Living with Madam Darling

@Madam Darling has required that I begin a journal here. She said she wasn't going to, but I accidentally let the moving truck take the new collar that I was supposed to begin wearing once we got to our new town. We got here, and she asked me where it was. I knew this would be a big deal to her. I was right.

She and I don't really live a lifestyle that anyone else would recognize as kinky. We have kids who live with us and we are careful so there is no way they will detect anything is different between us and other vanilla couples. But she will often tell me to do something for her--any kind of innocuous directive--and she'll give me her signature look that always gives me butterflies. If no one is around I'll say, "Yes Madam Darling" in a very quiet voice. Then she'll give me a look of approval that makes me proud.

We met in college about 7 years ago and I fell in love immediately. One of our first days of English class the instructor called for volunteers to step up in the front of the class and answer questions. Madam Darling's hand shot up and she went forward. She was the only volunteer and the instructor chose someone else at random. But Madam Darling's confidence and grace was awe-inspiring.

After class one day I walked her down to student parking. We had parked closely to one another. She got into a small SUV that had handcuffs hanging from the rearview mirror. This was all I could think about until I saw her next. Every spare moment my mind was wandering back to the handcuffs.

The rest of the class was largely uneventful. We had only spoken a few times, but the cuffs were always on my mind. I only knew her first name and didn't spend much time trying to find her. The next quarter at school we didn't have any classes together and I didn't see her around campus. Then a few weeks into the quarter I saw her run down the hallway by my world literature class. I heard someone call her name and I jumped up to see where she was going. I left class a couple minutes before class was over and waiting in the hallway hoping to see her.

Madam Darling came out of her class and she saw me and nodded. We walked down to the parking lot again. I said, "it's nice to see you again. Is it weird that I kinda missed you?" She said, "not at all. You're SO handsome." And I just let that sink in rather than return the compliment. Then I saw her get into a different car than she'd had before. I asked about the car with the handcuffs and she said she had borrowed it. I said, "oh, that's too bad. I was wondering if they would have been for me or for you." She got a sly look that I've come to recognize well and said, "Oh, they would have been for you."

After that we would meet after class every day and walk together down to the student parking. She saw my sport bike and got very excited one day that I had ridden it to school. She rides motorcycles, so that gave us another thing to talk about.

I'm sorry if this is not exciting enough, but this was a very crucial time for me in my life and if it's my journal I'll begin with this every time. I like remembering her back then because I thought this would be the most exciting our relationship could get. I had no idea that it would get more exciting than anything I'd experienced just a short time later.

 

In my previous marriage I had to be dominant in the relationship. She was a very, very conservative christian and subservience and obedience was in her nature as a part of her upbringing. Her pastor had said over and over, "if it doesn't involve kids or animals anything is open sexually in the marriage." The translation was to please your husband as long as it didn't violate the law.

I'd had discussions with my ex about chastity and it didn't go well. We tried it, but she hated it. She noticed that a lot of men wear panties who enjoy chastity. And while I didn't say anything to her about wearing them she piped up with "that will NEVER be okay." A short time later our marriage was over.

But then after meeting Madam Darling in college it was such a relief when she said those handcuffs would have been for me.

We eventually got together. We had begun texting and eventually met up at my place. I told her I had only had sex with one other person in my life and I was apprehensive to do anything physical until my previous marriage was officially over. I didn't realize what a long process that would be. Madam Darling mentioned the amount of time that meant I would likely be waiting and then she tried to seduce me. I told her I had no condoms because it was something that I didn't want to do yet. Two minutes later and she had convinced me to play "just the tip." I think I lost.

After this first experience we began getting together at her place. The second time we'd had sex she asked me if I would wear a garter belt and panties for her. I agreed, but on the inside I was ecstatic. What I didn't tell her was that I was transgender. When my ex told me that would "never be okay," she was commenting on my identity without knowing. When Madam Darling told me she wanted me to wear panties and a garter belt she couldn't have known how affirming that would be for me.

She told me that she's had all of her ex's except one wear her panties before. The most affirming thing about this was that she was the one requesting it. She wasn't doing it to make me happy, but she obviously had her own opinions in bed and she was not shy about voicing them at all.

Her only request was that I be confident if I wear them. Which I was. Until I had an orgasm. Then I immediately became ashamed and kicked them off as quickly as I could. This was something the two of us have spent time working through, but now I'm in a position where I can wear anything anytime and it's never really a problem for me.

 

A few times during sex I'd tied Madam Darling up. I tied her with a rope around her wrists holding them together in front of her. Her hands were together in a praying type position. I had her get onto our tall bed with a footboard made of thick solid cedar. It had several round boards that we very secure.

