The following story is intended for adult eyes only. If you are not at least 18, or are not supposed to be reading this, scram. This is a work of fiction, though I wish it were true.
The devil is in the details...part 1 of 5
Sunny and 70 are not usually the words used to describe the weather in St. Louis in January. Yet here it was, a beautiful Tuesday afternoon and I wasn't going to waste it hanging around my apartment. No...today was going to be fun. You see, I am a crossdresser...or at least I think I am. It might run deeper than that, but I have never taken the initiative to talk with any sort of professional about my feelings or desires to be a woman. Being 26, and pretty much entrenched in my job and family life, I have just come to accept that things will never go beyond crossdressing.
I knew when I was 13 that I didn't feel right in my body. I was a small guy...still am. At 5'7" and 130 pounds, I don't exactly make the most impressive picture of masculinity. But then, I never really wanted to. I started dressing in my younger sister's clothes at 15, and haven't stopped since.
At 21, I moved into my own apartment and tried the whole dating and relationship thing. I have had a few girlfriends along the way, and slept with a half dozen or so of them. But, I have never felt right in doing so. I guess you could say I was in a state of flux then, not really knowing what I wanted. I did know that I came from a rather large family, and was extremely careful not to let my crossdressing secret out.
Over the years after I moved out from my parents, I became more and more adept at my cross- dressing. Being able to scour the internet for tips and products was a God-send. Not only had I become passable as a woman, but I was able to completely blend in. I mean, it's one thing to go to a gay or TG bar and dress as a woman...everyone there knows your a "dresser". It's another to be able to shop, travel, and just enjoy everyday life as a woman and not get strange looks from people around you. That was how good I could dress and blend in.
Unfortunately for me, I also had a "regular life" as a man, so dressing wasn't something I could do with regularity. You see, dressing for me had become an artform almost. If I couldn't do it right, I didn't want to do it. And for me, doing it right meant waxing my legs, back, arms, even shaping my eyebrows. This meant that I would have to hide myself and my waxing from my co-workers. Can't run around with shaved legs in the summer time when you work outdoors. It gets hot in St. Louis in the summer. Don't want to have to wear long pants to the family BBQ on the fourth of July. This meant that most of my dressing days occurred in the winter time, when I could hide my shaved arms and legs under long clothing.
Which brings me back to that wonderful Tuesday in January. Here it was, an incredible day out and I was going to dress the part and get out amongst the people and enjoy the day as a woman. My day would start as a businesswoman. After applying my makeup and brown wig, I dressed in a white blouse, light blue blazer and matching knee length skirt. The two inch heels rounded out the ensemble. A Dab of Christiam Dior and I was off to downtown St. Louis.
I found the CitiCorp building on Jefferson an attractive spot to stop. 20 stories high, there would be a number of people working and milling about. Just the place to start to blend in. Pulling up to the garage, I extended my perfectly manicured french tipped nails to push the ticket button to enter the garage. Upon receiving my ticket, the gate moved upward and I proceeded forward. The parking attendant extended me a tip of the cap and a "Thank you, Ma'am" as I entered. I found a spot on the third floor of the garage. and parked. Exiting the car, I made my way to the stairs to the lobby entrance. The clicking of my heels on the concrete would soon be followed by the same clicking on the marble floor of the lobby. I'm not sure why, but that was the sound I always loved to hear. It was something of a reassurance that I was supposed to be this person, a woman, living a normal woman life.
But that's not why I came here. I was going to be someone's fantasy in the next ten minutes. Spying the bank of elevators, I moved quickly towards them. Pressing the 'UP" button, I stood and waited. The doors opened and an empty car awaited me. Steppping in, the doors slid shut behind me. The car rose from floor to floor, picking people up and letting them off. Me...I was waiting for someone. I didn't know who or when, I just knew I would know' him when I saw him. Riding down from the 16th floor, I was partaking in some small talk with a couple of other women. A 30 something woman asked me where I got my nails done. After telling her the salon, she thanked me and the group of them exited the elevator. As the door was closing, a hand reached in and stopped the doors from closing. As the doors opened again to let the stranger in, I was now in the company of a incredibly good-looking man. Maybe 35-40, 6' and 200 lbs.
