The New Pizza Girl

Laci stepped over to him once she had a break and whispered in his ear, "I just so happen to have an extra pair with me."

"You serious?"

The idea of wearing panties was not that exciting as was the prospect of the bet. It was a great betting chip but losing made it seem like it was not worth it now. Welching on a bet was not going to happen and the thought of wearing them was kinky in a way, but he also knew it gave Laci power over him since she would now know that he wore her panties.

"Yeah." She smiled wide as he liked that she was playing with him and opening up. The only issue was that he lost.

"Double or nothing," Sal upped the bet, not wanting to wear panties and wanting to play again.

She gave a big smile that made him enjoy betting with her even if he lost. "Okay..alright. I am game, but I am going to make it more interesting. But don't bitch about what the bet is then."

Not being in a position to argue and loving the excitement of gambling with her with a flirting nature he pushed on. "Deal...I will not bitch."

Laci looked around to see if people were looking on. "You lose and you have to do something I say."

"Okay, but if I win, I still want to see you in those jeans."

She gave a big smile at him like she was really enjoying this. "Deal, but like I said...no bitching and no going back."

Sal nodded and walked off to get back to work as the stream of customers was getting more and more. Just as it was getting crazy, he saw his mother walk from the back to him. He knew he was working and just nodded his head to her as she then walked to Laci. He didn't hear what was being said but figured that she was being asked to stay at the restaurant. He then saw Laci nod her head and knew that they both were working tonight.

At the end of the day and the line was died down enough, she walked outside while he was taking the trash out. "The bet is this. First one to spill water tonight loses."

"Shit, I got this," Sal joked as he knew he was good about not spilling water although it did happen on a number of occasions.

"Here is the bet though. I wear those jeans you want but if you lose, you have to wear a butt plug the rest of the shift tonight."

Sal did not expect her to say that, but he didn't care since he hadn't spilt a glass in over a month. "A fucking butt plug?"

"Yeah...I want to make this interesting," Laci joked back smiling.

"Fine, but win or lose, I still want you in those jeans. Also...where do you put your thing?" Sal joked back at her, flirting and making demands to at least get something from her.

Laci still kept her smile. "Fine, you lose, and I will tell you what... I will wear those jeans, but if you lose, you wear panties and put in the plug and yes...I will still wear those jeans no matter what."

"Deal...but it better not be one of those big fucking things and..." He looked around one more time to see if people were looking. "This is between us."

Laci gave a concerned look. "It better be between us two."

"Deal," Sal said walking away, needing to get back to work to close up for the day and start working in the restaurant.

***

The shop closed up and his dad was already in the restaurant helping cook. Laci got changed and he walked towards the restaurant to act as a waiter until the placed died down enough that he could go home.

Just as he got the first order, he saw Laci walk in wearing leggings. He quickly looked at her and then bumped into a table spilling some water. He looked up at her as she smiled wide at him. His face went flush knowing he lost and that she spiked the game with distracting him. He cleaned up the small spill and then walked towards the back but not in the kitchen.

Laci walked over and he saw that she had great legs too. She had a big shit-eating grin on her face as he knew she was happy that she won. "I bet you didn't expect that?"

"Fuck..you really want me to put something in my ass?" he fumed, mad at himself for getting distracted.

"Follow me," she cooed and walked back into the pizza parlor and to the back room where the bathroom was.

She reached into her purse and then pulled out a small bottle and a silver looking butt plug. It was small and had a red jewel at the end of it. She then handed it to him. "Go ahead...put it in. My panties are in the bathroom too."

"Jesus fuck," Sal cursed loud as he took the bottle and the plug, knowing that he was about to test the limits of his sexual experimentation tonight.

He stepped in to see a pair of light blue thong panties nicely folded on the sink. He pulled down his pants and popped the cap on the lube. He breathed in heavy and then applied lube to his anal ring and then more to the plug. The plug didn't look too big as it seemed narrower at the tip and then thicker at the base to hold it in. He aimed it the best he could and then gently rubbed it against his ring before stopping and applying more lube to both his anus and then plug.

