10 Amazing Years Serving Lady Madeline

Ten years ago today TP's life changed forever. On this date in 2003, TP had his very first session with Lady Madeline. Can you believe that? Ten years! TP would have never thought that session would lead to anything more than a fun and frightening hour, but here we are. Getting to serve Lady Madeline has been one of the most amazing experiences of TP's life.

Ten years ago TP was still new to San Francisco. TP had also decided he was done with BDSM. TP still felt submissive, and was a pervy little freak, but thought he shouldn't be sessioning anymore for some reason. Maybe it was the old catholic guilt. But as a new resident of the city it couldn't hurt to check out the local Dommes' websites... right? Well one website caught TP's attention, and TP kept going back and back and back until one day TP broke down and scheduled a session. It was the best decision TP ever made.

It's hard to believe that session was ten years ago. TP still remembers how amazing Lady Madeline looked when she opened the door to greet a very nervous loser with a little dick.

That session led to another, and then another, and then a shopping trip to Victoria's Secret... and soon Lady Madeline was controlling all of TP's orgasms. Then she allowed TP to be her delivery boy, bringing her breakfast on Saturday mornings. Eventually she let TP inside her apartment and gave TP chores to do... dishes, and sweeping and stuff like that.

Then she gave TP a collar.

TP was so happy. TP had not only become the property of an amazing Domme, but he was able to live out all the kinky fantasies he had in his perverted head.

But the main thing was getting to know Lady Madeline as a person. She is so smart and talented and TP considers her a friend. A friend that just happens to also own him!

After a couple years of serving as Lady Madeline's houseboy, life took TP back to Chicago. TP was heartbroken to leave his Mistress, but had no choice. So TP stopped serving for a couple years. We stayed in touch with emails every so often, but it wasn't the same.

Eventually TP got the BDSM bug again, and called a phone line Domme. It was fun, but TP missed his old Mistress. That phone Domme had some humiliating pictures of TP on her website, so TP decided to email Lady Madeline to show her. TP thought she would find it funny, but secretly TP wanted to admit to her that he had called another Domme. TP felt guilty, even though Lady Madeline did not do phone sessions. TP always felt loyal to Lady Madeline.

And then an email came from Lady Madeline suggesting what TP had been hoping for... she wanted to play again! She wanted me to serve long distance! She was semi-retired and missed having a pathetic slut to humiliate and suggested we start up again. TP had never been happier!

And here we are... after taking a break for a couple years, TP is still loyal to his amazing and beautiful owner. TP hopes to serve Lady Madeline forever, but even if for some reason the BDSM part stops someday, he knows he has a friend for life. A friend that pees on him, but a friend non the less.

Happy anniversary, Mistress.

Slave Memories: Chained to the Sink

One moment that Tiny remembers was something so simple and quick that Lady Madeline surely has no recollection of it, but it was exciting to me. One of my chores as Lady Madeline's houseboy was to do her dishes. That is probably the one thing Tiny did every time he was in her apartment. One day while washing her dirty plates, wearing nothing  but a pair of thong panties and my collar, Mistress walked into the kitchen and attached a leash to the collar. She then wrapped the end of the leash around a handle of a cabinet. She didn't tie it or lock it, just wrapped it. Tiny obviously could have moved, but of course Tiny would never unwrap the leash. Tiny was not going to move until she allowed it.

Tiny was only kept there for a short time while he did the dishes. And Mistress did not say much when she tied me there. But Tiny felt really secure. He felt so owned by her. Even with the ability to untie the leash, it felt as if Tiny was stuck in the most secure binding possible. He was stuck under the control of Lady Madeline, and it was the best feeling in the world.

Slave Memories: Helping Mistress Move

Part of the reason Lady Madeline chose me to be one of her houseboys many years ago was the close proximity of our apartments, so it was sad news to hear she was going to move into a new neighborhood. It seems silly now considering we live thousands of miles apart, but at the time living in another neighborhood seemed so far away.

Mistress has had a very busy summer this year, and she is currently busy with moving into a new place. That reminded me of her move in my houseboy days, and how she allowed me to help her move. It was such an honor to be trusted with all of her valuable possessions. Not every slave gets to be a part of an important day like that. In fact, the only other person that helped was a friend of hers. Tiny would be the only one wearing her collar that day as we lifted all of her furniture up the stairs to her new place. The funny thing is, it seemed like her friend was jealous of me! You could tell he wanted to wear a collar with a tag that had Lady Madeline's name on it. That made me feel extra special.

It was kind of odd to have her collar on all day in public. Most of the time was spent in her old and new apartment, but we did make one stop to pick up some couches she bought. The couches were at some guy's apartment, and he had been told about her life as a Dominatrix and that a slave might be stopping by to get the couches. So while he wasn't surprised to see me wearing a collar, it was still kind of strange to be so open about it in a stranger's house.

Moving is always a lot of work, and moving Mistress's things was no exception. Of course her two helpers did almost all of the work. She bossed us around while we did the heavy lifting....as if it would be any other way. She did let me have water, but only out of a bowl like a dog. Her friend got to drink out of a glass.

At the end of the day we went to return the truck she had rented. It was after hours so we were supposed to park it near the rental place. She was riding with me in the passenger seat as we pulled into a parking spot in a dark corner of the city behind a van. As we were about to get out of the truck she noticed the van moving in front of us. It was rocking back and forth.....and we could see people inside. They were fucking! The van in front of is was rocking back and forth as they fucked! Our trucks headlights were shining in the windows so they stopped and started yelling at us. Mistress started to slap my arm while yelling at me to get out of there! She assumed it was a prostitute in the van, and wanted to avoid any awkwardness. She kept yelling at me to back up, but her friend was right behind is in his car to give us a ride back. There was nowhere to go! We were stuck between a hooker in a van and her friend that couldn't see what was going on. We backed up anyway and he must have got the hint because he did too, and then we pulled away fast, with the trucks tires screeching, and found another place to leave the truck. It was a very bizarre ending to a long day.