I put Madam Darling on her knees on the bed. I tied her ankles to the footboard so her legs were spread wide. Then I took the rope from her praying hands and pulled tight to wrap the rope around the footboard then dropped the remaining rope to tie it to the bottom of the bed frame. She was still sitting up on her knees, but then I tied a rope around her neck and pulled her down so she was laying down on her chest. I tied the other end to the rope to the headboard. I pulled it tightly so her neck was being stretched out and secured out of reach, and her wrists were keeping her shoulders pulled down between her legs.

I watched her closely to make sure she was still breathing, but Madam Darling has a vein in her forehead that tells you when she is angry or under stress. This vein was talking a lot during this experiment of ours. I asked her several times if she was okay to continue and she agreed. The strain on her neck looked intense. And I imagined I was her. Even though she had told me that cuffs would always be for me we decided to experiment like this a couple of times.

And I kept imagining that I was her. And I climbed up on top of the bed and I had my way with her. The bouncing of her ass and the arching of her back and the tugging on her neck was all too much for me. I came quickly.

I asked her if she liked it and she said, "not really." We tried this again later, but it was obvious that our personal dynamic required something different.

 

Thank you. It seems to be great right now.

The first time I introduced Madam Darling to chastity she didn't really know what to make of it. I told her that I would love be denied an orgasm and have her tease me, but then keep me locked away so I couldn't relieve myself.

One of the things she mentioned is that she enjoys when men masturbate. This was a major difference between what I had in past relationships where it was perceived by my partner as sinful. Some of the play Madam Darling and I started with was her having me masturbate for her. She would regularly ask me when I had because she loved it when I was so horny I had to relieve myself.

So chastity was a bit foreign for her. I also don't think she understood how much of a pull something like this could have on a man. I tried to explain it as well as I could but I'm sure I didn't get my point across the first several times. But she knew after that that I fantasized about being teased and denied.

In the first year of being together we has sex 6-7 times per week. This left us a lot of time to experiment with each other and get to know our likes and dislikes. She was very adventurous and it felt great for her to tell me I was the best lover she'd had. She would never make something up to make someone feel good so I believe her and that made me feel extremely happy because I had wondered if I would be too much for her now that I had someone I could share all my sexual thoughts with.

Our first major kink experience was when she had me tie myself to a workbench in our basement. I was to do this after I got home from work. She still worked 2 more hours at work so she knew I would be there a long time. She set up the parental controls on my phone with a password so I couldn't do anything with my phone except text her if I had a problem.

Madam Darling told me to wear some pink panties she had bought for me and to tie my ankles to the feet of the workbench. This spread my feet wide apart. I was also to tie my knees to the legs of the bench so I couldn't close them at all. After that I was to tie my hands far out in front of me so I was laying across the bench in the center of the room. It was just a 4 legged island type workbench, but I was unable to move it while in this position. I secured my hands with a ratchet rope so that when I pulled the rope it would tighten and I was unable to free myself. Then I waited.

A couple of hours later I heard Madam Darling come home from work. Our floor upstairs was very creaky and I heard every step she had taken. Then she took a shower and took her time. It felt like I'd been kept waiting an extra two hours while she was getting herself ready for me. I head her go back to the bedroom and things were quiet for a while. I wasn't sure if she had gone to bed or if she was doing something else.

A short time later I heard her steps, but they were much louder this time. I heard her walk loudly to the door to the basement. It was completely dark but I saw her black motorcycle boots over her fishnet stockings coming down the stairs as the door closed behind her. The light was gone before I had a chance to see anything else. She made her way over to me and stood behind me. She then turned on her phone flashlight to a dim setting so I could barely see, but she could see enough to do what she wanted.

Madam Darling threw her boot onto my ass and she told me she had been working on a gift for me all day at work. She pulled out her Ben Wa balls that she had talked to me about in the past. Then she put them into my mouth and told me if I could hold them in my mouth until she was done in the basement she would take me upstairs and try to get me off.

Then she pulled my panties and down and I heard her open a bottle of lube. Then I heard her stroke her strap-on just before working it into me. Her strap-on has a center strap that goes between her legs and it has a toy that fills her while she works on me. Madam had her way for quite some time, but I haven't ever been able to have an orgasm from anal play. So she got me very worked up and continued to pound me.

