Sexual Roulette

Story Info
Two women play a sex game with a stranger.
3.5k words
3.83
27.4k
8
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
namelorb
namelorb
36 Followers

It was a little after 10: 00 pm when Serena & Connie entered the hotel bar. It was a bar that they had not been to before, but it was a routine that they both knew quite well.

Serena: (Spoken with confidence and self assurance) "So who will it be tonight?"

Connie: (Relaxed and Playful) "Lets pick someone that is in better shape this time. They do not have to be an athlete, but seriously."

Serena: "How about the man at the end of the bar? He looks like he will do."

Connie: (Spoken, as she was a bit pissed) "No! The ring! No married men!"

Serena: "And the guy next to him looks like he is too young. I would have to check his ID to confirm that he is old enough to be in this bar."

Connie: "How about the bald guy that is just getting a beer at the bar."

Serena: "He will do just fine. And he is not bald; I like the short stubbly hair. So let the games begin."

The ladies walked towards him, with their drinks in hand. They brushed lightly against him, one on each side, as they placed their drinks on the bar.

Connie: "What brings you to town?"

Serena: "What do you do for a living?

Connie: "You look fit, do you workout?"

They fired questions at him in rapid succession. His head moved back and forth between the ladies, first glance to their faces, his second glance to their chests and waists. He did not respond, but looked back to their faces again. The ladies paused for a moment and repeated his actions by glancing down at his midsection and back up to his face. Connie the more playful one of the two placed her hand on his shoulder and gave him a flirtatious smile.

But let's talk about the ladies for a moment;

Serena has solid, tight and muscular body. She works out doing cross fit on a regular basis. She has a perfectly round and perky butt, that is almost peeking out from beneath her short black skirt. Her legs are long and muscular to her 5' 9" frame. Her 'B' cup breasts are pushed up with the help of a good bra making her appear to be a 'C'. She has a beautiful round face with short brown hair. She works as a construction supervisor overseeing several work crews. She works hard at her job and is equally focused on her playing. When at work she dresses professionally for her position, but when she plays, she dresses in her sexiest short skirts and always shows full cleavage. Serena is the leader of the two women that are the best of friends. The fact that they are at this airport hotel is her plan, as she is much less likely to run into one of her coworkers out by the airport and in addition the airport is likely to have visitors that will be in town for only a short time frame. And as such they will likely not return or return very infrequently.

Connie is a bit shorter at 5' 4". She has a petite frame with quite large breasts for her height, at least a full 'C' and possibly a 'D'. She is not skinny, but is not overweight. Her hips are curvy and she crosses her feet over her centerline when she walks to accentuate the sway of her hips and butt. The guys melt at her playful and flirtatious style. She works as a pharmaceutical sales representation, which for her, is not like work at all. One has to be smart for this job, but being a beauty and a flirt make it more like playing than working. She allows Serena to take the lead in not only these situations, but in all aspects of their friendship. She is a more caring individual then her friend.

And Mel, he is a Sales Manager, and let's face it, most men are their work. He lives for his job. He is 6' tall with a standard build, but the ladies back home say that his tight butt is his best feature. He is confident in all aspects of his career, but lacks a little confidence with the ladies.

Serena: (spoken in a confident and professional manner) "Connie, let the man breath. I am sorry to be so direct. We are just out tonight having a bit of fun and would like to ask you to join us." She said as she motioned to a booth off to the side. He nodded and the couple moved over to a corner booth and the ladies slid into the seat around him from both sides. "Let's start with introductions, my name is Serena & this is Connie."

Mel: "My name is Mel, I am here for a business meeting, I am a Sales Manager and I do workout to stay fit."

Connie: "So, are you interested in playing a game?" She could tell that he was intrigued, but she did not wait for a response. "We have a game that we like to play, and it requires three players." She said as she looked over to Serena and then back at Mel. Then in a seductive voice she slowly spoke, "There are several rules, but the first one is that we all have to be naked before the game begins. The second rule is; you must wear a condom at all times. Does this sound like a game that you might be interested in playing?"

Mel had a shocked look on his face, but he did not respond.

Serena: "Do you have a room here?"

Mel: "Yes and Yes."

