Mistress Pops Slut's Anal Cherry!

Last night, I took something from a sissy that nobody else will ever be able to take - his anal virginity.

He had called Me to confess that he was new into the sissy world and had only be dressing up for a few weeks. When his girlfriend was out, he liked to slip into her stockings and lingerie and parade around the room as he admired himself. He admitted that this turned him on so much and made him feel like such a slut, and now he was ready to be treated like one.

"So, have you ever had anything inside your slut pussy?" I asked to which he admitted he was a virgin in that department, but very eager to try. Of course I couldn't resist - it should be Me that gives him his first anal experience, and I tingled at the thought of doing so.

Having made sure he had plenty of lube with him, I instructed him to get comfortable on the bed, remove his slutty panties, spread his legs and get himself ready. "I want you to lube yourself up very well," I told him. "You can never have too much lube."

He did as he was told, lubing up his middle finger in the process as I told him the importance of being relaxed. "If you're tense, this will hurt," I said. "And we don't want it to hurt. Not for your first experience. We want it to feel good for you."

He took some deep breaths and informed Me that he was ready to begin. As I instructed him to slide his lubed finger down to the valley between his buttocks I heard a shivered gasp from him. "I'm shaking Mistress," he breathed. "And my little sissy cock is dripping." This was exactly what I wanted. The more excited he was, the more he was going to enjoy this.

"Now," I began. "I want you to circle the tip of your finger of the ring of your pussy," and he did so, panting in excitement as he felt the new sensations of stroking his anus for the very first time.

"Are you opening up for Me?" I asked and he gasped his response. "Yes Mistress!" he replied and I knew he was ready. "Slide in the tip of your finger," I purred and he obeyed, slowly and gently sliding in just a centimetre of his finger. "Oh god!" he gasped. "I can't believe I'm finally fingering myself Mistress!"

"Don't get over excited yet!" I giggled. "We've only just begun! Now try sliding in a little more." Before long he was up to the first knuckle of his finger, as his gasps became moans of pleasure. "It feels so good Mistress," he moaned. "I'm fingering myself for you and it feels so good." He was ready for more so I instructed him to slowly push the rest of his finger inside. He told Me how his sissy cock was twitching wildly as more of his finger slipped inside that tight little hole.

"Now start to gently work that finger back and forth," I instructed and he gave another shivered gasp as he did as he was told. "This is like a dream!" he breathed. "I'm finally fingering myself. Oh god, I'm so turned on!"

"Just think," I slowly purred to him, "before long, you'll be taking another finger as we get you ready for more. Then you'll be taking a small plug. You'll be pushing it up there until your arse-hole closes around the narrow part."

"Oh god, yes Mistress!" was his panting response.

"And then," I continued, "we'll move on to a bigger plug, which will stretch you. I'll have you wear that for longer and longer periods of time. And you know what will happen after that, don't you slut?"

"What Mistress?!" he gasped, clearly now on the very edge of climax.

"You'll be ready to take My strap on," I whispered teasingly. "You'll be ready to spread your cheeks, show Me your sissy pussy for Me to fill with all 9 inches of My strap on cock. You'll be ready for Mistress to fuck you!"

This was just enough to tip him over the edge, and without even touching his sissy cock, he came hard, almost screaming in pleasure as he fingered himself faster and harder. "I'm coming!" he moaned, "I'm coming for you Mistress!" and while I listen to him in the throes of pleasure I smiled to Myself, knowing that through My instruction, I had taken his anal cherry and made him Mine. Never again would anybody have that pleasure - because I had taken it. I couldn't help but feel a sense of pride in doing that. I've only spoken to a handful of anal virgins in My time, and most have chickened out before we got to the crunch. This slave was different - he was ready and he wanted it, and boy did he get it!

Once he'd come back down and started to regulate his breathing he thanked Me over and over, his gratitude as great as the pleasure he'd just experienced. "I can't thank you enough Mistress," he said, and I could tell he was grinning like a Cheshire cat, "I can't believe it! I came with my finger up my arse!"

"Well believe it," I replied. "Because next time it will be two!" He gave a shivered sigh at that, the thought of it stirring in his groin. After thanking Me again, we said our goodbyes and he hung up, leaving Me with a very satisfied smile on My face. Yes, it had been a wonderful experience and as My heart swelled with pride I knew this had been a rare treat for Me.

Mistress Cristal - the taker of anal innocence!

A Voice From The Past!

It's funny how life is sometimes, isn't it?

Back in the day, when I was doing dispatch phone sex, I had a very loyal regular slave, who could take a lot of pain and humiliation. He used to call Me every single week without fail and he was always a pleasure to talk to. When I decided to leave dispatch phone work and branch out on My own, I always thought I would miss him, and for a time I did, until My Domme business took over.

So I was both surprised and thrilled to hear his voice in the phone last night! Yes, My favourite old regular had found Me! Of course I didn't let on who I was. Back then I was a totally different persona, and I get the feeling it would have shattered his fantasy bubble if I'd have explained who he was talking to. But nevertheless, before he'd even said his name, I KNEW it was him and I couldn't have been happier.

Now it's a good 7 or 8 years since I last spoke with him - that's how much of an impression he had left on Me. But after doing a few interview questions to work out if he'd moved on in his kinks, I decided to get all nostalgic and we were back to him suffering for My amusement. By the time I'd finished, his cock was bright red and sore from all the slapping and his balls were aching from the way I'd demanded he squeeze them. I could tell he was very much enjoying himself and to Me, it was heaven - hearing him moan in agony like he had so many times before.

Next up was his dildo - smaller than I would have liked (he'll be getting a bigger one in a few weeks - I intend to make sure of that!) and he was sucking and gagging on it like a good little whore before shoving it up his ass and riding it hard.

"Moan like a girl slut!" I demanded and he quickly obliged, giving high-pitched squeaks as his dildo drilled into him. When I finally did let him cum, I remembered how much he hated licking up his mess. He always struggled with that one, and I always enjoyed listening to him struggle. But who am I to resist? "You will be licking up your filth!" I ordered and off he went, lapping up the white muck in his hand, gagging in the process and telling Me how humiliated he felt. Oh it was wonderful!

Of course, it's not a case of picking up where we left off with him. Like I said; 8 years have passed since we last spoke and he doesn't know he's talking to his old Phone Mistress. So it's back to basics for him, starting from the very beginning as he proves himself worthy of moving along in his training. Before long, he'll have tasks to complete between our sessions - something he always enjoyed doing. Perhaps it may well twig with him that it's Me. But I'll leave that for him to work out. Either way, he was very happy at the end of our chat; happy, humiliated but somewhat satisfied - as he always was.