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Diary of my affairs: Chapter 1 Losing my virginity


If you don’t like a long story then move on!!! This is the
start of my sex diary and it tells EVERYTHING as best as I
can remember that led up to losing my virginity. The quotes
may not be exact, but some are, and the others are close enough.
I like to add all the elements so the reader gets the feel
of my thoughts and what I felt like.

Remember, anybody can write a short erotic story! Bob fucked
Mary! The end.

After finding out in my husband Wayne started keeping a
diary of our sex life, he let me read it so I could use it for
reference points when needed to write this diary. The reason
he started keeping the sex diary wasn’t for reading as
much as it was for him to confront me with the lack of sex in
our marriage at the time. However, once he let me have a few
affairs his notes came in handy for helping me write about
them, so here I am. All of the affairs he let me have happened
after we were married for 10 years except for one. The one
was an affair Wayne didn’t know about, but I let him know
about it after he let me have my first affair when I figured
the time seemed right for his forgiveness.

When I was fifteen I had a crush on a guy named Bob who lived
a a few blocks away. He was four years older than me and hung
around with my next door neighbor Jimmy. Whenever I saw
Bob hanging out next door, I’d go say hello and try to start
a conversation. A few times, he was there while I was sunbathing
in my bikini, and a few other times I purposely went out to
sunbathe if I saw him or knew he was there.

The next year I turned sixteen and one thing started leading
to another. Bob had just gotten a part time job as a painter,
which resulted in him having a lot of days off. It was the
middle of the summer when my dad offered to pay him to paint
our living room and basement, and he took dad up on it. The
day he started, I was excited that he’d be in my house,
and although there were the times I purposely wore my bikini
to sunbathe when I saw him next door, it was just to get his

Honestly, at sixteen it was puppy love. I didn’t want
him sexually and never even gave it a thought. Anyway while
dad was at work mom and I helped move a few things out of the
way and when she went to do some housecleaning, I stayed
in the living room talking to him and listening to the radio.
After a few hours I said I was going to go catch some rays and
headed upstairs to change. Purposely sunbathing where
he could see me out the living room window, I caught him looking
at me a few times.

Around noon mom called me in for lunch telling me to go change
and told Bob to clean up and get something to eat. I purposely
went to the living room first talking to him, but I was really
there to show off before I went to change. After lunch I got
a quick shower and spent the rest of the time in the living
room talking to him wearing a pair of short shorts and a shirt.

Yes, I had on underwear and a bra! I was sixteen, with puppy
love, not puppy lust! Well, not totally anyway, but even
though I wasn’t interested in sex I knew how to get a guys
attention. Turning off the radio I turned the TV on and laid
back in the recliner we’d moved so I could be looking one
way at the TV while he was behind me painting. From time to
time I’d catch him looking at me again, which excited
me, but mom kept coming in from time to time probably just
to check up on us. Other than that, the day was pretty uneventful
with him finishing the living room. A few days later he stopped
by and told my dad he’d come over in the morning to start
on the basement since he had the day off.

Although it didn’t matter since he was painting the basement,
I remember it was raining that morning which ruined me wearing
my bikini to sunbathe. Staying in the basement talking
to him instead, I later heard mom holler, “Mary, Nancy's

Nancy was my best friend who lived a few doors away and was
three years older than me, but she always treated me like
a little sister. Neither of us had any brothers or sisters,
and she knew I had a crush on Bob but wouldn’t say anything
to my parents about it or anyone else for that matter. Nancy
didn’t know Bob was there, but upon finding out, she made
her visit short and sweet.

After eating lunch mom headed for the grocery store since
the rain stopped and I was excited to be alone with Bob. She
was usually at the grocery for about an hour, and when she
left I stayed in the basement keeping him company. I remember
leaning against a part of the basement wall he hadn’t
painted yet, and before I knew it he had an arm on each side
of me slowly moving forward trying to kiss me. With my heart
starting to pound I couldn’t have stopped him even if
I wanted to! He’d already taken his shirt off to keep from
getting any paint on me and not having started painting
again yet, his hands were still clean from washing up before
eating. Wrapping his arms around me he began French kissing
me. It may have only lasted a minute, but it seemed longer.

