Double Trouble

In Honor of Hump Your Hand Day….Meet Tasha and I tonight in the chat room at 7pm pst…

This story was written for me by one of my sissies to go with this picture that babyryan had done for me

I hope all of you enjoy it as much as I

Mistress Sassa

ladysassa07-yahoo im

ladysassa07@yahoo.com
1-866-687-3717 ext 170 -LadySassa

1-866-687-3717 ext 156 -Miss Tasha

Ask us about our special “Double Trouble” rate

this week…..

DOUBLE TROUBLE

As I stood there, staring at the neatly hand-written note pinned to the door, my stomach flipped and I began having second thoughts… again. Coming here had seemed such a good idea… exciting, arousing, unusual. I had spoken with Lady Sassa several times on the phone, chatted online, and each time was incredible! She was a truly addictive mistress. So when she instructed me it was time to finally meet, I was so turned on by the thought, that of course I eagerly agreed! I mean, who wouldn’t, in my place? Our phone conversations were so exciting and arousing… she always knew just how far to take me… just how far to tease before leaving me helplessly begging for more, aching for release. Lady Sassa had me under her spell and I was helpless to resist her invitation to meet, especially after she had said, “I think you’re ready for the next step”. Next step??? What the hell did that mean??? I just had to find out, so here I was. Every now and then, since that call, I had been given to a little doubt and asked myself did I really want to do this? And each time, my answer had been yes! I DID!
So after following her instructions and directions carefully, I now stood there at her door, staring at that note and fighting my latest urge to turn back… to turn around, get back in my car and drive away. This was crazy! What the hell was I doing here? I read it again and let the words sink in, ‘Take off all of your clothes, leave them folded on the mat next to the door, get down on your knees and knock.’ Hesitantly, I decided I would go for it.
I looked nervously up and down the quiet street, hoping no one was out watering their lawn or walking their dog… no cars driving by. The street was empty on this quiet afternoon. Wondering how long my luck would hold out, I quickly began to strip right there on Lady Sassa’s porch! I folded my clothes, as directed, laying them neatly on the mat… my pants, my shirt, my socks tucked neatly into my shoes… and with a deep breath, I slid my underpants down and off and folded them on top of the pile. I was totally nude outside, and kneeling at Lady Sassa’s door. It was so arousing and exciting to be so helplessly exposed to anyone who might casually pass by and see me! I timidly knocked at the door and waited…. no sound. I knocked again… nothing. Was this a cruel joke? Was the point only to get me to strip naked and kneel there? Was she even home at all? All these thoughts raced through my brain as I knelt there for what seemed an eternity… but was actually only a moment… till I heard high heels clicking across the floor, towards the door. Was I relieved to here her approaching? Well, if she had not answered soon I might have gotten up, hurriedly dressed and escaped to safety. So although relieved, I also felt a heightened sense of nervousness and apprehension for what might happen next. No time to second guess now; the door was opening.
There stood Lady Sassa, looking down at me almost curiously. She wore a gorgeous red outfit. A red latex bra and panties and matching long gloves. She was as beautiful as in her pictures… much more so, in fact! Her black lace-topped stockings attracted my eye-level gaze and I could feel my penis stirring awake. Staring up into Lady Sassa’s gorgeous face, I saw her cock her head slightly to one side and raise her eyebrows in a questioning glance. Instinctively I read her expression, lowered my head and gazed at her shiny black boots with spike heels. Of course… I had not earned the right to look at her. Then I heard her softly chuckle and whisper approvingly, “that’s better”.
