Member Article:Our First Couple and how they took our cherry! Post Your Comment

MalePlaymate 62 M
12  Articles
Don't like So so Good Very Good Excellent

What do you think?


Our First Couple and how they took our cherry!


It was about 36 years ago for my first time swinging with
a couple. Actually it wasn’t just me; I had a girlfriend
I had dated for a couple of years during college. I was 22,
a year older than her. I was a tall lanky young guy, 6’1”
tall 170 lbs, and blond blue and above average in length
at 8” and corresponding thickness. Cher was about 5’3”
110 lbs, black hair, and green eyes. And man was she built.
Now when we started dating, she had some nice 32-33”-B
cups; after about 2 months of seeing each other, she let
me play with them for the first time. A couple of weeks later
I was fingering her hot, wet, and extremely tight little

The following weekend we had sex for the first time. I used
a condom since she wasn’t on birth control at that time.
It was hot and sweaty and lasting all night long; once it
started and we both became accustomed to each other’s
bodies, each others preferences, we were banging every
opportunity we could find. Soon she started taking birth
control and we no longer needed the condom. I think an added
benefit was that the pill caused her to tits to grow a full
size. On her small frame they were magnificent! This was
the 70’s so shaved pussy was rare, even in porn movies
at that time. Cher had shaved her pussy with the exception
of a very small patch right above her clit! I loved going
down on her sweet tasting pussy, and I could get her so hot
and wet she would demand for me to fuck her.

After about 2 years of normal young lovers’ sex, we decided
one night to go to a XXX movie theater, which back then, the
mid 70’s, was as generally a building full of older guys
hanging out in the dark theater stroking their boners.
We enjoyed the movies we saw; Cher was especially turned
on by the 2 guys-1 girl scenes, and she also liked the girl
on girl action. When we left the theater, and got back in
the car for the drive back to my apartment for sex, she had
my cock out before we were half way home and sucked me dry
which was her first time swallowing a load. A few weeks later
we went out to a local “nude beach” at the lake and saw
numerous naked men and women hanging out, so to speak. She
got turned on and finally took her bikini top off and spent
the rest of the afternoon topless, growing somewhat comfortable
with public nudity.

Now for how we met the couple we played with. I was out with
some frat buddies at one of the downtown drinking places
one Friday night, Cher was out with her sorority sisters,
doing the same thing just down the street. As the night of
drinking and partying went on, I noticed I was being eyed
by an older couple sitting alone over in a dark corner. I
was young and therefore likely didn’t pick up the signals
they might have been giving off, so I really didn’t give
it much thought.

At some point I went to the men’s room and was joined at
the next urinal by the older guy I noticed earlier in the
evening. He said hello, I responded in kind. He asked how
I was doing; just your regular BS and we struck up a quick
conversation. Being a guy and being in the men’s room,
I couldn’t help but slyly take a quick peek at his cock
and I was really surprised. The guy was small, about 5’6”
and maybe 155 lbs, but he was packing a very thick cock that
had to be about 8” and he wasn’t even hard. As we finished
our business in the men’s room, and exited, the conversation
continued down the hallway and back into the main bar, where
he asked if I wanted to join him and his wife for a drink. Not
sure what his deal was, but not being an asshole or jerk,
I said sure I would join them for a little while.

He was Jim and she was Kay. He was 38, she was 34, and they had
two young kids and were out on a date night. Jim was blond,
green eyes, and you already know his stats. Kay was about
Cher’s size, perhaps an inch shorter, maybe 5 lbs heavier,
but still a hot looking blond mother of 2 kids. Jim ordered
3 beers for us, and while we waited for the waitress to bring
them, Kay excused herself to the ladies room. They were
good! It was a plan to seduce a college kid to play with, which
I didn’t know at the time. Jim asked if I had a girl; I told
him she was down the street at another bar with her girlfriends.

He asked if we fooled around as a couple, and I being the hick
kid, said "yeah man, we fuck all the time."

He laughed and said, No, I mean do you two swap with other
couples. I was stunned for a second or two, but I quickly
assessed the situation and figured out the intent. I was
not sure Cher would go for what he was suggesting, but I thought
I would hear him out. He said Kay liked to fuck young college
guys and tonight I was her 1st choice; he liked to fuck young
college girls. He said they had been swapping-swinging
for most of their marriage, even lived in a commune for a
year when they were first together. I told him to be honest
I wasn’t sure my girlfriend was up for this, although
I quickly told him about her interest in alternative sex
when we had gone to the XXX movies a few weeks earlier. He
said we could play it slow and he was sure Kay could gently
bring Cher around, given the opportunity.

Now I was intrigued as Kay returned to the table and asked
what we boys had been talking about. He told her I was interested
in fucking her, and that I had a girlfriend at a bar up the
street that was curious about doing 2 guys at once and maybe
even a girl. Come to find out Kay was bi, not hardcore lesbian,
but definitely into the occasionally girl on girl action.
Kay suggested we go to the other bar and find Cher and then
they would invite us over to their house to drink and hang
out in their hot tub. I was game, so I went to tell my buddies
I was leaving to go find Cher and would see them back at the
frat house the next day.