He mentioned how he’d like to keep kissing me, but if mom
got back and saw he hadn’t painted much she’d wonder
why, so he went back to work, sneaking in a kiss every now
and then even after mom got home. Not getting the whole basement
finished that day, he said he'd return another time
to finish it. That night when Nancy inquired about me and
Bob, I couldn’t hold my excitement to myself and told
her what happened.

“You should ask him to go out for a pizza and a movie with
me and Paul, ” she said.

Knowing my parents would approve me going with her, I didn't
mention Bob and two days later on a Saturday I was in her car
heading to pick up Paul who didn’t have a car at the time.
On the way Nancy said, “Don’t mention to Bob that this
was my idea. Let him think it was your idea instead.”

Then after picking up Paul, we went to Bob’s seeing him
standing out front. “Hey Bob, ” Nancy yelled. “You
want to drive your car with Mary and meet us at the pizza parlor?”

“Sure, ” Bob replied and I couldn’t hop out of her
car and into his fast enough.

We met at the pizza place, and after eating Nancy said to
meet them at the drive-in and gave us a designated place
to meet after the movies were over. That way if my parents
were outside when I got home, they’d see Nancy dropping
me off.

Bob parked towards the back, and once it got dark and the
movie started we did more kissing than movie watching.
I got my first ever sexual rush when he stopped kissing me,
and we were actually watching part of the movie when he started
massaging my inner left thigh. He’d only go as high as
the hem of my shorts though, and then slowly start moving
down again whenever we weren’t kissing. I don’t know
what I’d have done if he’d have tried to go any further.

Once the movies were over we met Nancy to follow her dropping
Paul off at home and then went to Bob’s house where I kissed
him goodnight and hopped in with Nancy who asked, “Well,
how did it go?”

“More kissing than movie watching, ” I replied.

“We can do it again if you want, and if you ever want to know
anything about boys or sex all you have to do is ask.”

A month later I couldn’t hide things anymore about seeing
Bob because too many people found out. Soon it was a foregone
conclusion to my parents that we were seeing each other,
but they were cool with it. They both liked him, but mom was
getting a lot stricter with where I was going and when I had
to be back. One time I remember overhearing my Aunt Mae telling
my mom, ‘She’s not a baby anymore.’

Things moved on from there to where Bob was grabbing my tits
and ass freely when nobody could see, but it was always outside
my clothes, Then one night we parked in a secluded spot in
the neighborhood, and laying me down he went under my clothes
grabbing my bare tits. Halfheartedly trying to stop him,
my nipples were fully erect once he started sucking on them,
but that’s as far as it went. That night I went to sleep
starting to think about things with Bob in a sexual manner
wondering what I’d do or say, or how I should react if things
progressed any further.

Remembering Nancy offering to talk to me about boys and
sex I decided to try and ask her the next day in as casual a
way as I could. She ended up getting pretty graphic telling
me how she lost her virginity and warned me to put a few towels
underneath me when I knew it was going to happen. She also
talked about sucking a guys dick, the taste of cum and so
on. Those were things I really didn’t want to hear about,
but she went on to say, “When the day comes that a guy is
going to eat you just lay back and clear your mind of everything
so you can enjoy it, and the guy will probably keep doing
it to get you off a few times.”

“What’s it feel like to get ate, ” I asked?

“It feels like wetting your finger and rubbing yourself,
but only better because instead of your finger it’s a
guys tongue and he’s in control of what gets licked and
how fast or slow.”

“Why would a guy keep on eating me after getting me off?”

“Trust me, you have the kind of legs that drive guys wild!
Any guy who wouldn’t want to spend as much time as possible
burying their face down there would have to be a queer!”
That was the word back in the day. She went even further and
embarrassed me a little saying, “Hell if I was a lesbian
you’d be number one on my list and you’d have the cleanest
pussy in town.”

“What does an orgasm feel like from getting ate?”

