Swinging with Oscar and Friends Part 1
by Waldo Ataboy (ataboy@ameritech.net)


This story is fictional. It has no relationship to
anyone I know, I ever met or anyone I may hope to meet.
It came out of my own sick mind. It’s pornographic and
should not be read by anyone who doesn’t like this kind
of stuff. Also it should not be read if you are 18 years
of age or under. It’s probably not good for you and you
are not permitted to read this story.

This story may be copied or saved, if you want to.
However, no charge is permitted. If anyone copies it or
transmit it to another, this statement must be included.

Waldo Ataboy 1-15-01

Part 1: Swinging with Oscar

The bastard, Oscar, is a son of a bitch. He’s fucking
my wife without my consent. He’s doing it in the most
perverse way knowing that I know he’s doing it and
flaunting it before me with full knowledge that I can’t

I’m Henry P. III, and my family are prominent
socialites in New York. I’m 24, 5’10”, and 160 lbs.,
trim in good shape and a recent grad from law school;
work for a prestigious law firm in Manhattan in their
Probate and Trusts division. My family connections
helped me get my job.

Recently I married Jean who I knew since we were kids
and we moved in the same circles.
Her family is also well established. She’s 23 years old,
5’5″, and 110 lbs., also keeps in good shape, dirty
blond. She has nice boobs, plump tush, and has those
good looks that attract attention. She has a degree in
the fine arts and works as an assistant curator at a
museum here in Manhattan.

I met Oscar in the steam room of a health club where I
go to in the afternoon when I have free time to workout
after which I go to the steam room, shower and go home
for supper. It was in the steam room I first saw him on
a bench just opposite from me, stretched out with his
sheet wide-open, legs apart. A big man, maybe 35 years
old, over 200 lbs., all muscle, wide shoulders,
prominent nose and mustache. What attracted my attention
was his long fat moist dick with a big circumcised head
there on the bench. I couldn’t take my eyes off of it;
it raised an unnatural passion in me and my prick
responded by getting hard. Glancing up, I noticed that
he was looking at me with a big smile on his face.
Embarrassed I immediately looked away, wrapped my sheet
around myself and left to get control of myself under a
cold shower but I knew he knew of my admiration for his

He left also but I could not face him in the shower
room and I dallied so that he would leave before me and
he left before me in the locker room when I got dressed.
When I came out in the lobby he was there and came over
to me and said, “I’ve checked you out, and I’m told that
your family is important here in New York. I wonder if
you would give me the pleasure of your company and let
me buy you a drink? We can go to Dante’s which is just
around the corner.”

Sure, I could use a drink and obviously he wasn’t
making a big deal of my indiscreet admiration of his
cock in the steam room. Having heard of Dante’s I was
curious; it was known as an old fashion saloon where the
gays, lesbians and others with bizarre tastes would
gather and find others with the a similar bent. It was
dark when we entered with a long bar on one side and
tables on the other side and a large aisle in between;
it had fixtures and pictures from the turn of the
century. As we walked down the aisle the few patrons
seemed to know Oscar and greeted him as we walked by.
We went to the far end of the bar and sat on the stools.
The bar tender knew him also and when he came to serve
us, Oscar ordered his usual; he brought back a full
bottle of a fine Irish whiskey, a pitcher of water with
ice cubes, two whiskey glasses, two water glasses and a
plate of nuts.

“Is this drink OK with you?” Oscar asked.

“Sure,” I answered.

Oscar poured two shots, two chasers and pushed one to
me, and said, “Cheers.” We downed the drinks. He poured
another and pushed the bottle to me to pour my own. As
we drank and munched nuts he told me with pride about
himself describing how he pulled himself up as a dropout
from school to his present wealth. His father, a
dockworker, drank too much. He quit school at 16 in the
10th grade and went to work to help support his mother
and four younger sisters as a delivery boy to a
dressmaker in the Bronx who needed a strong and tough
kid to safe guard his shipments from mobsters offering
protection. As he acquired the contacts in the business
he opened up a shop for himself in the needle trade.

