Pleasing Josie (Surrender Book 5)

by Becca Jameson

  I rock forward and backward, moaning again.

  I’ve forgotten all about Master Quinten until he clears his throat, making me jerk my gaze to find him standing close, grinning. “Such a needy little girl.”

  I flush. Did I not have permission to get naked with Master Grayson? I’m uncertain and I glance back at Master Grayson.

  Master Quinten speaks again. “You’re not in trouble, princess. Master Grayson has full authority over you just as he always has. If he wants you to ride his cock, that’s what you’ll do.”

  I smile and then notice the plug in his hand. He tosses it up in the air a few times and catches it. It looks significantly larger than the last one and my eyes go wide.

  “I was going to have Master Grayson put this in you, but since you’re in this position, I think it would be best if you lean over the top of him and let me put it in. Now’s as good a time as any for you to find out what it’s like to have both holes filled at once.”

  I whimper, not certain I agree with him.

  Master Grayson slides his hands up my back and presses me forward so that I lie over him, my breasts flattening against his chest. His cock is nestled between my folds, teasing my clit.

  I tuck my arms up next to my breasts, my hands fisted. Even though I endured a plug earlier this morning, I’m nervous. This one’s larger, and the thought of wearing it while Master Grayson’s cock is inside me scares me a little.

  While Master Grayson holds me down, his large hands splayed on my shoulder blades, Master Quinten sets a palm on my lower back. A small popping noise I recognize as a bottle of lube resonates in the silence. When it trickles along my crack, I squeeze my eyes closed and tuck my face into Master Grayson’s neck.

  “Deep breaths, Josie,” he whispers. “You have nothing to fear. This plug is only a fraction larger than the one earlier. The purple jewels are going to look just as pretty against your bottom.”

  I shudder as Master Quinten spreads my cheeks, revealing my forbidden hole to his gaze. When he drags the tip of the cold metal plug through the lube, I squirm. I’m suddenly both nervous and eager. I’m not sure why the plugs make my heart pound like they do, but I think it’s because of the naughtiness. There’s something risqué about having anything up inside my tight hole.

  I’m fisting my hands and squeezing my eyes tighter as Master Quinten teases my rear hole with the toy. He pushes it in slightly and pulls it back out over and over. My legs are stiff, but I squirm back and forth anyway.

  Suddenly, in the still silence, I fully accept this side of myself. My little side. Not the submissive I usually am when I’m with Master Grayson, but my little. I love being little. I feel carefree and young and innocent and cute. I like how I feel when these two men take care of me. My regular submissive self wouldn’t be nearly as concerned about the plug as I’m feeling. Little Josie is trembling. Little Josie doesn’t want something in her bottom.

  I whimper. “I don’t like the plugs so much,” I whine as I squirm against Master Grayson.

  Master Grayson’s hands freeze on my back for a heartbeat while I hold my breath, and then he whispers, “Shhh. Be brave for me, Josie. Trust your Masters to make the right choices for you.”

  I’m panting now. Holy shit. We just crossed a line. Or I just crossed into new territory at least. And Master Grayson followed me. I’m not sure what this means for us. I’m still extremely concerned about Master Grayson being able to be a Daddy to me, but this is progress.

  Master Quinten’s fingers paused for a moment, too, and now he’s circling my tight hole with the metal plug. “Sometimes, it’s scary when we experience new things, princess, but that’s part of growing up.” He pushes the blunt end against my hole, and I squeeze it tight, not letting him inside.

  I’m shaking now, not from the plug but from the sudden change of course. I slid deeper into my little self and both men followed me. I’m not sure if I’m happy or freaking out.

  I whimper again, and Master Grayson soothes me with whispers against my ear. “Let Master Quinten put the pretty little plug in you and then I’ll reward you with my cock. You’ll like that, won’t you?”

  I nod against his neck and force myself to relax my rectal muscles.

  Master Quinten eases the plug in very slowly, stretching me open so far with the widest part of the metal that I suck in a breath that isn’t exaggerated. Finally, the toy is fully seated, and I’m glad he doesn’t pull it in and out because I’m shivering from the stress.