“It’s pretty much like when you finger yourself, but
a hundred times better.”

I didn’t want to tell her that I’d never done that since
I’d never actually had sexual fantasies before. My fantasies
only went as far as kissing a guy and recently at night I started
hugging my pillow pretending it was Bob.

“Sounds like you’re interested in Bob eating you?”

“I don’t know, ” I answered.

“Well if you ever let him eat you be prepared to suck his
dick because fair is fair.”

“I don’t think I can do that.”

“Don’t let it get far enough for him to eat you then unless
you’re prepared to do something for him. Sucking a dick
isn’t much different than sucking your thumb except
it’s a little bigger and more fun. If you have a problem
doing it get on top of him in a 69. The excitement of him eating
you while his dick is right there in your face will help nature
take its course.” I have to admit, that night when I went
to bed I remembered what Nancy said and sucked on my thumb,
but I didn’t try playing with myself.

“How will I know when the time is right?”

“The time will be right when you decide you don’t want
to resist his advances or you want to make advances yourself.
Expect to be nervous, but try and relax and let what happens
happen, but don’t let him do anything you don’t want
him to. If anything hurts tell him to stop or slow down, and
have him wear a condom or pull out before he gets off.”

The two of us sat there silent for a minute while I was thinking
over what she was saying when she asked, “Have you ever
been to his house to see him?”

“One time his mom invited me over for dinner. His parents
are divorced.”

“Why haven’t you gone over on a day he wasn’t working
while his mom’s gone?”

“I’m kind of afraid of what might happen if we were alone.
Plus mom would want to know where I was in case she needed

“Well if you ever need me to cover for you, you can say you
were with me as long as you let me know first so I can make some

A few weeks went by and she kept asking about us, but there
wasn’t much more to tell other than hugging and kissing.
There was another time Bob sucked my tits again, but I never
told her about those two times. It was getting close to time
for me to go back to school as the summer break was coming
to an end when dad was at work and mom hollered at me while
I was in the shower saying she was going somewhere. Getting
out I put on a halter top and shorts and about an hour later
I heard a knock at the door. It was Bob coming over to see me
and letting him in one thing led to another as we kissed on
the couch. While kissing me his hand went underneath to
play with my tits before lifting up my halter top to suck
them for the third time. Meanwhile, he started rubbing
my upper thighs, but this time he was trying to go higher
than the hem of my shorts, which were a little tight on me.

“I have to go to the bathroom, ” I said.

I really didn’t have to, but I used it as an excuse to go
to my room to grab a pair of shorts that weren't so tight.
I also took off my panties putting them back in my dresser
drawer and went to the bathroom grabbing a towel just in
case. Then I flushed the toilet so Bob would think I actually
had to pee and headed back to the couch.

It was the first time in my life that I actually felt horny
for sex. Bob was still laying there as I slyly dropped the
towel at the end of the couch on the floor. Laying on top of
him we kissed as he rolled me to where I was against the back
of the couch. With our arms wrapped around each other he
moved his free arm down to the outside of my upper thigh,
and my heart started racing. Feeling him slowly moving
higher up as if to see how far I’d let him go, I wasn’t
about to stop him!

Soon he was at my hemline and continued slowly going higher.
As I felt his hand going inside my shorts, I started French
kissing him harder not wanting him to stop. Soon his hand
was on my bare hip and he followed it up by squeezing my ass.
Moving his hand towards the center of my ass he had to notice
I didn’t even have a thong on, (I didn’t even own one.)

Pulling his hand out he put it on my stomach and started going
lower until he was inside my shorts. We were still kissing
the whole time, and even though I didn’t have much of a
stomach to hold in, I kept my eyes closed while trying to
give him room to go lower as I felt him make it to my bush. Next
I felt him reach my clit followed by rubbing my pussy and
my tongue was going into overdrive in his mouth. I soon had
a strange sensation that I’d find out later on that I was
actually close to having an orgasm just from the excitement.
Still kissing him, I took my free hand and undid my button
and then unzipped my shorts. With the sudden extra room,
Bob noticed because he couldn’t wait anymore and hopped
up grabbing my shorts and pulled them down. Now naked from
my waist down I got up and Bob asked what I was doing as I grabbed
the towel laying it in the middle of the couch.