Pushing it in again, he felt a pop as his anal ring let go and the plug seemingly popped in. It was a strange sensation of something in his ass. It wasn't a bad sensation, but definitely a new one. It was like there was pressure and a slight bit of fullness but nothing unpleasant. He then slipped on the panties feeling the thin material on his sack and shaft. It was better than he expected and the thong riding up his crack added a strange feminine feel to it as he thought it was almost kinky.

He then put his pants on and stepped out. Laci was all smiles as she reached towards him. He stepped back as she stopped. "I am checking to see if you really went through with it."

"Fine," he huffed out as she then reached back and began feeling his ass. Her fingers then pushed the toy in deeper giving him a strange feeling that something was being pushed in his ass. It was not uncomfortable, but new as he didn't want to say if felt good to her either.

"You did it. Now...just leave it in the sink when you are done."

She walked back to leave as he saw her ass in the leggings. He now wondered why she hid behind jeans as he knew for a girl or guy that she had a cute butt. It was curved out and she had narrow hips accentuating her ass bump even more. There was no fat on her thighs either, but only on the curve of her ass that looked hot with a bit of fat on it.

As he walked, the toy in his ass felt like something wanted to go further but couldn't. It was an odd feeling of wanting to take a shit and feeling good at the same time. The urge to push was always there an yet it felt stuck at the same time. His stare could not help but gaze at Laci's ass either as he questioned his sexual preference knowing that whatever she was, her ass was cute.

He only needed to work for two or three hours but each step made him feel the plug in his ass wanting to go deeper and yet couldn't while making him feel excited for having something in his ass too. The moment it got a little slow, Laci walked over to him. "Feels good?"

"No," he said, knowing it was a lie and that it did feel kind of good and that he would try it again and not tell anyone. The feeling of the panties was over the top and the thong riding up his ass was something he never knew would feel so erotic too.

"Okay," she replied with a smirk like she knew he was lying.

"Okay...tell me. Where do you put your...you know...dick?" he asked, wanting to know how the hell she was not showing her penis.

She looked around and then smiled back. "I tucked it. I do it if I am going out, but at work it's a pain and I don't like doing it all the time."

"So you still have it and all? I just assumed that you had it, but I know some of you get it removed."

"Yes...I still have it. And before you ask...yes, I like dick in my ass, so I use toys."

He saw the smirk on her face, but also knew by the sound of her voice that she wasn't pissed, but just tired like she was asked that question before. Not pushing the limits on more sexual questions, he decided to play it safe and just go with a compliment as he couldn't stop thinking about her ass in those leggings.

"By the way...your ass looks hot in those." Sal smiled to her wanting her to know that she was cute, and she was really pulling it off.

Laci smiled and rubbed his arm. "Thank you. I am glad you noticed. But be honest...does it feel good?"

"Yes. The toy and the panties" Sal admitted not wanting to tell her that the panties felt good too, but he was being honest and decided to just tell her.

"Have you ever had anal before...used toys or?" Laci asked as he knew that she was asking if he had a dick in his ass.

With a calm answer, he spoke as he liked that it was an honest and casual conversation. "No..never."

"Well...if you do like it. I can bring in a toy for you." Her eyes perked up.

"You joking?"

She then reached back again, pushing the toy in again, making him feel it nudge something deep.

"Yes...I know you fucking like it," she laughed back at him and began to walk away but waited at the door to walk back with him.

As he walked to the door, he gave a half serious, half joking look at her. "Nothing too big."

The entire shift he wondered why the toy felt so good in his ass. He knew he wasn't gay, but it did feel nice with the pressure and fullness from the toy as he walked and when he stood still. Even as he talked to the few customers, he always knew in the back of his mind that he was wearing panties with a butt plug in his ass. It was like a big secret and an erotic one at that.

Laci got caught up with customers and stayed a bit late and talking with her was not possible. The few words that they did speak was only about work and there was always someone close by too. By the end of the night he was pulling the plug out and putting his own clothes back on. Not getting a chance to say anything to her, he left knowing tomorrow he would talk to her.

