All Three Holes

Continued from: Quid Pro Quo

A Sarah Jane story

As I mentioned in the last post, I told all of you that I would just fast-forward to the party that Daddy let me attend. He didn't join me *pout*. He likes watching me with other women, but I suspect he's not too keen on seeing me taking down multiple cocks. In his absence, Mistress Andrea was to be my guide and controller for this particular evening. She looked stunning as usual, it was actually nice to see her again. Bella was there too, but this time it would be her as the more passive observer while I get to indulge. 

Mistress introduced me to a few of the men. My instructions were simple and a ritual I was very used to: Kneel directly in front of the men with my head down and palms on my thighs, then politely ask for permission to suck their dicks. If they say yes, find and expose the bare penis, kiss the tip and say, "thank you Sir," then directly into my mouth with it. 

If they cum on my face or into my mouth, again, a "thank you, Sir," after I have swallowed, and I kiss the tip of the penis. Easy peasy. Daddy has the same rules for me, when it comes to my oral worship of him. 

It mustn't have been more than an hour into the party and I had already sucked three cocks, ending with one facial and two full swallows. I felt like such a dirty whore and I was loving it. Mistress even made me wear the strange man's cum on my face as the evening continued. 

This was around the time that "SHE" came in. This tanned and stunning woman with dyed, blazing-red hair and the most adorable bangs. She was in heels and a collar only...nothing more. She just quietly sat at the feet of the man she was with. 

I had moved on to cock number four which was now in my mouth, only this time, I was shockingly aware that the red-head was watching me. The old me would have been super embarrassed and self-conscious but there was something about the setting, my attire and my sexpertise that actually had me showing off for her, for this random, naked female. I would look her way and arch my back just a little deeper, moan a little louder and allow my tits to flop about with the motion of being railed. 

I ended up being spit-roasted by two of the men, before this symphony of an evening reached the ultimate crescendo. I actually couldn't believe it was happening to me. All three of my holes were stuffed with hard dicks. I was so full and so turned on! "Red" continued to watch, occasionally smiling in my direction, as the man she arrived with fucked my asshole. 

Drool, slobber and cum were everywhere. This was such a hot mess but I was absolutely loving how degraded and abused I felt. All three of these stallions eventually came, but not at the same time. I'm pretty sure the gentleman underneath me came first, into my cunt, followed by a load for my throat from the second man and finally, a hot, squishy feeling, filled the inside my bum from the man behind me. 

I was spent. The men drained the last few droplets from their balls, onto my face and tits and I lay there panting. 

When I finally got to my feet on shaky legs and wobbly heels, I was permitted to go clean myself up and fix my smeared makeup and mascara runs. Bella was freed from her cage to begin sexually serving the guests and upon my return, I was gagged and bound and placed on display to wait to be used again. 

This was the moment that "Red" approached me for the first time. 

"I enjoyed watching you. You're very good at this." She said to me in her broken English. I think she was speaking in a German or Nordic-sounding accent. 

Then, without warning, she used her fingers to lasso a rope of drool that was hanging from my bottom lip, and glistened her pussy with it.

I was so embarrassed...

But that was probably the hottest fuckin' move I have EVER seen a woman do! I wanted to go down on her so badly, this mysterious European vixen. 

As she towered over me in her heels, in that moment, I actually didn't know if she was a top or a bottom. She had the confidence and control reminiscent of Mistress Andrea in that very moment.  

What she said next cleared this up for me, but boy was I ever confused as to what was going on. She leaned right in and whispered into my ear, scanning the room to ensure no one else would hear her. 

"Bid on me tonight...I'm begging you! Please help me!

Then she hastily clicked away from me in a clandestine manner. 

What in the actual fuck...was going on?!

Sarah Jane 

xoxo

Continued in: Paint the Town Red

  

 

Like Crazy

Continued from: The Fourth Guest

Last night I hosted a kink party in the Upper Floor space at my Facility. It was not only a chance for Sarah Jane to make her sex slave debut (or so she thought), but also an opportunity to treat Russell to an early release from the torment of his Locktober. 

