• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Katie's Journey

Katie's Journey

Prologue

I am groggy. I open my eyes and I do not know where I am. The room I am lying in is white. I am on a hospital bed, or gurney, and everything around me is white white. My body feels like it weighs a thousand pounds. I try to move, but I can't. Nothing is responding. Not my arms, not my hands, not my legs. I fear I am paralyzed. I try to speak, but there is something in my mouth, and as I gain consciousness I realize, with a start, that there is something in my throat. I must be intubated, I conclude. I start to panic. I must have been in a car accident. I try to make a noise, but the tube makes it impossible. Where is my wife. Where are my kids, I wonder. The overhead fluorescent lighting hurts my eyes, so I close them for a minute.

When I open my eyes again after a few minutes, I notice that a sheet has been draped right in front of me, effectively separating my head from the rest of my body, so I can not see the rest of me. I hear a noise repeating. A "whoosh, whoosh, whoosh"; over and over.

Time passes, and I slip in and out of consciousness. But each time I awaken, I feel a little less groggy.

I try to remember where I am - what happened. But my brain is fuzzy and the only thngs I remember a flashes. A woman screaming. I remember... I remember coming home from work. I remember stepping off my commuter train, into my parking lot late at night, and watching a van pull up to me. One of those vans without windows that painters and handymen use. And then... I vaguely remember the van pulling up, a beautiful woman opening the side panel door and... and then fuzz again.

I drift off to sleep. The gentle woosh woosh droning on around me as I begin to dream.

Chapter 1

I was born in 1972, in a small town in Italy. My parents came to America, in search of a better life, when I was just 5 years old. I remember little of my early years, but I know I was happy. I grew up in a normal house. With normal parents, no siblings and no immediate family anywhere near. I was always self-sufficient, so when my parents died in a tragic car accident when I was seventeen, despite the pain and fear and sadness I felt, I decided to petition the Court to allow me to take care of myself until my 18th birthday. The Court agreed to my request and, given that I was financially independent thanks to two large life insurance policies, I was able to simply resume my life.

I went to college a few months later, sold my house and everything I had, and put the money into accounts to live off of until I was able to graduate and get a job to support myself.

College was uneventful. Four years of studying, light partying, some dating and more studying. I had friends, a future as a lawyer, and despite missing my parents, I lived happily.

I first met Sara, my future wife, when I was 23 years old. We dated briefly, broke up and forgot about each other for five years, when suddenly we ran into each other on the streets of Manhattan once day, grabbed a drink, had some dinner, spent the next 8 months together and got married in a civil ceremony at City Hall in downtown New York City.

I was madly in love with Sara when we got married and that never changed. Sex was wonderful from the start. She is a beautiful, voluptuous woman. Irish heritage, black hair and green eyes, standing at 5'7", 120 lbs, nice C-cup boobs that she loved me to play with. And freckles. She drove me wild with passion and we couldn't get enough of each other.

The first few years were wonderful. We made love almost every night. We role played when we didn't feel like straight-old sex; used toys, and excited each other by talking about what we would do to each other. She was an addiction for me. Our marriage was great. We fought about stupid things, but always rallied when something important was afoot. I was going to live the rest of my life with Sara and our children, and finally, after a couple of years of trying, we were rewarded with a daughter. Life was beautiful.

But. And there is always a but in these stories. I had a secret. Well, not so much a secret as a fetish. A fetish I could not talk to her about. At least I didn't think so. I love pornography. Even though I was satisfied with my love life, I couldn't wait to get to my office each morning and load up some fetish porn. Big tits. Huge tits. Tits getting fucked. Facial videos. Anal. Especially first time anal videos. Cuckold videos. Gay cocksuckers. Trannies, lezzies, sissies, big cock videos, huge cock videos, first time videos, threesomes, foursomes, orgies... basically anything that would strike my fancy. Some days it was beautiful young girls giving head. Other days it was a gay guy sucking his first cock and getting his first cum bath. And so forth.

