What Might Have Been

John and Paul went to school together, and became best friends. John moved away after school, and they kept in contact. When the opportunity presented itself, they tried to meet up. Since high school it had only been once, but they were both in college. John was 21 now and was heading back to the Milwaukee area where Paul lived, and Paul was turning 21, so they made plans for John to stay with Paul when he was in the area.

Paul was working, so he asked his finance Sarah to pick him up from the hotel. He would not need a car. Sarah picked up John on a Wednesday afternoon. At first, Sarah was not a fan. As the day went on, Sarah saw something in John. Her thoughts changed. She understood why Paul was such good friends with him. Together, the three of them drank, camped, went to baseball games, played board games, and had a lot of fun over the next few days. Sarah and John just connected on the friend level.

Over the next year, Paul and John remained close, and a new friendship budded between Sarah and John. Since they were all in college still, John made it a habit to call both Paul and Sarah. They had a lot in common. Sarahs father grew up where John lived, and still had family there.

When John was looking for something to do the following summer, he thought about going to see Sarah and Paul for a week when Sarah had a break in her classes. She was a student at a Physican-Assistant school outside of Chicago. John called Sarah and Paul (who was living there in the summer with her while she was in school) to find out when her break was. Sarah had to tell him that it was a great idea, but that Paul would not be home all summer. He was going to work at a summer camp in Tennessee.

Paul was not really keen on the idea of his friend and his fiancé staying together for a week, but he trusted both his fiancé Sarah, and his good friend John, he thought what could happen.

Vacation was set for the week leading up to July 4 just outside of Chicago. John made the five hour drive and pulled up to the apartment complex around 3pm. John grabbed his duffle bag, climbed a few flights of stairs, and knocked on the door. Sarah answered, giving him a big hug. She had already been making dinner for the two of them. John asked to use the shower, as it had been a long drive.

In the shower, John stripped and got in the shower. It had been a long year. John had been broken up with his girlfriend for a few months. Not that it mattered. They had not had sex in almost 9 months. She was cheating on him again. John was cheated on the previous year, and decided to give it another go, mainly to give himself time to let go on his own terms.

As John was washing his hair, he began to think about Sarah. "Damn she looked good" he thought. She had a great set of 36C tits, a firm ass, perfect hips, and he knew she worked out all the time. He was thinking that he could have bounced a quarter off of her ass. As he thought this, his cock began to grow. This was not going to be an easy week. It was supposed to be hot, meaning Sarah would not be wearing a lot of clothes, mostly dresses to keep cool. He grabbed the conditioner, put some in his hair, worked it in, then put some more on his hand, and began to stroke his cock. Letting the water from the shower hit his back, it only took a few minutes before he had the familiar feeling. A couple more tugs, and a couple more visuals of what Sarah would look like naked, and his ass cheeks clenched and he unloaded four solid ropes of cum on the back wall of the shower.

As he came down from his orgasm, he thought he had better finish up and get out of the bathroom. Sarah was just finishing dinner. She had made some Mexican dish. Paired with a glass of wine, they both caught up with how things had been, how crappy John's love life was, how Paul was doing in school, and how Sarah liked PA school so far. She also gave him a rundown of the things they would do this week. Spend a day in Downtown Chicago, head to a family friends house for July 4 fireworks, and they could bum around town another day or two. Sarah had to study during her break. So she had to take one or two days and put her nose in the books.

As it got later in the evening, Sarah had already set aside two pillows, a blanket, and a sheet for John to make a bed on the couch. She went to the bathroom, cleaned her face, while John made his bed. Since it had been a long day, they both were sleeping soundly for a nice summer evening.

Day 2 - Chicago

Sarah was up early. She made her morning coffee, trying to be quiet, but John was a light sleeper. He was up when he heard the microwave go off. Sarah was not expecting him to be up, as she was only wearing her night t-shirt, thong panties, no bra. The A/C was on in the small apartment, and as she moved around the kitchen, getting breakfast ready, her nipples were straining against her t-shirt. While the shirt covered her, when she would bend over for a pan, or reach for the salt for the eggs she was making for breakfast, John would get some great glimpses of her cute ass. He had a thing for thongs. He loved them, and her ass looked amazing in them!

