Blackmail

"Do you still have your...your thing? Did you have reassignment surgery?" he asked knowing that that was a huge personal question.

Beth smiled wide and seemed to be holding back a giggle. "I still have it. I considered the surgery a few times, but it's just not me. I like who I am now."

"Ohhh, ok," he said, quickly wondering why the question seemed like it was no big deal.

Caleb knew the next question was big, but somehow felt he could ask it as things seemed good between the two of them. "Do you like it when guys fuck you, or when you fuck guys?"

Beth smiled and gave a slight giggle. "I bet that was the question you wanted to ask last year. Well, to answer you, I like to do both."

"Ohhh. I see," Caleb responded as he wondered who she might be with or might have been with at high school.

"Were you with anyone at school?"

"Noooo. I had a few relationships with people out of school, but never with anyone in school. Joe Wilson tried to get with me after prom, but I told him it was my period."

Thinking of Joe Wilson quickly, Caleb remembered that he did take her and that he was not bad looking. "Why? Joe isn't that bad looking."

"He was cute, and I would have too. The only issue was that Joe was not into girls like me, so he never even knew that he took a trans-girl to the prom. I even asked him if he wanted to go out on a date before, and he said he just needed a date for prom. I knew he was just looking to score, so I lied to him."

As Beth laughed at her story from last year, Caleb wondered if it was him and that he asked her out on a date instead of blackmailing her. The idea floated around in his head, but he knew he was dating Paige and that asking a girl out while dating was out of the question.

"Did you get started on the project yet?" Caleb threw out there, knowing it was ending the personal questions. He did not feel ready to admit that she was hot and that he thought about her in a relationship way.

"If you help me out, I will help you out," Beth said with a slight smile on her face.

"What help do you need? Do you need to switch roles on the project?"

"I know you are wanting ass play and I could help you out with that," Beth said softly but yet calmly like it was no big deal.

Caleb was not expecting that and took a breath, wondering how far they came in such a short time. "What?"

Not expecting her to jump right into sex, he quickly imagined what it would feel like for her to fuck him, thinking about what she looked like without clothes and how large or even small she was. Did she have large balls? Is she into rough sex, and what else did she like? All of the sick porn videos quickly flashed and now entered the realm of possibility.

"You help me with the project, and I will lend you a toy of mine. It's small and yet feels great so it won't hurt."

"Ohhhh. I thought it was something else."

"You thought I was going to say that I would fuck you?" Beth answered with her eyebrows up.

"Well yeah," he answered honestly, feeling guilty for thinking that and the loss of the possible images of her naked.

Beth gave a casual glance as she answered back, "Do you want me to?"

"I guess...I guess I will try it," Caleb replied, feeling that it was finally going to happen. His heart was racing as the thought of forbidden sex was now an option.

His heart was beating fast still and the ideas in his head were all trying to get into his brain. All of this thoughts of shemale porn came rushing to him and his own dick gave a twitch in excitement. He saw the seriousness in her face and his only thought was....finally, it was going to happen.

"Tonight then. It will have to be at your place though. I am assuming you are not going to tell Paige that you are taking a cock in your ass either," Beth said with a big laugh.

"Ohh God no. We can do it at my place," he said, knowing his dad was working very late and his mom was away on business for the week.

"Okay then. Text me your address then. I should swing by around five or six. Ohh, one more thing. A big thing too. I need you to be clean, and I mean not just a shower either. I need you to get an enema bag and clean yourself out. I can't stand sex without the other person being clean."

"Question...are you big? I mean I don't mean to be rude or anything. I was just wondering," he asked hoping not to cross the line, but still wanting to ease his curiosity.

Beth smiled. "You're not rude, I mean I am going to fuck your butt tonight. I am not super large, but I am not small. I never really measured myself, but it's a decent size."

"Ok, I just don't want to offend you. I still feel bad about last year," Caleb admitted knowing that she might have forgiven him and yet still might be holding resentment back.

Beth raised her hand and moved it as to show she was not bothered by it. "Please...stop, you're fine. I know now what you wanted and besides...you never said anything."

