Naughty Crossdressing Boytoy

Growing up in the San Fernando Valley was a challenge and a thrill. Any kind of trouble you wanted to get into, you could. It was also a place you would either thrive, or not. You would be able to experience many different things.

Another hot Saturday in the Valley and I didn't have much to do, but felt my young 19 year old hormones raging and needing some relief. I was tired of masturbating, and although i was really cute, way too shy to pick up girls and being bi-sexual, I was very picky on what kind of guys I liked. VERY.. I decided to go for a walk in an area known for cruising just to see who was around, and see if maybe. I also had a pantyhose fetish, and many times, wore them, and got into cross-dressing. I had also experimented 2 guys once, but then met someone I liked. Louie, was a much older man, average build, and had a huge cock. I met him at a bus stop. We made friends...and how we got to the point we were...another story. In the days before cell phones, you had to call someone's house, page them, or knock on the door. My walk was nice, but no luck.

I couldn't help but think about Lou and his huge cock, so I made my way over to his house. It was far, and quite the walk, but, I was horny, and couldn't stop thinking about Lou. I tried to call 2 times on my walk, but he didn't answer. I was going to go no matter what, but just in case he wasn't well or away, I tried to call. As I walked down his quiet street in North Hollywood, I saw his car was in the driveway. I was really excited...and I mean REALLY. I knocked but could hear music from the radio I went to the side and yelled over the fence. He was sunning himself in only shorts.

He was happy to see me as always and grabbed my crotch and smiled as I came in to the yard..

Louie and I sat on the couch as usual watching typical late 80's TV. It was a typically hot afternoon in the Valley. The window air conditioner in the apartment kept the living room cool enough, and the drapes in the bedroom stayed shut to keep it cool.

I didn't fool around with any other guys. I was always a little shy when I came over to see him, but he put me at ease every time before we fooled around.

I could see Louie was getting a little restless, and he was finishing his beer. He leaned closer to me and put his hand on me knee, slowly caressing it. He let out his signature deep "mmmm" as he stared down at my bulge hiding behind my shorts. I wasn't hard but I could tell he was getting more and more worked up.

I flirtily asked him, "what's the matter?" with a coy smile and teasingly reached over and touched his crotch through his jeans. He worked his hand up my leg to my cock and started to caress it over my shorts. I made circular movements with my palm over his dick at the same time.

"You want this?" I teasingly said quietly to him. He let out another deep moan and whispered "yeahhh" and my dick started to get hard from his touch.

I stood up and put my finger over his lips and said "then let's go shower."

Louie's drinking made it hard for him to get a hardon and a while to cum, but I knew also what to do and say to really get him going..

We got in the shower and washed each other. My cock was getting harder as he stroked it and moaned. Even soft, his dick was really thick and long. It really turned me on a lot too.

I soaped up my dick and began jacking off as he did the same thing. He held the base of his cock and squeezed it to get it hard and did the same..

"Let's go finish this in bed," I said to him as I teasingly jerked him off a few strokes. Louie always made me feel very feminine. I was petite and relatively hairless, and with him, I was a girl.

He had already laid out the skirt, heels, pantyhose I was going to wear and a wig. I was getting more aroused seeing that, and he sat on the bed, and began stoking his cock, moaning and staring lustfully. The sight of him, his big dick, even half hard, and getting dressed up for him really had me hard and more excited to get in bed with him.

I sensually put the pantyhose on and ribbed his dick with my nyloned foot. I put on my skirt, wig and lipstick.

I loved the feel of pantyhose on my legs and against my dick, but also loved the feel the nylons on his cock. I started by giving him a foot job and felt his dick harden more. I could feel his dick getting harder and bigger. I was even more turned on and less and less inhibited. I knew also just what to say to get his dick really hard, even if it was a short time.

We had one rule..no anal sex. He could finger my asshole, but no cock in there. Besides, he would have split me in half. I made sure I made up for it by sucking his dick and balls really well and the way he liked it. He put me on my back and grabbed my ankles, spread my legs and grinded on my sheer pantyhosed crotch like he was fucking me good, and the closer his fat cock was to my ass, the harder he got.

He moved up and shoved his dick in my mouth while reaching back and rubbing my legs and my dick.

My cock was throbbing and I was so excited. I hungrily sucked his dick and balls and stroking his shaft. His dick barely fit in my mouth and the slurping sounds I made made him start gyrating as I sucked back and forth, massaged his balls and stroked him. My pantyhose were soaked in my precum and his scent kept getting me more and more excited.

He flipped me over on my stomach and lifted my hips up and closed my legs and started fucking my inner thighs. He kept moaning "yeah girl... I love fucking your little man-pussy" imagining he was in my ass. I turned my head back and said "you wanna fuck my ass don't you?"

His dick became as hard as a log. He ripped my pantyhose from behind. I knew his cock wouldn't fit, but I wanted him to have a taste of what he imagined fucking me there would be.

I turned my head back to him and said "fuck me Louie, fuck my tight little ass baby!! I'm your bitch, fuck me!!!" He then thrust back and forth with his massive cock between my ass cheeks fast, as we both moaned and then he let out a "ahhhhhh!" and I felt him shudder and a hot stream of cum hit all the way to the back of my neck, and realized he was cumming hard..and lots! And it was only a few strokes. Two pump hump and dump.

I flipped over on my back and threw my legs on his shoulders as he pumped the rest of the cum out of him, and flipped another hole in my pantyhose so my cum would shoot out too. The sight of his massive dick, the feel of the pantyhose and like a I was hot slut, I shot my cum and hard! As I was cumming and we moaned together, he rubbed his cock in my cum on my stomach and pantyhose and shoved it in my mouth. I had another shuddering orgasm as I sucked my cum off his dick and the rest of his load out his.

We collapsed next to each other covered in sweat and cum...and drifted off...

Louie and I met up a few times a month for 3 years. Stay tuned for more of those stories.

I eventually moved away, and we lost contact. I never had sex with another guy since, and actually have been with some really hot ladies who indulge my fetish of pantyhose. I still do, once in a while, think about those encounters and relieve them in my head, and with my hand.