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29
Anonymous
@confessions
28 Dec 2022 11:14PM
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Friday Night….

On a warm Friday evening back in 2019, around 6p, I get a desperate call from my best friend… “Can you stay at the house this weekend, entertain her, please” he desperately begins the call with? “Her” is his wife… I chime in “yeah man, she’s definitely feeling lonely lately” I say as I push for specifics…

(her and I chat, he and I chat, offering my opinion is very common as this has been the topic of conversation for quite some time)

Ignoring me completely, he continues,

“She keeps busting my balls, calling every 10 mins. She feels isolated, alone, you know how she is!” Again, I chime in, “brother she’s 40, the kids are almost out of the house, she wants you to spend time with her, take her to dinner, do shit”. He wants to respond but has nothing, he knows I’m right. “Brother, you both can afford to go do things, she wants to go places, experience life”.

For the record, and totally off topic. this man’s wife has the greatest pair of big fat tits. For those who think “bigger is better”, this is the one! Furthermore,
she’s thick but tone with dirty blonde hair, about 5’7”. Thinking about it, she has Kitty Lee’s body with a much prettier face.. A very attractive woman with a body built for fucking.

(according to hubby, she has a high sex drive and is very open minded… Cocksucker hit the lotto for sure)

With a long sigh he annoyingly utters what I could see coming from a mile away, “I don’t have time for this, Bobby is about to go on, can you stay at my place and keep her off my back so I can enjoy myself?”

And there it is…..

Honestly, he’s frustrated, I get it. He plans ahead for this weekend long festival well in advance, keeps her in the loop through the entire process, it’s kind of fucked thats she’s laying this guilt trip on him while he’s hours away. I’m torn, he’s been dropping the ball with regard to their marriage for a while now.. Then again, this is his once a year “get fucked up and jam out with thousands of dirty hippies weekend, “I suppose she should honor that.

Regardless…

Reluctantly, I respond with Sure man, I’ll head up there now and hang with her….” (honestly, I just want to hang at home, rub one out and crash, it’s been a long week but fuck it, she’s good people and fun to drink with)

Relieved, he replies “text me when you get up there, I’ll call and let her know, thanks brother” and quickly hangs up.. I set the phone down, take a deep breath, collect my shit and prepare for my hour long trip….

A bit of background on the friendship. Buddy and his wife married young, 18-19, had kids, they’re in their teens. We’ve known each other for about 20 years and they are 4-5 years my senior.

For the last few years we do dinner on Friday evenings at their place, a modest spot in the middle of cow country. We smoke, drink and eat well. I normally stay the night, sometimes sticking around on Saturdays to help with ongoing renovation projects.

We’re all an open book by the way, we know everything about each other. It’s actually very nice, I enjoy their company, as they definitely enjoy mine..

I’m divorced, have a great job and a high school age kid. I also have a very comfortable couch and plenty of food in a decent suburban apartment.
An apartment I will enjoy some other time, my drive is complete..

Teresa (wife) is on the porch, shorts, tank top, drinking a rum and coke. She has her hair in a ponytail, which is new for her. She normally dresses like a Sunday school teacher. Her hair always down, outfits very conservative, “boring” is the best way to put it. She certainly doesn’t show off her figure, her gigantic tits always put away, which is a shame quite frankly..

With a hug and peck on the cheek, I make a sarcastic comment, as I normally do, “sweet handle bar, you’re missing one side”. Teresa gives me a “you’re not funny” smirk” and proceeds to tell me that she’s been “experimenting with new styles”.

I waste no time, “you got it, flaunt it, I know Sam (hubby) would like to see more of you experimenting”. She immediately lets out a laugh, like, a quick chuckle filled with doubt, if that makes sense?

Again, in a serious tone I proclaim, “seriously, switch it up, show him you still got it, let him see other men gawk at you, get that little head going…..” She looks at me defeated and says “he knows what I have, what he has access to. He chooses to ignore me” using her hands to outline her breasts and body, exactly how the Price is Right women would display a new prize.. “I’m lonely, tired of being treated like I don’t exist. Months ago I asked him to sit the festival out” she exclaimed. “I asked if we could go away, focus on us for a minute, that I needed him…” Starting to well up, she rhetorically asks “Where is he” as she walks into the house….

So here I am, barely been there 10 minutes, she’s already crying and I’m on the porch by myself thinking “you couldn’t of talked about something else, you had to immediately bring up her failing marriage, good job jackass”….

She’s a strong woman, emotional and poetic, but tough. It wasn’t long before I hear her calling my name from inside the house. I take a deep breath and head inside. Teresa is in the kitchen, she cleaned herself up and is mixing both of a strong cocktail. Without missing a beat, she hands me my drink, we cheers and take a sip as she immediately picks up from where we left off.

As she starts to speak I take a step forward and gently lean in to give her a warm, comforting hug. I definitely surprised the shit out of her. At first she was stiff as board, cold, surprised at my very forward act. It took a minute before you could feel her body relax…. Not saying a word, we stood there hugging, my arms around her upper shoulders, hers around d my waste. Both of us, a firm yet gentle embrace, you could tell it meant something. It was quite nice if I’m being honest.

(being a dude, I have to point out how great her tits felt pressed against my chest, I finally have visual confirmation, as well as touch, of just how fucking big they are. Her puffy hard nipples, pressed against my chest, perfecto!)

After what felt like 20 minutes, I now have a rock hard dick so I pull away. “You’re a smart, beautiful, sexy woman who deserves happiness” I say, as I try to conceal my very obvious excitement. She looks at me and smiles as I conclude my thought “ponytail and tank top, my new favorite look” as I look down, laser focused on her giant titties that were currently on display, hours and hours of fun, beautiful cleavage, no bra)

Remember when I said “we know everything about each other?” It’s no secret hubby and I both have a thing for huge giant titties, conversations she’s been privy too, normally just giggling and walking away.. Staring down at them was certainly knew, however, she was well aware of my infatuation, in general, for big natural breasts. Yeah, I’ve looked at her, but nothing more than looking, in my head she’s a no-go, off limits..

It’s at that moment, still in our embrace, she says “I have to come clean”. Oh boy” spews out of my mouth as I question her, not with words, but wi5 the look in my eyes….

“I’ve had a crush on you for the last 20 years.” And don’t worry, Sam knows, he thinks it’s funny. “But, I want you to know, I’ve always had a thing for you.” Shocked, I ask “When me and the ex visited you, is this why you treated her poorly? Shaking her head in agreement, Teresa responds “that bitch took you for granted, treated you like shit for years”, you deserved better, fuck her”.

I laugh out loud as I share “she’s my one and only bad lay, dead inside and in the sack, terribly boring with no enthusiasm, a waste……” Teresa chuckles and shares “well, at least Sam has a big dick but I fantasize about other people when he fucks me. The one or two times a month he does fuck me, I keep my eyes closed, I go through the motions to keep my life semi-normal, but I’m not in love with him anymore, too many years have gone by, I’m over it”.

“Teresa, I had no idea it was this bad, I know he can be a dick, but never thought it was on this level, what are you going to do?” Teresa takes a step back, grabs our drinks and confidently shares “Hanna has three years of school left” as she hands me my drink, “once she graduates and goes to college, I’m leaving”. Her eyes start to fill with tears as we both take a big gulp of intoxicatingly strong rum and cokes… She leans over, grabs a tissue and wipes her eyes as we both take a well deserved gulp of mind numbing spirits…

Our drinks polished off, Teresa quickly time for another” as she grabs my glass and heads for the counter…… Unsure of what to say, completely blown away with the last hour of my life, Teresa swings her head around, ponytail in the air, and says “I’m sorry if my confession has made you uncomfortable, that was not my intention, I just needed you to know” as she turned her head forward to focus on drinks.

I don’t know what came over me, but I felt this urge to hold her.. The last hour had quickly turned in an emotional adventure for the two of us. However, she had a minimum of three years of hell to go through, which saddened me. I had lived that life and it miserable, my heart ached for her.

Throwing caution to the wind, I walked over and wrapped my arms around her stomach, careful to stay below her breasts, resting my head on her shoulder. She took a deep breath and reached for my arms. I whispered in her ear, “I’m here for you” as she let out a whimper and sigh of relief.

It wasn’t long before my dick was coming to life.. She was absolutely pressing her ass just enough for my guy to feel it. Moving from side to side, T was knowingly trying to get me hard and I could care less. I whisper in her ear “I know what you’re doing”, as I begin to mirror her movements, moving my dick from side to side, pushing in….

With both a whimper and deep breath Teresa takes her hand and begins to run it along my covered dick.. “Oh yeah” she says as I let out a gentle moan, immediately, and slowly, moving my fingers to the base of her giant breasts. I think to myself, “Finally” as I open my hands and grab the biggest pair of tits I’ve ever felt. Teresa let’s out a soft moan, catching her breath enough to say “please fuck me!”

