This story is a work of fiction and completely made up. It's also got some stuff that the more prudish reader might not enjoy, including but not limited to: crossdressing/transgendered girls, lesbians, BDSM. If these things bother you, please immediately direct your browser to videos of cute kittens.
Additionally, this story is original work by me, so please don't steal it. It's a sequel to another story of mine, Meeting with Master, so please check that one out as well.
Finally, I love love love feedback-good, bad, indifferent, it doesn't matter. smithsmith2332[at]yahoo[dot]com
I've met some awesome people who read these stories, and they're the only reason I keep writing them. Thanks, and enjoy.
Meeting with Mistress
Our diapers made a crinkling sound as we writhed together, pressing only our bodies into each other as our lips battled furiously. Our arms were locked behind our backs in leather wrist cuffs. Coupled with the diapers we were wearing, there was no way we could do anything more than make out and dry-hump each other-Mistress didn't want us fucking and spending all our energy on each other while she was out of the house. Not that either of us minded, between the sexy thrill of playing with each other, the wonderful helplessness of being dressed as babies, and the promise that Mistress would have something planned for later tonight.
I suppose I should introduce myself-I'm Jessica, bisexual teenage sissy sub, trans-girl, and lover of all things kinky. I'm 16, almost seventeen, and going to be entering my senior year of high school. I'm out to my mom and my sister, who are both very supportive and have always encouraged me to be the girl that I am on the inside. I'll finish off high school as a boy with the plan of transitioning during the summer before heading off to college.
Last time I told you about one of my favorite sessions with my former master. I say former because it's hard to keep up a sexual partnership when one of the parties gets locked away in prison for ten years on tax evasion. I missed him for a while, certainly, but I wasn't ever in love with him nor am I particularly torn up about it now that I'm with my Mistress. He dug his own hole and now he has to live with it-besides, he gave me most of his kinky stuff before he was convicted. All of the sexy lingerie and fetish wear he bought for me to wear, all of his toys, most of the chains and restraints. He always was generous to me, even if he was stupid with his money otherwise.
Enough about him though, you're probably more interested in the girl next to me. That's my sister, Amy. She's 19 and back home this summer after her freshman year at college. We're not very similar physically: she's slim with firm C cup breasts, while I'm a bit chubby and make due, for now, with B cup falsies. My hair is a dark red, curly and medium length, while her hair is light red and cut short, pixie style with cute bangs over her green eyes. I was jealous of those eyes, my own being dull brown. Physical differences aside, we did share a few things in common: we were both bi, and we were both very kinky and submissive. We also shared a mistress in our very own loving mother.
Mom had known I was a girl before I did, and she's helped me every step along the way. The one secret I had regretfully hidden from her was my relationship with my master. She soon learned all about that one day when she found a box of restraints that I had hidden in the garage. Kind of a stupid place for them in hindsight, but I just didn't have the space to stash them in my bedroom. We had a long heart-to-heart, and she revealed her long-kept secret love of BDSM and told me about her time spent as a sexual slave, first to a senior sorority sister while in college, then later on to my very own father. She had been the submissive in those relationships, but she told me she had since become dominant. The biggest surprise of that conversation was when she told me that Becky, the girl from the next block over and my babysitter from when I was ten until I was twelve, had been my mom's slave slut from sixteen until she left for college two years later. The thought of my mom dominating Becky as a sexual plaything nearly made me cream my panties right there.
To make a long story short, later that night she ended up dressing me in a sexy leather teddy and fishnet stockings and proceeded to show me her skill with some of the restraints and toys I had. My silk bra felt like sandpaper against my nipples the next day, and my ass was so sore that it was hard to sit-though that may actually have been because I still had a plug locked inside of me thanks to a special belt I had.
