This is my first ever story, please let me know what you think
I've never been much of a "ladies man" but I've had a couple girlfriends over the years, however, things have been pretty uneventful for me in the last few months. I work nights and live alone, and have never had any desire to go out and find a "hook up" or go out to a bar or anything without going with a bunch of friends. So basically, I don't like talking to people, especially when it comes to my apartment building. I just have no desire to talk to anyone unless I have to. I'm just your average late 20's introvert I guess.
Living in the unit above mine is an older couple who make it sound like they're stomping their feet everywhere they go, across the hall from me is a really cute girl, I'm guessing late teens early/early twenties who seems come and go whenever, and next to me is a newlywed couple (I was forced to talk to them shortly after I moved in) who for the most part don't ever bother me. There's also an older (mid to late 40's) lady kitty-corner from me who's very nice and still has a decent body that I say hi to every morning as I'm coming home and she is headed out to go to work.
One morning after I came home from work, parked the car, said hi to the nice lady (I think her name is Miranda) as she headed toward her car to go to work, just as I was about to put the key into my deadbolt, I hear a sort of loud, but whispered "hey!". I turn around to see the cute teen across the hall poking her head out her door looking at me with an uneasy smile.
"uh, hi, everything OK?" I ask.
"yeah... well, no, I need to ask a favor. I need some help."
"um...oookay, what can I help you with"
She opens her door and I see her in full view now, standing on her tip toes in a tight retro Star Wars shirt (with no bra apparently... it was a chilly morning) and grey yoga pants. "I need a big favor, I really need some help. Your name's John, right? I'm Jemma."
"Yee-ah" I reply slowly, "Nice to meet you Jemma, so really, what can I help you with?"
"come on in and we'll talk about it" she says, opening her door for me to come.
After I walk in she immediately closes the door behind me and locks it.
"Look, I need to know if you're a stand-up guy. I need serious help and I need to know if you'll be cool and keep your hands to yourself and your mouth shut after this is all over"
"EXCUSE ME?" I ask, getting irritated at the bullshit.
She starts to look like she's about to cry, and then squeaks out "Please, I need help. Please promise you'll be a gentleman about this and not tell anyone after. Please, just promise me."
"Fine, whatever. I promise. Now can you please just tell me what the problem is? I've had a long night at work and want to go to bed."
She gets an irritated look on her face "please take this seriously, I really need help and I don't want you bragging to your friends or trying to cop a feel or anything"
I'm really intrigued now, what with the whole "cop a feel" thing, so I agree as gentlemanly as possible "Yes, I promise, I will be a perfect gentleman. I will not tell anybody about this, and I will not touch you in any way inappropriately.... unless you ask" I threw that last part in just to mess with her, because why not.
"Thanks, and no, I won't be asking for anything more than necessary".
"Okay, So really... what is it that you are asking for?"
She stares at me for a few seconds, and then walks over to the couch, turns around with her back to me, bends over, and then proceeds to put her thumbs in her waistbands. She pulls it down about an inch and then looks back at me. I am frozen, my mind just screaming "WTF?". Finally she says " I was playing with myself last night. I bought a new ...toy.... and accidentally fell asleep when I was done...... with it... still in... me."
"Um.., ok, what kind of "toy" (making finger quotations), and what do you mean, still in you?"
She then proceeded to take her yoga pants and panties (if she had any on) all the way down, exposing her beautiful, round ass to me. And it was then that I saw it. A buttplug. Clear Glass. Rather large handle. I tried to lower my head a little to see the pussy beneath, but as I did she barked out "HEY! I SAID NO PEEKING!"
"Sorry, I just was not expecting that. Not many women just go ahead and pull their pants down in front of me. So what is the problem?"
"I can't get the buttplug out. I fell asleep last night and ever since I woke up this morning it's just been stuck there and getting kinda sore. It hurts too much when I try to pull it out. It's like it needs lube on the inside or something. Please, just help me get it out". She was practically in tears at this point.
"um, ok, I just want to make sure we're clear on this. You want me to help get the buttplug out of your ass, but no feeling you up or sneaking a peek at anything. Is that what we're talking about?"
