The Sissy Life Ch. 04

The following weeks after Tom aka "Sir" had made me his 'bitch", he was not around. Our life returned to normal, I asked Barbara if she would like to return to the way things had been before Tom came into our lives. She looked at me like I was crazy, holding up my hand. I explained that it had been nice since the Friday night he was here. He had told her to release me from the chastity cage and that I was allowed to play with myself. I wanted more, our old life back, me having sex with my wife, even if I could not give her orgasms with my cock, I could with my mouth. She looked at me saying" Are you joking with me, I want a real man in my life, he makes me feel sexy and desirable like you never could". She continued "I know you love me and all that but he makes me feel so special and to be honest. I like how you submit to him, sucking his cock, cleaning my pussy and his cock after we have sex. Don`t tell me you don`t enjoy him being here as well, I know you liked him fucking you like a little slut in heat, I saw how your little thing, even in chastity squirted more cum than I had ever seen you squirt. You tell me who the real man is around here." I was so ashamed I went to my room with my head down and red faced and my little thing rock hard. I jacked off thinking about watching him fuck my wife and me cleaning up their orgasms, falling asleep with cum on my lips.

I am still sleeping in the guest room and only go to the master bedroom when she wants me to use my mouth to give her an orgasm. I found out the reason Sir has not been over, he has been in Washington closing a large government contract. He called me this morning and reminded me that he and my wife would be leaving for Europe this coming Monday and that they would be going out this Friday night to celebrate and I will be going with them. I am to wear a suit and tie but to pack an overnight bag with my school girl outfit in it. I have no idea what he has in mind for us. It makes no sense to me, anyway I don't have to suck his cock when he comes in or be locked in chastity anymore.

I told Barbara what he told me and she said she already knew and that he wants all of us to have a great weekend before they leave for Europe. I asked what the plans were for the weekend, she said it was something very special and I should accept it and enjoy myself. I asked what I was expected to "accept", she laughed saying " you will see, it is going to be wonderful and life changing." Friday evening came soon enough, I had no idea what was coming except my wife was very excited about it. " He is going to send a car for us 8 and you need to be shaved and clean, inside and out" she called from the master bedroom.

At 8 sharp came a knock at the door, there was a large man standing there in a chauffeur's uniform. He introduced himself as Jon, saying he was here in Tom`s limousine, to take us to dinner. We arrived at a 5 star hotel I had seen in the travel magazines. Jon held the door for Barbara and told me to get the overnight bags. When we got in he took them from me and they would be in our rooms. The place was amazing, huge chandeliers, velvet covered chairs, lush carpet on the floors. I was looking around when I heard Tom call out to my wife, she was dressed in a beautiful snug fitting knee length black dress, with black 4 inch heels. It made her ass look very inviting, even at her age she had a very firm body. The gym membership Tom got us was paying off, I had lost a few pounds and tightened my butt up with the special exercise his trainer had me doing.

A waiter in a tuxedo led us to a table in an area roped off in a private party area. It was in the far corner of the restaurant with red curtains around it. I guessed it was for large corporations to hold business meetings. The servers brought wine and appetizers to our table, there was shrimp cocktail and escargot. It was divine and the main course was wonderful, a steak and seafood feast. When dinner was finished and dessert was ordered, Jon returned and told me to follow him. I explained I had not had dessert, he told me that mine would be in the room. Sir told me to go with him and they would be up shortly.

When we got to the room, it was a suite with an adjoining bedroom. There was a king bed in the main room and a queen in the adjoining suite. Large walk in the shower, in the bath. My school outfit was laying on the queen bed with a pair of pink panties, a white button up blouse and some pink loafers with white socks. Jon told me that I was to take a shower and get dressed in my skirt and panties. He watched as I undressed and I heard him laugh when I dropped my shorts. He sat and watched as I showered and commented on what a nice ass I had for a guy.

When Sir and my wife came into the room I was dressed as instructed and sitting in an armchair in the corner of the room. With them was a guy more my size, maybe 5`6 or so, very muscular looking, like he was all muscle, ripped. Sir explained that these men were his personal assistance and that I was expected to show them the same respect as I did him and show them the same consideration, as I did him. He introduced them as Jon, who drove us here and Jack as his personal trainer.

Barbara had gone into the bath when they came in and now she came out in the sexiest gown I had ever seen. She kneels down in front of Sir, unbuckled and unzipped his pants, letting them fall to the floor. His shorts were next, it is something I had seen and done before but was always amazing to watch. Taking his cock in her hand she kissed the big head and let it slide down her throat. Jon walked up to them, she did the same to him except his cock was only about 7 inches and not as thick. Alternating between sucking a stroking she had both men hard and ready to go. Jack stood to the side watching like I was, he was rubbing the front of his pants and I was hard and my pink panties to the and let my little thing free. There was a tent in my skirt.

