Pleasing Josie (Surrender Book 5)

by Becca Jameson

  I stare at him. This is all so overwhelming. But I don’t need to think about it now. I need to sleep off the sub-drop. Because that’s what this is. I recognize it even though I’ve never experienced it.

  “Come.” Master Quinten rises and gathers my clothes. “Wrap the blanket around you until we get to your room.”

  I do as I’m told and follow him out of the office and up the stairs. He drops my clothes on the armchair and pulls back the covers on my bed. Just as he did last night, he intends to tuck me in. I let him take the blanket and climb under the covers. Naked. Again. Sated, too. Confused. My butt burning from the spanking. My head racing with the implications of what I’ve done. My heart pounding. My cock still hard.

  Master Quinten strokes my forehead. “You look very conflicted. Talk to me.”

  I glance away. “I enjoyed that,” I murmur.

  “Good. That was the idea. Why does it bother you so much? You don’t strike me as the kind of man who’s got some macho attitude that dudes can’t be submissive.”

  “I don’t, but…” I draw in a breath. “My father did.”

  “Your father?” He stops stroking my skin and leans close. His voice softens. “Tell me about that.” I hear his psychologist voice coming out. In a way it’s a good thing. It makes me feel safe to share.

  “I was a scrawny kid when I was young. Other kids picked on me. One big kid in particular tormented me.” I pull in a breath. This isn’t shit I’ve shared with anyone in my life besides my parents when I was a small child. I have no idea why it’s spilling out now.

  Master Quinten says nothing, but he cups my neck. He’s waiting patiently for me to continue.

  “My mother wanted to call the school. March to that kid’s house and yell at his parents. My father stopped her and scolded me. He said I needed to toughen up. Be a man.” My voice dips. “He said that I should never let anyone boss me around.”

  Master Quinten draws in a breath. “Babe, I’m so sorry. Thank you for sharing. I understand you much better now.”

  “I’m not judgmental,” I rush to explain. “I totally understand that some men are submissive. It’s just been pounded in me over and over that it’s not okay for me to ever be weak. It’s hard to shake.”

  Master Quinten blows out a breath. “You know being submissive has nothing to do with being weak. It takes incredible strength to submit to someone else.”

  I nod. “Intellectually, I know this, but deep inside I can still hear my father’s voice telling me I’m weak and stupid and wussy.”

  Master Quinten leans down and kisses my forehead, his lips lingering before he pulls back. “You’re none of those things. You’re a formidable Dom in your own right for one thing, but you have a very strong character, Grayson. No one would ever describe you with any of those terms. You have to know that.”

  “I do, but the damage is deep, and it creeps up sometimes.”

  “I’m honored that you submitted to me. It was a huge step for you. I hope you enjoyed it as much as I did.” His voice is softer at the end, as if he’s revealing more than he wanted.

  I stare at him. Maybe his expression is one he uses with any client in his office, but I don’t believe that. I think we have a connection. Does he know it? He’s so adamant about this being nothing more than one weekend. Now, I’m starting to fear he will have done far more harm than good when he lets us go.

  He seems to shake himself out of deep thoughts. “Sleep, babe. You’re exhausted.”

  I blow out a breath and close my eyes. He’s right. I need to rest. I assume I fall asleep quickly because I’m not aware of Master Quinten getting up and leaving my room. I’m not even sure if the second lingering kiss he gave me on the forehead was real or a dream.

  Chapter 19

  Josie

  I’m curled on my side, wide awake, when the door to my room opens. Master Quinten steps inside. He’s alone. He comes over and sits next to me, his hand landing on my hip. “Did you have a nice nap, princess?”

  I nod, snuggling in deeper. I’m cozy. It feels a little weird to be in bed wearing nothing but little girl panties and socks, but I did sleep for a while before waking up and wondering how long it would be until one of my Masters returned to get me.

  “Would you like to get up now? Maybe you’d like to come downstairs and have a snack?”

  I turn my head to fully face him, smiling. “What kind of snack?”

  He chuckles. “How about a popsicle?”