Before I could lie down he started kissing me, grabbing
my hand to put it on his crotch. Continuing to kiss me I started
squeezing his dick outside his pants and he put his arms
around me grabbing the back of my halter top before pulling
it up over my head leaving me standing there naked. “Turn
around slowly, ” he said and as I did he said, “You have
no idea how horny it makes me every time I see you in your bikini
showing off those long tanned legs. I always stare at them
whenever you’re sunbathing.”

Knowing he could see my tits too I nervously asked, “Is
there anything else you like?”

“Yes, but you have the best pair of legs I’ve ever seen
and I can’t believe I’m getting a full naked view of

After asking me to lay down on the couch, I laid there closing
my eyes wondering what would happen next thinking I was
going to get fucked right off the bat. Bob instead grabbed
my right leg putting my foot on the floor and started licking
my pussy. Remembering what Nancy told me I tried clearing
my mind to enjoy it. I couldn’t clear my mind of it, but
I sure as hell enjoyed feeling his tongue moving around
inside me.

Soon I was squeezing his head between my thighs not wanting
to let him go. In no time I had the same feeling I had when he
first touched my pussy, and seconds later fireworks were
going off in my head as I had my first ever orgasm from getting
ate. Like Nancy said he might, Bob kept on eating me getting
me off several times before asking me to hop up so he could
lay down and got me in a 69 putting his hands on my cheeks holding
my ass spread wide as he kept on eating me.

Bob had a pair of shorts on, so I started rubbing his crotch
area feeling his erection until I asked him to raise up so
I could play with him outside his underwear. When I unzipped
his shorts and pulled them down I could see the shape of his
dick and grabbed it to play with, but I never touched his
balls because I did know enough that I could hurt him. After
a while I couldn’t take it anymore, so I pulled his underwear
up to look at his dick thinking of how Nancy said it was just
like sucking my thumb but only bigger and more fun. I’d
never seen a live dick before other than changing my nephews
diaper a few times and there was Bob’s dick hard as a rock
nches from my face.

Continuing to eat me but knowing what I was doing he said,
Pull them down.”

“Raise up, ” I somehow managed to say and when he did
I pulled them down and just looked at his whole package right
there in front of me. With Bob knowing I was looking at his
dick, he sped up his pace eating me, and once I knew I was going
to cum again, I grabbed his dick and opened my mouth but couldn’t
pull the trigger in time.

I was cumming like a fire hose, and if I was a squirter I’d
have drowned him! That orgasm helped me finally get up my
nerve to start licking him, but I still couldn’t bring
myself to suck him.

“Put your arms under my legs and grab a ball with each hand, ”
he asked and when I did they felt weird the way they moved
around. I also noticed that when I pulled on his balls his
dick would raise straight up at me. Wanting to take his whole
dick in my mouth, and thinking I could, I didn’t because
I was afraid he’d cum in my mouth. Besides, I had no clue
what it would taste like, let alone how quick he’d cum,
so I kept licking every bit of his dick over and over until
he said, “Bite it."

Opening my mouth wide, I took it just past the head and lightly
bit his dick before returning to licking him. Soon I knew
I was about to cum again and opened my mouth wide pulling
on his balls pointing his dick at my mouth ready to take the
whole thing in my mouth, but again I couldn’t get myself
to do it. I can’t remember how many times I got off that
day, but I know for a fact that it may be the most times I got
off in about an hour from just getting my pussy ate.

Although I opened up quite a few times to take him in my mouth
again, I didn’t. The whole time Bob ate me I only bit him
the one time and just licked him the rest of the time. Somewhere
along the line I still had a ball in each hand when he asked
me to start squeezing them, so I did but not very hard. Then
he told me to keep doing it and give his balls a massage while
I was still licking his dick.

