A Natural Sissy Ch. 08

Author's note: This is a multi-part story about a young woman turning an older man into a compliant, sissified plaything. It is best understood if you read from the beginning. If that idea doesn't appeal to you, don't read the story. If you don't like this kind of story, but read it anyway, please don't bomb me. I warned you to go away. If you like the idea, read on, and don't forget to vote and leave a comment. More will be added if comments from readers justifies it. One reader suggested that I insert a cast of characters to make the story easier to follow. I can do that with the characters already in the story, but I have no idea where this story is going, so new characters will likely be introduced as Stacy is further humiliated. Not all the characters will appear in every chapter

CAST OF CHARACTERS

Gail -- narrator and lead female character. She is the one who controls Stacy's life.

Stacy -- an older man (the sissy) under the control of Gail. The subject of Gail's mischief.

Ralph -- A VERY close friend of Gail's, with privileges.

Amanda -- New neighbor to Gail and Stacy.

Joel/Joy/Jolie/Jolle -- Adriana's sissy husband.

Wanda and Shirley -- minor characters, friends of Gail, who once mentioned, may or may not reappear in future chapters.

Heather -- Gail's friend who operates a tattoo parlor.

Brut -- a released felon who now works for Heather as her bodyguard.

Other characters will be added, as required, to interface with Gail and Stacy as the adventure progresses.

*

Just as Stacy came back upstairs and told me the recreation room was ready for his tattoo application, the doorbell rang. "That's fine, Stacy. And just in the nick of time. That must be Heather at the door. Go let her in, please."

Stacy looked at me like he could stab me in the chest with his eyes, but he turned to answer the door. He was wearing only his bra, garter belt with stockings, and high heels. Not even a panty or wig. I just sat to see what would happen.

He ushered Heather into the living room, and I saw a very large black man follow them in. I knew of Brut, but had never met him. He just recently got out of prison after serving two years for raping a single white mother of two small children. Now he was working for Heather, who has known him for years.

Heather grabbed Stacy by the balls and pulled down hard as she said, "Stacy, dear, aren't you going to give me a nice welcoming kiss now that I've come to visit?" When he was kneeling, she grabbed his ears and pulled his face to her crotch, covered only by a very short mini skirt.

Poor Stacy. What a sissy must endure. He only said, "Yes, Miss Heather," before raising her skirt and beginning cunnilingus, thrusting his tongue into her pussy. Brut pulled a stopwatch out of his pocket to time the kiss. Heather didn't let go of Stacy's ears for a full six minutes while he "kissed" her. Then with a nudge from Brut she said, "that was a wonderful welcome, Stacy. I'm so glad we're such good friends. She helped him up, and continued, "I'd like you to meet my assistant, Stacy. This is Brut. I'm sure he'd like a nice welcome to your home as well."

Stacy sighed. He knew better than to question what was about to happen. He walked to Brut and without a word knelt, his face just inches from Brut's crotch. Brut was way ahead of him, with his trousers already down to his knees.

I knew immediately that this would not be a blow job. It would be a face fuck. Brut took Stacy's head in hand to hold him still, and started what would become a very lengthy face fuck. Heather came and sat by me as we watched Stacy try to take 13 inches of hard black cock in his mouth. Now the unsupported myth is that black men have much larger cocks than white men, but in Brut's case, it was no myth. He crammed his mammoth tool as far as Stacy could take it, to the point of asphyxiation. He only backed out when Stacy was at the point of passing out. Stacy is an accomplished deepthroater with any lesser cock, but this thing was enormous. After about twenty minutes Brut finally unloaded in Stacy's throat with a yell, "Yeah, man! That was a great welcome." He pulled out, grabbed Stacy under each arm and lifted him to a standing position. Next, he took Stacy's nipples, through the bra, between finger and thump, and twisted as he planted a sloppy wet kiss on Stacy's quivering lips. When he broke the kiss, Brut said, "Yeah, Stacy, I can tell we're gonna be good friends, Real good friends." Then he looked at Heather and asked, "Ma'am, are you ready?"

When he got an affirmative answer from Heather, he picked Stacy up, placed him securely under one arm, and said to me, "Lead the way, ma'am. You and I can get acquainted while Heather does her work. Now that was an offer I couldn't refuse. I led the pair downstairs, Brut with Stacy under one arm and a heavy, tool-laden kit in his other hand. Heather's tools of her trade, of course.

In no time at all, and over vigorous objections from Stacy that he could certainly have a tattoo applied without being strapped to a table, he was securely strapped down. Heather wasted no time getting her tools ready for the job at hand.

When she approached Stacy with a hypodermic needle, Stacy yelled, "What's that? What are you doing?"

