My fall from grace began in 2015, when I wrote this short story. I'm not going to lie, Lucky Stiff, does have it's flaws, the big one being that it's written in the first person. When writing smut, I find a more omnipresence voice works best. Regardless, I present this story here in it's entirety...
Thank god I’m almost home.
My erection hasn’t gone down for at least 20 minute, and shows no signs of giving up. Much to my relief, the bus is practically empty, and I have a seat to myself. I was lucky in that regard, but not so much in love.
I’m 25, and not a bad looking guy—by my own account.
The problem is, I’m social awkward especially when it comes to women.
Another thing working against me is I don’t have a car. I have a good job with the local government, but I also live in an expensive city. So a car payment is out of the question if I want a roof over my head and food to eat. Fortunately, there is a great bus system here, so I get along well enough.
Believe it or not the first time I kissed a girl was about 30 minutes ago—pretty sad that it took so long.
I meet Renee online. She had just moved up here from a small Southern town, and wanted to meet a nice guy to show her around. I guess I fit the bill—lucky me.
When we met in real life, I was so glad she was an actual woman that I looked past the fact that she was very large and very round.
Our first date had gone… okay, I guess. We agreed to meet downtown. I took her to a fancy restraint that wouldn’t put too much of a strain on my wallet. From there I took her to a movie. Her online profile said she was a big geek, which was a big turn on for me. She also said that Return of the Jedi was her favorite movie. It couldn’t have been more perfect, as one of the revival houses, here, happened to be showing Jedi that night. The theater had a modest crowd, and we found some seats near the front.
Now, I should have known something was up, when she started fidgeting in her seat. I ignored it, and continued to watch the movie. Half way through the film, she got up and walked out. I caught up with her outside, and asked her what was wrong.
“It wasn’t as good as I remember it,” she said.
I thought I’d blown it. But the next day, I got a text saying that she had had a wonderful time with me, and would like to see me again.
We went on a second date, and then a third. After each date, I thought I had completely blown it, but she sent me a text each time assuring me that she had had a wonderful time.
And that’s pretty much how our relationship went. I figured this was just how it was between men and women. My only relationship prior to this point had been porn and my hand—so I was glad for a change of pace.
But it didn’t feel right, and at the end of our first month together things started getting weird.
If I had been savvier with women, maybe I would have seen the red flags. The problem was that I was just so glad to have a real woman actually pay attention to me that I didn’t care.
What didn’t feel right was the fact that Renee never seemed to have any time for me. For some mysterious reason, she took a job on nights and weekends, which pretty much put the brakes on our dating life.
I would try to arrange a date and she’d always be working. Then out of the blue, she would call, want me drop everything and go out.
A couple of things stand out here.
One time, she called and I went over to her place. I saw her waiting outside her door. Next to her sat a computer.
“I remember you saying that you liked to fix computers…”
“Well mine’s broken. Call me when the computer’s ready.”
Then she quickly left for work.
I fixed the computer, and even paid for a new hard drive with my own money.
Another memorable incident came, when I finally was able to score a lunch date with her. The date went the same as it always did. She told me she had a nice time, and even asked if I would mail a letter for her—I happily obliged.
When I got home, something just didn’t feel right. I couldn’t put a finger on anything specific, but something felt off about that date.
So I decided to check the online dating site where we meet. I didn’t have a profile on there anymore, but Renee still did.
What do I see?
I see a recent post where she complained bitterly about how there were no nice guys in town. And the post went on and on about she was tired of going out on dates with losers.
That should have sent me running.
It didn’t, though. I guess I’m just a glutton for punishment. After all, Renee was the only woman paying attention to me. So I forgave and overlooked a lot.
And that’s a big reason why I’m in this embarrassing situation, right now—with a hard on that just won’t go away.
What happened was this.
Renee called me at work. She wanted to hang out, and I happily accepted the invitation.
“Where did you want to meet?” I ask
“At the library,” she answers in her Southern drawl.
“Do you want to get something to eat first?”
We agree to a time. I’m so excited that I don’t even hear Renee hang up.
It’s Friday, and in the back of mind, I’m thinking that maybe she and I can spend some time together over the weekend.
