Further Training as Sissy Lesbian

Dear readers,

This is a continuation of my story 'Miss Johnstone's Lesbian Sissy Slut' and I sincerely recommend reading that story first as it provides background for this one.

Enjoy and please take time to give me some feedback!

Theo

3. Intermission: Further training

Following the loss of my sissy virginity just after I had turned eighteen years old, my training in becoming a perfect lesbian sissy submissive continued.

Every night I slept with a soiled pair of Miss Johnstone's panties over my face and with a pair of headphones on, so I could hear her voice during my sleep, telling me what a lovely slutty lesbian sissy I was, how much I desired to please mature women, lick their wonderful pussies, suck their nipples, taste the forbidden musk of their delightful assholes. I was told how to be truly feminine, how to best pay respect to my elders, how to accept my identity as a sissy lesbian. She also gave numerous tips on make-up and dressing and on how a girl should move and walk.

I also had to sleep with tight, girlie panties on, and was totally forbidden to touch myself indecently. I had to sit down when peeing, and at all times only use very feminine and very tight panties. I was also trained with butt plugs, gradually expanding my sissy pussy and getting it used to the hard fuckings I was learning to crave.

The results were soon evident. I started seeing myself as a girl, and not just as any girl. I truly transformed into a slutty lesbian, living for those moments I could spend with Miss Johnstone in my Rita persona. I hated dressing and acting like a male, and avoided the other boys at school, who in turn avoided me and called me a sissy faggot. The sissy I could agree with, but not in being a faggot: I had no sexual feelings for males whatsoever. Girls my own age had also little interest, but I tried my best to emulate their movements and sometimes actively sought out their company.

Mostly, however, I wanted to be with older women and at all times tried to watch them and imagine how it would be if for example a woman I met at the mall, was to kiss me and fondle my feminized behind. How would she react to my tight, pink, frilly panties? And how would her female excretions taste if I was allowed to kiss her pantie covered crotch?

Miss Johnstone also started taking me out, as Rita. We would drive to nearby towns and visit various malls, partly to shop for clothes and accessories but mostly to publicly act as mother and daughter, so I could fall even more deeply under the spell of my dominant Mistress and familiarize myself with acting and behaving as a young woman. Miss Johnstone encouraged me to flirt with the mature women we met on our trips, and often I would receive an interested look back, when I tried to catch their eye by batting my lashes, looking at them sultrily or pursing my lips.

Most women were never aware of my interest, but quite a few looked me over with appreciation and I even, on a memorable occasion, had a lean fiftyish woman stand close behind me as I was looking into a store window and surreptitiously caress my scantily covered bottom as she whispered into my ear what a hot little slut I was and how much she would enjoy licking my sweet nookie. I was very much taken aback by this and before I could react she gave my butt a firm slap and then walked away, watching me over her shoulder with hot eyes. Afterwards I was extremely proud that such a beautiful, mature woman had found me hot and wanted to make love to me!

4. An unexpected seduction

A couple of months after Miss Johnstone had initially seduced me, my mother had to go for an extended business trip and my Granny came to stay with me and look after our house and me. My grandmother was in her early sixties. A well-kept and well dressed, tall and curvy woman with shoulder length grey hair and dark, penetrating eyes. She had always been there to take care of me, when mother did not have the time, and I was very comfortable around her.

I continued sleeping with my Mistress' panties over my face and dreaming about mature women and how to be a perfect lesbo sissy slut. But when Granny arrived I was totally unprepared for the surge of lust that engulfed me! I had not realized how much sexual energy she radiated and how it affected my befuddled sissy mind.

She was discretely made up, wore an expensive dove grey silk dress that seemed to cling to her womanly body and her perfume almost made me gasp with longing as I involuntarily imagined what it would be like to suck my Granny's delectable nipples or taste her female excretions. My conditioning was strong, facilitated by my strict training at the hands of the competent Miss Johnstone, and I was totally unable to suppress my rising desire. I became flustered and confused and quickly had to excuse myself, to go to my room and immerse myself into illicit fantasies involving my majestic grandmother and my sissy persona, Rita. Since I was not allowed to touch myself, I achieved no relief and my sissy clit was stiff as steel inside its tight pantie prison.

