Tabitha

Note: this is my first story about a crossdresser. If that's not your cup of tea, you may want to move along.

*****

Sean and I had grown close during our time in college. We were both computer science majors and both had struggles dating. We would hang out all the time, normally playing some games or watching movies, but I could always tell that Sean wished he had had more luck with the ladies.

I had always been more open sexually since I had gotten to college. I had short relationships with both guys and girls, though none of them ever felt "right."

Even then, the girls didn't exactly come running. At just 5'4" and all of about 110 pounds soaking wet, I wasn't exactly the model of masculinity. In fact, my long blonde hair and bright green eyes combined with my soft facial features had me frequently confused as a girl on campus.

As poor as my luck was, Sean's was even worse. He wasn't bad looking, but his shy nature kept him from really being attractive to girls on campus. He was about 5'9" tall and around 160 pounds, so he easily towered over me, but was not the "tall, dark and handsome" model most women look for.

We talked often about our desires, and Sean made it clear that he wanted to go on at least one real date before he graduated college. In fact, he became obsessed with the idea. Unhealthily so.

As our senior year rolled around, Sean doubled-down on the idea to the point of nearly making himself sick over it. Every time we'd go out to a bar, he'd freeze up when it came time to ask a girl out. This happened so frequently, that he eventually just gave up altogether. It was heartbreaking to watch.

One night in particular stands out, though.

"Tommy, I'm never going to be with anyone, am I?" Sean asked of me.

"Why do you say that Sean?" I replied, knowing exactly why he felt that way.

"I just can't do it. Girls aren't interested in me, and I can't even bring myself to talk to them. It's nerve-wracking. I'm going to graduate from college having never been on a real date. That's just pathetic. Truly, awfully pathetic," Sean added in a strong and depressing tone.

I could tell he had broken. Sean had finally had enough and my concern for him was as high as it ever was. I knew I needed to do something, but I wasn't sure exactly what.

I had tried asking girls for him, but that didn't seem to work and it only upset him more. If only he could "get over the hump," things would be so much better. I was convinced that if he could just go on one date, it would open up the floodgates for Sean. His confidence would be restored and he'd be able to stop obsessing over his dating life.

I don't know why, but my brain began to explore the wildest of thoughts - what if I acted as his first date? Not as myself, but as a woman.

I initially shook off the thought as crazy. What in the world was I thinking?

However, over the next few days, my mind just wouldn't leave the idea alone. I had been mistaken repeatedly for a girl throughout my time in college. This could actually work. If I could just learn some makeup tips, put together a small wardrobe, and learn to talk and carry myself as a woman this may be doable.

What once seemed crazy started to sound more reasonable the more I thought about it. This would be a one time thing for a friend in need. It didn't mean anything other than that. In hindsight, I can see now that my heart wanted it more than I was ready to admit.

One day in January I decided to bite the bullet. I bought a makeup kit online and began watching YouTube videos on how to apply make-up. The first few times I tried was a disaster. I looked more like a killer clown than a beautiful woman. Over time, though, I began to get the hang of it. After a week of practice, I could barely recognize myself when I looked in the mirror.

The more I played around, the more I wanted. I found favorites of all types: primers, foundations, highlights, and blush. I loved how eyeshadow and eyeliners made my green eyes pop and my favorite lipstick and gloss gave my lips a shiny, dark red seductiveness. My naturally thick lips looked absolutely stunning when colored.

Having a small frame made it easier to find women's clothing. I ordered tons of outfits online, using only stores with liberal return policies. Eventually, I settled on a few outfits including some pretty, lace nighties that felt so sexy when I wore them. I was falling in love with my new wardrobe and began looking forward to wearing those clothes in the evenings when I was alone.

The feel of the soft silk on my body was intoxicating. I often found myself wearing the nighties along with silk panties to go to sleep at night. I got easily turned on by the clothing and often masturbated vigorously while dressed as a woman. I began wearing women's panties all the time, preferring them to my cotton boxer briefs that I had used for years.

If I was going to go out as a woman, though, my body needed to look more feminine. So, during the days, I started wearing a corset to put some curves on my body. I made sure to wear baggy clothing to hide the device. It was painful and awful at first, but the results were hard to ignore. Combined with the fact that I already had a nice, tight bubble butt - the result of good genetics and a beneficial workout routine over the years.

