My D/s Relationship With Emmy

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d/s relationship

Indentured Domestic Servitude

My D/s relationship started with the best blowjob of my life. Her name was Emmy. She was beautiful and sexy. We had been together for 4 months before it became a D/s relationship. She promised me the world’s best blowjob. And it was. I’d never had one like it before, and, for reasons that are now obvious, I won’t have one like it again. Because it came with a caveat:

  • “I’ll handcuff your hands behind your back. I will rock your world with my lips. Then, I’ll put this cock cage on you. I’ll decide when it comes off. Do you agree?”

I asked questions.

  • Exactly how long? A day? A week? Will it hurt?

Plenty of questions. She just smiled and repeated what she had just said. I said no. Initially. She teased my dick, then stopped when it grew. I wavered. She held out the pink cage and giggled. My resolve held firm (but so did my dick):

  • “No way.”

She teased me again. She took off her bra and rubbed her breasts on my chest. She wiggled her ass. I begged. I pleaded. She held up the cock cage again. My dick won the battle of firmness over my resolve and I gave in. Without another word, I turned around and put my hands behind my back. I heard the handcuffs click.

My D/s Relationship Begins

My dick was as big and hard as it had ever been. She tickled my balls and said – playfully, I thought, “In a few minutes, these will be mine.” I barely heard her as she wrapped her lips around me.

Two minutes later, it was done. My legs buckled when I exploded. She grabbed a washcloth and rinsed me off. Then I watched her lock me up and attach the key to her ankle bracelet. A series of snaps and clicks and she had complete power over my life, for as long as it pleased her. This is where the vanilla relationship ended and the D/s relationship began.

Looking back, she was kind. She let me settle in for a few days before gradually introducing me to the servitude commonly found in a D/s relationship. Of course, I resisted at first, thinking she wasn’t really serious about keeping me locked up. After two weeks I realized she was. I gave her my bank account numbers and the stocks I owned, transferring them and making her the sole owner. I signed over my credit cards so that she became the main account holder. I had a decent job, so I continued to work, but my paycheck was sent via direct deposit into the account she now owned. On paper, I no longer owned anything or had any money of my own.

Feminization Over The Weekend

But I did have an owner. And I was in a D/s relationship. She decided I should do her housework. All of it. I told her I didn’t know how since I had a woman come to my apartment once a month to clean. She laughed.

  • “Don’t worry, sweetie, I’ll train you to clean better than she ever did.”

A week later she presented me with a maid’s uniform, and my first pair of panties. Shortly after, she decided that other than when I went to work, I should dress more like a woman.

  • “Why?” I asked.


  • “Because I want you to and I think you’ll look cute.”

She gave me an eclectic weekend wardrobe to start and ordered me to rotate outfits so she could “see what works for you and what doesn’t.” She gave me several pairs of shoes as well and I spent a humiliating weekend being taught to walk in a variety of heels and flats and learning the difference between slingbacks, espadrilles, pumps, mules, wedges, and dozens of other shoes.

She gave me my first set of spankings that weekend, as she grew frustrated with my inability to master walking in shoes that millions of women walk in each day. She must have enjoyed it or felt it motivated me to learn (she was right, as usual), because I have gotten spanked, paddled, hair brushed, strapped, or lashed at least twice a week since then. Now, it’s rare that my ass is it is originally white.

Expert At Servicing Her And Her Friends

Sex never stopped while she was turning me into her servant in our D/s relationship. I mean, it didn’t stop for her. Her appetite for my tongue was voracious. I adored her pussy several times per day. She had always loved when I went down on her, but I guess knowing she never had to reciprocate at ANYTHING fueled her imagination.

With her direction, I became an expert at ass licking, worshipping her ass when she got up in the morning and licking her ass to sleep at night. Each week, I spent hours worshipping her feet and toes. She peed on me. She spits in my mouth. She slapped my face. She told me she liked to look online and look at what other couples in a D/s relationship were doing to find ideas and try them out, because “why the f*ck not? It’s fun for ME.” Whenever I tried to object, she reminded me of my position by gently – or, not so gently, depending on her mood – kicking my cage.

She bought a strapon, and though she had never used one before, became quite adept with it. It hurt the first few times, but once I got stretched out, and realized that this big rubber dick was going to be the extent of my sex life, I didn’t mind it so much. She, on the other hand, loved the thrill and power of ramming it up to my ass and telling me to moan like a slut being fucked hard. I did my best to obey her by trying to mimic her own orgasm sounds.

Her New Personal Chef

I gave her full-body massages whenever she wished. She taught me how to give her mani-pedis and that became a weekly duty. With the help of many painful motivational spankings, she taught me how to properly wash, brush, and style her hair.

I cooked and served her meals on weekends, but because I worked, she didn’t have me cook dinner during the week. For a while, I brought home take-out and served it to her. She got tired of this, though, and decided to hire a personal chef (Of course, I paid for this – I paid for everything). The chef was an excellent cook, and was also “not just cute, but hot.”

