March Madness Ch. 05

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Stephan/Stephanie thinks he might die from frustration.
3k words
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Part 5 of the 10 part series

Updated 10/31/2022
Created 01/23/2009
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jbirdman
jbirdman
198 Followers

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 via the CONTACT link on his profile.

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Chapter 5: Saturday Surprises

We got up late on Saturday and Rachel had me make her breakfast in bed and pamper her most of the morning. When she was ready to get up, I drew her bath and helped her soak in the tub and when she was done with that she put on her silk dressing gown and had me give her a pedicure. I knelt before her and massaged her feet with lotion and even polished her toenails. It was a very pleasant morning and I was beginning to enjoy spending so much time tending to Rachel's needs without concern for my own. In the past, I would have fucked Rachel in the bathroom while she was bathing and then gone out and watched the basketball commentary on ESPN.

When I was done with Rachel's pedicure, she gave me permission to worship at her pussy. I gently parted her robe and kissed her legs up to her pussy and gently began to kiss and lick her.

"That's right Stephanie, take your time and let me build up slowly to my orgasm."

I had always enjoyed eating pussy, but my motivation in the past was to get Rachel all hot so I could fuck her. I was beginning to realize that my pace had been faster than Rachel preferred and she was now giving me the coaching I needed to become a better pussy licker. I ate Rachel's pussy for about an hour, before she had had enough.

"That was wonderful Stephanie, but now we have to get you ready for your basketball games!"

Rachel got out a clean set on lingerie for me to put on. Today everything was red. She slid the red hose up my legs and hooked them to a garter belt. Next came a lacy pair of tap panties that went over the straps from the garter belt. I had figured out why it was done this way yesterday, who would want to undo the garter straps every time you needed to go to the bathroom. Rachel lubed up the but plug and had a much easier time sliding it in today. I had worn it 10 or so hours yesterday and now it felt almost natural to have it stretching my asshole. Today she didn't mark it, because she was going to be home all day and didn't need a tamper proof seal. Next she slid a red silk slip over my head and had me turn around for her.

"Stephanie, it just does not hang right. Take it back off."

"Yes Miss Rachel."

Rachel went to the closet and took out a package and in the package was a red corset. It went from the hips to a half-cup bra and it was one of the fanciest corsets I had ever seen. It had hook and loop pearl buttons in the front and laces in the back. Rachel helped me remove the garter belt and wrapped the corset around me. Once all the small pearl buttons were secured in the loops, she had me turn around and stretch up my arms.

"Take a deep breath and let it out Stephanie."

When I finished exhaling I got a bit of a shock as Rachel pulled the laces tight.

"Please Miss Rachel, it is too tight!" I begged.

"Nonsense Stephanie, you just need to get used to it!"

Rachel gave me a few minutes to adjust and then she had me exhale all my air again and she pulled the laces even tighter.

"Now you have a bit of a shape!" Rachel said as she tied off the laces.

Next Rachel hooked up the garter straps from the corset to the hose and had me turn around again for her inspection.

"Better, but now you need something for your bra cups."

Back to the closet for a second package.

"Hannah gave us some manufacturer's samples for you to use!"

In Rachel's hands were two perfect flesh colored breasts, nipples and all.

"These are top of the line from a breast form manufacturer in Sweden, but the surgeons at Hannah's office decided that they didn't need a second supplier for their mastectomy patients. Aren't they lovely?"

"Yes Miss Rachel."

"Look at them, they even color the nipples and areolas so that they look more natural!"

"I see Miss Rachel."

"Close your eyes and I will put one of my breasts in one of your hands and the silicone breast in the other and you tell me what you think?"

I closed my eyes and a second later, a breast was in each hand. I felt the texture and density of the two breasts and even though I could tell the fake from the real, it was very close.

"The fake breast does not feel like real skin, but otherwise it is perfect Miss Rachel!"

"I know!"

Next Rachel coated the back of the breast with a clear liquid and slipped it into the cup of the corset bra. She adjusted it just the way she wanted it and in just a few seconds released her hold.

"The adhesive is waterproof, for swimming and will attach the breast form to you so that it will move naturally."

Rachel took the second breast form and just as quickly attached it to my chest.

"The European sizes run a little different than US, so the best we can figure is that you are somewhere between a C cup and a D with these forms. Now walk around for me and let me see how they move."

I paced back and forth a few times and I could definitely feel the breasts moving with me.

