My husband had repeatedly told me he would love to see me have sex with another man. I had made it clear on all such occasions that it was not going to happen.
We were on holiday in the Caribbean enjoying a lazy hot restful time when I found a young waiter extremely attractive. He was well over six foot tall, muscularly built and had a lovely smile. A smile that he used plenty whenever he was around me. He was gorgeous and after a couple of days I started to admit to myself that I wanted to fuck him. I tried to dismiss this thought but soon started to fantasize the most lurid fantasies. I did a little bit of discrete fact finding before approaching him. Not knowing how such things worked I simply asked him if he would be interested in fucking me while my husband watched. He flashed me his best smile yet while asking me to confirm that my husband would be comfortable with the arrangement but not allowed to join in.
We arranged that I would ring down for drinks to be delivered to our room and that Errol would deliver them. My husband knew nothing until after I made the phone call. I told Sam, my husband, then that if he wanted to watch me have sex with another man this was a one off opportunity. He could sit on the chair and watch but not join in or even say anything unless I told him he could.
He wanted to ask lots of questions but I said he had until the knock on the door to agree. I would not answer any questions and would be free to do whatever I chose. He protested saying that he wanted at least some say in events and who was involved. I made it clear that he would have no say and that this was a one off offer. If he didn't agree before the knock on the door then it would not happen that night or any other night. The confusion on his face was a sight to see. It was almost with a look of defeat that he agreed.
The couple of minutes before the knock on the door lasted forever. Sam was seated in the chair as I invited Errol into the room. The champagne had just two glasses with it. Errol set it down on the table and moved round behind me so that we were both facing Sam.
"Clare has asked me to spend the night with her. Do you understand and do you agree that we can do anything we wish to? I will not touch her unless you confirm that you agree."
His reply was a mumbled yes with his head dropped.
"You will look at us both and ask Errol to be kind enough to fuck the living daylights out of me. Make sure there is plenty of enthusiasm in your reply otherwise you will not get near me for the rest of the holiday. Do you understand?"
"Okay, okay, please Errol give my wife the fucking she quite clearly needs."
His answer sounded excited but a little scared and his eyes reflected this. My excitement level jumped up from it's already high level as Errol's hands cupped my small boobs from behind. His touch was light but took my breath away. He had found my nipples that instantly became rock hard through my tee shirt. It didn't take him long to take it off over my head. He didn't rush things but remained behind me and played beautifully with the nipples right in front of my husband.
I was enjoying both the touch and also the taunting of my helpless husband. I was very vocal in my appreciation so as to leave Sam in no doubt about my excitement. I relaxed and lent my head back onto Errol's chest. He immediately slipped one hand under the waistbands of my skirt and panties and found my pussy. I had been excited all afternoon but had not realized that my pussy had turned into a gooey mess.
"Fucking hell that feels so good. Play with me, rub that clit, oh lovely."
If I had felt like this with Sam, which would have been very unusual, I would have just wanted to be thrown on the bed and fucked to a very short and sweet orgasm. I would have loved that right now but wanted to bask in the joy of this gorgeous young man and the exhibitionism of the situation. I knew I had to take control, as the last thing I wanted was to orgasm on his fingers, skilled as they were.
I hadn't got close and personal with any other man let alone any other cock for over ten years. If the gossip amongst the staff was correct this cock was in proportion to the rest of his beautiful body. I have always enjoyed sex but at this moment the anticipation of discovering what was in his pants was overwhelming. I turned and pulled his shirt over his head. His hairless muscular frame was stunning, with skin that was smooth and radiant.
I pushed him onto the bed on his back. His shorts were off his feet in seconds and if he had underwear on I didn't see it. They were right his cock was magnificent even though it was yet to reach its full potential. Sam is proud of being a very good size. It was clear that this beauty would soon be significantly thicker and longer than Sam's. Knowing that from where he sat Sam would not be able to see Errol's prick I took the opportunity to describe in glowing terms. I eulogized how it was the biggest and most beautiful I had ever seen. Actually it was not true but I had never given Sam all the details of my previous boyfriends.
"My god I am looking forward to being fucked by that monster but I want to taste it first."
I was playing to both the men in the room. The size of their prick seems to be the most significant thing in most men's lives. I was massaging Errol's ego while keeping Sam in his place and humiliating him at the same time. I was loving it. I still had my skirt and panties on as I knelt over Errol's chest facing his feet. As I took his now fully erect cock towards my mouth my pantied bottom was out of reach of his mouth. His cock needed little encouragement to point to the ceiling thereby being partially visible to my husband. I licked and sucked the head as if it was an ice cream. I love teasing my husband but now I was teasing two men at the same time.
Like his whole body his prick was like velvet and very firm. His hands pulled the back of my panties down until they were stretched at the top of my legs unable to be pulled further as I was straddling his chest. I flattened myself against his chest making it difficult for his fingers to find my pussy. It had the desired effect as his fingers centered onto my anus. I love anal play and had realized that his girth would make penetration by his cock out of the question.
I was able to keep eye contact with Sam as I played with my newfound toy. The noises of appreciation from behind me confirmed that I was doing a lot right. I had to stop myself rubbing my clit against my rucked up panties and his chest as I was again getting close to orgasm. He shifted his position and somehow managed to find my anus with his tongue. This is something that is very special to me. Orgasms are the only thing that I enjoy more than being endlessly rimmed by an expert tongue. This tongue was very skilled.
