March Madness Ch. 06

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offended, stop reading and do something else. The author retains all rights to this story. You may re-post the story unchanged, provided there is no intent to profit from this story (it is not nice to make money from someone else's work).

The author enjoys comments on his web-published stories, so feel free to e-mail him through the link below.

Chapter 6:Sunday Morning Coming Down

I had very little sleep when Rachel invaded my gray matter.

"Time to get up and greet the day Stephanie! You have a busy day today."

I reluctantly stirred and opened my eyes. We repeated the morning bath and primping ritual and Rachel had me lick her asshole for about an hour for her wakeup orgasm. I was learning how to tongue fuck an asshole like a pro. I would trace circles on her rosebud and then push my tongue inside as far as it would go. I would pull my tongue out and use my teeth to gently nip her ass cheeks and then it was back to swirling and fucking in and out with my tongue. I had tried once to reach around and use my fingers on her pussy, but Rachel stopped me.

"Stephanie I want to see if you can get me off by just using your tongue on my asshole, no hands! You are going to learn how to be the best ass worshiper any woman could want for a lover."

Rachel was getting very excited and I could see the pussy juice dripping out of her. Her big climax had not come even though she had had several small ones. I was getting tired of kneeling with my face in her ass and my tongue was numb from all the action I was providing. When I thought she was going to give up on my tongue fucking because she was shifting around, I noticed that her asshole was starting to twitch. I pulled my head back and watched it open and close on its own until Rachel growled for me to get back to work with my tongue.

I pressed my mouth to her asshole and started pushing my tongue into her asshole as far and as fast as I could. A few seconds later her body shook as she had a powerful orgasm. I kept swirling my tongue over her asshole as she came down. It was not like her clit, her asshole was not so sensitive that licking was uncomfortable after a big climax, so I kept at it until she said I could stop.

Rachel gave me a short, black, silk kimono robe and she put on a matching red one. We went to the kitchen and made coffee and had a brunch of fresh fruit and croissants, which Rachel had picked up from a bakery. I started to clean up, but Rachel decided that I needed more time licking her pussy to improve my skills. I knelt between Rachel's long legs and began to lick her pussy as she leaned back in her chair.

"My ass needs some attention Stephanie, so I want you to fuck my asshole with your fingers while you lick me! All that tongue fucking has made me itch down there and now you are going to have to make the itch go away. And take your time, don't just go for my clit with your tongue!"

Rachel was having no trouble instructing me on how to make love to her. She had complete control over what I did, how fast I did it, how much force I used and how long I did it. I was learning what sexual servitude was. Not some fantasy and web site visit, but real sexual servitude. My dick was completely caged and I had no hope of relief before Rachel let me out of my cock prison. I had never been more horny in my life and the more I served her, the more I thought about sex. The only sex I was getting was for her benefit, but all I could think about was sex and serving Rachel was the best sex I could have. I was more sexually turned on then I have ever been and each day just added to my desire and motivation to please her.

I licked my finger and gently worked it into her asshole as I licked her pussy. Rachel's pubic hair was trimmed nice and short and that allowed me to give a lot of stimulation to the entire external area of her pussy. I started by licking her outer labia and every once in a while would slip my tongue between her pussy lips to get a taste of her nectar. The muscles in her leg would give a little twitch, as my tongue would slide through the folds of her pussy lips.

"Fuck my ass harder!" Rachel instructed.

Her asshole was way too tight for me to work my finger much past the first knuckle without more lubrication. I noticed the butter on the table so I got a good sized glob of the warm butter and started working it into her asshole. The warm butter was perfect and I was soon able to slide my finger all the way in to it's full length.

"Faster!" was all Rachel said.

I moved my oral worship from her outer labia to her inner lips and would swoop my tongue up to her clit. Her pussy juice was running out now and I kept swallowing it down to keep it from running down my face and onto my silk robe.

"My ass needs more in it, and since there is nobody around with a hard cock, use more fingers!"

