The Unexpected Anal Encounter


             Joe Kelley steered his car into the parking garage, found an open spot, turned the car off, and took a deep breath. It was the day of his annual physical. He had no reason to be nervous but anything medical caused him some anxiety. Joe made his way into the large medical office building and up to the 8th Floor to the office of Dr. John O’Connor. It took several minutes to check in with Judy, the office assistant. He knew the routine. Fill out the information sheet, give her the insurance card, and settle in for a wait. There were three other doctors in the office and two other people sat patiently waiting. He had the last appointment of the day and he hoped the wait would not be long.
                The time gave Joe a few minutes to reflect. Now 45 years old, he had been divorced for 3 years with 2 kids in high school. The kids were Sarah, 15, and Julie, 18 and they lived with his ex-wife, Paula. He saw them on most Wednesday evenings for dinner and every other weekend.   Joe was an accountant and had worked for a medium sized accounting and business consulting company for 18 years. He didn’t think of himself as a workaholic but the demands of his work had definitely taken a toll on his marriage.

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                Dr. O’Connor opened the door and interrupted his thoughts. He greeted Joe and invited him into his office. Joe had been seeing the doctor for several years and liked him. They were both in their mid 40’s and he had been very supportive during the divorce. As they entered his office Joe was surprised to see a young woman standing next to the desk.
                “Joe, this is Molly Grant. She’s a pre-med student at the University and has been sitting in with me today. If it’s ok with you, she will be observing your checkup. ”
                Molly smiled and Joe introduced himself.  Like most guys, he quickly checked out her appearance. She was medium height, dark haired, had a pretty face and carried a few extra pounds. Average, but not bad, was the thought that came to Joe’s mind. He turned to the Doctor, “It’s no problem Doc. She’s welcome to stay.

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                They all sat down and Dr. O’Connor went through a series of questions to update Joe’s history and to see if there had been any changes in his health. Most of it was routine and the doctor once again told him he needed to work some more exercise into his life. Joe acknowledged the shortcoming and turned to Molly and joked, “He can be a nag sometimes. ”
                Molly just smiled and the doctor then directed Joe to the examining room, “Strip down to your shorts. I’ll be back in a minute. ”
                Joe got undressed and sat on the examining table in his boxers. He was 5’10”, weighed 180, and was in reasonable shape for a guy in his mid 40’s. The door opened and Joe was a little surprised to see both Dr. O’Connor and Molly enter the room. He felt a little embarrassed and maybe a little thrilled to be standing in his underwear in front of Molly. The doctor spoke first, “Is it ok if she observes?”
                Joe nodded, “It’s fine. ”
                Dr. O’Connor started the exam as Molly stood off to the side of the room. He did the normal physical checks, conducted an EKG, and finally said he needed check for a hernia and do the prostate exam.


   Joe stood next to the examining table and slipped his boxers down to his knees. Dr. O’Connor hesitated for a minute and then said, “Oh, ok, I was going to ask Molly to leave for this but I guess it’s ok. ”
                The doctor did the hernia checks, examined Joe’s testicles, and then told him to bend over the exam table for the prostate exam. As he turned, Joe caught Molly’s eye and she gave a slight smile. Then he felt the lubricated finger slide up his ass. He thought to himself, “Well, she is sure getting the whole picture. ”
                With the exam completed, Joe dressed, spent a few minutes with the doctor, checked out, and headed down to the lobby. There was a coffee shop on the main floor and Joe went in to grab a cup for the ride home. He saw Molly standing at the counter, said hello, and offered to buy her a cup.
                After getting their coffee they sat at a table and she thanked him, “I needed this. It’s been a long day. ”
                “I hope you learned some things. ”
                “Most of it was kind of boring but it was nice to see what he actually does on a typical day. ”
                There was a moment of silence before Joe spoke, “I hope I didn’t embarrass you.

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   I thought you were there to see the complete exam. ”
                Molly gave a little laugh, “Well, it was a little unexpected, but …. . um” She hesitated.
                “But? But what?”
                “Oh, nothing. I don’t want you to think I’m weird. ”
                “Please, go ahead. Hey, you’ve already seen me in a pretty compromising position. ”
                “That I have. It’s just that it was kind of, well, erotic. ”
                Joe stopped and looked at Molly. “Erotic? I think you have to tell me more. ”
                “Ok, it wasn’t the fact that I saw you naked. I’ve seen guys naked before. No big deal.

