The layoffs were announced on Friday morning and by the afternoon, three of the men I had started work with a year ago were gone forever. I think they were all quite surprised that I was still on the payroll. It certainly didn’t make sense. I mean, what had I done to distinguish myself from them? But then, my wife had the given me an inside rail on the competition. And her sexual favors had pushed me over the finish line in first place. Frank Ballwell, the managing partner of the firm, had even promised me another raise within a few months. Even though my job was safe, I was apprehensive about what was going to happen this weekend. He was going to take my wife to a Broadway show and keep her out all night. I was supposed to stay home and wait for his Chief Financial Officer, Ted Crasnow, to come over and fuck me.
Late Friday afternoon, Frank’s secretary called and told me Frank wanted to talk with me in his office. I entered and closed the door behind me and sat in the plush chair across from his desk.
“Well, Sissy-boy,” that was the humiliating name Candy and he had chosen for me, “I just wanted to make sure we’re all set for tomorrow night. I’m really looking forward to taking your wife out and then to my place for the night. There’s no problem is there?” I think he took special pride in calling me that name. I was their little sissy-boy now. I know he was waiting for me to address him as ‘Master’.
“No, uh, Master, there’s no problem. None that I can think of.” I was a weak image of my former self.
“That’s great. By the way, Candy tells me that you’re wearing panties to work now and painting your toenails. Is that true?”
“Yes, yes it is.” He was silent as he stared at me.
“Yes, Master, yes it is.”
“That’s better, Sissyboy. Would you mind showing me?”
“Showing you?”
He was silent again and seemed to be a bit angry. “Sissy-boy, you need to learn how to address me properly.”
I was totally abashed. “You want me to show you, Master? What should I do? You don’t expect me to undress here do you?”
“Ah, but that’s exactly what I want you to do, Sissyboy. Candy tells me you look quite the little whore when you dress up.”
“But what about your secretary? What if she comes in?”
He reached over and pushed a button on his desk. A few seconds later his middle-aged secretary, Evelyn came in. Evelyn was about 50 years old and had kept her shape despite her years. For 50 years old she was still a very attractive woman.
“Please sit down, Evelyn, Sissyboy is going to put on a show for us.” Evelyn just looked over at me expectantly with a slight smile.
“Did you know Sissyboy wears panties to work, Evelyn? He was about to model them for me.” Evelyn didn’t say anything, but my face was red and I was starting to sweat. I couldn’t believe he would embarrass me like this.
“Well, let’s get started, Sissy-boy.” I just sat there.
“Evelyn, have we finalized the layoff list or can we add another name to it?”
“We could still add a name Mister Ballwell. It certainly would help the bottom line.”
By the way, I have a very interesting video that you would enjoy, Evelyn. Would you like to see it? It’s entirely X-rated” He was talking about the video of him fucking me at his house a few nights ago.
Frank looked at me to see if I would object. Slowly I started to take off my tie and unbutton my shirt. Instead of a t-shirt underneath, Candy had made me wear a camisole, a silky white cover with adjustable shoulder straps. I stood up and took off my shirt.
“Turn around, Sissyboy, model for us.” Slowly I turned around. I was totally humiliated.
“Well let’s see the rest, Sissy-boy, Evelyn and I are excited, aren’t we Evelyn?”
“Yes, Mister Ballwell, I think he’s cute. I didn’t know he was transsexual.”
I started to object, but Frank cut me off. “Just go on with the show, Sissyboy, Evelyn’s just teasing you.”
I took off my shoes and socks, stood up on bare feet, loosened my belt and lowered my pants and stepped out of them. I was wearing pink full-cut nylon panties with a frilly edge all around. I suddenly realized Candy must have picked them out knowing about this encounter with my boss.
“Gosh, Sissyboy, you’re really hot. Walk around, let’s see you from all sides. Model for us.”
I walked the length of his office wearing just the panties and the camisole. I turned and walked back. The shape of my penis was very visible through the panties as I walked.
“I’d like you to show Evelyn a bit more, Sissyboy. Wouldn’t you like to see more Evelyn?” I froze, fearing the worst. Evelyn just stared at me to see what I would do. Evidently, nothing amazed her.
“We’re waiting, Sissyboy.”
Slowly I lowered my panties and stepped out of them. My dick was semi-hard from rubbing against the nylon panties. They were staring at me.
“Evelyn, did I tell you I fucked Sissy-boy’s wife yesterday. He even helped me, didn’t you Sissyboy?”
