Kinky Secretary turns Domme Ch. 02

Story Info
Kinky Crossdressed Secretary turns Domme 2.
2.8k words
4.35
4.6k
1
0

Part 3 of the 3 part series

Updated 06/11/2023
Created 10/31/2021
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

The big day finally arrived. I was both excited and nervous. It seemed fitting it fell on Halloween given the outfits Jane and I would be wearing. We were supposed to be cat burglar jewel thieves who pulled off home heists in trademark outfits. I slipped into my skin tight black catsuit, thigh high pvc boots and a shiny waist cincher pulled tight with Mistress' help. I had on my Darla Crane wig, long luxurious red hair that hung nearly to my waist. Striking eye makeup with heavy liner above and below finished with a wing out from each eye courtesy of Mistress. All of this topped my fuck me red lipgloss. My nails were glued on. It wouldn't do to lose one as I tied up our victim. I pulled on my Catwoman style mask. The eyeholes were big enough for the eye makeup to pop through. I checked out my look in the mirror.

"You look good enough to eat baby. I'm not sure there are really burglars who dress like that but I'm sure your 'victim' will love it. Just remember to behave yourself. I'll know it if you don't."

Just then the doorbell rang and Jane walked in. She was in skin tight black leather pants and top over 4 inch spike heels and a matching mask.

"Well aren't we a sight. Thanks again for letting me borrow Darla. I'll keep a close eye on her, don't worry."

Well Jane, that's exactly what I am worried about. I'm not sure you know the meaning of 'behave'. You kids have fun and be safe."

We climbed into Jane's high end SUV. The kidnapping business must be really good. I lit a Winston and handed it to Jane before lighting one for me.

"Remember the scenario Darla and follow my lead. As for behaving, what happens with Jane stays with Jane. Sounds like a slogan, right. Someone should use it."

We drove out from the city and the houses got further and further apart. I spotted the mailbox with King on it. We turned onto a long gravel driveway that led to a stylish home that was completely secluded. No chance of someone seeing the cat burglars gaining entrance, particularly in the dark. We parked, gathered our equipment and went to the front door where we supposedly picked the lock to gain entry. Of course, it was unlocked. We each turned on flashlights and crept through the house to the master bedroom door. Just where it was supposed to be. Jane looked over at me.

"Ready?"

I nodded yes. We brandished our silver realistic water pistols and opened the door. Our victim sat up in bed, feigning surprise as the flashlights shone into her eyes.

"Who are you? What are you doing here? Get out now!"

"Sorry cookie, no can do. We'll leave but we're leaving with some of the goodies you have in your lovely home. Since we'll be here a while, you can call me Jane and my tall friend is Darla. What's your name, cutie?"

She stammered a bit before answering, clearly into her role. Jane and her henchwomen insisted that everyone stay in character.

"Penny, short for Penelope. Please don't hurt me."

"We have no intention of hurting you, just your bank account, honey. And what a name, Penny King. Just like Sky King's niece in the old TV show. She always managed to be captured by the bad guys and tied up before Sky rescued her. Unfortunately for you, Sky King is nowhere near here. Shed that nightgown, let's see what we've got here."

She pulled her nightgown over her head revealing a trim figure with average breasts. She was a brunette with a business like bob.

"Don't give us any trouble and we'll be in and out before you know it miss 'short for Penelope'. Tie her up Darla."

I reached into our rope bag and went to work while Jane brandished her pistol. Penny looked suitably apprehensive as I pulled her arms behind her, wrapped and cinched her wrists as MIstress had taught me to do. I did the same for her ankles and thighs before pulling her elbows together. She was quite flexible and they touched easily. I finished her bondage with rope around her chest, above and below her breasts, making them protrude and look bigger. Jane tossed me a penis gag which I buckled tightly into her waiting mouth.

"Sugar, we're going to look around and decide which treasures to relieve you of. You behave now, as if you have a choice."

Jane laughed at her own advice then placed a discreet tiny camera on the dresser before we walked out of the room and closed the door.

"She wanted to be tied up and left. A common fantasy as you no doubt know. Hence the camera. I'll check her on my phone. Safety first always Darla."

We walked into her well appointed den after stopping at the refrigerator and helping ourselves to a glass of excellent Sauvignon Blanc from Chile. Penny clearly had good taste. Jane checked her phone and grinned as she showed me Penny writhing on the bed, clearly enjoying herself by trying to get loose.

"Nice job Darla. Mistress taught you well. Since we're not really looking around for things to steal, tell me how you came to be who you are."

I lit a Winston and tossed the pack to Jane who did the same. I sipped my wine and thought back to how one comes to enjoy bondage and crossdressing fetishes.