Im so fucking hard I can’t stand it, as I respond “soon baby, soon” as I move my right hand inside her waistband, her pussy and clit my targets. She moans out again as I take my left hand, already squeezing and pinching her left nipple, I quickly grab her throat, pulling her head to my my face, forcefully, T whimpering away “How bad do do you want my dick in you” I whisper as she runs her tongue along her upper lip..

3 seconds later, and not missing a beat, Teresa, her hand in my pants now, my dick in hand……. Actually, it’s more like, “Teresa the magician, her hands suddenly down my pants, with a king fu grip on my dick, a grip so tight she could tell you how many beats per minute my heart was pumping” she’s rapid fire jerking me, it’s to tip, long strong stokes……

In return, my left hand still gripping her neck and my right hand buried in her pussy, I have two fingers fucking her pussy while rubbing and pressing her clit with her thumb.. T, well, she starts to moan and loudly and shake as she nutted all all over my fingers….

Teresa hadn’t been touched like this for some time, that was evident!

I nibble on her ear lobe, as she catches her breath, still feeling the effects of my fingers…. I whisper, “now you can have my dick”, slide me into your pussy” as I turn her to the right, and bend her over her kitchen table.. With my dick rock hard and still in her hand, I grab her ponytail and make my way for her opening.. With my left hand, now gripping the sexiest tits I’ve ever played with, I turn her head toward mine and say “that’s my pussy” as she loudly grunts out “take your pussy” as she rests my dickhead at the opening of her love canal..

Deep breath, deep breath as I tease Teresa with my dick, ready to push in fully, sliding in, the phone rang.. I pause, caught of guard by the phone, I say “fucking figures” as T slams her ass backwards and takes my dick…. “Yeah it does” she says as I quickly remember what my objective is….Pony-tail pulled back, left hand firmly holding a giant tit, sexy mom/wife panting as her wet pussy is ready to make a mess, I lay into to her, hard, deep, and aggressive, phone ringing off the hook…..

Let’s be honest… This didn’t last long… 5-6 minutes later, as our hearts race, Teresa screams out “you’re going to make me cum” in what I can only describe as a surprised tone.. “You’re pussy s soaked i murmur, ponytail still in hand, her back still arched, her moans and pants, now similar to a countdown. She’s ready to blow boys!! I give her everything I have, table creaking, both of us moaning loudly, Teresa’s pussy tightens…..

That’s all it took! In unison, I thrusted as deep as I could into her tightened pussy, and fucking unloaded as T let me know just how appreciative she was, nearly falling over as she came all over my dick. With her ponytail still in hand, left titty still firmly in my clutch, I bit on her ear and neck as we both appreciated just felt the effects of a fantastic nut……

A few minutes later, both of us, chuckling and giddy, completely spun from what just happened, get a drink of water. As I’m guzzling like a thirsty African baby, T pipes up and says “I haven’t came like that in years” as she stood back and took a sip of water, almost shocked at what happened. I ask if everything is ok and she quickly says “oh yes” as she intentionally spills water out of her mouth and down her huge jugs. “Thirsty” she asks as I quickly do what a man with a huge natural tit fetish does, as I grab both tits, in a loving embrace, pull them to my face, kiss her deeply and begin sucking her nipples………

Oh yeah, the ringing phone? That was Sam, I forgot to let him know I had arrived… No worries, 60 seconds after pumping his wife full of my nut, as I’m sucking her tits, Sam called back.. T answered, out of breath, Sam completely unfazed, he babbled away, praising me up and down to T, as she stroked my dick.

Sam, “so happy” that I “gave up my weekend to help him out”, requested me on the phone.. “Yo brother” I shout as he immediately thanks me then starts a long winded diatribe, excited to share the highlights of the bands, the setting and the great food. T, left to her own devices, grabs my dick, fat tits swinging, full naked body, she leads me by my dick to the couch as she holds up two fingers…. Sam, he’s still raving about his stress free hippy induced weekend, clueless to the fact that as I say ”sounds like so much fun brother” his wife is on her back, legs spread, pussy soaked, guiding my dick back in the very same spot Sam used to call home.. Round 2 has indeed started,,

Sam called back the next day, he and I on the phone for quite awhile. I remember him saying “its much more relaxed now” as he immediately started the process of repeating the same shit he said the night before, which led to him thanking me again for getting his wife off his back… “Yeah man, she seems happy to have company” I blurt out as he asks for me to put her on the phone…

“Oh man, she’s at the market” I say, as Sam chuckles quite loudly, blurting out “yeah she loves spending my money,” as he chuckled on, eventually saying “I’ll call later” as he hung up…. I’d imagine he saw a half naked dirty chick, or dudes eating shrooms, which is why he just hung up.. He was “on to the next one” ass they say…

Speaking of which…

I’m triple checking to make sure the phone is off screaming out “I can’t hold it anymore!” T, mouth soaked with saliva and spit, and clearly not at the market, grabs my nuts and slams her face to the base of my dick, not missing a beat, or drop, as she emptied my sack deep in her throat… Like a bitch, I screamed out as I felt every last drop empty my nuts. By the way, a second orgasm not long after a man’s first orgasm is quite intense, it’s quite nice!

Teresa enjoyed sucking my dick with her husband on the phone. Admittedly, I enjoyed it as well. The threat of getting caught is quite addictive. So much so, we test the limits of our sexual prowess weekly. I fuck my friends wife regularly, right under his nose..

Case in point-

Friday before Christmas, while Sam sits in his recliner, stoned out of his mind, eating cookies zoned out, Teresa and I will go for a night walk. Sam completely unfazed and happy to have the tv to himself, clueless that his wife and over night guest are 20 ft away, watching him watch tv, fucking like school kids. Me squeezing her nipples, smacking that ass, pulling her hair, drilling her pussy! Teresa, holding onto a tree, taking my dick from behind like the good girl she is, her fat little pussy tightening as she cums, while empty my seed deep into her, fully embraced, while hubby watches cartoons or some shit…

Or right now.. He just got in the shower. T, in a flannel, no bra, immediately goes in and grabs a tissue, making sure the coast is clear. Sam, fully engulfed in washing his ass has no idea his wife literally walked out of the bathroom, about 10ft, slide her pants down and sat on his buddies dick. Of course, I’m unbuttoning and pulling the monsters out, as the smell of Irish Spring permeates the air..


Till next time..

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10
Anonymous
@confessions
02 Oct 2024 2:07PM
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A while ago, my wife left me for another man - our relationship wasn't the best and we both knew it was over. It was a depressing time and it took me a while to get over the divorce. Luckily no kids were involved (even after 15 years of marriage). I coasted through life, turned 50, and really wasn't looking for a serious relationship... until I met this beautiful 24-year-old French girl, who was an art student visiting the USA.
I was a regular to a small dive of a coffee shop, I'd go in there and kick back, read a book and drink some coffee. She was in there a lot too. Eventually she approached me and talked to me.
"You know there's nothing more attractive than a guy reading a book... My name is Reine." She said in broken English with a heavy French accent. (It turns out her name means Queen in French)
I must have blushed, I wasn't used to talking to super attractive women at all - in fact most of the time if I was lonely I'd just find some ugly slut to fuck, or try Tinder which usually resulted in ugly sluts lol.
We talked for a while, got to know each other and she told me she's always had a kink for older men.
We started dating, I told her "You know I'm 26 years older than you so if we're still together when you're 50 I'll be 76 or dead."
She laughed it off, "We'll worry about that if and when we get there. Okay?"
I fell hard for her, I was head over heels in love. She was sweet, charming, and paid attention to me. What more could a guy ask for?
After a few days of getting to know her, we fucked - and let me tell you I've never had any sex that compared to what I've experienced with her. There was energy involved, it was like both of our souls met on a higher level and nothing else mattered.
I warned her that I was getting older, and I got some Cialis to make sure I could stay nice and hard for her.
It was probably about the fifth time we were fucking and she looked into my eyes as I plunged into her and spoke some French, but then translated it into English:
"I don't want you to pull out of me when you cum, I want you inside of me... deep inside of me forever my love."
I paused and all kinds of things flooded into my mind, especially if she was on birth control - and then I leaned forward and kissed her as I began thrusting into her beautiful body. I came deep inside of her, and she held me tight as my cum sprayed into her tight pussy.
It turns out, she had a creampie fetish - a breeding fetish.
This went on for months, and she ended up moving in with me. I'd fuck her almost daily, unless she was on her period. One day she looked a bit concerned and seemed to shut down, and she wouldn't talk to me about what the problem was. I went to work, and when I came back there was a note on the table from her.
"I didn't want to tell you, but I am pregnant and my visa has expired and it needs to be renewed so I need to return to France, I already had a flight booked and I was afraid to tell you. I love you very much and I don't know what to do. You are the most perfect man I have ever met, and I hope one day to be called your wife... but for now, I will return to France and get the visa renewed. I hate leaving you like this, it's stupid of me I know. But if you knew I was pregnant and returning to France, you would have stopped me. I will text you when I land and we will make plans to be together my love.
Always yours,
Reine"
I had a panic attack. I texted her, called her, and nothing. Days passed and depression set in for me.
While I loved this woman with all of my heart, I knew nothing about her family, or where she lived in France. All of her clothing was gone, and she didn't have too many personal items...
Sometimes we would sext each other when I was at work, and that's where the picture came from. I just miss her - and I have even thought about going to France to look for her - but how the hell would I even find her? It's such a big country. I don't even know what city or town she's from.
It all came to a head and I was about to do something stupid and hurt myself (hey depression sucks - and being this in love with someone... well it's like having your guts ripped out)... but I finally heard from her yesterday:
"I'm coming back, but I want you to promise me that we can be married. My father and mother disowned me, they're heavily Catholic. I am sorry I left the way I did, I am sorry for hurting you the way I did, I was just in a bad place - being pregnant, and knowing I have to tell my parents. I will see you soon, I still have a key."
Of course, I texted her back like "WTF WHERE ARE YOU" - hell I don't even know why I'm doing this - maybe out of revenge... but maybe for advice - she's so fucking stunning looking, she's so talented too. I'm broken without her, but I do know that will eventually pass - yet it's so hard to deal with such a loss. Sorry for rambling. Yeah I'll take her back... I might delete this later.