Involuntarily my dick got even harder remembering yesterday. “Look at that, Evelyn, Sissy-boy is getting excited. I’ll bet he’s thinking about yesterday. Have you ever met Candy?”
“Yes, I did Mr. Ballwell, at the summer picnic, a very sexy young girl. I’ll bet she’s a bit much for Jimmy.”
“Please let me get dressed.” I was almost ready to cry.
He must have had one soft spot left in his heart. “Okay, Sissyboy, that’s enough, get dressed and I’ll see you and Candy tomorrow night. Evelyn, thanks for sharing this with us.” Evelyn got up without a word and left the room.
I started to put my clothes back on wondering how much more of this I could take.
“See you and Candy tomorrow about eightish, Sissyboy. Thanks for the little show. We’ll have to do this more often. Loved the pink panties.”
I finished putting on my clothes and walked to the door. Before I could open it I herard, “Sissyboy, you didn’t say goodbye.”
“Good-bye, Master.”
“Good-bye, Sissy-boy.”
I couldn’t look at Evelyn as I passed her desk in the outside office, but I could hear her laugh as I went by.
* * * * * * * * * * * *
Saturday morning I woke up and stretched to loosen my muscles from the confining shape of the sofa and wondered what was in store for me tonight. The past week had seen a shocking life-change for me. I was no longer a person that I could respect. I belonged to my beautiful, but domineering wife and her new boyfriend, Frank Ballwell, my boss. I was sleeping on the sofa because of a game they were playing with me. They were turning me into their sissyboy.
Candy and Frank planned to go to a Broadway show together tonight. I was supposed to stay home and provide Frank’s CFO Ted Crasnow with a special kind of sexual favor for which I had very little experience or much desire. It was their way of keeping me busy and submissive while they did whatever they wanted with each other out of my sight. There was an extra feeling of personal humiliation on my part knowing that acquaintances would be seeing Frank and my wife together too, surmising what was going on. People would say, “Candy, you look wonderful in that dress, where’s that handsome husband of yours?” And Candy’s answer would be something like, “Oh thank you, Frank Ballwell bought me this dress, isn’t it sexy? And my husband’s home being fucked by a mutual friend.”
Despite the change in my situation, the change in Candy’s personality had been equally as dramatic. Like most husbands, I thought my wife was domesticated and compliant, a stay-at-home who cooked supper and waited anxiously for her husband to come home from the job that gave us a decent living. But when Candy dressed me up in women’s clothes, and slapped my face to make me comply with her wishes, she wasn’t that woman anymore. Something had transformed her, a deep, overwhelming need to take control of her life and mine, a need to discard a simple-minded, submissive wifely role and plunge into a world of kinky sexual adventure. It was surely a game, but a very serious game in which she played the queen and I played the pawn.
“Get cleaned up, we’re going out. You can use the upstairs bathroom now.” She was standing over me. The early morning sun flowed through the window at her back and cast a shadow over me, literally and figuratively.
We spent the day shopping. Candy had a few accessories to pick up for her date, a necklace and bracelet that would nudge the limit of my paycheck, some sexy underclothes and a few things for me that she wouldn’t show me until we got home. We ate lunch in a restaurant. The conversation was stilted. Candy was distracted, probably musing over what would happen at Frank’s place after the show. Before long it was late afternoon and we had to head home to get ready for what was to be a big night for both of us.
When we came in the front door, Candy immediately said, “Take off all your clothes and wait for me in the bathroom. I’m going to help you get ready. Be sure to shave close.” I had wondered how that was going to work. I certainly didn’t know anything about putting makeup on. “But you’re going to have to learn fast, Sissyboy. I can’t do this for you all the time. I have to get myself ready. ”
“Here.” She handed me a bag. “I bought you a book and some cheap makeup to help you practice and learn later on. You can put it on after work every night.” The bag was filled with all kinds of small packages in various bright and pastel shades. She pulled the book out of the bag and handed it to me. It was a guide to applying makeup. Evidently, this was going to be a regular thing. I wondered if I was ever going to able to fuck my wife in a normal way again.
“And I think you should grow your hair kind of long, wigs are so phony. I’ll style it for you for awhile, or I can take you to the beauty salon.”
“Candy, I can’t believe you’re going so far with this. What do you think I am? Why can’t we go back to being the way were?”
“The way we were ended when we gave into Frank, Sissyboy. I’m going to enjoy my life and you’d better learn to also. You may not understand, but you need me to tell you what to do. You’re so naïve, Jimmy.”
