Charlotte's Choice Ch. 01

I knelt in front of Ken, a guy Janet and I had met in a bar earlier that night. I unbuckled his belt as he stood in front of me and pulled down his khaki pants. I saw the bulge in his grey BVDs that revealed his hard on. Janet was standing beside me kissing him. I was about to participate in my first three-some with a man. I licked my lips thinking of Ken's hard-on and slid down his briefs.

Ken was staying at one of the luxury hotels in Vegas where we met him. After a drink we accepted his invitation to go up to his room. As soon as he closed the door Janet gave me a subtle nod to kneel in front of him.

Janet had been unbuttoning his shirt as they kissed. She then broke off the kiss and unzipped the back of my black A-line dress. His dick stuck out in front of me. The tip was glistening with pre-cum. I put my fist around it and pumped a few times, then licked the shaft and kissed the tip--getting a taste of his juice. Janet knelt beside me and pulled the sleeves of my dress off my arms, then unhooked my black bra. With a slight shake the bra fell to the floor in front of me.

Janet kissed my cheek then nibbled my ear as she cupped my small breast buds then pinched my nipples. I had been on hormones for three months so there had been some growth. I let Ken fuck my face as I took as much as I could in my mouth. After a minute I needed to breathe, so I pulled away and Janet and I switched.

"I can't wait for us to fuck him Charlotte," Janet whispered into my ear.

She was wearing a dark blue lace A-line dress. As she started to suck on his cock I massaged her breasts from behind her. She alternated letting him fuck her face with licking the shaft for a few minutes, then got up. Ken pulled her dress up and off her once she stood. Mine had already fallen to the floor.

I glanced at each of us via the desk light that was on in the corner of the room. Ken had flipped off his shoes and stepped out of his pants and underwear that were around his ankles. Janet had already taken off his shirt. He was deftly pulling off his dress socks. Short with curly hair and a fair bit of chest hair, he had a flat stomach that showed he did do the 1000 crunches a day as he claimed at the bar. Janet was in just her blue thong, with a gold Figaro bracelet and matching necklace and gold stud earrings. Her red hair was long and wavy and she looked a little like Kim Cattrall. Thanks to a mirror, I could look at myself too. My hair was straight and blond, thanks to a wig, and I vaguely resembled Jennifer Aniston. I had small pearl stud earrings and a matching necklace and bracelet. Otherwise, I was only wearing a pair of black lace bikini panties, but they were hiding something.

Ken knew about it--we made sure to tell him at the bar so there wouldn't be any surprises. He took our hands and led us to the bed.

Janet said to me, "Are you ready to be fucked Princess?" That was her pet name for me.

"I can't wait to feel his warmth inside me, thrusting in and out, hitting my G spot." I replied.

"I can't wait to make that happen." Ken added as he had me sit near the edge of the bed and then lay back over it. He pulled off my panties and I stepped out of them. My cocklet was as excited as it gets these days--just semi-erect. He got a condom out of the night stand and slipped it on. Janet grabbed her purse and pulled out lubricant. She then slipped my jeweled plug out and set it aside, then wiped the lube generously over my hole.

Thanks to my anal training, Ken was able to slip into me without any pain. "Good girl Princess," Janet said as she stood next to us and kissed Ken while she caressed my breasts. He took it easy in the beginning, slow and steady. He then picked up the rhythm and his thighs began smacking mine. The pounding was causing my little cocklet to swing and flop around. I was very turned on, being made into the slut I always wanted to be. I was moaning with delight. I began dripping, and Janet noticed. She'd collect some in her hand and made me lick it as Ken fucked me.

Ken then slipped out, and we switched positions. Ken sat on the bed and I sat on top of him, taking his cock in my hole. Janet encouraged us as she began touching her pussy, "Fuck that ass Ken, Yeah. Are you enjoying it Princess?"

"Yes, yes!" I answered in between moans. My moaning became more frantic as I felt the excitement building in me. Janet sensed it. She leaned over and began playing with my nipples. The feeling washed over me as I came, but just a few more drops of clear liquid came out. Janet made sure to collect the drops and have me eat it. But I wasn't satisfied. I increased the pace as I felt another wave coming then a third and a fourth.

Finally I sat up and Ken slipped out again. "Your turn," I said to Janet.

"I want it from behind Ken, as I make out with Charlotte. Charlotte lay back on the bed." I did and Janet laid down on top of me. Ken lined up behind her. He grabbed a new condom and slipped it on, then entered her. Janet and I kissed and caressed each other non-stop as she was fucked. She moaned between kisses.

We gave him a break... she rolled over and I ate her out as she began sucking him. Then he slipped back into her in a classic missionary position as I licked her breasts. Her moaning increased and her whole body shook as she came. He continued as she rode out her long orgasm.

Once she finished, she tapped him out and said, "Why don't you cum in our mouths? Charlotte needs to feel that too." So we knelt in front of him like two good sluts should. We took turns sucking and licking him, as well as kissing each other. When he was in my mouth I felt him quivering and he began to cum. I tasted the first two squirts of warm cum, then wanted to make sure I shared, so I took him out. A squirt hit my cheek and part of Janet's as she got the rest in her mouth.

When he pulled out of Janet's mouth, she and I kissed sharing the cum, then we swallowed. We then licked it off each other's cheeks and swallowed again. We kissed him a thank you, got dressed, said our goodbyes, then went back to our room.

