Chapter 2

To all outside appearances, the young woman standing somewhat impatiently next to the mailbox was just like any other woman. She was slightly above average height at about five foot six and had long, curly brown hair, which, much to her distress, tended to be a mess in the morning. Now, however, it fell gracefully to frame her face in soft curls. Her skin was fairer than many of the other Southern California girls but that is not to say she was pale, simply that she was not so tanned.

Like most young women, Jessica was highly critical of her own body. She thought her breasts were to small, her waist to wide, or her butt not round enough. In reality, she had none of these flaws. The many boys that developed whiplash when she walked by were certainly proof to the contrary. Her ass was nicely rounded into a beautiful upside down heart. Though not super skinny, her waist was definitely smaller than her hips giving her a gorgeous hourglass shape. And though she was only at a B cup, her breasts were still growing and already created quite a pretty sight when she wore a tight shirt, which she often did.

Much of Jessica's troubles, however, didn't come from what people saw on the outside. They came from what she hid from everyone's eyes. Unlike most girls, Jessica had a penis. This was because, up until a few months ago, Jessica had been Jason. As Jason, she has been bullied almost everyday for her soft, delicate features. After one bully had videotaped her in a compromising position, he had forced her to have sex with him. At the time, Jessica had been experimenting with dressing as a girl and the bully had taken full advantage of this. In the end, Jessica had decided that she should have been born a girl and started down the path towards womanhood.

It was a warm sunny day, as April tends to be in Southern California. Jessica was barely able to contain her excitement while she waited for the postman to appear. For the last several days she had waited eagerly for his arrival. She had heard that the colleges she applied to, specifically the University of California at Littlestown, were sending out their acceptance letters. She couldn't wait for the chance to leave this town. Though she was under no misconceptions that people were any less judging in college, there would be nobody there that knew her previous life and that was what Jessica desperately wanted to escape.

Jessica had sent in her applications a number of months ago, when she had finished taking her tests. She was pretty confident of her chances of getting accepted but she couldn't help feeling giddy about holding that official letter in her hands.

The mailman came around the far corner of her street and began making his slow way up towards her. She watched him come, wondering not for the first time if he was purposely going slower because he knew she was waiting for him.

He was smiling when he finally drove up to her house. She grinned back, flashing him one of those smiles designed to melt men's hearts. He handed her a stack of envelopes and stood waiting for her. She wondered for a moment why he wasn't leaving until she saw the letter on top of the stack. With jerky, desperate movements she tore the letter from the envelope and scanned over it quickly

"Thank you, thank you, thank you," she said, whooping with joy. She threw her arms around the much taller mailman before stepping back awkwardly. The man didn't seem to mind the hug but he did turn around quickly and return to his vehicle. She heard him chuckling to himself as she raced back into the house.

"Mom, mom, mom!" she shouted as she burst through the front door. Her mom was sitting in the living room, watching TV. Jessica ran up to her and shoved the letter into her lap, not bothering to keep her excitement in check.


"Congratulations, honey," her mom said, smiling up at her and pulling her into a hug.

"Thank you!" said Jessica. "Oh there is so much to plan now!"

"Don't worry about it, honey. Your father and I have already been planning a little. We both took a week of vacation at the end of August to help you move to wherever you were going to be going. Now it looks like they need you to finalize your application and they will send out your room assignments. It says classes start at the beginning of September so we have plenty of time to get this all figure out. Why don't you go tell all your friends alright?"

Jessica nodded and gave her mother another hug before racing off to tell everyone the good news.

Jessica's cellphone rang as she entered her room. It was local number but unfamiliar to her. She answered, figuring it was one of her friends using something other than their cell.

"Ah, may I speak with Jessica please?" a vaguely familiar male voice came through the speaker.

"This is Jessica, who is this?" she responded, trying to figure out who the voice belonged to.

"Um, it's Cliff," he said. Jessica froze. Cliff was the bully that had raped her a few months ago and she had not wanted to ever hear his voice again nor did she think he would ever dare to call her. She waited, quiet, wondering what he wanted and why she wasn't simply hanging up the phone. "Jessica?" he asked as the silence lengthened.

"What?" she responded, her tone not nearly as bitter as she wanted.

