He was now seated and I had to get on my hands and knees to suck him off. As I got to work again I felt a similar sensation in my rear, "Oooh what a tight little sissy hole we have here. I'm gonna have to really work it for the plug to fit in." I couldn't believe she just said plug. I knew it was on the list but I didn't think I'd have to wear it already. As she kept fingering my ass I continued to suck on this man's cock. This man whose name I did not know and had only met moments ago. I really was a slut.
"Okay baby girl, here it comes, just relax and it'll go in nice and easy." Gina cooed as she slid the plug inside me, slowly at first. I let out a big moan with a cock still in my mouth. It still wasn't all the way in. I didn't know if I could take it.
"Oh fuck I'm gonna cum, you better catch it all you little slut!" the man commanded. I didn't have to swallow Daryl's load earlier, but I knew I'd have to swallow this one. I started jerking his cock as fast as I could, and while Gina popped that plug in my tight asshole, I shoved his member deep down my throat as he shot thick globs of cum into my mouth. "Oh fuck yeah that's a good sissy slut!"
I swallowed it as soon as I could, but I couldn't help but cough afterwards. Gina giggled. As I looked up at the man he seemed pleased. "Oh I think you'll do just fine for Daryl. Now that you've swallowed my load, you may call Pete. Well for you it's Master Pete, or really just master or sir will do fine. Anyways, Gina will get you all sorted out and I assume you'll do well enough for Daryl tonight that Gina here or one of the other girls will see you back her on Saturday. Now if you'll excuse me, I need to go call your Daddy little girl."
As Pete left I coughed a few more times and Gina helped me to my feet. She started saying, "I'm so excited for you! I bet you're nervous huh? And scared? Oh sweetie don't worry you'll do great! Now here, I picked out some new undies for you, here's tonight's pair," she handed me a pair of pink panties with a little bow on the front. "Daryl like his new girls to wear pink at first, he finds it helps them feel less like a man. And this bag has more naughty things for you like that little plug that's in your boi pussy!" she giggled again. More naughty things? Did she mean the dildo? I hope there's not more than that.
"You don't need to worry about paying for anything right now, your daddy will take care of everything! You just focus on being a good little sissy tonight! Do you have any questions?" Gina asked, very sincerely.
I was so dumbfounded by this whole situation, I wanted to ask her how I got here, how she got here, was this going to be my life now? All I could muster was, "Will it hurt?"
"Only at first baby, but soon you'll be begging him to fuck you harder. In fact even if it still hurts, you should beg. They really like it when you beg." She said with a wink
"Umm, will I need um....other clothes? Like girly clothes?" I asked, standing there naked, holding a pair of pink panties.
"Oh no not tonight! He's gonna want the full experience of breaking you tonight. But I love that you're already thinking of that! No don't worry, on Saturday Myself or one of the other girls will take you shopping for some cute new clothes, and of course a lot of slutty clothes. We'd get fired or something if we didn't get you looking like a proper slut for Daryl, that's usually how he likes them." Gina assured me. It sounds funny but when she said it all I found it very comforting, even thought this whole situation was bat shit crazy.
"Um, can it be you on Saturday?" I asked sheepishly.
"Aw, you got a crush on me or something? Sure thing sweetie, if that'll help ease you. But if you're not a good girl tonight you won't get to see me. So why don't you let that motivate you tonight," she said with a wink "Of course you may regret that decision, we won't just be shopping Saturday, and you haven't seen my bossy side" she giggled. I felt myself getting hard at the thought of her bossing me around. And she noticed, after all I was naked. "Now now missy, don't get too excited, you have a big night ahead of you," As she said this she took the panties from my hand and bent down and started lifting my leg to put them on me. She slid them up my legs as she said, "Now you go home and be a good girl and let your daddy fuck you like a cheap whore," she slid them over my cock and my plugged ass as she whispered in my ear, "And then I promise I'll fuck you myself on Saturday." And then she slapped me hard on the ass. I yelped and she giggled once more.
"Bye Sissy!"