My Ruined Alone Time

Description:

Alex has developed a bit of a problem. Dressing up as a girl and masturbating 3 times a day. On a regular Friday night, Isabel comes knocking. Unable to stop her from interrupting, Alex soon finds himself uncontrollably revealing everything to her. And in turn, awakens something in her.

----

Alex laid on the uncomfortable mattress. A black and white skirt was wrapped around his feminine hips. A small bra with a flower design wrapped around his otherwise naked chest. His room was lit only by a small lamp. It gave out a yellow glow that made his dorm room seem like a damp cave. His toes curled and he bit his lip to quiet his moans. A small little black vibrator was currently in his ass. Mentally, he called it his pussy. He stretched and kicked his small hairless legs as it brought him closer to climax. He cried out quietly to himself and rolled his head on the bed. He always had intense orgasms. Ones that would put him in a fever state. His body would become hot and the world would spin. His mind would shut down and he'd imagine himself plowing a girl. A girl that looked like himself. He failed to see how fucked up he was. Porn and constant masturbation had led him here.

For a time, his fantasies were of him as a normal guy. A bit taller. A bigger dick. A masculine face and body. Hair that grew more than a few centimeters. But as he continued to age, he realized this wasn't going to happen. Comments about his feminine body had always hurt him. He would have been happy to be somewhere in the middle. Half feminine, half masculine. But instead, he had to deal with the fact that his body always seemed to misplace his fat. It would go straight to his butt.

Girls made jokes that he could borrow their clothing if he wanted. That he was always invited to the sleep overs. He never went to them. Then at some point, he found himself stumbling onto anime drawings of femboys. It became an obsession reading hentai about femboys. Then eventually, Amazon dropped off some female clothing. Many nights of staring at himself in the mirrors came and went. Eventually, he got to the present. A fucked up amalgamation of his fantasies where he was the guy and the girl.

His hands trailed up his soft stomach and then dug their way into the bra. He yanked and pinched his nipples. His eyes were closed and he began to shake his head back and forth. His long hair spread across the pillow and as he shook, strands of it covered his face and got in his mouth. His hair was a dirty blonde. He was only a minute or so away from achieving his orgasm.

But, his dream world was suddenly shattered by a knock at the door. His eyes burst open and his breath quickened. It was a Friday night. He had no friends. Sometimes he heard light knocks that had echoed from other rooms and was unsure if that's what this was.

Then the knocks came again and he was sure it was for him. His hand rushed to his butt and pushed down on the button to turn it off. He saw no need to remove it since whoever was here was most likely at the wrong room. He just needed to guide them away.

Another knock.

"Uh, one sec!" He yelled out. He stumbled off his bed and rushed for his sweatpants. Quickly pulling it over his skirt and then rushing a black shirt over his bra. His face was sweaty and a bit sticky and he threw back his hair. He locked his computer that was filled with porn and then approached the door.

He pushed the handle down and then gently opened the door, poking only his head out and keeping his body hidden.

"Um, hello?" He said before he had seen the person who was disturbing him.

In front of him stood Isabel. She wore a light brown hoodie with the university name stitched onto it. The hoodie was a bit small on her and he could see her bellybutton. Below that was grey shorts that clung around her wide hips. She had long tan legs and wore flip flops. He had taken a bit too long to look her up and down and was about to apologize but she spoke first.

"Alex, hey, did you do the math homework?" They were both math majors and had shared a few classes at this point. A few words had been exchanged in the past but nothing more. He wasn't even sure how she knew this was his dorm.

He hesitated to respond and only got a pitiful "uhhhh" out. His mind was still whirling. He had been so close to his desired orgasm. Somehow, she took this as an invitation in and pushed the door open. Unsure of what to do, he simply moved out of her way and opened the door further.

His room was a bit of a mess but wasn't horrible. It was a square dorm and so every facet of the room could be seen immediately. Articles of his regular male clothing laid on the ground. His female clothing hung comfortably in the currently closed closet. Isabel moved forward and dropped her backpack onto his bed. The blankets were a mess and she pushed them into the corner making room for herself.

Still standing, she turned and looked at him. She had a sharp jawline that scared many men. A thin nose with small nostrils. Long black hair that fell over her shoulders and little strands of hair that formed her bangs. Thick eyebrows and long eyelashes. Her eyes were tall and stretched out far. Eyeliner, that was now more than 12 hours old, made them stretch further. Her eye contact had always made men a bit nervous but it never truly concerned her. She was used to their anxiety. And so when Alex looked back at her with fearful eyes that begged for her to leave, she ignored it.

