Cindy’s Humiliation


Cindy’s Humiliation
Mr. Simpleton

“Please don’t make me do this. I beg you, Carlton, please don’t make me do this again.” I looked hard into her eyes and saw more humiliation than I did fear. I didn’t want her to fear me. Cindy chose to come to this place, and in accepting the security I could offer her, she knew the price she would have to pay was to consent to my demands. For her to disobey me meant that she would have to leave, and that would mean certain death. Not by my hands, but at the hands of the ones she was running from.

Back in the cities the streets were very dangerous, especially for young women. Gangs of hoodlums roamed from dusk till dawn, scavenging for their sustenance. They traveled in small groups of 10 or 20, looking for anything they could find, and killing anyone who stood in their way. Cindy knew that she was much safer with me than she would be by herself back in the cities. I knew I had this advantage over her. I would never hurt Cindy, I still loved her very much. But humiliation was another thing all-together.

I continued to fill the water tank in the make-shift shower located outside of my cabin. Her pleas were music to my ears and I responded to them with only with my eyes. She could read my eyes and knew they were saying “shut up and strip.” I could sense her helplessness as she acquiesced to her condition and continued to remove her clothing. She was dirty from nearly two weeks of wandering through the woods on her journey to get here. Her clothes were torn and her skin was scratched and bruised. Who knows how long it had been since she had taken a proper shower. Even before she had escaped her captors back in the city, there had been no running water to shower with for some time. The collapse had brought with it a hardship for everyone who was dependent on the system of things. No water, no electricity, no grocery stores, and no safety.

I climbed down off the ladder carrying the empty bucket and walked to where Cindy was standing, naked. She tried to cover herself as best she could, but to no avail. She knew it didn’t really matter anyway as I was going to see her naked body as she showered. I set the bucket at her feet, looked her directly in the eyes and said “bathe.” Reaching up I pulled the chain to release the water onto Cindy’s head as I walked away. She gasped as the water splashed onto her bare skin. I began the process of heating another pail of water and watched from the corner of my eye as she soaped and scrubbed her body. As she washed, the dirty water ran off her skin and puddled on the ground at her feet. She tried to ignore me, but she knew I was watching.

“Don’t forget to wash between your legs” I instructed her with a half-assed smile on my face. Cindy glared at me knowing that she had no choice but to obey. “Spread ’em wide so I can get a good look” I chuckled, humiliating her even more with my demand. She didn’t even look at me this time, she just spread her feet wide and began to wash her pussy. When the water was hot enough, I carried the bucket over and asked if she was ready to be rinsed off. She braced herself without even a nod and I began to pour the water over her head. The soap and dirt was now washed away and I could finally see the firm beautiful body of the woman I remembered. Her nipples hardened in the breeze as Cindy wrung the water from her long hair. I reached our and pinched one of them between my fingers. Cindy pulled back and cut a cold look at me.

“Happy, now?” she smirked, wiping the water from her eyes and shivering like a wet puppy. I just smiled and tossed her a towel. She was as beautiful as I remembered her being years ago when we dated. “It’s funny” I said, “that you would think to come to me when you got yourself in trouble. Seems like I remember you saying something about never leaving the city, never joining me out here in the wilderness no matter how bad things were.”

“Well, things have changed” she snapped, continuing to dry herself. “And you were the only person I could think of who would have a safe place to hide.”

“You’re right about that, woman. Now get over here and let’s get this over with” I ordered, picking up another pail of warm water off the fire and placing it on the ground next to the bench. Cindy reluctantly followed me over to a small bench I had set up near the shower. I removed my shirt, boots and pants, then took a seat. Cindy stood naked in front of me knowing what was about to happen. She tried not to look at me but I could feel her eyes on my cock as it began to harden. I looked up at her and took a moment to enjoy her helplessness before speaking. “You know the drill, woman. Now turn around and assume the position.” Eyes turned downward, she turned around and lowered her bottom onto my lap, positioning her legs on the outside of mine. I reached one hand around in front of her and slipped a finger between her legs, tickling her clit. I spread my legs, causing her legs to spread even wider while I circled my finger around her clit, dipping it once or twice inside of her vagina.

