Gabby Takes Control

Gabby Takes Control

Despite references to high school, all characters involved have finished their final year of high school and are aged at least 18 or over. This story contains heavy elements of femdom, such as pegging and short-term chastity. If you are uncomfortable with these elements, then do not read this story. Otherwise, enjoy.

***

The Williams household stood quiet and undisturbed on Rose Berry Lane that sunny July afternoon. Most of the family had left for their annual summer vacation, happy to escape the heart of predominantly white, middle-class American suburbia, if only for a short while, before they returned to the routine of their daily lives. In the meantime, the residents of Rose Berry Lane strolled past the well-kept garden and white picket fence and, justifiably, thought of how deserted and empty the house seemed without its owners, before continuing to walk past without a second thought. However, they weren't entirely correct, as the house was only almost empty. The only signs of live existed hidden away in one of the upstairs bedrooms, in which the eldest son of the Williams household was receiving a handjob from his hot little Latina girlfriend.

Paul slowly ran his fingers through the mess of his sandy blonde hair, kept his hands held behind his head and gave short moans of pleasure as the girl sitting on the bed between his legs expertly teased the head of his cock with her nimble fingers.

Paul Williams was the eldest child of Peter and Penny Williams, a successful insurance salesman and a housewife who had a position on the board of governors for the local high school that her children all attended, the infamous Foxtown High. However, Paul did not the fit the typical image of the 'eldest son'. He was not tall, nor broad shouldered like his father, and instead had seemed to inherit many of his physical features from his mother, with a pretty face and slender, feminine body (which was currently stark naked with his legs spread wide on his bed). Perhaps the most embarrassing of these physical features was his soft, round ass, which had been described before as a 'bubble butt' by not only his girlfriend but also some of the guys in the changing rooms. He was definitely an attractive boy, but certainly not masculine or intimidating.

Paul was quiet and shy, with average intelligence and popularity at school. He was considered cute, but not exactly hot. Due to his reserved nature and willingness to please, he often put others before him and did exactly as he was told. It did favours for him with authority figures, but it meant that sometimes he'd be a considered a bit of a pushover, and some of the harsher types at school often tried to take advantage of it. He was often told by his parents to speak up and be more assertive, but Paul found that he was happy the way he was.

Life seemed to be working out fine so far, he thought, as he looked up at the gorgeous brunette pleasuring him. Her deep, brown eyes were focused on his pretty penis as she worked away at it with her skilled hands.

Gabrielle 'Gabby' Martinez was a feisty little spitfire of a woman. Raised in a Mexican family but having lived most of her life in the US, she had always been a bubbly, confident little ball of energy. She was outgoing and spontaneous, the antithesis to Paul. She was also beautiful, with long, shiny brown hair, a curvy but petite 5ft, 1 figure and a tan complexion. She currently wore only a tiny black thong which rode quite far up her ass and an old t-shirt tied off just below her perky C-cup breasts, leaving her flat stomach, slender legs and most of her thick ass exposed. In any aspect of life where Gabby couldn't get by on her looks, she simply had to use her mouth.

Not in that way, you pervs.

Gabby was a very chatty girl. She talked a lot, and she was good at it. She had mastered the art of the conversation, and more importantly, the art of persuasion. She would have been head of the debate team at school if she hadn't considered it too nerdy. She had a silver tongue that would always find a way to encourage anyone to do anything for her, which, combined with her beautiful looks and a bat of her big brown eyes, allowed her to wield a special kind of control over most men.

So, if Paul and Gabby were such polar opposites to each other, how did they come to be in this position, with Gabby giving the full length of Paul's cock a slow and sensual massage?

Well, these young lovebirds were actually childhood friends. Many years ago, the Martinez family moved into Rose Berry Lane, and on the very first day their daughter Gabby, only a young girl at the time, encountered a young Paul Williams minding his own business. The story goes that Gabby punched him in the arm because he 'gave her a weird look', and when Paul tried to push her away, she threw herself on him and tried to wrestle him to the ground. The Martinez household were petrified since they had only just moved in and were already going to be landed with a horrible reputation in the area, or even worse, a lawsuit. They immediately took Gabby round to the Williams house to make sure that she apologised and to try their best to smooth things over. The Williams parents were unsure at first, but Paul pushed passed them and told Gabby that he forgave her and asked if she would like to play. Gabby agreed, the two households became very close and Paul and Gabby had been childhood friends ever since.

