Chapter 9

Back in High School

Looking at Kelly today, it is hard to imagine a time when she was not attractive and confident. That was the case in her years at Madison High School. She was a late bloomer and was nothing out of the ordinary in school. Her schoolwork was only in the average range and other than being on the cheerleader team, she had few other interests in school activities. She did try out for the senior play and the talent show one time but failed to be picked for either.

She was pretty enough, but she felt wearing braces and glasses put her in the slightly less than ordinary category. She actually was cute, but it would be years later before most of the guys in her class would notice.

She had a few girlfriends and a longtime, sort of boyfriend, Gary. He was a year older and a class ahead of her. He lived two houses down the street. Gary was also on the immature side. He and Kelly were on and off again girlfriend-boyfriend until he went off to college.

Gary was her high school date to most events including the Junior Prom and his Senior Ball. They had grown up together and eventually became lovers. Gary was not the fastest mover in the romance department. They did hold hands early on, but she was a senior by the time he kissed her the first time.

Their relationship was always hit and miss, and it slowed when he graduated high school and went to the local community college. Not being in the same school and sharing school activities, was as if he was grown up, and she was still a kid. He still lived two houses down the street, and they did still go out frequently. She was eighteen years old and a senior, yet she may have been the only girl in her class that had not seen a hard cock…let alone been fucked by one.

***

One New Year’s Eve, her parents and Gary’s parents had gone out for the evening celebrating. Gary came over to spend time with her. For the last several months, they had been kissing and making out, but there was no tongue involved. Gary had no idea you could use a tongue for anything more than licking an ice cream cone. They had been getting a little bolder the last few weeks but nothing you could call intimate. It had started with giving back rubs. The back rubs were through her blouse but still more than they had done in the past. This New Year’s Eve things will change.

Kelly is lying on the sofa on her tummy. Gary is rubbing her back on top of her blouse. Kelly decides to make the first move. “I thought you were going to rub my back; you’re rubbing my blouse.”

Gary does not even answer. Her blouse is not tucked in and is loose around the waist. He slips one hand under it and continues rubbing the actual skin of her back. Gary had gotten hard during their make out sessions, but tonight with his hand on her bareback makes him rigid. In addition, he can feel the snap of her bra when he moves his hand up and down her back. For a nineteen-year-old boy that had almost no experience with a woman, this is very naughty.

Kelly is enjoying the massage and hopes he might get a little bolder. She feels his finger linger on the snap of her bra. He makes sure he touches the back of her bra on each pass up and down her back. Then he stops right on the snap. “Would you mind if I undid this? It would make it easier to rub your back.”

“I would like that.” Gary fumbles with the snap for a while, and Kelly has to help him. She pulls up her blouse to be able to get to the snap. She quickly undoes it and leaves her blouse pulled up to her shoulders. Not only is her bra strap gone, but also Kelly’s bare back is visible to Gary. He goes to work with both hands. He is breathing shallow. Kelly is turned on and would be fine if he does more. She raises herself off the sofa a couple inches and unbuttons her blouse. He helps her remove it.

She is still on her tummy and naked from the waist up. Gary has not seen her breasts yet, but he knows they are right around the corner from her back. He continues the massage of her back, but now he includes each side of her upper body. He does not get around to her breasts, but he is getting closer. Kelly whimpers softly to let him know she is enjoying the attention. One of Gary’s fingertips finally touches the softness of her breast.

Kelly lifts up off the sofa a couple inches, supporting her weight with her elbows. Her smaller titties are within reach of Gary’s hands. It takes him several passes touching the edge of them, until one time his hand slips over one breast. Kelly moans and squirms in delight. He squeezes a woman’s breast for the first time. Kelly sits up on the sofa, and Gary massages both of her titties. He kisses her several times and holds her close.

They do not go any further this evening. They both had an exciting time. Kelly wonders what would happen on their next date.

A couple years later, Kelly will reminisce and figures he ejaculated in his pants from this first partially intimate experience

***

Most of Kelly and Gary’s dates had been either to a miniature golf course or to a drive-in movie. If it was a movie, they always kissed and made out with no fondling or touching. The drive-in movie was ideal for young people to fool around. Especially in the winter with the window of the car all fogged up. Kelly was anxious for their next date after their New Year’s intimacy. Gary called and suggested a movie. Perfect, Kelly thought, figuring he is probably thinking of touching her titties again…if not more. She did not want to be too forward about all this, but she liked Gary, and she liked the feeling of him touching her.

It is Saturday night, not even a week since New Year’s Eve. Gary picks her up in his car, and they are off to the drive-in. They do not even know what movie is playing. It does not matter, they are mostly interested in a semi-private place they can be alone. The movie starts, and the evening begins similar to the other drive-in dates. Kelly slides next to Gary. He puts his arm around her. After a while, he kisses her, which is much like a normal date. Then he kisses her and moves his hand to her breast. This is a first. Kelly makes the kiss as passionate as she can, so he will know she likes his hand on her titties. She would eventually remove her bra, and he would touch her bare titties again.

Kelly does not feel the drive-in is private enough to do more. Gary does not attempt more at the drive-in. He drives her home, parking in a dark place on the street in front of her house. They kiss again. This time, it is dark, and they are alone. They kiss passionately, and his hands are all over her titties.