u/realCrystalVeeyant

It was like a dream come true up to this point. I’d been hired on as an executive assistant two years ago, advanced rapidly to the company president’s junior assistant, watched my salary go from $50K to $150K, my car from a used Honda to a company car—a Mercedes—and my shitty apartment to a condo with an ocean view. Best of all, I’d gone from humping my fist to loving a beautiful, brilliant, upper-class Stanford graduate a year younger than my twenty-four years.

Better than that, Brittany was also my boss’ daughter and she was as in love with me as I was with her. My big worry was how Mr. Edward Martindale would take to a middle-class dude like me as a son-in-law, even if I had graduated UCLA with honors? I worked closely with “Ed” every day and I had met his wife, Beatrice, many times, so I knew they liked me as a person.

But as a son-in-law?

Tonight was the night I would find out. Brittany had gotten me invited as a dinner guest to break the news to them. I went all-out and rented a tuxedo. This was my chance to make a big impression on my in-laws to be. I also brought along a gift, a $100 bottle of pinot noir. I left nothing to chance.

Their butler, Lucian, a handsome black man big enough to play football or to be a bouncer at a nudie joint, answered the door and escorted me to the living room where Ed and Bea waited for me on the sofa. They both wore pricey silk bathrobes. A beautiful, buxom young maid, not much older than me, dusted a bookcase wearing a risqué French maid’s uniform and tall high heels.

“That will be all, Evelyn,” Ed told the maid, who departed immediately.

I looked at them in confusion, still standing by the sofa. “Where’s Britt?”

“She’ll be here shortly,” Ed explained. He patted my knee with amusement and stood. “Nice tux.”

“See you in a little while,” Bea said, as her husband left the room. She gestured beside her. “Take a seat, Mikey. Have a chat with Mommy.”

“Mike or Michael, please,” I said as I sat beside her.

“You’ll answer to whatever name I give you. Would you like it to be Michelle?” her tone wasn’t cutting but her gaze could etch stainless steel.

“I’m sorry, I don’t understand. Have I done something wrong?”

“You’ve stepped well past your social boundaries. You should know you’re unworthy of a young woman of Brittany’s standing.”

“I—we don’t believe in all that elitist crap. She loves me. She’s said so many times,” I protested.

“I have no doubt she’s drawn to you. However, you’ve misjudged why.”

I stood. “I don’t have time for these games. Where is she?”

“Oh, this is not a game, Michelle,” she smirked. She undid the sash of her robe, parting it enough to show she was fully nude underneath. “This is a major life decision. You have sixty seconds to make it… take off all your clothes. Right. Now!”

“You can’t be serious, Beatrice.”

She stood and slapped me. Hard. “Call me Mommy! Fifty seconds.”

“This is totally crazy.”

“If you don’t follow my orders, you’ll lose your job and we’ll bring criminal charges for embezzling. Ed has been preparing the frame-up for weeks.” She glanced at her $10K wristwatch. “Forty seconds.”

I felt nauseous. “Nobody will believe it! I’ll hire the best lawyer!”

“The last two men we did this too said the same thing. One of them is in prison now. Thirty seconds.”

She gazed at me with hard, pitiless eyes. “But why?”

“On the other hand, if you get through tonight, you’ll get a new, better job, a far better place to live, and you’ll be with Brittany. That’s a no-brainer.” She studied her watch.  “Fifteen seconds. Strip.”

I tore off my clothes as quickly as I could while I wondered why she was doing this. Her exposed nudity made me realize she probably wanted to do stuff with me. Bea was a total MILF, but her potentially being my mother-in-law made it more creepy than sexy. No way would I let it turn me on. Whatever the fuck kind of game she was playing, I’d just get it over with and…

I tugged off my boxer shorts as she counted down to one. There I was, right in front of her, buck-ass nude and sitting on the very expensive carpet with my underpants hanging from one toe. She smiled smugly and ordered me to my knees. She stared into my eyes until I looked down in defeat and assumed the position she ordered. As soon as I had, she whipped off the robe and sat on the edge of the sofa.

“Look at it, Michelle,” she simpered, spreading her knees wide.

