Sissy/Femdom... Dream to Reality

Story Info
Mistress and Sissy.
2k words
4.38
10.7k
8
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
sissy171
sissy171
536 Followers

We are boating/camping on the Lake.

I've just finished shaving my legs, finally overcoming my fears.

I'd been afraid to be one of those guys with bald legs. People would think,

"Is that natural, or does he shave them?"

I already have a petite girly body, but my leg hair stymied my femboy fantasies. My primary fetish, Femboys with bikini bra tan. I loved my tanned, sexy, girly, sissy bikini body, and now, smooth, hairless legs.

My "girlfriend", Sara, has allowed my inner sissy/slave to "evolve".

Sara dates whomever she chooses, while I date/serve Sara exclusively.

When I admitted I was a sub-sissy, she didn't want to continue our relationship.

I begged her to let me serve her, in whatever manner she chose. She agreed on a "trial" basis, and began enjoying her real-life slave, so she's kept me on.

I am her (owned) cuck-sissy-slave, and she's become comfortable with our relationship.

She could have ordered me to shave sooner, but we've simply allowed my inner sissy to emerge.

I LOVED my new hairless legs, and was getting excited.

Freshly shaved, wearing my sexy bikini, I lay on her towel next to her.

"You make such a cute sissy-girl," and I make a girly coo, while my manly cock hardens.

Sara is naked; unlike me, she wants no tan lines.

She knows I'm aroused....at my absolute most submissive.

My bikini bottom contains my cock nicely. It can be situated to either side fully erect, (and remain that way for as long as she dictates).

I am dying to cum.

"Do my feet," she orders. She loves her feet massaged.

I apply lotion, and she groans with pleasure, and my mouth waters, her freshly shaved pussy, mere inches away.

Our rules are clear, as I work up her legs, I am to massage only to the edge of her

pussy, but no touching/worshiping until she says so. She turns over; her ass is just as sexy.

Again, I start at her feet. I massage; she bends her knee so her toes are at my mouth. I kiss, and suck her toes; I suck like they were a cock.

She smiles, "That's a good girl. Practice your cock-sucking on my toes. You're a good little cock sucker, right?"

"Yes Mistress," I whisper.

I work up her legs, to her ass. She loves her ass cheeks massaged. I kneed each cheek, and she moans. I let a finger drift a bit between her cheeks, and get no resistance, so I apply more lotion, and work my finger to her rear hole, and tease lightly. She moans, "Hmmm, tongue."

I bury my face between her cheeks, and tongue-probe her lotioned hole, and she moans.

She rolls over, "On your back."

She straddles my face with her ass and grinds on my tongue. I can't see it, but I know she's rubbing her clit. She likes to cum this way.

She growls, "That's a good little sissy. Worship sissy! You are going to serve me for life! Ahhhh! Ahhhh!" And she cums, she cums hard, twitching, trembling.

She falls next to me, quiet in her afterglow, while my hard cock is nestled against her. I nestle and softly grind, yearning for friction. My cock is so hard; just minimal friction, and I can cum. "That's a good girl," Mistress whispers, and I know what it means. I'm dying to fuck, but instead she softly orders, "In you go."

I shudder upon her order, and ease into the snow-melt lake; the water is really cold!

Soon my hard-on is reduced to a little sissy-nub, and my balls have regressed.

Now I am still horny, but the imperious need to cum is tempered. When I am hard, my male-ness urges are still prevalent. Mistress has learned the power of bringing me to the edge, and then not allowing my orgasm. This is my true sissy-sub space, shrunken, closer to a clit than a cock...but still horny.

I am my most feminine, when my peepee is soft and tiny.

I play dress-up, but I'm not a girl, just girly. When I am "girly" I am inherently submissive.

I am not a typical "male", and not a girl, not gay, but a sub-sissy...serving a Mistress.

That said:

I practice my cock sucking on a dildo, while Mistress films me.

It's working, I have begun fantasizing a real cock blowing cum into my mouth.

