It took only a second for me to recognize her at the
other end of the bar, because she looked the same,
even though I hadn’t seen her for 20 years.
I felt a stirring at my crotch, and it made me laugh
to myself. Catherine was turning me on as if I were
still a pimply teenager. I had aged a lot more than
she had, and I wondered if she recognized me. She was
with a large, well-built young man.
As I looked at her, I daydreamed. I had never hooked
up with her, although I had wanted to. And from my
conversations with her, she had, too. She was probably
the most beautiful girl in school, as well as the most
developed. And she was insatiable at a time when most
girls were scared of sex.
She was notorious for offering herself to every boy
who crossed her path. She didn’t seem to discriminate
by race or looks, although I heard that she did turn
down bullies and conceited rich guys.
And the funny thing was that while the girls hated
her, all of the guys treated her with respect. The
ones who had been with her told me that she was
incredible and they were always ready whenever she
would summon them. I noticed none of them ever put her
down or made fun of her.
Why didn’t I ever get together with her? I guess it
was because I was just too busy with advanced
placement classes and extra science projects. Several
times she had made an overture, but something
interfered each time.
I saw she was still looking at me. She had certainly
held up well. I would jump at the chance to take her
to bed, except it was too late. I was happily married,
and even though I was out of town at a hotel where
nobody knew me, I would never cheat on my wife. Not
that I didn’t fantasize. After a day packed with
meetings, I usually ended up at the bar for a drink
before I turned in. I saw a lot of beautiful women,
most of them probably hookers, and I imagined things,
but I never approached anyone. I was polite but not
encouraging to the ones who approached me.
I saw Catherine and her friend get up. They were
walking toward me. I smiled at her. “Hi Catherine,” I
said.
“Hi Ronnie,” she said. “How are you?”
“Great,” I said. “And you?”
“I’m fine. This is my friend, Harold. I was telling
him that we were friends in high school, and I wanted
to hook up with you, but we never did.”
“Why didn’t we?” I said. “I wanted to also, but it
never happened. I’m sorry for talking like this in
front of you, Harold.”
“Oh, don’t worry,” he said. “I’ve heard all about high
school from Catherine and other classmates she runs
into. I don’t know how she ever graduated because all
her homework time was spent in bed.”
Catherine laughed. “I have to admit I was a real
slut,” she said. “Did you ever wonder why, Ronnie?”
“Yes, and all the other guys did too, because you were
such a classy looking girl. Now that I’m not so
stupid, I’m sure there was a sad story at home behind
what you did, even though you always seemed so
positive and happy.”
“The strange thing is that I wasn’t abused or raped or
anything like that,” she said. “My family was as
American as apple pie, and my brother and sister were
just like all the other kids. But for some reason, sex
education in seventh grade really turned me on, and I
started experimenting. And then I couldn’t get enough
of it. I still can’t.”
“Do you live here?” I said, trying to change the
subject.
“No, I’m staying at the hotel and leaving tomorrow?
How about you?”
“Me too,” I said. “I’ve been in town making business
calls. It was an exhausting day and I better get to
bed. It was nice running into you. Let me buy you and
Harold a drink before I leave.”
“Why thank you,” said Catherine. “But that’s not
necessary.”
“It’s my pleasure,” I said. “Bartender, would you
please take an order from this couple and put it on
Room 5023. Thanks. Goodbye, Catherine, bye Harold.”
They said good night to me, and I went up to my room.
A minute after I got there, I was already undressing
when I heard a knock on the door. I opened it a crack.
It was Catherine. “Look what Harold found,” she said,
holding up my wallet.
“Oh my god,” I said. “Thank you so much.” I waited for
her to hand it to me, but she had stepped back from
the door waiting for me to open it. I was in my
underwear, and I didn’t want any misunderstandings, so
I said, “Wait a minute,” and shut the door. I quickly
pulled my pants on and opened the door.
As I did so, something big grabbed me and lifted me in
the air, carried me to one of the two queen-size beds,
dropped me onto it and held me down. Then something
covered my face and I couldn’t see anything. After
that, I felt some bare skin pushing into my face. And
then I could see again.