"Jump up and down a few times!"

As I jumped up and down, I could feel the breasts bouncing just like a swimsuit model running on the beach.

"Oh Stephanie, they move perfectly! When Hannah said that they were the best, she wasn't kidding. What do you think Stephanie?"

"They are wonderful Miss Rachel, thank you."

"Your welcome Stephanie, but you will have to give Hannah a special thank you later!"

"Yes Miss Rachel."

"Now come and sit at my makeup table so I can fix your face a little!"

I sat down and jumped back up immediately!

"You have to keep you back straight when you wear a stiff corset Stephanie!"

I sat down carefully, keeping my back very straight. It was uncomfortable, but in a few seconds I adjusted to the posture. I had to force myself to breathe regularly with much more shallow breaths than I was used to.

"Don't worry, no woman has ever died from wearing a corset, just relax and you will get used to it!"

Next Rachel worked on my eyebrows a little and since I didn't have heavy eyebrows, she didn't have to do very much to give them a little shape.

"Don't worry Stephanie, without eye makeup nobody will even notice that I gave your eyebrows some shape, they are a very light colored and nobody will notice the little plucking I did!"

Rachel spent the next 10 minutes or so putting makeup on my face. She used a little foundation; some blush, made up my eyes and put on a thick coat of lipstick that matched the red color of my lingerie. When she was done, she had me turn toward the mirror.

"See how you look now Stephanie!"

I was in shock at the image in the mirror. I could see from the top of the corset up and for the most part I looked like a woman. The biggest problem was from my eyes up. With my haircut I looked like a man in drag.

"What do you think Stephanie?"

"I look like a man in drag!"

"Well I think we can softer the look a little with a wig!"

Back to the closet she went and came back with a strawberry blonde wig cut like Nicole Kidman's. The next thing I knew Rachel had it on me and I was staring into the face of good-looking woman, not beautiful, but not bad.

"You look beautiful Stephanie! You have always had fine features for a guy and with a little makeup, I think you could pass!"

I sat there staring.

"Well what do you think Stephanie?"

"I can't believe it Miss Rachel, you have done the impossible."

"I think you look fantastic, better than I hoped! Now let's get you situated for basketball games."

We went to the den and Rachel had me sit on a hard stool in front of the TV. Next she put on the padded cuffs, both hands and feet. She locked the leg cuffs to the stool legs and then ran a chain down from the wrist cuffs to the chain connecting the ankle cuffs. I wasn't going anywhere before Rachel decided to let me up. The hard stool was jamming the buttplug into my ass and the corset was forcing me to sit very straight, which contributed to the pressure on the buttplug.

"I checked the schedule and the Arizona game does not come on for 2 hours, so I got something to keep you busy in the interim."

Rachel put a tape in the VCR and put it in repeat mode. When she pressed play, the introduction to a porno movie started playing. It was a movie I had seen advertised on the web with a story line of a wife turning her husband into a sissy slave and lesbian lover; then forcing him to eat her pussy after she got fucked by a real man. I had gotten excited reading the description and had even watched a short promotion "AVI" file on the web page, several times.

"I figured you wanted your own copy of this video, since you visited the web page so often."

I must have been staring again.

"Aren't you going to thank me Stephanie for you special video?"

"Thank you Miss Rachel for ordering my favorite video." I said as I blushed.

"And one more thing Stephanie, I will come back and turn off the TV and let you up anytime you want, but the TV stays off the rest of the day. I will come back when the Arizona game starts and shut off the VCR so you can see your Wildcats play! Call me if you decide that you are done watching TV for the day."

With that Rachel was gone and I was staring at my fantasy porno movie. The woman looked a lot like Rachel, except that she had fake boobs and she was putting her husband through just about the same treatment I had been going through. He was increasingly feminized, had to lick pussy constantly and he was being denied any relief. His cock was caged with a solid metal tube and it was attached to his dick with a large piercing in the head of his cock.

As the movie progressed, his wife/mistress decided that his tongue worship and vibrator fucking was not enough, so she brought a lover to the house. As it always turns out in porno movies, he was hung like a horse and proceeded to fuck her every way possible. When the stud was done fucking her brains out, she made her sissy husband beg to clean her pussy. The camera had a close-up of her lowering her creampie pussy to his face and if my cock had been free, I would have been jacking off furiously.

The tape was on it's third play when Rachel came back.

