Training His Butt

Geena wants to do lots of things to Mike's ass. However, she must first train him to take whatever she wants to shove up his...
This Story Includes: butt play

Reading Time: 11 minutes

Written By Mike

A freshman at the State University, Mike is head over heels in love with Geena, and thoroughly enjoys their sessions where she's in control. He is powerless to refuse her anything she wants! ... Read Full Author Bio

Cracking open a book, I try to get myself comfortable on the sad excuse for a twin-sized bed. The springs creak and complain under me, but the bed is the least of my worries. I really thought I had read enough Steinbeck in high school to last a lifetime, but apparently not, as my professor had told us to get started on East of Eden in class this morning. The first few pages nearly make me go cross-eyed with boredom, and I groan, laying the book over my face and trying to pretend to be anywhere else than here.

If Steinbeck wasn’t bad enough, Kyle, my boneheaded roommate was doing bicep curls and blasting “The Chronic” through the speakers of his shitty radio, trying to pump himself up for his game tomorrow, even though he was in English 101 with me. He should suffer through just as much high school level reading as I am, but priorities I guess.

I’m daydreaming behind the musty pages of my book, fantasizing about dropping out and joining a trade school devoid of wishy-washy Americana novels when there is a pounding at the door. I sit up with a start, book flying onto the floor as Kyle loudly drops his weight and pulls the door open with gusto.

There is another Kyle-type on the other side of the door, and I hear them discussing God knows what, interspersed with enthusiastic high fives, before Kyle comes back to speak to me.

“Dude, we’re going out! There’s a kegger at one of the fraternity houses and there are, like, loads of chicks. You in, Mikey?”

“It’s Mike, and no. We have homework.” I nudge the book with my foot to make a point.

Kyle slowly computes my rejection before shaking his head.

“Nah, man. A girl in my lab said that they can print off these things called cliff notes for any book you want, so you don’t have to read the whole thing.” Kyle whispered, as if our English prof was in the other room with her ear pressed to the wall listening.

“I’m good, dude. Have fun.” I tell him, and Kyle shrugs, waving goodbye as he heads out the door.

I flop back onto my creaky bed and stare at the cinderblock walls, considering my fate in life. Rolling over I notice a long dark hair on my pillow. I pick it up, wrapping it around my finger. At least there was one bright spot to university. Geena.

It had been a few days since I had seen her. We had hurried, pretty vanilla sex here on this bed and fallen asleep in each other’s arms for a quick respite between classes. I’d take anything I could get with Geena: A movie at her apartment with her head on my lap, quick missionary between classes, or, Geena’s favorite, elaborate, kinky fucking. Was it crazier than any sex I had experienced before? Yes. Was it the greatest time of my life? Also, yes.

Out loud, I don’t think I could ever say the things that she and I did. Outrageous penthouse letters type things. I could feel a flush creeping up my neck just thinking about them. Also, Geena seemed to have something up her sleeve that I haven’t quite deciphered yet. It was just in the sneaky smirks she kept sending me every time I saw her, and at her insistence I tell her I trust her, and would do whatever she told me to. In the bedroom, it didn’t matter how much bigger than Geena I was. She was the boss, and that was that.

I untwist the hair from my finger, letting it float to the floor. I grab my book and try to get back into it when someone knocks on my door again. This time it’s soft but insistent, and my heart leaps. Who else would be here looking for me besides my girl?

I open the door to Geena’s smiling face. She’s wearing a short pair of distressed denim shorts and an oversized white t-shirt that she tied in a knot in the back, letting a little sliver of her midriff show as she moved. Her dark, luscious hair falls in curls around her shoulders, and as I follow it down, I can see she isn’t wearing a bra, her berry-dark nipples pushing against the fabric of the shirt. She has a black backpack slung over her shoulder and something skitters down my spine at the sight of it. No bra, mysterious bag. Geena was up to something.

“Are you just going to stand there or let me in, Mike?” She says, humor in her voice.

“Ah, yeah. Sorry. I’m just glad to see you.” I wave her into my dorm and make a mental note of myself locking the deadbolt on the room. No one but Kyle or myself could get in or out now, and if I’m lucky, Kyle will be asleep on some mystery lawn tonight, leaving the room to Geena and me. I’m lucky that it’s a Thursday night, and no one was in the hallway dicking around when Geena showed up. The guys on my floor were always moderately respectful when Geena walked to my room, but as soon as the elevator doors close on her leaving they can’t contain themselves. The wolf whistles and rude gestures are almost comical. It’s like they can’t believe this… this Aphrodite was coming to Mike’s dorm. Chubby, hairy Mike, when she had an entire hall of studs to pick from? Thankfully, they seem almost proud of me, slapping me on the back and hollering down the hallway to congratulate me.