It was in the rag business (that’s what they call the
fabricating of women’s apparel) where he met his wife,
Maria. She was a seamstress who worked for him from
Spanish Harlem but acquired the knack for discovering
the coming spring and fall fashion in women’s clothing
and could make the patterns to make cheap copies to be
sold in department stores and dress shops to the public.
If they were right for the season’s production they made
big profits and if wrong they would be stuck with unsold
merchandise. Not only was she tall and good looking but
also necessary for business so he married her. They knew
their stuff and became extremely wealthy.

With the second bottle I lost my normal restraint to
talk about myself and from his urging I told him about
my wife and myself. Getting a little tipsy, he insisted
on taking me home by cab to my apartment. Releasing the
cab he helped me in where he met Jean and accepted her
offer to a cup of coffee while I plopped down on the
couch and fell asleep. I don’t know how long he stayed
and talked to Jean but he was gone when I awoke hungry.
Jean gave me supper cold and rattled on how she was
impressed with my new friend, Oscar. She accepted his
offer to join him and his wife to go out some evening.
Maria was to contact her to make plans.

Friday my wife called me at work and told me that Maria
did call and made a date for tonight and we will be
picked up by Oscar at 7 to go for a meal at a gourmet
restaurant, then to a disco for some dancing to follow
that with a nightcap at their place all at his expense.
We were ready when the buzzer to our apartment rang;
Oscar downstairs was waiting for us, and we came down
Jean in her tight short evening dress with slits on the
sides with a wrap, and I had on my regular dark suit.
Oscar gallantly held the rear door to his Mercedes for
us and off we went to a fancy French restaurant in

Oscar made it a point to sit next to my wife when we
were seated at the restaurant while I sat next to Maria.
The food was great but I couldn’t help noticing that
Oscar was toying with my wife under the table while Jean
pretended to resist and was obviously enjoying it. Maria
asked me if I knew Kendrick and Margaret Vander K.. I
told her, “Their family came from the original Dutch
settlers in New Amsterdam and are prominent among the
elite here. We knew them well as we grew up together.”

“As you no doubt know, they moved to Toronto just
recently and we were sorry to see them go,” Maria said
and she nonchalantly continued, “We were swinging with
them and we are now looking for a nice young couple to
swing with again.” Jean giggled but I didn’t have the
slightest idea what Maria was talking about.

After supper when Oscar and Maria went to get the car
and I had Jean alone I asked her, “What’s this swinging
bit anyway?”

“Everyone knows that, swinging is where two couples
exchange spouses from time to time for sex and intimate
sharing,” explained Jean.

“No way will I go for that,” I insisted, “I’m not going
to let Oscar screw you. I’m no pervert.”

“Don’t be a prude,” chuckled my wife, “Besides how do
you know it’s Oscar that wants to screw me, maybe it’s

“That’s sick,” I sputtered, “We’re not going to
participate in that kind of stuff, I will not have it.”

Our disagreement was interrupted when Oscar drove up;
he got out to let us in and away we drove in the
Mercedes to a disco. I was pissed as Oscar plied Jean
with drinks to break down her resistance at the disco
where he took liberties pawing her at every opportunity
both on and off the dance floor. In fact, she seemed to
like his attention and made it a point to nuzzle up to
him. I was going to put a stop to it when fortunately he
said, “Let’s go to my place for a nightcap.”

We drove to an area in Battery Park City Development
where the most expensive condominiums were overlooking
the Hudson River and parked in a secured parking area
under their building. They had a unit on the 7th floor
and Oscar bragged that it cost him a « million for his
unit unfinished and he contracted to complete it himself
at great expense. Their unit was spacious and well
furnished. Their hired help to maintain it and serve
them were not about when we arrived a little after 11 in
the evening.

