Jamie is a cute, twenty-one-year-old guy with a secret: back in high school, he and his best friend Miles used to get very stoned and play truth-or-dare where one of them would put on panties and give the other one a blowjob. Since then, Miles's stepsister Helen had turned Miles into Millie, whose stepdad turned into his own sissy slut and whore. Millie wanted to get back together with Jamie for sexy fun, but Jamie is freaked out by his big-titted ex-buddy.

Now Jamie is back from college, and his stepsister Diana, 19, is having a sleepover with some of her hot friends: stepsisters Chandler and Shanna, Neesha, Maria and ~Helen~. Jamie just has to see the all of these hot young women in lingerie or nude—maybe even some lesbian action!—so he hides a webcam in his sister's room. Soon the girls start drinking and smoking pot. Jamie can't wait to see!

Finally they sounded rowdy enough to switch on. I gasped at the sight: they wore mostly just bra and panties—skimpy designer stuff that showed more than it concealed—except for Helen who wore only the tiniest thong. She kept eyeing my sister with sly grins. Would she?!

Then Helen whispered in Diana’s ear and my sister giggled. Diana looked at her best friend and nodded. Oh fuck!

“Let’s take a picture!” Helen suggested. “All nude!”

“I’ll need another couple shots to do that,” Maria laughed. “But let’s try a few topless!”

“Are we going to take a big selfie?” Diana asked. “I don’t have a stick. I could ask my brother…”

“To take the picture?” Helen barked a laugh. “He’d wear out his dick jerking it afterward!” She licked her lips. “I’d kind of like that.”

“No!” Diana protested laughing. “To borrow his selfie stick.”

“Why don’t you just take some from over there?” Helen said. “We’ll do some poses, taking off our tops and stuff, and you go crazy with the camera,” Helen said. “Then we’ll figure out a group shot!”

I was disappointed when my sister hopped off the bed with her phone. She was out of webcam range, so I couldn’t see if she was taking off her top or not. I quit caring about that when the other girls started posing. Helen kissed Neesha’s neck and slid off her bra.

“That’s perfect!” Diana said off-camera. “Slide it off slowly.”

Neesha’s bare breasts were sweet brown and huge with thick, erect nipples. I’d earlier put on panties I’d stolen from Diana to enhance my viewing. I was now fully erect in the rose-colored silk that still smelled faintly of her pussy. I took out my cock and started jacking off.

There was an electronic click just behind me. I turned and froze with my boner in my fist at the sight of my sister aiming her phone at me. There was another click and she chuckled behind the lens.

“That was perfect! I got your boner, the panties and you spying on the girls in my room.” Her eyes gleamed with dominance. “So that’s where those went! I couldn’t find them when I washed my lingerie earlier today.” She waited a moment. “Nothing to say?”

What was there to say? An apology after being totally caught in the act? To beg her not show anyone out of the kindness of her heart? Then I realized if I wanted to ask anything it was—

“I figured you’d try something like this, Jamie,” she smirked. “And it wasn’t hard to find when I guessed what you’d most want to see. Some college girl lesbo action on my bed? Your own sister naked?!”

“What do you want?” I sighed in defeat.

She looked at me almost kindly. “I think it’s really what you want.”

Diana led me into her bedroom wearing only her panties which bulged with my erection that hadn’t gone down. They were all topless, the most perfect tits ever on display, and they all looked at me with big, eager smiles. It’s like they already had a plan for me.

“He needs a good buzz,” Helen said. “It will make the first part a lot easier on him if he’s more pliable.” She walked up to me and cupped my boner through the panties. “I know your secret.”

“Wh-what secret is that?” I whined. But I could guess. Miles told.

Soon I had downed three shots of $50-a-liter tequila and as many deep hits of $900 an ounce weed. My head spun a bit but I was lucid.

They all led me to her bathroom where cold wax strips had been set up. I was grateful to have sparse chest, leg and arm hair; it would have hurt much worse if I’d been really hairy. My buzz made it more tolerable too. Under Helen’s guidance I stood naked in front of the mirror and close-shaved with skin lotion until no trace of a beard was left. I was smooth as a girl!

And my cock was still fully hard.

“Back when Millie was a boy, she and Jamie used to take turns, dressing in panties and cocksucking,” Helen told everyone. “Millie said he chickened out, didn’t want to play sissy any longer.” She winked knowingly. “From the sight of that raging boy-clit, I think Jamie is having a change of heart.”

I blushed deeply at having our—my—shameful secret revealed.

“Jamie!” Neesha said. “It’s both a boy and a girl name.”

“I think he should have a real girly name,” Diana said.

“You might have to change pronouns,” Helen said. “Your brother might end up being your sister, like Millie. Any ideas for a name?”

“Let’s ask her!” Maria chimed in. The sweet Latina’s nipples were hard as she stepped up and pressed her large tits into my back. She reached around and teased my throbbing cock. “What girl name would you like for yourself, sissy?” she asked.

I knew I had to play along. “Ashly,” I said automatically, thinking of the porn star. She was girl-next-door beautiful and super sexy.

Diana kissed me deeply for a moment and then smiled brightly. “Ashly it is, big sister!” She turned to her friends. “Makeover!”