Lady Sassa then instructed me to crawl across the threshold and follow her into the house. I obediently followed her, noticing that she did not retrieve my clothes from her porch, nor instruct me to do so. She merely closed the door, which left me feeling even more vulnerable and helpless. I crawled on hands and knees to the middle of the beautifully finished hardwood floor and stopped there, on her word. Lady Sassa then proceeded to slowly walk around me a few times; I supposed she was checking me out and assessing my worthiness. I did not dare to look up or to ask any questions, but just knelt there watching her boots circle me, with the click-tap, click-tap of her spike heel and toe echoing in the room. Every now and then I felt something drag slowly across my skin; I decided they were the leather cords of some sort of whip. Mostly they played on my exposed ass. Finally, she instructed me to kneel up and stare straight ahead. I did so, aware that I was now even more on display. As Lady Sassa passed by, continuing her circling inspection, I saw that it was indeed a small leather whip, its cords dangling harmlessly, for now. She eased the cords across my shoulders as she passed, letting them drag across my skin. My penis stirred to attention as Lady Sassa inspected me. Noticing my arousal, she stopped in front of me, bent over slightly, reached out and bounced my penis gently up and down on two of her red-gloved fingers.
“Did I give permission to your little baby peepee to get hard”, she asked.
“No, Lady Sassa”, I whispered apologetically.
“Mmm-hmmm”, she answered.. And that was all.
Lady Sassa turned and left the room, her heels clicking away and leaving me there alone. A few minutes passed. ‘Was that it?’, I thought? ‘Was it over? Had I failed some sort of preliminary test by starting to get excited in front of her?’
At that point I heard Lady Sassa’s beautiful southern drawl. “Get up off your knees and follow my voice.”
I obeyed, feeling a slight stiffness in my knees from having knelt so long on the hardwood floor. I tentatively eased forward in the direction from which I decided the voice had come. Every now and then an occasional “this way“ or “that’s right” kept me headed in the right direction. I passed from the luxurious living room into a dining room and up a hardwood staircase to the richly carpeted upstairs. I wandered into a hallway and past several beautiful bedrooms before seeing Lady Sassa standing in the bathroom doorway. I entered as she looked me up and down. I was painfully aware of my total nakedness and she chuckled with a superior tone. Lady Sassa instructed me to shower and then come to a spare bedroom down the hall, then she left me. I looked around and saw she had laid out some shower gel, shampoo and a thick, incredibly soft bath towel. I showered as quickly, but as thoroughly as I could, dried myself off, brushed my hair neatly and walked back down the hallway to the only open door I saw… the spare bedroom. Not knowing what to expect, I entered, ready for anything.
Anything, that is, except what I found! There was Lady Sassa, sitting patiently in a deep beautiful armchair. But across a coffee table from her was another chair… and another woman!
“It’s about time you finished”, Lady Sassa snapped. “I don’t like to be kept waiting, and neither do my guests. Stand here in front of us.”
I slowly walked forward, staring at the beautiful woman sitting there with Lady Sassa as both of them eyed me up and down appraisingly. AS I stood there and bowed my head, the other woman rose and walked around me, as Lady Sassa had done. “Hmmmmmmmm”… she muttered nondescriptly. She too was dressed for arousal. She wore a latex bra and panty set, similar to Lady Sassa, except hers were black, with matching long black gloves and high black boots. She also wore a totally sheer wispy black skirt with pink trim, allowing a clear view of her panties and thighs.
“Say hello to Miss Tasha”, Lady Sassa instructed.
“Hello, Miss Tasha”, I repeated, respectfully. I stopped at that, not sure what else to say without permission.