Jean gave her wrap to Oscar and he threw it over a
chair, and Maria induced me to give her my coat and tie
to get more comfortable throwing them over the same
chair. Oscar asked if martinis were OK and he proceeded
to shake some in a decanter and poured us each a drink.
We were in the playroom as Oscar called it; it had a
small bar in a corner and a music center where Oscar put
on some slow dance music. Jean downed her drink and
Oscar led her to the dance area for some intimate
dancing placing one arm around her back and the other
hand in front in the slit of her dress on to her hip.
Inhibitions gone by the alcohol Jean wrapped her arms
around Oscar’s muscular wide shoulders and rested her
head in the nape of his neck. When Oscar slipped his
hand from Jean’s hip to her crotch that was going too
far and I would have stopped him then and there but for
the fact my own cock awakened to contradict my wishes
and tented up in my pants.

Maria seeing my condition said, “Let them have some
innocent fun, and besides let me show you some amusing
toys I have at the other end of the room.” Maria took my
hand so that instead of stopping him I follow her to the
wall directly opposite to them. She pressed a button
that caused a panel in the wall to slide open disclosing
objects hanging behind it. Taking from the wall a pair
of cuffs separated by a chain about two feet long she
clamped them shut on my wrists and being caught by
surprise I failed to stop her.

“Wait a minute,” I said, “This is not my thing.”
Ignoring me she spun me around and slipped a thin strap
around my elbows and pulled it tight in back fastening
my arms to my sides immobilizing me. I protested, “Stop
right now and release me.”

Not paying any attention, she turned me around again
and unbuckled my belt, unbuttoned my pants, down came my
zipper and she yanked my pants and shorts to my hips
causing my erect cock to be exposed. “Oh my,” she said,
“We have to do something about that, we don’t want you
to have a premature ejaculation and messing up my rug.”
Still protesting she took a leather cockring with snaps
from the wall, wrapped the thin adjustable leather band
tightly around the base of my prick together with
another thin strap under my scrotum so that my prick and
balls engorged stood hard in front of me but prevented
me from releasing a load.

Turning around I observed Oscar and my wife; he had her
spread out face down on a lounge with her legs out over
the end, her dress pulled up to her waist, her panties
off, and her plump ass available to be penetrated.
Sheathed with a well-greased rubber the bastard placed
his thick, long cock to her asshole and with a thrust
proceeded to bugger her. Jean gyrated and yelped with
pleasure and pushed back to take the whole darn thing up
her ass. I was so turned on by the sight that my own
cock would have shot but for the cockring I was wearing.

“Your wife’s a real slut,” Maria chuckled, “Let’s see
how much we can get out of you. Bend over boy and we’ll
see if you can take it as well as Kendrick.” Maria took
from the wall a fancy strap; about 3 feet long with a
multi-braided handle, pulled me over and let me have it
hard across my ass.

“Yeow,” I screamed, “I don’t go for this at all.”

“I don’t care; it is fun to break you,” she said as
she let me have two more times hard across my ass.

“Yeow,” I screamed again, “Stop immediately; this is
painful and I’m no masochist.”

“Aux contraire, you really want it and need it. All you
rich pampered young men want to be controlled and
abused,” she replied, and her wicked whip landed across
my ass again as the sadist continued her torment. “After
all Kendrick didn’t like it either,” she continued, “But
he accepted it for me.” I could see out of the corner of
my eye that Oscar having finished fucking my wife’s ass,
with her in his arms walked over to watch us. He had a
big smile on his face as he whispered something in my
wife’s ear.

As Maria laid it on I lost all will to resist; it was
painfully but exhilarating and I knew I was hers to play
with and obey. Deciding to disrobe me she released my
hands from their bounds, my shirt and undershirt were
pulled off; my pants were pulled down and removed with
my shoes, socks so that with my prick erect in front of
me restricted by the cockring aching to climax I was
completely naked. I was humiliated and aroused at the
same time; my adrenaline was flowing.

“Enough of this fun time for you,” Maria said, “On your
knees, boy, it is time for you to satisfy me.” and she
put her hands on my shoulders and pushed me down.
Placing a collar around my neck with a leash she led me
on my knees to a chair; with her dress up and panties
down she sat and yanked me so that I directly faced her
hairy twat. Pulling my head in she pressed my lips to
her wet smelly pussy and said “Lick me good.”

