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m,f/M,f,mast,first time

By Typoman

Do not repost this story without my header.
Do not remove my name from this story.

This story is about me and two lovers. One turned out bad,
the other great. You might have to wade through a little bit
to get to the sex parts, But they are in here

This story contains true life adventures of me as a boy/man
of 17-19 years. It describes sex acts between minors and/or
adults. If you are offended by stories like this, or you are
under the legal age (21) to view material such as this, do
not read any farther.



I was a virgin when I got my first cherry. In a way, I
was fooled into screwing my girlfriend. Later on I found out
that she was one conniving little bitch. The world was a
soap opera to her. Karen was her name. She lived just down
the block from me. They had just moved to Arizona from New
Joisey. I spied her while driving by her house. Our eyes
met, and I was hooked. This was my first real girlfriend. We
started seeing each other regularly after that. We would go
over to my neighbor's house and make out in the basement. My
older brother didn't like her. He told me that whatever I
did, don't screw her. Well I took his advice at first. She
had the kind of breasts that I learned to dislike. They were
big floppy ones with an areola that just sorta blended into
her tit. She was 16 at the time and I was just about ready
to turn 18 and graduate high school. Even at that young age,
her tits were starting to sag. She was maybe about 30 lbs.
Overweight at the time. Soon after she turned into a real
heifer (that's a type of cow if you don't know). Of course
at the time, I was getting a great make out with her and she
was really the first one that I got intimate with. I sucked and played with those titties till she was sore and we had
to stop. I realize now that I could have fucked her at any
time. One time we were swimming in my parents pool at night.
I got her swimsuit off. She was sitting on the side of the
pool by the steps with her legs in the water. The very first
thing that I did was to eat her pussy. She started to quiver
and shake about three seconds after I dived in to her box.
Her pussy tasted a little like salmon and sulfur mixed
together. I got past the taste pretty easily. After all, I
was in front of a real live pussy. I hadn't seen one that
close since I was about 7 years old. Back then, All I knew
to do was to look at the girl standing there with her dress
pulled up, panties off, legs spread wide and a stream of
piss coming out of her. Eating Karen out made me realize
just how it can affect a woman, I was hooked. Of course I
had always wanted to try it. She didn't ask me to eat her
and really wasn't expecting it either. She had a great
orgasm. I showed her how to suck me off. That was pretty
good, but not NEARLY as good as my second cherry, now my
wife and lover of 23 years. That's the good part, so just
hang in there till I get to her please.
Karen, Trish (my wife) and several others hung out
together at school. At that time, I was not interested in
Trish at all. She was a little smartass and always had a
jibe ready to deliver to any unsuspecting person. Karen and
I had a little bit of a stormy relationship. I got tired of
her and she was seeing other people. Of course she told me
all about the people she was going out with. It was just
innocent friends from her old Catholic school. This dweeb
(Miles) had some horses and Karen liked to ride. Anyway, my
brother kept giving me hell about Karen. He called her
"Karenal Kissy Face". What a fitting name it turned out to
One day after we broke up, she called me and sounded
upset. She told me that she thought that she might be
pregnant. Well, I knew that I wasn't the father, I never
fucked her. I went over to her house and picked her up so we
could talk. The story that she gave me was that she really
didn't even know if Miles the dweeb had actually gotten his
little prick inside her. He just made a few jabs at her
pussy and came all over her.
I now realize that this was just one of her little
ploys to get me to screw her. Well, I fell for it and before
the night was out, We were no longer virgins. Now, Taking a
girls virginity is supposed to be a real thriller. It ISN'T.
When I broke the hymen of both girls in this story, it hurt them. There is also a responsibility that goes along with
it. Karen told me later "You may not know it now Larry, but
one of these days we are gonna be married!" Now that was a
scary thought. I didn't want to marry her, I just wanted
pussy! We had screwed the first time in the back of my car.
I didn't blow a nut right away like my brother said I would
do. But I couldn't get my prick all the way in her either.
I'm not hung like a horse. Just normal sized, with a thick shaft. I remember that we went to her house afterwards and
