One Week Ch. 01 Second Edition

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Louise69
Louise69
328 Followers

She kissed my forehead maternally and with a soft "Goodnight", went to bed, leaving me in a state of shock.

Chapter 6

I woke early the next day and had a long, hot shower, before moisturising myself all over. I was getting into the routine now and loved it. Wearing my silk kimono, I sat in front of the dresser mirror and applied my make-up. I put on a deeper, sexier red than usual and grinned as I realised what I was doing. I stepped into my magic wardrobe and selected a figure hugging red satin dress that stretched down to just above my knees and had a high, Chinese style neck, but no sleeves. I wouldn't have been able to fit into it without the corset and it made going up and down steps very difficult, but I found it to be the sexiest thing I could wear.

I chose a strappy pair of heels with a five inch stiletto and started to get dressed. Putting on the corset myself was second nature now, and I could tie the knot at the back without effort. I chose my sexiest corset, red, to go with my dress and a red, padded strapless bra to give myself a bit more bust. I spent some time gluing my breast forms to my chest and smoothing the tell-tale edges so that the forms melded naturally with my chest. As I stepped into the dress, Jackie walked in, wearing a severe business suit, and marveled at what I was wearing. "Beautiful Louise. I love that dress and knew you would as well. I bought two!" She stepped behind me and hooked the latch at the back of the neck before zipping me up. I held my breath as the dress closed up around me, loving how it completely encased my body. The feeling you get when the zip is drawn up your back and the whole dress tightens your buttocks and presses your breasts closer to your chest was one I would never lose the pleasure of.

Dressing in such alluring clothing had two such disparate emotions. On the one hand, the dress was so tight and the heels so high, that I felt vulnerable, yet at the same time I felt so empowered. My forced feminisation had been the most empowering and liberating thing I'd done. Lost in my thoughts, I barely registered a soft snikt! and Jackie chuckling in her husky voice. "What was that?!" I asked. Jackie showed me a small key. "I thought you'd seen it," she replied innocently. "It's a little lock at the back. Bit of fun." She popped it into her handbag and gave me a wink. "Want to look your best for Jade hun? You look stunning. Have a great day." She winked again, kissed me on the cheek and left. I groped behind my neck and, sure enough, found a small lock behind a small flap that I'd missed. I was well and truly stuck! I shrugged, not really minding. I chose to wear this dress. I looked in the mirror and grinned again at what Jackie had turned me into. I made a far better woman than I did man. I hope Jade likes it, I thought and then blushed. I'm a straight man, hoping that a pre-op transsexual will find me attractive whilst dressed as a woman!

It was pretty confusing, so I decided to not even think about it. What will be, will be, I thought as I did the straps on my shoes and mastered the art of going downstairs in a dress that didn't let you move your legs above the knee and stiletto heels that were dangerous enough on a flat surface. As I reached the bottom, the doorbell rang. My heart fluttered as I realised that it was Jade. Nervously smoothing my dress in the hallway mirror and checking every detail in punishing detail, I quailed in fear and self doubt. My hair is wrong, my make-up doesn't work, I look like a man, there's a bulge down there, my waist is too narrow, it looks stupid, shut up, shut up, shut up!!!

I closed my eyes and clasped my hands in front of my face, calming my breathing and steadying my heart. After a few moments, I opened my eyes and appraised myself once more. Hair great, make up stunning, no bulge, perfect hourglass and stunningly dressed. Before I could convince myself otherwise, I emptied my mind and took the plunge, not even thinking about what I was doing and opened the front door. Jade looked stunning. She wore a short tight skirt and a red silk blouse that revealed ample cleavage. She wore a long leather coat that reached down to her knees and high heeled court shoes. For the first time she didn't tower above me as I wore heels of the same height. She held some files under the same arm that she had her handbag hooked into. Her sensuous lips were parted in a lazy smile as she greeted me. "Wow. Louise, you look fantastic. I would never have guessed. You pass better than me. You could go back to work tomorrow and no one would know." I shook my head as I disagreed. Jade was so stunning, she took my breath away and it wasn't until now that I saw a different beauty in her other than her looks. She was so pleased to see me and dropped her bag and files on the atrium table so that she could have me twirl around for her.