Even though I am a genetic man, standing there as a woman, I felt a weakness in my legs, my heart started to beat faster. This was the guy I was looking for. This was why I wanted to be a woman. No woman ever makes me feel like I did in this man's presence, if that makes any sense. A quick glance revealed no rings on his fingers....perfect!
"Glad I didn't miss the elevator" he said, as he looked me over. "You work in the building, or just visiting?"
"Just visiting." I said, giving him a sly look out of the corner of my eyes, not quite facing him.
"Didn't think I recognized you. I think I know pretty much everyone from the 4th floor up" he said.
This time I said nothing. Instead, I let an awkward silence come over us. As most people do, he just assumed that I wasn't interested in small talk and instead, turned and faced the closed elevator doors waiting for his floor to arrive. I knew I had to act quick, as you don't get a whole lot of alone time on an elevator. I again glanced over at him, giving him another little mischievious grin and batted my eyes.
"What??!" he said half laughing. "Why did you look at me like that" he asked.
I glanced over at the control panel, then looked back at him, smiling. He still looked at me with bewilderment. Reaching back to the control panel, I pushed the STOP button, bringing the car to a screeching halt that knocked us both a little off balance.
"What are you...." he started to say as I turned and faced him. I closed the small distance between us and threw my arms around his shoulders.
"Oh...hellllooooo" he said, maybe finally realizing what I had in mind. Running my fingers through the back of his hair, I pulled him closer to me. Our lips met and a shiver ran down my spine. After a quick touch he pulled away slightly, then came back to me. What started as a soft peck quickly became a forceful and passionate exchange. I opened my mouth to let him explore me with his tongue. Oh how I loved this feeling, but time is wasting. I slid my right hand down to his now awakening package. Unbuttoning his pants, and undoing his zipper, I got my hands on him.
"YOu don't waste any time" he said
"Shhhhhh" I said holding my index finger to my mouth. I looked him in the eye, and held that look as I decended down his chest to his erect manhood. A tiny glistening of precum had accumulated on the tip of his penis. With a quick lick, I got a taste of what was to come. His knees buckled a bit, but he regained his composure. I began to lick around his shaft while carressing his boys ever so gently. His head tilted back and his eyes closed. He was mine now.
I worked my tongue back to the head of his penis. MOre juices were flowing out the tip. Swirling my tongue around the tip I finally took the plunge and took him completely into my mouth. Again my victim buckled at the knees and leaned back against the wall of the elevator. With my free hands, I reached around him and grabbed his butt, all but encouraging him to fuck my face. He got the idea and slowly made thrusting motions, each time burying his cock down my throat a little further. This was heaven! Each time he would pull out from my throat, I would give him a little moan, pressing my tongue onto his cock, and in he would push again. His thrusting became more feverish and I knew I was getting him where I wanted.
"Cum in my mouth.... I want every drop" I said during a brief moment when he wasn't pounding my face.
"As you wish" he said. It took about 5 more thrusts and I felt his ass tighten up. With a low moan, he made one final thrust deep into the back of my mouth. Cum came shooting out and I let it fill my mouth. I wanted to savor the taste while keeping his shaft inside me. Swallowing a little at a time while continuing to tease the underside of his penis with my tongue, I slowly cleaned him all up, finally letting his cock leave my mouth. With a few final licks, I placed his beautiful, now limp, member back into his shorts. I placed his boxers back up, zipped him up and re-buttoned his pants. After pressing the RESUME button, I assumed my position next to him as we awaited for the lobby to arrive. Neither of us said a word.
The doors opened revealing the lobby, where I would exit. As I stepped out, I turned to my anonymous lover, still inside the car. I smiled and winked at him. He shot a smile back.
"Do I at least get to know your name?" he asked as the door was closing.
I shook my head no as the two steel doors came together. But for what it's worth, I like to go by Jennifer, I thought to myself. My reflection in the doors was one of satisfaction. But I had bigger fish to fry. I turned and made my way to the parking garage, with that familiar clicking of my heels. I was feeling more like a woman today than I had ever, but little did I know what was in store for me later. As they say, be careful what you wish for.