While Sarah as cooking, John got up and tried to make his way to the bathroom down the hall while hiding his morning erection. He is pretty sure that Sarah saw him trying to hide it when he was walking, and he thought she had a little smile while looking down, but he was not certain. John was not too confident with his size. He was average at best, only about 5-5.5 inches. Up to this point, he had only been with two women, and neither had complained. He was not porn star big, but he knew how to use it.

After coming out of the bathroom where John had brushed his teeth and used the toilet, and washed his face, he was disappointed that Sarah had put some shorts on. They made sure that he did not catch any peaks that were not intended.

After breakfast, they both dressed and got ready for a day trip on the train to downtown Chicago. When Sarah came out of the room, John was already ready to go. He had on a pair of golf shorts, golf shirt, and some tennis shoes. Sarah was dressed in a wide strapped white dress that came down to her mid thigh. She had checked the weather and knew it was going to be hot that day, almost 95 degrees in the Windy City. They were going to do a lot of walking, and she wanted to be as cool as possible. As they make their way to the car for the short drive to the train stop, John was able to see that Sarah had chosen to wear a white thong. Her dress became almost see through as the sun hit her. After a few quick glances, he noticed that she had on a cute lace bra. When the sun hit just the right angle, he thought he could see the darkness of her nipples. He did not want to stare, but he could not help but look at her ass every chance he got.

For the rest of the day, they explored the Miracle Mile, Navy Pier, Water Tower Place, and other landmarks in downtown Chicago. It was super hot, they were both exhausted because of the heat, so they cut their day trip a little short and figured they would head back before dinner, pick up carry-out on the way back, and cool off in Sarah's apartment.

After they got to her apartment, they both needed a cool shower. Sarah went first. She just grabbed a towel from the closet and went a got in the shower. A quick shower for her and when she was done, she ducked into her room in her towel to put some clean clothes on. John was so hot he had not even noticed and simply went to the bathroom to take a cool shower. The temps had reached over 100 degrees, and they were both exhausted. John turned the shower on, brushed his teeth, and as he was taking off his shirt, he instinctively opened the dirty clothes hamper. On top of the dirty clothes was Sarah's thong. John was hot, but he was so horny from looking at her ass all day he grabbed her thong and gave it a quick smell. It had all of her pheromones. The smell only made his already growing cock grow even more. He took the white cotton panties, wrapped them around his member, and began to stroke. With the views he had all day, it took less than 2 minutes before he released rope after rope of thick, warm cum. Most landed on his belly, but a few went right on her thong. John simply wiped up the cum, placed the panties back in the dirty clothes, jumped in the shower, and finished. He needed that. Now he could at least eat dinner and not have to think about standing up in basketball shorts and her seeing his erection.

When he came out of the shower, Sarah had plated the food they picked up, and they sat at the table and ate dinner. After dinner, and a game of scrabble, Sarah was beyond tired. The heat had done her in. They were supposed to go hang out with some of her friends from school the next day, but she was too tired to even think about it. One of them called Sarah and they decided to put it off until the next day. She was going to use tomorrow to sleep in and study. John was going to just bum around, maybe go for a walk in the park, but he too was tired from the heat. He had rules to review for a hockey tournament he was working in the next few weeks, so he would just use tomorrow to catch up on those. It was still over 85 degrees outside, and the A/C in the apartment was struggling to keep up. Sarah asked John if he minded if she set the temperature to 77. It was warmer than they both liked it, but she did not want to burn out the A/C unit in the apartment. They had both agreed, as the heat was unbearable outside, and it would not go lower than it was now.

Sarah called it an early night around 10pm. She had gone to bed, and left John up. He was tired, but not yet ready for bed, so he turned the TV on and was watching for about an hour or so. As he was making his couch bed for the night, all of the water he was drinking was catching up with him and he had to use the bathroom. It was still over 85 degrees outside, and the A/C in the apartment was struggling to keep up.

