The Secret Life of John and Sara is based on a true story. I’ve fictionalized it to protect the identities of my friends John and Sara, whose ‘secret life’ is secret for a very good reason. John is a Silicon Valley CEO, [...]]]>

This is Part Nine of The Secret Life of John and Sara, started here.

The Secret Life of John and Sara is based on a true story. I’ve fictionalized it to protect the identities of my friends John and Sara, whose ‘secret life’ is secret for a very good reason. John is a Silicon Valley CEO, a sissy and a cuckold, and Sara is a 40-something nymphomaniac Nurse Administrator. Here is their story:

“I won’t tell The Major if you won’t,” I said to John, mostly for effect.

Daddy already knew how I was.

An uncle figured it out when I was 10 or 11 and I overheard him saying to my father, “She can’t be trained like the others, Simon, she’s not going to just take orders. She’s spirited, like my stud, or my lead mare. She’s going to take careful handling. You’ve got a little dominatrix on your hands, mark my words.”

But John didn’t know that Daddy knew, and in saying that, I’d gained his trust. He thought we both had something we wanted kept from The Major, and that gave us a bond.

“I need to ask you some questions, John, and I want you to answer honestly. I have some ideas, but I need more information.”

John agreed with great relief, and I asked him a plethora of questions while he made us virgin mojitos and we moved out onto the deck that faced north, toward the bay.

The picture that I constructed after my battery of questions and his candid answers was this: He and Sara had dabbled in dominance and submission, had even gone to The Citadel in the City once in a while. Yes, Sara seemed to enjoy being submissive, and no, she’d not shown any inclinations toward dominance until the past year. No, being submissive didn’t arouse him, not the way being feminized did. When I asked him about his cross-dressing, I learned quite a lot. He’d gotten started with an ex-girl friend’s panties–jerking off into them. Then he jerked off wearing the panties. He liked the softness of the fabric. And there was something about the fear of discovery that added extra spice to it. As he’d gotten older and building his business became more stressful, he sometimes sought refuge in dressing like a woman, because when he was dressed like a woman he could find emotional release from the tension by crying, acting frivolous and care-free, or simply allowing himself to feel helpless.

But in the past 6 months Sara had taken him places he never wanted to go, places he wasn’t sure he wanted to visit ever again. Forced feminization had really pushed the line, but with cuckolding and chastity she’d taken things way too far — and now he wasn’t sure how to get his marriage back on track.

When he finished talking, I asked him a question that surprised him. Had Sara ever been with another woman?

His affirmative answer had me going “Yes!” A plan had been forming in my mind, and that final bit of information had me fairly confident of success.
To be continued tomorrow…

I grabbed him by the hair and leaned forward, pressing his face into the wood of the desk while I forced a finger into his ass.  I told him he was mine to do with [...]]]> This entry is a continuation of previous posts.  If you haven’t read them yet, it is probvably best to start here.

I grabbed him by the hair and leaned forward, pressing his face into the wood of the desk while I forced a finger into his ass.  I told him he was mine to do with as I pleased, and seeing as he had been such a bad boy recently, cheating on his wife and nailing every pieces of ass in sight, I was going to rape his ass. Give him what he deserved. He moaned, diving deeper into sub-space with every word I spoke. He was completely naked, with me standing over him in my bustier and stockings, and he ate it up.

I told him how much I was going to make it hurt, and how he was going to take every inch of my strap-on, and that he was going to take it with his mouth closed, no screaming, and that the only thing I would permit him to do was to grip the edges of the desk to brace himself. If he did anything else, if he screamed too loudly, if he moved to resist me at all, I’d leave. I’d take my strap-on and my bag of tricks and I’d walk out on him, leaving his ass hungry for what it really wanted.

Then with a final rub of his face into the wood of the desk, I released his head. I moved around behind him, deliberately dragging the strap-on down the length of his body.  I scratched at his welts with my fingernails, which made him whimper and  dance his ass around. And then I stood behind him, with the head of my big black strap-on pressed up against the puckered rosebud of his anus and I said, “Tell me how much you want me to fuck your ass.”