Mistress has transformed my mind. Someday, I will suck a cock, and I'll be fucked in my sissy pussy.

Because of Mistress Sara, I now spend hours upon hours in "sissy-mode".

Pre-Mistress, I'd masturbate, merely fantasizing sissy-life, perhaps 15 minutes, an orgasm, then back to "male-mode".

Mistress's terms, I fully embrace sissification.

She has "male" boyfriends ad-nauseum, but I'm her "sissy" boyfriend. She's embraced me as her sissy, (and more...as her SLAVE).

I work from home, so I'm in sissy-dress all day. I wear panties, and a bra with realistic (water-filled) boobies. I usually wear a skirt and tight top with spaghetti straps, and high heels.

My eyebrows are thinned, and I am proficient with makeup. I can pass as a woman except from a short distance. Up close, I'm not just some guy in drag, I am a feminized sissy. I spend entire days in sissy-mode, even after I've masturbated...especially after I've cum, (which NEVER happens without permission...and I always send her a vid of the entire experience...including my cum lick-up).

Mistress can be away for days, or weeks, with some boyfriend, hardly thinking of me. She can be fucking the guy, and smile to herself, knowing her little sissy is at home, waiting for her....and no one else.

Back to the moment at hand...

We are on the lake, in my luxurious speedboat.

It has a sumptuous sleeping cabin, and a bed-like tanning deck, that is below where other boaters could see us, so she can lay around naked all day long...and she does!

Mistress just enjoyed an orgasm, and is satiated.

She lays on her side, and I stroke her body, and she mewls, and we drift off for a nap, the sun baking in our tans.

I awaken with a raging hardon.

I may be a sissy, but an adequately endowed sissy.

I slip down my bikini bottom. I need to cum!

I spoon Mistress, and she feels my hard cock nestled between her butt cheeks, and merely raises a leg, giving me access to her divine pussy.

Her pussy is already wet; (we've both enjoyed the tease, but now it's time for real FUCKING!) My cock head enters and we both groan, savoring this divine moment.

There's no hurry, and I ease in at her comfort level. She's now on her back and me on my side. Her leg raised, and my legs scissoring her other leg; this is our favorite fucking position. She slips a hand down to her clit, and soon she'll experience simultaneous clitoral and vaginal orgasms, and hopefully, I'll cum at the same time. This is our (orgasmic) sexual goal....every time we fuck.

"I'm getting close!"

"Me too!"

And we both freeze....in a moment of ecstasy! I feel her pussy gushing as my cock is exploding. We're both quietly groaning, and mewling, and chirping. It's life's finest moment, and then it subsides, and we exhale.

The sun is baking our freshly fucked skin.

My bikini bottom is laying next to us, but I'm still wearing my bikini top.

We just fucked like men and women fuck, but I'm still Her sissy-slave.

Early on, I told her that she should ALWAYS make me lick her clean.

We have evolved. Initially it was fun, her ordering me to "clean-up", but now, I am expected to lick her clean with zero prodding.

We lay quietly in afterglow.

Like a typical male, I just came, I don't want to lick her pussy, but as soon as she stirs, I slide down. Her pussy is glistening, with a large dollop of my cum collected at her opening. I lick the dollop, and taste my salty cum. Once I've made the first lick, my mind returns to full sissy-mode.

I love that I'm still wearing my bikini bra while I lick Mistress's pussy.

When I am finished, we jump into the water, which gives us goosebumps, and we're quickly back into the boat.

I pull on my bikini bottom.

My bikini is stretchy, and fits snuggly, so the tan lines are always the same, stark and unmistakable.

The following weekend, at Mistress's house, She invited her friend Crissy over.

I served them, and Crissy noticed my sub nature, and Mistress casually told Crissy I was her sissy slave.

Crissy inquired, "How so?"

"Take off your pants," Mistress ordered, and I did, revealing my shaved legs, and my panties. Crissy was mildly amused, but panties on a boy were hardly a surprise. "Now the panties," and Crissy was appreciative of my panty-tan, and shaved pubes, but still only mildly.

