“Oh my god it came!” He bounced up and down in front of the open packages, the phone pressed to his ear.
“Willy it came!” He couldn’t hold back his excitement.
Willa chuckled to herself on the other end of the line, “that is how the mail works, Jer.”
Jeremy laughed and could barely hold himself together, “I know, I know. I’m just excited. I wasn’t sure when I ordered it but now I’m excited. The clothes came yesterday and now this. Oh my god I can’t wait to try it out. Willy, you have to watch.”
“Yeah, I’m going to unbox tonight on cam. Highest tip gets a private viewing of first use. I’ll even let them pick out what outfit I wear. It’s going to be so much fun!”
Willa laughed on the line, “oh absolutely. I’ll watch. I wouldn’t miss it. You’ve taken to camming so well. I’m proud of how popular you’ve gotten. Not as good as me but-,” she laughed again.
There was no response to that from Jeremy though. His eyes were admiring his new toy; the thick, brown dildo encased in the plastic packaging. It was long and he couldn’t help but lick his lips at the sight of it. If he didn’t have a plan to wage a bidding war tonight on cam he would have opened it right then and there and give Willa a show for herself.
“So, you’re dressing up then Jer?”
He nodded, unconsciously, forgetting she was on the phone. He dashed over to the closet and pulled out a bunch of outfits already sorted on hangers, tossing them on the bed.
“Uh huh. I’ve already got a few outfits picked out,” he snapped a pic and sent it to her, “I’ll let the highest tipper decide what I wear and how quickly it comes off. I’m hoping it goes well.”
“So,” she let the word run off of her lips for a few seconds as if there was a question lingering, “are you going to finally transition then?”
Jeremy stopped and stared off into space, thinking of the question. Willa caught his hesitation and continued on her thought.
“Because it would be a great time if you did. You know you’re more likely to get the bidding up if you finally just do it. You can wear a wig for now and then if you, I don’t know, look into the hormones. You could really turn this into something.”
Jeremy still didn’t respond. He was nervous talking about it, even if Willa made him more calm than anyone.
She was the first one who introduced him to this side of him. He had never really thought about camming or even dressing in women’s clothes, but when he saw her on twitter and started viewing her on her cam site he got really into it. There was a deep eroticism that stirred in him whenever he would watch other people tip her.
One evening, when he was doing his usual voyeuristic hobby and watching her she offered a private show for the highest tipper. She encouraged the lurkers to come out and throw their hat in the ring. She said they wouldn’t regret it. Then she stood up so her waist was in line with the camera. She pulled her panties down to her knees and flipped her plaid skirt up and started stroking her cock. Jeremy stared wide-eyed at it. His erection was bursting out of his pants. That was all it took.
He tipped for the first time, and he tipped a lot. He won the private show and Willa thought he was adorably nervous. She talked to him for a little while before engaging in her erotic activities. She was kind and sweet. She told him he was adorable with how shy he was being. She took control of the conversation that led to them both stroking their cocks and cumming intensely at nearly the same time. She kissed the camera and told him goodnight. Jeremy has logged on nearly every night since then.
“Wasn’t this what you wanted anyway? What was the point of buying the clothing, the toys and setting yourself up online anyway? You even picked out a name, remember?”
Willa tried to be coercing but not forceful. She wanted to bring him along slowly and not seem like she was pushing it too hard. She saw potential in him and wanted to see how far it would go. He loved it too. A man doesn’t spend every evening jerking off to trans girl porn if he isn’t into it. Willa was just helping him get past the stigma of societal thinking.
“What was the name again, Jer? Come on, let me call you it.”
He stammered it out, “Je-Jessica.”
“Yessssss, Jessica,” he could hear her smile on the other end of the line.
“I always loved calling you Jessssssssica. Drawing out the ‘s’ sound is so sexy. And think, if you’re ever feeling really dirty you can get the guys to call you Jessicum.”
Willa giggled and Jeremy couldn’t help but laugh a little too.
