San Francisco Adventure

Mistress had instructed me to be ready for her arrival. Accordingly, I had shaved my genitals and pubic region, making them clean and smooth. I had rubbed baby oil gel all over the shaved area and then placed my CB-3000 male chastity belt on, locking it firmly in place. I then had put KY Gel on my butt plug and carefully inserted it into my rectum. Next came the tight fitting blue lace panties, which covered my chastity device, plugged ass and shaved groin. I pulled on my pants and tucked in my shirt and awaited my Mistress.

Soon Mistress knocked on my hotel room door and I opened it, greeting her with a smile and a warm embrace. She moved to the chair and took a seat. "Are you ready for me?" she asked. I nodded. "Then take off your pants and shirt and let me see," she said. I did as instructed. "Oh, I like the blue panties," she said. "Now pull them down so I can see everything else."

After inspecting me to insure that I had completely followed her instructions, Mistress opened a bag she had brought with her and took out a lacy, white body briefer with bra cups and suspenders. She had me pull it on, covering my panties, stomach and chest. I pulled the bra straps over my shoulders. "There," she said, "how does that feel?"

"Wonderful, Mistress," I replied.

"Good, because we will now go shopping for breast forms to fill those cups and give you a new look," she said. With that, she had me pull my pants on and put on my button down Brooks Brothers white and blue striped shirt over the white, lacy body briefer with its large 42 C-cup bra. "Put on your sport coat but keep your top shirt buttons unbuttoned," she commanded. "I want people to be able to catch a glimpse of the white lace."

We left the hotel and caught a cab. Mistress told the driver the address of the shop where I would soon be buying breasts. I kept trying to sit in a way that kept the butt plug in, the chastity belt from pinching my encaged genitals and the coat covering my chest so the cab driver could not see what I was wearing underneath. It was a challenge.

When we arrived at the store, Mistress walked straight in and told the young female clerk we were there to buy breast forms. "They are for him," she said, motioning to me. At the back of the store in a glass display case we found several kinds and sizes. Mistress chose two kinds: a set made from cloth, and a set made from silicone. We moved to a fitting room.

"Take off your coat and shirt," she instructed. I did as I was told. She then filled my bra cups with the cloth breast forms and had me pose for her, turning this way and that to see how my new breasts would look from each angle, how big they would look from a frontal view and from a profile. She then removed the first set and filled my cups with the silicone forms, which looked, felt and weighed more like real breasts.

"I like these better," she told me. "How do they feel?" I smiled. "Good, I will go pay for them and you can wear them out of the store. Get dressed."

When she returned she led me out of the store, now sporting breasts, pinned against my hairy male chest by the white lace body-briefing garment. We walked down the sidewalk and people stared, One male gave me a suggestive smile.

Mistress decided I needed a different top. Some female form-fitting top that would replace my button down shirt and display some cleavage and show off my breasts. She wanted others to witness my growing submission to her and my growing transformation into a sissy. We walked into several women's clothing stores. While Mistress scoured the racks for a blouse that would work, I stood patiently, pondering my growing humiliation. Mistress had me enter another fitting room, trying on several tops, before finding a low cut white clinging one with some lace at the cleavage area.

"This should work," she said, as I tried it on. Mistress liked what she saw. "I'll pay for it and you can wear it to dinner," she said. "My God," I thought. "People will see I am wearing a women's blouse and that I had fairly large fake breasts underneath it."

Mistress had me place my male shirt in the sales bag and we walked from the store. I was mortified, yet excited. And strangely at ease, obeying my mistress even as her orders brought my humiliation.

We entered a nearby restaurant. It was clear to the hostess and waitress that I was a male (I have a beard after all) but that I had breasts and a cute little top that barely covered them. To their credit they did not stare or laugh, at least not that I noticed. (This was San Francisco - a fairly tolerant place.)

We were seated at a table with my back to the door. But other wait staff and a few customers did notice. Mistress ordered our dinner, while I thought how often had I stared at women's chests, obsessed with their breasts, large and small, and their nipples. Now the shoe was on the other foot. People were staring at my breasts. I could feel myself blush like the school girl Mistress was transforming me into.

After dinner we grabbed a cab back to the hotel. Mistress made me keep my coat open and my arms down so anyone who came past could see me for what I had become.

When we reached my room, she again had me strip. This time I stood with no pants, or shirt or socks. I did have on the CB, butt plug, panties and body briefer. She had me remove my new blouse and then commanded me to step into a pair of white fishnet stockings, which she fastened to the garter suspenders that hung from my body briefer.

"Get on your knees, I am going to spank you," she said. I kneeled before the bed. She then opened her bag and took out several new butt plugs. She took the largest one and disappeared into the bathroom where I heard the tap water running, as I knelt with my face on the bed, awaiting my fate. When she returned she held it in front of my face. "Do you think this is large," she asked. "It's not as big as a dildo or a real penis, but it will do.

"I want you to take it you mouth and keep it there while I spank you," she said. "I want you get in practice for the real thing." With that, she pushed the large butt plug into my mouth like some disembodied penis and began spanking my bottom, at first with her hands, then with my own belt. I kept the fake penis firmly between my teeth and gums. And tried not to cry as she tanned my bottom a bright red.

After a while, she finished the spanking. She took the butt plug from my mouth. "I am getting you ready for the day when you will suck a real penis while dressed like the sissy you are," she said. "Now I want you to show me how you will suck a man," and she pushed the plug in and out of my mouth, like someone was fucking my face. I licked and sucked and tried to swallow it with abandon. I am not gay. I have never had sex with another male. But Mistress had commanded me to become a sissy cock-sucker and I was obeying without a second thought.

When she tired of that part of my training, Mistress placed my face between her pants-covered legs as I knelt before her. I longed for her to command me to worship her sexual power with my tongue, but instead, she had me remove my face from her warm, safe, sweet smelling harbor, and place myself across her knees so she could resume spanking me. When finished, she had me strip to CB and panties and she tucked me into bed.

"You must remain like this for the night," she told me, before tucking me in, turning off the lights and leaving me to consider myself - an adult male being turned into a chastised, lingerie-wearing, cock-sucking sissy, submissive to a beautiful, powerful mistress. I wanted desperately to cum, to relieve the sexual tension the night had created, but I lay there, locked in my CB. Glad that I belonged to Mistress and happy I could please her.

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Page last updated 05-Aug-29 by: Altairboy@aol.com