Chapter 8
CHAPTER 8
Caleb
Out of all the things I thought I’d be experiencing today, being restrained and sensually tortured wasn’t one of them.
Seems like Ivy was bringing all kinds of new experiences into my life.
Sure, I’d messed around with being tied up before, but it just didn’t do it for me.
Or at least, usually it didn’t.
Right now, my dick was rock hard and aching thanks to the gorgeous woman giving me a look that promised all kinds of dirty things. Mistress Susan leaned over Ivy’s shoulder to whisper into her ear for a little bit before Ivy nodded. To my left, Tyler wheeled over the cloth-covered table with a big smile.
While Mistress Susan continued to whisper to Ivy, Tyler lifted the cloth so the women could see beneath it, but I couldn’t.
That I didn’t like. I was used to being in control, to being the one calling the shots and setting the scene. This change of roles unbalanced me a bit and I found myself pulling at my restraints. Of course I knew all I had to do was say the word and they’d be removed at once, but the stubborn part of me wasn’t going to give Mistress Susan the satisfaction. I’d take my punishment, deserved or not, because Ivy was delivering it.
Ivy gave an adorable little clap and jumped a bit, her heels clacking on the stage. Mistress Susan stepped back and Tyler joined her, both of them leaning against the edge of her desk as they watched us.
I was by no means sexually sheltered, but I’d never been the focus of so many people’s attention in a sexual situation like this before. Sure, I’d experienced an orgy and all the fun that came with it, but it was with a select group of friends in a private setting. Here I felt exposed and out of place. The only one restrained and shirtless in a room full of clothed people.
Ivy tilted her head to the side, studying me as she slowly approached, her hips swaying with each step.
The scent of her baby-powder perfume reached me before her breath tickled my neck as she said, “If at any point you feel like this is too much and you want it to stop, just let me know. No safe word needed, okay?”
I turned my head so my lips brushed along her jaw as I replied, “Isn’t that my line?”
She giggled, backing up slightly as she ran her hands over my shoulders and chest with a rather greedy gleam in her eyes. “Not today. Today you get to put your trust in me. I promise I won’t hurt you too bad. And if I do, you’ll like it.”
Her sassy attitude made me itch to spank her, but I loved it. “Bring it on, little girl.” Louder I added, “You may have me tied up and at your mercy, but I’ll never beg. I’ve known you your whole life, Ivy. You don’t have what it takes to make me beg. You’re just an inexperienced little girl.”
Ivy smiled bigger, clearly getting into her role as she said, “I’ll make you beg, you deserve it after cockblocking me. Any guy who tried to talk to me, you chased away. Leaving me sexually frustrated as hell. Well, now you’re the one who is going to know what it feels like to be unsatisfied.”
I stared hard at her, fighting a smile as I really got into my role. “You think I don’t know what frustration feels like? All those times you spent walking around in front of me in your tiny bathing suits, asking me for back rubs and flirting with me. Every time I spent the night you’d find the smallest pajamas you owned and parade around in front of me. All those hugs where I pretended not to notice that you held on a little extra longer than you should. I wanted to give you what you were begging for, a hard fuck, but your brother would have killed me. You were too young, but you’re not anymore, are you? You’re all grown up, aren’t you, Ivy.” I held her gaze, owning her even though I was the one in restraints. “You think you can make me beg? Good luck.”
Just as I intended, that certainly fired her up and I thought I heard subdued laughter from the class.
I swear sparks flamed in her eyes as she leaned forward and caressed my face as she said in a loud and clear voice, “Either you beg, or you don’t come.”
My competitive side, driven by the testosterone raging through me, had me giving her a cold smile as I whispered back, “Consequences.”
“Now,” Mistress Susan said as she lightly ran her fingers through Tyler’s hair as he knelt at her feet, “he is yours to enjoy, Ivy. Any part you wish to touch, to taste, are available to you. Start with his mouth. He seems fascinated with yours.”
Ivy flushed a little as she hesitated before taking a seat in my lap. I angled my head toward her, more than eager for a taste of her lips. When her mouth met mine it was bliss and I fell almost instantly into her, closing my eyes and absorbing the feeling of her mouth on mine. She kissed me slowly, softly, and I followed suit as she ran her hands over my body like she couldn’t get enough of me.
I had a moment to think about how I was glad I hit the gym on a regular basis before her lips moved away from mine and found my neck. That area of my body had never been particularly sensitive, but when she teased my skin with sharp little bites my hips bucked of their own accord.
