My wife was a woman in a bit of an emotional or moral
turmoil. On one hand she wanted to explore but on the
other she was a complete prude. When we were at home she
dressed in a very conservative manner seeming uptight
all the time. The only exception was when we went on
holidays when she would loosen up and wear bikinis and
somewhat revealing clothes not much mind you but
certainly more than she did at home.
We had discussed going to Key West for Fantasy Fest a
number of times and looked at the information on the
web. Karen was interested in the pictures of the men and
women walking around in broad daylight with very little
else on other than body paint, but said there was no way
she would do that. Personally I thought she would be a
hit, she has a slender figure, not overly endowed on the
top but certainly enough to enjoy a full B-cup. Her
legs and ass were her best assets and could easily have
belonged to a top lingerie model.
We finally booked the trip and left to see what it was
all about. Our hotel was a couple of blocks off Duval
Street where we knew the action was. We arrived there
about 6:00 in the afternoon and got ready to start
wandering around. In spite of the warm weather Karen
wore a dress that would have looked good on her
grandmother. We wandered from one bar to the next for a
little while just watching the sights. Karen wasn’t very
good at holding her liquor so was starting to get high.
By the time it got dark we were starting to do more
watching and walking than drinking as Karen had pretty
well reached her limit and when we passed a very
discreet looking store that seemed to sell lingerie and
sex aids we decided to go in. The store was run by a
very classy woman probably in her 60’s with a name tag
that said “Anne”.
She took Karen under her wing and started showing her
all the different toys. Karen was blushing and trying
not to look interested. Anne finally pointed to a dish
on the counter with pills in it and said “You need one
of those.” Karen asked what they were and Anne told her
they were pain killers called Percocet and said they
would relax her, give her a sense of euphoria and let
her enjoy Key West more. Before I could say anything
Karen had taken one and quickly swallowed it.
As the sex toys didn’t seem to be of much interest to
Karen, Anne started showing her nightgowns and other
lingerie. The obvious sex oriented outfits were quickly
passed over but she did seem to be interested in the
nightgowns. Finally Anne talked her into trying one on
and, after a few minutes in the changing room Karen came
out with knee length nightie that looked very nice but
was about as transparent as a burlap sack. Even Karen
seemed a little disappointed and much to my surprise
said, “You can’t even see me through it; I could wear it
Anne went to the rack and pulled another one off and
handed it to her saying “Try this.” Karen was back in a
few minutes wearing the new one. I could see her bra and
panties through it reasonably clearly. She said “I like
the way this one looks but it’s very itchy.” Anne never
hesitated and pulled a third nightie off and handed it
This time Karen was gone awhile longer and when she came
back giggling it was obvious she had taken her bra off.
In fact everything was obvious. She might as well have
been standing there in her panties. The nightie just
provided a slight blue tinge to her body. Her nipples
were very erect and she was breathing a little hard.
This was not a Karen I had seen before. She turned to
Anne and asked, “Do you think I would be safe wearing
this out on the street? Its dark now and it won’t be
like it is here in the store will it?”
Anne, bless her soul, said of course she would be safe
but it would be better if she took her panties off as
well. Anne stepped forward and crouched in front of
“May I?” she said.
Karen just nodded and Anne reached up under the nightie,
grasped the waist band of Karen’s panties and pulled
them gently down. When she had them down to the floor
level she waited for Karen to step out of them her eyes
locked on Karen’s vagina which was only about a foot
away from her nose. Karen placed her hand on Anne to
keep her balance while she stepped out of the panties.
She almost lost her balance anyway when she tried to
shake the panties off her right leg and Anne quickly
slid her hands up both sides of Karen’s left leg somehow
managing to get them under the nightie and steadied her.
I noticed that the top of her right hand was right
against Karen’s vagina and her thumb looked like it was
searching for her clitoris. Karen stood there for a
moment and then stepped back giggling again as Anne let
her hands drop.
As far as I knew Karen had never had a lesbian encounter
and I had no idea how she felt about this latest
experience but she certainly looked like she was ready
for anything. Her breasts and nipples were on display
and her vagina was clearly visible. She had never had
very much pubic hair, just a sprinkling above her slit
and the top of her vagina lips could be seen quite
plainly through the nightgown.