I was lying on the bed and Catherine’s naked butt was
on my face. Harold was standing next to the bed
holding a few balloons.
I heard a voice from above. “Ronnie,” it said, “I’m
going to move on top of your mouth right now, so you
won’t be able to speak, but I’m going to lean forward
so that your nose isn’t covered and you can breathe.
It may be tangled up a little in my ass hair, but you
shouldn’t have any trouble. Harold will check to make
sure you’re all right.”
She shifted, and I felt her vagina move on top of my
mouth. As she lowered herself, it pushed against me
and the lips opened. Out came a flood of juices,
covering my mouth and face. She must be really excited
by this, I thought, trying to keep my mouth shut so
nothing got inside. My nose was being tickled by the
hairs between her cheeks, but I could breathe.
“I’m sorry about this, Ronnie,” said her voice from
above. “I was hoping you’d make a pass at me and we
would come up to your room together, without Harold.
But you’re a faithful husband and I compliment you on
that. And this way works too. You’re probably
wondering what’s going on, so I’ll explain before we
start.
“For some reason, despite being obsessed with sex, my
brain has room for other stuff. Only my counselor and
the teachers who saw my IQ score knew this in high
school. They were always telling me that my wild
behavior could ruin a great career. I didn’t listen to
them and I didn’t go to college. Instead, I went to
beauty school, where I learned a trade and found out
that there is more sex of every variety available in
that industry than probably in all the others
combined. Maybe that’s why I was unconsciously drawn
to it. You wouldn’t believe some of the things I did
with men, women and everything in between. I finally
found a place where I was average, maybe even below
average, in my sex drive.
“I graduated from beauty school and went to work at
one of the big chains cutting hair. Because of some
suggestions I made to improve things, the boss made me
assistant manager, and when he was promoted, I took
over. I made some changes, and my store won the award
for the most productivity that year.
“A vice president showed up one day and took me to
lunch and pumped me for ideas. The following week, he
called me and asked if I’d be willing to move to
corporate headquarters as his assistant. I found out
corporate headquarters are almost as wild as beauty
school and hair salons. I moved up fast. I suppose it
helped that in addition to being good at work, I also
slept with nearly every man and woman in the office.
When they found out that I didn’t ask for anything in
return, they gave me more than I could have ever asked
for. They were all happy when the president of the
company got an offer from a competitor and the board,
which I’d also gotten to know intimately, selected me
to be the CEO.
“I made so much money for that company that the
stockholders kept voting me bigger and bigger bonuses.
I bought a big house and brought lots of men and some
women there for amazing evenings. I had everything
money could buy. Then one morning I woke up feeling
strange.
“I suddenly realized there was more to life than money
and power. I had all the money I could spend in five
lifetimes, but was I really happy? There was something
missing for me, and I finally figured it out when I
read that book about 100 places to see before you die.
“I was still relatively young, but I had dreams. There
were some things I thought about after I graduated
from high school and beauty school, but I knew they
were only fantasies and that I could never do them.
Now they came back to me, and I realized that with my
money, maybe they were possible. So I handed in my
resignation, and after the board gave me an obscene
amount of money, I stayed on for one year. But even
though they offered even more to me after that, I had
to let go to pursue my dream.
“During that last year, I spent my spare time working
on my list of 100, but I could only get to 53, so I’m
rounding it off and calling it ‘Fifty Men to Do Before
I Die.’
“You are one of the 50, Ronnie. I wanted to hook up
with you badly in high school, but as you said, it
just never worked out. You probably don’t care, but it
was frustrating to me. All the things I did with some
of your friends and the other boys never felt
humiliating or demeaning. I did them enthusiastically,
and I didn’t care what anyone thought.
“But the guys who turned me down or never followed
through when I approached them, they were the ones who
made me cry. I realized they thought I wasn’t good
enough for them. They looked down on me, and that made
me cry in my pillow many nights. I never showed it at
school, because I didn’t want them to see, and most of
the time I was very happy. But those boys who I wanted
to have and never seemed to get to… I could never
get them out of my mind completely.