"I think some of it is in our genes. I really do. I remember being turned on as a little kid with the detective magazine covers in the drug stores though I never wanted the women to in true jeopardy. Of course, the comic books were there too. Superman, Batman and all the rest. Lois Lane always had to be rescued. Then I suppose it was TV shows like Sky King and the old westerns where Penny and the other heroines always managed to get themselves tied up. When I was older it was shows like Honey West, the female detective. Not only did she get tied up but kicked ass when she got free. I loved the combination of vulnerability and strength. Superman went from the comics to TV and sure enough, Lois still got herself tied up. That girl constantly needed rescuing but she also was kind of a kick ass reporter. Then I found adult book stores. Are there any left? Everything's on line now. I loved Bondage Life where the bondage was always voluntary and fun. Darla Crane was one of their top models and I simply loved her look. Who didn't? They also had a men in bondage section with many crossdressed. I found that increasingly I loved looking at Darla and the rest but wanted it to be me in bondage."

I paused to take another sip of the excellent wine.

"Hold those thoughts, honey. I think our captive is trying to escape."

Indeed, Penny had maneuvered to the edge of the bed and was in the process of standing and taking a couple of hops toward the door.

"Let's make her a little less comfortable, shall we?"

We opened the bedroom door and each took an elbow and hopped her back to the bed before pushing her face first on the soft mattress.

"Sweetheart, I'm disappointed in you. You really should have behaved. We've got a few more things to load up so let's make sure you don't go anywhere. Hogtie her Darla."

I pulled a piece of rope from the bag and looped it through her ankle ropes before tying it to her chest harness, careful to put the knot far above her wrists.

"Just to make sure your mind isn't on escape, we've got a couple of other things to distract you."

Jane reached into the bag and pulled out a pair of clover clamps. What cat burglar leaves home without them? Penny's nipples were already firm from her clearly enjoyable predicament. She moaned as Jane applied the clamps. She reached into the bag and brought out a blindfold with a nose cutout. She put it on tightly, plunging Penny into darkness.

"Just one more thing, sugar. Let's mix some pleasure with the pain. The last thing on your mind will be giving us trouble."

Jane handed me a wand vibrator and had me tie it in place touching her already drenched sex. She jumped as I turned it on.

"Have fun now honeybunch. We'll finish up. You have so many nice things. It's hard to choose."

We went back into the den and Jane checked on Penny who was clearly already in the throes of an orgasm.

"We'll let her have a couple more then have some fun ourselves. Now where were you?"

I lit a Winston and continued. "I desperately wanted to live the fantasies I told you about. That's where Mistress comes in. I found her on line and looking at her pictures I just knew I had to meet her. Of course I was nervous and really, my first efforts at dressing and makeup were pretty pathetic looking back on it. She was patient, helping me with makeup, clothes, walking. She even taught me to smoke seductively, obviously another fetish of mine. I really don't that much but when I'm dressed it just seems so sexy and naughty that I can't help it. The added benefit is Mistress getting upset when I pull out my Winstons instead of Virginia Slims. She feels compelled to punish me which is of course, what I have in mind."

I took a long drag and sent out a plume slowly toward the ceiling. "What about you, Jane. Where did you go so delightfully wrong?"

"Another time, but a lot of the same things Darla. I've always been bi but mostly like women. That's why you're such fun baby. Right now we've got work to do. I think Penny is more than ready for us. As for you behaving, forget it. Penny wants a forced bondage blow job and judging from the bulge in your catsuit, so do you."

We walked back into the bedroom as Penny finished another forced orgasm. She had a light sheen of sweat and panted as she tried to catch her breath.

"Sweetness, we're about ready to leave. I hope you're well insured but before we go, you really shouldn't have tried to escape. We can't let that go unpunished."

Jane had me take her out of the hogtie and help her to her knees. I took off her blindfold before unzipping my catsuit, freeing my erection. I paused to light a Winston. I had fantasized about smoking a cigarette as an attractive woman took me in her mouth and now it was coming true.

"Take off the blindfold. Let's let the little lady see what's coming. Take it all doll, we don't want to piss Darla off do we? Think of it as a high protein snack. You need the nourishment after all that writhing around."

I looked down at Penny sliding her lips up and down Mistress' clit. I took a last drag and reached down, holding Penny's head firmly in place as I shot my load into her. I sat back heavily. Another fantasy realized. Jane brought me out of my reverie.

"Help me here, Darla. Untie her legs and put her face down on the edge of the bed."

I did as she said and looked around at a monstrous strap on that Jane was lubricating before plunging it into Penny's waiting soaking pussy. She started slowly and motioned for me to spank Penny between her thrusts.

