Adventures of Hiking

"That's it...that's it. Just stay relaxed as your ass adjusts. Just breath softly. No pushing either...just let it happen. Stay totally still and calm," she said as he focuses on not moving or letting his instincts kick in and push her out.

"Ohhhh, okay," he replied, feeling the "Trust me, it will get easy and feel amazing speech."

The pressure was intense as the full feeling never dulled like the initial pain of her pushing in did. The sensation to push out the intruder was so strong too, as he reminded himself to stay calm and relaxed. "Why do gay guys like this?" He thought as he felt no real pleasure of having her cock up his ass either.

As Jessie pulled out a little, he wondered if that was it and it was all over. Just as he thought about what was happening, he felt her slide back in again and once again felt her waist on his ass confirming she was all the way in. The full sensation of being stuffed with her girl cock still did not fade but he could now tell that his ass muscles stopped having the urge to expel her girl member from his anal cavity.

"Mmmmmyess...Ohhh fuck your ass feels nice and tight. Is it hurting?" she cooed at him as he felt her slowly pushing in and out of his ass in a fucking motion as he felt something building in him.

"Nooo...it just feels weird," he admitted as it was like an unmovable pressure in his ass that was no longer painful but had a weird sensation inside of him that he could not pinpoint.

"It gets better," she said as she pulled out and pushed back before finding a steady rhythm.

It was not fast, but he still felt her hips bucking against him as her girl rod slid deep in him. Her cock felt thick and yet his asshole was easily taking it. It seemed to glide through his lubed ass muscles with pure ease she pushed back deep in him each time. The in and out sensation of her cock felt like she was in total control too, as it was her pace controlling everything too.

"Ohhh fuck...that's it...ohh fuck your ass feels so good," she moaned out as she picked up her pace letting his ass feel like it was being fucked.

All his thoughts of wrongdoing ended as he felt a numbing feeling that was now pleasurable. It was like her cock head was nudging on something in his ass that felt really good. The more she pushed in, the more he felt the urge to push back so it could be rubbed harder. Each time her girl rod slid in, he swore he could feel each inch claim his hole too.

He knew his curiosity was now appeased as was his understanding of why some guys loved anal sex. Jessie was pounding away and all he could do was let loose a series of soft grunts and moans too. Each time she plunged into his ass he let go a soft moan like he was confirming she was right about getting a cock in his ass too.

"Fuck...fuckkk. Your ass feels so fucking good. Ohhh fuck yes," she moaned out as he felt her body now slamming home against his backside, feeling her girl cock piston out of his anal tunnel.

There was no doubt now as he knew he was truly feeling what it was like to be butt fucked. Her girth was not even a problem now as he felt open for her without thinking about keeping his anal muscled relaxed. The open feeling and full sensation of her plunging her girl cock in his ass seemed easy now as she pumped away. He just stayed still and relaxed giving up his ass for her dick as he felt his anal hole had been claimed by her now.

"Ohhhhfuckkkkk," Greg gave in and moaned out, still staying relaxed and yet giving into the building pleasure of her cock as it pounded away. He knew there was no denying it now to her as he felt his brain go drunk on pleasure confirming that his ass wanted it now.

"You like it?" she moaned back as she was full on fucking him now with the sound of her body pounding against his backside filling the small trailer.

"Yess...yeah. Ohhhhfuckk!" Greg cried out as her cock was fucking his ass full force now and yet he knew he was taking it feeling only pleasure. There was a sense of giving up that came over him that he loved now as he felt like he was the one being fucked and that her cock was the instrument of his enjoyment.

"You want me to talk dirty?" she asked as he felt her hips pounding at his ass hard, feeling her girl muscle pump in and out of his now open ass.

"Yesss." He gave in as he never knew his ass being fucked could feel so good.

"Ohhhhyesss...you feel my big cock fucking you? You like big girl cock?" she moaned out as his brain seemed to be like mush now only thinking about how amazing it felt to feel her meaty cock plow into his asshole as if it was a pussy to be fucked.

There was no resistance now as he felt like his ass was an open fuck tunnel now for cock. His ass muscles felt numb and stretched open without the ability to close even if he wanted to. His own cock was throbbing hard as he wanted to reach down and play with it too. Her cock tip felt like a spear that was hitting a spot in him making him think she knew exactly where his prostate was. Denying the pleasure would be a crime as he knew that her trans girl cock was now the pleasure wand for his ass.

