Adventures of Hiking Ch. 02

***You will need to read Chapter I to understand Chapter II. Don't be that person who reads the second part and then complains about to knowing what is going on. There is more to this story but I have not yet written it.

Greg thought about her offer and although he said yes, he was thinking about the whole night and the next day's hike. With the gorgeous scenery of the mountains, he let his mind drift to the right and wrong of having sexual relations with a transsexual. He knew he didn't feel gay, but he also couldn't stop thinking about how great it felt to feel her take his anal virginity too.

The guide was calling out trees and plants while Greg was feeling Jessie's panties holding in his privates as it was a constant reminder that he was wearing her panties and that there was more of her he would have to see. It was like there was more to her story and more to their relationship and yet he didn't know if there was a relationship either.

He thought constantly about how she fucked him and how it felt for her to have a dick inside of him. He could feel part of him question his sexual preference, but he still saw her as a girl, just with something extra. He repeated questions in his head he wanted to ask her and then knew it was strange to ask her and that he could have said no at any time. He also knew the worst part was he liked wearing her panties as it reminded him of her in a kinky way.

With his mind finally settling, he then began snapping pictures like his camera was a gun and he was in battle. From birds to scenic scenes he took photos of everything he saw as beautiful. Nothing was left undocumented. He felt as he was getting his money's worth. The liberating experience of the outdoors was all around him and yet he couldn't shake the erotic thought that his ass was fucked and ejaculated in by a transexual.

The guide took them far out but then told them they were heading back. He knew there was more to see and explore as the trail they were on continued. Not wasting a moment, he began taking pictures on the way back as well sucking up the time away. Each night he set up his tent thinking about how good Jessie's dick felt to fuck him. Each morning his erection was filled with the memory of what they did.

When the guide began to bring them back, he knew he was going to see her again soon. He wanted to be grossed out and feel disgusted with what he did but he knew it felt amazing, like a drug that had no side effects even. Greg finally gave up the wrong doing idea and settled on the erotic memory of feeling her girl dick unload cum in his ass. He felt his arousal from the memory and thought that she pumped his ass full with a creamy load and left him wearing panties for his trip.

As he walked the tour guide spoke, but his thoughts were about Jessie. The feeling of wearing the panties was like a leash to bring his thoughts back to her. Even while wearing the second pair of panties, Greg let his mind drift to Jessie as they were almost back. He knew there was no saying no to her as he felt himself get an erection from thinking about her and her girl dick. He wondered if he should go further as his mind now put her genitalia in the "spank bank" portion of his brain.

Never before did he ever think about sucking a dick or even playing with one; now he couldn't get it out of his mind. Questions came to him about what he did and yet he knew deep down that it felt good, and he liked spending time with her. His whole body felt the strange nervous energy when he thought that Jessie was going to ejaculate in his ass again. He knew deep down that he wasn't going to say no, it was just a matter of sucking her dick and possibly swallowing her girl cum if she came.

He still had a half day of hiking to get to the pickup location he told Jessie aboutas he wondered if she was going to even offer sex. Wondering if she wanted him now nagged at him as he knew she was the catch and not him. Greg thought about himself and then wondered why he should be the catch for her. In the end, he knew he was rationalizing something more.

Just as he walked closer to the meeting spot, he saw his Jeep. As he got closer, he felt his heart beating knowing she was there too. As he closed the distance, he saw her get out of the Jeep and lean against the hood as if belonged to her. Not wanting to make a big deal of it and yet so happy she was there he just waved to her smiling wide.

He wanted to hug and kiss her but ended up just smiling wide and being cautious. "Thank you for doing this."

"Well, you did promise me money."

"I did, I did. Well worth it too," he joked as he knew it saved his trip.

As he got in the Jeep, she adjusted the radio back to a normal level since she was blasting it while waiting. "Get something to eat or head back to my place?"

"Any place good?" he said as the thought of a sit down meal sounded like heaven to him as all he ate was rations and some canned food.

"I know a good place. It's a drive, but better than the shit they serve around here," she joked as he finally got the Jeep moving to leave.