I watch Geena settle on the bed, rummaging through her bag, and think to myself that I can’t believe she chose me, either. Damn, she’s stunning.

I sit next to her, and she snuggles into my side, still pawing through the backpack. Finally, she pulls out a bottle of lube and smiles coyly up at me before pulling my head down for a kiss.

“How about a back massage tonight, love?” She asks, shaking the bottle temptingly.

I narrow my eyes. “What are you up to?”

“Shush. You want that back massage or not?”

I sigh and nod. “Yeah, it sounds nice,” I tell her reluctantly. Her smile widens, and she stands, pulling my hands so I stand, too. She put her hands under my shirt, running her fingers through my chest hair as she leans in to whisper into my ear.

“Only if you do everything I say.” She breathes, and I feel her hot breath in my ear, causing me to shiver.

Ah, we’re doing that tonight. More and more Geena has been taking complete control during our sexual escapades. She’s the master, and I’m to do as I’m told. She never loses her sweet, kind demeanor, but she also never takes no for an answer. It’s hot as fuck, and something I’d never thought I’d be into, but something about relinquishing control of my body to the confident, self-assured Geena gets me harder than steel.

I turn to face her, kissing her quickly before responding, “Yes, ma’am. Of course.”

Geena’s eyelids lower, and she has me lift my arms to discard my shirt before pushing down my basketball shorts, leaving me completely nude in the middle of the dorm. This part always freaks me out, because within seconds Kyle could open the door and display me to the entire hall if he came home. Geena seems to get a kick out of the extra danger, so I do my best to breathe deeply and stay calm.

I can feel a blush rising from my neck up to my face as Geena walks a slow circle around me, seeming to look me over, and it causes her to giggle.

“You’re still blushing around me, Mike? I thought we were past all that.” She circled behind me, and I felt her hands grabbing my asscheeks and squeezing. Of course, this only made me blush brighter.

She circles back to my front and taps her lips as she considers something. Finally, she loops her arms around my waist, and I can feel myself growing harder at her nearness.

“Since I still make you so nervous, I think I need to work you up to what I want to do to you soon. So,” She kisses me quickly, and it almost seems like it’s softening the blow of what she’s about to say, “We’re going to train your ass, so I can fuck it next time.”

I tense up, but don’t pull back. Just the words make my heart beat faster. Geena has slipped a finger into me once or twice during a blow job, but fucking? As in with a strapon? It sounds like a lot.

“Are you ready to get started, love?” Geena asks, her eyes bright and excited.

“Y-yes, ma’am.” I answer.

Geena pulls out a case with a set of what looks to be three pointed glass bulbs, ranging from small to large. It only takes me a second before I realize what they are: butt plugs. Geena has me lay flat on the bed, face down, and she straddles my back right above my ass facing towards my feet. I press my face into the mattress as I feel her spreading my cheeks and squirting lube on my hole, and then before I can even request that she take it slowly, she’s slipping the smallest glass plug into me.

“Easy, baby,” she coos as she works it into me. I grit my teeth, fighting against tapping out at the burning sensation, but then it’s finally in. I’m gripping fistfuls of the blanket when Geena turns around, and I see her shirt fall to the floor.

“Now, while you’re getting used to that, I’ll give you that massage.” She tells me.

I feel her lubed-up hands land on my lower back, and she works at my stiff muscles expertly. All the knots from the endless hours in a too-small chair during lectures melt under her fingers, and the relief of it definitely distracts me from the plug in my ass. She kneads my shoulders, and when she leans forward to get a better angle, I can feel her bare tits pressing against me. It’s all really wonderful, the plug really has slipped my mind, until I feel Geena grab the flared base and turn it a few times before pulling it out. I hiss, arching my back, but Geena is using her firm hands to massage my asscheeks just like she did my back, and I’m able to lay flat again.

“You’re doing so good for me,” Geena murmurs, and I hear her unzipping the plug case again. “Deep breath in this time, baby.”

I clench my teeth and breath in slowly, but it’s no use. When Geena starts to slip the second plug in I nearly rocket off the bed. Geena pushes me down with a firm hand on my lower back, twisting the plug back and forth as she works in into my asshole. The burning sensation is worse, but the fullness when the plug is completely seated isn’t so bad. Actually, it could be nice.

“Now,” Geena begins, “Sit on the bed and stroke yourself.”

“Yes, Geena.”

