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.

Come on in.”

I explained the party had already started but I was sure he would be accepted with open arms.

As before, I dropped to my knees and removed his shorts as he pulled off his shirt. I then removed his undershorts and saw a fine young penis staring back at me.

He was 6 inches and soft with big hanging balls and to my surprise just as hairless as his head. In fact he had no body hair at all.

Ray explained he needed a shower as he was working all day. He went to shower and I went back to see what was happening in the bedroom.

Ann asked, “Who was that, your waiter friend from the pool?"

“How did you know?” I asked. 

Her reply was, “Oh please, you are such a sissy slut, as soon as I saw you only order our drinks from him I knew you wanted to suck his cock.”

I was embarrassed. My cheeks flushed and turned red. Many times she recounted her black male lovers from college as we made love and it always got me hot. So she knew I had always wanted to be with a black man.

Ann said, “When he finishes showering have him join us but do not touch his cock until I instruct you. Remember," she said, "I am always first and you get the leftovers.”

When I returned with squeaky clean Ray, Ann was nude and on top of Ben in a reverse cowgirl position. Josh was standing at the foot of the bed with his long cock in Ann’s mouth. Ann looked up and pulled Josh’s cock from her throat and gave an approving moan when she saw Ray.

Ray looked at the scene on the bed and his cock sprang to attention. Ann told him to come close so she could taste his fine young cock.

As Ann kissed and licked Ray’s manhood she told me to keep Josh hard. I couldn’t get to my knees fast enough as I anticipated the feel of his spongy cockhead going in my mouth.

After a few minutes Ann broke her assault on Ray’s cock and told me to take some pictures. She also told Ray to get on the bed and lube up her ass and his cock. Josh put his hard cock back in Ann’s mouth as Ray climbed on the bed and put a knee on each side of Ben’s chest.

Ann told me to hold Ray’s cock and line it up to her rosebud. I reached over and held his cock for the first time. His cock felt so good in my hand, I only wished it was in my mouth. Ray’s cock had grown to a full 8 inches.

I had his cock at the entrance of Ann’s tight rear tunnel when he pushed forward. After initial resistance, he entered her until his heavy balls rested on her ass cheeks.

Then the fucking began. Ann did most of the movement. With a cock in every hole, she moved back and forth and slightly up and down. Ben reached in and fondled Ray’s swinging balls and even put a finger in Ray’s asshole.

Josh was first to explode. He screamed out and shot his pent up cum in Ann’s willing mouth. She swallowed repeatedly, not missing a drop of his tasty man juice. That set both Ben and Ray off. They grunted and moaned out as they shot their loads in my wife’s cunt and ass.

Ann couldn’t take it any longer, feeling her lovers fill her with their potent seed. When Ann’s climax swept over her she screamed out with joy and pain. She later described it as the most intense orgasm she had ever had.

When they caught their breath, Ann ordered me to clean everyone up. She didn’t mean with soap, water and a towel either. All three guys were lying on the bed on their backs. I crawled over first to Ben and took his flaccid penis in my mouth and sucked Ann’s and his cum off and then gladly swallowed. Then I moved to Josh and licked off the remainder of his cum that was dripping from his pee hole.

When I got to Ray, everyone looked as I took his still hard cock that was just in Ann’s asshole and took it to my lips. I put my thumb and forefinger at the base of his cock and forced out the remaining cum by moving my fingers toward the tip of his cock. I then sucked his nectar into my eager mouth. He tasted like salty walnuts and I savored it before swallowing.

My turn to clean Ann. She instructed me to lie on my back as she squatted over my head. She lowered her cunt and ass to my lips. When she squeezed her anal muscles, huge amounts of Ray’s cum gushed out and flooded my face. I was aware pictures were being taken as I began to lick it all up. Ann then let all the cum from her cunt flow out into my waiting mouth. I clamped my mouth around her pussy lips and drank all her and Ben’s copious amount of body juice.

At the same time I flicked my tongue back and forth rapidly over Ann’s clit and in no time she was shaking with another orgasm. This forced out more cum that I swallowed with great joy.

My cock was now aching for attention. I begged Ann to give me relief by sucking me or letting me jerk off.

Instead of giving me a blow job, she got mad. She ordered me to get my paddle. She told me to lower my panties and then had me lie over Ben’s legs, placing my hard cock between his thighs. Ben squeezed my cock with his powerful legs, thus preventing me from coming.

Ann also placed Ray next to Ben with my head at his crotch. She told me I was a bad little sissy boy for wanting to cum so soon. She told me to suck Ray’s cock as she started to rain down the paddle on my ass. She must have spanked me a hundred times. My ass was on fire. Each time she spanked my bare bottom it sent electric shocks to my trapped penis tip.

She asked Josh if he wanted to spank me, and he quickly said yes. His hits were harder than Ann’s but spaced out further.

The pain and humiliation of being spanked in front of her lovers, and then having Josh also spank me, put me in cuckold sissy boy submissive heaven. I wanted to cum so badly I thought I would die from the lack of release.

Ann was laughing when she said to Josh, “Hand me the lube, please.” She then proceeded to spread lube on my asshole and Josh’s cock.

Josh got in position as Ann spread my ass cheeks. He then pushed forward and his cock slipped easily into my willing man pussy.

Now I was sucking Ray. My cock was in a vice grip between Ben’s thighs while Josh fucked my ass. He was not gentle. He pounded into me with great force over and over again until I felt his cock swell up and dump his cum deep in my bowels. This set Ray off. His powerfull streams of cum that hit the back of my throat. 

I was gagging and swallowing at the same time because I knew if I missed a drop of his cum Ann would severely punish me. I was able to swallow it all. I also enjoyed the ass pounding I received from Josh.

When I was allowed to get up Ann told me I could now jerk off onto her cunt. I quickly moved between her legs and aimed my swollen cock at her puffy red cunt lips. I grabbed my cock and stroked it and was soon shooting rope after rope of cum out my pee hole onto her cunt.

I was exhausted when I finished but knew my job was not done. I bent forward and licked up my own cum as I heard the sound of laughter and pictures being taken. I was humiliated but very happy.

Yes, I was a cuckold, cum sucking, sissy boy, submissive, cocksucker and I loved it.

Look for, “Day two of our mini vacation” coming soon.