"LOOK, I KNOW THIS IS STRANGE. but please" her voice softened "I need this out, it's getting really sore. Please. Pretty please, just do what you need to do to get it out. I'll even help you out when it's all over, just please help".
"help me out?" I asked, not expecting that.
"yeah, I'm sure you'll want to go jerk off or whatever after seeing and doing all this, so I'll just jerk you off instead, deal?"
"uh......" I mumbled out, not really sure what to say. I was going to help her out, but having her offering to jerk me off out of nowhere just kind of threw me off.
"FINE, I'LL FUCKING BLOW YOU, JUST GET THIS FUCKING THING OUT OF MY FUCKING ASS! FUCKING PLEASE!!!!"
And that was all I needed. "You have a deal. Do you have any lube around?"
"yeah, nightstand drawer" she said as she pointed back to her bedroom.
I walked back to the room and opened the drawer and found a decent size tube of astroglide. Walking back to the living room, I put a bit on my index and middle finger, and then swabbed it around so that all my fingers were coated. I put a few drops around her anus, and then began to start rubbing it around the entrance to her ass, eliciting a slight moan from Jemma.
"Does that feel good or something?" I ask, as I keep rubbing the outer edges of her anus, my cock rock hard now.
"mmm yes, of course it does. Can you just get on with it?"
"As you wish" I replied snarkily, rubbing a bit harder around the meeting area of the buttplug and her ass, hearing her moan even louder now. I slowly slip a finger under the skin in between it and the plug, this time drawing a small squeal from Jemma. "OH GOD, that feels good."
"Are you sure you want it out, or should I just keep doing this?" I say as I keep moving my finger around inside her ass.
"Just shut up and keep working" she says in a labored voice.
I continue to slide my finger around the plug, lubing it up as best as I could, while Jemma continues to moan, even starting to rock her hips back and forth as my index finger moves in and out and all around her asshole. As I move to the bottom, close to her pussy, I take a small advantage of the situation and lower my head down to sneak a peek. I almost stop what I'm doing as I am finally able to get a good look at her amazing , glistening wet pussy lips.
"What are you...ah... doing down there? Sneaking a peek like I told you not too?"
"Just making sure I'm getting you lubed up as much as possible" I respond with a slight smile.
"mmm hmm. sure. hope you liked what you saw"
I bring my head back up, and slip a second finger in her ass and continue moving them in and out, bringing them around back to the top, this time putting a little more pressure on her anus. "ugh, oh, ahhh my god, are you ready yet?" she asks, her head buried in her sofa pillow as she's pushing her ass into my hand.
"almost ready" i pull my fingers out, wipe them off, and grab ahold of the plugs handle. "Get ready" I tell her as I give it a small tug to let her know what's coming.
"ahhhhh.... go for it... ugh"
I start pulling the plug out, her ass not wanting to let go.
"OH MY GOD. OH GOD FUCK. HURRY UP!"
I pull a little harder, but her ass still will not give it up.
"OH FUCK THAT HURTS!" She screams, yet still moans as I let up a little.
"here, let me try something" I say, with a new approach in mind.
"anything, just do anything"
I start pulling on the plug again, and use my free hand to reach down and under her, my fingers finding her clit and start rubbing.
"HOLY FUCK WHAT THE FUCK ARE DOING? OH GOD FUCK"
Rubbing her clit even harder now, I start pulling even harder, finally getting some movement from the plug.
"OH MY FUCKING GOD HOLY SHIT IT FUCKING HURTS BUT IT FEELS SO GOOD! FUCK KEEP GOING OH FUCK OH FUCK OH FUCK"
I stick two fingers in her pussy as my thumb keeps working on her clit, and finally get the plug to come free, her ass just a huge gaping hole now. Jemma's whole body spasms as she screams, bucking her hips as hard as possible. i eventually let up on her pussy, and sit down in on the sofa next to her. She slowly stops bucking, still breathing very hard. "HOLY SHIT. I have NEVER cum that hard. FUCK."
She looks back at me, smiles, and slides down off of the sofa to kneel in front of me.
"You better be fucking hard" she says as she immediately starts unbuckling my belt and opening my pants.
"Oh yeah, you have no idea, that was fucking hot" I say, happily anticipating my reward.
