Change of Fate

Foolish choices fill most every persons life at least part of the time. Most of these choices are harmless enough, and don't leave much of an effect on our lives. Other times, like this, we make a choice that forever changes our lives...

I used to be a normal guy, like many others, at least for the most part. I dated normal women, and did normal things. The only thing I did, that was perhaps not normal, was cross-dress.

You see, I was always in good shape, from swimming mostly, along with biking and other aerobic exercises. This kept my muscles toned but not large. This, combined with being short and slim, kept me from being what you would call manly. I didn't have trouble attracting the ladies, but I think it was mostly because I was their size and they didn't feel threatened by me.

I started cross-dressing at an early age, mostly out of curiosity. I realized early on that I was closer to most women then men in shape, and I wanted to see how I could look. It started out as you might imagine, with me borrowing small items of my mother's lingerie from the laundry. I would be careful, and I only did it when I could be sure that no one would be home for several hours at the least.

At first, I just tried on the lingerie I could borrow, with predicable results. I looked like a small guy wearing lingerie, which didn't make me happy. Soon enough, I moved up to wearing some makeup with the lingerie, as well as stuffing the cups with breast forms my mother had. This made me look better, but it still wasn't quite right. I progressed to wearing stockings with a garter belt, as well as wearing a wig. This finally had me looking feminine, which would get me very aroused. I even went so far as to join the swim team as an excuse to shave off my body hair. I once even went all the way, putting on the lingerie, makeup, a dress, high-heeled shoes, and a wig. I only did it the one time though, as wearing the whole get-up made me paranoid, and as pleasurable as it was, I could never work up the nerve to dress up all the way again until after I graduated.

In collage, I was able to get my own place, so I was able to dress up as often as I liked. With some discrete shopping on the Internet, I had all the feminine wardrobe I could want. I had many selections of lingerie, dresses, pants and blouses, stockings, and a corset. I bought make-up of my own, large breast forms, and several different styles of wig. I bought many pairs of shoes to compliment my growing wardrobe.

I wouldn't dress up more than a couple of times per week, but when I did I felt more alive than I ever had before.

Now, through this all, I never was attracted to guys, not at all. I was always attracted to women, but I always wanted to be with them as a woman, instead of being a man. I could never become very satisfied in a relationship when I wanted to share myself as a woman with my girlfriend. This eventually led to my relationships ending quickly most of the time. The only time I tried to share my feelings with a girl she rejected me utterly, but she was still kind enough to not spread around the fact that I was a cross-dresser.

I graduated collage, and moved into the city, where I got a job working from home maintaining web sites other online programming. This allowed me to live however I wanted. It also allowed me plenty of extra cash to spend at bars, which helped me attract women, which otherwise would probably have been difficult. Most of my relationships were one-night stands, but eventually I met someone worth working to keep.

Her name is Erin, and she is the most wonderful woman I have ever met. First off, she has a wonderful personality, perky and upbeat, curious and adventurous, and willing to listen. Secondly, she is absolutely gorgeous, easily beautiful enough to become a professional model if she wanted to. She has long blond hair, full lips, wonderful green eyes, a cute nose, and a long, slender neck. Her arms are graceful with delicate, long fingered hands, connected to her with beautiful shoulders. Her breasts are perky, and just larger than you can easily hold with one hand. This leads down to her waist, which is toned and sexy. Her hips are nice and wide, perfectly sized to compliment her frame. And then there are her legs, which are so toned and shapely as to seem endless.

Now, when I first met her all I could tell was that she was pretty, as she was wearing plain clothing to suit the cold winter day. We met on the subway, sharing a seat, as the rest of the seats were full. Being the friendly person she is, she soon had me engaged in conversation with her. After talking for a while, she invited me to go out for a drink with her, which is where she was headed. Not needing much encouragement, I agreed to her request. After drinking for a while, she invited me over to her apartment, where we could chat and drink more comfortably.

It didn't take us very long once in her apartment to start kissing, which naturally enough led us to her bedroom, where we hungrily undressed each other and landed on the bed. Being the energetic type, with me being somewhat submissive, she naturally enough rode me, with me holding on to her hips, and her massaging her breasts erotically, until we both climaxed together, and promptly fell asleep.