It was a longer drive then anticipated but he used the time to talk about the pictures he took and how relaxing it was. Jessie seemed to listen and then added the things she liked about hiking and what she saw in the past. She seemed to joke about him spending money on a hike that he could have done for free though.

The place looked like a bar that was used for biker rallies, but Jessie insisted it was a good place to eat. Greg wondered about it though as he did see a line of motorcycles parked by the front to add to his assumption too. The inside seemed to match the outside as it looked like they could film a biker movie inside.

Jessie walked to the side booth away from people as he sat across from her. The waitress looked like a trailer park queen from back in the day, but she was sweet and took their orders quite quickly. He looked over at Jessie wondering what place she took him to.

"You sure about this place?" he wondered, looking around as everyone seemed to be a biker or some sort of trucker.

"Yeah...my friend Amy works here. Place has good food and is way better than anywhere by me."

Not going to be deterred by his instincts, he gave in and continued the conversation about hiking. Jessie then talked about places she had been to in the mountains that the trail guides don't know about. Greg thought it was a good question but knew it could be sensitive as he ventured asking her about her web work.

Jessie shrugged it off as something she only did for the money and that she just wanted enough money to get her tattoo business going. Not asking more questions, he switched over to heading back home as Jessie seemed to laugh at the idea he would travel a dozen states to hike.

Greg wondered if sex was going to come up as he looked at her thinking about how they already had anal sex. She had all the facial features of a girl and a neck that was both thin and sexy. If he didn't already know the answer, he would never have guessed she had a dick between her legs. Even her mannerisms were that of a girl as he wondered how much practice she had at it.

The food was not bad as he could feel it was a greasy option to a good meal and it was still better than the trail food. Just as Jessie was finished, she looked up at him with a serious look. He wondered if she was pissed maybe since he brought up her webcam work.

"You still want to fuck tonight?" she asked keeping her dead stare on him.

"I...did think about it. I was hoping we could." He knew it sounded weak and not manly, but he still could not get it out of his head that she had a dick he wanted in his ass again.

"Good. But I have some rules. First, no hitting my ass. I ain't into that. Second, if I say stop you stop."

He put his hands up and replied quickly as he knew she was thinking he was some sort of man that liked rough sex and he knew he wasn't. "Sure. I am not into the rough stuff at all."

"You like kissing?" she shot back quickly with a face like she was a dog ready to attack.

"Yeah. I love to kiss," he admitted as making out was something he liked to do a lot with his former girlfriends.

"No kissing. I don't kiss," she snapped back shaking her head to emphasis it.

"Okay. No kissing," he replied wondering if she was mad at him.

She then softened her look at him. "Okay. Let's head back to my place."

The drive back was quieter as the conversation seemed to be more on sex than other things. He knew it was awkward when she turned to him and asked. "So. Did you think about what we did? Do you still think it's gay?

He knew he thought a lot about it but felt it was a complicated answer and that he was still attracted to girls. He knew that she was not a girl in the technical aspect of it but also knew that no matter what he was attracted to her. He also felt like she was somebody to talk with and have fun with too and it was more than just a dick in the ass relationship, if there was a relationship.

"Well...I am not gay. I mean, I like girls and find them attractive. What we did was experiment...right? I mean, I don't see you as a guy and you are attractive so...does that answer it?" his voice sounding worried that she would be pissed.

"Fair enough. And thank you. But did you think I was a girl when you talked with me? I mean some guys can tell, then some guys only hit on me because I am trans too. You said before you thought I was not a trans...I am just trying to see if you were really telling the truth."

He knew the question was kind of loaded but he decided to just lay his chips on the table and be honest. He still wanted to try new things but if it didn't happen then it wasn't the end of the world he felt.

"I really didn't know...honest. I just wanted my Jeep fixed and when agreed to it, I was like great. I really wasn't expecting anything else. I just thought you were a girl that worked at the gas station."

"Did you like it? Some guys like it and some just try it and then never do it again. Oh, and you still owe me money."

"I did like it...just never did anything like it before," Greg answered honestly, still thinking he was walking on eggshells with her not wanting to upset her.