My sister became involved with our play only a few weeks later. She had gotten a ride home from school with her roommate and had wanted to surprise us. As you might guess, the surprise was all hers when she found me, dressed in nothing but PVC stockings and crotchless panties, tied over a padded bench in the living room getting fucked by Mistress with one of her strap-on dildos. Instead of freaking out, Amy immediately slid her skirt down, revealing a lacy yellow bikini panty that, shockingly, I realized belonged to me. Instead of me wearing my sister's clothes, like most young crossdressers, my sister had stolen some of mine-and that fact couldn't be hotter to me! She didn't stop there, though. She slid off the panties she was wearing, walked over to my face, and shoved the underwear into my open mouth, gagging me with my own stolen panties. Panties that tasted heavily like her pussy, I might add. She then turned to my Mommy Mistress and asked that it be her turn on the horse next. Mom just smiled and told her to run upstairs and put on something fitting for a horny lesbian sub-slut.
That first kinky day with my family was months ago, and things have only gotten better since. We converted our formerly unfinished basement into a full-blown BDSM playroom. That's where Amy and I were now, on the bed in the playroom, trying desperately to relieve our horniness, knowing that Mistress had set things up so we couldn't.
"Oh fuck Jess, the vib in my pussy just kicked up to the next level!" Amy said. I answered with only a long moan, as my vibrating butt plug had also kicked up, about thirty seconds earlier. The plug was huge, and my sissy-pussy felt so full. Couple that with the wireless vibrating control and I was rock hard in my diaper. Mom must be almost home, I thought. And she's getting us ready for whatever she has planned. Mistress had stripped me out of my diaper, removed my plug, and placed me on my back on our padded bench with my legs in the air, spread eagle and locked. Amy, on the other hand, was still diapered with her hands cuffed behind her back, with the addition of chained nipple clamps that were now swinging back-and-forth as she fucked my ass with a ten-inch strap-on. Mistress was getting herself warmed up by sitting on my face, making me alternate between eating her pussy and her ass all while calling me filthy names.
"Oh yes, my dirty little girly-boy... Sissy slut son! Eat your mommy's dirty holes, please your mistress like the fuck toy you are!"
Needless to say, I was hard, to the point that it hurt. Well, that and she was working my girly-cock with a short riding crop as she brought herself to her first loud orgasm.
Mistress decided to change things up after that. I was unlocked, put into a tight black corset with lacy trim (which I loved, thanks to the figure it gave a chubby girl like me) and thong panties, gagged, then chained by my hands to the X-rack on the wall. Amy had her diaper and vibrator removed and mistress helped her into a pair of tall, locking ballet-style heels that would keep her feet painfully flexed. Mistress then put a pair of metal cuffs with a soft black-fuzzy lining around Amy's wrists and attached them to a set of chains hanging from the ceiling, which were then hoisted up so Amy's already flexed toes were just touching the floor.
Mistress walked around my sister's helpless form, caressing her softly, whispering how beautiful her slave's sexy body was before finally stopping at Amy's cute ass. Kneeling down, mistress spread Amy's cheeks and started to tongue Amy's hole, softly at first, then more and more insistently. Amy was moaning like the slut she was as our mom played with her sensitive ass. Finally, mistress stood up, and grabbed a good-sized butt plug from the toy shelf, quickly lubed it, and started to roughly force it into Amy's asshole. Amy's moans turned to whimpers until the plug finally slid in to rest tightly inside her. The plug was followed by a set of weights hung on the chain of the nipple clamps. Between the shoes, the chains on her arms, the plug, and the weighted clamps, I could only imagine the pain that Amy was in. I was more than a little jealous.
Mistress grabbed a leather-bound paddle from the toy shelf and proceeded to work over Amy's immobile body, starting with her ankles, working up the thighs, lightly on her breasts, and finally hard on her ass.
"Oh yeah slave, do you like that? Do you like my paddle driving that plug harder into your ass?"
"Yes mistress, I fucking love it! Oh fuck, I'm so wet, fuck I need to cum soon, mistress!" Amy shouted.