Yes, he got let out early on good behaviour. Additionally, I felt bad for him having to endure the month-long added torment of having to deal with the cuteness overload of Summer, and the abrasive fury of Cassandra. 

He didn't realize however, until last night, that this was all an elaborate masquerade, planned and executed by yours truly. 😈

For the first time ever, Russell has graciously offered to write this post. He is far more of a hopeless romantic than I am...and I'm a little too choked-up to type right now. So...without further adieu, take it away Russ...

**********************

Good day everyone. From what I understand I guess I have been a "regular", in Mistress Andrea's blog for a bit? This is both humbling and a bit embarrassing, especially now that I realize that I've been duped, for the entire month of October. Not duped in a bad way. Duped by the creatively devious mind of Mistress Andrea and her two minions. 

To Summer,

I know that you were not my keyholder for this Locktober experience but it was a pleasure serving you.

I can't say that I have ever met someone who can run the full spectrum from absolutely adorable and "little", to the confident feminine strides of your Flight Attendant attire. You're so delightfully cute that I want a miniature version of you to hang from my rear-view mirror!

I took great pleasure in getting to know you better this past month, despite your tormenting approach to things. Take good care of Andrea for me, as I know you will. She is very special to me and from what I've seen, you two are perfect for each other. 

I know you were just playing your role, when you told me to take this photo of you for my "spank bank". 

Kinda difficult to indulge when my penis was locked in a cage, don't you think? Oh, and it tickled when you began massaging my cock cage with your furry socks. You're cruel! In the best possible way, but I no longer need to keep this photo. 

Take care Summer. Until we meet again...

To Cassandra, 

It's a relief to know that with you around, The Facility will never be short on crazy! Haha. 

You just keep being you, regardless of what anyone thinks. You are mature beyond your years and even though your personal mantra is, "I hate every guy I meet", there's someone out there for you. Just try not to break them on the first date, ok? 

Thank you...I think, for your involvement in my chastity sentence. I know you were not my keyholder.

Keep an eye on Mistress Andrea for me. As much as you need her and her strict lap, for your own therapeutic needs, she needs you too. You've become her enforcer, her safety blanket and her second in command. It's a good role for you. 

If I'm ever feeling like I need to pay dearly or suffer, just for being male, I'll look you up, but for now, I'm good!

To my dearest Andrea, 

I knew what I had to do last night, I just didn't know if I'd have the strength to do it...To finally say goodbye to you. 

Long ago, you and I both agreed that the tough thing about following your heart, is that sometimes it takes you places you shouldn't be. Places that are as scary as they are exciting, and as dangerous as they are alluring. 

And sometimes, your heart takes you places that may never lead to a happy ending...

********************

Last night, after throwing on a suit and preparing to head to the Upper Floor party, I was intercepted by Mistress Andrea on the way there. She told me that I had done well during Locktober and that she felt a little bad that she used Summer and Cassie as weapons, to make my denied state even more excruciating.

I 100% believed that Andrea was my keyholder all along, until, to my surprise, she told me she was not.

"Your true keyholder is waiting for you in my room. You're free, Russell." She seductively cooed to me. 

I was sensing some symbolism behind all of this, or subliminal messages in her choice of words. It all made sense when we both made our way to Andrea's bedroom, where I found Sarah Jane bound to the bed, gagged and blindfolded. 

Initially I was puzzled, until I moved closer and saw what was around her neck. Ahhh. Now I get it...

Very clever Andrea, well done!

Andrea stayed silent, gesturing with her hand around her own neck and her other hand motioning to rip the necklace off. Then she nodded her head toward the bound and helpless Sarah.

Sarah gasped when I grabbed her by the neck, then I grabbed the thin chain that contained the key to my chastity device. I stripped it right off her in one fluid motion, breaking the chain in the process. 

Mistress smiled and nodded at me. It was her implied consent to go ahead and unlock myself. I undid my belt, my zipper and accessed the rigid, metal device. For the first time in almost a month, my cock was bare and free.