I knew what to do although I never licked pussy before
and started slowly on the outside of her pussy lips and
licked causing a reaction as she twitched. Slowly I
worked my way along her puffy lips and tasted the
wetness of her flow. As she moaned, I moved in and
lapped up the increased moisture that accumulated. She
was now bucking and moaning even louder. I dug in and
pressed my tongue, nose and face as far as I could go so
that I tasted and smelled her nectar and she yelped,
moaned and pressed my head in as she climaxed. “Well
done,” Maria complemented me, “You’re a good pussy
licker.” I know I shouldn’t have been but I was aroused
and proud of myself.

“You did well,” Maria said, “I’m going to reward you.
Stand up, boy,” and as I stood up she and removed the
cock ring relieving the pressure that the darn thing
placed on my prick and balls. On her left hand she put
on a latex glove and greased two fingers before
inserting them into my asshole; grabbing my cock with
her right hand wiggled the fingers in my asshole, I
pumped and shot my load onto my pants that was on the
floor at my feet. “You certainly made a mess on your
clothes, take them and go to the bathroom; wash up so
that we can all retire.”

There in the bathroom on a chair neatly folded were a
pair of pajamas and after my shower I put them on. They
fit. As I walked out I yelled, “Hello, where is

“In here,” came Maria’s response, “The second door to
your left is our master bedroom.”

Entering, there was my wife in a skimpy nightie in the
arms of Maria half under the covers in a large king-size
bed and Oscar emerging from an adjoining bathroom in
only a pajama top with his large cock in front of him.
Wishing me a good night he got in bed and pressed
himself to the back of my wife so that she was
sandwiched between the two of them. “I’m sorry there
isn’t enough room for you in bed with us,” Marie said,
“But you can sleep on the cot along the wall or in our
guest bedroom next door.” I choose the cot. Marie
switched off the lights so that only the night-light
remained on.

In the dim light I could see under the covers Oscar had
penetrated my wife in her rear while the two girls were
toying with each other’s crotch with their hands. The
silence was broken by the grunts of Oscar and the
passionate yelps of the girls. As they climaxed I
masturbated in my sheet above me in bed. The room again
went silent as I pushed away my messed up sheet and
under the remaining covers I dozed off to a well-needed

When I awoke in the morning, the three of them were
gone but pinned to my pillow was a note that said, “You
will find in the adjoining bathroom all that you will
need to clean up, a razor, toothbrush, mouthwash and
etc. After you clean up join us for breakfast in the
dinning room.” In the bathroom I discarded my pajamas
and proceeded to wash and shave and in walked a young,
beautiful, dark-skinned maid carrying on a hanger
clothes for me. Being naked, I was shocked by her
unannounced intrusion and tried to cover my private

She took it all in stride and said, “I’ll hang your
clothes on the hock here on the wall. Oh my, I see the
whip marks across your bottom that Maria must have
placed. I got just the thing for that.” In the medicine
cabinet behind me she took out a jar; opening it up and
taking a glob of ointment in her hand she proceeded to
rub the soothing lotion on my ass cheeks. It felt good
but notwithstanding I was humiliated and my prick
responded by getting aroused. Fortunately she left me
without further words or attention.

The clothes fit well, and I wondered how they could
discover my size and get them for me so fast; in tan
slacks, a fancy sport shirt and a herringbone sports
jacket I looked quite dapper when I joined my hosts in
the dinning room for breakfast. Both Oscar and Maria
acted as if nothing unusual occurred the previous night
and insisted I sit with them and my wife to be served by
a young butler who offered to get me any breakfast I

At breakfast Jean dressed in slacks and a blouse that
our hosts must have supplied, told me that she and Maria
were planning to spend the afternoon having their hair
done and shopping and will see me back at our apartment
at about suppertime. Oscar said that he would have spent
the afternoon with me but unfortunately he had to show a
very important buyer for a chain of department stores
his wares in women’s clothing but would drive me back to
my apartment before picking up the buyer.