"Look I know you must hate me..."

"You got that right."

"And I completely understand. I did something wrong to you and I really shouldn't have. It was a big mistake and I wanted to say ... I wanted to say I'm sorry."

"Are you saying this because you're really sorry or because you have to ask Megan to take your cage off any time you want to cum?" Jessica snapped. One of the things Jessica's friends had done when they helped her get back at him was put him in a chastity belt and videotape him getting fucked by their strapons. Cliff had to ask to help him cum any time he needed to.

Jessica was coming out of her shock and she was angry that he had dared to talk to her.

"No, it's not that, I'm really sorry. Yes Megan and the others have been showing me the ... error of my ways, but I've still come to understand that what I did really hurt you. For whatever it's worth, I'm sorry. I'll ... I'll leave you alone now."

"Wait no, don't hang up," Jessica said. There was a pause on the other end and Jessica waited to see if he had heard her.

"Yes?" Cliff replied, sounding a little happier then before.

"Look Cliff, what you did was a terrible thing. I sincerely hope you remember that for the rest of your life. But I also know that people can change or I wouldn't be like I am today. I guess what I'm trying to say is ... I forgive you. Good bye Cliff," she finished and hung up the phone before he could reply.

Jessica sat on her bed for a time thinking. She was still mad at Cliff but as she thought more on it she realized that Cliff had been paying his penalty for a number of months now. Jessica knew Cliff was calling on Megan or her friends a few times a week. She often heard them talking about what they did to him but she had never asked to participate. Maybe it was time she changed that, maybe it was time she freed him.

She flipped open her cellphone and called up Megan.

They were using Becca's house this time because her parents were going to be out that night. When they went on dates, which was pretty often, they liked to go to dinner and a movie and typically stayed out very late into the night.

The girls all arrived at around five, just after Becca's parents had left the house. Megan brought Jessica with her. Jessica had spent a good two hours making sure she looked perfect for tonight. She had straightened her hair and wore it long and flowing. Megan had helped her with the make up and she looked gorgeous with her pouty lips and radiant eyes. She was sure to make an impression on Cliff.

They girls prepared as they usually did. They lit a joint and passed it around while they made sure they had the various restraints and toys that they would be using. They all dressed in black latex and wore their hair up in ponytails. Jessica didn't dress like them but she was only going to watch, for a while.

Cliff showed up at six o'clock. He knocked on the door and waited sheepishly to be let in. The three girls stood at the entrance of the house, watching him silently. They each had some sort of domination toy in their hand. He knew exactly what he was to do. Upon entering he took off all his clothes, piled them next to the door, and knelt before his mistresses.


"May I please have the pleasure of serving you, my mistresses?" he asked submissively. Megan, the leader as always, was the first to approach. She strode confidently towards him, her heels striking the tile loudly. She flicked her riding crop against her leather boots in time with her steps.

"Stand up you pitiful excuse for a man," she said. He immediately obeyed, rising to his face but keeping his eyes downcast. "Today we have a new person in attendance, Jessica has asked to be a participant today."

Cliff's eyes snapped up at the comment. He searched for Jessica, finding her standing in the back behind the two other girls. They locked eyes for a moment, Cliff trying to find any reason in her expression as to why she had come today. Jessica looked back, her eyes only showing her strength in her newly discovered sexuality.

"Eyes down in our presents, slave!" Megan screamed at him. She brought the crop down on his backside, leaving an angry red patch on his smooth, muscled flank. Cliff cried out, dropping his head immediately to look at the floor. Jessica could see his muscles clenching up, waiting for another lash to fall.

"I was going to tell you to be on your best behavior but it looks like you already fucked that up. Follow us to the playroom, slave, and make sure you do a better job," commanded Megan as she prodded him forward with her crop. Cliff followed Becca and Casey, his hand held meekly over his caged manhood.

The playroom was really Becca's room. They had moved her bed out of the corner and into the center of the room where they would all be free to move about whoever was in the middle. Typically this was Cliff but there had been others. There was a black blanket thrown over it and scarves dangled each of the four bedposts.

"Stand by the side of the bed and put your hands on it, stick your ass out," Megan commanded.