their little dog kept sniffing my hand, then her pussy, and
my crotch. The little bastard was trying to squeal us out.
The second time I screwed her I managed to get my prick all
the way inside her. The third time I swear by all the gods
her pussy was loose! It stayed loose too! Well I was young and stupid and horny so I didn't know the difference. We
were soon screwing regularly, I was eating pussy and getting
head too. Then Karen told me that sucking my cock made her
sick to her stomach. She stopped giving me head. Of course I
then stopped eating her pussy and just fucked her. The
little bitch lied when she told me that she came when I just
did the straight sex. She wasn't smart enough to even fake
an orgasm. I never even asked her if she came because I knew
she hadn't. after a while of no licking, she asked me why I
stopped. I told her that "It made me sick!" she got the
hint! Pretty soon she was back to polishing my knob like she
used to.
You men out there that don't eat pussy are really
missing out. A pussy eating induced orgasm is about the most
powerful orgasm that a woman can have. If she has never had
her pussy licked before, she's yours for life. How can a man have a good time screwing a woman if she hasn't already had
her pussy licked till she came her brains out then tried to
buck you out of the saddle! Once she's had her first good
orgasm, the second or the third or fourth etc. are really
easy for her. The greatest feeling of power and control is
when a woman is in the throws of orgasm. Especially while
your prick is buried deep inside her. Nowadays, getting a
woman off is what really drives me to orgasm.
Well. Sorry about that lecture, back to the story.
One morning Karen snuck through my bedroom window and
we fucked in my bed. Later on I came back homed to find my
bed all made up and the covers turned down to expose a big
pussy juice stain! I was busted! My mother never said a word
about it, but she definitely knew!
One time at an all night party at the river, Karen was
stoned along with most everyone else. We were in a double
sleeping bag together right at the fire and everyone else.
She got horny and ducked inside the sleeping bag and started
to blow me. Everyone could tell what was happening because
of her head bobbing up and down under the bag. Naturally, I
was a little embarrassed but hey! I was getting a blow job
so I didn't even want to stop her. Someone yelled out, "Hey
Karen! What the hell are you doing under there?" She flopped
the top of the bag back and yelled out "SHADDAP!" in that
New Joisey accent that was more than just a little
Later on, we moved our bag away from the crowd and she
asked me to fuck her up the ass. Naturally, I went for it. I
didn't know about how to properly prepare a butt for anal
sex, also we had no lube. Of course that stopped my only
chance to ever have anal sex so far. She stopped the action
right quick after! I got about half way up her rectum.
One time while we were broke up, she came over to my
house and told me that her father had choked her and kicked
her out of the house. Later she amended the story. She fled
the house in fear of her life. She was still underage. Like
a real dumass, I fell for it and we got back together. I
called my sister Nancy and she said that Karen could stay
with her until she worked something out. Nancy lived about
50 miles away. I took Karen there and we spent the night
together. I went over to her parent's house that same day so
they wouldn't suspect that I had the little conniving bitch
with me. Naturally, her father and mother were worried sick
about her and hadn't the faintest idea why she had run away.
Wouldn't you know it, as a result of that night she turned
up pregnant! I told her that I would marry her. (Sounds like
deja vu?) Well, later on everyone convinced her that an
abortion was the smartest thing to do. I was off the hook!
We broke up again.
By then I was sharing an apartment with a couple of
friends. She wanted to move in with us really badly,
although she never asked. She was still only 17 and still in
school. She would call me up and ask if she could come over.
I would tell her that I couldn't pick her up. She got
desperate enough that she would ride her bike the 6 miles to
my place. By then I was getting pretty tired of her,
especially after she cooked me a meal!
Occasionally I would get desperate from lack of pussy and seek her out. She tried to play the "Look here! I have
two men after me and I just don't know what to do!" game. I
refused to play, and would leave. The competition was little
Miles that couldn't break a cherry. He was not what I
considered fair competition. We were broke up for good it
A few years and a couple of one nighters with different
women would pass before I encountered the girl that turned
out to be the love of my life once again.
Enter Trish

