The Daddy P.I. Casefiles: The First Collection

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The Daddy P.I. Casefiles: The First Collection Page 11

by Frost, E J


  “That’s my girl. Have you worn a plug before?”

  “No, Daddy.”

  Matthew wasn’t interested in anal play and I’ve made it a hard limit with my other Doms. Why, why, why didn’t I make it a hard limit with Logan?

  “Bend over the sink, pull up your skirt and pull down your panties.”

  I squeeze my eyes closed for a second, then I turn and do exactly as he’s said.

  He makes me stand bare-assed for a long minute, not saying anything, although I can hear his steady breathing. My sphincter keeps twitching, which I’m sure he can see. He can probably also see how wet I’m getting.

  “Sir,” I finally whimper. “I’m very, very sorry I disrespected you. It wasn’t intentional. It won’t happen again. I’ll be more focused.”

  “How will you stay focused, Emily?” he asks softly.

  Oh, God, I think that soft tone of his is worse than anything else. It feels like a lash across my brain.

  “I’ll remember this, sir. I’ll remember how angry you are. I don’t want you to be angry with me. I want to be your good girl.”

  “You are very responsive to praise,” he says. “But I think you might need a bit more to help you focus. Have you done any anal training, Emily?”

  My sphincter doesn’t just twitch, it locks up like a fist. “I haven’t done an enema or anything. I’m not prepared.”

  “You won’t need one tonight. I’ll always tell you if you need to do something to prepare.”

  I hear him move, a soft shifting of fabric, that tailored suit he’s wearing that makes him look like a million bucks, so much classier than Rick in his pimp suit. Then I hear the tear of foil. Is that a condom? Is he going to fuck me? I thought he said he wanted privacy for our first time together. I don’t want it to be in a bathroom. And I really, really don’t want our first time to be in my ass.

  But what touches me through the latex isn’t his cock, it’s a fingertip. The condom’s lubricated, and he works the slickness over and over my sphincter with the pad of his finger. I don’t know when I start whimpering, only that by the time he presses his finger into me, I’m making lost, helpless noises and gripping the edges of the sink.

  “What experience have you had with this, Emily?” he asks, and his voice isn’t soft anymore. It’s rough and hot.

  “I tried anal sex twice with my ex-husband.” I gulp at the memory. It didn’t go well. We were both drunk each time: Ash because he wouldn’t push me for anal unless he’d been out drinking with the guys, me because I wouldn’t agree to it without a lot of liquid courage. The first time, he didn’t get it in and we gave up and just had regular sex. The second time he was more determined. He rammed it in and my rectum prolapsed as he pulled back. After a half-hour of sobbing and bleeding on the bathroom floor, I finally managed to stuff it back inside. That’s not an experience I want to repeat. “One of my Doms used anal beads.”

  “Did you like the love beads?”

  “Yes.” I did, despite my trepidation, and Ben praised me for weeks for overcoming my fears. Then he got himself a younger, blonder model, presumably without my hang-ups.

  “We’re going to do anal training, Emily. I think it will keep you very focused.”

  Oh, God, isn’t there a better way to keep me focused? I shake my head, dropping it to hang between my shoulders as I brace against the sink.

  “We’re going to start with thirty minutes tonight,” he continues. “I’ll check in with you every five minutes. If you feel like you’re going to lose control of your bowels, you have permission to immediately go to the bathroom. I’ll follow and help you as soon as I see you go. You don’t need to wait. Do you understand?”

  “Yes, sir.” But I don’t. Are we going to walk around for a half an hour with his finger up my ass? If so, he’ll be the first one to know if I lose control of my bowels.

  “Good girl. I feel you getting very tense with my finger in you. I want you to brace your forearms against the backsplash and try to loosen-up your shoulders. Focus on your neck and shoulders and getting each muscle to relax. Can you do that for me?”

  “I’ll try, sir.” There’s a wide, white lip of tile at the back of the sink. I cross my arms on the lip and rest my forehead on them. Leaning forward and taking the weight off my shoulders is actually a much better position, and I feel some of the strain drain out of my back.

  “Better?” Logan asks, beginning to move his finger in and out.