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                Joe tried to look offended, “Thanks. You know how to hurt a guy. ”
                Molly smiled, “No, no, I’m not saying I didn’t like that part of it too. It’s just that I didn’t expect to be affected by the anal thing. ”
                Joe was surprised to suddenly find himself in a sexual discussion with a young woman. He loved the openness and he wanted to continue it. He wanted to see where it was headed, “Did you like seeing the doc have his way with me?”
                Molly was intrigued too. This open talk wasn’t something she had done before. “I’m not sure how to explain this. I’ve been with guys before but, well, I guess most of what I have done is pretty normal. You know, just sex. ”
                “Did you sort of wish it had been you instead of the doc doing the exam?”
                Molly blushed slightly, “The thought crossed my mind. You probably think I’m being a little silly. I mean you were married. I’m sure you had a chance to do all kinds of things with your wife.

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                Joe looked down and did a quick reflection on his married sex life. The truth was it had not been that great. Paula was a nice looking woman but not all that enthusiastic or adventurous about sex. She did not like anything out of the ordinary and that included any anal activity. Even oral sex became infrequent during those last years together. He looked up at Molly, “You might be surprised. I don’t think my ex would have found that scene erotic at all. I must say though that the idea of you doing exam is very appealing. How long before you become a doctor?”
                He saw a grin on her face, “Maybe we don’t have to wait that long. ”
                “Are you saying what I think you are saying? You know I’m almost old enough to be your father. ”
                “Joe, I know this is a little weird but I like you and for some reason you have made me instantly comfortable. I can’t believe what we just talked about. You’re divorced. I’m not involved with anyone. Why not have some fun.

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   You don’t seem bothered by my interest in this. ”
                “Why don’t we go and grab some dinner? That will give us some time to get to know each other better and decide where we want to go with this. ”
                “I like that idea. It’s been awhile since anyone asked me to dinner. ”
                They left the coffee shop and drove to an Olive Garden a few miles away. It was a Tuesday night and the restaurant was not busy. Dinner went well and they both enjoyed doing something purely social for a change. Molly had been focused on her pre-med program trying to increase her chances of getting into med school. Joe had filled the void created by his divorce by just working more and more. Even though they had just met there was a level of trust and intimacy in their conversation.
                Leaving the restaurant, Joe walked Molly to her car where she turned to face him. He gave her a kiss and she smiled. He thanked her for an enjoyable dinner and asked, “Would you like to join me at my apartment?”
                “Will I get to play doctor?”
                “Absolutely. Anything you want. ”
                Molly followed him to his apartment and they walked to the front door together.

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   He unlocked it and allowed her to step inside. After closing and locking the door he turned and she was in his arms, kissing him. He held her and they kissed for several minutes, her body pressed against him and his hands caressing her back. Joe then directed her to his bedroom, “You’ve seen me naked. I want to undress you. ”
                “Let’s undress together. ” Molly began to unbutton her blouse. Joe followed her lead and unbuttoned his dress shirt. They slipped their shirts off together and Joe’s eyes were drawn to Molly’s white bra with her nipples pushing through the thin material. She reached behind to unhook it as Joe lifted his t-shirt over his head. The bra fell away exposing Molly’s beautiful, nicely sized breasts. He took a deep breath, “Molly, you are beautiful. ”
                She ran her hands over her breasts and gently held her hardened nipples between her fingers. She then reached down and began to undo her slacks. Joe again followed and they pushed there pants down their legs together.

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   Molly saw Joe’s obviously hard cock pushing the front of his boxers out and smiled. Joe was focused on the white silky panties worn by Molly. She hooked her thumbs under the waistband and said, “Let’s do it. ”
                The underwear slid away and they stood naked facing one another. Joe took her into his arms feeling her skin against his. They kissed and caressed and he pressed his hardness into her.
                Molly was medium height, 5’5”, and weighed about 140. She had nice sized breasts with smallish nipples and carried a little extra weight around her middle. Her pubic hair was full and matched the short dark hair on her head. In her 21 years she had had sex with a total of 3 guys, one in high school and two in college. In her estimation, the first and last had been about average and the middle guy a little better. The relationships had not lasted long and the sex did not progress beyond some oral and intercourse.
                Joe would definitely be the most experienced (and oldest) lover she had been with. As they embraced she reached down and took his hardness into her hand. She slowly stroked him loving the feel of his fully erect cock, loving that he was excited for her.

