Her hand then went to the crotch of her jeans rubbing it. He wondered why as there was no visible indication that she was anything other than female. Was she small? Did she have it removed?
As Jessie looked at the camera, she then began to perform for it. Her voice then got softer and sounded sexy as she spoke, "I know you were thinking about sucking on me. I want you to think about it. Mmmmm yessss. Think about how hard I am going to get in your mouth. How my girl cock is going to get hard for you in your mouth. Mmmmmm yessss. You know I love your lips around my tip too. Ohhhhhh, yessss."
He knew she wasn't talking to him but with her being so close, it felt like it. Jessie then pulled down her jeans slowly revealing simple black panties. The more she pulled down her jeans, the more Greg knew that he was going to see something. Looking away was not an option as she was only a few feet from him, and his curiosity was now in high gear. He didn't know if it was the fact that she was performing or if he really wanted to see what a dick would look like on a girl.
With her jeans kicked away, Jessie opened her legs and reached down before pulling aside her panties. As she reached down between her legs, he saw her pull her member out revealing to him that she was a girl with extra parts. She now was giving Greg an up close view of her girl dick and nut sack. It was way longer than his and she was soft still. Although he knew he was a good six inches, she was so much bigger he thought. Her two plums were hanging slightly but not overly large either.
She continued to look at the camera not paying him attention as she moved her fingernails alongside her soft prick. "Is this the cock you want baby? Mmmm yes. My balls are full too. Going to unload all of my hot cum right in that dirty cock sucking mouth of yours."
With a slow tug of her panties, there was nothing now blocking him from a perfect view of her girl cock and hanging balls. She was devoid of hair and it almost seemed to make her long dick even larger to him. The crown of her dick was fully pronounced like a spear ready to enter anything it wanted too. Her sack hung down probably full with a big load he thought. She then reached for the base of her cock and stroked it in an almost teasing manner.
"Mmmm yesss. Think about my cock baby. Think about how my hot creamy girl cum is going to taste when I shoot it into your mouth. Mmmm, yesss...I am going to cum in your mouth tonight." She then purred as she slowly stroked her girl dick as it throbbed for more attention.
Looking away was not an option as all he could think about was how well formed her dick was. It wasn't a penis he thought, but a big cock that happened to be on a girl. She looked like a girl and even had the movements of a female, but she had a big cock on her, he thought. Looking away could not happen as he felt mesmerized by her voice and by her girthy cock that she seemed to be teasing just for him.
"Ohhhh that's it...mmmm suck it. Think about how my cock tastes. Think about...ohhhhh that's it. Suck the tip...lick the precum you dirty slut," she moaned as she did half strokes now, pointing her member right at the camera as to make it seem like the viewer was sucking her off.
Greg wanted to look away, but just stared at her erect cock like it had magical powers over him. He felt his own dick harden fast too as he listened to her words and stared at her as she masturbated in front of the camera. There was no denying it as he felt the pressure in his jeans. His dick needed to be freed as it was pushing painfully against his jeans. A bit of guilt now came to him as he knew he was aroused by it.
"Mmmmmyessss baby. Your gonna love feeling my girl cock unload in your dirty mouth. That hot cum taste...Yess. That's it...OHHHHH yess. Fucking suck it," she purred again as she stroked herself.
'Was she talking to him?' Greg thought as her voice echoed in his head like he needed to suck her cock. 'Would a guy suck on her? Would it feel good to suck on her?' He thought not knowing but thinking about her in a sexual way now as he contemplated what it would be like now. It wasn't a gross feeling of thinking about sucking her cock but an experimental one he thought too.
He knew he needed to adjust his sitting position as it was painful how his dick was. Knowing that if he touched anywhere near his crotch it would give it away that he got hard. He leaned back hoping his member would just slide into position if he contorted his body slightly. The idea of a seamless body movement could hide his erection now seemed the way to go.
Jessie looked over and Greg instinctively looked up making eye contact with her. She then reached for the camera stopping it. "Did I get you hard?" she asked smiling.
He thought about lying and hiding it but decided without thinking just to admit it. "A little."