To make this part shorter, we quickly found Cher and her
friends, I cut her out of the herd of girls and after about
30 minutes of meet and greet we were off to their house. Cher
was with me in my car as we followed the couple to their West
Austin home. I didn’t give her any details of the previous
conversation I had with this new found couple, not wanting
to spook her before Kay had the chance to divine her interest.

It was in a nice neighborhood where they lived; as it turned
out Jim was a contractor and had built their home; it was
on a large lot, with excellent privacy. Kay took Cher on
a tour of the house while Jim and I got beers for everyone
and adjourned to the back deck. It was a warm spring night,
so we opened our beers and were soon joined by the girls.
The girls had changed from their clothes into light robes
and were carrying a stack of towels. Apparently Kay had
made a very good impression on Cher; they were laughing
and Cher seemed extremely relaxed with her new gal pal.
Kay said they were going to get in the hot tub and suggested
that Jim show me the house before joining them.

Jim took me inside and showed me the ground floor before
we went up the back stairs to a room which ended up being directly
over their garage. It was a second den/office/playroom
according to Jim. He asked me to give him a hand as he opened
a semi hidden closet door tucked in the corner of the room
under the stairs. He pulled out a huge thick down filled
mattress, and I helped him unfold it and lay it out in front
of a small couch which was against the wall. He pulled out
a comforter and asked me to spread it out over the mattres.
He pulled out a large suitcase, placing it on the table in
the opposite corner of the room. He opened it and removed
some video tapes; remember this was the 70’s before DVD’s.
He took one and inserted it into the VCR under the TV on a stand
in the corner and pushed play. As a movie showing a young
woman being fucked by two guys with huge cocks began to play,
Jim began to pull out sex toys, vibrators, nipple clamps,
and huge tub of Astrolube. He took out a pan with some rolling
papers and some weed, handed it to me and asked if we were
interested. Not being a completed babe in the woods, I had
smoked a joint once in a while over the years, and I knew Cher
wasn’t adverse to it either. I rolled a fat one and lit
it with a lighter I found in the pan. I turned to hand it to
Jim, who took it and suggested we get undressed and join
the girls down stairs in the hot tub. Having played high
school sports, and not wanting to appear to be a wimp, I agreed
and began to remove my clothes. Within a minute we were both
naked. Jim reached into a small black bag he had removed
from the large case and took out something. He stroked his
cock which was already getting hard and then rolled a black
ring onto his cock, all the way to the base. It seemed to immediately
make his cock get even harder, and definitely bigger. He
stroked his cock a few more times and he was hard and huge,
I guessed 10”, maybe even more, and thick as my wrist.
He looked over at me and asked if I wanted one. Being 22 and
perpetually hard, I hesitated for a second then said sure
I would give it a try. Having just watched him place the ring
on his cock, I followed his lead and placed the tight ring
over the head of my own cock, rolling it down the shaft until
I had it positioned against my pelvic bone at the base. I
tugged and pulled on it until I had it as far back as it would
go, then I stroked myself a few times and was rewarded by
even more blood filling my already swollen cock until it
was a good half inch longer and maybe ¾” to a full inch
thicker. The head was even larger than usual, swollen and
looking like it was dark pink balloon.

Jim just smiled and said "that will not only keep you
hard for a longer period, it will help keep you from cumming
so soon; a young guy like you could stay hard all night-fuck
several women and not cum until you take it off." He
sort of chuckled, and added, "a young guy like you,
the first load might hit the ceiling when you finally let
loose. Now let’s go join the ladies and share these cocks
with them."

He picked up the joint from the ashtray, grabbed his beer
and I followed him down the stairs, through the kitchen
and out onto the deck where the girls were already playing
in the hot tub. As we walked out on the deck I noticed that where the hot tub
was located at the back of the deck had stairs on either side
of the tub which lead down to a lower deck which surrounded
an in ground swimming pool. That was about all I was able
to survey of the landscape when to my surprise, and delight,
I saw Cher was sitting up on the edge of the small pool and
Kay was in the water, between Cher’s legs, lapping at
her wet pussy. Jim turned and smiled.

"See I told you Kay would be able to convince her to
explore her sexuality."

Boy was he right. Cher had both hands tightly gripping the
edge of the tub and her legs were up to the point that her knees
were out of the water, her legs spread as wide as she could
and retain her balance. Kay had her hands on either side
of Cher’s pussy, spreading the lips and she was sucking
on the younger girls’ clit. Cher’s head was rolling
around and she had her eyes closed, very much enjoying the
carnal pleasure that Kay was giving her. She had no idea
that we had returned.

Jim slowly eased up to the tub, turned and sat backwards
on the edge, swung his feet up and in, then turned and sat
on the opposite side of where the girls were playing. I followed
him in to the tub and took a place on the same side next to him.
He lit the joint, lay the lighter on a bench/table like portion
of the deck that was behind us, took a long hit, held it and
passed it to me. As I took a long hit, he drew a tug off his beer
and sat it back on the same bench as the lighter. I mimicked
his actions, exhaling the smoke, tugging on my beer and
sitting it on the back table. We relaxed and turned our attention
to the girl on girl action going right in front of us. I was
sure both of the girls were by now aware of our presence in
the tub with them. About that time Cher let loose a long,
low guttural moan as she apparently reached what was to
become her first of many orgasms that night. For some weird
reason my eyes caught a glimpse of a clock on the wall in the
kitchen behind the girls and saw that it was 12:30 AM. It
had only been about 2 hours since I first encountered Jim
in the men’s room of the downtown bar.