Part 2 of 5
Making my way back home, I drove down I-66. I always seemed to grab the attention of the occasional truck driver who could see into my tiny convertible. Perverts. But who am I to talk...I just blew a stranger in an elevator. But I guess I loved the attention they gave me anyway. Just another part of being a woman....getting the occasional unwanted attention. My plan was to go back home and change for a drive in the countryside. You can drive about 45 minutes outside St. Louis and come into some real nice countryside. I wanted to put the top down and let my hair blow in the wind, and this was the perfect day to do it.
Upon getting home, I decided to go for a more casual look. I had a pair of size 6 stretch jeans that really made my ass look great. Lucky me, I had a great female shape there. No padding was needed. I used a waist cincher to give me a more hourglass figure, and of course, a pair of detachable breasts, but otherwise it was all me. I could only imagine how good I would look if I ever decided to go the hormone route. In any event, I wore the stretch pants, a soft pink camisole and decided to go blonde. Unlike my brown wig, I loved the blonde. Very passable, almost real to me. It was almost waist long down my back and i was looking forward to feeling the hair blow all around me when I took the top down.
Leaving home again, I took off west towards Jefferson county. Highway 100 is a great place to put the top down and drive without the worry of too many people. I actually decided to go braless as well. The top I wore was tight around me, giving the hint of cleavage, but you could never tell what was underneath wasn't real. Having my shoulders all but exposed in the open was always a welcome feeling when dressed. Arriving outside the hustle and bustle of the city was welcome. I pulled over and pressed the button to lower the convertible top. As it recoiled above me, I felt the warmth of the sun on my face and shoulders. There was an occasional car passing by. but for the most part it was just me by myself. A little alone time as a woman. Picking up speed, the wind started to whip my blonde locks around. My hoop earrings also jostled about a little, but the wind wasn't so severe that I was distracted.
I started thinking about how I felt at that moment. How peaceful I was. I wondered how my family would react if I told them about how I felt. Would it be so bad? What about all my friends and co-workers? Would they accept that I wanted to be a woman? Could I transition without losing everything I had worked for? I know that I had a deep desire to be a parent. Not adoption, but a biological parent. With sex change, that wouldn't be possible. Oh, I could store some sperm and have it used invitro with another egg donor and then have that planted into some other woman to have a "biological child", but that's not what I was looking for. No...I wanted my experience of parenthood to be much more personal than that. And in this lifetime, that would only happen as a man.
The problem with daydreaming like that is you don't pay a whole lot of attention to the road. I should have been. With the wind and the sun, and feeling so feminine at that point, I almost didn't see the deer in the road ahead of me. As reality snapped back into me, I pulled the steering wheel hard left and slammed my foot on the brakes. Now sliding sideways, I felt the car come up off the roadway. I was going to flip. All I remember was just one little blip of time where I seemed to be airborne. No control, no power, no feeling...nothing. Then lights out.
I came to, laying in a grassy area. My first thought was not to move. I might have been seriously injured and didn't want to compound problems. Slowly I took inventory of my body. Wiggling my toes first....they are O.K. Now my legs....everything fine so far. Pushing my arms against the ground caused no pain either. Pushing myself off my stomach and rolling into a seated position, I was amazed that I wasn't seemingly injured at all. I pulled the blonde hair off my face and saw my car. Rolled onto its side, it was wedged up against a tree, the undercarriage facing me. Turning the other way, the road I was just on was some 50 yards away. This was bad. "Oh crap" I thought to myself. Clearing my head, I remebered that I always kept a change of male clothes in my trunk, should I ever need them. And boy was I gonna need them now. As I started to my feet a voice called out from an outcropping of rocks to my left.
"Need any help there....." it cackled and continued "....Jennifer!!!"
Hearing my female persona name called out like that stopped me in my tracks. Turning, I saw a man of 50 or 60, dressed smartly in a black tuxedo complete with top hat. Hardly the attire of a farmer or country boy. I didn't know who he was, but I knew I was busted. How was I going to get out of this.
Part 3 of 5
"I had a wreck" was all I could muster to say.
"Well now isn't THAT obvious" the man said, making his way off the outcropping of rocks he was perched on. "Do I call you Jennifer, or is Jenny allright?" he asked.
