Perverts 'R' Us

More Carlos, 1965

By Walter Howard ( M/m, mast, anal )

Author's note: All my stories are semi-biographical. They all happened to me in some way or the other. Names, dates and participants may or may not have changed. If you like my recollections, please respond to "Wahobac@email.com". Thank you

It was a week after my private birthday party with 17-year-old Carlos, and I knew I had to see him again, because, quite simply, I was lusting for his body. I knew that I wanted him to do two things for me. I wanted him to dress up like a girl and I wanted to fuck his ass.

I called him up and we talked. I thanked him again for the good time we had the week before and how much I enjoyed fucking his 8-year-old cousin, Emil. I also told him I wanted to take him to an adult movie house in San Francisco. He liked that idea, because he had never been to one because he thought that he was too young to get in. I assured him that he could get in with me if he dressed up like a girl and acted like my date. He stated that he didn't have any girl clothes.

We talked for awhile, and I said I would bring some with me if he would wear them. I hung up after agreeing to pick him up at 11 the next morning and headed for the local Salvation Army thrift store to see what I could pick up. 1965 was hippie time in the City, so I assumed almost anything would do.

I found a short leather skirt, a small bra, some cool red panties and a loose pull over tie-dyed top. I also scored a small leather hand bag and some patterned thigh high hose. I figured he could wear his own tennis shoes. Carlos already had fairly long hair, so I thought if he fit into what I had bought, put on some of his grandmother's lipstick and brushed his hair forward, he would be pretty cute.

I screwed my wife that night, fantasizing about Carlos and Emil. As usual, she just lay there, but I brought her to climax three times while I was ass-fucking in my mind. The next morning, I made a few sales calls, and then headed over to meet Carlos.

I opened my briefcase and showed him what I had bought. He stripped down to put them on. I asked him to put on the hose first. He looked real sexy in them and my cock was already beginning to stir with anticipation. The bra I bought fit loosely over his flat hairless chest. The red panties were a good fit and as I rubbed his cock through the cloth, it started to stiffen up and filled them up really well. He put on the skirt and the top, and there standing in front of me was this cute little girl who looked good enough to fuck.

Carlos was getting into the cross dressing and brushed his hair and put on some lipstick he had found. He put on his shoes and we left the house hand in hand. As we headed across the Bay Bridge, I told Carlos that we were going to one of my favorite theaters. It was located on Turk Street and had two screens. One showed gay movies and the other showed stag movies. I told him that there were a lot of couples that went there to watch the movies and that no one seemed to care if they were getting each other off. Last time I had been there by myself, I was able to jack off several times and had to turn away one old guy that wanted to help.

As usual, it was a bitch finding a parking place, but I found one only a block and a half away. I fed the meter and we walked arm in arm to the theater. I noticed several guys giving Carlos a look over. He noticed it too and started swinging his hips and getting into his girl thing.

The cashier didn't even glance up as I bought two tickets, as we went inside. It was very dark and it took awhile for our eyes to adjust. The theater wasn't very crowded and we found some seats near the back with no one around and settled in. The screen on the right was showing a truck driver type with his hand and arm up a young man's ass. The screen on the left was showing a blond lady wearing only panties, but she had them pulled really tight into her pussy and was pulling the tightly stretched cloth back and forth across her enlarged clit.

I put my right arm around Carlos and started stroking the inside of his leg with my left hand. Carlos spread his legs apart and moved a little forward in the seat. His eyes kept going from screen to screen as he was trying to take in everything going on. I slid my hand up and massaged his cock through the silky panties. He grinned and moved his hand over to my crotch. I told him to wait and just enjoy himself for awhile. I pulled his skirt up a bit and pulled his panties down to release his hard little prick.

I slowly jacked it as I pulled him closer. I put my other hand down inside his shirt and slipped it under his bra and started rubbing his nipple. On the right screen three guys were daisy-chaining and on the left, a naked busty chick was having her tits sucked by a guy and a gal. We watched and I stroked for awhile. Then I could tell by the way Carlos was breathing that he was about to shoot his wad, so I got down in my knees, put my head under his skirt and sucked him off.