The group grabbed their drinks and walked out of the bar with their drinks in hand. They knew that most bars do not allow you to leave with their drinks, but they still confidently walked down through the lobby. As they entered Mel's room, mike removed his wallet and phone and placed it into the room safe.

Serena: "Connie, would you please cover the rules?"

Connie: "The game is called 'Sexual Roulette'. We ladies are each assigned a random amount of time and the key to this game is for us to have as many orgasms as possible, but not to get shot by you and your orgasm.

-+1 points for each lady orgasm,

--2 points to the lady that is shot by your orgasm,

-There is a roll of the dice and a switch time of 20 seconds maximum, the other lady must mount your penis before 20 seconds have elapsed from the others dismount,

-2 white dice indicate the ladies length of time and the red die indicates the position for the man during each turn by both ladies.

They had a card with the position for the man:

1. Belly

-2. Back

-3.Knees

-4.Standing

-5.Side

-6.Woman's Choice

Do you have any questions about the rules?"

Mel: (A bit shocked yet excited) "Wow! This sounds incredible, did you ladies come up with the game on your own?"

Serena: "It is out little invention."

Connie went to her large purse and pulled out a timer and some dice and set them on the end table, along with a card that indicated the 6 position that the man would be assigned. But Mel hardly noticed Connie as Serena began to undress and that drew all of his attention. Serena did not waste any time and quickly removed her skirt and blouse and snapped off her bra and placed her clothes in a small pile on the desk. As she finished she walked over to Connie wearing only her panties and assisted in unbuttoning Connie's blouse. Serena dropped her skirt then she kicked it onto the chair and then tossed her blouse on top of it. Connie reached behind her back and unclasped her bra and added it to her stack of clothes on the chair. Mel was a bit shocked by all of this, as they were quite seductive and sexy just moments ago, but now they had the appearance of an athlete preparing for the big game. They were confident with their own bodies by stripping with all the lights on. They were in the zone.

Mel was caught in a bit of a trance as his eyes were locked onto these ladies that were both topless in front of him, when only a few moments ago they were all down in the hotel bar with their initial greeting. He adjusted his gaze from one lady then to the other. He was admiring the bounce of their breasts, the curve of their hips. But then he realized that they both stopped moving and were staring at him. Serena pointed an open hand at his genitals, in a gesture to get busy and get undressed for the game. He made quick work of removing his clothes and kicking them anywhere around the room. He did not even pause but immediately dropped his boxers to the ground and gave them a kick. He stood their sporting a partial erection that continued to grow. After all, there were two naked ladies, well almost naked, walking around in front of him. The ladies followed his lead and removed their final garments to Mel's great pleasure. Connie had completely shaved her pubes while Serena had the smallest of a little tuft of hair just above her clitoris. Mel was mesmerized by these two naked women, as he enjoyed the beauty of the female form. He marveled at their silky smooth skin and gorgeous round butts. He was in heaven.

One could tell that the ladies were taking this quite seriously, after all they had bragging rights on the line for this evening, but the bragging rights only between the two of them, as no one else would know about it. Serena squeezed a bit of lubricant into her hand and then some into Connie's hand. Both of the ladies reached down in unison and lubricated their vaginas fully. Serena then placed the lube on the table next to the dice.

Serena: (back to the playful voice)"Are you ready sport?" As she turned to Connie, "I am going to win big, just wait!"

Connie: "Here we go!" And with this both ladies sat down on the edge of the large king sized bed and they began to massage their clits. "W-A-R-M U-P Time!" She said slowly as she stroked her clitoris. Mel just stood there at the end of the bed watching as these two beautiful women opened their legs wide and stroked themselves. He could hardly wait to get started. "You first girl." She said as she motioned to Serena. And with this Serena rolled the dice; a 1 & 3 with a red 3. "On your knees sport," She demanded.

Mel was very eager to comply, as he climbed up on the bed and knelt in the center of the bed as his erection throbbed in the air in front of him. Serena positioned herself on her belly facing away from Mel, with her butt high in the air. Mel scooted forward to her and placed one hand on top of her butt. Serena had returned her hand to her clit and resumed her stroking.

Serena: "We will handle the insertions Mel. Feel free to do your thing." She turned her focus to Connie. "Ready!" She exclaimed for the games to begin.