After a while, we fell onto a weekday pattern. He cooked dinner. When I got home from work, I’d change into my maid’s outfit, and serve both of them a leisurely dinner. They chatted, ate, and laughed at me. They would drop bits of the dinner onto the floor and have me scurry over to eat it. That was MY dinner.

d/s relationship

Sissy Cuckold

After I cleared the table and cleaned up the kitchen, I’d follow them upstairs, where Emmy would make me kneel by the bed, and watch them have rip-roaring sex. After it was done, he would leave, and I would, once again, “clean up.” Occasionally, Emmy would make me suck his dick and swallow his load. She said she wanted him to last longer when he got into her, but I suspect she enjoyed humiliating me, watching me sucking dick like a greedy slut in my maid’s outfit. It is hard to forget both of them laughing their asses off at me all night long.

During that time, she got it into her head that since her chef/boyfriend got to see me in action as her slave, a girlfriend should as well. She invited her friend Jennifer, who I had known when I was still a functional man. A pretty woman, fun-loving, sometimes nice, but sometimes a real bitch. She used to flirt with me, daring me to come on to her, probably so she could tell Emmy. When Emmy was out of the room, she’d bend over, “Oh, I dropped my lipstick” to give me a perfect view of her lovely ass. Even after a few of these occurrences, I still wasn’t sure it was on purpose, until one time she turned around quickly, caught me looking, and smiled. She drove me crazy.

Showing off My Maid Skills To Her Friends

Wanting it to be a surprise, Emmy hadn’t told Jennifer about my transformation. So when I answered the door in my maid’s uniform and saw Jennifer – along with two of HER friends she had decided to bring along – there were surprises all around. After they got over their initial shock, and after 5 or 10 minutes of laughing their asses off, the women calmed down fairly quickly. Of course, it wasn’t the last time they laughed that night.

Emmy showed off my maid skills, had me put on a fashion show with all my outfits (I had about 10 by then), showed them with my cock cage on (“fuckin hilarious” was the group sentiment), had me give them all a generous sample of my ass licking skills, and they gave me a long night of spanking, which, because of mathematics, was 4 times as painful as the spankings I was used to. Before they left, Emmy promised to have them over on a regular basis and this is a promise she has kept for the past 2 1/2 years. By now, I see these 3 women – Jennifer, Barb, and Nicole – as surrogate “Emmys.” She will occasionally lend me out to help them with housework, or to clean up their houses after a holiday party – and I am no longer embarrassed by serving them.

Sometimes I Get To Cum

The chef is long gone but has been replaced by a series of different men (and 2 women). I have served and serviced them all, one way or another. I continue to evolve as a servant to my queen in our D/s relationship, whose power over me grows each day. Does she ever let me out of my cock cage? Of course, she does. She knows it’s unhealthy for a man to go too long without release. Once a month – maybe twice if I’ve been exceptional – she cuffs my hands behind my back, removes my cage, puts on a pair of rubber gloves, and massages my prostate.

I feel little if any pleasure from this, though as I watch my semen drip out, I imagine I do. On occasion, when she is giving my ass a good workout with her strapon, my locked dick strains against the cage, and I can actually come a little; this feels better than the prostate massage, though the part of my brain which is still heterosexual man revolts against the idea of getting pleasure from a dick up my ass. But I DO still get to occasionally cum, even if it isn’t very enjoyable.

Would I Do It All Over Again If Given A Second Chance

I am occasionally asked THE BIG QUESTION: “If you had the chance, knowing what you know now, would you do it again? Would you be in a D/s relationship?” Usually, it’s Jennifer, Barb, or Nicole who asks, or one of Emmy’s boyfriends or female lovers. I usually hem a bit, and haw some more, generally answering “I don’t really know, so much has happened, who knows where I’d be now, blah blah blah,” because my (still!) stubborn male pride doesn’t want to admit the truth: I’d do it again in a heartbeat. I adore Emmy. I love serving her. I love licking her ass. I love licking her friends’ asses because SHE loves it. All my money is hers to spend. I’ll suck dicks and do her housework, and wear panties, dresses, and heels forever if she’ll let me.

Once, seemingly long ago, she knelt in front of me and gave me the best blowjob of my life. I thought that was what I wanted. But my cock cage has since taught me that what I really wanted was for our positions to be reversed. The only place I ever want to be is on my knees, in front of her, begging to serve her. I don’t want anything else. Hopefully, neither does she.

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3 thoughts on “My D/s Relationship With Emmy”

  1. The story maybe fiction but, I could see this happening. I’m a senior sub male and serve a Mistress. What I’ve earned all my life, I wouldn’t turn it over to my Mistress. I love her but, not that much. Besides, there’s a big age difference between us. She gets her tribute from me and for me that’s more than enough.

  2. i love this very much! i would give it all up for this kind of D/s relationship with the right Mistress. i would love to be feminized and wear a cage and serve Her and Her friends. Serving is my love language. love it, this one is very arousing.

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