Movement is tedious as I try not to jostle the intruding buttplug, but eventually, I’m sitting normally on my bed. I can still feel it obviously inside of me, but as long as I don’t move too much, it doesn’t bother me. That is, until I touch myself. I didn’t realize how much my body tenses up when I jerk off, but as soon as I put my hand on my dick all my muscles tighten, including the ones holding the plug in place.

Having Geena’s eye on me and the buttplug in place makes this one of the more difficult jerk-off sessions of my life. Geena whispers “faster,” or “slower,” periodically, but never comes over to touch me. It shouldn’t have embarrassed me to touch myself in front of her anymore, but it still did. I can see the lust slowly overtaking her features, and I can’t help but lower my eyes.

“Look at me.” Geena orders.

I drag my eyes back up to hers, my hand never ceasing to move. The sensations from where the buttplug is filling me, and occasionally bumping into what could only be my prostate, added to the mounting pleasure of my hand and the shame mixed with exhilaration from Geena watching me was getting me closer to the finish line than I had expected. I make a strangled sound, toes curling, and that’s when Geena stops me.

“Hands off.” She crosses her arms, pushing her breasts together as she considers the sight of me. Finally, she twirls her finger in a circle.

“Turn around.” She tells me as she retrieves the final buttplug. I tried not to look at it. I’m sure it will never fit inside of me. Still, I follow directions and stand, placing my hands on the bed and bending over. Shivers shoot up my spine as she pulls the current plug out. She skates her hands up and down my back calmingly as she explains what will happen next.

“I’m going to put this last one in, and then you’re going to lie down on this bed and I’m going to ride you while you have this plug…” she runs the cold, glass tip of it over my asscheeks as she speaks, “Deep inside you while I do. I might even let you come.”

“Please,” I hiss out. I am so full of pent up energy and sexual frustration that I don’t care how it happens, I just want to come.

“Since you asked so nicely,” Geena purs, holding my right cheek aside as she works the biggest plug in. Fuck, it’s huge. The pain is shocking at first, rough and unyielding, and my brain really wants me to pull back. But I don’t. I grab fistfuls of the sheets again and breathe through it. Geena is soft with me, her hands gentle and patient, stroking my burning hot skin in comfort until the plug is finally, blessedly all the way in. I stay frozen, dreading when she asks me to move, and at the same time, frantic to be inside of her..

“On the bed now, love,” she says, and I stiffly roll onto my back on the bed. I am completely full, and instinctively I want to arch my back off the bed. I watch Geena shimmy out of her shorts and saunter over to me, throwing one leg over my hips. Her boobs bounce, nipples hard in the cold dorm air, and my palms itch to touch her soft skin.

“Can I touch you?” I ask, not daring to make assumptions. Geena smiles warmly, taking my hands in hers and pressing them to her chest.

The erection I had when I was jerking off had wilted, but the feeling of her pointy nipples and heavy breasts filling my hands has me hard again in seconds. Geena hums her pleasure as I pluck her nipples, and she raises herself over me before settling down on my cock. She is hot, wet, and heavenly, but the extra weight of her on my lap brings the pressure of the plug to the forefront of my mind again.

It’s a cacophony of sensations: the plug stretching me and pushing on my prostate with every forward motion Geena makes, the clenching of Geena’s pussy around me, and the feeling of her under my hands as I palm her tits and eventually work her clit. My climax is rushing forward, coming straight from my asshole to my cock and combining into a storm surge I know is going to be intense.

Geena has let her control slip, too, and has her head thrown back and her hands braced on my thighs as she rides me, leaning back so I have full access to her clit. I’m trying to focus, but everything is pulling me under.

“Can I come? Please, ma’am?” I beg, and Geena seems surprised, almost forgetting that she is the boss as she finds her pleasure on me. She nods, too distracted to speak, and I can feel why. She forces herself down onto me hard, slamming the plug against my prostate, and then she’s coming with abandon. I feel the warm rush of her juices, and combined with everything else, it sends me over the edge too.

My vision blurs with the force of it blasting down my nerve endings as I finish inside Geena. I hold her hips as she rides out her own orgasm, but even after she comes down from the high, I’m still reeling from the aftershocks. To my embarrassment, I’m almost sobbing her name when I finally come back to myself fully. Geena lowers herself down so we are body-to-body and kisses me softly. I kiss her back, but she’s asleep in seconds, and I don’t have it in me to wake her. I roll us until she’s cradled in my arms and try to relax. It’s hard with the buttplug still in me, but I wouldn’t want to disappoint her by taking it out without her permission. With a deep sigh, I will myself into a nap, still uncomfortably full, but satisfied.

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@mikelovesgeena

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