Over the years the two friends matured, and Paul began to notice Gabby as more than just a friend. She was 18 now, and he believed that he had started to develop a strong crush on his closest friend. As his hormones ran wild the simplest activities they had done as kids became so much more sexually charged now that they were both 18. Sleepovers in particular had become torturous for the poor boy, as Gabby would wear only a small cropped t-shirt and tight booty shorts as pyjamas. Paul didn't stand a chance, and sometimes when they would wrestle like the old days and they were rubbing their bodies close together he would often have no choice but to excuse himself to the bathroom so that her could work off his sexual frustration.

Eventually, in their final year, their relationship reached a boiling point. All their friends wouldn't shut up about how obvious it was that they wanted to be with each other, and even then, Paul couldn't work up the courage to make the first move. It took Gabby confronting him in the canteen at lunch in front of everyone before they admitted their feelings towards each other, and officially started dating. Soon after, Gabby convinced Paul to sneak off from classes to his house, and while Paul was very reluctant to break the rules, he soon discovered that Gabby had been planning for them to wrestle each other like the good old days, except with less clothes on. They ended up spending that afternoon working off their sexual frustration in a much more satisfying way.

The school year continued, and the end drew near. It was at this point that Mr and Mrs Williams realised that they had made a terrible mistake and had not accounted for Paul's end of year exams. Paul urged them all to go anyway, assuring them that he would be fine on his own and perhaps it would help him focus for the exams to be alone in the house. His parents reluctantly agreed and left for the holiday, leaving Paul on his own. The exams came and went, and Paul still had the house basically to himself for the summer.

Gabby, always one to spot an opportunity, had basically moved in at the start of the summer, and the two had spent their final summer before college fucking each other's brains out as much as humanly possible. Their days consisted of fucking, eating, sleeping, chilling out and then some more fucking. Gabby had made herself at home, treating the house as if it were hers, but Paul wasn't exactly complaining. He was in a paradise in which he was almost constantly having hot, passionate sex with his gorgeous girlfriend. This was going to be a good summer.

We rejoin our young lovebirds in the middle of this summer as Paul was enjoying his afternoon handjob. Gabby increased her pace, just a little, and Paul let out a slow moan in appreciation.

"You like that, baby?" Gabby looked up into his bright blue eyes and ran her tongue over her lips. She found him so cute when he expressed pleasure like this. "That feel good, yeah?" She gave his shaft a short, firm squeeze just to rouse him a little.

"Unnngh... Yeah, oh yeah, you're so good Gabby, it feels so good, fuck..." Paul moaned and squirmed as Gabby changed up her pace and started to fondle his balls with her spare hand. Over the months they had been together, Paul and Gabby had practised and perfected their sexual skills on each other, and now they both knew exactly what to do to each other to maximise each other's pleasure. Paul had become an expert at eating Gabby's pussy, sometimes licking her to several orgasms over a long period of time, and Gabby knew all the tips and tricks to turn on Paul when jerking or sucking his cock, usually leading to Paul shooting a huge load over a mind-shattering orgasm.

Gabby threw her hair back and giggled, not stopping her stroking for a second. She loved it when her cute boyfriend was entirely under her sexual spell. Then she bit her lip and her smile took a slightly wicked tone. "Are you feeling nervous about this, Paul?"

Paul blushed a little amidst the pleasure. "Ungh, erm, a little, yeah..."

"It's gonna be just fine, baby." Gabby reassured him, moving her hand that was on his balls to massage his pecs and give his nipple a little pinch. "C'mon, you did promise me we could try it..."

***

The previous day...

"I'm not sure, Gabby, I don't know if I'm going to like it..."

"Oh, come on, Paul, how can you say you're not gonna like it if you're never gonna try it?" Gabby spread out a bit further on the couch. "You should have an open mind. Loads of guys I know have done it, and it doesn't make them any less of a man. More so, really."

"Loads of guys?" Paul sat awkwardly on the other side of the couch and tried to refocus his attention to the TV rather than this uncomfortable conversation.