I could feel her body begin to tense at my invasion and then placed my other hand on her back, pushing her body forward, all the way forward until her head and shoulders were touching the ground in front of us. Then, pulling her legs up around my waist, I helped position her torso between my own legs. In this position she was trapped, her head resting upside down on her outstretched arms, and her body nestled tightly between my legs. Her ass was now positioned so sweetly on my lap. She couldn’t move. If she tried to wiggle free, all I had to do was wrap my legs around her body and hold her in place. She was so helpless and vulnerable in this position. Her anus and vagina so openly on display, as though I was resting a TV tray on my knees. There was also an added benefit of her being held in this position, that being that the underside of my cock could now rub against her clitoris and vaginal lips. I knew she was dying of embarrassment, and I also knew she was loving every minute of it.

“Ready?” I asked. Cindy didn’t say a word. I knew she would never be ready so there was no sense in her responding to me. I suppose that was her way of passively rebelling against what she knew she could not prevent. I just chuckled to myself and began to massage her ass cheeks while I enjoyed the view in front of me. Her bottom was so beautiful. Her ass-cheeks so firm, yet so soft. I spread her ass wide so as to get a good look at her lips and her sweet little anus. My cock began to grow harder and I knew she could feel it starting to pulse against her clit. I wondered if she could feel the sun’s warmth on her anus, and if it woke up any sexual desire in her.

I began my humiliation of Cindy by circling her anus with my thumb, starting at the center and massaging little waves outward. From time to time I would press my finger inward to add a little pressure. As my thumb caressed her puckering little anal ring, I reached down next the bench and began to coat the middle finger of my other hand with some bacon grease I had brought from the cabin. Once covered, I now began to massage her anus with the lubricant. Round and round in small circles I covered the outside of her ass-hole, pressing my finger into her little bottom. I felt her tighten up, trying to stop my invasion. “You know that won’t get you anywhere, woman” I said. “Now just relax and let me in.”

Cindy tried hard to relax her anus, but it was obviously not easy. I could plainly see her anal muscle puckering and relaxing as she attempted to gain control over her body’s natural instinct to keep my finger out. I smothered her anus with more grease and finally worked my way inside. After several minutes of the in and out motions of my finger, Cindy had relaxed enough to accept a second finger. I noticed the glistening mucus on her vaginal lips and took advantage of her natural lubrication by slipping my thumb deep inside. Her body tightened and I heard a small moan escape her. “I think you’re ready for your enema now” I smiled, knowing how much she hated that word. Cindy just kept her silence. The word “enema” could freeze Cindy in her tracks. She had a real love/hate relationship with them and I used this knowledge to my benefit.

Picking up an old funnel, I placed the tip against her ass-hole. “You know if you relax this will go a lot easier” I said. I watched Cindy trying so hard to control her anus and open it up enough to accept the funnel. I continued to apply pressure to the funnel until finally I felt it slip past her sphincter. I pushed it all the way in until the wide mouth prevented it from going any further. “Good girl” I said. “Now tighten up and hold that in place.” I saw her anal muscle constrict around the funnel as she followed my command. Reaching inside the bucket of water I had placed at my feet, I pulled out a tin coffee cup and began to pour its contents into the funnel. My cock pulsed now with each beat of my heart and I watched the water swirling in a cyclonic motion round and round in the funnel. I poured another cup full of water into her bottom followed by another, and then another.

After the forth cupful had circled its way into Cindy’s behind, I heard her begin to moan. “Please hurry up and get this over with” she cried. “This is so humiliating!”

“You’ve got four more to go young lady” I said “so just you be patient.” I felt her trying to adjust her body between my legs so I tightened my grip on her. “Hold still” I ordered. I refilled the cup and poured it again into the funnel. As the water worked its way into her bottom, Cindy began to rub her clit against my cock. Her own lubrication was enough to make the sensation very nice for both of us. Wet and sticky her juices glistened in the sunshine and made a lovely sight for a guy who had been alone for so long. I finished pouring the last three cups of water into her and Cindy continued to work her clitoris up and down against the underside of my shaft, driving me wild with delight.

