Due to personal issues, it's been a while since I've posted. Thanks for the support and with some luck I'll post again in the very near future.
I received 3 enemas from Janice, each one followed by a cold shower. I was happy that I didn't get a surprise from "mommy" as she had suggested. I walked into Jack's den and was pleasantly surprised when he threw my shorts at me and told me to leave.
I walked across the street and into my home to find Cindy naked in the large leather chair, playing with herself. She motioned me over and told me to kneel in front of her. As I did, she spread her legs and scooted in the chair so her ass was on the edge.
"All of today's activities have made me very horny. I'm going out tonight but don't want to wait. Use your tongue on me, make me cum." I did as I was told, at first trying to rub her G spot, then concentrating on her clit trying to make her cum.
"Slow down you idiot, that's not a dick your sucking on, make it last." I slowed my pace moving from her pussy to her clit and back and forth. After 30 minutes or so, she clamped her legs around my head, keeping me glued to her clit and came with a scream.
"Lie down on your back" she said. She walked over, put a foot on each side of my head, glared down at me and said, "Your mouth is the only thing worthwhile on you." With that, she sat on my face and told me to clean the mess I'd made. "Don't lick you fool, suck my pussy clean."
After Cindy had finished with me she told me to run a bath, in my bathroom. As the tub was filing, she added some type of bath salt and perfume. She told me to relax in the tub until she returned. She came back about 30 minutes later, it was obvious she had showered while I was in the tub, her hair was wet and she was naked. "Get out, dry off and come into my bathroom."
I was told to sit on the stool, which had been placed in front of the large mirror. Cindy then applied a gel to my hair and combed it straight back, the effect was that my hair was plastered to my head. As she reached in one of the drawers, there was a knock at the front door. Cindy put on a very sexy, see - through robe and went to answer the door, telling me to stay put as she left the bathroom. I was mortified, sitting naked as Cindy walked in the bathroom and introduced this stranger as Ms. Erin.
"So this is the cock sucking little slut," Erin asked.
"Yes, that's him," replied Cindy. "Stand up boy," Ms. Erin ordered. She then reached down and played with my cock cage, rolling it over in her hand. She then looked at Cindy and said, "It's a very small cage isn't it?" Cindy replied, "There just isn't any reason for a larger one." Both women had a good laugh at my expense.
"Well, lets see what we can make him," Erin stated. 45 minutes later and for the second time in my life, I had make up on, complete with bright red lipstick and a blonde wig. I was then put in a pair of white lace thongs, white stockings, fake boobs were put on my chest using double sided tape, and they put me in a French Maid type outfit which barely covered my ass and then added 5" high heels to complete my outfit.
Steeping back and slowly looking at me from head to toe, Ms. Erin said, "If I had a cock, I'd let her suck it."
"She is kind of cute, isn't she," Cindy and Erin both had good laugh and my humiliation continued at the hands of my own wife.
Cindy told me, "Go to Jack's house."
"Please ma'am, don't make me go outside dressed like this."
"It's almost dark and I need to get dressed to go out. Now get out of my house," was her reply. I could hear Ms. Erin giggling as I left.
I walked across the street, rang Jack's doorbell and waited. He left me standing there for at least 5 minutes before opening the door and letting me in.
"Don't you look cute. Turn around and let me look at you." As I turned, he grabbed my ass and rubbed it saying, "I think we're going to have some fun tonight." He explained that he was playing poker with a few of his friends and I was going to serve them and be the entertainment. Somehow, I knew this wasn't going to be a good night.
As instructed, I put snacks on the table and filled the ice bucket in the wet bar. The first person to arrive was George, the junior partner from Cindy's law firm and the second dick I had sucked. After saying hello to Jack, he walked over to where I was standing, grabbed my balls with one hand and lightly rubbed his fingers around my lipstick covered mouth, "such a hot mouth on a pretty slut and I look forward to using it tonight." George squeezed my balls making me jump and told me to fix him a drink.
As I handed the drink to George, he told me to turn around, spread my legs wide and bend over. "Now, spread your ass checks." I felt so embarrassed in that position; the only thing hiding my hole was a thin piece of material from the thong Cindy had put me in. I then felt a hand on my ass and the thong was pulled away and I felt something pushing against my ass. "Just relax and this wont hurt," George said and I could hear the enjoyment in his voice. Within a minute, a butt plug had been inserted in my ass. I felt my sphincter muscle clamp around it and hold it in place.
"Stand up and straighten up your clothes, slut," was the order from Jack, he had been watching the whole episode.
In the next few minutes, three other men arrived. Two, I didn't know and one was the big black man from earlier. I was introduced as slut and each man was introduced to me as, Sir.
During the next hour or so, the men played cards and I served drinks. Each time I neared one of the men to serve a drink, my ass or balls were fondled and crude remarks were made about my outfit and me. Although they were only playing, nickel, dime, quarter, Jack was losing and was not happy.
"Time to liven up this party. Slut, take off your panties and show my guest what you're hiding under there." I did as I was told; the maid outfit stopped right above my crotch and the cock cage was clearly visible.
"Come here bitch." I walked over and stood next to Jack. He turned me so I was facing the other four men, grabbed my balls and said, "I own this poor excuse for a man, he's going to suck my dick and each of you can have a turn with him. With that, Jack stood up and told me to kneel.
"Remove my pants and underwear boy." I pulled down his pants and he sat down on the chair. "Leave me out of a hand or two, I'm want to enjoy this blow job."
Within the next hour, I had sucked four of the men swallowing their cum. The only one left was the big black man. He grinned at me and said, "come here white boy." I knelt in front of him and without being told, pulled his shorts down. Only inches from my face, hanging straight down, was the biggest and meanest looking cock I had ever seen. He put his hand on the back of my wig-covered head and pulled me to his groin. I opened my mouth, praying that it wouldn't get any bigger when it was hard. Much to my disappointment, it did grow. It had to be 10 – 11" long and half as thick around as a beer can. It actually stretched my mouth and was very uncomfortable.
He sat down and informed me that I could do all the work for a while. I'm guessing 30 minutes of hard sucking and pumping, he stood up, put both hands on my head and started fucking my face. His final thrust buried his cock in my throat, cutting off all air. He must have squirted 6 to 7 times right down my throat. When he finally let go of my head, I fell to the floor exhausted.
I was allowed to relax for 15 minutes before being ordered to freshen everybody's drinks. All five men were in the den, watching porn and naked from the waist down. I was hoping five blowjobs would be enough but I was sadly mistaken.
Two and half-hours after I stared giving the first blowjob and an hour after the last one, Jack was ready for more. Jack motioned to George; evidently, they had discussed the next set of events prior to this. George called me over to the table where they had been playing cards and told me to bend over. My ass and the butt plug were now completely exposed to all. George told me to reach behind and spread my checks and not to let go. He kicked my ankles and I spread my legs wider and wider. He then reached up and yanked the butt plug from my ass. The relief was instant; I felt like my ass had been stuffed all night.