A Natural Sissy

Author's note: This is a story about a woman turning a man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you like the idea, read on, and don't forget to vote and leave a comment. More will be added if comments from readers justifies it.

A Natural Sissy – Ch. 01

Stacy is a natural sissy. I knew it the first time I laid eyes on him when he came to visit at my request on an Internet forum. After 3 months of Internet chat, I was ready to implement my plan. I knew he had money. He inherited most of it from his parents when they died in horrible automobile accident a few years ago. I knew he was well educated, too, with a doctorate in electronics, but he was retired now that he was rich. He drove six hours to get to my home from his. When he knocked on my door he had two dozen roses behind his back, and when I opened the door to let him in, he stuttered his name, and brought the roses from behind him to hand them to me.

"Hello, Gail. I'm... I'm... St... Sta... Stacy. I brought you some roses." He looked concerned that I might not like roses.

"Well, thank you, Stacy. The roses are lovely. Please come in." I took the offered roses, filled a vase with water, and placed them on the bookcase at the far wall of my living room. "Would you like some wine? Or a beer?"

"Uh... thank you. Wine is good."

"Coming right up." I brought out a bottle of Chablis and poured two flutes, handing him one as I sat beside him on the sofa. I purposely sat so that my thigh brushed against his, and I put my hand on his leg just above the knee. I could see that he was quite nervous, and I hoped the wine would settle him a bit. You can't train a skittish horse, and you can't train a skittish man, either. As we continued our conversation, I continued to refill his wine flute, while nursing my own with small sips to avoid getting high myself. My object was to seduce the poor widower of two years who probably hadn't had sex since his wife's death. At 46, he was twenty years my senior, just the way I like my boi toys.

His build was almost exactly what I had expected from information gathered during our Internet chats. At six feet tall and weighing about 155 pounds, he was slender, and I noticed he had very little stubble on his face, so I expected to see only a minimum of body hair. He was taller than my 5 feet 5 inches, and heavier by 50 pounds, but that wouldn't be a problem. He'd be perfect for what I had in mind. It was going to be fun turning him into a plaything for my friends and me.

We continued to talk, about everything and nothing, and I inserted some seemingly innocuous questions to gain more information without appearing to. After several flutes of wine he began slurring words, so it was time to set my plan into motion.

I began stroking his thigh, moving higher and closer to his crotch as I continued our conversation. I could see that his cock was growing, and from the bulge it appeared that he was well hung. Even better than I expected. A sissy with a large cock had advantages not inherent in a minimally endowed boi toy.

"Are you tired from the drive down from Atlanta?"

"I think the wine is making me sleepy, Gail. I'm sorry to be such a dullard."

"Oh, you're not dull, Stacy. I find you quite the opposite." Yeah, right. But that would change. "Why don't we go to the bedroom, and you can lie down and rest a bit. We have time before we go for dinner." I stood and took his hand, pulling him up beside me.

He followed me like the puppy he would become as I pulled him along toward the bedroom. I stood him beside the king size bed and faced him. "Let me just get your shirt off so it won't wrinkle, okay?"

"Okay..."

I took his shirt, and placed it over a nearby occasional chair, and went back. "Now, just sit on the bed and let me get those shoes off for you." He didn't object as he sat. When his shoes and socks were off and shoved under the bed, I unbuckled his belt, told him to rise up a bit so I could pull his slacks off, he sleepily complied. I put them with his shirt and then pushed him onto his back on the bed.

"Just close your eyes now and have a little nap. I'll wake you in time to get ready for dinner."

I watched for a moment before shedding my sundress and shoes. He blinked. So, he was watching as I took a place beside him on the bed. I saw his cock throbbing. Just what I wanted, without even trying. He closed his eyes again, pretending to sleep.

So there he was in t-shirt and boxer shorts, and I was down to my 32C bra and matching bikini panties. I put my hand through the fly of his boxers and found his still growing cock. I pulled it through the opening and took it in my mouth, sucking gently on the tip while I jacked the staff slowly. His eyes flew open as he lifted his hips trying to put more of his cock in my moist, warm mouth. I put a hand on his stomach and pushed his hips back down as I took more and more of his now fully erect cock to the back of my mouth, just grazing my throat. There was still three inches to go. Wonderful. This was going to be even better that I had hoped for.

