Boyfriend to Bride

by Ms Kathy

 

(Part Two)

 

After we were done at the salon, we went shopping to get Billie his maids out fit. After the salon experience, Billie was in a daze. It was almost like he was drugged. He did not speak unless he was spoken to. He was very docile, even for him. He did everything we asked with out question, no matter how humiliating. He was told to address all women with as Ms and then their first name.

The next stop was a lingerie store that sold the maid outfits. The store had for ladies that worked there and the manager. I asked to speak to the manager and let her know what we were doing and what Billie’s situation was. I also said that this was to be very humiliating for Billie and I would like to have as many female customers and employees involved as possible. She was delighted to help in any way she could.

The manager and I took Billie back to the back of the store. They had a large dressing area with lots of mirrors. Dressing booths were on either side of the common dressing area, which had no privacy from the main part of the store. Billie would not be allowed to use the booths. The store manager told Billie to get naked so he could be measured. Once he was naked, the manager noticed that his penis was locked in the back position. I explained that Billie’s penis was under my control and that this way he would have a nice smooth panty line. She smiled at Billie and gave his locked penis and balls a soft stroke with her fingernails, looked him right in the eyes and said, "This would feel so good only if you could enjoy it." Billie shuddered in humiliation and frustration. She thought it would be best to try on the black high heels that would go with the very formal French maid outfit first. She instructed each clerk to bring back on pair of heels and try them on Billie to see which style I licked best. So with Billie naked, each girl would strap a pair on Billie with his locked penis at their eye level. Each girl would also give his penis a nice soft brush of the fingertips to keep Billie frustrated and dazed. I choose a nice black pair of four-inch heels that showed off Billie’s pedicure best. Next came the stocking and garters. They were tried on in the same manner with each girl taking a turn. By the time we had Billie in his heels, stockings and garters and panties; he was trembling with frustration. The girls were doing a great job at teasing and humiliating poor sissy Billie. Next came the actual very formal French maids uniform. It was very short with lots of ruffles. Billie looked adorable. We also choose some nice sheer baby doll nighties with matching panties. By the time we left, Billie was displayed to all the employees and about 15 different female customers. What a great experience that was once again caught on tape by Ms Martha. Billie was once again dressed back into his capries and sandals and off our next stop.

Our next stop was a late lunch. Billie had a salad, which I ordered. Martha and I openly discussed the day’s events and the waitress had a good laugh. Not much else to tell about lunch.

The next stop after lunch was an Adult Fetish store that Martha had scouted out. She found one that catered to the S&M and bondage crowd. We had a great time there. We would pick up different cuffs and paddles and crops and test them out on poor humiliated Billie in front of everyone there. Billie was so humiliated but still he remained obedient and docile. I did make a number of purchases. I bought a nice collar and wrist cuff that will lock Billie’s hands up in the middle of his back, a bondage sleeve for Billie’s armes. I also picked up a neat pair of vibrating nipple clamps. But what really caught Billie’s attention were the vibrating butt plugs I picked up. I choose three different ones all different sizes. I also picked up an inflatable butt plug that can be locked in place with a small chain. After the Fetish shop, Martha and I decided it was time to take Billie home for a little fun (mild punishment session) and an orgasm for enduring such humiliation with out complaining.

Things are going so well. I now have a sissy boyfriend at my beck and call. My business is doing very well. And my sex life could not be better.

When we got home, Martha and I had Billie prepare dinner while we discussed the plan for tonight’s session. Billie was quite the hostess. I was very pleased. He is definitely marriage material. After dinner, we got Billie ready for his session. We had him strip naked, but had him wear the pair of high heels. We took Billie to the family room where I had installed a hook in the ceiling to hang Billie from. Martha had a better idea. We put Billie into the bondage sleeve with his arms behind his back. We attached his arms to the hook with a rope and hoisted his harms up in the air. Billie had to bend over at the waist. This left his butt nice and exposed for either the plugs or the crops, or both. We then put a spreader bar between Billie’s ankles. This kept his legs spread far apart. Now Billie was ready. I took a riding crop and started to worm Billie’s bottom. I started slow. Martha noticed that Billie kept bending at the knees to try to avoid the smacks of the crop. She got an idea to stop that. We unlocked Billie’s penis and she took a strong piece of string and tied it to his Prince Albert piercing. Then she pulled it straight back between his legs, up his ass crack and through the hook on the ceiling. She pulled it tight and tied it off. Now Billie had to keep his knees straight. He was truly immobile. I attached the vibrating nipple clamps and inserted the smallest vibrating butt plug. Billie was now ready. We really gave him a good spanking. Not to hard, but enough to turn his but red. When we would take breaks, I would talk to Billie and explain how life was going to be.

Here were the new rules:

He would acknowledge that all women were superior and treat them accordingly.

He would were what I said from now on. (Even at work)

He would be punished when I thought he needed it. (Even at work)

His status would be very public.

After we were done, it was time for Billie’s reward. So we released Billie’s penis from the string and he instantly got hard. And with butt plug and nipple clamps humming away I started to slow stroke his penis while Martha leisure spanked Billie’s ass. I had a cup to catch his load. (That was another rule, He would eat his own cum.) Billie was trembling. Finally he started to grunt and groan and had a very powerful orgasm. Once he was done he drank his own cum and thanked us both for a wonderful evening.

Martha left and I took Billie to bed after I locked his penis back up. He gave me two wonderful orgasms that evening with his tongue.

As I drifted off to sleep, I dreamed about the wonderful life we had ahead of us.

 

Next part is Billie’s first day at work dressed as a woman.

 

 

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© 2002 by Ms Kathy. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.