Pleasing Josie (Surrender Book 5)

by Becca Jameson

  He spanks me again, his palm hitting my clit this time. It stings. It’s a sensation I’ve never dreamed of. It’s so fucking good. What’s wrong with me?

  Now he’s stroking my folds again, my wetness leaking out copiously. My body is shaking. “Please. Master Quinten. Please do it again. Let me come.”

  He obliges me with another hard spank to my pussy before thrusting two fingers into my channel and pressing his thumb to my clit. “Such a good girl. Come for me, princess. Come around my fingers.”

  I shatter, my vision blurring completely while my mouth drops open and my vaginal muscles grip his fingers. He rubs my clit rapidly, not stopping while the orgasm consumes me. He doesn’t let up until I shudder.

  “That’s a good girl. I’m so proud of you.” He leans down and kisses my pulsing pussy reverently.

  Chapter 14

  Josie

  Master Quinten is smiling proudly at me while he wipes my pussy with a warm damp cloth and releases my wrists. He lifts me into his arms and carries me across the room to sit in the rocking chair. He cradles my shaking, naked body against his chest while he rocks me, stroking my back and whispering over and over what a good girl I am.

  When I finally calm down and relax, he kisses my forehead. “Better?”

  “Yes, Sir.”

  “Ready to get dressed? I bet Master Grayson has a nice breakfast waiting for us.”

  I giggle and tip my head back. “I’ve never seen him cook. I’m not sure I’d have very high hopes.”

  He chuckles, his chest vibrating against me, and then he pats my naked bottom. “Up with you.” He stands and sets me on my feet.

  I’m still unnerved by my nudity but less than last night.

  He takes my hand, leads me to the bathroom, patting my bottom. “Use the bathroom while I choose something for you to wear.”

  I flush, but scurry inside and shut the door. I draw in a deep breath as I head for the toilet first and then the sink. After brushing my teeth and washing my face, I open the door.

  Master Quinten is sitting on the edge of my bed with a pile of clothes in his lap. He rises and joins me in the bathroom. His expression is serious. “I want you to wear a plug this morning, princess. It will help make you aware of your bottom and start to stretch you.”

  I automatically clench my butt cheeks together at the thought, and then I take a deep breath. I came here for the weekend to explore new things, examine my preferences. I can’t know if I will like something until I try it. “Okay, Sir.”

  He beams. “That’s my brave girl.” He turns me to face the tub. “Lean over, princess. Hands on the side of the tub. Legs parted.”

  I’m shaking as I do as I’m told. It’s impossible to keep from clenching my bottom. My breasts are hanging in front of me, too. My nipples are stiff. It’s hard to believe I had an earth-shattering orgasm ten minutes ago.

  I’m wet and horny and nervous at the same time.

  Master Quinten opens a drawer and removes a few things. I don’t look, but I hear him set them on the counter. A moment later, he sets a hand on the small of my back and uses his fingers to part my cheeks.

  I hold my breath while he dribbles lubricant on my crack. It runs down to my tight hole, and he sets his finger on it and massages it into my puckered skin. “Breathe for me, princess. I promise this won’t hurt. The plug I’m going to use is barely larger than my finger. Relax your bottom for me.”

  I try because I want to please him. I like it when he says I’m a good girl.

  He picks up the plug and reaches around to show it to me. “See? It’s very small.”

  It’s shiny and silver with a pink jewel. It looks heavy.

  Without hesitation, he lines it up with my bottom and pushes against the ring of nerves. “Don’t clench, princess.”

  I inhale slowly and relax as I exhale.

  He slides the plug into me. “There. See? That wasn’t so bad, was it?” He helps me stand.

  “No, Sir.” It feels awkward though. And even though I saw it, my bottom feels stretched and full. I know the sparkly pink jewel is flat against my tight hole, hiding it. When I take a step, it feels odd. I’m overly aware of it.

  Master Quinten washes his hands and then lifts a pair of panties from the vanity. “How about these?” he asks, holding up a pair of pink panties that have little bows all around the waistband.

  I smile and nod.