***

It was Friday and Joey sent a text with an order and then money electronically to pay for it. He walked to work and then opened up like normal and saw Laci twenty minutes early. She wore leggings and not the jeans. Sal didn't care that she wasn't wearing jeans as promised because the leggings showed so much more.

"Wow," commented as she smiled at him as if she knew he liked her ass in them.

"I don't normally like wearing these for a long time, but I wore these for you.

"Ohhh, thank you."

"I came in early to let you have this." Laci then opened her bag showing a pale formless dildo. It was about six inches and thin like the other one.

Sal's eyes grew wide as he did not expect to be given a dildo. "You are giving me a dildo?"

"I know you want to experiment. Just try it," she added and then gave him a small packet of lube.

Not knowing what to say, he kept quiet and found a hiding place. The parlor opened up and the customers began streaming in like any other day. At lunch, he gave the order to Laci for the delivery. When she came back, she handed over two hundred to him for his share of the tip. He felt it was like their secret thing now and he found it easier to do with her than when he did it by himself.

Friday was busier than any other weekday and this one was even busier than a normal Friday. He wanted to talk more to Laci about life as a transgender but never found the right time as being alone was hard. He did look at her ass quite often and never even tried to hide it. The curve of her ass and the meat on it with the leggings hiding nothing was just what he needed to make a tough day better. He wondered how big she was to hide it as there was no bulge in the front. What he did realize was that he was going to look up tranny porn tonight as it intrigued him so much.

Every time he looked at her, his eyes went to her ass or her crotch hoping to see more of her knowing there was more to show. Sal could feel his imagination go wild with the questions about her size or how she liked to have sex and even what it felt like. The toy was a secret thing, and he could feel the build up of experimentation with it.

Having sex was not too much a big deal but it did always put him on the crosshairs of having a relationship and then her wanting more than he wanted to give. Christina was his last ex. She wanted to move in and have him go to college to be respectable. She never complained that he always had money on him and bought her nice things. Sal knew that what he was about to do tonight was a personal adventure with the toy and nobody was going to help.

The day ended and he still didn't have alone time with Laci, but when she walked past him, she smiled. "Let me know how it goes this weekend."

Sal knew it was a direct question about him using the toy and just answered quickly, "I will."

When he got home, he looked up what to do and how it feels. The taboo of venturing to sites that had girls with cocks was something new, but he found it didn't turn him off like he thought. He did see a number of girls that looked really hot, even thought they were packing a dick between their legs.

After a nice long shower, he lubricated himself and then the toy, breathing deep and feeling dirty doing it and then liking the dirty feeling of doing something wrong and taboo. The toy was small compared to what he saw online, but figured it was a good start or end if he didn't like it.

The toy slipped in just slightly and then with more lube he pushed it in suddenly feeling it all the way in. It was not like the plug as it had a thicker, full feeling to him and deeper too. When he pulled it out slightly and pushed it back in, a soothing full feeling came over him. Feeling his anal muscles try to push it out, he pushed back in feeling a fucking sensation and that the toy was going deep too. The more he pushed in and out a calm came over him as did the enjoyment or feeling it penetrate him.

It was only five minutes of slow motions as Sal felt that it was enough that he knew he liked it. Not wanting to hurt himself, he stopped and cleaned up ready to admit that a toy in his ass did feel really good even though it was only for a few minutes. To finish himself off, he found a video of a cute transexual fucking a guy and knew that he was liking it way more than he should or thought he would.

The rest of the weekend he found himself watching more videos of transgendered girls having sex with guys. Some of the videos were mixed where the guy fucked the girl, but Sal liked the ones where the girl was pounding the guys. Questioning his sexuality came to him a few times but he knew that he liked girls and found his new found kink to be just a side fetish.

Monday, he opened the shop like normal as he knew his dad liked to sleep in and often said that if he wanted to take over, he would need to get used to more responsibilities. It was an hour before the parlor opened and a few things needed to be done like normal. The second he hit the lights the door opened, and he saw Laci there.

