Our First Couples Experience

I can’t provide video or photo content of this experience to protect the other couple, but I still wanted to share this as it was transformational in my slave’s journey of becoming a real sissy girl. This experience is true, and I will share it to the best of my recollection.

To give you an idea of how the day went... let's just say dinner required formal wear followed by a fashion show! Hehe

I decided to take Sissy’s progression to the next level and got together with another mistress and sissy (husband/wife) couple who share our values. We created a time and space for our sissies to get together and comfortably be sissy girls together. Jack and I got to know the couple through some cocktails and laughs initially. Mistress Victoria and I thought the best way to allow our sissies to discover that next level of sissy self would be to allow them to explore each other with their mouths… while blindfolded.

Both our sissies were at the point where they needed to learn to be proper sissy girls… what better way than together, turning fantasy into real life.

As we mistresses sat in our thrones sipping our old fashions, we watched as our sissies began kissing and licking each other’s titties, slowly moving their mouths around down to their clitties, which are currently locked up in pussy cages.

As they took a break to sip their shirley temples, we allowed them to caress each other’s balls. They needed to know what it felt like to have that first taste of forbidden fruit, bringing out the true naughty of a sissy girl. The elation all over my sissy girl’s (Jack’s) face as she felt and tasted another sissy’s balls was the assurance this mistress needed that this experiment was going the direction I was hoping.

I began to feel wet and felt the need to touch myself, but as I placed my finger into my pussy, Mistress Victoria noticed, kissed my neck, and drug her tongue along my ear and whispered, “allow me.”

Our sissy girls noticed out of the corner of their eyes our touches, but before they could get distracted by us, we had them crawl over to us… we then unlocked their clitties and instructed them to lay on their sides in a 69 position on the floor at our feet and take each clitty into their mouths, pleasuring each other. I’ll admit seeing this in real life was a greater turn-on than I thought it would be.

My wetness only became more apparent as I got extremely turned on by my sissy girl sucking another sissy’s clitty. Mistress Victoria’s fingers were drenched in my love juices as I stared intently at my sissy’s clitty going in and out of the other sissy girl’s mouth. The mistress couldn’t take my wetness anymore and decided to take me in her mouth. As she got on her knees to pleasure my pussy with her tongue, I saw the excitement coming from my sissy girl’s face as she was edging with the other sissy’s (Sissy Candy’s) mouth. I couldn’t help how turned on I was and moaned in ecstasy as I came with the other mistress’s tongue inside me… at the same time, my sissy girl came in Sissy Candy’s mouth. Cum is a reward in our household, and a very important aspect to becoming a true sissy girl, so as the other sissy sat up with Jack’s cum in her mouth, Mistress Victoria and I looked at each other in agreement as she ordered them to kiss and share that cum, swallowing a little bit with each kiss. It was something magical!

I decided it was time for us all to come up for air, so I instructed both sissy girls to refill our old fashions… after all, that what sissy maids are for. After such an enjoyable cum, Mistress Victoria and I laughed at our naughtiness, noting how much fun it was to order our sissy girls to explore each other’s pathetic clitties.

Once our sissy maids handed us our drinks, we sat back in our thrones as they assumed their standard positions of being on all fours as our footstools facing each other as they awaited further instructions.

It was time for the ultimate sissy girl act… as we continued to sip our cocktails, our pretty girls were told to take off their panties. I wanted Jack to finally feel the tightness of having real cock in her pussy. I had been holding back on this for quite some time, as I wanted my sissy to become a true sissy slut under my supervision. Once we met this other mistress sissy couple, I knew this was the perfect time.

I took my sissy girl’s chin in my hand, looking deep into her eyes, and whispered “go fuck that cock, sissy girl.” My sissy knew exactly what to do as we have spent years practicing with Mistress’s cock. Her ass rose in the air, still on the floor in front of our thrones, facing sideways in front of us while begrudgingly looking at herself in the mirror I had placed earlier. Sissy Candy, hard from watching my sissy’s ass rise into the air, slathered her clitty with lube looking to her mistress for approval. Mistress Victoria smirked and nodded; my pretty girl gasped as that cock slid into her pussy. Jack looked forward into the mirror, seeing Sissy Candy staring back while mounting her ass and blew her a kiss. I couldn’t help but feel proud as a mistress but could tell my pretty girl was a bit hesitate. As Jack’s mistress, I knew just what she needed… I bent over, drink in one hand giving my sissy girl a good spanking with the other hand and stated calmly but firmly “watch yourself graduate into a real sissy girl.”

My sissy nodded in acknowledgement, saying “yes Mistress” and continued to look forward into the mirror as she felt her ass being pounded with every thrust. Mistress Victoria seemed to be extra turned on by my demand and took it upon herself to suck on my tits while her fingers slipped back into my pussy. I tilted my head back for a few minutes, enjoying the sensation from the other mistress to the sounds of my sissy girl’s moans and balls slapping. I was so in the moment I didn’t realize until it was too late that Mistress Victoria had put her strap-on on and slipped it into my pussy. I opened my eyes, looked into her eyes and wrapped my lips around hers until I came on her cock. As my cum dripped, I glanced over her shoulder to find my sissy stroking her clitty. I firmly said, “no stroking that worthless clitty without Mistress’s permission.” While conceding and saying, “yes Mistress,” I could tell my sissy just needed more dick. I whispered to the other mistress “it’s time” … she pulled out of me, took a moment to lick up my juices, and then proceeded to walk over and face fuck my sissy. I sat back in my throne, enjoying the view of the spit-roast.

My sissy was finally getting what she deserved… cock in both holes, balls slapping against her own balls. I could see the connection the other couple shared as they winked at each other while taking my sissy together. It was oddly titillating for me to touch myself and watch, to see all my hard work of training my sissy girl finally coming to fruition.

Their cocks continued to thrust, in and out, back and forth. My sissy glanced over at me and asked the inevitable question, “Mistress, may I stroke my clitty?” I took a sip of my old fashion, calmly looked at the other sissy, and instructed her to give some lube to my girl. It didn’t take long for Jack to reach climax. Within a few minutes, she moaned out, “may I please cum, Mistress?!” I knelt, kissed my sissy’s cheek, and whispered “cum, my pretty girl.” As my slut finally became a true sissy girl, Sissy Candy was so turned on that her mistress allowed her to breed my sissy’s pussy.💦

Mistress Victoria had a final thrust in my girl’s throat and then both cocks slowly pulled out. I turned my sissy’s head toward me as she blushed in ecstasy with some embarrassment, and kissed her, reassuring her that I was a proud mistress. The other mistress took her sissy by the hand and instructed Jack to clean Sissy Candy’s clitty. Upon licking up and swallowing the last of the cum, they slowly got up from the floor, we took the last sips of our drinks and enjoyed a few more laughs… and it wasn’t even awkward. The other couple then thanked us for the fun time and left, leaving us with a pleasurable experience and a direction for our future.

An enormous thank you to Mistress Victoria and Sissy Slave Candy for a wonderful day. We look forward to tasting you again... this Mommy Mistress approves!

-Mistress Jill