Tomboy Takes Charge

Note: This is inspired by an old favorite of mine here on Literotica, Dr. Lucky 13's "Handcuffed Handjob" that is now something like 21 years old (wow, I feel old...). I have no clue if that author is still active at all, but if so, I hope they find this a worthy tribute to their piece.

While most girls starting becoming clique-ish and self-segregated from the boys, Jessie kept playing soccer, tackle football, and capture the flag with her guy friends. While the girls that she used to have sleepovers with turned towards singing along to Taylor Swift, painting their nails, and fiddling with their hair, Jessie spat out Iron Maiden lyrics, broke her nails rock climbing, and plaited her shoulder length hair into a warrior braid. Her mother Jessica worried a bit about her not connecting with her sisterhood of female peers, but her father Brad thought it was great that she continued to join him fishing on the weekends, shouting along to Meatloaf on the old pickup truck's cassette player.

She never really felt like she was missing anything, and besides, she still spent some time with her gal pals; she played field hockey with them and still got along when she did show up at the rare all-girls slumber party. She was never ostracized for being a 'Tom Boy'.

And then standardized tests and college visits demanded attention, and the get-togethers were less frequent. Jessie, Randy, Nick, Karl, and the rest became first juniors and then seniors. They each celebrated becoming adults at 18 with raucous parties. The guys all signed up for Selective Service (to Jessie's good natured cajoles about not having to go die in China or Russia during World War 3), and everyone registered to vote when Jessie drove them all a carload at a time to the elections office.

Spring Break was happening now, and the high school seniors' spring break just so happened to coincide with Robbie's--Robbie being Randy's hunky older brother that Jessie crushed quite hard on. Randy had warned his friends that Robbie was a little salty about being back home. He had wanted to join his college friends water skiing in the Caribbean, but money was tight (Randy and Robbie had a younger set of twin brothers) so if Robbie wanted to go skiing, he needed to pay his own way. That dose of financial reality led to him working odd job gigs during this Spring Break, Randy had explained.

To Jessie's tickled interest, then, Robbie was going to be around for the day's--and evening's--fun. She felt the giddiness in her stomach jump when he walked out onto the porch while folks were still arriving. He gave his customary "hey" and "sup" to Jessie, and she returned a nod and a deep voiced "sup" to him. (Good God, why did she try to lower her voice? He probably thought she was making fun of him...) Her eyes roamed over his body as he made some small talk with the other guys. He obviously was taking advantage of the campus gym, because while he was still thin, there was some very clear definition to his pecs and abs under his tight t-shirt. Jessie feigned a need for a can of soda and leaned close to Robbie to reach into the cooler. He smelled good, not of cologne but more like clean? Clean yet...manly. Maybe they would be playing on opposing teams for football and soccer today? How good would his sweat smell?

Robbie apologized and twisted out of the way. Jessie's eyes drifted lower. Wow, is this what the guys meant when they said an ass wouldn't quit? She bit her lip to avoid blurting something out. Clearly squats and deadlifts were part of his regular routine at the gym, too. Sure, the guys had each been developing into men, but Robbie was just beyond the others. Maybe it helped that he was so distant with her while everyone else was so chummy?

The day started with soccer in the afternoon, during which Robbie and Jessie were on the same team. Jessie bloodied her knee with one crazy slide to kick the ball into the net--to cheering success, and Robbie proved pretty capable at blocking the wild shots the younger guys were sending at the net. After one last stretching block, Jessie seized on the excitement of the moment to slap Robbie on the ass with an "attaboy" and hoots and laughs from everyone else.

They broke for a late lunch, and while they roasted some hot dogs and grilled some hamburgers, Jessie started to mull over a plan. Originally, Jessie had been thinking to indulge her bit of a klepto side by carrying off one of Robbie's shirts when the opportunity presented itself. That was before she knew Robbie himself, that whole slice of manhood, was going to be around today.

