This will probably be the last reflections post. A big thank you to everyone has taken the time to read them. A big thank you to Lady Grey for giving me the inspiration to take on this endeavor.
There are two events I have shared with T that shook me on the same level that my early experiences did. One of them was a shopping trip where we bought some skirts, garters, and stockings at a local store that caters mostly to strippers. It's basically a repeat of awkwardness that I have recounted a couple of times already and not all that interesting.
The other event has a bit of history behind it. There were some things in D/s that I just didn't like the idea of or care to experience. While my initial list of hard limits I composed for K had shrunk by now to only a few things, those limits did still exist. T hadn't quite developed the tools to break me in those mattes, so we sort of just let them go. Basically, I agreed that with certain things, I was okay if she played with other subs to make them happen if they were important to her.
T had a couple of subs she had played with semi-regularly before I met her. They were not romantic interests and they were into things I didn't care for, so it let it go. As long as she didn't have intercourse with them or perform fellatio, I was pretty much fine with whatever and wasn't jealous about it.
One of the subs had two things he really enjoyed: cleaning with inspection and being badly beaten. It ended up being a win win for him, and a win win for T. e.g. When she moved, he helped do the cleaning in exchange for a beating. Unfortunately, his form of cleaning was more of a Femdom fantasy cleaning and less of a practical cleaning. She asked him to clean the bathroom. He got on his hands and knees with a toothbrush. 4 hours later, he had successfully thoroughly scrubbed about 1/10th of the bathroom and then had to leave with the remaining 9/10ths unfinished. I don't particularly enjoy cleaning or pain, so if he wanted to do that and she wanted to whip him until he bled, hey, better him than me.
However, T had another major fetish: pegging. This didn't really bode well for my nothing up the butt hard limit. A few years ago I started frequenting the Fur Fashion Guide forums, which was a VERY active fur fetish site with many fur Dommes and subs in the mix. I decided to put my location on my profile and after making an introduction post I was contacted by one of the admins who was also local. He had a very large fur collection and begged me to chain him to a horse and fuck him up the ass. I declined. He kept pressing. That type of interaction is of no interest to me and on top of it, I can't even get it up unless I'm the bottom. He continued and offered up a fur coat as payment for it. At this time T had gone several years without any form of anal play for my sake, so I took a shot in the dark and responded I might know a woman that would be interested in pegging you for a fur coat. I think he almost crapped his pants as that was what he actually wanted and was willing to have a man fuck him if that was his only outlet for it. He sent me pictures of the coats she would be allowed to choose from. I told him I would get back to him.
When I approached T I told her I didn't mean to pimp her out, but a local guy on a fur forum is offering a fur coat if you'll peg him. Her eyes lit up and she was very interested. We set up for a dinner meeting to get to know each other. We ate dinner and talked and had a pretty good time. He was a decently fun guy to spend time with, which made me question why he came off as strongly as he did via internet chat. We ended up going over to our place and he took a look at her furs (as well as mine).
We picked a date for the event that would happen at his home. He had the equipment and a brand new Feeldoe he had been saving for this day. T wanted to make a production out of it. So we planned things out a bit in advance.
When we arrived we went to a room to change. T put on her Domme clothing and fur (corset, stockings, boots, gloves, etc.). She had me dressed up in full (fur items, sweater, stripper skirt, stockings, garters, boots, a fur jock strap that left my ass exposed, and a black bondage mask) including a collar, cuffs, gag, and bondage belt. When we went downstairs he had porn going on the TV. T had secured my wrists to the side rings of the bondage belt, restrained my ankles, gagged me, and was leading me around by a leash. This was my first time ever being seen by an "outsider" while dressed, but he was wearing something so similar it didn't bother me. T plopped me down on the couch facing away from the horse, put a vibrating egg in my jock, and turned it on before walking away to "do the deed."
It must have been about an hour before she returned to me and turned off the egg. The nerves in my penis were so overstimulated that it hurt. She led me over to the horse, unlocked the chains and locked me to the horse. T ended up whipping me with a few things, spending most of her time with a crop but also a switch and paddle. Afterwards, we changed and when we got home we went at it voraciously in the shower. For a while, this improved our sex life. We had some play with the other guy a few more times before I started noticing some changes in her behavior.
T started being gone more often. She would "go to the store" and not return for 6 hours, telling me later she was with him. T is the type that easily loses track of time and will often forget to text saying when she is going to be late. Some days we would plan on going out for dinner but she wouldn't come home until 9:30pm because she was with him and lost track of time. Eventually we had less time together and he was getting the majority of her free time. I let her know it was bothering me but she replied that she was just doing what I said was okay to do.
This continued for several months. By then we were barely getting any time together and she was seeing him 2-4 times a week. It capped off one year on new year's day when I woke up and she wasn't there and didn't answer calls or respond to texts. She came home at 3:30pm. She had gone over to peg him at 6am and lost track of time. My feelings were hurt and I let her know that. I don't think she understood what it was doing to me. I hardened my resolve and decided to do something about it. I chose a day when I knew she wasn't working and asked her to save that day. After dinner I told her to come to the bedroom in 15 minutes and I went in and closed the door. I had to act fast as I wasn't sure just how logistically difficult it would be to get it all together.