And he did. He begged, he pleaded, he told me in lurid detail how he wanted me to ream him out, how he’d cleaned himself for me, how he was such a bad boy and deserved what was coming, every last inch of it.  And in the middle of one of his sentances, I leaned hard into him and forced the head of my strap-on into his ass. He gasped and sucked in air and then his teeth clicked together and he moaned mightily, his fingers gripping the edge of the desk until his knuckles turned white. The cocoa butter creme gave his ass and my dildo an awesome slipperiness that allowed me to push smoothly into him, even as his body tensed, even as he resisted my efforts to penetrate him. And penetrate him I did, diving inexorably into his ass until every one of the 10 inches was inside him and my harness was abrading his welts.

And oh how me moaned! How he wriggled his ass! He cried, his tears pooling on the desktop, but I didn’t stop.  He wanted to be violated, wanted to be taken hard and fast, and so that is what I did. I set my feet in those 4″ heels, grabbed his hips, and fucked his ass with unrestrained violence. I unleashed a tempest of passion on him, and as I invaded him, I subjugated him with my voice, with my words, telling him he was a pathetic excuse for a man, and that he’d never fuck me again, not with his small little penis that was incapable of satisfying me like Simon could with his big thick cock. And I described Simon’s wondrous cock, the cock that produced the copious amounts of cum that Pilot had recently cleaned out of me.

I leaned forward onto Pilot, my palms balanced on his low back so the angle of penetration made it possible for me to hit his prostate, and as I jabbed my hips into him, I told him to cum, demanded that he empty himself without a single stroke of his cock, and he did.  He came hard, with open-mouthed cries, his whole body rigid, as I sawed the head of my strap-on against his prostate.

Such a good little anal whore.

My pilot friend met me in the lobby. We hugged hello, and when his arms wrapped around me he said, “I’ve been dreaming about worshipping your ass all week.” I purred, flush with memories. A closet submissive with a guilty conscience, the man had a serious thing [...]]]> This blog entry is a continuation of this post.

My pilot friend met me in the lobby. We hugged hello, and when his arms wrapped around me he said, “I’ve been dreaming about worshipping your ass all week.” I purred, flush with memories. A closet submissive with a guilty conscience, the man had a serious thing for asses and freshly-worn panties.

We had drinks and some appetizers in the hotel bar and talked about all sorts of things.  We talked about his work, and how being an airline pilot still qualified him as a pussy magnet.  I learned a lot about the sexual habits of airline personnel, who were apparently uninhibited by marriage in their activities. Apparently pilots and flight attendants are constitutionally unable to be monogamous. Every overnight was like staying in Vegas. Apparently, what happens on an overnight never happened.

Within two hours we were upstairs in his hotel room, my black leather dufflebag sitting prominently on the bed. He kept glancing at my little bag of tricks, growing progressively more excited. I grabbed the bag and walked toward the bathroom, telling him that when I came out, I expected him to be ready for me.

In the bathroom, I disrobed, carefully hanging my litle black dress on a hook. I pulled my harness out of the bag, located the dildo, and gave it a quick soap-and-water rinse.  I noticed the Fleet’s enema packaging in the garbage, so I knew it wasn’t necessary to hang up my old-fashioned enema bag — my pilot had already prepared himself for the evening’s adventures. I adjusted my black satin bikini-bottom panties, making sure they fit snugly into the crack of my ass, plumped my breasts in the bustier, and headed back into the room with the dildo and hardness in one hand and my bag of tricks in the other.

Pilot was on his knees  by the desk, utterly naked and fully erect.  When he saw me, he moaned. I set the bag and toys on the bed and sauntered over to him. When I reached him I grabbed him by the hair and forced his face up against my panty-covered pussy. He rubbed his face against the satin, breathed deeply, and sighed. His hands caressed my legs on their way up to my ass, which he cupped worshipfully in his palms as if each cheek was made of Ming china. I told him that I’d had sex with Simon a few hours ago, and that he’d cum in my pussy and my ass, so I had some cuckold clean-up work for him. Which he proceeded to do with enthusiasm. Simon sucked the crotch of my panties and then cleaned my pussy and ass with his tongue like the good little submissive ass-worshipper he was.