As soft but firm feminine hands guided me to my sister’s vanity, part of my daze began to break. The initial shock of being caught, outnumbered by the women, and my high had all got me through everything up to this point. Now a part of me wanted to rebel.

You’re naked in front of your sister and her friends! Now they want to put makeup on you and probably a wig and sexy clothes. Then who knows what they’ll make you do!

Miles and I never did makeup before Helen transformed him. He knew better than to suggest it last time. He knew I wasn’t a sissy or a fag. How come these girls don’t see that? But deep down part of me fantasized maybe they’d let me have sex with them if…

If you let them take away your manhood? Miles’ sister “pegs” him. You want these girls—maybe your sister!—to fuck you in the ass*?!!! Stand up for yourself! … Who are you kidding? Those pictures…

As the girls worked on my makeup, I knew all was lost. If I tried to refuse, Diana would post those pictures of me on every subReddit and social media service I ever used. Meekly submitting like a BDSM submissive would keep it private. I hoped.

After fifteen minutes I was astonished what the girls did. Mine was the face of every porn starlet I ever jacked off over. I looked like… a girl!

“Damn, that’s good work, girls,” Diana said. “She looks like an Ashly.” She grinned at Helen. “Let’s get her ready to be Ashly!”

From Helen’s gym bag, they dressed me in an expensive, frilly pink Merry Widow with garter straps that left my cock and ass exposed. The matching panties had the crotch cut out to provide access to my cock and asshole. They strapped me into a matching bra and fed silicone breast forms into the cups. Finally, pink fishnet stockings!

“Come to the mirror,” Diana commanded.

She stood by a full-length dressing mirror and beckoned me with a huge grin. I went meekly and gasped at the sight. Save for my boyish haircut, I looked like a fuckable slut… with a raging boner.

Why is it so hard?! I don’t want this to turn me on!

“Rock hard,” Helen smugly observed. “I knew it.”

From the bag they pulled a big, bleached blonde wig and firmly clipped it to my own hair. Finally they put me into stripper’s four-inch platform sandals, also pink. Now the image in the mirror made me ragingly horny. Deep down I looked forward to whatever they—

Helen opened my sister’s bedroom door and said, “She’s ready.”

In strolled Miles—Millie, she really is a Millie!—dressed identically to me with one exception: she had real breasts. They were D-cups that rode high and nearly spilled out of her bra cups.

She saw me staring. “Daddy bought me these tits,” Millie purred, meaning her stepdad.

Weak with shock and desire I wavered in my platforms. Diana and Helen caught me and helped me to my knees while Millie explained.

“My stepdad makes good money pimping me at his poker games. Now I’m whoring,” she said. “I could have gone back to college as Millie, but being a sissy is all I want to do! And when Mike asked if I wanted to be a real shemale I kissed him!”

She got breast implants a week after our last visit. A month later, she started doing outcall prostitution to Beverly Hills, Bel-Air, Brentwood and every other exclusive zip code within a half-hour drive. And she would shoot her first shemale porno next week.

Millie looked so beautiful and desirable. How could I not lust after her? I had loved Miles as my closest buddy but this was so much better. The reflection of us in the mirror, two gorgeous, sexy sissies, filled me with deep desire and sudden acceptance. I was like her.

She stood over me, her hard cock inches from my face I told her how beautiful and sexy she was. She said she loved me.

“I love you too, Millie,” I sighed. I bit my lip. “May I...?”

She touched her cock to my lips. In front of my sister and all of her friends, I took my shemale buddy’s cock into my mouth and began sucking her off with all the pent-up passion I must have always had, without and shame at all.

“Oh God, that is hot!” Neesha said. “Your own brother!”

“Not anymore, I think,” Helen said. “Are you okay, Diana?”

“There’s no one word to describe how I feel. Delighted. Thrilled. Affectionate,” my sister said. “I feel like… in helping Ashly find herself, well I guess I am finding myself too.”

“Does anyone else think it’s funny he put the camera in here to see some lesbian action and he became the lesbian action… so to speak?” Chandler said.

“We should respect her new gender,” her stepsister Shanna said. “If she really wants to be Ashly.”

My sister, naked save for panties, took a knee next to me as I gave my best friend a passionate blowjob. “Do you, big brother?” Diana asked. “Would you rather be my big sister, Ashly?”

I pulled off Millie’s cock and looked at Diana with such love and gratitude. “Yes, Diana,” I sighed with happiness. “I would.”

My sister put her lips to mine and we kissed deeply, our tongues dancing playfully as our sublimated passion burst to the surface. All of her friends sighed deeply at the sight of our taboo kiss.

“Well fuck it then,” I heard Chandler say. “If they can do it in the open… Come to me baby.”

The blonde stepsisters crushed their topless bodies together and kissed like longtime lovers. They sank to the carpet in a feverish lesbian sixty-nine, forgetting all about the rest of us.

Helen produced a ten-inch dildo on a harness and handed it to Diana. “I did Millie. It’s only right you turn Ashly into a proper sissy.”

For a moment I couldn’t breathe. Then I looked at my sister with pleading eyes. “Fuck me, little sister. Turn me into your Ashly.”

- from T-GIRL TALES - Family Values