She was not wearing her normal baggy clothes and the apron though. She was hiding nothing as her ass was in full view as she wore skin tight black leggings and the shop shirt that showed off her chest. "So. Did you like it?"

Sal turned his head still making sure nobody was around as the fear of getting caught was too much. "Yeah...it's not bad. Strange though."

He didn't want to fully admit that he liked it a lot more than he told her and that he jerked off to girls fucking guys with their dicks. He didn't like losing power to her and giving away all of his personal sexual secrets.

"Honest? You just found it strange? Come 'on, tell me the fucking truth," she joked back as he could see that she was detecting his bullshit.

"Jesus fucking Christ." Sal shook his head knowing that he was going to have to come out with the truth.

He walked over to the prep table and grabbed an apron. "It was good. I liked it. Is that what you want?"

Her tone got overly chipper as she sounded happy. "I knew it. So you going to have one of your girlfriends use the toy on you...maybe buy a strap-on."

The idea of having a girl play with his ass never crossed his mind as he knew it would end any relationship he ever had. The fear of the girl knowing he was into ass play was also a deal breaker as he felt it was a personal secret.

"No...never. I am not dating anyone, nor would I ask them," Sal huffed, knowing that Laci knew so much personal sexual stuff about him.

"Aww. I feel bad. It's better when you share it with another person."

As she went to help him set up, he decided to turn the tables on her to get some information so she wouldn't be the only person who had all the dirt. "So...does it hurt when you tuck? Is it...big or small?"

Laci walked over casually to him. "Are you really asking to see my dick?"

"No..no. I was just asking about how you hide it is all," Sal said as he felt that the casual flirting was now hitting a second gear and heating up. He only saw part of her shaft last time but not the entire thing. It was that he was desperate to see it, but now that it was brought up his curiosity took.

"Well, I use tape to make sure it doesn't go anywhere." She smiled at him making him feel at ease that she wasn't so upset about asking a personal question.

"When did you know...you know about you not thinking you were a guy and all? You said young, but what age actually."

Laci was still smiling but turned and leaned back on the counter. "I don't know...about five or six, I think. I always knew something was off. Parents put me in therapy and the more I was there, the more I knew I was a girl. Went on hormones young and then that's it."

"Ohh, but you are into guys, right?" Sal wondered and needed to ask thinking that he was at a good spot with her telling him more.

Laci chuckled and smiled wider making it seem that she was enjoying the questions. "I like guys...always have."

"Ohhh. So you do date guys?"

Laci shifted her weight keeping her smile. "You thinking of dating a trans?"

"No...I am just curious that's all," Sal answered as he knew he was naive about trans people and just wanted to know more.

"Why? You have something against trans? You wouldn't consider dating one?" she questioned no longer smiling but not showing that she was angry.

"I don't know...maybe. Why...you have any trans friends that are cute?" Sal joked back as he started heating up the ovens with coal.

"Maybe," Laci answered and then quickly walked to the bathroom.

As Laci was in the bathroom, he figured she was getting ready and adjusting stuff and went about his work doing the opening up procedures. The oven was coal fired and he wanted to set them up for the day as usual. Just as he did, he started a pot of coffee in the back and then saw Laci walking out with her makeup done over again.

"I can open up," she said as she walked to the front of the parlor.

Once everyone started coming in, the customers began piling up like any other day. Sal was at work as was Laci, but he still let his eyes wander to her ass thinking that she should wear leggings more often as she had a cute bubble ass and nice hips too. Without the apron he got a better look at her chest and figured that she was at least a C cup maybe a small D. The only question was if they were real but not caring either was as they looked good on her.

When it began to get slow at the end of the day and Laci was alone with him, she walked over with a serious look about her. "You really wanting to date a trans or just have sex with one?"

Taken back by her direct approach, he figured he would keep the honesty going. He never saw himself with a trans, but still wanted to experiment sexually. The only natural answer he felt was to just have sex with one. "I don't know...sex and then go from there."

"Well, I have a friend that will just have sex with you if you want that."