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Gidding
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@confessions
08 Mar 2013 1:27AM
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I confess...I have a fetish for older women that has only gotten stronger as the years have passed. The reason for this is the best (actually the ONLY *really* good) sex story I have.

This was 8 years ago, the summer of 2005. I was 15 and it was the July 4th holiday. My parents had a little pool/barbecue party for the block. I was swimming for a little while. When the sun started to go down I decided that was enough so I went upstairs to change. I dried off and got into a pair of my gym shorts, just for the time being so I could hang my suit in the bathroom and get a shirt and some sandals.

I went to the bathroom and was waiting. I thought- weird, the only people I figured would be using the upstairs bathroom was my mom or dad or sisters but they were all outside. The door opened after a minute. It was Mrs. Batelli, who was my mom's friend from the block. When she came out, she was adjusting the top of her sundress- really nice dress, orange with a pretty good cut, and I'm sure you know exactly where my eyes went. She was probably about 41-44 and she was nicely proportioned, probably around 145 and 5'6" or 5'7". Shoulder length auburn hair. Had a good tan on by that point in the summer. Her name was kind of deceptive, she wasn't Italian at all, that was her husband's name. I think she was some kind of European little-bit-of-everything mutt, but the tan was pretty far from her natural skin color. And it looked good. She had the legs out, nice shape- not very long but hey. Her tits were very nice, very perky for her age. Not huge, probably a small C or large B. I was staring dead at those suckers because in adjusting herself she was really moving them around and hadn't noticed me. In fact, I think she was about 6 inches away from bumping into me before she realized I was there.

She just went "Ooh!" and stepped back, definitely startled.

I just stood there, probably with some idiotic look on my face because I just got to watch a solid 6 seconds of tits bouncing around.

I expected her to react adversely, but she put her hand on her chest and started laughing- actually quite hard, much harder than the situation probably warranted.

She was like "Shit!" and kept laughing. I had no clue what to say, just kept smiling like an ass.

So she takes two steps, stumbles right into me and gives me this big half hug with one arm so that those firm tits and pressed right into me and she goes "You scared the HELL out of me!" and just kept laughing. I had still not said anything!

This is when it dawned on me- how long she'd been here, since noon, I wasn't keeping track of her drinking but she was fairly petite- this lady was HAMMERED.

So I think I said something like "Glad to see to you too,"

She said, "You didn't talk to me all day!"

We exchanged bullshit for about two minutes, none of it is interesting. Finally she said, "Your house is nice. I'm staying here. I'm going to sleep over."

I was kind of chuckling at this point and I just wanted to humor her so I said "Cool!"

She goes "Let's have a sleepover party" and I answer "Sure, that sounds like fun."

And then out of nowhere, she goes "Do you trust me?" all serious all of a sudden and I answer "Of course," because I think she's going to tell me something weird or something.

But no, as soon as I say it, she comes right up, pulls me in and gives me this deep, fucking awesome tongue kiss. Let me tell you. I had NO clue what was happening. She was working her tongue all over my mouth and I got instantly hard. She tasted like spearmint and- I didn't know at the time, but now, unmistakably- rum. And lots of it. Captain Morgan and Doublemint. I'll never forget it.

After about twenty seconds, she pulls back and goes "Somebody's gonna see this" and I think "FUCK! Come on!" but I was very happily mistaken because she grabbed my hand and pulled me into the bathroom.

I threw my towel and suit into the tub. She locked the door and put on the lights and the fan (cover up noise? I dunno) and she pulls me into the sink, falling, so that we both hip-check the counter. More tongue kissing. Fucking awesome, none of that awkward high school bullshit.

Her tits were right up on me and after a minute I started feeling bold so I slowly raised my hand up the back her leg and felt on her thigh. She had damn good skin for a middle aged woman, must have lotioned up all the time. I was wary, and frankly, a little worried that a wrong move on my part would blow the whole thing and I'd kick myself forever. But I was also horny as fuck at this point and just wanted to touch all her bits. But, to my delight, as I felt on her thigh she pulled my hand and guided it right up the dress onto her nice, firm ass. She was wearing the high-cut bikini panties. Guess she hadn't embraced the thong yet. I didn't care. It wasn't a big ass, but the texture was fantastic. Firm, but soft. Not muscular but not flabby. I was throbbing at this point.

She must have known, because she grinding the top of her leg against my shorts. She had me salivating. I pulled my other hand up her dress and onto the other ass cheek. Fantastic.

Then she reached down and fondled me through my shorts and gave me a little squeal. It was a lovely little sound. She stopped to spin me so I was up against the counter then back away and pulled her dress over her head (with surprising grace) to show off her body. She had a nice figure, cut pretty well for her years. Her bra was white and strapless. She whipped it right off. I got my third really good look at some live tits. This was the epitome of awesome. I felt like a fucking champ. But it was only the beginning.

She sauntered over to me and smiled and said "Show me" in the hottest voice I'd ever heard. I immediately dropped my shorts. I'm not going to brag about my cock. I'm no mandingo, but I was hard as a motherfucker. She said "Nice" and dropped her panties.

Her pussy was beautiful, symmetrical. None of the curtains you might expect on an older mother of two. She was shaved smooth. I'm pretty sure I audibly said "Fuck"- as in "Fuck, I am going to wake up any second now."

She came up to me and put her lips back to mine, and as she did she cradled my balls and started carefully to appraise my cock. She was teasing me. My heart was beating like it was going to explode. Then she got up on her toes and slid her pussy over the top of my shaft. It was like heaven. I don't know how I didn't cum right then and there. She leans into me and I think she asked "Do you want to help me cum?" and I just nodded "Yes" even though I didn't hear her completely. Whatever, she could have asked me to to stand on my head.

So she grabs my head and moves me so I'm about eye level with her tits and pulls me into them and says "Kiss my nipple like I kissed you". I tried my ass off to be good. Who knows if I was. Soon, she was purring like a kitten. She dipped her hand down into her snatch and started playing with her clit. I could hear how wet she was. I told myself "Shit, good, I'm doing it right."

She took my hand and guided it to her pussy. Her slit was so wet. She used just my fingers at first, but soon she was using my whole palm- long strokes, she had me cup it hard and my whole palm was getting slick.

Then she asked, "Do you have a condom?"

- FUCK -

I mean of course I didn't. I wasn't sexually active. My heart sank. I was abut to lose my virginity and I didn't have a fucking rubber.

I said, "No". She said, "It's okay."

My cock was denied entrance, but she balled up my hand and slid my index and middle fingers inside her and fucked away, vigorously. I went back to licking her nipples, harder and faster with the rhythm of her body. She came, I felt her snatch tighten as she squeezed and she threw her head back.

It was something to behold, indeed, but fuck man, did I regret not having a condom.

"Thank you," she said, with kind of a giggle.

