tagTranssexuals & CrossdressersTransformation Ch. 04

Transformation Ch. 04

bystillconfused©

I was just lying back on the bed and enjoying how very good life can be. My wife Cat, Catherine to everyone else but me, and I had been playing our new game for about three months. If you have read the earlier tales you will know that after losing a bet to her I began a new and exciting lifestyle.

The feeling of her mouth on me, slowly moving up and down my shaft, helped to stimulate the memories of our recent adventures. I lay there with my head propped up on the pillows watching her at work. Watching Cat's mouth slide up and down my cock is one of the most thrilling sights I can think of.

I reminisced about our girl's nights out when she and I would dress in our best and go dancing at a local club, teasing the boys and each other. I recalled our shopping trips where we would spend the day selecting and trying on outfit after outfit, flirt mercilessly with the sales staff, both male and female, and talk intimately as only two close girlfriends can.

Becoming my wife's best girlfriend, her confidant and playmate has been the most exciting things I have ever done. To have remained her husband in all ways at the same time made the arrangement perfect.

I was enjoying life, in both of my personas. My closet was half full of beautiful female attire ranging from pants to hot skirts, from business suits to shorts and halters. My dresser had surrendered half of its draws to lingerie. And, I was getting a fantastic blowjob.

I felt Cat's head rise from me and through half closed eyes looked at her. She was beautiful. Her face was shinning with the enjoyment that she was getting from pleasing me. Her tongue was sticking out just a little and licking her lips which shone with the moisture that was leaking from me. Her eyes were bright and full of mischief.

"Have you ever tried this?" she asked in an almost whisper.

I heard, but the question didn't immediately register with me. "Back to work lover," I coached her.

She took a quick swallow of me and then returned to stare into my eyes, now open as my mind was jerked back to the present by a growing fear of some unknown danger pending.

"I asked," she repeated for me, "have you ever done this?

I looked at her. Damn she was beautiful. She was supporting herself with her arms on top of my legs, her hair dangled onto my thighs and tickled sensually, her fist was wrapped around the bottom of my hard dick and the shaft of it was wet and glistened from her mouth.

I tried my best to play dumb, "Done what?"

"This!" she said as she lowered her mouth over me again taking in all of my cock that stuck above her gripping hand. She held me deep in her mouth and sucked, bringing me closer to the inevitable orgasm. She had held me on the brink for about 20 minutes now and it wouldn't take much to push me over to an explosion in her mouth.

"This," she said again after releasing me as I trembled close to cuming. "Have you ever had a cock in your mouth, have you ever given someone a blowjob?"

"Show me again what you mean?" I asked teasing her, hoping to divert her back to my main interest right now.

"No more until I get an answer,' she smiled and then licked the head of me.

"Come on baby," I pleaded, "that's no question to ask now, or ever for that matter."

"Tell me," she teased, "have you ever done it?"

I guess I was blushing a little, or something else gave her the telltale sign she needed. She almost screamed as she jumped up and sat next to me.

"You have!" she cried, "Oh my God you have, haven't you?"

"Come on Cat, you can't stop now," I begged her, partly because I was so near an orgasm and partly because I certainly didn't want to talk about this particular topic.

"Oh no you don't buster, you're not getting out of this! You're going to tell me all about it sooner or later so you might as well get it over with!"

"Oh come on Cat, don't do this to me, please!" I pleaded.

"Look, if I have to dress you up in panties and heels so we can talk about this as girlfriends I will, but you are going to tell me," she insisted.

"It was nothing Cat, honestly, it was just dumb kid shit!"

"Yeah, well for dumb kid shit you sure are getting red in the face!"

She was relentless when she wanted something and this was going to be one of those times. I finally just took a deep breath and started to tell her what she wanted to hear.

"It happened when I was still in puberty. There used to be some woods behind our old neighborhood and you know how kids are, we had all of these new feelings and weird things happening to us that we just didn't understand. Well a couple of us experimented a little. We didn't even know what we were doing. I mean we didn't even have words yet for what we felt or did."

Cat was smiling at me and she looked so soft and loving. "There, that wasn't so bad was it?"