“Why are you calling me that?”

She slapped me. “You want to be a son-in-law? Call me Mommy. Now look at my cunt, Michelle.”

“Yes, Mommy.”

Hers was the pussy of a thirty-something porn star: thin, tight pink minor labia, swollen major labia and an erect clitoris protruding from the meaty hood. Then the vaginal entry popped open and my six inches began to get hard, as much for how beautiful it was but also how I was totally helpless. She popped an index finger in her mouth and slid it into her twat. In and out and in and out…

She knelt on the sofa, facing away from me, parting her soft, ample asscheeks and exposed the brown-pink swirl of her asshole. I’d jacked off so many times to fantasies of rimming a porn starlet or Brittany. The few times we’d made love, I had almost planted my tongue into her butthole, but something always held be back—how nasty it was. Yet that nastiness was what turned me on so much!

“Get in there, Michelle.”

“Wh-why? What for—”

She slapped me hard. “That’s for hesitating."

She opened her asscheeks again. This time I was quick to press my lips to her asshole and give it a hard lick. The taste was even more acrid and dank, yet also sweet. I kept licking her asshole until it loosened up and my tongue easily pushed inside. The flavor got stronger.

She pulled her ass away and ordered me to the back of the sofa, where she had me spread my legs wide and bend over the back. I steadied myself by planting my hands onto the seat cushion. I heard a squishy noise behind me. Then a moment later I felt a slippery fingertip trace firm circles on my asshole, making me shiver. I groaned as she slowly, gently slid it all the way in. Before long she had three fingers in me and my cock was harder than it had ever been before. I couldn’t help my sounds of pleasure.

“Feels good, doesn’t it, Michelle?” she cooed.

“Why do you keep calling me that, Mrs. Martindale?”

She reached around with her free hand and slapped me, just enough to hurt. “I told you to call me Mommy, didn’t I Michelle? Now ask me properly.”

“Why do you keep calling me Michelle, Mommy?”

“Because I’m fucking you like a girl, and you’re moaning like a girl, baby,” she purred.

“I wouldn’t say she’s being fucked like a girl just quite yet,” came my boss’ voice across the room.

“But she sure sounds like one,” laughed my fiancée.

Bea anticipated me trying to get up, holding me down with a hand squarely on my back while she kept slow-fucking my butthole. I turned my head and saw Ed leading in Brittany. Both of them wore robes. My girl carried a massive dildo, at least twelve inches, attached to a leather harness. I whined in frustration as my mother-in-law to be pulled her fingers from my butt and peeled off a latex glove onto the table.

“Take over while I strap on, darling,” she told my fiancée. “She needs a little more opening up.”

Brittany stripped off her robe. Underneath was a PVC teddy with her large breasts protruding from cutouts. She grinned at me as she pulled on a rubber glove. “I’ve been so looking forward to this.”

“I… I don’t understand, darling. You’re my fiancée. We’re going to be married! We—” I moaned as she shoved three fingers into me.

“Silly boy. I could never marry someone as common as you. When my true love comes along, he’ll come to accept the Mistress-sissy relationship I have with you. Then he’ll enjoy its benefits!”

Bea stood in front of me and greased up the mega-dildo. She smiled patiently, even kindly, at my puzzled look. “You’re going to be her toy, Michelle. Our toy, really. Now get ready to earn your new name! Are you excited to earn your new name, Michelle?”

“Please… please don’t do this—Mommy.”

“It’s done, darling. Reward her with a kiss, Britt.”

As my fiancée smashed her mouth to mine and thrust in her tongue, her mother touched the dildo head to my bunghole and eased it inch-by-inch all the way into me. My dick was so hard it ached and my balls felt like they would explode with pleasure. When Mommy started thrusting, I moaned so loudly.

“Let me in there, baby,” Ed chuckled, stepping in. “I’ve been looking for forward to this!”

My boss had stripped off his robe. His nine thick inches jutted like a flagpole from a building, inches away from my mouth. I was hypnotized by the sight of it. When he touched it to my lips, I couldn’t help that my tongue darted out on its own and licked the big glob of precum leaking out. The flavor detonated in my mouth, spurring me to open wide and take his dick into my mouth.

