Ivana Pushing Sissy's Limits

Story Info
Wearing a dress to a Christmas Party wasn't enough.
5.4k words
4.06
102.2k
38
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
frezrevup
frezrevup
407 Followers

"You look ravishing," my wife Ivana said as I stood before her in a short red velvet dress with white tights and black Blahnik mary janes heels. She walked over to put a hair band in my long black hair. It was down to my shoulders now, flat-ironed straight.

We stood together in front of the mirror after she was done. In her heels, Ivana was four inches taller. We looked like the perfect man and wife, except I was the wife.

Ivana was stunningly svelte. She exemplified grace in her fitted shirt, tailored wool slacks and leopard pumps. No matter the situation, Ivana, in dress, manner and demeanor left no doubt who ran our relationship.

"What's wrong, Leslie?" Ivana asked as I helped her on with her coat.

"This is the first time I'll be wearing a dress," I said following her out to the car. "There will be fifty couples. All the other executives and their spouses, we've never met many of them. I've never had to attend a party in a dress before. These people are all rednecks. This isn't Napa Valley. They use the N-word like it's no big deal."

"Baby, where is all this coming from?" Ivana asked as she started her Aston Martin. "All the girls are so excited to see it. You worked for months making it. Your girlfriend Karen would be so disappointed if you didn't wear it. We've been here six months now and everyone has been really accepting of your feminization."

That word, that terrible word. Ivana bandied it about like it wasn't in any way evocative.

"The guys ignore me," I said as the pressure of a freak out built inside me.

"Normally, I'd cut you off and that would be the end of it," Ivana reminded me then turned to look at me as we waited at a stoplight. "Leslie, I'm a little hurt. We're a team and you're excelling at the submissive role has vaulted my career. Don't you think showing up in this pretty dress sends a message about me, about us? Don't you still want to be a team?"

"I'll quit whining," I said though my insides churned at the idea of parading in front of people in a dress. "I'm sorry, Ivana."

"No, Baby," Ivana said. "I'm allowing you to say your peace. But, wasn't I right when I told you that you couldn't handle the stress of being the leader in our relationship? Don't you feel better with all the pressure on me?"

"Yes."

"Wasn't I right when I told you that you'd make a great homemaker? Wasn't I right when I said that you'd feel much better in panties and with smooth skin?"

"Yes."

"And when your ass was filled with that first big black cock, didn't you cum harder than you'd ever cum before? Aren't you a little black cock slut now?"

"Yes."

"Is there anything more fulfilling that submitting to a thick black cock?" Ivana asked. "Can you please a man wearing a stained t-shirt and five o'clock stubble?"

I giggled.

"So what's all this boy talk, Baby?" Ivana asked. "Are you going to try to pee standing up? Are you going to start eating Doritos and drinking beer? I bet you'd love all that orange gunk on your manicured hands."

"Stop teasing me about wanting to be so prissy and tidy," I said. "I'm sorry for freaking out. You're always right."

"Baby, don't slouch," Ivana said to get me back into line.

"I'm sorry, Ivana," I answered and bowed my head.

"I'm very proud of you," Ivana said as she lifted my chin. "Your yoga studio is doing so well right now. Looking so great in that dress, you should be able to lock up some new clients. Everyone is always complimenting your pretty little body."

"I do like hanging around with the girls," I said.

Ivana laughed and squeezed my hand.

"I'm not going to let your craving to be on your knees for cock fool me. You're still a little pussy hound," she said before poking my ribs until I let out a girlie squeal. "You've got over a hundred hot women paying you a hundred eighty bucks a month to put your hands all over them under the guise of it being a yoga session. All the other wives ask you out on day dates and hug and kiss on you. Karen is the hottest piece of Asian ass around and she'd fuck the cock off of you. What guy at the party has more pussy on their hands?"

"I'm sorry for not being able to overcome my fear of humiliation," I said.

"No," Ivana said. "I know it's hard, Sweetie. You've got all those silly man notions in your head, but seeing you in that dress soaks my panties."

Suddenly I felt emboldened. "It does?"

"It's not the dress," Ivana said. "You're acknowledging how much you love me by willingly suffering extreme humiliation to make me happy. These bitches all want to steal you away because they see that devotion. Those assholes that tease you are just jealous."

