The New Pizza Girl

Not expecting her response, he questioned it thinking that he was never so lucking getting laid like this and not having to pay for it with multiple dates first. "Really...you have a friend that will just have sex with me?"

"Yeah...that's her thing. Sasha actually likes topping guys."

"I guess," Sal said quickly as he was still wondering how he would handle it and if he would really like to make a leap from anonymous toys to a real live cock.

Laci pulled out her phone and finally exchanged numbers with him. She then put in another name and then looked up at him. "She is an escort...but I will tell her you are a friend. I will make sure she doesn't charge you."

"You're giving me your hooker friend's number and setting us up?" Sal questioned as he had no idea she was going to offer him that.

In the back of his mind he thought that it was worth a try. The initial idea of being with a prostitute was off putting as he was never with one before. He quickly thought about the trans people he knew to hit on and then realized that a sex worker was his only option. Laci knowing this person made it seem safe and as he knew it was,yet he hated telling her for fear of judgement that he was going to be fucked by a transgendered sex worker.

"She is sweet and really hot," Laci said calmly not missing a beat.

As Laci was entering the contact in his phone, he wondered just how hot this friend was. "Is she as hot as you?"

Laci looked up smiling wide. "Aw, thank you...I guess. She does have long blonde hair and has a good looking body."

Not wanting to make it seem that his life goal was to date and be with transexuals, he wanted to make it known that he was just experimenting. "This is just a one-time thing you know...I just want to try it. Nothing else."

"I know," her soft response came as she handed him his phone back. "I will have Sasha text you."

When she left, Sal let his eyes gaze upon Laci's ass knowing that she did have a cute body and a great butt. He liked that she was showing it off more and acting more like a normal girl than some shy emo girl with those oversized clothes. Not that he was friends with the other people that worked there, but he felt the deeper friendship with her now.

The day ended quietly, and Sal found himself at his apartment wondering if his new sexual kink was really worth it. It plagued his mind and like a virus spread as he found himself looking at it online more and more. The fear of the unknown with Laci's friend Sasha now weighed heavy on his mind.

Once he began to relax, his phone buzzed. Looking at it, he saw the first name Sasha. With a fast heartbeat he texted back. The texts started out as friendly as they just exchanged basic information. As the night moved on, it went from normal to sexually explicit. They exchanged kinks and then photos as he told her that he was new and wanted to experiment. She texted back that she loved fucking guys that were new and would meet with him.

He delved into what he wanted, and she agreed to come over tonight, which shocked him as it was quick. The picture she sent comforted him as she was really cute too. He did know that he was in a tight spot as she knew a lot about him and that he was going to have an actual dick in his ass tonight and not some fake toy.

After a long hot shower, he put on a t-shirt and sweatpants feeling clean in spots he never felt clean before. He followed Sasha's prep instructions carefully and then the nervousness set in. Sal never once thought about having a cock in his ass and now the realization of it happening was settling in. The only thing stopping him from canceling was knowing it felt good when he did it and the hope a real dick would feel even better.

The knock on the door brought even more nervousness to him as he knew the person on the other side of the door had a dick that was going to be put in his ass. Not backing down, he opened the door and laid his eyes on her.

Sasha had long blonde hair that had nice big curls to it. Her makeup was done like she was about to go out to a fancy restaurant as her eyeliner showed off her nice blue eyes. Her smile warmed him as she stepped in. She was wearing leggings and had a loose blouse on. When she walked past him, he saw that she had an amazingly tight ass with a perfect curve to it. Her breasts were large, and her feminine form would have tricked anyone. Her face had narrow define lines and her voice sounded spot on like a girl.

"You look even better in person. I am going to love this," Sasha cooed as she ran a finger across his chest.

"Well, you look really hot yourself...wow," Sal commented back, feeling like his decision to do this was the right one.

"Thank you, I spent a lot of time and money to make sure I look good. I like it when a guy notices."

"Money well spent," Sal smiled back as he couldn't imagine that she had extra parts since she looked so natural.

"So you want to do this in the bedroom?"

"Yeah...I guess," Sal answered as the moment of truth was now coming up. He could feel his nerves going crazy but seeing Sasha all hot and calm made him feel a little less nervous.

As he walked to his room, she followed listening to her compliment his decor. He looked at her ready for her to act first.

She pulled her blouse off revealing a large set of breasts held up by her black bra. She then pulled his shirt up and off for him taking the initiative. "Ohhh, you work out."