Mistress then dropped the bomb, "Now remove your shirt," and I answered, "Yes Mistress, as I pulled my tee-shirt over my shoulders.

Crissy shrieked! "A bra tan! What's he do at the Doctor?! Who else knows about this???" Crissy is a Doctor, (now my MD), and Sara answered, "You'll be her Doctor, and she wants to be on hormones....(or shall we say whoremones)," laughing.

Crissy looked at me, "Is this true?"

I nodded, "Yes," and she smiled, "So be it."

Fully naked, shaved, with hands locked behind my neck, Mistress tossed some heels to me, and rather than bend over, I raised my foot to the arm of the couch to put each one on. Heels are a major turn-on, and I was hard by the time they were buckled on. Crissy looked on, "I've never made the connection, until now, but I love the idea of male-sissy-slaves."

Mistress said, "Let's have my slave serve us for the rest of the day."

Crissy smiled and nodded.

Mistress ordered, "Play with your nipples."

Crissy watched, as my nipples hardened along with my hard cock.

Mistress commented, "Sissy has a man-sized cock. Watch this!"

Mistress squirted lotion into my hand, and I knew what to do. Kneeling with legs spread, I dabbed a finger into the lotion and began stroking my sissy-pussy. The other hand went to my cock, which was super-hard, now spewing pre-cum, which I dabbed into my mouth.

Crissy commented, "He DOES have a nice tool."

I stared at Crissy, eyes half mast, knowing Mistress wouldn't allow me to cum, knowing Her directive was forthcoming, and sure enough, she said, "That's enough."

I immediately removed my hands and locked them behind my neck, "Yes Mistress," my cock throbbing, yearning.

Mistress said to Crissy, "She makes a better Sissy when she's revved up."

Looking to me, "Make it cold, my little sissy. And be quick!"

She smiled at Crissy, "Now for her sissy clittie. Sissy-clitties are so cute."

Cold meant a cold shower.

Mere seconds later, with goose bumps, I returned, naked, my hairless cock a shrunken sissy clittie, holding my Sissy-maid outfit.

My "V"-neck top, sheer, see-thru, skin-tight, half covering my shoulders, stopping just below my sissy breasts, my thong panties also sheer and see-thru; my nub clitty tucked nicely. A satin tutu, thigh-high fishnet stockings, 3" high heels, and a choker collar. Last, a cheap, shiny, tiara, which would fall off if I moved quickly. It forced me to keep my head level, and take measured steps.

Crissy commented, "His tummy is so tiny! He really does look like a girl!"

Mistress corrected, "HER, tummy. For now, she IS a girl."

I retrieved my make-up kit, and vanity mirror, and on my knees, in front of my Mistresses, completed my look.

Mistress smiled, "Now the plug."

It made me flush. I retrieved my 1-1/2" butt plug, and with minimal lube, Crissy watched in amazement as I eased it into my sissy pussy.

I spent the afternoon mincing around, serving my Mistresses drinks and food, quietly answering, "Yes Mistress," all afternoon.

When not following orders, I cleaned.

Mistress's house stays very clean.

Crissy commented, "She cleans really well! Can I borrow her?"

"Absolutely," smiles Mistress, "You can keep her until your house...(and pussy), are nice and clean."

Now I serve two Mistresses.

I have cute little (hormone induced) boi-boobies...highlighted by my bra tan.

Crissy has a bi-boi-friend...I'm soon to meet.

Soon I will experience my first cock....blasting cum down my throat.

sissy171
sissy171
536 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

story TAGS

Similar Stories

Training My Sissy Body Lucy finds a new man to train her as a sissy.in Transgender & Crossdressers
Monica Turns Me Out My domme ex girlfriend finishes what she started.in Transgender & Crossdressers
Made Into His Girl Luke is tricked into chastity by Sissy and her brother Jake.in Transgender & Crossdressers
Sissified Ch. 01 Young boy is helped by his hot tutor in his transformation.in Transgender & Crossdressers
My Sissification Sissification evolution.in Transgender & Crossdressers
More Stories