Gay Erotic Stories

My brother Danny and I had convinced our recently widowed father to begin to try gay sex. It had been almost a week since he had spent the night with an escort we had arranged for him, a great guy named Jason. Now dad had called and said he wanted another night with Jason but wanted to meet him and the two of us at a bar in our part of town. It would be his first visit to a gay bar.

The three of us got there a little early so we could be prepared for dad when he came. It is one of our favorite places, very hot, great eye candy and with sex in the air. Dad had been sort of vague about what he had done during the week, but had said he had been working on what this change in his lifestyle would mean. We discussed how we were worried that this was going to be tough thing for dad to do and we had to really gentle with him as we coxed him along into our gay world.

When we saw him come through the door, none of us could believe what we saw. Our almost fifty year old dad looked totally remade. His brown sort of bland hair was now a deep black with streaks of white. He had daimond studs in his ears, and was dressed in an open necked silk shirt and an incredible pair of denim and leather jeans, tight but not too tight, really hot, but still age appropriate.

"Dad, you are so great looking," was all I could manage to say. "What did you do?"

He began his tale with a wicked smile on his face as he started in the Scotch we had ordered for him. "You know me well enought that if I am going to do something I need to do it right. So I decided I wanted to find someone to help me do three things. I called around to some of my accountant friends [dad is an accouantant] who are gay and got the name of a place and person called Joe/Josephine. You can't just go there and they don't take new clients easily."

Danny interrupted, "Dad, Joe/Josephine is the most private and expensive stylist in the city. No one, No one, just calls them."

"Well, I did and told Joe/Josephine my story and what I wanted. I got an appointment and went down to the address. I really had no idea what to expect, but had been promised that all three things I wanted could be done.

"The door was opened by a young man named Lars, who had beautiful make-up on his face, deep red lipstick, and a blond mohawk with a pink bow in it. He took me in to the salon where Joe was working that day. Joe explained to me that some days he was Joe and some days he was Josephine, depending on how he felt that day. Lars was both his assistant and his lover and was sometimes Loretta. Since Joe was Joe today so Lars was Lars.

"Joe looked me over and decided I need to have black hair with white streaks with a whole new cut and style. He got to work on my hair. That was the first thing. The second was I wanted my ears pierced so I could wear a pair of Karen earings and he did that as well. While that was all going on, Lars did a manicure and a pedicure, first time for either of those for me. He really wanted me to allow some nair polish with a little color in it, but I choose just clear.

"The third thing I wanted was someone to take me to a clothing store for all new clothes. Joe had said on the phone that he would arrange a special showing in a private store, and he had done so. Lars was to go with me and help teach me how to dress like a middle aged gay man.

"The store was a couple of blocks away and we drove there. We went in an met Chester who was waiting for us. With my new hair and earings he had something to work with and between the two of them they picked out a whole new wardrobe for me, like the pants and shirt I have on now.

Danny interrupted, "Dad, those clothes cost a fortune. They are so hot."

"Yea, I did spend a lot of money that day. But, if I am going to do this, I am going to do it right." Anyway, when we left the store I asked Lars if I could take the clothes home before taking him back to Joe/Josephine. He said he would like that.

"We got to the house and went in and he loved the house, with all the old furnitue and things. Along the way we had talked about what you boys had done and about my one night with Jason. Lars was facinated that I had only had sex with one man and said he found me really hot and did I want to make it two men.

"By this time we were in the bedroom and he reached out and kissed me. It was strange to kiss a man who looked like a woman, but I was horney and when he reached down to feel my cock I knew I wanted it. Lars, undressed me in sort of slow erotic way, kissing each new part of me as the clothes came off. He then gently lowered me onto the bed and began to suck my cock. This time there had been no Scotch and I realized I was totally comfortable with this blow job.

"But I wanted him as well, and began to suck him. It just seemed so natural and so easy. He was very oral and kissed and sucked me all over my body and ate my ass before fucking me. It really didn't hurt and I did like it. Then I fucked him, and he said he was in heaven.

When we were done I suddenly thought of something, and asked him if he wanted to go through Karen's clothes and take anything he might like. He was so excited and found that he and Karen had so many things in common in their taste for dresses. He tried on a couple of her bras and then dressed for me in one of her favorites, a red silk dress with great cleavage and a split up the side. This man I had just had sex with looked stunning as a woman.

"When I gave him four dresses and some of her jewelry, and her panties and other underwear he was in heaven. He said the Josephine was going to be so jealous, and he, Loretta, was going to love that. Then I took him back to his place and let him out. We plan to get together next week sometime when I will take Loretta and Josephine out to dinner and then who knows what."

The three of us just sat there stunned. A week ago dad was a straight man who had never had sex with another man. Now he was a man who had done things that Danny not I, and probably Jason as well, had never done. And he was totally comfortable in his new life. He knew we were blown away and on his third drink he simply added, "Oh, and I am selling the house and am buying something in this part of town. I am not sure where yet, but since I have never seen your place I want to do that first so I am not too close and not too far away."

We must have talked for another hour and then he said that he really wanted to get on with his night with Jason. He was horney and needed some good sex. With that he and Jason left. As they got up and walked through the bar, now pretty crowed, you could see guys looking at him with eager longing. Danny and I just sat there. Dad was going to be a big hit in our world.