Bringing Out Kimmie Ch. 02

The next morning I made breakfast for my wife as usual, kissed her goodbye as she went off to work and went to my computer to try and get some work done. After an hour there was a knock at the door. I knew it had to be Seth. My hands were shaking as I opened the door.

"Good morning, Kimmie. I hope you slept well with visions of being a fairy dancing in your head."

I let him in, and looked up and down the hall, hoping nobody was out there to hear what he said. Luckily, the corridor was empty. Seth was carrying a shopping bag as he stepped in.

"What do you want?" I asked him.

He smiled and said "Oh, I have a lot of ideas. But really the question is what do you want?"

"I want you to leave me alone. I want to forget what happened yesterday. And I want you to delete that video."

"Oh, I don't think any of those things are going to happen, Kimmie. I set up that video system to record what goes on in my bedroom. I use it for my work, or to safeguard myself against claims of nonconsensual sex, or just to have a recording of really hot things, like yesterday. I knew when I turned it on when I went to get you your costume that I would have a lot of fun watching it over and over."

"Why are you doing this to me?"

"Two reasons: One, because I can. Two, because I sensed in our limited elevator conversations that you were probably a sissy. And last week I saw you in the hallway going to the trash chute, and it was pretty clear you were wearing a bra under your shirt. So I set up the scenario yesterday. You see, my practice and my writings explore the outer bands of sexual practices. Which is fortunate because that's where I like to play as well. I might use that video in a conference. I'm sure Carole would love to attend, don't you think?"

"You said you'd never tell her if I did what you asked!" I was nearly sobbing, and this came out in a whining, unmanly voice."

"And I won't tell her, but that doesn't mean she might not stumble across the video somewhere. Perhaps on the internet if I upload it, perhaps she'd hear about it from one of your friends who would attend my lecture."

"Please. I'll do anything for you if you just promise to keep that video between us. What is it you want?"

"Again, the question is really what you want, Kimmie. You were quite explicit when you were getting into your fantasies yesterday. You may think you're being coerced, but I know that deep down this is what you've been dreaming of. So, again what is it that you want?"

I sighed. He actually was right. I'd had deep fantasies that I tried hard to push down. I was very happy married to Carole and our sex life was satisfying. I'd never told her before we married that I liked to wear women's clothes, and it seemed that if I were to tell her now she'd be angry that I hid it from her, regardless of what she thought about my actually dressing. But the fact was that that desire was very much a part of me.

"Kimmie wants a man to show her how to be a girl, to take charge of her, and make Kimmie his compliant sissy, and to show Kimmie what a slut she can be. But Kimmie can't do this. Her marriage means more to her than any silly fantasy."

"Your fantasies aren't silly, Kimmie. They're part of what and who you are. If you were my client I'd advise you to explore them to the fullest. So, instead of paying me $225 an hour to tell you that, you get me helping you actually explore them for free. And we'll be very careful so as not to let your wife know, until you decide otherwise. Now I want you to strip completely"

As I took off my clothes Seth reached into the shopping bag he's brought. The first thing he handed me was a pair of black control panties, like a mini girdle.

"These will be the only panties you will wear from now on, Kimmie. No matter how many times you cum in them, no matter how cum-stained they become, you will not wash them."

Next he handed me a black bra, followed by the same white blouse I'd worn yesterday. And I put them on he came up to me and massaged my tits, making me moan with pleasure. "For now, Kimmie, we will leave your bra empty. But we will get some bra inserts to flesh out your figure. And who knows -- maybe someday you'll get those huge F-cup tits you want."

Seth next handed me the pair of high heels from the day before, and then knelt down and tied my feet together with plastic strap ties. I was now so hard even the control panties couldn't stop my tenting. Next Seth pulled out a video camera. I thought of protesting but lacked the will to challenge him anymore. Finally, out came a large, realistic dildo. He handed it to me and I took it.

"Now, Kimmie, for the camera, tell us how much you love that dildo."

"Kimmie loves to practice her skills on dildos especially ones that look like a real man's cock. Watch as Kimmie shows off her skills." I took the dildo in my mouth and proceeded to give it a blow job, licking it up and down and taking it into my mouth.

"Why do you like big cocks, Kimmie?" Seth asked.

"Kimmie is a sissy faggot whose only purpose in life is to please real men. Men who have big cocks and know how to really take care of a woman, not like Kimmie's little clit."