“And don’t tell me you didn’t look down on me, Ronnie.
Actions speak louder than words. You put your projects
or grades or whatever ahead of a beautiful girl who
was offering her amazing body to you. You had
priorities, and my feelings were way down on your
list. Can you imagine how humiliating it was for me to
realize you wouldn’t give up one night of homework for
me?
“I started with an expensive detective agency, but now
I’m finding most of the men with the help of the guys
I’ve already tracked down. Your friend, Jim, helped me
find you after I did him, and I know you’ll help me
find others. I’m determined to find all my 50 men
before I die and do them, like I’ll be doing you
tonight. Life is unpredictable and even though I’m
still not that old, I could be run over tomorrow, so
I’m moving ahead on this.
“I think that explains it for you. After we’re done,
I’ll be glad to answer any questions. My friend
Harold, who just turned on all the lights, will be
doing a video of us for a remembrance. He’s very
talented. He’s a magician and his hands are so fast
that he can remove a wallet no matter where you carry
it. Don’t worry. I’m the only one who will ever see
the video. My goal is to do 50 men, not destroy their
lives.
“I think you will probably want to get this over with
as soon as possible, so the best thing you can do is
follow my instructions. If you don’t, it will just
take longer to do the same thing. Lick my pussy if you
heard me.”
I was still trying to deal with what she said before,
and I didn’t respond. I felt her hands unzipping my
fly and getting into my boxers. They cupped my
testicles and began squeezing slowly.
“Can you hear me now?” she said. “If you can, lick my
pussy.”
The hands were squeezing tighter. I quickly licked
her, and my testicles were freed.
“Good,” she said. “Harold is pulling off your pants
and boxers right now. Then I’m going to hold your
jewels while he pulls off your shirt. If you try to
yell, it’s going to hurt a lot.”
When I was naked, she moved back on top of me, facing
my feet. “Now, I’m going to give you a blow job, while
you eat out my ass,” she said. “Don’t worry, I’ve
cleaned it, so you won’t find any surprises. I’m going
to pull my cheeks apart and put it right over your
mouth. Start by licking all around it, and then when I
give you the signal, push your tongue in as deep as it
will go. If you can hear me, start licking my
asshole.”
I licked her hole and tried not to gag. I felt her
squirming on my tongue.
“OK,” she said, “Now I’m going to push, and it will
allow you to stick your tongue inside. Push it in as
far as you can go by pressing your face between my
cheeks. You should be able to get your head so far
into my ass that your ears are almost covered. It
looks awesome on video. OK, here I go.”
I couldn’t get myself to follow the instructions until
I felt the hands on my testicles again. Then I put my
tongue inside her anus and pressed my face into her
cheeks to push it deeper. She was still while I was
doing it, but once I stopped, she lifted up her ass a
few inches and then pressed it down, pushing my face
further in and my tongue deeper. She kept doing this
until her ass cheeks did get up to my ears. My nose
was also pressed tight into her cheeks and I was
having more and more trouble breathing. When she
finally lifted up, I was gasping for air.
“That was good,” she said. “Now go to work on my pussy
while I work on you.” I felt her mouth suck me in as
she shifted over me to place her vagina over my mouth.
The juices were still flowing from it like water from
a faucet. At first, my nose was pressed into her anus
and I couldn’t breathe, but then she moved a little to
free my nose. When she finally stopped, my nose was
only partially into her anus and my mouth covered her
vagina. I stuck out my tongue and began moving it
around inside her.
In her mouth, my penis grew hard as a rock. I felt her
fingers push something onto it. It wasn’t a condom.
“I’m putting a cock ring on you,” she said. “It’s just
a tight band that I’m pushing all the way up to where
your balls meet your cock. It will keep you from
coming. Don’t worry, you’ll get to come later.”
As I continued to lick, she leaned forward so my
tongue was caressing her clitoris. That got her body
moving. I heard sounds coming from her mouth, and now
she was moving in a rhythm of her own. She was rolling
back and forth over my mouth and pressing down harder.
