I Dare You
I dated Kay in grad school. While the “Soxer” was 11
years older than I was, she was fun to be with at times
and had a wild streak in her when it came to sex. She
liked to role-play, have sex in interesting place,
loved to exchange fantasies, and watch porno together.
The best thing was that she could deep-throat me and I
am not small (a little over 7.5 inches).
She liked to suck my cock and liked it when I came in
her mouth. Kay was 5’9″, 140 pound. She had 38c tits
and a nice pussy. I am a little over 6’00”, about 175
pounds. She said having sex with me was fun for many
reasons but mostly because I have an adventurous spirit
and I could make her have an orgasm by licking her
The Soxer had an aunt and uncle who lived about 45
minutes away, and we visited them several times while
we dated. Once, on a hot and humid early evening on our
way back to school, we stopped on a small side road in
heavily wooded area and practiced “parking.” I had
never done this before but always dreamt about it. We
started off hot and heavy in the front seat (my 2-door
car did not make the back seat conducive to these
While I played with her tits through her button-down
shirt, she massaged my dick. Eventually we stripped off
our shorts and began to fuck, but the steering wheel
began to cramp us. I backed out of the car and she hung
the lower half of her body out of the car. I rammed my
cock in and out of her causing her pussy to get hotter
I pulled her out of my Fairmont and leaned Kay up
against the car and penetrated her again. She wrapped
one, than both of her legs around my body-I kept her
pinned against the car while I pumped in and out of her
for a few minutes. Wrapping my arms around her, I
picked her up and slowly walked toward the hood.
All this time, I kept my cock inside her. Once at the
hood, I lay her back and started fucking her hard. My
hands drifted to her tits (still enclosed in her shirt
and bra) and eventually Kay’s clit. She began to
breathe harder and harder until I knew she was on the
edge of cumming. I sped up my strokes, pulling my cock
all the way out and slamming it back in. She came. Her
body gyrated. She sighed over and over “Oh my God!
Ohmygod!! How can you do this to me?!!” It was
I left my cock in her for another minute or so. After
pulling out, I was still mostly hard, but had yet to
cum. After a moment of rest, Kay came alive. She sat up
and after kissing me, softly said, “Thank you. That was
one of the best orgasms I have had in a very long time.
I guess it is time to take care of you. How can I get
I whisper back, “I want you to suck my cock. I want to
cum in your mouth.” She kissed me and slid off the
hood. Kay knelt before me. She softly held my cock, wet
from her pussy.
Looking at me in the eyes, she said, “You like it when
I lick your cock, don’t you?”
“Yes,” I hissed. She circled her tongue around the head
of my dick. As I grew to full size, she slid her mouth
along the sides of my cock, cleaning her juices off.
Then she started to suck on my cock. At first, the
Soxer just put my head in her mouth and circled her
tongue around my head. The whole scene was sexy; both
of us without pants, but still wearing our shoes. Me
with a t-shirt on; her shirt unbuttoned about half way.
Kay with my dick in her mouth. Just thinking about it
made my harder. I asked, “What if someone drives by?”
“Let them watch to see how it is done correctly.” She
took my cock deeper in her mouth with every pass.
Eventually, she shoved the whole thing in her mouth. I
felt my member hit the back of her throat and continue
down. She could only hold it there for a moment or two,
before she made me back out. I placed my hands on the
back of her head and played with her hair. Eventually,
I started to fuck her mouth. My orgasm approached. As I
got to the “point of no return,” I pulled my cock from
While pulling on my own dick, I held it about four
inches from her still open mouth. I came. I came in 5
big squirts. The first landed mostly in her mouth. The
second hit just under her nose. The third, on her chin.
The fourth and fifth I sprayed on her neck and down her
chest. She swallowed, then put my cock back in her
mouth and sucked me dry. After she released me, still
on her knees, she looked up and smiled. I will never
forget that scene: her mouth, chin, neck and chest
sticky with cum.