Waking up with Erin cuddled up to me was the best thing I could have imagined. Gently kissing her awake, we proceeded to talk, getting to know each other better. It turned out that we had many of the same interests, and that we genuinely liked each other. This made us both very happy, as we had both found a special someone in a place where love wasn't easy to find.

Over the following weeks, we spent a lot of time together, on dates, seeing the sites, having walks while we chatted, and in the bedroom. It turned out Erin was a devil in the sack, had an insatiable sexual appetite, and wanted to try everything. We tried every sexual position, bondage, role-play, and even sex toys. It was wonderful, and we shared everything with each other. Everything except my cross-dressing that is.

I still had the desire to be with a woman as a woman, but I didn't want to jeopardize my relationship with Erin, so I didn't tell her. I figured I could still do it when I knew she would be at work or if she was spending the day with a friend. I didn't see how she could find out, as I never dressed up outside of my apartment, and I always locked the door and closed the curtains. I thought my secret was safe, and that nothing would tip her off. It turned out I was wrong, and I would find out first hand how she would react.

It was a Friday, around noon, and I was dressed up in a bra and panties, with matching garter belt and stockings. I had my breast forms on, was wearing makeup, had on a brunette wig, and was wearing a skirt and blouse. I was sitting on my couch, with my skirt up around my waist, rubbing my erection through my panties. I was oblivious to the world, which is why I didn't hear my door open up.

You see, I was in love with Erin, so I had given her a key to my apartment, so she could come by and visit whenever she wanted. I hadn't figured that she would be by today, as she said she would be in business meetings all day long, and she was always tired at the end of long meetings and was never in a romantic mood. That was why I figured this time to be a perfect opportunity for me to dress up, when I knew I wouldn't be interrupted. That is why I was so surprised to hear Erin's voice.

She said, in an angry voice, "What do you think you are doing?"

I quickly stopped rubbing myself, looking up in shock.

In a confused voice, she said, "who are you, and why are you masturbating in my boy....friend's....apartment?" After a few seconds looking at me, she got a look of amazed comprehension on her face. "Sam, is that you?" she asked.

Standing quickly, I stammered, "....I....uh....didn't expect you....uh....what are you doing here?"

In a quiet voice, she said, "the meetings went much faster than anyone expected, and since it was a nice day, my boss sent everyone home. I decided I should come over and surprise you, and it seems like I succeeded."

"....I....um....can explain."

With a small smirk on her face, she said, "what's to explain? You like to dress up like a woman, and I don't have a problem with that."

"You don't?" I said in a surprised voice.

"No, I don't. Many people have a fetish or two, and yours happens to be cross-dressing. It isn't that odd, there are lots of people that do it. At least you do a good job of it, and look good dressed like that."

"Really? You think I look good?"

Walking up to me, she said in a sexy voice, "You look very good, and I like it." She then pushed me back onto the couch, straddled me, grabbed my head, and started kissing me hard. After showing me who's boss, she pushed my skirt up to my waist again, and pulled my panties down, pulling my cock out. She then pushed her own skirt up, and stuck my cock into her dripping wet pussy. Hearing me gasp at the abrupt feeling, she said throatily, "I took off my panties in my car. I figured I could play the naughty secretary and you could be my boss. You were going to spank me for being bad, and have rough sex with me as punishment. Now, however, it seems I'm the boss this time and you are the bitch, so fuck me hard, or you'll be sorry."

Hearing the playful tone in her otherwise angry sounding voice, I said in a submissive girls voice, "yes master, I'll make sure you enjoy yourself." I then proceeded to put all of my effort into our fuck, ramming my cock as deep into her as I could, holding tightly to her hips. After only a few minutes of this, she started moaning loudly and pinching her nipples through her blouse. She then ripped it open, unhooked her front opening bra, and cupped her breasts roughly, pinching her nipples even harder. A few seconds later, she tensed up, and screamed her pleasure out, the walls of her pussy clenching my cock hard, milking me in rhythmic pulses. That was all I could take, and I blasted load after load of my cum deep into her, which only set her off even more.