Ivy, the bold little thing she was, reached between us and rubbed her hand over my erection. “I’ve never really seen one before, Caleb.”
Her eyes went large and liquid, innocence shining in them despite her kiss-swollen lips and reddened cheeks.
I licked my lips, tasting her gloss on them and had to clear my throat before I answered. “You’ve never seen what? A cock?”
She nodded, all wide-eyed innocence, and damned if that didn’t turn me on. “Yeah. I don’t know what to do. Will you let me experiment with you?”
“Absolutely.”
Off to the side, Mistress Susan laughed and said something to the class, but I paid them no mind. This was indeed the first time Ivy would get to touch me, and if she wanted me to tell her what to do, I was more than happy to oblige. Even though I was the one who was currently restrained, Ivy still gave me power over her. Beneath the attitude, she really did have a submissive heart.
Kissing her way down my neck she reached my chest, sliding easily down my body to kneel between my spread legs. The length of my cock hurt as she rubbed it through my jeans, confined and wanting out. Looking up at me through her lashes, she licked her lips as she began to unbutton my jeans, then slowly lowered the zipper.
All of my attention was on her slender, pale hand with her sparkly red nails as she lowered the zipper, then reached inside my white boxer briefs. When her hand closed around my girth, she made a little sound of approval and gave me a squeeze. That one motion had me seeing stars, and I lifted my ass as much as I could while she shimmied my jeans down my hips far enough to expose my pelvis.
“Mmmm,” she said with a playful smile as she rubbed my aching dick. “You are so hard. Is this normal? To have a man feel so firm?”
“I’ve only ever been like this around you,” I replied honestly. “You make me harder than any other girl ever has. You drive me crazy.”
“Sure,” she replied while continuing to delicately stroke my shaft through my briefs in a light, teasing motion. “Like I believe that.”
“You should. Take me out of my underwear and you’ll be able to see how hard I am. How much precum has dripped out of my dick just from having you kneel between my legs. You look so fucking pretty down there. And I cannot wait to feel your lips around my cock. The first time I kissed you, I knew I couldn’t ignore you any longer. Little sister or not, you taste too good to give up.”
Half her mouth cocked up in a smile and she leaned forward, gently biting my dick. “And what do I taste like?”
I had to clear my throat before I could say, “Cotton candy and some kind of fruit maybe? I don’t know how to label it, but underneath all the sweetness I can taste you. And you taste… I can’t even describe it. All I know is I can’t wait to taste all of you. You have no idea how long I’ve fantasized about you. I’m obsessed with you.”
She stood up and glanced over at Mistress Susan who gave her an encouraging nod. With that Ivy took a step back, leaving me with my erection straining against my underwear. I swear you could see my dick move slightly with the rapid beat of my heart. When I’d told her I was obsessed, I’d meant it. Being this close to her and not being able to freely touch the object of my desires sucked.
Then Ivy began to slowly remove her dress and I changed my mind.
This woman could do whatever she wanted to me and I’d beg for more.
With a soft swish of fabric the dress fell into a puddle around her feet, revealing a lacy navy blue bra and panty set that highlighted her slender figure. Then again, she did have a nice, rounded ass that she flashed me as she gathered up her dress and set it neatly to the side. I inwardly smiled at that action, making note of everything she did. When I got my hands on her after this, I’d used everything I’d learn during our encounter to send her so deep into sub space she’d float for hours.
And I’d be there with her. Holding her, cuddling her, keeping her safe and warm in my bed. I could already feel her exhausted body slumped against mine, her muscles relaxed and a smile on her face even in her sleep. Without a doubt I’d soon join her in the best sleep of my life, curled together on a cold late winter night.
My daydream was interrupted by a sensual, deep bass-filled music coming from the speakers. Before me, Ivy began to unbraid her hair, letting the now wavy red hair fluff out around her face. In her heels, she began to move to the music, and I admired her toned, yet still soft body. When she turned and pressed her full ass, exposed by her thong, against my dick, I thrust up as best I could, wishing I could bury myself between her cheeks.
At some point, I was going to spend some serious time playing with those soft, white orbs.
Ivy leaned back, and I suspected she had some kind of dance training as she ground against me.
Or maybe she took yoga.
Either way, she undulated against me in a way that let me know she was going to be an amazing fuck once I got her beneath me. The position put her neck by my mouth, and I turned my head so I could lick along her pulse. She stiffened for a moment, then her moan vibrated through her throat and against my lips. That’s right, sweetheart, the heat cuts both ways between us. I gave her a small, possessive bite and she shuddered, reminding me how easily she came.