Sasha then moved him to the bed as he sat while she was standing in front of him. "I think it's cute you're nervous. Well, I will be gentle with you. Laci said that you are a sweetheart and to be really good with you."

Before he could answer, she pulled down her leggings revealing a little something extra in her black panties. She then pulled them down and moved her penis out in front of him ending the illusion that she was born a girl. It was thin and not long, but it was definitely a circumcised penis she had, maybe five or six inches he assumed it would get.

"You like?" Sasha said softly as Sal could not help but not like it.

Her body was devoid of all hair and her penis looked girly too. Her balls were there, but smaller than his. Her heavy perfume was fooling him into thinking it was normal for a girl to have the same parts as him too. He looked up at her confident in his answer and that he wasn't lying. "You look really hot."

"Bend over for me so I can see your ass baby."

Thinking that she was going to go into foreplay and have him suck her dick, he was shocked that she just wanted to bend him over. He complied and when he was in position, she pulled down his sweatpants quickly.

"Mmmmm, you do have a nice ass. I will be gentle of your first time," she cooed as he faced the headboard of his bed not knowing what she was doing.

He then heard her open a condom wrapper and then listen to a bottle cap popping. His heart raced knowing that his virgin ass was about to be taken. He was crossing the line that straight men don't cross and the curiosity of having a real cock in his ass was too much to say no to now.

"Here move down a bit," Sasha said as she adjusted him to go lower. While doing it, he heard her other hand stroking something in latex as he assumed she was getting herself erect.

"Now, breathing is important, so breath out and relax. You have to relax, or it will hurt," she then said in a soft tone as he felt something move against his ass cheeks.

Sal relaxed his body breathing in calmly like she said, awaiting the moment that his anal virginity would be popped. He then felt something nudging at his anal rim knowing it was her cock head wanting in so it could fuck him. The chance to say no was going as he felt the sexual excitement build in him. The taboo of butt sex was all he could think about too and that he was on the receiving end of the butt sex too.

He then felt it, the sensation of her crown popping his ring came to him as the lube made it easy for her to take his anal virginity. The stretching feeling was quick, and it was quickly following by a full sensation. There was no pain but the pressure of having her cock in his anal passage was the only thing he could focus on. The slight discomfort of his rectal muscles stretching was there as was the knowledge that an actual cock was penetrating him.

"Ohhh, I am in. Love how tight you are," Sasha moaned softly as he was again reminded that a transsexual had her girl cock in his once virgin ass and was getting pleasure from it.

"Ohhhh....shit...feels big," Sal moaned back, feeling the distinct sensation of fullness like his ass was stuffed tight.

"Shhh, relax, don't fight it. I will go slow but I need you to relax. Trust me baby, you will love it," she said as he felt her hands caressing his hips and then easing his journey into the world of being a bottom to anal sex.

Doing as she said, he relaxed his body the best he could while feeling her length inside of him, almost wanting to push it out. Just as he got relaxed, he felt her move in and out as the definite feeling of something sliding in his ass was so profound. He knew that this was no toy or finger but a real cock. A real cock was fucking him and the sliding motion going in and out of his asshole was something new and yet erotic.

Not fighting it, he let Sasha continue to fuck him in the ass, getting pleasure from his tight hole while he let sink in that it did feel really good. Sasha was not going fast but he could feel that she was going deep and was being forceful with her girl rod too, making sure it was fully embedded in his anal cavity.

The toy he used in the past was nothing compared to feeling and knowledge a real dick was inside his ass. It was like his breath was knocked out of him and yet he was still breathing. The stretching to fit her size was there but not painful either. Sal knew a whole world of pleasure now lay before him, knowing that his ass felt good to have something in it.

"That's it baby...you're doing good. Mmmm, you're doing real good," she commented in a low sensual tone as she kept ramming home deep as Sal let go of his body, letting it be taken like he was some girl being fucked for the first time.

"Ohhh shit....fuck," he moaned as the sensation of being butt fucked now came on strong, knowing that his ass was properly stuffed with girl dick.

The urge to push was dying down as he felt his ass muscles just give up and accept that a cock was fucking his ass. The relaxing feeling came easier as the pleasure came slow in like the tide. Her thrusts were still increasing as she continued to push against his butt like there was more of her cock that needed to be in him.