At my desk, I can’t concentrate. I need to walk around for a little bit, and clear my head. I decided to head downstairs and get something out of the vending machine. My boss is cool, and didn’t mind if we took little breaks throughout the day, as long as we get our work done.
I’m so lost in my own little world that I didn’t even notice my co-worker until I run into her. Anna is five years older than me, but she is beautiful. Not beautiful in the super model way, since she wasn’t lean or tall. No Anna was short and curvy. She was also Native American which gave her something of an exotic quality. She had short black hair that curled around her ears, and big brown eyes that you could get lost in. My eyes darted up briefly, and I noticed the sweater she’s wearing. The front is stretched out, and can barely contain her breasts. I quickly look away—praying that she didn’t see me take a quick peak.
“Sorry,” I said quietly. I kept my eyes focused on the ground, and start helping her pick up the papers that she dropped.
“It’s okay,” she answered, “I was hoping to run into you.”
She smiles at me then, and I notice her tuck a few strands of hair behind her ear.
I wasn’t sure what to make of that, so I quickly excused myself and head downstairs.
Downstairs, I can’t stop thinking about how good Anna looked in that sweater.
But I put any more sinful thoughts out of my mind. A woman like Anna would never want to have anything to do with a guy like me.
After work, I head over to the library.
Renee is twenty minutes late.
“Sorry,” she says, “my shift went long.”
“No problem,” I answered.
“I’m glad you’re here,” she said. “See the library only allows you to use the computer for 30 minutes, and I wanted to look for a new job. With you here I can use the computer for an hour.”
“What happened to your computer,” I ask
“Gave it away to a friend,” she answers. “Look are you going to help me or not?”
So for about an hour, I watch as my girlfriend looks and applies for a few jobs online. All the while, I’m bored at out of my mind.
But I stay, and my reward is that I get to walk her home. I hold her hand, and as we walk I can feel a stir in my pants. By the time we reach her place, I’m ready to throw her down, and have my way with her right there in the drive way.
Instead, I nervously asked: “Would it be all right if I kissed you?”
She sighs, and then puckers her lips.
I kiss her. I want it too last forever, but she quickly pulls away.
I feel light head, and dizzy—the whole world feels like it’s spinning around me.
I see Renee look down at my crotch. And, when I look at her again I swear I can see a trace of a smile on her lips, and not a pretty one—there is something smug about it.
“Well,” she says, “You’d better get going. Don’t want to miss your bus, right?”
Before I can respond, she is already inside, and closes the door behind her.
I’m still stiff, as the bus pulls up to my stop. Fortunately, the stop is right outside my apartment. I step off the bus, and sigh—resigning to relieve myself in the shower, and then spend another night alone.
Across the street, there is a bar. And, strangely, I think I see someone waving at me. It looks like my co-worker Anna.
My head tells me to just go upstairs. But, I’m not thinking with my head at the moment, so I walk across the street.
Anna smiles as I approach and I see her tuck a few strands of hair behind her ear.
“What are you doing her,” she asks.
Anna looks amazing. She wears a one piece form fitting dress. And, it’s only now that I see just how full her breasts are. If I wasn’t already hard I would be now. Still I feel a pain in pants, as my erection begs to be set free.
“I…uh…live across the street,” I say. My throat feels dry, and I struggle with the words.
“I’m glad you’re her,” she says, “Can I confess something?”
“This is the first time I’ve gone out of the town, since my divorce. I actually was about to leave…”
She moves in a little closer, and I can feel my heart race.
“I was kind of embarrassed to go in, you know. I don’t really have anybody to go in with me.”
Her eyes drift down.
Oh god, I think, she is going to see my…
She looks up, and stares at me for a moment. Her expression is hard to read—stern, perhaps or possibly angry.
“Buy me a drink,” she says. Her voice is hoarse and throaty.
We barely touch our drinks, and our conversation is sporadic.
But, I do catch her looking down at my crotch several times.
“You know,” she says, “all I really want is a nice and decent guy.”
She smiles at me, and touches my arm.
The sensation is electric. And I want her more than anything else in the world.
“Those seem to be in short supply,” I say. I don’t mean to sound as bitter as I do, but the bitterness is there nonetheless.