I wondered if I could make her come while cuffed to a chair.
The lights dimmed around Ivy and I, leaving us more in the shadows than exposed to the room.
Glancing over at Tyler who was standing over by the light switch, I saw him give me a wink before rejoining Mistress Susan who had gone quiet at this point, watching Ivy do her thing.
I couldn’t blame her. Ivy was a sight to behold as she moved to the music, her elfin features soft with pleasure as she cupped her own breasts and rubbed herself against me. Turning abruptly, she adjusted something on the chair so I lay back a little and my legs were spread wider. Curious, I watched her as she adjusted me to her pleasure, then smiled as she danced her way onto my lap.
Her panty covered sex settled over the underwear and she placed her hands on my shoulders, settling herself. With her calves curved over my thighs and her legs spread over my hips, she appeared both delicate and crazy hot. The dim lighting made her hair glow while obscuring her features, highlighting the image of her body rather than the detail.
I reminded myself to thank Tyler later. While I enjoyed fulfilling her obvious love of having sexual encounters in public, I didn’t want to share her body with strangers. Not when I’d barely had a chance to explore it myself. And what a tight, flexible little body it was. I looked down, trying to see the pouty lips of her sex through her lacy panties, but it was obscured as she rubbed her clit against my cock.
Damn, she was not holding back.
I watched her face, noting how her nipples had beaded into rock hard circles beneath her bra, how her fingers were curling into the muscles on the back of my neck. Her jaw went tense, and her hips rocked against me in a rapid motion.
“Does that feel good?” I said in a low voice meant for her ears only. “It must because you are soaking my underwear. After you come, you’ll take me out and suck me clean. Understood.”
“You”—she shuddered, so on edge I could feel it in the way her body moved oh so sensually against mine—“you aren’t in charge.”
“Come on, Ivy,” I cajoled. “I’m offering you an orgasm. Is that a horrible thing?”
“I…” She tried to focus on me, but her lovely eyes were showing the signs of slipping away from the real world and into subspace.
“Just say yes, Master,” I urged her. “Do what I tell you and I promise you’ll come so hard.”
She slowed down for a moment, then that mischievous smile of hers that I loved so much began to appear. I knew by now it meant she was going to misbehave, but so far I’d enjoyed it when she did. And I’d meant it when I’d told her I would keep a mental tally of her transgressions and there would be consequences. Nothing too terrible as we hadn’t outlined rules or even really negotiated, but I did plan on letting her know that even if I found her irresistible, I was still her Master.
“I don’t need to call you Master to come hard,” she said with a saucy smile that begged for a spanking. “You’re tied up and at my mercy.”
Little did she know the restraints were breakaway, most classroom restraints were for safety reasons, but I let her cling to her illusion of control.
“Ivy,” I lifted my chin, motioning her closer. “Kiss me.”
She started toward me, then stopped and said, “I’m only kissing you because I want to. So I can tease you.”
“Of course,” I leaned up as much as I could so I could capture her lower lip in a quick, nipping bite. “Whatever you say.”
She smiled as she rubbed her cheek against mine in a surprisingly affectionate gesture. “You feel so good, Caleb. Why does touching you feel so different? I mean, it almost seems like I’ve had a couple shots whenever I’m in your presence. I get all distracted and the only thing I’m able to focus on is you.”
Her words warmed my heart and I rewarded her with a nuzzle in return, my lips brushing along her temple as I said, “You belong to me, simple as that. Your body knows it, even if your brain is still catching up on the fact.”
She stiffened a little against me and I pulled back a bit, realizing I was rushing things.
“You’ve always been mine, Ivy. Why do you think I chased all those limp dick losers away from you? Every inch of you belongs to me, just like every inch of me belongs to you.” I placed a kiss on the shell of her ear while whispering, “While you can make out with other pretty little female submissives, your orgasms belong to me. You only have them when and where I allow them. If I want you to come on a girl’s face, you will. But otherwise every time you come I want it to be with me.”
She ground against me and had an orgasm right there on the spot.
Oh yeah, we were compatible.
With her face buried in my neck, and her hands roaming over my torso, she ground her way through a rather nice climax, her moans soft and warm instead of the broken and screaming orgasms I’d given her.
They were probably mildly satisfying, but now that she knew what I could do for her, I was hoping she’d give me a chance to take charge.
I’d fucking love to get her little bubble butt strapped into this chair.
“Give me your mouth,” I urged. “And ride me. I don’t care how sensitive you are.”
