Heads, Tails, and Oops: The Three Sides of a Strange Coin.

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When the phone rang, he didn’t think anything about it. He thought it was one of the guys trying to get him to go to the club later that night. “I’m trying to reach Shawn Randolph,” the female voice said. “This is Shawn,” he answered. The voice sounded familiar, but he couldn’t quite put a name or a face with it. “Oh my God, I can’t believe I finally reached you.” the voice said. “Who IS this?” Shawn replied. “Do you remember Orlando?” the voice said. “The concert after-party.” she continued. All at once it came back to him. It had been over 15 years ago. He was at the refreshment table getting a soda when he heard a voice behind him say, “Whoa, better slow down on those Cokes if you’re driving home later.” When he turned around, he was staring in the face of who he thought was the most gorgeous woman he had ever seen in his young life. “Uh uh, yeah. I’ve had quite a few tonight hunh,” he replied. They both laughed. “Hi my name is Shawn,” he said. “I’m Christina,” she replied. As they shook hands, there was an obvious attraction between them. Shawn never stuttered or stammered his words. But when he saw her, he almost forgot how to talk. Christina wasn’t shy by any means, but it was a huge change for her to initiate conversation with a man. After their initial introductions, they took their drinks and stepped outside to talk in a less crowded area. The two spent the next couple of hours getting to know one another. She learned that he was only 19 years old, and had driven up from college in South Florida for the concert with some friends. He learned that she 22 years old, already finished with college, and was in town visiting from St. Louis. Unfortunately, their night was cut short by Christina’s friends urging her to leave. “Can I call you?” Shawn asked. “Sure, but I have to tell you, I do have a boyfriend.” Christina replied. “I understand, but does that mean we can’t be friends?” asked Shawn. Christina smiled and gave a small laugh, then reached in her purse for something to write her number down on.  As she reached to hand him the small slip of paper, he stepped forward and gave her a hug. As the hug ended their eyes met, and he leaned in for a kiss. In that moment when their lips met, she forgot about her friends waiting on her. She forgot about her boyfriend. She forgot who she was, where she was, and why she was about to walk away from this man who was in the process of taking her breath away with a kiss. As the kiss ended, she just stood there in shock. If it had not been for one of her friends grabbing her by the hand and dragging her away, she may have even passed out from the shock. Shawn was just as shocked as she was. He couldn’t believe what he had just done. It was as if he was having an out of body experience and watching someone else was in control of his body. “I cannot believe I just did that……….but I’m so glad I did,” he thought to himself.

