tagTransgender & CrossdressersIn Time for Summer

In Time for Summer

byScumDumpster69©

"Sarah...?"

Elliot couldn't believe his eyes. The very same person he had called his girlfriend no less than a week before, strutting into his apartment, drunk and giddy, with his lesbian roommate in tow.

"Hi, Elliot!" Sarah exclaimed with a giggle, without any thought of the poor boy's feelings. "It's good to be back!"

"What are you doing here?" Elliot asked, a foolish question he immediately realized.

"What do you think she's doing here?" With an arm around Sarah's waist, reaching all the way down to her pussy which she began shamelessly fondling, his roommate stood behind his ex, grinning at him. Jenna was her name.

It wasn't the first time she had brought home a girl from the club on a friday night, in fact, that's an understatement. Elliot wasn't keeping tabs, but to him it seemed to be happening almost every week. And it wasn't hard to see why. Jenna was an absolutely stunning girl, tall and slender with an hourglass-shaped body, an angelic face and just the right amount of athletic features to enhance her femininity to the max.

"Poor Sarah here told me she hasn't had a real orgasm in several months, so I thought I'd do the honor." Her grin widened from ear to ear in what seemed like an attempt to piss Elliot off. "We're gonna head on over to my room." She held Sarah in her arms and planted a kiss on her head, much to the delight of the giggling blonde, before turning her sly gaze to Elliot.

"Hopefully we won't keep you awake too long."

"Have fun with your video games or whatever!" Sarah shouted mockingly as they turned around and headed for their soon-to-be love nest.

As soon as they were out of sight, Elliot clenched his teeth and balled his fists in anger. Not only was he again going to be forced to listen to the endless moans and squeaks from Jenna's room, but now, his ex-girlfriend would be the one moaning, something he had never heard in their short relationship.

He should have seen the break-up coming. Thinking back to it, Sarah never showed much interest in him, it almost seemed like she had decided to date him out of boredom, or perhaps as some sort of experiment. He wasn't exactly of the manly type, which he assumed was the reason that Sarah broke up with him. Not that there was any way for him to know, as she abruptly broke up with him over text without stating a reason.

When they were dating, Sarah had came over a couple of times and had hit if off with Jenna instantly. Ever since then, Elliot's relationship with Sarah had only become more strained, for reasons initially unknown to him. It only now dawned on him that the two girls might have hit it off a bit too well when they first met.

He had always known that Jenna was a bit of a player, or perhaps more accurate, a slut. But the fact that she would go as far as to steal his girlfriend filled him with both rage and grief. Her and Elliot weren't even particularly compatible as roommates, let alone friends, but he had always trusted and respected her. Now, all that was thrown out the window.

An hour passed since they had come home, and just as expected, the moans and screams echoed throughout the apartment the entire time. Elliot had gone to bed, wanting nothing more than to fall asleep and be free from the torment, but it was impossible to escape the noises, despite the fact that there was an entire kitchen and two closed doors between their rooms. Tears streamed down his cheeks as he folded his pillow over his head in an attempt to muffle the sounds. Sounds indicating that Jenna was giving his ex more pleasure than he ever could have.

He had no idea what Jenna did to her partners to always elicit such kinky screams from them, but Sarah seemed to be the loudest of them all.

"Fuck yeah, you like that tight pussy?!" he heard her shout once, followed by "Oh my god, fuck me with harder with that huge cock!"

Jesus christ, Elliot thought. Were they seriously using a strap-on?

Perhaps that had been Elliot's determining shortcoming, his lack of size where it mattered. For some time he had thought that his penis was about average, but his time spent in locker rooms and on pornsites had taught him that such was not the case. In addition to his grief, shame washed over him as he realized that a woman with a toy made for a better lover than him.

It took him another whole hour to finally fall asleep, but the noises continued even beyond that. If he had stayed awake longer he would surely have questioned the sanity of his horny ex-girlfriend, as every minute of love-making with the beautiful Jenna only drew out more depraved phrases from her.

Many hours and a night of restless sleep later, the warm rays of the afternoon sun hit Elliot's window like searing lasers, quickly heating up his room to a degree far beyond what anyone would have considered pleasant. Despite only being mid-may, the weather made it seem like it could just as easily have been in the height of summer, or as if he lived in a tropical paradise.

