As She fucked me, She ran Her hands over my body, alternating between lightly touching me with Her fingertips, and lightly scratching me with Her nails. She occasionally grabbed my hips for leverage. Sometimes She would reach around and play with my package a little bit.
She would occasionally pull the dildo out and use Her fingers instead. I could feel Her spreading and stretching my asshole out with Her fingers. Later She told me that She almost got Her whole hand inside. Someday, I hope She will.
She fucked me laying on my stomach on the bed, my neck bent, my head and hands pressing against the wall. Then She had me get up on my knees and fucked me some more. “Oh god. Oh fuck. Oh yes. Thank you Ma’am!” was all I could say to Her.
When She tired of fucking me with the strapon, She had me fetch my large double ended dildo. This dildo is about eighteen inches long, with one end tapering down to about one inch in diameter and the other side being a solid two inches thick. “Which side is mine?” She said.
“Whichever one you want Ma’am! Probably the thicker one, ” I replied. She concurred with a smile.
She lay on Her back with Her legs spread. I lubed up the double dildo and inserted the thicker end into Her pussy. She had me hand Her multi-tailed whip to Her before allowing me to mount the other end of the dildo. I got on my knees with my back facing Her and lowered myself down onto the tapered end of the dildo. The backs of my thighs pressed against the backs of Hers.
I bounced up and down on the dildo, which easily slid deep inside my ass, slightly penetrating my sigmoid colon. She occasionally flogged me with Her multi-tailed whip. I rode the dildo harder as She struck me. Both my ass and Her pussy were being fucked by the dildo as I bounced. She nearly came three times, but sadly we were not able to get Her over the edge. Such a tease.
When She had given up the double-ended dildo, She directed me to don my chastity device. She told me She wanted to watch me cum while caged. I had recently admitted to Her that I had made myself cum a couple of times while She had me locked in chastity. Despite Her initially being justifiably upset by my transgressions, Her curiosity had been piqued.
It took several minutes to get myself into the chastity cage. I had to soak my balls in warm water before they would drop enough to get them through the ring, as usual. I am hoping warmer weather will make that process easier. I struggled, but I was finally able to get my genitalia securely locked in the device.
I inserted my remote controlled vibrating butt plug into my ass and set it to Sound mode. In Sound mode, the frequency and intensity of the plug’s vibrations are controlled by whatever sounds are picked up by my cell phone’s mic. I put some porn on the bedroom TV to get the anal vibrations going. Then I turned on my Hitachi “massage” wand and placed it against the tip of my caged cock. The vibes from the Hitachi are fairly intense, even on the lower setting.
I sat on the bed for several minutes and tried to cum while my Owner watched, but it wasn’t happening, not even close. She allowed me to relocate to the living room, in front of my computer, where I had been the last couple of times I had made myself cum this way. I set the computer to play on the big TV and surround sound. I queued up a song that is special to my Domme and I, set it on repeat, then pressed play on some prostate-induced orgasm porn.
The song played on repeat several times. I was positioned so I could see both the TV and my Owner, and She could see everything that I was doing. The butt plug vibrated to the sounds of the music and the porn. I held my vibrating Hitachi wand against my caged package.
For the most part, I closed my eyes and ignored the porn. Porn is usually just inspiration for me. It’s mostly just to help get my imagination going, which is where the real fun usually happens. Occasionally, I would open my eyes and see my Domme staring back at me. Being watched that way was incredibly hot, but I definitely had some performance anxiety.
Finally, I was getting close to climaxing. I was right on the edge of an orgasm for at least thirty seconds. Then finally I came, incredibly fucking hard. The sensations of pleasure echoed back and forth between my cock and prostate for half a minute or so as I moaned and cum pumped from my caged cock and pooled on the floor. I looked up to see my Owner smiling. I cleaned up my mess.
I was relieved that I had been able to show Her how I could cum in the cage. I almost didn’t think that I was going to be able to get there with Her watching. She told me that She knew when I was about to cum and almost had commanded me to stop right before I did. That would have been so mean! We laughed about the idea together. I was thankful that Her curiosity had outweighed Her sadism in this case.
After I cleaned up, we returned to the bedroom. She had me use my fingers to bring Her to orgasm several times. Then She allowed me to clean Her pussy with my mouth. I made Her cum several more times before She decided She’d had enough. I will never get tired of serving Her pussy.
We got cleaned up, and She taught me how to make Her shepherd’s pie. It was probably the best shepherd’s pie I’ve ever had. I made bacon-wrapped jalapeno poppers, another recipe She taught me. They were incredibly delicious. We snuggled and watched TV together and sipped wine while we ate. She lay on me for a time while we watched one of O/our favorite shows.
When She was tired of TV, we migrated back to the bedroom. She allowed me to massage Her for a while, and rub lotion all over Her body. I love when She allows me to massage Her ass. I could worship Her plump, round ass all day long. When She was sufficiently relaxed, we lay in bed and talked for a little while before falling asleep. My ear that She had bitten hurt any time it was even lightly touched, and kept waking me up throughout the night.
We lay in bed and snuggled for a bit when we woke up. I had to go to work that day, but She didn’t. She had me finger Her to orgasm several times before I had to get ready for work. When She’d had enough, She allowed me to lick Her juices from my fingers.
I went through my normal routine of getting ready for work while She stayed in bed. My ear had a dark purple bruise where She had bitten me, and the rest of the cartilage was a deep red. You could see where one of Her teeth had broken the skin. Even the lightest touches to my ear caused acute pain in the spot where She had bitten me. Showering was very uncomfortable, with the water constantly pattering against my ear.
When I was about ready to leave, my Owner allowed me to clean Her pussy with my mouth. I was eager to oblige. I cleaned Her pussy well enough to provide Her with one more orgasm before I had to go. I snuggled Her and kissed Her goodbye before I left. When I returned from work later, I was pleased to find that She left a lipstick kiss on my notepad for me. She can be so sweet when She wants to be. My bitten ear was still bruised and sore over a week later.
My Owner later asked me what my favorite part of the night was. I’m still not entirely sure. I loved being pegged by Her. I loved feeling Her fingers stretching out my asshole. I loved sharing the double-ended dildo with Her while She flogged me. I loved making myself cum in chastity while She watched. I loved massaging Her, and bringing Her to orgasm with my fingers and mouth. I loved when She kissed me. I loved having dinner and watching TV with Her. I loved cuddling and sleeping next to Her.
Of all the things I loved about that night, I think my favorite things were the things that gave Her the most enjoyment. She loved stretching out my ass with Her fingers. I can’t wait to feel Her whole hand inside me. She loved sharing the pink double-dildo with me. I only wish I was able to make Her cum that way. She loved watching me make myself cum in chastity. I loved opening up my eyes to see Her staring at me.
What did I really love the most about that night? It was probably all of the attention that my Owner gave me.