I continued on, trying to mitigate the past actions. "I think it was kind of normal for kids at that age to experiment."

Cat cocked her head a little, "Well if it was so normal why are you so embarrassed?"

"Aw Cat you're killing me here!" I moaned. "Look it was a long time ago and while it may have been normal then it isn't now, ok? It's not like I'm queer or anything."

"Did you like it?" she asked with her evil grin.

"Damn, jeez Cat, what do you want from me? Yeah! I liked it! It was the most thrilling thing I had ever felt up until that point in my life." I blurted out. "Somehow I knew that it was wrong and that only made it more exciting for me."

Cat moved back between my legs and took my still hard cock back into her mouth and went to work on me. Slowly I settled down again to enjoy her special talent and just as I was really getting back into the fun of it she raised her head again.

"Do you ever think about it?"

She lowered her head back slipping her mouth over me in a long slow motion that electrified my brain and removed my inhibitions.

"I have, a few times. Please don't stop."

Her mouth came off me again. "What did you like better, doing or getting?"

Down went her mouth again and up came my blood in a rush of pleasure.

"Both, I liked both. Oh God Cat that feels so good!"

For some reason the admissions she was dragging from me only excited me more and with one last long slip of her mouth she had me erupting. I jerked my hips to her as I unloaded into her accepting mouth. I wasn't an expert, I mean I hadn't had blowjobs from very many women, but I was sure that Cat had to rank with the very best of them.

I shook all over as I came and the orgasm seemed to come from deep inside of me, so intense that it almost hurt.

The very first weekend we had spent as girlfriends Cat had instituted sharing. Anytime that she brought me to a climax with her mouth she would slip up my body and cover my mouth with hers and share my cum with me. I hadn't objected that first time and I didn't object this time. It seemed like a natural finish, to share the fruits of her efforts.

When we had finished I leaned back from her and asked, "Have you ever done that with anyone else?"

She smiled at me. You have to know Cat to learn about her smile. It can be mischievous, heartwarming, stimulating or threatening. This time it was full of the joy of her mischief.

"You know I think that might be a conversation best left for a girlfriend. What say we get dressed and go get a drink and talk a little."

Cat and I showered and changed. A little while later I slipped into our car wearing a nice pair of slacks that hugged my hips, a pull over blouse and short heels. Cat drove, reminding me again that I drove like a drunk when I wore heels in the car.

We had developed a comfortable lifestyle in the few short months that I had been crossdressing. Several nights a week I was en femme. Sometimes we stayed home and just watched a movie, cuddled and talked. Some nights we went out to dinner or for a couple of drinks. A couple of times we had returned to the same club I first visited as a girl and enjoyed a few hours of dancing and flirting. I was still a little uncomfortable when dressed as a lady, but was getting more accustomed to it with each experience.

If it hadn't been for the perpetually hard nipples on my fake breasts poking little tents in my blouse no one would have given us a second look as we walked into the quiet little club.

Cat has offered to cut the prominent protrusions off my breasts forms but I had declined. Gradually I was getting used to having guy's attention drawn to my chest. Even at times like this when I was not trying to be sexy or seductive it gave me a thrill to know that I turned on the guys.

We took our place at a tiny table and ordered our usual wine. Once the waiter left Cat turned to me and said. "You look cuter every time I see you sweetheart."

I smiled into her eyes and covered her hand with mine and replied, "Thank you."

We chatted for a few minutes, adjusting to the atmosphere of the place and each other.

Finally I worked up the nerve to ask the question, "So, have you ever done that before?"

Cat just looked at me a minute, then smiled her conspiratorial grin.

"Honey not like I do with you and Jessup. If that's what you mean."

Our relationship suffered from a split personality. Well maybe benefited from it would be a better term. Whenever I was dressed up as Jessie Cat would talk to me as a very intimate girlfriend. She would tell me things that Jessup would never get to hear, many of them about him and their relationship. Somehow or other when I took off my panties and makeup I was suppose to leave all of the secrets behind with the female personality. While that may seem difficult and confusing to a lot of people it worked amazing well for us.

Cat continued, "Now if you are asking if I ever gave head before well of course I have. I almost never let the guy cum in my mouth but sometimes I did, if I really liked them."

