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My What if Guy

Finally hooking up with me is not what he expected
I was over at his place during the summer, just hanging out. Both of us were miraculously, concurrently single, which had never happened in the time we’d known each other. I’ve always found Roland attractive, with his sandy blond hair, tempting muscle definition, and his physical presence. He’s not the tallest guy, but big enough to make me feel petite, which I often forget I am. I’m 5’2” and have always been athletic. As a result, I have rather nice ass and flat stomach, with c-cups to top it off.

Just a note: Roland has always been my “what if” guy. We've never had the chance to be together but he and I have this chemistry that I imagine would translate fantastically in the bedroom. However, I’ve also found him to be rather passive aggressive, or alternatively, smug, and there’s something about him that makes me just want to tie him to a bed, humiliate and have my way with him. I wanted to wipe that smug, know-it-all look from his face. You can believe that when I headed over to his place that day, I was rather happily anticipating what might happen.

Anyway, he asked for a back massage. He sat in front of me and we chatted as I rubbed his back and neck. We started talking about our exes and sex - nothing out of the ordinary since we’ve always been comfortable talking about that sort of thing with each other. Then I started rubbing down his arms and had to lean closer to him, with my breasts resting against his back and my head nearly touching his. Before I was finished, he moved back and grabbed my arms so that I was held against him. I moved my head away as he turned his and gave him a quizzical look.

“What?” I asked.

“You’ve always found me attractive right?” he countered.

“Yeah, what about it?

“Well, we’re both here and single. Would you, perhaps, want to, uummm, have a little fun?”

I just stared at him for a bit, not because I was considering it, but because I wanted him to feel uncomfortable. He stared back with those big, persuasive eyes he uses to charm people. Right as he was opening his mouth to talk again, I kissed him. God it felt good! After years of sexual tension, we were finally doing something besides making jokes or “accidentally” brushing against each other.

The first kiss was light, but they quickly deepened. He pulled me around to his front. I wrapped my hands around his neck and started threading my fingers through his hair, which I know he loves. Meanwhile, he was feeling along my back, getting lower and lower. He hesitated above my ass, and I finally grabbed his hands and pushed them down. I shifted so that I was straddling his legs. As he was kneading my ass, I moved my hands along his back and arms and finally the hard muscles of his chest.

At this point, I started getting impatient. It felt like I was in heat. I reached and started pulling up his shirt. He helped with getting it the rest of the way off. He started trying to grab my shirt, but before he could, I began kissing down his neck, licking his ear and down his pecs.

“Kaley, let me take your shirt off. I’ve wanted to feel your tits since that time at the beach when your top came off.”

I laughed. “I know. Let’s take this into your bedroom.”

I stand up and lead him by the hand into his bedroom. After the door is closed, I push him onto his bed, straddling him again, and pull my light tank top off to reveal my white lace bra. Roland hissed and reached up to grab my breasts, groping them.

“Take your bra off,” he commands. I comply, but laugh to myself that this may be one of the last exercises of free will he will be allowed for a while. My bra comes off.

“Mmm, seeing both is better than seeing just the one,” he comments.

“And for longer too,” I add. I push him out of the way and begin kissing his neck and chest again. His hands are moving all over my back as I work my way down toward his stomach and cock, which I can feel pressing into me. As I kiss him, I unbutton and unzip his shorts. I pull them off and move back up his body to kiss his mouth.

“Do you want me to suck your cock?” I ask him as I rub my tits against his chest and my hands through his hair.

“Oh god yes! Melanie (his ex) never did that.” I move lower again and slowly remove his boxers. His cock springs up, fully erect. It’s slightly larger than normal and looks delicious. I grasp the base of it with one hand and start licking around it, teasing him. I take his balls in my mouth one at a time and bath them with my tongue. I move to his shaft, slowly moving my mouth up it, not touching it, but letting my breath caress it. He’s groaning, but I want him to beg.

“Do you want to be in my mouth?”

“Yes! Please.”

“Wait just one second then.” I get off the bed and turn around so my back is facing him. I slip my shorts over my ass, revealing the thong underneath. I hear him gasp and I remove the thong as well. I spin around and kiss him, then grab his cock and lightly stroke it as I whisper in his ear,

“Do you trust me?” He doesn’t quite know what to make of this, but I have his cock in my hand, so he’s not in a distrustful mood.

“Sure,” he says. Quickly I reach into my backpack, which I placed at the side of his bed earlier. I grab out some ties and start to secure his hand to the bedpost.

“What are you doing?” he asks, alarmed, but doesn’t pull his hand away.

“Relax, baby. I won’t do anything you won’t like. Trust me.” I say this as I begin stroking his cock again. This calms him down and I secure his other hand. The ties I use for his feet are slightly longer and give him some room to move. Once I’m done tying him up, I sit on his legs and kiss his body and mouth again. I rub my tits against his chest and stomach and then along his cock.