About this time, the girls came up for air, if you will; Kay
stood up between Cher’s legs and leaned to give her a very
passionate kiss, while hugging her. Cher responded in
kind to the passion and they remained lip locked for what
was about a full minute. When they broke from each other’s
embrace, Cher giggled and said "my pussy does taste
sweet." having encountered own juices that were
smeared all over Kay’s mouth, lips and chin.

Kay asked Jim for her beer which was like ours, behind us
on the table. I fetched Cher’s for her, and moved over
next to her as we both sat back in the tub, side by side.

"So, how are you enjoying the little party we have
stumbled on tonight?"

She turned her head, gave me the same deep passionate kiss
she had just given to Kay, and replied "that she was
having a wonderful time with our new found friends."

Then out of the blue she asked me a question.

"Are you ok with me fucking both of them?"

I hadn’t really thought of it as being a problem, so I answered
her question with one of my own.

"And you’re ok with me fucking Kay?"

She laughed, before saying, "are you still going
to love me in the morning?"

"I don’t see how I could love you more than I do right
now, so I certainly wouldn’t love you any less."

"Good answer Mr., " she smiled.

One more question she queried, "Kay asked if we had
any limits as to what we will or won’t do, sexually speaking.
I told her I couldn’t speak for you, but we are both young
and fairly inexperienced so we likely don’t know what
our limits are." Kay said nothing happens to anyone if they don’t want
it to happen, so I told her I was open to pretty much anything.
Game on!"

I laughed and said, "well I am not sure what all they
will want to do, but if I don’t like it or feel comfortable
with it, I will certainly decline the request. And with
that, I kissed her deeply, and said Game on!"

Jim broke up our quiet discussion by asking if we were ready
to take the party up to the playroom. Cher gave me a peck on
the lips, and replied for both of us.

"We are ready for whatever you guys have in mind, let’s
get this party started!"

We all stood, picked up all accessories from the bench and
left the tub. Towels were passed around and everyone dried
off good, before heading upstairs. Cher was impressed
with the room, and immediately sat her beer down, fell into
the middle of the big mattress on the floor and seeing the
2 guys-1 girl video playing on the TV, announced that she
was read to fuck.

Kay gave Jim a kiss and told him "she was going to the
bathroom to pee and you two should give this girl what she

With that, Kay turned went up two steps into the adjoining
bathroom and pushed the door closed, but not before I noticed
how damn hot her ass was, considering that she had born two
kids, she had a narrow, round tight butt that screamed fuck
me. I had to do her doggy style before the night was over’;
that would be awesome.

Jim brought my attention back to the task at hand.

"Cher if you will get up on the couch on your hands and
knees, we will fill you on both ends."

She scrambled up and was in position in a flash. He guided
her to where I was standing at the end of the couch with my
cock in her face and she didn’t need to be told what to do.
She reached to take my cock in her hand, pulled me to where
it was at her lips and engulfed my cock. Jim took a handful
of the lube from the big tub and rubbed some on Cher’s pussy
to get her instantly moist, then got on the couch behind
her and before placing his huge cock in her, assured her
he would go extra slow to give her tight young pussy plenty
of time to adjust to his thickness and length. She just mumbled
and nodded in agreement without ever taking my cock from
her mouth. Jim slowly pushed until his cock head was inside
her cunt lips. She murmured and he held his position, giving
her time to adjust to the size. Slowly he pushed in a little,
pulled back out, gently working in inch after inch of his
length. It took a couple of minutes, but before she knew
it, Cher had his groin firmly against her ass checks, the
result was he had all 10 1/2” buried to hilt.

Just as she had done when Kay was sucking her clit in the hot
tub, she let a long, low moan of pleasure. I started to rock
my hips back and forth, pushing my cock in until I hit the
back of her throat, then pulling back out until only the
head of my cock was between her lips. Jim pulled out to where
his cock head was between her pussy lips, and I pushed in,
this time going past her mouth and into her neck. When I pulled
out, Jim pushed into her pussy until he hit bottom again.
Her whole body shivered. A mini orgasm! He pulled back out,
I pushed in again. I went as far as I could. Jim and I were in
sync and we were giving her a really good fucking, from both
ends. In the position I was in, I saw Kay quietly come back
down the steps from the bathroom. She stopped next the desk
at the bottom of the steps and picked up small camera from
the desk. She smiled at me and then raised and pointed the
camera in our direction. She began to snap a picture, and
move, snap another and move. She took about 5 or 6 pics of
Cher’s first time having two guys giving her cock at the
same time.

