Blackmail Ch. 02

With the drive less than a few minutes, Caleb found himself in his bed laying down thinking of what just happened. His memory recalled every second of what went down and the sensations of having sex with her and then sucking her off. The guilt of swallowing sperm was not there, and it shocked him as did the exciting memory of what it tasted like. The feeling that it was her cum he swallowed seemed to make it right. His erection poked up and he decided to text Beth.

"Thinking of you." Caleb texted with a picture of the outline of his jeans showing his bulge that begged to be set free.

Beth sent back a smiling face with the words. "I can come over right now and help you with that."

"You would?"

"It's my job to handle my boyfriend's cock, so yes, I can come right now." Beth texted quickly.

"LOL. I have college work to handle since I was out for two days. I would so take you up on that though."

Beth texted back emojis and a picture of her face smiling. He wondered if she would send a few nude pictures but then realized that she might not be into that. He did think about jerking off but then knew that he could save it for tomorrow. He just did not know if she wanted to fuck him or he would fuck her. He also contemplated that maybe both could happen.

The rest of the day and night Caleb ran through what happened. The memory of fucking Beth in her tight ass to the memory of how her cum tasted as it spurted on his tongue. He could still remember the outline of her curves in leggings and how it seemed unreal that her ass was sculpted.

The next morning and afternoon were books and papers followed up by typing up his college work to submit online for the makeup dates. Beth texted him that she was thinking of him and he did the same. His dad was home tonight so having her over seemed not the right time.

Still wanting to see her, he texted her about the movies and possibly a bite to eat after that. Beth texted back that it seemed perfect. He wanted to inquire about sex but the thought that he did not want it to seem that that's all he wanted. Then again, he figured he might get lucky and decided to do a full cleaning before going out.

Worried about Paige finding out he was dating so soon made him feel guilty. She knew a lot of people in the town and all his friends knew her as well. She could easily cause a big uproar of problems if she found out he was over her so quickly or if she found out he was messing around with Beth while they were still together. He also knew deep down that if Paige found out Beth was a transsexual his life would be over.

With the worry in his head, he still picked up Beth and prepared to meet her family. He was shocked when she was waiting outside as to bypass meeting the parent's routine. Even though they were not teenagers in high school, they both still lived at home. He knew her parents were like his, very conservative and old school.

As he stopped to let her in, he could see her wearing a tight black skirt that seemed to accentuate her legs. She had a formfitted white top on that he knew would show off the curves of her breasts that he knew were real. She had a small jacket covering her chest keeping a somewhat modest appearance.

Beth got in his car smiling wide. "Hey...nice car. I always wanted to ride in it too."

"Thank you...you look really hot tonight," he admitted, knowing that she did look stunning.

"Ohhh, thank you. I thought I would wear something nice since we are going out on our first date."

As he drove to the restaurant, he wondered about how comfortable she was with that skirt on knowing she had to have tucked in her package. He looked to her when they pulled into the parking lot. "Does it hurt when you...wear clothes like that?"

She gave an honest look back that was not neutral and not seemingly bothered by the question. "I am used to it, but I love dressing up. I love that I can wear these clothes and that I feel comfortable wearing them."

"Okay...I thought it might hurt and all, but I do think you look really hot in them."

"Aww...you like me dressing up?"

"I thought you looked hot wearing the sweatpants the other day and when you came into class, I couldn't help but stare," he admitted, smiling that he really did stare at her ass.

"I know. I saw you staring at it. I liked that you were looking too. Guess wearing those leggings had an effect," she answered with a big devious grin.

"You knew? God...do you know how good your ass looks in those. Fuck, I spent an entire class period staring at your ass."

Her smile grew wide. "I know...and you got to fuck it the other day too."

Caleb got out from the car letting her out playing the perfect gentleman. He then opened the door to the restaurant and played the perfect boyfriend like he always did with Paige. He had her order first and then he did the same before going into a conversation about what she liked.

Beth divulged that she was a huge fan of movies and that she read more books than he ever did. She was interested in the sports he played in high school and why he decided to go to community college over a big university. He smiled and asked her the same question about college.