She frowns and takes a sip from her drink.
“You’re not very good at this are you?”
I shake my head. And, figure I’ve completely blown it.
She sighs. And, I watch as her breasts momentarily raise up, and then down as she lets out her breath.
“It’s okay,” she says, “I’m nervous too—nervous and excited.”
She takes another sip of her drink, and then looks me in the eye.
God those beautiful brown eyes.
“You said you live across the street.”
She puts a hand on my thigh. And, I feel my cock suddenly twinge in my pants.
“Then what are we waiting for?” Her voice is low and throaty, and I need no further hint.
The elevator ride is long, but mercifully we are alone. We’re both silent.
Sometimes I look down at her, and when she catches me she smiles and turns away. I do likewise when I catch her looking up at me.
It’s not until half way up that I realize that she is holding my hand. Anna’s hand is cold. Renee’s hand had been warm, and she sweated constantly.
I open the door to my apartment, and fumble for the light switch.
I hear the door close behind me, and then I hear the deadbolt lock into place.
I turn to look at Anna. Her back is against the front door.
On her face, she wears a mischievous grin.
For a moment, I wonder what I have got myself into.
But, before I can say anything, she grabs the back of my neck and pulls me down.
Her lips are warm and soft.
I feel her tongue push inside my mouth, and I can taste the wine she drank as our tongues dance together.
I feel drunk, and everything about her is intoxicating. When she finally pulls away, both of us are out of breath—now that’s a kiss.
I reach out, but then hesitate.
She understands what I want, and pushes her chest forward.
I cup her soft breasts, and find to my delight that she not wearing a bra.
I run my thumbs across her nipples, and even through the fabric I can feel them start to get hard.
She moans softly, as I continue to play with her breasts.
She sighs, and then I hear her say: “Pull the top down.”
It doesn’t take me long for me to grasp what she is saying.
I peel the top of her dress down, exposing her big chocolate colored breasts.
I go a little crazy then, as I drink in her breasts. I kiss the cleavage of breast, and gradually work my way down to her dark brown nipples. When I reach the nipples I lick the nub—first the left then the right. Then I pop her right nipple in mouth, and begin to suck. She moans in response. I wiggle my tongue around the nub causing her moan even louder.
Her other breast looks lonely, and I give it a good squeeze, and she gasps. I lean in, but she lifts my head up by the chin, and gives me a quick kiss.
She places a hand on my crotch, and rubs my stiff cock through my pants. It feels amazing, but I want more.
She must be able to read my mind. She unbuttons the top of my pants, pulls down the zipper, and fishes my cock out of my boxers.
Her eyes bulge at my now exposed cock. I’m a little surprised too—it’s bigger than I’ve ever seen it before.
She slowly strokes the shaft up and down, and now it’s my turn to moan. God I can’t believe how good it feels. But, I’m about to feel a hell of a lot better.
Anna lets go of my shaft.
She turns around, and now faces the front door. She bends over, and hikes up the bottom of her skirt. This gives me a perfect view of her beautiful round ass. My thoughts are sinful, as I stare down. Only a thin black strip of underwear keeps me from reaching the promise land.
I don’t need any encouragement to know what she needs, because I want it too.
I approach, and with a hand pull her panties aside to expose the folds of her pussy.
I take in her scent, and I can see she is dripping wet.
I fumble a bit, trying to find entry, and then…
I forget to breath. My senses are completely overwhelmed. And as I thrust forward, I realize that right now at this moment I’m truly alive, and I love every minute of it.
I’m just sane enough to go slow as I don’t want hurt her.
“Fuck! Yes!” She screams.
That’s all I need. I let go of her underwear, and grab her by the hips. I pull her back, as I thrust forward.
She lays her hands flat against my front door to steady herself.
Underneath me, I hear her continue to scream: “Yes! Oh God! Yes!”
I pump harder and faster.
At some point, she has stop screaming, and now all I hear is a steady chant of: “Oh god! Oh god! Oh god!”
I swell with pride, but I don’t know how much longer I can last.
Without warning Anna suddenly straightens up and wiggles free.
