tagTransgender & CrossdressersA Natural Sissy Ch. 02

A Natural Sissy Ch. 02


Author's note: This is a story about a woman who turns an older 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. You will need to read the previous chapter to see how we got where we are in this one. More will be added if comments from readers justify it.

A Natural Sissy Ch. 02 – The party

Just before we reached the entrance, which was manned by a doorman, I said, "Now remember, Stacy, you just do what I tell you, and everything will be fine."

"Ok... okay." His nervousness was showing, but that was to be expected. He had no idea what was going to meet him on the other side of the door.

As we entered the ballroom where the party was already underway, we were swarmed by a group of my friends, some who already had met Stacy, and some who hadn't. We exchanged the normal greetings, and most of the girls who had met Stacy before gave him a hug and showered him with kisses and then two of them sandwiched him between them and led him into the large room, filled with people. I followed along, allowing my two friends with Stacy lead the way. They took him around the room introducing him as Stacy, Gail's new boy toi. Everyone welcomed him, some kissing his cheek, and a few with hot, sensual kisses on his lips. I noticed how he blushed at the reception he was getting. Such a sweet, innocent sissy. Someone had thought to bring us drinks from the free bar, and I took Stacy from his escorts and led him to the patio just outside the ballroom. "Take these with a sip of your drink, Stacy." I handed him the Viagra and the GHB. He downed them both without argument. The lighting outside was subdued, in contrast to the brilliant lighting inside.

I steered Stacy over to one of my male friends, Ralph, and introduced Stacy to him.

"Stacy, this is my very dear friend Ralph. Suck his cock." Very dear friend indeed. We met once a week for a marathon fuck.

"Wh... what?" replied Stacy, in a tone that showed displeasure.

"What part of 'suck his cock' do you not understand, Stacy?"

"I can't do that! I don't like men, I like girls. I wont do it."

"Yes, you can do it. And you will. I told you to do what I said and everything would be fine. Would you rather that Ralph use you as a punching bag?" I watched Stacy size Ralph up, and I knew he wouldn't want to cross a heavyweight wrestler like Ralph.

"Don't let him hit me, Gail. Please."

"Then I guess that settles it. Suck his cock. And beg him to let you do it, since you're being such an ass about it."

Stacy looked back and forth at Ralph and me. Ralph had a slight grin of amusement on his face. Then he turned to Ralph, and said, "Ralph, may I... may I ... suck your cock?" The GHB has started to work on Stacy's inhibitions.

"Sure, sweetie. Just kneel down on this cushion so your stockings won't run, and take my cock out for me." Ralph had, of course, been briefed that this was going to happen, and he threw a cushion from one of the nearby lounge chairs on the floor.

Stacy hesitated a moment, then knelt on the cushion and reached for Ralph's zipper. He pulled it down slowly, trying to delay the inevitable, but soon had no option but to fish the large, growing cock from within. He stared at it as it grew, trying to determine how to approach the situation.

"Stacy, this is easy. Just suck it like you do my strapon when I fuck you. Lick it all up and down to get it wet like you've learned to do, and then take the head in your mouth and go from there."

Stacy finally took the cockhead in his mouth and started swirling his tongue around it, getting it wet, and then took more of the shaft in, and began moving his head up and down, stroking the shaft not in his mouth in rhythm with his head movement. Ralph put a hand on either side of Stacy's head and began slowly fucking my boi toi's mouth.

It looked like Stacy was getting excited, and started really enjoying the job he was doing. A small crowd began to form, watching Stacy's initiation to blowing a real cock. There were softly spoken words between those watching, and even a few bets on how long before Ralph would fuck him in his boi pussy. I had to smile at that, because that was next on my planned agenda, with Ralph's agreement. It wasn't long coming.

Ralph was getting turned on, and he pulled his cock from Stacy's mouth and said, "Stacy, get over there and lean over the back of that lounge chair. I'm gonna fuck your ass now."

Stacy looked up in horror, and tears began to form at the corners of his wide eyes. "Please don't. You'll hurt me. I don't want to get hurt."

I spoke up then, "Stacy, honey, Ralph isn't going to hurt you. He's just going to do what I've been doing with my strapon, except he'll be using the real thing. You'll love it."