I paid for the nightie and Anne said she would mention
to friends to keep an eye out for us and make sure we
didn’t get into trouble. Taking Karen by the hand we
walked out into the night. In the dark of the street
Karen’s nightie seemed a little less transparent. In
fact you had to look closely to see she was naked under
The gown was full length and I guess she pretended she
was fully covered. She actually got more attention than
the women that were walking around naked with just body
paint. Any time I got behind her I reached under her arm
and cupped her breast. At first she objected but then
seemed to get into the swing of things and didn’t mind.
In fact when we stopped to look in a window I stepped up
behind her and reached around and cupped both breasts
tweaking her nipples which were getting very hard.
A couple of times men stopped us and asked if they could
take pictures of her. The first time she just stood
there almost covering herself with her arms. But by the
time the third man asked she grabbed the nightie at the
sides and pulled it tight around her body. Her breasts,
her by now very erect nipples and vagina were fully on
He asked her if she would drop one shoulder strap which
she did without hesitation and one breast was completely
exposed; the nipple standing proudly erect. After her
“photo shoot” we moved on.
At one point we were stuck in the middle of the street
in a crowd that wasn’t moving, we were just standing
there watching a juggler. I was just to her right and
behind her. A man who was directly behind her put his
hand on her ass and I thought shit, she is going to kill
him. She glanced at me and saw it wasn’t my hand and
turned to the front again. The crowd wasn’t moving and
the guy started to move his hand up over her hip and
under her arm.
She actually lifted her arm to accommodate him. He
reached around and cupped her right breast. We stood
there with him fondling her breast and playing with her
nipple with his right hand. His left hand was now on her
ass. I saw him trying to get it between her legs but she
wouldn’t move them apart to let him. The only other
person who noticed was a woman on her other side. She
was smiling as she watched the performance.
Finally, after a couple of minutes, he let go of her
breast and moved closer behind her and reached around
her other side with his left hand and, I guess, started
playing with her vagina. I couldn’t see what he was
doing but the other woman turned towards Karen and
reached out and started playing with Karen’s other
Soon Karen started humping her hips forward in a jerky,
uneven movement and finally spread her legs. At first
she had her feet about a foot apart but then she moved
again and her feet were about three feet apart and she
was still humping her hips forward, now with a more even
pumping action. It was obvious she was trying to fuck
something. She started to crouch. It seemed she was
trying to get her knees farther apart. I pushed ahead a
little so I could see what the man was doing to her.
I guess he had “walked” her nightie up with his fingers
and his middle finger was pushing slowly in and out of
her cunt in time with her humping. The other woman was
holding the nightie up for him and Karen’s cunt was in
plain view for anyone who cared to look. God, she was
fucking his finger.
The man reached down and under the nightie and back up
to Karen’s ass. He spread her cheeks and started rubbing
her asshole. Her head was down and she started to wobble
on her feet and I was afraid she was going to fall down.
The other woman let go of her breast and put her hand on
her shoulder to steady her.
Karen looked at her and grabbed hold of the woman’s
jacket for balance. She started to moan and whimper and
her breath was catching but she never lost eye contact
with the other woman. It was almost like she was looking
for approval for what she was doing. She grabbed the
man’s wrist and pumped his hand harder. She was staring
into the other woman’s eyes when she came and grunted,
“Uh! Uh! Uh!” in time with the thrusts of the finger she
was fucking. Nobody else seemed to notice and the woman
just smiled and quietly clapped her hands.
The crowd started moving and so did we, me leading a
rather dazed Karen. We soon stopped again. This time she
was facing me. Another man was standing beside me also
facing her. I saw him looking up and down her body. Then
he reached in his pocket and pulled out his car keys
which had a small flashlight attached. He held the light
up, looked at me as if asking for permission.
I nodded my head and shrugged. He turned the light on
and played it across her breasts which were clearly in
view in the light. I noticed Karen had her eyes closed
and it appeared she was not paying any attention to the
man. She was just standing there with arms down at her
The man just looked for a minute then slowly reached out
with his other hand and touched her breast. He kneaded
it gently and pulled on her nipple. He reached up and
slid her left shoulder strap down and gently uncovered
her breast. Bending over he took her nipple in his mouth
and sucked gently as he bunched her breast up with both
hands, his palms almost flat on her chest, the sides of
his hands squeezing her breast up and out.