Well I could have a hard cock if only Rachel would take this damn cage off! I was working a second finger into her asshole and she was opening up to this added thickness. Now I was licking her pussy as fast as I could and was spending a lot of time working her hard clit with my tongue. Rachel was shaking all over and I could tell that she was having a series of small orgasms as I finger fucked her asshole and ate her pussy.

"I need more in my asshole!" she moaned.

I got some more butter and was soon fucking her with three fingers. Rachel was shaking harder and a strong moan was coming from her as I used my fingers and tongue on her. Then I slipped my forth finger into her asshole and was working my hand in and out as fast as I could all the way up to end of my fingers.

"Yesssssssssssssssssss" was all that escaped Rachel's lips as her body was racked with a strong orgasm. I went back to gently licking her outer pussy lips and gently finger fucked her ass with one finger as she calmed down. I could feel her asshole spasm on my finger and after a while her asshole began to relax and the spasms slowed down.

Rachel pulled her legs up into the seat of the chair and this rotated her ass so that her rosebud was looking right at my mouth.

"Stephanie, you better get that butter cleaned up before it gets on my silk robe!"

I gently began to clean up the butter from her asshole as Rachel relaxed in the afterglow from her second strong orgasm of the morning. You can not imagine how hard it is to clean up butter mixed with pussy juice from a woman's ass with just your tongue. It took me a good 15 minutes to get enough licked off to know that she would not get a stain on her robe.

"Stephanie, you are finally learning how to make love to me! When you are out of the cock cage all you can think about is your own pleasure, but now you only can have sex by pleasing me! Isn't it great?"

"Yes Miss Rachel." I groaned.

I got up off my knees and again started to clean up the kitchen when Rachel informed me that Hannah would be coming over soon and that she wanted me to wait a bit to clean up the kitchen so that I could enjoy my new surprise. I didn't know what to think as Rachel and I relaxed with some more coffee and read the morning paper. Well anyway Rachel relaxed; I was too horny and too worried about my next surprise to relax.

It wasn't long before Hannah drove up, but it took forever by my mental clock.

Rachel went to the door and let Hannah in. I waited in the kitchen as Rachel had instructed me. Again the time passed ever so slowly in my mind with total mental anguish for me, but I am sure it was only a few minutes before they summoned me to the living room.

"Stephanie, since you are going to be Miss Hannah's maid next weekend, we thought we should get you ready by helping you practice today. Isn't that very nice of Hannah to come over and help you get ready for next weekend?"

"Thank you Miss Hannah for helping me learn how to be a better maid." I stated with as much enthusiasm as I could muster.

"Your welcome Stephanie and I must say that those breast forms look great under that robe, I can hardly wait to check them out." Hannah said with a very amused smile on her face.

My two tormentors had me pick up several shopping bags and follow them into our spare bedroom. We had turned this extra bedroom into an exercise room and we had our workout equipment and such installed there. After removing my robe, they had me reach up to the pull-up and they used our bondage wrist cuff to tie my hands overhead.

"Those breast forms look great!" was the only comment Hannah made once I was stretched out.

"I know, you can hardly see the edges of the form where I glued them to Stephanie's chest!"

The two women went on talking like that for some time, commenting on my body and what they could do to further improve my look for next weekend. First they took out a heavily boned black corset and wrapped it around my torso and started lacing. I groaned when Hannah pulled the laces tight and that seamed to put the off a bit.

"Stephanie, if you can't cooperate with us and quit making all those noises, we will just have to gag you." The two of them informed me.

They let me rest a moment and as I was getting adjusted a bit to the tightness, Hannah gave a second pull on the laces just as I had exhaled. It took me by surprise and it was almost like getting the wind knocked out of you. The damn thing was so tight that I felt like I was going to pass out! Once I was able to suck in a little air, I started complaining.

"Please Miss Rachel and Miss Hannah, don't lace me so tight!" I begged.

"We have a lot of work to do and we can't be putting up with all these interruptions!" Rachel informed me.

Rachel started searching through her bags and a queasiness joined the tightness from the corset joined the feeling in my gut.

"Look what I found just for a mouthy sissy boy!"

