away from Todd who then laid back against the couch, looking
down at me as I stroked his stiff dick and waited impatiently for Nancy to join
in. She kneeled to the side of him, leaning over and taking his wet dick in her
mouth as I held it by the base of the shaft to steady it. Her incredible boobs
rested on his thigh as she bobbed a few times on his dick before letting it
loose and grinning at me.
“Shit, he DOES have a nice dick,” she said as she paused to get her breath back,
talking to me as if he wasn't there to hear her.
I took the opportunity to take him back in my mouth once again and for a while
we just swapped back and worth, once of us sucking his dick while the other
leaned back and watched. Meanwhile, Todd was watching everything with his hands
to his side, letting us do all the work. He didn’t say a word, probably because
he couldn't believe what was happening! This was the sort of situation he had
probably dreamed about many times when he masturbated. I could imagine how it
must seem almost unreal to him that one of his jerk-off fantasies was coming
true.
“So Todd, ever have TWO girls sucking your dick at the same time?” I asked. He
didn't answer but shook his head vigorously to indicate he hadn’t. Well,
something told me that he would remember this time for the rest of his life.
Nancy was clearly enjoying his cock so I took the opportunity to strip off my
jeans and shoes while Todd watched. Standing up, I worked the tight jeans over
my hips and finally got them off. This particular pair of jeans was more
accurate at measuring my weight than any scale. It didn't even take an excess
pound to make them virtually unwearable so they kept me honest when it came to
watching my weight! Of course, there was no way I would be caught dead wearing
panties under my jeans, no matter where I was or who I was going out with so
with my jeans off that left me nude for Scott to take in an eyeful of before I
sat down at the end of the couch and turned to face him. Spreading my legs wide
apart, I let him see my pussy like I was some cheap whore exposing herself on
stage.
“Since you masturbate thinking about me, I guess it’s only fair I return the
favor” I said in a teasing tone.
Of course, to be honest I had never actually SEEN him masturbate but then did it
make any difference? As Nancy continued to suck his dick, I started playing
with myself, at first just running my fingers over my horny pussy and then
slowly working them in tighter inside my pussy lips, spreading them apart until
he could finally see my wet pussy hole. When it came to masturbation, there was
only one thing I liked more than touching myself and that was to have someone
WATCH me touching myself. Sometimes I think I get more turned on being watched
than the actual physical stimulation! The mind and imagination can be more
powerful than the finger when it comes to making yourself feel good.
It also didn't hurt I was able to watch Nancy as she give Todd one incredible
BJ. She was stroking his dick with her hand as she sucked on the upper portions
of it, bobbing an twisting on his shaft with her beautiful full lips. I gasped
involuntarily as I pushed my middle finger up inside my pussy. The more I
watched them the more I debated what I wanted more, Todd’s dick in me or Nancy
licking my pussy. Actually, in the end it was a no-brainer. How could I EVER
choose NOT to take a guy’s dick? Sure I loved it when a girl ate me out, but
NOTHING beats being fucked by a real cock. For the moment, though, Nancy was in
control of his dick so the best I could do was plunge my finger deep inside of
me and wish it was Todd’s cock instead.
“Fuck her,” I heard myself saying, allowing myself to get a bit carried away,
“Fuck Nancy for me Todd.”
Personally, I would have preferred to have been the first to get his dick in my
pussy but then it WAS Nancy who had set this all up so she deserved it – I
guess. For the moment it was just me and my finger as I watched my friend in
action.
“You ready to fuck me now?” Nancy taunted Todd. The poor guy was totally in
shock but there are some things a guy can do in his sleep and fucking was one of
them.
“Come here,” he said in a soft but surprisingly strong voice.
Todd reached out and took Nancy by the waist with both hands and helped her to
climb up on his lap, his hard dick poking straight up like a missile ready for
launch. Nancy straddled him and squatted over his steel-rod dick. As her pussy
wet his dick, she paused and leaned over to kiss him briefly.
“God I can’t wait to get your dick in me,” I heard her whisper to him.