“Stop,” he said smiling.
“You don’t want me to stop, do you?”
He was silent.
“Well, Jessica? Jess? Do you?”
He shook his head.
“I can’t hear you,” she responded after a few seconds.
“No, I don’t.”
“There you go, girrrl. I know what you like. You can’t hide it from me. You’re a bad bitch just waiting to come out.”
He blushed on his end of the phone. She did know how to pull it out of him. Willa seemed to know exactly what he wanted and helped him in thinking it was normal. His dirty little secret that he hid from his friends turned into something he spoke openly with her about.
At first he would buy time from her in the evenings and they would talk until she said she was horny and needed to jerk off. He would always join her and it would become almost a nightly ritual that they would cum together. As time went on he would talk to her and they wouldn’t even touch their erections. He would just ramble on about how he wished he was as attractive as she was. How gorgeous she looks in all of her clothes and make-up and how he wished he could be like her. He made himself very vulnerable to her and she always made him feel good about himself by the end of it.
“You could look just like me if you wanted, you know,” Willa would always tell him.
“All you have to do is try. Change what clothes you buy. Change your work out habits. Watch make-up tutorials online. It’s not really that hard, if its something you want to do.”
Jeremy did want to do it. He even picked out a name, Jessica, that he’d like to go by in his fantasy world where he was a girl. Willa told him that was perfect. She said her given name was William and it made it so much easier to answer to something that was feminine but sounded like the name she grew up hearing.
“Now,” she went further, “if you ever want to feel good about yourself what you really need to do is get on cam and let other men jerk off to you. Even when you’re feeling gross you’ll have plenty of horny guys wanting to beat their meat to your naked body if you play along with them.”
Willa would press this button every once in a while when they had their private conversations. She would tease Jeremy and tell him he needed to get on cam and, “be a dirty little cum whore.”
She would also use her time on cam to try and get other men to tell Jeremy it was a good idea.
“So, I need all of your help. I’ve got a good friend on here that’s thinking of being a total whore but he’s too shy. I need you all to tell him that you would totally jerk off to his cute little dick if he were to dress up and get on here. Come on, I’ve been telling him for weeks now and he won’t listen to me.”
The screen filled with positive messages. Some simple and encouraging while others were lewd and lascivious. They were all eager to see Willa’s friend get on cam and preform for them though.
Within a couple of weeks of Willa’s online efforts she had Jeremy online and shyly conversing with strange men asking to see his dick, to see him cum and various other sexual acts. At first it was sporadic, but the more he went on the more comfortable he felt.
The messages made him feel sexy and he enjoyed it. He began ordering women’s underwear and logging on wearing just a bra and panties. They didn’t last long in place though, as he would be asked to pull the bra straps off his shoulders and expose his nipples. Sit back on the bed and jerk off with his panties pulled to the side. He loved the requests too. It made him feel like he was incredibly attractive that they all wanted to see him pleasure himself.
The tips continued to trickle in as well. He wasn’t making a ton of money doing it but it all added up.
Will joked, “you know since I got you into this you should be tipping me.”
Jeremy had a real connection to her and genuinely responded, “if you want them, they’re yours!”
“No, I was just kidding,” she would tell him.
“I don’t mind. I don’t need the money or anything. I’m only doing this because you said it would be fun and build my confidence. You were right. It’s yours. I’ll send you anything I get. I owe it to you.”
“Oh my god, you’re going to make me cry, Jer. You’re too nice!”
“What are friends for, Willy?”
He took to calling her a pet name after that. She didn’t mind at all, she even gave him her personal number to call as they got closer. Jeremy was more than just a random person online that tipped her. They were becoming friends.
So, when Willa suggested he finally transition to Jessica full time he had her in the back of his mind as he considered it. She sat silently on the other end of the phone, letting him come to the conclusion himself.