I didn’t say anything, I just turned and headed upstairs to take a shower, shave and wait for her.
When I stepped out of the shower, Candy was waiting. The sink was covered with all kinds of makeup in shades of pink, red and lavender. She sat me down in the chair she normally used for herself and started applying makeup. Eventually my face was covered with cream and foundation, rouge, eye-shadow, eyeliner, fake oversized lashes and finally a sultry shade of shiny pink lipstick. When she was done, she admonished me loudly not to ‘mess it up’, handed me a small pink bottle, told me to go paint my fingernails and toenails and to wait for them to dry properly, then to get dressed and wait for her downstairs.
As I looked at myself in the mirror I had to admit that she was an artist. The result was professional. I didn’t look like a hooker, I looked more like a young girl who was ready for a heavy date and wanted to impress.
All the clothes were laid out on the bed, the same French maid’s outfit I had tried on a couple of days ago, the blonde wig, high heels and lingerie that went with it. There was a fake pearl necklace and bracelet too. I put them all on and walked carefully downstairs to have a couple of strong drinks. I felt somewhat like a clown with all that stuff on my face, but somehow it felt sexy and had me aroused, especially the nylon panties pressing my penis against my abdomen. Had I always been this way? Could I remember anything from my childhood that would make me like this? Was I enjoying being submissive? I wasn’t sure, but there was a kind of comfort in letting someone else take control; letting someone else tell you what you are and what you should want. I wasn’t totally opposed to what was happening. And I had to admit that I felt sexy in a submissive feminine sort of way.
I sat and watched TV and had a couple of martinis while I waited for Candy to come down. I didn’t know what time Frank and Ted were going to arrive, or whether they would come together or separately. But I surely had quite a buzz on when I started into my third drink.
And the doorbell chimed. My insides panicked. Was it Frank or Ted? And what would happen when I opened the door dressed in drag?
Standing up slowly and wobbly on my high heels I started walking towards the front door. I knew I should have practiced with these high heels a lot more! I almost fell a couple of times and had to reach my hand out to catch the doorknob to steady myself. I had trouble forcing my hand and mind to turn the knob, but I couldn’t stand there forever. I swung the door open slowly. It was Ted. I stood there not knowing what to say. He stood there staring at me. Amazingly, he produced a bouquet of red roses from behind his back and handed them to me.
“Hi, Sweety, how they hangin’? You look great!” I really didn’t think that was funny.
And then I heard Candy’s voice from upstairs, “Who is it, Jimmy?”
“It’s Ted Crasnow.” I shouted in an all too self-conscious masculine voice.
She was at the top of the staircase in a half-open robe, her breasts almost falling out, looking down at me in the doorway. “Well make him a drink. Don’t just stand there, Sissyboy.” God, I had to get another name even if it was feminine. Sissyboy was entirely too demeaning, even for me.
I turned around. Ted stepped in and put his arm around my waist. “Hey, what’s this Sissyboy stuff?” he said as he tightened his arm around me steadying me on my feet. He was strong and had no trouble at all holding me straight. I found his arm to be comforting, his scent sweet and enticing. Was I giving in to him already?
I looked up and Candy was just turning around as Ted walked me into the living room and seated me on the sofa. “How about that drink, or should I make it myself, Sissyboy?” He laughed and headed to the kitchen as I settled back on the plush pillows. He seemed to know his way around and in a couple of minutes was back with a martini. He took a couple of sips, sat down close beside me and put his drink on the coffee table. He slipped his arm around my shoulders and pulled me to him and kissed me full on the lips. His other hand roamed down to my leg, under my dress and up and down the front of my panties. I tried pulling away, but I was already half drunk, very horny and weakening fast. I hadn’t said a word yet, and it didn’t look like I was going to get much chance to. I thought he would at least wait till Frank and Candy left.
And then the doorbell rang again. Ted just looked at me. “Do you want me to get that, Sissyboy. You don’t look too steady.”
“Yes, please,” I replied, thankful for the interruption.
Of course it was Frank Ballwell. Ted opened the door and Frank cruised in like he owned the place. Maybe he did.
“Where’s Candy?” And then he saw me sitting on the sofa dressed like a French Maid. His laugh was loud and embarrassing. “Hey, Sissyboy, you look really beautiful tonight. Maybe I’ll take you to the show instead of Candy.”
