Discovery in Chicago
Caution: This Sex Story contains strong sexual content, including Ma/Fa, Mult, Reluctant, Cheating, Slut Wife, Voyeurism,
Desc: Sex Story: Chapter 1 - Story about a happily married woman who has never experienced sex outside of her marraige. Out of town at a business conference, her world turns upside down as she discovers a new side to her sexuality. First of a series.
Scott and Cheryl were high school sweethearts and both virgins when they married at the ripe old age of 21. Despite their lack of experience, they managed to learn about each other's tastes and desires over the years and after 17 years of marriage; they still enjoyed each other in bed. Scott tried to keep the sex interesting by reading erotic magazines and watching adult films to get new ideas to bring into their lovemaking. Cheryl, initially very naive about sex, seemed to open up more and more as the years went by and Scott was pleased that their sex life seemed to be constantly evolving.
It always amazed Scott that Cheryl didn't seem to realize how sexy she was or how desirable she could be to other men. At 38, Cheryl was still very attractive with long slender legs, small breasts with large sensitive nipples and full sensuous lips. During their lovemaking, Scott would often whisper to her how sexy she was and how any man would love to bury his cock into her pussy as he was doing. Cheryl would get embarrassed and tell Scott that she only wanted him and that she would be too nervous and scared to be with another man. Scott was extremely turned on by the fantasy of his wife with another man and was almost positive that he didn't want it to happen in real life. Scott was totally confident that Cheryl would never cheat on him or even think about another man sexually.
Cheryl had been asked to attend a conference in Chicago along with 3 other women from her office. Although she had always avoided these meetings in the past, Scott encouraged her to go and she finally relented. The women were asked to share rooms and Cheryl seemed pleased that she had been paired with Audrey, a close friend over the years.
After attending the usual boring lectures and seminars, Cheryl and Audrey had dinner with some colleagues from another state. When dinner was over they said good-bye to the group and decided to have a quick nightcap in the hotel bar where they were staying. Audrey made a quick call to her husband to make sure all was well and then relaxed with Cheryl in the dimly lit bar. After a couple of rounds, two gentlemen approached their table and asked both of them to dance. Audrey hesitated for only a moment before she stood up and said yes but Cheryl gave a firm and polite "no" to the offer. Audrey left with her partner and the other gentleman asked awkwardly if he could sit at their table until his friend returned. Cheryl said yes and he introduced himself as Bob, a marketing director from Dallas in town on business. The other gentleman was his partner Frank. Cheryl couldn't help but notice that he was a very good-looking man, about 6 feet tall and in excellent shape.
After about a half-hour of light conversation and another round of drinks, Bob again asked Cheryl to dance and this time she agreed. Audrey seemed to be having a good time dancing with Frank and both men seemed pretty harmless. After a couple of fast songs the house trio slowed things down and before Cheryl could move off the floor, Bob asked her to dance one last song. He held her fairly close as they slowly moved on the crowded floor. Cheryl, a little bit dizzy, realized that she was starting to feel her last two drinks. Bob gently moved her against him with his hand at the small of her back. Cheryl thought she felt a very brief brush of something hard against her thigh. She began to get a little anxious about the situation but told herself that she was over-reacting and that she was probably mistaken. Ever so slightly, Bob moved himself against her once more and this time there was no doubt in her mind that Bob had an erection and he was pressing right against her pussy.
The song finally finished and Cheryl quickly moved out of Bob's arms and went to look for Audrey. When they got back to the table Audrey was getting her purse and leaving with Frank.
"Audrey, where are you going?" asked Cheryl.
"Frank asked me to take a walk and I think the fresh air will do me good" replied Audrey. "I'll catch up with you later".
Cheryl was slightly angry at being left alone with Bob but felt she could handle the situation. She agreed to one more drink. Actually, she needed a drink badly. The brief exchange on the dance floor had shaken her up and she had to fight to keep her hand from shaking as she picked up her glass.
Manufacturing a yawn, Cheryl stood up and thanked Bob for the drink and told him that she was tired and ready to sleep. Bob, ever the gentleman, offered to escort her to her room.
"That won't be necessary," said Cheryl.
"It would be my pleasure," said Bob.
Cheryl was still nervous about what had happened on the dance floor but she allowed Bob to see her to her room. Once outside her door, she thanked Bob, primly shook hands, and said good night.