"Je...Jenny is fine.....how....how do you know my name?" I stammered.
"Well Jenny.....I meet a lot of people in this here area, but I've got to admit, you're a first for me." He said as he came up next to me. "But none-the-less, I think I can help you out if you would like me too. Would you like my help...Jenny"
"Sure." I answered. "Could you help me try to right my car back onto it's wheels. I don't know if it's driveable or not, but at least I could get into my trunk....I really need to get into my trunk."
He laughed. I know it wouldn't have been the easiest thing to do, But I really thought the two of us could push the car back onto it's wheels without too much of a problem. Yet he just laughed, almost in a sinister way.
"I don't think you understood what I was asking you, Jenny." He said. " I meant, can I help you with your problem."
I still didn't understand him. My problem was I was dressed as a woman, just flipped my car and would like to get into some other attire before someone else sees me. That was the only problem I understood at the time.
"I guess not....I'll just do it myself. Wouldn't want you to mess up your nice suit anyway" I said turning to make my way to my car.
"Oh....now Jenny, I don't think you be wanting to go over there to that car, you might not like what you find." the stranger said, in a slow southern drawl.
"Whatever" I said waving him off. I didn't need that old weirdo's help anyway. I could do this without him. How hard could it be anyway. I figured I could rock it back and forth a little to get it going. Then one good push to get it on its wheels...no problem.
Arriving at the car, I made my way around to the topside of the car that was facing away from me. One good push should do it I thought. That's when I noticed a body. Facing down, with the feet trapped up underneath the steering wheel. Blonde hair waving ever so gently in the breeze. Pink camisole and stretch jeans, and one dis-lodged breast form laying against the passenger door. Blood everywhere.
IT WAS ME!
"Told you, you didn't want to see that Jenny" the stranger said from right next to me, appearing as if out of nowhere.
"Wha...what's going on here?" I asked, now clearly frightened. "Who's that?....who am I?.. what's going on? And who ARE you?"
Again he laughed. His amusement of my situation was starting to really piss me off.
"Oh, I think you've heard of me, Jenny." He said as he smiled. A smile so wide I swear every one of his teeth showed. " You see, I been doing business on this stretch of highway for a number of years now, but I usually don't run across someone needing your kind of help. But to try to answer your questions...what's going on here is that you just rolled your car 13 times down this embankment. That person in the car is YOU. The person I am looking at and talking to is also, YOU. What's going on is....YOU DEAD, or so it would seem. And who am I?" he said finishing up," I'm the guy that can help you out of your little mess."
The dumbfounded look on my face must have been funny to him, because he just started laughing again.
"I'm dead." I muttered, almost asking rather than saying it.
"Well of course you are silly woman." He laughed. "NObody rolls their car thirteen times down this hill and lives. Geez, I think you hit your head on the pavement up there, those rocks over there, the steering wheel, the windshield...I'm surprised you even stayed in the car. I bet you brain is scrambled eggs in there. Suddenly he turned serious. "NOw listen to me again because I'm not going to say this again. I know you ain't no woman, but I know you have always wanted to be one. You were just thinking about it as you were driving down this here road. Now look at you." he pointed to my dead body in the car. "All dressed up just waiting for family and friends to find you. This will be how they all remember you...do you really want that? I'll tell you again, I can help you. And don't play me like you don't know who I am."
He was right. I was beginning to understand. The reality was setting in that I was, in fact, dead there in the car. I must have been in some sort of limbo state. Not sure of my next move, he continued talking.
"Now here's the deal....you want to be a woman, I can arrange that. I can right that car and put the both of you back onto that highway like nothing happened...not a scratch on you or the car. But I need an answer now....times a-wastin'. You see, in a little over two minutes, a pickup truck is going to come around that corner there, and the couple in the truck are going to see your car there and come to your aid. Of course, they'll be too late. Bottom line is, once they see your car, I'm powerless to help you. So, what's it going to be?"
He folded his arms and looked at me with a wicked grin. A million questions came to my mind. Did I want to make a "deal" with him? Or did I want my family to see me like this?
No, I couldn't make a deal...wouldn't make a deal. I knew who he was and wasn't going to sell my soul for a deal.