When she finished with the pictures, she returned the camera
to the desk and then walks over and knelt down on the mattress
right in front of the couch. She reached under Cher with
her left hand and began to fondle her tits, playing close
attention to her young, hard nipples. Cher shivered again.
With her right hand, Kay reached under Cher and found her
clit, and began to rub the swollen love button. Cher went
over the edge; she lunged backwards into Jims’ cock,
driving it as deep as she could into her hot, wet twat. She
also sucked even harder on my cock, literally sucking back
into her throat. With that, she launched into a full body

She went limp, her entire body began to quiver and shake,
her pussy began to squirt juices all over Jim’s cock,
in addition to Kay’s hand and I know for a fact the spend
was so intense that she lost consciousness for few moments.
Her eyes rolled back in her head, and then she just collapsed
in a pile on the couch. Both the cocks slipped from her body,
and Jim and I were both amazed at her intense response to
the stimulus she had just received. Kay leaned over to stroke
her hair, and kissed her gently on the shoulder.

Kay gently whispered to her, "that was awesome and
I am so glad you are getting to experience new and erotic

Jim had gotten up from the couch, and wander over to the table
to roll another joint, but I noticed that first he began
to dig around in his little black bag. I moved over near him
to observe what he might be up to and he said he some other
party favors, if we were interested. Curious, but remaining
silent, I waited until he explained. He held up small bottle
of sorts which appeared to contain a large crystalline
“rock” with some loose white powder in the bottom of
the bottle, and quietly said, we like to take a bump of this
once in a while when we party. I didn’t have to ask, I knew
that he what he was offering. Again, having been around
different people with various habits, I wasn’t totally
uninformed as to the drug. Kay finished comforting Cher
and the two of them ventured up the stairs into the bathroom.

Jim pulled a mirror from the other side of the table, opened
the bottle and poured the contents out on it. He took a small
razor blade from his bag, and began to shave flakes of powder
from the rock adding to the small pile already there. He
placed the rock back in the bottle and proceeded to chop
the flakes into powder. Then with swift movements he started
to cut and divide the pile into longer lines across the mirror.
He reached back into his bag and removed a small gold colored
straw tube.

"You want to try a little" he asked?

Taking the straw from him, I didn’t reply. I leaned over
the mirror, lined the straw up at the end of the first of the
lines, and inhaled as I moved the straw up the line. It disappeared
into my nose. He nodded and said to try one in the other side.
I repeated the process and then handed the straw to him.
He immediately did just as I had. I felt and immediate clearing
of my head, from all the beer and weed we had ingested over
the last few hours. I also felt the rush through my body,
but mostly I felt it in my cock. What a blast!

Kay and Cher came down the stairs and came to us. Jim took
Cher by the hand as she walked up and offered her the straw.
She hesitated, and he hugged her close and assured her that
it wouldn’t hurt her, and that in fact, she would enjoy
the effects it had on her body during sex. He explained to
her how to do it, and she bent over and inhaled a line; he said
she should change nostrils and do another. She did! She
stepped back and he took the straw and handed it to Kay who
knew exactly what to do. She did a couple of lines and then
Jim licked his finger and rubbed it across the mirror, getting
a small amount of the powder on his finger tip. He pulled
Cher closer to him, and bent over to lick her nipples, one
after another. When they were properly wet, he rubbed the
powder on his finger all around her right nipple, repeated
the process of getting more on his finger and rubbed it around
on her left nipple. Then he took a 3rd dip of his finger onto
the mirror, and reached down to rub Cher’s pussy this
time. He rubbed it all over her clit and continued to rub
until she shivered with a small orgasm.

Not to be outdone, I bent over and licked his wife’s nipples
to moisten them, then began to repeat what he had done, in
fingering her nipples and clit with the powder. Same result
as I rubbed her clit, a small intense orgasm. Kay then licked
her finger and touched it to the powder on the mirror, but
surprised me when the lowered her hand and began to rub the
powder onto the head of my cock. The warm tingling feeling
intensified as she did this. I leaned over to hug and kiss
her, to show my appreciation for her gift.

She pulled me over to the mattress and down with her as she
got in on all fours and wiggled her ass at me.

"Want to do it doggy style?"

She didn’t have to ask me twice. Jim leaned over and offered
the tub of lube to me; I took a glob on my finger tips and stroked
my cock a couple of times, which was hard and throbbing for
Kay’s pussy, then I reached under her and rubbed the lube
around and into her hot pussy. I placed the head against
her twat lips and slowly entered her. I went all the way in,
until my hips were firmly against her ass checks and held
onto her hips. She shivered slightly and as I had said before
the game was on!

Jim smiled and nodded to me as he escorted Cher out of the
room and down the backstairs. I figured they were going
back to the hot tub for some sucking and fucking. In the meantime,
I had Kay all to myself. I began to slowly plunge in and out
of her wet hole. She started to respond; I could feel her
tighten her inner muscles on each out stroke, as if to hold
onto my cock head as I hesitated before slowly pushing back
in. I continued the slow pace for maybe 10 minutes, slow
and steady, but I could tell that she wanted me to speed up
a little. I did! Not too much, just enough for her body to
recognize the difference. This caused her to push back
against me each time I bumped into her ass with my hips.

Then she asked me to stop for a moment. She leaned forward
enough to break our connection and shuffled a few steps
on her hands and knees until she reached the couch, where
she stood up and leaned forward, placing the palms of her
hands down to balance herself. I got up and walked up behind
her and leaned over to pull her hair off the back of her neck
and kiss and nibble on her neck. Then with one hand, I positioned
my cock and slowly pushed back into her warm, wet pussy.
Still leaning over her, I reached around and under her and
rubbed her tits in a circular motion. I tweaked her nipples
between two fingers. Then to really get her attention,
I squeezed her nipples firmly and pulled them downward,
stretching them a bit. At the same moment, I pulled my hips
back and then shoved my cock firmly back to the hilt.