In Rachel's hand was a penis gag. It was about 4 inches long and very thick. Attached to the base was a strap for wrapping around your head.

"Please Miss Rachel, I can be quiet!" I begged.

"You had your chance and besides, I want to try out my new toy."

With that she pressed the tip to my lips. I held my lips closed, but Rachel grabbed my balls and gave them a firm squeeze. I immediately opened my mouth and Rachel pushed the gag in. It filled my mouth completely. My jaws were straining and it pressed back so far in my mouth that I was almost gagging. It was a very realistic cock gag with veins, ridges and a swollen glans. While it was not as long as my cock, it was very thick. I was gaining an appreciation for why women were hesitant to let me fuck their mouths with my thick cock. Rachel would give me head, but she always kept her hand on the base of my cock to make sure that I didn't jam it in harder or faster than she wanted. And she almost always made me lay back and not move when she gave me head. If I started thrusting up she would just pull back her mouth until I quit. I enjoyed her technique, because it was more of a teasing blowjob and she could drag out my orgasm for quite some time that way.

"This was an expensive cock gag, but it had several special features that I liked!" Rachel pointed out to Hannah as she buckled the strap. "It is a great length, it completely fills the victims mouth, it is even thicker than Stephen's so it will make Stephanie's stretch wide to accommodate it and it has a couple of surprises. There are two special holes in it. One is an air passage so that you don't have to worry about the safety if you leave it in for long periods and the second is for this feeding tube!"

Rachel and Hannah were examining the feeding tube and getting excited by the possibilities.

"You can feed liquids so that Stephanie doesn't get dehydrated!"

"Yes, and think of all the possibilities we could use besides water, things that Stephen would hesitate to take can now be fed without a protest, can you imagine this hooked up to a load of sperm! It would drip down the tube and there would be nothing Stephanie could do to keep from swallowing it!"

"But were would we get a load, Stephen's not going to be cumming, so he won't be the donor!"

"I have an idea that we can get Stephen to help out even if he doesn't want to. In nursing school, they told us about prostate massage and I think it may be just the ticket!"

"I read about that on one of the web pages Stephen visited. They said it reduces the sperm fluid buildup without reducing the horniness! The information on the technique was provided from a couple where the man was in a chastity belt for long periods and his wife used the technique to help insure prostate health! I think he had not been allowed to cum for about 2 years and he got a milking about once a month!"

"I couldn't go without a good fucking for 2 months, let alone 2 years!"

"Well she didn't! She would have her husband fuck her with a strap-on cock and she had some boyfriends on the side! When she got horny, she would invite a boyfriend over and have her husband serve them a meal. Then she made her husband help the boyfriend fuck his own wife. He had to lick her pussy to get her ready and if the boyfriend was not hard, she made him use his hands and mouth to get the boyfriend ready! Then she made her husband put the boyfriends cock against her pussy and rub the head up and down her pussy to get it good and wet and when she was ready, he had to guide the boyfriends cock into her pussy!"

"You're kidding?"

"No, and when the boyfriend was done fucking her, she made her husband eat her pussy to clean out the boyfriend's sperm, she called it a creampie!"

"Man this is making me horny, can I borrow Stephanie's tongue, I had a good fucking this morning before I came over and I am sure a little bit of a creampie is still in me?"

"I think that would only be fair for all the help you are giving Stephanie! Besides, I am all orgasmed out from Stephanie's tongue and my clit is too tender for any more action right now. But first let's finish getting her dressed to see if his costume for your sweet sixteen party fits."

The two women worked the laces again on the corset and I felt the blood rush to my head and I was having to concentrate on my breathing, but after a bit I adjusted and was able to breath without panic. Next came a pair of black seamed hose that they slid up my legs and adjusted to make sure the seams were straight. I wished the hose were on Rachel, because they had a fancy pattern in the weave that would have made her sexy legs look fantastic. Once they had the garters attached from the corset, they took my costume out of a box. It was a classic French maid's costume, black satin with all the trim in white lace and stiff petticoats. They had me lift my legs to step through and with some difficulty, they slid the tight dress over my newly busty chest. When Rachel slid the zipper closed, it fit like the proverbial glove.

