It all began three years ago, in October. I remember because my wife was visiting her sick mother for an extended period of time.
Feeling unusually alone and commonly horny I had too much time on my hands to consider the most satisfying ways to shoot jizz.
After many lonely nights of jerking off I reflected on the odd realization that many of my fantasies involved scenarios in which I found myself sucking cock. I'm not gay and I find men repulsive, but a meaty cock has always been a great fascination for me.
I always sneak a peek in the locker room - just to compare. Anyway, that's what I have always told myself. In the end, I concluded that I might like to try cock-sucking. Maybe. Of course, I knew no one I could approach to fulfill my emerging wish.
If I were a girl I would have no problem finding a big dick to lick. Even an ugly girl can get laid whenever she wants. But, as a guy I stood a snowballs chance in hell of asking some stud to let me blow him and having him agree.
Thinking that if I dressed like a woman I could have a taste of forbidden fruit, I tried on my wife's clothes. They fit fine and my butt and legs looked great. In fact, from the waist down and behind, I looked like a knockout. But my too broad shoulders, large hands, and rough face were ghastly.
Sadly, there was just no way I could make my more masculine features look feminine.
So I turned my focus toward other ways to find someone who would let me service his schlong. Sadly, I couldn't think of a single plan that would work.
Resigned to a life without ever tasting a "man banana" I put the idea on a shelf and decided I would go out and see if I could pick up a cutie of the female variety for a one-night stand.
It would be Halloween in a couple of weeks and I could be completely anonymous. I searched online for costume ideas when the solution to my problem hit me all at once. It was so simple!
I pieced together a woman's costume that would cover my manly attributes. What I ended up with was a disguise in which I was a man - dressed as a woman - dressed like a football player. I was pretty pleased with my own ingenuity.
On Halloween, I shaved my legs and face really close. Then I put on my wife's panties, jeans, socks, bra, and halter-top. I had to buy shoes. I choose flat tennis shoes because at 5' 7" I was an average sized man but a tall "woman" and flats seemed best.
Next, I put on football shoulder pads and a powder puff jersey with the pink numbers "52." Lastly, I wore one of those full-face rubber Halloween masks with an attached blonde wig, a football helmet minus the faceplate and women's opera gloves.
Looking in the mirror I definitely looked like a girl. Tim had become Tammy.
The secret was in the details. For example, when some unsuspecting man saw me instead of seeing a wig he saw beautiful curls emerging from beneath a helmet. Men who dressed like women on Halloween wore skirts, but not me; I had panty lines. It was a more subtle and more deceptive subterfuge.
There could be no doubt I was a girl dressed like a football player. I wouldn't win any contests for best costume but I could get into a bar and easily pass as female.
Later, as I entered the bar I ran into an unanticipated obstacle; the Bouncer wanted to see my I.D. I suddenly realized I had a man's I.D. and a man's voice. I really hadn't thought this through.
The fear of getting caught petrified me. "Maybe I should just go home." I thought. As I fumbled through my purse to buy some time the line behind me started to get long and the bouncer just waved me in.
Once in the bar I sat on a stool and with a shaky hand pointed to a picture on the coaster of a strawberry daiquiri to place my order.
It was a little hard sitting comfortably with my dick stuffed between my legs and I squirmed a bit. Needing to stand, despite my wobbly legs, I walked over to the brass rail by the dance floor to watch the action.
I was feeling edgy but glad that I was so "passable". I was also really confident that my butt looked better than the oversized tushes of most of the women in the bar.
I guess I wasn't the only one to think my ass looked great because it was only a moment before a man in a surgeons costume offered to buy me a drink. I nodded my head and watched him walk over to the bar to buy me my first ever gifted drink.
Now I started to feel the feelings, and think the thoughts that women must, at times like this.
I looked at the guy who was buying me a drink (surely with the expectation of something in return) and I began to wonder what he was like. What did he do for a living? Was he rich? What was his cock like?
All I knew was that he was tall and broad, with a firm butt and a rugged face. Wow, I couldn't believe I was evaluating a guys looks. Even though I questioned if I wanted his cock, or any cock for that matter, I suspected that I didn't want a cock that belonged to a fat ugly man.
Anyway, he looked all right. The one thing I was sure of was that he would give me his cock without a second thought.
When he came back I was nervous and giddy, like a schoolgirl. Was I really going to do this? Would I really let him put his cock in my mouth?
Meanwhile, I couldn't talk or I would give myself away. But John (that was his name) never seemed to notice. He was so cocky that he did all the talking.
It was real easy to figure out in what ways he was successful, in what ways he was a jerk, what made him cool, and what his flaws were. I had a new perspective as a female.
His hands were all over me and he was standing so close I would have socked him if I had been dressed in my everyday clothes. I was really feeling felt up, when I decided to go with it and react as a slut would.
As soon as I leaned in and put my hands on his arms, it was like I had turned on a green light. If I thought I was being groped before - I was wrong. His hands were on the sides of my (fake) breasts and his fingers were in the crack of my ass. If we weren't in public he would surely have discovered I had a dick too.