Now comes the good part. Thanks for being patient with
my ramblings so far. As I have said before, I met Trish
through Karen. I remember one night, the Gang was spending
the night partying at the river.
Randy, one of my friends, took an interest in Trish. He
was pretty slick and usually had no problem getting into a
woman's pants. He told me that night that he thought Trish
had a really nice pair of titties and was gonna make a try
for her. He spent all that night making out with Trish and
hardly got her halter top off. He gave up after that.
Trish was great at defending her virginity. Not that
she was a prude. She just wanted to wait till the right
person came along. Her parents were very happily married and
Trish knew what a great relationship could be like.
One night my brother and I were cruising Main Street
with this big old school bus that were going to convert into
a recreational vehicle. We had parked that big old monster
right on the main drag and were sitting up on the roof
watching the cruisers. I heard someone call my name. It was
Trish. She was cruising with Darlene, her sister in law. I
waved to them and invited them up on the roof with us. boy had she changed. She was a different girl when apart from
her closest friend at the time (My future sister in law
Christine). I felt an immediate attraction to her. She was
also interested in me. We chatted for a short while then she
had to leave. She gave me her number when I asker for it. I
told her that I would call her. It took about two weeks
until I finally got a hold of her. Either she was out when I
called, or I was out when she returned my call. Well, we
finally talked and she invited me over to another friend's
house for a party. She asked me to bring a friend so the
boy/girl numbers would be even. I brought Randy with me.
Randy had told me to forget about Trish cause he couldn't
get very far with her. He never would tell me just how far
he got but he sorta intimated that he got her top off and
that was about it.
Randy and I showed up and we started to party. Trish's
brother was there. This guy is huge! He stands about 6 foot
3. At that time he had hair down to his shoulders like mine.
He also has a bad eye that sorta stares off a little into
space that makes him look even meaner. Fortunately, I'm over
6 foot tall myself and wasn't easily intimidated. We got
along well and became great friends.
Randy and Donna hooked up almost immediately. Trish
made the first move on me. That really helped cause I have a
hard time making the first move. Here we were all alone in
Donna's parent's house for the night. Trish's brother and
his girlfriend (Christine) left early. Christine and Karen
and Trish were friends at school. Trish and Christine
weren't such close friends since she started going out with
her brother She thought she had graduated to the big league
by roping in Trish's older brother. As a result, Trish
wasn't nearly so quick with the zinger insults.
I found out later that Karen was telling both Trish and
Christine some whopping tales about me, and our relationship
together. I learned later that Karen thrived on trouble
(real or imagined). According to Karen, we were always
having knockdown fights and the next day or a little
afterwards we would make up. That was why Trish was so catty
with me when I was going out with Karen.
Back to Trish. Any male with just a little experience
knows a virgin when they meet and talk to one. Trish was
like that. We made out a little that night. I didn't get
very far, and didn't try that hard either. I told Trish
right off the bat that she didn't have to worry about me. I
was safe and she could trust me. This made her ask "What do
you mean?" I told her that I knew that she was still cherry
and that she could trust me. "How can you tell if I'm a
virgin?" she asked with a flabbergasted look on her face.
Well, I had been around her for a while and just knew, apart
from my friend's experiences with her. I told her "Guy's
sometimes can just see it" . I also said that there are a
lot of ways to have a great time and not lose your
virginity. This got her interest perked.
Most the guy's she went out with before, made a play
for the pussy. They would get mad and not take her out again
after they realized she wouldn't give it up.
We slept together in the same bed that night and I was
the gentleman. I got to feel those luscious titties of hers.
We slept together in the back to front "spoon" position.. I
had passed the first test.
A couple of days later, I went over to her house. After
her parents had gone to bed. I was able to get her totally
naked. She felt pretty safe with her parents close by in
their bedroom. She was sitting in a upholstered chair, and I
was on my knees in front of her. I got her to slide close to
the front and eventually her legs were apart. The very first
thing that I did was to slowly and gently lick her pussy.
Her reaction to my lingual ministrations was spontaneous.
Waves of pleasure racked her body. It wasn't very long
before she had her first tongue induced orgasm. Now this is
the god's honest truth, when she came, it was so hard that
she fainted dead away. She was out of it for about two
minutes! After she came to her senses, she was amazed at the
intensity of that experience! She told me later that she had
started masturbating at an early age like I had. She was
quite familiar with orgasms as was I. Trish has the best
tasting pussy that I've ever experienced. No salmon at all.
Forget the sulfur. It has a sorta sweet taste. She got me
off by hand later and it was really intense. I fell in love!
A few days later she was giving me the best blowjobs that
I've ever had and swallowing my come. She swallowed my load
right from the start. I found out later that she had given a
few lucky guys blowjobs before. We hit it off so well. I
could play her pussy like a grand piano. We seemed to know
right from the start just how far we could take each other
into orgasmic ecstasy before it got too intense to handle.
Much to my amazement she asked me to spend the night
with her. I was flabbergasted. Here she was, a 17 year old girl living with her parents and she expected me to take a
