I felt the bed begin to loosen and unwrap me as I was able to turn my head and see Jim getting me out. He asked how I slept and I told him the best ever. Jim told me it was only about 5 am and that he had not slept much thinking about my ass and watching Pierre fuck me last night. As my final binds were unfastened from the bed device Jim led me over to a chair and pushed me to my knees in front of him as he sat down. Jim was naked and I could see his cock was semi erect and I put my mouth around his shaft and started sucking him. I could feel him growing almost instantly and it did not take long before I could not hold his full cock inside my mouth. He had me suck and mouth both of his large balls and then he pulled me up to him and began kissing me deeply as his tongue explored my mouth. I grasped his cock and could feel he was leaking precum. I tried to go back down on him but he said no and picked me up and carried me over to the spanking rack where he lay me with my head down and ass up standing behind me between my spread legs. With one firm push he pushed himself fully inside me using Pierre’s cum as lubricant. I gasped as his cock hit bottom and he began to use one of his hands to slap my ass with stinging blows as he picked up his pace fucking me. He was enjoying himself and was groaning and hollering in ecstasy with every thrusts and every slap that echoed through the small building.
I was grunting in pleasure and my cock was straining against the confines of its cage. I felt Jim move his hands up to my nipples and he tightly pinched them both making me cry out. It hurt so bad and felt so good at the same time I told him that my cock was leaking cum and would not stop despite not being hard. It was the weirdest feeling ever, my cock was leaking a massive amount of cum but I was not having an orgasm like I have ever known one. With each inward thrusts Jim made I felt a while new rope of cum leak from my confined cock. Jim finally blew his load deep inside me adding to what was there from Pierre a few hours earlier. When he pulled out my ass was sore and it was hard for me to walk to the kitchen area outside the pool. Jim carried a glass bowel half filled with cum along with us, it had been placed beneath me and had caught every drop of my ejaculation.
Once at the table both Jim and Pierre remarked on how much cum I had leaked. They teased that my balls had to have been full and painful. I was given two waffles for breakfast and was told that instead of getting butter or syrup I would restore what I had “leaked” earlier and the cum was poured over my waffles. After the first bite the taste was not really bad and I was so hungry I ate everything on my plate.
After breakfast I went and showered trying my best to clean myself. I used a bottle enema solution and did not think I would ever get all the cum out of my ass. I got the best I could and then shaved my body a fresh time since I had some stubble coming up on my legs and chest. By the time I was done I was covered in lotion and my body was as smooth as silk. I was getting used to being a submissive and was liking the feeling and emotion it gave me. My mind was wondering what I would be in store for today, my third day. A part of me hoped for a relaxing day of lying in the sun alone with a drink and the other side of me was hoping I was going to experience a lot more of what had turned out so far to be great new experiences. I felt totally safe and secure with both Jim and Pierre and had built a bond of trust with them knowing that they were not going to let anything happen to me that I was not wanting. My thoughts were interrupted by a harsh knock at the bathroom door and I opened the door to find Pierre and Jim both standing outside. They looked me over and rubbed my body, remarking about how smooth and hairless I was. It was a stark contrast to their hairy bodies in the mirror next to me. The small cage containing my cock looked puny in comparison to Jim’s massive fat cock jetting forward from beneath his hairy belly and wide hips. “Just like a woman, spend all day in the bathroom getting herself all pretty. Pierre, get Tammy here dressed and ready for our company today while I go ice down some beer and get ready.” Hearing Jim refer to me as Tammy was a turn on for me.
Pierre led me to a room inside the house where there was a closet filled with lingerie. Pierre teased let’s get you dressed like the little slut you really are referring to me as Tammy the whole time. When he was done I was wearing a pink lace bra with a matching pink lace panty. The material was very delicate and very feminine and surprising felt great against my smooth skin. I was also wearing a pair of white fishnet hose with a pink garter making my legs look longer and even more slender than they really were. I had never worn women’s clothing and had never had any desire to do so. I was very masculine and usually the dominant one in full control. This whole experience of giving full control and now being dressed in ladies lingerie was causing a while new wave of emotion and feelings I had not experienced before.