As hot as I was for Todd, seeing my supposedly shy friend morphing into an
outright slut right in front of my eyes was REALLY hot for me. Nancy wasn't
paying any attention to her audience, namely me. The only thing that she seemed
to care about at the moment was the fleshy pole that was bending just a little
as she dropped down onto it until it suddenly slipped inside of her and the head
disappeared from sight. Her head dropped back as she moaned softly and closed
her eyes tightly as his dick disappeared into her cunt like a snake into it’s
hole.
“That’s it Todd, fuck her deeper,” I encouraged him, as if any encouragement was
necessary.
Nancy was clearly enjoying herself but then what girl in her right mind wouldn’t
love riding a dick like Todd’s? She gripped the back of the couch behind him as
she rode his dick like the finals of a championship bull-riding contest. Todd’s
eyes were also closed as he concentrated totally on Nancy’s hot pussy as it
slide up and down around his dick, rubbing him and stimulating him in was that
his hand could never do. Her hips would sometimes swing around with his dick
barely in her, like she was trying to keep a hula hoop going and then at other
times she would drop down until her weight was completely on him and then grind
her shaved pussy into his hairy crotch, burying him as deep inside of her as
possible. Todd started to groan louder and his head fell back against the
couch. From the quickening efforts of Nancy, I knew she was as aware as I was
of what was about to erupt!
“Cum in her, Todd,” I whispered hoarsely, not really caring if he heard me or
not but more like a wish for myself as I watched him fuck my friend.
“Oh fuck!” he finally gasped, his eyes widening as he approached his climax.
Nancy dropped down on him again and started to swivel her hips around, literally
stirring his cock around inside of her pussy.
“Oh yeah, do it!” Nancy whispered as I saw Todd’s ass clench and then his body
shook and jerked as he started to cum inside of her. God, he was so deep in her
that his cum had to be way up inside of her!
I tried to imagine the sensations Nancy must be feeling now as his hot sperm
shot from the end of his throbbing cock to be deposited inside her pussy. It
was enough to make my own orgasm finally take off. My pussy felt like it was on
fire when my hips rose up automatically, as if I was trying to get Todd to bury
himself deeper in to me instead. My orgasm struck me like a Mack truck, taking
away my breath as I squeezed my eyes shut and it was like stars were exploding
in front of me. Low moans escaped from my lips as waves of pure pleasure hit me
like I was standing in the water at a beach after a storm. When I finally
opened my eyes, I saw the two of them were watching me, both smiling as Nancy
remained perched on his dick like she had been mounted there like an insect on a
pin.
“I think somebody’s ready to be fucked, Todd,” Nancy said as she turned back to
him.
She lifted herself off of him and my eyes remained fixed on his wet dick as it
slipped out of her dripping pussy. It was covered with his cum mixed with her
pussy juices, looking like the most delicious thing I’d seen in a long time! I
wanted to suck and taste it but even more than that, my pussy was practically
screaming for it to be in me.
I could barely breath with anticipation as Scott made his way over the couch and
kneeled between my legs. I hadn’t moved from the position I was in when I was
masturbating before and my soaking wet pussy was wide open, waiting for him. I
tried to look him in the eyes but he was staring at my pussy like a hungry kid
looking through the window at a candy store. Damn, the guy had just fucked
Nancy but he was still as horny as ever! Todd lowered himself down over me
until his dick was poised at the entrance to my pussy.
“Put it in me, dammit,” I growled at him, impatient now and wanting him to fuck
me and stop fooling around. There comes a time when you just want to be fucked,
when you NEED to be fucked and I was way past that time already.
Scott just grinned, any hints of shyness seemed to have disappeared now that he
had two girls begging to be fucked by him. Amazing how that works. Then
without any warning, he suddenly rammed his still stiff dick forward, driving it
into me all the way to the hilt in one swift motion. I thought I would scream
it felt so incredible! One second my pussy was empty, pleading for him to fill
it, and then the next it was like I’d been stuffed by some huge object, making
me feel all swollen and full. The dramatic change in such a brief moment,
coupled with the remaining vestiges of my earlier masturbation, set me off again
and I came instantly, before he even had a chance to start stroking himself in
and out of me.
“Oh fuck that feels so damn good,” I cried out as my legs reached up and tried
to wrap around him so as to pull him deeper into me if that were even possible.