Cheryl entered the room quietly and as she turned the corner, she was shocked to see her friend Audrey naked, on her hands and knees, sucking Frank's cock. Cheryl stood transfixed as Audrey, oblivious to her surroundings, was making loud sucking noises as she moved her mouth up and down his glistening shaft. Frank started to gently thrust his cock in and out of Audrey's mouth. He looked up and saw Cheryl standing there. Cheryl thought he might suddenly stop out of sheer embarrassment but Frank only smiled at her and kept fucking Audrey's mouth. Still on her hands and knees, Audrey suddenly climbed on the bed, spread her legs, and told Frank to fuck her from behind. Cheryl tried to leave but her legs would not carry her. Frank moved into position behind Audrey and guided his cock to her slick opening. He placed his hands on Audrey's hips and slowly started to enter her, going a little deeper with each stroke until his entire length was buried in her pussy. Cheryl heard Audrey gasp "Ohhhhh... fuck me Frank... fill me with that cock!" Frank started to fuck Audrey with long powerful strokes.
Cheryl watched her friend's breasts sway back and forth with each thrust. She couldn't help but stare at the long thick cock that was moving in and out of her friend. She had never seen another erect cock, let alone one this large, and she could not look away. Audrey started grunt with each roll of Frank's hips. Frank turned his head slowly toward Cheryl as he kept a steady rhythm in and out of Audrey's pussy. He looked directly in her eyes and nodded his head in Cheryl's direction as if asking, "do you want some of this too?". Audrey started moaning loudly, slamming her ass back at Frank and Cheryl could see that she was having a massive orgasm.
Cheryl finally found her feet and quickly opened the door and left the room. She was sure that Audrey never saw her but even if she did, Cheryl didn't think it would have made any difference. She leaned against the wall to catch her breath. The image of Frank's cock plunging in and out of Audrey's pussy was branded into her mind. She had never seen anything so powerful... so erotic... so hypnotizing in her life. It seemed like she had been in the room a long time but realized that it had only been about five minutes when she checked her watch.
"Now what do I do?" thought Cheryl "I can't go back in there and I have nowhere else to go!"
She started walking toward the elevator and was surprised to see Bob standing there.
"What happened? Asked Bob.
"Nothing... really... I just forgot something at the bar" lied Cheryl "why are you still here?" she asked.
"Well", stammered Bob, "I know Frank pretty well and I figured he was with Audrey in your room so I was just waiting around to see if you were ok".
Bob put his hand on Cheryl's shoulder and said quietly "and by the look on your face I'd say I guessed right, didn't I"?
Cheryl just nodded.
"Tell you what" he said "why don't you just wait it out in my room? I promise to be a good boy and it may be a while before Frank is through."
Cheryl didn't really have any other options, so she agreed as Bob pressed the elevator button.
They reached Bob's room and as they stepped inside, Bob told Cheryl to relax and help herself to the mini-bar while he changed into more comfortable clothes. Cheryl made herself a quick drink and sat on the bed and tried to calm her nerves. She couldn't seem to get the picture of Audrey and Frank out of her mind. The way he drove his cock into her friend, the slick sounds of her pussy getting fucked, the way Audrey urged him on in language she had never heard her friend use in all the 20 years they had known each other.
Bob came out of the bathroom in a T-shirt and a loose pair of shorts.
"Feeling better?" he asked.
Cheryl jumped off the bed quickly "Yes, I think so" she said as she moved to stand by the dresser.
Bob said "You know, to be honest, I was kind of hoping you and I could have got togeth..."
Cheryl stopped him cold. "I don't think so" she said. "I told you I'm married and I love my husband very much."
"Who said anything about love?" asked Bob. "I'm talking about having sex just for the fun of it. Haven't you ever been so horny that you just wanted to fuck?"
Cheryl colored visibly. "I think I'd better be leaving," she said as she moved toward the door.
Bob moved quickly to her side and tried to apologize.
"I'm truly sorry," he said and before Cheryl could stop him he swiftly moved his hand under her dress to the front of her panties.
"You might say want to leave... but your soaking wet pussy is telling me something else."
Cheryl froze as Bob started to slowly stroke up and down her panty covered slit. She was frightened by this sudden turn of events and felt herself getting weaker with each stroke of Bob's hand.
"Please... I want to go" whispered Cheryl.
Bob responded by grabbing her hand and forcing it down the front of his shorts. He wrapped her fingers around his cock.
"Go ahead and feel how much you turn me on" Bob urged.
Cheryl refused to move her hand. Keeping her trapped, Bob gently pushed aside the damp crotch of her panties with his other hand and started to stroke her bare pussy.
"Please" whimpered Cheryl "I... I... can't do this I...".
Bob felt her legs start to move apart. He began to slowly move Cheryl's hand up and down his cock. Ever so gently, he released her hand and almost in a trance, Cheryl continued to stroke his shaft on her own. It was about the same length as her husband's but thicker... much thicker. The head of his cock seemed enormous and she shuddered at the thought of it entering her pussy. Her legs began to buckle as Bob continued to stroke her with more confidence.
