Kinky Secretary Date Night

Story Info
Kinky Crossdressed Secretary and Mistress have a Date Night.
1.6k words
4.4
6k
4
0

Part 19 of the 56 part series

Updated 06/11/2023
Created 10/11/2021
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
cdDarla
cdDarla
115 Followers

"That's a wrap for the day Darla. We got a lot done today thanks to my Secretary."

I smiled at the compliment. We spent the day answering emails and arranging for Mistress' book signings. I was dressed in my secretary garb. A hot pink silk blouse over a black pencil skirt that stopped just above my knees. I wore opaque black hose and lower than usual 3 inch heels since I had been dressed all day. My makeup was more subdued than usual and I had pearls around my neck instead of a collar. Small pearl stud earrings instead of more extravagant ones were in my pierced ears. I did have my long red wig ala Darla Crane. My hair hung far down my back. We had a light supper and Mistress instructed me to freshen my makeup and change into my 4 inch stilettos. I put on heavier eyeliner and a generous coat of glossy red lipstick of the 'fuck me' variety since I hoped that would happen later.

We settled onto the love seat in front of the smart TV. Mistress scrolled through the movie options. I snuck a peek at my phone. There was a game on I really wanted to follow. What a contradiction. I loved being dressed en femme and serving as Mistress' secretary but also loved sports of all kinds which tended to drive Mistress to distraction.

"What do you think you are doing? It's our date night. Put that phone up right now. We're going to watch the movie with no distractions."

Mistress got up to use the powder room before starting the movie and I couldn't help myself. I snuck another look. Hey, it was a critical time in the game. Unfortunately, I didn't hear Mistress come back into the room. She had shed her sexy heels and padded into the room in stocking feet. She was livid!

"Go get the leather straps Darla. Right now!"

She grabbed my phone and turned it off as I went to the closet where we kept our restraints. We had a complete set of straps and cuffs along with gags of every style. She had me put on my leather cuffs and used a zip tie to join them together behind my back. She belted my legs together at the ankles, below and above the knees. She pulled each one very tight. Next came the leather cuffs that went above my elbows. She fastened them together, pulling my elbows closer together. She finished with a strap under my DD's pinning my arms tightly to my chest. Completely superfluous given the other restraints but it added to my feeling of helplessness.

"Now that I have your undivided attention, let's pick out a movie."

She scrolled through the choices and settled on a romantic comedy that unfortunately I had seen before. She clicked to start the movie.

"Mistress, can we please watch something else. I've seen this one. Maybe something with a little more action. Please!"

"First you try to watch your stupid game and now you whine about the movie I want to watch. I've missed the opening with you talking over the movie. Since you've seen it, you shouldn't mind if I watch it and I've got just the thing to make sure I can watch it without your complaining."

Mistress paused the movie and got up, leaving me helplessly bound and wondering what she had in mind. I groaned as she walked back in carrying the sensory deprivation hood she had bought at the fetish festival we had recently attended.

"This will keep you quiet for sure. I had planned on us getting turned on with the movie. Some wine, a Winston for you, Virginia Slim for me, lipstick on lipstick kisses before we hurried to the bedroom. But no, thanks to you. I may or may not enjoy your clit but you'll be deaf, blind, dumb and passive. We could have made out like school kids. It would have been such fun."

With that, Mistress first put foam earplugs in each ear before threading my long red hair through the hole in the top. She lowered the hood, sliding the large ballgag into my mouth. She tightened the ponytail opening to make sure there was no light or sound then proceeded to lace the hood tightly closed, plunging me into darkness. I felt her tighten the external strap driving the gag deep into my mouth before closing it around my neck. I couldn't hear a thing. I sensed her sliding back to her side of the love seat and I assumed she had started the movie. I caught the scent of one of her Virginia Slims and wished I hadn't looked at the game. I would have loved a Winston and a glass of the South African Sauvignon Blanc I knew she was enjoying.

Time crawls when all senses are taken away. I squirmed, trying to get comfortable and was rewarded by a crop to my upper thigh. I settled in for the long haul. It was not a short movie.