“I’ll be down in a minute, Frank, fix yourself a drink.” Candy’s voice floated down from somewhere upstairs.
“The stuff’s in the kitchen, Frank, have a martini on me,” Ted laughed too.
As Frank moved out of sight, Ted started mauling me again. This guy was ready for some serious playtime.
“What’s going on over there?” It was Candy at the top of the stairs in the most beautiful gown I had ever seen. It clung like a snakeskin and shimmered like blue-cut diamonds as it caught the light moving over her sinewy voluptuous body. It was low-cut to the point that it appeared that her nipples would be exposed as her breasts bounced gently in rhythm with her body descending the stairs.
She was looking at Ted with one arm around my shoulders and the other burying itself under my petticoats. She smiled and looked ready to laugh. “I guess I don’t have to worry about you two. Looks like your going to get along just fine.”
She walked into the kitchen to look for Frank. As soon as she passed, Ted renewed his attack on what was left of my virtue. One part of my mind was trying to hear and figure out what was going on in the kitchen and the other trying to figure out what to do about Ted. I had a vision of Frank’s hands roaming around Candy like Ted’s were around me. But with Ted’s hand rubbing my dick through the nylon panties, I was getting aroused in spite of myself.
In a minute, Frank and Candy came into the living room hand-in-hand and sat down together on the love-seat across from Ted and I. They each had a drink, but managed to kiss each other lightly so as not to mess up Candy’s lipstick.
“Well, Sissyboy,” Frank said, “I hope you have a good time with Ted tonight, because I’m going to fuck the living daylights out of this lovely lady beside me.”
Candy laughed, “Frank, you shouldn’t rub it in. He’s still getting used to the idea that he belongs to us. Poor little boy, or is it poor little girl, Sissyboy?” they both laughed as I sat there staring at them, my heart constricting tightly in my chest. I lowered my head trying to think of something to say to get back at them, but it’s hard to argue when you’re dressed as a French maid and someone has his hand up your skirt. I was hoping they would just leave so that I could deal with Ted in my own way. I’m wasn’t sure about what I was going to do, but I thought I could handle it better alone.
Then Candy spoke up, “Frank, don’t you think Jimmy’s so pretty tonight. Wouldn’t it be a shame to waste all that loveliness. Let’s have him put on a show. We have time don’t we?”
“Plenty of time, Candy, I’d love to see if he’s learned anything too. Whaddya say Teddy?”
They didn’t even ask me. Teddy spoke right up, “Gosh, he is pretty isn’t he?
“Stand up, Sissyboy and turn around. Let everyone see how good you look,” Candy said.
I stood up and slowly turned around in a circle, a bit more confident on my high heels, even though I was still a bit unsteady from the martinis.”
Frank spoke, “What’s he wearing underneath, Candy? I’d like to see.”
“Lift your skirt, Sissyboy. Let everyone see your pussy.” Candy said, looking straight into my eyes, daring me to challenge her.
I lifted my skirt as I turned around again. The panties were shear black see-through. They could all see my hardon. And then Ted stood up behind me and put his hand on my dick, rubbing up and down, squeezing me tightly with his other arm. He worked his hand inside my panties and pulled them down in front to show Candy and Frank.
“I’m going to fuck you right in front of your wife and her lover, Sissyboy, got any objections?”
“Please don’t,” I said as I ineffectively tried to struggle away. He had his hand on my dick and was holding tight, jerking up and down.
“Gonna come now, Sissyboy? Come on let’s see you squirt.” Frank and Candy were smiling, sipping their martini’s, reveling in my discomfort as Ted’s hand worked it’s way tightly up and down on me.
“How about Doggie-style, Baby. Get down on all fours.” He put his hand on my back and pushed me slowly down. I was in a kneeling position, then on my hands and knees with my panties down around my thighs and he was lifting my skirt. I heard his zipper go down and then I felt his dick in the crack of my ass. It was already hard. I was going to have to let Frank and Candy watch him fuck me. He must have spit on his dick, because it was moist as I felt him pushing against my opening. It took a couple of minutes, but he worked it up inside me slowly. And then he started pushing me over to where Frank and Candy were sitting.
When I was very close to Frank Ballwell, between his legs, he unzipped his pants and pulled out his dick close to my mouth. “Do a good job, Jimmy-Baby. Just enough to get me warmed up for your wife.”
I mouthed his dick as Candy watched me, still taking sips from her drink. I saw her light up a cigarette and take a deep draw and then blow it in my direction.