Chapter 6
Why am I back in Dr. John’s waiting room again this week, with a butt plug filling my ass? That is the question.
I don’t have a good answer, even for myself. That’ll probably take a lot more therapy.
I’m terrified and turned on. I masturbated a lot this past week. Both with and without the plug. Sometimes I even fucked my own ass with it. So why not use it all the time?
Part of me is hoping that means he’ll put off fucking my ass as ‘punishment’, the way he did with my pussy. Part of me is hoping he won’t. I’m so mixed up, I don’t know what I want at this point.
But I’m here.
As always, he’s behind his desk when I walk in. I close the door behind me. I can feel the plug shifting inside me with every step. Reminding me of his intention. What I’m risking just by being here.
Excitement rises and falls in my core, along with my uncertainty.
“Stay right there, Traci,” he says, not looking up, and I freeze in place, closer to the armchair he normally sits in during my appointments than to the couch where I usually sit. My butt clenches around the plug, making my pussy throb.
After a moment, he lifts his gaze away from the computer monitor to look at me instead. There’s banked heat in his dark eyes and it sets my heart racing. I feel my mouth go dry as my pussy gets even wetter.
“Did you masturbate without the plug this week?”
I lift my chin up defiantly.
“Sometimes.”
See what he makes of that. What’s he going to do, not fuck my ass? Oh no.
But my butt clenches around the plug again as my heart rate picks up. I’m testing him and I know it.
He nods once slowly, like it’s what he expected.
“How many times?” he asks.
“What?” I wasn’t really expecting follow-up questions, and I also need a moment to think because it’s not like I kept count.
“How many times did you masturbate without the plug in your ass?”
The calm way he says such filthy things sets off all sorts of reactions in my body. I swear I can feel my nipples hardening as I squirm in front of him, pressing my thighs together so my slick pussy libs rub against each other.
“Um… ten?” I’m totally guessing, but that seems about right. I definitely got myself off multiple times a day, sometimes with the plug and sometimes without it. Sometimes one right after the other. “Ish?”
He nods again, his gaze somehow both cool and hot at the same time. “Take off your clothes and put your hands on the coffee table. Keep your feet together when you do so.”
I start stripping, but he’s not even watching.
The tapping of the keys on his keyboard is the accompaniment to me peeling off my dress.
Which just makes me hotter, even as my face burns with shame.
I turn to the coffee table and bend over, keeping my legs together as he ordered, which means my ass is high in the air while I’m bent forward at an angle.
My tits hang underneath me, my nipples hard and pointy, and not just because of the AC. I can feel how wet my pussy is, and it’s a relief that I can still put pressure on my clit by squeezing my thighs together.
The seconds pass and all I want to do is squirm.
I know this is part of my punishment. The question is whether or not he’s going to fuck my ass at the end of it or if I’ve escaped that part of this session.
I truly don’t know which way it’s going to go and that’s fucking with both my head and my arousal at the same time.
He stops typing and my heart skips a little beat. I can hear the sound of his chair rolling over carpet as he pushes away from the desk. Every nerve in my body feels like it perks up in anticipation and my ass automatically clenches around the plug, feeling every centimeter of the toy invading me.
The only sounds in the room are my panting breaths and the soft shush of his shoes against the carpet as he comes up behind me.
I gasp when his hand touches my ass, caressing my skin.
He finds the base of the plug and twists it inside me, making me moan as all the little nerve endings there come to life.
I hadn’t known how sensitive that hole was until this past week.
“Wise decision to wear this today,” he murmurs. “You’re going to need it.”
My chest clenches along with my ass this time. He’s definitely going to fuck my virgin ass. I should run. I should run right now. But I’m frozen in place.
“First, your punishment.”
What, like fucking my ass isn’t punishment enough?
The sound of leather sliding through cloth belt loops is the only warning I get before hot pain slices across my ass. I rock forward and then jump up, my hands coming back to cover my poor cheeks, a sharp cry caught in my throat.
“That’s one. Back in position, Traci.”
Tears have sprung into my eyes as the burning sting recedes to a hot throbbing, which really isn’t all that much better.
Scream and run. Run as fast as you can.
The voice in my head is right.
But I don’t listen to it.
