Blackmail

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Ahhh...ahhhh," Beth moaned as Caleb began to stroke his erection fast.

Focused on how great it felt to be butt fucked by her cock, he already felt his balls preparing for a quick orgasm. It was not even five minutes and he felt the telltale sign of his cum about to be ejaculated.

Stroking fast as he felt the pressure and sensation of her cock pounding away at his ass like it was a hole to be fucked too much. He stroked to the point where he needed to cum and then let out his moan. "OHHHHHHHH FUCKK!!!"

His cum blasted on the sheets with a hard force stream like there was a blockage that just burst. Beth pushed in, holding it. "You cumming already?"

Beth pulled out as he looked her in the eyes, almost worn out as his orgasm took everything out of him. "Ohhhh, yes. It was amazing too."

"Well. I'm glad I could help," Beth said softly.

"Did you like it? I heard you moaning," he asked, wondering if she did like it, hoping that if she did she would do it again.

"I did...but I didn't cum," Beth admitted with a sorrow in her eyes.

"Ohh...shit. Did you want to cum now?"

"Do you mind? I mean I can wait until later," Beth replied with hesitation in her tone.

"Do you jerk off or do you do something else?" Caleb asked, wondering how she got off.

"I just jerk off, like you do."

"Ohhh, go ahead. Please, cum for me," he said, thinking he should have known and felt guilty inside for not realizing something so easy.

"You don't mind?" Beth asked, still hesitant as he saw her erection dying down in the condom.

"Ohhh, yeah. I don't mind. Do you need to watch something or use a toy or anything?"

"Do you mind if I look at you?" Beth asked as she pulled off the condom showing her semi-hard girl dick.

"I guess, do you want me to do anything?" Caleb asked, wondering what turned her on. The idea of bending over to show his ass to her came to him and then wondered if she wanted to fuck him until she got off.

"No. Just lay on your back."

Caleb did as she asked, and he watched her slowly stroke her member. It was not as hard as it was when she entered him, but it was gaining life back. He looked at her eyes to see she was looking right at his limp sperm covered manhood. Her gaze was unflinching as she stroked her meat to his own cock.

Beth was stroking her dick faster and harder. Her breathing was becoming short and labored as he knew she was in full masturbation mode. He wanted to help her as both the thought of her stroking off to his member and watching her was having an effect on his own cock.

Caleb took his fingers grabbing his cock and flopped it side to side as it made a wet slapping noise from it being covered in sperm. "You want me to jerk it off for you?"

Beth smiled wide and nodded her head quickly. "Pllleeease."

Caleb began gliding his hand over his shaft feeling the sticking mess on it. It was still warm and felt gooey to the touch. He slid his body closer so as if she could get a better look. The tips of their swords were inches away from touching each other as they both stroked to a different pace. Caleb was moving slower as to let her watch his cock move in his hand while she pounded her girl dick trying to get off fast.

"You going to cum?" Caleb enticed her as she just nodded her head seemingly unable to talk in her excitement of masturbation.

His slimy cock now feeling like it was a slick pole in his hands; he could see Beth about ready to cum. She moved closer almost touching her tip against his. She then looked him in the eyes as he knew she was moments away from exploding.

"Ahhhhhh," Beth cried out as Caleb stopped stroking to witness her cum weakly ejaculating right on his hand and his dick.

Beth kept stroking as a second spurt just dribbled out covering the tip of his dick adding to the cum that was already on it. Caleb felt the warmth of her girl sperm on his hand and dick as his own member twitched with excitement.

"Ohhh shit."

Beth gave a look of horror as she looked at him. "I am sorry...it just turned me on. I didn't mean to cum on you like that. Please don't be mad...I can clean it up."

"It's fine. Did you cum good?" Caleb asked smiling, wanting her to feel calm as he secretly got turned on by watching her.

"Yeah. I came really hard. Are you sure you're okay? I didn't know if you were into that and all."

"Oh, you're good. To tell you the truth, I got turned on by watching you...and I kinda liked you cumming too."

Beth smiled as she answered back, "You liked it? I can do more if you're okay with it."

"More? You mean you can cum again?"

"No. I was thinking maybe you would like me to go down on you. I don't mind sucking your dick. I am not sure if you want to because of Paige and all though."

