Starting a FemDom marriage in the Vanilla Kingdom

History - Mistress Debbie

Previously on timid boy:  After the separation of my wife and I, I started hanging out at a variety of swingers parties around San Diego.  It wasn’t long before a met one of the fixtures of the Heart On San Diego BBS, Mistress Debbie.

I remember our first meeting vividly.  I was sitting on a couch sipping a beer and wondering if I should get naked and join the group of cute women that just headed into the pool when this woman came over and sat down right next to me.  She introduced herself, then told me her on-line handle.  It turns out we had actually been chatting on-line and I had told her about my interest in D/s and my dissatisfaction with finding a suitable partner.  Like most people you meet on-line, Mistress Debbie was nothing like how I pictured her.  She was little over 10 years my senior and was a fairly "Rubenesque" woman with gigantic anime-worthy breasts which she assured me were all natural.  (I hadn’t even asked, something that should have probably been a warning sign…)

She was married, but had an open relationship and was looking for a new "pet" to play with.  She was not a professional lifestyle Domme, but did have some experience and she was a central player in San Diego’s swinger’s scene.  She then told me to strip and sit back on the couch (which I did) and she proceeded to straddle my lap, pinning my arms back with her hands while she placed her lips against my ear and started describing in graphic detail what I could expect if I visited her at home the next day.

Needless to say, I took her up on her offer.

On the surface, Mistress Debbie looked like a dream come true.  We started playing together quite a bit and I quickly became known as "Debbie’s Pet" at the local parties.  She had a make-shift dungeon set up in her garage and I was frequently left hanging by my arms while being subjected to all sorts of flogging and spanking.  We also played some games with her husband, their favorite being to strip me naked then tie me to a chair at their bedside, after which they would engage in some of the raunchiest sex I’ve ever been witness to.  If I was good, she would usually stroke me to a climax and then let me sleep at the foot of their bed like the family dog.

It only took a few months, however, before the shiny veneer cracked and I started to see what Mistress Debbie was really made of.  First, she was very well off, even by SoCal standards.  She used her money to ensnare people into her service.  Any favor or financial assistance she offered usually meant that you were hers, whether you were a sub or just a friend.  While that worked in the D/s setting, I started to see many of her friends start to distance themselves as she acted more and more superior to those around her.  The money, I soon discovered, came from a lawsuit when her adopted son suffered brain damage after strangling on his wheelchair harness due to an inexperienced bus driver.  That made it the most evil kind of blood money possible, especially considering how she threw it around and used it as a manipulation tool.

Another thing that didn’t seem like too big a deal at the time was her taste for drugs and friends that enjoyed the same.  I would become well acquainted with one of her friends, another amateur Domme named Mistress Bonnie.  Mistress Bonnie had a full-time live-in, her husband Robert.  While at home, he would be her full-time sub, performing housework and basically just doting on his Domme.  Mistress Debbie loaned me out to her on occasion, usually to be put into a French Maid’s outfit and clean her house.  As a reward after one housecleaning, she tied me down in a stirrups-type position after which she told Robert to shave my cock and balls then bring me to orgasm orally.  (Man, that was hhhhhhhhhhhhot…)

While all that was great fun, Mistress Bonnie introduced me to an even harsher Domme, Crystal Meth.  While I wouldn’t end up hooked until almost a year later, tweaking out during her sessions started me down a slippery slope which would end in full-blown drug addiction.  [More on that later…]

What finally ended my relationship with Mistress Debbie is when she did the unthinkable - she broke our trust.

I was doing pet duty at a private party in the ballroom of a ritzy local hotel and Mistress said she had a surprise for me.  She took me up to her hotel room and tied me up.  She then said she’d be right back and proceeded to leave the room, returning about 15 minutes later with a man I’d never seen before.  She then offered me to him as a gift to do with as he pleased.  Now, up until this point, I only had a few other "bi" experiences, and since my first was a semi-consensual session with my Scoutmaster when I was 14, I immediately started to freak out.  (Oral sex is one thing, but he made it clear he intended to use me in every possible way.)  It was right then that I did the one thing that I hadn’t done before or since - I said the "safe word", the one previously agreed upon phrase that was supposed to stop the session.

As you can probably guess, Mistress Debbie completely disregarded the safe word and things moved forward.

The guy fondled me for a little bit and started to lick and suck various parts of my body, but before things went much farther, Mistress Debbie decided she was sick of my carrying on and told the guy to stop.  The two of them went at it on the bed for awhile and then she sent him away.  I actually didn’t know what to say to Mistress Debbie right then, but she acted like it was just another session.  A few days later, I called her and said I wouldn’t be coming by any longer.  She tried to use some money she had "loaned me" to guilt me into staying (she paid for a new transmission on my car to replace the one her sister destroyed after she had borrowed it without my permission - not really my fault nor a loan, but there you go), but I managed to stay firm and stay away.

Through the grapevine, I heard that Mistress Debbie took my rejection really hard and didn’t understand at all why I was upset or walked away from her.  She supposedly started doing things to try and please me, including getting gastric bypass and some plastic surgery (including breast implants), something that further proved that she didn’t know me at all because (a) I like big girls and (b) I hate fake breasts more than anything.  (I like breasts of any size as long as they are real.)

Free of Mistress Debbie, I dropped out of the scene for a little bit.  Further exploring my "I must be gay" theory, I actually tried dating a few guys.  One guy, Master Luke, ran a video production company where he tied up guys on camera.  We didn’t last long nor ever try a D/s scene, which is probably good because our first session was to be a filmed feature.  (He did give me the option of wearing a mask, but said he would pay me extra if I agreed to show my face.)

After that, my bad life choices got exponentially worse.  In one case, I started rooming with a lesbian couple, only to discover that one of the girls was actually bi and kind of sweet on me.  We started a relationship behind her girlfriend’s back which ended in tears and bad feelings for everyone.

I also hit the end of my Civil Service contract and stopped working for the government all together.  (I had a pretty hefty security clearance and they said staying on would mean upgrading to a higher level, something that would mean an FBI background check.  Given all of the above, I really wasn’t keen about having my sexcapades on my permanent record.)  After a little looking around, I found a job at an Internet startup company (this was just when the web started to go commercial) with little money and fewer clients.  I threw my heart and soul into my job, something that would come back to bite me during the months that followed.

Next time, on timid boy:  After not getting paid by the company, I start sleeping in my office and, since I was the only programmer left at the company, began using meth so I could program for 72 - 80 hour stretches without stopping.  I would then meet Mistress Natalie, the one woman who would show me the light and finally make me understand what subspace is all about.

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