Once I was fully dressed in the lingerie I was led outside to the pool area. I wanted to run back inside when I saw there was now a group of probably 20 men, all very masculine and solidly built milling around the pool drinking beer and talking. I was introduced as “Tammy” and everyone was told that I was a cock slut there for their full enjoyment. I would estimate the guys all to have been ranging in age from mid fifty to late sixties. The feeling of humiliation as I stood in front of this group dressed in slinky lacy lingerie complete with my shaved hairless body and a spray of very feminine smelling perfume was overwhelming and a invigorating at the same time. A wave of emotion raced through my body, what if I saw one of these guys outside of here? If I had been a part of this group I would have been the alpha male trying to prove my masculinity but the roles were changed and I was now being paraded in front of this group of men and presented as their sex toy for the day. I was referred to as “Tammy” and as “she” in every reference which only enhanced my full humiliation. On one side as I was being introduced with my ass being slapped randomly and the sly comments about my femininity I wanted to play the role fully but on the other side I wanted to give the disclaimer that this was all just a role play. I remained quiet and curt as I was introduced and in an almost surreal way was like I was looking at myself as events happened. I think the combination of my cock being confined inside its small cage, being totally shaved and adorned in lingerie complete with nail polish and perfume I felt feminine around these guys and was acting the part.
Once the introductions were complete and the cat calls and leers subsided the guys went back to their conversations with each other and I was approached by a stranger who asked if he could buy a lady a drink. I accepted and he ordered me a gin and tonic without consulting what I may have wanted. As he made small talk my mind raced wondering if the guys here knew what was going on or did they think I really was this person who dressed this way and acted this way brought here solely for their entertainment. My attention retuned when my suitor, Alan, asked “so, do you put out on the first date?” and followed up with a laugh. Alan was a large man, standing about 6’4” and had a shape like a refrigerator box. He said he knew Jim from the gym and always enjoyed his parties. Alan was wearing a pair of speedo bikini bottoms that were covered by an oversized tank top. I could tell he was a hairy man and not somebody you would want to mess with. He ordered me a second drink and I drank it faster out of nervousness than I wanted. When I finished my last sip Alan led me to a corner of the pool that was a little secluded and he sat on a chair and said “Tammy, why don’t we see what that hot little mouth of yours can do on this log.” I was not sure what to expect as I lowered myself to my knees in front of him as I had not really had any view of what he was packing. I pulled his shirt up and then pulled his speedo bottoms off his hips as he raised his hips to assist. Alan had a smaller sized cock that probably only stuck out about four inches, it was not exceptionally large around and looked to be a perfect mouthful. His balls were hidden by a nest of long pubic hair that had probably never been trimmed but were smaller sized. Alan had a strong smell of musk emanating from his groin and as soon as I went down on him he started groaning and hollering about how good it was and for me not to stop. It did not last long and Alan announced he was going to cum and I moved my mouth off his groin and jacked him off until his cock was drained. I knelt between Alan’s legs and he said he needed a nap now and as I got up I saw that I had attracted an audience and was getting lots of comments.
I wanted another drink but as I walked toward the bar in my heels I was grabbed by another large man and pushed roughly to a poolside sofa and pushed onto my back. He pulled my pink panties off my legs and left me in my fishnet hose and heels as he pushed my legs back over my head and pushed his cock toward the entrance of my ass. He paused and pulled a condom on and then pushed the top of a tube of lube into my ass and pushed some of the lube up inside me. Without pausing he pushed his cock to my entrance and pushed in one effort. A bolt of lightning felt as if it had entered my anus and shot all the way to my brain as this unknown man had just pushed the full length of his six inch cock as deep inside me as he could. I cried out and he laughed saying “take it like a good girl” and without pausing started fucking me as hard as he could. I heard Jim telling people that anyone who was issued a green wrist band had a clean medical report and was not required to use any protection. My suitor must have heard this at the same time as he pulled out and pulled the condom off and then pushed himself back inside me and resumed his pace without missing a stroke. I was crying out in a mix of pain and pleasure with every thrust as I felt a cock being pushed into my face. I took the cock into my mouth and was now getting it from both ends as I could hear comments about what a good little cock slut I was and how tight my man pussy was. The guy inside my ass pushed inside me and released a bucket load of cum into me and then was immediately replaced by another hard cock who took his position. I lost count with the number of cocks I had sucked off and taken anally after the first ones but finally the last one filed my mouth and moved away. I could see a lot of the guys standing around stroking their hard cocks and my own cock was straining against the tight confines of my cage. I got up and was wobbly on my feet as a guy helped me over to the bar where he ordered a drink for me. I sat and sipped on the tequila sunrise he gave me and rested for a few minutes.