Chapter 1

How did I get there? Well, it had definitely been a journey! My name was Charlie. I was in my late 40's, married to my wife Janet, and our kids had moved off to school. To be honest over the years we had sort of drifted apart--perhaps it was a combination of different interests and not sharing enough.

But it really started at the end of September when I came back home to northern Virginia from a business trip. I walked in the door and called out to her, "Janet, I'm home."

"I'm upstairs in our room." I walked up to meet her. She was sitting on the bed. Next to her was a collection of sexy clothing and toys: A small butt plug, stockings, corset, garter, lacy panties and matching bra, short black tennis skirt, and burgundy halter top.

"Wow, did you miss me?" I asked as I looked her over. She too was wearing a short tennis skirt and halter top--white for the skirt and lavender for the top. Her long curly red hair reached her shoulder blades.

She laughed and pointed at the bed, "What this? No, this is all for you. See, while you were away I had to use your computer and when I started typing in a web address that started with 'sis' all this sissy stuff popped up in the address bar. Then I started checking more of your history and I saw transgender stuff as well."

I wasn't ready for this. Yes, I had been questioning my gender for a while, but had been scared to tell Janet. I had almost told her a couple years before but I chickened out.

"I... I... " I stammered. "I wanted to tell you. But I was so afraid you wouldn't approve."

"I did a lot of thinking over the past couple of days and decided I'd embrace it--either you'd get it out of your system, or you'd become like a sister to me, or maybe I'd even enjoy it. Then the more I read and saw pictures and, to be honest, watched, the more turned on I became. So I read up on it as much as I could and picked up these things for you."

"Wow. I wasn't prepared for this."

She added, "And I did experiment a bit with one of my roommates in college--maybe this is your turn to experiment?" I did remember her talking about having a fling with Sharon.

"Well, do you want to try it?" She asked.

My brain had been turning since the moment I saw everything on the bed. I had been thinking about how to react as she talked. At this point with both kids grown, what did I have to lose? So I answered, "Yes, yes I do."

"Alright. Let's not waste a minute." She started undressing me. My shirt came off, then my pants.

As my pants came off, she saw I was already wearing panties--simple white high-cut panties with a bit of lace. "Well, it seems you've already been exploring this."

"Yes," I admitted.

"Do you have a name in mind?" She asked.

"Yes, I've been liking Charlotte for a while."

Once I slipped my panties and socks off, she said, "Next stop, the bathroom. You'll see a bottle of Nair in there. Rub it all over your hair that is below your neck. Everything besides the hair on your head. It takes a few minutes to set in, so while that's happening get a good close shave. Then shower all the Nair and hair off. Dry off, then come out here."

I followed her instructions and stepped out of the bathroom with the towel wrapped around my waist.

"No, don't wrap the towel around your waist. If you're going to be a princess, you've got to act like it and do all the little things too. Wrap the towel across your chest."

I started to do so, but then she just pulled it off and said, "We've got to get you dressed anyway, so don't worry about it. But what I just said makes me think maybe my new nickname for you should be 'princess'. What do you think?"

I felt butterflies even the first time she shat it. "I like it a lot," I replied as I slipped on the black lace panties

"Oh wait, it looks like we forgot something. I want to keep my princess a nice and horny little slut." She picked up the small butt plug and grabbed a bit of lubricant to put on it, then pulled aside my panties and slipped it into me as I bent over.

"OK then, princess, now let's get you dressed." I put on the matching bra and garter set. I carefully slipped on the stockings "It looks like you've done that before," she commented and added, "Let me help you attach the straps to the stockings." I then pulled the short black tennis skirt up and burgundy halter top over.

"Good princess." She gave me a quick kiss then walked me over to her makeup table. "Next we've got to try to make your face more feminine. She explained each step as she went along, but I didn't absorb any of it as I was so engrossed in my feelings.

A blond wig completed my look. "I love it!" Janet said and asked me what I thought.

"I have to admit if I squint, from a distance I might be unsure if I was a boy or girl."

"Yes, and imagine what things can be like with more time and practice?" She asked rhetorically. She then changed subjects. "Now that I've indulged your fantasy, I want some gurl-cock." She kissed my lipstick covered lips and maneuvered me to the bed. I laid back onto it. She lifted my tennis skirt and pulled my panties to the side. She then slipped hers off and guided me into her pussy as she straddled me.

"Moan like a girl." She commanded as she was doing so. Since I had only had sex as a guy I was being silent as I always had. I began to moan as she had in the past. She joined in as she slid up and down my 'gurlcock'.

The feeling of fucking her as I wore a skirt, panties, bra, and makeup was too much. I exploded inside her within three minutes.

"What?!" Janet exclaimed, a little upset. She got off me and sat back against the pillows. "I wasn't even close. Fine. Now you've got to eat me until I cum, cream and all." I hadn't ever done that after cumming inside her, but considering the circumstances, and even though I was already having a bit of post-sex guilt, I put my head between her legs and began searching for her clit with my tongue. I reached for one of her breasts with my right hand and wrapped my left around her thigh for balance.

I found her clit and massaged it with my tongue. After a minute she pushed my head down and said, "Now clean up my pussy with your tongue." I scooped up some cum with my tongue. "Now swallow," She directed.

After I did so she added, "Good." I continued to explore her pussy as Janet began to finger her clit herself. After several more minutes her moaning intensified and she climaxed for what seemed like a full minute. Then she had a smaller orgasm a moment later.

She pulled me up to put my head on the pillow and we dozed off blissfully.