  “Yes, sir.” It’s a little strangled, but talking normally when you have a huge man digit in your ass is a challenge.

  “Good girl. I’m going to take my finger out now and put a plug in. When you feel the plug press against your sphincter, I want you to bear down and then relax.”

  Fuck, no. Oh, fuck, no. He’s going to plug me. I’ve seen women plugged. I’ve been to parties with those crazy pony-girls trotting around with a tail plug in, shaking their asses so their silky tails swish everywhere. I’ve also seen their butts when the plug is taken out. You could drive a bulldozer up there. I really, really do not want that to be me.

  “Please, sir, please, no. I don’t want to wear a plug. I’ll be very focused. I promise, sir. I promise.” I sob the last few words.

  “Why don’t you want to wear a plug?” he asks, as he draws his finger out, and I sob with relief.

  “I had a prolapse once. With my ex. It was painful and really horrible. I don’t want that to happen again. Please, Logan, please. I’m really scared.”

  “Did he prepare you for the anal penetration?” he asks.

  I can hear him doing something behind me. I don’t know what he’s doing but it sounds like he’s getting ready to shove the plug in me. Fuck, fuck! I grab at the lip of the backsplash as my shoulders start to shake.

  “Emily.” He puts his hand on my back, presses so I feel the warmth of his palm. “Calm down. Take a deep breath, hold it in for a count of two, and then let it out slowly.”

  “I-I—“

  “Emily, follow my instruction. Deep breath. Hold it, one, two, then let it out slowly.”

  I do, counting to two as I hold it, and five as I let it out.

  “Another,” he says.

  Breathe in. One, two. Out. One, two, three, four, five.

  He strokes my back. “Again.”

  As I let it out, I feel something wet push between my cheeks.

  “No! No! Oh, God, Logan, please no!”

  “That’s just my finger, Emily. You’ve already had it in you. Breathe, baby.”

  He presses his finger against my sphincter and holds it there while I breathe.

  “Sir, I can’t do this,” I say, after a dozen breaths.

  “Do you need to use your safe word?”

  I don’t want to. Not on our first date. “I d-don’t think I can do this.”

  “I believe you can, if you trust me. Let’s go back to your prolapse. Were you prepared for the anal penetration?”

  “No, sir.”

  “How big was your ex’s dick?”

  Not nearly as big as Logan’s. I hold up my hand and curl my forefinger against the knuckle of my thumb to illustrate Ashley’s girth. “It hurt like, like heck. Honestly, I can’t do this.”

  “This is not going to hurt. Turn your head to the left and open your eyes.”

  How does he know I’ve squeezed my eyes shut? I follow his command and look over my shoulder.

  Logan slides his hand from between my shoulders, picks up something he’s left lying on the small of my back, and holds it out so I can see it. It’s a purple butt plug, very short and slim. Maybe two inches long and an inch wide. Logan turns it so I can see the little purple gem on the hilt.

  “One of the reasons I had to get back yesterday was so I could buy fresh toys for you. This is Morris. Morris is not going to hurt you.”

  “M-Morris?”

  He named the purple butt plug Morris?

  “Coach Morris was my high school football coach. He taught me a lot about being focused. W
hen we screwed up, he used to dump buckets of ice over our heads. I’m not going to do that to you, but I think a little time with Morris every day will help keep you focused. Coach Morris also turned purple when he yelled, so it fits.”

  I laugh, although it’s still tearful.

  “I’m going to put a condom on Morris now and introduce him. It’s not going to hurt, baby doll. This is a small plug. At the very worst, it will burn a little. That’s absolutely normal. But you might not even feel that. I promise, sweetie. I’ve trained a dozen subs. I’ve had anal sex . . . well, many times. I’ve never once made a woman prolapse, or even tear. I’m sure you already know this, since you divorced him, but your ex was a careless fuckwad.”

  “Yes, I did know that.” I take another deep breath, hold it and let it out slowly. “I’ll try, sir. I’ll try for you.”

  “Good girl.” He strokes his hand down my back. “Breathe again for me and when you feel Morris press in, bear down.”