"I'm just going to administer a light sedative so you won't feel the pain, sweetheart. Everything will be okay." She unceremoniously jabbed the needle into Stacy's thigh and pushed the plunger. Stacy was out like a light in just seconds. Then she looked at me and said, "He'll be out until morning, Gail. Are you sure you want me to do everything we talked about earlier?'

"Certainly, honey. The works. Now, unless you need Brut here, I'll take him upstairs and entertain him while you work."

"Go right ahead. Brut is my bodyguard, not my assistant. I'm in no danger here. Have fun."

I have absolutely no idea what Heather did, except that she took a good part of the rest of the day doing it. Well, I know she would do what I asked her to do, but how she did it is beyond me. Brut and I, on the other hand, had quite a time. Amanda brought Joelie over as we had planned, and that's what I'm going to tell you about. I'll get back to Stacy later.

Brut had me pinned naked to the sofa when the doorbell announced the arrival of my neighbors. He pulled his cock from my pussy in exasperation, and said, "Who the fuck? Can't a guy get some sweet white pussy without being interrupted anymore?"

I was as exasperated as he was, because he had me at the peak of an orgasm when the bell rang. "Crap," I replied. "Isn't that just like Amanda, to interrupt the best fuck I've had in years?"

I threw the door open, startling Joelie so that he backed away quickly. Only Amanda's quick response saved the high-heeled sissy from falling. Joelie was dressed as a full-blown sissy, in pink skintight trousers with no crotch, so the leash attached to his ball harness was free of any encumbrance.

I quickly took the offered leash from Amanda and pulled it taught, forcing the ball harness forward, with Joelie's balls now stretched along with the harness. "Come on sissy boi. Let's get inside so I can introduce you to someone special."

Brut was standing, still naked, his huge cock throbbing, when we entered the living room. I stopped with Joelie right in front of Brut. "Joelie, this is Brut. Suck his cock."

Joelie looked briefly at Amanda for any sign of rescue, but Amanda gave none. As she and I started for the kitchen to fetch a bottle of wine, Brut pushed Joelie down on his knees, saying, "Gail didn't tell me your name, boy, so I'll just call you Cocksucker until she does. Get busy."

When Amanda and I returned with the wine and three flutes, Brut had put Joelie face up on the coffee table, his head hanging off the end. It was obvious that, by kneeling, Brut had a straight passage down Joelie's throat at the angle presented. He wasted no time forcing his huge cock in as far as it would go. He held it in place until Joelie was about to pass out from lack of air, then backed out enough for the sissy to take a breath, then he forced his cock in again. It was a game for Brut. He continued this action over and over for almost ten minutes before he unloaded in Joelie's throat. The poor sissy almost drowned. When Brut released his victim and reached for the filled wine flute I offered, Joelie was gasping and coughing. Finally, Joelie was able to recover normal breating, and rolled himself from the coffee table onto the floor, sitting with his legs crossed like an Indian.

He kept trying to ask a question, but was interrupted for quite some time. Finally, exasperated he continued with his question anyway. "May I have something to drink? I need to rinse my mouth."

"Well, I don't know, Joelie." Then looking at Amanda, I asked, "Can the sissy have something to drink?"

"Sure. I brought his bottle." She rummaged through a satchel she had with her and pulled out a baby bottle filled with what looked like a slightly milky substance. The nipple of the bottle was a miniature cock about two inches long. "Here, sissy. Here's you bottle. Drink it all down like a good boi." She handed the bottle to him and he started sucking the cock-shaped nipple.

Brut asked before I could, "What's in the bottle?"

"His cum from a week of milkings. I save it in the refrigerator, and when the bottle's full, I give it to him to drink."

Brut spewed wine as he started laughing. Then he spoke. "I've heard of that, but I'm not sure how it's done." He broke out laughing again.

Amanda picked up the conversation. "It's not a secret. The way I do it is put him face down naked on the bed with his cockhead in a cup to catch the cum. Then I go into his rectum with my fingers and massage his prostrate gland until the cum spills into the cup. In Joelie's case there is never an orgasm, and that's why I do it. It robs him of semen when he masturbates while he thinks I'm not paying attention."

Brut and I both burst out laughing. Joelie was not pleased at our laughter, but what the hell. Sissies are not to be pleased, they are to please.

The evening continued with more humiliation for Joelie. We had him model many of Stacy's dresses and lingerie, and when any of us didn't like the way he performed he got some kind of punishment and the need to make up for his deficiency by sucking cock or cunt.

Late in the evening, Heather came up and asked Brut to bring Stacy up from the recreation room. When that was done we all inspected the magnificent work that Heather had done. But I was getting sleepy, so I asked Amanda to take Joelie home so I could rest. Heather and Brut stayed the night just to be sure Stacy was okay. I could hear them fucking through the night in the guest bedroom. It was obviously a mistress handling her subject.

The next installment will reveal what Stacy had done to him.