Is it Gay?

Continued from: Home Sweet Home

So, what's the verdict here...is it gay? 

Your Dominatrix mashes a penis extender over your chastity cage then makes you fuck a dude with it. Does that absolve you from homosexuality? There's of course nothing wrong with homosexuality but these two men, in the clutches of Cassandra, do not identify as such. 

The idea itself is brilliantly creative, terribly humiliating and emasculating.

Both these guys have safewords they haven't used, so I guess it's game on. Summer and I settled into the couch to watch the performance. By the colour of one of their bums, the maid-sissy seems like he needed a little motivation to go through with this. 

Cassie began the scene by having the one male kneel, after the other was fitted with the hot pink, fake dick. She offered her kind words of support, by gently cooing and encouraging the man to "get him hard". 

I was embarrassed for them! Just watching this. 

Cassandra was relentless in her orders, now instructing the kneeling man to "take him into your mouth". Caressing his spanked bottom while he sucked that cock was a little gay, I must admit. Look at his hand placement! Ha 

"He's nice and hard for you, show him your pussy, baby. Let him take you like a girl," Cassie continued to coo. 

The man in the lingerie set got into a very slutty doggy-style pose, arching his back deeply and presenting his asshole. 

And in it went *plop*. The spanked maid was fucking this other guy, wearing a penis extension over his cock cage. Amazing! I love what denial and desperation does to these silly men. 

Holding the other man's hips to assist in pile-driving his asshole...that seems a little gay. But is it?! It's not his actual cock...no one will be ejaculating into anyone's bum here. This is still safe, partially sane, and consensual, heterosexual bdsm, no?

Jesus. He was really goin' to town on this poor guy. Maybe the cock-sleeve was providing some stimulus? Some sensation to his locked-up penis that felt good? Does that make it gayer? If maid-boi is feeling pleasure from this? Or if hands-and-knees boy is feeling pleasure from being fucked? 

Although this was awesome to watch and listen to, I had seen enough. I can only assume Cassie would make the giver become the receiver soon, so they both get to experience the two perspectives of whether or not this was gay. Still, no safewords were spoken by these two, as Summer and I excused ourselves from the show. 

We went out back to soak the travel off us for awhile. Conveniently, we still had a decent view of the show going on inside. Hmm, looks like Cassie did make them switch places. 

Riding the cock-sleeve, while holding each other's bras and looking into each other's eyes. Things are getting gayer in here...

"Cassandra, send the dark-haired one up to my room when you're done with him. Have the other one mop up this water mess we just made," I said to Cassie, who was continuing to orchestrate the scene before her.

Summer giggled at my authoritative commands. She knew I was up to something, probably for her benefit. We had just spent a romantic week in Paris and we didn't pack a strap-on, purposely. We focused on the tender romance of our mouths, tongues and touches, when we had sex together. It was beautiful and fantastic and I love her so much...but I could tell she needed some dick. 

Real dick? The dark-haired guy I asked Cassie to send upstairs? Hell NO!

His humiliation and emasculation can continue, this time with my gorgeous wife! I posed her on the bed as I heard this non-gay dude coming up the stairs.

She was looking irresistible as always.

 

Cassandra sent dark-hair boi upstairs, still wearing his lingerie and heels. Summer very bluntly asked if he would fuck her, while they both looked down at the penis extension he was shamefully wearing over his metal cock cage. Yes, we ARE that cruel!

Go ahead sissy! Fuck my beautiful wife while I watch. Hehe...

You're welcome Summer! 

Mistress Andrea

xoxo

Continued in: Uniformity

 

 

The Three Bears

Continued from: Shell Game

Locked-up, chastity boys tend to rediscover their tongues, when they can no longer use their dicks. 

How convenient for the three woman who all hold the key to Russell's obedience, through the month of Locktober! 

If you recall, between Summer, Cassandra and I, one of us has the real key to his cock cage, two of us have a placebo key. It must be extra frustrating for poor Russ, not knowing who his actual keyholder is. The girls were eager to begin using and abusing their newfound power over him. I wasn't shy, I did the honours first! 

I made Russell kneel and kiss my ass, then a lovely greeting to my asshole, while I was dressed in something I knew would be like kryptonite to his poor penis. 

Yep! That's the tongue of a chastity boy...

I greedily indulged myself in several orgasms, reminding him that I could be his REAL keyholder. 

"You better make love to my pussy with your mouth, pet, or Locktober will be the only month you ever know!" I teasingly threatened. 

"Maybe my ebony hairbrush will help motivate that tongue of yours, hmm..?" 

He did a good job. I petted his hair and cooed, "good boy," to him, as I enjoyed the sight of me glistening off his lips. 

Between Summer's yoga stunt outside and my oral indulgences, I think we had tortured Russell enough for one day. I bid him farewell with some instructions for tomorrow. 

"I think Summer wants to spend some time with you tomorrow, sweetie...maybe some more yoga?" I hissed to him in a devious chuckle. 