I was never a particularly hairy person, but what little hair I did have on my body was waxed off periodically. I couldn't resist the feel of my silky smooth skin rubbing against my luscious silk clothing. I would get very stiff just feeling the silk rub against my skin. I even bought a home laser hair removal kit to make some of the changes permanent.

My hair had never looked better, either. I let it grow out even longer, though I kept it tied back during the days. I began regularly using nicer shampoos and conditioners and took better care of my long, blonde locks. I played around with making my hair wavy, and loved how full and feminine it looked. As Tommy, though, I'd mostly wear baseball caps to hide what I had done with my hair.

I also learned to walk in high heels and had developed a more feminine gait. I had never had a very deep voice - puberty only made a quick pitstop in my teen years - so learning to speak in a higher, more feminine voice was quite easy. I practiced by calling people I knew on the phone to see if I could fool them. Over time, I became quite adept at speaking as a woman.

By the time April had rolled around, I had become an expert in all of these things. I didn't realize it then, but I felt so sexy and "at home" whenever I was living - even if privately - as a woman. I kept telling myself that I was doing all of this for Sean, but the reality was that I enjoyed every last bit of becoming a woman.

As the end of the school year drew closer and closer, I became more and more concerned about Sean, though. Even though I had spent the last couple of months finding ways to become a believable girl, getting Sean to buy in would be a different matter altogether. I decided I needed some practice in the real world before presenting myself to my friend.

Going out on the town

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I decided that I needed to see how believable I would be as a woman before approaching Sean with my idea. If I couldn't make other people believe I was a woman, Sean would be mortified at the idea of going out in public with me.

Rather than run the risk of someone I knew seeing me, I opted to drive 60 miles north of the city to a small town to give my new looks a dry-run in one of the local bars.

I went the whole 9 yards for the first outing. The corset had succeeded in giving me a more feminine figure over the past several months, which excited me greatly. I tucked my cock between my legs and used flash tape to keep it in place, wearing a pair of silk pink panties on top of them. I put B-sized silicone enhancers in my bra to give me the illusion of having breasts. All of this was encased in a tight, red dress that stopped right above my knees and showed off my perfect bubble butt wonderfully. My hair was thick, wavy and perfect while my lips looked delectable with their shiny dark red color.

As I looked in the mirror, I didn't recognize myself. I was my own harshest critic, and even I was fooled. I felt confident as I got into my car and made the drive north for the next hour.

As I walked into the "Chasers" bar, my heart began pounding furiously. I began questioning myself and what I was doing. It was one thing to dress up in the security of my own apartment, but being out in the world like this was another thing altogether.

Just as the doubts and fears were convincing me to go back home, a tall, fair-skinned man with dark brown eyes and jet black hair approached me.

"Can I buy you a drink?" he asked me.

I nervously responded, "Sure."

He smiled and walked me over to the bar. He turned to face me again and asked, "What's your fancy?"

"Dirty martini, please," I responded.

After we got our drinks, we sat together in a booth in the corner. The bar was surprisingly well lit, unlike many I had been to. I felt relatively confident that if I could pass this test in this lighting, I'd pass the test nearly anywhere.

"So, what's your name beautiful?" the man asked me as we sat.

"I'm Tabitha. What's your name?" I responded.

"I'm Rich, but my friends call me Dick. You can call me whichever you'd like," he smiled and responded.

"Ok Rich. That was pretty forward of you to offer me a drink. How did you know I wasn't here for someone?" I asked him.

"Oh, I didn't care if you were. I saw a gorgeous blonde walk in and I didn't want to run the risk of someone else jumping in front of me," Rich responded, making me blush considerably.

"You're too sweet," I responded back sheepishly.

Over the next hour, Rich and I spoke about a variety of topics. He was a lawyer and recently divorced. I told him I was a student, but didn't share which college I was at - obviously.

As the night progressed, our bodies slowly drew closer and closer. After a couple of hours, Rich made his move. He leaned in for a kiss. I hadn't intended to go this far with anyone, but this would be an incredible test. I leaned in as well and our lips met.

