Introduction: John Riley had been married for nearly 10 years when his wife filed for divorce. She had claimed that the lack of romance was to blame, but John suspected there was something else going on. John had hired a private investigator to follow around his soon to be ex-wife and find out if she was with another man. After following his wife for only a few hours, the P.I. found her in bed with another man. This tore a gaping hole into John’s heart. He swore that he would never let this happen again.
After the divorce was finalized and several months of blind dates set up by friends later, John felt that he would never find love again. He knew he would never find another woman that he loved the same way he had loved his wife, but thought that someone out there had to be a woman who he could share the rest of his life with.
John signed up for several internet dating sites after the failed attempts of his friends to find him a woman. Still, months went by with only empty promises left by one night stands. John was about to give up on love when he received a message from a young girl named Charlotte. Being a 45 year-old, nearly overweight man, John didn’t think he’d have a chance with this beautiful blonde 18 year-old college student. From her profile picture, he could see that she was athletic with curly blonde hair that fell halfway down her back. Her modest clothing didn’t reveal much about her body, other than she was a beautiful tanned blonde.
John, being of average height and slightly overweight, didn’t think that she would be interested in going out on a date with him, but she had sent him a message so he decided to go for it. He responded to the general ‘hello’ message and told her a short version of his life story. Charlotte seemed nervous, but John figured she would be, since she was barely of legal age. They began chatting about casual things, but soon things started escalating to a more intimate conversation. The two would share pictures of themselves naked and even started having phone sex. John was enjoying every second of the attention, but began to think that things were too good to be true.
Several times John had tried to arrange for Charlotte to come see him. He offered her the spare bedroom to ease her nerves about being intimate with someone she had never met. She would agree, but then at the last minute she would cancel without a reason. John was beginning to accept that she may not be who she said she was and that they may never meet.
Things all changed about 6 months into their online relationship. Charlotte expressed to John that the reason she had canceled all of the meeting arrangements was because she was embarrassed that she was so young. She told him that she didn’t want to feel like a little kid with her father. John reassured her that he thought of her as a grown woman and would never think of her as a child, especially not his own!
Charlotte felt a little more comfortable and agreed to meet for dinner one night, but nothing more. John happily agreed and they set up to meet for a movie and then dinner for two at an upscale restaurant.
The days crept by as the date approached. John prepared himself by getting a haircut and trimming up his untidy “lumberjack” beard. He decided it was time for some new clothes to really complete the look, so he went out and bought a nice pair of dress pants and button up shirt for dinner the following night.
To ease her nerves a bit, John and Charlotte had decided it would be best to meet up at the theater instead of giving their addresses. John knew Charlotte was nervous and didn’t want to make her any more uncomfortable than she already was. As John pulled up to the theater, Charlotte was nowhere to be seen. John thought that maybe she had bailed on him again. With less than a minute until the movie was scheduled to start, John saw Charlotte for the first time.
The petite blonde figure was walking his way. John was trying to conceal his nerves as the beautiful woman approached. Her pictures hadn’t done her justice. He could see right away that her breasts were not the meager B-cup she proclaimed, but were almost a D! Her short flowered skirt showed just enough leg to be respectable yet sexy at the same time. Her thin white blouse showcased her upper body amazingly. With her curly blonde hair down her back, she looked like a real movie star.
John walked up to her and introduced himself to the stunning young lady. She nervously looked him over and gave a shy smile and apologized for being late. John suggested they go catch the movie quick before the previews ended.
Throughout the movie, John caught himself staring at Charlotte. Planet of the Apes was a background to the show John was enjoying. Every giggle and exclamation Charlotte expressed gave John the most genuine smile he’d ever given. Everything about her was perfect in his mind. He caught her glancing at him every few minutes and quickly turn away when she realized he was watching her.
When the movie concluded, John offered Charlotte his hand and asked her if she was ready for dinner. She took his hand and agreed that she was starving. As they climbed into John’s car, John noticed Charlotte adjusting her makeup in the mirror. He had never appreciated how beautiful a woman could be. He could never remember a time when he just watched his wife as he was watching Charlotte now. He began to feel guilty that he had never given his wife the attention a woman deserves.
The short drive to the restaurant opened a quick conversation about the movie. John embarrassingly hadn’t been paying much attention to the movie and was glad when they arrived at the restaurant. After finding their reservations, the couple sat down in a booth in a secluded corner of the restaurant. The waitress came and took their orders. Charlotte was looking down at the table. John asked her if she was nervous and she quickly shook her head ‘yes’. After their food and drinks had arrived, Charlotte started opening up a bit more. John noticed they were making eye contact and even held hands across the table briefly. John had just started to give the punch line to the joke he had just told when Charlotte interrupted him by saying that she wanted to go home with him that night.
John was shocked. He thought the date was going pretty well, but never imagined she would be up for spending the night already. He quietly told her that if that’s what she wanted, then he’d be happy to oblige. She shook her head and said that the only way to get over her fears were to face them head-on. John was excited and nervous at the same time. He hadn’t planned on Charlotte staying the night and was quickly taking inventory in his head of all of the things he didn’t clean around the house.
John told Charlotte that the spare room was clean, but there was quite a mess in the living room from his at-home business. She waved her hand at him and told him that she’d just like to sleep in his bed if he didn’t mind. Of course John didn’t mind, he just wasn’t looking forward to sleeping on the couch the whole night.