Mother left on her trip and I managed to cool down enough to endure a dinner with my Granny. I still kept imagining how it would be to have my sissy ass spanked by her, and how much I wanted to taste her matronly breasts and mature pussy. I could not look her into the eyes, they seemed to gleam with a secret understanding. I escaped after dinner, excused myself by saying I wanted to chat with my friends on my laptop, but instead I lost myself in my Mistress' soiled panties breathing in her heady scent and licking the stained gusset, imagining I was servicing my stern grandmother.

My sissy clit dribbled juice but I did not dare touch it and could only tweak and tease my stiff nipples, knowing even this would earn me a sound spanking from my Mistress. But I couldn't help myself: My mature Granny had fired all my lesbian sissy desires, which had been so deviously shaped by Miss Johnstone to be directed only towards mature women who would to treat me as a little submissive slut.

That night, I fell asleep with my headphones on and Miss Johnstone's used panties over my face. Miss Johnstone had supplied me with a series of recordings of her voice to further enhance my submission to her. Thus I did not register that my Granny, who of course had noticed my aberrant behavior, sneaked into my room and stood for a long time watching me sleep as she caressed her breasts and pinched her erect throbbing nipples, aroused at the sight of her grandson as a sissy pantie slave.

Then she bent over my sleeping form and I woke up with a start as she kissed me forcefully through Miss Johnstone's black, frilly silk panties and her hands started exploring my body. I could only kiss her back, submissively, and enjoy her sensuous manipulations, since I was totally immobilized with shock and surprise and soon I was moaning helplessly into my dominant Granny's mouth.

"So, you are a sissy slut, Richard! A true pantie slave who sleeps with his Mistress' panties over his face every night and listens to her voice telling him what a sweet little girl he is, I bet!"

She took the headphones and listened for a short while.

"Well, I'll be damned! That is Violetta's voice, so you're her little new lesbo sissy lover! My... my...!"

I was mortified that Miss Johnstone - whose first name was indeed Violetta - was known to my Granny, little realizing that women with the same tastes as my teacher and my grandmother had ways of communicating and sharing their desires.

"Oh, you sweet sissy darling! I would just love to see you all dressed up in your slutty feminine finery and showing off your delectable sweet body... Mmmm.. yes, kiss Granny you little naughty slut! I bet Violetta has you well trained... and well spanked... eh... Let me see... and of course, you are wearing a butt plug like all good sissies should... Mmm yes... such stiff and eager nipples... And that hard clit... which you are not allowed to touch... All hot and bothered... Do you want Granny to give you some release.. eh? Do you? Does my sweet sissy grandson want a true sissy cum at the hands of his Granny Mistress... oh, you such a sweetie, but I want you all dolled up and ready to please me, so dress up while I phone that Mistress of yours..."

I was totally befuddled as Granny had me find my secret stash of girly clothes. She asked me what my sissy name was and complimented my nice spankable ass when my filly pink panties were revealed. I was ordered to dress up as a sexy schoolgirl in tartan short skirt, tight white blouse, knee socks and black high heeled boots. Meanwhile, Granny talked with Miss Johnstone and an agreement was reached: I was to be homeschooled for the next few weeks, giving Granny and her a chance of training and disciplining me full time as Rita. I shuddered in anticipation, overwhelmed at suddenly having two Mistresses and at being kept as a sissy slave girl full time.

"Oh my, you are a real slutty little lesbian sweetie!" Grandma said when I stood before her, in my schoolgirl outfit and made up as a slutty doll. She embraced me and I drowned in her female smell.

"You need a very hard spanking now, over my lap, with a wooden hairbrush. You have been naughty and touched and played with your sissy nipples and for that you must be disciplined."

I was to receive ten barehanded spanks on each pantie clad buttock and then ten on my naked skin with a hairbrush, and I felt a dark thrill at being so intimately punished my very own grandmother. My sissy clittie was stiff and drooling viscous precum, so Grandma prudently tied a silken ribbon round the base and also around my sissy plums, making me ache with desire. Then she felt me all over, indecently fondling me and all the time telling me how lovely a sissy slut I was, how much she wanted to caress me and kiss me all over, how much she longed to have my delicate face between her strong legs, licking her leaking cunt and tight anus.

I was overwhelmed at having my imposing grandmother fondling my slight, girlish frame but also with the pure fiery lust her caresses and the whole situation awoke in me. Having to submit to her punishment, dressed as a schoolgirl and forced to lie over her lap as she had her way with me, was a fantastic turn on, especially as I had been so thoroughly pre-conditioned by the devious Miss Johnstone's seduction. I was truly a sissy lesbian, loving to be indecently fondled and intimately aroused by older women lusting after a young sweet sissy. I wriggled in anticipation on the cool silk of my grandmother's lap and was awarded a hard spank on my resilient right buttock.

