I had the day off from work today so last night was the first time in a while when I didn't have to go to bed kind of early. My job requires that I be up and rolling at an ungodly early hour so 11pm is usually bed time for me. We both intended on staying up a little later last night, initially because we were going to get into some kinky fun but when that did seem to be in the cards, just hanging out seemed like a good plan B. Well our chill out night quickly slipped back into some kink. The bottle of Everclear I opened for myself may have had some part in that too, but I digress.
Miss H gave the word to get dressed and it only took a hot minute before I was in stockings, platforms, and a short little dress. She then told me to run into the other room and get two rubber gloves, a bottle of penis numbing gel, my inflatable sex doll, and two condoms. Wasn't really sure what she had in mind but after being locked up for days without the slightest bit of attention being paid to the cock, I was desperate for anything, whether it was a plastic pussy or the real thing. I placed the doll across the bottom of the bed and gave her the rest of the supplies. She took the gel, squirted some into her gloved hand and began stroking me. I was writhing in pleasure, thrilled that she was finally touching me again. I felt a slight tingle from the cream but was still enjoying myself even though I could tell it was starting to work somewhat.
Miss H then slipped on the first condom, the feel of it rolling down my shaft making me groan with sheer joy. Then she unrolled the second one down the quivering cock before her. I was rock hard and out of my mind horny but I tried to remain still. I knew that if I tried to touch her or move she would get pissed and stop. I sat there frozen as I watched her squirt a big load of lube into the blow up dolls pussy. "You have one minute to fuck that doll as hard as you want. You're free to cum if you want and I don't mean a ruined orgasm either. You can have a full blown orgasm in it if you can. Your time starts now", she calmly explained to me.
I was shocked at how nice I thought she was being so I ended up mumbling something like "a real orgasm?". "Yes, but you better hurry up, you've already wasted some of your time", she replied. Like a hungry cheetah going after a wounded gazelle, I pounced on the doll immediately and furiously began fucking it for all I was worth. Miss H just sat back and watched with a smirk on her face as I attacked that plastic hole like a mad man in heat. Between the multiple condoms, the numbing gel, and the alcohol, it was hard to feel all that much so even though I normally can't last for more then maybe 20 seconds, here I was almost a full minute into it and wasn't even getting close. At one point I thought I might cum but I'm so used to holding back that I temporarily stopped just for a split second, but that was enough to break my momentum and the opportunity was lost.
"Time! Pull out now!", she yelled with a mix of amusement and disgust.
I did what I was told and pulled out. What I thought was her being nice was actually just cold blooded shit, for lack of a more precise term. When she told me I could fuck the doll till I came, my biggest concern I thought was going to be managing the post orgasm let down, but instead it turned out to be the frustration of physically not being able to do something I was given free reign to do. I know I must have sounded like a hurt little puppy when I pulled out because I was begging and pleading, whining and almost crying I was so horny and desperate for relief. "Aw, poor baby", she said sarcastically, "would you like another two minutes?". My eyes lit up and I pleaded for the opportunity even though I figured she was just toying with me and would soon say no.
"Ok, why not", was her reply. "Thank you Mistress", I blurted out before reentering the slick plastic folds of the doll. I pumped into it over and over again, sure that I would finally be able to feel the release I so desperately desired. Harder and harder I fucked it, grabbing her fake tits and like an animal slamming into it nonstop, occasionally looking over at Miss H while she just sat there with a look of utter disdain on her face.
"Done!", she shouted as I pulled out even more frustrated then before.
I had now gone three entire minutes without cumming which may not seem like much to most people, but was absolutely herculean for me. I rolled over to Miss H hoping that perhaps she would be in the mood to maybe touch me herself but she quickly put an end to that idea. "No, I don't think so", she dismissed me with her hand, pushing me away. "You can get into a diaper now, I'm done with you for the night". Not exactly what I wanted to hear but I did what I was told.
I soon returned and laid up against her after removing the condoms and diapering. I tried dry humping her leg a bit, hoping she might at least let me do that for a few minutes as a reward for being so compliant tonight. After a few seconds of rubbing against her outer thigh she leaned over and in a quite voice gently spoke, "how'd you like to cum in that diaper?". "Yes Mistress, I would love a ruined orgasm", I eagerly replied. "Not a ruined, a real one", was her response. It was almost to good to be true. I dry humped her leg from inside my thickly padded diaper while she verbally degraded me, calling me every humiliating name she could think off. It took a little while but eventually I felt an orgasm rising up and went for it. I could feel the I was cumming but the orgasm itself was very, very weak. I must have had so much numbing gel still on me that although I technically came I could barely feel it. I fell asleep soon afterwards, my cum filled diaper and lingerie making me feel so warm and content inside.