On the way back to my apartment Oscar asked if I
enjoyed hockey and if so he had a couple of tickets for
tonight’s game. He offered to pick me up around 7 for
the game after which we could get a corn beef sandwich
and beer at a deli and call it quits for the night since
he gets up early on Sunday for Mass, he and Maria being
observant Catholics. This was fine with me for I was
pleased that he was willing to never mind the previous
night when Maria sexually abused me and Oscar fucked my
wife. Let bygones be bygones.

When I got home to our apartment and after giving it a
great deal of thought I came to the conclusion that we
could be friends but in no way will I swing with them;
after all I’m straight and not a sexual deviant. When
Jean came home about 5 with packages, she suggested
pizza as she didn’t want to bother with supper and with
a little rest was planning to go out this very night
with Maria cruising; what in the hell is cruising? I
ordered the pizza.

After supper when they arrived Maria and my wife went
cruising in the roadster that they came in and Oscar and
I went by cab to the hockey game. Oscar was quite
friendly and outgoing both at the game and at the deli
and acted as if nothing untoward had occurred. He was
both civil and considerate and I was left with the
impression that when I explained to him I just wanted to
be friends he would be agreeable.

Jean got home from cruising about midnight and was
euphoric from her junket to the S&M and gay bars that
Maria took her to. She couldn’t stop talking about her
experiences and whom she ran into. To her surprise some
of our best friends were participants who begged my wife
not to disclose their proclivities, one was a cross
dresser and another was a faggot. Maria and Jean had a
great time by judiciously applying a strap on the bare
bottoms of some of them who were turned on by the
whipping. When we went to bed Jean took the initiative
for sex; got on top and wore me out.

On Sunday I told Jean that we would put an end to this
swinging thing. No self-respecting man would or should
condone his wife having intercourse with another. Jean
insisted as a liberated woman she had the right to swing
if she wanted to since it was widely practiced among
people who were chic and it need not threaten our
marriage. “After all,” she stated, “Oscar doesn’t take
it seriously, Maria doesn’t mind, and besides, Henry,
you have to admit you enjoyed sex with Maria.”

“It is perverse, what kind of man do you think I am?” I
said, “and I will not put up with it.” I was getting
nowhere with her and I realized that there is no way to
reason rationally with a woman. I resolved that I would
settle this with Oscar directly since as a man he will

On Monday I communicated to Oscar at his place of
business by E-Mail the following, “It is most important
that we get together as I have a very important matter I
wish to discuss with you. Can we meet at 4:30 this
afternoon at Dante’s? If no, E-Mail me a reply that you
can’t make it.” Not having received a reply I showed up
at 4:30 and went to the end of the bar, and found Oscar
talking to a large man there. He waived me over and
introduced me to Tony a big man and business associate
and pointed to the Irish whiskey and suggested I have a
drink. Indicating to Tony that he had something private
to discuss with me, Tony excused himself and left.

Having full confidence I knew Oscar would understand my
position in regard to swinging and I presented my
objections. Oscar listened patiently but voiced no
comment to what I was saying.
Pouring another shot in our whiskey glasses he put some
water in both our water glasses about half full. To my
amazement took my water glass to the fly of his pants,
he opened it and pulled out his large thick cock and
squirted some piss into my water glass and placed the
water with piss down in front of me. I couldn’t have
been more shocked by what he had done. Putting his cock
back in his pants, he picked up his drink and said
“Cheers,” and drank it together with his chaser. It was
totally unreal; I didn’t know what to do as he watched
to see what I would do.

Downing my whiskey I picked up my water glass with piss
and hesitated, what to do; should I put the disgusting
mixture down and leave or show my submission and drink
it? Undecided I couldn’t make up my mind. Impulsively, I
drank it. A big smile appeared on Oscars face as he
said, “I thought so; I knew what you wanted the first
time I saw you admiring my cock in the steam room. Come
so that we can continue our conversation in private.” He
took my hand and led me to a long hallway in back of the
bar that led outside. On one side of the hallway were
the men and women’s bathrooms and opposite were a couple
of doors to separate rooms that the patrons of the bar
used to do their thing unobserved. Oscar led me into the
first private room and turned on the light.