Cliff obeyed, bending over to expose himself to their punishment. Megan was the first to approach. She flicked him with the crop. The suddenness of it made Cliff jerk and cry out. Megan slowly paced behind him. Her boots letting Cliff know she was still there. Occasionally she would bring the crop down on his ass.

"Blindfold him, we don't want him to see Becca's pussy while he licks her," Megan ordered and Becca jumped up to wrap a blindfold over his eyes. She nodded again at Becca who climbed up onto the bed. She had pulled her pants off and she positioned herself before Cliff, her pussy already glistening.

"Lick Becca while you receive your punishment. We won't stop until she cums."

Casey stepped up behind Cliff and lay her flogger on his back, dragging it down his ass so that he felt the many leather threads. She slapped it gently against his balls. Not hard enough to hurt but enough to scare him with the threat. She began flicking it around in a circle, striking one side of his ass and then the other until he was bright red. She slowly worked her way up from light brushes to brutal, full strength licks. As Cliff's legs began to give out from the pain, Becca cried out in orgasm and clamped her thighs around his head. He sagged to the ground, not having the energy to lift his face from her pussy.

Megan and Casey lifted him up and helped him onto the bed on his back. They tied his arms and legs to the bedposts over his head, pushing his legs up over his body and using a pillow to prop up his ass. Becca slide off the edge and knelt by his side as Casey strapped a ball gag over his mouth. Megan took the key to his chastity belt from around her neck. She let it fall to his chest and dragged it down to his cock.

"Are you read to be free, slave?" whispered Becca in Cliff's ear.

"How long has it been again? Two, three weeks without release?" asked Casey in his other ear. Cliff groaned, his cock straining to be free of the plastic device.

Megan slid the key into the little lock and gently pulled the assembly from around Cliff's already stiffening penis.

"Today is gonna be a little different," said Megan. She started to tease Cliff by gently stroking him, her fingers barely touching his cock. "Today you're gonna get fucked but not by us. Jessica has asked to help out today and we think the perfect way to send her off is with a nice hard fucking. Well, fucking you nice and hard."

Cliff moaned through his gag and tried to pull out of his bonds but they held fast. His penis, however, stiffened and glistened with precum.

"Don't try to tell us you don't want this," Casey whispered. "We can see how hard your cock is. I bet your asshole is quivering with desire too." She licked along his ear and gently nibbled on his earlobe.

"Jessica, why don't you come in here while we get him ready."

Jessica walked in and began to take off her clothes. Her little cock was already rock hard in anticipation of the tight, hot hole it would be in momentarily. Megan lubed his ass up well and slowly slid her fingers in to loosen him up. His ass could take them easily after a few months of practice. He moaned into his gag, rolling his hips to try to get Megan's fingers in deeper.

Jessica climbed up on the bed and took Megan's place. She slid her cock up and down Cliff's ass, lubing it and using it to tease Cliff's hole. His body tensed up and he tried to lift his ass away but there was nowhere for him to go. He whipped his head back and forth, moaning urgently into the gag but it was no use. His hardon bounced around, drooling precum from the tip.

When he grew to tired from thrashing about he relaxed in his bonds and sank down.

Right onto Jessica's cock.

His tight asshole slid easily over the head of her dick. Jessica let loose a girlish moan as she sank fully into him. Cliff's ass tightened as he was suddenly filled up but he was through with resisting now. He lay, resigned, and let Jessica have her way with him.

His cock, however, was anything but resigned and certainly didn't lie.

"Oh yeah, we knew you would like that. A nice warm cock in your asshole. I bet you can't wait for her to start fucking you!" Becca murmured to him and Jessica began to do just that.

"Oh he's so god damn tight!" she groaned. She slid her hips forward, fucking his ass slowly as she enjoyed the very first time something other than her own hand was getting her off. She giggled at the thought that she was finally loosing her male virginity ... as a girl.

She rested one hand on his thigh and grabbed his cock with the other, using as leverage to pull herself into him harder and jerking him off at the same time. His cock twitched appreciatively in her hand. Jessica could tell he was near the point of release but she kept her pace slow enough that he wouldn't go over the edge.