"Stunning. Simply divine," she cooed as she admired the new me. "I'm not sure about that, but thank you. And I believe I have you to thank for this as well," I replied, suddenly feeling very awkward and self-conscious. Deep down, my heart soared at the compliment and I wondered at how quickly I'd become Louise. Jade shrugged elegantly. "I knew what you were even if you didn't. Jackie did too, so I can't take all the credit. Anyway," she said, suddenly business like. "We have work to do and I need to use that great mind of yours. I hope it still works as well as it used to." She shrugged off her leather jacket and made her way to the study. She'd clearly been here before and knew her way around.

For the next hour, she took me through the new case, a corporate fraud battle worth millions for us if we succeeded and picked my brain. I'd done a similar case a year ago and it was a good precedent but I was struggling to keep focused. I realised that Jade wore the same perfume as Jackie, but on her it smelled dizzying. Every time she leaned over to get another file, her breasts brushed against the satin of my dress and I felt my nerves tingle with joy. After a while, she put her pen down and sighed heavily. "That'll do for now," she said, with a faint smile. "How about you show me your new wardrobe?" I nodded, glad to get away from the monotony of work and led her upstairs to show her my new world. She squealed with delight at some of my shoes and noted how Jackie had added to her selection with a few items of her own choosing. "You're one lucky girl Louise," cried Jade as she wrapped a silk shawl round her shoulders in front of the mirror. She made it so effortlessly sexy and sensual that I didn't think she noticed the effect she had on me. Jade beckoned me over to try it on for her with a sensual "come hither" sign with her finger. She eyed me seductively and the atmosphere in the room suddenly changed. I felt a charge race up my spine and a surge of adrenalin made my heart beat too fast and too loud.

As I made my way over, I slowed, exaggerating the swivel of my hips and smoothing the dress over my thighs as it gave a soft satin rustle. Stepping closer, Jade smiled and my heart melted. When I was close enough, she tossed the shawl over my head and used it to pull me into a deep kiss. I could feel my heart pounding and was sure that she would feel it too. My cock was straining in its pouch, and I was amazed by the fact that even though I knew she was a transsexual, it only made her more attractive to me. She whispered softly in my ear while her hands stroked my satin clad body, sending electric sparks coursing through me, setting my nerves on fire and fogging my mind with lust.

She pulled away for one brief second and I could see her emerald eyes searching mine, looking for any signs that I was uncomfortable with this. She didn't find any. "Kiss me some more," she said and I did. Her lips were soft and full and she kissed with abandon and fearless passion, unbuttoning her blouse to reveal a lacy black Basque that cupped her wonderful breasts. She stepped away from me, smiling at my reaction at her pulling away from the kiss and took off her blouse and dropped her skirt and knickers with such grace and elegance. The Basque held up sheer stockings and she kept her shoes on as she stepped back to me. I couldn't take my eyes from her cock. It was huge and hung loosely between her legs. A week ago, I would have said that such a sight would be disgusting, but my world view had shifted.

She was still beautiful.

She chuckled as she appraised me and her hands, with some effort, managed to lift my dress to my waist and pull down my knickers. My erection shot up and she grinned again as she led me to the bed with one hand holding my pulsing shaft and sat me down. She kneeled in front of me and took my cock in her mouth, adjusting herself so that she took it all in, deep into her throat.

I groaned in ecstasy, and felt myself quickly beginning to cum as she sucked my cock, her tongue lapping at my pre-cum. It had been so long since I'd had sex and Jade was working my cock and teasing my balls better than anyone had ever done before. Coupled with the feel of my stockings on smooth legs, the tightness of the corset, the sexy shoes and the luxurious satin dress I was wearing all brought me to the greatest climax I'd ever experienced.

I screamed in pleasure as I came down Jade's throat. She lapped it up, swallowing more and more as I came, not spilling a drop. She looked up, her eyes ablaze with lust as I slumped backwards and laughed out loud with sheer joy. "That was amazing," I said as she stood up and straddled me. Jade gave one of her cheeky winks, whilst brushing a strand of hair from her face. "I've barely started Louise," she replied as she leaned over and reached for her bag that she'd dumped on the bed earlier. "Turn over," she ordered, and I complied. As I started to pull my dress back down and my knickers up, she slapped my hand away and rummaged around in her bag, telling me to get on all fours so that I faced away from her.