  Master Quinten spins the jewel around several times, making me hyper-aware of the sensitive skin inside my rectum. I squirm again, and he pats my bottom. “Good girl. I’m proud of you. See? That wasn’t so bad was it, princess?”

  Master Grayson slides his hands to my shoulders and lifts me so that I’m sitting, straddling him again. I keep my hands fisted, pulling them between my breasts, pressing my forearms against my nipples.

  Master Quinten brushes a loose strand of hair from my temple and kisses me in the same spot. “What a brave girl.”

  I nod, my lip quivering, my eyes wide as I meet his. Moments pass while I know both men are adjusting to my abrupt game-changer. I’ve slid much deeper into my little. We are all processing my change.

  Master Quinten smiles and then leans down and kisses my lips. Gently. It’s the first time he’s kissed me, and I know he’s telling me he approves of my decision. He reaches for my fists and lowers them from my chest. “You deserve a reward for being so brave.”

  I nod, keeping my eyes wide.

  Master Grayson’s hands slide to my breasts and he thumbs my nipples, making me arch. I squirm, lifting my hands to shove playfully at his. “That tickles.”

  Master Grayson smiles. “Does it?” He lifts a brow and continues teasing my nipples. He glances at Master Quinten. “Help me out here?”

  “Gladly.” Master Quinten reaches around me from behind and pulls my wrists to my lower back. He holds both of them in one of his hands. The new position forces my shoulders back and makes my breasts rise.

  I moan when Master Grayson strokes my nipples again.

  Master Quinten lifts my closest breast with one hand and leans down to suck the tip into his mouth. He flicks it rapidly with his tongue, making me wiggle as I struggle against his grip on my wrists. He’s smiling, a twinkle in his eyes, when he releases my nipple to kiss my lips again. “So pretty.”

  My pussy is leaking, coating Master Grayson’s erection. I need him inside me so badly that I don’t even care about the plug anymore.

  Master Quinten looks at Master Grayson, who nods in response to some unspoken communication. Master Quinten flattens his hand on my belly and lifts me several inches.

  I let out a little squeal as Master Grayson takes his cock in his hand and lines it up with my greedy pussy. I have no control at all as Master Quinten eases me down over the thick length. When I’m fully seated, I’m panting. The stretch feels so good. I’ve had sex with Master Grayson hundreds of times, but suddenly here, today, in this weird experimental scene, every inch of my body is quivering with desire.

  “You like that, don’t you, princess? You like having Master Grayson’s cock buried inside you.”

  I nod, unable to speak. He’s still holding me at the front and the back, his fingers splayed across my belly, his other hand gripping my wrists. He’s controlling my every move, including how much cock I get and how much pleasure I feel.

  Master Grayson reaches for my breasts again and plays with my nipples, alternating between pinching them, pulling them, twisting them, and soothing them with gentle flicks. They’re so stiff and sensitive that I think I might come. “Please,” I beg.

  “Please what, princess?”

  “Please let me come.”

  Master Quinten lifts me a few inches, and Master Grayson thrusts up into me from below. Over and over. The position is so erotic. So naughty. My arousal climbs fast. I’m restrained. I’m being held aloft. This is the first time I’ve ever had sex with someone else
in the room. Master Quinten isn’t just in the room, he’s participating.

  The plug in my bottom makes every stroke of Master Grayson’s cock seem tighter. The thin membrane between the toy and his erection is very sensitive.

  I gasp, my vision swimming. And then Master Grayson’s fingers are on my clit, and I’m coming. Hard. Gripping his cock with so much force. Master Grayson is also coming. I can feel his release while he also moans in that familiar way that tells me he is right there with me.

  Every bounce makes my breasts jiggle up and down until finally, Master Quinten lowers me fully onto Master Grayson’s cock a final time. He’s still hard inside me.

  In a flash of motion, I’m no longer restrained, and Master Grayson is holding me against him like before, his arms around me, his hands everywhere, soothing me, whispering words I can’t hear.

  Master Quinten’s hand is on the back of my thighs and my bottom. Rubbing. Patting. Squeezing.

  I can’t catch my breath.