"W-what homework?" He responded in a soft voice.

"The discrete structures homework. Did you do it already?" His mind was slowly reforming and finally was able to muster an actual reply.

"Uhm, yeah yeah I did that already. I, uhm, how did you know this was my dorm?" He inquired

She was pulling her notebook out and opening the textbook and seemed to not hear the question.

"Well, I need help with it. You can close the door now." She seemed to command him but her eyes never actually raised to look at him or the door. He pushed it in until he heard it click. He had never had a girl in his dorm. Not this one, not the one he had last year.

He was so used to always wearing a bra and panties that he had almost forgotten about what he actually had on. She seemed unconcerned with his mild fidgeting and awkward pose.

"Okay so, question 5, what the fuck do you even do? I understand induction... kinda but I don't understand how you actually write this proof."

His mind had become so warped and broken that he couldn't see anything past his eluded orgasm. He had accepted long ago that girls weren't something he would ever understand. The only girl he understood was the one he had created in himself. And he was desperate to see her again.

"Isabel, I'm kind of bus-"

"No." She flatly stated. Finally she looked at him. "You're not."

He lasted only half a second before he had to avert his gaze. Her lips were curled in annoyance. Her eyes gave the impression that she knew everything about him. That she might blink and activate some sort of x-ray vision and see past his first layer of clothing.

"Well. I-I didn't even know how to do that question." His mind provided him another excuse failing to realize that he had now proven that her last statement was true.

"Dude, why won't you help me?" She was getting frustrated. She was a good student and always had amazing grades. But that didn't mean she was afraid of asking for help. If a question popped into her mind, she always asked it. She was a blunt person.

For many people, they found her cruel and mean. Yet, she always had a revolving group of friends that clung to her. It helped that she was incredibly hot and cared about how she looked.

He stuttered out nothings. Chattering his teeth, looking for some sort of reply.

"Well, I mean, uhm, I don't kn-, can't you, well I'm-, it's Friday."

She let out a frustrated sigh and tossed her textbook onto the bed. She stood up and walked over to him. He was still next to the door and as she approached, he felt he should bring his arms up to protect his face. That she might punch him. He felt cornered.

She got within a few inches of him and then looked back at the room. Inspecting every detail. She was trying to figure out why the hell he didn't want to help her. Then, she swiveled back to him. She was an inch or two taller than him and so his eyes matched with her nose.

"Were you jerking off?" She said as loudly as she had said everything else.

His face turned red and he brought his arms up to his chest. Folding them around the bra. He felt naked and not in the way he liked. His throat closed up and his mouth parted a bit. He was in shock at how she had confronted him. She hadn't hesitated for a moment. He had never been this close to a girl before. She looked like she might rip off his head and fear pumped through his veins. His small penis jumped a bit. The pink panties below his skirt were wet. His dick had shriveled up and all the precum had oozed outwards.

While he refused to meet her eyes, he still stared at her face. He found her incredibly beautiful. She had a dominant face that could force you to do anything. For a moment, he even thought of what it might be like to fuck her. Like she had activated some long gone masculine identity within him. That was soon overpowered with the thought of what it might be like for her to fuck him.

She rolled her eyes. "Get over it." And then grabbed at his arm and yanked him forward. He tried to resist but she had incredible strength. He lurched forward with her and tried to pull back. She could have easily pulled him further but instead let him fall.

He went down to the ground and landed on his large bubble butt. Just hard enough that the power button on the vibrator was hit.

The quiet room suddenly was filled with a light buzzing sound. He shook as it revved back up.

She swiftly turned to look back at him. He looked up at her tall imposing stature. Her long body glowing in the lamp light. She looked angry but simultaneously puzzled. Unsure of what had just happened. She wondered what that sound was and why he looked like he might pee his pants. Why suddenly beads of sweat began to pop up on his face. Why his legs were beginning to shake.

She loomed over him as he attempted to stand up. His knees buckled and trembled. He was trying to get up but the vibrator had lodged itself further into him. The humiliation of the moment was contributing to his pleasure. His mind began to spin once again. Ecstasy took over and his brain became numb. Instinctively, he grabbed at his chest and squeezed the bra. This only pulled him further away from reality.

