A Dad’s Fantasy

A Dad’s Fantasy
Prologue
Have you ever dreamt that your life was completely different? I know, foolish question. Who hasn’t? But I am not talking about being richer, wiser, and healthier or the other typical mundane things we have control over. I am talking about being a completely different person. That’s my fantasy. To be a different person, so much so that I physically dream I am different. I love that nighttime vision that I need to share it.
I am a 38 year old fat (330 lbs. or 150kg for the metric user readers) white guy. I stand 5’ 9” (175cm). I have short chestnut brown hair that is in a slow race off the top of my head so I no longer have a forehead but rather a “five” or “six” head. The color is only slightly softened by the sporadic appearance of wiry white, not grey, hairs. I have several chipped teeth that only make my small enamels smaller. Then to top it off I have short legs and a huge barrel chest and no ass to speak of or so I have been told. I am a mix-mash of body parts.
My best features are my expressive sea-foam green eyes that change to a cerulean blue when passionate or angry and my “bulge.” One of my gay friends and a wife of another constantly make comments of how they want to see the cause of my bulge. I don’t understand the curiosity. So I tell them, “It’s bigger than average, and smaller than porn star.” It’s nuts. (Ha, a pun). Sorry. The truth is I’m about 8” fully erect and rather thick. My girth is not baseball bat thick but I would probably compare the girth to that of a long fluorescent light bulb.
I didn’t always look like this. There was a time that I was well fit. That was 20 years ago. I still wasn’t six-pack ripped jock but I was half the weight, more hair and better looking smile. But even in my heyday, I still wasn’t happy with who I was.
I am a closet cross dresser. I have been since I was 6 or 7. I have been caught from time to time, but I would give it up for a long enough period of time that people just thought I went through a short phase. The truth is much deeper than being a transvestite, and no, I am not gay. I love to have my dick buried in a nice wet tight pussy. Bi-sexual isn’t it either. I think I’d say I’m a lesbian or a she-male trapped in an all man’s body.
I don’t know if I’d still want to keep my dick if I was given the opportunity to change. I love the feeling of sex. The pleasure of my penis being squeezed by a women’s vagina in the throes of orgasm is rapturous. The thing is that for as long as I have been cross dressing, I have fantasized of being a complete woman. I even found that my nipples are very sensitive, and I am more turned on by subtle foreplay techniques or a sexily dressed woman than an undressed one or a woman gratuitously grabbing my cock or rubbing her naked body parts in my face.
I remember dressing up in some of my mom’s sexy clothes and then lying in bed pretending to be a girl. There were times I would imagine being fucked by a man with a big cock, but those fantasies didn’t compare to the ones I had of being a girl with a girl. My orgasms were tremendous. I still have a hard time matching those feelings of ecstasy. Over time, my fantasies have become more of me being a functioning she-male with natural tits and a very feminine appearance, or of being a whole woman with a woman with a strap-on. Sometimes I imagine I’m all woman and being with a man or a she-male and having them fill all my orifices with hot cum. There have even been thoughts of becoming pregnant and giving birth.
I haven’t told anyone this until now. What wouldn’t I give to be a young 18 year old girl; to have a 5’4”-5’6” frame with long legs, a flat tummy and narrow waist, 34C-36D perky breasts, long silky hair, soft smooth creamy tanned skin that was blemish free, big bedroom eyes with long thick full lashes, soft kissable lips, a small button nose, and an elegant long neck, and to have a vagina, long thick dick or both? Alas, I am not, but that leads to me putting to type the following story. Some aspects are true: others are purely fictional. The people for the most part are real, just not their names.
Chapter 1: Getting caught again, this time it’s different.
There I was at home, alone. My daughter, Tasha (actually my step-daughter), my only family left, was out at a slumber party with some of her girlfriends from high school. I am the only child of deceased parents as was my wife. I say, “was my wife” because I am a widower.
Janet died when Tasha (my step-daughter) was 14. I willingly ended up with sole custody of Tasha because her biological father wanted nothing to do with her. The courts actually had to forcefully summon him regarding her care after her mom died. He actually said under oath that Tasha and her mom were the “biggest mistakes” in his life. That comment and the fact that he had not been in Tasha’s life since she was 7 helped the Judge decide to allow me sole guardianship. Tasha, to honor her mom, asked the judge to let her change her last name from her biological father’s to Janet’s. The Judge granted her request.
That was a little over 4 years ago.
Now being alone for the night, I decided to enjoy my secret fetish. So secret, my departed wife did not know of it. If she did, she never told me she knew and kept my secret for herself. On and off for the last 30 years of my life I have cross dressed. I love the feeling of silks, satins, nylon, and other smooth cool fabrics against my hairless skin. The only hair I allow is my chestnut brown, wavy locks cut to a long business length. The rest of my body is completely smooth. I used the excuse of being an avid swimmer but the truth was I wanted to enjoy the feeling of women’s clothes when I dressed.
I was able to keep my secret from my wife because I kept my stash of girly clothes at work. I own and operate a live stage theater and concert venue nightclub. I had a few overnight rooms installed for late night rehearsals and technical stage craft workers. That way they could work late nights and still get a full night’s sleep. Most of the technical workers work one show at a time for about 2-3 weeks while still holding down a full time job. Then they have to compete for stage space with directors, choreographers, actors, dancers, etc. They tend to work until the wee hours of the morning. So I allow them to use the overnight rooms that have full size beds to sleep if needed and the dressing room showers. The overnight rooms also help with the night club. Frequently a guest becomes intoxicated and they have no ride and refuse take a cab home leaving their car behind. I allow them to use the overnight rooms.
It is in these rooms on occasion, using a late night at work or at the stage as an excuse, I would spend the night fulfilling my urges. My clothing stash is easy to hide at the theater because we have our own costume storage and stock of accessories including: real and costume jewelry, wigs, shoes, boots, sandals, undergarments, purses, and much more.
Once my wife died, much of my favorite items were brought to the house and stored in my walking closet. Blouses, skirts, and dresses were stored in opaque garment bags while undergarments, nylons, wigs, make-up and other smaller items were locked in file cabinets. I had told Tasha, that I just kept copies of important work records as back-up there. As far as I knew, she never doubted me, and never snooped.
There I was stripped naked in my walk-in closet. I grabbed a pair of satin panties with a slightly gathered ass line. I slipped them up my smooth skin and felt a shiver of excitement. Quickly and expertly I tucked my penis and folded my sack up and back and snuggly pulled the panties all the way up. Next came the custom breast forms I made on my own.
I used my theater special effects make-up knowledge to create my very own breasts. First I made a positive mold of my own natural chest. Then I sculpted the size and shape breasts I wanted and looked best on me. Then I created a negative mold of the sculpture so I could create the breast forms. The breasts were made using actual silicone breast implants in cyberskin latex foam. The result was a pair of perfectly matched tits and painted to match my skin tone, that were reusable, and realistic in texture and movement.
I carefully glued the forms in place and smoothed out the seams so they were almost invisible. Then I pulled on a crimson corset top with black Victorian rose lace overlay. I had to put it on backward then cautiously maneuver it around and then stuffed my fake tits into the cups. The whale bones and they previously adjusted side ties helped pull what little of my beer gut I had into a more hourglass figure.
Next I pulled on a short satin skirt with a ruffled hem line. It was frilly, black and snug in the hips and my altered waist. I made sure that the attached garters for the corset were tucked properly into the skirt.