I realized this was not only a surprise for me but it would be a special moment for Sarah Jane as well. Apparently she assumed she was going to be serving in the Upper Floor as a sex slave tonight and that some random "client" was about to savagely ravage her. 

I'll do the honours, thank you very much! 

I grabbed a rose and moved in. 

Goosebumps consumed Sarah's entire body, as I ran the soft petals of the rose, up her tummy and onto her breasts. I circled the flesh of the petals around her nipples, back down her stomach and across her pussy. The rise and fall of her chest intensified, before I finally removed her blindfold. 

DAAAAAAADDDDDDYYYYY!!

She squealed out through her gag, as I watched her eyes, once filled with lust and desperation, begin to fill with tears. 

I got her quickly un-bound and got the gag out of her mouth. The little snuggle-bug jumped into my arms and just squeezed me, gently sobbing tears of complete joy. 

Mistress, who was witness to all of this, began to speak very softly, in her best "Mommy" tone.  

"Sarah huni...You have the choice of coming with me, to the Upper Floor, where you can continue your journey as a sex slave of this Facility. 

Or...

"You can stay here with Russell, and be HIS!"

Sarah didn't even hesitate. She kissed my lips and had the biggest smile on her face. 

"Daddy I love you! I wanna stay with you, Daddy!" 

I looked over at Andrea and caught her dabbing a tissue against her eyes. I knew it was time to let her go. I knew in my heart, that what was most important to me was right in front of me, in my arms actually! 

"I love you. I love you like crazy, little one" I told Sarah for the first time. 

Andrea just smiled at the pair of us, and clicked out of the room. 

I cradled Sarah in my arms and gently dropped her onto the bed. We giggled and kissed and tangled into each other until Sarah finally spoke.

"Daddy...can you tie me up again and take me? I'm all YOURS!" 

Russell

xoxo

Continued in: Minute Man

 

  

  

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

No Turning Back

Continued from: The Wedding Party

The wedding of Summer and I was going to be a small gathering, as we wanted it. We selected a hipster, brew-pub downtown that had an intimate, rooftop veranda. 

Cute huh? 

When the wedding music started, I had a huge lump in my throat. We decided that I would be the one to wait at the front, under the arbor while pilots, Lance and Eric, in their official dress uniforms, walked Summer down the aisle to me (I still don't know which one is Lance and which one is Eric).

As soon as I saw my little Summer, in her wedding gown, framed perfectly by the two studs on either side of her, tears were rolling down my cheeks. There was no turning back now!

After exchanging our vows, we sealed the deal with a kiss, to the thunderous applause of our guests. 

I was so utterly content. My heart was finally full, and would now be forever. 

I played Summer a classic, from one of our most intimate slow-dances ever, the night in New Orleans where I told her I was madly in love with her.  

"I can't help falling in love with you." Elvis originally, I believe. 

She sat beside me on the piano stool and laid her head against my shoulder, crying tears of joy as I played. It was a beautiful moment on such a beautiful day, but the day was still young. 

All of the guests either knew or were briefed, on why every member of my side of the wedding party were in slave collars. Our tight group of friends are very open and understanding, it turns out the pilots and Vanessa were too. No one would ever judge our lifestyle choices.  

The reception was planned at the Facility, a.k.a. our matrimonial home, in the upper floor of course. We hired a caterer, Cassandra was going to dance for us again and given the environment, the guests were aware that "things" from the kink world, may happen. 

Summer and I could both sense that some wild adventures may occur tonight, we both noticed it from our seat at the piano. 

The booze was flowing liberally and people were starting to get a little handsy. 

"Do you think the sissies are crushing on the pilots?" I asked Summer. 

"It could be the other way around Mistress", she replied? 

"REALLY?!" I declared, sounding absolutely shocked. 

"Oh ya", Summer said. 

"Eric is for sure bisexual and Lance, he's just a huge swordsman. It wouldn't surprise me if they tried. They know Vanessa and I won't touch the two of them, even though they've attempted multiple times on our flights and I assume Bella is probably not permitted to." Summer went on to explain. 

