This story is about two roommates I used to know and one
of their sexual adventures I shared in. There are many
more stories to tell about Joan and Cory, especially
Joan. The roommates could have been female version of
the “Odd Couple”, especially in how they portray their
sexuality.
I met Cory first. She is a somewhat petite blonde with a
tomboy personality. Cory portrays a sense of innocence
in both her dress and social interactions, although her
sense of style augments her body well and her
“innocence” is a turn-on for many of her male and female
pursuers. However, as you get to know her suspicion
builds she is not as innocent as she first seems. For
example, you notice how snuggly her dress hugs her hips,
how her skirts are just a little too high for a prude
and how her choice in swimwear is somewhat revealing.
Cory likes to talk about sex. However, it usually
involves her roommate Joan’s antics or something she has
heard about. I believed her until this night and to this
day do not know if this was an awakening of her wild
side or the real Cory showing through. She grew up in
Bakersfield, California and picked up a certain amount
of toughness and ability to interact with guys on their
terms through her youth. She attended Chico State
University for the “academics” and not the partying, she
says. However, I should have known someone that new
birth control pills would give her a rash in high school
and which foods made semen taste which way probably had
not had such an simple upbringing.
I had heard about Joan through Cory’s stories long
before I met her. The sexual tramp I thought she was did
indeed turn out to be real, as I will tell you about now
and in other stories. However, Joan turned out to be
much more. An orphaned child Joan was not as much a
tramp. Rather, she is much more sexually free than most
people you meet in the corporate world are. Something I
learned to appreciate.
I met Joan when I transferred to her site. A cute
brunette her two most stunning features are her face and
her breasts. Specifically she has a smile that can knock
you over and eyes that communicate an inner strength yet
show vulnerability at the same time. Her breasts are
simply spectacular. They are the nicest set of 34D’s you
will ever lay eyes upon. Joan also carries herself with
a good posture, which only accents her assets.
I had known Joan for several months and already had
several exciting sexual adventures with her before the
night I am going to tell you about. The night started
somewhat innocently with a get together at the local
microbrew pub with a mixed group of acquaintances from
work, the gym and mutual friends. Around 11 p.m. a group
of ten to fifteen adjourned to the apartment I shared
with two roommates as was normal. The margaritas were
flowing and eventually the party drifted down to about
five people.
The group being three single women and three single guys
eventually the conversation turned to sex. Specifically
the orgasmic difference between guys and girls. Cory and
Carol, another friend from work, both expressed sorrow
for guys only being able to orgasm once while women were
multi-orgasmic. My roommate and I nodded our head in
recognition of this but did our male best at boasting
how we each could cum many times in a session (although
neither of us had had the opportunity).
Joan had been quite up to this point but did have a
devious smile on her face. “I can make a guy cum twice
in a row!” She looked up and exclaimed.
“No you can’t. You’re always bragging but I don’t think
you can get a guy to cum twice in a row.” Cory
challenges back.
“Maybe you can’t but I can.” Joan teases her roommate.
“You can not. And just because he spurts twice that’s
not the same as cumming twice.” Carol adds.
“OK, if you ladies can’t, I bet you I can.” Joan
responds, not being dragged into further discussion.
“How much do you want to bet?” Cory chides back.
“A hundred dollars?”
“OK, and the winner gets the master bedroom. Obviously
they’ll make better use of it.” Joan responds.
“Deal!” replies Cory.
“That’s all good and well ladies, but how are you going
to settle this bet?” Carol asks, somewhat oblivious to
the little tents us guys were growing.
“We’ll use him,” Joan mentions pointing at me. “In fact,
to make it even harder I’ll bet you that I can make him
cum quicker the second time around than she can the
first time.”
“I’ll take that bet!” Cory replies.
“Are you game?” The women look over at me. I was
hesitant. But, the sexually wanton stares of the women,
the alcohol enabled weakening of the inhibition and my
building horniness made me agree.
The women set the rules. Cory did not want to perform in
public so it was agreed that we would use my bedroom.
The time was to start when we entered the bedroom and
would stop once the woman exited with clear evidence I
had cum. Cory was set that she did not want to have
intercourse so the contest would be limited to hands and
oral pleasures.
I thought the night was already good enough when Joan
leaned over and whispered in my ear, “I really, really
want to win tonight. You try and hold out really long
with Cory and I’ll make it worth your while. I’ll treat
you right and you’ll get to fuck Cory tonight in
addition to cumming twice.” With a wink she moved away.
“Hey, no cheating” Cory responded seeing us talking.
“How could I cheat?” Joan shrugged. “And you get to go
first. How much more of an advantage do you want.”
Cory took me by the hand and we went to my room. She
shut the door behind us as I sat on the edge of the bed.