Ivana was right. I sucked at being a man and did have women hanging all over me. It made me grin. All men talked nonsense about doing anything for their wives, I was about to prove it. I could endure stares and comments. It was no big deal. Karen's constant promotions and fat salary proved that my being the sissy behind the woman worked.

"There's my happy girl," Ivana said as we pulled up next to the curb in front of Mary and John's house. "You are so fucking pretty and have been a girl so long, you really trick me sometimes. The girls and I forget you have a cock. Then something like this happens and you're spouting off, being all macho. We still have so much work to do. This is all my fault, baby. I promise to keep pushing your limits."

"It's my fault," I interrupted.

"Shhh," Ivana scolded. "Stop your impertinence or you'll wear a handprint on your cheek. This is my fault and I promise to redouble my efforts to keep pushing you until we wring out all of that miserable fuck clinging to the walls inside you. I've just been too easy on you because I love you so much and you're so fucking pretty."

Karen turned off the car and let out a breathy sigh. "Damn, all this fag talk about your love of cock has gotten me horny. Let's go inside before I have to put you on your back and fuck you in the car. I'm going to have to keep my mind on ways to push you or I'll end up humping some husband in the corner tonight."

As always, I should have just kept my mouth shut. It wasn't good for the last thought in Ivana's head being about breaking down my barriers.

My nerves were ragged again by the time we reached the door. Some stuffy jerk I'd never met answered the door and launched a disapproving stare at me when Karen referred to me as her spouse.

My whole body blushed and I averted my eyes. I wanted to die. There was no way I could make it four hours.

Then I heard the sound of Karen's voice. As the traditional Japanese wife, we shared so much in common, we instantly bonded. In our area, there were few other Asians for her or submissive feminized husbands for me to relate to, so we stuck together.

Her husband, Burke, was a hairy, hulking brute that ran one of the hospitals in Ivana's company. Like the other husbands, he mostly ignored me and since I was always grouped with the women, we rarely did anything but greet each other. Back during the summer at a topless pool party among the five couples in our inner circle, I caught him staring at my little A cup breasts a couple of times, but never thought any more of it. I guessed he liked them since I was slender and small up top like Karen.

Because I'm such an anomaly in the South, and I play the role of the traditional Southern Belle, women take right to me. The new ladies welcomed me into the group. The guys split off to go watch football downstairs and we gathered around the kitchen and everyone helped.

They were blown away by my culinary skills. In addition to two years of culinary school, when we were in San Diego, Ivana's boyfriend, CP, who was an award winning chef at a local restaurant, used to give me private lessons three times a week. To tell the whole truth, most of the time, he had me on my knees or was up my ass during the private lessons. He kept me in nothing but an apron so there was easy access.

All the new faces got us gabbing too much and drinking too much. We were late getting everything started. The girls sent me downstairs with chips and dip to hold off the guys for a while longer. On my way back to the kitchen, I passed through the archway under the mistletoe at the same time as Karen was rushing toward the pantry.

She was a buzzed. She stopped and kissed me on the lips a little too long.

"Lezbos," Mary joked as Karen broke off the kiss.

Everyone laughed.

"We all want to do it," Cindy, one of the new wives said. "Leslie's just so darling."

The women had danced around it before, but once they saw I took teasing without getting angry, they unleashed a barrage of questions about my lifestyle. Soon it worked its way into a discussion about Karen and me and our crush. Finally, the alcohol took over and many of the wives admitting to wanting to catch me under the mistletoe. Inhibitions vanished.

The word worked its way down to the guys and people became acutely aware of passing each other under the arch.

The drinks kept coming and without any substantial food to sop it up, the party had the feeling it was on the verge of getting out of control.

Karen's kiss started all the women getting a little handsy with me. When a bunch of repressed women got the green light to explore their sexuality, it quickly escalated into going overboard. They kept corralling me under the mistletoe to get a taste of my lipstick and I can't say that I was resisting. Somebody was going to end up getting fucked before the night was over.

As the end of halftime neared, the hot food was finally ready. The guys all rushed upstairs to fill a plate before the third quarter started. I was hurrying to get some of the guys a beer when Burke passed me under the mistletoe. His mouth was on mine before I knew what was happening. I had a beer in both hands and he had me gathered up so I couldn't get away until he was done, and believe me, he explored my mouth thoroughly.

People didn't know what to say. It sobered everyone and for a while the girls talked around it. Ivana saw the whole thing but never said a word.