“That’s my good cocksucker, Michelle. Suck Daddy’s dick. Maybe I’ll get you to drink my cum.”

Suddenly I was in a freefall of giddy abandon, sucking this powerful man’s dick while his wife fucked me deeply up my ass with a monster silicone phallus. And then I felt their daughter gently jacking me off, a gloved hand cupped around the head to catch my load. Their economic blackmail was perfect—I bet rich folks like these had even nastier tricks they could pull—so I was helpless to defy them.

Please let me know what you think! 

If you'd told me long ago, when I first started crosdressing, that I would end up being a prolific writer of the same kind of sissy/CD erotica that got me started, but also that would get on hormones, transition fully, and become the same kind of top I used to dream about while I played with myself... well, I've have said that was impossible. Now I'm living the dream!

I wrote it over ten years ago and got a bit scared of it and so I took it off my Amazon shelf. Given that "stepcest" is now big in porn, I figure it's time to bring it back out so I did, then made it even raunchier and released it as a paperback. I'll be honest here... I used to have the hots for my own stepmother, who could have posed for Playboy. Hers was the very first lingerie I ever tried on, so this hits close to home!

Chapter 1

“Dude, I can’t believe we’re doing this!” I whispered hoarsely.

My cousin Chazz and I sat together on the king-sized bed in his stepmother’s bedroom, wearing her bras and panties. Our boners tented the pure silk of French-cut bikinis that smelled of Aunt Louisa’s lovely sweat and her musky-sweet pussy. Most eighteen-year-old guys jerked off to hot stepmother fantasies. We had taken lingerie out of hot stepmother’s laundry hamper and put it on.

“Woody, you’re the one who’s been talking about this every night for a month.”

“I know, but…”

“We’re just a couple buddies having kinky fun, right?” He finished his reassurance by reaching into my panties and encircling my stiff cock.

My dick swelled even harder at his touch, making me groan with pleasure. “Oh fuck that feels so different!”

“From what?”

“From when we usually mess around. Something about being all dressed up in Aunt Louisa’s stuff… y’know?”

“Yeah,” Chazz smiled. His look turned serious. “No cumming in my mom’s panties, okay?”

“You still calling her ‘Mom?’”

“That’s what she wants me to call her. Look, my stepmom gives me an allowance of a hundred bucks a week. I’ll call her anything she wants!”

“Okay, cuz,” I chuckled.

He and I weren’t blood cousins; his stepmom was my mom’s sister. Louisa and Elena were two sexy sisters in their late thirties who looked ten years younger. They must have been majorly hot when they were our age. Sometimes playing with myself late at night I’d think of my mom and feel very guilty. My cousin actually admitted the same to me about Aunt Louisa, but that was different. She was only a stepmother.

For the last three summers Chazz and I enjoyed our little jackoff sessions, but we had only watched each other do it. However, that changed two months ago. When Mom and I came down here on spring break, Chazz and I did our first mutual masturbation. We felt no guilt afterward, so we had totally looked forward to this annual summer visit. There were so many things we could try!

What had made the wait especially exciting had been Chazz’s recent discovery: a big trove of crossdresser, shemale and femdom porn. Four weeks before Mom and I drove down from Las Vegas, Chazz emailed me a bunch of his new jackoff material. We talked about it online every night, agreeing it might be exciting to try it out. We promised each other to wait until this visit before we tried getting dressed up.

Ever since Mom and I arrived here in Riverside yesterday, Chazz and I couldn’t wait for Aunt Louisa and my mother’s annual, day-long mall trip. The pair had left about twenty minutes ago. With the two MILF sisters out on their half-day shopping trip in Palm Springs, which was forty minutes away, we could have at least three or four hours of kinky fun.

Still moaning as my cousin jacked me off inside the silken bikini, I reached into his see-thru silkies and stroked him too. I marveled at how even softer and hotter his dick was compared with my own. Finally I couldn’t help it and I snugged down the waistband so I could see my stepcousin’s cock as I stroked it off. Before I knew it the sight of that lovely boner made me do something I wanted to do since Chazz sent me that first shemale video.

