Betting on the Cum

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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 these Joan and Cory, especially Joan. The roommates could be a 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 portrays. For example, you notice how snuggly her dress hugs her hips, her skirts are just high enough and her choice in swimwear 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 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 probably had other things on her mind.

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. The margaritas were flowing and eventually the party drifted down to about five people.

The group consisted of three single women and two single guys so the conversation eventually 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. Your 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.” 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 winner gets the master bedroom suite. Obviously they’ll make better use of it.” Joan responds.

“Deal” replies Cory.

“That’s all good ladies, but how are you going to settle this bet?” Carol asks, somewhat oblivious to the little tents the guys are growing.

“We’ll use him” Joan mentions pointing at me. “In fact, to make it even better I’ll bet Cory that I can make him cum quicker the second time around than she can the first time. Proving a guy can cum twice and I’m better!”

“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 going to be good enough when Joan leaned over and whispered in my ear, “I güvenilir canlı bahis siteleri 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 can not 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 no 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 getting up for her turn. She surprises everyone as she removes her shirt and bra. My eyes are fixed on the motion of her naked breasts jiggling with her stride. I do not take notice of 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 and 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 we 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 dress. 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. My hands play with her soft breasts as they dangle 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 of my 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, güvenilir illegal bahis siteleri 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 and 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 can not 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 make her way into the kitchen. I smile over at Cory and she weakly smiles back. She is pretty sitting in a partially shade as only one light is on in the area. 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 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, güvenilir bahis şirketleri “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 bikini’s 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 directs Cory onto the bed. “Tease him with the smell of your pussy?” Cory is hesitant until Joan has me clarify how nice it smells to a man. Cory straddles me, her mouth over my cock and her knees on either side of my head. My hands work her nice back and ass before landing on her wonderfully firm tits. Joan coaches her to tease my cock with her tongue. Her action on my member and the smell and visual stimulation of her vaginal lips dancing in front of my face bring me close. I raise my head and slowly lick her labia.

Cory pulls away. “Oh no? You don’t want to do that?” She asks.

“Cory, get over it. Guys love a nice pussy like yours. Relax and enjoy it!” Joan coaches, answering for me.

My hands reach for her hips and pull her dripping hole back to my mouth. I confirm Joan’s comments as I eagerly work the pussy in front of me. Letting her know just how much I wanted to do this each and every day I saw her at work. Cory is in heaven as I work her labia and inner lips before moving onto her clit.

“Work his cock if you want him to cum!” Joan coaches Cory. She does and I cum very quickly. Cory takes a small amount in her mouth but the rest drips over her chin and onto me. She is lost in my licking and cooing heavily. I feel her spasms as I bring her to her first orgasm. She keeps pushing backwards and I keep nibbling and suckling her little nub. Soon she has cum again before relaxing forward, lying on top of me.

“See, you can make him cum in a couple of minutes too!” Joan comments. “And, it’s a lot more fun this way.”

“Oh God! That was great!” Cory comments, “My pussy is on fire. I need to be fucked!”

“I know!” I say, my eyes fixated on her hand. It has drifted back under her legs and started to masturbate her pussy only inches from my face. Cory is temporarily embarrassed but a little encouragement keeps her hand in place.

“Do you want him to fuck you?” Joan asks. Cory nods but is worried about my member, now only semi-flaccid in front of her. “Let’s see what we can do about that!” Joan comments.

Joan whispers in my ear, “Remember, one hour of could pussy licking tomorrow.” She then stands up and pulls her skirt off. She kisses me deeply before lying on the bed, her head down at my crotch and her torso to the left of me. She instructs me to enjoy playing with her and Cory’s tits as they both lick and suck me. Joan makes loud slurping noises as she licks the cum from my stomach and Cory’s chin.

She sees my interest in this and surprises everyone as she licks Cory’s tits briefly. “Relax and enjoy.” She instructs as I feel her tongue on my cock and Cory’s on my balls. She whispers something to Cory and quickly they are both playing with their pussies in front of me.

All too soon my cock is hard again. Joan asks Cory if she still wants to be fucked. Cory nods affirmatively and Joan asks her to assume her favorite position. Cory rolls off me and onto her back. She pulls her ankles up, forming a “V” and presenting a wide-open pussy to me. Joan rolls off and smile at me.

I bounce toward her and position myself on my knees at her ass. I rub my pussy over her folds a couple of times before plunging in. Her pussy is wetter and more open than I imagined and my full-length slides in easily. She is better than I imagined in my dreams. I slide in and out, enjoying my fantasy come true.

Cory moans in satisfaction as I fill her. I pound her solidly as I enjoy her pleasure and the sensation of her warm, tight pussy on my cock. She pulls her legs apart, almost forming the splits. Her pussy is so wide and deep I can hardly control myself even after the two magnificent “69’s.” I plow her faster and faster as she disappears deeper and deeper into her feelings.

With a free hand I work her clit, bringing her to a quick orgasm. I push my cock in and out of her tightened pussy muscles and keep fucking her. Her arms relax back over her head as she enjoys the long hard fucking. Her legs wrap around my hips as I continue to fuck her pussy, now tighter from her change in positions.

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