"Come on honeybunch, I'm doing all the work here."

Penny grunted into her gag and started actively meeting each of Jane's increasingly violent plunges. Jane clicked on the vibrator, making sure she got her own pleasure. I had been on the receiving end of Jane's attentions and licked my lips. I had to admit I was a bit jealous. Penny shuddered as Jane finished her off and stumbled backward, both overcome by the raw eroticism of the moment.

Jane slipped out of character finally. "Let's get you untied Penny. I hope you've had enough. You managed to wear both of us out."

Penny nodded yes and I started untying her. I unbuckled the penis gag and Penny surprised me by pulling me into a deep kiss before doing the same to Jane. She really was bi, for sure.

"We'll wait for you in the den, Penny."

We walked out of the bedroom and shed our masks. I felt fantastic but exhausted by the intensity of the scene. Jane and I lit Winstons and went back to our wine. Penny walked out in a silk dressing gown, poured a glass of wine and reached for my pack.

"I really don't smoke, but if there was ever a time.....".

We chatted for a while. Penny was effusive in her praise. She said it was everything she could have hoped for and more. I couldn't have agreed more.

"Next time I'd love be tied up with Darla and you. No gags or blindfolds. I'm wet again thinking about going back and forth between the two of you."

Penny was seriously twisted. Clearly a match for either or both of us.

"We'll have to clear that with Darla's Mistress. She's likely in trouble already after promising to behave. But really, Mistress won't be surprised. Will she, Darla."

Penny thought for a minute. "Maybe Mistress would be more kindly disposed if we were to make it easy for her to punish Darla. If I were her, I would appreciate my slut being delivered already bound, gagged and helpless for whatever punishment I chose to dish out. And really, I'd love to help. I'm pretty handy with ropes myself."

I didn't think it would matter, but what the hell. I had fantasized about being 'delivered' to Mistress after my own kidnapping experiences. I would be her Halloween present and if she wasn't inclined, she could just leave me tied up and ignore me. A winner either way. Jane collected the rope and supervised Penny as she tied me surprisingly tightly in the same way I had tied her.

"Let me show you something else to try. It will make the present hopefully a little more appealing."

Jane unzipped me and brought my clit out. She took thin cord and took several wraps around my scrotum, pulling my 'ovaries' down before twisting the cord and separating them. I started to harden despite my earlier adventure.

"Penny, please do the honor with the gag."

"My pleasure Jane."

She buckled it, smiled and tightened it another notch as I looked over at Jane and her phone.

"Mistress, just wanted to let you know we're on our way back. I hate to tell you this but in the spirit of full disclosure, Darla was a very, very naughty girl. So naughty I had to tie her up. She threatened to run away but Penny and I managed to overpower her. Yes, Penny is our client. You'd love her. Such a sport and very good with rope herself. Ciao, see you soon."

She hung up and looked over at me thoughtfully. "Penny, how is Darla going to get to the car? We could untie her legs. What do you think?"

"I think Darla should hop to the car so I can watch her clit bounce up and down and when we get there I'm going to hogtie her for the trip back."

They each took an elbow and hopped me to the SUV. Jane opened the hatch and put the seats down. They heaved me in on my stomach and Penny hogtied me, pulling the rope extra tight. This girl was something. Jane waved a last good bye and started home, keeping a running one way dialog about what Mistress was likely to do to me. We pulled into the garage at home. Jane undid the hogtie rope and pulled me by the ankles out of her car. I steadied myself and hopped through the door. Mistress was a vision in a leather dress and boots. Perfect makeup and hair. She motioned Jane toward my low backed chair and had her secure me to it. Jane quickly exited, trying to avoid Mistress' wrath though I knew she would love to have watched.

"Well, well Missy. What do you have to say for yourself? Never mind, I don't want to hear it and besides, that gag looks really tight. While I appreciate the package in your crotch, you'll be lucky to use it for quite a while indeed. You need to be reminded that your clit isn't really yours. It's mine! Let's get started, shall we?"

I groaned behind the gag. It was going to be a long night but isn't she wonderful!

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

Bad Brat Girl Domme Sarah needs Daddy's help to reach her submissive side.in BDSM
The Big Tits Club Ch. 01-04 A virgin teenager and his six busty best friends.in Group Sex
Demon Queened Ch. 01 Jacob is reborn as Devilla - the villainess of a porn game!?in Lesbian Sex
Sophie's Wedding Day Even home-made brides have to get married.in Transgender & Crossdressers
An Unsuspecting Daddy A not-so-chance meeting, with a surprising woman...in Transgender & Crossdressers
More Stories