After some more small talk, Charlotte suggested that they head to his apartment before it got too late. John paid the bill and helped Charlotte up as they headed for the door. John had seen a dramatic change in Charlotte in the past hour. She was much more cheerful and talkative. She even told him that she had played with herself all morning thinking about him. John was starting to get turned on as she described her morning to him.
When they arrived at John’s apartment, Charlotte reminded John of all of the sexual fantasies John had described to her online. She told him that she had been thinking about them all week and that she wanted him to make her a woman by taking her virginity that night.
John helped her out of the car and up the stairs to his apartment. Outside the door, he turned to Charlotte and asked if she was sure she wanted to do this. She responded by pulling his lips to her’s and kissing him passionately on the lips. John was startled, but had never been more aroused in his life.
She sat on the edge of the bed, nervous about what was about to happen. All of the promises John had made came flooding into her head at once. She felt her breathing flutter for a moment as she realized she was about to get the pounding of a lifetime.
John quickly, but meaningfully, grasped the bottom hem of Charlotte’s blouse and gently pulled it up over her head. Her arms lingered above her for a moment as John took in the view of her beautiful bra-clad chest. He got down on his knees between her thighs and reached around for her bra clasp as she lowered her hands to his shoulders.
After fidgeting with the clasp for a moment, her milky white breasts came bouncing loose as the support finally gave way. John slowly pulled her bra off of her arms and gently tossed it to the side. He instructed Charlotte to raise her hands as they had been before so he could admire them in their fullness. Charlotte exhaled as she raised her arms above her head, flattening her lightly toned stomach.
John leaned forward and kissed her stomach right below her breasts as he lightly caressed her engorged nipples in his hands. After a moment of fondling, John slowly started leaning Charlotte back onto the bed. Grabbing her hips, he gently pulled her to the edge of the bed. John slid his finger into the waistband of her flower-print skirt and slowly pulled them down her legs as she raised her beautiful tight ass off of the bed.
John tossed the skirt to the side to join her blouse and began kissing her knees, working his way up her thighs. He could already smell her musky scent as he was halfway to his target. John could feel the heat radiating from her still panty-clad pussy. He wanted to take her right then, but used all the self control he possessed to hold himself back. He was going to make her beg for it.
Charlotte’s mind was completely empty. As she lay back, she let all of her thoughts fade away as she just allowed herself to feel the sensations John’s body was giving her. She could feel herself getting wetter by the very touch of his lips to her thighs. She took her breasts into her hands and slowly started massaging her nipples, lightly rolling them between her manicured fingers.
As John was inches from her lips, he leaned back onto the backs of his feet and reached to her sides to slide her panties down her long tanned legs. After tossing her panties, John separated her knees and stared into her glistening wet pussy. Again he started at her knees and began working his way up her thighs, planting a kiss every other inch of the way.
Charlotte was burning up inside with the desire to pull John as deep into her as she possibly could. The closer John got to her pussy, the harder she found herself pinching her nipples. The need was getting stronger and stronger with every advancement he made. Finally she felt John reach his destination and plant a kiss right above her clit. This was too much for Charlotte to contain any longer and she let out a long moan, encouraging John to continue.
Using his tongue, John softly parted her slippery lips and gently flicked his tongue over her engorged clit. He felt her shutter under him. John took a long suck on her clit as he primed his finger for entry. Slowly, John inserted his middle finger deep into Charlotte’s pussy. Pulling out his finger, he offered it to Charlotte to taste.
“Do you like the taste of your pussy?” he asked her as he inserted his finger into her mouth. Charlotte moaned in approval as she started sucking her juices off of his finger. John knew that she was a virgin and didn’t want to overwhelm her body. He pulled his finger back and started gently pumping his finger into her pussy as he lapped at her clit. John could hear Charlotte’s breathing quicken and felt her getting even wetter than before. John inserted another finger into her already full snatch.
Charlotte gave another moan of approval as John started quickening his pace. Soon he had both fingers deep in her pussy, feeling her hymen stretching around his knuckles. When Charlotte’s moans started becoming more pronounced, he withdrew his fingers and pulled away from her soaking pussy. He instructed her to sit up. As she was raising herself up into a sitting position, John pulled off his shirt. Charlotte smiled and began to unbutton his dress pants.
As she unzipped his pants and began pulling them down, John’s 9 and a half inch cock nearly hit her in the face as it sprang to life, now free from its constraints. Charlotte giggled a bit as she watched it spring from his pants. John quickly kicked his pants and boxers off and stood between Charlotte’s thighs.
Charlotte reached up and grasped his engorged cock in both hands. She could feel its warmth as it pulsated in her fingers. She heard John groan as she started sliding her hands up and down his shaft. She slowly made her way towards his bulging head with her lips. As she pressed her mouth against his head, she felt him run his fingers through her hair. This slight encouragement gave Charlotte the confidence she needed to take his member into her warm mouth.
John felt her tongue exploring the head of his penis as he stroked her hair. He knew he wouldn’t last long with this beautiful woman sucking his cock. He gently started thrusting into her mouth, silently begging for her to go deeper. Feeling his desire, Charlotte took one breath of air before taking 7 inches of his beautiful cock into her mouth.
John didn’t want to finish just yet, so he gently pulled her off of himself and asked her to lay back onto the bed. Charlotte did as she was asked and prepared herself to be deflowered by this throbbing piece of meat.
To be continued…