As you will recall from the last part of my story, Wes and I had reached the top of the hill, a 200 yard walk. Although I was dressed in very little clothing, I was rather warm, I assume it was a combination of the mental rush and anxiety and the fact I had just walked 200 yards, uphill, in 6" heels, with my hands cuffed together, being swatted with a riding crop every 20 yards.
As we stood at the top of the hill we were in front of the family home, specifically the garage, which was open. Wes grabbed me by the arm and pulled me close to him and gave me a huge kiss, running his tongue deep into my mouth.
Wes then said, "I am going to take your cuffs off and put them and my other toys in garage. However, if you misbehave at all I will come back and get them and put them to use in front of everyone here. It is not open for discussion, tonight you are my date. I expect you to play the role of Michelle like you have never played it in the past. I want you to be all over me like a dog in heat. You will tolerate everything I say and do and comply with my requests completely."
With that he took my handcuffs off and instructed me to wait right where I was. Wes then took the bag containing the toys and his riding crop into the garage. When he returned, he took be gently by the hand and led me toward the front door of the house. As we approached the door of the house, we saw a note that read:
"Come on in, the party is in the back of the house. Make yourself comfortable and cum join us for a great night."
Wes opened the door for me and in we walked. There was no one else in the entrance area, and Wes led me right to family room which opened onto a deck in the back. As we opened the door and walked onto the deck I was shocked. There were well over a 100 people there. Most of the men were dressed in tuxes, and the women were in long formal evening gowns, micro-mini dresses like mine, some leather harnesses, and some in bikini bathing suits. A few of the men were dressed in some bizarre outfits as well, some with leather harnesses, some were being led around by a leash, and some had their hands tightly bound together. Of course who am I to say much about being dressed strange, after all I am a guy in 6" heels and a mini-dress.
At any rate, Wes immediately got himself a drink, a scotch, and me a martini. Now I don't really like hard liquor, but Wes said we were to be sophisticated. He led me around and introduced me to people as his girlfriend, Michelle. He made sure my glass was full and kept me walking and meeting people. During this whole time, he was either holding my hand, had his arm around my waist, or had his hand on my ass massaging it, and occasionally pinching it. When he introduced me to Ron and Melissa, he simply introduced me as his girlfriend. Both Ron and Melissa gave me that simple host and hostess greeting hug and kiss and acted as if they had never met me.
Then the next shock came when we came upon Yvonne and Denise. Wes said hello to Denise and introduced me as his girlfriend, then Denise introduced Yvonne as her new girlfriend and gave her a kiss on the lips right there in front of me. I could hardly stand myself when Ron put his huge hand on my ass and squeezed very hard, ensuring I got the message to behave myself.
Denise went on to say how nice a pleasure it was meeting me, and with that she and Yvonne walked away. My feet were already aching, and it was only about 7:30 PM. We continued to walk, and meet people while constantly drinking. After a bit we were talking to another couple, probably in their mid 50s. The wife was thin and wearing a very straight evening gown, also very expensive. The husband was in a nice tux, and he asked me dance. I said I didn't think so, when Wes said, "Go and dance with him, it will keep you out of trouble."
I knew exactly what he meant. The gentlemen, Brian, and I went to the little dance area they had set up and danced to a nice easy slow song. Everything was going fine, and the music ended. I began to walk back toward Wes when Brian said we should dance some more. We were the only couple on the dance floor and soon we were joined by another couple or two. When the dance ended we walked back to Wes and Brian's wife, Shelly.
Shelly looked at me and just about floored me when she said, "You look awfully pretty for being such a gentleman."
I didn't know what to say, I just sort of stood there. Wes then said something that made me unsure about where the evening was going. Wes said, "Yes she sure looks good, but we have yet to see if she can satisfy her man."
I didn't say a thing.
Over the next four hours or so I danced almost constantly, as Wes had me meeting and greeting people non-stop. At the conclusion of each dance Wes was certain to hand me a drink, play with my ass, and make some comment about his little lady. It was nearing midnight, and I could hardly walk as my feet were hurting so bad. I made the big mistake of telling Wes my feet were hurting.
He simply said, "I told you not to complain, come with me."
He then led me around the corner of the house where there were some tables and chairs. He sat down in a chair, and turned me over his knee. He then began to give me a terrible spanking. I never remember being spanked like that in the past.
When he had finished he said, "Now, if you complain again, I am going to do the same thing in front of everyone, do you understand me?"
I immediately responded, "Yes Sir."
He then led me back to the party. As he talked, I struggled to dance. Finally about 1:00 AM the music ended. I was tired and could hardly stand. I thought about going home and collapsing, but I had no car and Yvonne was no where to be seen. As people left Wes, Ron, Melissa and I all stood saying good-by. Finally, it was just the four of us.
We all then walked into the house. Finally Wes said I could take my shoes off, which I did quickly. It felt so good to be standing on my feet instead of my toes.
After sitting and talking about 15 minutes, Melissa took me by the hand and said I needed to go with her. She led me to the bedroom where she gave me a little teddy to wear to bed since I would be spending the night there, and she showed me the bedroom I would be sleeping in. I crawled into bed and was asleep almost immediately.
About 5:00 AM, just a few hours since I crawled into bed, I felt a hand massaging my thigh, I knew immediately whose it was, Wes's. As he massaged my thigh, he also began to slip his hand inside of the little panties I was wearing. I was so tired I just laid there. I guess my inaction must not have been what he was looking for. He took his hand and forced my panties down by my knees and began to play with my male tool, which could have cared less. However, even being a guy in a teddy it began to awaken.