Connie placed 40 seconds on the timer and pressed start, to the sounds of a short beep. Serena reached back and grabbed the shaft of his penis and inserted it into her well lubricated vagina. Mel did not need any more instruction and began to thrust into her steady at first and then hard and fast.

Serena: (In a calm voice) "It's a marathon not a sprint." And with this Mel slowed his pace a bit, while Serena continued her clitoral stimulation. In no time at all, the sharp 'Ding' of the timer went off. Serena slid herself forward and off of Mel's shaft, leaving Mel kneeling there with his erect penis pointing high. She moved off to one side of the bed while Connie slid in from the other side and positioned herself in the same doggie style position with her pussy right next to his engorged penis. Connie returned to her clitoral stroking but did not grab for his penis right away. Mel was asking himself, 'what is she waiting for'? Serena was standing by the timer, but had not pressed the start button yet. Within a few seconds she reached for this penis, held it firmly, while still stoking herself, and plunged his penis in, with a simultaneous beep of the timer. Mel then realized that she was getting in a few extra strokes on her clit before her time was to begin. Mel resumed his steady strokes and in no time at all, the bell rang out again and Connie pulled herself forward right with the ding.

It was Serena's turn and the roll was a 6 & 1 with a red 1.

Serena: "On your belly," She demanded. And with this she slid face up in front of Mel. She continued to massage herself for an additional 15 seconds and then grabbed his shaft and pulled him on top of her, keeping her hand on her clit. She would massage herself on the upswing and then let Mel mash her hand into her clitoris. She erupted with an orgasm directly in the middle of her allotted time, while never breaking her concentration she worked for another. But the bell dinged at 70 seconds.

Connie jumped into position and almost pushed Serena out of the way as she continued her focus with her fingers. She did not waste any time but immediately grabbed his penis and shoved it into herself. Mel could almost immediately feel her muscles throbbing as she orgasmed quickly and without any hand stimulation. She reached up with her hand and pulled Mel hard into her at a slow to somewhat moderate pace. She was conducting his thrusts with her hands, setting the pace and the pressure of his passions. A short time later she erupted again and this one was more power as she began to buck up and down. There was still time left and she continued her movements, but she also began to rub her hands gently across his back and butt. Then the ding of the bell.

Score: Serena: 1

Connie: 2

The dice were rolled again; 6 & 4 with a red 2.

Serena: "Down on your back!" she demanded.

Connie rubbed her hands across his chest as she slid out from under Mel and off the bed. And with that he rolled onto the bed and settled back into the bed as requested. Serena moved on top of him straddling him as she knelt above him. She paused for a moment and then grabbed his penis and lowered herself onto him, to the start of the timer. She began to drive hard into him to apply solid pressure on her clit. Serena kept up her movements and with a steady pace. After a bit Mel observed that she closed her eyes and her lips began to quiver, and yes, a short time later she was enjoying the great release of orgasm. She continued to swing her hips down and forward and squeezed out another orgasm just before the bell rang, but she continued to stroke a few more times beyond the bell.

Connie rubbed her hands gently across Mel's chest as she adjusted from kneeling alongside him, to straddling him. She continued by swirling his chest hair with a single finger before grasping his shaft and lowering herself onto him. As she did, Mel let out a slight gasp and then his mind wandered for a moment; Connie was doing those small little extra things to him, like playing with his chest. She was not just into having sex, but she was into improving the pleasure of his sexual experience. Serena was a bit colder and to her it was all about her orgasm and her experience and Mel was just a tool to be used. But as he looked in Connie's eyes she could see real attraction through her gaze. Just then he was snapped back to reality of the joys of having sex with a beautiful woman. He had a feeling that the time was about to run out on the timer, but Connie began to vary her breathing and she exploded into a glorious orgasm. As she did Mel could feel the throbbing of her vaginal muscles and he joined her in orgasm. But he did so quietly and without any outward signs that he had shot his load. As the bell rang he pulled her down to him and gave her a passionate kiss.

Serena pushed Connie off of Mel breaking their kiss. Serena rolled the dice; 2 & 3 with a red 2.

Serena: "Alright, same position with a tied score. Let's do this!"

