Chapter I
This is the story of me before Debra, I was a man's man, all my friends worshiped me and the women wanted me. I could pick any person in a bar and have them in bed with me, I lived the good life. I had a job selling and buying stock, and had quite a knack for spotting a good opportunity. Then I met Debra and my whole world changed, but I'm getting ahead of myself, here is the story of how Rob died, and Tiffany was born.
As I crept out of the bed of his latest "victim", quietly got dressed, and snuck out of the house to my car to head home, I noticed that lights were still on a few houses over, but thought nothing of it. None of my friends quiet understood how I was so good at charming women. There was nothing truly special about me, I was 23 years old, average height, standing at 6'1", not particularly built muscular wise, and was only slightly above average for endowment. However, I had a way of getting a woman to leave with me any time he tried. If my friends managed to convince me I would swing a couple women their way, making sure it was a sure thing first of course, but I always saved the best for myself.
One night my friends, Michael and Tim asked me to go out with them and help them get laid. I agreed, feeling the urge to bang a chick as well.
"C'mon Rob, hurry, we're gonna be late." Rushed Tim.
"Late for what? It's not like the girls are gonna expire." I laughed as I pulled on my shoes and grabbed the keys.
Tim and Michael were already waiting by the door ready to head out, eager to let me friend work my magic. As they rode up to the usual club, The Ruby, I immediately noticed that it would be "slim pickins" tonight. Tim and Michael didn't seem to notice a different because to them a girl was a girl, but with my expertise I only went for the best, and the best of these girls was only slightly more than average. We walked into the club and Tim and Michael immediately picked out "their" girls, one a blonde with a white sparkling dress with B cup breasts and shoulder length hair. I thought she lacked a real behind worth looking at, but it was for Michael so I didn't care much. The second girl was a redhead wearing a black strapless dress that came down to her mid-thigh, she had slightly larger breasts and a more impressive behind, but still below my standards. As I walked over to the blond, I learned her name was Kimberly, she like butterflies, and enjoyed horror movies. "What a catch..." I thought. I slowly directed her attention over to Michael, sure enough before long she was walking over to him. I did the same with Brittney, the brunette, and with even more ease, she was walking over to Tim.
Now that I was warmed up, it was my turn, I turned and slowly scanned the room, just out of the corner of my eye I saw her, the best of the best walking into the club. She wore a deep purple halter top dress with beige pantyhose, black stiletto heels, with long black slightly curly hair. She had perfect slightly smaller than D breasts, and a behind that you could bounce a dime off of. Her eyes however were a deep brown, with slighted eyes that almost drew me in on their own. This woman was truly to be one of the best I would ever bang, so I wanted to put considerable effort into this one. I walked over to her, feeling confident as usual.
"Hi, my name's Rob, let me buy you a drink."
The woman stared at me with reading eyes, it seemed as if she saw right through me, she could see everything I was and had done.
"Tell you what Rob, why don't we skip the pleasantries, we both know why you are here, and why I'm here. Wanna get outta here?"
I couldn't believe how easy this was, a little too easy, but who cared, what could possibly go wrong. So we headed out to her car. I left my car and keys with my friends tonight so they could get their dates home. I would just call a cab. We got her car, a very nice Corvette with every bell and whistle you could possibly imagine. I couldn't help but think, "Damn, this girl must have a wealthy family or have a great job." She lived only a couple miles outside town in a huge Victorian mansion, or at least it was a mansion by a normal person's standards. It seemed odd that a woman of such wealth would go to a club like The Ruby just for a quick bang but, I was not about pass it up. We entered into a huge entry way with twin spiral staircases with beautiful painting on the way of gorgeous women that I assumed were family. There were finely crafted tables at each side of the long, broad hallway that went back into the main part of the house. She took my hand and led me up the stairs; we proceeded down a long hallway with more beautiful woman side by side with handsome men. It was a wonder she was so beautiful, her entire family lineage was wrought with beautiful men and women. She then opened a door into a large room with antique furniture each probably worth more than everything I owned. "This is amazing."
The woman stopped near the bed and let me go, then looked at me with those eyes, "So Rob, before we get started I do have a kind of fetish, and I won't sleep with you unless you do as I wish, I will understand if you choose not to and leave however."
No way in hell was I going to pass with up, she was gorgeous, and no fetish short of painful things was going to keep me from this, so I agreed eagerly to whatever it was.
She lit up with excitement as I agreed and said, "Ok, wait here and undress, I'll be right back."
I had no idea what she was going to do or bring back, but I didn't hesitate and had all my clothes off only a second after the door closed. She entered in a short time holding what looked like a pair of pantyhose.
"If you would wear these for me, it would turn me on so much and make me so happy." She said holding out the white pantyhose.