I stand there with my cock in the air wondering if I’ve done something wrong.
But then I see. I see Anna walk toward the bed, stripping off the rest of her clothes as she goes. I quickly follow suit.
We sit naked on the bed. God she’s so beautiful. Her brown body drips with sweat, and all I want to do is lick it off of her. She runs a hand through her dark hair, slicking it back.
She looks up at me, and smiles.
“No reason for us to be shy now,” she says.
She gives me a quick kiss, and then tells me to lie on my back.
Once on my back, she straddles me. She reaches behind her, and grabs hold of my stiff cock.
She lifts herself up slightly and guides my cock in. Then she slams down hard, we both yelp, as she impaling herself on my spear.
It isn’t long before she’s furiously grinding her hips, and riding my cock.
I just lay back and enjoy the ride, letting her do all the work.
But I’m greedy, and want more. I sit up slightly, being careful not pull out. This new position gives me a perfect view of her tits, and I sit mesmerized as they bounce lightly up and down. I reach up grab a handful, and she lets out a loud moan.
Then I do something that I’ve seen guys in porn do. While she grinds her hips, I thrust up into her. I do it again, and again. She howls.
My thrusts become even more aggressive.
We are both beyond words at this point. I grunt, she screams.
I feel her body tense, her screams turn into a long continuous moan, and then I feel her legs shake.
There is a popping sound as she lifts herself off of me.
She lays down next to me. Her breath is heavy and labored, and she doesn’t say anything for a long time. When she does, it comes out as a pant.
“Wow,” she says, “that was… just wow.”
She lightly taps her fingers on my chest, and then she strokes her fingers down, until they reach my cock. Her eyes go wide.
“Oh my god,” she says, “You’re still hard?”
I can feel her jerking my shaft up and down. Oh please, I pray, don’t let her stop.
“Poor baby,” she says, pouting. “My pussy is still pretty sensitive after the pounding it took…”
She smiles, and I smile back.
“Still there are other things we can do. Sit up.”
I do as I’m told.
She rolls off the bed, and then kneels down before me.
She suggests something that I would’ve have sworn only existed in a porno movie.
“I know you like these,” she says as she pushes her chocolate colored breasts together. “Put your thing between them.
The sensation is amazing. My thing, as she calls it, glides in and out between her chocolate colored breasts. It is soft and warm in that forbidden valley and I know I won’t last much longer.
A few more gentle thrusts, and I’m ready to explode.
Anna looks up at me both worried and confused as I pull out, and hold my cock in my hand.
I pump my hand a couple of times and aim for her breasts.
I cum hard. White goo splashes across her breasts and the bottom half of her face.
Anna laughs, and holds up her hands. She quickly turns her face away, as another blast splashes across the side of her face. Another hits her cleavage.
Cautiously, she turns to look back at me.
“Marking your territory,” she asks, as big globs of cum drip off her breasts and onto her knees.
Out of breath, I nod.
God, she looks so fucking sexy.
With a finger she scopes up some of the cum off her cleavage, and tastes it with her tongue.
“Mmm,” she says.
She leans forward, and kisses the tip of cock.
Then she stands, and makes her way to the bathroom.
I lay down on the bed.
I can’t believe my luck.
When I hear the shower running, I feel myself stiffen again.
“What are you doing,” Anna asks, as I pull back the shower curtain.
She looks down at my crotch.
“Oh,” she says, “I see.”
I step into the shower, and position myself behind her.
She lightly kisses the line of my jaw, as I cup her breasts. I fondle them, and sigh—remembering how good they looked covered in my cum.
I snake a hand down to her pussy. There is a little hair there, but it’s neatly trimmed. When my fingers reach their target I start to rub her clit.
She responds with a series of enthusiastic moans.
I want to finish what we started back at the front door. So I gently push on the small of her back. She guesses what I want, and bends over. She reaches out to her side and places a hand on the wall to support herself.
It’s easier to slip in this time, but it feels just as good—hell better than good.
I’m not gentle this time, and once I’m in I pound her hard.
“Fuck!” She screams over and over again.
I’m not gentle, as I said, and neither one of is quiet.
I grab her hips and thrust her back, so that I can go in deeper.