"Ohhh, I didn't think you were into trans girls."
"I am not, but...you do sound sexy," he replied trying to get himself out of admitting he found her sexy.
"I seee. Well, if you want to jerk off while I finish you can. I don't mind," she answered as she reached over to get a small plastic bottle that was on the ledge.
"I am good. I won't need to."
"Suit yourself, but I really don't mind," she replied as she then poured lube on the top of her shaft making it shine.
Greg leaned back adjusting his member as he could see the outline of his own dick in his jeans as he did it. He felt his erection throbbing with need too but decided to leave it be. He wanted to look away but the sight of her hand now gliding across her lubricated shaft only made it more enticing to stare.
Jessie hit the button on the camera again and continued. "Keep sucking slut boy...Ohhhhh YESSSS. That's it...ohhh fuck that's it...keep sucking my cock. Ohhhh yessss...suck me. Suck my cock just like that, ohhh yeah."
Her moans as she stroked her cock filled the trailer as Greg could not look away. He felt his own cock screaming for attention as it was pulsing in his jeans. His eyes were glued on his shaft as her hand slide up and down her shaft before rubbing her big crown each time. His mouth dropped as he could not understand what was happening to him. He felt she was talking to him and that he should just do what she was said.
Jessie hit the button again and looked at him like he was being bad. "I can see you need to jerk off. Just do it. You shy or something? You don't want me to see your dick, is that it?"
Without a word he unzipped his jeans and then pulled them down. "See that wasn't so hard," she said encouraging him as he was down to his tight underwear.
He wanted to say something, but he froze up on what to stay. When he pulled down the last inch, his dick sprung free finally releasing it as it throbbed with need. He then saw Jessie smile at him as she looked at his dick. "Ohhh...that's a nice dick."
"Thank you," Greg said quickly as it came out almost too quick.
She turned to the camera again turning it on as her hand then went to her cock. "Ohhh yesssss...suck my cock. Think about all that hot girl cum in your mouth. Mmmmmm yeesssss. I am going to cum in your...ohhhh put your tongue in my piss hole...yesss."
Greg stroked himself slowly as she teased her cock. Her voice calling out to him and his dick responding with pleasure as he watched. Never before was he turned on by watching a dick being stroked but he couldn't stop thinking about it now, how she played to the camera as if the other person was doing it. His erection was fully engorged in his hand as he stroked to her roleplay.
It didn't matter what she was now as all he thought about was he was the guy sucking her. That she was commanding him what to do. He stroked his dick in a steady rhythm, but his mouth dropped open as he just thought that he was sucking her off. He never thought about a cock before, but he now felt that it would not be so bad now.
She stopped the video and looked at him as he stopped stroking in response. "It looks like you are liking this."
"I didn't think I would. It's kinda hot listening to you," he admitted, breathing heavy not wanting to say that he found her touching herself even more exciting.
"And you never been with a tranny before?" she asked smiling as he saw her cock looking at him like it was a weapon.
"Look, if you want to experiment, I'm cool with that. I can see that you seem to want to suck me off too," she said with a sly look to her.
"Nooo, no. I just like watching is all," he replied not wanting to admit that he thought about how it would feel in his mouth.
"Oh please. I see you looking at it. It's normal to experiment. Don't worry...just touch it," she pushed as she moved a bit closer as her swinging meat was now less than a foot away.
"I don't know...maybe." Greg caved in as he could not take his eyes off her fleshy beast.
"That's it...give in. It won't bite. I can give you a blowjob after too if you want to suck on me," she answered as his smile made it seem like it was the right thing to do now.
"Okkkay...I guess I can," he stuttered as he knew he was saying that he was going to actually take a real cock in his mouth. It was just experimenting anyway, and he figured it could not be that bad as it did look like a nice cock...and it was on a girl.
"Here's the deal. This lube stays on for a while and doesn't taste too good. I would need to take a shower for it to really come off."
"I guess I can wait."
"Since your cool about this and...your hard because of it. I can fuck your ass if you want." His eyes opened up as she offered her cock for his ass.