He thought it would be a big change, but really all he had to do was keep it online when he was on came and when he was at home around the house. It didn’t really have to leave there. Jeremy reasoned that would be perfectly fine and he still wouldn’t have to announce to anyone else in his real life what he was doing in his spare time, which was the scariest part for him. He wanted to fully transition but the idea of having to look people in the eye and tell them was mortifying. He was just a shy little dweeb-y guy and didn’t like hearing negative things about himself. Willa always joked that he was basically a girl already, he had the anxiety level of most women.
“I guess, yeah. It does make sense,” he finally came back to her on the phone.
“That’s great Jer, I mean Jess. Or would you prefer Jessi as a cute nickname?” She always knew how to lighten the mood and make things fun.
“Whatever, I like them both,” he was blushing.
“Sounds great, Jess.”
“Thank you, Willy.”
Jessica debuted that night on cam and she was a hit. She had went out and bought a blonde wig with pigtails. She wore a cute blouse and a short skirt. She spoke in a soft voice to cover up the manly tone. Underneath her clothing she wore a matching red lace bra-lette and red boy shorts with his penis tucked between his legs as she started.
Willa logged on and even tipped with the other men telling her to take off her blouse and skirt. She urged Jessica to SHOW US YOUR DICK! followed by a laughing/crying emoji. The request was followed by a screen full of SHOW US YOUR DICK! comments from everyone else too. The tips were the highest Jessica had ever gotten. Shortly after her boy shorts came down and her dick was peeled forward from between her legs.
Willa continued to help, telling the other men they need to keep on Jessica. Giving a bit of private information that made Jessica’s eyes bug out slightly but the encouraging responses settled her quickly.
“Guys, we need to encourage Jess to go full girl. Hormones and the whole she-bang. What do you say?” Willa was finally pushing. She could sense Jessica was on the edge but was going to need a big burst to push her over. She got it with the continued responses from the tippers.
They all wanted to hear her girly voice. They wanted to see her get a nice set of tits. They wanted her body to take on a more feminine shape and see her natural hair grow out. They were all hungry and eager to see Jessica develop into a woman. Jessica was flattered and nearly cried on cam. She received heart emoji’s and xoxo’s from everyone. The next day she called to start the procedure. As the days went on whenever she was feeling nervous about it she went online and would be reassured.
Still, every tip she got she forwarded to Willa. It became second nature, at the end of the night she would send every tip she got to Willa. The unboxing of her giant, chocolate colored dildo was a huge hit and the private show bidding was very active. Even during the private show where Jessica unboxed her dildo, sucked on it and fucked herself on the bed with it, then jerked herself off until she came with it still in her ass the man who won the bidding tipped her again after. The entire tip went to Willa as well.
As time went on the hormones were taking their effect and she was becoming a girl. The testosterone in Jessica was dropping and the estrogen was rising. Her nipples were sore. Her voice was softening with therapy. She began tucking her penis back and learned to tape it to avoid any unwanted lumps in her new clothing choices. She dressed feminine nearly all the time now. She had the body type and face shape that made her easily passable for a girl and she was enjoying the attention.
She enjoyed the attention so much that random offers started to intrigue her.
Men would proposition her when she was on cam for private meet ups for additional services. At first Jessica laughed these off but the more they happened the more she started to wonder. She asked Willa, her best friend and confidante.
“So, Willy, has anyone ever offered you a meet up for something extra?”
Willa laughed, “oh yes, all the time. You know what men are like, anything to help them get off.”
They both laughed.
“So like-, you’ve never done it then?” Jessica tried to keep her curiosity in check but it wasn’t done very well.
“No, never. Why, do you want to? Oh my god, you should!”
“I mean, I don’t know. I don’t want to get murdered or anything but it sounds kind of hot.”
“Jess you fucking whore!” Willa laughed.
“Just, if you do, tell them to send the money to me. Like, Venmo it to me or something. Or they can come on and tip me a bunch of nights or whatever. You don’t want to take cash or whatever and get caught for soliciting.”