But then I realize she is pushing herself back. I stop thrusting, and let her do all the work—as she repeatedly impales herself on my cock.
Then I reassert myself, and hammer away at her again.
Her legs begin to shake. Suddenly she stands up and pulls herself free.
I look at her with a mixture of anger and confusion.
“Sorry,” she pants, “You made me weak in the knees. If we kept going, I would have fallen over.”
I understand, and it’s porn that comes to the rescue and gives me an idea.
I push her gently back against the wall. I move in close. Her wonderful breasts push up again my bare chest. I have her lift up a leg, and I cradle that leg in my arm.
She understands what I want now, and throws her arms around my neck, at the same time she showers me with a series of quick little kisses.
We look deep into each other’s eyes, and I see those big brown eyes go wide as I guide my cock into her.
I want her. I want her so badly that I can’t stand it.
She gasps, as I piston up into her.
I leave her speechless, and all she can do is groan.
I jackhammer my way into her, never letting up.
I’m focused, and the intensity of the act blinds me to how close I am.
She lets out a throaty: “Jesus!”
And, I blast a load into her. I’m past the point of no return as I shoot rope after rope of cum into her.
I’ve never cum so much in life. I wonder if I’ll ever stop.
Two more shot fire, and I’m completely spent.
I can’t read her face, and wonder if she’s mad at me for what happened. She just stares at me, with her mouth slightly open.
Then she lungs forward, nearly knocking me of the shower.
She kisses me hard on the lips. We drink each other in. There is a slight salty taste on her tongue—perhaps from my cum.
We drop to our knees, still kissing.
We finally pull away.
She lays her head on my shoulder, and I curl an arm behind her back.
We sit there until the water goes cold.
I help her dry off with a towel. In any other situation this probably would have sent us off on another fuck session, but we’re both exhausted.
And it’s nearly dawn.
We quickly get dressed. I offer to buy her breakfast, but she declines with a: “I’m just going to go home and sleep for a thousand years.”
I walk her to her car.
Neither one of us says very much, but then I’m not sure there is anything else to be said. To say something now would just run the moment.
But when we get to her car, it feels like I should say something.
“So…um… I’d really like to see you again, and not just at work.”
Some of my shyness has returned, and I feel kind of goofy asking.
She smiles, and tucks a few strands of hair behind her ear.
“Let me see your phone,” she says.
Shit, did I remember to bring it? I check my pockets, and breathe a sigh of relief as my fingers tap the plastic case.
I hand the phone over.
She taps a few buttons and hands it back.
I look down.
Wow, not only her phone number but her address too—which happily isn’t that far away, even by foot.
She gets into her car.
The last thing I see, before she drives away, are those big browns eyes staring back at me in the rear view mirror.
I tell myself that there is no way I’ll be able to sleep. I’m way too wired.
But as soon as my head hits my pillow I’m out.
I wake up around six that evening.
The first thing I do is check my phone.
I can’t believe it. There must be over a hundred messages all from Renee.
Truth be told, I’d forgotten all about Renee. And, my mind wanders briefly as I think about the night I just spent with Anna.
I start scrolling through the messages.
The messages begin at 8AM, and start off generic enough.
“Hey are you awake?”
“Are you there?”
I scroll down a little further.
“Do you want to take me to that new Chinese place? I heard they were good. Real fancy.”
I scroll down more.
“Fine. Don’t answer, jerk.”
“That’s what I get for dating some loser who doesn’t even own a car.”
“I can’t believe I let you kiss me.”
“Biggest mistake in my life.”
A little further down, and I read:
“You’re going to give me a good reference, right?”
“I’m not going to lose out on a good job, just because you can only think about yourself.”
I delete the rest of the messages, and block Renee’s number.
I have no idea what will happen with Anna and me. Maybe it was a onetime thing. God willing, maybe it will be something more.
But Anna did teach me one thing, though. That I sure as hell can do better than someone like Renee.
I call Anna.
She answers with a groggy hello. When she hears my voice, her tone brightens.
“Are you doing anything tonight?” I say.
“What did you have in mind,” she asks.
And all ready I can feel my pants tighten as my erection begins to grow.