  He leans down, and I set my hands on his shoulders to step into them. After he pulls them up my body, he grabs a dress next. The material is white and sheer. There are several layers of it. He gathers it up and lifts it over my head. “Arms up, princess.”

  I lift my arms, and he pulls it over my head. It’s sleeveless. The part that rests on my shoulders is no more than two inches wide. And it has no other definition. It’s what I would call a loose-fitting tank dress. An adult could wear it, with a few exceptions. For one, I’m not wearing a bra, so the soft, thin material is teasing my nipples. It’s also short. Barely long enough to cover my panties. If I twirled around, it would flair out.

  It’s very feminine though, and I like how it looks on me.

  Master Quinten hands me white socks that fold down with excessive ruffles on them, and the white Mary Janes. “Go sit on your rug and put your shoes and socks on.”

  I do as I’m told, sucking in a breath as I take my first steps with the plug inside me. When I lower to the floor, I’m even more aware of the jewel pressing against my bottom, so I hurry to put my shoes and socks on.

  Master Quinten is waiting for me in the bathroom, and he’s got a comb, brush, and ribbons on the counter now. He pulls out my messy buns that I slept in and carefully brushes my tangled locks before parting my hair and efficiently braiding it on both sides.

  He’s very good at arranging hair, which makes me wonder how many little girls he’s taken care of before. How many girls have used this room? I have a twinge of jealousy before I chase it away.

  “Let’s go downstairs now, shall we?” He takes my hand and leads me down to the kitchen.

  When we enter, Master Grayson is sitting on a stool at the island with a cup of coffee. Esther is at the stove. He winces dramatically as we enter. “Esther showed up as I was burning the bacon, and she took over.”

  I giggle and glance at Master Quinten. “I warned you.”

  He chuckles and pats my bottom, reminding me of the plug. “You did indeed. Go show Master Grayson what took us so long while I grab a cup of coffee.”

  I flush as I shuffle closer to my Master, hands clasped in front of me, my gait slightly awkward from the plug.

  Master Grayson cups my chin and lifts my gaze when I reach him. “What do you want to show me, Josie?”

  I don’t want to show him anything, especially not with Esther in the room. I’m struggling to breathe, in fact. Each inhale causes my breasts to rise and fall, my nipples grazing the filmy material of my loose dress. I’m not sure I can do this task.

  Master Quinten comes to my side with a steaming mug of coffee, and even though I don’t normally drink coffee because it makes me hyper, I consider taking it from him and swallowing a long drink to calm my nerves. I lift my gaze to his. “May I have some coffee, Sir?”

  He smiles and pats my head. “No, you may not, princess. Coffee is for grownups. You may have a glass of milk, but you’re stalling. What did I ask you to do?”

  I’m conflicted because my panties are growing wet as I stand here. It’s madness that I would become aroused at the idea of showing Master Grayson my bottom right in the kitchen in front of a woman I hardly know. I actually crave the odd humiliation.

  “Turn around, Josie. Bend over and lift your dress.” Master Quinten’s words are firm.

  I slowly spin so that I’m facing away from them and lean over. The front of my dress is so loose that it’s hanging away from my breasts.

  Master Quinten lifts the material over my bottom and tugs my panties down over my cheeks.

  Master Grayson’s hand
cups my naked butt cheek, and then he taps the jewel. “That’s so pretty, Josie. I love it.”

  I hold my breath while Master Grayson spins the jewel around. My legs start shaking, and I’m not sure they will hold me up. Finally, he pulls my panties back up and helps me stand. He tugs me into his embrace between his legs and kisses me gently on the lips. “Why have I never plugged your bottom before now?”

  I flush. There’s something different about him. He’s…changing somehow.

  “Breakfast is ready,” Esther cheerfully states. “I’m going to start a load of laundry while you all eat.” She bustles from the room, and I pray she hasn’t paid enough attention to my bottom as it was displayed.

  Chapter 15

  Master Grayson

  I pull a chair out for Josie and push her in after she sits. She squirms in her seat for several seconds, undoubtedly overwhelmingly aware of the little plug in her bottom. There is no denying she’s sexy as fuck in this sheer dress that hides nothing. Her tits jiggle as she moves, and I find myself wanting to reach out and grip them, thumb her sensitive nipples through the material.