She surprised me by reaching between us and arranging my cock so it pointed straight to my belly button. The head and a good three inches poked out of the top of the white boxer briefs I wore, and rested against my tensed abs. Even in the dim lighting I could see the way the tip glistened and Ivy must have seen it as well. She began to move off of my lap, and before I could protest, once again knelt between my legs.
Except this time she grabbed my dick and plunged her mouth down over the head.
I made some kind of choked growl that had been jerked from deep in my chest as her skilled mouth closed over my tip and sucked. My toes curled when she pumped my shaft, one hand holding her hair pulled back and allowing me a stellar view. My underwear was still mostly on, but I could have cared less. I could feel her hunger as she worked me with her mouth and it made me want to fuck her through the nearest wall.
“Get up here,” I ordered, “slide those panties over and ride me.”
She released my dick from her mouth with a pop, and I bit back a moan of disappointment at the loss of suction. “Nope.”
“What?” I glared at her. “I want that pussy on my dick, now.”
She laved the head of my cock with her tongue, her eyes holding mine the whole time. “No. Then I’d fail the class, and I can’t have that. I have to tease you, not please you. And my pussy is so good you’d come right away. Don’t worry. There’s only five minutes left. I’m sure you won’t be begging by the end of it. Right?”
I locked my jaw and clenched my teeth as she proceeded to show me that she could not only deep throat but hold her breath for a very long time. When Mistress Susan announced the three minute mark I was shaking, and when she called out two, I let out a steady stream of moans and swearing. My balls were drawn up so tight they ached, yet my dick was in heaven as she worshiped me.
Without warning she released me and climbed on my lap, fastening her hot and wet mouth to mine. I paid no attention to the faint taste of my precum on her tongue, instead losing myself in kissing her. We were both sweaty by this point, and her body slid against mine as she straddled me, her slit pressing against my cock. Even through her panties I could feel how soaked she was, and I gave her as much of a rock with my hips as I could.
She moved so the head of my cock pressed against the section of her panties guarding her hole from my penetration.
Pressing her hands on my chest, she leaned back and whispered, “Beg me.”
The countdown had almost reached its end, thank God, because another minute of being almost inside of her would have me promising my soul to the devil for a taste of her. Her hair flared around her in waves as she pressed her hips down, those damn panties stretching around the overly sensitive skin of my dick.
As the countdown finally ended, I smiled as Ivy fell forward, clearly exhausted.
She placed a series of lazy kisses along my neck, then let out a deep sigh before whispering, “I’ll see you at Josh’s party tonight, okay?”
“If you think I’m letting you leave this room without my dick inside of you, you’ve lost your mind,” I told her with complete sincerity.
She placed her fingertips on my lips and leaned up so I could see her expression. “Caleb, please. I need a few hours to myself. Today has been intense and I need some rest, okay?”
My whole body ached with the need to fuck, but I ignored the pounding in my groin. Or at least I tried to. With her hot, wet pussy pressed so close to me I had to clench my hands into fists to keep from ripping free from my restraints. The bell rang, and with a sigh Ivy rose, then took off her heels with a wry smile. She slipped back into her dress, with the help of Mistress Susan. When she finished dressing, she finally looked at me again. Tyler had placed a blanket over my lower half but had whispered that his Mistress wanted me restrained until Ivy left the room. He said it was for my own good but I doubted it.
Blowing me a kiss, Ivy said, “I’ll see you at the party. Remember, Josh doesn’t want a bunch of people there. His parents are out of town, and we’ll be down in the basement and there is only so much room. I promised Jennifer I’d come with her and I really want to go. So can you please meet me there?”
I, of course, nodded at once, “I’ll be there. Might run a little late because I have a previous engagement I can’t miss, but I’ll be there.”
Her little wave goodbye was adorable, and I went to return it, then sighed when the restraint held.
I followed Ivy’s slender figure out the door, waiting for Tyler to remove the restraints for me. He and Mistress Susan appeared to be having a serious conversation with a weeping man, so I started to work the safety pull when a woman’s hand covered mine. I followed the hand, covered in lace gloves, up to a white leather bustier and then into a beautiful and familiar face. Arched dark brows, pouty lips, and big brown eyes, she had a rounded figure that made a man think of grabbing her tight and holding on.
“Hey, Mia,” I said to a woman I’d made out with a few months ago in Rawhide’s bar inside the Dungeon.