This really seemed to stimulate her; it drew a moan from
her as she threw her head back and said, "oh yeah, that’s
it baby, fuck me harder. Now we were getting going!"

I picked up the pace and began to pump my cock in and out of
her, each time getting a little faster, banging into her
a little rougher. Each increase brought an mmm, or a yesss,
or an oh shit that feels so good. Within a matter of minutes
I was hammering her from behind, very fast and very hard;
while still tugging and pulling on her thick, hard nipples.
The pounding continued like this for maybe 3-4 minutes,
until she began to cum. It was a spectacular cum, too! She
was banging her ass back against me as roughly as I was banging
into her tight pussy. Her pussy was gripping and releasing
my cock in a steady rhythm. Her pussy was dripping wet; I
could hear the sloppy noises and feel the wetness on my cock.
With that, she orgasmed; hard, too! She fell forward onto
the couch and my cock popped out of her. She was moaning and
saying oh shit yeah, that was fucking great! Not wanting
her to end her orgasm, gently rolled her over, climbed onto
the couch, pulled her legs up and over my arms and plunged
my cock back into her roughly. I started to jackhammer her
cunt with all my strength. She immediately began to cum,
again and again. It was incredible to feel her body respond
to my actions. She lifted her hips to meet each thrust, banging
her pelvic bone into mine. She pulled on my ass, as if to get
my cock even deeper into her. Then she went way over the edge.

She shrieked a very long "EEEEEHHHHH! YYYEEEEESSSS!"

And with that her body went limp. I rose up, letting her legs
fall to my sides, leaving about half my cock still inside
of her, but letting her rest. She was breathing very hard
and giggling between each breath. That was great, you do
know how to fuck a girl she complimented me. It occurred
to me that my balls were aching, that I still hadn’t cum!
Incredible! It took about 5 minutes, but she soon recovered.
I looked over at a clock on the VCR. It was close to 3 in the
morning, I had been sucked by Cher, and fucked Kay long and
hard and I still hadn’t cum. Not to be too egotistic, but
I was pretty impressed at my performance. I leaned back
a little, needing to stretch my legs, my cock slid out of
her and she stretched her legs out as I stepped up and off
the couch.

I wondered what Jim and Cher were doing down stairs. Kay
said that she was going to pee. I picked up a beer and told
her I was going down to see what the other two were doing.
I went down quietly and slowly, so as not to interrupt any
fun they might be involved in. I wasn’t disappointed.

As I came through the kitchen and stopped at the open door
to see what was going on, I saw that they were in the hot tub.
Cher was standing, but leaning over at the waist, her hands
were firmly on edge of the tub, with Jim standing behind
her, his huge cock was buried inside her. But it noticed
that it wasn’t her pussy that he was in. His cock was up
between her ass checks. I will be damned, I thought. He got
her to take it up the ass! He wasn’t really moving in and
out of her, so I assumed it had taken all this time for him
to gently stretch her asshole and get that monster cock
deep in her tight young ass. About that time, Kay came up
behind me and quietly put her arm around my waist, as she
stood beside me and just stood there watching the same thing
I was seeing. We watched for a few minutes; Jim would very
slowly pull his cock out until just the head remained inside
Cher’s tight young ass, then he would just as slowly push
back in, until he his groin gently bumped against her ass
checks; he was indeed, balls deep inside her.

Kay stood on her toes and whispered in my ear, "looks
like he broke her cherry!"

I just smiled and nodded in agreement.

She said "they seem to be fine, let’s go back up stairs;
I want to try something new with you."

I just nodded yes, and we quietly turned and went back up

Kay told me to sit down on the mattress and lie back with my
head on the pillows against the bottom of the couch. She
went to the table and got the mirror, brought it over and
offered me some lines. She took a couple for herself; she
sat the mirror down on the couch behind my head. She kneeled
between my legs and took a firm grip on my cock and began to
stroke it. Lowering her head, she licked and sucked, but
just the head. Then she reached over me and got some powder
on her finger. She rubbed it all over the head of my cock,
and then repeated the process with her nipples and her clit.

To my great surprise, she had one last thing she wanted to
do. She took her finger and rolled it around in a line from
the mirror, when she showed it to me, her finger was entirely
covered with white powder. She said for me lean back and
to close my eyes. I wasn’t sure what she had in mind, but
I wasn’t about to tell her to stop. She took my balls in
her hand, lifted them up and with the finger she had the line
of powder on, began to run the tip around the rim of my asshole;
it immediately tingled and went a little numb. She continued
to circle the rim, until she reached the center hole. I had
a thought as to what was about to take place, but again, I
wasn’t prepared to stop her. She slowly began to push
her finger into my ass. As she did, she rotated her finger
in both directions, spreading the powder around inside
of me. As she did, the sting just evaporated.