When he took his mouth away after a while her nipple was
standing up hard and red and her breast was squeezed
between his thumbs and forefingers on both hands. He
stared at his erotic display for about 15 seconds then
let go of her breast and gently raised her shoulder
strap. I was surprised when he turned to me, said,
“Thanks,” and as he moved on I noticed a stain spreading
on the crotch of his pants.
Again the crowd started moving and we began walking
again. Karen was starting to wobble on her feet and I
was getting worried she was going to fall. All of a
sudden there was another couple walking beside us. The
man, a small fellow with glasses about fifty years old
said that Anne was worried about Karen as she had
allowed her to take the pill. His partner, a woman who
looked in her forties, said that Anne had suggested they
come and find us and take us back to Anne’s apartment
above the store.
At that moment Karen started to wobble and giggle more
than before and I readily agreed as I didn’t want to try
to carry her all the way back to our hotel.
The man introduced himself as Michael and we each took
one of Karen’s arms. The woman introduced herself as
Kathy and walked in front trying to clear a path as we
led Karen back to where the store was.
It took us about 10 minutes to get back and head up the
outside stairs to Anne’s apartment. We were only about
half way up when the door at the top opened and Anne
appeared wearing a dressing gown. “I was starting to get
worried about you guys; I should never have let her take
We helped Karen into the apartment and Anne directed us
to sit her on the bed. By this time she was giggling and
babbling away and sat on the edge of the bed with a
silly grin on her face partly drunk and partly something
else. Anne went over and sat beside her. Karen giggled
and asked her if she was going to stop her from falling
Anne asked “Do you want me to?” and she looked at me
inquisitively. I nodded and said that was fine with me.
Karen jumped to her feet, spun around to face Anne and
said “here I go, stop me” as she lifted one leg in the
air sideways. Anne quickly reached under the nightie and
ran her hands up Karen’s other leg until they stopped at
her ass and her crotch. Her right hand was wedged tight
against Karen’s pussy and as I watched I saw her thump
slip easily between her lips and up into her cunt.
Anne moved her hands away and Karen stood quietly in
front of her smiling. Kathy walked over and sat down
beside Anne. She reached down and lifted Karen’s nightie
up and slowly pulled it over her head. I realized now
that they were both lesbians and things were going to
get interesting. Kathy dropped the nightie on the floor
and reached up and placed her hands on Karen’s breasts.
I looked over at Michael and noticed he was staring
intently at Karen and thought, ‘Thank god he isn’t gay
Anne grasped Karen’s hips in her hands, guided her
around and eased her backwards onto the bed between
herself and Kathy. Karen lay down contentedly with a
sigh on top of some towels spread on the bed. Her feet
were on the floor and she started pumping her hips up
and down raising and lowering her mound in some kind of
Kathy stood and quickly striped off her clothes. I had
to revise my estimate on her age. She had the body of a
very fit woman in her late thirties or early forties.
Her breasts were very small, similar to a young girl.
About the size of half an orange they were hardly more
than nipples. She was cleanly shaven. In the meantime
Anne had removed her dressing gown and was lying beside
Karen in a nightie very similar to the one Karen had
I have never before and will probably never again see
something so blatantly sexual.
Anne looked at me and said, “Obviously we would all like
to fuck her and my question is would you like to go
“No,” I replied. “I certainly want to watch, though, and
if Michael is included he’ll have to wear a condom.”
“No problem,” Michael replied. “I already have it on.”
I looked over at Michael on the other side of the room
and saw for the first time that he had quietly stripped
his clothes off while the action was going on at the
bed. As I mentioned he was a small man, only about 5 ft.
3 in. In fact both Anne and Kathy were bigger than him
though Kathy not by much, and, for that matter, so was
He was standing there with his penis, it seem odd to
call anything that dainty a cock, stuck straight out and
up from his body. What he lacked in size he certainly
made up for in rigidity. I swear he could have poked
holes in the drywall with it. It was only about 3-1/2 to
4 inches long. He was a perfect match for Kathy, two
middle aged adults in children’s bodies.
Anne told him to come on over and we can get started.