Beth explained that she wanted to be a writer, but also thought about being a lawyer like her father. She explained how she could not decide and that a community college might help her without making the big commitment. Caleb smiled saying that it was a good idea before he told her that the car was his reason and then he watched as she laughed, calling him an idiot because he knew that big universities would have accepted him.

The food came and he felt so comfortable talking to her that he did not look at the time as they missed the show time. "Shit...we missed the movie."

"It's okay. We can go see a later show, or did you want to go somewhere and fool around?" she said smirking.

"I would like to do both, but I really do want to make this a date, so let's catch a later showing."

"Can I ask you a serious question?" she said as she pushed the plate of food away from her.

"Sure."

"Let's go in the car so we can have some privacy," Beth responded as she stood up looking around.

Caleb nodded leaving cash on the table and walking her out thinking that he was supposed to say fool around instead of the movies. He felt it was wrong to assume sex and he knew it was no big deal to eat anyway as she would put out when his parents were not home anyway.

As she closed the door giving them privacy, she looked at him serious. "I knew some people in there and did not want people to overhear us. I don't mind us being fuck friends and keeping what we have secret. I don't mind us being secret boyfriend and girlfriend, but are you ready to announce we are a couple? I don't think your parents would like you dating a girl like me."

"I thought wewere dating?" Caleb asked, confused to why she would think they were not dating after the last time.

"I mean, we are fucking...and kinda dating, but I don't think you consider me your girlfriend like you would Paige."

"I am ready for that...I mean in a week or two I can tell people once Paige leaves for her missions' trip."

"Are you ready for people calling you a fag or gay? People wondering about your sexuality in this town because you're dating a tranny?" she said, looking at his eyes almost hurt.

"I don't know...not really, but I want to date you though."

"You want to fuck me and have me fuck you, but I don't think you want to date me. It's, okay...I don't mind keeping it the way we have it. But dating out in the open is not something you are ready to handle."

"I don't want it to be just about the sex though. I really do like you and do enjoy spending time with you," he confessed again, feeling she was easy to get along with and an amazing person to be around. His mind quickly thought that dating her was a lot easier than dating Paige. Paige loved the drama and would put herself in it just to have something to do sometimes.

"You're sweet. Let's just keep it a secret for now."

"Okay, but I still am going to consider you my girlfriend and want to take you out."

Beth leaned in kissing him and he felt her soft lips against his. "Okay. We are dating, but in secret. I don't think the movies are a good idea though. You know people are going to see us there."

"My dad is home tonight so we can't go there."

Beth gave a disappointed look back. "My parents are home too."

"We could go to the campgrounds. Nobody is there at this time."

"You want a blowjob?" she asked with a smile.

"I could go down on you if you want," Caleb answered, feeling that he really wouldn't mind sucking her dick again.

"I have a poolhouse that we could use. It has a bed and privacy. My parents can't see the lights when they are on and we could go there."

"Okay," Caleb said feeling that he was okay with getting and giving head.

As the car was moving, he felt her hand touch his pants and then grip his thigh. He looked over at her quickly as she smiled back. He could not help but think that he was dating her, and they had to keep it a secret. He now wondered what things she wanted to do.

As they pulled down their road she looked at him. "Park at your house. We can quietly walk to my backyard. It's only a few blocks and most people are asleep. We can then sneak into my backyard."

He followed her lead and they walked down to her house under the cover of darkness. He watched as she looked around and made it to her fence and opened it without a noise being made. She motioned with her finger to be silent and he followed her deeper into her backyard and then into the secured pool house she had.

The door to the poolhouse was closed. She flipped on the lights to reveal a small two room building that had a bed, a kitchen, and a bathroom. It was nicely decorated and seemed more like a guest house.

Beth quickly jumped over to him and planted a kiss right on his lips. His hands went to her waist and then hers went to his pants. Before he could stop the kiss, her hands were on his pants to get them off.

With his pants down, Beth quickly pulled down his underwear and knelt down. "Do you want me to suck you off first and then maybe you can do it to me or jerk me off? If you don't, that's okay. I don't want to seem like I am forcing you into something you're not comfortable doing."

