Replaced Chapter Seven

Replaced Chapter seven

Unlocking day.

I had no idea what to expect. What I did know was that there had been plenty of time for Vince to think about how to make my precious little window of sissy penis freedom interesting. I had been unlocked many times for hygiene, but each of those times I had been closely supervised, locking myself back up and giving the key back to Vince immediately. But this was different. For the first time since he moved in, Vince had finally told me I earned a true release.

The kids were playing in the neighbors’ yard and wouldn’t be back for over an hour. I couldn’t stop trembling from excitement. Vince walked ominously behind me down the stairs and instructed me to open the door to my room.

There was Kate…completely naked, lying on my maid’s room bed on her back, with her legs spread. I thought I would lose my mind at the sight. She looked impossibly tantalizing, and impossibly delicious. I could already imagine how it would feel to bury my rock hard three inches into that sweet pussy. She smiled at me and winked, and my heart fluttered.

I started to make my move.

“Not so fast maid. You’ve earned a release, but not quite that easy of one.” Vince closed the door behind him and locked it. I really really really did not like him at all at that moment.

“You do get to cum, but only if you follow the rules. Got it?”

“Yes Sir.”

I was so entranced with the sight of my naked wife that I had failed to notice the crazy contraption laying on a towel on the floor. Either Vince or Kate had taken a large ice bag and drawn a feminine cartoon face at one end, with huge exaggerated eyelashes and big fat lips. At the other end a small slit had been cut, with little curly pubic hairs drawn above it.

“Maid, meet your new girlfriend” Vince said, his voice rolling with sadistic amusement. “Don’t worry, I know you can be intimidated by beautiful women, but Icy here is right at your level. I’m sure you won’t have any trouble seducing her.”

He chuckled, giving my ass a smack. “Don’t be shy sissy…go give her a kiss.”

I blushed, getting on all fours over the ice bag and lowering my head to kiss the ridiculous lips drawn on with red marker. Kate didn’t stifle her giggles. This was quality entertainment.

“Good sissy. See, isn’t she sweet?”

“Yes Sir” I said, my lips now cold and a little sticky.

Vince took a slightly more serious tone. “You have two options maid. The first is to put your little excuse of a penis into Kate. If you choose that option, you will have one extra month in chastity for every tiny thrust in her pussy.” He paused for a second. “I know these things are hard for your little sissy mind, but just to make sure you understand, can you tell me how long you will be in chastity if you push your penis into her six times?”

“Yes Sir, six months.”

“Very good.” He directed my attention to Icy, laying on the now damp towel as her contents slowly started to melt. “Your second option is to spend your unlocked time with your new girlfriend. You two can make passionate love for the next hour if you want, exploring each other’s bodies…” he stopped, turning sternly to me. “One hard rule with both options…your penis absolutely cannot touch anything other than your girlfriend’s pussy or your wife’s pussy. I’ll be watching. You try to rub against anything else and I will lock you back up immediately and spank your balls. Got it?”

I nodded weakly, whimpering as I started to understand my predicament. “Sir may I put my penis in both of them?”

He thought for a second. “No. Pick one.”

I whimpered again. It was a cruel choice. I tried to guess how many strokes it would take to cum in Kate’s pussy…could I do it in four…six…ten? It had been so long; surely it would take almost nothing for me to spurt my load. But what if I thrust three or four times and didn’t cum? I would have to go back into chastity with no relief, and then have to wait any extra bunch of months just for another chance.

Kate wasn’t helping. She pursed her lips playfully at me, her fingers tantalizingly dancing around her pussy lips.

“Come get it big boy.” She said seductively. “You know you want it.” I regretted those years of telling her I craved for her to be a heartless mean bitch to me. She was now just giving me what I had asked for, and enjoying it as well apparently. I dreamt of being on top of her, thrusting over and over, pumping my little load as deep as I could.

I couldn’t do it. I couldn’t risk the horrible predicament of being six strokes in and unable to cum. I looked down at Icy, noticing Vince had drawn cartoonish little breasts on her. I gulped, taking one last look at my beautiful naked wife before taking my position on the floor, hovering over my new girlfriend.

Kate laughed as I made the choice, and they both laughed hysterically as I started the awkward process of trying to penetrate the ice bag.

The “vagina” slit was small, but I had no problem getting the rock hard tip of my penis through the exterior of the bag. But once I was inside, my little rod was met with crunchy cold chunks of ice cubes clinging together in obstinate clusters. I probed and poked to try to find a soft enough spot to really be able to thrust, the harsh ice incredibly cold against my skin. I whimpered and groaned as they laughed, trying desperately to find anywhere in Icy’s pussy that I could feel anything other than the sting of cold hard blocks of ice.

Finally, thank God…a little seam between rocky ice clusters. I desperately thrust deep into the ice, my hips grinding against poor Icy. My wife and her lover erupted into a new shower of laughter as I started pumping, my ass bouncing up and down as I fucked the ice bag.

“Not much of a gentleman is he?!” Vince laughed, now sitting on the bed beside Kate. “Good thing Icy gives it up on the first date!”

Kate was laughing harder than she should have. I didn’t find it that particularly funny.

I felt my penis starting to soften from the extreme cold of being buried deep in the ice bag. I knew I needed to cum before it was too late.

I whimpered pathetically as I managed to spurt my little load into Icy, with my wife’s amused laughter ringing cruelly in my ears. It was an orgasm at least though. I did feel some semblance of relief, even through the intense shame and humiliation.

I immediately rolled off Icy and knelt at Vince’s feet.

“Thank you Sir for letting me cum.”

“Good maid.” He said with a chuckle. “Now, be a good sissy and clean up your girlfriend’s pussy.”

I nodded, getting down on all fours again, this time burying my face into my girlfriend’s pussy, licking up globs of sticky cum from between the blocks of ice.

“Aww…so sweet. What a good sissy.” My wife said as I swallowed my own cum.