"You like that Cliff? Do you like getting fucked by a real cock? Your cock sure likes it. It's all hard and throbbing. I can feel the cum boiling in your balls. Humm? Don't you need to cum sooo bad?" Jessica asked to him. His groans had reached a higher pitch and he was rotating his hips, thrusting back at her invading cock.

"Oh it looks like you sure do!" she exclaimed. She released his cock and planted her hands under his secure arms. She leaned down over him so her hair spilled over them both and his cock was trapped against her smooth belly. She pulled off his blindfold so he could see her as she fucked him and she began thrusting into him hard and fast. She could plainly see the mixed desire in his eyes.

"Cliff," Jessica whispered to him. "Consider this a going away present. If you cum right now I'll tell the girls to release you permanently from your chastity. You will never have to come to them again. What do you say big boy? Will you cum? Will you cum for me with my cock buried in your ass?"

Cliff closed his eyes and his chest heaved as he tried to fuck himself harder on her cock. Her cock was small but it was long enough to reach his prostate. Jessica leaned forward and found his mouth with her lips, kissing him deeply and letting her tongue slid into his mouth.

"Oh, Oh I'm gonna cum in your asshole! Cum for me. Cum with me!" she moaned as her cock began to release a hot load of jiss into Cliff's quivering ass. He screeched behind the gag and his cock lurched, spilling cum all over his chest. Jessica reached down between them, grabbing his cock and stroking him through the best orgasm of his life.

He seemed to cum forever and when the stream of jiss finally began to slow, all the muscles in his abs still spasmed.

Megan took Jessica's place as she got up to clean herself off. She was holding the chastity cage but Jessica stopped her.

"No, I think he has learned his lesson. No more chastity cage for him." Megan looked at her questioningly.

"You sure Jessica?" she asked.

"Yes. He called me a few days ago and apologized. I think he knows what he did was wrong. He also came just now so I'm sure he also realizes that he can find pleasure in many different ways."

"Very well," Megan said. She got off the bed leaving Cliff's cock uncaged. The girls released Cliff and took the ball gag out of his mouth. Jessica took a moment to clean the cum from his chest.

"Here," Megan said, holding a bag out to Cliff. "This is your chastity cage. Consider it our gift for you to remember us by. Now get out of here."

Cliff nodded, murmuring 'thank you's as he stumbled the room. The girls all sat around quietly after he had left.

"Well," Becca said, finally breaking the silence. "If he doesn't come back to us there is a freshman cheerleader I know of that we could probably turn into our slut."

Jessica could barely keep her excitement in check during the long road trip to Littlestown. Her parents had each taken a week of vacation off from work so they could drive her, leaving Megan alone at home to fend for herself. Megan had certainly been excited about that, even though her parents had specified 'no parties' while they were gone. Jessica knew Megan better than that and figured Megan would have a few girls and boys over the very night they were gone.

The drive to Littlestown was longer than Jessica would have liked but the miles flew by and soon they were in Littlestown. Once in Littlestown, Jessica's parents soon had her checked into her new dorm. It was in the LGBT dorm facility, a separate building just for students who identified as Lesbian, Gay, Bisexual, or Transgender.

The dorm she was assigned was empty when she entered. Apparently, her roommate hadn't arrived yet. Seeing as how classes didn't start for a week, Jessica wasn't surprised. 


Her parents helped her move everything into the room. She got to choose the bed she wanted because she was there first. She picked the one around the corner from the door. It wasn't immediately visible when the door was opened. They soon had her desk and bed set up and clothes hung in the closet and folded in the dresser. She had lots of girl clothes now. Her mom had jumped at the chance to go shopping with her a daughter again. They had gone a little crazy but Jessica was excited to try everything on.


After a few trips to the local supermarket, a tour of the campus and a fancy goodbye dinner, Jessica's parents finally said their farewells and left for home. It was early in the morning when they left and the dorms were still pretty empty. Jessica dug out her new makeup bag and went down the hall to the bathroom.

First, she took a shower and made sure she was extra clean. She teased her little cock, enjoying the feeling of her soapy hand sliding up and down the shaft. She stopped short of cumming though because she liked feeling horny all day. Next she washed her hair and used some blonde dye to add some highlights to her thick brown locks. She stood before the mirror in the bathroom, wrapped in a towel up to her armpits, her little penis tenting the front, and carefully applied a thin layer of makeup.