"Yeah, totally. Most of them enjoy it too." Gabby sipped on an ice-cold coke. She was truly relaxed and at home here. She then sat up a bit and began to assume a more authoritative position. "It's a zone of pleasure that goes mostly unexplored by the majority of guys. Really, it's a disservice to yourself not to experiment with it. Also-", Gabby shifted in her seat as she began to basically lecture him, "I think it's your duty to undergo this experience as a man, so that you can feel even a little bit of what it feels like to be a woman, and therefore develop a deeper level of empathy with me, your girlfriend that you worship and adore." She ended this with a playful smile. Her argument was ironclad, she had bombarded him with points and evidence and wrapped it all of with a little bit of light-hearted banter and teasing. She really was an expert at persuasion.

"I'm a little worried though. What if it like, hurts?" Paul clenched a little at the thought and tried to ignore how good Gabby looked wearing his old, small t-shirt and nothing else.

"Aww, honey, don't worry, I'll be gentle with you." Gabby cooed. She moved over to him and started to run her hands around his shoulders, trying to massage any of tension out of his body. She needed him nice and loose if he was going to give her what she wanted. "Don't you trust me?"

"Of course, I trust you, I just-"

"Well you've got nothing to worry about then." Gabby lifted a finger to his chin and turn his face so that he had no choice but to look her directly in the eyes. "Paul, it would really mean a lot to me if you were willing to at least try this. It would show me how much you're willing to be vulnerable and intimate with me." She maintained eye contact and made sure to slowly blink a couple times. She really could pile it on when she wanted.

"It... It really means this much to you?" Paul was already stammering from her being so up close and personal to him. Even after all the months they had been together the simple stuff still got to him. The feeling of her breath on his cheek. Her pleading puppy eyes. He felt himself loosening up under her firm grip.

"Of course." Gabby cuddled up nice and close to him. "Remember, we can stop at any time if you feel uncomfortable. Not that we'll need to, I reckon you're gonna love it." She playfully bit his ear, eliciting a little squeal from Paul. "So, what do you say? If you're really not ok with it then we won't, of course. But I really want to try this with you, and I think it could be so fun. For both of us."

Paul looked at the beautiful woman he was lucky enough to call his girlfriend as she held him tight, and he figured that he might be falling in love with her.

"Paul?"

Paul took a deep breath in and out before answering. "Sure, ok. I'll give it a go. For you."

Gabby jumped up in delight. "Really? You mean it? Ah, yes, Paul you're the best!" She leapt back on the couch and wrestled Paul into a tight bear hug. She'd always been a little bit stronger than him, and he knew this, so he stopped resisting and let her have his way with him.

Then she jumped back up and began to pace up and down the room as she explained her thoughts out loud. "Ok, I need to get some stuff ready for the big event, so we'll do it tomorrow. I want you in tip top shape for it, Paul, so that means no cumming for the next 24 hours, ok? I'm sure you can at least manage that." She stopped pacing and winked at her bemused boyfriend at that last part.

Paul was a little disappointed. 24 hours wasn't long, but he had grown used to orgasming a few times a day what with all the constant sex they'd been having the last couple of weeks. He was also a little surprised at how enthusiastic Gabby seemed. "You're... really excited for this, aren't you?"

"Yeah, well, I dunno..." Gabby shifted a little awkwardly on the spot. "It just... just makes me really horny, thinking about it."

"Oh yeah?" Paul sensed an opportunity and rose from the couch. He came close to her and immediately started making out with her, lustfully groping and squeezing whatever parts of her body he could, any rational thought blocked out by the horny fog of his mind.

Gabby squealed a little in surprise, but was soon compliant, kissing back and feeling her hands all over her man's body passionately. Soon enough, her hands felt their way down to his cock, and she felt it rock hard and already at 100% attention. She pulled away sharp.

"Uh, uh, uh, naughty boy. No cumming for you, remember?" Gabby smirked as Paul whined a little. "I know what you can do, though."

Without waiting for a response, Gabby pulled off the old t-shirt with both hands, leaving her completely naked. Then she threw herself back on the couch, and adopted a wide, relaxed stance with her legs wide open. With one hand she began to play with one of her nipples, and with the other hand she took a sip of her drink before setting it back down and making a beckoning motion with her fingers.