I swallowed it all and sat back into my seat. I quickly glanced around, but no one seemed to notice or even care what we were doing. I smiled at Carlos as I unzipped and told him it was his turn. I didn't have any underwear on, so my 8 inches jumped out of my pants into his eager hand. I told him to take it slow while we enjoyed the movies. Watching Carlos, dressed as a girl, slowly beating me off while I was watching porno was really turning me on and I was ready to come sooner than I wanted too.

I told Carlos I was ready and he leaned over and took my cock into his lipsticked mouth. I came long and hard, but Carlos managed to get it all down. We both sat back in our seats kind of exhausted. Carlos laid his head on my shoulder and we just watched the screens for awhile.

In a few minutes we both had our hands around each other's cock again as our erections came back. I moved my hand under his cock and started playing with his asshole and massaging his balls. He was having a hard time concentrating on three things at once, so told him to leave my prick alone for awhile and just enjoy the movies. I continued to play with his ass, balls and penis and I was watching the right screen showing three guys jacking off watching another guy stuff a big dildo up a fifth kid's ass. Then they each took turns fucking him.

I pulled Carlos's panties off and wrapped them around his dick. I jacked him off into his panties. After Carlos had spent his wad into the panties, I put them to my mouth and sucked all his teen cum out of them. I French kissed Carlos and we pushed his jism back and forth before we both swallowed. I put his soiled panties into his purse. Carlos wanted my cock in hand again, but I told him I would rather go back to his place and wanted to leave before the traffic got too bad across the bridge.

Carlos realized he had no panties under his skirt and flashed his ass to a middle-aged guy coming into the theater as we were on our way out. I could see that he was really getting into this cross-dressing thing.

We got back to his place about 3:30. His grandma would be home about 5:30, so we had some more time to play. I told Carlos that after fucking his cousin in the ass that I really wanted to fuck him. Carlos told me that after watching Emil get fucked by my big cock, all he could think about was having my cock up his ass.

We each got out of our clothes except I asked him to keep on his thigh-highs. He looked sexier with them on. I took a tube of KY out of my briefcase and sat it on the bed. I wanted to start by eating out Carlos' ass like I had Emil's, so I had him bend over the side of the bed. I got down on my knees and started giving him a good, long rim job. In one of the times I came up for air, I asked Carlos if he had ever had anyone or anything up his ass before. He said he hadn't, so I was going to fuck a virgin ass. I told Carlos that he was in for a fantastic experience and a feeling he wouldn't believe.

I put some KY on my fingers and slid one easily into his wet anal passage. I then pushed the second one home. After a few minutes I had the first two fingers of each hand pumping and stretching his loosening rectum. I was good and hard again and mixed KY with the pre-cum in my cock and placed the head in the brown hole.

Carlos moaned as I slid in with one big push. Hot damn. I could feel my cock sliding past his prostate. I pumped for a few minutes. I pulled out and asked Carlos to lie on his back at the end of the bed because I wanted to see his cock. I held his legs apart and pushed my prick home again. His anal passage wasn't as small as Emil's, but it was tight and slick.

As I pumped, I could watch his semi-erect penis shooting out cum with every stroke I made past his gland. He had an amazed look on his face and I could tell he was getting a thrill out of his first asshole climax. I started to cum and plunged in my 8 inches as deep as I could. I came with wave after wave of spunk deep into his bowels.

I reluctantly pulled out and took his dripping cock into my mouth and licked him clean. I cleaned myself up and looked down at Carlos spread-eagled on the bed. Damn, he looked good.

I told Carlos I had to go, but that I wanted to see him and fuck him again. I asked him if I could give him some money to buy some sexy clothes for our next date. He agreed and I handed him $50. I told him I would call him next week.

As I drove home I went over what had happened during the past week. I had gone from a faithful married man to a male ass fucker/fuckee with a transvestite trainee. I knew that my life was going to change for the better. I had a new attitude and a new life ahead.

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