Blackmail Most Foul

Watch out letting strangers into your  homes...

Mary always made more money than me, even when we first got married.  She worked hard for it though and had to spend many weekends traveling.  My only complaint was spending all that time alone.  Mary, the thoughtful soul that she is, arranged to have one of her colleagues come stay with me.  Olive was an up and coming staff writer at Mary’s company and made it clear that she’d do anything to stay in Mary’s good graces.  When I found her trying to hack into Mary’s desktop computer I told her that it wasn’t anything personal but I’d have to ask her to leave, but that if she took this as an adult I’d keep it away from my wife.  I can look back now and realize that trusting this woman to cook us dinner is where all my woe started.  I wasn’t four drinks into the glass of chardonnay before the world grew fuzzy and I passed out. 

 

When I came to I thought I was in some kind of kinky dream.  I was on Mary’s and my bed with my ankles and wrists tied to the bedposts.  Olive was straddling me and bouncing up and down on my cock.  When I tried to ask her what she was doing she just smiled down on me, pulled off my manhood, crawled up my body, and lowered her wet and stretched pussy down over my face.  Later that night when she showed me the video, I was beyond flabbergasted.  Not only had she filmed us, but she did it in a way that hid away my bindings.  Most of the time I was silent with just a drug induced smile on my face, but it told a story.  A story that I was a willing participant.   A story that I was cheating on my loving wife. 

 

Olive had me over a barrel and she knew it.  Letting Mary know about ‘my indiscretion’ might ruin her career, but it would most certainly ruin my marriage.  And while I was certainly worried about the financial impact that a breakup would bring, I was far more concerned with the heartbreak it would bring Mary.  So, I succumbed.  Olive, the shark that she was, smelled blood in the water.  Soon enough she was taking over parts of my life that I didn’t’ know I had to give.  When Mary left for her next business trip Olive made sure to get herself invited over again, but this time Mary was gone for a week.  For a week, I served Olive however she asked.  I cooked her meals, I cleaned up her meals, and I even laid in my marriage bed and ate her wet quivering pussy out for what felt like hours on end. 

 

She reveled in her power over me and where I hoped my submission would satisfy that part of her, it only made her hungrier.  She started purposefully making messes for me to clean up in front of her.  She had me remove my clothes and serve her with just a tie on.  She had me shave my body smooth for her.  She put a pair of handcuffs on me and bound them to my belt so serving her was all that much more difficult.  The night before Mary came home, she had me put on a pair of thigh high stockings, a pair of panties, and a bra stuffed with socks before filming me kneeling and eating her out while she called me sissy.  I bore down and made it through every indignation knowing that seeing Mary’s heart break would be worse. 

 

When Olive got herself invited over to our barbeque party, I hoped that I’d just be able to avoid her, but she made sure to sit right next to Mary and I.  I’m not exactly sure how she manipulated the conversation in this direction but she ended up admitting she was getting evicted out of her apartment.  Mary seemed particularly sympathetic when Olive said she had missed several side gigs when she’d come over and ‘babysit’ me.  Mary truly was a saint so it was no surprise when she invited Olive to stay with us until she was back up on her feet.  Olive wasted no time in demanding more from me as I practically had to pack her up and move all her belongings by myself.  With Olive in the spare room my humiliation was increased from the occasional long weekend to every single time Mary worked late.  I was always so scared of discovery but Olive seemed to know exactly when Mary was coming home.  And while she was living up the life that paying no rent afforded her, she also spent money on me.  On my continued subservience and humiliation.

 

When Mary next went overseas for business, I spent the entire time she was a away being feminized by Olive.  Panties and stockings were only the beginning.  Olive had a wicked corset that she tied onto me so tightly that I could barely breath.  She slipped in some realistic false breasts into the top before covering it all up with a latex maid’s outfit.  She spent an hour with me sitting in front of the vanity mirror, making my face up as femininely as possible.  I hated admitting it, but as I flitted from one room to the next with my ankles bound by a 10 inch chain, my feet locked into a pair of fetish high heels, and a feather duster in my hand, I couldn’t help seeing myself in the various mirrors.  I obviously wasn’t a woman, but in a single day she’d brought me further into a feminine form than I ever thought possible. 

 

This continued for nearly a year and it was getting harder and harder to explain the changes in my body to my wife.  When I had lied and said I liked my body smooth for her that first night so long ago, it made it impossible to ever turn back as Mary liked me smooth too.  But explaining why my eyebrows got plucked and why I colored my hair was troublesome.  Explaining why I was letting my hair grow out longer as well as my fingernails was tough.  I tried saying that my red toenails was just a joke when I forgot to wash off the polish one night, but I thought Mary was getting close to figuring something out.   I was at my wit’s end and Olive was just living the good life. 

