Gay Skirt Stories

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Taking the Neighbor Ch. 09

by jjdtx on Apr 30, 2018
Gay Male

Allen came downstairs from taking his shower, he was naked and reached for his shorts. "Wait," I said, "You won't be wearing those." I beckoned him over to me, I placed a cock ring around his cock and balls, snapped it into place. "I love these!" He said, as I stroked his hard cock. I then handed him a t-shirt, plain, black, with no logos or emblems. He...

After School Fun

by Michele G on Sep 14, 2017
Gay Male

It was my Senior year in high school when I finally succumbed to the urge that I had only fantasized when I masturbated. Billy and I were both 18 and he was going to go to college out of town, so it was now or never. Since my parents wouldn't be home all day, I invited Billy over to my house to do homework together. I wore my short green plaid skirt. The h...

Turning the Teacher Ch. 03

by Dave933 on Aug 18, 2017
Gay Male

Finally, we had everything I had been looking for, and 'Charlotte' and I loaded back into the car, and I drove us back to the home she owned as Charles Wild. It was mid-afternoon. "Okay Charlotte, I think you should wear one of your sexy new outfits this afternoon, but I'll let you pick. Tennis girl or Hawaiian beach babe?" "Um - I think tennis girl," she...

Co-worker's Man Ch. 22

by rmdexter on Sep 14, 2017
Gay Male

I hurried back into my building and rode the elevator up to our floor. As I returned to my desk I noticed it was only a couple of minutes past my lunch hour so nobody would have taken any notice. I realized that I was starving for some real food as the only thing I'd had to eat since breakfast was a few loads of cum washed down with some of Mr. Wolfe's piss....

Could I Spank Another Guy?

by JRob on Aug 18, 2017
Gay Male

It was a depressing time, as my wife Anna was going through hell at work and brought it home each and every night. We needed her income, she made due with the work problems, but they carried over to the bedroom. We hardly ever made love, once every three months at best. It was depressing. Oh, there was Mr. Hand, and he did a nice job when I needed him t...

The Pictures Ch. 04

by Mike Cindy on Aug 17, 2017
Gay Male

I had a slightly lesser chance of being arrested dressed in female clothing than I did leaving the hotel completely naked. I remove the clothes and started getting dressed. Black garter belt and black fish net stockings. Black bra that had padding in it. As I was pulling up the black mini skirt, Mr. R said "stop, take it off." I let the skirt drop to the fl...

Michael in the Mirror

by cmike on Aug 18, 2017
Gay Male

As James approached the front door he reached absently for the keys in his back jeans pocket, striding up the steps to the door. Without thinking he reached for the door handle, and to his surprise it opened without any need for the key. He paused momentarily. Strange. Even if Michael was at home it was unlikely that he would have left it unlocked. James cu...

My Gay Crossdressing Vacation Ch. 04

by Flame666 on May 11, 2020
Gay Male

I slowly opened my eyes, remembering what had just happened over the past 24 hours, I woke up looked at the time, it was just before 7 pm. Earlier I had decided to start getting ready for my date with Paul and John around 7:30 so I got out of bed to get started. I was going to start with a shower and because I had a bit of extra time decided to take off my b...

Family Offerings Ch. 03

by walterio on May 23, 2018
Gay Male

START OF ANOTHER WEEK On Tuesday morning after Martha left for work Aaron arrived at the house. Now that he had fucked Martha, he would have to figure out have to balance his time between mother and son. He took of his clothes and left them in the family room before heading to Chris' bedroom. Aaron got in bed and slipped under the covers. He felt the slen...

Truckstop Young Wife Neighbor

by Alluring_Crimson_Shifter on Jun 12, 2019
Gay Male

Wendy lived with her husband in a middle class neighborhood. It was a comfortable neighborhood with a convenience store within walking distance. There was a retail strip nearby with hair salon, a barber shop, parts store, and a book store with an arcade. Also there was a truck stop next to the neighborhood across a wooded area. On this sun shiny day Wendy w...