"Now-" she said, and dropped down to her knees. I put my palms flat against the counter. She pulled my hips forward, grabbed my butt a little, and then slid her lips over my cock. I'm a little biased, but it's still the best head I ever got. Her skilled tongue lapped over my head and shaft and she gently caressed my balls. It was like waves of electric everytime she bobbed. She took the whole thing. I only lasted two minutes, having been dying for release for so long by this point. I came buckets and she moved down even deeper as I did so that it ran down her throat. She swallowed every last drop and cleaned me off with her tongue as she pulled back.

The whole encounter lasted less than twenty minutes. After I came, she started to dress herself again and said "Don't tell anybody, ok?" I nodded, lightheaded.

She left, and I laid in my bed for a few minutes to recuperate. When I went back downstairs, she was gone. Her husband was too, so I guess he decided they'd had enough and they were going home. I have a lot of theories- the husband was some kind of professional, like a lawyer or something. I first thought she was neglected but later I found out that he was most likely cheating on her. I never found out, but what does it matter?

Naturally, I kicked myself for not having a condom. It was about nine months later when I finally lost my V-Card.

After the encounter, I saw her less. I always wanted to try to see if she would ever be alone so I could ask her about it, but the opportunity never presented itself. Later, I thought about maybe trying to blackmail her, but I had a pang of consciousness and thought it would be shitty of me to do that to the lady who gave me my first great sexual experience out of the blue with no strings. I still have mixed feelings. I wish I would have hit it.

Eventually, she divorced the husband and moved away, out of the state and remarried. I haven't talked to her.

I took a few things away from this- first and foremost ALWAYS HAVE A RUBBER. you never know when your mom's friend will suddenly and for no reason decide to get frisky with you. Secondly, I still love the older ladies. I've only had a couple of other experiences after, but the first one was the best and most special. I still frequently knock one out thinking about that blowjob and fantasizing about what could have been.

Oh well, the inexperience of youth, etc.

That's it. This story is 100% true and I hoped you enjoyed it.

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The room was a bit crowded at Whorefest 2024, it was mostly middle aged men lusting after younger women, but there were a few women in the crowd too. I made my way to an empty chair as a young woman stood on stage, completely naked only for the purple thigh high ‘fuck me boots she wore, I gawked at her sexy exposed perky breasts. She spoke with enthusiasm and pride, walking from the left of the stage to the right and engaging with the audience.

“It’s not about how you look, it’s about how you make me feel when you touch me. I don’t give a fuck if you’re fat, ugly, old, or whatever stereotype society has given you. You can be an old man, or even a mid-twenties businessman, or hell even a middle aged woman – I simply don’t give a fuck. We meet for pleasure, your pleasure! And my job is to satisfy your needs. I’m that slut your mom warned you about, I’m not a dinner date, I am dinner.”

Some of the audience clapped, a man next to me grunted in approval. She continued on.
“Now I know what some of you might be saying, that we’re all about using condoms and safe sex – and for a lot of people that is a really big turn off… lots of people like it raw, no barriers – and that’s why I’ve come up with various tiers on my regulars list. If you can prove to me that you’re clean, and you don’t have any diseases, you won’t have to use a condom. Hell, I’ll even let you empty your nuts inside me,” she laughs and shakes her head, “hell that’s kind of a fetish of mine. I love creampies. Of course there are requirements, I’ll definitely follow up with your doctor’s office and make sure everything is legit. Once I know, you’re in. Literally in.”
She points to her pussy, which has a tuff of dark pubic hair.

“Now you’re probably asking yourself, fuck how much is that going to cost? Bareback creampies should be affordable to everyone – so I charge a lower rate for that than most of the providers here. My prices are non-negotiable, they’re locked in for a reason – trying to barter will get you removed from my fuck list, even if you are a regular of mine.”

A few people in the crowd clapped lazily. She was trying hard to win them over.
“The raffle will begin in a few minutes, and I hope all of you get who you desire!”
I uttered, “Raffle?”

The man next to me heard me and explained, “Yeah we all got raffle tickets when we came in, check your gift bag bro.”

I thanked him and looked inside, condoms, a few weird pencils and a raffle ticket. I shrugged my shoulders and continued to listen to the lady on stage.
“Have a great rest of the evening, and fuck you later!” She blew a kiss to the audience and walked off stage, her little tits jiggling with each step.

A woman got up from the crowd, barreling towards her waving her hands, “Lucia! Lucia! Here’s my number call me!”

The woman handed her a piece of paper and Lucia smirked and winked at her, nodding in agreement.
The last speaker was an older woman, she was very reserved and had a smoker’s voice. The guy next to me was very excited as she spoke about her sexual exploits.
“I’ve always dreamed of fucking Mistress Sheila, she’s a 60 year old goddess,” he said to me blushing.

I didn’t say anything, she was a bit too old for me.
She finished talking and they started calling the raffle tickets, they called my number for Mistress Sheila, and I turned to the guy next to me, handing him the ticket, “hey you won!”
His eyes lit up as he looked at my ticket, “are you sure? Holy shit!”
Grabbed the ticket and put it up in the air, “I won!!” I patted him on the back.
He handed me his ticket, “here, I hope you get someone good if you win!”
The raffle seemed to go on forever, and there were only two ladies left, one of them was Lucia.
They called my numbers for the raffle, I won a night with Lucia. I was told to walk over to her booth to make arrangements to meet her, and I did.

Her booth was small, it had black curtains around it that I moved aside and stepped in, two security guards were just outside of the curtained booth. I saw a single chair and sat down. Lucia walked in and sat behind a desk, she was now fully clothed. She smiled at me and looked a bit nervous.
“Hi, I’m Mike,” I said nervously.

“I’m Lucia, it’s nice to meet you Mike. So you won a night with me huh?”
I smiled a bit, “I did…”

“Let’s get to know each other,” Lucia said as she picked up a pen and slide a notebook closer to her, she began writing.

It seemed like a job interview, she asked me what I did for a living, about politics, about religion, and then about my sexual preferences.

I was very forthcoming about all of the information she asked me about.
“Favorite sexual position?”

“I like it when the woman is on top so I can view her better, and touch her breasts and look into her eyes too…”

“Ah, standard cowgirl, gotcha… ok,” she penned it down.

“Any fetishes?” she asked, her eyes locking onto mine.

“Um…” I felt really nervous, “I- like…”

“You don’t need to be shy with me, Mike. I’m here for you, ok?”

I nodded, “I like the same fetish you do, cumming inside… creampies. It’s the only type of porn I like to watch – seeing a pussy filled up with cum to me is so fucking beautiful and perfect… but I know I don’t have my medical records with me, and I know that won’t happen…” I trailed off.

“Yes, creampies… feeling that pulsating dick and the rush of hot sperm pumping deep in me, there’s nothing like it… so I understand, but yes we will be wearing protection, ok? You can cum inside of me with a condom on.”

I nodded, “I totally understand, and I feel the same way about it.”

“How old are you, Mike?”

“I’m 52 years old, getting older, how old are you?” I asked.
She smirked a little, “I just turned 22, you dirty old man. Oh don’t worry, I like older men – with your peppery hair and refined look. Hell, I’d probably hit on you if I saw you at a bar.”

Lucia took out a business card and wrote on the back of it, “Meet me here at 8:00 tonight. I’ll take you out to eat – my treat, and then we’ll head back to my hotel and have some fun.”

I took the card and saw the address she wanted me to meet her at, she put a heart around it.
I went back home and cleaned up, took a nice warm shower and made sure I was ready for action. I opened up my bottle of Cialis and took one, then thought about wanting to be ultra hard for her so I took another pill and broke it in half and took it too.

Lucia had a limo pick me up at my hotel, when I opened the door I didn’t expect her to be inside, but she was. I was greeted with a hug and a kiss, “Mike! This is going to be so much fun!!”

We had a great dinner and a great conversation. I asked her if there were any other rules I needed to know, like if kissing was allowed. She was very open and kind, it really did seem like we were on a date getting to know each other.

“A lot of providers don’t allow kissing, but to me – that’s the spark. A lot of them don’t like it because it’s too intimate and they’ll get feelings for their clients, but that’s exactly what I want. I want to have feelings – I don’t want to be dead inside about the people I’m fucking.”

I was stunned by how mature she was, and even wondered how the hell she could afford such a luxurious restaurant.

“You must have a lot of clients to afford eating here… it’s easily $250 a plate…” I said, trying not to be offensive.

“I actually am pretty new to the whole scene, just been in it for 4 months. Thing about me is, this isn’t a job it’s a hobby. I don’t even have to work, my family is rich as hell. Perhaps this is my act of rebellion, but it’s a rebellion that is fun!” She laughed and took a sip of wine, “let’s go back to my room Mike….”

The limousine drove Lucia and I to her hotel, she had a very fancy p********ial suite. I watched her walk over to her bed, and let her short black leather skirt fall to the floor, and then she pulled her top off over her head. She sat on the bed and spread her legs.