After lying together for a few minutes, she sat up, my cock still lodged deep into her pussy, only slightly softened. Looking deeply into my eyes, she said, "How was it?"

Grabbing her and pulling her close for a long kiss, I said, "It was amazing! That was the most amazing sex I've ever had. I've never had sex while dressed like a woman, and I didn't know it would be so different. It added a whole new level of excitement to the experience. I have never cum so hard as I did just now!"

Smiling, she said, "Good, because being so in control made it so much better to me too, so I think we'll have to do this again, and soon. Now, I want you to model for me, show me everything you own. I want to see just how sexy you can be."

Laughing, I said, "I'd be happy to model for you, wait right here and I'll go dress up for you!"

After getting up and heading to my room, I started picking out outfits that I thought Erin would like. Dressing up in a skimpy French maid's outfit, I walked out to find Erin sitting on the couch, completely nude, slowly fingering herself, while watching me. Smiling at her, I sexily strutted past her, bending over to pick up an imaginary item on the floor, shaking my ass at her. I then stood on my toes to dust at imaginary dust high up, making sure she could see up my skirt. Turning around, I saw her beckoning me to come over, so I strutted to her.

Once she had me close, she pulled me to her for a hot kiss, which lasted several minutes. When she was getting horny again, she pulled me down until I was kissing my way down her body, starting with her sensitive neck, down to her delicious breasts, which I sucked at for a few wonderful seconds. By this time I was getting really horny myself, so I was really getting into pleasuring her, so much so that when she pulled me all the way south, to her pussy, I didn't hesitate to start eating her out, even though her pussy was still filled with our mingled juices.

I started by licking her labia, up and down, in every spot, until they were clean, and then started on her clit. I licked it until it too was clean, and then dived into her honey pot. I stuck my tongue deep in, licking every drop of our juices out, and kept licking deep and alternating to her clit, until she came hard on my face, drenching me in her delicious juices and the remains of our lovemaking. She then pulled me up quickly and started kissing me hard again, almost sucking my efforts off of my face. She then stood up and pushed me onto the couch, and lifted up my skirt and pulled down my panties to get at my cock.

She proceeded to lick the crown clean of my precum, licking her way down my shaft until she was sucking my balls, one at a time. Once she had them clean, she licked her way down to my asshole, which she started tonguing. Finding it more pleasurable than I expected, I let her continue. Once she had my hole nice and wet, she stuck her tongue deeply into it, which caused me to moan in pleasure. She then returned to my cock, first licking the crown, then sucking it gently into her mouth, she soon had me deep into her throat, never missing a beat and not gagging at all. She sucked me hard and long, until I was almost ready to burst, and then she suddenly stuck her finger deep into my ass, which set me off explosively into her mouth. My cum spurting quickly into her mouth, she continued to suck, swallowing it all.

Once I was spent, she climbed on top of me, kissed me tenderly, and we fell asleep together.

Week after week, we continued to play around with my cross-dressing habits, with me wearing various outfits for our role-playing. I played the frightened slave girl, the naughty secretary, the criminal in need of a sexy punishing, and others. I kept up the submissive roles, and Erin excelled in the role of the Boss, or the master, or whatever role it was required, always in charge, always dominant.

She kept me ordering new submissive outfits for me, and dominant outfits for her. Our roles kept being further defined, until I was completely submissive in our sexual relationship. Outside my apartment, we looked like an ordinary couple; acting like any other couple deeply in love would, dressed normally. Except I was always wearing a bra and panty set underneath my male clothing, and I had begun to wear a butt plug too. Erin Kept wearing the normal clothing she always did, but in the bedroom she would often wear leather dominatrix outfits, and had even progressed to using a strap-on dildo on me, which I had grown to love.

It became common for her to come home to me, pull up her skirt, and command me to pleasure her until she had an orgasm or two before we even talked. She had also started browsing fetish-clothing stores, and small shops I'd never heard of in the seedy part of town, always looking for the next experience for us.

