Jack and Jill Jack Off

Background

This is a work of FICTION – nothing more than an expression of mutual physical attraction (LUST) between two friends!

So the chatting and flirting went on and on, getting ever closer to outright "sexting" or "cybersex", but not going the entire way. That was until Jill texted Jack about seeing a man who looked like him holding a melon and bringing it close, smelling the ripe fruit. She said it reminded her of him, and he asked her if she was stroking a banana at the same time. This was their usual banter – melons and bananas, sexual innuendo.

It had been going on for a couple of years, and, as far as Jack was concerned, was the only sex he got. Although he loved his wife, there was NO sex, and Jack reverted to masturbation, a LOT. Most of his fantasies revolved around Jill. Jill - sexy, mature, blond, robust, busty, and a great ass! And a sense of humor to go with it, as well as a healthy (apparently) sexual appetite. She made Jack's cock hard. Every thick average inch! Jack loved watching her walking in the hall way, her large breasts bouncing, and he loved pointing out how the T and N in Trojan lined up perfectly with her nipples! She wore boots on occasion, which added to her sexiness in her jeans. Although she never wore a dress to school, Jack knew she had a feminine side, this based upon the time when it was "switch" day at school, and many of the young boys dressed like girls. Jack teased that his "pantyhose" were in a bunch (not that he was really wearing them – but just testing the waters for a "kinky" side to Jill), when Jill stated that she preferred stocking – a major turn on for Jack.

So, as time went on, the sexual innuendo got more and more blunt and straight to the point. Jack was always turned on by this sexy woman. But it was the latest time that took it to the next level. The banter went back and forth when Jack mentioned "flat" about a coworker and his wife. Jill asked what he meant by "flat" and Jack told her no boobies. Jill laughed (lol) and said she already knew but she wanted to hear him say it. She told him to tell it like it is. So he did. He told her that he loved her boobs. He went further, with her prodding, to tell her that she made him hard, and that his cock was hard right now. Jack was blushing and embarrassed, but he felt "relieved" that he finally told the "truth" about what Jill did to him. He confessed to having many fantasies about having sex with her, and she confessed to having thoughts of him on occasion (but declined to give any details).

A weekend passed. Jack finally got the courage to text her again, confessing his embarrassment and hoping he had not jeopardized their friendship. Jill said that he had not, and wondered about why he was embarrassed. He told her that it was because he was so "blunt" about how he felt. She said not to worry, and told him that as long as it was just physical fun and no "feelings" involved, then she was okay. This suited Jack fine, as he was all about "no strings" "sex" (even if it was just fantasy, sexting, cyber). Finally, Jack asked Jill if she would always think he was "undressing" her with his eyes, and she said no, but it was okay for them to undress each other. (A, tease, of course, but one that planted a fantasy in Jack's mind.) He told Jill so, and that he would write a story for himself to jack off too, (she thought it would be hard to stroke and type) and this is where we are now!

The Fantasy

So Jill and Jack, after a couple of years of sexual banter and teasing, finally decided to go to the next level. They would meet at a secluded spot and masturbate together. They agreed that they could touch each other while undressing each other, but no kissing and no intercourse. Jack suggested the coach's office at the soccer complex, later in the evening, as it was the "dead period" and no student would be around. Plus, there was a shower and a bathroom in the office, if needed.

The evening arrived. Jack told his wife that he had to go and finish an online class, and at the office he could do so in a few hours without distraction. Jill told her husband something along the same lines. Jack arrived first and unlocked the door. He parked a distance away and walked, so that their two vehicles wouldn't be seen at the same location and raise questions. Jill arrived a bit later, and Jack closed the door and locked it.