"No." I said, although not real convincingly. I had to admit, the thought was tantalizing.
"Oh...." he said unimpressed. "Let me show you what you might be missing."
He snapped a finger and suddenly I was there naked in front of him. Except I was no lomger a man. My feet had shrunk two sizes, my hips flaired out and my breasts....my breasts were real. I reached to touch them, not sure of what to expect. No longer something attached with adhesives, they were smooth...perky and firm. My large nipples standing out in the cool breeze. I pinched them and the feeling was electric, sending a shockwave through my now female body.
"You think that feels good, try this on for size." he said. With that, he snapped his finger again and I suddenly felt a rush of heat and a wetness between my legs. My manhood was gone, replaced by the soft folds and slit of my new vagina. I wasn't sure what he was doing to me, but it felt great. The burning was building ever more quickly in my body.
"Touch it" he all but commanded me.
I complied. Slowly feeling my way through the soft folds surrounded by my perfectly groomed blonde bush. One finger...then two. Using my thumb and middle finger, I parted my fleshy lips and inserted my index finger into my dripping love canal. The feeling was so intense, I had to drop to my knees I was so weak, but still I probed inward. I sent another finger into myself deeper this time. I found that bundle of nerves that sent my head spinning so bad I had to close my eyes. The shockwave from that sent me sprawling to the ground. On my back with my legs high in the air, I was jamming my fingers in and out furiously. I needed a release so badly, I was litterally screaming with anticipation. Suddenly it happened. With my hips bucking wildly, I pulled my fingers out. I screamed out as the burning in me turned into a tingling wave that rushed from my drenced pussy to my head and toes. Wave after wave it came. It seemed like there were 15 to 20 waves....each one diminishing a little until I was completely spent. Laying there in the grass, I was at once exhausted, content, happy and utterly unable to get up. Completely spent, I finally opened my eyes. Standing there was the tuxedo-clad man.
"You have one minute to decide."
Part 4 of 5
The questions came quickly.
"Will my friends and family know me?" I asked
"They will only know you as Jenny...they have always known you as Jenny. Only you retain any memory of your male self." he answered. "Everything about your first 26 years will be reflected as though you were always a woman. I will give you memories of your first kiss, your high school years, your first period, being on the cheerleading team. Everything. But you will also retain memories of your former male self just long enough to help you get used to your new body and self. The only memory I can't give you is your first time with a man. You are for all intents and purposes, a virgin."
"Am I really a woman...can I have kids....is this the body I get to keep?"
"Yes...yes...and yes" he answered. Again he snapped his fingers and a full length mirror appeared in front of me. "Do you like what you see?"
Staring back at me was the hottest blonde I had ever laid eyes on....and it was really me. I had explored myself earlier, but now seeing the entire package in front of me was incredible. My face had softened, my nose smaller, my lips full and pouty. My brows perfectly arched and much lighter in shade matching my now real flowing blonde hair. My waste had shrunk to a very tight and sexy 25 inches, my stomach firm and defined. My hips swelled out to 36 inches. And though I liked my ass as a man, Jenny's ass was to die for...round and soft, with a small butterfly tattoo on the small of my back. I wasn't just hot. I was smokin' hot.
Then it occurred to me. "What do you get out of this?" I asked, already knowing the answer.
He smiled that big smile again and looked me up and down.
"You know what? I like you and as I said, you're not my usual customer, so to speak. So here's the deal....I mentioned you are a virgin. No man has ever penetrated you. If you can keep that tight little pussy of yours under wraps for the next 30 days, not allowing any man inside you in any way, then your new body, your new life....it's all yours to live out happily ever after. You owe me nothing! Should any man get himself inside you before that....well, you know what I get out of this. But I actually have faith in you that you can do this, so I do ask one thing of you. No matter the outcome of the 30 days, you must spread the word of what I can do here. I see a whole new customer base here. And I think I am going to be seeing a lot of new faces, with your help of course. You're down to 8 seconds left...do we have a deal?"
I quickly thought to myself.....dead and shamed, or, 26 years old...a knockout blonde with my whole life ahead of me, still have my career, my car, my money, my family and friends... I just can't have sex with a man for 30 days.