royal ass whuppin from her father as soon as he got up in
the morning and found us together. Well she convinced me
that her parents would much rather know where she was than
having her go off god knows where. "Besides" She said, "My
brothers have had their girlfriends stay overnight and we
would be right here in the living room with all our clothes
on. I got brave and stayed.
I woke up to her father sitting in his favorite chair
having a cup of coffee and looking at me. I pretended to be
asleep and sorta nonchalantly pull the afghan we were using
back over me. Her father just grinned and said "So Larry,
You want a cup of coffee?" Trish had been right after all.
I relished the feel of her hymen when I put my finger
up her. She didn't want me to push very hard on it cause it
felt really strange to have that pressure on it. It took a
few years before she really got any intense feelings from
intercourse itself. All her nerve endings were tuned in to
her clit. Not true now.
Christine and Trish's brother had been giving Trish
hell for quite a while about being a virgin. She also caught
hell about her small breasts. Speaking of breasts, Now is a
good time to describe those lovely orbs that I have loved
right from the start. They weren't small even back then when
she was 17 and hadn't had any children. Those titties were
just about as close to perfect as two titties can get. The
size of them was just right. Not so big that they would hang
like half full sacks when she got older. They stuck out
proud! No droop! (Very little droop even today after two
kids) They never have gone "north and south" when she is
laying on her back like some titties that I have known. Her
nips would stick out when going braless in a tee shirt. The
areolas are about silver dollar size. They end very
distinctly, no blending into the white flesh as some are
known to do. Her butt was like Jamie Lee Curtis's butt in
that movie where someone described it as "The butt of a 10
year old boy!" Interestingly enough, her gorgeous legs just
happened to go ALL the way up to her pussy.
We talked about everything. She told me about all the
guys that tried to screw her. One time this guy wouldn't
take no for an answer at a drive in. She found a 7 up bottle
under the seat while she was pinned on her back and brained
the bastard with it. Then she walked down the road to a
phone and called her brother. While on the phone she saw him
drive down Main street to the Jack in the Box. Needless to
say, the dickhead got a royal ass beating right in front of
all his friends. He steered a wide path around Trish at
school after that.
It really turned me on to hear her tell about the
people that she had gone out with. I would ask her to tell
me just how far they got. One guy that she still had
feelings for had the opportunity to take her virginity.
Trish wanted him to be her first. I really respect this man even though I never met him. He worked in a traveling
carnival and wouldn't do it cause he was going to leave. I
knew that I was in love with her practically from the start
and told her so. It took a while before she got over him and
admitted that she loved me.
After a few months I told her that I wanted to make
love to her. We decided that we were gonna "do the deed" on
her 18th birthday. I had to wait about a month for that to
happen. My brother loaned me his bus, which was now finished
and occupied by him. On that fateful night Trish made dinner
at the bus. We took a leisurely shower together, then got
into bed. I gave her a few orgasms orally before I put on a
rubber and did what had to be done. Trish is definitely not
into pain! She has a small pussy and was apprehensive about
the whole affair. I used KY jelly to make things easier on
her. I guided myself into her entrance, did a couple of
shallow strokes. Trish was becoming nervous. I read
somewhere that when breaking a hymen, it was a good idea to
draw the woman's attention away from what was about to
happen by biting just hard enough on her earlobe to cause
pain. That's what I did. I didn't tell her that I was going
to do it before hand. This was a serious matter to both of
us. I bit her ear then gave the thrust that broke through
her barrier and she cried out. After a few thrusts, I saw
the pain on her face when I was only a little over half way
inside her. Seeing her in pain caused my cock to go limp.
This had never happened to Herkimer before. He was famous for staying very hard, even after orgasm. I pulled out of
her without an orgasm.
She cried in my embrace afterwards, not so much from
pain but because it finally happened. The rubber I used had
torn as I thought it might. After a while, we talked and
cuddled. She gave me one of those tremendous blowjobs to
finish me off. We went back to her parent's house.
The second time we had real sex was a couple of days
later. I managed to get it most of the way inside her. It
was still uncomfortable for her so I stopped before orgasm.
The third time it was bearable for her and I managed to
bottom out. I came but pulled out just before it was too
late. It took quite a while before I could bring my love to
orgasm during sex. Even though I always brought her off with
my tongue before entering her.
Now her pussy is very sensitive to being fucked. She
just doesn't really feel "completely satisfied" unless she
has a good stiff prick in her, no matter how many times I've
brought her off beforehand. We have explored just about
every avenue thinkable except anal sex.
After 21 years of marriage and being together for 24
years we still fuck like bunnies. We even catch hell from
our grown kids about the noise that comes from our bedroom.
Throughout my married life, I have had a few
opportunities to play around with other women. Although the
temptation sometimes has been great, I seriously doubt that
sex with someone else can come even close to the pleasure
that I've received with my wife. I haven't strayed.

If you have comments, gripes, or suggestions about my
works, please reply to the newsgroup that I posted it in. My
email addy is fictitious and I wish to remain anonymous.


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