Caleb smiled feeling that his worries about her feelings were all in his mind. He finished with helping her setup for the project and let his mind try to refocus to help her.

On the way home he was thinking of how she was going to look like nude and how she was going to fuck him. The fear of it hurting came to him and he was just hoping it would feel good and have little or no pain. From videos online, it was all about how great it felt so that eased most of his concerns.

Stopping at the store he picked up the cleaning kit hoping nobody would question him. Once home, Caleb quickly headed towards the shower to clean up. With a mind full of possibilities and a text to Beth, he figured tonight would be great. Paige was a text away telling her he was busy tonight and everything else was set.

The ring of the doorbell confirmed that he was going to feel the pleasures of anal intercourse. Opening the door, he saw Beth was wearing a summer dress. It was light blue and showed off her breasts. Her face and hair looked like time was well spent and her face gleamed with a smile.

Caleb wearing only sweatpants and a running shirt felt the twinge of guilt for not getting more dressed up, but still smiled as she looked stunning. "Come in...come in."

"Your parent's house is nice. Did you know we live in the same neighborhood?"

Caleb walked her to his room and commented at her question as he really did not know. "I had no idea." He knew her dad was a lawyer and had money but did not know she lived close by.

Once in the room, Caleb sat on the bed as if to wait for instructions. Beth walked in and looked around as if to take in her surroundings and inspect his room. She then looked at him smiling. "Get naked...I want to see your butt."

Caleb felt the thrill and excitement of what was about to happen. He reached for the condoms he picked up today and handed them to her. Beth took them smiling and then he removed his shorts and the cold air hit his softened penis. His ass felt the room air as well as he discarded his shorts and looked back at Beth dying to see her cock.

"You have a nice dick," Beth commented as she pulled her dress up over her body exposing her body to him.

Caleb let his eyes feast on her stomach, bra covered breasts and her semi-hard cock. She was longer than him by a couple of inches but not as thick. Her balls were not as large as his but still hung down. She was cut like him and her helmet was visible and seemingly ready to conquer his virgin ass.

"Wow...you look really hot," he answered back with his own compliment. She looked like any other girl and had a better body than his girlfriend Paige too. Her breasts looked real although she still had her bra on.

"Awww, thank you and they are real. You look hot yourself. Do you want to kiss beforehand or just do it?" Beth asked with a soft soothing voice.

"I don't think we need to kiss."

"Okay then. Just get on the bed and I will do the rest," she said looking down at her member, stroking it slowly now before pulling out a condom.

Caleb nodded and got on the bed and knelt down. He felt his ass cheeks part as he leaned for-ward using the pillow as a resting point. Beth got on the bed and moved his legs more open, dropping his height down and forcing him to a more vulnerable position as his ass felt wide open.

He heard a bottle cap snap open and then felt a cold liquid drip on his virgin asshole, making it slick. Then he felt her fingers rub around his anus before her one finger slipped in.

"Ohh," he moaned softly, feeling her slender finger slide into his hole.

She only pushed in slightly up to her first knuckle and he felt the penetration and then sensations of something foreign in his asshole. Caleb held in a bigger moan as she did not penetrate him with her dick yet, but it was the start of anal sex.

"You need to stay as relaxed as possible. Just breathe in when I push in and don't think about it. Just let go and stay relaxed."

Caleb felt the loss of her finger and then something larger touch his asshole. The sensitive skin alerted him that something was touching it and about to enter him. The touching sensation got more intense as he felt something trying to enter him. The pressure of her crown pushing in grew more and then finally it popped in.

"Ohhhhhh," Caleb moaned in a deep but soft tone.

"Shhhh...just relax. Just let go and enjoy," Beth soothed him as he felt her still pushing in.

There was no pain, but an uncomfortable and unfamiliar fullness inside of him. It was pressure of something being inserted in him that he was unable to push out. He felt her tip take his anal cherry and now she slid into the point where he felt her body against his ass.

"I am all the way in. I am going to go really slow and I need you to stay relaxed. Don't push either."

Caleb relaxed the best he could as he felt her girl dick slide out a little only to push back in. The fullness was so overwhelming, the instinct to push out needed to be suppressed. The more she pushed in and retreated, the more the sensation of being anally fucked came to him. His cock grew hard as the pleasure of her girl cock sent a tidal wave of pleasure to his own dick.

