Small Penis Humiliation & Enforced Chastity
(The challenge continues, as Merry looks for anything that will humiliate or embarrass Shilo)
“So, today, Judy is coming over for a counseling session.”
“Oh, it that what you’re calling it now?”
Merry chuckled. “Yes, of course. Seems appropriate. Judy’s problem is, she’s been married to Jack for … about six months, I think. They waited until the wedding night, to have sex the first time, and that’s when she found out that Jack has a small penis, I mean, as she says it, REALLY small. It doesn’t satisfy her at all, and she says, he’s not very skilled, orally either. So, we’re going to pretend that you also have small penis, and, um, well, here’s a list of items I want you to have ready, for when I tell you to fetch them.”
I looked at the list, smiled weakly, and nodded.
Judy arrived, and Merry showed her in.
They sat down, and Merry said, “If it’s okay, I would like Shilo present for this, as it’s very helpful to have a male point of view on this.”
“Well, if you think so…”
“Good. Shilo, come in, and join us.”
I entered the room, and sat down.
“So, Judy, the problem, from the beginning..?”
“Well, Jack and I decided it would be romantic to wait for our wedding night to have our first sexual relations. ”
She held her right thumb and forefinger apart about three inches, and went on, “And that’s when I saw that his penis is about this big when it’s erect. He wanted oral to get started, and I gave it to him. Then he gave me oral, for all of two minutes, I swear, then he got on top of me. I could hardly feel it inside of me, and in three minutes he was done, and he got off of me, gasping, and said, “WOW that was good. Hope it was good for you.” I said, “Yeah sure,” as I lay on my back, thinking, “Oh MY GOD.”
“The scene repeated several times throughout the night, many times through the honeymoon, and from start to finish, never lasted more than ten minutes, and it left him gasping, and me totally unsatisfied. ”
“I’ve asked him to maybe slow down, spend a bit more time with his head between my legs, and he says, ‘Oh babe what for, don’t you like it better when I fuck you?'”
“And that’s the way it’s been every single time. He loves to have sex, three, four, five times a week. I don’t deny him any, because I know, it’s only gonna take ten minutes, but I don’t enjoy it.”
“So,” said Merry, “You’ve never climaxed during sex with him?”
“Never. Lately, when he falls asleep afterwards, which he does quickly, I get out my vibrator and get myself off.”
“Well,” said Merry, “Same thing with Shilo.”
“We were having sex before we got married. So I knew what he had, or doesn’t have, as is the case. And I told him, I would only marry him on one … well more than one …but one primary condition.”
“Since his penis is of no value to me, I keep it locked up, in a chastity device. I control his orgasms, I decide when and how often. He gives me oral service, he learns what I want, he gives it to me until I say I’ve had enough. Trust me, when he’s locked up with you in control, he’ll give you what you want, while hoping he gets what he gets sometime.”
“A chastity device, you say…” Judy mused, looking at me.
Merry said, “Get undressed, Shilo.”
I obediently stood up, and began stripping, until I wore nothing but socks and a chastity device. I continued standing, while Judy looked at me, up and down.
“How long do you … keep it on him?”
“Well, this stretch has been slightly over three months, and still counting,” Merry replied, telling the lie with a straight face. “With a weekly removal supervised by me, for cleaning, inspection, and shaving.”
“He goes that long without cumming?”
“Well, certainly without intercourse. It’s been … since we got married, that I allowed him that privilege. I have other ways I allow him an orgasm, every couple of weeks, maybe.”
“You … unlock him, and let him masturbate?”
“In a special way, supervised, while I watch.”
“Would you like to see?”
“Shilo, special masturbation, you know what to fetch.”
I got up, went to the bedroom, and returned, with the kitchen stool, the rubber dong with a suction cup at the base, a jar of lube, and a condom.
“Right there,” said Merry.
I stopped, and stood, in front of the stool.
I attached the suction cup of the dong firmly to the base of the stool.
I smeared lube from the dong onto the tip and first three inches of the dong.
“Stand in front of me.”
I did. She produced the key, undid the lock, took it off, pulled the cage down and off my penis, then opened the cock ring and took it off.
“Sit down, and begin.”
I stepped back to the stool, opened my cheeks and guided my anus onto the tip of the dong, and sat down, as it entered my rectum.
Once fully seated, she said, “Begin.”
I began stroking my penis, while lifting my butt off the seat and back down again, fucking my own ass while I stroked my hard cock.
I felt myself getting very close, and stopped, long enough to open the condom packet, and I slipped the condom over the first two inches of my penis, then I resumed fucking my ass while stroking my penis,
I let out a gasp, as I shot my cum into the condom, and pushed down hard on the dong, twisting my buttocks into the seat.
After the twitching in my cock subsided, Merry said, “Eat it.”
I pulled the condom off, and held to my mouth, and turned it inside out, dripping my cum into my mouth, and I swallowed it.
“Go wash up, hurry up.”
I got up, and went to the bathroom.
“His penis did not look all that small to me,” said Judy, quietly.
“I’m used to bigger ones,” said Merry.
I returned to stand in front of Merry.
She handed me the cock ring, and I put it around the base of my cock and scrotum. She handed me the cage, and I slid my flaccid penis into it. She set the lock in place.
I removed the stool from the room, and returned, standing in place, at attention.
“I … don’t know what to get from all this,” said Judy.
“Well, you begin with a conversation with him, telling him how unsatisfied you are. You have to be honest. You tell him, you’ll give him no more sex. You tell him, he has to learn how to give you oral pleasure. You tell him, THIS is the way to do it, that you are taking charge of his orgasms. He has had it HIS way long enough, and this is the way it’s got to be from now on. You have that conversation, and stay in touch with me, and I’ll coach you moving forward.”
“Does it have to include… THIS?”
“Well, no, it’s whatever you decide. You can give him free time to masturbate however he wants. But he has to earn the free time, by pleasing you first.”
“Ah. Well, thank you, this has been very enlightening.”
She got up to leave. “Thanks again, for everything, and the show.”
“My pleasure,” said Merry, and she showed Judy to the door.
The door closed, and Merry turned to me, grinning.
“So, how was THAT on your S & H scale?”
I laughed. “That was FUN. I’ll do all that again, anytime.”
She shook her head, grinning. “You know, this really is quite a challenge.”
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