"Thank me for your spanking, you naughty sissy!"

"Th.. thank.. you... Mistress ... Grandma..."

"You're most welcome, my sweet slut! Here's another!"

My grandmother was a very competent and strict disciplinarian, as I soon found out. Her spanks were hand and unrelenting, and even though she gave me a few breaks while she stroked and fondled my hot bottom, I was soon crying and sniffling incoherently. My sissy clittie was very stiff and exited, though, and the constant rubbing over my Granny's lap kept my arousal thrumming and humming. She let me up the barehanded spanking, and had me remove my panties and stand in front of her, showing off my heated, red ass and she even had me spread my cheeks, making it possible for her to gently fuck me with the butt plug still residing inside my pussy.

"Now, darling Rita, you must get ready for your hairbrush punishment! But first let me kiss those hot, sissy cheeks... Mmm... yes, dear, wriggle that sissy bum as I lick your hot skin... Mistress Granny can be so good to her little slut... as you took your initial spanking very well, my love...!"

I blushed at her indecent praise, and wriggled my naughty behind, wanting her to give more kisses and licks on the tortured cheeks. But it was time, and soon I was again over her lap, this time with red and naked buttocks bared for her pleasure, and once again I had to ask nicely for each hard spank to be delivered. Granny used the wooden side of the hairbrush with great competence, and in between spanks she would gently rub my inflamed orbs with the bristles, bringing me almost to orgasmic release as she teased my bound sissy plums between my spread legs. Oh, yes! My Mistress Granny knew how to excite a naughty sissy and make her beg for more!

Through tears and a haze of lust I begged to be punished, to feel her hand spanks on my vulnerable behind and when it was over, a heated throbbing and flowing warmth engulfed my ass as Grandma let her fingers dance over the spanked flesh and cooling my fires. I felt my little sissy clittie could explode, so hard and sensitive it was, fueled by the pain and pleasure in my bottom.

"Mmmm - I can see your Mistress has trained you well! You took your spanking very nicely and your adorable arse is a wonderful shade of red now! And the nice and thrilling warmth is spreading into your sexy sissy bummy cheeks, is it not? Making your slutty lesbian sissy pussy and clittie tingle and throb? Mmm... you love being spanked, you sweet sissy slut! Don't you? Especially by an older woman! I makes you very excited to have your very own Granny punish you and fondle your bum. Doesn't it, you little sissy pervert?"

What could I say? It was true, so very true! My whole body was trembling with lust and longing to be touched and fondled by this mature imposing lesbian woman, who also happened to be my grandmother! The incestuous implications made it all more exciting. My mind exploded with the realization that I was also a pervert: A young man who longed for the illicit touches and manipulations that older women would subject me to, while I was dressed up as a slutty lesbian.

I squiggled on my Mistress Granny's lap as she slowly fucked my overexcited sissy pussy with the plug and roughly pummeled my spanked nether cheeks. Tears dripped from my eyes, but the pain was forgotten in the rush of pleasure following with degrading subjugation. I was a feminized eighteen-year-old schoolgirl slut, deserving of hard punishment, meant to serve mature Mistresses, including my very own grandmother. I wanted to please her, to serve her, and I suddenly realized that the scent of her arousal was very evident. She pushed me off her lap, and I obediently kissed her hand and thanked her for my punishment.

"Thank you Mistress, for spanking my naughty sissy bummy and for punishing me because I touched and fondled my stiff sissy nipples"

"You are welcome, sweet Rita. And now you may adore and service my majestic behind."

Delirious with the privilege, I adoringly kissed every square inch of my Granny's ample and fleshy behind, almost fainting as her powerful, aroused smell, mixed with her exquisite female perfume, titillated my nose. Her panties were light grey silk and she wore old fashioned garters and black silk stockings. I was in pure sissy lesbian heaven as I kissed the warm buttocks of my new Mistress and even more so when she bared her majestic rump and allowed me to kiss her naked flesh! Then I was urged to lick up and down her anal crease and to sniff and adore the scent from her anus. My questing tongue gently probed and licked her crinkled hole, rimming her sphincter and I was even allowed to taster her fully as my tongue penetrated into her velvet innards, brimming with her most secret musk.