The air was charged with sexual electricity. Jack, upon Jill's arrival, and already began to swell in his shorts. Jack wore his "coaching" outfit, as Jill at commented before that she found it "sexy". Jill was wearing jeans and a blouse. Jack told Jill that they should take turns removing a piece of clothing on each other. Jill agreed. Jack approached Jill and had her turn around and face away. He placed his hands on her shoulder and began a gentle massage, moving to the neck. Jill approved. He continued, moving to the front, and, teasingly, touched her everywhere but her large breasts. Her breathing began to get shallow. Finally, Jack began to unbutton her blouse, from the bottom up. Until it was open. He turned her around. He was very please, as he was gazing upon a very large set of breast in a very sexy sheer bra. Her nipples were erect and the sight made Jack erect. Jack told Jill how much he loved her boobs, removed her blouse, and reached up and caressed are large breasts through the silky fabric. Jill said it was her turn.

Jill went for Jack's soccer shorts. She squatted before Jack and slowly pulled his shorts down. Jack was wearing his "sliders" under, white ones that clearly showed the outline of his erect cock. Although Jack was not "hung" average, and on the thick side (just like his height and width!). Jill didn't seem to mind, and she had repeatedly told him that "size does not matter". As Jill pulled his shorts down, her hand grazed on his cock, making him throb and a spot of precum appear. She smiled, then squeezed his erection.

Jack's turn. Jack then unbuttoned Jill's pants (again, from behind) and slid her jeans off. He was very pleased! She was wearing stockings and a garter belt, but no panties. It seemed Jill was ready to play! She kicked off her shoes and slid the jeans all the way off. Jack then pulled her close to him, his hard cock pressing against her sexy ass. His cock was very hard, and Jill pressed against it, while at the same time Jack reached around and cupped her ample breasts. The sexual heat was rising!

Jill turned, and it was her turn again. She squatted before him once again, and this time slowly pulled his sliders down, releasing his hard on. It "popped" free, precum collecting from the head. Jill said one word, "nice."

She stood, and cupped his balls, big, heavy, and full of cum. He moaned. She moaned as the head pressed against her mount.

Jack stated, "Let's watch each other jack off now. I want to watch you cum, and I want to cum for you Jill."

Jack gave Jill the chair while he stood. Jill sat, and spread her legs over the arms. Her pussy was damp with juices, and Jack's cock responded by throbbing oozing more precum. He moved and stood by Jill's legs. He reached down and grabbed her feet and began to massage them. Jack loved feet, and even had a foot fetish, having always fantasized about cumming on stocking covered feet after getting a foot job. But that was, maybe, for another time. Tonight it was about jacking off for each other. So, after a massage of her sexy little feet, which she loved and which turned her on even more so, she began to caress her breasts, pinch her nipples gently, and massage her wet pussy. To smell of pussy and Jack's precum filled the air and increased the desire of both.

Jill told Jack, "Stroke you cock for me Jack, I want to watch you."

Jack stood there before Jill and began to stroke his cock. All the while Jill was touching herself, bringing herself closer and closer to cumming. Jack continue to stroke, squeeze and massage his hard cock, precum leaving a trail like his cock was drooling. He was close to cumming. "Closer Jack." Jill wanted him closer, so he moved between her spread legs, his thighs against the chair, his cock a mere foot from her breasts. "Where do you want me to cum Jill?" Jack was stroking harder and harder, faster and faster as he matched Jill's manipulations of her wet pussy. The sight of Jill's body and her masturbation was making his balls "boil". "Cum on my feet! Here!" Jill brought her feet to Jack's hard cock, placing them together around his shaft. Jack grasped her toes and began to squeeze and massage as he used her feet to stroke his cock. Jill was on the edge! Jack was on the edge! "Let's cum Jill, cum for each other!"

Jill began her orgasm as Jack began to spurt his cum on her feet. For Jack, it was the best orgasm in a long, long time. He couldn't speak for Jill, but she seemed to enjoy it quite enough.

After they came down from their bout with ecstasy, they began to giggle and laugh. Maybe we can do this again, both chimed in at the same time. Jack hoped so!