Cream Puff Ch. 01

Never borrow money you can't pay back right away. When I got in trouble with the IRS, I borrowed money from my wife's brother Larry, and I struggled to pay it back.

We were drinking at his house a few weeks before his wedding when he brought it up.

Larry: Hey cream puff, I know you don't have the cash to pay me back right now, how about doing a job for me to work off your debt?

Once when she was drunk, my wife Sally told her brother that she liked to dominate me sexually by pegging me with a strap on. Ever since he'd always jokingly called me emasculating names, like cream puff or sissy or girly boy. The Irony is that Larry is actual gay. He's engaged to a very brawny man named Roger.

Me: Sure Larry, I'd love to get out from under this. It's taking forever to pay it down. What's the job?

Larry: Well, next week Roger and I are having a joint bachelor party and we haven't hired a stripper yet. I thought you might like to dress up in some girly lingerie and give us a show.

My wife was so caught off guard by the suggestion she laughed beer out of her nose.

Me: I don't know Larry, I mean that's not really something I'm into... I'm not... well you know, I'm straight.

Larry: You're not completely straight if you let my little sister hump your ass with a rubber dick. Besides, it's just a bit of fun. Some of the guests are straight too you know. Gay people can have straight friends. Come on. It'll be fucking hilarious for Roger and me to have you giving lap dances in a mini skirt. Plus, I'll wipe out your debt. I don't want a money problem hanging over or relationship. It's not healthy.

With the promise of having our debt gone Sally said yes for me. She giggled drunkenly as she promised to have me all cleaned up and ready for my performance.

Monday was busy at work and I nearly forgot my commitment until Sally texted me just at the end of shift instructing me to meet at her salon. Not sure what she had in mind I arrived directly after work. She had two salon technicians waiting for me.

Her plan, hair removal. My entire body from the neck down was waxed. I'd like to say I handled like a man, but when they ripped the curly hairs from by wrinkled scrotum, I shed tears like a baby. It really hurt. The whole thing took three hours and cost me $250. I was supposed to be working off my debt and here I was charging a torture session to my already abused credit card.

I would be lying if I said it didn't feel incredible. Having all the hair removed from my body felt electric and sensual. Walking and feeling the smoothness of my thighs on my penis was a huge turn on.

It was dark when they finally finished with me, but I wasn't done yet. Sally instructed me to do some shopping on my way home. She returned home and I went to the mall.

The first stop was a shoe store. Her instructions were clear; sexy, stiletto, and open toe. I was red faced and mortified when I found the right shoes and asked the attendant if she had them in my size. She didn't bat an eye though and quickly helped me measure my feet, then returned with the right size. I'm not a particularly large man. In fact, the opposite is true, but I was still surprised to find out I wore a size 9 in women's shoes. That was only slightly larger than Sally's size.

The second store was a lingerie boutique. Again, Sally had instructed me. One-piece body suit, sheer, snaps in the crotch. Also, fishnet stockings and a garter. I found what I needed on the shelf and was out in less than five minutes.

My final stop was the most awkward. In the women's bra section of a large department store they sold silicon rubber breasts. They were meant to be used by women who'd lost their breast to cancer, but Sally ordered me to buy a pair of my own. She told me to buy the largest pair they had, which turned out to be double D. The lady at the counter gave me dirty looks throughout the entire purchasing process. I left quickly, afraid she was going to report me to the police as some kind of pervert.

At home I put my purchases in our closet and then ate dinner with my wife. Sally didn't bring up the evenings activates, but a dreadful anticipation hung in the air, like an elephant in the room.

That night in bed Sally rubbed my hairless balls and cock as she teased me about my pending performance.

Sally: Do you think you'll like giving lap dances? Felling their cocks between your ass cheeks?

Me: Oh god, I don't know if I can really go through with it. I'm gonna need to be pretty drunk, I think.

Sally: That might not be the best plan. What if they take advantage of your drunkenness and try to put their dirty cocks in your little girly mouth?

Sally was working my shaft at a very steady pace and I was getting turned on. Whenever she speaks dominantly toward me, or treats me in a feminine manner it takes my arousal to the next level. I have a powerfully erotic attraction to submitting and being emasculated. The feeling of being owned or controlled is sexually liberating. Almost like I can do anything because it's not my choice. I have to comply with my master's orders.