Then, one week, she came home all excited, carrying a large package in her arms. I was on my knees as soon as she came in, but she pulled me to my feet and told me, "not tonight love, I have something even better planned for us, something I know you will enjoy. I was browsing a small shop selling occult things for people that practice witchcraft and sorcery, and I found something we will have a lot of fun with."

Curious, I watched as she started pulling things out of the box. First, she pulled out a strap on dildo, one of the type that has a dildo in the harness that goes into the user's pussy, as well as the one that goes into the other participant. It was odd, because the straps were very thing and skin colored, and the dildo sticking off of the front appeared almost lifelike, about a foot long, but was not erect looking.

She then started pulling out a set of women's clothing, starting with a skimpy lace bra, a matching pair of lace thong-cut panties, a full leather corset, sexy silk seamed stockings, and a pair of lace up high-heeled shoes. After that she pulled out a blond wig, and to top it all off, a leather collar, with a ring sewn right into it.

She told me, in an extremely excited and horny voice, "put on the collar, the clothes, the wig, and the shoes, saving the panties for last. I'll put on this dildo, and we'll have a very good time."

Putting on the collar, I could feel a tingly sensation spread throughout my body. Lifting the wig onto my head, I could feel my hair disappearing and the wig attaching itself to my scalp. Looking in the mirror, I could see I now had a head full of beautiful blond hair. Getting excited, I put on the bra next. As soon as I had it on all the way, I could feel my shoulders and arms change shape, and I quickly grew a large pair of breasts, around the size of large honeydew melons. I pulled the stockings on, and I could feel my legs changing shape, into a pair of sexy women's legs. I then put on the corset, and I could feel my waist and hips reshaping themselves into bottom half of the hourglass shape, fitting my new top half perfectly. I put on the shoes, lacing them up, and could feel my feet change shape to those of a woman's, sexy and petite. Grabbing the panties, I slowly stepped into them, and pulled them up. Holding my breath in excitement, I could feel my balls draw up into my body and transform into ovaries, and my cock sort of inverted itself, forming into my new pussy.

I looked over at Erin, and could see her wearing the dildo, which was hardening like my cock once did at the site of the new me. I could see the other end lodged deep into her pussy, filling it completely, with no room for even a drop of juices to leak out. At the moment I could see the straps had become part of her skin, with only a raised outline of them hinting at where they were. Walking up to her, I gently started kissing her, then slowly started kissing my way down her body. After giving her breasts a thorough kissing, I made my way down to her strap-on. Grabbing hold of it, I could feel it's heat, just like a real one, and I could even feel a heart beat from it. I then gently started licking the tip, which caused a small amount of precum to leak out. I licked it off, and found it to be delicious, much different than I had thought of the taste of my own when I ate it out of Erin's pussy. I licked my way down the shaft, sucking first one than the other of the strap-on's balls, now Erin's, into my mouth.

After sucking on them thoroughly, I moved my way back to the crown of the dildo/cock. I started first by sucking just the head, and found its taste to be divine, and sucked about half of it into my mouth. Soon enough I had most of it, then all of it down my throat. I started sucking hard, licking around the base and her balls, until I could feel it tightening and trembling. Sucking with even more enthusiasm, I felt her hit the point of no return, and tasted the first of her cum shoot straight down my throat. Not wanting to miss out, I pulled her cock almost all the way out of my mouth, until only the head was in, and kept sucking, getting load after load of her cum on my mouth. The taste was somehow intoxicating and sweet, and it was driving me crazy with lust.

Erin pulled out of my mouth, and started shooting even more cum out of her cock, all over my face and breasts, with me trying to catch as much of it in my mouth as possible. Once she had stopped shooting her load, Erin pulled me up and kissed me hard, licking the cum off of my face and the tops of my breasts. She then pulled back, and said roughly, "Get on your hands and knees bitch, and hold your ass high, I need a piece of that!"

Obeying her, I got on my hands and knees, holding my ass in the air, the scent of my dripping wet pussy permeating the air. Smelling it, she said, "Oh, so you want a piece of my cock, do you bitch? Well, you're gonna get more than you can handle, I guarantee it!" Reaching around to my chest, she freed my large breasts from my bra, and roughly fondled them, which caused me to moan loudly.