A coat of primer went on first, to smooth out her skin, followed by foundation to give her a nice, even complexion. She followed that with some eyeshadow and eyeliner to show off her bright blue eyes. Next, she applied mascara and finished up with a coat of pink lip-gloss and a little blush on her cheeks. With a smirk on her lips and a sway in her steps she walked back to her dormroom wrapped only in her towel. On the way she drew a few astonished looks from boys and girls that happened to have their doors open as she walked by. She noticed a few cute ones that she wouldn't mind discovering what they had hidden under their clothes.

Once back in her dormroom, she donned a sexy black baby doll t-shirt and a short plaid pink miniskirt that went down to mid thigh. Under the skirt she had on a pair of pink panties with the words, 'Eat Me', on the front over her little boy cock. She brushed out her hair, tied it back in a high pony tail and went out to meet her new classmates.



The dorms in her area were set up in a square formation with the grassy lawn between them. There were trees spaced out around the grassy area and walkways criss crossed it from corner to corner. There were more dorms in other areas around the campus since roughly 30,000 students attended the school.

Jessica left her dorm and walked across the lawn to one of the boy's dorms. There were some boys playing Frisbee on the lawn and one of them whistled as she walked by. She grinned at him and threw a sway into her hips for his benefit. At the boys dorm she held open the dorm for some guys carrying in a sofa and snuck in after them.

Jessica wandered through the halls, stopping at open doors and chatting and flirting with the boys she found. They all had a good time talking with her, many were bored or looking for an excuse to take a break from moving in to chat. She gave her phone number out more than a few times.

One room she peaked her head into was empty but clearly someone had already been there from the decorations on the walls. There were posters coving half of the room. Jessica recognized most of the bands, they were ones she loved herself.

"Ah ... Hello. Can I help you?" said a voice from behind her. "Are you a relative of Jason's or something?" Jessica jumped, shocked that anyone had recognized her already, and spun around to see who it was.

"Ah, no, I'm Jason. Do I know you? I don't recognize you from school," she asked after she saw the dark, shaggy haired stranger. He had a small scar running down his cheek. A puzzled expression pinched his brow. Jessica found she liked the scar actually. It gave his face character; a dangerous look and she found herself wanting to know the story behind it.

"Ah, no, I don't think I've seen you before. What do you mean you're Jason, you're my roommate?" Adam said in surprise, obviously eager at the prospect of having a female roommate and momentarily forgetting that this was an all mens dorm. The only dorm where that type of pairing was possible was in the LGBT dorm but then there was a good chance he probably wouldn't get to do all the fun stuff he was imagining if lived there with a girl. 


"Oh, uh, no, I mean yes ... I don't know," Jessica shrugged. The man laughed at her.

"Woah, woah, woah, slow down girl. Are you saying yes that you're my roommate?" he asked. Jessica shook her head. He scratched his head for a moment.

"So your name is Jason then?" he asked. Jessica shrugged, blinking at him innocently. She was afraid to speak, afraid she'd make herself sound stupid in front of this man she found very attractive.

"Sorry, I don't speak shrug. You're gonna have to explain that one to me."


"Well, it was Jason, now my name is Jessica," she said, waiting for the man to figure out what she wasn't saying. He looked at her for a second.

"Why would your parents name you Jason. That seems kind of harsh."

"Well ... at the time it wasn't so strange."

He paused, thinking. "So ... are you a dude then?"

"Sorta?" she said blushing and her voice wavered. She really didn't want to ruin it with this boy already but she was afraid she had. "I mean yeah, I'm a transsexual. I wanted to be a girl all my life and I switched about a few months ago. I still have boy parts but I'm taking hormones and stuff," she explained. "I can show you if you don't believe me?" She immediately regretted saying it and blushed bright red, hiding her face in her hands.

"Ah, no that's alright, I believe you."

"Wait! How did you know my boy name if you don't know me then! And you haven't even told me your name yet."

He chuckled, obviously enjoying watching her make a fool of herself.