When I was beginning to moisten in my vaginal cannel, I pulled away from his cock with a loud 'plop'. He wasn't sleepy anymore. I straddled him, facing the headboard, sank my pussy down on his throbbing cock, and rode him like that for thirty minutes or so, admonishing him not to cum until I said he could. Step one in his training as a boi toy. Obey your superiors, who would be any female, of course. And any male who weren't a sissy, and maybe a few who were. We'd establish that pecker... er, pecking order as the training progressed.

After bringing myself to three orgasms I decided to let him spurt. "Okay, Stacy, you can cum now, if you're ready." The last word was barely out of my mouth when I felt him convulse and send a series of roped cum deep inside my pussy. I leaned forward and whispered in his ear, "Good boi." I'm sure he heard "Good boy," not "Good boi," but he would soon learn.

When we recovered, I headed for the shower, pulling Stacy along behind by his wilting cock. We showered together, and under my tutelage he learned to bathe me properly as a good boi toy should.

We dined that evening at an upscale Italian place I liked, at Stacy's expense, of course, and by the time we returned to my house; Stacy was committed to selling his house in Atlanta, and moving in with me. Little did he know what that meant.

But three months later he began to understand. He sold his house in Atlanta, moved in with me, where he follows me around like the good bimbo puppy he is going to be, hoping I'll let him fuck me again. And I just may, as a reward, if he trains well. He does have a nice cock. But for now it's just teasing and training, and learning how to put on his makeup properly. He's doing well in selecting his lingerie and feminine outerwear when we go out for parties and such. He's down to one day a month dressing as a male now, and that will cease very, very soon. As soon as the hormones make his breasts too large to hide. They're coming up on 38B now. I catch him fondling them occasionally.

"Stacy! Where are you? It's time to dress for dinner." When I walked into his bedroom, I found him already at the vanity applying eyeliner. He had his lingerie on already, and I must say it is as feminine as any I've ever seen. The lavender bra was lacy with an open nipple design, and his pierced nipples were as visible as his erect cock, with its little gold ring at the base just where it joins the ball sac. The matching open crotch panties allowed attaching a leash to the ring when I wanted to lead him along behind me. His garter belt held his lavender stockings ended in purple patent pumps with four-inch stiletto heels. I guess the only thing not ultra feminine was his hair. I kept it cut in a man's short, almost crew, cut just so he and anyone else would no he was not a woman, but a sissy.

"I'm getting ready, Gail. I won't be much longer."

I was dressed to the nines in a smart sequined cocktail dress with a hemline just long enough to hide my ass cheeks. Stacy's was only inches longer, but he looked sexy as hell with the open nipple bra showing through the gauze bodice of his almost skin tight strapless sheath. His dress was of course pink, the mandatory color for introducing a sissy to your friends. I suppressed a smile as I gazed at the earrings dangling nearly to his shoulders, the turquoise and silver contrasting, and catching the light just as I had hoped. And it matched his silver and turquoise choker necklace perfectly. The sterling chain suspended from nipple to nipple added to the boi toy image I was going for tonight. I had told him to go heavy on his makeup, because everyone at the party tonight would do the same.

I would wait until we were at the party before feeding him a couple of Viagra tablets to assure that his cock would lift his dress enough to be noticeable.

I put him in the passenger seat of his fully loaded, top-of-the-line Mercedes and we were off. "You'll love this party, Stacy. All of my friends will be there, and I'll introduce you to those you haven't yet met."

"I'm sure it will be nice," he answered with a bit of trepidation in his voice. I suppose that was to be expected of a sissy about to be exposed to the world for the first time. At least it was with my other four bio toys.

I made a mental note to give him a GHB along with the Viagra to assure that he was compliant once we were there. He would know what it was, of course, because I used it extensively during his training to keep him agreeable to the things I was doing to him. But there wasn't a damn thing he could do about it.

"Oh, believe me, Stacy, you will absolutely love it."

He was silent. I could almost see the wheels turning in his mind. I let it go. Ten minutes later I handed the car keys to the valet with a caution to park the Mercedes in a safe spot away from other vehicles to avoid small dents caused by careless people. I emphasized my instructions with a fifty-dollar bill from Stacy's evening purse.

We walked side by side under the plush canopy covering the entrance to the club. Stacy's hips were swinging as he tried to navigate in his 5-inch stiletto heels. I could hardly suppress my glee. What a fun night this would be. For me, anyway. Stacy might have a different opinion, but it had to be done.