  “Yes, sir.” I take a deep breath, hold it, and as I’m letting it out, the cool, slick tip of the plug presses against my sphincter. I begin to shake, and as hard as I try to relax my shoulders, the shaking spreads down my back, through my legs. I squeeze my thighs together to control the shaking, but nothing helps. I’m shaking all over like I’ve got palsy and he hasn’t even put the plug in me, yet.

  “Emily, bear down for me.”

  I sob with fear and humiliation and discomfort, but do as he commands and bear down.

  “Good girl. That’s excellent, Emily. Now let go.”

  As soon as I release, he slides the plug into me. There’s a little burn and a heavy, full sensation when he pulls back on the plug, but it goes in even more easily than his finger. Then he covers my ass with his palm and just holds it there.

  I gulp down my tears. “Is it in?”

  “Yes, Emily. That’s a good girl. Stay calm and relaxed. How does it feel?”

  Like I have the world’s worst constipation, in all honesty, but I don’t think that’s what he wants to hear. “It burns a little.”

  “That’s normal. Your thirty minutes starts now.” I hear something click and he moves around behind me. The toilet flushes. “Can you walk with it in?”

  He wants to me walk around while I have this thing up my butt? “Can’t I just wait in here?”

  “No. Moving with the plug in is part of the training.” He reaches down and draws my panties back up my legs. His warm fingers expertly settle the band back into place around my hips, and I wish he’d leave his hands there, but he smoothes down my skirt and the tail of my blazer instead. “Try standing up, sweetheart. I’m right here behind you. You’re not going to fall.”

  “Yes, sir.” I push up with my hands against the tile lip, but my arms shake too hard. I can’t push myself up.

  Logan’s big hands smooth down my arms. His weight settles against my back. He wraps his hands around my forearms and gathers me in, hugging my back against his front. Then he straightens, pulling me upright with him.

  “I’ve got you,” he whispers to me.

  “Thank you, Daddy.” I close my eyes and melt back against him, using the strength of his big body to brace my wobbly knees, my strained back and shaking shoulders. He wraps his arms around me and holds me tight to his chest.

  “How does it feel when you’re standing up?” he asks, his breath warm against my temple.

  “Like there’s a thing in my butt,” I say truthfully.

  He chuckles. “Fair enough. Is it hurting?”

  Not really, but I’d like it out. “How long has it been so far?”

  Logan holds up his right wrist so I can see the fancy diver’s watch on his wrist. The blue metal face has a dial with hands, but there’s also a digital inset with a timer that’s running. 01:17.

  “Oh,” I say.

  Logan chuckles at my obvious disappointment. “Try walking over to the far wall and back. I’m right here. I won’t let you fall.”

  “Yes, sir.” I straighten slowly. Logan rests his hands on my shoulders until I begin moving away from him. The plug is a strange fullness in me, like gas, but—contrary to my expectations—it doesn’t hurt, and just produces a little friction when I walk, although I’m not sure if I’ll be able to sit down with it in. I reach the tiled wall and pause for a moment, before turning around and walking back to Logan.

  He’s watching me with a very big smile. He opens his arms when I reach him and pulls me to his chest. He tips my chin up and taps the tip of my nose with this finger and I spare a second to wonder if that’s the finger he had inside my ass. “How’re you doing?”

  “Okay, sir.” Which is, surprisingly, the truth.

  “Good girl. I want to recap later—”

  “Recap?” I know the sports term but have no idea how it applies to anal training.

  “Mm-hmm. I want to talk about what that little panic was all about. But we’ll do that later. Now, before we go, open your shirt for me. I want to check on your breasts.”

  My breasts? Oh, the nipple clamps. I’d almost forgotten them in light of the whole sticking Morris up my butt thing, but now that he mentions them, my nipples throb.

  While he washes his hands—and is he humming “Twinkle, Twinkle, Little Star” as he does it?—I take off my tie and stuff it in my blazer pocket, then unbutton the shirt and hold it open so he can inspect his handiwork. He takes off each clamp, massages my nipple, then puts the clamp back in place. “How do these feel?”

  “Achy.”

  “Good. They’ll help keep you focused, too. Wash your face, blow your nose, button up, put your tie back on and we’ll go upstairs.”

