M.I.L.F. vs Stud Ch. 06

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After my cute - but spent- brother went on his way (chest covered with dripping cum), I texted Sotoya a snapshot of his Abercrombie ass as he walked out of the room. I told her that we were following her plan. I could only hope that it would help him.

As it turns out, it did help him. For the first time, Kyle took a bronze medal home that weekend. Oh, and after two weeks of finishing in second, I walked away with the gold!

TINA:

After leaving the kids, I just couldn't help but wonder if Katye might take her brother too close to the edge. I didn't mind her toying with him, but he hadn't had release in nearly ten days, so it wouldn't take much for the inexperienced boy to go over the edge. I don't think Katye would give him release on purpose unless I gave her permission, but it could happen accidentally very easily.

Maize had suggested that I have Kyle sleep in a chastity device to eliminate any temptation to masturbate, but I had decided against it. Kyle had proven to be obedient and resisted the temptation so far. But I saw the look in his eye as his sister was playing with him. He just might talk her into doing something she wouldn't otherwise do.

I walked back down the hallway when Kyle came out of his room wearing something different than he was wearing when I left him only a few minutes prior. He was wearing the French cut panties that I would sometimes have him wear while doing housework. The French cut back rode up his ass very nicely, covering only the top of his muscular ass in a V-shape. But I had to wonder why he was wearing these instead of his Unicos.

"Stop right there, young man. Turn around."

Reluctantly, the eighteen year old teenage boy turned around to face me. He held a small pile of clothes in his hands, which he put down to his side.

"Nice to see they still fit you," I commented, testing the front pouch for its elasticity. They still held to his body without a gap. "Why did you change?"

"I have to do chores today, and I know you like to have me wearing these when I do them," Kyle responded nervously.

Something wasn't right. I asked to look at the clothes he was holding, the jeans, T-shirt and underwear he had just been wearing. I picked up his white Unicos and discovered the problem. His underwear was covered in his semen.

"Oh my god, boy! How many times did you cum in these?"

"Just once."

"This is just one load?" I asked, lifting my cum covered fingers from the underwear.

"Yes, ma'am."

By this time, Katye had come running out of her room to see what the fuss was all about.

"Katye, did you have anything to do with this?"

"No, it was just me. She wouldn't help me so I did it in my room," Kyle said before Katye could answer.

"You march yourself into my bedroom right now!" I growled. "I want you standing in the corner, hands clasped behind your head. We'll be back in one hour! You have some time to think about what you did."

I needed an hour to get my temper under control and to let Kyle recover. I wanted to take this opportunity to teach both Kyle and Katye a lesson. I returned in exactly sixty minutes with Katye in tow.

I ordered my boy to strip and lay across my lap. Reluctantly, he complied, letting his bound sex rest against the outside of my left thigh. I removed the restraint to allow his sex to hang free for the first time in over a week.

With one hand, I held my boy steady by the neck, and with the other, I spanked his bare ass as hard as I could until his cheeks became crimson red. He was screaming with each slap by the time I was done.

When I finished, I held him there, caressing his back. I listened to him quietly sob. I spread his plump ass cheeks apart with my right hand and pressed the middle finger of my left hand against his anus. I listened to his sobs turn to a moan. I massaged his opening for a moment before entering him. He gasped and his cock began to grow against my leg. I made sure Katye was positioned well to view his reaction.

I pushed one finger in followed by my index finger. Slowly, I massaged his prostrate. It was not nearly as full as it had been an hour ago, but I was still able to coax a fair amount of precum out.

"See Katye? Fingering a boy makes him hard. This is how you milk a boy. Ah, there we go. Look at the flow," I said, referring to the free flow of fresh precum from the tip of his over-sized penis head. It dripped in thick long strands before snapping and pooling on my hardwood floor. "It gives him some physical release while still denying him the mental pleasure of an orgasm. In time he'll become used to this form of release. See how it calms him, too?" I stroked his sweat covered hair and upper back. "That's my boy. You're doing great, Kyle."

I reached between Kyle's legs and cupped his testicles in the palm of my hand. I massaged his large eggs to help quiet him. I looked Katye in the eye to make sure she understood the enormity of the situation. She seemed to be fully engrossed, standing with her legs crossed and nervously biting the necklace she wore.

"Kyle, I have to impress upon you the importance of you not having an orgasm whenever you want it," I explained. I gripped his testicles firmly until his body seemed to freeze under the pressure. I needed to have his full attention. "I understand these require release on an almost daily basis. But you need to be strong enough to overcome the urge to release. And if you can't do it by yourself, then come to me for help. I don't want to have to do this again."

"Yes, ma'am," my teenage boy grunted through the pressure in his testicles.