I was not longer an ass virgin. She had her whole finger inside
of me. She wiggled the finger around and the feeling went
from apprehension to incredible pleasure. Then she really
surprised me. She reached with her other hand and began
to slowly pull the cock ring up and finally off of me. What
amazed me was that my cock was still as hard as it had ever
been. She wiggled her finger some more and stroked my cock
up and down slowly. What a feeling! Then she lowered her
head and took my cock in her mouth. She sucked on the head
while her hand slowly gripped and stroked up and down the
shaft. Still wiggling her finger in my ass, I felt the pressure
in my balls begin to build. About this time, Kay wiggled
a second finger into my ass, still sucking and stroking
my cock. Then she let go of my cock, and took more of it into
her mouth; moving her free hand down and began to squeeze
my balls. The pressure just got more intense! She sucked
harder, squeezed my balls harder and in a real surprise,
started to fuck my ass with two fingers. No more wiggling,
she was slowly pushing her fingers in and out of me. I wasn’t
going to last much longer. And then she stopped, pulled
her fingers out of me, let my cock fall away from her mouth,
quickly reached for the cock ring and replaced around the
base of my cock. I was in agony and ecstasy at the same time. " Why did you stop, I was about to cum."

I know baby, but I want to fuck you some more."

With that she climbed up on me and lowered her dripping wet
pussy over my cock and sunk down until I was fully inside
of her. She leaned over and kissed me; and not a gently kiss,
it was hot and passionate, out tongues did battle with one
another, our lips and teeth pecked, sucked and played games
with each other. Kay began to slide up and down, back and
forth on my cock. She would rub her clit against my pelvis,
rise up until just the head remained inside of her, and then
slowly slide back to the bottom. It was hot, but she wanted

She looked me straight in the eye, and said "you and
Cher are going to be different after tonight. You will want
to explore more and more sexual adventures, together,
and perhaps even without each other. If she wants to do another
girl, or another guy, you are going to have to allow her the
freedom to do so. You may not know it yet, but I expect you
will want to explore your sexuality as well."

"What do you mean by that?"

"If you expect Cher to let you fuck her ass, then you
are going to have to expect that she may want to do the same
to you?"


"You seemed to enjoy it, and very much so, when I had
two fingers in your ass-well if you get to do her, then she
gets to do you if she wants to."

"What?" I must have had a panic look on my face
by this time so Kay held my head in a reassurring manner and

"With a strap on! AND, I am thinking that before Cher
gets to try it, I get to break your cherry!"

"What are you talking about?"

"I have a strap on in the case over there, I think you
should get on your down hands and knees in the middle of the
mattress and let me take your ass, right now!"

"I don’t know if I can handle that."

"You can, and you’re ready. I could see it in your
eyes, and feel you body respond when I fingered your ass."

"If you say so, I guess I can trust you in this."

"Well OK then, let’s do this! But you are going to
need a good deal more powder and some additional stretching
to take my toy."

"Again, I trust you, so show me what to do."

She bounced off my cock and on to her feet in an instant. She
got out the bottle, poured the rock onto the mirror, took
the blade and shaved off a goodly amount of powder. She prepared
a dozen or so lines, replaced the rock into the bottle and
put it away.

She handed me the straw and said "two lines up each
nostril, please and thank you!"

I followed her instructions and took one line, then the
other, then back to the other side for another, and finished
with the final one in the other nostril. I closed my eyes,
took a deep breath and allowed the rush to flow through my
body. Kay said for me to get on my hands and knees in the middle
of the mattress. I did as I was told. She came up behind me
and I felt her rubbing more of the powder on the rim and stick
her finger in to rub even more inside. Then she touched me
with what I knew wasn’t her finger. I hadn’t noticed,
but while I was taking the lines she had taken a vibrator
from the case, dipped it in lube and now had turned it on and
it was buzzing against my asshole. She circled it around
a few times, then pressed it against the center. She pushed
a little more firmly and it slipped in an inch or so.

She said, "oh yeah baby, you so ready for this, "
and with that, she slowly pushed it all the way in.

It stung for just a second or two. The sting passed as quickly
as the stinging had begun, it ended. And I was engulfed in
flood of pleasure. From head to toe to asshole, my entire
body began to tingle. The vibrator was designed for this,
it was a firm, but soft rubber composition and it had a grove
around the base, which my asshole clamped onto and made
it stay in place. Kay said I should stay still and she would
be right back.

I could see her in front of me as she went to the case and removed
what was a harness like rig and put in on. Then she took a 7
or 8” cock colored dildo from the case, dipped it in the
lube and snapped it into place. I watching all this and my
blood was rising; to my head, to my cock, to my entire body.

She looked down at me and asked if I was ready for this? I nodded
with a sheepish smile.

"Relax, you will love this and you will never forget
losing your cherry to an older woman!

She got back down behind me, slowly pulled the toy from my
ass, smacked me on the ass and giggled. I felt the head of
her “cock” pressing against my asshole. I couldn’t
believe this was about to happen. She pushed and the head
slid past my tight sphincter muscle with a popping feeling.
She was in.

She hesitated, asking if I was ok. I took a very deep breath
and nodded yes. She pushed in further and didn’t stop.
I felt her hips bump into my ass and she was all the way in.
She patted me on the ass, then ran her hand up onto my lower
back, more like a mother assures a child than a woman banging
a young guy in the ass with a strap on.