“Are you afraid?” She said grinning, sliding a slender finger down her clitoris and into her pussy. My cock jumped, as if to say “what the fuck are you doing dude, get in there!”

I pulled my clothing off as quickly as I could, stumbling to the bed as Lucia kept using her finger to play with herself. My cock throbbed, so my hand instinctively gripped onto it and I started stroking to her.

“ohhh no, you bad boy, you’re not getting off that easy!” she leaned over and put the finger she was playing with herself inside my mouth. I felt her soft warm hand clasp on to my cock and start tugging it gently. Her mouth met mine, her tongue thrusting deep into my mouth – we both moaned in pleasure.

Lucia pushed me down onto the bed and she started kissing my nipples, then my belly all the way down to my cock. I felt her wet warm mouth take all of me inside her. Her soft hands gripped my waist as her head bobbed up and down frantically. She came up for air, licking the tip of my dick, playing with the precum.

“Fuck you’re hard, such a nice dick!” she started tugging on it and sucking it at the same time, looking up at me, making eye contact – I was hooked. This woman was amazing. I stopped her, and pushed her down on the bed, spreading her legs open wide. I licked her erect nipples, and made my way down to her navel – she giggled as my tongue tickled her. I pushed her legs back more and my face dove into her sweet glistening pussy, my tongue lapping at her clit, and occasionally diving into her cunt hole. She smelled and tasted great, she was sweet, like honey.

Her body began to convulse, and she screamed out “FUCK!!! MIKE HOLY FUCK!”

Lucia nearly passed out, so I stopped licking her and cuddled into her as she recovered.
“Holy fuck, who are you?” she asked groggily.

I just chuckled. I felt her hand on my chest as she rested her head on my arm. I kissed her forehead and just relaxed. She began to stroke my cock softly, our lips met again, and she climbed on top of me. I felt her tight little dripping pussy slowly swallow my cock.

“Oh shit, the condom?” I said as she looked deep into my soul.
“Fuck the condom,” Her mouth was on mine as she started riding me, her small tits jiggling on my chest.

I could feel her energy, so sexual, so young, so loving, it was tantric. She moaned as my cock pushed deeper inside of her, I could feel her pussy muscles milking my cock as she slid it in and out of her.
“You feel so perfect,” I said, panting cupping her little tits in the palms of my hands.
“So do you…” she moaned, her eyes fluttering as she quickened the pace of her thrusts.
I pushed upwards with each thrust to go deeper, she was so tight I knew I wouldn’t last long, and I didn’t. I grabbed on to her waist, then her ass and I felt my cock start to throb, the warmth of my cum sprayed deep inside of her, the ejaculations pushing the limits of my consciousness, I held her tightly as she drained every single drop. She collapsed on top of me and we both fell asleep.
We woke up in the morning and kissed, had coffee and ended up spending the day together. She didn’t want me to leave, and I didn’t want to leave either…. So I don’t know where this is going to take either of us, but it’s definitely going to be one hell of a ride.


*Yes, this story is fiction. Parts of it were taken from my own personal life – but no, I never met a woman at a place called WhoreFest lol. I hope everyone enjoyed the read. Peace!

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My neighbor moved in with her husband 2 years ago. Her husband is an over the road truck driver, so he’s gone 6 days out of the week mostly. Sometimes he’ll be home for the weekend but for the most part he’s gone a lot. When he’s home he drinks until he passes out in the backyard, or go out to a bar. They have no children, so she’s all alone when he’s gone.
When he would leave, she would ask me to help her with little things, and being a good neighbor, I would always help the little lady. I’m 52 and my wife decided to leave me a good 10 years ago, so instead of going through a shit ton of financial loss (again), and having my heart break (again) I just decided that I didn’t want any relationships and that I’d just play the field and fuck whoever came my way. My neighbor (we’ll call her Jessica) is 36, and always wanted to chat me up when she saw me outside. I’d always be nice and friendly, talking about the weather, and just general bullshit going on.
We grew into pretty good friends, if she seen me outside sometimes she’d call over to me to help her with something – usually some handyman issue that her husband never fixed. Things really took an interesting turn 6 months ago, she called me over to see why her stove wasn’t working and I immediately found that the gas was intentionally turned off to the stove.
She knew I knew, and she knew she was caught. Jessica was embarrassed, and sat down on a chair in the kitchen and started to cry.
“I’m just so fucking lonely. I’m sorry for bugging you.”
I consoled her, told her that I was her friend and that she could always talk to me.
She got up, and hugged me really tight, I could feel her pushing her tits against me and her hands gripping on to my shirt as she sobbed.
“I’m really fucking lonely…” she murmured. Our eyes met, we kissed, and we fucked.
As you can see from the picture, Jessica isn’t a bad looking woman. Her raven black hair, her lovely tits – she’s got a lot going on for her. Since we first fucked, when her husband is away, she’s always over at my house and even spends the night sometimes. She’s admitted she has deep feelings for me, and I have to say I do have feelings for her too. We’ve been fucking behind her hubbies back for a good 5 months now, and I’ve never used protection. Little lady has a bit of a fetish for creampies, she says her husband never touches her anymore and they’ve been married for 8 years. She awkwardly admitted that she can’t remember the last time he came inside her.
She’s been talking about filing for divorce, selling the house and getting an apartment – but I told her that she didn’t need to get an apartment because she’s basically living with me when her hubby is away. Hell, my bedroom has bras and panties laying around half the time because she leaves her clothes at my house half the time.
When I told her that she didn’t need an apartment, she lit up and was excited.
“I totally would love to be in your arms every fucking night,” she paused, and blushed.
“I’m so fucked,” she said as a tear rolled down her face.
I was confused, “what? What is wrong?”
“You don’t want to know, I just realized something.”
I shook my head, “what is it babe?” And then I panicked a bit, “are you pregnant?”
She laughed, “no… not at all. I just realized I’m in love with you and it’s not just any little crush, I’m madly in love with you and I don’t know what the fuck to do about all this shit, I need to get a divorce. I’ll go see a lawyer tomorrow.”
My heart stopped, fucking hell time stopped, but words came out of my mouth that I wasn’t even trying to say, “I love you too.”
I fucked her again, looking into her eyes as I came inside her.
Currently she has filed for divorce; her husband didn’t seem to mind and doesn’t even know I’m banging his wife. He’s talked to me a couple times over the fence of our properties.
“You’ve been a good neighbor bro, but the house is up for sale and I’m moving away. She can go do whatever. We really lost our connection a while ago, she got mad because she found used condoms that I forgot to throw away in my truck. I mean you’re a man right? When you’re on the road and some cracked out lot lizard is pounding on your door for a $20 fuck, why deny it.”
I just nodded my head, “yeah men have needs.”
He grunted, “yeah, the fuck she think happens on the road? She’s a dead fuck anyway, fuck we haven’t fucked in probably two years.”
That was the last time I saw him. Jessica is living in the house until it’s sold, but always comes over – she has a key to my house. Every night we’re having fun, she makes me feel like I’m 18 years old again. I’m not sure that we’ll get married or anything like that, but it sure is nice to have a beautiful woman in my arms every night. Jessica is planning on getting off her birth control pills, she did ask me if I wanted to be a father – and I told her that I’d love nothing more than to inseminate her beautiful body with my cum. So, I might be breeding her soon. Fucked up thing is, that’s her word for it, “breed me daddy.”
She likes to be on top and loves doggy style too. Gripping her soft tits while I cum inside her is fucking amazing.
She knows I go on porn sites, we’ve discussed it because I brought it up a while ago. Jessica actually loves watching porn, and doesn’t care that I take her picture. I hope Jessica stays with me for a while. She’s a very nice woman, literally tells me what’s on her mind, we talk about all kinds of shit, 100% open and honest with each other too.
Sometimes life sucks, but if you wait and let it flow, it will reward you.

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Starting in June of 2006. i graduated HS in 2005. I'm 25 now, this was when i was 19. I had a rough school year that year, i studied my ass off and was struggling all year in school, when i got to the point where i said fuck it, and just dropped every class. i got a job apprenticing at a tattoo shop (not really a job, i didn't get paid i just got free tats and was first learning how to be a tattoo artist myself) when i started smoking weed a lot more than i ever really did before. I also tried coke for the first time, and would drink regularly.