  I grin wider. I haven’t had a popsicle in years. Why do adults give up all the good stuff just because they’re older?

  Master Quinten pulls back the covers and lifts me up, setting me on my feet in front of him. He reaches for my dress and tugs it over my head. “You want to take your socks off and go barefoot? We could go out on the patio while you eat your popsicle.”

  I nod and bend down to remove them.

  Master Quinten takes my hand and leads me from the room.

  “Where is Master Grayson?” I ask as we pass his closed door.

  “He’s taking a nap.”

  I giggle. “Is he little, too?” The thought unnerves me. I’ve noticed that he seems to follow Master Quinten’s instructions, but I can’t wrap my head around him possibly being little also. I’ve been hoping after the way he spanked me and then took care of me that he might be able to fulfill some of my needs.

  Master Quinten chuckles. “No, princess. He’s not little. He’s just tired.”

  “Oh.” That’s good. If he’s not a little, does that mean he could be a Daddy though? I skip down the stairs and follow Master Quinten into the kitchen.

  He opens the freezer. “What color would you like?”

  “Purple,” I exclaim, practically bouncing on my toes.

  Master Quinten grabs the popsicle from the freezer and leads me outside. It’s the kind with two sticks in it, and my mouth is watering at the idea of licking it. He sits on one of the outdoor sofas and sets the popsicle on the end table before turning to face me again. He reaches for the hem of my dress. “Let’s take this back off while you’re eating so you don’t dribble purple juice down the front.”

  I lift my arms, but as soon as I’m left standing in front of him in nothing but my pink panties with the dainty little bows, I feel exposed. I glance around.

  Master Quinten chuckles. “No one can see you in my backyard, princess. Don’t worry.”

  I shiver at the thought while I wait for Master Quinten to give me my popsicle. I’m nearly bouncing on my bare feet as he unwraps it but I stop when my breasts jiggle.

  He hands me the popsicle and then surprises me by lifting me onto his lap so that I sit between his thighs. I’m small enough that I can pull my feet up and set them on the sofa between his legs.

  I moan around the first taste of grape and then lick quickly as the popsicle starts to melt.

  Master Quinten smiles at me indulgently, his hand wrapped around my waist, his fingers teasing the outside of my breast.

  I arch out of his touch and giggle. “That tickles.”

  When he laughs, his eyes wrinkle at the corners, and his body shakes. I’ve never felt more comfortable than I do at this moment on Master Quinten’s lap eating a popsicle with nothing but babyish panties on.

  Guilt seeps into me as I think of Master Grayson. I’ve come here for the weekend to repair my relationship with him, and in less than a day, I’m falling for another man. A man who is only mine for the weekend.

  I can’t keep up with the dripping popsicle, and the juice runs down my arm. When I try to stick too much of it in my mouth, it runs down the corners of my lips and onto my chin. The first drips to hit my breasts make me flinch from the cold.

  “What a messy little girl you are, princess. You’ve got more of that popsicle on you than in you.”

  When the last of it is finally gone, Master Quinten takes the sticks from me and sets them on the wrapper. He then surprises me by leaning in and licking the sticky juice off my chin.

&n
bsp; I gasp at the intimacy. The rest of my body jumps to attention, wanting more. Wanting him to lick my breasts, too.

  He doesn’t though. Instead, he sets me on my feet and grabs the trash. “Let’s get you cleaned up, princess.”

  I follow him inside, holding my sticky arms out from my body, licking my lips even though I’m pretty sure I’m just spreading the mess. My mouth is probably purple.

  When we get to the kitchen, Master Quinten throws the wrapper and sticks in the trash and then grabs me by the waist and lifts me onto the counter. He wets a washcloth and wipes my face and neck first. Next, he runs the terrycloth all down my arms. And last, he wipes my breasts.

  I whimper when he strokes my nipples. They were already hard, but now they are even stiffer.

  When he finally sets the cloth aside, he tickles me again, just below my armpits, teasing the edges of my breasts.

  I giggle and writhe, trying to avoid his fingers. Finally, he stops tickling me and holds me steady with his hands gripping my torso. His thumbs are stroking my breasts though, and I arch into his touch.