Caleb thought about Paige quickly and knew that forbidden anal play he wanted was something Paige would never do or want to hear about. It was like a taboo secret he could keep without the guilt of cheating. With Beth offering oral, it was a step into the realm of cheating as Paige was already giving him oral when he wanted it.

"You don't have to. I like what we are doing. I don't mind you jerking off on me either if it helps you getting off."

Not wanting to upset her, he thought of an answer that was more neutral. The idea of her getting off to him and on him was a thrill too. Being the object of sexual desire made it seem like a fantasy that was playing out in real life. He looked at her as she was still wearing a t-shirt and wondered what her breasts looked like, still amazed that she had a dick.

"I guess I am going to get going."

Caleb wanted to ask her more questions but also knew that time was limited. He walked her to the door asking for her number and then telling her that he was really turned on by what happened. Seeing her face light up let him know that she needed to hear that too. He watched her leave and wondered if he should have taken her up on the offer for head.

With a shower needed, he felt the water rinse off his cum and hers as well. The idea that he was fooling around with a real life transsexual made his heart race to a thundering pace. His memories phased from seeing her undress to watching her face in the throes of an orgasm as she shot her cum on him.

The next day he wondered if he should tell Paige that he messed around. He did not feel it was really messing around since it was something that he wanted to keep secret anyway. The idea of wanting more sexually from her came to him, but he did not know how to say that he wanted her to use toys on him or that he wanted to have sex with her.

Caleb knew Paige was very religious and the commitment to saving herself for marriage was not just words as she would not even let him touch her sex or even look at it. She was okay with hand-jobs and giving a blowjob was something special that he might get once a month if she was in a really good mood.

The two classes he had were done before noon and it wasn't until next week that he would have biology class with Beth again. Paige was doing her charity work and boredom left him with texting a message to Beth saying that he liked what she did. He hoped it would be less weird for her to do it again.

"I wanted to tell you that I liked what we did. Everything including you cumming."

Beth replied with. "I did not know if you were into seeing me naked. I just thought you liked what I did for you."

Caleb had to admit she had a gorgeous body that had all the right feminine curves to it. "You do have a hot body. I don't mind if we do it again."

"You think I am hot? Would you want me to jerk off with you again?" Beth replied with a bunch of smiley faces after her response.

"I don't mind." Caleb answered thinking about how hot it was to see her cum.

"Do you still want me to suck you off?" She texted as he weighed the pros and cons of having another girl go down on him.

He like her wanting him but knew that it was not necessary and that she was already doing a lot. "You don't have to."

"I want to."

"Do you really want to?" Caleb answered, wondering how far she wanted to go with him.

"Yes."

"So, we would stop what we are doing and you would just suck me off from now on?" Caleb questioned, hoping that she did not want to give him anal and that she was only into giving head.

"We don't have to stop the other things. I will just suck you whenever you want."

"You serious...whenever?" The taboo of what he was doing with her and the thrill of her wanting to give him a blowjob took a hold of his willpower.

"I will do it right now."

Taking a deep breath, he wondered if she was playing with him. The only thing he could do was to call her bluff. "Ok...right now. Come over and blow me."

Beth replied. "Be there in 5 minutes."

The idea of her coming over for a blowjob booty call was exciting, and he knew it. He had to beg Paige for her to suck him off and now Beth was willing to just come over to service him. There was a bit of guilt, but he could also feel the thrill of getting a blowjob and the excitement of being with Beth again.

With his dad home and in his study, he did not want him to know a girl was coming over that was not Paige. Like the rest of the community, he was religious and also loved that he was with Paige who was waiting for marriage. Beth needed to be intercepted and led to his room quietly.

Caleb waited outside and figured he would intercept her and walk her around back. His father's office was downstairs and going in the back would bypass his office. He watched her pull up in her new looking car and it reminded him that she was well off like he was and not some street girl.

Beth stepped out wearing a t-shirt and sweatpants and he motioned for her to come around back. She did and all he could think of was that this pretty girl was going to suck his dick. Every-thing else did not matter as she looked cute to him even though she was not dressed up or even wearing makeup.

