Anna's Anal Awakening

by Daisy Desiree

Copyright© 2019 by Daisy Desiree

Erotica Sex Story: A stranger awakens a desire I didn't know I have until he fulfills me.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Anal Sex   .

“That will be $52.27,” I say to the woman. She puts her credit card into the point-of-sale terminal and I watch my screen to make sure it processes correctly. No problem like normal.

“Hi, Anna,” a friendly voice says.

As the previous shopper wheels her bagged groceries away, I look up and smile. He’s a regular customer here at Food Marketeer and I notice he almost always chooses my line. As usual he’s wearing sunglasses and a ball cap with the logo of one of our local sports teams but I don’t know which one since I don’t care about sports. He looks to be in his mid-30s.

“Hi,” I return the greeting. He knows my name because of my name tag but I don’t know his name because he always pays cash. I don’t ask because if a customer wants me to know his or her name, they will tell me.

“Good day?” he asks.

“Yes,” I shrug.

“Getting off soon?”

I glance at the time in the bottom right corner of my screen. 1:03 pm. “One more hour,” I reply.

I work Friday through Tuesday almost always with the mostly steady schedule of 7 am to 2 pm. I’ve been a cashier at Food Marketeer for over 2 years and worked here since I was 17, first as a bagger and cart attendant. I’m 22 now.

“Hope it goes quick,” he says.

I nod. It usually does.

He hands me a twenty and I process his change.

“I love what you did to your hair.”

“Thank you,” I reply. He told me that the last time he was here. Actually, the last two times I’m almost certain. All I did is cut my straight brown hair. Before it went halfway down my back. Now my hair is shoulder-length on my 5 foot 4 thin body.

I give him his change and say, “Have a great day!”

“You too, Anna.”


I drive home in my 12-year old Corolla. Weather has rusted the hood and roof of my car so it’s not the prettiest thing but it gets my where I need to go which is mostly back and forth to work.

I live in my mom’s two-bedroom condo located on the first floor of the complex. I’ve lived here as long as I can remember. My mom bought the place when I was five so I have no memory of before. I also have no memory of my father. He left us when I was only 18 months. He just seems to have vanished as I can’t find anyone who might be him on social media and if mom knows anything she isn’t saying.

Our place opens into the living room with the kitchen behind. To the left is my mom’s room and to the right is my room. I head toward my room.

Going through the door into my room, my double bed is in the corner taking up most of the room and my dresser is next to that. There’s not a lot of space but it’s my space.

I head to my dresser and pull off my ugly lime green Food Marketeer shirt. I have two identical shirts that I make last the five work days before I do laundry. I fold my shirt and open the second drawer to put it away.

“Don’t stop undressing,” a low male voice says.

I jump and my heart races. I slowly turn.

I see a man closing and locking my bedroom door then turn back toward me.

A naked man.

A naked man with a hard and erect dick sticking about 6 inches outward from his body. He looks be in his late 40s.

I tremble. There is no question what this man wants from me.

“Turn back around and take off your bra,” he says again in his deep voice.

I am not sure why he wants me to face away but I am glad not to look at him looking at me as I comply.

I reach behind and remove my bra. I am a small B size. I instinctively cover them with my hands even though I’m turned away.

“All the way,” he says. “Shoes, socks, pants, panties.”

I crouch down. My fingers shake as I undo my shoes. I slip them off followed by my socks. I stand and undo the button to my pants then unzip. I pause. I inhale deeply, hold it for moment then loudly release in a sound of resignation. I am not a virgin but I’ve only been with one guy and that was with a former co-worker when I was 18.

Thoughts go through my head. Why does he want to do this? Stupid question. Obvious answer. Why me? That is a better question but I have no answer.

“Are you going to continue or should I wait for your mom to come home and fuck her?”

I swallow. My mom? I can’t imagine my mom having to deal with this man. She’s never dated since dad disappeared. 20 years without sex.

Without hesitation, I pull my pants over my hips and drop them. I step out of them. My underwear is plain white. I don’t feel a need to feel sexy at work. I put my fingers into the elastic and down they go. I step out and now I’m naked.