"That's it Cheryl" he whispered "just let yourself go and I'll make you come like you've never come before."
Cheryl let him move her to the bed as she felt her legs give way. Bob quickly began to strip off her clothes and his own. When he got to her panties her literally tore them from her body in his haste to get at her.
"Spread your legs" he commanded.
She did. Bob was mesmerized at the site of her wet pussy lips and engorged clitoris. He could see her juices running down the inside of her thighs. With only a slight pause, Bob pulled her ass to the edge of the bed, dropped to his knees and quickly plunged his face and tongue right up her hole. After only a minute he moved his tongue up her slit and began a slow circular motion around her clit.
"Oh God" moaned Cheryl "Oh God, Oh God, Oh God... I'm coming!!"
Cheryl rode the wave of orgasm and she felt herself humping against Bob's tongue. "Ohhhhhhhhhhh" she moaned as she grabbed his head. She had never come that fast before.
Bob quickly moved up, placed her legs over his shoulders and edged his large cock head to her wide-open pussy.
He whispered to her "Do you want to get fucked Cheryl"?
"P... Please... I... I..." she gasped "No one but my husband has ever...".
"You have to ask me for it" continued Bob "Do you want my hot thick cock buried deep in your steaming cunt?
Bob was moving the head of his cock up and down Cheryl's wet slit.
"Oh... oh... damn you... damn you..." Cheryl said.
Bob continued his teasing motion.
"DO IT!" she screamed "Fuck me... just give me your cock and fuck me. Make me come again and again you bastard. Is that what you want to hear?"
Bob answered by driving his entire length deep into her pussy. He heard Cheryl gasp.
"Oh god-d-dd" she groaned as her pussy lips wrapped around his shaft.
Bob began to fuck her with deep strokes.
"Uh, uh, uh" Cheryl started to grunt and thrust her cunt back to meet his every stroke.
She had never felt such pure lust in all her life. She felt like an animal in heat. Bob increased his rhythm and Cheryl responded like she never had before.
"Fuck me hard... don't stop... it feels sooo good... "she moaned.
Bob moved up on the bed as Cheryl wrapped her arms and legs around him. She hung on for dear life as Bob continued to pound away. She felt his cock start to throb and knew he was close.
"Oh fuck... oh fuck..." she panted.
Cheryl started to come hard as Bob made one final thrust before reaching his own climax deep within her womb.
Cheryl was shaken to her very core. She couldn't believe how she had responded to Bob. Never in her life had she thought she would be capable of such passion with someone other that her husband. Bob pulled out of her slowly and Cheryl felt a huge gush of liquid flow out of her pussy. Almost without thinking, she moved down Bob's body and started to kiss and suck the organ that had given her so much pleasure. After only a few minutes Bob's cock began to respond. Cheryl got up on her hands and knees to get into a 69 position. Before she was able to move however, she felt another pair of hands spreading her legs from behind. "Oh god... Frank!" she thought and she tried to move off the bed. Frank held her fast and quickly moved his cock into position.
"Audrey's passed out but it looks like you still need some attention" said Frank.
He easily plunged his hard cock deep into her freshly fucked pussy. Cheryl started to protest but knew it was useless now. Bob moved her head back to his cock and the two of them began to rock her back and forth between them. Cheryl was shocked to feel the wave of yet another orgasm starting to build within her. She had never come more than once in any lovemaking session before and now she was heading for her third one of the evening.
Bob and Frank continued their movements as Cheryl felt their hands on her rock hard nipples and engorged clit. She felt like such a slut yet the pleasure she was feeling was undeniable. Bob started to groan that he was coming. She pulled her mouth off him and let him spray all over her breasts. Frank moved out of her pussy and positioned Cheryl to lie on her back against Bob. Bob reached down and spread her legs wide and told her to watch. Cheryl opened her eyes and looked down her body to see Frank's cock once again enter her. She saw her pussy lips stretch wide to accommodate his girth. She was totally in their command now and was almost eager to give Frank the ride of his life. Cheryl met Frank's every thrust as their movements got faster and faster. Finally, Cheryl grabbed Frank's ass and pulled him in as deep as he could go. She ground her pussy against the root of his cock and felt a gush of liquid as Frank emptied himself deep within her.
All three collapsed on the bed. Cheryl was totally spent and had trouble catching her breath. After a while she quietly left the two dozing men, gathered what was left of her clothes, and made her way back to her room. Cheryl slipped her card into the door slot and hoped that Audrey was asleep. She was relieved when her friend didn't move a muscle as she made her way into the room. Cheryl quickly slipped into bed and drifted slowly toward sleep. As she closed her eyes for the last time that night she thought to herself "I wonder if I'll ever be the same after this?"