“Well, he’s obedient anyway”, Miss Tasha complimented. Then she looked down at my semi-erection, grasped it in her hand and asked, “and what do you call this”?
Confused a second, I decided to answer plainly, “my penis, Miss Tasha”. Both women laughed.
“You call that a penis?”, Miss Tasha teased. I wasn’t sure how to answer.
“No, no, sweetie”, Lady Sassa reminded me. “What is it now? Come on… think.”
Then I remembered what Lady Sassa had said earlier and replied, “it’s my little baby peepee”.
Lady Sassa and Miss Tasha now laughed approvingly as I blushed.
“That’s right”, Sassa smiled. “I’d say it’s only about 3 inches, so from now on, it’s your little baby peepee. Now say it. Tell us about your little baby peepee and how much you like to play with it”.
“I have a little baby peepe”, I began.
“No”, Miss Tasha interrupted. “Not in a big boy voice. You have a little 3 inch baby peepee, so tell us in a cute little baby voice.”
I hesitated a second, and then obeyed, speaking in a cute, high baby voice, “I have a little baby peepee. It’s so little and cute. I like my little baby peepee and I have so much fun playing with it.”
Both women laughed, giggled and cooed sweetly. “Awwww… little beby peepee! Sweet little peepee! Hahahha!”
Then Tasha laughed, “well, if he’s such a little baby, then all that man hair will have to go.”
Sassa agreed and they led me back to the bathroom, where they worked together to lather and shave me all over. My legs, my arms, my chest… soon everything was smooth and hairless. Then they led me back to the bedroom, laid me out on a towel on the bed, and proceeded to clip away my pubic hair with a pair of manicuring scissors, and then lather and shave me completely smooth and hairless. All the while they spoke, laughed and giggled as if I was not even there. When they finished they wiped me with a warm, wet washcloth and dried me with a soft fluffy towel. Sassa and Tasha then had me stand and look at myself in the mirror. I blushed with embarrassment as I saw my body clean shaven, smooth and hairless, my penis now at full attention from the humiliation of having my manhood shaved away by these two gorgeous women.
Lady Sassa then led the way back downstairs to the living room where she and Miss Tasha reclined in two comfortable armchairs. She instructed me to go into the kitchen where I would find a chilled bottle of wine and two glasses. I was to pour the wine and serve it to the two ladies.
“And don’t forget to put on the apron”, Lady Sassa added as I entered the kitchen.
Sure enough, there on the counter, an apron was laid out for me. It was white and sheer, with pink ruffly lace edges and a pink ribbon to wrap around me and tie into a bow. I put it on and tied the bow as best as I could alone, then poured the wine, set the glasses onto the tray Sassa had provided, and walked back to the living room where Sassa and Tasha chatted away. As soon as I entered the room, their conversation stopped and both women erupted in laughter and approval. I blushed as my penis rose to full attention and poked at the front of my sheer, pretty apron.
“You know, baby”, Sassa giggled to Tasha, “he looks so-o-o-o sweet and cute with that little apron on, I’m not sure if that’s a little baby peepee or a little girlie clitty!”
Miss Tasha doubled her laughter at me as I stood there helplessly.
“A little girlie clitty! That’s right,” she laughed. “Walk around for us like a pretty little girlie”, she instructed me.
“Go on, obey Miss Tasha”, Sassa agreed.
Not sure exactly what to do, I thought a second and did my best improvisation. I began walking around slowly, swaying my hips back and forth, as both women laughed mockingly at me. Encouraged that I was on the right track, I then placed one hand on my hip, the other straight to my side and swayed my hipe even more as I walked.
“More girlie! More sexy!”, Lady Sassa laughed.