"Ohhhh fuck...yesss. Yyess," he cried out, feeling her girl dick piston in and out of him like she was a sex machine for his ass. Her body was slamming home as he felt his hips absorb the blows with each one confirming he was the one being fucked.

Her body was thumping away as her cock burrowed itself in his butt hole over and over again. He felt she was relentless in fucking his tunnel and when he tried clenching it, it was no use. He could feel his rectal muscles stretched and loose from her fucking him too. It didn't matter either as he just wanted her to keep fucking his ass.

"You're taking my cock so good too. It's like your ass was made for me. You're sure this is your first time?"

"Never...Ohhh never," he moaned, feeling her body thrust against him as her girl member pumped in and out of his ass freely.

She pulled out as he felt the loss of her cock and yet still felt open at the same time. "Sit on the couch. Gonna fuck you like a bitch now."

Greg moved into position as he saw his underwear covered with lube and a small spot of cum. Not caring about it, he sat on the couch as she grabbed his legs opening them and holding them up at the same time. She pulled him back and then pushed his legs back so his ass was up in the air.

She then grabbed his dick and looked at him. "You came a little."

"I did?" he questioned as he didn't feel his orgasm yet and still felt his dick was hard like a stone.

"You did a little. Either that or you precum a lot," she said as she maneuvered her helmet towards his open ass, pushing easily back inside of him.

She then reached down holding his underwear that showed a large wet spot on it. "I didn't feel that I came though."

Jessie put his hand on the base of his own dick. It was very slippery as if he came but it was clear so he knew that he precame, but the amount was almost unreal. "Wow...it is a lot."

"It's good too...lets you know that you your ass likes it." She smiled back at him.

She then pushed in further as his eyes almost rolled back with the utter blissful fulfillment of her thick cock plunging back into his anal hole once again. "Did you ever think you would have a tranny cock in your ass?"

Shaking his head and feeling spread out like a girl he replied, "Nooo...nooo."

She pushed in and then held it as he saw a look of lust in her eyes. He smiled back at her panting. "It does feel fucking good. Fuck it feels good."

She smiled back at him as she pulled out and held it before pushing back in with a hard confirming thrust. "I swear your ass is making my dick feel soo good."

Once again, she found her rhythm as he felt her pound away inside of his ass like it was a home for her dick. He felt lost in ecstasy as she was pounding away, fucking him like he was a girl with her legs up. "Mmmm you're doing good...I can feel you cock pulsating as I fuck you too. You're a natural bottom too. Love that. Love bottom bitches who can cum while being fucked."

Her body became still just as he felt the rising of his climax. He didn't even need for her to stroke him as he felt the urge to spew his load. She just held his dick calmly speaking, "Don't cum yet. Hold it for a while. I want to fuck more and then you can cum...but only after I cum."

"Okay...okay," he moaned, feeling the urge to ejaculate bad too.

"Is it what you expected?" Jessie asked as he still felt her cock wedged deep in his ass moving slowly but not moving her hand from his base like she was delaying him.

"No...feels good...really good," he admitted, knowing full well that he would seek out anal sex in the future, that trans porn was now on his watch list after feeling her fuck him. The memory of this now would be relived in his thoughts each time he was seeing a trans girl now.

She smiled at his answer and then moved her hands caressing his ball sack. "I made sure to use enough lube in your butt to make sure it wouldn't hurt."

He felt her pull out and then push back in as it felt different and yet better as she plowed into his anal hole once again. She stroked his cock slowly as she banged her slender body against his making sure her girth was buried deep each time.

"Ohhhyesss...make me fucking cum." She moved as Greg just gave in and let his ass be the hole for her cock to fuck.

He nodded his head giving into the fact he was spread open being pounding like a girl would be, and he loved each glorious thrust her cock gave him. The idea he was her bitch now was being confirmed in his thoughts now. Her hand was stroking him slowly, almost making him want to push back as the combination of pleasure was unreal.

He saw her eyes close as she was now going full speed with her hips slamming home deep with her girl cock. "I am gonna cummmm...Ohhh fuck yessssss."

