Involuntary Sissy Pt. 05

If my boyfriend thought that becoming my fiancé would temper my need to humiliate him he was not deluded for long.

It's true that I granted him more freedom to choose what he wears on his outer layers but the key to his dignity has always been his underwear.

Apart from wearing knickers every day and nightdresses in bed he agreed to fortnightly role plays to explore what I regard as his deepest desires.

The one we had tonight took some effort on my part but it certainly paid off.

Ever since we agreed to marry I have been devoting much of my time to planning our wedding while he is at work. We have agreed on the date and I have found the perfect venue. I presented him with the guest list and have made sundry other arrangements while he has done little more than agree to my plans.

In truth this is how I like it, but I am not so daft as to miss the opportunity to use his lack of organisational activity against him. I heaped on the guilt one evening this week as he put on his pink satin chemise before bed. "What have you done about the wedding, then?" I asked.

He looked startled. He had done nothing, he said. Should he have done?

I put on my passive-aggressive act. "No. Why should I expect you to lift a finger? You just carry on as if nothing's happening."

He offered an apology, which I did not accept, and said that he wanted to help in any way he could. Could I set him some tasks so he could do his bit?

"I'm too angry to talk about it," I said, and refused to speak to him for the rest of the night.

He's terrible with confrontation and the next morning he pleaded with me to let him do something to help.

I told him that I was too busy trying to organise my engagement party with my friends at the end of the week, for which I had not been able to arrange a caterer because I had been taking responsibility for everything else. There was no one available to serve drinks and dinner at this short notice.

He offered to take the day off work to do the cooking and then he could wait on us.

I snorted. "A guy at a girls' night in? How would that work?"

He kept quiet.

"Alright," I said after an uncomfortable silence. "I'll give you a shopping list and we'll see if you can manage it."

He put his all into the party preparation and I was secretly impressed, although I couldn't let it show.

It wasn't till the afternoon of the party that I hung the French maid's costume on the peg by the front door where I leave his role play outfits. When he found it, he didn't put it on unquestioningly in the way he usually did for our fantasies. He brought it to me in the bedroom and said he couldn't do it.

"I knew you would let me down," I said with as much bitterness in my voice as I could muster.

It wasn't that, he said. He just couldn't dress up in front of...

I interrupted him. "If you'd checked, you'd have seen that there's a veil to cover your face. But if you can't do this one little thing then I guess I'll have to be the waitress at my own engagement party. My friends will be arriving soon. You can just stay in the bedroom. This is a girls-only party."

I slammed the bedroom door and hoped that I had done enough.

I was busying myself with the final touches, even though there was little left to do, when I heard the bedroom door open. There he stood in his shiny black high-necked dress and white pinny. The dress had exaggerated puff sleeves with a tight stretch satin body and full-circle skirt. A white petticoat pushed the skirt outwards so that it was possible from a low angle to see the black suspender belt that held up his opaque black stockings.

The only exception to his monochrome colouring were his shocking pink satin knickers, chosen to make any accidental flash immediately obvious.

It was hard to see if he was blushing beneath the black lace veil that hung over his face. I promised myself a look just as soon as I had delivered the final part of his outfit.

The box containing his new shoes was at the back of the wardrobe. I never usually bother with feminine footwear but he would need them tonight. I helped him slip them on. They were black patent leather with ribbon ankle ties, which I secured for him as he stood unsteadily in his first pair of high heels.

"You'll have to be a fast learner tonight," I said, rising to look beneath his veil at what I imagined would be a deliciously ashamed expression.

The doorbell rang. I sighed. "I'd better get that. You need to get used to those shoes."

Sally was the first to arrive, vivacious as ever. "Congratulations on your engagement, darling," she said as we kissed.

She's a full-figured woman but has never lacked confidence about her body or anything else. "What do you think of the dress?" she asked. "Is it too much?" I've noticed that she either wears them short or low cut, but tonight's leopard-print number was daring at both ends.

"You look divine," I said. "It's a good thing lover boy isn't here to see you. He wouldn't know where to look."

He never quite knows what to do when Sally flirts with him, which she does with everybody and outrageously. One of my former boyfriends was once so distracted by her cleavage during a cocktail party that he spent most of it talking to her chest. Every time he looked away she pulled her dress down a bit further and moved a bit closer on the sofa. With a wink to me she curled her hand around the back of his neck and pulled his face into her bosom. He was so mortified that she was able to hold him there for half a minute. When she released him she asked: "Did you find what you were looking for?"