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   After caressing him for a minute Molly whispered into Joe’s ear, “Do you have any KY?”
                He pulled away, walked toward the nightstand, and chuckled, “Actually I do. I was a great Boy Scout. Always be prepared. ”
                Molly took the KY and instructed him to bend over the edge of the bed. Joe positioned himself and she paused, looking at his ass. This was what she had always thought sex could be, a chance for two people to explore, to be playful, and be open to new experiences. Molly spread his cheeks and ran her finger over his ass. Joe jumped and moaned. She applied some KY and massaged his dark hole before sliding her finger in. The feeling was not new. She had had her finger in her own ass in the shower but there was a thrill to be doing this to a man.
                “How’s that?” She asked.
                “I like that it is you. ”
                “I love the feel. So tight.


   So different. ” She moved her finger moved slowly in and out for a minute or two and then paused and asked him to lie on his back. Joe scooted onto the bed and Molly joined him. She took his cock in her hand, stroked him, and leaned down to take him into her mouth.
                Joe moaned as Molly sucked him. He felt her tongue move over the head of his cock and then the gentle pressure as took as much as she could into her mouth. Molly had always liked pleasing a guy like this. She knew how intense the feeling could be for a man and she liked the feeling of control it gave her. As she sucked him her finger moved back to his ass and she slipped it into the tight hole.
                “Oh God, yes. ” Joe tried to push his cock further into her mouth as her finger moved in his ass. The combined feeling was incredible and he knew he was going to cum. He wanted it to last but Molly’s wonderful pressure on his cock pushed him over the edge and he cried out as the first jets of cum shot into her warm mouth. Joe’s body shook and jerked and she held him in her mouth swallowing his cum. It had been a long time since he had felt an orgasm anywhere near as intense.

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   When he relaxed, she moved up and kissed him.
                Joe spoke first, “I’m speechless. You really got me going. That ass thing is wild. ”
                “It was awesome. I could feel it in your ass when you came. I can’t believe we did that. ”
                Joe kissed her, a slight taste of semen in her mouth, “Can I return the favor?”
                Molly lay back, “I want you to. That got me so hot. ”
                Joe kissed his way to her breasts while his fingers moved between her legs. He took her nipples into his mouth and she moaned softly as he sucked gently. His fingers slipped through the curls of her pubic hair and he touched the soft lips of her pussy.
    Pushing a finger between them he could feel her wetness. Wanting to taste her he moved between her legs and let his tongue slowly move up and down her slit.
                    It had been a long time since Joe had been with a woman this young.

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       He wanted to take it slow and really enjoy her. She still had that youthful fascination and joy with sex.   Joe had always loved giving a woman oral and he really loved it when he was able to make them cum. It had happened very rarely with his wife and hoped he could experience it with Molly. He looked up at her and said, “This is good. Your pussy is beautiful. ”
                    Molly closed her eyes, relaxed and let herself just enjoy the sensations. Joe was really hitting all the right spots. His tongue was inside, then it was on her clit. She was moving and he seemed to be in the same rhythm touching her just where she wanted it and with just the right pressure. It had been some time since a guy had his face between her legs and before long she knew she was going to cum.
                    “Oh Joe, oh my God, yes, that’s it, oh God. ”
                    He knew she was close and he focused on her clit, gently sucking it into his mouth, then flicking it with his tongue. Her hands caressed her nipples and then he felt it. She tensed and moaned and the waves of her orgasm took over.