“Oh god, why did I let you do this? I want to touch you so bad” he groans. I lean down, running my hands through his hair and along his chest.

I kiss his neck and whisper in his ear, “You can touch me, but only when I say so. You like this, don’t lie. I know you, Roland, and you’ve always wanted to let someone do this to you, to take control.” And with that I push my breasts into his face:

“Suck on them. Lick my nipples.”

He obliges. His touch is light, too light. I push them harder against his mouth and he gets the picture. He begins abusing what he can reach with his tongue. The heat of his mouth and then the cool wetness he leaves behind are exquisite sensations. I lift up a bit.

“Have you ever eaten pussy before, Rol?”

“…”

I situate myself so that we are in a 69 position and tell him that I’ll keep sucking as long as he keeps eating. With that, I take him into my mouth and begin running my tongue all over his hard head and shaft. He hisses and begins to lick my pussy. I’m surprised because it actually feels pretty good. I don’t usually get off when someone licks me, so this is new. As he licks faster, I suck harder. I’ve been keeping it light though and I reach my peak before he’s too close. Waves of pleasure wrack my body, leaving me gasping and quivering. I feel him moving under me, trying to wipe his face off on my ass and legs. The odd sensation makes me giggle.

“Damn woman, you came like a train. This isn’t working very well; can you clean my face off?”

I’ve recovered by then and instead of responding, I return my mouth to his cock.

“Kaley, wait, just get a towel real qui-"

He starts moaning as I reach down to caress his nuts. He forgets his face for a while as I’m sucking his cock down my throat (a useful trick I’d learned with my last boyfriend) and playing with his balls. They begin to clench up and suddenly I shift off of him and abandon his cock right before his orgasm.

“You bitch! I was right about to come!” he exclaims needlessly. I turn around and lay on top of him, running my hands along his body and through his hair, careful not to touch his sensitive member.

“Duh, silly. But I just didn’t feel like you should waste that lovely come in my mouth. Wouldn’t you rather have it in my pussy?”

“Oh god, yes, just fuck me til I come.”

“Hey now, you’re going to have to be a tad more polite if you want that sort of treatment.”

“Please. Please ride me. I want to come inside you!”

“Better. You’d better keep it that way too or else you won’t get to fill me up like you want to.”

I move my body down. My pussy is dripping at this point and I rub it all over his dick, using my juice and spit to lubricate it and my hand to set it at the entrance of my pussy. Slowly, I lower myself down his shaft, centimeters at a time. All the while he is groaning from my tightness, wetness and heat. He is large, and I can’t help but moan as well. I can feel the ridges of his hardness as they move within me. Finally, I bottom out, our hips meeting and my clit rubbing up against his pelvis. I stay there for several moments, getting used to the feeling as it has been a while. I also want him to start squirming. It takes less time than I imagined. He starts moving his hips, hoping to make me move in the process. I pull off and he stops.

“Do you want me to free your hands, Rol? Do you want to touch me… to fuck me?”

“Yes, please! Untie me so I can feel you.” He gasps, the idea of release has him captive now. I lean down, pressing body to his and kiss him passionately.

“You already can feel me. I know what you want though.”

I begin to raise and lower myself on his dick, squeezing my pussy muscles as I drop down. He watches me, fixating on my breasts. His head rolls back as he groans.

“You like watching my tits bounce?”

He doesn’t look at me or answer, just nods. I pull off him so that just the tip is touching me and stop. That gets his attention.

“Answer me bitch! If you want me to continue fucking you, you will answer my questions. Do you like watching me ride you?”

“Yes, your tits are amazing and you feel so good around me. Don’t stop!”

“Good.” I resume bouncing on him. With one hand, I reach back and gently grab his balls. He gasps and I start to move my hands lower til I’m touching his little hole. I feel it clench and his eyes open wide. Now he’s really begging.

“Not there. No, no, no, no. Kaley, please don’t do this.” I smile down at him and remove my hand back to his balls. He sighs in relief and I begin moving faster on his dick. His sigh quickly turns back into groaning and I know he won’t last long. I’d imagined numerous endings to this encounter, but ultimately left the ending unplanned. I know I want to keep having sex with Roland, because he’s always turned me on, and even with him helpless, this session has been hot. That’s why, right before he comes, I grab the ties holding his arms and use the tab I had left free to quickly undo the knots. It takes a second for him to realize he’s free, but when he does, he attacks me. He grabs my hips and bucks up into me. I play with my clit and lose myself in the pleasurable sensations. We are both gasping and shaking, rapidly approaching our climaxes. He thrusts up into me one last time and groans. His orgasm triggers mine and I begin convulsing, squeezing around him, crying out for what seems like five minutes.

Eventually, his hands on my hips loosen and I relax and settle down on top of him. My mouth finds his, gently kissing. His hands roam my back while mine explore his hair. He breaks off the kisses,

“You had me scared for a while, but that was incredible.”

I smile. “Exactly.”
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