A Whole New 'Woman'

I was out of town on a business trip. Work ran late at the client's office and I was a little tired, but really wanted a drink. Not knowing the area, I just drove around until I found a decent-looking bar.

As I made my way in, I only noticed that the lights were dim and the bar was set up like a relaxed club. The theme was very post-modern and there was electronic music playing in the background, but nothing too loud.

I streamlined my way to the bar and asked for a drink. As soon as the bartender brought over my beer, I pounded it and he brought over another. This one I decided to take my time with. It had been a long day and I just wanted to relax now. As I stared in to nothingness, I realized someone was talking to me.

"Anyone sitting here?"

"Oh, no. It's yours," I said.

The woman who sat down next to me was tall and blonde. Her eyes were a beautiful brown, her lips a deep red, and she was wearing a very sexy, tight shirt that showed off her somewhat large cleavage. I would guess her at around a 36D. The lacy skirt she was wearing was showing off her legs and when she sat, I could even see a little bit of her ass. She was actually a surprisingly attractive woman. This was not something I was planning for and brought me out of my exhaustion a little.

The woman who was now sitting next to me grabbed a mixed drink and then turned to me.

"So, what are you doing here? Are you here alone? Oh, and I'm Jess, by the way." she began.

"I'm Greg and it was a late night at work. I was just looking to get a drink, but didn't expect to run across someone as gorgeous as you."

"I could say the same. Tell me about yourself."

As we continued talking, the two of us got to know a good amount about each other. We were both single. Both interested in each other. We started to move closer to each other at the bar and I noticed her hand on my leg. I imagine she could see the bulge in my pants at this point. Her hand ran up my leg and mine reached behind her and grabbed her firm ass. We moved closer and we reached our tongues in to each other's mouths. Her hand was rubbing my crotch under the bar. I had never been this horny. She was absolutely amazing.

Before I knew it, this girl grabbed my hand and pulled me toward the back of the bar. I couldn't take my eyes off her rear as it moved with her stride. What an incredible body she had!

She pulled me right in to the men's bathroom and locked the two of us together in a stall. My pants were down faster than I could blink and she was on her knees. My cock was harder than it had ever been before and was standing at full attention for her.

Her gorgeous eyes looking straight up at me, she took my throbbing member in to her mouth and swirled her tongue around the tip. Her hand moved to my shaft and started moving up and down it in sync with her mouth. The feeling was incredible. I had a hard time handling it and blew my load in her mouth in just minutes.

Jess stood up and swallowed some of my hot cum. The rest was still in her mouth when she reached her tongue down my throat again. I could taste myself in my mouth. It wasn't as bad as I had expected.

She turned around and opened the stall door. While walking away, she handed me a piece of paper with a number and an address on it.

"Meet me at my place tomorrow night. 6 PM. Make sure the rest of your evening is free."

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I showed up at Jess's place a few minutes early. The entire ride over, I was having mixed feelings of nerves and excitement. She had left me with no ideas of what she had in store for the evening, but if it was as good as last night, I just didn't care.

I knocked on the door and she showed up with a purple corset and a matching pair of purple boy shorts. I knew this would be a great evening.

Jess pulled me inside and shut the door behind me. I was already rock hard and ready for whatever she had in store. She led me in to the kitchen and handed me a glass of water that was poured ahead of time.

"You'll need this." She smiled an odd smile as she handed the drink to me.

I noticed something sort of powdery floating in the water, but I figured it was just hard water. All I could think of was the excitement of the night before and I wasn't worried about anything else. Immediately, I drank all the water so we could move on with this evening.

As soon as I finished, her tongue was in my mouth. When she pulled away, she looked me in the eye and said, "For the rest of the night, you will do as I say. Understood?" I didn't think twice about it before nodding my head. I was nervous and unsure of her reasons for this, but couldn't seem to stop myself from agreeing to it.

"Follow me," she said as she took my arm. We walked in to another room and I couldn't keep myself from thinking about what she might have in store for me.

"Take off all your clothes." I immediately obliged and stood in front of her, once again, hard and ready. A little bit of precum was sitting on my tip.

She backed me up toward a chair in the corner, but I kept my eyes locked on hers'. She told me to sit down, but to sit slowly and not stop until I was fully seated. These directions were so specific, it confused me, but I soon understood why. When I got close enough to the chair, I felt something pressing between my cheeks. My eyes opened wide and my heart began to race. Something started to slip inside my asshole. She was kinkier than I thought! This was NOT something I was interested in and I wanted to tell her, but I didn't seem to have control over my body. I was doing everything she said without question. I could feel the object getting wider and wider, spreading my hole open. Then, all-of-a-sudden, it popped the rest of the way in. I could feel the object filling my insides and it seemed to be lodged in place.

"How does it feel to have a plug in you for the first time?"