Not saying a word as they snuck up the stairs, he led her to his room and closed the door. She sat right on the bed looking at him. "I guess you're not telling your parents about me. Is it because I am trans?"

Caleb instantly thought about what she said as the realization was brought to his attention. He knew what she was, but just didn't think about it. He also knew that it was not because of that. "No. It's just that my parents are friends with Paige's parents."

"Ohhh, so you're sneaking around getting blowjobs from different girls?" Beth said with a smirk on her face.

"Not different girls, just you. To tell you the truth, I never fooled around with anyone other than Paige. She was the only person who I was with...or almost with."

"Oh. So, do you still want to go through with this?"

"I do."

"Okay. Get on the bed," Beth commanded.

He switched positions and sat on the bed. Beth immediately kneeled down and unbuckled his jeans. Once the zipper was halfway down, she looked up with a big smile. "You do have a nice dick."

Before he could reply, he felt her lips against his tip as she was kissing it. The kiss was quick, and he felt her lips press against his tip, giving him the sensation that it was getting attention. Beth then opened her mouth and moved her mouth further down taking his entire member. The softness of his manhood getting quickly excited as she moved back up to his crown licking hard inside his pee slit was turning him on.

Beth moved back and forth as he felt his blood giving serious life to his cock. It pulsed rapidly a few times as she was no longer able to go deep anymore as his shaft thickened and lengthened as his erection grew to full strength. Beth did not stop as her tight seal with her mouth moved back and forth, gliding on her salvia as his shaft had a hefty coat of her spit on it.

"Ohhhhhh GODDDD," Caleb moaned deep as he felt all the nerve endings on his dick being stimulated at the same time.

Beth looked up at his eyes as she moved quicker with her mouth. Not using her hands, all the pleasure he received was from her lips as she was giving a true blowjob. The feeling of her soft lips pressing hard and then sliding up his slick rod was intense as he felt it throb.

Caleb was giving soft yet deep short moans as Beth would move up every so often to press her lips and tongue against his helmet, making it pulse from the direct pressure. The muscles in his body were tightening up as he felt the building of his orgasm. It was getting closer but not there yet as Beth moved back down his shaft almost taking him deep, only to move back up to the tip, stopping to only slide down fast again.

"Rgggg." Caleb let loose his guttural sound as he knew he was on the verge of exploding. This was like nothing he felt before as it was only a few minutes into it, and she was good enough to work his orgasm out of him.

The end was near as he felt the point where it was no longer able to stop. His orgasm was approaching as Beth was now moving up and down his salvia covered shaft in long and fast motions. He did not know if she would swallow, but still wanted to warn her.

"I am going to cum," Caleb moaned out as he felt the urgent need to expel his essence with great force.

Beth moved back up to where his crown was in her mouth only. Her hand finally gripped his shaft for the first time and began to jerk with great speed. Caleb could not hold out and slammed his body against the bed then the intense demand all his muscles work taut in ejaculating inside her mouth.

"OHHHHHHHH FUCKKKKKK!" Caleb cried out as he felt the direct pressure on his cock head and her hand milking him like he was meant to give her his warm cream.

Beth moved back as he watched her swallow his cum. She then smiled and licked her lips. "You came hard."

Caleb exhaled deep and felt weak as his body had nothing left in him. "Ohhh fuck. That was good."

"I am glad you liked it," Beth answered smiling.

"Do you need to get off?" he asked, wondering if she was hard and needed to cum too. He figured she would just jerk off on him again and he could see her dick spurt off again.

"I can go home and do it. You don't have to worry about me," Beth answered quickly and with a hesitant tone.

"I don't mind. I kinda like knowing you get off."

"You do? I was thinking you just tolerated me doing it."

"I did like it. I liked seeing you, and knowing you got off."

"So, you don't mind me looking at you when I do it?"

"Ohh that. You really liked looking at me?" Caleb asked, wondering if he really did turn her on. He wondered why it turned her on and not Paige.

"I do. I think you're cute. Do you mind?"

"I don't mind at all. Do you want to cum on me again?"

"I would like that," Beth answered softly as her face smiled.

"Okay, you can cum wherever you want to," Caleb replied as he opened his legs and moved his hand to his limp, exhausted member so it now flopped over his leg.