Before we were done he said, “Squeeze my nuts as hard as
you can, but don’t let me know when you’re going to do

“Won’t that hurt?” I asked?

“That’s the whole idea. I want to feel you break my balls
until I yell for you to stop.”

I thought it was weird, but after a few minutes I started
squeezing them harder and harder when he said, “Stop.
I don’t want you to build up to it. Just do it real fast as
hard as you can and don’t stop until I yell, but don’t
let me know when you’re going to do it.”

Although I was kind of afraid to do it, I kept telling myself
that he was the one who asked for it. A minute later still
with one in each hand I closed my fists as fast and as hard
as I could around them and broke his balls causing him to
yell right away. I let go immediately, but almost laughed
out loud. I guess it’s like how my husband Wayne feels
when he squeezes the shit out of my tits even though I’ve
never asked him to. I also have to admit I liked breaking
Bob’s balls, but I was worried that I hurt him and asked,
“Are you ok?”

“Yes, ” he groaned. “But don’t do it again for
a while!”

Looking at his dick I wanted him to fuck me but his tongue
felt so good licking my pussy I never asked him. Over an hour
had passed since he came to my house and he was still giving
me orgasms while I licked him and squeezed his balls hard
a few more times. Soon I heard my mom pulling in the driveway
and jumped up grabbing my clothes and the towel running
to put it back in the bathroom and got dressed.

By the time mom came in, Bob and I were sitting on the couch
watching television. She was polite saying hello to him, but
when he left she gave me the third degree saying from now
on if he came over and dad wasn’t home we’d better be
outside. I lied saying he just got there, but I got the feeling
she didn’t believe me. I don’t think she ever told dad
because knowing him he’d have gotten his two cents in
too. However, mom did let me continue to date Bob.

That night I went to bed thinking about sucking my thumb
again, but I started feeling guilty about what we’d done.
The next day he called asking if I wanted to go out to eat after
he got off work, so I asked mom thinking she’d say no, but
she said ok as long as I was home before dark.

Bob picked me up around six to go to a burger joint to eat and
then we just cruised around. He started rubbing my thigh
talking about what we did yesterday saying, “You were
squeezing my head like it was a pimple yesterday when I first
started eating you.”

“It felt so good I didn’t want you to stop, ” I replied.

“For more than a year now I’ve thought about wanting
to feel the best pair of thighs on the planet on the sides
of my face.”

“The real reason I went to the bathroom was to put on a looser
pair of shorts and take off my panties.”

“I didn’t notice you changed shorts, but I kept eating
you because I was hoping you’d suck me.”

“I wanted to take the whole thing in my mouth, but I couldn’t
get myself to do it. I tried to do it a few times, but I never

“You can try it now if you want, ” he said unzipping
his pants, but I declined.

“Why did you want me to squeeze your balls so hard?”

“It’s always been a fantasy of mine for a beautiful
girl to break my balls.”

“Well I liked doing it, but don’t try it on my tits.”

Bob laughed and with his pants still unzipped he pulled
dick out asking me to play with it, and still being a little
horny from yesterday I did, except to cover him up with his
shirt when somebody pulled up beside us. “I don’t have
to work tomorrow if you’d like to come over while mom’s
at work.”

“I’d like to, but mom’s been pretty protective of
me lately. She always wants to know where I’m going, why
I’m going and when I’ll be back.”

“Well my mom doesn’t get home until around six so if
you get the chance come on over.”

I kept playing with his dick off and on until it started to
get dark out when we headed towards my house. Kissing me
goodbye on the front porch he asked, “Did you mean what
you said about wanting to take my whole cock in your mouth?”

“Yes. Why?”

“I want you to look at me and say you wanted to suck me.”

Looking him dead in the eye I said, “I wanted to suck your
dick, ” and his tongue was immediately searching for
my tonsils.

“See if you can come over tomorrow. I need to fuck you, ”
he said before leaving!

Bob had never so much as cussed in front of me before, but
something about how he said he wanted to fuck me didn’t
seem right to me. With Nancy out on her front porch she came
running over to see me as soon as he pulled away. Going to
my room she asked, “Anything new to tell me about?”