I looked down to see I was now only clad in the bra and heels. At some point I lost my garter and fishnets. I was also covered in cum and leaking from all my orifices. The guy I was with was telling me how hot I was and how he would love to have a girl like me. We talked for about half an hour and he asked if he could take me someplace private and have sex with me. I told him yes and he pulled my stool out and we went inside the house to a bedroom and he closed the door behind us. Robert, was a 63-year-old man in great shape, he had salt and pepper wavy hair and had a muscular but very fit body. As he closed and locked the door he pulled me to him and kissed me deeply for several minutes. He was gentle and passionate and was making me melt to his touch. As I slowly removed Robert’s clothes his cock finally sprang free. He had a shaved pubic area and his cock was rock hard and about six inches long and a perfect girth. Robert was amazing in bed and we spent about an hour together. Robert was able to cum twice and said he would love to make me cum but was restricted with my chastity device. Once he was finished Robert said he would love to spend a weekend alone making love to me. He asked me if I had many more of my sexy outfits and I told him I would buy whatever he liked. We made a plan to meet about six weeks later and to spend a weekend at a mountain retreat. Robert said he had access to the honeymoon suite at this resort and promised to make me the happiest girl in the world. As we departed the room and walked back outside Robert said he would leave all his information with Jim and Pierre and tell them to give it to me and to contact him as soon as this weekend was over. My mind was racing, I had never dressed like this before and now I have a date to meet this hot stud and to be his “girl” for the weekend.
Back outside things had chilled down and most the guys were either playing a game of corn hole off to the side or sitting around the pool eating BBQ and talking. Jim made sure I had a plate and got plenty to eat.
A little later I was once again restrained on the spanking bench and given another spanking. I could feel my ass on fire from the leather strap and knew I also had handprints on my ass from the bare handed spankings I had received. While my ass cheeks were on fire and stinging like crazy it also had me fully aroused and I heard myself begging for somebody to fuck me and to stick a cock in my mouth. I did not have to ask more than once and received a cock in both ends. For the rest of the evening I was kept restrained on the bench providing open access to anyone who wanted me. My humiliation continued as I was left spread wide open and totally vulnerable to anyone. I had taken so many large loads of cum inside my rectum that my gut was filled with air and I was unable to control the release of air from my ass or the ropes of cum that accompanied it. This embarrassed and humiliated me greatly but was a huge source of pleasure from the crowd still gathered as they commented about how full her little pussy is and maybe she needed a little more or maybe I needed a plug. At least three guys came over during the evening and fucked me hard while being cheered on by their buddies. Each also left me with another load of cum. I was enjoying every minute of my debacle on one level but dying inside of humiliation on another. It was one of the most intense, erotic and orgasmic feelings I have ever experienced.
Finally, after dark the group started to depart and I heard the music stop. I had drifted off to sleep on the bench still restrained. Jim and Pierre unfastened me and helped me to the table and gave me food and water. They told me I was sleeping in the private room tonight and would not disturbed till morning. Once I retired to the room and spent an hour in the shower trying to wash the cum from my body. I finally gave up on getting it all out of me and lay a towel on the bed to catch the endless river leaking from me. My ass was so sore and stretched I wondered if it would ever be the same. I applied lotion to my entire body and then climbed into the bed. My mind was on Robert and the connection I felt I had made with him as I drifted off to sleep quickly.