Like glued to the bed, Elliot woke up with sweat covering every inch of his body. For a second he was annoyed only by said fact, before the voices coming from the kitchen made him remember the night before. He heard Jenna speaking in a sultry tone and Sarah responding with a girly giggle, a sound that Elliot had now quickly come to hate.

He felt a bitter taste in his mouth, twisting and turning away from the direction of the sound in the sticky bed sheets, finding it impossible to block out the noise without childishly covering his ears with his hands. He refused to get out of his room while they were still in the apartment, he didn't want to risk any further humiliation.

This was a first, the girl Jenna having brought home still being in the apartment in the morning, and Elliot did not like it one bit. It was perhaps a sign that Jenna liked her a bit more than any of the other ones who had spent the night with her, meaning that they would most likely be seeing eachother again. That said, Elliot had just discovered the true natures of both his ex and Jenna, so it was definitely a possibility that they were occupying the kitchen only to rub in his face that his girlfriend had essentially been stolen from him.

He wasn't left alone for long, though. After what couldn't have been more than 15 minutes of flat out suffering in the hot, sweaty bed, Jenna violently swung his door open, holding Sarah with one hand.

"Hey, Elliot!" she said, brimming with joy. "We're going to the beach, wanna tag along?"

Surprised and annoyed by their entry, Elliot slowly turned to them with a frown, eyeing their swimsuit-clad bodies of the two girls, Jenna admittedly being the significantly prettier one. Not that Sarah wasn't pretty herself, but Jenna was just an absurdly attractive girl.

Sarah was dressed in a slutty, white string bikini which left little to the imagination, while Jenna wore a surprisingly modest suit in comparison. A black one piece with a short, ruffled skirt, almost a bit childish looking, which strangely enough went very well with her slender, womanly curves.

Elliot's eyes went from looking at their bodies to their faces, noticing the teasing grins they had put on, clearly making fun of him. There was no way they were expecting a yes from Elliot, and they wouldn't get one either of course. He was already pissed off enough from starting the day off with them in his presence.

"No," he dryly replied, turning his back to them. A soft giggle could be heard from Sarah, whereas Jenna stayed silent.

"What, you're just gonna stay in bed and sulk?" she said after a moment, in a taunting voice that agitated Elliot even more, almost to the point of drawing out a retort from him but ultimately he decided not to. "Alright, suit yourself," Jenna continued. "Later!"

Nonchalantly leaving the door to his room open, the two girls strutted out of the apartment without a care in the world, leaving Elliot alone to sort out his feelings. Feelings of betrayal and hatred. Sarah had seem like a bit of a bitch even when they were dating, so it wasn't that surprising that she would pull something like this. But Jenna? What could she possibly stand to gain by making an enemy out of her roommate?

The more he thought about it, the more mentally exhausted he became. With weak, trembling limbs he crawled out of bed, feeling completely dead inside, needing something to ease his mind. He sighed deeply as he pulled off the sheets off the bed to prepare them for laundry, figuring he might as well do something productive to prevent himself from becoming a depressed wreck, being all alone with a mind filled with angry thoughts on this beautiful saturday that just begged to be enjoyed to the fullest.

For the several hours that his roommate was gone, Elliot did everything he could to think of other things, finding that it became increasingly difficult for every minute that passed. Doing the laundry, cleaning and cooking could only do so much to distract him, his bitter thoughts from before ending up catching up to him again.

When his chores were finally done, the evening had already settled in. After taking a shower, Elliot was sat by the kitchen table with a freshly cooked meal in front of him, a somewhat disappointing plate of spaghetti bolognese that he had half-assedly thrown together. As he started aggressively shoveling the food into his mouth, he found himself overwhelmed with anger once again. He wanted to break something, contemplating for a second letting that something be the dinner plate in front of him, but thankfully settling on slamming his fist into the table instead. He cursed his slut of a roommate, cursed his slut of an ex, cursed his parents for his garbage genetics that no woman would ever want to pass on. Cursed everything for the way his life had turned out.

Then, all of a sudden he snapped out of it when he heard the sound of the front door opening. There was no time to mentally prepare for more humiliation at the hands of Jenna and his ex, making him break down into a cold sweat as the door swung open. However, luckily and surprisingly, the only person standing in the doorway was Jenna. She was still wearing her black swimsuit, her lightly freckled face ever so slightly tanned from the unflinching sun, and her beautiful brown hair hanging long and messy.