His mouth opened up as she said it, hearing her moan loud at the end. He wanted to be worried and possibly be disturbed that his rectum was going to have actual sperm in it. The thought that a cock would spew semen in his butt would be gross and a turn off now became a curiosity to be tried. The idea seemed so gross and literally gay, but he could not help but think it would feel good and be a great ending.

Her body was now slamming harder as he felt powerless under her, like his job was to be a fuck hole for her cock and take her load in him. Her thick flesh rod was pulsating too as he knew that she had to be really close to her climax. There was no denying that he was both loving it and enjoying how his ass had stretched to her fat cock size.

"Ohhhhhfuckk!" Jessie bellowed loud again as he could feel her cock stiffen and stop moving. Her body was almost shaking as he knew she was depositing her girl sperm in his ass.

She pushed her body hard against him, holding him in place. He wanted to feel it but only felt her body against hers. He knew that her girl cock was unloading all the content of her balls right in his ass like it was a pussy to be inseminated. She was balls deep as he then felt her cock flex again and again. His own dick pulsed as he thought about the fact there was actually sperm being spurted in his anus and her thick cock was the tool to deliver it.

"Ohh shit...I am still cumming!" she moaned again, still holding her body against his as he felt her cock just pump away like it was not done making sure his anal hole was properly filled with her warm trans cum.

"You ready to cum now?" Jessie asked still keeping her cock fully impaled as her hand was now fully stroking his dick.

Greg nodded as his eyes rolled back in his head. The sensation of her cock impaled in his rectum while her hand stroked his dick was almost too much. The feeling of direct pressure on his crown while her girl cock just stayed erect in his ass was almost too much. He instinctively clenched to the best of his ability, but it felt like her dick was even bigger now.

"OHHHHH FUCKKKKK!!" he screamed as his ass wanted to clench but couldn't from her cock and her hand stroking his dick.

Greg never had a body shaking orgasm, but his hands now scrambled to grab anything to hold onto. Jessie was not stroking him but squeezing and sliding her palm on his crown making sure his sensitive tip was feeling pleasure. Her cock felt thick in him and without the ability to push her out only added to the intensity.

"That's it...Ohhh fuck you're close...I can feel it," she moaned as he finally let go as his body shook.

His eyes closed and he felt like he was having a seizure as his climax was riding through him like a tornado of pure ecstasy. Her cock was still wedged in his ass as he just felt his own dick just spewing out its cream into her hand as nothing else mattered. She stroked slowly as she felt like he was now being milked.

Jessie finally stopped stroking and he opened his eyes feeling the euphoria of his greatest orgasm rob him of all energy. "You came. You came ALOT too," she calmly stated as he then looked down to see her hand covered in his cum.

"I am so tired. I never had an orgasm like that," he mumbled, almost feeling drunk from the pleasure.

"Okay. Don't move. I am going to pull out, and don't move."

As she pulled out, he felt the loss of her dick and yet still felt open from being fucked. Wanting to clean up quickly, all he saw was his underwear. Not thinking, he grabbed it and wiped the base of his dick clean.

Jessie then came back to him and handed him a washcloth. "You might want to clean your ass too. I didn't see a lot come out, but it will probably come out later."

"Okay," he mumbled, finally standing up and yet unsure if he could walk at all.

"You can crash in my bed with me, but you need to keep that washcloth between your...here let me," she said as he felt her wedge the washcloth between his ass crack like it was a makeshift diaper for him.

"I don't want to wash my sheets because your ass leaks out."

He followed her into the bedroom noticing it was covered in tattoo drawings. He wanted to ask questions but felt his words not being able to form. He just fell into bed as she did the same holding him. He turned to her, giving her a sensual yet weak kiss.

"I hoped you liked it," he said, wanting to say something more profound but was still shocked he even spoke since he was so tired and almost delirious from sex.

"I did. I hope you liked me fucking you. Not too many straight guys will admit that they liked it."

Greg closed his eyes and murmured, "It felt good and I didn't think it would."

***

The ring and vibration of his phone woke him up as he looked at the caller. It was the tour guide. He then looked at the time. It was seven and he had all his alarms set. They were not even snoozed as he slept through both of them. The ringer stopped as he realized that she hung up and that there was no chance he was going to get there in time.