I met a guy through the shop, who i will refer to as "Mark". mark was like 30 something at the time, working as a piercer there. he always had girls coming in and getting piercings from him, going in his booth for up to 20 minutes at a time, and i never saw money exchange hands. a lot of the time, the girls definitely didn't look 18, and I'm sure their parents weren't there letting this happen. my suspicions got the better of me after being there about 2 months and i walked into his booth to borrow his cell phone charger, and he's getting a blow job from a girl while her other friend was sitting at watching and laughing. he told me to come in, and i was just standing in the doorway, with the curtain over my shoulder, unsure as to what to do. he told the other girl i was a tattoo artist there, and that she should hook up with me. without really any hesitation, she got up and started to come over to me and kiss me. i kissed her back for about 10 seconds, before i pushed her off and walked out. after a couple minutes they all came out of the booth and the girls left and mark came back over to me. he was laughing lightly and simply asked me why i didn't get a blow job or fuck her or whatever. and i was like well man, i have a girlfriend, you know that. and plus i don't even think those girls were legal. and he said and ill never forget exactly what he said to me that day. "who fucking cares about their ages man? they want dick just as much as any girl". and i was totally about to debate him, but i had no valid argument. i agreed.

I've always known deep down i find younger girls (around 14 - 18) attractive, but never really fantasized about doing anything about it. but i definitely realize their beauty. working at the tattoo shop i got to see a lot of girls, and after picking up piercing in 2008, i got to pierce a lot of tits. some clits, but they were older women and 20 something year olds. the 17 year olds coming in getting their tits pierced was awesome as fuck though, and even one time, a mother and daughter both got them done at the same time. mothers tits were saggy as fuck and gross though.

now i apologize to anybody thinking this is the extent of my confession. that was only the beginning, I'm trying to give you a light history as to how this whole thing happened. i was exposed to younger girls for a couple years. i worked with mark off and on, at two different shops together. we shared girls and even had a foursome with two girls somewhere along the lines, but after awhile, it wasn't cutting it for me. i wanted more excitement, i wanted more passion.

i started using cocaine heavily at this point, winter 2009. it wasn't to the point i was beating anybody for drugs or stealing or anything, but a lot of my income (at that time i was making around 60k a year) was going to blow. i was constantly working, i co owned a shop with a friend of mine from high school, and we were doing ok. he also did coke, and i was the one who sold it to him. He became ALOT worse than me at it, and he would go on binges of 2 or 3 days without sleep or food. he was to the point it was almost sickening to watch.

well after awhile of this behavior from him, he started messing around trying to get a lot more coke than he could afford, trying to sell it. he was cutting it so much, he couldn't even sell it to anyone because it was shit, and secondly, i was selling to everyone he was trying to sell it to. this pissed me off, but i let it slide and kind of helped him out and would give him more than i would give anyone else.

well i remember the day, he calls me at like 2:45am. i shoulda said i remember the night, but oh well. early morning. he sounded like fucking shit, like he had just blown an eight ball and called me a second later. he was talking fast as hell rambling on about fucking up horribly. this was normal for me, i would listen, mumble every things gonna be ok, and tell him id see him tomorrow. well he started to yell, then get quiet and say to himself no don't yell don't yell. he said dude you have to come over my house. you have to come over right now. and i kept asking him why, what was so important? he just basically broke down and said he couldn't tell me, but he needed me to come over. so i got on my clothes i took off about a half hour before to try to get a couple hours of sleep, and headed to his apartment. it was only 4 blocks away so i ran.

i go in his building and up to his floor and knocked on his door. he let me in after it sounded like he was moving shit around, and i came in took off my jacket and said what the fuck was the big deal?

he lead me into his family room and sat me down on the couch. at this point I'm pissed that he's all coked out, hasn't paid me yet for any of it, and is probably going to rant on about how he needs more or something. well he looks at me and is like, we need to go to the store. we need a lot of things. and i look at him and say dude, what the hell are you talking about? i get up, and I'm walking over to the kitchen to at least drink a beer because I'm awake, and i almost fell over. i fucking kicked a body laying on the ground.

under me, on the hardwood floor, was a girl, half naked, with only pajama pants and socks on. laying on the floor. no blood, no wounds or anything. I'm thinking ok so she's passed out drunk or something. maybe she's sleeping and he wanted her to leave. but then it occurred to me. why the fuck would he call me, tell me to come over in such a rush and say we needed to go to the store to buy things? I'm pretty sure this bitch is dead at this point. i back away. i almost vomited. i sat back down. i asked him to explain how the fuck this was happening.

he told me he got the ball from me earlier in the night when we were leaving the shop (around 1030, it was a slow weekday night) and he went to his friends house. his friend apparently didn't have any money to do the blow, so he came up with an idea. he was going to get my friend some pussy for some coke. my friend of course said ok, that would be fine. the other guy said he would have to go out and call his friend and for my friend to come with. they both hopped in the car, and while they were driving through the city, the other guy randomly stopped on side street. a girl they had passed was walking past the side street, and didn't walk down it, and kept walking. the guy then turned the car back on, and pulled onto the main street then onto another side street. he turned off the car, and got out this time. the girl walked down the side street, and apparently the guy struck a conversation with the girl.

my friend is thinking at this point that the girl is this guys friend, and she's going to come and fuck him later. well, the guy takes out a rag, puts it over her mouth, yells at my friend to open the back door, they throw her in the car, and they drive off back to his friends house. when they get to the house, for one reason or another, the guy didn't want to stay there, so they went to my friends house. the one who's living room I'm sitting in now wondering why theres a body on the floor.

so once inside, my friend started to scream at the guy and all this shit, and the guy casually explains, he found someone my friend could fuck, and when he was done, all they'd have to do is put her somewhere out of the city after feeding her a bunch of xanax and she wouldn't be the wiser. well how coked up my friend was, he went along with it. he said he and his friend fucked her for an hour or two, and then his friend left unexpectedly to let my friend deal with the girl. my friend said he couldn't drag her out of his apartment alone or drive her anywhere because he didn't have a car. so this was apparently where came in. well the first thing i did once i knew the whole story, i went back over to her. checked her pulse. thank fucking god she was alive.

second thing i did, was ask if he had any xanax. and he said of course. i asked if he had fed her any yet. he hadn't. so i crushed up two 1mg pills put it in a shot of water mixed it around, i layed her on her back and poured it down her throat. good, now she will be out for a little longer. i wasn't trying to have her wake up in the middle of my brainstorming.

now i know what you think. yeah this guy couldn't have been so calm and collected during this. I'm writing this years later, describing what i was DOING. my mind was absolute shit at this point. i had vivid hallucinations of police running through the door arresting us both. this girl looked 16 or so, she was half naked drugged and unconscious on my friends floor, and i just fed her anti anxiety pills commonly used for date rape.

i look at my friend after i gave her the zannies. i said i need to go home and get my car. we need to do this quick, before its like 5 or 6 am, and more people are leaving their apartments going to work or whatever the fuck their doing. anybody up at this hour is most likely drunk or fucked up so we should be fine if we get her to my car in 4 minutes and nobody sees. so I'm about to walk out the door. when it occurs to me.

i look back over at the floor, see this girl laying there. its too easy. as I'm walking over to her I'm taking my belt off. my friend looks at me like I'm crazy and is like what the hell are you doing?! we have to get her out of here man! and I look back and say, dude, if you don't shut the fuck up, you'll be the one laying on this goddamn floor. I'm tired, i got a bunch of shit to do tomorrow morning, you call me over here for the weirdest fucking request anyone has ever asked me, I'm going to fuck this girl. because if i don't, and we get fucked for this, i would totally regret not doing it. he started to argue me, i said stfu a couple more times, and he sat back down.

i got down on the ground, i took off her pajama pants. stared at her pubic hair airstrip down to her nice pussy. just looked at it for a minute. i licked my fingers, and slid two of them up and down her slit. i started to put them inside her, and it felt so weird. whenever i fingered a girl before, it was responsive, and would tighten up however i moved my fingers. with her, there was nothing. i was still rock hard, I've had a sleep fetish forever and this was pretty damn close to that. a girl who is laying there susceptible to whatever you want to dish out, taking it all no matter what.

i whipped my dick out and rubbed it along her clit, and as I'm doing this, i suddenly yelled to my friend, go and grab my fucking car and bring it back here. i threw him my keys. he got up and ran out the door. i looked back down at her, laying on her back, i started to slap her tits around. nice B cups, and bent down and sucked on the left one. then i guided my cock up to her pussy, and rubbed the head of it up and down her slit. i really had to spit on my dick like three times to get it wet enough to get it inside. once it was in, i just really pounded it like how you would beat off when you really just wanted to cum as quick as possible. after about two minutes of thrusting, i felt the cum building up.

i pulled out right before i busted, and i opened her mouth, and came into her throat. i took more water from a cup on the coffee table, and poured a little in her mouth. i put my clothes back on, washed my hands, washed my face with water, then i went and grabbed a bunch of baby wipes from the bathroom. yeah, i knew my friend had those, he docent use toilet paper he docent like it he uses those like old wet baby wipes. weird, but in this situation i was thankful. i put one around my fingers, and shoved it up her pussy. rubbed it around the edges, and rubbed her face with it. i ended up grabbing around 10 more, rubbing her whole body down with them. i don't really know if that would destroy evidence, but i did it anyway.