It was crazy but the feeling was so intense that I didn’t
wait, I told her to fuck me. She did.

She pulled out and went back in slow, this time I felt her
touch my prostate gland and it was an incredible feeling.
I wanted, I needed to cum, but with the cock ring holding
back my jism, the feeling of pleasure was intense. She started
to acquire a rhythm and began to fuck me faster and harder.
Then she reached under me and grasped my balls. I hadn’t
heard them, but Jim and Cher had quietly come back upstairs
and were standing behind can watching the show.

I first heard Cher quietly tell Jim, "I know what he
is feeling right now."

Jim, replied, "yeah, it’s a great feeling when
someone buries a big one in your in your ass."

Cher giggled in agreement.

Jim then told her she should get down under me and suck my
cock. She didn’t waste any time. Next thing I know she
has wiggled under me and has my cock in her mouth. She replaced
Kay’s hand with hers, on my balls. She began to squeeze
them while sucking hard on my cock. Kay in the meantime had
taken both her hands and gotten a tight grip on my hips at
the waist. She began to increase her speed and intensity
of fucking me; pulling me back towards her each time she
thrust into me.

About this time, Jim appeared on his knees right in front
of me. I looked up to see him smiling and stroking his monster

"Pretty damn hot, right buddy?" I just nodded
in agreement.

"Well, you have gone this far, so you might as well
go all the way – you should suck my cock!"

I heard Kay and Cher murmur their agreement in unison. At
this point, with Kay banging me hard and fast while Cher
squeezed by balls and sucked my cock, my mind was spinning.

I opened wide and he pushed it into my mouth. Well, here I
was, Kay banging my virgin ass, just as Jim had just done
to Cher, while Cher was under me, squeezing my balls and
sucking my raging hard on, and I was sucking one of the largest
cocks I had ever seen! He pushed and pulled, he was fucking
my mouth, just as I had done to both the women earlier in the
evening. He hit the back of the throat few times before finally
pushing past and right into my neck.

Then it happened. I had an orgasm, but I didn’t cum in the
normal way. My body shook, I sucked on his cock, as Cher continued
to suck mine, while Kay slammed into me with her dildo one
last time, buried to hilt in my tight ass. It was fucking
awesome. Then all of sudden they all stopped and moved away
from me I rolled over on my back in the middle of the mattress.
I was so fucking high and the feeling was so intense, I could
just make out them talking in the background.

Jim said "I was no longer a ass virgin, and neither
was Cher."

Cher agreed and said "I can’t wait for him to fuck
my ass and me to fuck his."

That was when I heard Kay tell them both there will plenty
of time for that.

"It’s Friday night, actually very early Saturday
morning, our kids are at the grandparents for the rest of
weekend, and if you two don’t have to be anywhere, you
should stay here all weekend, stay nude, fucking, sucking!
We have plenty of food when everyone gets hungry there is
plenty of beer, wine, and liquor, as well as weed and blow."

Jim agreed and my head started to clear as I looked up to see
Cher giving a Kay a big, wet, sloppy kiss as she accepted
the invitation.

Jim looked down at me and asked if I was ok with the plans we
just made.

I smiled and nodded ok. But I have a question/

"Are you 3 ever going to let me blow my load! My balls
feel like they are going to explode any second now."

We all laughed as it was decided that Cher and I were going
to spend the next couple of days at our new friends’ home.

Jim suggested that we all needed a swim, followed by a relaxing
dip in the hot tub, and maybe a couple of hours of rest. He
started to remove the rings from his cock and balls; I did
the same and well headed out to the pool. After a good 20 minutes
or so of swimming, one by one we went to the hot tub.

As we were sitting there quietly relaxing, Kay asked if
anyone was interested in mixing up the sleeping arrangements.
Cher was the first to speak.

"That sounds like fun!"

Before she could express her preference, Kay asked if Cher
would like to sleep with Jim.

Cher leaned over and kissed her and said that would be great.

Kay then spoke to me.

"Are you alright with Jim spending the rest of the
night with his big cock buried in Cher?"

As I nodded in agreement, she completed her plan.

"And just so you know, I will let you blow your load
in me; on me, pretty much any hole or any place you want!"

We all got out of the tub, dried off; Cher kissed me good night,
telling me she loved me and thanks for a great time tonight,
and then she and Jim disappeared up the stairs to the master
bedroom. Kay and I followed close behind, stopping to clean
up the empty beer bottles, empty the ashtray, and grab a
drink of water.

She asked if I wanted anything, and again, I said, "boy
I would love to cum before I grab a little sleep."

She smiled and said "I can help you with that. But first
you need one more thing."

She grabbed some pillows, a couple of sheets and blankets
from the closet and pitched them on the couch.

"I thought we might just sleep in here if that’s
ok with you."

"Fine with me" I replied.

She told me to lie down and get comfortable as she walked
to the case on the table and slyly retrieved a dildo looking
item and dipped it into the lube. Kneeling down she asked
me to pull my legs up and back.

She said, "this is a butt plug and it will gently stretch
you while you sleep, not mention with it in your ass, you
will come like a racehorse when I suck you off."

