Pretty Please

Continued from: A Punishment Spanking

In the days following Russell's punishment spanking, I was little more micro-managerial as it related to the office. I would make frequent visits and ask the girls what they had been tasked with. 

It seems I walked-in on "break-time", during one of the said tasks. 

"You didn't want to do the honours yourself Russell?" I teased, while looking down at his mid-section. 

He blushed and whispered back to me, "no Ma'am." 

Clearly his bare bum was still in no shape to be visibly exposed to his two subordinates. You're going to be feeling this for a week is what I was going for during his punishment the other day. I think I achieved my goal. 

"Well, lets take a seat for a moment, Russ. Don't you just love that she's forced to watch her own boobs in the mirror, flopping and dangling about?" I said, as we both sat and watched on.

"Bella huni, if she looks away from the mirror again, slap her." I instructed.  

We watched for a little while longer. 

"Just make sure it's not an all day break, ladies," I sternly counselled. 

"Yes Ma'am," they both replied. 

"Russ, the girls are almost home from the airport. Lets go help them with their luggage." I said. 

He whispered out a little, "yes Ma'am" to me. Hoping his Secretaries wouldn't hear. He must have thought they did hear him, because he felt the need to reassert his dominance as we walked out of the office. Silly man!

"Five more minutes ladies." He called out. "Then you can kneel and clean off that cock, Sarah Jane. After that, it's back to your desks, ok?" 

"Yes Sir," they both moaned out loud. 

Russell and I left them to their business. I was excited to see Summer and secretly excited to see Goddess Vanessa as I now call her. I wonder if she has any new tales about cuckolding her sissy husband?!

Russell helped the two of them with their carry-ons and after kissing Summer passionately, I went to greet the supreme Goddess who is my newest girl crush. 

"Hello Goddess Vanessa," I purred to her, as I embraced her into my arms. 

She giggled and blushed. "Ohhh Mistress, you're too much!" 

Meanwhile, I watched Summer do her best "Daddy's little girl" move, slithering herself onto Russell's lap. She must want something. Ha. 

I heard her crying out "pretty pleasssssse" to him in a baby voice, yet I didn't catch what she had actually asked him. She was bouncing up and down on his lap at this point.

With the added weight of Summer on his lap, I noticed Russell wince a little, adjusting his tender buttocks against the hard chair. 

"You better ask Mistress," I heard him say to Summer. 

Instantly, I get a "Mommmieeeee?" From her. 

*Sigh*...

"Yes sweetheart?" 

"Can Russell come shoot some content with us? We need a pilot for a new idea.” She mewed out. 

"Feet only?" I asked her. 

She looked over at Vanessa. 

"Maybe some bum too." Vanessa said. 

I nodded my head in a gesture toward Russ, then looked at Summer while raising an eyebrow and said, "soumis?" 

"Oui Maîtresse." Summer replied. 

Haha! Summer taught me some French. I can talk about Russell right in front of him now 😈!

Preserving the essence of their long flight in hosiery and heels, the girls clicked off down the hall to their special space to grab some film equipment and sealed baggies to eventually package up their tights. 

I took Russell up to my bedroom to brief him on what was about to go down. 

"Russell, I don't image you wish to end up over my knee again, do you?" I spoke firmly. 

"No Ma'am," he replied as he lowered his gaze. 

"The girls want to dress you like a pilot and create some content relating to their feet and high heels. I expect you to do whatever they say, is that understood?" 

"Yes Ma'am," he peeped out. 

"You used to worship my feet for hours back in the day, remember? This should be a breeze for you." I reassured him. 

We got Russell into the pilot outfit while the girls were setting up the video equipment in my room. 

There was a nice fire in the background, making their stilettos glow. This was of course complimented by a silly man on his hands and knees, where he belongs, in the presence of such elegance and beauty. 

Lets hope Sarah Jane doesn't walk in on this, and see her "Daddy" in such a compromised position. 

"He's all yours girls. Don't bother being gentle." I purred to them. 

Mistress Andrea

xoxo

Continued in: French Cut

A Punishment Spanking

Continued from: "Forced" Labour

I walked into the room deliberately slow but commandingly. I wanted my heel-clicks to thunder off the hardwood and echo throughout the room. Russell used to know this sound well, years ago, and when I saw him begin to tremble in the corner, I could tell I still had the same effect on him.

I clicked into the room a few times, again, deliberately. I didn't say a word and left it to his ears and his butterflies to determine what I was tinkering around with behind him. 