"Deep throat that cock, Kimmie. Take it all the way in."

The dildo was 10 inches, and quite thick. I tried to take it all in, but at just the halfway point I gagged. And had to pull it back out.

"Oh, Kimmie, Kimmie. You didn't do what you were told. That means some punishment for my little sissy."

Seth reached into the shopping bag and pulled out a pair of cloverleaf nipple clamps with a chain attached. He clamped them onto my nipples over the bra. My already hard cock strained against the control panties. Seth pulled the chain to make me stand, which wasn't easy with my feet tied together in high heels. He then spun me around to face the bed and bent me over.

"Bend over and put your hands on the bed, Kimmie. Put that cute little sissy ass in the air." I did as he said, and he took the chain from the nipple clamps and put it under my hand. "Now don't let go of that chain, Kimmie, or the punishment you're about to receive will be just a small taste of what you'll get."

Seth went into the closet in the bedroom and brought out one of my wife's shoes, a flat loafer. He positioned himself behind me and said "Okay, Kimmie, as I punish you for not obeying me, I want you to tell me what you will do to make amends for your failure. When I'm satisfied the spanking will end."

As he spanked my ass hard with the shoe each blow made me flinch, which pulled the chain attached to the nipple clamps. I tried to think of what would make Seth happy enough to stop.

"Sir, Kimmie will do anything to please her master. Kimmie will suck his cock whenever he wants!"

"Well, Kimmie, you're going to do that anyway. What else?"

"Sir, Kimmie will suck any cock master tells her to! Kimmie will go anywhere with Master to suck cock."

That apparently wasn't enough, as the spanking, and the torture on my nipples, continued.

"Sir, Kimmie asks that Master be her pimp! Kimmie will dress in her hooker outfit and sell her mouth and pussy on the street to earn money for Kimmie's master!"

"That's better, sissy. Now one more thing will stop this punishment. You have to cum in your panties without touching yourself."

I thought of what would make me cum, and I fantasized about having those huge breast implants, and being fucked in a parking lot by multiple men. As the spanking got harder I was getting closer, and then I added to the hooker scenario having my wife watch me getting gang-banged and laughing at what a sissy faggot her husband turned out to be. As I envisioned this I arched my back, pulling the chain on my nipples hard, and exploded into my panties with a truly explosive orgasm. I fell forward onto the bed, facedown, spent and exhausted.

Seth sat down next to me and gently rubbed my ass. "Excellent, Kimmie. But tell me what it was that sent you over the edge. Was it the spanking, the hooker fantasy, or the nipple clamps?"

"Sir, it was all three. But I also, I mean Kimmie also thought about Carole seeing Kimmie and laughing at her for being such a sissy fag."

"Ah, so you're ready to bring her up to date with the truth?"

"No, Sir. Kimmie will never be ready for that."

"Well, Kimmie, from my experience -- and the fact that you just came thinking of it -- I think that is an integral part of your fantasies. But I will not force that on you. When you're ready it will happen. But now, since you've cum, I think it's my turn, don't you? Stand up again, and bend over the bed."

He helped me up and positioned me over the bed. He then unzipped his pants and got behind me and placed his hard cock against my ass. He started rubbing it up and down my crack.

"Now, Kimmie, it's my turn to share my fantasy of how we're going to proceed. You know the Adonis Theater on Sansom Street? It's a few blocks from here, and I'm sure you've passed it many times. It's a gay theater of course, but really the best action is downstairs in the basement. It's dark and there are no inhibitions down there."

"I'm going to dress you in hooker platform heels and fishnet stockings. You'll wear a schoolgirl skirt that just barely covers your black panties which will be very cum-stained by then. Your red bra will be filled with very large breast forms. Not quite the F's you dream of, but DD's. You'll wear a pink gauze blouse that lets your bra be seen, tied up to expose your midriff. You'll have heavy hooker makeup on, but no wig. You'll clearly be seen as a sissy fag as we walk the four blocks from here to there. You worry that you'll be recognized by somebody you know."

Seth was now rubbing his cock on my ass faster and faster. I pushed back against his cock to feel it harder against me.