Although she’d been up front with me and explained her
sex life in explicit details, I couldn’t be that open
about telling her what Bob and I did except for kissing.
“He asked me to come over tomorrow while his mom was at
work, but mom won’t let me do that.”

“I told you I’d cover for you if you want me to.”

“How are you going to do that, ” I asked?

“I’m not working tomorrow. I’m going shopping,
so I can pick you up at noon and drop you off at Bob’s if you

“I don’t know, ” I said being a little unsure. Although
I was fine with what Bob and I did, I wasn’t sure about getting
fucked. Maybe it’s a girl thing?

“This might be your last chance for a while since you start
school again next week.”

Thinking it over before she left, I asked mom if I could go
with Nancy tomorrow and she said ok. Then we went to her house
so I could call Bob without my parents hearing, but her dad
was on the phone, so we decided to walk over to his house.
“Don’t say anything about our arrangement to get you
free from your mom’s grasp. Just let him think you’re
there because you want to be no matter what your mom thinks
about it.”

Bob wasn’t outside, and I didn’t have the nerve to knock
knowing his mom was home, so we returned to her house and
this time I got to use the phone. When he answered I told him
I’d come over tomorrow around noon. I can still remember
the surprise in his voice when he said “Really, how did
you manage that?”

“Mom’s going somewhere tomorrow at noon so I’ll
have time to come by for a while.” I lied about mom, but
I wasn’t going to let him know it along with anything about
Nancy’s involvement.

When I hung up I don’t know who was happier, Nancy, Bob
or me. Staying at her house we watched TV until it was time
for me to go home and I ended up sucking my thumb again like
I was practicing on sucking Bob’s dick. Over and over
I kept promising myself that if I got the chance tomorrow
I would force myself to suck him

The next day I was a little nervous while waiting on Nancy
wondering what might happen. I kept promising myself that
if the opportunity was there I would blow Bob, and although
I knew I might get fucked, I tried not to think about it. Finally
hearing her blow her horn, I got in her car and she said the
earliest she could be back was three o’clock. “Make
it three-thirty, ” I said.

“Alright, I’ll be parked on the corner down at Jefferson
Court, ” she said before reminding me of a bunch of things
she’d already told me including that I didn’t have
to do anything I didn’t want to and handed me a couple condoms.

“Where did you get these, ” I asked?

“Boys aren’t the only ones who carry them, ” she
replied. Then dropping me off a few houses away, she gave
me the names of two major chain stores to use in case mom asked
where we went shopping.

Getting out, I walked the few houses to Bob’s and just
as I opened his gate he appeared at the door waiting for me.
Going inside we started kissing as soon as he closed the
door, and leading me to his bedroom I noticed the covers
were pulled down with a couple of towels in the middle of
the bed, and a few folded ones by his pillow.

Bob had his clothes off in no time, but I just stood there
frozen. A part of me wanted to do this so bad, but now that
the time had come I couldn’t move. Standing there naked
in front of me hard as a rock, he grabbed me laying me on the
bed and quickly pulled off my shorts. I almost grabbed my
panties before he could take them off too, not being sure
now that I wanted to do this, but it was too late. No sooner
than he pulled my shorts off he jerked my panties off too
diving between my legs, forcing them apart to eat me. Naturally
it felt good, but I was more nervous than before knowing
I’d probably get fucked. I was so tense at first that it
took me longer to get off than it did the first time he ate
me two days ago.

Letting him do his thing I never moved a muscle until I started
having what seemed more like convulsions when I realized
I was going to cum and somehow managed to take off my top joining
him in being naked except that I still had my shoes on. Eating
me off a few more times I finally settled down and kicked
my shoes off when Bob rolled over saying, “Suck me.”

“I will, but I want to do it in a 69, ” I said, but it wasn't
to ‘Let nature take its course, ’ as Nancy had said.
The truth was I’d actually gotten a little stingy loving
getting my pussy eaten and wanted to feel him eating me as
much as possible.

