Delightful Decadence
Dec
12
2018
PPSS Saga - The Day Had Finally Come, Part 1 By: Bofors57

Disclaimer: Erotic Fiction for the Avid Reader. 

Please note, that these are erotic fiction stories only. They are posted here annonmously. I have permission from all of the authors to post them here.

These are not reviews and do not depict real life occurances or people in any way.  Any resemblance to real life people is merely coincidental.    

Enjoy you nasty minded freaks!

MM

Introduction - Welcome to the PPSS (Pervy Private Sissy Slut) series.  As the series begins, PPSS is very much a novice sub.  While he clearly is titillated by his submissive nature and very much enjoys fantasizing about it, it embarrasses him greatly and he is hesitant about acting on it.  He has been experimenting with his submissive nature by meeting with a local lady, Mistress Sabrinah, who is a budding domme.  Through her he meets a new mistress, Mistress Macayle, who both intrigues and, to be frank, intimidates him (Macayle is Gaelic for strong-willed and fiery).  The series tells the story of his voyage of self-discovery, learning more about his subservient nature and his sexual orientation under Mistress Macayle’s tutelage.

PPSS Saga #1 - The Day Had Finally Come, Part 1

The Descent

 

While attempting to muster the courage to suck a cock for Mistress Macayle, PPSS recalls the long, circuitous path that took him to this point.

The day had finally come; he was going to suck a man’s cock for his Mistress.  Or was he?  The very thought gave him butterflies.  Could he actually go through with it?

How had he come to this point?  He wasn’t exactly sure; it had been a long, circuitous path, many years in the making.  It had started innocently enough, about 20 years ago.  He had been visiting with a very pretty lady, who, shortly after the visit had begun, asked him “Would you like me to play with your ass?”  He was puzzled and afraid to admit to her that he had no idea what she was talking about.  So instead he tentatively nodded yes and then was startled when she inserted a finger into his rectum.  He was experiencing his first prostate massage.  It took him a little while to relax, but once he did, he noticed how pleasurable it was.  He visited with her several more times over the next year or so, and the prostate massage was a staple of their time together.  And then she moved away.

It was another decade before he took the next step – or actually a repeat of the first step.  He had retired and moved across country.  There he met another lovely lady who passed through his town every 2 or 3 months.  They got together whenever she was in town and they grew ever more comfortable in discussing and experiencing their desires with one another.  One day she asked him if there was anything else he would like to try.  Recalling his experience from 10 years past, he asked if she would do that for him.  She smiled and said “Of course Sweetie!”  And, again, this became a staple of their time together, until she too moved away. 

His reignited fascination with prostate massage began to shape his internet searches of porn sites – and that was when he discovered strap-on sex.  He was mesmerized – the thought of his ass being violated by a beautiful woman wearing a strap-on was so arousing that he began to search for a way to fulfill this fantasy.  And while he didn’t realize it at the time, this was his first step towards becoming a sub.

But how to meet a lady who would help him realize his fantasy?  He began perusing personals web sites that helped connect individuals interested in kinky activities.  His search led him to a young lady who expressed an interest in strap-on play.  Heart in throat, he asked to meet with her.  He was so nervous that he couldn’t even tell her what he wanted; instead, he handed her note that detailed his fantasy.  She smiled and said “I know what you want.”  She proceeded to gently introduce him into the world of strap-on sex.  He was captivated and saw her several times a year for the next few years.  During that time she introduced him to other marvelous activities – spanking, face-sitting, ass worship, edging, mild cock and ball torture and golden showers.  She was not a hard-core domme; rather she was sweet and playful about it all.  But she was clearly in charge – her number 1 rule was that before anything else happened, he had to make her come.  But that was okay with him; he loved orally pleasuring ladies.

His fascination with strap-on sex and ass play led him to begin viewing trans-lady porn.  He was entranced by the sight of beautiful ladies with that special surprise.  He actually surprised himself by how turned on he was at the sight of their rigid cocks.  He knew he had to try this, but it took him quite some time to work up the courage.  Finally he drove several hours to visit with a trans-lady.  He sucked her cock and allowed her to top him (actually, he begged her to top him).  Afterwards he wasn’t sure what to do with his experience.  He had been very turned on.  But he also found the experience to be very unsettling because of his strict religious upbringing.  Would he repeat?  He simply didn’t know.