I figured, what the hell, it's no big deal, I'm sure I had either thought of or done weirder things for sex before. So I slid them on, they were a little difficult as I had never put anything like them on before, they were very tight and very difficult to move or make comfortable, but it was for sex, no greater purpose in my mind. I could feel her watching me every inch of the way. As I finally pulled the waistband up and over my very erect penis, the whole room seemed to shift for a second. I felt a little light headed but nothing more, I figured was just from standing too quickly and passed it off. She then moved towards the bed, I followed like a love sick puppy. As we climbed in, she pulled off the robe she had changed into while she fetched the hose. She was wearing a black corset, the same beige stockings with garters and a matching black lace bra and pantie set. She was breathtakingly beautiful. She stopped me as I went to climb on top of her and start my work. She then moved to run my pantyhose clad legs; she rubbed every inch of then except for area covering my bursting erection. "Why won't she touch me where it matters, I'm gonna have to force my hand in a second if this doesn't go somewhere quick."
Just as I finished the thought I felt her hand moving up my leg slowly to my erection. When she finally touched every inch of the erection, I felt odd. As if out of nowhere I wasn't in the mood anymore, I just wanted to sit and let her keep caressing my legs, so I did. Within a few moments my, before bursting, erection slowly returned to its flaccid state. She asked me to spend the night with her, which I gladly accepted if it meant her rubbing my legs.
For another hour or so, she rubbed and caressed. Then she got up and walked to the door and left. It was ok, I was comfortable there in the bed, the sheets I noticed were exceptionally soft, and probably worth more than my car and the pillows seems to welcome my head to them. I couldn't figure out why but I felt very comfortable there in the bed, it was almost homey. I had strange dreams that night, my mind seemed to replay me sliding on the pantyhose and the woman, whose name I still had not discovered, rubbing and caressing them. I then woke suddenly; it felt damp between my legs. I reached under the covers and felt sticky goo, which only meant one thing, a wet dream. I felt so embarrassed; I had not had a wet dream since I was a teenager. I then realized it was daylight outside, I scrambled out of bed, wondering what time it was, I couldn't find a clock anywhere and my clothes seemed to have disappeared with my cell in the jean pocket. I looked down and noticed I was still wearing the pantyhose from the previous night, I laughed that I had actually fallen asleep in them and slowly pulled them off. When they were completely off, I felt strange, like I was more naked than usual. I didn't care though; I then wrapped the blanket over me and walked to the door. As it opened a smell of apples came rushing in, "I wonder if that smell was there before."
I walked out and wondered down the stairs that I had journeyed up last night and towards the wonderful smell. I found what was I assume the kitchen, big enough to be industrial. I looked and saw the woman standing near the counter cutting apples.
As she looked up she frowned, "Where are your pantyhose?" "My pantyhose? Well I suppose she did give them to me." "I took them off because I was going to change, but I can't seem to find my clothes." She looked almost disappointed, "I washed them and hung them in the closet in the room."
I felt so stupid that I didn't think to look there first before dragging the blanket around looking like a fool. I hurried back to the room, again feeling the homey sense, and found the closet at the far end of the room. I opened it to see a much larger inside that what I thought would be. There were hundreds of shoes and clothes, both male and female. I assumed from all her relatives that stayed here on holiday, or possibly the clothes of the maids and servers in the house. Whatever the case I found my shirt, pants and shoes. But I couldn't seem to find my underwear or socks anywhere. I then spotted a large dresser at the end of the closet, I opened the first drawer to see, neatly folded, bras. "Nope." I opened the second to find the same. I kept searching through every drawer, only to find nothing but panties, pantyhose and bras. So I, feeling a bit sheepish, I found a pair of white opaque pantyhose, thinking they could double as socks if nobody took a good look, and a pair of cotton boy cut panties. As I slid the panties on, my penis got caught on the back end of the waistband and tucked back. I chuckled at what had happened and looked down. "Oh look now I am a girl." I laughed to myself a little more, but decided not to worry about the tucked penis and just get going, so I slid the tights up, these were much easier, as they were thicker and less delicate. As soon as the waistband hit my hips I felt a tight squeeze. I figured since they were thicker, they would feel tighter, so I then put my pants, shirt and shoes on and headed for the room door.
I figured I would never see this strange woman again, so I would keep my little accident a secret and let her maids deal with it. I headed back to the kitchen to see the woman still chopping apples and bade her farewell and thanked her for washing my clothes and letting me stay the night.
She looked up and smiled, I again felt as if she was looking right through me, and said, "By midnights chime, thou shalt return to me as a child past her bed time."
"This woman is insane, girl? Bed time? What in the world was she talking about." Si smiled and waved, I then walked to the door and felt a tiny tinkling feeling in my crotch. "God I need to get home, these pantyhose and panties are itchy."