This wasn't like other kisses. This kiss was electric, and sent cold shivers down my spine. I had kissed other guys before, but not like this. Rich was kissing me as a woman. He was attracted to me as a woman. That feeling invigorated and excited me in a way I had never experienced before.

It excited me so much that my body began to respond. I could feel my cock beginning to stiffen, which awoke me out of my trance.

I broke the kiss and pushed myself back and away from Rich. "I'm so sorry, Rich, but I can't do this," I said as I hurried to get up from the table. My cock was still stiffening and making me incredibly uncomfortable.

"Was it something I did? I'm sorry, I thought we were connecting," Rich responded, clearly confused and concerned.

"You're amazing. It's not you. Not at all. I have to go," I said, as I hurried out the door of the bar. I quickly jumped in my car and took off, only to see Rich come out the door of the bar from my rear view mirror.

I reached between my legs and into my panties to pull off the flash tape. My 7 inch cock sprung forward, as stiff as it had ever been.

I had gone much further with my experiment than I had intended. Rich clearly thought I was a woman - a gorgeous one at that - and his kiss lit me up inside. That one kiss set my mind off in a thousand different directions. I was confused and excited all at once.

Once I got home, I rushed into my apartment, collapsed onto my bed and took my cock into my hand to relieve the pressure. The electricity was still surging through me, even after the hour long drive.

I had passed my first test and had learned some things about myself in the process. It was time to make plans with Sean.

Reluctant

------

While the experience at the bar convinced me that I could pass as a woman in public, convincing Sean to go out with me would be a new, different challenge. I decided the only way to make it happen would be to approach him as Tabitha. I had to show him first hand that it could work. Trying to convince him as Tommy would be fruitless.

On a beautiful May afternoon, I returned to my apartment and began my transformation. I opted to wear the same red dress as I had to the bar. I expertly applied my makeup and prepped my blonde wavy locks.

It was finally time.

Around 5 that evening, I hopped in my car and drove over to Sean's apartment. I made my way to his door and knocked three times. My heart was pounding like a bass drum in my chest.

Sean opened the door and I saw his eyes grow big, as if from shock.

"Hi Sean," I said in my feminine voice as he stared at me, his mouth agape.

"Uh, hi," he responded, gulping noticeably after squeaking the words out.

"Do you know who I am?" I asked him.

"I'm sorry, I don't. Should I?" he responded.

"I'm your date for the evening Sean. You're going to take me out to dinner and dancing," I responded enthusiastically.

"Oh, did Tommy put you up to this?" Sean said, with a slight look of dejection on his face, his eyes turning to the ground in front of him.

"Sean ... I am Tommy," I responded. His eyes lifted up and met mine. He stared at me for a moment before the realization hit him.

"Tommy?" Sean said in disbelief.

"Actually, you can call me Tabitha. I'd prefer if you called me Tabitha," I responded.

"Tommy, what the hell man? What are you doing?" Sean said in an agitated voice.

"Sean, you're going to take me out on a date. Not as Tommy, but as Tabitha," I responded strongly.

He stared at me for a long moment before responding, "Come in. We need to talk about this."

We both sat on the couch in his living room, but he couldn't take his eyes off of me.

"Why are you doing this?" he finally asked me, before adding, "This is insane. This is really, truly insane."

"Sean, you've been so depressed this year. You're a good guy and you need a boost of confidence. We've known each other for so long that I figured this would be a good way to get your confidence built back up with someone you trust," I told him.

"This is insane," Sean said quietly.

I continued, "It's nothing more than one evening out on the town. You and Tabitha. Dinner, dancing and that's it. After tonight, you'll never have to see Tabitha again."

"I didn't recognize you. You're so ... you're so beautiful," Sean said quietly.

"Are you going to make me sit here all night or are we going to go have some fun?" I poked at him, nervously hoping he'd finally come around.

He stared at me for what felt like an eternity. He finally broke his gaze, shook his head and said, "Oh hell. What have I got to lose? My dignity was lost a long time ago anyhow. Give me a minute to get dressed, Tommy."

"Tabitha," I responded.