Me: You don't think they'll do that, will they? Am I going to have to suck cock to pay off my debt?

Sally: Would you like that you little sissy? Huh? Do you want to rub your girly ass on the real men's cocks until they're hard and then slip those beefy dicks into your wet hungry mouth?

Me: Oh no. Do you think the powerful men will want me to suck cocks? Am I going to have to work my debt off on my knees? What if I don't suck cock good enough? What if my virgin mouth doesn't please them?

Sally: Don't worry little sissy, real men will take control and fuck your mouth with their hard cocks until they shoot hot cum down your throat. Once you put their dicks in your mouth you better be ready for them to get what they want out of you.

Her hand was pumping fast now and her teasing and emasculating words had the desired effect. Ropes of white semen shot out from my penis and coated my stomach as well as Sally's hand.

She held my shrinking penis in her hand as my breathing returned to normal. The moment or arousal had past and the thought of actually sucking a cock now seemed disgusting to me.

Sally: I hope you're ready to really suck cock. It's very likely some of the guest are going to want more than a lap dance, and I think Larry had that plan all along.

She wasn't being sexy now, she was giving me a warning. In the back of my mind I guess I suspected the same thing all along. Larry was family and for the most part a great guy, but he did have a tendency to push things. Plus, Roger was going to be there, and he always made jokes about me kneeling in front of him or bending over for him. It was all in fun, but sometimes I thought there was some truth to his jests.

Sally brought her cum cover hand to my mouth and touched it to my lips.

Sally: Here, taste this. You need to be ready for the taste in case you do have to suck some cocks. It's not very pleasant, but it's easier to deal with if you know what to expect.

My stomach knotted up as my tongue licked the goo from her hand. It was salty and slimy and repugnant. I had to force myself to swallow it. I nearly retched. She used her fingers to scoop more cum from my body and fed it to me, repeating the process until there wasn't anything left to clean up. Quiet tears rolled out of my eyes as I ate my own cum.

The next day when I got home from work Sally instructed me to shower and get my new outfit on. The sheer body suit felt fabulous against my hairless torso. The connected panties snapped shut against my man parts, and the thong stretched tightly into my ass crack.

The fake boobs were stuck in place using cosmetic double-sided tape, and the weight of them against my body felt real. When I walked, they bounced and sagged and they pulled my skin as they moved. Within a few minutes they felt completely real and natural. I loved them.

Sally finished me off with a long curly black wig she kept for dressing up. She then spent nearly an hour working on my make-up. She tried different colors and combinations, cleaning some off and trying other shades until she was satisfied with the results. I did not recognize myself in the mirror. The face was mine, but a much softer, more submissive version of me.

Sally: Alright, now you practice. Before dinner you need to walk up the hallway and back three hundred times in those shoes. You only have four days and you need to be able to walk and dance in them.

For the first few laps Sally watch me, coaching me on how to hold my hips and how to place my feet in order for my walk to look natural and feminine. She also instructed me how to shift my hips to exaggerate the movement of my ass cheeks. She then left me to practice as she watched her programs.

Back and forth, over and over. My feet hurt from the pinched toe of the shoe, and my calves were trembling trying to balance on six-inch heels. Still I pranced back and forth for hours, shaking my ass and swinging my hips. The velvet texture of the stockings rubbed my thighs and kept me in a constant state of arousal.

After dinner, with my girly outfit carefully put away I laid naked on my bed and once again Sally took advantage of me.

Sally: I can't wait to hear how those strong me use your mouth. I get so excited knowing you're going to get used by real men. Does it turn you on knowing you have to submit to Larry's guests to pay off your debt? Do you feel like a whore yet?

Me: Oh god yes. I feel so slutty. I know Larry is going to make me suck Roger's cock. I think that's what he wanted all along. I think this stripper idea is just his way of making me his bitch.

Sally: Oh, I know you're going to have Roger's dick inside you, but what if he doesn't want to throat fuck you sweetie? Roger is very strong and masculine. He might not want your mouth after you have already sucked off all his guests. He might want something fresher. Maybe Larry is going to offer your virgin asshole to Roger as a wedding present.

