If you have read my profile you would know that I am married with three kids, and no privacy.
That being said, I try to indulge in my favorite pastime of cross dressing whenever and wherever I can. I was working as a manager for a convenience store where I would have to get up early in the morning to open the store. It was a 24 hour store, so I just had to get there to send the graveyard person home and do paperwork.
One morning, I got up a little earlier than usual, and since the wife was working the night shift at the hospital, I decided to put on some stockings and panties under my slacks before I left for work. I grabbed my black stilettos from their hiding place and headed out the door. Once in my truck, I slid my loafers off, removed my trousers and put on my high heels. The commute to work was only fifteen minutes, so I basically had an hour to kill.
I loved the feeling of the stockings on my legs, and the heels on my feet made me fell super sexy while driving. I took the long way to the neighborhood where the store was located and parked in the back lot of ranch supply store that was close by and had a good view of the road.
I eased the seat back and started caressing my legs. I was about to reach for my swollen cock when I saw a police car crossing the road and head straight to where I was parked. He lit up his lights and headed my way. Panicked, I kicked off my heels and struggled to get my trousers back on. I managed to get them up finally but was not able to get my loafers on.
The cop got out of his car and headed towards my truck. I rolled down my window and I asked, "Is anything wrong, officer?"
"You are trespassing on private property, and well, this is where prostitutes do their business sometimes."
"Oh, I didn't realize that, I was just relaxing until I had to get to work right there at that store."
He turned to look at the store and then asked for my identification, which I handed to him. He headed to his cruiser, used his radio, turned off his lights and returned within five minutes.
"Your story checks out sir, please be careful where you hang out," and handed me my identification. That being done, he relaxed a bit and nervously asked, "What are you doing out here really?"
"Off the record?" I asked, and I started to feel a bit naughty.
"Yes", he replied.
I looked him over and decided that he was pretty good looking. I took a deep breath and said, "I don't have any privacy at home," as I slid my slacks down my legs, "and I really like the way panties and stockings feel..." I put my heels back on my feet. "...and these heels make me feel real sexy."
I could tell he liked what he saw, as he reached to touch my leg that was closest to him. I grabbed his hand and slid it across my leg. It felt wonderful, and the nervousness I had been feeling a short time ago was replaced by arousal. He took a deep breath and caressed my legs with both hands.
I looked down at his crotch and noticed a nice bulge. I pulled him closer so I could reach for his zipper, and he started to rub the outsides of my thighs and grabbing my ass. I unzipped his trousers and pulled out his cock, which was more than a handful. I started to tug on his meat and we kissed tentatively at first. I felt his tongue press between my lips and I started sucking on it gently.
I broke free from his grasping hands and slid down to my knees to take his cock into my mouth. I kissed the tip and slid my tongue down the underside. The head came back to my lips, which I parted to engulf his cock. I tried to deep throat him on the first try, but I was a little out of practice, so resigned myself to slow down and enjoy his dick in my mouth.
He placed his hands on the sides of my head and gently pulled me back and forth as he fucked my mouth. I could feel his cock getting bigger as he slid in and out of my mouth and down my throat, and my nostrils were filled with the smell of his sex. I want him to cum in my mouth, but I have not had a dick in my ass in so long. I pulled back and asked him if he would cum in my ass, and he said yes.
I stood up, turned around and yanked my panties down. I stuck two finger in my mouth to get them wet and lubed my asshole with my spit.
He pushed me down by the back of the neck and I raised my ass up instinctively. My elbows were resting on the seat of my truck as I braced myself for the invader which would be piercing my ass.
The head feels huge as it passed my sphincter and I grit my teeth. The rest of his cock slid in, and I felt his balls rest on mine. He pulled almost all the way out and slammed it back in to the hilt, his huge cock head stimulated my prostate every time it passed by and I started to moan. His rhythm increased as well as the ferocity of his thrusts, and he reached around to jack my dick.
I came almost immediately and let loose with a huge load and a low howl. He grunted several times and slammed his hard dick into my ass. I could felt every pulse of his cock as he dumped his load deep into my bowels. We were both spasming as he put all his weight on me for a final thrust, I turned my head to look at him and he gave me a deep kiss.
He placed his hands on my ass and eased his cock out of me. Already I felt empty but satisfied, and I purred as I pulled my panties up. I wrapped my hands behind his neck and pulled him close for a kiss.
We kissed and hugged like long time lovers, and as he started to put himself away, he asked if I had ever done that before. I told him that he was the only one to ever see me dressed, but it had been along time since I was with another man. He said he hadn't done it with another man for a long time as well. We told each other how much fun it was and that we should do it again sometime.
Not too soon, because it wouldn't be as good, we both agreed.
We continued to see each other off and on for about a year until his schedule changed.
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