She had heard through the rumor mill at school that two of her classmates had tricked their way into a regular 'friends with benefits' situation with one of the hottest cheerleaders at their school. Maybe Jessie could insinuate her way into Robbie's pants? But how? Through eavesdropping, Jessie had picked up that Robbie's room was really Randy's now: he only kept the closet there for himself to store what he didn't take to campus. When he was home during the summer or winter breaks, he slept in their den down in the finished basement. Not a bad setup, but that meant he wouldn't be alone in his room for Jessie to slip in and work her seduction. Oh well. As she was considering images of Robbie laid out before her, her erotic desires were overcoming any practical or ethical qualms. It was going to happen, and the potential to be caught by the others--since everyone staying over would probably be sleeping in that same den--just was salt to season the excitement. And, dammit, she was going to snag the shirt he was wearing today, too. That cologne of his musk would keep her going for a long, long time.

After lunch, they all returned to the field and started in with a couple games of football. She slyly angled herself into playing against Robbie's team in the hopes that Robbie might just so happen to lay her out on the field. Jessie proved pretty capable as a quarterback or a receiver, her being more agile in dodging the attempts at sacks and interceptions. Robbie's height made him a solid receiver, as well, and was quite competent at swatting away passes.

Two twinges of eroticism plucked at Jessie during the football games: the first was when Randy was running the ball and Nick dove to stop the pending touchdown. Nick's grasp slipped from around Randy's torso but took hold again just below the waistband of his shorts--which naturally led to Nick de-pantsing Randy to the hoots and shouts of the other players. Jessie, herself, called out, especially because Randy was wearing a jockstrap that framed his perky pale booty, and the giddiness Jessie felt in her chest signaled a waxing recognition on her part that seeing a guy strip or be stripped was exciting for her.

The second moment happened a few plays later when Robbie was now running the ball. Jessie leapt at him, but her scant weight was not enough to bring him down. Instead, she found herself clung to him like a baby monkey. Bryan, probably the nerdiest of the crew, called Jessie riding Robbie 'Master Blaster', but Jessie didn't bother puzzling the reference. She was enjoying the feeling of Robbie's muscles churning and working between her legs squeezing his torso. She made half-hearted attempts to swat the football out of Robbie's tight hold against his chest, but in reality, Jessie just wanted to keep Robbie's body between her legs and held close. At the endzone, Robbie spiked the ball and then flipped Jessie off his back and onto the ground. Feeling those big hands grab her shoulders and then pull her into a flip made her stomach flip pleasantly. If she could spend all day jumping on Robbie and being thrown around by him, she would have considered it a pretty darn good day. She could still smell the traces of Robbie's sweat as she lay in the flattened grass.

As the daylight faded, the group then turned to some capture the flag, which was a bit less thrilling on account of the lack of places to set ambushes and practice some tactical planning. Jessie did get to show off a bit when she climbed down from a tree to attempt a snatch of the other team's flag, stretching out her legs as far as possible and then using a bare foot to pluck at the flag with her limber toes. For a while then, several of the guys started referring to her as 'Monkey Foot.'

Eventually, even all of the teenaged energy was pretty well spent, and the group came back to the porch for dinner, pizzas with just about all the toppings you could consider--the contentious social justice issue of the age, pineapple on pizza, was a fairly even split amongst the crew of guys and Jessie, so they only had one medium Hawaiian pizza. As they ate, Randy fired up a fighting video game for a tournament bracket, and finally around midnight, a couple guys left to go home while the remainder made some preparations for bed, which really just meant changing into sleep clothes (maybe), laying out sleeping bags or blankets, and putting something gory or funny on the tv to stream.

Robbie's makeshift bed these days was one of the couches in the basement den, which was where everyone was chilling. He laid back and watched the tv for a while before closing his eyes as Jessie took note. After a few minutes, Robbie's eyes snapped open.

"It is going to be impossible to sleep with that tv blaring and flashing every second," he complained and then added to his brother. "Can you turn it off?" Randy threw a piece of popcorn at his brother.

"Get fucked, Roberto," Randy laughed. "You don't work until the evening tomorrow, and it is our spring break, too." Robbie sighed.

"You get fucked, Ran-dick," Robbie retorted. "You think mom and dad are going to be able to sleep if you guys keep it up?" He lifted his eyebrows at Randy, who shrugged and nodded his head. Randy turned the volume down to a reasonable level and had Chris who was close to the wall switches turn off the overhead lights. Jessie watched Robbie blink a couple times from her nearby spot.