"Good..." she says, still breathing heavily, pulling my pants and boxers down in one swoop, grabbing my rock hard cock and strokes it a couple times "..because you're not getting blown" she quickly says as she lowers her head and wraps her lips around the tip of my dick, licking the head in the process.
"Ahh, god, what?" I ask, feeling a little overwhelmed as she lowers her all the way down, practically swallowing my whole cock, and then slides back up, lubing my cock with her spit in the process. She goes down on my cock a couple more times, and then finally slides back up, keeping just the tip in her mouth, sucking harder while swirling her tongue around on the very tip, then letting go while licking my pisshole at the end of my dick, and then looks up to me with a huge smile and says "you're not getting blown, 'cause you're getting fucked". She stands up, lifts her shirt over her head and tosses it aside, steps forward, lowers herself to my lap, grabs hold of my cock, and inserts it into her glorious, hot and wet as fuck pussy, and then slides herself all the way down to the base of my cock.
"ooohhhh fuck, that cock feels good" she moans, as she starts moving her hips back on forth, stroking my rod with that hot pussy.
I finally start realizing that this wasn't a dream, and slowly bring my hands up to her chest, staring at those beautiful tits, just waiting to get my hands on them.
"mmm yeah, grab my tits" she says as I ease my hands around those glorious melons, running my thumbs over her perky little nipples. "OOH YEAH, just like that baby" she moans as she starts moving faster up and down on my cock. I lean forward and take one of the nipples in my mouth, licking, biting, and in the end slowly sucking on it "OH FUCK THAT'S NICE" she screams, up and down on my cock, reaching back behind her, down past her ass, until she finds her goal. As she keeps fucking my cock while I suck and fondle her tits, she begins to massage my balls.
"oh damn, yeah, keep doing that" i tell her, enjoying the sensation. I move my free hand down to her ass, squeezing it.
"hmm, you like that ass?" she asks.
"Oh yeah, I love that ass" I reply, and I draw my hand back a bit. SMACK. I slap her ass and she barks, started. "OH, FUCK, do that again!" SMACK! "OH, OH GOD" I take my other hand and slap her other ass cheek, and then slap her other check again. "OH FUCK! OH OH OH OH, OH GOD" I grab both her ass cheeks and pull her into me, slamming her onto my cock, over and over "OH GOD OH GOD OH GOD OH FUUUUUUCK!" Her body spasms as she cums, her pussy drenching my lap (and her couch) and her tits just bouncing in my face. Finally, she stops moving, and falls down onto my chest, breathing very heavily.
After a couple of minutes, she looks up at me. "You didn't cum"
"No, not yet"
"I guess we'll have to fix that" she says, smiles coyly, and goes down to the floor, on her hands and knees. "How does my ass look? Is it still wide open from the plug?"
I take a good look, her asshole still nice and gaping from the unusually large buttplug she had accidentally left in her ass all night. "Oh yeah, nice and big".
"Then take that cock and stick it in there. Fuck that hole"
"Yes ma'am" I say, practically jumping off the couch for the chance to fuck that ass. I grab ahold of her hips, line my cock up with her asshole (not that it needed much help) and drilled it into her.
"UUUHHHHGGG FUCK. Holy shit, that cock feels good" she begins pressing her ass back into me, as I begin plowing my dick into her, fucking that gorgeous ass.
After a couple of minutes I can feel my balls start to tingle. I reach down and start fondling her pussy, and she starts moaning louder, shouting obscenities as I fuck her ass even harder.
"OH MY GOD, OH MY GOD, OH MY GOOOOD" she screams as her body tenses up, her asshole squeezing my cock in the process, as I finally blow, unloading my cum deep into her ass, my fingers buried in her pussy, absolutely drenched by her juices.
After we both come down from our post coital high, I pull my softening dick from her ass, and remove my hand from her now completely soaked pussy lips. Jemma moans softly and repositions herself on the floor in a more comfortable position. I curl up next to her, lightly massaging her back and arms.
"mmm, that feels good. I could lay here forever."
"me too, but I need to clean up a little first" I say, really wanting to clean my dick off before I fall asleep.
"Let's go take a shower" she replies, as we stand, and she starts walking to the bathroom, gently leading me by dick, looking back with a smile.
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