As they pulled into her place, she shifted it into park and looked at him seriously. "I haven't had a guy fuck me in awhile. I use toys sometimes, but my work gets me off, so I don't get out much to find guys. The ones I do find all want to be bottoms too."

"Okay. Whatever you want is fine."

"You really want to do this?" she asked with a curious look on her face as if what he said was not clicking with her.

"Yeah. I kinda liked it," Greg answered as he knew he was not telling the whole truth. He knew he could not stop thinking about how it felt for her to ejaculate inside of his ass.

"Fair enough," she replied and then got out of her car.

With his gear stashed, he sat and waited for her Jessie to get out of the shower. When she did, she was naked with her soft member hanging in full view as a reminder that she was a girl with extra parts. The excitement of the taboo came to him again as he smiled looking at her.

"Clean up. I want to fuck you still."

"Okay," Greg replied feeling the sexual excitement come to him as he knew he wanted it more than he let on.

He walked into the bathroom and started to close the door only to have Jessie put her hand out stopping it from closing and peering in. She smiled as he knew she wanted to watch him get undressed. Not being bothered by it, he removed his shirt and then his pants. When he got his pants down, he could see the big smile on her face as he was now down to her panties.

"You like wearing them?" she asked with a big grin on her face.

"Not bad," Greg replied, not wanting to admit it did feel kinda nice.

Her devious smile seemed to know that he liked wearing them. "Mmm, I bet you liked it."

"A little," Greg gave in as he turned the water on.

"You can keep them if you want. Wear them or just keep them as a reminder," she commented as he smiled at her knowing to him it was both.

Jessie walked away as he got cleaned up for sex. All the while his brain was going crazy with the idea that she was going to fuck him. He was going to get her cock in his ass again with the full intention that it would spurt warm cum in him. The girl he could not stop thinking about during his trip had a real life cock and he wanted it in him. The dirty taboo of it all was only adding to the idea that he wanted it too. All the wrong thoughts of what was going to happen and what did happen now shuffled into the enjoyment column on his brain.

When the shower and cleaning were done, he saw Jessie on her bed drawing in her sketchpad. She was completely naked laying on her stomach with her ass in plain sight. The curve of her ass was all girl to him too. She had the hips and then bubble shape of a girl's ass and if he didn't know any better, he would never have guessed anything else either.

She then turned over and then sat on the edge of the bed. "Ready?"

"I guess," Greg replied wondering who was going to make the first move.

Jessie then pulled him closer and opened her mouth taking in his limp penis. The instant sensation of getting head came to him. For all things considered, Greg never remembered a girl who could suck on him as good as she did right away. Her tongue instantly swirled around the ridge of his crown as her mouth took him in deep as his erection grew in her mouth.

"Ohhhh...shit," he murmured as Jessie was working her hand from the base and her mouth from his tip so her hand and mouth would meet.

Her tongue went along the sensitive underside as her lips gave attention to his crown, so it was getting the intimate feel of having a blow job. Her hand was stroking his shaft giving it the feel- ing of having sex too, while her mouth was bringing his climax closer and closer.

As she continued, he felt her lips mimicking sex while her hands stroked him like she was giving him a hand job. She then stopped with her mouth and swirled her tongue around the ridge of his crown while still stroking him. He could feel the intense feeling of it all as she seemed to know exactly what to do and where to put her tongue.

Jessie then pulled away and bent over on the bed. "Fuck me now."

As Greg got on the bed and positioned himself, Jessie pulled some pillows to her chest for leverage as she moved down so her ass was higher for him giving him a perfect view of her asshole. Her anal entrance was both pink and glistening like she was prepared for a cock to fuck it hard too. There was not a single hair to be found on her smooth ass crack or balls that were hanging just slightly. Her rose bud was ready for his cock as he aimed his tip right for it like a target.

"Need to be kinda gentle going in. Don't just go jamming it in me," she commented as Greg moved his mushroomed tip right towards her pink anal cherry.

