Alice's New Life Pt. 01

Alex was taking notes at his desk while the Zoom class played in the background. Online schooling was hard to stay focused and motivated and the only time he could was during class. There was a knock at the door to his single apartment, just loud enough to get his attention. He sauntered over wondering who it was. Usually, his friends just barged into his apartment without announcing themselves. He would often wake up to his friends already in his living room. He looked through the peephole and saw a cute blonde girl in a short pink skirt and white tank top. He opened the door without hesitation.

"Hey, hope I'm not bothering you but I'm your new neighbor and I was wondering if you wanted to go to my cabin up north with my friends and I next week. I don't know many people and it'd be fun to get to know the person next door to us! There's wifi there so you can still do your classes and everything. What do you say?"

Alex couldn't say no, but he didn't want to sound desperate either. "Uhh, ya that should be fine, I think I can go." He couldn't take his eyes off of the beautiful girl in front of him while they exchanged phone numbers. She said her name was Tessa and Alex stared as her ass swayed while she walked two doors down to her apartment.

They texted on and off for the next two days until Friday came and they were set to leave campus at noon when their classes were done. He had packed for six days, with a couple swimsuits and condoms in his bag in case he got lucky.

He walked a couple doors down to their apartment and knocked. The door opened to two tall and busty brunette girls in matching black leggings and black tank tops.

They giggled in unison and the one on the left said, "You must be Alex, I'm Jenna and this is Sasha." Alex was on the shorter side at 5'2", but both of these girls were easily 6 feet tall and towered over him. It was quite an intimidating sight, but their smiles were so welcoming. They ushered him in and he saw Tessa bending over the couch. Her toned legs and her bubble butt on display as her tiny skirt covered nothing and the red thong lay nestled between her cheeks. She stood back up and turned around, Alex's cheeks turned red hoping she hadn't noticed he was staring at her exposed ass. She smiled and her blue eyes and large red lips melted Alex's heart. He was obsessed.

"Hey Alex! I'm so glad you could join us, we're going to have so much fun this weekend!" She grabbed two large suitcases and headed down the stairs to a black Cadillac Escalade with several suitcases already packed. How many things could three girls bring for a week trip?

He slept for most of the car ride, dreaming of Tessa. Her blonde hair, perfect tits, and an ass to die for. This week would give him many chances to get her alone.

They arrived at a mansion at around 8 at night. It was a massive estate with a circle drive, complete with a fountain, leading up to a marble staircase. The "cabin" was actually a palace. It looked like royalty lived here. Turns out Jenna's family comes from money. Alex was excited to see what kind of toys they had here, hopefully he could drive a jetski.

Sasha went to the kitchen, which could fit about thirty people, and she grabbed two bottles of champagne. When she returned, a cheer went up from the four of them and two bottles of champagne were popped open. Drinks went down one after another until they were all trashed and sitting on the rug in the middle of the tv room. Jenna excitedly had the idea to play Mariokart.

The game was set up and everyone had their controllers and a drink. Jenna stopped everyone before the game started, "Alex wanna make a bet on the game?"

He couldn't back down from a challenge, especially not while he was so intoxicated. "What kind of bet?"

She smiled knowingly back at him, "Whoever wins gets to choose what the other wears or doesn't wear for the rest of the night. You in?"

They shook hands as he confidently said, "Deal!"

Three minutes later and Alex had taken last place in the game, Toad had let him down in a big way, he just didn't realize how big of a mistake it was. The girls all laughed as Jenna asked, "Who wants to help me doll Alex up?" They ushered Alex upstairs to the master bedroom, where Tessa and Sasha began looking through all of the clothes. Jenna grabbed Alex by the arm and took him to the bathroom.

He asked, "What are we doing?" to which she simply responded, "Shaving your body hair, silly."

He was pretty drunk so he just went along with it, not fully realizing what was happening. Jenna stripped him down and took a razor and some shaving cream and carefully rid his body of any hairs. He was completely smooth from the neck down, including his armpits, his pubic hair, and the hair in between his ass cheeks.