I placed a sturdy chair in the centre of the room and laid out some heavy hairbrushes and paddles. When I checked my timer it was counting up to the 32 minute mark. It was time! 

"Well, well young man. It's been quite some time since I've seen you like this."

"Andrea, is this really necessary." Russell tilted his head to the left and spoke. 

"Use my given name again young man, and I'll have your two slutty Secretaries down here to watch you sobbing over my knee!" 

"I'm sorry Ma'am." 

"Rest assured young man, you will be sobbing very soon, now turn around and come here." 

To ensure I kept this punishment as real and meaningful as possible, I wanted him bare naked for this. Not a single stich of modestly left. 

"Take off your shirt and socks Russell." 

"Yes Ma'am." He complied. 

"I don't imagine you would have forgotten that I am right-handed. Come around to my right side." 

"Yes Ma'am." 

Oh! I heard a crack in his voice there. Stripped of all his clothing with me fully dressed, thirty minutes in the corner and now he caught a glimpse of the tissues and lotion, along with the hairbrushes I had laid out on the table. Things just got very real for him. Perfect time for a good scolding. I remembered to use the dreaded 'D' word too!

“Russell, I understand you have Sarah Jane to train and condition as a slutty Secretary. But you need to understand that I am also running a business here." 

"I trusted you to manage not only yourself, but also Bella and Sarah, to achieve the objectives of my various portfolios and revenue streams."

"I think you took advantage of me. I'm disappointed in you, young man."

There goes the bottom lip! I watched Russell's eyes gloss over with tears and waited a moment for my words to sink in before patting my lap. 

He lowered his head in shame and mumbled out a, "I'm sorry Ma'am." 

"Over you go. We're going to ensure this doesn't happen again."

His vantage-point, similar to the image below, leaves no ambiguity about the reality of his situation. The reality that he is a grown man currently on the verge of tears, naked and draped over a women's lap, about to be given a spanking. 

The view in undeniably feminine and beautiful, but intimidating at the same time. 

I started off in this classic OTK, straight-backed chair position using only my hand, as I begin most all of my spankings, regardless of who the recipient is. It is too important to skip this part. 

I did a little scolding throughout the spanking, to reinforce my disappointment in him, as I changed up our positions and began to layer him with the wooden implements. 

His tears and apologizing returned when I began a very sound paddling of his sit-spots. 

The true sobbing didn't begin until I swapped out the wooden paddle for my ebony hairbrush, a truly dreadful implement. 

By the time I was finished I could see the sweat glistening on his back as he collapsed to his knees and sobbed into the cushions of the couch. 

I returned to the spanking chair with the bottle of soothing lotion. With gentle and maternal care, I patted my lap to invite him back into an OTK and vulnerable position. He crawled over and laid his head in my lap. I heard a genuine apology through is sniffles. 

I gently massaged some cool lotion onto his burning bottom, all while he was jackknifed over my knee. When he had calmed down I led him to the corner and helped him into a kneeling position. 

"Thirty minutes young man, hands glued to your sides." I instructed. 

He bowed his head in defeat, not looking forward to the embarrassment and boredom of such a lengthy timeout. 

Nevertheless, he sniffed out a reluctant, "yes Ma'am." 

I was satisfied with the consequences for his actions. I'm sure that colour will occupy his sit-spots for a week!

He'll be too embarrassed about the state of his bum to undress in-front of his two Secretaries. I guess I solved the spending all day fucking your Secretaries problem. Even if it's only for a week. 

However, I suppose it won’t stop him from making them fuck each other while he gingerly sits to watch them. 

Oh well. I tried. *shrug* 

Mistress Andrea

xoxo

Continued in: Pretty Please

 

Chastity Belts or a Spanking?

Continued from: The Countess of Monte Cristo

What would you chose, as an incredibly sexy and aroused young lady? Turning over the key to your arousal, literally, and having your aching cunt locked up in a chastity belt? Perhaps not knowing when or if, in the foreseeable future, it will be unlocked. 

Or do you take your lumps and submit to a painful and humiliating spanking on your bare bottom, in hopes that maybe your pussy will get some attention afterwards? 

I like to give my naughty girls, naughty male slaves and sissies options to choose from. It fucks with their minds. The embarrassing predicament of having to chose from the lesser or two evils. Or at least what you think is the lesser of the two. 

I approached my two girls and cut right to the chase. 

"What's it gonna be ladies...your chastity belts or a spanking?" 