After that night, Shawn and Christina talked on the phone with one another at least 3 times a week. It wasn’t long before Christina was all the social life Shawn had. He didn’t go out much before he met her, but now he was all about school and Christina. Christina on the other hand was still dating her boyfriend, but would make time for those special phone calls from Shawn. At first their conversations were innocent. This is mainly because Shawn knew she had a boyfriend and didn’t want to cross a line that might end their friendship. One night however, he crossed that line and their relationship changed. “Hello,” she said answering the phone. “Hey Chris. Whatcha up to tonight?” Shawn asked. “You caught me in the tub Shawn, can I call you back?” Christina replied. “You don’t have to hang up. You can just put the phone down beside the tub. I like to listen,” Shawn said. “Listen to what? she asked. “Listen to you bathe. That way I can imagine I was your soap,” Shawn said. “You are so silly. Don’t you mean my wash cloth?” she asked. “Unh unh. I want to be your soap. I want to be slathered all over you, “ he said. When she heard this, her clit started to throb, and her nipples began to stiffen. “Oh really,” she said. “Oh yeah. That way I could enjoy all of you at once,” he said. The throb of her clit had begun to increase. “But then again, being your wash cloth would have its advantages as well,” he continued. “Although it would only represent one thing,” he said. “And what would that be?” she asked. “My tongue slowly moving all over your body,” he replied. By this time, Christina was already rubbing her clit, but when she heard this, she let out the slightest moan. Shawn heard it, and knew she liked what she was hearing. As he continued, she followed his words with her fingers, and imagined him actually performing the acts. When he kissed her in his description, she slowly rubbed her fingers across her lips and kissed and licked her fingers as if she were kissing him. When he talked about kissing her neck, she slowly and lightly rubbed her fingers across her neck. Her fingers represented his mouth and tongue licking and sucking on her nipples. They were his tongue slowly moving down her belly, past her belly button. “I’d take your clit into my mouth, and slowly lick and suck on it,” he said. She followed with her fingers. “I’d drink all the juices that came with it baby, “ he said. She began to move her hips slightly. “When I can feel you getting close, I’d slide two of my fingers into you and rub your G-spot while I continue to lick and suck your clit,” he said. Christina by this time, has completely lost herself in the moment. She is stroking her clit with her thumb, and ever so slightly rubbing her G-spot with two fingers from the same hand. “You clutch the back of my head as you cum in my mouth, down my throat, and all over my face………” he never even got the chance to finish that statement before Christina came all over her fingers. It was the most powerful orgasm she had ever had. Her entire body convulsed. Shawn could hear her scream his name. Then there was just moaning. Then just heavy breathing. When her orgasm was over, Christina was stroking the area around her clit with her fingers still. She didn’t dare touch her clit because it was too sensitive. “And when your orgasm is finished, I raise up to look you in your eyes, slide my tongue in your mouth and kiss you deeply. When our kiss is complete, you see my take those fingers and slide them in my mouth to drink what’s left of your orgasm…………..” he didn’t finish that one either before she came a second time. This time however, she hung up the phone. Shawn never knew if she hung up on purpose or by accident.  When she spoke to him the next day, she told him that they couldn’t talk anymore. “Why?” he asked. “If it’s about last night…..” before he could finish she cut him off. “We’re getting married Shawn,” she said. “My boyfriend is now my fiancé,” she continued. Shawn was silent. He didn’t know what to say. “I’m sorry Shawn, this has to be good bye,” she said. Before he could get a word out, she hung up and he didn’t hear from her again until he answered a phone call…………….17 years later. “Chris? Is that you?” he asked. “Yep, it’s me,” she replied. “Bet you thought you’d never hear my voice again,” she continued. “Uh, wow! How are you?” he asked. “I’m okay. How are you?” she asked. “I’m shocked right now. I never in a million years expected to hear from you again,” he said. “I know. I’m sorry for the way things ended. I hope you can forgive me,” she said. “No, no, it’s okay. I understood completely. I was just shocked when you told me you were getting married,” he said. “I know. I meant to tell you the last time you called me but our conversation went in another direction before I could,” she said. “Oh yeah, I’m sorry about that,” Shawn said. “I’m not,” Christina replied. “I’ve thought about that phone call a lot over all these years Shawn. No man had EVER made me feel that way, and no man has since,” she said. “I had to cut you off and try to forget about you because if I didn’t, my marriage would never work,” she continued. “But how could I affect your marriage? We’ve only met in person once. The rest of our friendship was over the phone. I hardly think one kiss and one session of phone sex is enough to affect a marriage,” Shawn said. “And yet it has. Like I said, I’ve thought about that conversation a lot. One nights when my husband doesn’t satisfy me, I wait until he goes to sleep and pleasure myself by thinking of you Shawn. Now, I’m at a point where my husband can’t satisfy me at all. I’m not saying he can’t bring me to a climax, but it’s just not the same. I don’t get excited about being with him. The sound of his voice doesn’t affect me. Shawn, my clit throbbed as soon as you said ‘Hello.’ Shawn was silent for a moment. He didn’t know what to say at first. “Are you two still together?” he asked. “Yes we are. We’re separated right now, but we are working on it. I still love him Shawn. I’m still in love with him, but I have to deal with this situation between you and I. I have to get you out of my system,” she said. “How do you propose to do that?” he asked. “I’m going to Vegas in two weeks with some girlfriends of mine. Can you meet me there?” she asked. “It’s too late for me to put in vacation time,” he replied. “You don’t have to. I just need you there for the weekend. I’ll even pay for your plane ticket and hotel room,” she said. “Well, ok. I’ll be there,” he replied. “I just confirmed all the reservations online. I’ll be staying at the Luxor hotel. Room 732. I want you to come to my room at midnight the day you arrive,” she said. “Okay. Do you want me to bring anything?” he asked. “No. You just need to be there. Listen Shawn, I’m not trying to mean or harsh when I say this, but all I need you to do is fuck me. I’ll leave the door open. I just need you to come in, fuck me, and leave. You don’t even have to talk to me. I don’t want to catch up on old times. I don’t even care if you’re married and have kids. Fuck me and leave, and I promise you will never hear from me again,” she said. “Wow. Uh okay. But I have to ask, why did you choose this way to get me out of your system?” he asked. “It’s what my sex therapist recommended. In other words, ‘Doctor’s orders,’ she replied. After they hung up, Shawn sat at the end of his bed. He was completely stunned. What she didn’t know was that Shawn had become a totally different man because of that phone call so many years ago. He had never married. Had no kids, and had never dated the same woman for longer than 3 months. He liked being a bachelor. He could pick up and leave anytime he wanted. So the opportunity to fly to Vegas and fuck some new pussy on someone else’s dime was not a problem for him. In fact, he looked forward to it.

