A Natural Sissy Ch. 04

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The next day, Friday.
2.4k words
4.18
164.4k
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Part 4 of the 8 part series

Updated 10/30/2022
Created 06/01/2007
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harv069
harv069
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Author's note: This is a story about a woman who turns an older man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you like the idea, read on, and don't forget to vote and leave a comment. You will need to read the previous chapter to see how we got where we are in this one. More will be added if comments from readers justify it.

Chapter 04. The Next Day

I was up early, and called to set up a surgery for Stacy’s breast enhancement. The hormones were working but his tits seemed to have stopped growing at a B cup. I wanted him really top heavy. At least a D cup, maybe a DD. I let the exhausted sissy sleep.

As I was finishing up my third coffee after breakfast, Stacy entered the kitchen, dressed to the nines as a very pretty lady. But this was Friday, and he should have been dressed as a sissy.

Stacy said as he walked in, “Good morn…”

I faked rage, saying, “What the fuck do you think you’re doing, sissy? This is Friday, damn it.”

His face went pale with fear as he stood just inside the dining room, balanced on his five-inch high-heeled pumps. “It’s… its Fri… Friday?” he stammered.

“Fucking right it’s Friday. You have earned some serious correction, you stupid ass,” I bellowed, suppressing my glee at catching him in error. “Now, you have 30 minutes to correct the situation, and then go to the rec room and lie face up on the pool table. Go!”

***

Stacy hastily ran to the bedroom to redress. He stripped the makeup from his face, disrobed, slinging his feminine attire across the room, some landing on the bed, the rest on the floor. He carefully placed the expensive blonde wig on its form, and began digging out some of his sissy attire. Fishnet crotch-less pantyhose in off-black, low heel open toe patent pumps, and an off-black training bra with the cups cut out. He had to search for the ball spreader, but finally found it in one of Gail’s drawers.

As he began to attach his gaudy imitation gold dangling earrings, those that almost grazed his shoulders, he discovered that he was still wearing his precious 2ct. diamond studs, and hastily removed them. Then he noticed that his fingernails and toenails were all wrong for a sissy. They had to be pale pink, not the ruby red he had on. He quickly removed the offending color and replaced it with pale pink. He matched that with the same shade of lip-gloss, followed by just a hint of rouge on his cheeks. Matching rouge on the nipples peeking through the cupless bra. Then just a light application of mascara, hardly noticeable to the untrained eye. But he knew Gail’s eyes were trained, and heaven forbid she find anything else to criticize. He was already in enough trouble as it was. Before he donned his pumps, he pulled on a pair of fancy ladies socks with a red bow in the back. “Garish,” he thought, “but I do what I must to please Gail.”

He was finished in just under the 30 minutes allotted, and he was wearing all he was allowed unless he was going outside, when he could wear unisex slacks (no front zipper), and a see through white shirt that buttoned like a blouse (which is what it was). On his way out he stopped briefly in the bathroom and swallowed two Viagra pills.

***

I was waiting for Stacy in the rec room, and he made it just in time to meet the 30-minute time allotted. He climbed onto the pool table, assuming a prone position, face up, legs spread just as he was supposed to do. I had already set up the IV, with the saline in place. I was fooling with the tubing when Stacy came in, more to call his attention to the apparatus that anything necessary for the procedure I was about to administer. He was as nervous as a cornered rat. Perspiration began to form all over his scantily clad body. Good. Just the reaction I hoped for.

“Stacy, you know I have to punish you when you make mistakes as serious as the one you made a few minutes ago, don’t you?”

“Yes, ma’am.”

This is going to hurt me as much as it will you, because you have violated our agreement. You know that, don’t you?”

“Yes, ma’am. Wha… wha… what are you going to do?”

“It’s just something to remind you not to screw up again. I’m going to inflate your ball sac with saline. It won’t cause any damage, and your body will eventually absorb the saline and the inflation will recede to normal. But until it does the inflation will remind you of your grave error this morning. Are you ready?”

“How… how long will that take? To get back to normal, I mean?”

