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Handjob Fascination

"A woman enjoys manually pleasuring men"

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Author's Notes

"I wrote this story several years ago. It was my first attempt at writing something erotic. <p> [ADVERT] </p>Wrote a few more afterwards but then grew tired of it or got a case of "writers block"."

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.

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After fifteen or twenty seconds of that, Carli told her to start softly squeezing the cock as she moved her hand up and down. Jenna noticed a big drop of clear liquid at the tip. Carli said to smear the clear stuff all over the cock and to continue stroking. Jenna noticed how slippery it had become.

"Move your head a little closer so you can watch the cock, and start pumping faster...he's getting close," Carli told her, obviously recognizing the signs of Tim's rapid breathing and moaning.

Jenna did as she was told. Within moments, she noticed how Tim's balls tightened, how his cock pulsated and how she felt a surge from the base of his cock as she saw cum explode out of the hole and land on his chest, stomach, and even a little on her hair. Jenna couldn't stop milking Tim's cock and probably would've continued for several moments if she hadn't heard Carli saying it was time for Tim to clean up and get going. Remembering what she saw Carli do, Jenna then rubbed Tim's cum into his belly and chest. Carli encouraged her, "Taste it. It's good." So, Jenna got a little on her fingertip and tasted cum for the first time.

These memorable experiences helped Jenna after meeting her boyfriend, Will, in the fall of her freshman year at college. Will was a senior. They dated several times before their fondness for each other led to necking and petting. While she was initially hesitant about oral sex and having intercourse, she was eager to perform handjobs. Sometimes, she would masturbate as she was jerking him. The sight of this would often make him come quickly.

She and Will agreed to break up later that year when Will started talking about getting engaged. Jenna wanted to "play the field" instead of being involved in a more serious relationship and thought that would be better for her studies. She began to date other men throughout her college years. From that, she learned to better enjoy intercourse and oral sex but, while she loved the orgasms they brought, for some reason the handjob thrilled her most. She loved the feeling of power that it gave her as she watched a guy's face and how it made him tremble or convulse before her in orgasm.

She had experimented and learned to use different techniques. Sometimes she made her hand real wet with saliva, body lotion or even cooking oil. Sometimes she would just use a dry one-finger rub, up and down along the underside of the cock. Sometimes it was gripping and pumping the cock at its base from underneath the scrotum. She was successful at bringing a guy off by gently rolling his nuts with no cock contact at all. She had learned, from having watched Carli's dad that one time, to use her other hand to stimulate other parts of the male body. She discovered that the most forceful ejaculations occurred when she pressed her finger ever so slightly into his asshole. These ejaculations would explode from the lucky guy's cock - the distance that the cum traveled surprising Jenna every time.

After grad school and starting her career, Jenna fell in love with and got married at age twenty-four to a man she met at a training seminar. Giving him handjobs was an intimate part of their courtship in the year that they had dated. Jenna discovered the excitement of giving handjobs in public during that time. She pleasured him on an airplane, at a restaurant, and even one evening as he lay on the first green of golf course they frequented.

Once married, it became a very regular part of their sex life. Her delight at doing so made for a happy marriage because even if she wasn't in the mood to fuck or perform oral, her husband could always count on being expertly stroked off when needed.

Jenna recalled those eyewitness episodes while in high school and brought them into her marriage. Sometimes she would ask her husband to jerk off for her. After ejaculating, he would see how excited she had gotten from watching. She would lie back and begin playing with her pussy - the sight of which would soon have him hard again and lead to a furious fuck. One thing Jenna had noticed when her husband jerked off was how he always reached for the Kleenex after cumming. Remembering the experience with Tim, she asked if he ever just rubbed his cum into his skin like lotion. He realized he never did, and Jenna convinced him to do it by saying that it was good for his skin.

Remembering what she saw Carli's father do, Jenna even taught her husband to eat his own cum. Early on in their marriage, she had asked him if he had ever tasted himself. His reply was no, but since the conversation was occurring while Jenna jerked him off wearing a sexy, black soft-leather glove, she easily encouraged him to try. The first time for him was a few days later when he came in Jenna's mouth. She had swallowed but then they French kissed. She asked if he could taste his cum in her mouth and he said he did a little. A couple days later, she jerked him off and then got some of his cum on her fingertip. He was hesitant but Jenna told him it usually had a sweet taste with just a little salt mixed in. He reluctantly licked the cum off her finger. She gave him another sample and he did the same. This turned Jenna on and she wanted to see him do it on his own.

So a few days later when they got into bed, she used the remote to start a porn DVD on their television. She told her husband she wanted him to watch the movie and masturbate. Jenna got out of bed and her husband asked where she was going. She told him she was going just outside the room to watch from behind the door. Seeing her husband this way was another flashback to her teenage experiences, and the thought made her wet. She watched him as she played with her pussy and before long, she knew her husband was ready to cum. Jenna re-entered the room and got back into bed just as his cum was landing on his belly. She told him that she wanted him to use his fingers to taste it. This time, there was no hesitation. First, he used a finger to get a little bit. After licking it off, his hand returned to scoop up every last drop. When he took his hand from his mouth, Jenna immediately kissed him and could taste his taste on his breath.

Now forty-seven years old, Jenna was at the family vacation home on Cape Cod for a few days. Her husband had stayed at home with their two daughters, but her twenty-year-old son, Jason, was staying with her at the Cape along with a couple of his college buddies. The house was on the water and Jenna was up early, as her routine was to take a run on the beach before breakfast. It was gorgeous out and knowing that her son and friends would probably sleep in since they'd gotten in late, she took a long leisurely run. She got back to the house sweaty from her run and decided to sit on the deck to cool off and enjoy the view of Pleasant Bay before going in for a shower. She was a little surprised when Jason came out on the deck with one of his friends and told her they were going to take the sailboat out for a short sail before breakfast.

"What about Luke?" she asked.

Jason told her that he wanted to sleep in a little longer since they'd have the whole weekend for water fun. Jenna watched as they got the Sunfish ready and for a few minutes once they got sailing. She then went inside and was headed for the master bedroom to shower when she happened to notice that the door to one of the guestrooms was slightly open. Movement within caught her eye. She couldn't help herself as she snuck to the side of the doorframe to peek in. Her son's friend Luke was on the bed naked, stroking his cock.

As quietly as she could, Jenna pushed the door open a little more to get a better view. Jenna stared as Luke stroked with his eyes closed, lost in some unknown fantasy and was soon rewarded with what she considered to be one of life's most beautiful sights: cum exploding from the hard cock of an attractive man. Jenna couldn't remember ever seeing so much cum shoot out of a guy and almost gasped as she stood there watching the young man rub it into his skin. She snapped out of her trance and as she was turning to tiptoe on to her bedroom for that much-needed shower, she happened to glance up at the young man's face. Luke was looking right at her with a satisfied grin.

In the shower, Jenna contemplated what had just happened a few minutes earlier. Running her soapy hands over her breasts and then into the excited wetness of her pussy, Jenna imagined it was her hand on that cock and was pleased to realize she would always have a fascination for handjobs.

 

Published 
Written by 2020Vision
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