I swayed around the room, both hands now on my hips, stopping now and then to pose, crooking my legs and giving them a sultry gaze as I lowered my chin daintily to my chest. At the ladies’ instruction, I even blew little kisses, turned and smiled at them over my shoulder, my ass sticking out under the bow of my pretty apron and my lips curled into a sultry little circle as I lightly gave one ass cheek a little slap. To top it off, they had me speak in a sexy, sultry whisper, “Ooooo, I feel so-o-o pretty.” And then a high, squeeky Ooooo! Ooooo!” By now they were both roaring with laughter at me and my penis was achingly hard.
“That’s it”, Lady Sassa decided through tears of laughter. “He’s a much better girlie than he is a baby. You’re going to be our little girlie bitch!”
“Our sweet little slut-honey”, Miss Tasha added, wiping her eyes.
Lady Sassa then took me by the hand and led me back upstairs, leaving Tasha alone awhile, to relax with her wine. There in the bedroom she laid out some things and instructed me to sit quietly in the chair at the vanity while she prepared. I sat there obediently, looking into the mirror, as she approached me and turned on the vanity lights. She opened a drawer, revealing it was filled with makeup! I couldn’t believe this was happening to me, but as I sat there totally nude, Lady Sassa began applying girlie makeup to me! Soon I looked into the mirror, shocked at what I saw staring back at me. It was my face alright, but now with eyeliner and mascara, false eyelashes, blush and lipstick! Lady Sassa giggled at her handiwork and had me blow little kisses to myself in the mirror, for practice. I felt my eyes welling up with shame.
“Oh, don’t cry, sweetheart”, she cooed gently. “You’ll make your mascara run and we’ll have to start all over”. I subdued myself resolutely as Sassa went to the closet and pulled out what appeared to be a hat box. She returned to the chair next to me, set the box on the table and pulled out a wig! It was a blonde wig, very “little girl” looking, with long pony tails on both sides, secured at the top with a pink bow each! Lady Sassa had me turn to face her, and began trying to fit the wig securely. She was having a little trouble and each time she thought she had it right, she would sit back to have a look, scowl and begin again.
“I can’t seem to get this just right”, she said. Your hair is so thick, the wig doesn’t want to settle nicely like it should.” Another try, another look and another scowl before she adjusted it yet again.
“Hmmmm” she muttered reflectively, then she smiled. “Maybe I should just shave your head so your wig will sit perfectly.” At this suggestion, my eyes widened in fright!
“Lady Sassa… p-p-please don’t”, I helplessly whimpered. She looked at me and giggled at my pleading.
“What’s the matter, honey? You don’t want Miss Sassa to shave your head bald? Awwww, you’d look so-o cu-u-u-ute… my little baldy sissy girl. Hahahahahahaha!”
I pictured myself sitting there, with Lady Sassa shaving me completely bald! I pictured going down and having Miss Tasha see me like that… naked and bald headed, in sissy makeup. I pictured both women laughing and taunting me, running their gloved hands slowly over my bald scalp while I sat there crying! ! And afterwards… when it was all over! Leaving the house and everyone else seeing me like that! It was too much to take and I pleaded with her, “P-p-p-please don’t, Miss Sassa. P-p-le-e-e-e-ease.”
Sassa chuckled as she continued working on the wig. Finally, to my great relief, “There”, she announced triumphantly. “That will do for now… you’re all pretty”
I turned and looked at myself again in the mirror. The wig fit nicely, and my makeup job was startling. Startlingly soft and realistic! I looked like a little girl!
Lady Sassa now stood there, laughing at me, “ok honey… I don’t have to shave your head bald”. Then with a wickedly menacing chuckle, added, “for now at least. We’ll see some other time.”
Again, my stomach did a flip. But at least I was safe… for now, whatever that meant. I let it go.
“Now put on everything I have laid out for you and come back downstairs right away. Don’t keep Miss Tasha and me waiting long, sissy”, Sassa ordered, and left me there. I stared a second at the outfit she had left me, took a deep breath, and then slowly began.