Her look was focused as she knelt in front of me and
quickly unzipped my pants. As her hands pulled my semi-
flaccid member out I saw it was 12:30 in the morning. I
try to remember Joan’s whispered promise as I feel
Cory’s mouth enclose my cock. I focus on other non-
sexual thoughts as much as I can as Cory’s head bobs in
my lap. She is not bad and I cannot stop myself from
becoming fully erect and moving closer to orgasm. I
watch her head bopping up and down as I feel myself
disappearing into her warm, wet mouth. I had daydreamed
exactly this event at work many times as I sat through
meetings with Cory.
I held back as Cory’s inexperience showed. She continued
to only mouth my cock and with the same rhythm. Fifteen
minutes passed before an exasperated Cory pulled back.
Her hand was still on my cock as she looked up at me.
She looked frustrated and I encouraged her to try again
but with variety. Her tongue licked the underside of my
cock as her hand started to masturbate me. She sensed my
stimulation and stroked harder and deeper as her mouth
worked only the head of my cock. This was too much for
me and I came.
Cory had little warning and most of it struck her in the
face and front of her shirt. She bounced up from her
knees and headed towards the door. As her head poked out
she called time. Twenty-two minutes had passed. I zipped
up my pants and headed back out to the living room
thinking I had never seen a woman that happy with me
spooging on her face.
“Ok, your turn.” Cory stammered at Joan. “And know
waiting around, this is suppose to be back to back
orgasms!”
“I think I can beat twenty-two minutes.” Joan answered
as she handed Cory a towel. “Hopefully you can clean the
sperm off you before I get back.” I had reached the
living room and met Joan as she was getting up for her
turn. She surprises everyone as she removes her shirt
and bra. My eyes are fixed on the motion of her breasts
jiggling with her stride and only slightly notice Cory
complaining. “No fair.”
“It’s fair, we’re on our way to the bedroom.” Joan
responds. At the same time she guides my hands to her
breasts. I cup them and feel her nipples tightening as
she turns to continue to the bedroom. She has me hug her
from behind, my hands still fondling her glorious mounds
as she whispers in my ear. “I want you to lick my pussy
good, finger me, do whatever you want to me. As an added
treat just do me one favor. If I get you to cum four or
more times or a chance to do Cory and me at the same
time I want a promise from you. Tomorrow, I want you to
promise to eat me out and lick my hot cunt for an hour!”
I nod my head in agreement as we close the door. Quickly
Joan has my clothes off and has me flat on the bed. She
gives me a big deep french kiss before smothering my
face in her breasts. I suckle for all I am worth not
noticing she has dropped her skirt. Seductively she
turns her back to me and lowers her panties. Her nice
pussy stares at me as she bends fully at the waist and
pushes her panties to the floor. “Remember, my tits and
my pussy are yours honey!” Joan whispers as her knees
straddle my head. I stare at her pussy hovering
enticingly above me. My hands instinctively reach for
her breasts. They play with her soft mounds as they
dangle freely from her chests. My fingers flicking over
her nipples while my hands knead that special flesh. Her
mouth sucks my cock in aggressively.
“Don’t worry about cumming, remember the deal. You cum
now and you will see a lot more pussy tonight.” Joan
says as her hand masterfully strokes me. Her hips edge
towards me and I accept her invitation. I feel her hand
fondling my balls as her mouth sucks me. The smell of
her pussy enticing my tongue reaches for her and starts
to lick. I bury myself in her as she sucks and strokes
me expertly.
The tension is already building in my balls when Joan’s
fingers rake across the skin under my balls and around
my asshole. My head falls back on the pillow as my
orgasm starts. Joan senses it as she strokes harder and
sucks much more firmly on my cock’s head. My hands grip
her breasts firmly as I tell her I’m going to cum. My
balls squeeze and release their fluid as Joan lowers her
tits to my cock to receive my load. I spray her tits
with my first bursts. She uses her hand to milk the rest
out of me and into her other hand.
“How much time?” she asks.
“Five minutes or so, we came in at about 1 am.” I
respond. “Good, no hurry.” She replies. “Help me with my
clothes will you.” She requests as she unwinds herself
from our sexual position and gets her feet on the floor.
I start to pick up her panties and other clothes she
corrects me, “no just the skirt.”
I kneel on the floor and open the top of her skirt so
she can step in. Her pussy is inches from my face and I
cannot help but lick it. “That’s a good boy…you’ll get
lot’s of chances to do that!” She smirks. I pull her
skirt back over her hips and reach for her shirt but she
is already out the door.
“Five minutes!” She screams as she bounds into the
living room. Carol, Cory and my roommate stare at her in
wonder. Is it the five minutes or is it that she is
topless with cum dripping from her tits. “Looks like I
win!” “Yeah, wonderful.” Cory responds, pouting about
her loss. The time is late and Carol asks my roommate to
drive her home. Something about being a little too
drunk, although I think Carol might have had something
else on her mind by this point.