"Only two options left", I said, in a cheerful tone. 

"Two options who have been in chastity cages for months right?" Summer quipped. 

We both giggled, and agreed to do our hardest to try and make it happen, without pushing or breaking anyone's limits. 

"Once they let two men fuck them, there will be no turning back," I concluded. 

It turns out, this one is Lance, the swordsman, who happens to have a thing for redheads. 

Hehe! 

To be continued...

Mistress Andrea

xoxo

Continued in: Bridesmaids

 

Hall Pass

Continued from: House Warming

The party was going smashingly if I do say so myself. Cassandra's dancing was so beautiful and sexual, everyone literally stopped everything else they were doing, just to come over and watch her.

She'd do a three-song set up on the pole, then come down to mix some drinks and tease the guests and tantalize my fiancée, Summer. 

Summer however, had started to take a liking to Nancy, which doesn't surprise me. Summer gravitates toward more mature women and caring Mommy-figures. Nancy is older than I am, so again, I wasn't surprised to see Summer flirting with her and sitting on her lap occasionally. 

During Nancy's Sunday school session, Summer got to see her dressed up like a schoolgirl and spanked on the bare bum. This could also have something to do with the way Summer was now lusting for her. 

After a bit more champagne and some looser inhibitions, Summer sweetly took my hand and whispered to me, asking me if it was ok to have sex with Nancy. 

"Of course Babygirl, hall pass remember, but I think Nancy is straight." I replied to her. 

"So's spaghetti, until it gets wet", she blurted out. 

I think she totally just stole my line. I think I've used that exact line before. I laughed, then gave her a judgey-face. 

"Thank you Mistress, you're the best", she said as she kissed me on the cheek and skipped off to find Nancy. 

Summer doesn't fool around when she wants something. I heard her from across the room, walk right up to Nancy and say, 

"Excuse me Nancy, would it be ok if I went down on you?" 

I saw Nancy smile and nod her head. Summer took her by the hand and led her over to the VIP couch. 

Just then, Tiffany clicked back into the room in his high heels. I guess Kaylee drew the short straw on this one. The next time Cole goes for a pee, he can get his dick sucked if he wants. 

Gawd, how humiliating is this?? But such a good gurl!

Kaylee would have knelt down and flipped the light switch to his left. Now he has to just wait, for a little treat to pop through that hole. 

It wasn't lost on Cole, as he was washing his hands, that the red light above him was on.  

What's the harm? He thought to himself. Katrina unlocked Cole's penis before this party, just for a moment like this. I guess he had a hall pass tonight too.  

Speaking of which, Summer had Nancy peeled out of a few layers and was just goin' to town on her. 

Down the hall in the urinals, Cole took the plunge and guided his dick through the glory hole, which Kaylee reluctantly took deeply into his mouth. 

According to what Kaylee told me the next morning over coffee, Cole must have been a little pent-up from the chastity device. I guess the load of ejaculate that Kaylee had to swallow was enormous. 

Nancy had cum once already too. I knew this because I was in the same room watching my little Summer in action. I think she was going in for seconds. 

Summer would lick and kiss her pussy for a bit, then crawl up on Nancy's lap to straddle her and kiss her mouth, transferring her pussy flavour onto her lips. Then she'd once again kneel, and get back to work on her hot, puffy, clit. 

I can't speak for the two sissies, but everyone else seemed to be having a great time! Haha...

As the party was wrapping up, Cassie and Summer had enough booze in them that they fucked-off somewhere. I can only imagine what they're getting into.

I treated the remaining guests and one sissy, to some lovely piano. Mahler. Piano quartet in A minor. Although I was missing three pieces to the quartet. 

It still sounded lovely nevertheless. 

Cole was ordering up an Uber on his phone, and from what I heard later, made another trip to the gloryhole before he left. Poor Kaylee.

Competing with the sound of my piano playing, was my future matrimonial bed, thumping against the wall from the other room!

Aren't hall passes fun? 

Mistress Andrea

xoxo

Continued in: The Maid of Honour