"It fits perfectly, you did well in giving the seamstress the measurements." Hannah offered.

"Yes, I knew what I was able to get his waist down to in the other corset and this one is an inch smaller. Then I knew his other measurements from a custom shirt order we placed from last month and his new tits we knew from the spec sheet you had!"

"The girls are going to be thrilled with Stephanie at my party!"

I was feeling seriously light headed. I was incredibly turned on and my dick was swelling as much as the cock cage would allow. All the pussy licking I had been doing and my lack of any orgasms for me coupled with Rachel making me live out my masturbation fantasies was causing me sex overload. There was a large mirror installed in our workout room and I could see how fantastic I looked from the neck down. With the fake tits and tight corset, I was a sex fetish mind-fuck and if my cock were free it would be hard as a rock.

The skirt on the dress was only long enough to cover my ass and the stiff sewn in petticoats pushed it out almost as much as it hung down. If I bent over in this outfit, my ass would show completely. I actually had enough curves that I didn't just look like a man in drag.

"Now for the shoes!" Rachel stated and broke my trance. "I found these on-line and they had a cross reference to men's sizes and they should fit perfectly!"

The shoes were a shinny black leather and had about 3 inch heals. They were a classic looking woman's high-heal with ankle straps. Rachel had me lift my feet and she placed the shoes on me. I knew that many women complained about wearing heals and I instantly could tell I would not enjoy these shoes. The height of the heals changed my balance and tightened my calf muscles more than was comfortable. My body weight was now much more on the balls of my feet instead of my heals and I knew that my feet would get sore long before I ever got used to these shoes. And even standing still, I felt unstable!

"The ankle straps have loops in the buckle so that you can put a small padlock through them, but I got these little bells to put in the loops. Now when Stephanie walks around we will be able to keep track of her and if the bells quit jingling, we will know she has taken them off!"

"Look at his dick, he is dripping cum and he isn't hard and nobody is even touching him!"

It was true, I looked down and I couldn't see my dick with all the petticoats and skirt, but I could see drips of cum on the floor.

"I guess we better give Stephanie her milking before she ruins her maid outfit. I can't believe how much she likes her fantasy now that we are helping her experience it for real!"

If I didn't have this cock gag in my mouth I would have argued that all the pussy and assholes I had licked coupled with the fact that I wasn't getting any orgasms of my own had more to do with it than any costume they were putting me in!

"I think it will be easier to milk her if she is bent over." Hannah offered.

The women released my hands from the overhead bar and after making sure that I didn't fall over in my new shoes, they hooked the wrist cuffs together behind my back. Then I was bent me over as far as the corset and tight dress would allow and the wrist cuffs were tied to the bar. I tried to push the cock gag out of my mouth so I could complain about my uncomfortable position, but it would not budge. I was bent over almost 90 degrees and with the corset I could hardly breath. It was so uncomfortable that tears came to my eyes.

"I have never done this, but in nursing school they said that by massaging the prostate rectally, you can push out the seminal fluids."

"I printed out the instructions from the web page on milking a man's prostate, so that might help!"

"Read them to me."

So Rachel read them for Hannah.

The seminal vessels, ampulla and prostate can also be emptied by massage of these glands through the rectum. Rhythmically massaging the organs in an in-and-out motion with an anal dildo is one way. But perhaps a more reliable way is to simply use either the middle finger or the middle finger and index finger together (well lubricated), to apply a firm slow massage over the nodules of the glands inside the rectum. The massage will force the seminal fluid and sperm past the valves in the ejaculatory ducts, and empty the prostate (which discharges directly into the urethra). If arousal is low or penile stimulation is stopped for a brief time before the prostate massage begins, draining of the ejaculate into the urethra will not trigger orgasm. Once ejaculate appears at the meatus, it will help to empty the urethra by running a finger firmly up the underside of the penis from the root to the head, pushing the ejaculate in front of it.