"Sorry. Tabitha," he replied.

After a few minutes, Sean emerged. He was wearing dark blue jeans with black boots and a nice white button up shirt. He made up his dirty brown hair and had an attractive 5 o'clock shadow that showed off his facial features well.

"Ready to go, Tabitha?" he asked.

"Let's do this," I responded excitedly.

We made our way out of his apartment and to a local tapas place. As we walked in, I noticed quite a few guys shift their gazes in my direction. One guy in particular got a slap on the arm from his lady friend who didn't like him looking my way. I felt so beautiful in that moment, as multiple sets of eyes scanned my body up and down. I made a point to turn my hips to show off my perfectly toned butt.

Sean and I got a table and proceeded to order some food and drink.

"So, Tabitha, tell me a little about yourself," Sean said in a sarcastic and funny tone.

"Well Sean, I'm one of the most beautiful women in this bar and I'm here for you. You should feel special. Every guy in here has checked me out at least once tonight," I deadpanned.

"You truly are the most beautiful woman here. There's no doubt in my mind about that," Sean responded.

I blushed deeply at the compliment. After that point, our conversation opened up. Sean never referred to me as Tommy and treated me like I was truly a new woman he had just met. For some reason, that set me at ease as well and our evening progressed even better than I imagined. In some ways, I think he completely forgot who I was, which was perfect.

After we finished dinner, we made our way to a local club for some dancing - something neither of us had ever done before. For the next couple of hours, Sean let loose in a way that he never had before. He seemed so confident and carefree. This entire experiment was clearly working. He even danced with several other women at the club, which had the unexpected impact of making me jealous.

On one such occasion, a buxom brunette was getting a little too close to Sean for my tastes. I made my way over and cut in on the dance, as if to claim him as my man. I got very close to Sean, our faces only a breath apart. He reached behind me and firmly grabbed one of my butt cheeks to pull my body close to his. Our bodies began grinding together in unison with the pounding music. The other women looked on jealously as my body pressed hard into his.

I could tell Sean was now only seeing Tabitha, and he liked what he saw. My body felt electric as we moved on the dance floor together. I don't know how long we were out there, but it felt like years. As the music died off, we made our way to a private booth in the corner.

"So, are you having fun?" I asked Sean, who looked relaxed and content.

"I'm having an amazing time. What about you Tabitha?" he responded.

"I'm in heaven," I said, meaning every single word.

We sat closely together in that booth for several minutes. Our bodies gravitated towards one another and before long, I found myself resting my head against his chest and shoulder. He put his arm around me and pulled me close to him. It felt warm and inviting and I could have fallen asleep there with him.

After a while of sitting there together, Sean finally said, "Tabitha, do you want to go back to my place?"

I turned my head to look into his eyes to determine his intent. Our eyes locked together. I felt a surge of passion that I knew he felt as well. Without thinking I responded, "Absolutely."

We made our way outside quickly, jumping into Sean's car and speeding back to his apartment. My body grew tingly from the excitement. I didn't know what was going to happen, but I sensed that Sean wanted more and I knew I wanted to give it to him.

As we got back to the apartment, Sean opened the door for me, letting me walk inside first. As I turned around to face him, he grabbed me tightly and pulled me into a long, passionate kiss. My body melted in his grasp as his arms straddled around me, with one hand cupping my backside firmly. We kissed for at least a minute, before I finally realized what was happening.

I had gotten so caught up in the energy, I forgot I wasn't fully a woman and Sean was not gay. I suspected that Sean had forgotten as well.

I stopped the kiss and held Sean at arm's length and asked him, "I'm so sorry Sean. Think about this. Are you sure you want to do this? You do remember who I am, right?"

"I do remember. Right now, you're Tabitha. And I want you badly," he responded.

"Are you sure this is what you want," I asked him one more time. The look in his eyes was all the answer I needed. He knew what he wanted - me.

I loosened my arms and he proceeded to pick me up onto his waist. Instinctively, I wrapped my legs around him. I could feel his cock stiffening in his jeans against the bottom of my leg. The sensation only turned me on further. My own cock was beginning to stiffen, held at bay by the flash tape I had applied earlier in the evening.