Two weeks later, Shawn is walking into the Luxor hotel. It’s a short cab ride from the Bellagio where he is staying. After exiting the elevator on the 7th floor, he begins searching for room 732. He doesn’t see many people moving around. In fact the only person he saw on the floor was a man who looked as if he had just snuck out of his room. The man was carrying a black leather jacket and shoes, and kept looking back as if to see if someone was following him. The cigar he was smoking was awful. Shawn fanned the air trying to keep the smoke from settling on his clothes. Finally, he reached room 732. The doors of the rooms have an electric key card, but he didn’t need it because he noticed the door wasn’t all the way closed. He slowly pushed the door open and walked in. He quietly closed the door behind him and walked into the suite. It was very nice. The lights were low. The mood was set. He could see her lying in bed. She was lying face down on her stomach. He undressed and slid in bed beside her. He slid his hand across her ass and up her back until he reached her neck. She moaned lightly. He then straddled her legs and softly began to kiss her thighs, slowly moving upward. He kissed and licked her ass. He slid his tongue across the crack of her ass making sure to only slightly part the cheeks. Her moans grew louder. He slid his tongue up the center of her back, leaving a wet trail up to her neck. He could see her clutch the sheets as he reached the top of her back. As he began to kiss her neck, he noticed she was wearing a blindfold. “Damn, she doesn’t even want to see me,” he thought to himself. He could feel her grinding her ass against him as he was kissing and licking her neck. He made his way back down to her ass with his tongue. When he reached her ass, he buried his face between her lower cheeks until he could taste her pussy. She was so wet. He pulled her ass in the air and started licking her from behind. He could tell she loved every minute of it because she was pushing her pussy back on his face. Finally, her first orgasm exploded from her. She buried her face in a pillow let out a very loud, very deep moan. After he licked up as much of her excess juices as he could, he raised up and slowly slid his dick inside her. As the last of his shaft entered her, she raised up on all four, thrust her ass into his waist to get the rest of it. He started a ferocious stroke. You could hear her ass clap against him with every stroke. He could tell she wasn’t use to getting it like this. She reached up for the head board and moaned. “YES. YES Just like that. That’s the stroke I’ve been waiting for!!” she said. He didn’t say a word. He just continued to fuck her pussy with all his might. Minutes later her second orgasm rang out. He slowed his stroke, giving her a few minutes to recoup. While maintaining that slow stroke, he began to rub his finger across her asshole. He heard her gasp slightly when he did this, but she did not object. He licked his finger, and slowly penetrated her ass. She let out a painful moan, but still did not object. Slowly, he began to move his finger in and out of her ass. Going slightly deeper with each stroke. Her moans sounded painful, but pleasurable at the same time. He could tell by the tightness that she had never been fucked in her ass before. That would soon change. His dick was dripping wet from her second orgasm. He pulled out of her pussy, and slowly slid the head of his dick into her ass. The moan she let out sounded excruciating, but still she did not object. Relief seemed to come when he finally got the head all the way in. Slowly he began to fuck her ass. With each stroke going a little bit deeper. With each thrust she screamed into her pillow. As he started inserting his whole dick in her ass, she started rubbing her clit. He could feel her ass begin to relax. It was so tight around his shaft. As he got closer to cumming, the head of his dick started to swell. She seemed love this. She started throwing that ass back at him. “I want to feel you cum in my ass,” she screamed. That did it. He exploded inside her. She screamed from the top of her lungs. At first he thought he had really hurt her, but soon he would realize that she had cum for a third time. As the head of his dick slid out of her ass, she collapsed on her pillow. Moaning. Repeating over and over “Oh my God, that was so good.” Shawn cleaned himself off, got dressed and left the room. As he walked down the hallway he knew he would never see or speak to Christina again. “What happens in Vegas…..” he said to himself. As he entered the elevator he realized he had left his cell phone in his room. “No big deal. I’ll get someone at the front desk to call me a cab,” he said. As the elevator door opened, he walked passed the gentleman he saw on the 7th floor. He jumped in the elevator Shawn had just vacated. He looked as if he had had a good night in the casino. He was all smiles. Tonight was a good night for both of them. When Shawn finally got back to his room, he noticed his cell phone was blinking. He had one missed call.