Back then she’d been here for a leather conference and had a thing for white leather. Now I guess she was here for the 80s party and once again wore white leather. This time she resembled a heavy metal groupie with her dark hair teased into a silky halo around her face. Silver bangles jingled on her wrists as she began to undo one of the restraints.
“Poor Master Caleb, let me get you free and I’ll take care of you.” She released one of my hands and bent down to my foot. “You can come wherever you want inside or on me.”
“Thank you, Mia,” I replied as kindly as I could then lowered my voice as a few people lingered here and there, “but no thank you. I’m spoken for.”
“But you’re still wearing your ring,” she glanced at my right hand. “That means you’re available.”
“I know, and I’m realizing how much of a problem that is. While I thank you for your offer, I must decline,” I told her as she removed my other restrained hand.
As soon as both of my hands were free I reached beneath the blanket, forcing my engorged dick back into my pants. It was an unpleasant experience to say the least, but I managed to have myself covered by the time I was completely free. Tyler joined us, shooing off Mia and handing me the rest of my clothes.
As I dressed, Mistress Susan joined us and gave me an actual hug. Then, to make things even more surreal, she complimented me on the way I’d handled things. In her books, I was worthy of the title Master.
Whoopee.
I didn’t say that aloud, but by the time I got out of the classroom, I only had three hours before the party started. That gave me enough time to jerk off in the shower and get a few hours of rest. And fuck if I didn’t need it. Ivy had worn me out today, first with getting her off, then with teasing me until I nearly broke. The memory of her grinding her clit against my cock through her panties would forever be seared perfectly into my memory.
When I exited the room, I was surprised to find a group of around seven guys lingering in the hallway. A few I recognized from the class, but I didn’t really know any of them by name. They all turned as one as I came out of the classroom, making me pause.
“Can I help you?” I asked as I glanced around the still busy hallway.
An older man wearing a varsity football jacket came over and held out his hand. “Name’s Charlie, my wife and sub Jennifer is friends with Ivy. My friends and I were impressed with the way you held out back there. And even more so when you let her go. She’s with Jennifer right now, getting pampered at the spa. We thought that while the girls are busy, we’d give you some advice about what’s going to happen tonight at Josh’s party. We’re on the Spirit Week committee and we work with the Ranch to help brainstorm ideas for the event.”
Another man, this one in his early thirties wearing a beat up baseball cap and an Aerosmith t-shirt joined us. “I came up with a few ideas for tonight, like spin the bottle.”
Charlie tilted his head and gave me a small grin. “You ever hear of the game called seven minutes in heaven?”
I laughed and nodded. “Might have even played it a time or two.”
“Well, we’re going to give you a hell of a lot more than seven minutes,” the guy in the baseball cap said with a big smile. “And we’re not going to shove you in a closet. There will be a big couch in there, along with some other fun stuff, but no lights in keeping with the closet theme. You have that room for as long as you need to get your ring on that pretty submissive who obviously adores you. We all hope that when you come out your balls are drained to dust and that pretty girl is wearing your ring.”
Rubbing my face with both hands, I laughed and looked up at the ceiling, “Well, I’m not going to turn down an offer like that.”
Beaming at me, Charlie leaned forward and whispered, “Rail the hell out of her, Caleb. That little cock tease is begging for a hard spank and a harder fuck. My Jennifer is strong-willed like Ivy and needs a firm hand to make her happy.”
“But not too firm,” baseball cap guy added. “Thing with Middles is you need to recognize they are becoming adults and give them a little more freedom to make mistakes.”
I chuckled then made a point of looking at my watch. “Thanks for the advice, but I have to go take care of a few things.”
“Of course,” Charlie said as he started to make his way back to his group of friends. “Just know, we’re all rooting for you.”
“Thanks,” I replied in what I hoped was a normal voice.
What the hell had my life become? I was getting ready to go to a party supposedly in the basement of someone’s house, and I was excited as a kid about it. Shit, I couldn’t remember the last time I’d been this excited about anything. Working in the entertainment business as a talent scout took me to a lot of what people would typically think of as being fun events. But for me they were work, and my free time and work time seemed to mingle until I wasn’t sure where one started and the other ended.
When had I last been to a party where I didn’t feel like I needed to be “on” for it? Where I didn’t feel like I had to network or try to impress someone. True, I wasn’t going to a traditional party, but I knew it wouldn’t only be about sexual gratification. It would be about hanging out. Talking and getting to know each other. Then drinking games and the adult fun would begin.
I walked a little faster, a smile plastered across my face as I realized that soon I’d finally get to experience my own personal seven minutes in heaven.