"That's it...going a bit faster now. Are you liking it?" she asked as he felt her hand on his hips now.

"Yesss...ohhh it feels so fucking good," Caleb admitted as the sensation of her girl rod sliding through his anal cavity was sending pleasure through his body like he had another orgasm spot in his body other than his own dick.

Beth was going faster now, bumping her small frame against him, moaning softly with each bump. Every inch of her girl prick was now being felt. She was not ramming him, but quickly gliding in and out of his now stretched anal tunnel. His ass muscles had now been accustomed to her girth and his butt offered no resistance now. It was like a soothing sensation on his rectal muscles as her member was pushing in and out of his ass, rubbing against his anal muscles in the process.

Caleb began stroking his cock to the rhythm of her thrusts. Each time her body bumped against his, he stroked fast. He was utterly shocked at how fast he felt his orgasm approaching. He stopped stroking as it was coming on so fast. The tip of his member dripped with precum as Beth was fucking him.

"Ohhhh," Beth moaned softly as she was now going faster. Her girl cock was not fully withdrawing before she pushed it back in. Her short thrusts felt like she was really fucking him.

Caleb could not hold out and felt the dire need to jerk off. His cock throbbed with the most intent desire to be touched. The full sensation was there, but that too was intensified as he felt her shaft sliding in and out of him. It was everything he dreamed it would be as there was no pain, but only pleasure as her cock was now pounding deep.

Reaching for his cock, he stroked it a few times and then before he could tell her how great it was feeling his orgasm was there. "OHHHHHHH FUCKKKK!" Caleb bellowed out as a large heavy blast of his orgasm shot out and landed on his sheets.

"Your cumming?" Beth asked as she was still bouncing her body off his ass; he felt she was still full on fucking him.

"OHHHH Fuckk...yesssss," Caleb moaned again as he continued to shoot out his cream orgasm on his bed, not realizing that the sheets had a large pool of white cum on them now. He never remembered ejaculating so quick in his life, but it was too much stimulation and he knew he just had to let go.

Moving forward quick, he felt the loss of Beth's member as he moved away from her. Turning around, he saw her still hard cock covered with a slimy lube covered condom. He then looked up at her hoping it was good for her. Even though she was not inside of his butt, Caleb could still feel the looseness in his rectum, telling him something opened him up.

"Ohh...fuck that felt good. Did you like it?" he smiled, wanting to tell her that it was everything he hoped it would be.

"I did. I guess it was what you expected," Beth answered quietly.

Caleb got off the bed grabbing a washcloth on the nightstand. "I did some of your project for you. That way you don't have to worry about the hard stuff."

Beth pulled off the condom quickly and slipped her dress on covering her erection that poked out from it. "I guess I will see you at class then," she said as she was making her way towards the door.

Walking her out, he hoped that nobody saw her as it would let everyone know that he cheated on Paige. To make matters worse was that Beth had a penis and she fucked him. Caleb watched her drive away struggling with the guilt of it and then wondering if it was right or wrong.

***

Beth was waiting at the lab table when he got to class. He smiled at seeing her wearing a nice loose shirt and leggings that showed off her bottom half, although the shirt covered her ass. He thought about how her dick fucked him and the thought stirred an attempt at an erection only stifled by the thought it was not the right time.

"Hey, I got your project for you," he said, sliding a flash drive towards her. He smelt her perfume and saw her makeup done to perfection and her hair nicely brushed and put in a ponytail.

"Thank you," she replied quickly and with her sweet tone.

"Do you need another study session for the final?" he asked, knowing that the final was going to have parts on it that she struggled with.

"Alright. We can do it today after class."

Caleb took that as another possible chance to feel her girl dick inside of her. The sensation of butt sex had died out, but the memory of how it felt was now ingrained in his permanent memory for all time. The idea of getting it again was more than just a fetish thing but an itch that needed to be scratched.

