Alex's Fateful Feminization

Headphones in and sun out, Alex was oblivious to anything around him as he blissfully made the routine walk from the basketball courts to his apartment complex. Several nice suburbs lay east of the main road that cut through town, and just on the other side of the strip mall opposing the neighborhoods, stood a small apartment complex. It was quite nice, and to Alex's benefit, it was close to campus. He knew the owner of the building and made out like a bandit, only having to pay half price for a two bedroom apartment that was far more luxurious than he could have afforded anywhere else. After walking home from the courts dozens of times, he didn't notice any of the minute details of the walk home. This time, he arrived back to the building to a surprise. His landlord was bent over the front of a police car, handcuffs around his wrists, and being read his rights.

A few days later, an email was sent out to all of the tenants of the newly renovated, white building. Someone new had bought the building, and they would be raising rent by twenty percent. Alex was in school and had a student job, but he could not afford an apartment at increased, not to mention full, rates. So, he put out a few ads on online forums:

In need of a roommate

Two bedroom one bath

Smoker friendly

He also left his phone number for people to contact him. He only had two weeks to find someone or he would have to move somewhere cheaper. At this point, it didn't even really matter who it was. Alex was a friendly guy, and quite easy to get along with. He didn't make much of a mess and was willing to cooperate with most demands. He had a girlfriend who often spent the night, but that's why they had their own rooms after all.

Two days passed and no message, but on the third day, his phone lit up early in the morning. When he woke up around 7:30 to begin the day, he rolled over and found the message. His heart fluttered for a brief second, maybe, just maybe, he could stay in his luxury apartment. If his relationship with Talia was more serious, he probably would have moved in with her, but they had only been dating a few months. The screen was bright and illuminated his face in the shy lighting of the morning.

Hi! My friend and I are in need of a place near campus and we wouldn't mind sharing a room if you are still looking for a roommate. Please let us know and we can arrange to meet up and get to know each other first!

He read it twice. Two people had not been what he expected, but he had the room, and certainly wouldn't mind having an extra hand to help with housekeeping and such. He quickly responded.

Hey, sounds good to me, I can meet for lunch today if that works for you?

They responded quickly.

Great! How ab noon at Mark's Midtown?

He liked the message and began his morning routine, curious as to who he would be meeting at the coney island. The rest of the morning was filled with a brief workout and cleaning the apartment. He was fit, but not shredded. Mainly, he teetered on the fence of skinny and lean, which at a meager 5' 6" made him quite unintimidating, but his confidence kept him in the game with girls.

Lunch time eventually rolled around and he sat in the corner booth of a mostly empty coney island. Like every coney island to ever exist, a woman with reddish hair in her 50's came by to take his order and he asked for three coffees. He sipped his subpar caffeine filled drink and scrolled mindlessly through social media, awaiting his guests. Each time the door opened, which was not very often, he quickly shut his phone and looked up to the door. Around 12:15, the bell rang to announce a new customer once more, and Alex darted his eyes toward the door. Standing in the doorway were two women, gorgeous and quite obviously aware of it. They wore black leggings to show off their long, slender legs, and they each had a tight shirt on, one a light blue and one black. The blonde had blue eyes that lit up the room and contrasted her golden skin, and the brunette had large brown anime eyes that drew everyone's attention.

The two girls scanned the room and found Alex, alone in a corner booth, sporting three coffees and ogling the both of them. They headed towards him and he noticed how tall both of them were, at least 5'10" each. They slid into the booth and the brunette promptly spoke, "I assume you're Alex, the one looking for roommates?"

His heart pounded and his blood rushed through his body, no way had he gotten this lucky. He stammered out a meek "yes" before she continued speaking.

"Great. I'm Julia, and this is Demi. We can move in today if that works for you, all of our stuff is in the truck." The stunning brunette extended a finger, pointing to a large black Cadillac Escalade in the parking lot. Alex tried to look, but it was hard to tear his eyes away from both large sets of tits in front of him. He nodded and told them to follow him after lunch. They spent the rest of the time getting to know each other. He learned that Demi was quieter and rarely spoke unless spoken to, and Julia was quite commanding. Julia owned a large cosmetics and plastic surgery company and they moved to the area to open a new location. They were very well off in terms of money, which was just fine by Alex. He could not tell if they were a couple or just two friends, he hoped the first so his girlfriend wouldn't be so jealous, but secretly he wished they weren't.

After lunch, they followed him to his apartment and he showed them how to get in. The place had been cleaned up, and he was very glad he had done so now. He helped the girls unload their many bags and boxes, but the girls proved to be much stronger than he, something he was a little embarrassed about. Once everything was unloaded, he went to take a nap.