I don't know. I was a little buzzed too so I didn't get freaked out about it once we started eating and the conversation eased back to normal.

The party was supposed to be over at ten and a few people went home but the house was still packed and the booze recklessly flowed. The guys played pool and video poker and watched the second game while a few of us girls decided to dance.

Sheila was a tall skinny blonde and she was fascinated with me. She wanted to lead and kept running her hands over me. During a slow song, she pressed against me to feel for my cock. Somewhere in the middle of a song, Burke tapped on Sheila's shoulder and started dancing with me.

The three girls with me took off upstairs to get the rest of the wives. I was trying to be nice about it, but Burke was rough and controlling. He moved me over until we were next to the bathroom door then pushed me inside and pinned me to the wall with one of his huge hands.

After locking the door, Burke slammed all his weight against me and went for my mouth.

I don't like white guys or hairy guys or guys with average size cocks. Burke had his out and was trying to tug down my tights as he roughly bit at my neck and tried to kiss me. Outweighing me by at least a hundred and fifty pounds, there was little I could do. Once, early on, I got my hand on some shelves and pulled them down, but he locked me up tight from then on.

As Burke ripped a hole in my tights, there was a knock on the door. Burke kicked my legs apart and pulled me up off the ground to sit me on his cock, but stopped when someone shouted for him to open the door.

When he didn't respond, Ivana kicked it open.

"Get off of Leslie," was all Ivana had to say to make Burke put me down. No one ever fucked with her.

Before too many stares and too much gossip killed the mood at the party, Ivana led all of us to one of the spare bedrooms on the top floor.

Karen was there and so were Mary and her husband, John.

"We're all drinking," John said. "Boys will be boys. I'm sure Burke is sorry for any misunderstanding."

That fight instinct in a male surged up in me. If I'd had a gun, I would have shot Burke. That fucker tried to rape me and John's bullshit comment made it worse. I was ready to call the police.

"Take a deep breath, Baby," Ivana said to me then looked over at Burke.

"Leslie, I apologize," Burke said staring right at me.

He did seem sorry.

"You've been at all these parties dressed up and looking pretty," Burke said. "Tonight, you're so demure and elegant, so diminutive and graceful. I got so drunk I started wondering what it would be like to fuck you. Then you let me dance with you."

"That sends a message to a man," John chimed in. "You have to be careful."

"You did let him kiss you for a long time," Ivana said.

I wasn't having it and Ivana immediately sensed me about to tell everyone to fuck off. Burke was drunk and full of shit. They were making it seem like it was my fault.

"Leslie does look very pretty tonight," Ivana said to get everyone in the room to acknowledge it. At that moment, I knew Ivana was about to test my limit. I was as scared as I was insulted and angry.

"And you are sorry, aren't you?" Ivana asked Burke. "There's no excuse, right?"

"Oh, you're right," Burke said. "Leslie, that was totally uncool of me."

"Leslie," Ivana said. "Do you accept his apology?"

"Yes," I said having no other alternative.

"Mary and John, I think we can handle this," Ivana said. "We don't want to keep you from your guests any longer."

I had to hug Mary and shake John's hand before they left.

Burke stood with his hands on his hips at the end of the bed. I was on the opposite wall pressed against the curtains. Ivana and Karen stood next to each other at the door.

"Leslie, go ahead and pull off your tights," Ivana instructed me. "Karen, let's leave the boys alone and let nature take its course."

A wry grin sprouted on Burke's block head. Karen looked worried and resisted a little until Ivana moved her out of the room. I was so mad and so hurt I didn't know what to do first.

"Are you wearing a bra under that dress?" Burke asked me. "Do you need a bra for those perky little titties?"

"Yes," I said as I stooped to unbuckle my shoes.

"No, Leslie," Burke said as he walked over and sat in a chair and crossed his legs. "Strip for me like a pretty girl. Show me how a yoga girl can do it. I love to watch you be so feminine."

I just wanted to get it over with. There was nothing sexy about it. I sat up on the bed and put my legs under me and unbuckled my shoe then twisted around running my hands down my leg to remove it.

"You fucking cunt," Burke said uncrossing his legs then putting his hand over his zipper. "You move that little body better than Karen. Do you take cock?"

"Yes," I said as I undid the other strap. With my shoes off, I put my legs together and held my feet so that he could see my painted toes.