 

I don’t know why I told this wicked woman that I was going to come clean with Mary.  I was going to admit to having sex… getting raped… by Olive and that afterwards I’d tried to hide it, but also tell her that I’d done it all to spare her heartbreak and that if she wanted to throw me out, I’d completely understand.  There were a few hours there that I thought I’d won.  Olive was furious but knew I was serious when I started laying out all the feminizing gear on the bed to show Mary all what I’d gone through for her.  I even called my wife and left her a voice mail saying that I had something important to tell her when she got home and that it involved both Olive and I. 

 

It was a play straight out of her playbook that I should have seen coming from a mile away, but when the world started to grow dim I still cursed myself for letting Olive drug me again.  The sound that I awoke to this time was Olive and Mary talking.  I tried to say something…. Anything… but quickly found that a gag was stretching my lips wide leaving me with only the ability to moan and groan.  I tried to move, but found that I was bound.  Not only bound, I was hogtied in the middle of our bed. 

 

My hair must have been tied to my arms as I couldn’t look away if I’d wanted to and as my vision came clear I found myself staring at out television showing me.  Me dressing up as a woman.  Me prancing around the house in my maid’s outfit.  Me kneeling and kissing Olive’s boots.  Me bent at the waist while dusting and Olive walking by and casually giving me a spanking that I didn’t move away from.  And all the while Olive was giving Mary her version of history.  That I’d come to her that first weekend and blackmailed her into sex.  That I’d begged and pleaded for her to dress me up and play as my mistress but that the blackmail finally forced her to participate.  That I’d set her up to lose her secondary gigs and ended up forcing her no other option but to move into our home. 

 

I’d known that Olive had plenty of video of me dressed up.  But most of it was me sullenly going as I was told or being obviously and overtly humiliated by it.  I’d wager that she had scrubbed through all of that footage and found the only 10 minutes of me not seeing desperate for the humiliation to stop and when you only saw that… I not only looked accepting of it, I looked downright excited by it.  Not only did I have a forced front row seat of my humiliation, I was in clear earshot of Olive setting up the next stage of my blackmail.  She got Mary apologizing on my behalf for forcing her into this but also thanking her for showing her this side of me.  When she said she’d be not only accepting of it but downright excited to lead our marriage on in this way. 

 

When Mary stepped out of the room and left Olive and I alone, Olive wasted no time in letting me know how this was going to play out.  She’d already convinced Mary to buy her silence as any hint of this would likely get Mary fired.  She also convinced her to keep her in the loop as to my new life, saying she wanted to see that I was completely feminized and not a threat to anybody ever again.  She whispered the next part into my ear, making me shiver as I realized this was the final nail in the coffin.  As soon as I could speak, I could still tell my story.  Even with the video, everything else was my word vs hers and we both know who Mary would believe.  But if I did that, a copy of the video we’d been watching plus a video of our current conversation would be mailed to the company and both Mary’s and my family.  I’d be fine with the humiliation as I could explain it away, but having Mary offer Olive a pay off to keep quiet?  That was beyond embarrassment, that was criminal bribery.   

 

So when Mary came back in, dressed in lather and lace, and pulled the red ball gag from my mouth I did as Olive bade me to do.  I admitted to my wife that I’d not only forced her to do this to me, but that I’d wanted this to be part of my life since before we were married.  Pursing my lips and kissing my wife’s shoe was soul crushing as she accepted becoming my mistress.  But worse than that was the look in my wife’s eyes.  She not only accepted this from me…. She was truly excited by it. 

 

Mary had paid Olive plenty enough money to move out on her own, but she insisted on staying on for a couple more months.  She acted scared of me and gave Mary every indication she was just watching to make sure I was going to love my wife and now mistress instead of coming after her, but she and I knew why she was there.  She was making sure I didn’t try to talk my way out of this lie.  That I laid the framework thick and strong enough that any ‘truth’ later would seem like a lie.  She witnessed me begging my wife to dress me.  Me pleading for her to use a strap on to fuck me.  Me urging her to get me started on hormones.  I’m not sure where the point of no return occurred.  It could have been the hormone treatments that smoothed out my skin and gave me a small pert pair of breasts.  It could have been Mary taking me out to her salon to get a make-over and being seen as her ‘sissy maid’ by all her friends.  It could have been admitting that my hormone shriveled cock couldn’t get hard anymore and accepting that she’d take on another man as a sex partner.  It may have been by this guy Dylan not only fucking my wife in front of me but having me clean up after both of them.  It could have been him agreeing that he liked being blown by me more than by my own wife and being given the job of sucking him off at least once upon each visit. 

 

But if none of those were the point of no return, this was it.  Dylan wastes no time in turning me around and pulling my dress down as soon as Mary walk out to the Uber waiting for her.  Her trip this time was three weeks in Japan and as she didn’t want me to be on my own and getting bored, she’d invited Dylan over to babysit me. 

source:  fuskator