I just looked at her waiting for her to continue.

"Does that bother you? You know that I was a virgin when Jessup and I meet? The way I stayed one was hand jobs and blow jobs."

I remembered that when we first started dating she would do that for me. It wasn't until we moved in together that we actually had sex. Remember, our President said that blowjobs weren't sex, who am I to argue?

Cat had just a little more to say, "The sharing thing was just for you. I thought that you and Jessup would enjoy feeling and tasting some of the pleasure that I got."

I cupped her face with my hand and told her that she had been right, as usual.

I hadn't polished my nails before leaving the house, but the tips of my fingers were well manicured and looked very feminine. As Jessup I left my nails bare, but well shaped. No one had noticed as far as I could tell.

We talked a while longer and had another wine before Cat got to the topic she had on her mind. Again she spoke as if her husband, Jessup, was at home.

"Sweetie, you know that Jess has been trying to get me out of the office and into the field selling our services with him. He claims that a lot of customers would respond better to a woman, especially a good looking one. I accused him of wanting to pimp me for sales. He claims that I would only be eye candy. What do you think?"

I thought this was a chance to get something I had wanted a long time and knew my answer immediately, but faked thoughtful consideration for a moment.

"You know Cat, he is probably right. Face it girl, this is still a man's world for the most part and a lot of them would be an easier sale for a cute gal like you. If you were willing to dress nice, you know heels and a skirt, and maybe show a little cleavage you could do some real good for the company. If you didn't mind flirting a little it could be a big plus."

"You think so?"

"Yeah, I do, really."

"Well I'm glad you feel that way! Now don't take this wrong honey, but you have been with us 3 months now and I think it is time you did a little something to support yourself. The job is yours!"

"What!" I still had trouble with my voice when I got surprised and this came out a low, but definite male growl.

"Oh I'm not talking about full time, maybe two days a week to help Jessup sell those tough accounts, the ones he thinks a girl could do better at."

I was speechless. I just stared at her waiting for the thoughts to focus in my head. I had never been out of the house without Cat when I was Jessica. Now she wanted me to call on customers?

Cat held my hand on the table top. "I have been watching you Jessie, you're doing great. You wouldn't have any trouble at all with this if you just believe that you can do it. Besides, you love to flirt! Oh yes! I've watched you show a little leg, or rub against the guy when you dance, or bat your eyes at them. You just love it don't you?"

Well she was right about that, I did enjoy my new role and the games that came with it.

"Cat you're right, I do enjoy it, and I have thought about going to work like this, but only to someone who didn't know Jessup well, had only met him once maybe. Just don't know if I am ready for regular outside job, being around people that much."

"You don't have any trouble here do you, around all these people?"

"Cat, you're here with me, that makes a big difference to me!"

She looked at me with sad eyes. "Well, Sweetie, I love having you around, but I can't abide a freeloader, so you either have to start earning your way or I am going to have to ask you to move out."

My mouth dropped open. What was she telling me? I could either do this or we would stop playing? I had thought about it, but I was afraid. There was so much that could go wrong in a situation where I would be alone, without her guidance or protection.

She continued in a more encouraging vein. "We know that you're every bit as smart as Jessup and have all the computer skills you need, so that part of it would be second nature to you. All you would have to really work on is the people skills."

"You mean the flirting!" I quipped harshly.

"Yes," she laughed, "the flirting! My darling husband thought it was ok for me, so I am sure he would agree to his sister doing it. It is for the good of the company and all that."

I just shook my head, I knew that I was stuck and honestly wasn't planning to fight it very hard no matter how badly it scared me.

"Good," she said, "you can start Thursday."

I was still reeling from my new job offer and sipping a little wine when Cat's next shocker got me.

"Do you think Jessup has sucked any dick since he was a kid?"

I spit wine on the table, choking on her question. She burst into laughter as she handed me a napkin to wipe my chin.

"What?" she said, " is that not a question to ask his sister?"

"No," I muttered as I wiped, "it is definitely not a question to ask his sister, but I am very sure that he hasn't!"

She wasn't giving up, "Do you think he has thought about it?"