Eventually I started making a lot of noise. A very high pitched sound that I didn't expect. I'd experimented with anal toys, but not much. I had no idea how good this could feel while still being unable to get over the edge. I asked her to stop and she simply said, "no." I kept squeaking and squealing as she changed how she was thrusting and changing angles. After quite some time she asked me if I would like to go upstairs and try some more.

She removed the Ben Wa balls from my mouth and she untied me. I followed her upstairs and she bent me over the edge of her bed. She made her way back inside of me and pounded more until I was back to making a lot of noise. I couldn't stop myself from making these sounds and that made the experience even hotter.

After some time Madam Darling began hitting my ass even more furiously than she had all night. I begged her, "please, please stop. Please stop!" and again she said, "no." She thrusted harder and faster until the thrusts became very very deep, but much slower. She hit me with as much power as she could while she finally had her orgasm. Then she fell onto my back, covered in sweat. She rolled off onto the bed and asked me to get her some water and a towel which I was glad to do.

Once I had brought her the water and a towel she talked about how much fun she'd had and she told me to go take a shower to get cleaned up. Once I made it out of the shower Madam Darling was naked and sleeping. I crawled into bed knowing exactly what it was like to be used as just a hole for someone else's pleasure as I fell asleep.

 

She’s amazing in several different ways. Not only is she articulate and sincere, but I’ve never seen confidence and humility so perfectly consummated in the mind of one person.

 

I'd mentioned that I had brought up wearing chastity a few times with Madam Darling. This was earlier in our relationship. After the birth of our son, she was also completing her bachelors degree. This was a stressful time for her and she stopped requiring sex. Almost overnight we went from 6 nights per week to 6 times per year. Over the next few years the frequency would lower to about 3-4 times per year. While chastity play is exciting to me I don't handle being ignored well. And we hadn't began a FLR, technically.

After she had finished her 4 year degree the frequency hadn't improved and she was applying to several medical programs to finish her post grad studies. At this point, I quit my job and moved with her to the other side of our state to stay home with the kids while she completed her studies. We stayed with a friend of mine along with our kids so the house was very crowded. We were in the house for 6 months and we were only intimate one time during that time.

Because of personal conflicts with living with another person, we had decided to move out and rent a house of our own. We were told when we moved in that the house may only be available for 6 months. The timing turned out to be perfect because my wife wound up transferring schools 6 months later when we would move to Arizona.

But the home we had found was a very large 6 bedroom house. It was about 2,500 square feet, and it had a finished basement. One room was a utility room that was all concrete. It was the "creepy" room in the house so the kids never really wanted to go in. Still, we added a locking hasp on the door to allow me the space to build BDSM furniture at the request of Madam Darling.

The first thing I built for her was a pillory. It was a small platform of about 24x24 inches. It had two uprights on the corners made of 4x4's. Then it had a flat board, about 1/4x1" that fastened to the tops of the 4x4's at a height that allowed me to drape my balls across the board when I was wearing heels. There was another 1/4x1" board that would fasten on top of the penis and balls that would be pulled down with wing nuts. Then there was a hole that was drilled in through those boards directly adjacent to the wing nuts that would allow for a lock to slide through. The lock would prevent the wing nuts from being unscrewed. So even if my hands were freed, (which they never were) I still wouldn't be able to pull my balls from the pillory.

The two boards that ran across from one upright to the other were also easily removed so that it could be used as a humbler which we used a few times for spankings. My wrist cuffs would lock onto the ends by the wing nuts and I wasn't able to cover my ass to prevent the punishments.

Another thing I built for Madam Darling was called "the rack." I had a 4x4 that I laid down on the floor. It was tall enough that when I was on my hands and knees it ran from the hands all the way down to my feet. I used an auger bit to drill holes in the 4x4 that were the perfect size to hammer a 1 1/2" dowel through. It ran through very tightly and wouldn't turn no matter how hard I tried. I ran two dowels, one for the wrists and one for the ankles.

Then while it was laying down, I used the auger bit to drill more holes for dowels right where my penis and balls would hang, then another around the point where my neck would be. I put short dowels in there as well. Then I took another section of 4x4 and I cut it just a little longer than the span of the upright dowels. I used the auger bit to drill holes in that 4x4, and hammered it onto the upright dowels. This raised 4x4 was tall enough that I could rest my stomach and chest onto it to relax and make it less strenuous to be on all fours.

So now I could be on all fours and lock my ankles, wrists, we could anchor my balls to the raised 4x4 with a light bar clamp that we bought from amazon, we could zip tie around my waist and the raised 4x4, and zip tie around my neck and attached it to the raised 4x4.

In "the rack," I've been pegged by her and by our fucking machine, but most of what she used it for was spanking so that she could do anything she wanted without the possibility of escape. She also used the fucking machine in my mouth for at least an hour.