Victoria was really pissed at her husband.  They had come to Vegas for their anniversary, supposedly to spend some quality time together.  James, her husband, had spent more time with the pit bosses of the casino than he had with her.  Well, the day had finally come for them to leave, and wouldn’t you know it, James won a free night in the hotel.  James wanted use the extra night while they were there. Victoria was totally against it. “How can we? Our flight leaves tonight,” she said. “The hotel has already taken care of it. They paid for all the charges for changing our reservation,” he replied. She had no choice. She was stuck in Vegas for another night.  At this point she was fed up. They had been in Vegas 3 days, and James hadn’t touched her. He spent his time with the pit bosses. She spent her time with BOB (battery operated boyfriend). “Okay. Fine!!” she shouted.  “We can stay, but you’re gonna spend some time with me today. No more casinos. We’re gonna go out see a show, have dinner, and go to bed. And maybe if I’m lucky, you might even make love to me,” she said. “What are you talking about Victoria?” he asked. “You don’t touch me like you use to.  You just lay in bed slide your dick in for a few minutes, make a mess on my sheets and roll over!!! I can’t even remember the last time you made me cum!!!!” she yelled. “What about last weekend?” he asked. “I faked it just to get you off of me! You smelled like cigar smoke, and you know I hate that!!!” she said. “Shit!! Fine. Fine. We’ll go out, and if I’m in the mood we’ll……..ya know. Do it,” he said. “Sounds so romantic,” she replied sarcastically. Later that evening, they went out to see a Vegas Show and had dinner. While they were out, James made sure to put as much to drink in front of Victoria as he could. His hope was that she would be too tired for sex later and would fall asleep. Later when they returned to the room, Victoria was definitely tipsy. But being tipsy just made her hornier.  She immediately stripped out of her clothes and tried to make James do the same. “Vikki, I’m not in the mood babe,” he said. She tried to force the issue. She unzipped his pants, pulled his dick out and shoved it into her mouth.  She slowly slid her mouth up and down on it.  His dick became hard as a rock.  She gripped the base of his shaft and began to stroke it while she sucked on the head. He stood there with his eyes closed and just enjoyed it.  He was really into it at first, then his mind drifted to the casino and he went limp like a wet noodle. Victoria felt him go limp and pushed him away. “Just go. Go be with the people you love. Apparently none of them are here in this room,” she said. “No baby, it’s not like that. I’m just tired that’s all. Let me lay down for a few minutes and we can continue where we left off. Okay?” he said. “Sure James,” she said. She put her blindfold on, rolled over and just laid there. James laid in bed beside her fully dressed and waited. After about an hour, he nudged her to see if she was asleep. No response. He got up, grabbed his jacket and shoes and snuck out the door. He made sure not to close the door all the way so that he wouldn’t have to use the key to get back in. Outside the room, he lit his cigar and headed for the casino.  Little did he know, Victoria was not asleep. She heard him leave. She was pissed that he had chosen to leave. Just once she wanted him to choose her over something or someone else. She wanted to come to Vegas to let loose. She wanted to go crazy with James. Do some freaky stuff they had never done before. That was the first time she had sucked his dick in years. She was going to keep sucking until he came in her mouth. Then she would get him to eat he pussy like he use to. Even if he didn’t do it anymore after tonight, she could chalk it up to a ‘What happens in Vegas…..’ thing. But no, he chose the casino. She felt like crying. Just then she heard the door open.  He came back. “He probably forgot his wallet,” she thought. Then she felt his hand slide across her ass. She had goose bumps. She heard him get undressed and then slide in bed with her. She caught the faint smell of his cigar. “He just stepped out for a quick smoke,” she thought to herself.  When his tongue slid across her ass, up her back to her neck, it felt so good to her. He hadn’t touched her like that in ages. She moaned slightly.  She got wet instantly when she felt him kissing her body.  