"There you go, much better and so smooth." She brought him into the bedroom where Sasha and Tessa had arranged some clothes. Tessa seemed very excited, "Ok we have two options for you to choose from. The first is this set." She held a black bra with a lacy black thong, matched with a short white latex skirt and tight pink crop top. She grabbed the second set, a pink thong and bra with a short, tight black dress and black stockings. "Or you can go with this one, which do you prefer?"

Alex looked at the two and figured he would be more covered up with the second option. "I'll take the dress, I guess." The girls laughed and commented on how cute he was going to look.

They handed him the thong, then helped him roll the stockings up his leg. It didn't go unnoticed that he was rock hard the whole time, and the girls kept "accidentally" brushing their hands over it. Jenna clipped the bra on him, then stopped, "Wait, I have just the thing to complete this." She ran out of the room and came back a couple minutes later with two breast forms and an adhesive. She immediately put the cold gel against his chest and held the forms to his skin for a couple minutes. When she let go, Alex had two very realistic breasts. She put the bra back on and then grabbed the dress. It was much shorter than Alex had initially thought. He squirmed to get into it, then when Sasha zipped it up in the back, it hardly covered his ass, and his new tits were prominently on display.

Tessa grabbed his ass and laughed, "Oh my you're so cute, I can't wait to have a piece of you." She handed him a pair of black 5 inch stilettos, "These will go well with that dress, make your legs and ass look better too." She helped him into them and he could barely stand in the heels with the alcohol in him. He teetered over to the bathroom where he saw himself in the mirror. From the head down, he was a curvy and quite sexy girl wearing an albeit slutty outfit. When he turned, he could see the bottom of his ass and the pink thong nestled in between his cheeks. The girls sat him down and began their work on his face. They put a blonde wig on with blue contacts, then started his makeup. They did a full makeup job with long lashes, large red lips, and even contour.

After thirty minutes, they had completely transformed Alex into a girl. The makeup and wig made him unrecognizable as he had been before. They headed back downstairs after a very impressive transformation. Tessa teased, "We did such a good job, I don't think we can even call you Alex anymore. How about, Alice?" The girls all laughed.

"Please don't call me Alice, my name is Alex." He whined, "I'm just going along with the bet."

They sat back down in their seats with their drinks. Alex suddenly became aware that he needed to cross his legs while dressed like this. Tessa sat next to Alex on the couch, close enough that their legs were touching. She put a hand on his thigh and began to sensually rub it, "Hey Alice, how about we make a bet on this game, huh?"

Alex smiled, "I think I'm good, I've already lost enough of my dignity tonight."

Tessa grabbed Alex's swelling member and gave it a light squeeze, "Oh come on, you look so sexy, plus you're really going to love the next bet."

They stared each other in the eyes, Tessa making a puppy dog face and pleading.

"Ok, what is the bet, then I'll decide." Tessa squeezed his erection once more. "Yay! Ok, this one's for everyone. Whoever loses, has to go down on everyone else." The girls cooed and Alex looked around with a smile. He felt like that was a win-win no matter what happened. He grinned, "Ok, I'm in." He was a junior in college and still a virgin, mostly due to his height and his scrawny body. He had never been a lady killer, and so he was very excited for this, even if he was dressed like a girl while it happened.

They started the race and Alex quickly fell behind again. He got a bullet bill, which pushed him to second place as he neared the final lap. He got so excited thinking about any one of the girls giving him head. He had never actually had a blowjob before, and he hadn't seen a vagina before, so it was new and exciting territory either way. He was rounding the last few turns and Sasha and Tessa were inches behind him. He was about to win when Tessa grabbed Alex and pulled him into a kiss. He let go of his controller and gave into the kiss. Her soft lips against his turned him on even more than he already was. He heard laughing from the girls and Tessa pulled out of the kiss. Alex was confused why they were laughing until he saw the screen. Toad had stopped driving when Tessa kissed him, he had lost.