I started to sweat, suddenly feeling very nervous. I suspected what she was going to do -- a week ago, I'd have laughed at anyone who suggested such a thing -- but I realised that I was an excited kind of nervous. "This may hurt a bit," she said "I'm going to take it very slowly and you need to relax as much as you can. Your G-spot is right up your arse and I'm going to show you what a real orgasm feels like." I felt a cold lube around my anus and was suddenly glad that Jackie had insisted on having the whole area properly waxed.

I gasped as I felt her finger push up my arse. She gave a throaty chuckle and pushed another finger in. I pushed back. After a while the pain went away and the feel of her in me turned me on even more than I thought possible. She reached round and stroked my shaft as she removed her fingers from me. I groaned in disappointment. "Don't worry Louise. That was just to get you ready. Now it's time for the butt plug" I started looking around, but she pushed my head back. I felt a pressure on my arse as she started to push the plug into me. I yelped in agony as I felt myself being split in two, but Jade kept pushing slowly, bringing it out and then pushing it slowly in again. Again, the pain went away, but as she pushed it deeper and deeper into me, I wondered how much more I could take.

As it got deeper in, it hit my G-spot and my whole body shuddered with pure ecstasy as the plug slid past. Suddenly the pressure eased as she pushed it all the way in, my sphincter closing around the narrow base of the plug. "There," cried Jade with a satisfied air. "All in. Now, if I do this..." Without warning, the plug started vibrating, and I bucked with pleasure, groaning at the sensation. She turned me over and had me sit on the plug, driving it deeper inside me. I'd never felt anything like it before in all my life. I also knew that it wouldn't be the last time either.

I kissed Jade passionately and stroked her cock. Flaccid, it was as big as mine was when erect and, as I stroked it, I was amazed at how thick and long it was. I had her lay on the bed, and with the plug still vibrating inside me, stared to kiss her breasts and pinch the nipples through the sheer fabric of the Basque.

Jade gasped in pleasure, arching her back with joy. I moved down and before I could rationalise what I was doing, kissed the shaft of her cock, licking the tip and toying with her balls. I tried putting it all in my mouth, but it was too big, and I could only get half way down the shaft. "Here, like this." Jade showed me how to adjust my head and I found that I could get the whole shaft down my throat. I suckled hard, moving up and down the cock, getting a steady rhythm going and enjoying the taste of it. Suddenly, Jade moved, lifted my head off her cock and shifted me so I was now lying over her, enabling Jade to take my cock in her mouth as I took hers, again fitting the whole thing in. I moaned as I felt myself beginning to cum again, Jade reaching around with one hand and pushing the plug in deeper, the other hand stroking my balls as she sucked.

Jade started to cum too, and I felt her buck underneath me as she came. I was unprepared for how much cum she had and quickly choked as my mouth and throat filled with her cum, trying to swallow as much as I could. I started to cum myself, and she'd been right. The vibrating plug up my arse brought me to a climax that made the one earlier seem insignificant. My whole body vibrated and shook with pleasure as I reached a lengthy climax, sucking greedily at Jade's cock and swallowing as much cum as I could as she climaxed.

My anus pulsed, the sphincter contracting rapidly around the plug as if trying to pull it in further. I barely had time to wonder at how much she could produce as Jade easily managed to swallow all of my cum without spilling a drop. Soon I was done, and I slumped onto my back once more as Jade gave a contented purr. "Louise. You're a natural", she said as she stroked my now flaccid cock. I gave her a smile and she giggled. Not once, ever, had I thought that what I had just done would ever turn me on and I felt sure that, normally, I would feel ashamed now, but I didn't. It had been the best sex I'd ever had and Jade was the most beautiful person I'd had it with.

I kissed her again and she kissed me back, our cum mixing with each other's. Again, I felt no revulsion as I once thought I would. Instead, I felt my cock begin to harden. The plug was still vibrating and doing its magic. Jade quickly straddled me and adjusted my cock so that she could sit on it, the shaft sliding up her smooth, tight arse.