He can fall asleep tonight, unable to masturbate about the mental image of my wife, which I'm sure is burned into his mind:

And then there's that pesky morning boner. If only he could relieve the pressure, all over the small of Summer's back maybe? That lovely little void, just above the dimples on her back, where all that cum could pool and collect? 

I know, I know. I'm cruel...

But this is what these Locktober boys want! From my experience, chastity is a male-initiated fantasy for most couples and playmates who use cock cages. All I'm doing is making them pay for it! 

I think Russ was a little shocked to see Summer playing a "little" the next morning when he came to see her. I basically told the girls they could do whatever they want with Russell, during Locktober, provided it's all S.S.C. 

"Ummm, ahhh...Hi, I mean, good morning Miss Summer." 

"Oh Dadddddddy! You don't have to call me that." 

"I've missed you, Daddy!"

Summer purred to Russell in her baby voice, latching onto him like a true little, longing for her caregiver. 

She laid it on thick and I'm sure she had his poor cock throbbing in those metal bars. 

"Can you give me special Daddy kisses? It aches down there again, Daddy!"

"But I've been such a naughty girl Daddy, I think I need a spanking first!" 

She continued her relentless attack of cuteness, as poor Russell indulged in her taboo fetish. She slid across his knee like a snake, and hoisted her beautiful ass in the air, all while speaking to Russ in her baby voice. 

"Daddy...can I hold my stuffie while you spank me...in case it hurts..."

I think Summer has Daddy wrapped around her little finger!

He came to see me before he left for the day. 

"Did you spend some time with Summer?" I innocently asked, like I didn't know. 

"I did Mistress, thank you. She's....ummm, she's very soft." 

I chuckled and didn't respond to that. Instead, I told him to come back tomorrow as Cassie was interested in seeing him. 

Time to unleash Cassandra the wildcat! Poor Russ is in deep shit now! 

I could faintly hear like German death metal music, pounding from upstairs and the sounds of Cassandra occasionally screaming at Russell. 

Sheesh! The poor girl, she must have a lot to emotionally unpack...

I was laying in bed with Summer, we were minding our own business, when Cassie clicked into the room asking to borrow the bullwhip. She had a bit of a crazed look in her eyes. 

"Remember, Cassie...we use safewords in this house!" I called out to her.

I think she murmured something about hating men, under her breath as she left. Eeeek! I was starting to feel sorry for Russell. 

I must say, he was pretty vulnerable and sheepish when Cassie was done with him and he creeped into my office. He sat down a little...gingerly I would describe it as. Hehe.

"That little one, Mistress...She's too hard!" 

"Awww, my baby. Are you ok?" I cooed to Russell in my 'Mommy' voice. 

"Yes Ma'am, it's just...this Locktober thing, I thought it would be only YOU who..."

I shushed him with my fingertip against his lips and began to coo to him and make kissy-lips at him.

"Shhh...shhhh huni. Mommy will make it all better young man. We can go upstairs and you can get Mommy's slippers for me, hmm? The ones with the firm, rubber soles?" 

"Then you can go across Mommy's knee for a little while..."

"You can thank me with your tongue when it's all over...hmm? How does that sound, sweetie? 

"Mmmm, That sounds just right, Mommy." 

Mistress Andrea

xoxo

  

Shell Game

Continued from: Happy Locktober

I had a fun and devious idea for Russell, as he navigates the challenges of the month of Locktober. My idea was to simply make it more challenging. Ha! 

Instead of follow the pea, it was going to be...follow the key!

It wasn't until October 4th, yesterday, that I could get Cassandra over to the Facility, Summer home from work and to get Russell freed-up so he could report to my office. I think he was a little shocked when he saw all three of us waiting for him. 

His eyes lowered in our presence, looking at our feet and heels first. This is what Russell was conditioned to do in the presence of female dominance, so it took him a few moments before he noticed the keys. 

The internal brass locks of modern chastity devices have very distinctive keys. 

To the enlightened, those fortunate enough to play in the BDSM world, the key is unmistakably telling, when observed on a woman's necklace or anklet.  

Russ, now in the presence of three beautiful women and feeling very vulnerable, just noticed that each of us were wearing a chastity key. 

Without hesitation, I explained to him how his Locktober experience would unfold. 

"Russell honey..."

"One of us, is wearing the actual key to your chastity cage. Which means only one of us has the ability to unlock you at the end of the month." 

"Oh...ummm, yes Mistress Andrea."

"And as you are well aware young man, the 31st of October doesn't mean you instantly earn your release. Rather, the end of the month is a time to assess and reflect on your behaviour during the month and your devotion and service to your keyholder, correct? 

"Yes, Mistress Andrea." 

"But since you don't know which one of us is your actual keyholder, you should likely be on your best behaviour around all of us? 

Russell finally got it now. It took a minute for this predicament to sink in, before he truly absorbed his peril. He groaned out loud, as I began to escalated his torment.

"If Miss Summer needs her toes sucked on after a long day at work, your reply to her will be...?"

"Yes, Miss Summer." Russell replied to me while looking at her. 