"Hey, made any food for me?" she asked, casually slamming the door behind her and strutting in.

"No..." Elliot replied barely audible, as Jenna pulled out a chair and sat down on the opposite side of the table.

"Why's that? Are you mad at me?"

Elliot knew it was a bait, he hardly ever made food for her in the first place. Without answering, and without even looking at her, he just kept eating his food, while Jenna let out an amused chuckle.

"Aww, are you upset because I stole your slut of a girlfriend? Is that it? Come on, say something, you've been so quiet lately."

Still not giving in to her taunts, Elliot stayed silent. But there was no denying that her words hurt. This was the first time Jenna actually acknowledged what she had done, and how she had so casually, downright humiliatingly done it spoke volumes about what kind of person she really was.

"You realize it was inevitable, right?" she added, without skipping a beat. "You should be happy that she even went out with you in the first place. I mean, if she was gonna date a little girly boy like you it makes more sense for me to have her, don't you think?"

"Shut up..." Elliot mumbled, looking down at his plate, his face covered by his long, raven hair. Jenna went on to cross her legs and lay them out over the table, close enough to Elliot's plate to be considered rude by any sensible person.

"She talked a lot about you, you know," she continued, ignoring Elliot's weak protests. "About how she could never be with a man shorter than herself. About how skinny and weak you are, and how you don't even have any body hair like a real man."

At this point, it was becoming too much to bear. He tried his best to ignore her, but hearing her make fun of everything Elliot was insecure about made it hard to hold back tears. He knew he was short, he knew he was skinny and weak despite trying his hardest to put on muscle in the gym. And he knew he would never be enough for any self-respecting woman.

To prevent Jenna from seeing his discomposed, teary face, he got up from his seat and carried his plate and utensils to the sink, hanging his head low the entire time. With a shaking hand he reached out to turn on the tap water to wash the plate off, eager to storm off into his room and cool his thoughts. He could feel Jenna's belittling gaze burn holes into the back of his head, watching his every movement, taking in his frustration.

"Oh, right. She mentioned your dick as well. How big was it? Three inches? Three and a half?" Her words were blunt and straight to the point, with no trace of amusement in her tone, which somehow made it worse, as if she just had to casually mention his size for no apparent reason. "Either way, that's not nearly enough for... well, any girl, really."

That was the last drop. Elliot had been thoroughly reminded of just how pathetic he was in every way, by his roommate no less. His will was broken, his body was trembling, and his face had been reduced to a clenched up, teary mess. Slowly, he brought his hand up to cover his eyes, all the while sniffling loudly, trying not to break out into a full-on bawling.

Jenna had gone quiet, realizing that she had brought Elliot to the tipping point. She decided to just stare at him for a while, awaiting his response. There was no way he wasn't going to say something back, she knew that. They may only have known each other for half a year, but Jenna had quickly learned that Elliot wasn't the type of person to simply take abuse without fighting back.

That's why even she was taken aback when his reply finally came. "... How can you be so cruel?" he murmured, struggling to hold back his crying-induced hiccups. "I know I'm pathetic. You don't need to remind me."

Jenna sat dumbstruck for several long seconds, before finally collecting herself and putting on a satisfied grin. In one swift, graceful movement she swung her legs down from the table and stood tall, with her arms crossed under her shapely breasts, raising them up to show off a slight cleavage in the black swimsuit.

"Oh, but I do need to remind you," she said, taking a few slow steps towards the still turned away Elliot. "I'm not doing this out of cruelty, you know. I just want you to accept yourself for what you are."

"What difference does it make? Why do you care?" He finally mustered up enough courage to turn around and face his roommate, despite his sorry state.

"It makes all the difference in the world to me, Elliot." She had stopped a few feet in front of Elliot, now with her hands on her hips. "You have to realize that you'll never please any girl through normal means."

Elliot bit his quivering lip in frustration. He had never had violent urges, but now it was difficult to resist punching Jenna in the face. Of course, he knew that he didn't stand a chance against her. She stood about as tall as the average man, a couple of inches or so short of six feet, whereas Elliot wasn't even as tall as the average woman. Not to mention Jenna being in far better shape than him.