  “Yes, sir.” I follow each of his instructions carefully. As I check my hair in the mirror, I see a smile I wasn’t aware of. It’s a dreamy smile, which is crazy when my whole body’s aching. But it’s there all the same.

  When I turn back to Logan, he’s watching me, his hands in the pockets of his dress pants, leaning against the door. His face is relaxed, unsmiling, and the only way you’d know he just put a plug in my ass is from the intensity in his eyes. I move to him, stand very close and look right up into those amazing dark eyes. “Thank you very much, sir.”

  He lifts an eyebrow. “For?”

  Mostly it’s for checking on the clamps. But it’s also for everything else. From the way he commands me so precisely, to his control when he was angry with me, to buying me a little purple butt plug called Morris. “Everything.”

  “Good girl.” He kisses me gently, flicking the tip of his tongue across my lower lip, which makes me shiver. “How’s the focus?”

  “Good, sir.” I definitely wouldn’t reach for the check now. My mind’s quiet and calm. I’m actually not thinking about much, just feeling the constant sizzle of my nerves.

  “Remember, if you feel like you’re going to lose control of your bowels, straight to the bathroom. You don’t need to ask permission. I’ll check in with you in five minutes.”

  I nod. I remember. He could give me instructions for assembling a jet engine right now and I’d remember every word.

  He gives me one last kiss, then opens the door and ushers me out.

  Chapter Five

  Logan

  The first person we meet upstairs is Rachel. Of course.

  She’s standing on the landing at the top of the stairs as I help Emily up them. My little girl’s struggling with the butt-plug, grasping the bannister with one hand and my arm with the other as she tries to climb the stairs. I’d be able to tell from a mile away that she’s plugged, and I’m sure Rachel can, too.

  I refuse to remember teaching Rachel to walk while plugged.

  Whatever Rachel’s remembering, she’s got her face under control by the time we reach the top of the stairs. Rachel’s one of those women who has a different hairstyle every time I see her. Tonight, she’s pulled the hair around her face up into a high ponytail. The rest falls in caramel ringlets to her shoulders. It’s pretty, but it’s a little too styled fo
r me. I prefer Emily’s long, loose curls that I can run my hands through.

  I also prefer Emily’s school-girl uniform to the black leather basque set that Rachel’s filling out. The uniform reminds me of school in Morecambe, where I fit in, had good friends and played rugby and cricket. Those aren’t sexy memories, but they’re rich and warm.

  They’re much better memories than the memories of my last few weeks with Rachel. That’s when she started wearing the basque set of a house sub. That’s also when she made me and Sante compete for her. I push those memories aside. We’ve both moved on. All the heat, hurt, anger and remorse that was between us can stay in its grave.

  Rachel waits until we reach the landing, where I pause to let Emily catch her breath. Rachel steps forward, kneels and prostrates herself at my feet, the way I taught her to do whenever her Master entered a room.

  “Master,” she says into the carpet. “Welcome home.”

  I’m not amused. I snap my fingers at her. “Get up, Rachel.”

  “Yes, Master.” She rises and takes a step back. There’s a little bloom on her high cheeks, but that could just be blusher, since she’s made up like she’s about to hit a catwalk. Sante’s generous. I never let her wear anything but mascara, so I could see the black streaks running down her cheeks when I made her cry.

  “Rachel, this is Emily. Emily, Rachel.”

  Rachel’s deep brown eyes flick to Emily and then back to me. She doesn’t greet Emily or acknowledge her, a little discourtesy that’s getting reported to her Master.

  “We’ll be using the Library play space for about an hour,” I tell her.

  After she became exclusive with Sante, Rachel moved from house submissive to hostess for the playrooms. It’s a good fit for her skills. Rachel’s very organized; in her life outside the club, she’s a wedding planner. But it’s a move that left a lot of my brothers, and guests like Rick, very disgruntled at the loss of Rachel as a play-mate.

  “Yes, Master,” she says. She doesn’t consult a clipboard, or the flatscreen that’s mounted on the landing wall, showing the various rooms in use. Rachel can keep hundreds of details in her head, even during the harshest of scenes.

 

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