after what seemed like eternity, my friend comes rushing in the door. he wants to know how were going to get her out of the apartment, and into the car. i asked where he parked, and he said out front. i said no you dumb fuck, theres a camera out front your building remember? we need to take her out the back in to the alley. I'm going to find some girls clothes and dress her up. he didn't have any clothes from girls or anything like that, so i put her in a big hoodie and picked her up. i said i would pretend she was sick and i would mutter how she needs to feel better and wed be home soon down the hallways so if anyone came out their door they would think i was ushering a sick girl home to her own bed. i said go now, get the car, and pull up out back. it took me about 10 minutes to carry her down 4 flights of stairs to the back door. thank god the only person who saw me was an old lady who was walking her dog to the end of the hallway to piss on her neighbors door. dumb bitch. everyone in the building hated her. she would probably forget in ten minutes i even passed her. i finally get outside, my friend has my car idling there. he opens the back door, i throw her in the seat, and i hop in and he gets in the back seat. i was going to say get up front, but it made more sense. when i pull over, he can just open the door and push her out.

i have no idea where I'm going to go to do this in a secluded area. so i just drive. i got on the highway, and i drove a couple exits till i wasn't in the actual city. every red light i was debating just doing it right there. but eventually, we got to a stretch of road that wasn't well lit and it was secluded. woods on both sides. so i pulled over real quick, and he opened his door, and kind of slid her off the seat. he told me i was good to go, and i drove forward, and he shut the door. i looked in the rear view mirror, she was about 3 feet off the shoulder on the grass, not super visible, but if you drove by, you would definitely see. no cars were coming, so i sped down the road and back onto another more lit road and drove around till i found the highway again.

by the way, he took off his hoodie i put on her, pretty much last second before i pulled over. thank god, because that might have been evidence against him.

so long story short, or should i say long story even longer, was we finally got back to his apartment, by this time, it was pretty much light out. we both get upstairs and i laid down on his couch. for what had happened, i was surprisingly calm. i felt pretty damn good. i told him it was fucked up to get into a situation like that, but hey, i was just as guilty as he was for going along with it. we drank a couple beers, decided on not opening the shop in a couple hours, and went to sleep.

i really never forgot about it like i woke up the next day and rehashed it so many times n my head, fucking her, pounding what felt like her lifeless body, and nutting all in her mouth. i knew my friend would never tell anyone either, i mean, why risk it? but anyway, the next night, we were at a bar we tend to frequent for a couple drinks a couple nights a week. somebody was talking about how someone they knew heard about someone THEY knew who got "kidnapped" and then was found outside the city the next day. me and my friend looked at each other, and asked the guy what he knew, and seemed mesmerized something like this would happen. it was almost funny in an eerie sort of way.

needless to say, nothing has ever come of it, and I've since quit all drugs completely, my friend still smokes weed and we both drink but other than that, were doing ok. the guy who actually grabbed the girl in the first place is in jail now apparently according to my friend. armed robbery. could of seen that coming.

well i feel a lot better, I'm confident that this won't get back to me, unless someone does a shitton of digging and finds out the actual incident, but i don't even think it was reported to the police or in the paper or anything. so good luck.

ONE LAST FINAL NOTE. to anybody who says pics or any bullshit, i totally would of taken pics and vids of her and me fucking her, but i still wouldntve posted them on here. maybe a pic if i blurred the face, but yeah ir egret not having a camera. well my hands fucking hurt like shit from typing this up so franticly. at least if you think its fake, you read the whole thing and enjoyed it. i know what i did. i don't care what you anonymous people think. the more people who think its fake, the better off i am anyway.

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Anonymous
@confessions
15 Jun 2022 2:53PM
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[ − ] thread [ 39 replies ]

I confess I've been fucking a homeless woman for the past 5 days, and have been paying for her cheap hotel room, buying her food too.
It all started last Friday on the 11th of June. I went to the store and this woman was on the sidewalk, her head between her hands looking down at the ground. She had a small sign that read, "hungry and homeless please help." She had dark brown hair, tan skin - and from what I could see a nice figure. She looked to be in her mid 20s, and I approached her, put $5 in her cup and turned around to go inside the store.
I heard a soft, "thank you."
Not looking back I casually said, "no problem, I hope things get better for you."
I went in the store and bought some items, but also thought I should get her something to eat too. So I did. They had sub sandwiches for $5, and I got her one, plus a box of chocolate chip cookies as a desert.
I got out of the store, and she was still there, head between her hands. I placed the sandwich and box of cookies next to her and turned around to walk away.
"Why are you being so nice to me?" she asked, with her soft voice.
I turned around and she was no longer sulking, or hiding her face. She had no makeup on, but was absolutely beautiful. Her blue eyes penetrated me, and then I noticed she had a black eye and a few bruises on her neck.
"Holy shit," I was horrified, "are you okay?"
"I- I am fine. I don't need your pity. This is what happens when you hook up with an abusive asshole. Thank you, god bless you for helping me."
"Look, whoever did that to you..." I searched for the right words, "I hope you don't have any contact with them anymore."
"I don't, that's why I'm homeless. I don't want to go to a shelter, I tried that and someone stole everything I had."
Someone walked by smoking a cigarette, and she asked to bum one.
"Get a job," the guy mumbled.
I pulled out my wallet, "here's two dollars for a cig."
He stopped and pulled a cigarette out and gave me one.
"Be more empathetic," I told him. He shrugged and walked away mumbling under his breath.
I handed her the cigarette, she already had a lighter and with a tiny flick of her thumb it was lit.
She inhaled it deeply, and I noticed she seemed far off and distant for a second as if she was thinking of a better time.
"Not too many people give a fuck about people like me..." she said.
"I try to - but the way society is, well we're all pretty much fucked." I told her.
"Yeah, well you probably got a white picket fence and a house, and me - well I make a lot of bad decisions, as you can tell." She lifted up the cigarette gesturing that smoking was one of them.
My dick started thinking for me at this point. She was pretty, had a nice body, nice tits. Her face was rounded with nice cheek bones. She was a bit dirty. Her shirt was stained, and she obviously wasn't wearing a bra. Her jean shorts were faded and ripped.
I was attracted to this woman, and blurted out, "If you need a place to stay..." I stopped myself. I didn't know her, and certainly couldn't invite her back to my place.
She looked me in the eyes and I could tell she was about to cry.
"If you need a place to stay I could get you a hotel for a few nights. Get you some food, try to help you get on your feet. Help you apply for jobs."
She smirked as a tear rolled down her dirty face, "No. I don't need you to be my savior. I'll be okay, really."
"I'm not looking to be your savior, nothing like that. I try to help people as much as I can. I don't have anyone in my life that I have to pay for, I'm a 38 year old loser to be honest. Sure I have a good paying job, I have my own place - but... well. What do I have to show for it."
"You have a house, probably a wife, kids..." She said looking down at the sidewalk.
"I don't, that's what I mean - I don't have anything to show for all of my accomplishments... so if I can help you, it makes me feel better about my life. Understand?"
She put her cigarette out on the sidewalk, grabbed her backpack and got up. She was sexy, with toned legs, nice hips, perky full breasts - her nipples poking through her stained shirt. If she took a nice hot shower, she would clean up well. Perfect 10 in my book.
"I'm in a bad situation, I guess I need all the help I can get at this point."
We walked to my car and I opened the door for her, she laughed a little.
"And they say chivalry is dead," she said as she shut the door.
I got in and started my car. I knew there was a cheap hotel a few miles down the road. We had a bit of small talk, she said she went to college for finances but dropped out because she met her ex that she 'fell madly in love with,' but that the relationship turned out to be a complete nightmare.
I asked if she had parents, or siblings that could help her out, and she got pretty quite.