Without replying, I pulled my knees up to my chest and grabbed
my checks, spreading my ass wide. She slowly twisted and
pushed until the plug popped into my ass. Then she pulled
my legs down and asked if I was comfortable. I nodded a yes.

She then picked up my half hard cock, removed the cock ring
and jacked it a few times. That was all it took….I was completely
hard again. She moved around and climbed on top of me, lowering
her pussy down to my mouth. I began to lick on her very swollen
clit. I swirled one way, reversed and swirled back in the
other direction, and then just to make sure she knew I was
still down there, I would plunge my tongue in and out of her
slit in a very rapid motion, going in as far as I could go.

She was literally flooding my mouth and chin with her juices.
I guess I was doing something she liked. While all of this
was going on, she had taken my throbbing cock and was slowly
sliding her hand up and down the shaft, with just the head
in her mouth. Not to diminish her effort, she was sucking
so hard I was beginning to feel the suction all the way to
my swollen balls. Not for nothing, she was also swirling
her tongue around and around the head of my cock.

She was about to see the result of her actions. She and her
hubby, not to mention Cher had not allowed me to cum all night.
My load was full and I was ready to burst. If felt my balls
tingle first, then the feeling increased as the first shot
hit the back of her throat. She squeezed by balls and sucked
harder, not that she needed to. Like a volcano I erupted
in her mouth, I think I remember moaning very loudly but
since my mouth was attached to her pussy it was muffled.

Time after time, I really lost count at 5-6 squirts and it
just kept coming. More and more of my sticky cum shot into
her mouth and I vaguely recall her swallow, breath, swallow,
breath, as she took more and more cum. I was lost in my orgasm,
but for some reason, it occurred to me to see if I could send
her over the edge with me. I sucked on to her clit with what
must have seemed like a vacuum. I repeatedly hit just the
tip of her clit with my tongue and in a final effort I remember
moving my hand up to her ass, finding her hole, and plunging
first two, then a third finger deep in her asshole.

Again, I guess I did something right. She started to fuck
my mouth with her pussy. She shook and vibrated, rubbed
and ground her cunt all over my mouth. She couldn’t move
too much, due to my fingers having her pinned to the position
she was in. She just let loose with almost as much girl cum
in my mouth, almost as much as I had just pumped into her mouth.
It was fucking incredible! I barely remember both of us
just collapsing in a sweaty pile. She was still on top of
me, her pussy had a slow warm trickle of juice still running
out of her, I could feel the warm liquid still flowing on
my chin.

She started to come back to reality at about that same time.
I patted her on her lovely ass to let her know I was still under
her. She rose up and as she looked back over her should towards
me, she smiled and spoke first.

"Did you cum, sweetie?" She laughed loudly.

"That was fucking amazing."

"I have sucked off many guys over the years, and I am
telling you now, I have never in my life seen a guy cum so much
and for so long. I thought you were not going to stop cumming.
And Jeez, sweetie, you made me cum like crazy; that little
move you made there at the end…Fucking Amazing!"

She scrambled to get next to me, placed her head next to mine
on the pillow, pulled a cover up over both of us, kissed me
on the cheek, and said get some rest.

"You are going to need it for tomorrow. I have plans
for you and your little girl friend.

"Do tell" I said sleepily.

"I am going to spend some time with Cher, fucking her
holes, and sucking that sweet little pussy of hers, assuming
Jim doesn’t wear it out tonight."

"And for you, I think you need to suck Jim’s big cock
and let him blow a big load in your mouth. You will enjoy that,
I think, almost as much as you will having him do your tight
little ass, just like I did earlier. You two will never forget
these two nights and days with Jim and I!"

With one last peck on my cheek, she snuggled up close to me.
Sleep tight baby, and thanks for a wonderful evening. Those
were the last words I heard before we both drifted off to
sleep. I was trying to imagine what Jim and Cher were doing
now, and what Cher and I had stumbled into with the new friends
we had just made.

Post Your Comment | Mark As Favorite

Member Responses Post Your Comment

Members can vote on this response!

Great story.

You ought to write more, put things like this in the Swinging
section too


Members can vote on this response!

Still a working man, but when I retire I will try to write
more. FYI-99% of my stories are actual, factual events,
with names changed of course;, as I try not to embellish
while taking a small amount to literary license to make
the stories as interesting to read as they were for me to
experience. I have had some crazy times since I left the
small town in Texas where I grew up.

Working on a supplemental piece about getting to have the
girlfriends older sister, her very first time with a man.
Will get it posted as soon as I edit the draft. Glad to hear
from all who enjoy. Thanks to all!


Members can vote on this response!

Did you and Cher stay together afterward??


Members can vote on this response!

This story was centrinly over the top.. very errotic.


Members can vote on this response!

fuck, that's one of the best stories I've ever
read on here. and I've real a lot of them..... thanks


Trapper69 61 G
Score 5.8

Members can vote on this response!

Hot Hot Hot!!!!!!!!!!


Members can vote on this response!

Great Story! I'm Still Hard!


OpenMan 56 M
Score 0.9

Members can vote on this response!

Awesome!! Can 't wait to find out if you were able to
take that fat cock up your own ass! Did K fuck Cher, too?


Members can vote on this response!

THAT is what sex is all about!


Members can vote on this response!

that was a great story !