Slowly she stood up. We kissed. I actually like the
taste of my own cum, so I licked her chin and around
her mouth. We parted, “I guess we had better get back
to town.” I don’t know if she did it purposely, or the
humidity just fooled into thinking it was just sweat,
but the Soxer did not clean my cum off her neck and
chin. In fact, some of my cum soaked into her shirt.
She attempted to button up her shirt but I stopped her.
“Leave it unbuttoned like it is,” I said.
“Aren’t we stopping at the supermarket on our way
home?” she asked.
“Yes. But I want people to see your big tits, lust
after you and be jealous of me.” She looked a little
hesitant. “I dare you.” We were always doing these
“Okay, but I have a dare too; I dare you to leave your
underwear off.” I agreed.
We dressed and drove back to town. We glowing and
feeling pretty giddy. The humidity did not allow my cum
to dry on her neck and shirt. At the supermarket, I
noticed how both men and women looked at Kay. It was
obvious that she was covered in cum. Some gave look of
disgust, but most looked at her with lust. Several guys
spent a lot time examining produce while she leaned
over while picking out apples. I even got a thumb’s up
from one guy.
My cock started to grow again. As we proceed through
the store, she kept making me examining items on lower
shelves. As I squatted looking at some cans of soup, my
dick slid out of my shorts. Kay was staring at me with
a big grin. She was enjoying my display. We moved to
the next aisle, and I did it again.
This time, the Soxer whispered in my ear, “I love
seeing your cock. This is really turning me on.” Two
aisles later we ran across a friend of Kay’s from
church. She was a very attractive woman in her mid-
forties named Trish. As she smiled, she asked what we
had been doing, all the while staring at Kay’s chest
and neck. “Oh nothing,” Kay said with a wink.
Being a little brave, I decided to give her friend a
little show. I squatted and began to examining some
items. My now rock-hard dick sprung out. Trish stared
and put a very big smile on her face. I stayed down for
a good two minutes. After which, she said in a hush to
Kay, “You are so lucky to have a boyfriend like CJ.”
And then she winked at me. We parted. Kay kissed me.
Once we got home, we fucked like rabbits.
Several weeks later, we returned to Kay’s relatives.
Although we did not discuss it overtly, we both want to
repeat our previous encounter. To that end, I asked her
to wear only a loose fitting tank top with a plunging
neckline, and shorts without underwear. She made me
wear a similar outfit-tank top and the same shorts that
I wore before, without underwear of course.
We couldn’t be dressed like that at her aunt’s, so we
each wore a shirt over the tank tops. Because we were
only eating an early dinner with them, it was not
necessary to wear different shorts. Departing her
aunt’s, we both removed our shirts, and played each
other’s chests through our shirts. I could tell that
she was hot for me. I was equally excited for my cock
had already sprang to action.
She took a different route back to school, and had
little luck finding an isolated road. With light
fading, we got on I-94 with disappointment in our
faces. As the Soxer drove, I reached over and began to
rub her inner thighs. After a few miles, she exited the
freeway. “Why are you getting off here,” I inquired. “I
thought we might pick up a video.”
I looked up, and realized that she had pulled into a
XXX shop. Its parking lot was more than half full.
“Kay, are you sure you want to go in there?”
“What, CJ is getting chicken?”
“Well, I am just concerned about you,” I lied; I wanted
to go in badly, but I did not want her to feel she had
She looked me dead in the eye and said, “I dare you.”
That was all I needed.
We got out of the car and walked toward the entrance.
Kay still wore only the tank top, shorts and shoes. The
signs on the front door warned that “You must be 18 to
“Ah-oh,” I said, “do you think we should bring our
ids?” She giggled and just opened the door. We walked
into a bright room full of sex videos and “marital
aides.” All the 8 guys in the store looked at us while
we examined the titles. Kay and I would showing each
other video boxes with silly titles like “Edward Penis-
hands,” and “Sperms of Endearment.”
We giggled quietly with one another. At one point, I
quietly said to her, “The other customers are staring
at you.” She grinned. “I dare you to lean over and let
them see down you shirt.” She looked at me and winked.