"If Miss Cassandra tells you to strip bare and get across her knee, you will say...?"

"Yes, Miss Cassandra, right away, Ma'am." 

That one really had Russell blushing and humiliated. Cassie is like 20 years younger than him!  

"Good boy." I praised. 

"Now, I think Summer needed your help lifting something. Would you mind, young man?" 

"Of course, Mistress." 

This part was all scripted, I was holding back a giggle fit. Summer had since left my office to go change into her "yoga wear"...if you wanna call it that. Here's the actual Summer below: 

And she was waiting for Russell outside by the lawn.

"I thought you wanted me to lift something, Miss Summer?" Russell said to her in a puzzled but desperate manner. 

"I do," she replied in her most innocent tone, "my legs...help lift my legs. It's a yoga pose, silly." 

Haha! That's my little minion! Her arse and legs in those pants are just breathtaking. 

Poor Russell! 

The tip of his chastity cage in his pants was literally resting on Summer's sit-spots. 

That's it, my girl, spread those legs for Russell! He's probably just horrified with frustration right now, and it's only day 4!

😈

Things didn't get much better for him when the yoga was over and he came back inside. I had changed clothing too!

"Ooopsie. I dropped a pencil." 

Hehe. 

Mistress Andrea

xoxo

Continued in: The Three Bears

  

Happy Locktober

Continued from: She-Devil

Ladies, I hope all of you dug out the cages the other day, from whence you keep them. Nightside tables, playrooms or in the kitchen drawer where the garlic press is kept. Or better yet, it's already on your partner's cock and never comes off. Maybe for Locktober you swap out for a tiny, little nub cage to celebrate the month? 

As I eluded to in my previous post, I was planning on starting Locktober for poor Russell, one day earlier, on the newly coined "she-devil night".

Summer was away on a multi-leg flight on September 30th so the timing was perfect. She knew what I was planning on doing with Russ, on the eve of Locktober. She giggled and called me something in French that sounded like maleficent...maybe malfaisante?

Which I think means evil woman. Moi? Evil? 

*blush* nawwww...

When Russell and I used to travel quite a bit, back in the day, we would dress up real nice and explore the local food scenes in these cities. I think it was at a lovely steakhouse in Minneapolis called Murray's, when I produced his very first chastity cage from my purse and handed it to him right across the table. 

Amidst the dim glow of candles and bustle of a busy steakhouse, I told him to go to the gentleman's room and to lock the device on his penis, then return to me with the key. 

The waiter who brought our tableside Chateaubriand, definitely noticed the key that was now on my necklace, proudly displayed. Russell blushed cutely and squirmed in his seat throughout the entire meal. He wanted the hell outta there! I think I ordered dessert then a Spanish coffee on top of that, just to prolong his torment even further. 

Back at the hotel that night, was the first time I dropped the line, "what are you going to do, to earn this key?"

His tongue had me clawing at the bedsheets for hours! He definitely earned his freedom that night. I unlocked him and we fucked until exhaustion and alcohol put us to sleep.

This is what I planned for the night of the 30th, for she-devil night. I invited him for dinner and simply messaged him: "Let's pretend we're back at Murray's. Do you remember, Minnesota?"

Russ was a complete gentleman as always. Pulling out my chair, standing if I got up, gazing across the table into my eyes. We even danced at one point. It was easy to fall in love with him again. It's a shame that he'll have to endure my cruelty and the wrath of this she-devil.

Just like Minnesota, all those years ago, I gave him a spanking when we got back to the hotel room after dinner. A bare naked, firm spanking with my hand and purse-brush, while I remained in my stunning dress, stockings and heels. No hotel this time, my bedroom would have to do!

After Russell's trip across my lap, I restrained him to the bed and slowly began to edge his cock. I was torturing the hell out of him, reminding him that for the next month, he won't even be able to get erect. 

I reminded him that a month in chastity, is the price he has to pay for fucking me, which he was about to do again. I started by enjoying his tongue while he was still restrained, first into my bum hole while I used a wand, then he licked my pussy to a second orgasm as I continued to ride his face. 

Russell fucked me good and hard, for as long as he could hold out before desperately begging me to cum. 

I kept saying no, and denying him orgasm, because it felt so good to be taken by him again. Eventually he was at the breaking point, shaking and trembling in his attempts to fight off the imminent eruption. 

His last orgasm for at least a month. I allowed it...he exploded into my pussy. 

I cleaned myself off his dick, giving him one final act of the comfort of my mouth, before it's replaced by steel, metal bars.

He whimpered as we both watched his turgid manhood begin to list and wilt before our eyes. Soon it was flaccid enough for me to mash into a cage and quickly get it locked up.

*click*

Perfection! I went with a medium-sized metal for Russell. 

Since he just came, his head wasn't into any of this anymore. I sent him on his way. His torment would begin on the 1st of October, when I illicited the help of my minions. 

Russell was in for a BIG surprise!

Happy Locktober everyone! 

Mistress Andrea

xoxo

Continued in: Shell Game