"When I was a teen, my family went on a road trip that I refused to go on. They didn't even leave the city and their car was hit by a drunk driver. I lost my mom, my dad and my brother. The police showed up at the house and that's how I found out. So I got put into the foster care system until I reached 18... then I left. No aunts or uncles, nobody. Grandparents passed when I was a child, I don't remember them. I'm all by myself, and I have been since my parents died. My foster parents were loaded. They paid for all of my college, but when I dropped out because of my ex, they pulled all their funding and disowned me... which is completely understandable but I just can't forgive them for turning their backs on me. I know I'm not even their own flesh and blood, so they didn't even need to pay anything after I left."
I didn't say anything. I felt bad for her. She was completely alone.
We got to the hotel, $55 a night, which wasn't bad. I could surely afford to house her there for a few days.
I went in and paid for 5 days. With tax it was just under $300. I got the key and went back to my car and handed it to her.
"It's all yours. Just don't trash the place okay?" I said laughing.
She laughed, "Hey you're welcome to come in, I like talking to you. I haven't talked about this shit in a very long time."
My dick woke the fuck up, "Sure, it's good to get bad things we've experienced out of our systems. I'd be happy to talk to you about anything you want!"
We went to the designated room and she unlocked it, she went in first and I followed her.
Someone had the air conditioner cranking full blast, and the room felt like it was 50F degrees.
She turned it off, then turned around towards me.
"Look at me, inviting a guy to a hotel room and I don't even know his name..."
"I'm Jason, nice to meet you..." I left it open because I didn't know her name either.
"Judy," she said as she plopped her backpack on the bed. She opened up her backpack and pulled out some red and white underwear and walked over to the sink. She turned on the water and soaked them, using soap to scrub them.
"Ugh, I barely ever get to wear clean clothes - so I do my best to keep at least my underwear clean!"
"I mean, yeah - I'd probably do the same thing too if I was in your situation."
She stopped washing them and hung them over the ledge of the counter near the sink to dry. Judy tried to fix her hair up in the mirror as best she could, but she really needed a brush.
"Hey, if you want I can buy you a brush or whatever... do you need anything else?"
She paused and looked in the mirror at my reflection still standing by the door.
"Am I a kept woman now? Are you going to buy me all these things and keep me locked away in your tower?" She seemed a bit agitated.
"No! I'm not like that, I just wanted to help you out. Look, I'll let you be - I just really understand how things can really get bad."
I turned to open the door, "Take care of yourself, ok?"
"Hey wait, I'm sorry... I'm just... No one has ever tried to help me like you have... tell you what, you can get me deodorant and a brush. Maybe some red lipstick and some blush? A toothbrush and toothpaste? See, I'm getting greedy now." She was smiling.
"Ok, consider it done!"
"I'm going to take a shower, clean up - can you go get that stuff? I'd love to sit down and talk to you more."
I did. I went to a store and got her everything she asked for. I thought about getting a pack of condoms but then thought there wasn't any point. I was there to help her, not fuck her. Yes I wanted to fuck her but given she was abused, she's probably not going to want to have sex. So about 25 minutes later I was back at the hotel room, and knocked on her door.
She opened the door, her hair was still wet, she changed her shirt to a black shirt that revealed a lot more cleavage, and I could see a perfect outline of her tits. Her nipples were very obviously erect. She also changed her pants to jogging pants. She smelled of hotel room soap and shampoo. Her eyes caught me checking out her tits, but she didn't say anything at all. She was very beautiful all around.
I went in and sat down in the single chair that occupied the hotel room. She bounced on the bed and found the TV remote on the side table, clicking the TV on. She flipped through some channels and then turned to me, ignoring the TV.
"So what's a nice guy like you single for? I mean not that I'm any catch or anything like that... but honestly - no girlfriend? No wife? What's up with that?"
"Judy, sometimes life throws bullshit at you, ya know?" I said, kinda looking down, a bit embarrassed about being single.
"I was engaged once. I was going to marry someone but she decided she liked a fat tow truck driver instead... so one day I came home early from work and this fat greasy bearded ugly dude was fucking my fiancé, right on the bed. She yelled at me like it was my fault. Her tow truck driver fuck buddy got off her and charged at me, so I got into a huge fight with him. He fractured 2 of my ribs, I busted his eye socket and jaw. Cops came, he was arrested for assault. That was 10 years ago."
"Oh damn Jason, I'm so sorry. People are such assholes."
"That, they are."
She pointed to her black eye, "see this? This is what happened to me when I caught my ex doing meth. I smelled something funny and when I found him he was smoking it. Something broke in him, idk what happened because the next thing I remember I was waking up on the floor with a pounding headache. That was a few days ago. I packed a bag and left. It's not like things were good between us anyway. He was fucking this other woman, I really didn't care because I'm bisexual and ok with open relationships, but he started paying more attention to her. Turns out she was doing heroine, and he started to do it too. Then they got into meth, and I warned him that I'd leave him if he didn't clean himself up. It got worse, and I fell out of love with him. I just stayed there because I had no where else to go, and no one else to turn to. Well, after waking up when he knocked me out I knew it was time to leave." Judy looked sad as she remembered the traumatic events.
"Hey, I'm sorry that shit happened to you, but you're safe now ok? Judy look at me."
She did.
"You are safe now," I said again.
"Hey Jay, come over here and join me on the bed so we can watch some stupid program that we don't even give a fuck about," she said wiping a tear away.
I sat on the bed, away from her.
"Get over here!" she pointed to the empty spot next to her, "damn you're so fucking shy it's cute!"
I moved next to her. She put my arm around her and snuggled into my chest. She put the remote down and looked up at me, and kissed me. I felt her bite my lower lip, and then her tongue (which was pretty long) push deep into my mouth. My tongue found hers, and I pulled her body close to mine. My cock was throbbing hard. Poking through my jeans. I didn't want to make any moves, I wanted to take things slow, out of respect for her - but she had other plans.
Her hand found my cock, she unzipped and unbuttoned my pants. She took her shirt off revealing perfect breasts. I slid my pants off, then took my shirt off as we passionately embraced each other.
She took off her jogging pants, revealing that she hadn't shaved her pussy in a while.
"I haven't fucked anyone in 6 months," she panted. I laughed and she gave me a confused look.
"I haven't fucked anyone in over 5 years," I told her.
Our lips met again, my hands cupping her breasts. They were so soft! My hand glided down to her beautiful round ass, which was just as soft as her succulent tits! She pulled away from my kiss and licked and sucked my neck. Judy pushed me down on the bed and engulfed my cock in her mouth.
She moaned as her mouth slid up and down my shaft. My hand found her pussy and I slipped a finger inside her. She was soaking wet and dripping. Judy began to ride my finger, and I put another one inside her. I felt her muscles clench around my fingers as her tongue licked and flicked the tip of my cock. Then she mounted me. When she did, she screamed with pleasure. I grabbed on to her waist, looking up at her perfect body.
"Oh Jason, yessss" she moaned.
I was already feeling like I was going to cum, it was building up and my dick was getting even harder inside her.
"Oh Judy, slow it down babe, it's been a while..." I panted.
She sped up, she tightened her juicy cunt around my cock and smiled.
"Ohhh you're going to like this Jay..." she said, sliding me in and out perfectly.
And I did. I liked it. I came so hard in her I nearly passed out. All of my nerves convulsed, I could feel each ejaculation pumping inside her, filling her."
She could feel me too, and she loved it. She kept bucking as I came, and moaned louder. My erection didn't go down and she kept fucking me. I turned her over and started drilling her missionary. I kissed her lips as her nice tits bounced to each thrust I pumped inside her. I must have cum inside her a lot, I could feel it dripping down my balls.
"Oh right there," she moaned.
So I kept pumping her in the same spot. Her body twitched and her eyes rolled back.
"JASON, I'm going to cum all over that cock!" I increased thrusts and started pumping her harder and harder, I was going to cum again, I was going to cum too!
I filled her again.
We laid down and held each other for hours.
The first thing out of my mouth, "obviously you're not on the pill..."
"Obviously," she said as if it was a stupid question.
I stayed the night in her arms. Saturday, Sunday, and Monday I fucked her and came inside her even more. I offered to pay for her hotel a few more nights, but then decided to let her stay at my place.
"Would you like to come home with me? I mean, I just am offering..."

So that's where I'm at. She agreed to give it a try, to see if it will work out. I asked her to be my girlfriend, she said yes. Today is Wednesday, she's at my house - I'm at work. She's looking for a job.
So what do you think? I've never been with a woman that is so sexy. She cleaned up really well. I've gotten her more clothes, and she puts makeup on even though I tell her she doesn't need it.

I do have feelings for her, and even my brain is teasing that I have a future with her - maybe even marriage... but I asked her something...
"Why would you even be interested in me, I'm not handsome."
"Feelings have nothing to do with looks, and honestly you're not ugly at all, give yourself some credit. Plus, I have a fetish for older guys and you fit my fetish quite nicely, daddy."
I laughed.
"No, I'm serious - it's a kink. If we're going to be together we need to be open and honest with each other. If you ever want to fuck another woman, now that we're in a relationship, we'll have to have that talk ok? Don't get me jealous, it's hard to do but being deceitful will wreck what we have."
"Honestly, you're the first woman I've been with in a very long time Judy."
SO that's where we are at rn. In some ways, I kind of hope I got her pregnant... but I'm also worried that she's gonna run back to her old boyfriend and leave me. I know it's a long story, and for that I do apologize... peace.

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