I didn't know what to say. I blushed and looked down. I still seemed to be hard! Was I enjoying this? No.. I just didn't have any control over my own actions! It must have been the stuff in the drink. She was controlling me with it!

Next, she stood me back up. "Leave it inside yourself. It'll take some getting used to, but you'll enjoy it after a while. And if you try to do anything funny..." She pressed a button on a small remote in her hand and my insides began to vibrate. I quivered and fell to my knees. She turned it back off and I realized, I clearly had no choice but to go along with this.

She took me to the bathroom and pulled out a razor. I didn't like where this was going at all, but again had no choice but to go along with it. She shaved my entire body, except my scalp, hairless. I felt so humiliated! She seemed to be enjoying how I looked, though.

She now grabbed my arm again, while I was still completely naked and vulnerable, kissed me on the lips and then walked me to yet another room. This room was full of women's clothing. I figured it was all hers'. She definitely had a lot of clothes!

Jess started rummaging through the clothes while I waited, helpless, to see what was going to happen next. She pulled out a pair of stretchy lace see-through panties and handed them to me.

"Put them on."

I slipped them on and, strangely, they fit my package without a problem and held it right up against me. I didn't think they made women's underwear to fit a man! Then she handed me a bra with two inserts. She was going to dress me up like a woman! She wanted me to cross dress!

I started feeling very uncomfortable, but was going along with everything in spite of my own will.

I put on the bra and inserts and then slipped on the light blue cami she handed me. Next was a pair of black tights and a short jean skirt over them. I could still feel the plug in my hole. It was being pressed in by the underwear and tights. I shivered a little from it.

Jess handed me a pair of women's flats and a long, brunette wig. I must have looked surprisingly feminine now! The only thing I was missing was... She grabbed me by the arm again and dragged me back to the bathroom.

Jess sat me down in a chair. I could feel the toy in my ass shift a little and it must have hit my prostate. I felt some precum seep up my shaft. Before I could even respond, Jess told me to sit still and started applying eye shadow and blush. She really went all-out with the make-up.

Finally, it seemed Jess had accomplished her goal. She looked at me with a big smile and said, "I knew I'd picked the right one..." She took me in to the living room, where she had a full-length mirror and I got the first glimpse at myself. I couldn't believe what I saw. I didn't even recognize the person staring back! I looked like a woman... And I looked hot!

Right as I was processing this, I felt the toy inside me start to vibrate. I fell to my knees in pleasure and reached for my hard cock.

"I think you've done quite well so far, darling. Now it's time for the real fun! Wait for me while I get changed."

I obeyed her every wish.

Moments later, she returned in an outfit that seemed appropriate for going out in. A beautiful black dress and heels. I didn't understand why until moments later...

Jess asked me to follow her and we walked out of the front door. I started to get really nervous.

"Where are we going?"

"I want to go get some dinner."

"But I'm still dressed like this and my ass is still plugged!"

"I know. Just walk like I do and see if you can make your voice sound a little more feminine. No one will know!"

I wanted to argue, but I still didn't seem to have the ability to. Whatever was in that drink was strong and was doing its job.

We got to the restaurant and sat down. The plug shifted inside me a little again and I cringed with delight. The waiter came over and seemed to check us both out. He took our orders and walked away. Throughout the meal, Jess just talked to me like I was one of her girlfriends. I tried to play it off as best I could. I started noticing that guys in the restaurant were looking at me. I hate to say it, but I was sort of enjoying it.

When the waiter came back with our food, I began to say 'thank you', but it came out a little shaky because at the same time, Jess pressed her little button and I shook with pleasure. The waiter looked at me strangely and Jess giggled. I was getting harder with every passing second.

Throughout dinner, Jess purchased some wine for us. We shared glass after glass and I could feel myself getting a little buzzed. I think the drugs from earlier had worn off, but it didn't make a difference anymore because my inhibitions were gone from the alcohol anyway.

Every once in a while, Jess would turn on the vibrating plug just for fun and to keep me on my toes. The feeling got better every time. I never thought this would cross my mind, but my ass felt amazing!

Finally, we finished our dinner and prepared to leave. On our way out of the restaurant, Jess stopped and kissed me again on the lips. "You've been a good girl all night. I think we can go back home and reward you now." My face turned red, but I wanted whatever she had in store for me. This was the most thrilling experience of my life!

The whole ride home, I could feel my hard cock throbbing inside my panties. I tried to grab at it, but Jess took my hand when I reached for it, turned on the plug again, and slid my fingers in her mouth.

"You have to wait til we get home," she said as she licked my fingers provocatively, as though she was playing with my cock.

When we got back to her house, I couldn't walk fast enough. I wanted to get inside and find out what else this amazing woman had in mind for me.

We got inside; Jess closed the door behind us, spun around, shoved me against the wall and shoved her tongue down my throat again.

"How badly do you want me?" she asked.