"No, I won't," cried Stacy. "I don't like men. I like girls. I didn't try to stop you, 'cause I love you, but I don't love any man."

I took Stacy in my arms and hugged him tightly, moving his to the lounge chair. I took his hard cock in my hand and said, "Stacy, you need to do this. It's in the training manual for sissies. It's what they do, and you know you're a sissy, so you have to do it. How about if I give you a nice handjob while Ralph fucks you?"

Stacy wiped away the tears, and said, "Only if you won't let him hurt me, Gail. I'm afraid."

"I promise you I won't let Ralph hurt you, sweetie. Now bend over the back of the chair like a good sissy." I started stroking his cock as I pushed him over the chair.

Ralph took over and started pushing his cock into the rosebud, and slowly worked just the head inside. Then he waited, giving Stacy time to calm down and adjust to the presence in his ass. After a moment or two he started pushing in deeper and deeper, waiting after each lunge, until he was fully buried in Stacy's ass. Then he started in earnest, fucking my boi's ass faster and faster until Stacy squealed with delight. Ralph continued until Stacy was almost in ecstasy, and then he erupted, filling Stacy's ass with cum until his cock began to go flaccid. This part of the initiation came to a close as money passed hands among the bettors.

I pulled Stacy to his feet and praised him for a job well done. "That was wonderful, Stacy. You did a great job there. I'm going to give you a big reward when we get home."

Stacy's eyes widened, and he broke into a wide grin. :"I did good?"

"Yes you did, sweetheart. You did a wonderful job." I took his head in my hands and planted a long, hard, sloppy kiss on his mouth. "Now I want you to go with Wanda and Shirley and get cleaned up a little. Your hair is a mess, your lipstick and mascara are ruined, and your cock spilled cum all over, and I'm not even going to make you lick it up like I usually do." Now git." I slapped him on his ass and pushed him into Wanda's arms.

As Wanda and Shirley guided him into the ballroom and toward the ladies room, I heard his quietly saying to the two girls, "Gail said I did good, and I'm going to get a reward when we get home," his voice filled with pride. The girls smiled sweetly in response.

Wendy attended to getting Stacy's face back in order, applying slutty makeup to the extreme. Stacy looked like a whore. Shirley had spent the time toying with Stacy's cock and balls, keeping his cock rock hard.

A few minutes later, everyone was back inside when Stacy returned to my side, looking very much refreshed, his hard cock tenting the short skirt he wore.

"Oh, there you are Stacy. I've been waiting for you. We're going to play a game now, and you'll be a prize for the winner. I pulled his skirt hem up exposing his cock and started pumping it slowly to keep him from thinking too much about what I had just told him.

"Okay, Gail," he smiled broadly. "What do I have to do?"

"Whatever the winner of the game wants you to do. It won't be hard." I led him by his cock, to the amusement of all who had gathered, and took him behind a portable folding partition. There was a bed and a chair there. "Just sit in the chair and wait. The winner will be here very soon."

I left him sitting in the chair and went back to the other side of the partition. There would be no game. Only a lot of laughing and shouting to simulate that a game was in progress. I placed numbers in a hat, and everyone drew one. Whoever got number one would go first, and so on. The first "winner" was a girl named Roberta. She went behind the partition, and a silence fell on the crowd. They all wanted to hear what was happening behind the partition.

Oral sex. Pure and simple. She blew him, and he sucked her off. Numbers two, three and four followed every twenty minutes with similar results. Then the façade of a game evaporated and people just lined up in plain view of Stacy. They took their turn as they became first in line, sometimes one on one with Stacy, sometimes a gangbang. Poor Stacy's mouth and ass took a real beating, but he was enjoying every minute of it. Every once in a while I took him another drink to wash down the cum accumulated in his mouth.

Then it was over. The last of the group had finished playing with my boi toy, and everyone started drifting out to go somewhere else, most just to go home.

I led Stacy outside in the usual manner, by his cock, and handed the valet the keys to Stacy's Mercedes. On the way home I couldn't have gotten a word in edgewise. Stacy jabbered continuously about how much he enjoyed the party, and when could we have another?

The next chapter will begin with Stacy's promised "reward."

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