I never acted on the videos. Although sometimes I needed more, and I would start chats with women. We would flirt, talk about what we would do to each other, and I would jerk off (always intending to eat my cum afterwards but never doing it as the wish to eat cum would vanish, as soon as I came...). But I never actually met anyone, never actually touched anyone other than my wife. Because in my mind I felt that, although the harmless flirting and sexting with strangers was a slight violation of my marriage vows, anything further would be cheating and a betrayal. So, with that spurious reasoning, I continued to flirt and sext online, and then I would work out the sexual frustrations with my wife when I got home.

In retrospect, maybe I should have talked to my wife. But I couldn't. And, as I progressed, my fetish became darker; my fantasies - dirtier. I began to pretend to be gay, and to pick up men (online). We would talk, exchange pictures and fantasies and often masturbate together on-line. Although I never wanted to be with a man, I found myself describing submissive acts that I promised I would do to strange gay men.

And so, one day, I found myself taking to "Jack" on line. He was an alpha male. Bisexual, dominant and demanding. He described himself as 6'5" tall, 250 pounds and ripped. As I sat alone in my office, he ordered me to remove my clothes, and to play with my nipples. Twist them. Pinch them. Try to lick them. He ordered me to jerk off, and to eat my cum. He was sexy, clearly not a novice and, against my better judgment, I found myself listening to, and following every direction given to me by this on-line master. I was mezmerized. i enjoyed letting go, giving someone else the power to order me around, to make me cum. The fantasy was one of the hottest I'd ever had. I would do anything for him, and after a couple of hours of on-line playing, I said goodbye, telling him I hoped to see him again. But by the time I finished typing he was gone.

I cleaned up the left-over cum. As I wiped myself, I couldn't help but taste the cum on my lips. In my throat. I usually shied away from eating cum, but I was still turned on by my conversation with Jake and I slowly sucked on my fingers as they gathered the left-over splatters. After I cleaned up, erased my search history and put myself together I caught the train home. And then my life changed.

As I walked to the car a chill ran up my spine. It was later than usual, and I had called ahead to tell my wife that I'd be late, and not to worry. The lot was deserted and I was the only one there. I saw something move from the corner of my eye. That's when I first noticed the van. It was white, with the letters K&G Painters stenciled on the side. The van had no windows in the rear, and the front windows were tinted to give the passengers all the privacy they would need. I hurried, towards my car, unlocked the doors and, just as the van pulled up along-side me, I opened my car door.

I heard the high-pitched excuse me just as I sat down. I looked, and a beautiful young woman was exiting the van. "Sorry to bother you sir," she said. I looked at her carefully. Maybe 35 years old. About 5'2" tall, no more than 100 lbs and nice little boobs poking out from her shirt. The hard nipples and shape of the breasts gave me the impression that she was bra-less. She wore tight shorts, and flip-flops.

"We are lost. Can yo help us?" she asked. The roadways around were confusing, and directions were not a strange request.

"Sure," I smiled and replied. "Who's we?" I then asked.

"Oh, sorry. It's me and my friends." The side door to the van slid open, and three more girls were revealed. All about the same age. All beautiful.

"Hi," I smiled sheepishly.

The girls waved and smiled, and one from the rear seat asked "Can you take us to the highway?" I stepped forward smiling, looking at each of the girls, and mentally taking pictures of these girls, for use later, at home in my mind. The one who asked me for help was especially beautiful. Blonde hair, big big boobs, long legs and a smile to die for. I put my hands on the side of the van, intending to give directions, when suddenly I felt a pin prick in my neck. A mosquito? A wasp? My neck began to burn, and the world started to spin.

As I fell forward, one of the girls grabbed me and, the last thing I heard was a man's voice saying "Perfect. Good job, ladies. He'll do perfectly." And the world went black.

*****

Comments are wanted and welcome. Thank you.

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Katie's Journey

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 28 milliseconds