Bob agreed and let me crawl on top of him, so I wrapped my arms
around his legs grabbing a ball in each hand and pulled to
aim his dick at my mouth. Starting to lick his dick all over,
I also stuck my thumb up and sucked it instead for a minute
with his dick grazing the side of my face. Opening my mouth
wide I finally did it as I dove down taking his whole dick
in my mouth in one quick thrust, but backed off just as quick.

“That felt good. Do it again, ” he said.

Taking him to the root again I instead slowly slid my lips
off of his dick. I was so turned on having taken the whole
thing in my mouth that I started doing it over and over always
slowly sliding my lips off of it and going back. I had no idea
of how to give a blowjob and was pretty much improvising.
One time while having him deep throated I squeezed the shit
out of his balls and as expected he yelled, but he loved it.

When I knew I was ready to cum again, I started sliding my
lips up and down on his dick like a mad woman. I was now actually
sucking his dick and the more I did it the more I loved it.
The thought of him cumming soon entered my mind, but I wasn’t
planning on stopping. I actually started hoping that he'd
explode in my mouth just as I started cumming. For some reason
that seemed like it was the best thing that could happen
and just the thought of it sped up my orgasm. As if being naked
with him in a 69 with over three hours to fuck wasn’t enough,
I was drunk on sex and wanted to find out what it was like for
him to cum in my mouth. Seconds later I was quivering like
a fish out of water, still sucking him as if my life depended
on him cumming in my mouth.

Surprisingly to me, Bob asked me to roll off of him so I did
and he was soon spreading my legs to lay on top of me. Figuring
I was about to get fucked, I closed my eyes forgetting about
the condoms Nancy gave me. Laying there feeling his dick
poking around near my pussy while he kissed me, it took a
few tries before I felt his dick hit its target.

I guess my pussy being so wet kind of helped him along because
after I felt him barely inside he pretty much slammed the
rest in and I screamed. Not taking it out he froze and asked,
“Are you ok?”

“It hurts, ” I said.

“That’s natural. I won’t move until you say to.”

While waiting he raised my legs putting them on his shoulders
to massage them until without asking, he started slowly
fucking me. Putting my legs back down and laying on top of
me he kept on grinding away slowly as we kissed and I moaned,
sometimes in pain, until I knew I was about to cum. Wrapping
my legs around him, I soon had my first orgasm from getting
fucked. Suddenly I remembered the condoms Nancy gave me
and not knowing what to expect when he got off I asked, “Did
you get off?”

“No, I’m not going to cum in your pussy because I don’t
want to get you pregnant.”

Continuing to fuck me at a slow pace while kissing, he got
me off again before putting my legs on his shoulders when
he went from making love to me to fucking me. With his dick
having already found its target, he was about to destroy
it! Rolling me up in a ball he started pounding me as fast
as he could go and I was moaning my life away desperately
trying not to be so loud that his neighbors could hear. Hearing
his balls smacking against my ass at a maddening pace it
only lasted about two minutes before he pulled out. With
me still rolled up, and him holding himself up with his hands
he started moaning while cumming all over my stomach with
a couple of squirts hitting my tits. Grabbing one of the
towels by the pillow to wipe himself off, I did the same,
but I was surprised to see that there wasn’t as much blood
on the towels we fucked on as I thought there would be. Going
to the bathroom to wash up he followed me with the towels
asking, “So how did you like it?”

“It was great after I got used to it.”

Once we washed up he went to put the towels in the washer and
met me back in the bedroom. As I was laying there I remember
looking at his alarm clock noticing we still had over two
hours until Nancy would be coming and wondered what else
we would do to kill the time. Part of my wondering was answered
by Bob when he laid on the bed and said, “Suck me hard again
so I can fuck you some more.”

He wasn’t as hard as before, but he looked plenty hard
enough for another go at it, or so I thought anyway. Figuring
how he said to fuck some more I didn’t worry about the cum
in my mouth factor. As I sucked him he asked me to start flicking
my tongue back and forth on the underside of his dick. Suddenly
I remembered Nancy having mentioned the underside of a
guys dick to me, but since I’d only sucked him in a 69 my
tongue was on the wrong side.