She was masturbatng against my face. Then she screamed
and began slamming her vagina hard against my mouth. I
gave up licking and just tried to pull back as she hit
me like a punching bag. She almost knocked me out
before she finally stopped and sat down hard on my
face. My nose was now pushed deep into her ass and I
couldn’t breathe. I held my breath as long as I could,
and just as I gave up, she lifted off of me.
She got off the bed and leaned over me. “That was
terrific, Ronnie,” she said. “I think I had eight or
nine orgasms there. Now it’s time for the cowgirl to
ride the big bull.”
She got back on the bed and lowered herself onto my
shaft and began riding, slowly at first and then
faster and harder. She was slamming her body so hard
on top of me that my testicles were flying in all
directions. My body responded and tried to come, but
it couldn’t, and the frustration of being held back
became painful. Then she slowed down a little, and I
felt her vagina spasm around my pole. I tried to count
the orgasms, but I couldn’t keep up.
When they stopped, she sank forward, and I felt her
lungs heaving through the large breasts pressing
against my chest. It took her at least five minutes to
recover. Then she got up off me, and as she did, I saw
Harold bend over me. He was holding the end of a
balloon with two fingers, and he stuck the fingers
into my mouth and released the balloon. I felt the air
from the balloon exploding into my lungs, and then his
fingers were gone.
Catherine began talking again. “Ronnie, you’ve been
the best one so far, and I’m keeping good notes on
each of the 50,” she said. “I really wish you had
invited me up here, because then we’d be finished, but
in order to get Harold’s help I had to make a deal
with him.
“See, Harold also has a goal in life. He’s gay, but
straight guys turn him on more than anything else. His
goal is to initiate 200 virgin asses in his life, and
I promised to help him, if he’d help me. We agreed
that when one of my 50 responded to my overtures, all
he would do is film us. But if I had to use him to get
them to cooperate, I would help him with his goal.”
I started to say something, but I stopped right away.
My voice was tiny and shrill and sounded like a duck.
“Don’t be startled, Ronnie. That’s the helium from the
balloon, and we have a few more in case you need a
refill. Harold likes to hear his virgins responding,
so rather than use a gag, this lets you get all your
feelings out without being too loud. It also makes you
seem effeminate on the video, which is helpful, as
I’ll explain later.
“I see you’re flinching. Yes, that was Harold’s finger
pushing some lube into you, and now he’s working a
long tube into you very carefully. After it’s in as
deep as it can go, he’ll turn a little spigot and
he’ll fill you full of soapy water. When we see from
your body language that you can’t hold it in any
longer, he’ll take you to the bathroom, so you can let
it all out. He’ll do that two more times, once more
with soapy water to finish cleaning you and then the
last time with lubricant.
“The lubricant won’t make you want to expel right
away, but eventually your asshole will begin spasming,
and it will start coming out. When it spasms, it will
also make it a lot easier for Harold to get his thing
in you.
“I see you’re starting to fill up. Look at Harold
taking off his clothes. He’s not even aroused yet, and
his thing is already scary. It’s like a big, long,
thick snake. I’m glad he only likes men.
“After you’re filled with lube, he’ll release you, and
then the fun begins. I’ll be videotaping. You know,
this part of doing my 50 has become more and more
exciting to me. Maybe it’s that frightened look in
their eyes as they try to escape Harold. Maybe it’s
that look of humiliation and emasculation as he pushes
into them when their ass spasms. Maybe it’s the pain
and degradation in their expressions as he pounds them
relentlessly in various positions.
“While he’s got your legs over his shoulders and your
ass in the air, he’ll slam into you in the piledriver
position, but then he’ll slow down and do it more
gently. You’ll be caressing him and kissing him as he
does. You’ll look like two affectionate lovers.
“I know you’re not gay or bisexual, but you’ll do your
best to convince Harold how much you love him, because
until you do, he’ll keep destroying your asshole. He’s
strong and can go a long time before he gets tired or
comes. If you cooperate and pretend you’re his
lovebird, he finishes a lot faster.
