Ever since she was in her late teens, Jenna had been fascinated with handjobs. Not only giving them, but also watching men doing themselves. It was a rush to see and hear the reactions of a man when he masturbated - even more so if the guy didn't know she was watching. This is how it started.
Jenna was eighteen and was nearing the end of her senior year in high school. Her best friend, Carli, lived a few houses up the street from her. Both girls were well-liked at school. They were good students and good athletes, playing on the girl's basketball team and running for the coed track team. Both were pretty. Jenna had strawberry blonde hair and some freckles, Carli had dark brown hair. They were about the same height, 5'7" and had developed similar appealing figures. The major difference between them was that Carli had a more outgoing personality. She had dated several different boys since her junior year and her personality seemed to make her more forward with them. Both girls had been accepted to colleges but they were in different parts of the country so, as the school year drew to a close, both knew that, even though they'd been best buds since they were toddlers, changes were coming.
Both girls loved to talk about boys and were very curious about sex. Since many of these discussions occurred over the past year during sleepovers, it often led to masturbation. Mostly, they just masturbated at the same time, but there were occasions when they stimulated and satisfied each other. They thought nothing of it since they were such good friends and very interested in the opposite sex.
A couple incidents happened for Jenna near the end of that senior year that became defining moments for her sex life. About a month before the end of the school year, Carli quickly handed Jenna a note between classes that read: If you want to see something real neat, come over to my house about ten minutes after we get dropped off by the school bus (p.s. Be sneaky quiet).
The school bus dropped them off and they walked towards their perspective houses. What was different about this afternoon was that a boy named Tim, also a senior who also lived in the neighborhood, was walking along with them. Both girls knew Tim for several years and thought he was cute, but also knew him to be very shy around girls. Jenna knew that Carli was also dating someone else and gave her a questioning look. Carli explained that Tim had asked her to give him some quick help with something. Jenna accepted it as probably school work and then went inside her house, had a glass of OJ, checked emails, and then went over to Carli's.
Since they lived nearby to each other and growing up were often eager to be together (at times against their parents' wishes), they sometimes had to sneak in and out of each other's houses. So when Carli had said to be "sneaky quiet", Jenna knew exactly what to do. She quietly entered the backdoor, removed her sandals and tiptoed towards Carli's voice in the living room. She heard Carli saying, "Mmmmm, you like that, don't you..."
Quickly moving to the entrance to the living room, she stopped dead in her tracks when she saw Tim lying on the couch with his jeans and boxers on the floor next to it. Carli was sitting on the couch beside him facing Jenna. Seeing her at the entrance, Carli gave her a quick wink and put a finger to her lips, signaling for her to be still. Tim was facing away from Jenna and probably had his eyes closed since Carli had his cock in her hand and was stroking it while cooing things like: "Your cock is soooo hard" and "C'mon Tim, let's see that cum..." Carli masturbated him - first stroking slowly and then furiously pumping his cock - as Jenna stood there totally engrossed, listening to Tim's breathing become louder.
Suddenly, he was moaning and Jenna then witnessed cum flying out of his cock, spraying his chest and stomach. She saw Carli rub his "lotion" into his skin, occasionally licking her fingers. Carli then picked up Tim's clothes and said, "You'd better get going, my sister will be home soon." Jenna knew that wasn't true and knew Carli was just using it as an excuse to get him to leave. Once Tim grabbed his backpack and left the house, Jenna and Carli both rushed upstairs to Carli's bedroom.
"I can't believe what I just saw," gushed Jenna, "that was soooooo hot!"
Carli laughed and said, "I know and I'm soooo wet."
Jenna was wet too, but also curious. She asked Carli what it felt like. Carli told her to come over to the bed, take her shorts and panties off, and to spread her legs. Jenna did as she was told and as Carli described the sensation of jerking a boy's cock off, she slid her expert fingers up and down Jenna's hot wet slit, making her explode in orgasm within what felt like a matter of seconds. Jenna then rolled off the bed and got on her knees between Carli's legs. Pushing her skirt up, she quickly masturbated her best friend through her soaked panties.
It was about two weeks after that when a second incident occurred. Jenna's parents went away for the weekend and she was spending the night at Carli's. They watched a movie and didn't stay up too late because Carli had to get up that morning to go to a two-hour Driver's Ed class. Jenna heard Carli leave but was still tired, so she slept a little longer. She woke up about an hour later, got a bathrobe on and was headed for the bathroom to shower down the hall when she heard a woman's voice coming from the direction of Carli's parents' bedroom. She thought she remembered Carli's mom saying she'd wake her at 8:30 and drop her off at class on her way to get coffee and go to the grocery store, so Jenna was a little confused.
As she approached, she saw that the bedroom door was half open - which allowed her to directly see the television in Carli's parents' room. A porn movie was on the screen - explaining the woman's voice she had heard. What was on the screen really didn't matter to her. Knowing that the half-open door blocked the bed, she knew she could probably look through the space between door and door frame that the hinges allowed to actually see the bed without being seen. She was right. She got a clear view of Carli's dad naked on the bed slowly pulling on his cock.
The difference between what she saw watching this and the experience with Tim was that when she had witnessed Carli and Tim, it almost seemed to be a rush to get to the results. There was some furiousness to it. Carli's dad was taking his time. One hand was on his cock, the other was sensually visiting other parts of his body. She saw him pinching his nipples, gently running his hand over his stomach and the inside of his thighs. She even saw him raise his hips off the bed to allow a finger to massage his asshole. After about five minutes, she could tell by his breathing that Carli's dad was going to cum. She watched his face as the moment approached. He did not close his eyes but instead stared blankly towards the television - his mouth slightly open as he moaned and his ejaculation spilled onto his belly and pubic hair. She remembered how Tim's ejaculate flew, while Carli's dad's spilled out of his cock. She also noticed - and was surprised - when Carli's dad got some cum on his fingers and then licked it off.
Of course, these two memorable incidents of Tim getting jerked off and then Carli's dad doing himself, fed her fantasies - as she often imagined her hand on the cocks being stroked - and probably led to her obsession with handjobs. She couldn't get over what she had witnessed on those two occasions. She, of course, knew what a penis looked like from health class and from watching some porn videos that Carli had found in her parents' bedroom. But it was different seeing it live. The excitement was like having front-row seats at a major sporting event, and Jenna became obsessed with the images.
She masturbated more frequently than ever thinking about it. Jenna would never mention having seen Carli's dad, but did ask Carli whether Tim might be invited over again so that she could try doing it to him. Of course, it didn't take much to convince Tim. When Carli asked him, he said he was busy the next few days but was very willing to come over early the following week. He seemed a little surprised, however, when, after getting off the school bus, Jenna walked with them to Carli's instead of going to her own house.
Once inside, Carli took charge - telling Tim to sit down on the couch and take his clothes off. She then told him that Jenna wanted to learn how to jerk off a cock and that he should just lie down and enjoy it. She told Jenna to sit down next to him and to take his cock - which was semi-hard - in her hand. Jenna did as she was told. Carli then said to make a semi-circle with her thumb and fingers and to gently glide them up and down Tim's cock. Jenna did that and noticed Tim's cock got bigger, harder in response.