She and Kathy lifted Karen’s feet up off the floor and
brought her legs up to her chest and then spread her
Karen’s only response was to say, “I hope someone is
going to fuck me soon.” And she waved her feet in the
air. I moved around so I could see between her legs. Her
vagina was spread open and the pink insides were
starting to show. I couldn’t believe she was lying
there looking like that and apparently enjoying it.
Anne reached into the bedside table with her free hand
and came out with the trusty KY jelly which she spread
in a line from the top of Karen’s pussy lips to her
anus. She than started to rub it in and Karen began
When Anne got to Karen’s anus I noticed she paid
particular attention to making sure it was well
lubricated. Karen had never allowed me to enter her
there but Anne slid a finger into that hole with no
objection and slowly worked it around.
I noticed Karen had a strange look on her face and then
she said “That feels good. I never knew it would feel
like that. Go deeper.” Anne complied and soon she had
all of her finger wedged up Karen’s bum hole. She
started moving it in and out and Karen started to moan
“Do you like that?” Anne asked.
“Yes, please don’t stop, ummm, it’s wonderful,” Karen
replied. But Anne grabbed a towel and discretely cleaned
her finger as she pulled it out.
“Don’t worry,” she said. “Michael is here.”
Michael moved up to Karen’s ass and placed the head of
his cock against her anus. He pushed gently and the head
“Oh!” groaned Karen. “Is he going to fuck my bum?”
Michael took over supporting Karen’s legs and slowly and
gently worked his penis into her asshole until he was
imbedded its full length.
In the meantime Kathy had been busy. She had strapped on
a rather large dildo. It was about seven inches long but
very thick. I asked her if it was something she used on
herself but she replied that she never put anything into
her vagina that was larger than Michael’s cock. That way
they could enjoy each other with no problems.
Kathy stepped over to the bed and lay down on her back.
She called to Michael, “I’m ready if you are.” Michael
pulled out of Karen with a popping noise which caused
her to complain that she didn’t want it to stop.
“Don’t worry,” Anne said. “We have lots more fun for
you. See Kathy there. I want you to sit on that nice big
cock she has.”
Karen looked at the dildo apprehensively. “I don’t think
it will fit. I’ll never get it in me. Do you have a
“Just try,” Anne replied.
Karen climbed up on the bed and stepped across Kathy,
positioned herself over the dildo and started to crouch
until it touched the lips of her pussy and then paused.
Anne moved over to her side and signalled me to get on
her other side.
“Help her down.”
We each took an arm and gently pushed her down.
“Oh shit, it’s starting in. Fuck it’s big.” Karen slowly
let herself down. “Oh fuck… oh god… shit, shit,
shit! Aarrg! Oh fuck! Fuck! Fuck!” Finally Karen was
sitting on Kathy’s hips. Kathy reached out and pulled
Karen down to her.
“Just relax,” Kathy said. “Let your cunt get used to
Karen was still muttering, “Fuck… fuck… fuck…
fuck!” over and over. Finally she stopped and just lay
with her head on Kathy’s shoulder.
Kathy waited for a while and then reached down and
grasped Karen’s hips. Anne and I joined in and we lifted
Karen up about two inches and let her down. That started
the “Fuck fuck Fuck” again. We kept lifting her hips
and letting her down. Soon we realized that Karen was
now doing the work. She was lifting herself up and
dropping back on dildo that was stuffed up her vagina.
Soon she picked up speed and lifted more and more. When
the head of the dildo was almost coming out of her
vagina on each lift she cried out, “Fuck, I’m coming!”
and started making the same grunting noise that she had
in the street when she was being finger fucked. She came
with a few loud grunts and collapsed onto Kathy.
Anne said, “You’re not finished yet,” and signalled to
Michael who stepped up on the bed behind Karen and
placed the head of his penis against her bum hole.
Karen looked up startled and said, “God no, not both
holes, I won’t be able to stand it.”
But stand it she did as Michael pushed his penis up into
her ass. He started to work it back and forth in a
smooth motion and soon Karen was starting to grunt
again. Just as Michael tensed and I knew he was coming
she let out a yell, “Fuck me! Fuck me!” and a shudder
ran through her body.
Things slowed down after that. I found Karen’s dress but
not her underwear. As she put it on I said goodbye to
the other three and we walked to the door. As we were
leaving Anne called out, “Will we see you tomorrow