The couch where he was sleeping was positioned on a wall that was shared with Sarah's bedroom. About 4 feet down the hall on the right was the door to her bedroom. The bathroom was on the left at the end of the hall. John had turned off the lights in the living room before he moved down the hallway. When he did, he noticed that Sarah's bedroom door was not closed all of the way. It was only about 2-3 inches, but enough that there was some light coming out of her room, probably from a small night light she had on her night stand.

As John walked by, he could see right in the room, right on the bed. Sarah was sleeping on her stomach. She must have changed before bed, because she now had on a short t-shirt, one that would just fall below her breasts (most likely when Paul was home), and she had on a light blue Victoria Secret cotton thong. She was sleeping on her stomach, and her left leg was positioned at a 90 degree angle so that her mound was perfectly visible to John in the pale light. He stopped and stared for a minute, maybe two.

As he was admiring the view, he really had to pee. He quickly went to the bathroom, and came back. In that short amount of time, Sarah had shifted. She had rolled on her back, her legs in a perfect V. The shirt she had on no longer covered her breasts. They had the perfect naturalness to them. Sarah had been using a light sheet to cover up, but since the temperature was up in the apartment, the sheet was in a pile on the side of the bed. John was looking at beauty. He was so hard now.

He thought about going in the room. He had seen the way Sarah looked at him this morning. She was engaged to one of his best friends. There is no way he could do it. He was not going to be the reason they would have problems. He was not one to do that type of thing. Paul was his good friend, and he did not want to do that to Sarah.

As John was thinking all of this through, his cock was standing at attention. He was slowing stroking it, watching. He loved to watch. Her nipples were now hard and protruding, and the closer he looked, he could see that Sarah had a bald pussy. There did not appear to be a lick of hair. Seeing her like this, as his thumb came to the tip of his cock, it got really slick with the glob of precum that had leaked out. He thought about it, but John did not want to take advantage of the situation any more, and went back to lay down. He needed to be good. Instead of cumming again that day, he tried to be good and put himself away and go to bed. He tried to clear his head, and when he did, he was sleeping within a few minutes.

Sarah woke up early, around 6am. Before she left her room for the bathroom, she made sure to change shirts and put some shorts on. A quick tinkle, and she needed her morning coffee. On her way from the bathroom, she decided to drop the temp back to 72 for the day. It was going to be another hot one. It was a small apartment and it was going to cool quick. As she entered the kitchen, she glanced at John on the couch. He was sound asleep. She quietly made her coffee and grabbed her anatomy book to study muscles of the arms and legs. Even though she was on break, she still needed to learn and study.

It was almost 7am and the apartment was cooling very fast. Sarah got out of her chair to grab a blanket and cover up John while he slept. When she did, she could not help but notice that John had a very erect penis. It was straining against his underwear, but she could easily make out the mushroom head. As she covered him up, she got a very familiar tingle in her loins.

She brushed it off, and went back to studies and coffee at the kitchen table. As she looked at the muscles of the right leg, she could not get the sight of his erection out of her head, and she could feel her panties getting damp and her nipples were beginning to harden. She was trying to get the thoughts out of her head, so she stood up, grabbed her coffee, and went into her bedroom to make her bed and grab some more books to study.

When John heard her door close, it woke him from his sleep. He awoke to the same sights in his head that he had when he went to sleep. Sarah in all her glory. He figured she had just taken a shower, and would be getting ready for a few minutes. He was still really horny, and his morning erection was telling him that he needed some relief.

He figured Sarah would not know, so he began to stroke him already throbbing member. John wanted this orgasm to be a good one, not like the previous one in the bathroom, which was way too quick for him.

John slid his underwear off, and slowly started to stroke himself. He must have gotten lost in his thoughts, as he did not hear the bedroom door open. Sarah had done it quietly, as she thought John would still be sleeping.

As she tip-toed out of the room with her books she saw John masturbating on the couch. His underwear around his ankles, he had already taken his t-shirt off so that he could keep it from getting cum on it. As he was stroking his erect cock and slowing rubbing in the leaking pre-cum that was dribbling out of the tip, Sarah stopped in her tracks. He had no idea she was there.