  “That was amazing, Josie.” Master Grayson brushes loose hairs off my forehead and kisses me there.

  “Gorgeous, princess. So very precious.” Master Quinten’s voice is reverent. “And see? You liked the plug, didn’t you?”

  I nod, unable to form words.

  Chapter 20

  Master Quinten

  I’m not sure I’ve ever seen anything so fucking beautiful in my life. My heart is pounding from emotions that are all over the place and not entirely welcome. I can’t fall for these two guests. I can’t. It’s out of the question. And yet, I have.

  When Josie slid deeper into being a little, I nearly choked. I’ve had relationships with littles before, but it’s been a long time, and I didn’t see Josie letting herself so fully embrace her little as she has in one day.

  She’s precious. There is no other word.

  Even though my cock is hard, I don’t mind that my role in their coupling just now was peripheral. I enjoyed every moment, but now I feel a deep need to be a part of it, and I know just what to do.

  I wait until Josie has caught her breath and then I lift her off Grayson’s erection and carefully flip her onto her back next to him. I climb onto the bed from the foot and crawl toward them.

  They are both watching me, sated looks on their faces.

  The first thing I do is lean over Grayson’s semi-hard length and drag my tongue up from the base to the tip, tasting him while he groans in satisfaction. His body twitches as I shift myself over to Josie, push her legs apart, and lower my lips to her pussy. I lap at her, dragging the combination of their come into my mouth and swallowing it. Going back for more. Over and over, I devour this precious gift.

  Until Grayson’s hand lands on my back, I’m unaware of the fact that I have flattened myself between Josie’s legs and eaten her so thoroughly that nothing of Grayson is left. She’s writhing beneath me, her fists gripping the sheets.

  I suck her clit and flick my tongue over it, holding her down, knowing she would shoot off the bed if I let her.

  Grayson’s hand on my back is soothing, encouraging, comforting. “Make her come,” he requests. “I love watching her come.”

  I double my efforts, thrusting my tongue into her, and then circling her clit. I reach my fingers under her thighs and press against the plug. That does it. She cries out as her pussy pulses against my mouth.

  I’ve never seen a woman squirm as much as Josie. No wonder Grayson often restrains her. She’s explosive when she comes.

  Finally, I lift my face, wipe my lips with the back of my hand, and smile at her.

  She is flushed and heaving for breaths.

  Grayson’s hand is on my shirt. He climbs behind me and slowly eases it up my chest. “May I, Sir?”

  I glance over my shoulder at him and nod.

  He shoves my shirt over my head, tossing it aside. As I rise onto my hands and knees, crawling up to kiss Josie, Grayson reaches around for my fly and undoes my jeans. My cock pops free, and I moan as I glance back at him again.

  “I think we’ll take turns,” he teases with a twinkle in his eyes. “How about you lie down and let us service you?”

  I hesitate. He’s directing me. So precariously close to topping me. I lift a brow.

  He swallows. “If it pleases you, Sir.”

  My arms shake at his tone and his expression. Fuck me. He’s submitting to me in front of Josie. It’s fucking hot. It’s a huge step for him. I nod and continue my course, kissing Josie reverently on the lips before dropping onto my back in the spot Grayson had occupied.

  Grayson pulls my jeans and underwear over my hips and shoves them off my body.

  Josie rolls toward me, snuggling into my side, one leg reaching up to push between mine. She sets her cheek on my chest, low enough that she can watch my cock as she wraps her fingers around it and strokes from base to tip.

  I draw in a deep breath and set my hand on her back while I watch Grayson lower himself between my legs. He wastes no time drawing my erection into his mouth, Josie’s small hand still wrapped around the base. No one would know we’d never done this before.

  My breath hitches as Grayson sucks me just right. It’s not surprising. Men give amazing blow jobs. We know what we like.

  Josie wiggles her body closer so that her face is inches from Grayson’s, inches from my cock. The feel of her fingers around me is almost as good as Grayson’s lips.

  I’m not going to last. I’ve been hard since I woke Josie up this morning, and harder than ever while watching the two of them fuck. Now I’m straining to hold back my release. I’m going to come embarrassingly fast, and there’s no stopping it.