“I’m not sure. Probably a few hours, at least. Let’s get on with it.” I inserted a needle into his ball sac attached the feed tube, and started the IV at full flow. He would take the entire liter of saline. I sat at his side while the IV emptied, wiping his brow as sweat poured from it. His eyes tired up a few times, and I wiped away the tears, all the while praising him for taking his punishment like a real sissy should, speaking like a mother to a small child. I even stroked his hard cock a few times here and there during the drip.

When the IV was empty, his ball sac had swollen to a size approximating a large cantaloupe. I removed the needle, and then lifted his balls to test the weight and it was about the same as the liter that had been injected. Just one more thing to do, and then I can send Stacy up to get lunch ready. I inserted a stainless steel rod into his urethra until only the tip remained showing. The rod was just under nine inches long and about 1/8th inch in diameter, so it was a near perfect fit in his cock. The tip left showing had a place to attach two delicate gold chains, the other end of each to be connected to a nipple clamp and fitted to Stacy’s rouged nipples. This would hold the cock up, away from the swollen ball sac, so the enlarged sac would be entirely visible.

“Okay, Stacy, you may go and prepare lunch for us. We’ll take it on the patio in an hour.” I got up and walked away leaving him to deal with the swollen balls. I planned to grab a bottle of champagne and some cheese and crackers to pass the time until lunch on the patio.

I watched Stacy try to walk with his ball sac so filled with saline that he could hardly manage to take a step without causing the sac to wobble back and forth with each stride. I laughed to myself at the sissy’s consternation.

Stacy brought the lunch to the patio about five minutes before the hour was up. Mine on a serving tray, his in a dog bowl.

“Oh, Stacy, dear, I forgot. You can eat at the table with me for lunch. Go get a real lunch and join me at table.”

His eyes lit up like light bulbs, as he turned to return to get himself a real lunch. When he returned, we ate together like the best of friends, chatting about this and that until the meal was finished.

Just as Stacy finished cleaning up after lunch the doorbell sounded. “Stacy, get the door, please.”

“Dressed like this, Gail?”

“Certainly, like that. You are appropriately dressed for sissy day, and whoever is at the door is probably just one of my friends. And they all know about you. Now go.”

A moment later, I heard Ralph let out a boisterous laugh that rocked the house. I knew it would be Ralph, and I knew he would do what he could to belittle my sissy. I tuned in to the conversation at the door.

“Well, hello, there, Stacy, my man. How the hell are you? And what happened to your balls? They look pretty swollen. Nice gold chains you have there, too. Are they real gold?” Ralph casually slapped Stacy’s balls a couple of times just for the hell of it.

Stacy cringed at the slaps and ignored the question about the gold chains. “I… I … screwed up this morning, and Gail inflated my sac with saline.”

Another boisterous laugh from Ralph as he pushed past Stacy and entered the living room where I was waiting. He swept me up in his arms and headed for the bedroom just as our script required. He looked back over his shoulder as I was giggling and squirming in his arms, and said, “Come on Stacy. I’m gonna show you how a real man fucks a pretty lady. I might even let you help.”

“…let you help” registered in Stacy’s mind as a good thing. He eagerly followed Ralph to the bedroom and watched as I was unceremoniously dumped on the bed.

Then Ralph said, “Okay, Stacy, you can get Gail naked while I strip off.” Dutifully, Stacy started removing Gail’s clothes until she was down to stockings and shoes. “That’s far enough, Stacy. I like my women to wear stockings and heels when I’m fucking them. But I seem to have a problem here. Do you see what it is?”

Stacy glanced at Ralph, seeing that he was totally nude, but didn’t see anything wrong. “No, I don’t see a problem, Ralph.”

“Well, Stacy, do you think I can fuck Gail with a limp cock?”

“Oh. No, I guess not.”

“Then what do we need to do to get it hard, Stacy?”

“Well… I usually stroke mine.”

“Nah, that won’t work for me. What else might get it hard?”

“Maybe you could get Gail to suck it?”

I broke in at that. “I’m not doing that. That thing would choke a horse.”

Ralph feigned a confused look. “Well, I guess that’s out. She doesn’t want to suck me. What can we do now, Stacy?”