“Oh good point! Thanks! It’s just so funny that men actually want to like, I don’t know, fuck me or whatever. I’ve never thought of myself as that attractive.”
“Jessica! Girl you are hot. Why don’t you see it?”
“Shut up, Willy, I am not.”
“Yes, you are! Yeah, guys will fuck anything, but they aren’t going to pay for anything. If you’re getting offers then you absolutely are hot, girl.”
They both laughed and within a week Jessica was sucking dick for money on the side. Her new self was a hit and she couldn’t get enough of the attention. She reveled in it too. She had gone from a loser male who nobody wanted to a hot woman that was getting offers for sex nightly. She felt gorgeous and sexy. She felt like every man wanted her and she never wanted to lose that feeling.
Nearly every man did want her too. Her name got around so much that even men that didn’t watch her on cam were sending her messages to meet up. She would vet them all to make sure they were safe, of course, but some didn’t always tell the truth to hide their true identity and what they were looking for because their wives, girlfriends, families or personal lives would be turned upside down if they found out. As Jessica would find out shortly.
A man had offered Jessica a healthy sum of money for a special meeting. He asked that the room be dark. Jessica said it could be dim but not dark, she wouldn’t meet a stranger in a room with no light. He agreed but wanted the curtains pulled and the lights dimmed. She agreed to that and arranged a hotel room and gave him the special knock pattern to signal at the door when he had arrived.
Jessica dolled herself up in both make-up and her outfit. Her breasts were a nice A cup and she had a new lingerie body suit under her clothing for her suitor to enjoy. It was black and lacy with a lot of see through fabric, the kind of stuff that made Jessica feel incredibly sexy.
When she got to the room she decided to have on just the body suit and a robe, so she could get right to him enjoying her. He was right on time, to the minute.
She opened the door and he swiftly moved inside and walked over to the bed. She closed and locked it, pulling the latch shut for the extra precaution for any errant cleaning crew.
“Um hi,” Jessica offered.
The man stood at the bed with his back to her, turning back slightly and offering a curt, “hello.”
“So uh, what would you like to do?”
Jessica walked across the room towards him. She had her nails done for the occasion as well. She was painted and primped perfectly, and couldn’t wait to get started.
When he turned around and looked at her she stopped in her tracks and her heart began to race. She pulled her hand up to her lips and called out, “David?!”
Jessica was in complete shock to see her boss standing in front of her. She was out everywhere except at work, the people she had to see on a daily basis. She wore baggy clothing to hide her chest and began working her hair in a ponytail as if she were trying a new style. She had always spoke softly and didn’t have to interact with many people so her voice change was never noticed, or commented on.
“Jeremy?” He stretched his neck out and his own eyes were wide.
“I’ll go. I’m sorry. This is-,” Jessica panicked and walked past him to grab her clothes.
David reached out and grabbed her arm, “wait no. I’ve already paid for this meeting. It’s happening. Jessica is it?”
She stopped in his grip and looked at him, nervous, not knowing what to do.
“Jessica. That’s your name now, right?”
“Nothings changed, except well, I know something about you now,” he hinted at something she wasn’t quite sure what it meant.
“So I think maybe you should just do what I paid you to do and keep that surprisingly pretty little mouth of yours shut, hm?”
He pulled her towards him and pushed her robe off of her shoulders.
“Let me see what you look like under this. What kind of body you’ve got that you’ve been hiding from me.”
Jessica nodded meekly. She moved in front of him, keeping her head down and not wanting to make eye contact. Feeling nervous and anxious at him and how comfortable he felt with her and knowing both sides of her.
The robe fell to the floor and he made a satisfying moan.
“That will do perfectly. You’ve got a great little body on you. Lets see what it looks like while gagging on my cock now, shall we?”
Jessica fell to her knees and began undoing David’s pants. He pulled out a massive cock, one of the biggest she’s ever dealt with and something he was very proud of, “you like that? Most girls do. Most trans girls love it. Go ahead, enjoy.”
