A Harmless Favor

"You don't think this is too much?" I asked Susie. "I feel like a hooker."

"Good, because you look like one also. Jim is going to love it. Now, sit over there while I get ready. They're due here any minute."

Susie put on her usual bikini and blouse. "Wait up here until I tell you to come down." With that she went down to prepare the refreshments.

Minutes later I heard Marjory and Jim arrive. There was an extended moment of silence, which I knew meant that Susie and Marjory were having an elaborate greeting kiss. Then some talking and then I heard Susie walk to the bottom of the stairs and call for me to come down. I was shaking I was so nervous.

As I approached the entry hall, I could hear Susie preparing them for my entrance. Their backs were to me listening to Susie, who was looking in my direction. I was in bare feet so Marjory and Jim didn't hear me as I entered; Susie looked up and smiled. "Here she is now."

I was taken aback by her referring to me as "she" but that was quickly forgotten when I saw the looks of approval on Marjory and Jim's face.

"Come here and let me look at you," squealed Marjory. "You are absolutely beautiful," and kissed me on the cheek. "Don't you think so, Jim?"

"Yes, I do. I really do. Jon, you look amazing. I never imagined you would take it this far; but I like it. Maybe I could get that greeting kiss from my friend?"

I was timid in response; bashful, actually. He took a step toward me and reached out a hand and raised my chin up till we were looking each other in our eyes. I could tell that he meant the compliment; I could tell that he was genuinely attracted to me.

"You do look amazing," he said again as he leaned down and gently kissed my lips. It took my breath away. He was so wonderful. I knew that Susie had made the right decision for me. All I wanted to do was be everything that Jim wanted. I waited breathlessly for a second kiss and when it finally landed I melted into his arms. I was so happy. Except that my response was creating sexual difficulties. I wanted to become erect but the cage was preventing any growth. It was becoming painful as Jim explored my mouth and let his hand drift down my back to my butt cheeks. God I wanted to rub against him but I didn't dare for fear of revealing my chastity cage.

"I bet Jon is feeling some discomfort right about now," commented Susie.

"What do you mean?" asked Marjory.

"You'll see shortly. OK, break it up. Let's all go out to the pool and relax."

When we got to the pool and all had sat down, the conversation turned to me and my appearance. Jim kept staring at me while Marjory was pestering me about my make-up and such. Finally Susie asserted that the no trunks rule was still in effect and that Jim and I had to disrobe from the waist down if we were going to stay out there. Jim quickly jumped up and took off his shirt and trunks. I noticed that he had a minor erection.

All three then looked at me. "Well?" said Marjory. "Your turn."

I was panicking. I had past the first appearance test; the second might be more difficult. Maybe they would think it was just a quirky treatment for the day.

"Jon, take off you dress right now." commanded Susie.

I timidly went over to Jim and had him unzip the dress and then let it slide down to the floor. I was facing away from all three.

"Turn around sweetie so we can all see."

I turned and faced all three, feeling more than humiliated and embarrassed. I was clearly emasculated by my wife, stripped of all traces of masculinity. I stood before them with my smallish penis encased in a pink chastity cage, topped by a cute pink ribbon.

"Jon has become my sissy husband." said Susie. "Isn't he adorable?"

"You are, Jon. And with that thing on your penis, you have no reason not to think, act and perform as a girl. Just lovely. What do you think, Jim."

"I'm fine with it if he is."

"I have the key so it's almost unnecessary for him to be nude, since he can't get an erection. But he is so pretty nude that I think he should stay that way. Don't you?" asked Susie.

"Definitely," responded Marjory. "Let's have a toast to the new Jon." We all grabbed our glass and drank up.

I was feeling a little more relaxed, but then I realized I was standing there in front of all three as if I were on display. Jim was next to his wife, who was next to Susie. I was alone and afraid. I was not used to being the center of attention; and certainly not comfortable with my pink chastity cage and pink ribbon. I was blushing and looked away, covering my groin with my hands. Suddenly I felt shame at my appearance, at what I had become.

"Look at us, sweetie," commanded Susie. I looked up but kept my hands in front of my penis.

"Take your hands away," ordered Susie. "You have nothing to be ashamed of; this is the choice you made. It's the choice that we both wanted. I want to say in front of our friends that I encouraged Jon in this and have no regrets. Jon, you are my husband, you are my sissy."

Tears were running down my cheeks. I looked at Jim; he smiled "Don't cry, Jon," said Susie. "I've known all along that this was your destiny; I'm just so proud of you for accepting your destiny. You make a much better sissy than you do a man. Don't you agree, Jim?"

Jim looked at Marjory, almost asking for approval to speak. She nodded slightly. Then Jim walked over to me and took my hands. "I think you are very special. Look what you do to me."