“Shit, she’s already cumming Todd!” I heard Nancy exclaim. I couldn't see her
with Todd hovering over me but I knew she had to be watching. We’d masturbated
together enough times over the years that she could recognize the signs, even if
I hadn’t said anything.
My pussy had clamped down on Todd’s dick, gripping him to keep him from escaping
to the point it was almost like having a cramp. Todd moaned and I didn't know
if it was from the pleasure of my orgasm or maybe even the pain of my pussy
squeezing his dick so hard. In any case, he didn't try to move for those first
few seconds when my orgasm first hit. Then, as my grip loosened just slightly,
his instincts took over and he started to stroke in and out of my pussy like a
steam engine piston. It had the effect of making my orgasm peak yet again and I
cried out loudly as again my pussy gripped him tight enough to keep him from
moving.
“Turn her over,” I heard Nancy say, acting as the director for our little show.
Todd acted as thought he didn't even hear her, slamming his dick into me as hard
as he could, driving me back onto the couch with a grunt as I felt the base of
his dick strike my pussy hard.
“Hey, I’m here too you know,” Nancy whined, “C’mon guys, turn over for me.”
Todd must have decided he’d better listen to her because just as abruptly as he
had shoved his hard cock into me, he pulled it out in one fast move, leaving my
pussy with this suddenly weird empty feeling, like something was missing. Well
duh, something WAS missing – Todd’s dick! Todd grabbed me by the waist, pulling
me up and flipping me over so I was facing Nancy now. He lifted up on my waist
and tucked a large pillow under my stomach to keep my ass up in the air, making
it easier for him to get to my dripping wet pussy.
As Todd maneuvered himself in behind me, Nancy was ready for me as well. She
was on her back with one leg draped over the back of the couch and the other
hanging over the side with her pussy just inches from my face.
“After last week I’ve been wanting to do this with you again so bad,” she said
to me, her voice filled with unexpected emotion.
I wasn't about to turn down the chance to eat her delicious pussy again and as I
started to lick her I felt Todd spread my butt cheeks apart and then the
relentless head of his dick started to push against my asshole. I quickly
lifted my head off of Nancy enough for him to hear me warn him.
“No Todd, not there!”
Thankfully, he didn’t try to press the issue and instead dropped his dick down
to where I really wanted it – my pussy once again. Once he had it in position,
he put his hands on my hips and pulled me against him as he pushed himself into
me. Once again, there was no hesitation or slow motion. His dick split me open
again and he drove it home in one quick motion. I gasped as I tried to suck on
Nancy’s clit but it was hard to keep my mouth in place with the force of Todd’s
dick ramming into me over and over again.
Eventually I just let him do the work, placing my tongue on Nancy’s pussy and
letting the motion created by Todd’s fucking of me to run my tongue up and down
her pussy. She was holding her boobs, massaging them and pulling on her nipples
as she enjoyed her pussy being licked.
Nancy’s freshly fucked pussy tasted wonderful! I could even make out the
remains of Todd’s sperm which was now mixed thoroughly with her pussy juices.
Damn, her pussy smelled so strong! My thoughts went back and forth between what
Todd was doing behind me to the way Nancy was squirming under my face. .Finally
she stiffened and then she pressed her pussy up against me as I held onto her
clit with my lips.
“Ooh Christ I’m cumming Kelly,” she moaned as her orgasm took her.
Once again I was a little surprised at her reaction. When we use to masturbate
together back in high school, Nancy was the one that never made a sound when she
came. The rest of us would be moaning and squirming like we possessed but cute
little Nancy would just stiffen up and smile. Well, not today, that was for
sure! No, today Nancy was practically screaming as her orgasm consumed her and
overwhelmed her. Damn, the neighbors would be calling the police if she didn't
calm down a little! If I didn't know better, I would never have known it was
Nancy with all the fuss she was making.
Apparently it was turning on Todd even more than me to witness Nancy’s reaction
as I felt his grip on me tighten and he pushed himself into me as far as he
could before finally cumming in me. The first shot was the biggest, creating a
quick bloom of warmth deep inside of me. Then he started to pull out of me and
for a brief moment I feared he was going to spray the rest of it on my ass and
back instead of leaving it inside of me. Fortunately that wasn’t his plan but
the rest of his sperm he shot off with his head barely inside of me. I knew
what he was doing and I wasn't going to complain. Somebody must have been
watching a few too many porn movies and wanted to see a “cream pie”.