  Grayson bounces on and off me faster. When he reaches between my legs to cup my balls, I’m done for. I stiffen, my entire body tight as I come in hard, forceful jets into the back of Grayson’s mouth. He swallows every drop, not releasing me until my muscles relax.

  The moment his mouth pops free, Josie leans closer and licks my dick. So fucking precious.

  For several moments, no one speaks. Josie snuggles back against me, her head nestled against my shoulder now. Grayson drops down onto his side behind her and wraps an arm around her, his hand landing on my belly.

  Finally, it’s Josie that breaks the silence. “I’ve died and gone to heaven,” she states in her adult voice.

  I smile and turn my face toward her to kiss the top of her head. “I think we all did.”

  “Agreed,” Grayson says.

  After a while, I swat Josie’s bottom and rise onto my elbow. “Let’s move to the master bath and shower. And then we need dinner. I’m starving.”

  I slide off the side of the bed, grab Josie around the waist, and toss her over my shoulder. She squeals, a sound I’m growing to love. As I head for the door, she squirms and switches back to her little voice. “Put me down.”

  I give her bottom a firm spank. “Not a chance.” I carry her into the master bathroom and set her on her feet so I can turn on the water. The shower is large, a walk-in. We will all fit just fine.

  Josie is shivering, but before I can say anything, Grayson wraps his arms around her from behind and walks her under the warm water.

  I step into the space and reach for the shower gel, squirting some into my hand while Grayson unravels Josie’s braids. I reach out and cup her breasts, washing her as if this is the filthiest part of her body and it needs a lot of attention.

  She bites her lip and arches her chest out.

  I lower to her feet and work my way up her legs next, being careful between her legs in case she’s sore. By the time I’m standing in front of her again, her hair is down, and I shampoo it next.

  While she stands under the spray of water, I move to Grayson. He reaches for the soap, but I swat his hand out of the way and flatten my palms on his chest just as I had with Josie.

  He closes his eyes and tips his head back, relinquishing control, pleasing me greatly. I let my hands wander all over his body much longer than necessary, finishing by sliding my pal
m up and down his cock until it’s fully erect.

  I release him and glance at Josie to find her watching intently, her expression blissful. When I reach around behind her to pat the plug, she yelps. “Hey…”

  I put conditioner in her hair next and then wash myself while she rinses off. When I turn off the shower, we all step out and grab towels.

  The silence isn’t uncomfortable. It’s pleasant. I know we’re all thinking about what we’ve experienced. Inside I’m freaking out. These two subs don’t belong to me. I keep reminding myself of this fact. Over and over. It’s not getting through to me. I crossed the line, joining them. What am I going to do?

  I pat Josie on the bottom again and lift her chin. “How about you go to your room and put some clean clothes on? Master Grayson and I will be there shortly.”

  “Yes, Sir.” She flushes as she turns to leave.

  When she’s gone, I grab Grayson by the waist and face him, our cocks nestled against each other behind towels. “That was intense. You okay?”

  “Yes. Josie…”

  “I know. We’ll give her a little time and then talk to her.”

  “She’s a little,” he declares as if just now realizing this.

  “Yes.” I reach for his shoulder and give him a slight shake. “You’re going to figure this out. You will. You care for her. Deeply. It’s obvious. And she feels the same about you.”

  “I love her.”

  “I know you do.”

  He’s breathing deeply. I know he’s worried. “I can’t be what she needs.”

  “Of course you can. You spanked her earlier and she loved it. You did great.”

  He’s shaking his head and lowers his gaze before muttering, “I hated it.”

  I stiffen. “Spanking her?”

  “Yes. I don’t have it in me. I didn’t say anything because I knew both of you were so pleased. I’m not that kind of Dom. I prefer the sensual side of things. Ropes and edging and screaming orgasms. I can’t strike her.”

  I swallow. Shit. I should have known this. My vision was clouded because I badly needed Grayson to be a Daddy figure for Josie. At least part time. If he could give her even some of what she craves, I had hoped they could pull this off together. I knew though. I’ve known all along. They need a damn third. And now they’re both attached to me. And I’m fucking attached to them. And I can’t be anyone’s third.