"I see you are still watching TV, do you want to go to the little girls room before the game starts?"

"Yes please Miss Rachel may I go potty!"

I was stiff from my forced posture, but with Rachel's help I was soon standing and on my way to the bathroom. When I started to move, I really felt the breasts. Every wiggle was producing a dull ache in my chest. When I complained to Rachel about it she just laughed and told me that women had to walk around with that weight on their chest all their adult life and men had no sympathy for them. She had no sympathy for me ether and I was going to remain in the corset and have these heavy tits glued to my chest.

After I returned to the den, Rachel chained me back to the chair and put the TV on the game. There was one little twist. The VCR was wired to play stereo movies through my sound system, so she turned the movie back on and turned the volume down on the TV. I would be watching the game, but the soundtrack from the porno movie would be playing on the stereo.

"You always say that the dumb announcers get in the way of the game with all their inane comments, so I thought you would enjoy the sound of the porno movie much more!"

This was a twist that I never expected. The announcers would have been better than the fucking sounds on the porno tape. Once in a while the fucking on the tape would match up with heavy action during the game and that was kind of entertaining. The game was very good and Arizona managed to win a close one with College of Charleston 73 to 69. Arizona was on to the sweet 16 and had avoided the early exit Lute's teams had been criticized for in the past.

When the Arizona game was over Rachel came back to see if I wanted to watch anymore TV. I figured that she would put on the porno tape again if I still wanted to watch and besides, even if she left the TV on basketball the fucking sounds from the tape were just too frustrating. It was a week since I had last had an orgasm and the frustration was driving me crazy. An entirely new meaning to the phrase "March Madness".

"Thank you Miss Rachel, but I have watched enough TV for today."

After I had a late lunch, Rachel took me to the bedroom and told me to make love to her like the sissy husband in the porno. I spent the next hour making love to Rachel like in the movie. My lips caressed every square inch of her body. I sucked her toes like they were Lucy's clit. I licked her pussy until she was almost comatose. I tongue fucked her asshole while fucking her pussy with the vibrator until she couldn't take anymore. When she was done, she had me hold her and rub my fake boobs against her.

We dozed for several hours and when we woke again it was late. Rachel was hungry, so we had a late night snack and watched a romantic movie of her choice on HBO.

When we finished the movie, Rachel had me change out of the corset stockings and wig, then gave me a baby-doll set to wear. The weight of my silicone tits was really starting to bother me and when Rachel removed the corset it hurt even more. My shoulders hurt and I felt like the tits were pulling me over at the waist. When Rachel removed the buttplug, I felt an emptiness that made me strangely regret not having my ass stuffed. The panties were loose enough to get on over my caged cock and the top fit me perfectly with my fake breasts glued in place. It was not a sexy sleep set, more like what a teenage girl would wear to a slumber party. I was very happy to have the corset off and be able to breathe normally again.

"Walk around and jog in place a little so I can see how your tits move when they are not supported by the corset." Rachel instructed.

As I move around, the breasts swayed under the baby-doll top like a teenaged boy's wet dream.

"Stephanie, I do believe they are just about as close to the real thing as science will ever produce, just amazing!"

I was starting to worry about my sanity. It was starting to seem normal to be dressed like a girl and my denied sexual release was making me pay attention to Rachel like never before. Her pleasure was becoming the most important thing in our sex life and my needs were not even a consideration until this damn cock basket gets removed.

I don't know if a man can die from horniness, but I had never gone without release more than 3 or 4 days since I discovered masturbation as a teenager. Even married to Rachel, I "cheated" on her with web porn and sex stories a couple of times a week. If sex was not convenient, I masturbated. Rachel had caught me a couple of times and it had upset her. She thought it meant that she didn't turn me on. I tried to explain that sometimes a guy just goes ahead and jerks-off rather than chasing other women. She always made me promise to stop, but I never had. She felt like it was cheating and I felt like it kept me from cheating. I think this is a common difference between men and women, what is sex and being faithful.

We got into bed and Rachel had me cuddle up behind her and press my "tits" into her back while I gently stroked from her breasts to her pussy. As she fell asleep, I was being flooded with emotions; lust, embarrassment, love and excitement. I was dreading what might be coming next and getting turned on by it at the same time. My wild thoughts and emotions kept me awake for hours as Rachel slept like a baby in my arms.

--- More in Chapter 6 ---

jbirdman
jbirdman
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