Downstairs Lady Sassa and Miss Tasha laughed and chatted away. I left the bedroom, walked down the hallway and paused at the top of the stairs before heading down. I only heard a few bits and clips of their conversation… enough to hear what I thought was “shaving bald” and “he’d love to do that to him”, but I couldn’t be sure. Anyway, I was too nervous and excited to care, right now. I stepped down the stairs carefully, so not to fall, hearing Sassa say, “here she comes, Tasha.” As I reached the bottom of the stairs, I turned and walked into the living room to present myself to the two ladies. Again, they laughed, giggled and cooed their amused approval at what they now saw! It was Miss Tasha’s first look at my girlie wig and pretty makeup. And now on top of that, I wore a cute little sissy outfit! A ruffly pink shoulder-strap midriff top and light pink sheer pantyhose. My tiny bald peepee was clearly visible, straining against the sheer material. To finish off the look, I wore pink high-heels with a pink bow on each shoe! I was completely transformed into a total little sissy girl! I had never imagined, coming to this house today, that this was even remotely possible! Yet, here I was, standing in front of these two ultra sexy women who were howling with laughter at me. I hung my head in shame and embarrassment as they teased and humiliated me. Then I was instructed to resume my sexy prancing around the room, hands on my hips and swaying my ass back and forth, posing, blowing kisses and cooing sweetly. I was totally mortified but totally turned on at the same time!
“Oh, baby, I can’t take anymore”, Miss Tasha laughed. “I have to have this hot baby girl now!”
“Me too”, Sassa agreed. They led me by the hand down more stairs into a carpeted finished basement. It was filled with all sorts of equipment… racks of whips and riding crops along the walls, cuffs dangling from the ceiling and walls, a very large carpeted dog cage… everything you could imagine! They led me to a table in the middle of the room and instructed me to lay down… and lift my feet into the stirrups. Once I had obeyed submissively, Lady Sassa clasped a cuff around each ankle and each wrist, so that I was now chained to the table and spread eagled before them!
Miss Tasha stood at the head of the table and I watched her sliding on a huge black strap-on dildo! Similarly, Lady Sassa stood at the foot of the table, doing the same! In sharp contrast to her beautifully sexy, feminine form, a huge black cock now stood out proudly and menacingly before Lady Sassa! I gulped as I awaited my obvious fate.
“Mmmmmmmm, are you ready, Tasha?” Sassa laughed.
“Mmmmmmmm, ready, baby, “Tasha purred.
“Beg for it!”, Sassa ordered me, sounding a little more cruel and demanding. I stared in fear.
“You heard Lady Sassa, beg us to fuck you! DO it, you little sissy bitch!”, Miss Tasha now roared.
“Please fuck me”, I obeyed, a bit half heartedly.
“You call that begging?”, Tasha slapped my face, taunting me. “Make it good! Fuckin’ BEG for our big hard manly cocks to fill you up!”
Sassa picked up that flail and lashed at my open thighs cruelly. “Beg us!”, she ordered, “or you’ll get more than you bargained for, you little cunt bitch!”
“You’re not a man”, Miss Tasha yelled. “You’re a whore! You’re our little sissy bitch whore, and you want it! You want us to fill you up with our big hard black cocks, don’t you?!!?”
“You’re a dirty little teenage bitch girl and you want big hard black cocks filling you up, stretching you and making you scream, DON’T you?!? DON’T you!!!???”
“Yes, yes!” I now yelled, too turned on the think or care.
“Yes WHAT?”, Tasha again slapped my face as Sassa raised her flail threateningly before me.
“Say it!”, Sassa ordered. “And make it good!”
“Yes”, I pleaded. “Yes, I want you to fuck me! Please fuck me like a little teenage girl! I’m your little cunt bitch whore and I want those big meaty black cocks inside me! Oh yes! Give it to me! Fuck me hard! Please, Lady Sassa! Please, Miss Tasha!”
Before I could go any further, Miss Tasha grabbed at my hair and pulled my face toward her. I instinctively opened my mouth and felt her sliding that big dildo past my lips, and then pushing it deep in my mouth! She slid it in and out, fucking my mouth, and making me lick, suck and worship her black cock! Meanwhile, I was able to look down and see Lady Sassa as she reached down, grabbed the thin sheer material of my panty hose and tore at it, rending it wide open so my little bald baby peepee was exposed, and so was my wide-spread ass hole! ‘Oh NO’, I thought for a second as she worked baby oil up and down the shaft of her cock, making it shimmer and gleam, and then squirted it onto my ass, starting at the base of my little balls and letting it drip down, soaking my waiting ass crack.