"If he did think about it what he thought was that it would be queer for him to do it! He's not queer!"

"Yeah, you're probably right." Then she grinned, "What about you, it's not queer for a girl to give a little blowjob, have you thought about it?"

I lied with as straight a face as I could manage. "No, I hadn't thought about it. I'm very happy with you."

She was cupping my face again as she asked, "Would you suck my cock if I had one?"

The image of Cat with a hard dick filled my mind and made me shiver. I leaned to her, "Yes, I would."

Cat moved to me and brushed her lips over mine, thrilling me to my core. She loved to make these little shows of lesbian affection in public, and I didn't mind one bit. I was her lover and didn't care who knew.

The following Thursday I went to work for the company as the new outside sales representative. I have got to say that it scared me to death the first time I walked into a client's office as Jessie. I wore a light gray skirt and blazer with a white blouse and a mauve camisole showing some pretty lace at the bodice. Over the months I had allowed my hair to grow out some and Cat had arranged it in a pretty bob for me. The short two inch heels were professional and comfortable, if not flagrantly sexy.

To my surprise and relief everything went well. No one noticed anything unusual about me, and a few even said that I was more knowledgeable about the business than Jessup.

Before the first day was over I had grown comfortable in my role and had begun to flirt a little with the guys in the offices I visited. The teasing comments I got in return made my day for me.

I was so excited when I finally got back home that I blathered on for hours to Cat. She was very patient with me. Listening to my ramblings about the clients and the people I had met that day. Soon though my excitement turn sexual and we ended up in a tangle of bodies on the couch, locked together by our lips and struggling to devour each other.

Cat led me upstairs. I quietly undressed her and laid her back on the bed. I wanted to love my wife as Jessie.

I had become very proficient at the art of loving her thanks to her gentle guidance and instruction. I set to my task with enthusiasm. I licked and nibbled and teased every part of her from toes to ears as I adored her with my whole being. Cat was soon riding the waves of her excitement to high sexual tension, climbing and receding only to climb again until she was at the crest of an orgasm.

I was trembling with the thrill of it too as I rubbed my still clothed body over hers, feeling the fabric of my skirt, blouse and hose on her bare skin. Her bare thighs were warm against my cheeks and her pussy was hot and wet under my mouth when she pushed me back.

She reached under her pillow and brought out a new toy. This was a two-headed fake cock about 12 inches long. She handed it to me without a word. It felt so real, looked so real as I held it in my hand. It had a skin like texture to it and the resilience matched the feel of my own dick when hard.

"Fuck me with that," she said to me.

I leaned back enough to be able to reach her then slipped one end of it into her opening. She was wet and loose and ready for it. Slowly I worked it into her, pushing and pulling back as I went. She was lifting to meet me, trying to get more as I teasingly only allowed her to have a few inches. She moaned and looked into my eyes pleading. I pushed it in until she couldn't take anymore.

Gripping the other headed end of it I pumped the cock in and out of her pussy as she moved and moaned under it. I was riveted by the life like dick in my hand as I fucked her. It looked like I was jacking her off. My painted nails contrasted with the flesh-toned shaft and purple head of it.

"Suck my cock!" she said.

I stared at the five inches of cock sticking from her. I remembered her asking me if she had a cock would I suck it. Now was the time to live up to my promise.

I lowered my mouth to it and opened as wide as I could. This manmade duplicate appeared to be about the same size as my own so I knew it was possible to get it in a mouth, Cat had done mine countless times.

As it passed my lips I could taste the synthetic material of it, but that seemed irrelevant, what seemed real was the shape and idea of it in my mouth. I lowered as far as I could before the gag reflex took over and then backed off a little. I started to slip up and down it as I had seen her do so many times.

Cat lifted to her elbows so she could watch me as I gave her a blowjob.

"Just relax your mouth, don't try to hold it open, let that hard cock do that for you."

I put my jaw muscles in neutral and she was right, it became easier to slip over her. I was taking about four inches into my mouth and twisting around her as I did it. I could feel it working inside her, moving slightly in and out and around as I moved my head and mouth.

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bystillconfused© 44 comments/ 117991 views/ 34 favorites

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