"When we get to Adonis, Kimmie, we are going to go downstairs to the basement. You will find a booth, and none of them have any doors. You will pick the booth with the most cum on the floor, and you will kneel in that booth. I will stand outside and tell all the men walking by that my sissy fag slave gives the best blow jobs they've ever had. And you will do that -- give a great blow job to every man who wants one. But you won't let them cum in your mouth -- they will only shoot their load on your face and tits until you are covered in cum. And then we will walk back to this apartment, with everybody seeing your cum-covered sissy self. And then you will present yourself to Carole and tell her that this is who you are, who you need to be, and that you will never be anything but a cum slut sissy faggot for real men, and she is free to find men, men with real cocks who will finally fuck her like she needs."

That must have been the high point for Seth, because he shot his load all over my ass. He then massaged it into my panties, back and front.

"Turn over, Kimmie, and lick my cock and hands clean." I did as I was told.

"So, Kimmie, are you going to ask the obvious question?"

"What question, Sir?

"Oh, my you truly are a bimbo. Obviously, the question is why I didn't fuck you in your pussy. I'm sure you're dying for it."

He was right, though it hadn't even occurred to me before. My ass clenched thinking of his huge cock plunging into me.

"Well, Kimmie, I will fuck you eventually, perhaps sooner, perhaps later. But before I do I am going to need you to train that pussy to take my huge cock. I am going to leave you with three dildos. One is 6 inches, one is 8 inches, and then there is the one I gave you earlier. All of them look like real cocks. You will practice with them. When the 6 inch goes in and out easily you will move to the next size, and when that one goes in an out easily you move to the biggest. You are to practice an hour a day, including working while you keep them inside you, and - this is very important -- you will not play with yourself while you do it. When you can fit the 10 incher inside you pussy easily and you cum just from having it there you will be ready to take my cock like a good girl. I have to go now; I have office hours this afternoon. I will leave you the panties, in addition to the dildos. I suggest you find a very good hiding place unless you want Carole to "accidentally" find them. I will be back tomorrow, sissy."

When Seth left my first thought was where to hide the goods. I went into my closet and dug out an old brief case with locking latches. I stripped off the panties and put them in. I was about to put the dildos in, too, but decided there was no time like the present to do my practicing.

I took the 6 incher and coated it with Vaseline my wife kept as a makeup remover. I put one foot up on a chair and tried to put it into my ass. It wasn't going at first, so I put some Vaseline in my finger and pushed it up my ass, coating the inside. I tried again, and with some hard pushing I was able to get the dildo in. Without the restraint of the control panties my cock became rock hard again.

I went back to my computer to get some work done. I put a towel over the chair and sat down. That drove the dildo further in, and I moaned with pleasure. I tried to get some work done, but it was difficult to concentrate. So I went to Literotica and searched for stories about forced crossdressing. As I read some of my favorites I bounced up and down, driving the dildo into may ass. Several times I came close to cumming but I stopped bouncing each time. I looked at the clock and realized I'd been at it over an hour. I got up and pulled the dildo out, cleaned it, and put all my toys and the panties in the briefcase, which I locked and put back in the closet.

I showered, dressed (with male underwear), and the rest of the day went as normal. When my wife came home we made a simple pasta dish. I had two glasses of wine, which I rarely do. As we watched TV Carole started running her hands along my thigh. This was always a clear sign from her that she was in the mood. We turned off the television and went to the bedroom. I was worried that I might have trouble getting it up. But as we cuddled, and Carole played with my nipples, the memory of the dildo in my ass made my cock very hard.

I made sure our foreplay included several orgasms for Carole before I started to get on top of her. But Carole decided she wanted something different. She straddled my head, facing my feet, and ground her pussy down on my mouth. I gave her all I had, tonguing her clit and driving my tongue deep into her. She was playing with my hard cock as I did this, and each time she came she squeezed it as hard as she could. As I felt I was about to cum I drove my tongue deep into her while pushing hard on her clit with my lip. She squeezed my head with her thighs and grabbed my cock like it was a handle keeping her from falling. Her grip was painful, but I loved it, and shot a huge stream of cum in the air. She collapsed, lying on top of me for several minutes before rolling off.

She looked at me and just said "Wow, lover." We cuddled up and as we drifted off to sleep I was happy that I could still please my wife so deeply, even as I thought about the feel of the dildo in my ass. I was a bit confused, but realized I would eventually have to be comfortable in both my roles.

Copyright by Willow Melody. Please do not share without attribution