“What a great ass!” he compliments.

I stand still and silent.

“Turn around.”

And now I am facing him standing as naked as he is. I watch his eyes go to my tits and down between my legs. I do keep my pussy hair free. I like the clean feel and everyone does it now. My pussy looks simpler than having a tangled mess of pubic hair and it’s easy to maintain once I knew what I am doing.

“Put your panties in your mouth,” he instructs.

I wrinkle my face. Did he just say what I thought he said? Disgusting!

He sees my reaction because he says, “You can choose clean ones.”

That is much better though I would rather not have any pair in my mouth. I open the top drawer, pull out a clean sister pair of panties, wad it up, and carefully stuff them into my mouth. I breath through my nose.

“Lie face down on the bed,” he tells.

I obey. I lie down straight as an arrow and turn my head to face the wall. He opens my legs a little then I feel the weight of this man’s body on my bed. I close my eyes. I never feel the mattress move with my mere 110 pounds. I feel him straddle my upper legs.

I expect to feel his dick. I don’t expect to feel it pushing at my ass. My hole begins to stretch open and I now know why the panties are in my mouth. I scream into them as the feel of the spongy yet firm head of his dick stretches my hole wider and wider. He continues to force his dick inside my ass and the pain is awful.

His dick breaches my opening and its entirety infiltrates me. The pain is slightly less now that he broke through.

“Oh fuck! Oh fuck! So tight!” he groans.

His dick throbs and I feel hot liquid in my ass followed by several more throbs with additional hot dick juice. His dick pops out of my ass and to my relief it is over already. He came instantly as soon as he was in me.

“Such a tight ass!” he gasps.

It sounds like he is in awe or amazement. It also sounds like he liked being in me.

I feel his release dripping out of my hole. I want to wipe it away but I stay motionless.

He lies on top of me, his chest directly against the skin of my back. I feel his breathing. It is not long before I feel his still hard, or already hard again, dick probing near my hole. Everything feels wet and sticky and gooey. His dick slides over my hole a couple of times then finds center. He pushes and I feel my hole reopening. I let out a painful grunt into my panties as he slides into me much quicker than before. My ass is filled again. I never knew so much width and length could be swallowed up by my body in that location.

“So tight,” he gasps. I shiver. I didn’t think how close his head is to mine right now.

He keeps pushing inward as if to keep it all inside me. He groans and gasps and continually pants “so tight.” He keeps slipping back so he pushes back in. I am not pushing him out. I am not resisting. He slides halfway back and pushes back in.

“Ohhhh!” he groans. He doesn’t try to stay all the way in this time. He repeats the motion and soon his thrusts are long and continual.

For the first time in my 22 years of life my ass is being fucked.

The motion is smooth and painless. There is his significant liquid from when he already came in my ass and there is also plenty of his drooling pre-cum to lubricate my anal walls. He groans and grunts and gasps as his strokes become quicker and more urgent. My ass constantly goes from feeling almost empty to completely full.

“Oh fuck! Oh fuck! Fuuuuuuck!” He holds his dick deep in my ass. A quick moment and I feel it throb hard inside me and now his release. More dick juice is put in my ass. With the second throb I feel a bigger release. The subsequent throbs feel smaller and after that if there is additional cum being deposited in my ass, I don’t feel it. His softening dick slips out and it pulls with it his sticky liquid to drip and cling to my body. His heavy breathing slows and he continues to lie on top of me. I keep my eyes closed just like I have done since the beginning.

Nothing happens. He just stays in the same position.

This nothing happens for a long time or it feels like a long time. I don’t know how long but it is more than five minutes and it is likely much longer.

I feel his gentle breathing and occasionally he’ll adjust his body but it always remains on top of mine.

During this time underneath this man, I relax and I seem to let his body sink my body into the mattress. In my thoughts, I feel safe as if he is protecting me. I try to shake the thought from my mind but it persists. Why would being trapped beneath this man where I have no choice but to remain until he moves feel safe? But I do. He is covering me.

His lower half moves and his dick is sliding around my ass again. It feels at half-strength but as he continues to poke and prod, he hardens. Soon his dick is positioned and with a firm, steady push, he is back inside my ass.