I looked down and Jim was fully erect. I looked up and our eyes met. An understanding was exchanged and then he kissed me gently. When he broke the kiss he turned to the wives.

"I think it's time for Jon and I to excuse ourselves." Jim took my hand and led me into the house, through the kitchen and upstairs to the guest bedroom. When he closed the door behind us, he said, "You are my sissy, too. Never forget that. As a sissy, it is your job to give me sexual pleasure. Do you understand?"

"Yes, I do."

"I will use you as I see fit, because you are a sissy. As a sissy, you will strive to be as feminine as possible at all times. If I ever catch you reverting to your old ways, I will punish you with a severe spanking. Do you understand?"

"Yes, I do."

"You will never deny me, you will never contradict me, you will never question me. Susie has created you for me but as a sissy, you can only get pleasure from pleasing me. And pleasing me means doing anything I ask. Because you are a sissy. Isn't that right? Tell me what you are"

"I am a sissy. I am your sissy and am here to serve you. Please allow me to serve you."

"Good, now get on your knees and worship my cock."

I dropped down in front of him and took his semi-erect penis in my mouth. It was heavenly. I felt like I was as I should be - completely subservient to an alpha male. Jim was magnificent in all respects, but more-so with his penis. At that moment I knew I loved being a sissy, I loved Jim, and I loved Jim's penis. His erection was stronger than I could remember. My erection was denied but the pain was nothing compared to the pleasure I felt in servicing Jim.

When he was fully erect, he told me to get on the bed. "Do you know what I am going to do to you, sissy?"

"I'm not sure."

"I'm going to fuck you, sissy. I'm going to complete your sissy transition. Once you feel my cock penetrate you and I deposit my sperm in you, you will never want to return to your old ways. You will be mine and will be begging me to fuck you again and again. But I will only do it if you entice me, if you are feminine enough, if you are girly enough, if you are sissy enough.

I was on my back as he was talking "Now, lift your legs up and grab your knees. I like you and I know this is your first time, so I'm going to prepare you properly. After today, it will be your job to be prepared at all times, ready to accepted me whenever the urge strikes me. Understand?"

"Yes"

"Yes, what?"

"Yes sir."

"That's better. Now how does this feel?" Jim had taken some K-Y jelly and smeared it around my pucker. He then slipped a finger in.

"Oh, that feels wonderful, sir."

"Good. I'm going to put two fingers in and then I want you to relax. When you feel my cock, I want you to push out."

He placed his hard penis against my pucker and I tried to push out. He pushed against me and in the head popped.

"Ouch, oh, oh, please. Oh it hurts." A burst of pain was sent through my body. Jim did not withdraw.

"Of course it hurts, sissy. This is your first time. Just be thankful I am allowing you to get used to it."

"Thank you, sir."

"It's going to continue to hurt for a while," he said as he pushed it in deeper.

"Oh, oh, you're so big. You're too big. Please."

"That's it sissy. Say please whenever you ask for something. And I am big, I'm the man of your dreams, aren't I sissy." He slid it in more.

"Yes, yes, but it hurts. I can't take anymore."

"Oh yes you can, sissy. You were made for this." He leaned down an kissed me deeply. "Now, can you take more?"

"Yes, yes."

He slid in more and kissed me more. "How does it feel now, sissy?" He had stopped and was holding before completing the final push. I didn't answer his question because he kissed me again, deeply, and then pushed the remainder in. I could feel his groin fully against mine; I could feel his scrotum against my butt cheeks. And slowly the pain subsided. He held it at full depth, our eyes locked as well.

And then he pulled it back, nearly exiting, and slammed it in fully. It nearly took my breath away. I put one hand on the back of his neck and the other around his mid-riff. "Fuck me, sir, fuck me. Make me your sissy forever."

And he did. He began working his erection like a magic wand, apply pressure throughout my anus. My penis no longer strained against its cage. I was as soft as possible but I had never had so much sexual pleasure. My whole body, not just my penis, was in ecstasy.

He was now pounding hard and fast. I could tell he was nearing climax and I began to work in rhythm with his strokes. He kissed me hard and deep and then drove in hard; he held it there and I felt the explosion of fluid inside me. I was so happy. I had caused him to have an orgasm, inside me. He got an erection because of me and he climaxed because of me. I was his forever.

He collapsed on me and our heavy breathing was in unison. I felt his penis begin to shrink, but he kept it in me. I kissed him on his cheek, and said "Thank you, I can't wait for the next time."

He chuckled. "You may regret saying that. You have no idea how big my sexual appetite is."

As I ran my fingers over his cheek, I said "I can only hope."

He took my hand and kissed my fingers, noticing for the first time the nail polish.

"Did you do this for me?"

"I did it all for you, Jim. My life changed with that first kiss. I don't want it to change back. I love you Jim."

"I love you too, sissy."

I felt his erection begin to return as he kissed me like it was the first time.