I bend over again, my tits hanging beneath me, stinging ass high in the air, my muscles clenching in spasms around the plug.
“Relax, or it will hurt more.” Dr. John rubs his hand over my ass and gives it a little smack. Easy for him to say, but somehow I manage it.
This time the pain is more expected. Less shocking. I know how bad it’s going to hurt. It doesn’t make it hurt less, but it does mean I’m able to brace and take it, rather than popping up.
“Good girl.” Dr. John’s hand smooths over the burning welts across my ass, and somehow both the caress and his words soothe some of the hurt. Make it more bearable.
My pussy pulses as his hand lifts and I know what’s coming.
I should have said less times.
The belt comes down again and again, laying new stripes across my ass. The fifth one is the worst, diagonal across the welts he’s already laid down. I manage not to scream but I am crying, the tears dripping down onto the coffee table in front of me.
I’m expecting another one, as he runs his hand over my ass again.
I go up on my toes, letting out a strangled cry as he gives my cheek a rough squeeze, fingers digging into my swollen flesh.
It hurts and yet my pussy pulses in response.
When he lets go, I can still feel the spot throbbing, and I whimper.
When he pulls the plug free from my ass, I’m now empty as well, and a new fear strikes my heart, which just turns me on even more.
“Good girl. Stay there.”
I can’t hear exactly what he’s doing behind me, but I can hear him sit down in his chair. I’m on tenterhooks, waiting for what he’s going to do next. Wondering if my punishment is over.
“Alright Traci. Come here. You’re going to sit on my cock.”
I’m partway up when he finishes his sentence and I freeze. My burning ass hurts so much already, and now he wants me to sit on his cock? I’m going to have to be the one to de-virginize my own ass? He has to be kidding.
I turn around to face him, my cheeks flaming almost as hot as my backside. He’s sitting in his chair, dark eyes on me, his pants open to reveal his shiny, lubricated dick sticking straight up. Waiting for me to come sit on it.
“I…”
“Come.” He nods his head at his lap.
It feels like some strange force has taken over my body as I take a step toward him, and then another. He makes a turning motioning with his finger, indicating that I need to spin around and face away from him.
I don’t know why I do it.
His hands touch my hips, pulling me backward.
My knees bend, my hands going out to find the armrests on the chair, gripping them to help keep my balance as I feel the tip of his cock at my tiny, virgin hole.
Feel my tight ring begin to stretch open for the thick rod.
His hands, which were helping hold me up, begin to slide up to my breasts, leaving it entirely up to me to fight gravity and keep my ass from being deflowered.
It’s an impossible task.
“Now then,” Dr. John says as he fills his palms with my tits, giving them a rough squeeze. “We left off at high school and that teacher you didn’t like. Mrs. Gray.”
He can’t be serious.
But he is.
As my muscles quiver and I slowly lose the fight to keep his cock out of my ass, my body slowly sliding down the thick length to impale my virgin ass on my therapist’s dick, he keeps asking me questions.
Acting like it’s a normal session. Not that any of our sessions have been normal for the past few weeks.
He fondles my breasts while I struggle to breathe as he fills my ass, which is now burning inside out and out.
The stretch is awful. So much worse than the plug.
Unlike the plug, there’s no narrow spot for my sphincter to settle into, it just remains stretched around his massive cock, which I swear gets thicker the further down I go.
Finally, my muscles give way and I fall down the last few inches, my burning cheeks landing on his lap and making me cry out.
I clench, my ass squeezing his cock tightly, and I hear his low moan as his hands tighten on my tits.
Hearing his pleasure would be a lot more enjoyable if I wasn’t throbbing inside and out.
Everything burns. My muscles are clenching non-stop, my ass trying to push out the invader while my pussy begs for it.
“Keep moving, Traci. Up and down.” His fingers close around my nipples, pulling them upward, and I cry out as the twin points of pain flash through me, straight to my pussy.
My thigh muscles burn, but I lift myself up.
Fall back down.
I’m fucking my own ass on his cock while he asks me questions about high school.
It’s not fast or hard. It’s as slow as I can make it while I whimper and answer him.
I know I need to move faster to get it over with, but I used up so much of my energy trying to stay off his dick, now that I’m here I don’t have much left.