I quickly stripped and put on a CB-6000. I followed with the entire "sissy whore" ensemble she had picked out: Thigh high stockings, garters, 4" heel knee boots with fur leg warmers over the top, a fur jock strap, a tiny micro-mini skirt, a prickly tight sweater, a cropped fur jacket, fur trimmed gloves, my collar, gag, fur pom pom hat, and earmuffs. A blindfold was in position to go and I had put in earplugs, which combined with the layer of the hat and earmuffs made me nearly deaf except for the sound of my own breathing and heartbeat. I buckled on the wrist and ankle restraints, quickly putting locks in each one's locking buckle along with the gag and collar. I put a leash on the collar and I attached an 18" spreader bar between the ankle restraints and stacked up some pillows on the bed and leaned over them as I climbed on. The last part was tricky. I pulled the blindfold over my eyes and proceeded to lock each wrist cuff directly to the ankle cuff.
My face was pressed on the bed, unable to see, speak, or hear. The pillows forced my butt up in the air. The spreader bar kept my legs from closing and I could barely move. I was completely vulnerable. I left a paper shopping bag in the middle of the floor and a note with big letters saying "PLEASE DO WHATEVER YOU WANT TO ME." I waited what felt like forever. T had lost track of time, but when she finally did arrive she was surprised. I'm sure she found the bag. Inside was her favorite crop and a paddle and a strap on harness.
I felt her hand caress my bare bottom. She slapped it a few times. I was breathing so hard that I couldn't hear anything else except the impact. Next came the crop. It struck my skin and I let out a grunt. Again and again it bit my flesh. I squealed from under the gag. I could feel my butt cheeks begin to heat up and swell. The strokes stopped for about a minute. They resumed but with a much sharper, more violent sting. I had guessed she changed devices over to a fiberglass switch that had a thin knotted rope at the tip. With each impact I felt a deeper bite into my skin. I could tell these were leaving marks and this was the hardest that T had ever hit me. I bit down on the gag and let out a muffled yelp with each strike. T continued to strike me for several minutes, moving the impact points around to give a large area of coverage. I began to cry. The impacts stopped. My entire buttocks region was burning, swollen, and covered in welts.
The next thing I felt were her hands on my waist. The tears were still flowing but I let out a whine. I felt her finger touch the crack of my ass and some fluid. She spread the fluid around. I cringed, closing my butt cheeks. My breathing became heavy and erratic. I began to sob and struggle but my movement was so limited by the restraints it didn't do much. I felt the tip of the dildo against my ass. Tears were flowing in full force by now. I tried to shout but the gag prevented the words from forming: "No, Stop!"
The tip entered me. "No, please stop! Stop!" I shouted against the gag. The earplugs translated it clearly back to me: "Mmmmmp! mm mm Mmmp!" She slid it in. I shrieked and wailed, fighting against my bonds. I was hyperventilating. "No!" She pressed on and stopped with it inside me. "Take it out! Please take it out!" I bawled. At that moment a new feeling appeared in me as I lay there with her dildo in my ass... the feeling of being ultimately violated.
She slid out and back in. I screamed and thrashed. Again in and out and back in, holding it there. I crumpled and went limp, completely defeated. T slowly pulled out from inside me. A few moments later I felt her undoing the gag. I wept and whimpered. "Please no more..."
I heard traces of her voice. "Earplugs," I gasped between sobs.
T pulled off the hat, earmuffs, and blindfold and removed the earplugs from my ears.
"Are you okay?"
"No... I'm broken..." I was breathing in gasps.
T undid the rest of the restraints and sat on the bed. I crumpled near her with my head on her lap. I couldn't stop crying. She ran her fingers through my hair and looked down at me with tears in her eyes.
"I shouldn't have done this..." she whispered.
"It's okay. I did this for you."
"But it's hurt you so badly..."
"I did this for you. So that I could be enough for you."
"I love you," she said with tears still in her eyes.
"I love you too. Did you like it?"
"I loved it."
We stayed like that for a while. I could tell that something inside me had changed. I now felt like I was willing to do anything to make her happy.
We took a shower together after that. She was covered in her own juices and I was covered in sweat and lube. In the shower I went down on her with a combination of fingers and tongue and made her cum until she didn't want to anymore. When it was time for my reward I placed my hands on the wall and spread my legs.
"Would this make you happy, Mistress?"
She inserted a finger inside of me. The feelings of violation returned and I began to weep.
"I don't like this, Mistress."
"Too bad, your ass belongs to me now."
She pulled my left arm behind my back and pinned it behind me with her body. She then moved her left arm around my neck and put me in a choke hold, while keeping her right hand's fingers in my ass.
"Now stroke it like a pathetic sissy whore who just got raped."
I did as instructed. My penis was already rock hard. I continued to cry.
"I love your tears, slut."
"Mistress, I don't like this..." I pleaded.
"Tough," she replied as she pressed her finger deeper.
"May I cum please, Mistress?" I sobbed.
I let out a wail as I came. T turned me around and held me close while I sobbed away. When I regained my composure I washed her body and hair and gave her a deep kiss.
In the aftermath, T asked me why I went so heavy on the bondage and the chastity device for that. I answered her honestly. If I had left any glimmer of daylight to escape it, I knew when faced with the situation I would have fought like hell to take it. By locking everything and being in an inescapable position, that choice was removed. The gag and blindfold were for her. I believed if she saw and heard just how upsetting it was for me that she would have stopped before her desires were fulfilled, and if that happened, there would have been no point in doing it in the first place. The CB was also for her. I knew T had a pretty strong fantasy for raping a man with a strap on and I figured removing any chance for sexual pleasure helped reinforce that fantasy.
After that, T started spending more and more time with me. While she would still visit him every so often, it was relatively infrequent and usually when I had made other plans as well. As painful as it was emotionally for me I felt good that I was able to be enough for her. In the time that followed, anal play became a regular part of our interactions. However, to this day, I still cry every time something gets put in my ass.