I rewarded him by bending him over the desk and thoroughly thrashing his ass with my crop. When he was nice and pink with lots of good welts, I massaged cocoa butter creme into his skin. He sighed so voluptuously that I couldn’t help but pinch his welts once in a while, seasoning his pleasure with jolts of pain that made him hiss and moan. Then I put on my harness, slid a polyurethane condom down the length of my big 10 inch strap-on, and rubbed more cocoa butter creme along its length.  I was making it very very slippery, so it would slide in easily, no matter how ready Pilot was. He liked the pain, the feeling of violation, and I was just the woman to give him what he craved. Oh yes, I certainly was.

Read the continuation of this story here.

Lets take Pantyboys, for example.

I’ve lost count of [...]]]> For most people, sex and fear are inextricably intertwined. At first glance I think most people miss it. Some would even deny it. But an examination of an individual’s sexuality will almost always uncover a host of fears. And the kinkier the person, the more interesting the fears.

Lets take Pantyboys, for example.

I’ve lost count of the number of times men have whispered to me “I like to wear women’s panties… does that mean I’m gay?”  I usually respond with a question of my own: “Are you sexually attracted exclusively to men?”  If they answer no, which is usually the case, then I tell them they are not gay. But they still don’t want to let go of that fear-linkage that wearing panties equals gay. Why?

Because the fear, even more than the panties, is the spice. Fear spikes the sexual punch. The forbidden (panties) makes it more exciting, but the fear (maybe this means I’m gay, or, what if someone catches me, or, does this mean I am a sissy) is the necessary ingredient for sexual satisfaction. The fear pushes the ejaculate button in most panty-boys. As a FemDom it is fun to figure out not the fetish (panties) but the fear intertwined with the fetish (what if my girlfriend catches me) and use it to push those buttons.

It is fun to play the girlfriend catching them in panties. It is fun to be angry and mocking. And sometimes its fun to threaten to take photos and ruin their lives if they don’t put on a nightie, too (sissification, anyone?).  Sometimes its fun to make them clean house wearing panties only, with the windows and curtains open so the neighbors might see (exhibitionism, humiliation). And sometimes it is most fun to threaten to invite a gay friend over to see the pantyboy and decide for himself if my boyfriend is gay.

For some, humiliation, degradation, and embarassment are the fear-linkages. For others, gay sexuality is the real erotic hot button.  What if the girlfriend finds me in panties and forces me to do things with another man? And that is where I come in.  Because I can “force” pantyboys to explore this fantasy in the safety of their minds at no risk to themselves, and very little cost. In many ways, when it comes to exploring fetishes, fear, and sex, having a FemDom in your life is priceless.

Working later hours last night went pretty well, and given that my lover was playing poker with the [...]]]> Every once in a while I get a foodie on the phone. Foodies are shy about their fetishes and sometimes it can take 20 minutes for them to get around to talking about what really turns them on. Food.

Working later hours last night went pretty well, and given that my lover was playing poker with the guys, I kept the lines open for an extra hour or two, and took some interesting calls. One of them was from a guy who had never eaten his own cum, and wanted me to ‘help’ him do so. Getting him worked up was not difficult.  All I have to do is open my mouth and most men are instantly hard. I’ve just got one of those voices that tickle men behind their balls. But I knew, as we were talking, as I teased him with different images like getting him off with my feet and making him lick his cum off my toes, or eating another man’s cum from a freshly shaved pussy, that he was holding back on me.  He wasn’t into body worship or cuckolding or humiliation. 

I was about ready to go the pantyboy route with him when he asked me if I’d ever heard of someone cumming on their food and eating it. And that was when I knew I had a foodie. I giggled and asked him if that is what it would take to get him to eat his own cum — did he want a bagel and schmeer? His breath caught and he tried to laugh, but it came out as a huff, the kind of huffing sound a guy makes when he’s been punched in the solar plexus — or when his sexual buttons have been pushed.

“Mmm…” I said, “Instead of a bagel, lets imagine a warm cinnamon roll. Wrap your cock up in that warm, googey goodness and stroke. Can you smell the cinnamon?”

The tension in his voice was beautiful. “Ooooh… If I had a cinnamon roll I’d go get one right now,” he gasped.

I mentioned the cinnamon roll warm and slippery like a pussy, and his cum the icing on the roll. And that was it. Bang! Over the edge he went, huffing and moaning and spewing into the imaginary gooeyness. He was only too happy to lick the cum off his fingers then!

Yes, foodies are fun.