Moving down the aisle about 5 feet, bent over at the
waist to look at some titles. The guys almost drooled
as they looked down Kay’s shirt at her big tits. She
did this about 3 times until all the guys had been
She returned to my side with a devilish smile on her
face. “I want you to squat like at the supermarket.” I
was a bit hesitant; flashing women was one thing, guys
was another. “I dare you,” the Soxer said. I proceeded
to the next aisle and squatted down. My dick popped out
of my shorts. The two men in my aisle gazed at my cock.
One smiled. Like Kay, I made sure I flashed everyone in
We were getting a little bored looking around, and then
I spotted the hallway, which lead to the “Private
Viewing Booths.” I had visited similar booths like
these once or twice before. I found them to be very
exciting. I motioned to Kay and nodded toward the hall.
She had a puzzled look on her face. I whispered in her
ear, “I dare you.”
She smiled and nodded yes. I got $5 worth of tokens
from the store attendant. The hallway was dark. On
either side were 7 booths. One or two guys were hanging
outside in the hall. Most of the booth’s lights
indicated that they were being used. The noises of the
videos filled the area. We proceeded down to end of the
hall and chose the second from the end on the left.
The little cubicle was crammed and dark. After closing
the door, we put the seat down. Kay and I were able to
sit side by side. I put the tokens in the illuminated
slot. The video screen sprung to life. The opening film
was of a woman being fucked doggy-style. Her huge tits
hung down and shook as the man pounded in and out of
her. Kay changed the channel. Looking around the booth,
I notice holes at crotch height on either side wall.
I knew instantly that these were “glory holes.” I had
read about them but never seen them before; they always
fascinated me. Kay settled on a movie that showed a
big-titted woman surrounded by 3 guys. While she sucked
one, she jacked-off the others. Kay’s breathing
increased, as did mine. I began to massage her thighs
and rub her tits. I nibbled on her neck, all the while
watching the screen.
Slowly, I moved my hand down to her pussy. I rubbed it
with the palm of my hand. The Soxer now grabbed my cock
through my pants. I pulled her shirt up and began to
knead her tits. Eventually, I lifted her shirt off. She
pulled my dick out. I pushed aside her shorts and began
to finger her.
I could tell that Kay was getting very excited. I
crouched down in front of her, put my tongue in pussy.
She moaned and kept her eyes on the video screen. I
worked her clit over while sliding 2 fingers in and out
of her. After a minute or two, I could tell that her
orgasm was approaching. I speed up my tempo. Kay came
hard, bucking on my face.
After a short rest, she looked down at me with a smile.
I sat back up on the bench on top of her shirt. With
her big tits swaying as she bent over, Kay began to
change channels. Eventually, she stopped on a gay movie
showing some guy sucking on a very large cock. She had
always been turned on by gay stories. I had confessed
to her that I had always wanted to try sucking a cock.
While we both watched the movie, she stroked my very
hard dick. She said in my ear, “You want to do that
sometime, don’t you?” I smiled at her.
Suddenly, as if on some cue, a cock came through the
glory hole on the left. We were both a little shocked.
She continued to stroke me. Looking at the faceless
dick and then at me, she said, “Now is your chance.” I
swallowed hard. It had been a fantasy, but reality? I
was a bit apprehensive. Again she said to me, “I dare
you,” and moved my head toward the cock. It was a nice
cock, about 6 inches long, fairly smooth and not too
much hair. My face was about 5 inches from it. Kay
repeated, “I dare you.”
I went for it. I wrapped my hand around it and licked
the head. A pearl of pre-cum oozed out. I licked that
off. Kay urged me on, “Run your tongue along it.” I
did. I came back to the head and swirled my tongue
around it. “Suck it!” she said. I let it enter my
mouth. I worked a few inches in my mouth. My head
bobbed up and down.
At one point I looked over at the Soxer, she was
squeezing her tits and playing with her nipples. I love
it when she does that. I sucked the dick with more
gusto. Suddenly, I felt it swell up. I knew he was
going to cum. I pulled off, but not quick enough. The
first shot entered my mouth. The rest hit my chin and
spread over my hand. I released the deflated dick. It
withdrew and I swallowed. The taste was not so bad. Kay
looked down at me very pleased, and in fact I was
pleased too. We exchanged gazes for a moment.