Jon picked Barbara up, putting her down gently on the bed, Sirs cock never leaving her mouth, he dropped to his knees, lifted her gown and dove into her pussy with his tongue. When Sir was hard he told Jon to trade places, he lifted her legs and pushed into her. I heard her gasp around Jon`s cock when he spread her open. He flipped her over and mounted her from behind, watching his huge balls swinging under him as he enjoyed my wife was mesmerizing. He must have fucked her for 20 minutes or so, I counted, she had 3 orgasms. Then I saw his balls begin to pull up tight as they almost danced as they released their contents into my wife.

When he pulled out it was a river of semen, he just looked at me and I knew my job. I licked and sucked all the cum I could out of her, then cleaned his cock and balls.

Barbara came out of the bath after freshening up, she was nude now. She asked Jon if he would like to finish what they started. I was in disbelief that my wife was going to have sex with another man and with Sir`s approval. How did she go from my wife to Sir`s slut. Here I am her husband, sitting in the corner, in a school girl uniform, watching this. I want to stop it, get up and say this is enough but I know I won't, as I look down at the small tent in my skirt.

Jon bent her over the edge of the bed and entered her, I watched as her breast swung in rhythm with his taking her. They changed positions several times before he emptied himself into her as well. Sir again motioned me over to do the clean up, I was getting to where I was looking forward to eating the creampie left behind and I asked myself "why".

I then noticed Jack was watching me clean them and was rubbing himself through his pants. My wife and Sir went to take showers while I sat in my chair trying to wrap my head around what I had just seen. Jack came over to me, putting his bulge in my face, telling me that since my wife was taking a break, I needed to take her place. I protested telling him I would not do it. Sir and my wife came out of the bath, in white bath robes. He reminded me of our conversation where he told me to show his assistance the same respect as him and show them the same consideration as him also, then he motioned for me to go with Jack

Jack led me to the guest suite, then he looked at me with a smile saying " well sissy boy looks like I will have you for the night" He left the door open for all to see. I could hear Sir, my wife and Jon laughing, with him telling me to be a good little slut.

I was sitting on the edge of the bed when Jack put both hands on my shoulders and pushed me to the floor on my knees. I knew what he wanted. I looked into the other room, Sir, Jon and my wife were watching. Sir said" don't let me down bitch" followed by my wife laughing.

I know that this is an important moment in my life and my marriage. Barbara told me that this evening would be life changing and now I knew she was right. I can get up and get dressed like a real man or do what Jack wants and be a cuckold sissy the rest of my life. Serving men and letting them use me for their pleasure. Enduring all the humiliation that goes with it, it is time to make a decision. As I sat there contemplating that, I reached under my skirt and felt my cock not only was I hard as a rock but dripping a little. I then realize this is who or what I am. Reaching up, I unbuckled his belt, unzipped his pants and let them fall.

His cock sprang out and hit me in the face, he may not be taller than me but his cock is huge. If you have heard or seen John Holmes, an adult film star from the 80's, you would understand. I met him once for real, he was no bigger than Jack in height but his cock was huge. FYI, I did not see John Holmes cock other than in his movies. I also met Ron Jeremy, that is a different story.

I took the head in my mouth, as I now know this is my true calling in my later life, to please men. Sucking it as far down my throat as possible I felt him begin to harden. I wanted him to cum in my mouth, I don't think my sissy pussy, as Sir calls it, can take this huge cock. I continued sucking him as he hardened, sucking on his balls as well. I was rewarded with a nice load of his semen in less than 15 minutes. He was not finished with me I soon discovered, much to my surprise he stayed hard. He picked me up, tossing me on the bed. Lifting my legs up like a girl, he pushed my skirt to the side. I was leaking like the sissy I am, he smeared some of my pre cum on his cock and began to push his way into my pussy. He is bigger than Sir, but I took it all and through the pain, slowly adjusted to it. He flipped me over onto all fours and took me again from behind. He slapped my ass telling all that I was his bitch and he intended to use me whenever he wanted. Reaching back I felt his large heavy balls swinging, then they began to pull up. I knew he was going to cum. I couldn't help but orgasm when I felt his cock pulse inside me, squirting my semen all over the bed as he emptied himself into me. I fell forward off his cock into my own semen and fell asleep. I woke up some hours later in a puddle of dried semen, I think most of it was his as it ran out of me. I have accepted my role in this world and am determined to be the best sissy cuckold and husband to my wife I can be. He just came back in for round two and Jon is with him.