Ninety Days Ch. 03

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Mistress begins making her slave a cuckold.
1.4k words
4.34
40.2k
6

Part 3 of the 4 part series

Updated 10/30/2022
Created 04/25/2007
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chasteguy
chasteguy
47 Followers

I busied myself throughout the evening with mundane tasks, trying to keep my mind off of Mistress and her date. It was nearly impossible and I paced through the house with a semi-erection all night as I imagined her on her date. I wondered what he was like; what he smelled like and tasted like. I let my mind wander to his imaginary cock, hoping it was stout and well-curved. I tried to imagine what it would feel like in my mouth and ass, and what his cum tasted like. I pictured too him pleasuring Mistress while I was left to watch, caged and trembling, wishing that Mistress would allow me to please her too but knowing my place was to never have intercourse again.

Around midnight Mistress called. "I should be on my way back there within the hour and I expect Amber to greet me," and then she hung up before I could say another word. I didn't know what to think. Was she bringing the boy with her? If not, why Amber? And how did she want Amber dressed?

I quickly set the phone down and immediately started getting ready. I was thankful my body was freshly shaved and my toenails newly painted. The first thing I did was make sure I was clean, for once not minding the slight hunger I felt brought on by my purposefully light appetite on days when Mistress may want to use me that way. But really, how did I know what she wanted? I had learned over the past four months that Mistress sometimes wanted the unexpected and it was one of the things I loved about her.

I selected my attire carefully, something mixed between sexy and subservient. Because of the ever present cage, I opted for garters and stockings under my short black and red teddy and because of the hour, a waist cincher instead of a corset. I applied my make-up carefully, spending extra time and effort on my eyes, giving them something of a sexy, sultry look that invited exploitation. For my lips I chose something sparkly and sexy that begged for cock but could look good without it. Because really, all I wanted was Mistress to find me wanting. Lastly, I selected my black bob wig, deciding to skip the shoes and wait for her in bed. But before retiring I checked my look one last time and decided that I was as beautiful as I was going to get.

I didn't have to wait long as I heard the door open somewhere around 12:45 am. My heart started pounding and I listened carefully for the number of footsteps and hearing only hers felt relieved and disappointed at the same time. She came directly into the bedroom looking slightly disheveled but wearing a happy grin. "Well hello," she said in a tone that almost suggested she hadn't expected to see Amber. I simply smiled at her. She went immediately to the toy closet and took the strap-on harness from its hook and then selected the second largest dildo. I watched all this somewhat incredulously as she seldom went straight at it like this. She also must have known I was extremely curious about how her evening went. She set the harness and dildo, as well as lube and two towels on the bed and then quickly undressed, still without saying a word.

She began pulling the harness up, tightening the straps on both sides and then affixing the long and thick black cock to the ring. She took a small bullet-type vibrator and wedged it between her clit and the harness where the pressure from thrusting would add to her pleasure. Without really looking at me she instructed, "Take off your panties and then get on your back." I did as I was told; wanting to ask her about her evening but sensing that now was not the time. I was trembling slightly as I assumed the position she required, hoping she would remove the cage but suspecting she wouldn't.

She took the lube and quickly greased my ass, then the dildo, and then with no other foreplay positioned her cock at my hole. She moved the large head of the cock in a circular motion and then pushed it inside me. I tensed and whimpered. She didn't seem to care and pushed in a little further. I was not opening up for her and the largeness of the cock felt like it was ripping me apart. She applied more lube and thrust in another inch or two. My ass began to loosen and she slid the remaining six inches in. I felt stretched and impaled although my body was becoming accustomed to the violation. Slowly she began thrusting, almost as if she was making love to me. I watched her, my body finding the rhythm that matched hers and the pleasure began to take hold. I moaned softly and wrapped my legs around waist.

With her eyes still closed she began speaking, her words sometimes interrupted by our mutual sighs of pleasure. "You'll need to get used to a big cock in your ass," she whispered as she continued rocking in and out of me. "Our boy has a lovely large cock. I stroked his cock in the car tonight before I came home. I could barely get my whole hand around it he was so hard and hot." She moaned a little louder and increased her pace. I met her thrusts and begged her in a whisper through clenched teeth to fuck me harder. My cock, stifled in the cage was tingling and the frustration and arousal caused my entire body to tremble. The feeling of her cock deep in my ass and the pressure it placed on my swollen prostate combined to make me feel like I would orgasm and I hoped that I would. She continued, "The expression on his face when he came was beautiful and the thick ropes of come he shot all over made me think of you. Aren't you glad that someone gets to come?" I moaned and in a pleading voice, "Yes, Mistress, yes. I am glad he came. He should cum often and you should too." She cut me off. "Oh, we will."

She started fucking me harder, more violently, her teeth gritted and her face contorted in concentration. "We will cum often, with each other, using you, however we want," she hissed, thrusting into me and moaning, breathing deeply. With her large cock deep inside me with each downward push I felt like I would be ripped apart but I didn't care. I returned her thrusts, grinding up into her with animalistic intensity, feeling closer to cumming and willing to do anything to make it happen. My pleading began anew, "Yes, Mistress, fuck me. Please fuck me. Fuck me harder and use me. I just want to be your bitch. Please, Mistress..." My words trailed off and the miraculous tremors of an orgasm denied these past four months began building inside. I knew it wouldn't take much more and I would finally have the release I was so madly craving.

Mistress was lost in her own place, thrusting and moaning, perhaps not even knowing who she was fucking. "Oh God!" she screamed and her body began shaking violently as she pressed into me and ground her cock as far as it would go but otherwise holding still as her orgasm swept through her body. I was almost there too and needed her to keep the thrusting motion going so I began moving my hips back and forth, hoping to bring the orgasm teetering on the edge inside me. Mistress whispered for me to hold still and despite her words I continued rocking slowly, trying to cum. She looked at me through squinted eyes and reached out, wrapping both of her hands around my throat, closing the air passage. My eyes widened and I watched her intently. "I said hold still," she repeated through labored breath as she met my gaze. She loosened her grip on my throat slightly and I gasped for air before she tightened the grip again. She thrust into me three more times, sending a spasm through my caged cock and then withdrew from me while releasing her hands from around my neck.

I bucked and moaned, begging her to let me cum, my head spinning and my entire body trembling. "No," she said, "there have been enough orgasms tonight. It's time for sleep."

chasteguy
chasteguy
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AnonymousAnonymousabout 3 years ago
Super cuckold training

I really love the cuckold life style. This story confirms this feeling and need.

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