A quiet descends after Carol and my roommate leave. I
relax on one end of the couch and Cory is on the other.
Joan offers to get beers and makes her way into the
kitchen. I smile over at Cory and she weakly smiles
back. She is pretty sitting the partial shade, the only
light coming from the kitchen.
The late evening and aurora of sex add to her
enchantment. She really is a cutie with her legs pulled
under her sitting comfortably. The slight smudge of
dried cum on her cheek and T-shirt doesn’t hurt either.
Joan returns and hands each of us a beer. She sits back
on the other chair and crosses her legs. She amazes me
as she nonchalantly adjusted her skirt to cover more of
her leg, seemingly oblivious that she is topless. She
notices Cory’ s pout as well, “What’s wrong?”
“I’m upset about losing the bet.” Cory explains.
“That’s OK, you don’t have to pay me or change rooms if
you don’t want to.”
Joan lets her off the hook.
“That’s not it….” Cory states, unable to complete her
statement. After a moment of awkward silence Joan
encourages the rest out of her. “I’m no good in bed!”
Cory finally stammers, “It took me twenty-two minutes
and I barely did it. No wonder nobody wants to sleep
with me.” I start to laugh at this until I notice the
harshness of her gaze. “Cory, I’m not laughing at you
just that you can’t possibly believe nobody wants to
sleep with you. How many guys hit on you everyday? I
know I’ve fantasized about you quite a bit.” I blurt out
the last piece without thinking. “Oh really” Cory asks
confrontationally, “Then how come it took twenty-two
minutes for you to cum.”
“It really wasn’t his fault Cory, I did cheat a little.”
Joan tries to help out.
“Did he fuck you!” Cory accuses, “That wasn’t allowed!
And God knows I could have used a good fucking tonight!”
her tone getting more agitated.
“No, no, I didn’t do that. But I did use my other assets
to get him done quickly. Remember, I was married before
and unfortunately perfected the art of the quickie.”
Joan responds.
“Did you like her doing you better?” Cory asks. “How can
I be better?” “Cory, it was different, not better. Joan
just took charge vs. you were more demur and loving.
Just different styles.” I respond. “Cory, if your are
really still horny why don’t I demonstrate what I did.”
Joan asks as she hands Cory another beer. “I know I
didn’t get off yet so I could use a little more.”
“Joan, why do you get a little more. You already used
him up.” Cory responds her frustration building. “Just
because I’m not good enough to get him going again.”
“You can do him if you’d like. And you are good enough
to get him going again.” Joan encourages. I shake my
head in disbelief. Joan has Cory demanding to have
another go with me.
“OK, Cory do you want to make love to him or just get
fucked?” Joan asks. “In other words, do you want to see
what I did or do you want to try something different.”
“I’d like to see what you did.” Cory responds.
As Joan passes by me she whispers in my ear “She’ll see
that and probably get fucked as well.”
“OK Cory, the 1st thing I did was try to get him excited
before we went inside. I know you think it is cheating
but it worked. Take of your shirt and bra.” Joan
requests. Cory hesitates slightly before compiling and
revealing her tantalizing B-cup titties. Cory starts to
cover up when Joan corrects her. “Don’t be shy about
your tits. Guys love them. Show them off and tease him
with them. Remember what I did?”
Cory thinks about it a minute and then walks over to me.
She surprises me as she tells me in a surprisingly
seductive voice, “Do you like my tits” and guides my
hands to them. They are soft sensuous little balls of
flesh. Easily fitting within the palm of my hands. I
squeeze and fondle them before lifting each nipple to my
mouth for a quick kiss. As I start to lick them I hear
Joan, “Cory, now that would have been cheating.”
Cory guides me behind her and I repeat the walk to the
bedroom, this time cupping Cory’s little mounds in my
hand. Joan follows behind and closes the door as we
enter. “The next thing I did was strip him.” Cory
hesitates and Joan follows up, “Just start taking his
clothes off. I don’t think he’ll mind.” She quickly has
my shirt off and lowers my pants and underwear to the
floor. The new approach taking direction she stops and
kneels and takes my cock in her mouth.
“You’re already hard again,” she looks up and exclaims,
my cock still marginally between her lips.
“Of course,” I reply, “Don’t you know every guy would
love to fuck you?”
She smiles and starts to go down on me again. Joan let’s
this go for a minute and then hints to Cory that this
is not “exactly” what she did.
Cory breaks free and we proceed. Once again I am guided
to the bed and lie back in anticipation. I watch as Cory
unzips her pants and pushes them down. She turns her
back to me and seductively slides her french-cut bikinis
off her hips and down her legs. Catching on to the
seduction she looks at me through her legs and mouths,
“Do you like my pussy?”
I nod yes.