"It is still really bright," Robbie declared.

"Well," Randy snarked, "go sleep in the furnace room or something." Robbie sighed and pulled his sheets and blanket off the couch and crawled back behind the furniture.

"Little kid me had the right idea," Robbie laughed. "At least back here is dark." Jessie couldn't believe her luck. Robbie sleeping on the couch was going to make things tough, what with the creaking from the springs anytime weight shifted on the furniture, so that was going to be tricky to sneak up against her prey. With Robbie now laid out behind the couch, pretty much no one was going to have him in their eyeline, and that carpeted cement slab floor wasn't going to creak and betray Jessie's creeping crawl into position. Now, it was just a matter of waiting out the night owls...

...Robbie was having a pleasant little dream. He was crawling through one of those big plastic tubes at the park playground, but there were feathery hands inside the tube tickling him. The feathers stroked his tummy and pet his thighs. They flicked his nipples and cupped his junk. It felt relaxing but also very arousing. It was everything he would want a girlfriend make him feel (and make that girlfriend feel). Work and class had pretty heartily dampened his social and romantic life. Sure, he had had wet dreams before when he was younger, and this was going to end up one if this continued...

By a bit after 2am, the last of the guys shut off the show on the tv and fell down to sleep. Jessie, for her part, had feigned sleeping (and had, regrettably, actually fallen asleep for a bit) while awaiting her moment. She waited now with her fingers pinching her side, listening to the breathing of her friends and counting her own breaths to keep her excitement in check. When she deemed that everyone was asleep, Jessie took her sheets and crept over to the hidden canyon behind the one couch where Robbie dozed. In the dim light of the moon spilling through the french doors, Jessie looked over her prize. One of his long legs was jutting out from under his blanket, and one of his arms laid at an angle over his head on the pillow. With a last look over her shoulder to check that none of her friends were watching her perverted act, she dropped to all fours and installed herself next to Robbie.

First, she brushed her fingertips up the exposed leg, starting at his large feet and moving up past his calf and knee. She rested her hand at his midthigh and then brushed to the side the blanket and sheet. Robbie's boxers were a soft cotton and crimson. The hem seemed pretty short to Jessie, almost like a pair of pajama shorts for a woman. Jessie's heart raced as she pulled the blanket back a little further to reveal Robbie's crotch. She bit her lip in excitement as ragged breaths rasped from her mouth. Something sizeable lay just within that cotton, and she was going to have it. Jessie inched her fingers up past the hemline and across the muscle of Robbie's upper thigh and splayed out her questing hand across the bulges entrancing her eyes in the dim light. As her fingers pressed into the enticing bulges before her, one of the two twitched under her caress.

'That was Robbie's penis, right?' she thought to herself. 'Did guys' balls move around, too?' Jessie tried to comb through her memories of the guys talking dirty locker room talk about their genitals and could only remember them laughing about Nick sitting on his balls once when he had gone commando under his school khakis. Plenty of talk about hard-ons and stiffies and boners getting in the way. She started petting her fingers back and forth across the bulge and felt the meat under the cotton elongate and stiffen and fill out his underwear. Jessie smiled to herself as she rubbed her treasure slowly back and forth until Robbie's member swelled all the way to his hip. It just kept growing and growing! Wow, what was said about feet and hands definitely seemed true.

Nick had talked before about how good it felt for his girlfriend Alyssa to tickle his balls, so Jessie next trailed her fingers to the lower bulge of his sack and circled her fingertips. The aroused penis behind the thin fabric jumped and throbbed with her administrations of his nads. Jessie felt her chest flush with excitement, and she felt that heat start to build between her legs. She was going to do more than just fondle her fantasy. He was going to wake up, but everything would be in her control. Later, when she would have some time to reflect, Jessie was going to realize that she had just jumpstarted something of a dominatrix side to herself, but for now, all she knew in her horned up state was that having this tall statue of virility within her grasp was like riding a quad at full throttle down an old railroad track: pure thrill.