With this she mounted him directly and began her thrusting. Mel waited only a short time and pretended to have an orgasm. He was only moderately successful in his acting performance. When the bell rang at 50 seconds, Serena dismounted and immediately reached for his condom pulling it off, holding up in the air to inspect it for semen. She was not happy to see that it was full of the creamy white evidence, showing proof of her loss in the contest.

Serena: "Well, I lost; Damn!"

Serena turned and walked away to sit down across the room. Mel watched her naked frame as her hips swayed with each step, but tore his eyes away from her and reached his hand out to Connie's had who had sat on the edge of the bed. She squeezed his hand and leaned in to give him another kiss, just as passionate as the one before. Serena reached over for the rest of her drink left over from the bar. Mel joined her by reaching over to the table and finishing off his drink. As he switched his view from one naked lady then back to the other. But, he found himself studying the finest details of every curve in their bodies. Mel began to search for something to say as a way to continue the evening. The ladies were not dressing, and he was enjoying that fact, but he was not ready for the evening to end.

Mel: "So, How did you ladies come up with this game?"

Connie: "We came up with this idea on a night, as we sat around our usual bar with the usual guys, that we are not interested in and we came to the realization that there are a lot of guys out there that would love to have sex with a beautiful woman with no strings attached, with no thought of long term relationship and two women together would make it a lifetime memory. I kind of like the idea of being a lifetime memory for someone."

Serena stepped into the bathroom and closed the door, Mel watched her all the way as she walked by, because, let's face it, she is a naked. And all men would not pass up an opportunity to observe and study every detail of a naked woman. As Serena entered the bathroom and closed the door, he did not waste any time and rushed his naked self over to Connie. She was facing away from him, so he placed a hand on her hip and spun her around.

Mel: "I am coming back in town in 4 weeks, and I absolutely have to see you again."

Connie: "We do this as a onetime event, without any long term relationship."

Mel: "I can tell that you are attracted to me. I can see it in your eyes. And I know that I am attracted to you, you are gorgeous. We do not have to tell Serena. Come on just you and me a night out on the town? What do you say?"

Connie: "Well, you are cute, but we have a rule, no relationships."

Mel: "But don't you want a relationship, if not now, sometime soon."

Connie: "I don't Know, I..." She stopped speaking as Serena reentered the room.

Mel was disappointed with her response, but he was interrupted as Serena returned from the bathroom. Serena walked over to the bag reached in and pulled out a vibrator.

Serena: "Who is ready for round two?"

++++++++++

Mel was thinking about this day 10 years later. He then realized that it was almost exactly 10 years ago, when those two ladies approached him in the bar. As he thought about that wonderful evening's adventures, he quickly sparked an erection, as that worked every time. A smile appeared on his face. He walked into the next room, approached his wife, placed a hand on her hip and spun her around.

Mel: "I love you Connie, so very, very much!"

He kissed her with a most passionate kiss, as she relaxed into his arms.

A Story by Jay Namelorb

*****

If you liked this story, you may consider reading;

1.Snows of Trout Lake

2.He Never Remembers

3.Retirement Village Visit

4.Drive Time

5.Iron Man Trist

6.College Roommates

namelorb
namelorb
36 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
Dr_James_Davies_DFDr_James_Davies_DFabout 1 year ago

A Lively Romp

Who can know where a likely three way lark will lead?

thomas_deanthomas_deanabout 1 year ago

One Never Knows Where Love Will Blossom

Connie intended and Serena intended to roust Mel and be done with him. After a lively round in bed, Mel asks to see Connie once again ... 10 years later... there are unanswered questions. Are there any children? What happened to Serena? It's a cute love story.

AnonymousAnonymousover 8 years ago
more action needed

This was well written but would have liked to read more action. Its a very quick read.

Share this Story

Similar Stories

My Sister Moves In Wife's sister needs a place to live and moves in.in Loving Wives
My Neighbor's Shenanigans View from my house is perfect for watching neighbors' pool.in Exhibitionist & Voyeur
Victoria's Secret the Banana Problem Victoria's price check in the slave market continues.in NonConsent/Reluctance
Naturism with the Neighbours Jim and Sarah explore nakedness with their neighbours.in Group Sex
Daisy's Resort Pt. 01 Old friends take a trip to a swinger's resort.in Group Sex
More Stories