"You serious? I am the one that asked for you to fuck me and you think I don't want to return the favor? I like experimenting with you. Besides, I already sucked your dick and swallowed."

Beth got up and then pulled off her jacket showing off her tight top that accentuated her chest. "I know, but I get worried is all."

"Worried? About what?" Caleb asked wondering what she was afraid of.

"I just think you're not going to like it is all."

"Well, I can tell you that it felt really good when you fucked my ass and jerked me off. I never came so hard in my life," Caleb admitted, remembering how quick he came from it and how amazing it was.

"Do you want me to fuck your ass again?" Beth asked smiling wide.

"Do you mind? I mean I can fuck you after or go down on you. I want it to feel good for you."

Beth gave a look of concern. "I don't have condoms though. Do you mind me fucking you bareback? I mean...I am clean and all, but I don't know if you want me to do that."

"Well, I guess this means we are going to be monogamous then," Caleb joked as he smiled at her to relieve her worried look.

"Better be. We are dating," Beth joked back with a smile.

"I didn't plan for us to do this. I need to run inside and grab some lube if we are going to do this. Do you need to shower and clean up?"

"No...I actually did it before I left. I had no idea we were going to do this, but I thought I would prepare for anything."

Beth smiled and hurried out the door. Caleb wondered what he got himself into and then thought how good it was that he was with her. He quickly let his mind rush with thoughts and second guesses to what he did and was about to do, but the sense of it being right came to him. That Beth was the right person for him.

Beth returned with a bottle of lube in her hand and smile on her face like she got something she wanted. Caleb looked at her wondering why she seemed so happy. She then closed the door and walked over to him. "You ready?"

"I am," he answered feeling the butterflies in his stomach, knowing her girl dick was about ready to take him.

Beth quickly undressed and he could see her panties showing no outline or bulge. He watched as she slipped down the thin material revealing a clear tape holding her real sex. He quickly stripped down and then moved in front of her before she removed the tape.

As Beth pulled the tape off, her girl member dropped down. It was thin and soft hanging there right in front of him. Not waiting to be told or to be told not to, he moved her by her hips closer and then reached out to touch it. With her soft rod in his hand, he moved his head closer and then opened his mouth accepting her tip between his lips.

"Ohhhhh...that feels so fucking good," Beth moaned softly.

Her skin smelled both clean and fresh while her member was soft and flexible. He slowly moved his tongue around her head and then moved his mouth down her shaft easily taking it all in as he pressed his nose against her waist. Once against her body, he could smell her perfume making him feel like he was pleasing his girlfriend.

Back and forth he went down her shaft feeling her silky skin expand and then grow in his mouth. When she was finally erect, he still was able to go deep loving how he knew it was his mouth that got her that way. All sense of morality was gone as his only thought were making sure she was getting enjoyment.

"Ohhhyess...just like that," Beth moaned out as he kept his lips tight feeling the skin of her girl shaft slide through his lips.

Beth finally pulled away. "Let me fuck your butt now."

Caleb got on the bed and turned over. Beth then gave his ass a playful slap. "Ohhh, love your ass. So fucking good looking."

As he positioned himself for anal sex, he kept his back arched and his face down. "Like this?" he asked feeling the flutters again, knowing her girl dick was about to be inserted in his rectum bareback. It was not fear but the anticipation of unknown pleasure.

"Let me get you ready," Beth replied as he felt a cold sensation right on his anus as the lube was being dripped on him.

She held his ass cheeks apart and then slid her two fingers over his anus and then all inside his ass crack. It felt like a wet massage and was very sensual as her fingers grazed his sensitive skin applying lubrication to his anal entrance.

He then heard her move closer to him and then felt her hands on his hips. Caleb felt his heart pound with excitement and his dick hardened at the idea his girlfriend was going to spear her girl dick inside his ass again. He then felt her crown at his rim and a split second later he felt his slippery anal muscles give in to the pressure being put on it from her tip.

"Ohhhhh...fuckkkkkk," Caleb moaned as he felt her shaft slide quickly inside of him, impaling him with her shaft.