He now began to plunge deeper down the rabbit hole.  After nearly 40 years in the military and being in-charge of others since his late teens, he relished relinquishing control and being subject to the whims of strong, beautiful ladies.  His searches began to focus on fetishes, especially femdom BDSM.  He was oh-so-pleasantly surprised to discover a local lady, Mistress Sabrinah, who described herself as a budding domme.  He contacted her and offered himself as a toy for her to practice on.  A very gratifying relationship ensued.  She solicited his fantasies, gave him embarrassing homework and demanded photograph proof of his obedience before he was allowed to submit to her in person.  She could read him very well; while they did much the same things as he had done with the previous lady, they were much more intense.  She was much more demanding and very adept at enticing him past what he thought were his boundaries.  She was so pleased with his progress into subservience that she gave him a pet nickname – pervy private sissy slut, or PPSS for short.

For his part, PPSS was in heaven; he began to search for ways to please his Mistress beyond what she had demanded of him.  For his first two visits she had ordered PPSS to present himself to her wearing sheer panties.  He so enjoyed the experience that for his third visit on his own initiative he shaved his legs and arrived wearing black thigh highs and a pair of black backless panties.  She loved it and they had a lot of fun that day.  Next he added a jeweled butt plug.  Did she seduce him into feminization?  Not overtly; she was simply testing his willingness to follow orders.  But, in doing so, she unlocked something in him that he didn’t know was there.  He thoroughly enjoyed dressing up for his Mistress!

It was through his relationship with Mistress Sabrinah that he met the lady for whom he was going to suck a cock – a man’s cock this time.  The new Mistress, Mistress Macayle, was Mistress Sabrinah’s mentor.  He read her posts and begged permission from both of them to be dommed by the two of them together.  It was exhilarating, but that’s another story.  During that session the Mistress Macayle had him on his knees, sucking her strap-on prior to fucking him with it.  She asked whether he had ever sucked a real cock and he told her about his experience with the trans-lady.  She smiled and invited him to read her posts of her experiences with trans-ladies.  She read him very well; she knew she had hooked him.

PPSS found the posts; they were amazingly erotic.  He found himself intrigued with this new Mistress.  She was both edgier and more self-confident than any woman he had ever met.  He began following her posts and it was there that he discovered her many posts on forced bi/MMF experiences.  It was evident that this turned her on greatly; she enjoyed forcing men to suck other men’s cocks for her.  PPSS read and re-read the posts until he almost had them memorized.  He was very turned on.  But, could he do this?  It was one thing to suck the cock of a beautiful trans-lady, but to suck a man’s cock?  He added forced bi and gay videos to his porn viewing and found he was very turned on indeed.  But was he turned on by imagining the humiliation of his Mistress forcing him to do something he wouldn’t otherwise do – suck a man’s cock?  Or was he turned on by the thought of actually sucking a man’s cock?  No, it had to be the former.  He wasn’t bi or gay.  Or was he?  When forced back into a tiny little corner from which there was no escape, what would he say?  He didn’t know.  But, nonetheless, he took the plunge and asked his Mistress Macayle for a forced bi/MMF visit.

It was arranged for some weeks hence.  In the back ‘n forth email, Mistress Macayle casually mentioned how well-endowed her friend, Ethan, was.  PPSS was stunned.  He realized he wasn’t at all prepared to service a cock of this size, so he bought a new, much larger dildo to practice with.  He spent quite a lot of time watching videos of ladies worshipping large cocks, mimicking their actions.  He fondled, kissed, licked and sucked the dildo, working hard to develop a natural flow to this new act he was learning.  Yet somehow he knew that when the moment came, all of his practice would fly right out of his head.  He would freeze and Mistress would have to apply some, hmmm, shall we say, motivation to get him moving.  But that really wouldn’t be bad, would it?  Being encouraged in that fashion might actually enhance the fantasy (Mistress had applied some rather forceful encouragement in their past interludes, which PPSS had found both rather exciting and more than a little painful, although the pain enhanced the excitement).  And, while he was practicing, he also practiced stretching himself with the new dildo, just in case . . .

And so the day was finally here.  But could he go through with it?  The thought of what was about to happen gave him butterflies – BIG butterflies.  His psyche was fighting a battle – no, waging a war - between his strict religious upbringing and his conviction that he wasn’t bi or gay, on the one hand, and his desire to please his new Mistress and humiliate himself for her  - and, to be honest, with the excitement of actually sucking a man’s cock, on the other.  What would happen?

 

Author:  bofors57