"What? I don't know...I mean playing around with oral is one thing...but you fucking my ass?" he answered, wondering if he was too deep with the idea of experimenting. He thought he just wanted to touch it and maybe put it in his mouth for a couple of seconds but anal was not even a thought before she mentioned it just now.
"Yeah, I figured you would want it," she said, still keeping her cock tip aimed at his face like it was a weapon.
"Really? I never thought about it. I just figured I would play with it for you."
"You serious? Never thought a guy would turn down a cock in their ass," she said then moved back a step.
"Why is that?" he asked, figuring that gay guys would want other men and not trans girls. He then thought she might offer her ass to him since she wanted to be a girl and the guy does the fucking.
Hey face showed a surprised expression. "Cause all of the guys that contact me want me to fuck them. Cause it feels good to have a dick in your ass. You really never seen tranny porn?"
"Just a couple of pictures," he admitted but not admitting to her that they were memes with trannys on them.
"Well, all of the requests I get are either for guys wanting to suck my dick or have me fuck them."
"Have you ever?"
"A couple of times," she admitted as she turned her body to the computer not giving him a clear view of her face or member now.
The idea of it hurting was the only thing he could think about now. The morality of it being gay was not there, just the pain of doing it and who was really getting the pleasure out of it. He never once had something in his ass, but he knew that it felt good for some guys. Greg also thought that only the gay guys liked it.
"Did it feel good?" he finally asked, still wanting to know more but also feeling like he was so clueless about things. He didn't want to come across as an asshole either, but he still felt clueless and embarrassed because of it.
She turned to him with a confused look like she knew he was clueless. "Please...of course it feels good. You really don't know about the prostate?"
Shaking off her look at him. "I do...I do. Just didn't think guys would want it so bad."
"You want to try? Cause your acting like you want to try it," she said finally moving towards him again showing that her girl cock still had strength to it.
Feeling pressure in his chest, Greg instantly felt his heart racing with doubt. What was he getting himself into? Anal sex? Nothing has ever been in his ass before and now this trans girl with her monster cock was going to put it right up in his ass. Would it hurt? Was it gay?
"I don't know. Maybe I should just shower and head to bed," Greg stuttered as he now debated in his brain what he was thinking and what he wanted.
She stepped over putting her hand on his shoulder. Her cock head was mere inches from his face as she spoke in a calming manner. "I will be gentle. Trust me, it will feel great. If it hurts, then I will stop. Come on, live a little."
His brain was screaming no, but he felt like his body was saying yes. Her cock looked so good as he stared at it. The butterflies in his body wanted to say yes and experiment and then he finally just let it out. "I guess...I can try it."
She stepped back smiling. "Let me finish this video then and you can clean yourself while I do it."
He looked at her and then around the room. Greg then stood up not knowing what to do or how he should clean himself for what she wanted. She then guided him to the small room that was the shower. She was right behind him and then caressed his ass cheek as he stepped into the room. "Mmmm, you do have a really cute ass."
He saw the room was filled with beauty products to the point of nothing else would fit on the sink. The room was clean, but it was very disorganized and cluttered. He turned to her as she was right behind her. "I never did anything like this."
With a quick kiss on the lips, he opened his eyes loving the small and sexual kiss that she gave him. "Don't think about it. Just enjoy and cum. Trust me...it will feel amazing."
As he stepped back, he looked at this trans girl as she still wore her work shirt and nothing else. Her erect dick still had life in it as his heart raced with anxiety of what was going to happen. Doubt was still there as it mixed with anticipation of what it would feel like.
She handed him a red rubber ball shaped item with a spout on it. "Use this like ten times to clean yourself. Then come out and I should be ready for you."
When she closed the door giving him privacy, he wandered what he got himself into and why was he so willing to take a real cock in his ass? Why did he say yes and why did his body seem to want it? His dick was hard from the thought as his thoughts of right and wrong were now scrambling between yes and no. The tension between going through with this and stopping was there but he could stop himself from going through the motions of cleaning his ass for a fucking.