"Feels good?" Beth moaned softly, keeping her rod deep in him and not moving as if to let him adjust.

"Sooo fucking good."

Beth pulled out a little only to push back in. He could feel her hard sex organ push in and stretch his rectum as if it was a sex toy for fucking. The pressure and fullness of having her inside his ass was sending pleasure to his body. There was no pain, just a little discomfort and a sensation of his ass being full and open.

Beth began rocking her hips back and forth sending his ass into a frenzy of being open and used. He relaxed and let it happen, feeling his ass just open up more and more until the discomfort was gone and it was just a pleasuring sensation of her girl dick fucking him.

"Ohh...ohhhh...ohhhh...fuckkkkk," Caleb moaned with each thrust she was giving. His idea of sexual release was now in question as he felt he was being fucked.

"AHHHhhhhhhh. Your ass feels so good baby. I am already close," Beth moaned in a girl voice as she pushed in and held it.

"Already?" he asked, feeling his body wanting more and wanting it harder.

"It feels so much better without the condom," Beth moaned.

"Keep going then...feels good for me," Caleb confessed as he felt his anal muscles had given up and were now the receptors of his sexual pleasure.

Beth pushed in hard and then grabbed his hips. He felt her girl dick impale his ass again and then again. He felt her hard girl muscle pushing through his anal passage with pure ease as she thrust home. His ass was giving no resistance whatsoever as he felt the openness of his asshole make it a sheath for her girl cock.

Caleb could not help but feel a build up inside of him as Beth's erection was punching something inside of him that was making him feel good. It was a mixture of pleasure and the urge to pee. Beth was just pumping away as her dick was like a machine. The urge to push was there and he could not help but do just that.

Caleb clenched his ass muscles and then tried to push her erection out just as she was pushing into him. There was no contest as Beth's dick won and continued to slide through his clenching rectum muscles. The pleasure of his rectum closing on her shaft only intensified the pleasure of her fucking him.

Her hand gripped his hips hard and her thrust became rapid just as he kept clenching while also trying not to. He felt her waist slamming against his over and over. He was able to take her thrusting slams as she positioned her dick right into his ass hard. He had no idea his ass could take such a pounding, but listening to her moan and breathe hard made him feel he was the reason she was getting pleasure.

"Ohhhh fuck...oh fuckkkkkk. I am cummmmming!" Beth moaned loud as she pushed deep and held it like she was making sure her girl cum was properly deposited in his ass.

He felt it deep in him as she held him close, feeling her body against his. Her dick was twitching inside of him as a slight sensation of warmth could be felt. It was so erotic he thought.

The idea of her blowing her girl cum in his ass sent alarm bells off of forbidden taboo. But it was too late, he felt her body shaking against him and he knew she had just ejaculated her girl sperm in his anal passage. He felt a little bit of warmth in his ass knowing that it was her spunk being pumped into him.

Beth quickly pulled out and he turned to see a look of horror on her face. "I am really sorry. Please don't be mad."

"Ohhh shit...you came in me," he commented, feeling a rush of what just happened as it was mixed with the loss of her dick from his ass.

"I am sorry...I couldn't help it. It just happened." Her facial expression looked both mortified and scared.

"It's okay...you're fine. Did it feel good?" Caleb said, calmly hoping to make her not worried about her putting sperm in his ass.

"It did...I did think I would like it, but it felt really good."

Caleb then looked down to see his own dick covered in slime. It was thinner than cum almost like precum, but it was all over his shaft and his ball sack. He leaned back, and looked at his member as it was soft and covered in thin cum.

"I think you came baby. It looks like you came from me fucking you," Beth said smiling as she turned to him.

"Did I? It felt weird, but in a good way. I think I can get hard again to fuck you if you want."

"It does feel different...I like it when I do it. How about I get you off really good?"

"How?" he asked, wondering what she was planning.

"I am going to stroke you like before and be inside of you. You came really hard last time wedid it too."

"I did...but what about you?" he asked, knowing he did cum hard but also feeling guilty about not fucking her knowing she wanted it.