My head was swirling in euphoria. The titillation of being jerked off and talked down to was driving me crazy. I could feel the shame of the words my dear wife was saying and I enjoyed every second of it.

Me: He's going to make me his bitch, isn't he? I'm going to have to spread my ass for his cock and get fucked like a slutty little bitch just to pay off what I owe, I'm going to be his prostitute. Your brother is going to turn me out for his future husband.

Sally stopped rubbing my cock and when I looked at her, she had an evil grin on her face.

Sally: Get your knees up over your head bitch. I'm going to jerk you off into your own mouth.

Twisting myself up I got situated with my penis dangling above me. My mouth wide open and Sally jerking me while pointing my dick hole at my face.

Sally: Open your cum dump you little pansy. Get ready to eat some ball batter. After those real men are done with you, you're going to swallow cum like it's your job. Come on hubby, show me what a little cream puff you are. Shoot your goo down your throat!

My orgasm was epic. I'd never felt more degraded and dominated in my life. spurt after spurt of white cream shot from the tip of my penis and painted the inside of my mouth. Only a couple drops missed and landed on my face.

Sally: Don't swallow yet sissy. You're going to brush your teeth with that before you're allowed to swallow.

The end of my orgasm was the end of my arousal, I felt deep shame and disgust with myself. Sally watched with a gleeful smile as I used my toothbrush to smear my own cum onto my teeth and gums. She urged me to keep going, get every surface, leave nothing unbrushed. Pitiful tears rimmed my eyes as I spent better than ten minutes cum brushing my mouth. Finally, I was ordered to swallow.

Wednesday, Thursday, and Friday were a repeat of the same. I practiced walking and dancing seductively in my new heels. Sally made a point of humiliating me constantly. She was getting more and more excited as Saturday approached. Each night she ridiculed and demeaned me as she jerked my cum into my mouth. Each time I was forced to scrub and gargle with the disgusting white goo before I was allowed to swallow it.

Saturday morning Sally woke me with an enema bag in her hand. Oh shit, I thought. This is really going to happen. She spent all day teasing me, driving me crazy with submissive desire, yet leaving me unsatisfied.

Sally: I bet you can't wait to get on your knees for real men, can you?

And

Sally: Do you think it will hurt when they throat fuck you?

And

Sally: After you get done fucking all that man meat, do you think you'll mind if I fuck some of it?

And

Sally: I want you to pay close attention when you're eating cum. I want you to tell me whose juice tastes the best.

When it was finally time to get ready, Sally used cosmetic adhesive to tape back my sack and prick. She pulled them backward as hard as she could and taped them into place. The effect was that once I was in my panties, I had a very female shape. The heavy rubber breasts were attached and as soon as I felt them against my body my penis tried to get hard. It was impossible, and painful.

On top of my outrageous lingerie, Sally presented me with a gift. A tiny little maid outfit. The top barely covered my bouncing boobs and my ass hung out of the tiniest of skirts. With my wig and makeup in place I was ready. As a man I looked ridiculous, but for a woman I was surprised how good I looked. Even Sally complimented me, and she wasn't teasing. I was sexy.

Sally dropped me off at her brother's house. She giggled as she instructed me to obey him, and have fun.

Roger: Good god man, you might be the best-looking woman I've seen this week. I'm not going to be able to control myself around you tonight.

Larry: You are such a puff. I guess both me and my sister are attracted to gay men huh?

There were no guests when I arrived so Larry put me to work in the kitchen getting snacks ready and setting up the bar.

As the guests arrived, I took their coats and brought them drinks. They all looked at me, then looked again, then smirked.

As the party progressed, I refreshed drinks and passed around the hors d'oeuvres. Then the music changed.

I started my show with a strip tease. Slowly discarding my top and skirt, then my heels and stockings and garter. When I opened my bodysuit at the crotch and stripped it off over my head the room was deafeningly loud with laughter and cheering. It was a wild feeling having these men (some of them straight) whoop and holler as I gyrated and bounced for them. I felt desired and it was intoxicating.