“Keep sucking girlie bitch”, Tasha ordered. Give me a hot blowjob! Worship my huge black cock, you dick-licking sissy-boy whore!”
I kept sucking hard and moaning as Sassa played the tip of her massive cock around my little puckered asshole… and then, slowly penetrated a little, then a little more… and then… shoved it deep inside! I moaned in pain and pleasure as Lady Sassa fucked my no longer virgin ass! She was the man in control, and I was the submissive little girl, getting my asshole filled and violated. Mmmmmm!!!
“More, more!”, I begged her. “Deeper! Deeper, Lady Sassa! Please fuck me harder! Yes! Yes! I‘m your little slave girl! I‘m a slave to your big black cock!, Lady Sassa!”
I lay there helplessly submissive and totally out of control as the gorgeous Lady Sassa and beautiful Miss Tasha aggressively fucked my girlie ass and my sissy mouth! My little bald baby peepee stood straight up, throbbing, aching for release as the two women laughed wickedly at me in my sweet little girlie wig, makeup and outfit, and at my sissy slave-girl submission.
Finally, Lady Sassa reached down and grasped my little hardon… but between her thumb and pointer finger. She held it just below the head, pressing gently but firmly into the sensitive underside. Up, down, up down… two little shakes was all it took and I felt the wave rising within my groin and surging up through my penis… I moaned… I groaned… and I erupted with squirts of cum shooting from my penis and onto my stomach! Lady Sassa and Miss Tasha laughed and taunted at my lack of control and staying power.
“Look, Tasha”, Sassa mocked, “the little sissy bitch couldn’t even last like a real man! She shot her little sissy load in a couple of seconds! I barely touched her! Hahahahaha!”
I now lay there, exhausted, as Lady Sassa and Miss Tasha withdrew their huge black cocks from my little asshole and puckered mouth. They laughed at my bald peepee, now soft, and limp once again. It flopped over into a puddle of cum I had shot onto my belly… tinier than ever. The women giggled and teased mercilessly.
“Well, now that our sissy has had his turn, let’s have some real fun”, Lady Sassa suggested. Miss Tasha eagerly agreed, and both women removed their strap on cocks and their bras, and lowered and stepped out of their panties, now both wearing only their gloves and boots. They stood there proudly and gloriously naked before me, looking down and laughing at their helpless, harmless little pussy-whipped sissy with the soft, tiny little girlie-clit limp between her legs. Lady Sassa and Miss Tasha removed my cuffs and let me up from the table. Tasha put her sheer little skirt on me, and they instructed me to get down onto the carpet, which I did, my legs spread and my little limp baby peepee on display.. Then Lady Sassa went to a drawer, opened it and selected two huge double headed dildos!
“Our turn, bitch”, she laughed as she approached, handing a long pink one to Tasha and keeping the long purple one for herself. The ladies positioned me again on my back, this time with Lady Sassa at my head. She slid the double headed dildo into her hot, gorgeous pussy and moved the other end toward my mouth. I sucked it in and began slowly moving up and down on it, back and forth, sucking hard while pleasuring Lady Sassa at the same time. She moaned her approval. Meanwhile, Miss Tasha slid one end of her dildo into her beautiful pussy and positioned herself on the floor between my legs, so that she could fuck my ass while watching my little bald peepee bouncing up and down under my sheer little skirt. She lubricated my end and this time I was an anxious and eager participant. I grabbed it firmly, directed it to my asshole and firmly helped Miss Tasha slide it in and shove it deep inside of me. We both moved back and forth on it, this time Miss Tasha moaning in pleasure as her pussy was fucked as well.
The two gorgeous mistresses, one at either end of me, enjoying the pleasurable sensations, and me between them, in my little sissy girl slut outfit, eagerly sucking on gorgeous Lady Sassa while being fucked up the ass by beautiful Miss Tasha… the scene is still etched in my brain. And the words of Lady Sassa to Miss Tasha… “I think we’ve got a good one here, baby”.
Miss Tasha simply purred… “mmmmmmm,. Yeah.”

Double Trouble