"Again, what the fuck does that have to do with you?" he seethed, with a voice still shaky from crying. "And what do you mean by 'normal means'?" His arms hung down his sides, with fists clenched in rage. He could see Jenna's grin grow even wider as she eyed him all over, amused by his aggressive stance that just came off as adorably pathetic. She knew she wasn't in any danger whatsoever.

"Say, aren't you curious to know how I manage to bring home a new girl every weekend?" she asked, tilting her head to the side slightly.

"I already know you're attractive. Can't exactly be difficult for you."

"Oh, Elliot, sweetie." she purred tauntingly. "Me being attractive is only part of the puzzle. Girls want something more than that, and that's where my little secret comes in."

"... What little secret? What are you talking about?"

A soft, but menacing giggle escaped Jenna's lips, watching Elliot's facial expression turn into a mix of anger and confusion. He was so adorably clueless. But he wouldn't stay like that for long.

Jenna proceeded to slowly run her hand past her swimsuit's ruffled skirt, down between her thighs, grabbing the fabric covering her genitalia and yanking it to the side. And the reaction to her reveal that came from Elliot was even better than she had hoped. His eyes went wide. His jaw dropped. His already tense body tensed up even harder, but for reasons far different from before.

Out of Jenna's swimsuit where it had been tucked back, her "little secret" had flopped out, except it wasn't little at all. A huge, flaccid piece of meat swinging low and hefty, with a pearl of precum about to drip off the tip. Behind, a set of smooth balls proportionate to the size of her cock hung just as low, completing her package that was far bigger than Elliot's, even in his erect state.

"That little dick of yours isn't going to make anyone orgasm," Jenna said in a sultry tone, showing off her teeth in a wide smile. "But that tight ass might."

"W-wait, Jenna, what the fuck?!" Elliot exclaimed, with a voice a bit more high pitched than usually.

"Don't you get it?" As if to show off her genitals on a platter, Jenna lifted up both her cock and testicles and held them out in the palm of her hand. "You were never meant to be manly. You're a natural bottom, that's the way it's always going to be. And the only thing you can do is accept it."

"W-wha..." Elliot stammered, his eyes fixed on the intimidating cock on display, not realizing that Jenna was slowly inching towards him. Before long, she stood right in front of him, finally making the quivering boy look up and meet her eyes while she sat her free hand down on the counter behind Elliot to show her dominance.

"You're the only one that I want, Elliot, that's why I got rid of that slut of a girlfriend for you. You weren't meant to be with her. You were meant to have my fat cock in your life. I'm not actually lesbian, you know."

"You... want me?" Elliot gulped meekly. He should have felt anger over having been reminded of his ex and confusion over seeing that Jenna apparently had a huge penis, but somehow, hearing her say that she was attracted to him seemed to drown out all other feelings. Never in his life had someone expressed a sexual or romantic interest in him, not even Sarah really, when he was dating her.

"Fuck yeah, I do," whispered Jenna, leaning over beside Elliot's ear. "You know, if you agree to become my boyfriend, I'll make you feel better than you could ever imagine. Provided that you let me fuck you, of course."

"No... I don't want that..." Elliot mumbled, turning his head away in shame upon hearing Jenna's proposition.

"Really? You really wanna miss out on what made all those sluts keep you up at night?"

Elliot fidgeted where he stood, visibly uncomfortable by the situation. He wanted to run away, but Jenna's predatory gaze made him feel anchored to the floor, and the fear of not knowing whether or not she would take no for an answer wasn't helping.

"Sarah enjoyed herself at least, let me tell ya," Jenna cooed, licking her lips inches from Elliot's face. "I lost count of how many times she squirted all over me. Damn near milked me dry too, you should've seen it."

"That's... gross..." Elliot cringed, his cheeks reddening in embarrassment. He kept moving his face away from Jenna's, who seemed to be inching closer and closer with every passing second. Moving her hand from her balls to her slowly stiffening cock, she began jerking it right in front of Elliot, only a few inches from poking him in the belly with it. Several drops of precum dripped from the moist, skin-covered head, hitting the floor right between Elliot's feet.

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byScumDumpster69© 17 comments/ 30098 views/ 104 favorites

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