Making Kristy Ch. 4

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The making of a woman continues.
2.1k words
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Part 4 of the 7 part series

Updated 10/29/2022
Created 03/22/2001
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Everything was happening so fast for me. First I had these newfound feelings of wanting all things feminine. Second, my wife had just told me that she had gotten pregnant by another man. What I really wanted was a little time to take it all in but unfortunately I didn’t have it. Richard and my wife were waiting for me at the restaurant.

When I arrived Richard stood like a gentleman and pulled out my chair.

I was actually a little taken aback by him. He was tall and had the darkest brown eyes imaginable. Even though he was a little on the chubby side I thought he was extremely good looking. No wonder my wife wanted to have his baby.

“You are right.” Richard said to Loraine. “He does make a very pretty woman.”

I sat down next to him and blushed a quiet “thank you.”

“I was telling Richard how much I loved you Kristy. I told him that no matter what happened I would be there for you.”

Even though I knew that nothing would come between my wife and I, it was nice hearing it from her every now and then.

“But at the same time I want you to know.” Loraine continued. “I am starting to fall in love with Richard also. I just want to make it clear that I love him for the man he is- I love you for the woman that you are.”

If that had been meant in a way to humiliate me it didn’t work. It felt good that my wife was referring to me as a woman. Richard smiled in my direction and then handed me a beautifully wrapped present. “I know your birthday was yesterday but I didn’t have a chance to give this to you then.” Richard said

I tore into it like a child. He must have spent a ton of money on it too because it was a 24 carrot heart-shaped locket with a one carrot diamond in the center.

“I figured since we all are going to be seeing each other quite a bit, might as well go all out for your birthday.”

I thanked him, leaned into him and then kissed him on the cheek. “Thank you so much.”

We settled in and started talking about the baby and possible names for it. I liked Richard’s suggestion of Kyle but my wife was pretty insistent on naming him, if it was a boy, after his father- Richard.

After we placed our dinner order, Richard asked Loraine to dance. It was strangely erotic watching them hold each other close, it was even more so when Richard leaned in and kissed her passionately.

“I noticed your friend’s kind of left you.” A voice from behind me whispered. “Would you like to dance?”

I turned around and was greeted by Mr. tall, dark and handsome. My heart skipped a beat. This guy, this complete stranger was actually looking at me like I was a real woman. I had a tough time working up the courage to answer him. Fears started racing through my mind. “What I don’t sound like a woman; what if he is disgusted by my voice; what if…”

I cleared my throat in a soft, womanly voice I answered, “um sure why not.”

It felt so nice being held and led around the dance floor. I was even wishing the song would never end. Even after the music had stopped he continued to dance with me. “Would you mind if I joined you and your friends?” He questioned.

“Let me check with them.” I answered. He introduced himself as Andy. Loraine smiled at me and winked. I could tell that she was excited that I had met someone new. In no time at all and with a little help from Loraine our once previous small talk turned a little erotic.

“I think we should all be upfront with each other. I’m sure that Kristy doesn’t want to discuss it but…” Loraine began.

I knew exactly what she was getting at. Being married to the same woman for so long can make you think on along the same lines. I was terrified. If she planned on giving away my little ‘secret’ I knew I would be mortified. I knew anything could happen. Andy could go off on me. I danced with him. He held me like a lady. “Oh god.” I thought. “This man could kill me.”

“We all have our little fetishes don’t we?” She asked.

“Sure we do.” Andy replied. “For as long as I can remember I knew that you never knew about what went on behind closed doors.” He laughed. “I guess everyone is a little different in the things that turns them on.”

“Even Mr. Straight lace himself can get a little kinky now and then- isn’t that right Richard.” She said as she smiled up at her lover.

I didn’t like where this conversation was leading. I wanted to get up and run out of the restaurant or at the very least bury my head in my hands and cry. But I just sat there waiting for it to be over- well actually I waited for Andy to stand up and punch me in the jaw.

“Well let me just come out with it. Kristy here- well she’s a boy.”

Andy turned a little red and his mouth fell open. I think at first he didn’t believe her but soon realized it must be true because I wasn’t defending myself.

“No way.” He said, as he looked me up and down. “There is no way she could be a guy. I mean look at her. Even her breasts are real.” Andy continued. “Any guy would be lucky to be out with a girl like this.” He said and then winked at me.

I was completely relieved. It appeared that not only was Andy not angry he seemed a little comfortable at the thought.

“He is most defiantly a guy- I know because I dressed him this morning.” Loraine laughed.

Things seemed to get a little easier. I was a little less tense about my woman voice so I started to open up a little bit more to my date. The rest of the evening was spent with me laughing at his jokes, touching his leg and hinting that I wanted more!

“I was thinking- would you and Richard like to finish this evening off at our place?” Loraine asked.

Both boys jumped at the chance.