Joan whispers into her ear and Cory moves according to
the direction she has received. I help guide Cory’s
knees to either side of my knees and position her pussy
over my face. My hands have just started to massage her
breasts when I feel her mouth engulf my hard cock. Her
technique has become noticeably more aggressive. Her
breasts are small enough one hand can stretch to cover
both nipples. I fondle and tease her tits with my left
hand as my right starts to stroke the nice vagina above
me.
I’m enjoying the sensation on my cock, the tight nipples
and breast in my hand and the sight of the vaginal lips
above become fuller as they open and the moisture starts
to seep out. Cory’s hand is soon working my cock as her
mouth and tongue concentrate on the tip of my penis. I
bury a finger in Cory’s opening and finger fuck her as I
feel her start to play with my balls. I know I will not
last much longer. My hand leaves her breasts and I place
them on her hips. In anticipation she lowers herself and
my tongue starts to dance over her labia. The smell,
taste and sense are too much. I let her know I am going
to explode and she hungrily picks up the pace of her
masturbation. I bury my tongue deep into her pussy as
the first squirt of jism strikes the back of her throat.
To my surprise she doesn’t let go but greedily sucks on
my cock, inhaling the juices I’m letting go. I hear Joan
tell her, “Four minutes, that’s very impressive your
little cock-sucker!” Her swallowing has turned me on
even more. I re-engage with her pussy and run my tongue
up and down her crack, pushing in as deep as I can go.
Cory moans in pleasure.
My orgasm subsiding I feel my cock slide out of her
mouth. She leans her hips back into me as her head falls
on my hip next to my drained penis. I lick for all I am
worth as I enjoy the feeling of her hair covering my
balls and partially deflated cock and her breath on my
balls. I am determined to pleasure her as I re-insert a
finger deep inside her. Her pussy now much wetter my
finger slides in easily as does the second. I start to
rub her inner canal vigorously as my tongue finds her
clit. Cory rocks back on me as I work her pussy. She
tenses as a wave of orgasm hits her but shows no sign of
wanting to leave.
I continue on licking her for the next several minutes,
occasionally reaching for her chest and tugging at her
hard nipples. Something she seems to enjoy. I am hard
again as she pushes free from my grip and rolls off onto
her back next to me.
She pants hard as her hand reaches down to her wet
middle and lightly strokes herself. I rise onto my
elbows and admire her. My view unique and unexpected.
Her legs spread and her middle completely soaked from
her prior orgasms and my tongue’s lashing. Her fingers
gingerly disappear in and out of her vagina. Her eyes
beckon me.
“I’m on the pill.” She lets me know. A clear invitation
I do not need to her twice.
I position myself between her legs and aim my re-
hardened cock at her wet opening. I rub my cock up and
down her lips and over her clit to tease her. She arches
her head back at the new sensation of my cock rubbing on
her aroused and sensitive clit. She shudders once or
twice before making eye contact again. Our eyes remained
locked as my cock pushes into her. Her pussy is at once
warm and inviting and I slide my full length easily into
her. I start to push more rapidly in and out as her eyes
finally close.
I settle into a firm strong rhythm and enjoy yet another
pleasant sensation on my cock. Cory spreads her legs
wider and I find myself going even deeper into her.
Eventually she pulls her legs back up to her shoulders
and I feel as if I am splitting her open. She rests her
knees on my shoulder and back and I continue to pound
her deepest recesses. Her vaginal walls tighten in
orgasm several times, squeezing my cock hard as she
convulses. Only the number of times I have cum gives me
the endurance to keep going.
I fuck Cory for the next thirty minutes. Or so Joan
would inform us.
Eventually Cory’s tight little pussy got the better of
me. As she clamps down yet again and I listened to her
moan in pleasure and I feel the welcoming tingle of
release start in my balls. I increased my speed and
reached orgasm, pulling out and delivering my load on
Cory’s stomach. I stare and admire the cum drying and
spreading out over Cory’s heaving stomach. Her pussy was
still wet, wide-open and spread as she started to close
her legs.
I curled up next to her and she kissed me broadly on the
lips and cuddled. A couple of minutes later she kissed
me again as she got up. “Thanks,” she said as she got
up. “Come on Joan, we need to get home. I’m meeting some
people at 7 for a bike ride.”
Joan was resting on the floor. Her skirt pulled up and
pussy wet. I can only guess she was masturbating to our
action. Cory got dressed quickly. Joan only threw on a
shirt, leaving her bra and panties behind.
As I lay on the bed naked and drained Joan had one
partying comment.
“Rest up lover. I’ll be back tomorrow afternoon.” Then
they were gone.
Joan came back the next afternoon. This was not the
worst debt I had to settle. I surprised her with a nice
long massage before we settled in to business. She got
every hour of the oral sex she was promised and even a
little more as a tip. Her pussy tasted really good that
day and I was in no hurry to stop. But, more on sex with
Joan later…