"My name is Adam and Jason is the name of my roommate. He hasn't shown up yet. When I saw you standing there I thought you were a sister or a friend or something," he laughed. Jessica giggled at the coincidence. She looked down at the ground and shuffled her feet. "What were you doing peaking in my room anyways?"

"Oh that, I'm just wandering around meeting all the new people. There was no one in your room but I saw your posters and I like the same music you do apparently. Those are your posters right?" Adam nodded, stepping into his room to look around.

"Yeah, King Diamond and The Agonist are my two favorite bands." He paused, thinking for a second. "Um ... You wanna help me bring in the last of my stuff?"

"Sure thing, honey," Jessica grinned, happy that he wanted to hang out with her still, and followed Adam out the door. They made their way through the throng of boys rough housing in the halls out to the parking lot. Jessica followed behind Adam, using the time to study his gorgeous backside the whole way. 


Adam led her over to his car. It was a last year's model Honda Civic in solid black. He popped the trunk open and began pulling out the rest of his stuff. In his haste accidentally he dropped a box marked 'school supplies'. Jessica quickly bent over to pick it up.


"Let me get that for you!" she said, bending down to grab the box. Her miniskirt slid over her ass and exposed her pink panties to Adam's stare. "Oops, I guess I should bend at the knees next time. Oh well," she flipped her hair over her shoulder and stepped back to wait for Adam. "You just gonna watch me all day sweetie, or do you wanna take some things inside?" she teased him when she caught him watching her. 


Adam shook the cobwebs from his mind and quickly gathered the rest of the bags. He grinned to himself, amused by Jessica's teasing attitude. He closed the trunk and moved off towards the dorm, deftly avoiding Jessica's hip check. He looked over his shoulder and grinned at her, laughing as she tried to recover her balance. He admired her long smooth legs and remembered the glimpse he had seen of her ass. Even if she had a dick, and he wasn't entirely sure she did, she was one hot babe. He could feel his cock start to harden and he hoped they could make it back to the dorm before he was at full mast. 


When they got back to the room, Jessica set Adam's things down, leaned against the other bed, and watched him. She immediately noticed Adam's hard cock straining to get out of his shorts. 


"My, you look like you are having some trouble, did I cause that?" Jessica murmured sensuously. "I could help you take care of that, if you want?" She caressed her lips with her fingers, slowly sliding one into her mouth and sucking on it. She sauntered over to Adam, her hips swaying from side to side. She sank to her knees and fished Adam's cock from his pants while Adam tried to find something to say. "Shhhh, don't say anything baby, just enjoy this." 


She wrapped her lips around the head of his cock, sucking hard. She used her tongue to coat the head in saliva and tease Adam's peehole, trying to lick all the precum out of it. She brought her hands up to Adam's balls and softly massaged them, rolling them through her fingers, feeling the soft flesh coving the tender globes. She ran her tongue down the underside of his dick, stroking the head with one hand. She slipped her lips around one of his balls and gently lapped it with her tongue.

Adam let out a groan and slid his hands into Jessica's hair. He guided her back to his dick and she took it into her mouth, letting it sink down into her throat. Her lips slid to the base and she could feel the head of his dick pressing against the back of her throat. She let out a groan, the vibrations sending pleasure through Adam's whole body and looked up at Adam with her vibrant blue eyes.


Jessica's cock was rock hard in her panties but she kept her hands on Adam. She could feel a wet spot spreading around the head and knew she was leaking precum horny teenager. She moaned, slowly humping her crotch against the air, imagining a nice hard dick in her ass while she made love to the one in her mouth. 


"Oh fuck, I'm gonna cum. Eat my cum you sexy bitch," Adam groaned out. Jessica moaned around his cock and pumped her lips faster up and down on the shaft. She gripped his muscled thigh with one hand, preparing for the torrent that was about to flood her mouth. Adam grunted out something unintelligible as he started to cum. Jessica opened her mouth and jacked Adam's cock, letting the cum spray fill her mouth. She swallowed quickly and moved his cock to send a few strands across her cheeks and forehead. As Adam's orgasm subsided, Jessica locked her lips around the head once again and sucked the remaining cum from it. She made sure Adam's cock was nice and clean before sitting back on her heels.