"Come here, baby."

Paul smiled. He knew what to do. He took his position, on his knees between her legs, his cock still sticking straight up, almost painfully erect.

Gabby smiled and looked down at him expectantly. Paul had started to kiss the inside of her thighs before he felt her hand guide his head impatiently to its destination. He got the hint, and obediently began to eat her pussy, guided by Gabby's controlling hand.

"Oh, fuck yeah baby. That's the good stuff." Gabby moaned and squeezed her legs together around Paul's head. Gabby then looked down and admired how her boyfriend was enthusiastically licking her, trying his best to bring her to orgasm, despite knowing that he was not allowed to cum until tomorrow. She began to rub her pussy across his face a little more aggressively, really getting into it.

"Oh, fuck yeah. Paul, you better prepare your ass." Gabby moaned as he found just the right spot. "Because tomorrow I'm gonna fuck it."

***

Present day...

"Yeah, yeah, I remember." Paul was now wishing he hadn't given in to her demands so easily, or at least gotten something promised in return. He'd really like to play with her ass, but she hadn't really let him near her asshole yet.

"Keep in mind, if you're not ok with this, we can always stop at any time. It's very important that you know that, Paul." Gabby reassured him while her fingers had stopped stroking his shaft and were now tracing around the sensitive head of his cock, sending shivers up and down Paul's body. "However, I would really, really like you to at least give it a go. I'm so excited for this!" Gabby smiled and all of Paul's worries subsided for a second.

"I understand. I think... I think I'm ready."

Gabby nodded. "Good. Then let's get started." Gabby coated her fingers in some lube she had kept nearby in preparation. Then she returned to the excruciatingly slow strokes of his cock, while with her other hand she started to trace her fingers down, over his balls, and towards his little, hairless asshole. Paul had never really been touched here, in this taboo area, so he shivered and spasmed at every small movement of Gabby's fingers.

"Calm down, baby!" Gabby giggled. "I haven't even got to the good bit yet, and you're already bucking around like a bitch in heat. Settle down, now." Paul tried to relax as she had instructed while Gabby removed the hand from his cock and used it to lift up his balls so she could get a better view.

"Lift up your legs a bit for me baby, just so I can get to it easier." Gabby smirked as he complied. "Wow. You're so cute right now, exposing your pretty little asshole to me like this."

Paul tried to ignore her comments as he raised his legs to allow her easier access to his asshole. The sooner this was over with, the better.

Gabby, on the other hand, seemed quite happy to take her time with this, and was very slowly and carefully tracing her finger in circles around his opening. Sometimes she would jerk her finger forwards a little as if she was going to suddenly penetrate him, and his body would jolt in surprise.

"Jeez, Gabby, what are you doing to me?" Paul whined.

"Just havin' a little fun, babe, calm down." Gabby gave him a little squeeze on the balls with her other hand to pacify him a little. "Didn't realise you were so eager to have your asshole played with." She smiled after teasing him and refocused her attention on his bare ass. She decided to stop toying with him, and on her next pass that her fingers made of his asshole she instead held her fingers there and applied a little bit of pressure. Immediately she felt Paul clench up around her touch.

"Shhh, relax baby. I'm gonna go slow but I need you to relax those muscles. Just let me in and it won't hurt so much, ok?" Gabby held her finger in place firm and solid, not letting the resistance from Paul's ass muscles stop her intrusion.

Paul took a deep breath. "Ok, I'll try." He exhaled, and as he did so, his muscles unclenched a little and he tried to accept the alien feeling of something penetrating his asshole.

"Good boy. Now just relax." Gabby slowly continued to apply pressure and her finger slowly started to inch into his ass. "Fuuuuck, you've got such a tight little ass, baby."

Paul could only whimper in response. Although he wasn't exactly comfortable, the feeling wasn't exactly painful either. Maybe once he got used to this it wouldn't be so bad.

Once she was a knuckle deep, Gabby paused for a second, allowing his ass to accommodate her finger, feeling it clench and relax around her in waves. Then, she slowly started to work a second finger in. She glanced at Paul, and his expression was a mix of confusion and bewilderment.