It returns to nothing happening but the feel of his body on top of mine except now it includes the feel of his hard dick deep inside my ass.

I don’t know how long time passes but during this time something happens inside my feelings and thoughts. I feel peace and comfort. I feel fulfilled. I feel like all is right in the world. He staying motionless on top of me is one level of contentment but adding his warm dick filling my ass brings it to an entirely higher level. It is a profound serenity. I would like to stay like this for a long, long, long time. I try to push that thought out of my head but it is very resistant. There is no denying or doubting what I feel. I like this!

The serene feelings continue. His dick deep in my stretched open ass, his body covering mine, my feelings of protection and comfort, my feelings of peace and calmness and a restful spirit.

Not unexpectedly, but sadly all the same, the time must come to an end. I knew he will need to cum again no matter how long he desires to stay inside my ass and so he starts doing small little pushes to try to stay all the way in and I hear his breathing now. He gasps and now does strokes that go half way out and as predictable his stimulation propels him to do full thrusts and I feel his dick go back and forth within my ass walls in an increasingly rapid tempo.

He completes my ass fucking with a groan followed by a throbbing dick and the release of only a small amount of additional fluid. I feel his panting as his dick softens and slips out. My ass is empty.

This time he gets off me. I lie still and listen. I only move after I hear my bedroom door open and close.

I roll to my back. He is gone. I sit up and a gush of cum pours out of my ass. He put so much in me. I am curious so I carefully put my finger into my ass. It slips in easily because of all the liquid he deposited. My ass grips my finger. How did his dick fit inside me?

I pull my blanket off my bed and throw it in the wash. I get into the shower. I squeeze my ass muscles. It is amazing how much more comes out of me before it goes down the drain.


I feel awkward during dinner with mom. I say nothing about this afternoon and I am lost in my thoughts. It should be an awful experience and it started that way but it ended wonderfully and I shouldn’t feel this way. Then again, why shouldn’t I feel this way? Is there anything wrong with ... liking it? Liking the feeling of satisfaction and peace and fulfillment and safety? What could be wrong with enjoying such positive feelings?

I tell mom I am tired and go to bed early. I want to experience those feelings again. I change into my night shirt but this time without panties. I put my finger into my ass. My finger is too small. It doesn’t fill me. I look around my room but I see nothing to satisfy the longing to fill my ass and alleviate its empty feeling. I might as well really go to bed.

I head to the bathroom. As I brush my teeth, I see my hairbrush. It has a round handle. It might work.

I return to my room. I don’t normally lock my door but I do tonight. I definitely don’t want my mom walking in on what I’m about to do. I pull my freshly clean blanket down to the end of the bed and lie down on my stomach just like I was earlier. I reach behind and push the brush handle at my hole. It doesn’t have a nice tapering end like a dick does nor is it a combination of soft firmness. The brush is hard. It begins to hurt but I am determined to have the feeling of a full ass again. With extra effort I finally penetrate and carefully push the brush deeper.

It is a poor substitute for a big warm dick but it is better than nothing. I clench my muscles around the brush. Not a dick but my ass is not empty. I roll over.

Ouch! I already forgot about the brush in my ass.

I jolt back to my stomach and slowly pull the brush out of my aching ass. I get up, turn off the light, and get back into bed. I put the brush back inside my ass.

I close my eyes to go to sleep but this doesn’t feel satisfying. I am uncovered. He is not on top of me. I once more take out the brush. I pull up my blanket and fold it so several layers are on my back. I reinsert the brush.

The blanket is a weight but just like the hair brush it is a poor substitute for the man lying on top of me and pinning me underneath his protective body so I am not able to move until he moves first.

I fall asleep but I roll in the night so I’m awakened by the hairbrush jabbing into my ass. After the third time waking up, I pull the brush out. It will not work.


“Hi Anna.” It is my regular customer, the man in the sunglasses and sports cap.

“Hi,” I mumble. I have not been myself today. My mind keeps going back to yesterday.

“You okay?” he asks.

“Sure,” I reply.

He shakes his head. “You’re not yourself.”

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