After what seemed like and eternity Mistress reached over and pulled my skirt up and panties down. I felt her using thin cord around the base of my clit and then tightly around the top of my sack before twisting the cord and separating my 'ovaries'. I groaned in frustration and her hands moved away. I desperately wanted her to sit on my clit and started thrusting upward but was rewarded by several sharp crop strikes to my now agonizingly sensitive clit. Then she left me alone, maddeningly alone.

Deprived of movement, sight, sound, speech and at the complete mercy of my Mistress lover, time crawled. I sensed her movement on the seat next to me and knew she was having a cigarette and I desperately wanted one. I could only sit quietly, a disembodied clit for her to use or not. Despite the frustration it was undeniably erotic. I could only hope she would use me for her pleasure and mine at some point.

I drifted into what I suppose was a fugue type state and sank back into the cushions. She must have sensed it and cropped my aching clit again before taking me in her mouth for just a few seconds to show me what I was missing. She continued to alternately ignore and stimulate me. If I had been free I would have picked her up and raced to the bedroom.

Finally I felt her unbuckling the neck and gag straps. She loosened the laces and removed the hood and ear plugs. I could see the movie credits rolling as I blinked against the sudden return of light.

"I hope you enjoyed that as much as I did. Such a fun movie and such a good lesson for you, Darla. I think next date night you'll leave your phone alone. Am I right?"

She certainly was and I quickly agreed.

"With all that said, that movie got me going and I have to admit the sight of you so helpless and hard did too. I just love the hood. Your red hair in a pony tail was so cute. I'll show you the pictures later. They'll be great for the blog. Since I'm turned on, I think I'll take advantage of you even if you don't deserve it."

She sat on my lap facing me, kissing me hard and deep. We both loved the lipstick on lipstick lesbian kisses. I didn't think my bound clit could get harder but it did. She used her finger to scoop some precum and fed it to my eager mouth. She then leaned down and took me in her mouth, covering my clit with smeared lipstick. I begged her to fuck me but she just laughed.

"Patience Darla, patience. This is all about what I want and I want you to suffer just a little longer."

She started kissing me again and again while she lightly stroked my almost painfully sensitive clit with one hand and stroked her own pussy with her other. She held out her hand for me to taste her intoxicating excitement before finally impaling herself on my clit. She sat still for a minute, flexing her pelvic muscles and driving me even wilder before rythmically moving up and down my bound member.

I so desperately wanted to cum but at the same time to enjoy her power and control over me for as long as I could. She plunged her tongue into my mouth and I in hers in a last violent kiss.

"Cum for me baby. Fill me up. I can't wait any longer."

I exploded into her as her head fell back and we dissolved into mutual ecstasy.

"Wow, baby. I need to use the hood on you more often. By the way, I planned it all along. If you hadn't checked your phone I would have come up with another excuse. That was exceptionally hot. Now let's get you cleaned up."

She got up and used a warm cloth to clean my clit after untying the cord binding it.

"I'm going to change into my nightgown. You sit tight and decompress. Just because you got to cum doesn't mean I'm not still in charge."

With that, she leaned over to kiss me once more and went into the bedroom. By this time I was desperate to get loose but wasn't about to say anything. She came back and finally untied me. I stretched my stiff limbs then took a sip of wine before lighting a post coital Winston.

"Now then, get undressed. I'm not through with you tonight!"

I stumbled toward the bedroom shedding my clothes. I certainly hoped she wanted more. I certainly did. It was much more tender and slow but just as satisfying. I drifted off to sleep with Mistress in my arms. I thought again I was the luckiest girl in the world and I couldn't wait for the next date night.

cdDarla
cdDarla
115 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

READ MORE OF THIS SERIES

Similar Stories

It All Goes Wrong, Pt. 01 Crossdressing fantasy adventure.in Transgender & Crossdressers
Maid for Hire Caught in my maid’s uniform by my GF.in Transgender & Crossdressers
Sissy Training Facility - Day 00 Jake checks out if "Sissy Training Facility" is a real place.in Transgender & Crossdressers
CD Vicky Lives Down the Hall Sound of CD Vicki's heels causes a problem.in Transgender & Crossdressers
My New Life in Lingerie Caught in panties I was moved to lingerie and more.in Transgender & Crossdressers
More Stories