Throughout the coarse of talking to all you beautiful boytoys, I have heard some serious whoppers. It's often difficult to tell which ones are true to life and which ones are just well thought-out fantasy, but every now and then you come across an individual with such a rare gem of an eye-popper that you can't help but believe it. The details are there, the answers are consistantly the same... this is the retelling of someone's actual life experience.
READER BEWARE - this is a long fucking story.
Such is the case with Sandy a.k.a., "Cassandra". Cassandra has been a sissy almost his entire life - Mommy Dearest took extra special care to see to that, as did his sisters. They'd dress him up and primp and pamper him until he knew deep down that all he wanted out of life was to be a pretty girl. He trudged through life pretending to be the boy that his body insisted he must be, went to college, got his degree, became an attorney, yadayadayada...
Enter Susan. Susan is (currently) Cassandra's wife... though not for much longer. ;) Susan was kind enough to embrace and dominate his feminine quirks, dressing him to her taste and fine-tuning the raw beginnings that his mother set in place. She, of course, continued to date and get fucked by real men while her sissy stayed home and played... housewife? Maid? Either way, as happy as everyone involved was with the situation, there always seemed to be something missing.
Now if it seems like I'm glazing over the facts a little bit, keep in mind... this is just the back story. The real story begins with Steve.
When Steve and Susan first started dating, Cassandra had no way of knowing that this particular match-up was about to change his entire life for good. How could he? His wife had been through tons of guys in the past - no big deal. None of them were really longterm material, just a bigger dick for her to fuck than the little clitty he had to work with... not that he ever did more than cum in his panties anyway. But after a few months of dating, Susan brought Steve home...
And insisted on Cassandra being the one to answer the door for him.
This was the first night I ever spoke to Cassandra. He was literally shaking with that intoxicating combination of fear and excitement; asking Me how he should greet Steve, and whether he should ask his gorgeous wife if he was to answer the door dressed as a man or a woman. What would Steve say? What would Steve DO? LOL! Finally I calmed him down enough for him to gather up his courage and approach Susan about dressing himself up as a woman (which was so obviously what he wanted to do anyway.) Susan was pleased, to say the least.
Later that night, Cassandra contacted me again to give me an update. Steve had shown up, apparently very pleased to see good ole Cassie dressed up like a proper lady, and proceeded to take full advantage of the situation. Translation: Cassie got fucked GOOD. It was kind of a big deal, actually. Up to this point, Cassandra had only ever played with toys. The thought of experiencing the real thing had been nothing more than a pipedream and he was filled to the brim with ideas of what might happen next. Funny thing is, he had every reason to be.
Again, I got a call. Same night, not too long after the first update - Susan and Steve were staying out late, and they were sending out a BABYSITTER for Cassandra. Um.. okay! LOL We tossed around a few options for potential "babysitters" that Susan might send to watch over him. A couple names were mentioned, but there was one name in particular that put dread in Sandy's voice - Dan.
Dan was the husband of Susan's friend, Karen. Dan was also a fellow attorney, working for a competitive law firm. Already, Dan and Sandy had faced their share of run-ins in the courtroom... almost always with Sandy on the losing end. He was an arrogant SOB that Sandy was incredibly intimidated by, and Susan knew it. It only makes sense that if a babysitter had to be brought in, it would be him.
And wouldn't you know, that's exactly who showed up at Sandy's door! Keep in mind, Dan already had some idea of what went on between Susan and Sandy. His wife was her best friend, after all, and well... girls talk. A lot. It would be fair to assume that what Dan didn't already know (if anything) Susan had filled him in on by the time he pulled up into the driveway. From there, Dan had the distinct pleasure of humiliating Sandy to the Nth degree. He stripped him down, fucked him, spanked him, and proceeded to give him a bath. Babysitting, huh? Well... I guess. Sandy certainly did get taken care of, at any rate! LOL Sandy was shaved clean, put in his nightgown, and put to bed, using Dan's cock as a pacifier. He awoke the next morning to witness his wife and her date standing over him laughing their asses off.
There is so much more story to tell, and trust me, it only gets weirder from this point on. Let me assure you, this is NOT a product of my imagination. If anything, I would say it was too much too quickly and a little overboard in terms of what is realistic and what's not. But then again, as the title says, sometimes fact really is stranger than fiction.
To Be Continued.....
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