He arched his back and pushed his groin up. He caught a glimpse of her before his eyes rolled back. Isabel had taken a seat. Watching the pitiful disgusting scene unfold in front of her.

He bit down on his lip and cried out soft petite moans. His masturbating sessions were always quite intense. As the girl inside him had begun to take form, he had found that a broken blank mind helped him cope. And so he had accepted it further and willingly encouraged the pleasure to rip his brain apart. Now, as he found himself with an audience of one, it was coming back to haunt him. He was pretty sure that her being here had made it worse...or better.

She watched him with curiosity. She felt herself getting a bit wet. She had always liked the smaller, more petite boys. The guys she observed at the gym alongside her always turned her off. The men who had the balls to approach and talk to her also disinterested her. She wasn't a virgin. She had had sex multiple times but often found a man's body hair annoying and gross. The way they attempted to control the entire sexual act pissed her off. The way an entitled guy would look at her would make her snap. She regularly called them out and would embarrass them.

Her body temperature was rising. She pulled off her hoodie having a white sports bra underneath. Her cleavage was relieved to feel the open air. They were large and heavy and jutted out from her chest. Had Alex noticed, he might have felt jealous considering his much tinier tits.

Isabel was never one to shy away from her own curiosity. It didn't matter how strange a situation was. If she was interested, she'd look closer. If she wasn't, she'd never think of it again.

Now she found herself interested. Staring as Alex got closer and closer to climax. The bra beneath his shirt was now obvious. She wondered what else he was wearing.

She got up and bent down to him. Placing a knee on the rug and then grabbing his shirt. His eyes came back to reality and looked at her. She had a hint of a smile on her face but even she didn't realize this. She pulled off his shirt to reveal his floral-patterned bra. Then yanked down his sweatpants to reveal his skirt.

Alex let out a soft, "Please." He wasn't sure what he was asking her to do. But he continued to repeat it.

Alex couldn't hold out any longer. His pussy was trembling and was sending shockwaves across his body. Isabel watched him perform a final act. His muscles tightened and he let out a long jagged cry. His cum spilled out. It had nowhere to go and so seeped into his panties and coated his dick. His cries were high pitched and feminine in nature.

If anyone had heard this, they would have been impressed. That the lonely virgin was actually making some girls' night. That would have been easier for them to believe than the reality of the situation.

His orgasm had finally finished but the vibrator continued. He reached his hand downward to attempt to turn it off or pull it out. But Isabel stopped him. She slapped his hand away.

"Please....leave me alone." He presumed that's what he had been trying to say earlier.

She ignored him and tried to take off his skirt. She wanted to see the vibrator that she had unknowingly turned back on. The vibrator that had forced him to cum in front of her.

"Stop please!" He cried out. She craned her neck to look at him and he felt terror. He covered his face with his hands and began to weep. She pushed him over and then ripped the skirt down. The pink panties stretched to accommodate his large ass. She pulled them to the side and finally found it. A tiny black vibrator. She could see the power icon. She touched his sensitive flesh and heard him whimper. Then, her fingers pressed around his hole so as to be able to grab the base. Slowly, it began to pull out.

Alex whined and cried and moaned as she pulled it from his pussy. It left him empty and depressed. He had planned to masturbate a few more times tonight.

Isabel held the vibrator in her hands. She turned it off before looking back at his ass. His tight hole winked at her as it attempted to find anything to fill it back up. A bit of lube still surrounded the area. Not skipping a beat, she plunged her finger into him.

Then two.

A little yelp and then a continuous moan was all he could reply with. A moan that was only broken up by his short quick breaths.

Finally, it all clicked for Isabel. It usually never took her this too long to figure out and decide what she wanted. But now, her large dark lips formed into a smirk. She pulled herself over Alex, standing on her knees. She began to drive her fingers deep into his ass. Flexing and curling inside him. His pussy had never been used like this before and he placed his palm over his mouth. Then she leaned forward. Her other hand grabbed a clump of his hair and yanked. His mind was beginning to swirl once again. She let out a devilish chuckle.

"You're mine now."

--

I hope you enjoyed this. Please rate and comment if you please.

This story is also written as a plea to FemFreak to please write more. Write anything. I'll read it. Or maybe continue Popping His Cherry. Or add a sequel to Wide Hips for a Guy. I'm begging, give me anything!

You've forced me to write this. Something not even comparable to what you've published.