       Molly’s body shivered and her hips moved as she came. Joe continued to lick her wanting to make it last for her. When he felt her relax he moved up to lie beside her.
                    Molly turned and smiled at him, “You’ve got a great tongue. ”
                    “It was my pleasure. ”
                    Even though Joe had just cum, giving Molly oral and seeing her orgasm had aroused him again. He knew that had almost never happened with his wife. He pulled her into his arms and hugged her. They hugged and caressed and Joe pushed his erection against her. Molly reached down and took him into her hand, slowly stroking him and whispered into his ear, “Look what woke up again. ”
                    “Seeing you cum like that got me going again. ”
                    Molly laughed, “What should we do with it. I can’t leave you like this. ”
                    “Not sure what you think but I have a real desire to do your ass. ”
                    “I’ve never had a cock there.

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                    “We don’t have to. ”
                    Molly thought about her past sexual experiences. Even though they had just met, she knew this was the first time she had felt truly relaxed and comfortable with a man. She had always worried about doing the wrong thing or something the guy had said or done had prevented her from relaxing. Maybe it was Joe’s age or his level of experience. She just knew that whatever she did would be ok with him. The thought of trying anal intercourse was new, exciting, and a little scary. It felt a little dirty, a little forbidden. She wanted to at least give it a try. Joe had thought she had given up on the idea when she spoke, “I want to give it a try. Just take it slow. ”
                    “I’ll be gentle, I promise. If you change you mind, I’ll stop. ” Joe smiled. He wasn’t sure why, but for some reason he wanted this.

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       He wanted to push his hard cock into Molly’s ass. Taking a deep breath, he told himself to relax.
                    Joe told Molly he would start with a massage. Molly turned on her stomach and Joe began to rub and caress her neck, shoulders, and back.   Straddling her, Joe’s hard cock rested between the soft cheeks of her ass. He rubbed against her and she responded with a soft moan. It felt good. Molly’s ass was soft, smooth, and a little large.
                    Moving down her body Joe massaged Molly’s lower back and then ran his hands over her ass. He massaged the cheeks and parted them to look at her beautiful brown rosebud nestled deep within. He touched it with his finger and he felt her tense slightly. Joe took the KY and began lubricating her tight hole. His finger gently massaged her slowly working its way in. She truly had a beautiful ass and he could feel her relax and begin to respond to the finger probing her.
                    “God, you have a great ass.

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       Paula would never have let me do anything like this. ”
                    Molly liked to finger her own ass in the shower but this was definitely different. She liked the attention and the compliments and felt totally open and exposed. Joe’s finger moved slowly in and out of her well lubricated butt hole and she moved with him. “Your finger feels good. I want to try your cock. ”
                    Joe stopped and rubbed some KY onto his rigid cock. He positioned himself and started to press his cock against her ass. He took a deep breath and asked if she was ready.
                    “Go for it. Just take it slow. ”
                    Joe pushed and felt his hardness slipping into her. It was tight but she took him much easier than he expected. There was a brief gasp from Molly as the head of his cock pushed past her tight sphincter and then he found himself fully inside her. It was an incredible feeling and he felt a rush of emotion as he slowly started to move in her.

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                    The ease with which Joe had entered her had caused most of Molly’s apprehension to disappear and she found herself excited. This was going to be something she did for his enjoyment but she liked the feeling of his cock in her. She reached back to rub her clit as Joe began moving in and out.
                    “Oh God, I love your ass. ” Joe sensed her comfort and began to thrust himself in and out of her.   This is what he wanted. His cock buried in this girl’s tight ass. Molly was moaning and moving to meet his thrusts. He knew the tightness on his cock would not allow him to last long. It just felt so good.
                    “Molly, I want to cum in your ass!”
                    “Give it to me! Do it!”
                    Joe had his hands on her hips and was moving himself in and out of her ass as Molly rubbed her clit and moved with him. She cried out as the first wave of her orgasm shook her body. Joe felt her shake and pushed deep inside her as the first shot of cum erupted from his cock. He continued to pump into her until they both collapsed on the bed.
                    They were both breathing hard.

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       Molly finally broke the silence, “Holy shit. That was intense. ”
                    Joe laughed, “Holy shit is right. That was unbelievable. ”
                    They relaxed for awhile, talking and laughing together before Molly dressed to go.
                    Joe walked her to the door, “Can I call you?”
                    “I’d like that. ”
                    “Maybe we can get together again sometime. ”
                    “I’d like that too. ”



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