If you're just joining in on this predicament bondage, Cassandra in the pillory, who was kind enough to offer my wife Summer, (on her back with legs forced open) some erotic dance lessons. They got themselves into full stripper heels and attire and while I worked away in the kitchen, I could hear the pounding of music from the strip-joint on the upper floor of our house.

I was preparing a delicious lunch for the three of us and when I returned upstairs, I caught the two of them about to embark on a delicious sixty-nine with each other's soaking pussies. 

Summer and I have a unique relationship and having her pussy devoured by my sexy Receptionist is not unheard of, but both of these naughty young ladies know they need my permission first. 

In this instance, I did not give it, nor was I asked. This is why Cassandra's face was forced to stare at my wife's pussy and inhale her sweet arousal for the past hour. It was a fitting punishment, but as they now realized, their punishments were not over. 

I would have loved to see these two desperately begging to be unlocked. Watching me openly masturbate and please myself with toys, as they pull and tug at their belts. I'd make them suck each other's nipples and make out in front of me. Watching their faces twist in frustration as the ache in their clits intensifies. 

Alas, not this time, they both chose to be spanked...

Unfortunately for them, I was still working in the kitchen. This means wooden spoons and spatulas are readily available and I think I used every wooden utensil in the holder!

I relieved them from their stripper outfits and marched them bare naked up to the kitchen and living room. I started with Summer first as Cassandra was forced to watch. 

After a nice long warm-up for both of them, I moved a dining chair into position and arranged my bouquet of wooden spoons, within my reach. 

Once Summer was howling and sobbing, promising not be a naughty girl again, it was Cassandra's turn. 

I asked her to choose which wooden utensil she would like (mind fuck again). When she hesitated I motivated her with my palm. 

I bent her over the kitchen counter and watched her do a little dance in her bare feet, as I soundly smacked her rosy bottom. 

She made her spoon selection without hesitation the next time I asked her to pick one. I then took her over my knee and finished her off in a frenzy of sobbing spoon slaps, blubbering apologies and kicking legs. 

I loved the fact that my large picture windows in the dining room, look out and IN...to the street below. The pair of them, both still crying liberally, mashed their tits and nipples as far as they could get them against the corner, in an attempt to hide their shame from the outside world. 

Now...I can sit and enjoy my fancy grilled cheese in peace...maybe I'll take some down to Sarah in her cell. These two will be facing that wall for the next hour at least...I wouldn't want my beautiful culinary creation to get cold or go to waste. 

"Next time girls, just ask me if you want to go down on each other, so I can at least watch or help. Sheesh!" 

Mistress Andrea

xoxo

Continued in: She was a Sk8er Girl

Bridesmaids

Continued from: No Turning Back

No speeches, no Macarena or chicken dance and the added possibility of random, intense sexual encounters cropping up. This was the best wedding reception I've ever been too, and it was mine! 

In the limo on the way back to the house, Summer told me that Vanessa had really taken a shine to Bella. Yes, like that type of shine. 

Without hesitation I gave Bella a slave pass, absolutely! Vanessa was a rocket. It was a wedding party gift from Summer and I. Bella could do what she wanted with Vanessa tonight, provided she was outwardly submissive toward Vanessa. 

As the night wore on, we danced, we drank, Summer and I spanked both of our sissy gurls at one point, right in front of everyone, then took them outside for some air and a brief chat. 

We first let them listen to us talking about unlocking their dicks, as a bridesmaid's gift from Summer and I. It was their glimmer of hope, that they may finally have a full orgasm with their penises. The last time this occurred was over six months ago, when Katrina and I had them 69 each other right in front of us, finishing the humiliating event by cumming into each other's mouths. 

Since that time, Kaylee has been blowing some of my male clients on a regular basis and Tiffany is in a three-way relationship with his girlfriend Katrina and her bull named Cole. Tiffany is no stranger to fluffing his cock and sucking him off, to prepare him for fucking Katrina. 

Sucking dick was no longer such a taboo or a big deal for these two cock-sluts, we had to raise the stakes a little. 

Meanwhile, Bella and Vanessa had slinked off to do their own thing, she was a good girl and kept her collar on, but it appeared that was the only thing she had on. 

Just over Vanessa's shoulder, at their three o'clock, two studs sat in wait. I had suggested to them when the night began to wind down, that my gurls would look after them. They were both game. 

The two sissy bridesmaids had a moment to deliberate, before it was time to make their decisions. 

"Well gurls, what's it gonna be?" I asked. 

"Entertain our handsome pilots and I do mean entertain, in any way they want, and you'll earn an unlocking. Or call it a night and I'll be keeping your chastity keys safely secured away, for a little while longer." I added, with a devious grin on my face. 