The sound of her body slapping against his got louder as he felt her thrusts getting more intense. She was going faster and with force behind her hips. The strange feeling in his anal passage was there but it was a pleasant one like it was massaging his insides while feeling full at the same time. He quickly thought there would be friction from her fucking his ass, but her length seemed to slide in and out as he swore he could feel every inch too.

"Ohhhhh....shit. Ohhh God," Sal moaned unable to hold back as the pleasure of his ass muscles being forced to take a cock now felt like there were reasons to do this again. The guilty feeling was now mixed with the regret of not using the toy Laci gave him more than once.

"Feels good, doesn't it?" Sasha cooed as he felt her continually plowing her length into his now well stretched asshole.

Sal moaned back his answer, not caring about the shame of having a cock in his ass as he knew it felt too good not to be honest, "Yessss."

Sasha purred as she pushed against him with shorter more powerful thrusts like she was truly fucking him. "Knew you would like it. Just stay relaxed and enjoy me fucking you."

Feeling his ass muscles give up and stay open like they were felt odd as each time he felt her girl rod slam into him the sense of enjoyment was confirmed. His soft moans confessed he was indeed enjoying it and the ecstasy made his member firm as a rock. The erotic nature of doing something so wrong while feeling her trans cock own his ass was almost too much. He felt that his moans were a confession of guilty pleasure of being ass fucked by a tranny and yet giving in felt too good to resist too.

Sal reached to jerk off as the need to release was building to a point where he needed to touch his own dick. "Dammm...ohhh damm," he called out as he never imagined his own dick would be so hard from being ass fucked.

"Mmm, I like that you're into it too. Your ass feels really good too," Sasha moaned back as her hands gripped tight, forcing him back in a rocking motion. Each thrust of her hard member was hitting a button in his insides that screamed to be touched by a dick.

Her thrusts got more powerful and yet Sal could feel that he was able to take it. There was no going back he felt as the stretched open feeling now dominated him. Each time he felt her thrust inward, the full sensation of being opened up came to him and all the ecstasy that it brought with it. Her thrilling pounding was consistently paced as he felt he couldn't do nothing but be used and ass fucked like it was his job to be the bottom to her cock and that her ejaculation was controlling the tempo of sex.

"Fuck, it feels good," Sal moaned out almost pushing back as he felt her cock head really hitting a sweet spot in his ass. Not ignorant to what happened if the prostate was touched but feeling it nudged and rubbed while mixing it with an open full feeling was something too good not to admit too.

"Mmmmyess. I am loving your ass baby. Fuck, you feel so good," Sasha moaned back as she was now bucking her hips and ramming her shaft deep in him. Each time she fully extended and pushed in, he felt like she was in control and giving out pleasure to both of them.

As Sasha kept plowing his she cock in his ass, Sal felt guilty knowing that he was being a bottom to a transexual and yet loving that his secret was feeling so good too. He stroked fast as he could feel Sasha's member sliding effortlessly past his anal muscles that offered no resistance whatsoever now. Before he could move the urge to cum was there. Faster than anything else, his climax ripped through him like a tidal wave.

"OHHHHH...FUCKKKK!" he cried out as he felt his cock emptying out a massive load. It just flowed through him as he then felt his ass muscles clench hard on Sasha's cock.

"You came?" she asked pulling out.

"Fuck...yesss," he moaned again flopping on the bed exhausted, totally wiped out from his orgasm. The blissful high of ejaculating was still lingering as he knew it was an amazing orgasm too.

"Did you like it?"

Sal turned over looking at the large cum spot on his bed nodding his answer. "Fucking amazing. Do you want to fuck me more or jerk off? I know you didn't cum," he asked, feeling a bit guilty that he didn't let her finish.

She waved him off with a smile. "It's all good babe. I got someplace to be anyway, and I will cum then."

She said as she then leaned in kissing his lips, "I like that you were so open to this. Laci said you were a great guy too."

He watched her get dressed and then he walked her out to the door. Just as she was about to leave, she turned to him. "I don't mind coming back in a couple of days if you want. Maybe next time, you can fuck me."

He instantly thought about it and imagined her staying the night talking and playing with her soft member too. The odd factor of her having a dick was interesting to the point of wanting to be more curious with her body. Staying the night talking with her seemed the perfect opportunity too.

"I would like that."

With an open out kiss and a smile she was off while Sal contemplated his sexual tastes knowing that transgendered girls were now on the plate for him. The idea of dating one went from not a chance to definitely possible now.

***There is a second part and will post soon***