I must take a little break from Reddit to do other work, so I leave you with this parting gift: a new slice of "Mommy's Sissy Slut". Enjoy, my sexy darlings!

In this story, Teddy—now named "Amber"—is the personal slave of his porn star stepmom, Cheryl. Amber has been financially blackmailed into it. Oddly enough, the eighteen-year-old sissy is turned on by the humiliation of being an out sissy, so Mom must find new ways to test those limits! Like, perhaps, making him fuck his old buddies from school...

Over the next month I put Amber on female hormones and into an electrolysis clinic so she’d never have to shave or wax her chest or arms again. I loved watching my sissy slave shave her legs so we kept that. And I got her stripper-sized silicone implants.

 Amber accompanied me everywhere as my personal assistant, always in barely legal outfits and a silver slave collar proclaiming her mine. She slept with me, except when we played slave-mistress games. I’d trained my stepson to be an expert pussy-eater, and we sixty-nined as much as we fucked, with me always on top.

 What I loved most was finding new ways to humiliate her ever more deeply. I hired a private investigator to track down Teddy’s closest buddies and find out who’d be willing to have sex with a sissy slave who was their old buddy.

 He found two of them, both very willing!

 Brad and Chuck had been varsity athletes who’d taken a liking to my slender, androgynous stepson in their last year in high school. Perhaps some subconscious attraction to the slut inside their pal.

 I answered the door in hot pants and a thin blouse tied under my breasts. My rigid nipples showed from my lack of a bra. They looked hypnotized as they came in and sat on my sofa. After brief introductions they were ready to see their old pal as a sissy slave.

 “We still get to be with you too, right?” Brad asked.

 “But of course. That’s part of the show,” I said, winking. “I have all kinds of naughty things planned.”

Chuck clapped his hands once. “Hell yeah! Let’s do it.”

 “Why don’t you take off your clothes while I get her?”

 I went to get my sissy stepdaughter in the bedroom. She knelt on the floor in front of our bed. She wore a garterbelt with stockings, a shelf bra propping up her huge tits and pierced nipples, and crotchless panties from which her rigid cock jutted.

“Time for you to lose you true virginity, baby,” I soothed. “Follow Mommy out to the living room.” 

* * *

 I blushed brick red when Mom made me follow her out to the living room on my hands and knees... leading me on a leash. They sat naked on the sofa, stroking their dicks. It was humiliating to have them see me this way and calling me a sissyfag and gloating how they’d cum in my mouth. And yet my clitty was fully hard.

 “Look at the precum dripping out of his cock!” Chuck sneered.

 “You make a good girl, Teddy,” Brad said. “I always knew you were a cocksucker. Big fag. Aren’t you, baby?” He looked to Mom. “You want us to call him Amber and ‘she’ instead, right?”

 “I want you to humiliate her, break her ego as much as possible. Make her feel like a lowly sissy slave. If calling her ‘he’ and ‘fag’ or ‘Teddy’ will do that, then go ahead.”

 Brad grinned and brandished his cock at me. “Come suck my dick, Teddy. Show your mom what a cock slut you are!”

 Burning equally with shame and pride, I crawled to the former star linebacker, my new tits dangling and swaying the whole way. He held his ten-inch, pulsing tool between his fingers and milked out a drop.

 “Somehow I knew you were a cocksucker, Teddy,” Brad said as I knelt right in front of him.

 “Please call me, ‘Amber,’” I begged. “That’s my name now.”

 “Maybe if you prove it. Now suck!”

 I’d seen his cock before many times in the showers in the boy’s locker room, but this was the first time seeing it hard. Now it was red and purple, swollen erect. I couldn’t take my eyes off it.

 “Oh God,” I sighed and opened my mouth.

 Brad groaned so loudly as I engulfed his pulsating prick. The feel of it in my mouth, the taste of his juices, the smell of his sex all made me excited. But remembering all the times we hung out after school, rode around in his car, went to the movies and such—this was my buddy and now I was sucking his dick.

 I’m so horny, so horny. Brad, cum in my mouth! Then fuck me!

I couldn’t believe how excited I was at this new low, being outed and humiliated as a sissy fag in front of my school buddies.

 “I’m getting horny watching,” Chuck said. “What’s it feel like?”

 “Like a chick is blowing me. Only no girl ever gave head so good. Amber’s a born cocksucker,” Brad groaned. “Want some?”

 “Hell yes!”

 “Get over here, man. I’m gonna give her a good fucking.”

 “Let me come over there and loosen her up for you.” Mom got up and slipped out of her blouse. “Don’t want to get lube on these.”

 For a moment my pals were transfixed as they watched her strip to a transparent thong that showed her pussy. They sighed in their excitement. I swelled with pride at how sexy my mom was.