All the girls were laughing, Tessa kissed him one more time then said, "A bet is a bet, time to pay up, on your knees." Alex got off the couch and on his knees in front of Tessa who was smiling ear to ear. "Oh, not me first, I'm flattered, but Jenna gets first dibs." Alex turned and saw Jenna with her hands in her leggings. He got up and walked over and got down on his knees, half excited for what he had to do. Until Jenna pulled down her leggings. Then Alex saw the bulge in her panties. He was frozen as she pulled out a seven inch dick, longer and thicker than his. He stuttered, "Uhh uh I'm not gay, I thought you were-"

"Quiet!", Tessa was standing behind Alex now with one hand on the back of his head, "Be a good girl now or face the consequences of breaking a fair bet." She pushed his head forward until he was staring at the dick in his face. Jenna pushed it against his closed mouth and pinched his nose. After a few seconds, he had to open his mouth to breathe and Tessa shoved his head down onto Jenna's throbbing member. She continued to push his head up and down onto Jenna for a few minutes, then she held him all the way down on her dick as he choked, his throat massaging her pulsating member. Jenna moaned, "I'm about to cum!" and Tessa shoved Alex's head roughly all the way down her dick as she shot a large load directly into his stomach. When Jenna sighed, Tessa pulled his head up, gasping for air.

She turned him to look at her, "If you're gonna be stubborn, we'll make it rough. Be a good girl and we'll be gentle, your choice." Sasha had replaced Jenna, stroking an eight inch dick, this one much thicker than Jenna's. He knew he had no choice but to suck it or he would be facefucked again. This time he pursed his lips and kissed the tip in front of him before wrapping his painted lips around the girth and bobbing his head up and down it. He used his tongue to swirl around the tip and shaft as he tried to get the blowjob over with as quickly as possible. Tessa stood behind him making little remarks, "Look at her, she's a natural," and "Those blowjob lips are so sexy." He hated hearing it, but he kept on going. He could feel Sasha getting close to finishing. Sasha yelled, "Swallow all of it slut!" as she unloaded her creamy cum into Alex's mouth. He gulped it down, struggling to not spill it. Eventually, she stopped and pulled out of his mouth. She laughed, "If you thought that was a big load, wait til you see what Tessa can do.

Alex turned to Tessa, who was still standing, and wiped a stream of cum that leaked down his chin. She pulled her small skirt up and pulled out a six inch dick. Alex sighed with relief, but Tessa just laughed, "Don't worry Alice, I'm quite the grower and I know how much you like big cocks. You won't be disappointed."

She started stroking it with one hand and motioning for Alex to turn and face her fully. He did as she asked and noticed her dick was already growing to nine inches. Tessa lined it up with his face and he began to bob up and down on it as he had seen in many porn videos before. Tessa stopped him and looked down, "Use your tongue and look at me while you do it." Alex licked up and down the shaft as he stared into her eyes. She smiled as he worshipped her now twelve inch cock, as thick as Sasha's. She trained him in the art of sucking dick, telling him to lick his balls, play with the tip, and training his deepthroating abilities. She got about eight inches into his throat as he cried and choked on it. Finally, with force, she shoved all twelve inches in, cutting off all his air bulging out his throat. She reached down and grabbed her dick through his throat as she laughed. He almost blacked out but she finally pulled out. He gasped for air as she put the tip back in and told her new toy to finish the job. He started back up and after another ten minutes, he started to feel her tense up and braced himself for what was coming. She held his head in place as she shot stream after stream of hot cum into his mouth. His mouth was overflowing as he tried to swallow it all, and she pulled out to shoot the last several shots all over his face. The girl he had been hoping to score had just covered his face in her cum after abusing his throat. She pushed his head back and laughed, "Such a good little slut already," She took a photo with her phone and said, "Smile! Alice's first facial!"

Alex was out of breath and tried to protest, "Please don't take a photo," but she didn't care. They had a drink more each and that was the last thing Alex remembered of the night.