Larry brought out a chair and placed it in the middle of the room, then he guided Roger to the seat and told me to work my magic on him. I had replaced my heels after stripping off my stockings, so I strutted as seductively as I could toward him. Turning away so that my ass was almost in his face I bent forward and backed into him. I rubbed myself on his chest and then settled on his lap. His erection was immediately obvious. As I rubbed my exposed ass checks on his cock through the thin fabric of his slacks, he whispered to me.

Roger: I hope you know you're mine tonight. I'm going to use you until you can't walk straight you prick tease little faggot.

I could feel the power in his body, in his cock, in his voice and it made me tremble with excitement.

Roger: Sally told us all about your prep work. When you were swallowing your own cum did you think of me? Did you wonder what my cum tastes like? Don't worry cream puff, you'll know soon enough.

No one could hear him but me, the guests were drunk and rowdy. They cheered as I dry humped their host with my ass. The energy was chaotic and empowering and I gave in. Completely.

Turning and dropping to my knees I pressed my face into Roger's crotch and used my lips to hug the outline of his dick. The fabric of his pants was rough on my lips, but before I could pull away his hand found the back of my head. Pulling my face against the hardness of his cock and rubbed himself on me, grinding against me. And then he stopped. He stood up and dragged a guest into the chair and I started my lap dance all over again.

Only seven of the men at the party sat in the chair for me, including Roger and Larry. Larry went last, and as I finished his dance by dipping my face into his groin, he scooped me up and placed me across his knees. The party erupted in jeers and laughter as he started spanking my bare ass cheeks.

At first it was only startling, feeling his strong hand smack my vulnerable flesh, but he continued, and continued. Each swat stung painfully and I could only imagine my ass cheeks were getting red. Still the crowd cheered him on, still my ass was assaulted by my brother-in-law.

Tears were forming in my eyes when he finally stopped. His hand rested on my ass and my skin was hot and sore.

Larry: Well pantie boy, I think you've paid off about half of what you owe me. What are we going to do to work off the rest?

I thought he was just teasing me, but he had paused and was waiting for me to answer. Even though the spanking had been uncomfortable, I was marinating in hypersexual ecstasy. Being dominated by a powerful man while other men watched and cheered was more erotic that anything I'd ever even fantasized about. I was beyond all inhibition.

Me: Whatever you want Sir. I'll do whatever you tell me to. I want to leave here debt free and I will do anything to make that happen. Anything you command.

My heart was racing and I was scared as much as I was horny. I knew at this point someone was going to fuck me before the end of the party. I was going to be a fag for my brother-in-law.

The party calmed down after my spanking. I couldn't find any of my clothes so I returned to my maid duties wearing nothing but my heels and my glued-on breasts. Most of the men groped my ass or gave me a soft spank as I filled their drinks or replaced their bottles. It was obvious to them all I was community property. Slowly though the party dwindled as guests made excuses and left for home.

By midnight only three guests remained. Larry got out the poker chips and a game started up. At first, I continued to serve the guests, but after a while Roger grabbed me and roughly pulled me into his lap. Wrapping his arm around my shoulders he pulled me to him.

Roger: I have the most chips, so you have to do what I say little girl. And I say you sit here and give me good luck.

He guided my hands to his groin and I carefully unzipped him and put my hand into his pants. As he continued to play cards I rubbed and stroked what had to be a massive cock. I had never seen Rogers dick, but I couldn't get my fingers all the way around it.

After twenty minutes or so Roger swore and threw down his cards. One of the other guests, a guy named Pete laughed. I guess I'm the chip leader now. Send that little tart over here. Pete made me kneel next to him and as he played, he slowly pushed one finger in and out of my mouth. For the next several hands I sucked a fat finger in front of all these real men. Pete loved the submission.

Pete: You like that little girl? You like putting things in your mouth? Maybe I'll put something else in there. Would you like that?

The card game continued and soon I was passed to another. He ordered me to kneel face down ass up and lick his shoes. His wingtips were mostly clean, so it was more humiliating that it was gross but as I licked his shoe, he rested his hand on my ass and strummed his fingers against my crack. Occasionally he would brush my rosebud with the tip of a finger. I hate how much I enjoyed licking that man's shoe while he teased my asshole.