 Mom worked two fingers in and out of my tingling asshole—a new level of thrilling humiliation, especially when the guys enthused how it looked and how my mom was so fuckable.

 “Only Amber gets to fuck me. Maybe we’ll show you later.”

 “You fuck your own son?” Chuck breathed.

 “She’s my stepson, so of course I do.” She pulled her fingers out of me. “She’s all ready for you, Brad. Spit-roast my slut for me.”

 Brad slid his big cock up my ass while Chuck boned my mouth. Tears of joy welled up at feeling my best friend’s long dick slid in and out of my asshole while I sucked my other friend’s pulsing tool.

 Of course, that was the moment my dominant stepmom made it even sexier. “Don’t mind me, boys,” she said.

Mom stripped off her thong and sat on a big, heavy stool right next to us. She spread her legs wide and fingered her pussy.

 “Oh, fuck you’re so sexy!” Chuck moaned. “I want you so fucking much. I hope maybe later?”

 What I could see of her face over Chuck’s hip suggested sexy mischief. Then I heard her say why didn’t he take a seat and let her give him a special lapdance. He pulled his cock out of my mouth so fast it was almost comical. I pouted, missing dick in my mouth.

 Brad spun me so I could see the lap dance. He eased his big meat back into my boi pussy and resumed fucking. Mom straddled Chuck, both of them totally nude, and began rubbing her large, round ass all over his throbbing cock. She moaned and sighed and writhed.

 Mom’s cucking you with Chuck. Right in your face!

 I was hypnotized by the sight of my gorgeous stepmom grinding her perfect, naked ass into my school friend’s hard dick. And the whole time my other buddy slowfucked my hungry asshole, taking my sissy virginity. I loved cock, sucking and getting fucked by it!

 “You’re such a sexy sissy whore,” Brad said as he cupped my large new breasts. “You like being owned by my cock, Amber?”

 “I love your cock! I want it deep up my ass and in my mouth!”

 “So, you want his cock in your mouth, baby?” Cheryl asked.

 “Yes, Mommy! Yes!” I whined.

 “Even though it’s in your ass right now?”

 The reality suddenly struck me. Was I ready for this?  “Mom?”

 “I’ll take that as a yes. Give my slutty sissy your cock, Brad. It’s time she learned her new place in the world.”

 Sucking Brad’s dank cock brought deep humiliation. It wasn’t just knowing I was doing this nasty thing in front of my buddies, but that they could tell I loved every single moment of it.

 An hour later, after they both busted their load in my mouth, Mom made me jack off myself in front of them and eat my jizz out of my hand and lick my fingers clean. It was so strange to be so humiliated and yet somehow proud at the same time! 

* * *

 A month later I was so proud of how far my sissy daughter had come along. Her breast implants had settled in nicely and she’d been so brave for the marathon electrolysis sessions to remove her facial and body hair. My stepdaughter was as beautiful as any girl except she had a lovely cock. How could I not love fucking her every night!

 We were eating a breakfast one Friday morning when the doorbell rang. Amber and I looked at each other in puzzlement.

 “Would my Mistress like me to get dressed to answer the door?”

 She wore only a thong panty that ill-concealed her clitty, fishnets, pumps and a see-thru babydoll nightie she used for doing housework. Her impressive jugs nestled in a push-up bra. She had not only gotten over embarrassment, she liked to show off her tranny body.

 “Look through the peephole first, baby. Make sure it isn’t some girl scout selling cookies before you expose yourself.”

 She bounced up. “Yes, Mom!”

 She sashayed out of the kitchen with that lovely ass shaking back and forth like a street hooker. A moment later the door opened.

 “Mom?” Her voice filtered uneasily from the foyer. “C’mere.”

 Our visitor turned to be a process server. No sooner had he shoved the big envelope in my hands than he spun about and walked away. I saw from the return address it was from my ex-husband’s lawyers.

 It became clear by the bottom of the first page that Amber’s dad was weaseling out of the agreement. Basically, he was cutting both Teddy-Amber’s allowance and my payments. At the very least I’d have to return full-time to porn and pro domme sessions, but that still wouldn’t be enough to keep the house.

 “The only way we keep our home is if you start working,” I said.

 “What can I do?” she pouted.

 “I’m going to pimp your shemale ass out at $300 an hour, and you’re going to do camgirl porn when you’re not turning tricks.”

 “This isn’t just a new humiliation then?” she shuddered, excited.

 “This is doing what your Mistress orders you to do,” I snapped.

 Oh, to be Amber… huh?

Just in case you missed it, here's part 1 of this story!

https://www.reddit.com/r/sexstories/comments/1fl83wx/mommys_sissy_slut/