He was cocky. He was full of himself. He was a typical alpha male showing his bravado in front of a girl, as if she couldn’t live without his dick.
Jessica was impressed by the size. She loved huge cocks and trying to fit them in her mouth. She enjoyed gagging on them and trying to push them as deep down her throat as she could. He was right, she did want it and she would generally have enjoyed it under different circumstances.
Jessica took his cock into her mouth and David’s hands ran through her hair, holding the back of her head against him. She gripped the base of his cock and began pumping him towards her. The other hand was having her nails delicately run along his testicles. He was moaning in seconds.
“You are a fucking pro at this. Fuck Jer-, er, Jessica. Fuck yes. Swallow my fucking cock, bitch.”
“Take it. Take it all. You want more, I know it. Take it all. Swallow it.”
He continued urging her to take as much as she could. He continued hitting the back of her throat, making her gag and pull back. She took a deep breath and pushed back onto it again, knowing she couldn’t take him all but he kept urging her to. He enjoyed when a girl couldn’t take all of his cock in her mouth, it made him feel like he was too big for a normal woman’s mouth. He would slam his cock to the back of her throat just to listen to her gag on it, knowing what would happen.
“Fuck. Fuck yes. Pull it out. Jerk me off. I want to paint that pretty face of yours. I want to see what a pretty little cum rag you make.”
He let go of Jessica’s head and pulled his cock from her lips. She continued stroking and teasing his balls until his cock jerked and his load of cum shot across her face in four different jolts. It streamed from her neck and began dripping down her chest, all the way to the top of her head and in her hair.
David grunted as the cum shot onto Jessica’s face. She closed her eyes until the shots of cum coated her and then she went into clean off the tip, causing his body to shiver from the sensitive head of his cock.
“Oh fuck baby. You’re a fucking great blow. This is going to be fun.”
“What is?” Jessica said inquisitively, her face still covered in his cum.
“This thing now. You and I. I’m going to love having you suck my dick whenever I want now. You know. I know you do this so you’re going to be my pretty little mouth on call whenever I want.”
She looked at him, confused and wondering why he thinks that’s going to happen.
“What do you mean? Why?”
“Oh come on. You don’t want anyone at work to know you’re a girl, right? You especially don’t want anyone to know you’re sucking cock for money. I think you’re smart enough to get what I’m saying.”
“But,” she didn’t know what else to say.
“But nothing. You’re my personal cum whore now. Don’t worry. I’m not going to take advantage of you. You won’t have to do much work anymore. In fact I’ll send you on errands frequently, daily. You can go to the gym to keep that sexy little body in shape for me. I might feel the need to fuck it from time to time.”
He pulled his pants up and walked around her towards the door.
“Who knows, I’ll probably want to see you in your feminine gym clothes and want a post work out blow job too. I bet you look good in a cute, high pony tail.”
Jessica was speechless. David was undoing the latch and moving through the door. She didn’t know what to say. She quickly texted Willa.
Willa. Omg. I don’t know what to do. My boss knows who I am. He just left after cumming all over my face. He said I’m going to be his private fuck toy. What the hell!
It only took a minute for Willa to respond.
I know Jess. I told him who you were. He was one of my regulars. I thought you’d enjoy it, being the eager little cock whore I’ve made you. Sorry, not sorry lol. Don’t worry, just keep going. It’s what you wanted. Every man wants to use you now. Just be a dumb cock hungry slut. Don’t think, just fuck. That can be your new motto. Anyways, keep sending me those tips. xoxo
Jessica read the text a few times over, stunned. Willa had been coaching her along all this time. Through the dressing and the hormones and everything.
Her mouth was open. She didn’t know how to react. The cum was still dripping down her face and chest. She was being blackmailed at work and used online. She was no longer a man, but a cock hungry girl that seemed insatiable. All of this was happening and the part that confused her the most was that she couldn’t help but be turned on by it.