He was fast asleep, but awoke to a slight knock. His groggy eyes recognized the blonde hair as Demi and shifted his body upright. Demi slipped in and closed the door behind her. She had a curious look on her face, but she didn't say anything. She started climbing onto his bed, which caused the tired Alex to ask, "Can I help you with something?"

She pulled the sheet away to reveal just his striped blue boxers, and seductively shushed him. He was in shock, and didn't move a muscle. She pulled away his boxers, revealing a small, flaccid penis. She dropped her head to it and began to lick as it quickly grew to full size at around four inches. She began bobbing her head up and down as he groaned in ecstasy. She licked as she came up and twirled her tongue around the tip, driving him crazy. He knew he wouldn't last much longer. She kept going, and as he was about to explode, the door opened. Julia stood in the doorway, quickly started filming, and then he gasped Julia's name. Demi stopped and looked up as he shot his load all over himself.

Julia started accusing him, "I thought you had a girlfriend? This place might not work out if we have to live with cheating scum like you!"

Alex, panicking over the video evidence of him cheating on his girlfriend, tried to talk his way out, "I didn't mean for this to happen! Please delete that video, my girlfriend can't know, please-"

"Quiet." Her tone silenced the room. She left and returned real quick. She walked up to Demi and handed her a pair of silver handcuffs. She turned to Alex, sitting up, cum dripping down his stomach, and asked him, "How badly do you not want her to find out?"

Pleadingly, and with a look of authenticity in his eyes, "Anything! I'll do anything!"

Julia smiled and grabbed his hand and handcuffed it to the bedpost as Demi did the same with his other hand. Demi got off the bed and grabbed his phone from the night dresser. Demi swiped it open and laughed when there was no password. She left the room with his phone and his attention turned back to Julia. She stood, with a domineering look of contempt on her face, and she spoke with authority resounding in her voice, "We're gonna make a little home video once Demi gets back, then we will unlock you and discuss future living arrangements." She stood there silently looking at his wilted dick, which was now covered in drying cum. Demi opened the door once more and announced, "All of his contacts and accounts are uploading right now," then she grabbed Julia's phone, the one with the evidence on it.

Julia spoke once more, "She is gonna count to three and then you will say the words, "My name is Alice and I am a cum loving sissy", then you will blow me until I finish on your face. If you refuse, we will send the video we already have to your lovely little girlfriend and then fuck your face anyways." As soon as she finished talking, she pulled down her leggings and panties to reveal a large hanging dick. It was at least an inch and a half thick and about six inches long while soft. He gasped as the sheer size of it, and the realization that he was going to have to suck a dick, even if it was attached to a very sexy girl, he was not into that.

Demi held the phone aloft as Julia got on the bed and lowered her hanging member in front of his face. She said, "3... 2... 1... go," and then she turned the camera to Alex. He stared into the camera and after a few seconds, he weakly said, "My name is Alice and I am a cum loving sissy." He turned to face the dick in front of his face and very begrudgingly wrapped his lips around it. He started to bob up and down like it was a popsicle. He hated the warm feeling of it in his mouth and could feel blood pulse through it as it slowly grew in size. He could only fit half in his mouth but he was sliding it between his lips quickly, trying to get it over with as fast as he could. This only elicited taunts from the girls like "look how cock hungry she is" and "oh she really is a slut" which just made him turn red with embarrassment and anger. After a couple minutes, Julia grabbed his head with both hands and pulled it forcefully onto her dick. He gagged as it filled his throat and he couldn't breathe. She held it there until he felt light headed and then let loose a little bit. He was producing a lot of saliva now and continued to give his first, and hopefully last, blowjob. This kept on for a while until finally she pulled out of his mouth and stroked her now 8 inch dick a few times until it shot rope after rope of pearly white cum onto his face. She covered his eyes, forehead, and cheeks as Demi excitedly remarked "Sissy's first facial!"

Julia used her dick to wipe up all of the cum off of his face and then held it in front of his face before telling him to "clean her off" which he reluctantly did. He hated the salty taste and was revolted at everything he had just done.

Julia was now standing at the side of the bed again, side by side with the other gorgeous girl who Alex now suspected also carried a secret dick. The brunette, looking satisfied, blissfully explained the new situation, "You will address us as Miss Julia or Miss Demi at all times, and your new name is Alice. You will do what we say, wear what we say, and if you disobey us you will be punished. If you disobey us too much, we will share that last video with your girlfriend, your friends, your boss, and even your family before we post it on the internet for all to see. We have an email set up to send the video out every 6 hours unless we stop it, so any attempt to escape or debilitate us will result in the video being sent out. If you play by our rules, no one will know and you will even still have a normal relationship with your girlfriend. Do you understand your new role?"

"Yes."

She slapped him across the face, leaving a red hand print where a mixture of tears, saliva, and cum had been.

"Yes, Miss Julia."