Jessie wanted so badly to see more, to touch him, to feel that lava hot skin hidden from her, and so she worked up the nerve to take her hands to the buttons of his boxers. Unlike the usual sort of basic boxers she saw her friends wear, these seemed to have a true button fly, with two small buttons at the waist, and so after unlocking the middle button he probably would have used to pee, she worked at the small, tight ones at his waist. She worked slowly--but urgently--nibbling her lip during the balancing act of unveiling her prize while not startling Robbie awake from too many odd touches. One button popped free in the moonlight...

Her head was resting alongside Robbie's chest, and when he grunted in his sleep, not yet quite awoken from his exhaustion during his erotic almost wet dreams, she held still and clenched her teeth. She was ready to pounce, if needed, for the next phase, but she wanted to explore more first. Robbie began to roll over, and she inched back to allow him the room. She was right against the back of the couch and could back away no further, and as Robbie turned and rolled, his arm swept over her chest, rubbing against Jessie's breasts. She bit back a little squeak as he made contact with her. Maybe it was anticipation, maybe the fact that she had chucked off her sports bra before laying down for movie time earlier, but that touch of his bicep against her was electric. He wiggled back under his blanket, now laying on his belly--and hiding away his cock! Jessie huffed inwardly but noticed that past his incidental touch of her bosom, she had had a whiff of his body's scent--salty and earthy from the day's games and sweating outside. Oh yes, she was certainly going to take that white undershirt of his. She'd wear it and have his scent all around her, and it would be just about as good as anything. Her eyes traveled down his body from his shoulders to his back to his shapely ass. Maybe...

Jessie shuffled lower and brought her eyes to his exposed thigh. Checking first that her arm was warm enough not to jolt him awake from the touch, she slipped her one arm under Robbie's blanket to slide her hand across his buttocks. Very firm, firmer than her own, which due to her womanhood had developed just a bit of jiggle over the muscles from running and climbing for so many years. She had nowhere near the sort of overflowing ass that seemed to always draw guys' eyes, but she bet it would be just the right sort of handful for Robbie to hold.

Just as she had slowly caressed and petted his perking penis minutes before, she now stroked his solid glutes. All sorts of images and scenarios went through her mind's eye like a bullet train: if she gave him a blowjob, would it be possible for her to bite his ass and leave teethmarks for him to see later? did guys enjoy that? was it even workable to silently blow him tonight? what about...the big event? could they...you know...fuck?

Jessie thought something felt...loose, and she pulled up the blanket with her free hand to look better at Robbie's rear. Oh! That last button must have come undone during his roll in his sleep! Luck was truly on Jessie's side tonight. Well, at least that part of luck. It was still unlucky that his genitals were hidden away by how he was laying now, but she could, at the least, feel the skin of his ass and thighs by carefully, carefully slipping her hand up under the leg of the boxers--or down from the now loose waistband.

A smile spread across her face as she sidled even closer to Robbie, his smell even stronger now, and snuck one blanket warmed hand up a boxer leg and the other past the waistband. She wasn't too surprised to feel the soft fuzz of his body hair on that hard group of muscles--she had seen enough of her guy friends mooning each other and her to know that it was pretty universal. Only Alex with his ancestry lacked body hair like that. If only Robbie's legs were more widely open, she could reach between his legs...

Just as she let slip a soft sigh from her tongue moistened lips, Robbie coughed. Oof, these shocks were difficult for her to handle, but she tried to steel herself so she wouldn't jerk her hands away and definitely wake the sleeping stud. Robbie started to move again, and Jessie contorted herself to slip her hands out of his underwear as he shifted in his half-awoken state. He rolled again now, and Jessie found herself pinned against the back of the couch, between it and Robbie's solid back. 'Mmmm,' Robbie hummed. Jessie could feel the vibration course through his torso and into her body. It felt wonderful. No wonder nymphos always talked about vibrators. One of her arms was just under Robbie's armpit, caught. The other lightly rested on Robbie's hip. 'Umm,' Robbie croaked, now waking. Jessie swallowed and whispered into Robbie's ear.

"Shhhh, you don't want to wake anyone up." Robbie jerked beside her, his head twisting around so one eye could peek at the startling close voice.

"What?" he gawped in something way more than a whisper. "Jess?"