  The panties she’s wearing made my mouth water, and that plug. God almighty. My cock is going to pop out of my jeans while we eat.

  I take my seat and dish up a plate of food while Quinten makes a plate for Josie and sets it in front of her. She has a glass of milk at her place, too. Correction—the glass is actually plastic, which makes me chuckle inside. Quinten misses nothing. When the man sets the stage, he goes all-out.

  We’ve nearly finished breakfast when Quinten clears his throat and speaks. He’s sitting at the head of the table. Josie and I are flanking him like we did last night. He glances at both of us. “I want this weekend to be all about finding yourselves and hopefully finding a path you can walk together. That being said, there also needs to be some transparency between all three of us. Anything that happens when you’re not together should be shared when you reconvene.”

  My heart is beating. I knew this moment was coming, and I also know Josie won’t be mad about my time with Quinten, but I’m unnerved to open this can of worms. Josie has only known me as a Dom. I’m concerned about what might happen to our dynamic if I start switching.

  “Josie, why don’t you start? Master Grayson can suspect that I let you come after I shaved your pussy, but I bet he’d like to hear the details.”

  I turn to face Josie, glad she is going first, though I’m curious what might have occurred that would be worth mentioning.

  She fidgets, wringing her hands together in her lap.

  I reach over and stroke her head, running my fingers down one of her cute braids. Who knew I would be so attracted to her like this? Or maybe I knew. That isn’t the issue. The problem is that I don’t have a clue how I could fill the shoes of a Daddy no matter how sexy I find it. “Tell me, Josie,” I coax.

  Her voice is small. “After Master Quinten shaved my, uh, pussy, he spanked me down there to make me come.”

  I lift her chin so she faces me. “He swatted your clit?”

  “Yes, Sir.”

  “And you liked it?”

  “Yes, Sir.” Her cheeks turn a deep red.

  “I’m sorry I missed that. Next time I want to watch. Would you like that?”

  She swallows before admitting, “Yes, Sir.”

  “Good girl,” Quinten declares. “Now, Grayson, what would you like to tell Josie?”

  I hold her gaze. There’s no need to feel insecure. I’m still her Master. “After we tucked you into bed last night, I showered with Master Quinten, and he helped me come with his hand around my cock.”

  She smiles broader, thank God, and licks her pink lips. “I’m sorry I missed that. Next time I want to watch.”

  I chuckle at the way she repeats my words back to me. Relief floods me. She’s open to this odd arrangement. Except what the hell even is this arrangement? We’re here for a weekend. The clock is ticking. And then what?

  I don’t see how this venture is going to help the two of us fix our issues. It seems as though so far we’ve gone a long way toward proving we aren’t compatible. Mostly because Josie needs more than I can give her, and I don’t have a clue what’s going on with me.

  I try to parse out this situation. There is no doubt I find Josie unbelievably sexy as a little. It would seem she’s at least open to seeing me get dominated—which still unnerves me some. How is this information helpful? Without Quinten who are we? I can’t be the Daddy Josie needs, and she sure can’t dominate me. It seems like a hot mess.

  It took me a long time to get to sleep last night. For one thing, I was naked. Quinten had essentially put me to bed like he’d done with Josie. My cock had been stiff, and I’d lain there for a long time slowly stroking the erection, edging myself. I probably could have come again even after the release I’d gotten in the shower. Instead, I enjoyed the arousal without giving myself permission to come.

  Part of me hadn’t been sure Quinten wouldn’t walk into the room and catch me. Granted, it wasn’t as if I was his submissive and he could order me around. Nor had he commanded me not to touch myself when he left me. Nevertheless, I’d sensed an unspoken vibe.

  Quinten stands, shaking me out of my thoughts. “Let’s go sit out back for a while. It’s a nice day. We can talk through some things on the patio.” As he speaks, he steps over to Josie and pulls her chair out. She jumps to her feet, her braids flying forward over her shoulders.

  I’m struck once again by how cute she is. Her entire demeanor has changed. From the moment we arrived, she has been a different person. She’s still Josie, but she’s lighter. Freer. Perhaps happier. As if a burden has lifted.