"Deal" I said with 2 seconds to spare.
"Done" he replied.
Driving along I noticed a deer in the road. I stopped and the animal slowly crossed in front of my car, disappearing into a wooded section by the highway. A pickup truck behind me honked its horn. Suddenly I felt dazed, even a little confused. I pulled to the side of the road, feeling a little dizzy. The pickup pulled alongside and an elderly woman leaned out.
"You allright, sweetie?" she asked me.
"Yeah...I'm fine." I said back to her. Funny, I thought. I usually had to really try to speak in a feminine voice, but now it was naturally feminine.
"well, you be careful out here, there are a lot of deer running around here this time of year." She said as the couple drove off.
"Thank you." I called out after them. Still feeling a little dizzy, I put my head into my hands. Almost immediately, I realized that something was different. My face was smaller, my hands smaller. Grabbing the rear view mirror, I turned it to reveal my newly female face. That's when I realized the events of the last 5 minutes or so were real. Everything about my conversation with the stranger came flooding back to me, instantly. I actually grabbed and squeezed my tits to be certain they were real. Undoing my seatbelt, I slid my hand down my pants to find my soft love mound still there...real as ever.
It was true....I was now Jenny. But was everything else about my new life, that the stranger promised, real? The next 30 days were going to be real strange. I turned my car around and headed home. Upon arriving, I quickly locked my car and headed to my 3rd floor apartment. Opening the door, I realized this was for real. My apartment, once a drab bachelor pad of sorts, had transformed into quite the fashionable place. Lots of pastels and pinks, very bright and coordinated. Pictures of me....that is Jenny, with a number of friends, family and the sort. The kind of things my male self never would have around. Entering my bedroom, I opened my closets to reveal clothes....and lots of them. Every imagineable outfit, skirt, blouse, pants and camisoles, tube tops and shorts...sandles, and shoes....Oh my were there shoes everywhere.
Opening a dresser drawer revealed bras and panties of every color. Thongs and regular panties, strapless bras and matching sets. Another drawer contained a light blue teddy set and stockings galore. My bed, once a headboard and a mattress, was now a canopy style bed decked out with white satin sheets with a lace trim and a feather soft down comforter. Driving home, I couldn't wait to get my clothes off and look over my new body again. I kicked off my shoes and all but tore off my pants and pink camisole. Looking in the mirror on my dresser, there I was again. I couldn't believe how beautiful I was. Slowly, I slid my hands across my body again. Every- thing was real. It set in to me that I was now Jenny. I launced myself onto my bed, bouncing up slightly as I hit. I was giggling...giddy with anticipation of what my life was now going to be like. I was a girl.....finally....it was really happening to me. Periods, pregnancy, doing my hair, my nails, shopping... I couldn't wait. And sex. Sex with a man. If my episode with the stranger was any indication, well, I just couldn't wait.
Suddenly I thought to myself, Do I have a boyfriend? Of course I do....his name is Mark, he's 28, a mortgage lender with sandy blonde hair and piercing blue eyes who completely supports my decision to not have sex with him until I am sure he is the man I want to spend the rest of my life with.
Huh? Wow, the stranger was right. Suddenly I was remembering events of a life that I hadn't really lived, yet the memories of them were very vivid to me. So much so that I began to question which life was real. Knowing that the stranger had made all this happen, I decided that when these little events happened, I would err to the side of my Jennifer memory. I think it would just be easier that way.
Laying there naked on the bed, I rolled over to look at a picture of Mark and me. Smiling together cheek to cheek, he was every girls dream. I felt bad about making him wait to have me, but he was very supportive. It was a good thing he wasn't here right now I thought. In my altered, and somewhat horny state of mind, I might have jumped him right then and there. But then the words of the stranger came back to me. 30 Days this body is off limits to him. I can't take a chance. Jumping up off the bed, I grabbed a desktop calender and marked off 30 days.The 30th day I marked off was Thursday February 13, meaning on Friday February 14th, I was free to have Mark. Valentine's Day...how perfect was that? Until then, I would have to find other ways to please myself.
Part 5 of 5...Thursday Feb 13, to be comming soon....
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