“God… that is SO hot,” he gasped as he pulled himself out of me and I
immediately felt his warm cum start to drain out of me. He was behind me,
evidently watching his own sperm as it emerged from inside of me.
I would have thought that Nancy was too exhausted from her own efforts to do
anything but as soon as she realized what Todd was doing she somehow got up and
off the couch and made her way behind me.
“Mmmmm, now THAT looks delicious,” she said in a sultry voice, “Want some Todd?”
I twisted my head around in time to see Todd grimace. What is it with guys that
they won’t eat their own cum anyway? It was really no matter as Nancy was just
being polite. She was the one who really wanted my cum and now she didn't want
to wait any longer for it. I felt her hands on my bare ass as she got her
balance and dipped her face into my ass so her tongue could go for the sperm as
it drained out of me.
“Wait, I have a better idea,” I offered, trying to get up.
The two of them looked at me, wondering what I was doing, and I grinned as I
explained to Nancy what my idea was. She laid on her back on the couch as I
straddled her face and lowered my pussy until it was just an inch or so from her
open mouth. Squeezing down like I was trying to take a pee, my pussy pushed
more of his cum out and it dripped down and into her open mouth. The cum
drained out of me in long strands of goo as she took it with her tongue and
tried to suck it down into her mouth. Todd was watching intently, his hand
subconsciously stroking his dick which was still as hard as ever.
“Mmmmm,” was all Nancy could say as her mouth filled with more cum.
Finally, the main part of his load seemed to have dripped out of me and Nancy
sat up. It was my turn to lay down now and she put her face over mine, letting
the cum drip from her mouth into my own. It was such a turn-on to have her
give me my own pussy cum and his sperm fresh from my pussy! Finally we both sat
up and while Todd watched, we kissed and exchanged his cum back and forth
between us before finally we both swallowed down what was left in out mouths.
“So you like watching us swap your cum?” Nancy teased Todd. He just rolled his
eyes and nodded as I doubt he even knew what to say at this point. Nancy
reached over to where his hand was rubbing his dick and took it in her own hand.
“You know, we can do it again if you can give us some more,” she offered.
Twice in a short time wasn't bad, although I knew guys who could cum a lot more
often than that and still stay hard. Todd’s dick was definitely softer, despite
his efforts to stroke himself hard again. He look exhausted so I thought maybe
Nancy and I needed to give him a break. I had never seen Nancy this way before
and I didn’t want to miss out on a golden opportunity. While Todd sat back and
slowly stroked his soft dick, Nancy and started making out on the couch, kissing
and touching each other.
Before the night was over, Todd managed to fuck each of us again. Well, actually
us both together by which I mean we each got up on the couch next to each other
on our hands and knees with our butts facing him and pussies available. Todd
would stick his dick in one of us and after a few stroked, switch over to the
other. It was like a slot machine, which one of us would he cum in? To my
chagrin it turned out to be Nancy but this time ate least I was the first go the
cum from her mouth as we did another exchange for Todd’s benefit.
Eventually we were all exhausted and got dressed to take Todd and me home. It
felt a little weird as Nancy drove to his house with him sitting alone in the
back seat. It was physically the same arrangement as when we were on our way to
Nancy’s place but it sure didn’t FEEL the same. Maybe I should have rode in
back with him and sucked him off!
After we dropped Todd off and had driven out of sight, both Nancy and I suddenly
started laughing and giggling.
“Oh my God, can you believe that!” Nancy squealed, “He’s gonna be jerking off
nonstop for the next week now.”
“Month as least,” I corrected her with a smile.
The rest of the way to my house we talked about what had happened. Both of us
skirted around whether or not we would ever do Todd again and the subject of the
two of us together was carefully avoided as well. I think we each knew this was
one of those “once in a lifetime” opportunities that we had taken advantage of,
but never expected to happen again. Would we? I guess only time will tell.
One of the best things, though, when I look back at this day was that I finally
got to fuck Todd after all these years. How often do you get to go back and
correct a mistake in your past? Well, now there was one less regret in my
little closet of secrets!
THE END
20070713 High School Regrets