I'll share several experiences here in the very near future. But this is where we really started to find our stride.

 

One of the reasons we knew penis banding would work for me is because one of the first times we used the ball pillory we just locked my penis into it without my balls. The two thin boards would pinch down hard enough that there was no way for me to pull my penis out once it was locked into place because it was way too tight.

Madam Darling told me to put on my 4 inch heels and she would meet me downstairs. She had me secure my penis with the locking mechanism, then she twisted the wing nuts a couple more turns until I started to make sounds and my knees began to buckle. She then locked my wrists to the eyelets on the two uprights by using very large zip ties around my wrists, then another from the zip tie to the eyelet. My wrists were completely secure, and no matter what I've tried, I haven't been able to break one of these zip ties in any way.

After I was secured, she told me she was going back upstairs to get the kids ready for bed. She left me in the cold concrete room standing in my heels. She turned off the lights and went back upstairs. I was there for about an hour before she returned. She turned a small, dim light on and I saw that she was wearing a full fishnet crotchless body suit with designs all over it. She had her phone in her hand and a small white twist handle for the horizontal blinds.

Madam Darling didn't say a word. She put her phone down and I saw her setting a timer, but I couldn't see how long. Once she hit the start button she began using the white stick to cane my ass. I really don't like pain, but Madam Darling refuses to use safe words. We have one in case I feel like I'll be injured in a way that might result in a hospital visit. Otherwise she won't allow one. She has told me in the past that she knows my limits better than I do. So far she's been right about that. Several times I would have stopped her at time that eventually ended in something like a religious experience. So I trust her to do as she intuits about my experience.

After I'd had my dick smashed for an hour while standing in uncomfortable heels I wasn't really in the mood to be caned. But I didn't protest. I just hung on and tried to make as little noise as possible while she took advantage of the opportunity to keep me still and unable to squirm too much. I kept involuntarily lifting my ankles and blocking her access to what she wanted to strike so she would give me an extra hard thwack to let me know I was doing the wrong thing and it would be punished.

After about 5 minutes or so the timer sounded. Madam Darling put down the white stick and took another zip tie to secure my ankles together just enough so I couldn't lift them. Then she grabbed her phone and again set the timer. She pushed start and pulled up a chair that was nearby. She put the chair directly in front of me with the back of the chair facing my dick still smashed in place and unable to get free. She got onto her knees on the chair and put her face near my dick. She arched her back and looked back at her perfect ass and kind of wagged her bottom a little. Then she said, "five minutes back there and five minutes up here. Do you think you can cum like this?"

Madam Darling then took the exposed tip of my penis into her mouth and began to suck on it. Luckily when I went to secure my penis in the mechanism I had pulled as much through as I could. I was still flaccid and now there was no way for me to get hard, but Madam Darling used as much of my penis as she could and began to bob her head sucking my dick at a fairly fast pace.

As she did this for about the next 5 minutes I felt my penis trying to get hard. I could tell the blood was flowing as far as it could, but there was no way for it to become engorged beyond the self-imposed damming that I had locked into place at her request. Still, the feeling was incredible and was the most sensation I had had in days. Once the timer sounded Madam Darling stopped and I found myself whimpering. I felt as if she would have continued for a couple more minutes I could have had an orgasm, but I'm sure it's not the case.

Madam Darling grabbed her improvised cane and went back behind me and began caning my ass. I could tell she had been there recently. I hate having my back touched and she started to make her way farther up my back. I started to become extremely angry with this, but she didn't care. She made her way up my shoulders and back down my spine and on my sides. I wanted to fight and I started giving her looks that she wasn't pleased with. Once she saw me looking at her like this she would give me a few solid hits on my ass again to let me know things could get much worse.

She went back and forth like this for another hour or so and by the last couple of times she had put her mouth on my penis I had noticed I couldn't feel as much I was earlier on. It still felt good, but it was extremely frustrating to be so horny and being unable to get hard even though I wasn't locked in a device. And although I could still feel my penis there wasn't nearly as much of a sensation.

Madam Darling told me I'd had enough and she began cutting me loose. We had only just started experimenting with chastity and it wasn't full time yet. The next day I wasn't locked up, but my penis was still largely numb. I started to look into the sensation a little and discovered a thread here about using electrical tape and a hose clamp for numbing which we would eventually incorporate into chastity play so Madam Darling could be certain that I wouldn't be able to cheat even if I'd wanted to.

 

Thanks very much. Nice to hear there may be some value to it.