  I reflect back on the night I picked her up at Kellen’s and how relaxed she’d been that night, too. Normally she’s more serious. Pensive. Reflective, I guess. She usually goes through her daily routine with tremendous structure. Our evenings run like clockwork. She cooks and cleans and comes to me to kneel at my side or between my legs.

  I know she finds our routine soothing. We have sex nearly every night, usually involving bondage and edging. She comes so hard she usually screams. I know I’m not the only one who enjoys our dynamic. But maybe she craves more. Hell, maybe I do too.

  “Take your dishes to the sink, princess. Esther will clean the kitchen, but you need to do your part to make her job easier.”

  “Yes, Sir.” Josie picks up her plate and cup. As she walks toward the sink, she moves slowly, balancing her fork on the plate as if it never occurred to her to clasp it with her thumb. I’m fascinated by her ability to so thoroughly slide into the headspace of a young girl.

  Quinten and I do the same with our dishes and then we all three head outside. The weather is perfect. Most of the patio is covered by a roof, which doesn’t surprise me considering how often it rains. In Seattle, it won’t do much good to have a nice outdoor kitchen if it’s not covered.

  There are several seating areas with outdoor sofas, chairs, coffee tables, and end tables. I notice a large flatscreen television mounted in the corner. A grill, sink, and small refrigerator extend several yards out from the back of the house with seating on the far side.

  “Will you be chilly, princess?” Quinten asks Josie. “I can grab you a sweater.”

  She shakes her head. “I’m fine, Sir.” She spots a hanging chair next to one of the sofa arrangements and her face lights up. “May I sit there, Master Quinten?”

  “Of course. Let me help you.” Quinten follows her to the round swinging chair and then grabs her by the waist and lifts her into it.

  Josie giggles as he gives it a little push.

  I can’t help but smile at her excitement. She holds onto the sides but leans back in the chair and sighs as if she’s in heaven. Maybe she is. When she shifts her weight several times in every direction, I imagine she’s once again adjusting around the plug.

  For a moment, I wonder what it might feel like to have a plug in my own ass. I’ve never once considered something lik
e that. Before last night, nothing had been inside my rectum, but the thought of Quinten putting his fingers or even a plug inside me makes me suck in a sharp breath. Would he suggest such a thing? Part of me craves his touch. Part of me is concerned about what I want from him.

  I’m not a little. I’ve told him this. It’s off the table. Not up for discussion. But is he right? Am I submissive on some level?

  Quinten points at one of the brown wicker chairs covered in forest green cushions, and I sit while he takes another one at an angle from me. We’re only a few feet from Josie, so any conversation we have will easily include her.

  “She’s adorable,” Quinten states.

  I realize I’m staring at her with a slight grin on my face and turn to look at Quinten who is doing the same. “Yes. She is. I’m not sure how I never noticed she needed something I wasn’t giving her. It’s so obvious. Even after one evening.”

  Josie leans to one side and lets her head hang sideways, but she looks at me. “Not your fault. I didn’t know it, either.”

  I feel a strong urge to hold her. I wish she were in my lap right now instead of several feet away. But she looks so comfortable that I don’t want to disturb her.

  I try to visualize myself parenting her the way Quinten is demonstrating. It’s hard to nail down in my head. For a moment, I lean my head back and close my eyes. Visions of Josie being bathed, tucked into bed, fed, scolded when necessary… So many things. My cock stiffens at the visuals, but I’m struggling to picture myself as the Daddy in this scenario. Watching Quinten handle her is fucking hot. What about me? Can I learn from Quinten and take over the task? I don’t think so.

  “I wish the chair would swing by itself,” Josie grumbles.

  When I lift my gaze, I find her seat has slowed to a stop.

  Quinten chuckles and then points out into the yard. “There’s a swing out there hanging from that huge oak tree. You’re welcome to go play.”

  Josie sits up fully, follows Quinten’s line of sight, and then jumps down from her chair. “Yay,” she exclaims as she races across the lawn. So damn carefree. Her braids are flying behind her, and the layers of her thin, nearly translucent white dress flutter in the breeze, also.