The class ended and Caleb went to the library meeting rooms and saw Beth waiting for him. She had a smile on her face as all of her books were open like she was hard at work studying. He walked in closing the door behind him and sat down. "Hey, you."

Beth quickly began asking questions about the project and the final. Caleb did most of it, but he knew she needed work to finish it. He thought she was going to ask questions about the other day and when she didn't, he wondered if he should bring it up.

"I wanted to tell you again that I really liked what we did," Caleb offered, wanting to reassure her that he did like it and maybe get her to offer it again.

"Can I ask you a question? It's about you and Paige."

"Sure." Caleb now wondered if she was going to guilt him into regretting what happened or worse, blackmail him.

"Does she know about what we did? Do you and her fool around...I mean have anal sex and stuff like that?"

His brain instantly felt relief that there was no blackmail or comments about her not liking it. "Wow. I've never really talked about it before, but I guess I can share with you. To tell you the truth...we never had sex. She is waiting for marriage. She does give me hand jobs and some-times gives me head, but mostly hand-jobs."

"Does she know that you like anal play?"

"Nooo. God no. She would freak out." He knew that she was anti-gay and spoke against people who liked that sort of stuff and would have flipped out in school if she found out a trans-girl was attending.

Beth looked down at her books and then up in his eyes but seemed to be shy when she spoke, "If you want to try it again, I wouldn't mind. I will keep it a secret too."

The feeling of excitement was running through his body as he stated, "I would like that."

The memory of sex with Beth came back to him as did his erection. The thought of what the second time would be like crept into his mind, strengthening his erection to the point of him having to adjust his pants. The idea that Beth wanted to fool around again was like a fantasy that was playing out.

Caleb cold see that Beth was acting shy and wondered why. He did not want to say anything for fear that he might ruin his chance at her fucking him again. He acted like there was nothing wrong and went back to helping her.

With Paige working late tonight, Caleb set a time with Beth to come over. His mom and dad were both working, and he would have at least four hours of alone time before they would come home. Beth agreed to the time and Caleb ran through in his mind what he needed to do and imagined how it was going to feel again.

With his long shower plus cleaning every inch of his body in and out, he was ready for Beth to come over. She rang the doorbell at the exact time and stepped in wearing a t-shirt and jeans. With only a towel wrapped around his waist, her eyes greeted his body with a smile before she even looked up at him.

With a smile on her face she stepped inside. "Ohhh, I see you're ready."

"You said to be clean."

"I did. And I see that you listened."

Caleb led her to his room and quickly closed the door. He thought of how it was going to feel and the orgasm he was going to have was already having an effect on his member. He watched her pull down her jeans to show her panties, although he wondered where her dick was as there was no outline or bulge of any kind.

Beth pulled down her panties and when she bent over a little, he saw her dick drop from between her legs as if it was tucked away for safekeeping. She then looked at him confused as his stare was obvious. "What?"

"Ohhh, nothing. I just did not know you did that with your dick is all."

With a caution in her voice, she answered back. "Sometimes. Depends on what I want to wear. Are you bothered by it?"

"No, not at all."

"Ok. You can get on the bed."

Getting on the bed, he thought about how he was ready to get fucked and cum. His dick was semi-erect and ready to be played with already. He felt movement on the bed and listened to Beth moving herself in position.

The familiar cold liquid of lubrication was being poured on his inner ass cheek and butt hole. It was then followed by her fingers as she was rubbing it into his skin. It stopped and then replaced with the sensation of her tip wanting to gain entrance.

Beth said nothing this time and then pushed in slowly. Caleb felt her girl helmet slip past his outer ring muscles and gain access to his anal cavity. There was no pain but only discomfort and fullness as she pushed more of her shaft in. The discomfort turned into pleasure as Beth retreated her cock and pushed back in confirming that he was indeed having butt sex.

"Ohhhhh," Beth moaned for the first time as it shocked him that she was being open about liking it and also reminding him that she had a dick inside of him.

Reaching for his cock, he found it already covered in precum. Beth was moving slowly but the tingles of his ass muscles loved the feeling of something soft yet hard in him. The nerve endings in his ass were going wild now. She was sliding in and out of his ass, making sure she plunged deep as her body now banged against his butt.