I led Sally through to the sitting room to meet our waitress. "Sally, this is Sugar, who will be serving us drinks tonight. I'm afraid she doesn't speak much English but she can understand gestures pretty well. Now, Sugar, how about some drinks?"

I made an exaggerated gesture of pouring wine into a glass. My fiancé nodded and tottered to the kitchen to do our bidding.

For a man unaccustomed to wearing high heels he did a commendable job of serving wine to the six of us but I wanted to keep up the pressure. "For goodness' sake," I said, poking my head into the kitchen as he dished up our first course. "You're the hired help. Turn on the charm a bit, will you? You're supposed to be tending to our every need. And make sure you bend prettily at the waist if you don't want them to guess you're a guy."

After serving each course he hovered about daintily with a bottle of champagne. Sally asked how I was getting on with my fiancé. "Oh, he still needs a bit of training, but I think he'll be just fine," I said.

The women laughed. "How's your love life?" I asked.

Sally is the most fluidly bisexual woman I've ever known. She said that she was waiting to see where the wind blew her.

I ordered my fiancé to fill our glasses. "How about Sugar, here?" I asked. As he bent over to pour I reached under his petticoat and gave him a gentle pat on the bottom. We agreed that our waitress was a catch. I smirked at Sally. When he bent over next to her I gestured for her to do as I had done.

Sally carefully cupped him and drew her hand away suddenly, wide-eyed. She lifted her hand to check him again. He trembled as he poured but did not spill.

Jemima, sitting opposite, registered Sally's reaction and raised an eyebrow.

"Jemima's glass now, Sugar," I instructed.

Sally and I looked at Jemima expectantly as he bent. She gingerly reached for his knickers.

"Oh, Sugar!" Jemima exclaimed.

The others wanted to know what was going on, so each of them in turn discovered his cock in our game of lucky dip.

Sally was giggling wildly. I told our waitress to refill her glass. "Slowly this time, Sugar," I warned her.

Sally asked if I minded. "Please," I said. "Help yourself."

Although her hand disappeared from view it was obvious from his quivering that she was fondling him expertly. The scarlet of his blush spread down to his neck. I wondered if he might protest, or whether he knew that would risk giving away his identity.

He groaned despite himself, prompting peals of laughter. Jemima wondered aloud if Sally could get him to do it again. Sally cocked her head to look at him. "Are you alright with this, Sugar?" she asked.

He put a hand on the table to steady himself as his legs threatened to buckle but he was speechless.

I shifted my chair around so I could join in the fun. I told him to stand upright and I lifted up the hem of his dress. His hands clutched the champagne bottle to his chest as I exposed the front of his pink knickers, taut against his straining cock. A small damp patch was forming.

I dragged my fingernails across his balls but it was Sally's careful teasing that matched the rhythm of the keening that rose from his throat.

Jemima found her mobile phone and began filming. "Can we see Sugar's face?" she asked.

I had been going to keep that secret, but she carried on. "I mean, we all know he's your fiancé, don't we?" she said.

He let out a long, low wail.

Sally laughed. "He's not," she said, disbelievingly. "You wouldn't want me to make him..."

He interrupted her with loud panting noises, much higher pitched than his groans and rising in tone.

"Get ready, girls," I said. I stood up and gently lifted the veil. Nobody could quite believe it.

Jemima clapped her hand to her mouth, then let it fall. "I was only joking," she said.

My lover opened his mouth to protest but the words were overtaken by shriek of pleasure as Sally brought him home.

His whole body shuddered. His knickers darkened, saturated and leaked onto the table. The room went quiet.

"Oh, Sugar," Sally said, biting her lip. She began to titter, setting the rest of us off.

I let the veil fall and sent him shuffling unsteadily out of the room.

"We promise not to tell," Sally called after him, laughing even harder. "Jemima, tell me you got it all."

Jemima nodded. "Yes. Better than that. We can watch him face in slow motion." Everyone gathered round for the action replay. I looked up to see him weeping gently as he closed the bedroom door. He would need my comfort tonight, but that could wait for a while. All in good time, Sugar, all in good time.