Loraine went with Richard in his car while I went with Andy in his. And even though we had just been through some open and frank conversations both of us seemed to be at a lack for words. I think maybe it was the fact that we were alone for the first time.

“So- um, you are really a guy under that makeup?” He questioned.

“Yep, really a guy.”

“Are you gay or something?” Actually yesterday I would have went to my grave arguing that I was straight but something had changed since yesterday. The question didn’t even irritate me. “I’m bi actually.” I replied “At least I think I’m bi.”

Andy put his arm around my shoulder and pulled me more toward the center of the seat. I found it natural to rest my hand on his inner thigh.

“Well I guess it doesn’t matter but I think you look really like a woman. I hope you don’t mind me saying so.”

I didn’t

I put my head on his shoulder as he concentrated on driving. My stomach felt a little funny. Don’t get me wrong- it was a good kind of funny. Slowly I worked up the courage to run the tip of my finger along his inseam. “I hope you don’t mind but- I kind of like you.” I smiled up at him.

He didn’t

His cock began to show itself underneath his slacks. I resisted the temptation to take it into my hand. I figured there would be plenty of time for that later.

When we all arrived home Loraine excused herself to the kitchen to get us all some drinks. I quickly became embarrassed when I noticed Andy staring at me. I recognized his glassy-eyed glare because I had, had that look myself plenty of times. It was lust.

“Seems you two are hitting it off.” Richard replied as he took his drink from Loraine.

“I think so.” Andy said and then moved in a little closer to me. I was beginning to pick up on the signals that men give. Even after only a short time I knew that Andy wanted to kiss me.

We were like animals, our hands explored each other’s back, ass and we kissed each other like any newfound love would.

“Oh- I wanna’ watch.” Loraine said as she made herself more comfortable on the couch.

And I wanted her to watch too.

Andy slowly worked my dress up to where it was around my waist and then pushed his hand down underneath my panties. I couldn’t help but moan when he worked his finger in between my ass and forged them inside of me.

I was a little nervous. It was one thing to give a blowjob; it was entirely different thing to have a man make love to me. Funny thing though, the anxiety I was having didn’t stop me one bit. I glanced over toward my wife and her boyfriend to find them cuddled up next to each other. I think they were enjoying the show.

“I want to make love you.” Andy commanded.

His words made me melt. This would be my last test of womanhood. If I could do this, I knew I could do anything that a woman could do.

Andy undid his pants and pulled out a nice seven-inch cock. I licked my lips and at the same time pulled down my panties. “I want you to make love to me too.” I responded.

I got down on my hands and knees and pointed my ass in his direction. I prepared myself for the most extreme pain I could ever imagine. Andy knelt down and slowly slid his hard cock slowly in between my legs. “Do you like that?” He groaned.

It was even better than sucking cock.

I felt the head of his prick start to push its way inside of me. I was surprised at how little it was hurting. Sure it was a little uncomfortable at first- but not anything like I had expected. I moaned my response and pushed ass more in his direction.


I looked over to find Loraine masturbating.

He fed my ass inch after inch of his beautiful tool- I was full but at the same time I was in ecstasy. His spit covered cock seemed to glide in and out of my backside effortlessly. “Oh baby- fuck me.” I said in my best sissy voice.

Roughly he picked me up and turned me over. Even though he didn’t say it- I knew- he wanted to fuck me like a woman, he wanted to take me in the missionary position.

All of my concentration was on my lover. I reached down to fondle my aching sack and realized that wasn’t the least bit hard. It wasn’t that I wasn’t enjoying it because I was. I think it was my desire to totally please Andy that kept me from thinking about my pleasure.

I never took my eyes off his. Little beads of sweat were forming on his brow as he continued his relentless pounding of my ass. “Fuck me baby.” I said as I dug my nails into his back. “God I love your cock.”

As my legs locked around Andy’s shoulders he leaned down to give me a kiss. The moment our tongues touched I felt is sperm flood my ass. The warm gush of fluid was incredible. “Oh yeah.” I said as I madly thrust my ass against his cock.

I never wanted it to end.

I turned around to find my wife staring opened-mouthed in my direction and Richard with a handful of cum. I was glad that they enjoyed the show.

“God baby, you are awesome.” Andy moaned as he pulled himself off of me.

I closed my eyes to concentrate on the feeling of his cum seeping from my ass.

Richard broke the momentary silence by clearing his throat. “Um, wow, would- um- you two like to join us in the other room- I think the bed would be a little more comfortable.

Erotic… Sexual… Womanly… I craved cock. I would have went anywhere, done anything. “Us four?” I said curiously.

Loraine pulled her fingers from her pussy and smiled wickedly at me. “Sure why not.”

“Damn, tonight is going to be awesome.” I thought to myself as I pulled up my panties and trotted toward the bedroom.

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