Suddenly, another cock appeared from the glory hole on
the right. This one was big-about 8 inches long. I said
to her, “You?” She just shook her head and nudged me
toward the pulsating cock. I licked the head, which was
dripping with pre-cum. Slowly I sucked the dick into my
mouth. It was so big, I had a hard time in getting it
Eventually, I was able to move about half of it in. I
moved up and down on it. Again, Kay played with her
tits. This guy came quickly, and this time it all went
into my mouth. I swallowed as much as I could, but some
of it dripped out of the corners of my mouth. The cock
I sat back up on the bench. We kissed and exchanged cum
from the strangers with our tongues. “I want to cum
now,” I announced. Kay moved down my body, but I
stopped her. I had something different in mind. “I want
you to suck me off through the hole.” She looked
puzzled. “I’ll go in the booth next door, and you suck
me off. But the kicker is that I want you to put on a
show so the guy in the other booth can see you through
the glory hole. And I want you let me cum in your mouth
and all over you tits.” Kay was hesitant. “I dare you.”
She said, “Okay.”
We stood and moved the bench up. I said, “I’ll be in
this booth.” I tapped on the left wall, and quickly
exited the booth. Just when I was closing the door, a
guy entered the booth on the left. I gulped. Now what?
The right booth was busy too. I stood there not knowing
what to do. After a couple, the right booth opened, and
a winded man walked out. I had just sucked him off!! He
walked past me and I ran into the booth.
I got situated and looked through the glory hole at
Kay. She was sucking the guy in the left booth!! She
must have thought it was me! I was concerned but also
very, very turned on. True to her word, Kay was putting
on a good show. She sucked with her head off to the
side. She kneaded her tits. I did not see it very
clearly, but I could tell that she was deep-throating
him at times. She put on a great show. I was so hard.
Soon, the guy started to cum. He came in her mouth and
on her tits. That is when I said through the hole, “Kay
what are doing? You’re sucking on the wrong cock!” She
immediately let go of the cock and sat back on the
bench. The Soxer looked a little dazed. I exited the
booth just as the guy in the left booth did. I ran into
the left booth. I looked through the hole and saw Kay
still sitting there. I heard another door close. She
looked down at the right hole and moved her face
towards it. She did not realize that I moved. A cock
appeared in the hole. I said, “Pssst.” She ignored me,
figuring I was a stranger. This cock was a monster-at
least 10 inches. She went to town on it.
Again, she gave me a good show. The cum of the previous
guy made her tits shinny. Kay did her best to swallow
this dick, but it was just too big. I continued to rub
my cock. I don’t think I have ever been so excited.
Soon the guy came; a huge load spattered all over her
face and tits. She looked very satisfied.
I exited my booth and knocked on Kay’s door, “Let me
in. It’s CJ.” After a moment of shuffling, she opened
the door and I stepped in.
She embraced me and deeply kissed me. She forced her
tongue in my mouth. I rubbed her soaked, slippery tits.
“That was fun,” she said.
“But Kay, you sucked the wrong cocks.”
“I knew that. I just wanted to put on a show for you!”
I was stunned, but still rock-hard.
“Suck me off now.” I sat on the bench and she knelt
before me. “You liked sucking those cocks, didn’t you?”
“Yes. And you loved watching me.” I did. Soon she was
deep-throating me. I was close and she knew it. She
pulled up and let me shoot on her tongue. She let it
pool there. I was spent. Kay crawled up to me and we
exchanged my cum.
We both rested for a few minutes. The Soxer put her
shirt back on; her chest was soaked so much cum that
her white tank top became almost see-though. Her
nipples stuck out. We both were a mess-cum all over our
faces and necks. “I guess we should get going.”
We got a few looks from guys as we walked down the
hall. The lights in the main room blinded us for a
moment. The clerk gave as a smirk and said, “I hope you
enjoyed yourself. Come back and see us again soon.”
Kay shocked me by answering, “Oh, we’ll be back soon!”