  Master Quinten lifts me up again. “Wrap your legs around my waist, princess.” He’s smiling and his voice is deeper, not his usual light unaffected tone. When his gaze meets mine in midair, I feel a connection. Am I making it up? Does he feel it too?

  As I circle my legs around him, he carries me from the kitchen and into the living room. He lowers himself into an armchair and puts his hands back on my torso, his thumbs once again absently stroking the undersides of my breasts. “I want to talk to you about something, princess.” His expression is more serious now.

  “Okay.”

  “Do you know what a switch is?”

  I nod. “You mean like someone who can be both Dominant and submissive?”

  “Yes. That’s exactly what I mean.”

  “Is Master Grayson a switch?” I’m not surprised by this. Even though I haven’t considered it a single time before we arrived here yesterday, I’ve watched Master Quinten with him since our arrival. Master Grayson has been quieter than usual. Serious. Thinking. He watches me like he wants to fuck me into tomorrow, but he restrains himself.

  “I think so, princess. Does that bother you?”

  “No.” I shake my head. “Will he still want to be my Master?” Or my Daddy? Tears form in the corners of my eyes.

  “Oh, princess, yes. I’m sure he still wants to be your Master, but I also think he needs a Master of his own.”

  I frown, my lip trembling. I’m not acting. I’m really nervous. “What does that mean?”

  “It can mean any number of things. We need to explore the possibilities.”

  I swallow over the lump in my throat. “Do you think Master Grayson can be my Daddy?”

  He shrugs. “I don’t know about that, little one. Maybe he can fulfill some of your needs though.”

  “But he’s not a little?” I’m trying to picture our dynamic. Master Grayson has a submissive side. How could he also be a Daddy?

  I think back to him spanking me earlier and get a tingle in my panties. I liked it. Did he enjoy it too? I wonder if Master Quinten has also spanked Master Grayson. Maybe earlier while I was napping. Maybe that’s why I wasn’t supposed to leave my room. Master Quinten needed time with Master Grayson. It makes sense. The idea doesn’t bother me, but it’s confusing. I try to picture Master Grayson submitting to Master Quinten and my mind bungles everything.

  “Nope. Master Grayson isn’t a little. He just has some submissive needs like you do. But he also enjoys being your Dom.”

  We sit in silence for a while. I try to picture this dynamic and come up short. I’m scared and nervous and worried. “Maybe you could be a Daddy to me and a Master to Master Grayson?”

  He shakes his head. “No, princess. I can’t be that person.”

  Now my tears fall, and I reach up to swipe at them. “But you like me and Master Grayson, and you don’t have a little girl of your own. Why can’t I be your little girl?”

  He gives me a squeeze and hugs me against his chest. “I do like you. Both of you. A lot. But I’m a busy man, princess. I can’t do you justice. My plate is very full. I won’t even be in town much for the rest of the year.”

  I cry silently, my tears falling down my cheeks because I can’t stop them. “I don’t want a different Daddy. I like being your little girl,” I whimper. I’m really scared. This experience with Master Quinten has been life-changing. I don’t see how another Master could possibly make me feel the way he does.

  Master Quinten smiles, but it doesn’t reach his eyes. He looks sad. His brow is drawn together and his voice is gravelly when he speaks. “You will, princess. The right Daddy will come along who can give you what you need and also be a Dom to Master Grayson. You just have to be patient.” He wipes my tears with his thumbs. “In the meantime, we’ll spend this weekend making sure you and Master Grayson can come up with a plan that fulfills both your needs. Not full-time, but part of the time. Do you think you can do that?”

  I nod. I know I can do it. I have to do it. I love Master Grayson. I’m worried though because now that I’ve had a taste of what it’s like to be little, I want to continue to explore this world.

  “One thing you can do is play with other people when you go to Surrender. I mentioned this idea to Master Grayson. I’m sure you’ve seen couples come in and then part ways. It’s common. You can fulfill your desire to have a Daddy, and Master Grayson can fulfill his need to submit.”