I moaned in delight and I think she knew the real answer. That's when she pulled down her panties and pulled my hand toward her crotch. I was so excited to finally get to this point, but I was immediately confused. There was a bulge where there should have been a recess. I looked her in the eye and she smiled.

Now everything came back to me. The club the night before wasn't just a normal bar. It was a gay bar! Jess was a transsexual! I immediately got nervous, but my inhibitions were so far gone and I was so horny, I wasn't about to argue at this point. Plus, the only thing that showed her masculinity at all was her penis! She was one of the most gorgeous women I had ever seen!

I started to slowly stroke her hard cock. She put her hand behind my head and pushed me down to my knees. I knew what to do almost instinctively. She pushed my head forward and I parted my lips just enough to let her large, hairless phallus inside my mouth. I licked around the tip and I could feel it throbbing against my tongue. I could even taste a little bit of the precum. I then began to thrust my head back and forth on her giant cock. I was surprised how much I could fit in my mouth at once. As I was thrusting, she held my head and was thrusting at the same time. I could feel her warmth inside my mouth and on my face. It was a feeling I had never felt before and I was ashamed to say... I liked it!

Suddenly, Jess pulled away from my face and stood me back up. She kissed me again and told me I was doing a great job. I felt so proud that she was enjoying it. She told me now it was my turn and told me to go in to the bedroom.

When we got in the bedroom, she shoved me down on the bed and started to grope my chest. She kissed my entire body with all my female clothing still on and when she got low enough, she pulled down my panties and started to lick my crotch and near my asshole, around the plug. She turned on the vibrator again as she was doing all this. There were so many new sensations and she was so good at everything she was doing! I already felt like I wanted to explode from everything going on this evening!

Finally, she stopped and pulled the plug out of me. She sat up, unbuttoned her bra from the back, and slipped off her dress. Her breasts were amazing. I couldn't believe they were fake. She then pulled my hands up to them and I was loving every second of this. I was pretty sure I knew what was next. I had never made love to another man! But this wasn't really a man, right? This was surely different. And with my asshole empty for the first time in hours, I felt empty inside and wanted to be filled back up!

"Are you ready?"

I was almost whimpering with how badly I wanted this now.

Jess bent over me, started to kiss me, and led her shaft inside my rear. It felt wonderful. I could feel it going deeper and deeper and my whole body seized up a little as it hit the back of my insides.

She began to slowly thrust. The feeling was completely new to me. It seemed to burn a little at first, but then it got better and better. It felt like somebody was jerking me off from inside. She must have been hitting my prostate! I had always heard men had a special spot inside their assholes, but I thought only gay men could enjoy it! This was the best feeling I had ever felt. My head started spinning from the feeling and all I could focus on was how amazing it was.

I began thrusting my asshole back and forth on Jess's rock hard cock and her tip just kept pressing on my prostate. Precum was seeping out of my tip now and it was amazing. I tried to reach for my cock and Jess pulled my hand back to her chest instead.

"This is your first time. I want you to know what a real orgasm feels like."

She pulled out and flipped me on all four.

"There, now your hands have to hold you up and you can't try that again!"

She slipped back inside me faster than before and went at me as fast as she could. She was grabbing at my chest like I was actually a woman. I could feel my penis pulsating with pleasure and every once in a while my stomach and asshole would tense up like I was about to orgasm, but wasn't quite there yet. I could feel the precum trickling out of me like a slow stream.

When I didn't think I could handle it anymore, I started to feel a sensation I'd never felt before. I couldn't stop myself from moaning like a girl. It even came out higher-pitched than usual.

Cum started spitting out of my penis in long, thick streams. My whole body was reeling with pleasure and tensing up over and over again as Jess continued to thrust.

"I'm close, too, she said."

Right then, she pulled out and told me to get on my knees. I felt so good that I couldn't stop myself from agreeing.

She pulled my head back to her cock, which would have normally grossed me out, but I was in the heat of the moment. I put it inside my mouth and went as fast as I could. Within moments, I felt her load shoot to the back of my throat. I swallowed quickly twice and got most of it. When I thought she was done, I continued to rub her with my hand, but pulled my mouth off and a little more squirted out and hit me on the cheek. I wiped it off with my hand and then licked it off my hand. I had come to love the taste!

Jess looked at me, kissed me again, and said, "You're the best girlfriend I've ever had!"

I felt my heart skip a beat. I realized I was still attracted to her, regardless of her penis or knowing she was actually a man. I realized I liked being in women's clothes and fucked in my ass. I made a decision right then and there. I wanted to move to this city and date a transsexual! I wanted her to dress me up every day when we went out together and I wanted to have her inside me every night.

The next week, I moved down and moved in with Jess. The two of us, from then on, role-played like this at least once a week. I was almost always the bottom with her and was introduced to her full toy collection. The two of us were very happy together from then on and drugs were no longer needed to get me to obey her every command.

This was my story of how I went from straight to being a cross dresser in love with a transsexual.