"Is the urge too great?" I asked.

Kyle sniffled then nodded. "Yeah."

I reached a little further and took his penis in my hand. He was almost completely hard. I squeezed it and felt it surge to its full length.

"What I'm about to do, I am doing for Katye's edification. Katye, I want you to watch back here as I take him to another orgasm." I pulling on his organ like a farmer would the utter of a cow. I could tell by his gasping and the heaving of his chest that his orgasm was near. "I want you to see how quickly a boy his age can recover with a new load."

I stroked him for nearly five minutes without success. His testicles were holding onto their load. I alternated between massaging his testicles roughly and stroking. Finally, he gave up and released his limited load.

"A boy can usually recover within an hour with a new load, although it won't be nearly as much. And now he's completely spent. Kyle, hun, why don't you go take a nap. You can finish your chores tomorrow."

The spent teenager, who is naturally over the age of eighteen, wearily lifted himself and walked from the room, his long limp cock smacking each thigh as he left the room. He had learned his lesson.

KATYE:

OMG. By the time I made it back to my room, the insides of my legs were so fucking wet. I got my vibrator out and took myself to two of the best orgasms I had had in ages. I didn't know Kyle could churn up another load that quickly. It wasn't nearly as much as what I got out of him, but it was decent.

Mom had me go wake him up two hours later.

"Hey, bro, time to wake up," I said quietly as I sat on the edge of his bed. I lifted the bed sheet off his body. I stroked his thigh as he came to. I lifted his balls in his wrinkly ball sac. "Hey, thanks for not ratting me out. It could have been me across her knee."

"Yeah, no problem. I needed what you did for me. It was worth it," he responded.

"Well, we'll see. You should put on those small boy-shorts she likes. Can't hurt."

I watched as my brother stuffed his cock and balls into the tight which square cuts which were barely long enough to reach his inseam. He looked nice. He looked very nice.

TINA:

I didn't make it to the next body building competition until it had just ended. I guess the awards had just been made and people were dispersing. I watched from a safe distance as Sotoya approached Katye and Kyle. It was then that I realized Kyle had a yellow ribbon attached to his thin waistband. And Katye had a blue ribbon!

Sotoya was much more hands on with Kyle this time. She feigned interest in his ribbon, allowing her fingers to dip inside his waistband and graze the base of his shaft. I saw the reaction on my boy's face. He felt it. She held her hand there, even with Katye standing beside her! She was talking intently to him, face to face. She had moved in front of him, blocking my view, but I could tell by Kyle's expression that her hand had most likely moved further inside.

He nodded a few times and then swallowed nervously. Katye was biting her lip, listening. Surely, Katye would tell me later what was said. Sotoya's hand reemerged to stroke his arm as she stepped back. It was then that another competitor joined the group. I guessed that it must have been her son. His back was too me but I was surprised to see that he was wearing a beige square cut instead of a bikini. I must admit, it did go well with his black skin tone. He leaned in and gave Katye a kiss.

I had seen enough. I needed to break this up. Sotoya's son stepped to the side as I joined the group. Sotoya and I glared at each other. She had her defenses up.

Katye tried to diffuse the situation. "Mom, hey, this is Tyrone, Sotoya's son."

I was ready to lay into Sotoya but I glanced at Tyrone first. I could not take my eyes off his body. It was so finely sculpted. He was absolutely beautiful as well. Our eyes met, and I felt the connection. There was just something about his eyes...and those lips. My heart thumped nearly out of my chest. I stammered for something to say.

I broke the gaze by looking down the rest of his body. I then understood why he didn't wear a bikini. The snake that lived between his legs was much too large for any bikini. While Kyle was well endowed, Tyrone was even larger. Sotoya looked at me with an air of superiority. She had given her son more than I had.

I was beat. I didn't bother to lay into her with a tirade. I just left with my two kids, a red face, and a fluttering heart.

I made it clear to Katye and Kyle that as long as Sotoya was a judge, they were forbidden from competing. This woman wanted more than to help them win gold. I saw it in her eye. She was dangerous.

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Lking4u2Lking4u2almost 9 years ago
sissy subs

Very interesting and provocative story.

Sound like both derrick and kyle are on their way to becoming feminized sissies who are going to service both men and women....................

mrsmillwoodmrsmillwoodover 9 years agoAuthor
Note from the author

Hello, please let me apologize for the note with which I started my story. My story, as originally written, was being rejected by Lit.com. They objected to my use of the word, "teenager." That's why, throughout my story, I had to refer to my "18 year old teenagers" or "teenagers of age." For the next chapter, please refer back to this comment section, because I may publish it elsewhere. If I do publish elsewhere, I will let you know where it is.

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