Bob was hard again in no time, and I thought he’d have me
get up to fuck, but he just kept saying how good my lips felt
on his dick. At first while he was half hard I had no problems
deep throating him, but as he stiffened it became harder
to do being below him because his dick was curved the other
direction. Starting to come up just a little short of deep
throating him, the longer I sucked him the more I wondered
if he was going to fuck me or just let me blow him. I had no clue
how long it would take for him to cum again and wondered how
I would react if he shot in my mouth. Deciding I was going
to suck him until he wanted to fuck or until I returned the
favor of him eating me off so many times, I was so horny thinking
he might cum in my mouth that I also decided if it didn’t
taste that bad I would try to swallow it.

That only lasted for about a minute more when he stopped
me and put another towel on the bed to fuck me doggie style.
Once again he was fucking me slowly, but for some reason
it wasn’t doing much for me in that position. I guess he
finally gave up waiting on me to cum because putting a death
grip on my hips he started jerking me back and forth until
he pulled out and shot all over my ass.

We spent the rest of our time kissing and fondling each other
along with more fucking and oral even though I never actually
sucked him off, and before we knew it, it was almost three-thirty.
Cleaning up real quick, I kissed him goodbye and went to
the corner where Nancy was already waiting on me.

Getting in her car she took one look at me and smiled while
asking, “You did it didn’t you?”

I didn’t answer, but I didn’t have to. Besides, lying
wouldn’t have done me any good because she knew me too
well and saw right through me. “I can tell by the look on
your face, ” she went on to say almost laughing. “We
better go to my house for a while to give you time to lose the
grin on your face.”

Going to her house she started asking questions, but all
I could muster at first was that I lost my virginity. Mentioning
the condoms I handed them back to her admitting he shot on
my stomach, tits and back. I finally let her know it all started
with him eating me and how he ate me off too many times to remember.

“Including Paul the first few times a guy ate me I’d
get off too quick. Most of the time they’d figure they
did their job and give me a quickie fuck getting off before
I even got close to cumming, or they’d just expect me to
blow them. I’d just end up sucking them a lot longer than
they ate me, but it doesn’t happen as much as it used to.”

“How come, ” I asked?

“I quit saying what felt good and started thinking of
other things like a TV show I watched or a movie, or something
else, anything that helps take my mind off them eating me
to make it last longer. It usually works, but not all the

I don’t know why, maybe it’s a woman thing, but that
night when I went to bed I started having second thoughts
about what I’d done and felt guilty about it crying myself
to sleep. Bob and I saw each other for another month or two
with him getting my panties down to my knees to eat me again
the next day, but it only lasted for a minute. For one thing
mom was upstairs, and for another as much as my pussy wanted
him to, I fought him off.

Our problem quickly became him wanting to fuck, but I couldn’t
let myself give in to it again still feeling guilty, which
caused a lot of arguing between us. Although we stayed friends
or at least I thought so, I still felt a little bitterness
from Bob whenever I saw him.

Thanks for reading,


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If you’re asking why I’m reposting this it’s because
for some reason the site tried making some kind of improvement
that backfired. Out of nowhere almost all of the stories
on here including mine were changed into one long messy
paragraph that’s hard to read, let alone understand.
As a result, to keep them in order and make mine readable
for those who never read them, I'll have to repost all
of them.


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It was still a cute story the second time around.


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quote willfreeus:
It was still a cute story the second time around.
Thank you very much.


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thinking back there are lots of parallels! Except my first
is still a good friend!


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Long story is very good it gave all of the emotion and insight
into what you were feeling and thinking, , great way to
do it.. and what fun reading about it all, ,


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Very Good job I look forward to reading more of your stories


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very good story thank you


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Okay that is a real short story. Wish they would fit the paragraph
spacing. Thank you for sharing.


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Great story, lots of details. Lucky guy.


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Great memories thanks for sharing and I look forward to
reading the rest of your diary