"Safewords are always an option too gurls," I finished with. 

Their desperation to cum and new-found lust for all things sissy and humiliating, made the decision for them. They had been conditioned into perfect little bimbos. 

Summer and I couldn't believe our eyes, this was amazing to watch. 

The gurls, although somewhat stoic, were doing an amazing job pleasing our guests. 

Then, in an incredible escalation of desire and sexual passion, it happened. Summer and I were about to witness Tiffany and Kaylee, lose their anal virginity. 

Kaylee had only ever taken my strap-on and toys, Tiffany also, and Katrina had reported to me previously, that her bull Cole, has never fucked Tiffany, only oral with him. 

So this was it. No safewords were spoken, not even reluctance. My two sissy bimbos actually wanted this to happen. 

It was cute to hear Kaylee's chastity cage, clacking and bouncing about between her legs, as Lance fucked her boi pussy. 

Tiffany's first experience was not too far behind. Summer and I both heard him groan like a whore, as Eric entered his smooth, hairless asshole. 

Kaylee was now riding Lance, moaning just as intensely...still not a breath of a safeword was spoken. 

All was right with the world, we left the studs to carry on and finish up, telling the two sissies to come find us when the pilots leave, to see about their bridesmaid gifts. 

Groomsmen gifts? I think our two pilots were capitalizing on those right now! Hehe. 

As for Summer and I, I had matrimonial duties to attend to. I had to consummate this marriage with Summer. Did watching those two studs fucking the two sissies make us super aroused? 

Mayyyyybe...

Who consummates a marriage of their beautiful bride, with bondage, a whip, a ballgag and a pair of nipple clamps? 

I did! All night long, until Kaylee and Tiffany darkened our doorway, faces blushing and likely clenching their bums, trying to hold in all the cum.

Mistress Andrea

xoxo

Continued in: Keyholder

The Wedding Party

Continued from: The Maid of Honour

The big day is approaching fast. Summer and I went dress shopping a few times and we still hadn't decided on how our same-sex, D/s dynamic wedding should play out. I didn't want Summer to feel like she's a spectacle for the eyes of others, we also talked about whether or not she should be in innocent, virginial white (hehe), maybe not so virginal but I like the white bride look. 

Should I be in a suit, or leathers...should Summer be in a collar? There were plenty of ideas floated around.

I really liked this one on her, a corseted, lingerie bride? 

Isn't she a freakin' hottie? 

But...I wanted to look like a bride too! Not a groom. I really liked this one and tried some latex gloves with it, as a nod to our kink lifestyle but not so kink that we enter into a full-blown, BDSM wedding. 

I think it was Natalie Mars, the very famous, sissy porn star, who got married to his/her Dominatrix. They went with a fun gender reversal, bride/groom feel. I wonder if Natalie's penis was locked up during this ceremony? The clamps are certainly a nice, decorative touch. 

I'm not sure if Natalie goes by her or him, I assume the former. No disrespect if I got it wrong.

Speaking of sissy slaves, was there ever any doubt, who my bridesmaids would be? Of course it's going to be Kaylee and Tiffany! This will be their ultimate humiliation and the ultimate point of no return for them. There will be absolutely no returning to being a man for these two, after this wedding.

Katrina let me "borrow" Tiffany for this event and this role. Kat is going to be attending anyway, with her alpha-bull, male submissive, Cole. 

Do you remember Vanessa? This little stunner...

Way, way back from the original post, where I first discovered that some Flight Attendants sell their used hosiery? That Vanessa.

Summer essentially learned their naughty little trade-secret from Vanessa, they have been partners in nylon fun and games and best friends ever since. This is who Summer selected as her Maid of Honour. 

Yep, she's about an 11, as I suspected she would be. 

As for the rest of Summer's side of the wedding party, she went with her actual flight crew from work, the pilot and co-pilot. 

I don't often get impressed by silly males, and these two are likely as silly as all the rest, but what a pair of studs these pilots were! Holy shit. Of course one of them is named Lance but I can't remember which one, the other is named Eric. 

Look at the machismo dripping off these two. They probably fly the plane with their cocks! Is that where the term cockpit comes from? Hehe.

We're definitely going to have a very handsome and gorgeous wedding party! 

When the day finally arrived, I was absolutely right, we were stunning! I hadn't seen Summer yet, the morning of. I had butterflies like crazy!

Alright, time to do this thing! Wish me luck. 

Mistress Andrea

xoxo

Continued in: No Turning Back