On July first I returned home from our health club. Ann was packing my suitcase for a mini vacation at a bayside resort. My suitcase was filled with all my girlie things: lubes, vibes, wrist and ankle restraints and the paddle she used on me when I was bad. She also said Ben, his brother Josh, and two others were joining us.
Before continuing, I should mention how I became the man I am and how Ann took charge of me.
My wife Ann and I met in college and had been married for twenty-five happy years. She was still very beautiful and could easily catch the eye of men and women.
Ann was in charge of me sexually, although it was not always the case. We started out like any other couple, sex every day and many times on weekends. She had many lovers before me and every time she had spoken of them I always ended up with a raging hard on.
Several years ago I suggested she dominate me the entire weekend. I said I wanted us to role play with her the Dom and me her Sub. I even offered we pretend her prior lovers were fucking her.
Ann was thrilled with the idea. She said my desires were very much in tune with hers.
To say she liked the role reversal would be a gross understatement. Ann loved telling me what to do. She would describe in detail what her lovers were doing to her. How big their cocks were and how she enjoyed fucking them. She would make me eat her pussy or use a vibrator for hours, bringing her to multiple orgasms while not allowing me to cum or even touch myself. Sometimes she would not let me cum for several days; all the while I would be servicing her every sexual need.
Then one weekend she said she wanted to introduce other men into our sexual games. She said a guy at our health club had been flirting with her for weeks. She also said she had drinks with him and they engaged in heavy petting in his car but didn’t have intercourse.
I was shocked yet excited as I realized I had an erection listening to her tell me all about Benjamin. He was younger than her, she explained, over 6 feet, great looking, a real hard body and a thick 8 inch cock.
She told me he was coming over for the evening. She told him that I would be home and it was okay with me if they had sex while I watched. That weekend I became a cuckold husband.
That wonderful weekend was over a year ago. Every day since, Ann had been getting bolder in her dominating role. She not only fucked other men as I watched but she also made me participate.
She said she loved to humiliate me by making me do nasty sexual things. She had me hold her lover's cocks as they inserted them in her mouth, cunt or bottom. She had me clean their cocks and her cunt after they finished fucking. She had me dress up in girlie clothes and wait on them serving drinks and food. She even told her lovers to fuck my ass or mouth and to make sure I swallowed every drop.
She said my humiliation has heightened her orgasms. She also said by her forcing me to do these things she has come to love me even more than before.
What Ann didn't know was, I secretly loved how she humiliated me. I loved dressing up in girlie things, I loved cleaning up her lover's cocks, I loved eating cum out of her well fucked cunt and bringing her to orgasm. I especially loved getting fucked in my ass and sucking their cocks until they exploded in my mouth or all over my face. Yes, it humiliated me but it also made my cock so hard it hurt. When she finally let me cum I nearly passed out from those intense orgasms.
Well, on July third we checked in to our hotel. Ann opted for a suite having a separate bedroom with bath, a kitchenette and living room area with a bath. We found that Ben and Josh were staying in the room right next to ours. However, Ann’s other two friends, Ben explained, bailed out on the fun.
After unpacking, we put on our swimsuits and headed to the pool to cool off and relax before the games began.
Ann, Ben and Josh paid almost no attention to me as they played in the pool or flirted with each other at pool side. My job, I was told, was to make sure they always had fresh drinks.
There were three young people waiting on the guests, two really cute twenty-something girls and also a gorgeous black guy. He stood 6 feet tall and was quite slim. His head was completely shaved like many athletes his age.
I was very attracted to him and every chance I got I flirted with him. I asked him when he got off work and he said 4 pm.
“Any chance of stopping by for a drink and…" I said.
He smiled and said, “Do I get to fuck your lady and you?”
“Anything you want,” was my answer.
At one o’clock the four of us left the pool to shower and change. Ann showered first and then I had my turn. I was ordered to make sure all my body hair was removed from my legs, arms, chest, crotch and ass. I had always kept my body hair to an absolute minimum anyway. Ann had her Epilady hair removal device on the counter for me to use plus my shave cream and razor.
When I came out of the bathroom clean and hairless, I saw Ann had laid out an outfit for me to wear. It was bra, panties and garter belt, all in pretty red. She applied my makeup and my blond wig. While I couldn’t really pass for a woman, I did look pretty good for a sissy girl.
Ann was dressed in a black see through teddy and crotchless black panties. She looked amazing!
There was a knock on the door and I was told to answer it just the way I was. I opened the door and to my relief it was Ben and Josh.
Both men smiled and Ben said, “Wow our sissy girl is all made up. Are you ready to service us, Tim?"
My answer was to invite them in and then drop to my knees in front of them. I began with Ben and removed his belt, then I unbuttoned his shorts and pulled down his zipper. I reached in and felt his cock through his boxers. I pulled down his shorts then his boxers to reveal his massive manhood. I stroked it several times then bent forward and kissed the tip of his growing cock.
Ann was busy undressing Josh but ordered me to finish the job. I turned and saw he was down to his boxers. His cock was sticking out the waistband reaching to his naval. I kissed the underside of his cockhead and pulled down his boxers. Josh’s cock stood out at a 45 degree angle and was already leaking pre-cum. I bent forward and licked his sweet juice.
Ann then told me to sit in the chair and asked her lovers to join her on the bed. Ben kissed her passionately as Josh kissed and fondled her perky breasts. Josh worked his way to her pussy and was busy bringing her to her first orgasm of the day as Ben moved up and had his cock in her very talented mouth.
I was taking pictures as they pleasured my wife when I heard a knock on the door.
I didn’t want to disturb them so I quietly went to the peep hole to see who it was. Holy shit, it was Ray, the black waiter from the pool!
I mustered up my courage and opened the door. Ray’s mouth dropped open and he was wordless when he saw how I was dressed.
I said, “Don’t just stand there.