Sarah was mesmerized. She had seen Paul masturbate himself before, but never anyone else. She was surprised but could not look away. It has been over a month since she had been laid, and over 3 days since she had been able to get herself off. She normally masturbated daily when Paul was not around, for she was someone with a very healthy sexy habit.

John was lost in his own thoughts, stroking away, Sarah's panties were getting wet. Her nipples started to get the type of hard that she knew if she tugged on them that it would go straight to her pussy. Without thinking about it, she reached down and rubbed the outside of her panties with her fingers. Damn it felt good for her. She quietly watched and slowly rubbed her clit through her panties.

She really liked what she saw. The more she stared, the more perfect his cock looked to her. She began to think that the head was perfect, a great shape. He was not that long, but damn, he looked thick. Thicker than Paul. She began to imagine what his cock tasted like. She thought about what it would be like to have him in her mouth. The more she rubbed, the wetter she got. Her panties were soaked through. As she rubbed with her right hand, her left hand instinctively grabbed at her nipple, and she gave a small little moan.

This small moan caught John by surprise. He quickly snapped his head back and their eyes met. John tried to cover up, but Sarah stopped him.

"Don't stop on my account" she said.

John stood up and walked toward Sarah, naked as a jay bird, and said "I think you are overdressed for today's planned activities, let me help you with that."

As John reached Sarah, who was only five feet away, their lips locked and their tongues danced. Sarah had not been kissed like that in a long time. As they kissed, John was slowly removing her shorts. She helped with those, and she removed her shirt. John moved from her lips to her nipples. Her perky breasts were calling his name. After a few minutes on one, he moved to the next. As his mouth played with her nipples, his fingers found the way inside her panties.

Wet does not begin to describe her. Johns hand was creamy. He found her slit, and slid a finger right inside her. She moaned, loudly. John was taking his time and she knew it. Sarah tried to reach and touch his cock, and he pulled away, and began to walk her to her bedroom. The bed was only about 10 steps away.

John layed her down on the bed and admired what he saw. He was right, she did shave her pussy, and this made his cock grow even more. This was going to be fun for him. Sarah scooted herself up on the bed. She was on her back, feeling vulnerable as they were both naked. She looked at John. His dick was leaking pre-cum, and she wanted a taste, but first John had other plans.

As she laid down, John lifted her legs up, and put his head in-between her legs. She smelled delicious. He was about to find out if she tasted the same. He dove in. He tongue running up and down her slit, nibbling on her clit. After what only seemed to be a few minutes, Sarah began to tense up. She flung her head back and grabbed John by the hair and pulled him into her. He was relentless. John was not going to stop until she came. That only took another minute. Sarah screamed Johns name as she clenched her thighs and almost cut off circulation to his head.

When John looked at her, his face was covered in her juices, and he loved every second of it. As John came up, he stopped at her nipples and gave each one a lick. John layed down next to Sarah. He could not believe where they were, but at the moment, he was not complaining.

Sarah rolled over John and sat on his chest. She was contemplating, did she want to slide down and get John inside her pussy, or did she want want to suck and taste him. She opted for the latter. Sarah reached for a hair tie, grabbed one, and slid down the bed. John knew what this meant. He was in for a blowjob of a lifetime.

Sarah put her hair in a pony-tail, and for a second, just stared at what she felt at that moment, was the perfect cock. It was not too big, not small by any means, and would fit perfectly in her mouth. She started at his balls, She licked the full underside. When she made her way to the tip, there was a lot of precum already, and she made sure to get it all on her tongue. She quickly made quick work of it as she swallowed it down.

Sarah moaned with delight as she savored the taste. She slowly licked down the side, and moved her mouth to come back up the other side. Then she did it, her lips circled his tip, going slowly at first, only about an inch. As she took him in her mouth, her tongue moved around the tip. Each time she came up, she went farther down. Before too long, she had John's whole cock in her mouth. Her tongue was working magic on John as she gave him the blowjob of his life.