Cross Dress Awakening For She-Cock: Part 1

by Dave (Hamilton, NJ)

I woke up Friday morning so horny I had to jump in a cold shower. Last night I promised myself that tomorrow I would go get my ass fucked by a shemale.

So I proceeded to act on my plan...but plans change, things happen, people just pop up in your life and how one reacts to all this is what can make everything magical or miserable.
I’m Dave, 50, 5’9” 150#. Long blond hair, blue eyes. Nice athletic body- I’ve always been skinny. I’ve been wearing girly panties and stockings with consistent frequency for about a year now. I love jerking off looking like a sissy cock sucking girl.

When I was 15-18 I had very frequent sex with my neighbor Steve. We progressed from watching each other jerk off to me wearing panties and him cumming in my ass. He loved sucking my cock in panties. (PLEASE read my story “First Time In A Long Time” on this site)

So I removed every hair from my body, this sways makes me super horny and this morning was no different . I proceeded to toy my ass with my large plug and edged myself right to the brink. I lapped up my pre-cum. Then I jumped in the shower.

I woke up Friday morning so horny I had to jump in a cold shower.Last night I promised myself that tomorrow I get my ass fucked by a shemale.

So I proceeded to act on my plan...but plans change, things happen, people just pop up in your life and how one reacts to all this is what can make everything magical or miserable.

I’m Dave, 50, 5’9” 150#. Long blond hair, blue eyes. Nice athletic body- I’ve always been skinny. I’ve been wearing girly panties and stockings with consistent frequency for about a year now. I love jerking off looking like a sissy cock sucking girl. When I was 15-18 I had very frequent sex with my neighbor Steve. We progressed from watching each other jerk off to me wearing panties and him cumming in my ass. He loved sucking my cock in panties. We’d cum kiss and...(PLEASE read my story “First Time In A Long Time On this site)

So I removed every hair from my body, this always makes me super horny and this morning was no different. After douching my ass, I proceeded to toy my ass with my large plug and edged myself right to the brink. I lapped up my pre-cum. Then I jumped in the shower. I got dressed in black stockings, black boi shorts& a silky white top that made my nipples really hard. Standing in front of the mirror admiring myself and rubbing my nipples, my dick got so hard. I edged myself again with a vibrator in my ass. Stopping abruptly.

Then I threw on tight jeans and a white Oxford shirt. I jumped in my car and headed over to this convenience store on the other side of town . I walked out with pineapple juice and one of those really long (12”) spiral rainbow lollipops. I got back in my car, took off my pants and toyed my ass with the lollipop for 5 minutes. I was very covert. I almost got busted-or maybe I did, I didn’t care. I was on a mission for she-cock.

In another town about 30 miles away is an alternative bar that opens at noon and I was going there. While on the way, a really cute guy in a nice convertible pulled up next to me on my left at a stop light. I saw him looking at me while I put on a little show sucking the candy. I turned my head quickly, catching him watching. He smiled and winked at me. Then he pulled out as the light turned. Two lights later he’s stopped on my right side this time. He looks over to see me with my stocking covered leg up on the dashboard and me pulling up my hose.. my window was down so I heard him say :”Holy shit, nice legs.” I look over and say : “Thanks, you should see what else I’m wearing.” “Sounds good!” He says.
So I follow him off the Main Street and into a empty strip mall parking lot. We park door to door and chat for a minute.

“Wow, you’re brave. Those are some nice legs.”

I open the door and put one foot out, revealing my sissy self to him. He commented on how nice I looked and that made me turn and put both feet on the blacktop, spreading my legs apart so he could see my crotch & tucked cock.. “Wow, now that’s HOT !”

He says. He opens his door and pulls out his dick thru his unbuckled suit pants. I tell him I like his dick too. Then he says how his boyfriend would be pissed if found out I stoped to talk to a guy in pantyhose. I didn’t care, I just said “Who’s gonna tell him?” He said he : “ couldn’t, they’re in a committed relationship now for two weeks. But “you’re so fucking hot and I want to suck you dick. Would it be okay if you watch me jerk off. That’s not cheating, right.”

So I spread my legs and take my cock out for him to see. TheI stand up between our cars and dance a little for him. He’s stroking it hard now. Then I turn around and bend over so he can see my tight round ass in these black boy short pantys. I grabbed my lollipop and started toying my ass. Then I push my dick between my legs behind me and stand 6”From his face. I felt his tongue and lips on my dick head, then he starts moaning and pulls away. He had cummed into his hand. I was so tempted to bend over & lick it up but I said to him:

“Go ahead, You lick it up. I dare you ,” so he did.

He said thanks a lot, this was really kinky and awesome but I gotta go. Then he zoomed out. Leaving me standing there in broad daylight. With my lollipop in my ass. I felt used and abused-perfect! The fact that this random guy just jerked off to me made me so horny, & confident. I sat back in my car and toyed my ass again, edging myself. Then I continued on my way to my next awakening. This moment is significant for me . On so many levels. I felt that I could be anything I wanted to. A straight guy , bi, a sissy faggot, a total cross dressing sissy slut, anything !

I drove around a bit as I had time to kill. I pulled into a gas station and while the guy was filling me up, I put my pants and shirt back on. Did he notice??? Again, I didn’t really care.

Part 2 to follow