"Mmm, my little slut, I can see that," mistress said as she ran her latex gloved hands over Amy's hairless pussy. I could see the glistening wetness on the shiny black surface as mistress brought her hand up to her slave's mouth and made Amy lick it clean. Mistress knelt down in front of my sexy sister, and proceeded to ravager her with her gloved hand. Two fingers, then three, four, and finally-with panting and loud moans from Amy-her whole fist. I watched in awe as my mom fist fucked my sister to body wrenching orgasm.
Mistress kept her hand inside of Amy until she stopped shaking and her breathing began to clam. With a wet pop!, mistress slid her hand out and began lowering the chains that held Amy's arms, massaging the poor slave's sore and abused body while helping Amy over to the bed. Amy was completely exhausted, covered in a sheen of sweat, but had a look of contentment on her face.
"You turn now, baby sis," she said as she smiled at me as she settled in to watch.
Mistress released my hands from the wall and ordered me to remove my ball gag.
"Wow, that was fucking hot!" I said once my mouth was free.
"Hush, my little sissy slave, and put that tongue to good use," mistress said as she held out her gloved hand, still covered in my sister's warm juices. I licked it clean as her other hand played with my girly-cock as it jutted out obscenely in my panties.
Grabbing me by my boi-clit, mistress led me over to the hanging chains and placed cuffs on me just as she had to Amy. Instead of cute boots, however, mistress placed my legs in a spreader bar. Then she pulled my arms behind me and attached the cuffs to the chains and began to hoist the chains up.
"Oh shit, that hurts mommy, please give me more!" I cried out. She stopped pulling on them, leaving me oddly balanced leaning forward with my arms above my lower back, legs spread wide and with everything on display.
"Mmm, my obscene little daughter has a big, hard clit here between her legs, doesn't she? Does she need mommy to make her girly-cock feel good?"
"Uh huh, yes mommy, please make me feel good!"
Mistress squirted some lube into her left hand and began slowly stroking me up and down while reaching around to play with my nipples through the corset with her other hand. She gradually built up speed, making my breath come quicker and bringing me to the edge before stopping. She repeated her edging torture four times, leaving me moaning for release, begging to come all over her sexy glove.
"No honey, you don't get to cum just yet. In fact, I'm going to make you cum without even touching yourself."
Spread more lube on her hand, she began to finger me just like she did Amy: starting with tow fingers, stretching me out gently before sliding in another. I was so excited-and nervous! I'd never been fisted before, and while I'd had some big toys in my ass-pussy before, a fist was in a whole league of its own. Three fingers, stretching and prodding, making me moan. Four fingers, teasing me for what was coming next. Finally, she brought her thumb down and began to press hard against my ass. I tried to relax, but it still hurt as she strained to get her hand inside me. Finally, with one last push, her entire hand slipped up inside of me to the wrist. The feeling was incredible-gone was the pain, replaced entirely by pleasure as she fist fucked me. Slowly at first, building up speed and making my girly-cock drip uncontrollably. With her other hand spanking my ass hard, I was now rocking back hard, trying to get as much of her arm as my teenage sissy ass could hold as I felt my orgasm building. Slowly at first, riding the waves of pleasure coming from my ass, then bam!, out of nowhere I was cumming harder than I had ever cum before. Four hard jets of cum spurted right into her waiting gloved hand. She slowly and gently removed her hand from my boi-pussy, and Amy came over, still somehow walking in those amazing shoes, to help me down from the chains and remove the spreader bar. Finally, mistress grabbed two butt plugs from the toy shelf and smeared my still warm cum all over them both.
Knowing full well what she intended, we both bent over the bed and presented our asses. Both well stretched by this point, the plugs popped right both of us and where quickly secured by two special belts that held the plugs in but still left our other equipment open for fun. We both kissed mistress deeply, thanking her for everything.
"Now girls, if you really want to thank me, you'll let me watch you fuck. I want to get off seeing my daughters going at it like the horny sluts you are."
We happily obliged.