With his member slicked up and covered in lube, he pushed in. Her tight sphincter held true but only for a split second before giving way and letting him enter her anal cavity. Her stretched anal muscles were now dealing with his girth as he was deep in her ass. The instant snug feeling came to him as he popped her anal rim muscles giving him access to her anal passage.

"Ohhh...ahhhhhhhh. Fuckkkkk. Fucking feels so goooood," Jessie moaned out in a satisfying way. His cock was fully immersed in her rectum as he was waiting to move it not wanting to rush it.

It was like her ass was overly tight and yet slippery enough to fuck. It was the tightest hole ever and yet slick enough to move in and out of. As he pushed in more before pulling out, he could feel the immediate pressure on his crown too. His tip was getting all the attention of her ass muscles as he moved the slightest inch too.

He went a little bit faster feeling her tight anal hole giving him the ultimate fuck tunnel to love. His body was bumping against her ass bone as he felt his shaft being gripped tightly by her ass too. Not going overly slow, he was asserting his power in her ass but not pounding it either. His hands weresteady around her waist as he pulled her towards him making sure he was fucking her and not the other way around.

"Ohhhhhh...fuckk. Oh God...Fuck. Fuckkkk," Jessie moaned loud as he thrusted a bit harder feeling her ass finally accept that his cock was owning it.

"You like it? Ohhh fuck...you like my ass?" she moaned again as he was pulling back and pushing forward giving her the full feeling of his entire length in her butt.

"Feels so good," Greg moaned as he knew it was better than fucking his ex-girlfriend too. Her ass was tight and yet easy to fuck giving his cock the most perfect hole to fuck.

Still holding onto her hips, he speared his length in and out of her with a nice steady rhythm. The sound of the flesh hitting flesh got louder and louder as he was pounding her anal hole for all its worth now. She moaned with each thrust like she was giving up and allowed him to take her ass. Her anal muscles were giving him an almost massage as he penetrated too not holding back as he gave her the full length of his manhood too.

Jessie pulled away for his dick to feel the cold air as he was no longer inside of her. "Ohhh fuck. I got to stop," she pleaded almost out of breath.

"Too hard? Did I hurt you?" he responded to her wanting to stop, fearing that he did something wrong.

"No. No. I fucking loved it. I just didn't want to cum though. I almost came from you fucking me. It was just that good," Jessie smiled with her response.

"You could have came. I want you to cum."

"I know. But I want to fuck you. I want to cum inside of you like last time. I get requests from guys all the time and that's what they want. All they talk about is having me cum in their ass. I want to do it for you though. I want you to enjoy it. Let me give you something every guy asks me to do to them."

"Okay. Can I ask you a question though?" He was not going to argue as he thought about it the whole trip. It was both erotic and the biggest taboo he could think of.

"Sure."

"How many guys have you came in?" He thought it was an honest question but knew it would be talking about her past.

"Just one other guy. He loved it but I didn't like him so it was just once."

Jessie got on her feet and grabbed the bottle of lube as she knew it was time for him to get into position to be taken. His heart pounded fast knowing that he was once again going to feel a cock in his ass. He swallowed hard knowing that her girl sperm was soon going to be in his rectum and most likely going to spend the night there.

As he got on top of the pillow and leaned forward, he could feel the cold air on his ass since it was now slightly elevated. He breathed in knowing it wasn't going to hurt but he was going to be ass fucked. There was no turning back and he knew it and was ready to take the lead of being a guy who loved cock in his ass.

Looking around he saw all her things from tattoo books to stuffed animals. He felt vulnerable as the cold lube was smeared on his anal rim. It was surreal as he knew he was in a girl's bedroom and yet he knew his ass was about to be fucked. It was shocking and yet he felt so turned on by her doing it.

She put the small syringe device in his ass and heard the click of plastic confirming lube was being inserted in his ass for the intent purpose of anal sex. "Guess you only need one dose this time," she commented as he felt wetness in his ass from it all.

The sound of the mattress compressing came to him as did the pressure of her cock tip wanting entrance into his anal cavity. His sphincter muscles gave in quite easily as the lube expedited the process. Jessie's tip speared into him as did half her dick as she plunged it past his sphincter.