“I… I… don’t know.”

“Well, if you want to watch me fuck Gail, you need to think of something.”

I could see the wheels ever so slowly turning in Stacy’s head, and he frowned. “Uh… I guess I could do it for you.”

Ralph almost shouted, “Yes. That’s it. Now why didn’t I think of that? Get to it Stacy. Hurry. Times a wasting.”

Poor Stacy was trapped. Now he had to get Ralph’s cock hard with a blowjob. Ralph sat on the edge of the bed and motioned Stacy over. “Okay, sport, kneel down here and get started. If you do it right, I’ll let you help me stick it to her.”

Stacy took that to mean that he and Ralph would double fuck Gail. But Ralph didn’t mean that at all. So when Stacy had sucked him until his cock was steel hard, he said, “Okay, I think I’m ready now. I’ll just climb over on top of Gail, and you can hold my cock and help me push it in. Then you can wank off while you watch me fuck her.”

“But… I thought we were both gonna fuck her, Ralph. Can’t we do that?”

“Nah. I don’t share my women while I’m fuckin ‘em. But I’ll tell you what. When I’m done, I’ll try to convince her to let you fuck her, okay?”

Stacy just nodded as he took Ralph’s cock in his hands and inserted the tip into Gail’s cunt. Ralph applied a bit of pressure and his rampart cock slid easily into my well-lubricated cunt.

“Thataway, Stacy. Ya did good. Now just stand right here beside the bed and watch what I do.

An hour and a half later, Ralph rolled off of Gail and reclined beside her. He had fucked her every way known to man, plus a few nobody had ever tried, and they were both sweating from the passion and intensity of the coupling.

“How we ding there, Stacy? Did you cum yet?” asked Ralph.

“Uh… no, I saved it so I could fuck Gail like you said.”

“Oh, yeah. I said that didn’t I? Well, Gail, what do you think? You want to give my helper here a little fuck?”

“Oh, Ralph, you know you wore me out. I’m just not up to it. Tell you what, though. I’ll let Stacy show you how he fucked me yesterday.” Gail motioned Stacy onto the bed. “Okay, sissy you can fuck my leg if you want. But go easy, ‘cause I’m really tired.”

Well, I could certainly tell that Stacy was disappointed, but I guess he decided my leg was better than nothing, so he took about fifteen minutes of massaging his cock on the calf of my left leg until he spurted his small load of cum onto my stocking. When he finished I pushed him away and said, “I think I’ll just stay here for the night. Anyone want to join me?”

Stacy’s eyes brightened, and he volunteered, “I do. I do.”

“You’re not anyone, sissy. Ralph is anyone.”

Ralph chimed in, “Aww, Gail, let’s give the guy a break.” Stacy didn’t see Ralph wink at me, but I knew Ralph must have an idea to further humiliate my sissy.

So I said, “What’s that, Ralph?”

“I’ll spend the night, and Stacy can sleep on the bed with us if he keeps my cock in his mouth the whole night. What do you think?”

I just smiled an evil smile. But Stacy, not having slept on a bed in quite a while was eager to accept the rules. “I… I’ll do it.” And he did. I woke up two or three times during the night, and Stacy’s head was right where he started, resting on Ralph’s upper thigh, with the cock in his mouth, sucking very, very gently, as if it were a teat. I think he was asleep the whole time. Things are coming along nicely with my plaything. I finally had to shoo him from the bed to get breakfast ready. He had cum dripping from his mouth. How very sweet.

What will sissy Stacy face today? Will Gail find more ways to humiliate the poor man? Stay tuned.


harv069
harv069
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AnonymousAnonymousalmost 8 years ago
nipple sissy wear

I think I would want to have clothespins attached at least till I was able to loose control and be spanked for that and not be allowed to remove them.

AnonymousAnonymousover 10 years ago
Why?

The story was going so well, And then we had to get cruel.

Why must it always go that way ? &A liter of saline, I can hardly believe that would be possible.Up to this point ,I was starting to envy Stacy.

I think not so much anymore.

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