"Oh, Rita! You're such a sweet slutty ass-girl! Loving to serve a woman's anus and to tongue fuck my dirty ass. Yes... more, you naughty slut! Fuck Granny's ass with that sissy tongue... Further in... faster!"

My whole face glistened with her ass juices as she turned me around and had me service her hairy pussy, licking and sucking on her delicate labia and prominent clit. Grandma pressed me to her soaking wetness and urged me on wordlessly, pulling on my pigtails to fasten my feminized schoolgirl face to her oozing cunt. She came with a chorus of wails as I sucked and teased her stiff clitoris, drowning in her ripe excretions. Then I was pressed to her ample bosom as she forcefully kissed my slick face and slid her tongue inside my mouth where our spit mingled with her pungent cuntal juices.

"Mmmmm. Yes... Rita, you darling sissy lesbo... let me kiss you... kiss Granny, you sweet slutty sissy girl... yes.. that's it... let me taste my juices from your mouth, you little lesbian... So eager to please... Such a darling feminized ass and pussy licker... "

Passively I let her fondle me, my schoolgirl uniform in disarray, my spanked bottom warm and hot as Grandma' held me close and played with the plug inside my sissy pussy. My sissy clit was stiff as glass and aching for release inside the tight pantie restraint.

"Oh... is Granny's little sissy's clit all stiff and excited.. oh yes... And leaking its juice out in those nice panties... such a naughty sissy... Getting all excited by licking her Grandma's sweet and slimy pussy... loving to service my pussy, tasting my female scent... Such a sweet slut... With a hot red ass from her spanking... and a plug up inside her tight sissy puss... Mmmm kiss me, slut... kiss Granny, you saucy lesbian ...!"

I melted in her embrace, willingly letting her fondle and lewdly caress my young sissified body. Longing to her lesbian slave girl, her sissy play toy.

"I'm going to rape you now, you little slut. With my tongue. Granny is going to lick and molest her sissy granddaughter and you will love it more than anything... you will come to crave and desire the things my mouth and tongue and fingers can do to you! Sissy sluts like you, my sweet Rita, soon learn that the ultimate pleasure they can only get from their Mistresses, from experienced women like me, who precisely know how to bring a girl right to the edge!

Oh, you'll beg for release my sweet, you'll pray and cry and plead to be allowed to cum - and when I grant you permission you'll be my obedient sissy slave forever! Nobody will ever make you feel the way you loving Granny can!"

I hung on to her very word, shivering in fearful anticipation of what my formidable grandmother was planning to subject me to. My sissy pussy constricted tightly over the plug, my nipples tingled in arousal and by mind was totally befuddled at this seditious talk and her forceful promise of raping my sissified body.

"So, you sexy schoolgirl lesbian. Stand up, takes those panties off, spread your legs and show me your cute bottom... yes, just so... bend over and touch your toes... and let me feel those cheeks... mmmm... You love being touched... yes... feel my fingers on you orbs... Let's get that plug out of the way...Oh yes, Rita, darling... Granny is going to eat your tight sissy pussy now... "

Her tongues delved between my tight buttocks and licked up and down my crease, playfully slobbering over my tight sphincter. Her right hand gripped my tied up sissy plums tightly, cupping them whilst slowly stroking the root of my stiff sissy clittie. She was very skilled, was my grandmother! She knew all about keeping a sissy in strict control while tongue fucking her tight pussy. She initially treated my anus to a long and loving lathering and then let her tongue penetrate into my innards, keeping a firm grip on my plums and even twisting my little pouch to make me yelp with pain, even as her tongue gave me exquisite pleasure, teasing my velvet pussy.

"Mmmm sissy Rita loves being tongue fucked by Granny... doesn't she? Oh yes... her little clit is all stiff and bothered... Her plums boiling with sissy juices..."

I pushed my behind closer to her face, wanting her to spear my delicate sissy pussy. That earned me a few hard slaps on my bared bottom and a strong painful twist on my delicate plum sack.

"Keep still slut! I'm in charge here!"

Grandma rimmed my pussy for a long time, causing strange and volatile sensations to build up inside me. Torrents boiled and I could barely manage to keep my arse still. Then she had me stand and turn around and to my chagrin she now sucked my aching plums into her warm mouth, engulfing the sensitive flesh and letting her tongue swirp over them and rolling my little plums as if they were almonds or candies in her mouth. At the same time her fingers drummed over my stiff clittie, even gently stroking it and baring the sensitive helmet, bathed in viscous precum.