  I try to picture this and come up empty. I don’t want a different Daddy. I bet Master Grayson has no interest in submitting for strangers, either. If he has been submitting to Master Quinten, this is a totally new journey for him. I’m certain he’s never done something like this before. He must be as attached to Master Quinten as I am. What does that say about the two of us?

  “Enough sadness, princess. There’s no reason to cry. We still have an entire day to figure out what will work best for both of you, okay?”

  I nod.

  “Can I get a smile?”

  I force a small one, and he tickles me again, making me laugh.

  “There’s my girl.” When he grips my waist again, he meets my gaze. “It’s time for you to get another plug inside your tight, little bottom, princess.”

  I clench my butt cheeks together and shake my head. “I don’t like the plugs, Sir.”

  He rolls his eyes. “That’s not true. You got used to the first one, and the second one will be only a tiny bit larger. You need to get used to the feeling of having something inside your bottom, princess, so that one day you can take a cock inside you there. Especially if you’re going to have two Doms.” He lifts a brow to make his point, but he stiffens at his words, too, and I have to wonder if he likes the thought of another man having sex with me.

  Master Quinten told me we needed to stretch my bottom so that I could experience having sex with two men—him and Master Grayson. I wonder if he still plans to fulfill that fantasy. It’s been in the back of my mind. My curiosity is piqued. I’ve visualized both of these Masters taking me at the same time. I don’t have any interest in some other man joining me and Master Grayson though. The thought makes me clench my butt cheeks.

  He pats my bottom. “Let’s go upstairs and wake up Master Grayson. He can put the second plug in. I know he liked seeing the little jewel between your sweet cheeks.”

  I shudder at the thought as Master Quinten sets me on my feet. “My dress is outside, Sir.”

  He snaps his fingers and heads that way. “I’ll be right back.” Seconds later, he returns and motions me to follow him.

  When we reach Master Grayson’s room, Master Quinten knocks on the door.

  “Come in,” Master Grayson’s strong voice calls.

  I follow Master Quinten into the masculine room and find Master Grayson stretching his long body out under a dark sheet. He has tossed the comforter aside. He smiles at me. “Come here, Josie.”

  I skip over to him, my breasts bo
uncing.

  He’s grinning as he reaches for me. “What happened to your dress? And why are your lips purple?”

  I giggle and stick out my tongue.

  “Wow, your entire mouth is purple. Did you have Kool-Aid?”

  I shake my head and announce, “A popsicle. Grape.”

  “Apparently.” He lifts me onto the bed so that I straddle his waist. His cock is hard and pressing against my pussy. I squirm, already aroused.

  He taps my arm and then my breast. “You dripped the popsicle all over your body, didn’t you?”

  Master Quinten chuckles. “You can’t imagine. I’m not sure she even ate any of it.” He holds up my dress. “Luckily I removed her dress first.” He has reached my side and tugs on one of my braids. “I told Josie it’s time for her next plug. I’m going to go grab it from her bathroom. I thought you’d like to put it in her.”

  Master Grayson wiggles his brows. “I’d love to.”

  I squirm again, and he grabs my hips. “Stay still, Josie.”

  “Sorry, Sir,” I murmur, even though I’m not. I was enjoying the friction against my clit.

  As Master Quinten leaves the room, Master Grayson sets his hands on my thighs and slides them up to my panties. When his thumbs rub against the pink cotton, I moan.

  “You’re wet, Josie.”

  I tuck my head to one side all coy-like. “Your fault,” I tell him.

  “Let’s get these wet panties off,” he says as he lifts me up and swings me over the side of the bed to set me on my feet once more. “Take them off and then climb back over me,” he demands.

  My nipples pucker at his tone. This is the Master I’m used to. In our bedroom, he makes my body hum every time. I quickly wiggle out of the pink cotton while Master Grayson tugs the sheets back to reveal his long naked body.

  When he lifts me back over his torso, I spread my legs and straddle him. I wish he would let me slide right down over his cock, but he doesn’t. He settles me so that his erection is captured between my lips, rubbing against my clit.