“After you’ve exchanged some deep kisses, he’ll stand
you up and move you around the room like a bumper car
while slamming into your ass from behind. Then he’ll
turn you around and lift you up by the thighs and
lower you onto him and bounce you up and down while he
carries you. Make sure you hug him around the neck
while he does this or you may fall over backwards and
hit your head on the floor. Number 6 almost did this.
We don’t want any brain injuries.
“While you have your arms affectionately around his
neck, you’re going to be giving him deep loving French
kisses as his hands on your cheeks lift you up and let
you drop on his rod.
“There will be a few other positions, but you’ll end
up on the bed sitting on his lap facing away from him.
By grabbing your thighs, he will rock you quickly on
and off his rod, and then he’ll pull back and his huge
thing will rip out of your asshole. That’s not just
painful, but it also opens up a gigantic black hole
called a gape. It looks fantastic on the video.
“As the gape starts to close, he’ll drop you back onto
his pole and begin the rocking again until he pulls
loose for another gape. Once you and he get in a good
gape rhythm, it will be time for the finale, in which
you’ll get to bring yourself off.
“I’ll remove the cock ring, and you’ll start pumping
your dick hard in order to come. There should be
plenty of lube covering it by that time from all the
stuff spurting out of you. If you wilt a little, I’ll
use my mouth and hands to get you hard again, but then
it’s up to you. Harold is going to keep gaping you
until you come, so I’m sure you’ll get right to work.
“Because of the cock ring, you’ve got stuff in there
that’s crazy to escape, and when you come, it will be
like Old Faithful in Yellowstone Park. It makes for a
great visual.
“Only one thing to do after that. You’ll get on your
back, on the bed, and Harold will get behind your
head. I’ll grasp your legs and pull them up and then
push them back until Harold can reach them. Then he
will slowly pull them back further while I push
pillows under you for back support. We’ll be very
careful, because if we’re not, we could pull your back
out. So don’t resist too much.
“When your anus is right above your mouth, we’ll align
it in the right position, and Harold will push inside
your ass and go at you until he comes. As you can see,
he has a huge package, and he spurts what seems like a
quart of semen.
“When it comes out, it will feel like a pressure hose
inside you, and there won’t enough room in your
intestines to hold it all, so it will come squirting
out of your hole all over your face. You’ll keep your
mouth shut tight, but it will cover your nose and go
into it, so you won’t be able to breathe, and
eventually your mouth will open and his come will fill
it up. You’ll be coughing and choking as it goes down
your windpipe unless you start swallowing fast.
“When Harold’s finished, he’ll pull out, and you’ll
enjoy a bunch more of his come pouring out as his
thing comes loose. Then I’m going to squirt a little
enema solution into you, and a few minutes later,
you’ll be releasing all the rest of his semen over
your face and into your nose and mouth. If you want, I
can send you a copy of the video. You won’t believe
it.”
“Once everything appears to be out, we’ll clean you
up, and we’ll order some coffee from room service.
Then we’ll relax and talk about old times. I’m
particularly interested if you’ve kept in contact with
any of my 50. I want to know everything about them,
especially where they live.
“You’ll be very helpful, just like the others, because
Harold and I will put together a specially edited
video. It will show you and Harold in the positions
where you look like you’re really enjoying each other
and even kissing. The finale of the video will be you
getting gaped while you pump yourself to orgasm.
You’ll be surprised how it really looks like you’re
enjoying doing it together with Harold.
“The video is for Harold and me only — and you, if
you want to see it — but if I think you’re not
cooperating in helping me find my 50 men to do before
I die, then I’m going to submit it to one of those
amateur sex video sites where it will probably go
viral. So I’m sure you’ll be helpful, Ronnie. If you
want, I can show you the video that we made of Jim
before he helped me find you.
“OK, I see you are starting to squirm and your lips is
squeezed together to help you hold in the liquid.
Harold will take you to the bathroom to finish your
preparations so we can get going on his video.
“Oh, and Ronnie, I want you to know, that when you
have a goal as big as mine, it takes a lot of people
working together to achieve it. I’m really grateful
for your support.”