The room was quite ordinary, a couple of easy chairs
with a table and lamp in the back, a large heavy oak
table in the center of the room and a lounge along a
wall with other chairs. Oscar removed his coat and tie
and instructed me to do likewise. I was still in a state
of shock by drinking that nasty brew and complied
without question. He turned me about and undressed me by
yanking my trousers and shorts down to my hips exposing
my prick and ass. Flustered, I objected, “Now wait a
minute, you said we would continue our conversation.
What are you doing?”

Pulling his belt out from the loops of his trousers he
said, “Bend over,” and gave me a lash across my ass.
“This to make the point that you are to serve me without
question,” he explained as he gave me two more.

“Yeow,” I screamed and he lashed me again across my
ass. “Please stop, this is unbearable,” I begged but he
paid no heed and gave me a couple more. My prick got
hard notwithstanding the pain and humiliation he was
inflicting on me.

“Spread your legs,” Oscar demanded, “We must get your
pants off to do this right.” Of course I obeyed as he
pulled down my pants making it easier for him to lash my
ass. No mercy shown as he applied that wicked belt
across my ass.

“No more,” I cried, “I can’t take no more.”

“Sure you can,” he generously said, “I’m not through
yet,” and he gave me some more across my ass. Being
satisfied he stopped and said, “Enough of this, now on
your knees, I’m going to teach you the fine art of cock
sucking. I do miss Kendrick. He became quite an
accomplished cocksucker after extensive practice; maybe
you can also if you put your mind to it.”

Not wishing to oppose him after my whipping, I dropped
to my knees to comply. Pulling out his magnificent cock
from his trousers he place the head of his penis to my
lips and said, “Open up and swallow my cock; you’ll like
it and take it all the way.”

Opening my mouth, I mumbled, “It’s much to big.

Pushing it in, he said, “You can handle it if you try.
Relax; you can handle it by swallowing it as it goes
down and concentrate. You’ll enjoy it, all my little
cocksuckers do.” He held my head with both his hands to
get the proper angle and pushed it down my throat; with
a great deal of effort I avoided chocking; savoring it,
I willingly accepted it to please him. As he reversed
direction I took a deep breath and sucked that enormous
cock as he pulled his cockhead to the front of my mouth.

Repeating the process I grabbed my own cock and back
down my throat his cock went. Pushing it in and out he
grunted with pleasure and he finally said, “I’m coming,
swallow, bon appetite.” And he shot copiously in my
mouth and I swallowed his discharge as I shot on my
pants that lay at my ankles beneath me.

Taking the tail of my shirt he wiped clean his cock and
said, “Clean up the mess you made with the paper towels
you will find in the cabinet there; get dressed, compose
yourself and meet me at the bar. We can have a drink and
continue our conversation at the bar.”

Having done the best I could in cleaning up under the
circumstance I joined him at the bar, I needed a drink
bad. I had mixed feelings from the experience; I never
even contemplated submitting myself to another man’s
carnal pleasure by sucking him off yet down deep I knew
I got a high from it but how could I now face him?

After I downed the drink that he poured me and offered
me a second, he said, “Don’t get me wrong, I can
understand your reluctance in seeing me fuck your wife.
I accept that. Besides I am willing to accommodate you
since I’m more interested in you then your wife. Besides
Maria likes your wife and wants to have her so that the
two of them can play together. It’s you that I want to
swing with. I especially like young society type guys
like you who appreciate the privilege of giving me head.
So don’t worry I’ll lay off your wife.” With these
comments and after another drink to calm down, we parted
with the understanding that we will get together again

I went home to my apartment to give this a great deal
of thought.

End of Part One

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2020-03-06 13:20:44

Swinging with Oscar and Friends

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