My ass burns and cramps as it’s filled with cock, over and over again…
though it’s getting easier to have him inside me as my body adjusts.
Even the burning of my butt cheeks has lessened.
I don’t know how long this goes on for before one of his hands drops down to start playing with my pussy. My soaking wet, eager-to-be-touched, traitorous pussy. I moan, clenching again as his fingers swirl through my creamy lips and find my clit, and arch my back as the need to come slams into me.
“Oh fuck…” I gasp, shuddering. Because it feels better than it has any right to.
He keeps asking me questions, and I answer him through the fog of pain and lust. Although it’s not really painful anymore. Just uncomfortable. And I can bear that.
As his fingers toy with my clit, I start to get new energy. Moving a little faster. A little easier. The feel of his cock sliding though my tight hole is turning me on more and more. I can only imagine what we look like… and the vision is hot as hell.
More questions, but I can feel my orgasm building, and I rock against his fingers, his cock feeling bigger than ever in my ass.
His other hand keeps playing with my breast and nipple, adding to the sensations coursing through me.
Pleasure grows and spirals, and then bursts inside me.
I cry out, leaning back against him, rubbing my pussy against his fingers while his cock throbs inside my tight ass.
I feel his teeth graze my neck, his tongue flicking over the spot, while I writhe against him in ecstasy.
I can’t believe I’m coming while his dick is in my ass.
It’s dirty and hot and oh so wrong, and part of me is loving every second of it.
But my orgasm ends, and his cock is still hard as ever inside me.
He doesn’t say a word, but he’s done with his questions too.
I feel myself being lifted up, and he somehow turns us around so that I’m now kneeling on the floor, my upper body supported by the seat of his chair, still warm from his body.
My breasts press against the warm leather, as does the side of my face.
I start to lift my head up, but his hand curls around my throat, holding me in place.
And then he starts to fuck my ass like there’s no tomorrow.
It hurts.
It feels good.
I’m so overly sensitized from my orgasm that the pain and pleasure blend together in exquisite agony as he uses my ass for his own pleasure. I cry out, my voice slightly muffled by the fingers wrapped around my throat and the way my head is pressed into the cushion.
He’s fucking my ass hard and fast, giving me no quarter, and all I can do is lay in place and take it as he slams himself against my burning cheeks, reigniting the sting from his belt while he reams my tight hole.
The sensations pile onto each other as I gasp for air, my hole clenching nonstop, trying to slow his pace and failing utterly.
It’s like my orgasm never quite ended, and this is adding on to the mountain of sensation.
He’s completely wrecking me and I’m loving it, even as I want to beg him to stop. My mouth opens, but all that comes out is a wild cry as a second, stronger orgasm barrels through me. I’m crying and coming and I can’t stop.
Burying himself in the grip of my ass, his body flush against my burning cheeks, I feel him throbbing within me while I’m coming.
I can feel each pulse of his cum as it forces its way past my tight ring and spurts deep inside me.
I can feel every flex of his cock as he shudders and rocks, my ass milking him of every last drop.
When his hand on my neck finally relaxes, I go completely limp. Wrung out. Almost insensible.
I feel him disengage, but I don’t even bother to try and see what he’s doing. My hole gapes in the cool air and I close my eyes, concentrating on my breathing. Wondering why that felt so damn good.
Why it was so damn hot.
Something pushes against my abused hole and I whimper.
“This is another plug. A little bigger than the one before to help you stay nice and stretched.” His voice is low, soothing.
Almost kind as he pushes the toy into me.
Even though it’s bigger than the previous plug, it’s not wider than his cock, and it settles easily inside me.
I realize it’s going to keep his cum in me while I walk out of the office and I don’t know if I’m grateful or humiliated.
“Make sure to wear it next week. I’m not sure which hole I’ll want to use.
” He chuckles. “Although, if you don’t wear it, it will definitely be your ass. ”
My body clenches at the thought of him using my ass like this again when it hasn’t been stretched and I whimper, nodding my head. I can feel my skin rubbing along the wet leather where my tears have pooled.
Dr. John gives my welted cheeks a good rub.
“Very good. I’ll see you next week, Traci.”
As I get to my wobbly feet, he’s already moving back behind his desk.
This time I don’t fool myself with pretense. I already know I’ll be back.
The End