She couldn’t believe it when he pulled her ass in the air and began licking her pussy from the back. She wanted to rip the blindfold off and kiss him, but the blindfold was actually part of what was turning her on.  It had been so long since her pussy had been eaten.  She wanted to scream so bad but she was trying to fight her orgasm from coming so fast. He was licking it so good she started pushing her pussy into his face until finally she came. “MMMMMMM” she moaned as she buried her face in her pillow. She could feel her juices running down her leg, but he was licking it up like a starving animal.  When she felt his dick slide in her she was shocked by how big he seemed tonight. She chalked it up to the fact that it had been so long since she had a dick inside her after she had had an orgasm. He started off slow, but then started fucking her like he was in some new pussy. She moaned and yelled, “YES. YES Just like that. That’s the stroke I’ve been waiting for!!” she said. She couldn’t believe she had just said that. Talking during sex was not something she had done in a long time. It just felt so good tonight. He was fucking her the way she wanted to be fucked. The way she needed it. Even if it was only for that night. His stroke drove her crazy. His stamina shocked her. She imagined James in his younger days. She remembered the time she looked into the mirror while James was fucking her doggystyle. She remembered how it looked as if he was a wild beast trying to shove his dick in her as far and as hard as he could. That memory plus the fact that he was hitting a spot in her pussy he had never reached caused her second orgasm to explode on his dick. The second orgasm exhausted her. But James was still stroking his massive throbbing dick in her. “He can fuck me until I pass out,” she thought to herself. He slowed his stroke, and now he’s rubbing her ass hole. This is new. It startled her at first, but tonight, he can have whatever he wants. He slid a bit of his finger in her ass. It hurt like hell, but he was very gentle, so she took the pain. He began to slowly stroke his finger in and out. Putting more and more in as he stroked. It still hurt, but not as bad as it did in the beginning. She knew he would put his dick in soon. She was ready. As the head started to go in, the pain was almost unbearable, but what really shocked her was how hard her nipples were. She was actually turned on by it. Her pussy was still dripping wet as well. The pain subsided once he got the head in. His stroke was slow. Steady. She moaned with every stroke. Her moans turned into all out screams. If not for the pillow she was clutching over her face, she would have awakened the entire floor. Each stroke was painful, but she found herself pushing her ass back on his dick. Her clit is throbbing. She doesn’t understand what she is feeling, but she refuses to stop it. Her clit was throbbing so much she started to stroke it. It felt so good. “FUCK MY ASS BABY!!!!” she screamed into the pillow. His stroke was magnificent. She could feel his dick swelling. He was about to cum. “I want to feel you cum in my ass!!” she screamed. As soon as she got it out she felt him explode inside her. His moan and that feeling caused her to cum for a third time. When his dick slid out of her ass, she collapsed on the bed. She didn’t move. She just laid there. She heard him clean up, get dressed and walk out the door. She didn’t have the strength to stop him. She wouldn’t have stopped him if she could. “Go have a good time baby. You earned it,” she said. She fell asleep. Exhausted. Sore. But happy.  The next morning, all she could do was smile at James as she watched him come out of the shower. “You’re not still mad at me are you Vikki?” he asked. She walked over to him, gave him a big kiss and said “After last night, how could I be?” She went back to packing her suit case. “I must have given her too much to drink last night,” he thought.




Shawn threw his jacket down on the bed and picked up his phone.  The missed call was from Christina. She called at 11:50pm. “Hey, I almost forgot to call you. Some guy decided to stay longer in my original room, so the Luxor had to change my room. I’m gonna be in Room 738 instead. See you soon.”




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Heads, Tails, and Oops: The Three Sides of a Strange Coin., 9.9 out of 10 based on 12 ratings

One Response to “Heads, Tails, and Oops: The Three Sides of a Strange Coin.”

  1. breeze

    I loved the twist in your tale!

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