The Pictures Ch. 07

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Mike's humiliation is complete.
3.1k words
4.43
63.2k
9

Part 7 of the 8 part series

Updated 11/02/2022
Created 11/25/2002
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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.

My relief was short lived. "Let go of your ass and put your arms on the table," it was Jack standing behind me. I heard something being squirted from a bottle and I felt something being pushed at the opening to my ass, it was his hard cock.

"Please Jack, No. Please don't."

"Shut up bitch. Relax and this will only hurt for a minute." I felt the head of his dick push into my virgin ass and the pain was unbearable. "Please Jack, don't do this, please, I'll do anything you want."

His answer was to pull the head of his cock out and push it in again. I closed my legs trying to protect my ass. "I tried to do this the easy way but have it your way," Jack said as he slapped my ass. My legs were forcibly pulled apart and each one secured to a leg of the table. With my legs secured wide apart and my upper body being held down, I was at their mercy.

"Please Jack, don't do this."

Jack replied, "I'm going to fuck your slut boy pussy just like I fucked your wife's pussy."

The head of his cock was in my ass again. Someone asked, "You fucked his wife?" As Jack was slowly rocking back and forth in my ass, going deeper and deeper, he answered, "I sure did, and this little slut watched and then cleaned my cock and his wife's pussy. That's the night she put the cock cage on his little dickie."

Jack was now in full gear ripping my ass open and I was actually sobbing like a little baby. I guess the tightness of my ass and the fact that it was virgin had Jack cumming in a matter of minutes. I could feel the hot cum filling my ass.

In the next 30 to 45 minutes, the other 3 men fucked me, all of them squirting hot cum in me. All I could think of was I hope the black guy isn't horny; there is no way my ass could take that massive cock. I was left alone, legs tied wide apart, ass in the air, and cum dripping on my balls and down my legs. 5, minutes, 10 minutes, I was praying that it was all over and I could go home. My mouth was sore, my ass checks hurt from all the slapping, and my poor hole felt like it was on fire. I knew I couldn't take any more of this abuse.

"Untie his legs," said the black man. "Turn him over." I was on my back on the table with the black man's cock at full attention between my legs. "I'm going to fuck you like the pussy bitch you are. Hold him down."

One man was holding each of my arms and shoulders firmly to the table. The other two each grabbed a leg, pulled them back and spread me wide. I cried real tears, "Please Sir, don't do this. Please let me suck your cock again, I promise I'll do a good job."

"Shut up bitch." I could feel the head of his massive cock at the entrance to my hole. He pushed the head in and I screamed and screamed. I had never felt such pain. A hand was clamped over my mouth and he continued his assault on my ass. I knew he was all the in my ass when I felt his body push against my balls. I yelled, "My balls, my balls." I didn't know which pain was worse, his giant cock buried deep in my ass or all his weight on my balls.

"Wait," Jack said. He started to pull out but Jack stopped him. "Don't pull out, just wait a minute. Jack returned and tied a slipknot in a string and placed it around my balls. He pulled it tight and placed the other end in my mouth. The effect was my balls were pulled up and out of the way but I had to hold my head off the table. If I let the string go, my balls would be mangled by the black mans body weight. If I laid my head down, I would be cutting off the blood flow to my nuts and stretching my balls beyond their limit. I was forced to watch him fuck me, adding to my total humiliation.

Having cum less than an hour before fucking me, he lasted for what seemed like hours. The pain was so intense, I was close to passing out. Just when I thought I couldn't take any more, he pulled out of me and started pumping his cock. He squirted 5 or 6 times, all over my stomach, cock, and balls.

"Damn, that bitch has a tight pussy."

I was pulled from the table and dragged into the bathroom where I had to wash and dry all five cocks. Then I had to hold each one while they pissed and suck the head to make sure they were clean.

After thanking each man, Jack told me to go home. I very gingerly walked across the street, the cool night air felt good on my naked ass but I felt like my hemorrhoids were hanging down around my knees. I was in tremendous pain.

Cindy had a bath ready for me, she said she added something to it and it would make me feel better. Lying in the tub, I realized Cindy knew what was going to happen to me that night, how else would she know to have a bath ready.

After drying off, Cindy had a tube in her hand. She said it would sting a little bit but would make me heal faster. She had me bend over and spread my ass checks. Again she said, "This is going to sting a little bit." Damn, she was right.

"Go in your room and put on the outfit on your bed and meet me in the den."

It was a pink, baby doll, type nightie. I hobbled into the den and Cindy was sitting in the same chair she had been earlier when I licked her beautiful pussy.

"Kneel," she said as she pointed to the floor in front of her chair. "I know recent events have been tough on you but it is your own fault. Jack has been trying to seduce me for over a year, with no luck. I confronted him one day and said it had to stop. I was married and I loved my husband. He commented that he thought he were gay or at least bi sexual. I told him he was nuts. After some conversation, we made a bet. If he could prove to me that you were gay, he could have me, within reason, for six months. If he couldn't prove it to me, he promised never to hit on me again. He had two weeks to prove it or not. You prove it for him."

My head was hanging low and I was crying. The SOB set me up.

Cindy continued, "Jack promised, if I kept my end of the bet, he would destroy all the pictures in six months. The problem you have, my dear husband, is that you have allowed me to experience this new life and I like it. I like the power and I like my man to be submissive. I'll give you two choices. If you want a divorce, I will give you a fair settlement. If you don't want a divorce, this is our new lifestyle. You will do as I say, period. I will do as I want. After Jack's six months with you, I will own you. You will be my property. You will have sex only if I say so and you will have it the way I say so. I on the other hand will fuck who and when I want and you will be happy about it. This is your doing so stop the damn crying."

"Your choice, I'll give you 5 minutes to make up your mind. If you want a divorce, so be it but I want you packed and out of this house tonight."

I was sobbing, I couldn't stop. "I love you Cindy, please let us go back to the way it was. I'm so sorry." I put a hand on her knee.

"Take your cum stained hands off me. Make your choice or I'll make it for you."

"I love you. Please don't make me leave."

"Have breakfast ready at 8:30 and set the table for two. Now go to bed." I stood and walked towards the hall. Cindy had picked up the phone but said to me, "sleep in that nightie and serve breakfast in it, you look very feminine."

As I turned to walk to my bedroom I heard her say, he is staying.

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AnonymousAnonymousalmost 19 years ago
it makes sense now...

this chapter finally explains how the whole story started. I also really like that Jack took it to the "next step" at the poker game! Can't wait for more!

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