As the last few droplets drained from the funnel, I tossed the cup back into the water bucket. I took a few moments to enjoy the sight in my lap, Cindy’s upturned ass spread open with the wide-mouthed funnel sticking out of it. I massaged her ass cheeks making sure I spread her wide enough for her to know I was staring at her ass-hole. I knew this humiliated her to no end, and brought me huge amounts of visual pleasure at the same time. “Well?” she groaned. “Are you going to take it out and let me get rid of this water?” I obliged, pulling the funnel from her ass, but did not release my grip on her until I had swatted her bottom a dozen times with my open palm. Her ass cheeks clenched, trying to lessen the sting of my hand, and helping her to hold in the enema water. I opened my legs and let her drop to the ground in front of me.
“Damn you!” she snarled, looking up at me. “I hope you enjoyed that.”

“Not nearly as much as I am going to enjoy watching you expel that water” I replied. I could see her eyes drop in shame, wondering what I had in mind now. I offered a hand, helping her to her feet. Cindy stood naked in front of me, head bowed and tummy swollen. “Look at your belly” I commanded. “You look pregnant.” Cindy rubbed her swollen tummy in shame. I knew the pressure was what she loved, though she would not admit it today. But I remember. “Now squat.” Cindy lowered her bottom close to the ground, causing her legs to spread wide, giving me an excellent view of her pussy. “Don’t you dare let any of that water out until I say you can. Do you understand me?” Cindy fought against the water begging to be released. I watched her face express the pain she felt in her belly.

With Cindy squatting in front of me, and her swollen belly screaming to be emptied, I decided to add a little extra aggravation to her predicament. I leaned back slightly and began to stroke my cock. Her face grew angry as I pleasured myself, so I met her anger with a taunting smile. After a few more strokes, and some well placed moans of pleasure, I stood up and moved closer to her. Instinctively she reached up with one hand and took my cock, guiding it into her mouth. With the other hand she began to massage herself to orgasm. Placing my hands gently on the back of her head I let her take my cock deep into her mouth. She continued to play with her pussy while she rocked back and forth on her heels, coaxing me to orgasm with her tongue. She worked hard for my orgasm knowing that the sooner I emptied my load into her mouth, the sooner she would be allowed to empty her bowels onto the ground. Cindy followed directions well. I felt her tongue dancing wildly on the underside of my shaft as she drew me further and further towards the back of her throat.

After a few moments she started sucking harder knowing that I would not be able to hold back any longer. She took my balls into her hand and began to massage them as though she were trying to squeeze the semen out of my cock. It didn’t take long before the semen flowed freely from the tip of my cock, coating her mouth and cascading over the back of her tongue, and down her throat. As she began to reach her own orgasm, I could hear the enema water splashing onto the ground under her. She had such wonderful control of her body, and such adoring obedience to my instruction. I knew how good releasing that water must have felt to her, just like how good it felt to me for the semen which had been pent up inside of my balls to be sucked down her throat.

After an unbelievable mutual release of sexual tension, we both caught our breath and began to relax a bit. I helped Cindy to her feet and pulled her close to me. Nestling her face into my chest, I could feel the tear drops of pleasure which had wetted her cheeks. She looked up into my eyes and I saw the pleasure from her I remembered from so long ago. “Thank you” she whispered softly. “It has been far too long since anyone has made me feel so humiliated, and so loved.” I knew exactly what Cindy needed, and I was more than happy to give it to her. We complimented each other in this way. I needed to give her enemas in the most humiliating way I could think of, and she needed to be humiliated in the worst possible way in order to feel needed. What a wonderfully perfect match we were.

I hugged her close to me and let my hands slip down to her ass, cupping both cheeks firmly. Cindy knew I was in love with her bottom, and she used that knowledge to get what she needed from me. “Are you ready for some diner?” I asked. She nodded and we gathered our clothes as we walked towards the cabin. We had a lot of catching up to do, and with the condition of the cities these days, I knew Cindy would not be leaving any time soon. I wanted to know more about her escape and how she managed to survive. I also wanted to know what her captors had done to her. In the back of my mind I had already begun to plan Cindy’s next encounter with my perverted imagination.

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