Beth slid down her sweatpants and revealed her semi-erect girl dick. Her clean-shaven private parts seem to highlight her feminine form even though she had a penis. Caleb could not think of a hotter girl he jerked off to online either. It was like she was the most perfect trans girl he ever saw.

He watched as she moved her hand along her shaft bringing more life to her erection. After a few long, slow strokes, she was fully aroused, and her tip seemed to be like a spear ready to penetrate anything.

"God, you look so fucking hot," Caleb commented as Beth kept her eyes on his body seemingly aroused by him.

Beth smiled at the compliment and continued to please her erection with long sensual strokes. Caleb could see that she was fully emerged in her masturbation when he asked, "Do you want to cum on my cock, or my chest."

"Your cock....I want to cum on your dick," Beth moaned out as she was stroking fast now.

"You want me to stroke you?" Caleb asked, wondering what it felt like to touch another dick.

He never saw himself as gay or even bisexual. Boys never once turned him on, but there was something about Elizabeth that stirred something in him. Her dick was slimmer than his, but something about it told him that it would be erotic to stroke. The idea seemed too perfect when he asked and now, he could not think of a reason why he should not stroke her off.

"You don't have to."

Not listening to her, he switched spots so she was sitting and he was kneeling down. Her girl dick was in front of him and her sleek tip was already showing a drop of precum. He reached out touching it and felt her soft yet hard girl stick.

It was almost surreal as he held it in his hand. The smooth texture of her skin was almost silky and feminine and yet it was a real-life penis. Her balls were not as big as his, but they were shaven and looking somewhat pretty. As he held it, he could not stop thinking about why he did not do it before.

Caleb began stroking it with long slow strokes feeling her dick pulse in his hand from what he assumed was her enjoying it. He looked up at her smiling because of it. "Do you like it? Am I doing it right?"

Beth nodded her head as her mouth was open. He knew she did not have to speak as he knew she was loving it. There was something beautiful about getting your dick played with and he knew it and now giving it to Beth was getting him excited all over again.

Stroking it fast, but not too fast, he felt her girl dick get hard to the point of making him wonder if she was going to cum. He looked up knowing it was only a few minutes of stroking. "You going to cum?"

"Yesssss...I can't help it. It feels really good," Beth moaned out as he knew he was doing some-thing right.

Back and forth he stroked, making sure he touched the tip and then stroked down. Her dick was throbbing now, letting him know she was close. He kept stroking not breaking his stride as he heard Beth's moans grow louder. It then finally happened as he watched her slit pour out her orgasm. It was warm on his hand as the thrill of knowing he stroked her off came to him.

Caleb looked at her smiling as she did the same. More of her warm cum dripped on his hand covering it as he did only short strokes near the bottom of her shaft. "Did you cum good."

"I did...really good."

He looked at his hand as it was covered in white jizz. "I don't mind doing to again if you want. I know you helped get me off. So, I figure I could do this for you after."

"You liked it?" Beth asked as she gave a confused look.

"I liked doing it for you. It was kind of a thrill."

"Okay then."

The noise downstairs made Caleb snap back into reality. He looked panicked at Beth. "Shit. He might have heard us."

"Do you want me to go?" Beth said as she pulled up her sweatpants as her erection only died down a little and was making a tent in her sweats.

"Yes. Can I text you later?"

"Yes," Beth answered as she snuck out of the room following Caleb as he led her downstairs to her car just as his father made his way around the house.

Just as he walked in, he wondered how far he went. Paige texted him and the thought of wrongdoing hit him now. She was texting and as he reached for his phone, he realized his cum covered hand was still sticky.

He texted Paige that he was going to bed and not feeling good. He then texted Beth that he liked what they did and would see her tomorrow in class. Paige texted him that she was praying for him and that she wanted to see him tomorrow. Beth replied just as Paige did with a picture of her wearing a bra.

Caleb could not let his thoughts of Beth go away. He loved the way she looked and wondered who else knew about her secret. It was a chance incident he found out and he knew his father did not even mention it to his mother.

It was before class began when he walked into the college cafeteria. The large open space was filled with people eating, talking and doing work on their computers. He normally skipped break-fast but today he decided to venture in and grab a bite while finishing up some work.