I got on my knees in front of Chazz. “Dude, I can’t help it,” I moaned. “I gotta know what it’s like.”

Chazz parted his knees. “Do it, man. Oh yeah.” He began breathing faster.

I stared at my cousin’s hard fleshy tool and hesitated only a second. I opened my mouth and took it in all at once before I could chicken out. His cock skin was soft as a girl’s lips and burning hot. It throbbed in my mouth. I allowed my cousin’s dick to rest on my tongue, getting used to the idea of what I was doing. Chazz’s soft moans filled my ears and overrode my hesitation. I began to suck hungrily on his teenaged cockmeat slurping and drinking down my saliva instead of spitting it out.

To my relief it didn’t taste strange at all, like sucking on a giant soft finger. Then it began trickling a salty taste into my mouth, but instead of grossing me out it turned me on even more. I went down on my cousin like I’d been waiting my entire life to do it, moaning and gulping like a passionate cocksucker. Right now I was so horny I didn’t care what happened.

I felt Chazz pull back and heard him gasp, and for a moment I was worried I’d bit down in my enthusiasm. I looked up into his eyes; the expression on my teenaged cousin’s face was one of shock as he looked toward the bedroom door. My mouth still wrapped around my cousin’s rigid dick I looked over and almost fainted. There stood my beautiful mom and aunt looking at the two of us with delight.

“It looks like you were right, Louisa,” my mom chuckled. “They are a pair of cocksucking sissies.”

“Aunt Elena!” Chazz moaned in dismay. “We’re not… not sissies!”

“Some very naughty sissies,” Aunt Louisa chuckled. “Wearing my good lingerie like that.”

I pulled off my cousin’s wilting boner and looked fearfully at the women. “I… I can explain.”

“I think they need to be punished, don’t you?” Aunt Louisa said to my mom as if she hadn’t heard me at all.

“I couldn’t agree more, Sis. Do you have any suggestions?”

Aunt Louisa appeared to think for a moment and then grinned evilly. “Well, since they want to dress up in ladies’ clothes I think we owe them the full girl experience.”

My mother returned the mischievous look. “For how long?”

Louisa shrugged. “I’ve always wanted a daughter. Until we get tired of it, I suppose. At least a week or two.”

This would be so weird—sissy training under my mother and aunt, right alongside my cousin. I was dizzy with shock at the realization they were serious, but I couldn’t understand why I was getting hard all over again. Then my mom’s hand encircled Chazz’s cock, which I’d been sucking only a minute ago. She stroked it until it was throbbing hard. She was just his step aunt but…

It’s still wrong!

“Your cousin needs your attention, Woody. Suck his dick and make sure we see him cum in your mouth. You want to wear my sister’s best panties, you earn it!”

I was in shock at not only the sight of my mom beating off my cousin but the look of lewd glee on her face when she ordered me to give head to him. “Mom!”

She let go of his dick and turned toward me, looking down into my eyes with her fists on her hips. “Do you want to know how fast I can yank your college tuition and kick you onto the street? I don’t think you’ll like being broke and homeless, Woody. You’ve seen how the homeless do in Vegas.”

My eyes filled with tears when I saw she was totally serious. My cock got even harder when she allowed herself a frosty smile of triumph.

I knelt back in front of my cousin while she and my aunt watched. As horrifying as this was supposed to be, I couldn’t wait to suck his cock again, even if I had to do it in front of Mom and Aunt Louisa. I looked up at the two MILF sisters watching me with terrible, hungry grins, and I thought back to how all of this had started—when Chazz called to tell me he’d discovered a stash of smut.

As lowered my mouth onto my cousin’s dick I marveled this kind of kinky thing was happening here in boring, middle class Riverside. The Inland Empire, the part-desert region between Los Angeles County and Palm Springs, didn’t seem like a place where this kind of thing happened. Considering how easily Mom and Aunt Louisa were doing this to us, I wondered what else I might not know.

You can read the rest of this for free on FetLife. The full-length incestuous novella is available and a ebook and paperback on Amazon. See comments for links!