As the water hit him, his mind seemed focused and yet the urge to go through with anal sex seemed to win out. All doubt was cleansed away as he cleaned himself out preparing his rectal muscles for an intruder. He wondered what the real thing would feel like and yet still wondered how he even got into this position. Greg knew that if he were older or had a heart condition, he would be dead as his heart beat like a racehorse from thinking about what was going to happen.
The thought of saying no was there but he felt he had gone too far in saying yes and there was no turning back. Jessie was cute and without her telling him that she was trans, he knew he would never know. He even knew that she was cute enough to hit on if he was in a different spot emotionally with his life too. With him this deep in the middle of nowhere, he really thought about how bad it could be compared to missing his trip and being forever lost in the woods?
He walked out and Jessie had the camera equipment off. He was butt naked drying off as he saw her glistening girl cock seemingly ready to spear into his anal cavity. She smiled at him pulling her shirt over her head. "You ready?"
"I guess," he stuttered out as his eyes locked on her bra.
Jessie unclipped her bra and let it fall as he saw the most perfectly shaped tits in his life. Her nipples were average size, but the perkiness of her tits was undeniably attractive. He wanted to reach out and play with them too. She pinched and pulled on her nipples making them erect a little.
"You like? I had them done a few years ago."
"Yesss. They are beautiful," he admitted as he then thought about how this was going to happen.
"Okay, bend over on the edge of the couch," she stated as she guided him into position.
Greg got down on his knees and then leaned forward as she gently guided his body downward, so his face was almost on the couch cushion. He then looked back to see her get up and put a blue looking syringe into a bottle of Astroglide. She pulled the plunger thing back and walked over to him.
"Normally the guy is prepared for this. But no worries, I am going to make sure it doesn't hurt. This will put lube right where it needs to go so...no pain," she said as he felt the tube enter his ass easily. It was small and his ass easily took it in. She then pushed as he heard the plastic on plastic sound confirming that his ass was now lubed from the inside.
"Normally one squirt should do it, but you never did this before, so I am going to give you more."
Greg said nothing and allowed his anal passage to be filled again with lubricant. She put it deep and then pulled out a little bit before he heard the plastic sound of her emptying it in his ass. He wondered why he didn't feel the lube in his ass but then tried not to think about it.
"Where are your condoms?" she asked as she stood over him putting more lube on her cock.
"I don't have any...I don't carry them on me," he answered, wondering if this was going to end it and all of his prepwork would be for nothing.
"I am clean, but I don't know if you want to do this bareback," she asked as he thought about it.
He quickly realized that if she was okay with it, then he should be too.
He didn't take her for a hooker and saying no now seemed like a major let down as he already knew his ass was lubricated. "I am clean too. Will it feel different?"
"Of course, it will feel different. Not for you, but for me," she said as he listened to her get behind him.
"You need to relax at first too. No pushing me out or it's gonna hurt. Just relax all the muscles in your body and give into it."
With a deep breath, Greg did what she said but could not help but feel nervous about the whole situation. He felt her hands on his ass cheeks as he relaxed as best as he could. Not thinking about what was going to happen was hard but he let his body go limp and relaxed more still feeling his heart beat fast with nervous energy. The idea that her giant girl cock was going to enter his ass now burned into his brain of something that could possibly be the worst thing he ever did.
The sensation of her tip hitting his outer ring sent a shiver down his spine that his ass was actually going to get fucked. "Is it gay?" Now rang in his head that having a cock in his ass was a gay act and he was letting it happen.
A stretching feeling in his ass came over him as he felt her pushing her bulbous crown into his sphincter with the intent purpose of fucking his rectum. The more she pushed, the more he felt his anal muscles give way until there was nothing but a full feeling. It was not that bad he thought as the initial sting went away quite quickly. The only sensation he could now feel was pressure in his ass like something was intruding in his butt that he had no control over, and the only instincts were to push it out.
"Ittttssss, ok...almost in. You're tight and need to relax...almost in," she purred at him as he did what she said, feeling his rectal muscles being stretched to the point of feeling it was going to tear.
Ohhhh...OHHHHHHH Goddddd," Greg moaned as he felt her just slide further into him feeling her body against his tailbone. There was no doubt in his mind that she was completely in him now.