He looked over at Jessie as she was sleeping next to him. "Fuckkkk."

She opened her eyes and looked at him without being worried that he cursed. "Did you sleep through your alarm?"

"Yes...fuck...they will leave without me. Shit...shit...fucking shit. I missed it. I fucking slept through my alarms," he cursed louder.

Jessie sat up as he looked at her breasts as she made no attempt to cover up. "If you want, I can take you to the meeting spot that all tours go through. It's a small cabin the Rangers use."

"What?" he asked.

"There is a meeting spot that most tour guides use. It's like a spot to take shelter in case of emergency and a place state police use to rescue lost hikers. We can take your Jeep too, so you won't miss them. Of course, we still need to get your car fixed."

"Really?" he said, thinking that his hike could be saved.

"Sure. I feel bad that you missed your tour."

"How long does it take?" he asked, feeling better that he could still get in most of the trip.

"I know a shortcut. With a Jeep, we can be there before dark tonight. Be there before your group gets there too, I bet."

"And you can take my Jeep back," he asked, not looking at her breasts but focusing on her face.

"Yeah sure."

Greg texted the tour guide apologizing for missing the deadline and then asked if they were stopping at a small cabin that the Rangers use. The tour guide was quick to text back that they could meet up at the cabin today and that they would be there about sunset."

He looked up at Jessie realizing that it was all solved. "Thank you so much."

"You know we have time to kill."

"Here let me show you what I am really working on. As she said that she reached under the bed and pulled out a binder.

"Sure," Greg answered seeing that the binder was elaborately decorated, and she must have spent a lot of time working on it.

She then flipped on her side and opened the book to reveal hand drawn tattoo designs. Each one looked beautifully done and something that you displayed as artwork themselves. "I want to open my own place. There is a place in Great Falls that says they might buy some of my pieces."

He flipped through the book as she pointed to each design and explained what it was and what she was thinking when she made it. Greg knew she just wanted to open herself up and talk about something other than sex. He listened and pointed to the ones he liked but also told her that he had no tattoos and was not into them.

She smiled back and then pointed to parts of her body that she wanted to tattoo. Greg then looked away and saw the parts of her body where she wanted them. As she pointed to her lower stomach he was still fixated on her limp member as it just hung there lifeless. Although soft, he instantly recalled it fully erect and plunging in his ass.

The strange concept of how a seemingly hot normal girl could have a cock on her still rattled around in his brain. He knew of trans girls and that shemale porn was out there, but he felt it was like seeing a bald eagle as it was not something you see or encounter every day. The touch feel notion came to him as he couldn't help but reach out and caress her shaved balls and penis.

"Ohhhh. Didn't think you wanted more," she said as she turned away from the book and now looked at him.

Looking at her he spoke hoping it wouldn't offend her, "It's just that I never felt another dick before...just being honest."

"It's fine. I know some guys just like to look, some experiment."

As his hand caressed her sack, it was strange feeling another set of balls and feeling one without hair too. The elastic stretching feeling and then moving over to a soft prick was so surreal he thought. She moved to allow him more access too as he saw her sack was smaller than his but still hung there as a reminder she had sperm and that he took it up his ass too.

"Mmmm...feels nice. Most guys just want to leave right after sex. I like this," she admitted as he now thought about how they had something different now.

"Do you sleep with a lot of guys?"

"Sometimes. You're the first to ever be at my place. I don't like to take guys home with me," she said as he thought about how lonely she must be since most guys probably thought about her just for sex.

"I don't sleep around with a lot of girls. My girlfriend dumped me over a month ago. You are the first person I have been with since. Also never had a dick in my ass either...guessing you knew that." Greg chuckled and smiled even though she could not see his face.

She pushed her butt against him as he felt like she was trying to get his soft dick between her ass cheeks. "I would let you fuck my ass if I wasn't so tired."

As Greg thought about it, he reached down to see if he could get hard. Jessie then turned halfway looking at him. "It's okay...I like just being next to you like this."

Greg moved his hands to her hips and then to her stomach. He could feel that she had more muscles than a girl should but also was absent of fat too as she was very slender. He didn't stop at her stomach and moved further down feeling her soft member again as it seemed so lifeless and yet exotic too. His fingers were gripping the softened shaft and then caressing her shaved balls again hoping it would get hard.