Wes then, put his lips close to my ear and whispered; "Now it is time for Michelle to experience what it is like to be with a real man."
He then pulled the gag he bought out and placed it in my mouth. Next he took my hands and pulled them behind my back, and bent my arms so my hands were between my shoulder blades, it was then he placed my wrists in the handcuffs. I was pretty much helpless. The next thing I heard was the sound of the riding crop cutting into my ass. Wes then said, that was just a warm-up and he was going to make my ass the same color as the red ball-gag I had in my mouth. He then began to use the riding crop and raised huge welts on my ass. He assured me there was no blood, but there were tears in my eyes.
After what seemed like an eternity, I felt the lubricant being applied to my anal opening; I could only guess what was next. It didn't take long before I found out. Wes began to use his stallion sized penis to spread my cheeks and before long he was fully inside of me. He asked if I was in pain. I nodded my head yes. Wes said he was sorry it hurt, but it was all a part of the evening plan. He then began to pump away for what seemed like an eternity. Finally, I could feel his fluids filling me. When he had finished, he turned me over onto my back, got off of the bed, slipped into a robe, and walked out of the room.
In a few moments, Melissa walked into the room. I was hurting, embarrassed, and still somewhat in shock about all that had happened. In a few moments Melissa began to massage my limpless cock and began to bring it back to life. She then mounted me and explained she had wanted to have me since she first heard of me, and now was her chance. Melissa continued to work on me until we had both reached our completion. She then dismounted me, turned me back onto my stomach, and looked at my ass, and remarked it looked awfully sore, but it was OK, and she then uncuffed me and told me to get undressed and stay in bed. I was more than happy to oblige.
I must have fallen back to sleep, but in about 30 minutes, Denise walked into my room. I was asleep when I felt someone touching my male tool. As I awakened, I was led into the bathroom where Denise and I showered. Denise scrubbed my face making sure all of my make-up was off. As we stepped out of the shower, I asked, "What time is it?"
Denise responded it was only 6:30 AM, and we needed to get busy as there was a lot to do. She began by drying my hair. Before long she had fixed my hair, and applied a light day-time make-up to my face. There I sat, a female hair style, make-up, and fake boobs. She then told me to come with her. She led me back into the bed room, and there on the bed was my outfit. A French Maid outfit, complete with 5" heels, the last thing my feet wanted to see. She told me to get dressed quickly and to go to the kitchen.
I complied with my instructions, and when I got to the kitchen it was nearly 7:00 AM. There in the kitchen was a note of instruction for me. Everyone else was on the patio, and I was to serve them breakfast. Everything needed was on the counter, cups, coffee, juice, pastries, etc. The instructions went on to say I was to go to the patio and pretend I was a waitress in a restaurant, so I had better do good.
As I walked onto the patio I noticed it was cool, but the sun was up and shining brightly. I greeted everyone, and went about my duties. It took me about an hour to get everyone served, and finally I was told I could now eat. I was starved, as I had not eaten much the night before.
Yvonne fixed my breakfast; I still remember it to this day. A piece of toast, ½ a banana, a cup of juice, and a cup of coffee. Yvonne told me they didn't want me bulking-up for the day. About 8:30 or so everyone finished. I was then told to clear the table, do the dishes and put everything away, then go to my bedroom. I began my tasks, and could hear everyone else showering, but I had no idea what was happening. Finally, About 9:15, I got everything done and headed upstairs. As I got to the top of the stairs, I could see everyone dressed in nice "Sunday" clothes. I walked into my bedroom, and there was a business suit. Denise came in, and said she would help me touch-up my make-up, which she did. I finished dressing and walked back down stairs to the patio. Everyone else was waiting form me. There I stood on a Sunday morning, in a pale blue suit where the skirt was about 5" above my knees, no blouse, with a white silk scarf, nude hose, and 4" white pumps.
Everyone got up and we headed to the garage. Since there were so many of us, it was obvious we had to go in two cars, so Yvonne and Denise went in one car, and the two "couples" went in another car. In about 15 minutes I was walking into church as Michelle, I was shocked at what was happening. I sat through a very uncomfortable church service and soon was walking out the door. Not only were my feet killing me, but my ass was aching from everything it had endured.
Ron then said we were going to lunch at a local restaurant. We walked into the restaurant, and sat down. When it came time to order, Wes ordered my lunch before I could even speak, a little salad, and water with lemon. He leaned over, gave me a kiss on the cheek and said, "I like my girls tiny."
I ate what little food I had, and walked out of the restaurant. On the way back to Ron's I just sat and relaxed. Since we were all dressed-up, the other ladies decided we should go shopping at the local mall. Of course I had to go along. So here we were walking around looking at all kinds of clothing, and finally we headed back to Ron and Melissa's home. When we got there it was about 5:00 PM, I could not walk. All of the ladies went to the upstairs where we once again changed clothing, this time into jeans, so we could go horseback riding. I was given a pair of Denise's jeans which were very tight, and caused my ass to hurt something terrible, and I was also wearing a pair of her riding boots. We went to the barn and got the horses and took off. The last thing I needed was to be bouncing up and down in a saddle; it really caused my ass to hurt even more.
Finally we returned to the house. We ate a light dinner, and finally about 7:30 Yvonne led me upstairs, there she gave me some clothes to wear. A simple little skirt, a T-top, and a pair of wedge sandals. We walked down stairs said our good-bys and headed home. I didn't speak on the way home, I was way too tired. When we got there, Yvonne said it was now time for Michael to have some fun, and she led me into her apartment. As tired as I was Yvonne took care of Michael and made him a very happy man.
Of course there is more to this story, but you will have to wait till next time.