"You little whore," Burke said. "You always have your toes painted like a hot fucking bitch. You think you can take this cock? Is that why you were afraid?"

I wanted to tell him I could five cocks his size at the same time but I batted my eyes and said, "Please be easy with me, Burke."

"Go on and take those tights off," Burke said. "I want to see your little pussy."

My job was to submit to Ivana's desire. If Burke didn't walk downstairs with a king-of-the-world strut, I was going to be severely punished.

I took it slow and slid the tights down one leg then the other. Burke couldn't take it. He pulled out his cock and stroked it as I daintily removed the material from my feet making sure to keep my legs in the sexiest position and turned so he could see my red thong.

"Hold on," he said as he stood and walked toward where I sat. "Get down on your knees and suck my cock with your pretty dress on, Baby."

I got down, but Burke caught sight of Mary's glasses on the nightstand and made me put them on.

A few seconds later, Burke proved why I hated white cock.

The guy had no ability to control himself. He clumsily crammed his five-incher down my throat and pumped away. His cock was so hairy I'd still be picking his pubes out of my teeth a month later. So much for the sexy striptease, he was leaking pre-cum like a teenager. It was all going to be over in a few seconds because after letting him fuck my mouth a few more times, I planned to suck him so good he'd nut in less than a minute.

"Oh Jesus," Burke blasphemed as he pushed away from my face. "Baby, not like that, you fucking whore. Damn you look so fucking sexy in those glasses. I'm so fucking wasted I can't believe I'm going to pop my wad from a blowjob."

He was done talking. He grabbed me and threw me on the bed on my stomach. He pushed my thong to the side and tried to ram me as he climbed on top of me.

"Let me get wet," I said so he'd move enough to free one of my hands.

Ivana always made me lube so I'd be prepared for cock at any time. All I needed for a thin reed like his was a touch-up with licked fingers.

I guided Burke to my opening. "Be easy with me, Burke."

The big ogre got off on thinking I was scared.

"Girls have always been afraid of this big monster," he assured me as he ran his hands over my ass and stared at my opening. "We'll take it an inch at a time, Leslie. I'll be good to you. I never meant to hurt you, Baby. You just got me out of control. You are such a submissive little bitch. It drives me crazy that you'd let Ivana run you around. All she had to do was tell you to take off those tights."

Burke pushed inside me until I was opened but it was him that let out a huge moan.

"Shit!" he grunted. "That is damn good pussy. Fuck me, I can't believe I'm fucking a girl in the ass."

"You feel so good," I said. "But I'm so scared."

"Think you can take a little more, Babe," he said as he cock continued to thicken. It wasn't the biggest cock in the world, but that thing was hard as steel.

"Yes, for you I can," I said. "All this time I've been watching you staring at me, I've wondered what it would be like."

Burke pushed in an inch deeper and that craving for cock that I could not quell aroused in me. Suddenly, my pussy took over and I was into it. When I gripped him to pull in more, Burke lost his fucking mind.

He pressed his full weight on me and rammed all he had inside. He put his hands up under my arms and locked over mine. His whiskey breath heaved out as he pounded away on my ass.

It wasn't going to last very long.

He started saying, "I'm sorry, Baby, but it's just too good. Damn, I fucking your ass and you're just laying there taking it so pretty for me. Take my cock you little faggot."

"Cum inside me," I said. "Please, I want to feel you filling me up." That was all it took. Burke blew his load making so much noise people a block away heard it.

He pulsed inside me for quite a while. I have to admit that the feeling of him burning up my pussy with cum got me leaking.

I laid there under him, feeling his weight, knowing that everyone at the party was talking about me being Burke's bitch. I was sick with humiliation thinking about having to go back downstairs with Burke's load inside me. This was a new low that I might never recover from.

"Shhh, Baby," Burke whispered into my ear. "I didn't hurt you did I, Baby?"

"I can still feel you cumming in me," I said. "You were cumming so strong. That makes me feel good that I was pleasing you. It feels good with you on top of me."

Burke kissed my ear and said, "Is there anything I can do for you, Leslie? I don't know what I'm doing here but just tell me and I'll give you anything you need."

The sweetness in his voice made it hard to hate him. A bull would have made me clean him up and walked out as soon as I finished.

frezrevup
frezrevup
407 Followers
12