She groaned in pleasure and swiveled her hips, bringing me close to orgasm again. She reached below, to the butt plug and pressed another button increasing the vibrations and bringing me to another explosive climax, Jade screaming with joy as I came inside her. My head began to swim - I was unsure how much more of this I could take! "My turn," said Jade and swiftly pulled the plug from my arse. I experienced a flare of pain as the thick bulbous section was pulled out, but it was soon replaced by a hollow feeling. I quickly turned over and showed Jade my arse. She grabbed my hips and quickly inserted her hard, swollen cock inside. It was much, much bigger than the plug had been and I cried out at the jolt of pain. It was soon replaced by pleasure as she began to thrust inside me, the lube and cum on her cock helping her to thrust smoothly into me. I pushed back with joy, loving the feel of her balls slapping against my stockinged leg and willing her to come inside me. She soon did and squealed with her orgasm as I felt the hot fluid fill me up, bringing me to another climax myself.

Soon the room was silent but for our heavy breathing as Jade removed her flaccid cock from me and lay down by my side, stroking my cheek as she did so. "That was wonderful," she gasped. I agreed, but was too out of breath to say so. My world had changed. I'd just had the best sex I'd ever thought possible, but it was nothing like any of my fantasies had been. They'd been so far removed from this, that my world order had changed once again. I'd never imagined that being fucked like that or sucking cock could be the most amazing experience and it made me question who I was. Jade seemed to sense this and rolled over to her side. She looked so beautiful with her long, dark hair, deep green eyes and sensuous lips. "It's ok Louise. Everyone can question themselves, wonder if they did the wrong thing or regret doing something. Do you want me to leave?" She asked so quietly, that I barely heard her. "No!" I cried, louder than intended. "No. Not at all. It was wonderful. The best that I've ever had. Sex had always been boring for me, just something that was expected in a relationship. But this was something else. I just need to digest a little. It's a lot for me to take in. Stay. Please. We still have a lot of work to do anyway." Jade gave her cheeky grin and slid off the satin sheets. "Come on hun, let's get ourselves fixed up, do some more work and then go out." I slid off the bed and winced at the pain in my arse. Jade chuckled. "It'll be like that the first few times, but you'll get used to it." We cleaned ourselves up, and I was amazed that nothing had gotten on my dress. I couldn't change it even if I wanted to, so was glad that I didn't have to.

I marvelled at how Jade fixed herself up so elegantly. I now knew why she always showed some cleavage. Most men looked at that and didn't stop to think about the rest of the package. Not that they'd notice anyway, she looked so much like a woman. We did some more work, relaxing and enjoying each other's company. Before we realised it, the sun had set and it was dark outside. My stomach grumbled -- not that I'd have been able to eat much in this corset -- and gratefully accepted Jade's offer of dinner in a local restaurant. I'd not been out yet as Louise and Jade quickly picked up on my nerves. "You'll be fine Louise, people really won't know the difference. You've only been doing this for a few days, but you are stunning. Believe me." She went upstairs while I finished sorting the work and came back down with a long Karren Millen jacket that came to the same length as my dress, a scarf and some gloves. As I put them on, she helped button up the jacket and adjust the scarf.

Checking that my Ted Baker purse was in my handbag along with my keys and a small umbrella, Jade showed me how to walk with the bag in the crook of my arm before looping her arm through mine and helping me out of the house. Jade made it so much easier to step out for the first time. I didn't need to pluck up the courage in front of a mirror, she just dragged me straight out without any preamble.

As soon as I stepped outside, a cool breeze swirling around my stockinged legs, sending shivers of joy through my body, I relaxed. At least until we stepped onto the gravel drive and I almost slipped in my heels. Grinning stupidly, we stopped each other from falling over, smoothed down our outfits and walked down the street. As we passed people, Jade chatted away as if without a care in the world. I was still unhappy with my voice, but Jade brushed my concerns away.

"You sound like a sexy, husky woman," she said and tilted my chin up to stop me subconsciously lowering my head whenever we passed people coming back from work. I enjoyed the walk, loving the sounds of our heels on the pavement and reveling in how the breeze cooled the nylon of my stockings and the satin of my dress, making them feel even more sensual. Jade said that the place was just around the corner and I soon realised that walking around the house in heels was far different from walking outside and long distances in heels. I'd picked a very high pair to wear and my feet soon felt sore. "You'll get used to it," murmured Jade quietly, sensing again my thoughts. "All things take time. I barely notice them! Here we are." We'd arrived at a cosy Italian place and walked through the front door, Jade easily taking the lead. The waiting staff immediately recognised her and gave us the warmest of welcomes. She gave me a wink and her best smile as we sat down to eat.

Louise69
Louise69
328 Followers