[M/F] I'm in love with this cougar... | 2016

This is going to be a long read so be prepared (but there's pictures in the comments if it's any consulation). Also, my obligatory disclaimer of no promises of everything being said as verbatim. I did my best off memory. A little prologue...

I've of recent, been actively pursuing casual sex after a chance happening a few weeks ago. About a week ago I found out that the girl I'd been fucking is married. She told me otherwise when we met, and while they weren't living together at the time, she admitted to screwing around with a few guys while she was supposed to be "working it out." She made it easy on me and pretty much told me she was done.

I was a little disappointed, but I understand. So anyways I realize I should use this opportunity to try to meet new people. I figure online would be the easiest and require less 'work' (my game isn't all that great). So I hit up Craigslist.

That's a fucking disaster.

Everyone that responds is either a prostitute, or shady as hell (I think a few were pretending to be women). I decide to solicit instead, but that's another fail. Even though I clearly say hetero, the only people that respond are dudes. Not sure if any guys have had luck, but I wont be trying that again. I tried adult friend finder but find out it costs money. I'm a cheap bastard and didn't wanna pay anything, so no dice there. Then I tried plently of fish. This worked for me, but not without effort, let me explain.

I feel like all time I spent on /r/Gonewild looking for girls that were down to swap pics prepared me for this. First off, the best strategy by far is to cover as much ground as possible. I would literally just send a pic and message to almost every post on Gonewild. It's not about appealing to a specific girl, but weeding out the girls that don't mean business. So anyways back to the story.

While there wasn't a lot of people in my city, there were a TON in the city I work in (large city in Northern CA). I sent probably 20 messages that night. When I didn't get a response by the next day, I broadened my range and literally sent out like 300 mass messages. It sounds drastic but the more seeds the better the yield, right? Occasionally I'd customize the message if I found the girl interesting or thought of something clever, but it didn't seem to make a difference on gonewild, so I kept that to a minimum. I actually got a decent amount of replies that day. But now that you've weeded through girls that will talk to you, you have to differentiate the women that just want an ego stroke, and the women that are down to fuck.

I started a dialog with a few. Some fun flirty banter that could possibly lead to something, but one quickly set herself apart from the rest. She was really direct, with most girls wanting to text and be pursued. Asked for a dick pic straight up, and made it clear she wasn't seeking a relationship. We started texting and decided to meet. While she made it clear that this was about sex, she still wanted to meet up before hand. So said I'd take her to lunch. It felt like an interview. I met her at a spot downtown (told her where I work).

She was older than I usually go for, a lot older actually. I was surprised she was interested in me considering she's in her mid 40's, and I'm 27, but I was kind of excited too.

So we meet up, and she looks a little older in person than in the pics I seen, but she's a pretty women. She's pretty slim, taller than I'm used to. Probably 5'10 with her boots on (to my 6'1). She has light brown hair with some blonde highlights. She has jeans, black boots and a white t-shirt on, nothing overly sexy. Her tits I'd say are on the smaller side, but they compliment her narrow torso well. We sit down and talk.

I was hoping it wouldn't be awkward (age difference paired with subject matter) and it's not. She says she has a thing for younger guys, and likes to pretend they are her son's friends (son is a couple years younger than me.) I tell her how I've never been with someone that much older than me, and how it's one of my fantasies (who doesn't have a MILF fantasy every now and again?) She tells me she's divorced with a few kids, the oldest in highschool. She's a student (unemployed). Pretty much answers any questions I have without flinching.

We flirt a bit but it's pretty tame. She says she's into latin guys (I'm half Mexican) which is somewhat ironic as I don't speak spanish and am not very tan. 3rd gen, pretty American. But I go with it. She's intelligent, funny, and surprisingly down to earth. She doesn't come off overtly sexual like the last girl I was hooking up with. By the time were leaving I realize it's been an hour.

As we leave she leaves it open to when/if we'll actually hook up. I tell her I'll text her, and go in for a kiss. I was expecting a peck, but she gives me a soft passionate kiss instead. I was a little embarrassed with people walking by, but it was hot. She tasted great (unlike the last girl I kissed, who always had smoker's breath). I head back to work. I think about texting her after I get off, but decide against it as I don't have my car anyways.

So I usually take the train to work, but the next day I decide to take my car just in case. Around noon I decide it's time to hit her up. I text her and ask what she's up to. About 20 minute's later she sends me this: http://i.imgur.com/r4hGjNt.jpg "Nothing. Wishing I had someone to play with : ("

Pretty much insta-boner.

I run off to the bathroom, snap a pic of her handy work, and text it to her. I Explain how I'm always the horniest in the middle of the day when I'm supposed to be working. She says she's at home and her youngest is at school.

It's go time.

I head out for lunch and navigate to her house. She lives in a nice area. I ponder how a unemployed single mother can live in the hills, but whatever, not my business. So I get to her house, only takes me like 15 minutes from my office. She opens the door in that sheer tunic from the pic. She looks so damn hot. She seems a lot shorter now as she's barefoot.

We go to her room and she sits down on the bed, and crosses her legs modestly. This turns me on fiercely for some reason. I ask her to see a little more, but she says me first. I take my shirt off and pull my quickly hardening dick through my zipper. She motions me over, and gently grabs my dick and slowly jerks me a bit from the bed.

"Your turn" I say.

I push her on her back, but she keeps her legs crossed. I gently pry her legs open to reveal her pussy. I was a little surprised to see a decent amount of hair, considering the pic she sent showed her bald. But I love a little bush from time to time, so I just say "mmmmm" and ask if I can touch. She tells me no.

"I was actually working out when you texted, but I've been waiting for you to text, I didn't wanna miss you." She says she sent me a pic she had in her phone already, and that she's gonna need a shower before I can touch. She figured maybe I'd like to join her.

At this point I realize I'm not going to be having an afternoon quickie. So I pull my phone out and call my boss standing right there.

'I had an emergency come up and am going to have to head home for the day, sorry boss." I say as I'm looking her in the eyes. Not gonna lie, I felt smooth as fuck hanging up the phone. But I hoped that she didn't take it as I was gonna last all afternoon, because I'm not that guy lol.

I crawl on the bed at this point and head toward her. I lean over her ( shes laying on her back) and kiss her softly. We make out for a sec, with her stroking me from below. She tastes so good. I start feeling up her thigh but she stops me as I get underneath her tunic.

I protest. She says she wants it shaved and squeaky clean for me before I'm allowed to touch it.

"But I love how you look with hair" I say.

"You'll love it even more nice and smooth, I want you to shave it for me." She responds.

I'm surprised she's so trusting as I'm pretty much a stranger, but the thought excites me, as I've never done that before.

"If only there was some type of contraption that could allow me to remember your natural look..." the last girl was pretty cool with pictures, so I figured I'd give it a shot. She says she loves pictures, and as long as her face isn't in them, I can take as many as I want. (Yay!).

So I get completely naked per her request, and snap some shots of her on the bed with my phone. She's teasing me, having a great time. She lays her head down toward the foot of the bed (where I'm standing). She starts jerking me upside down. She has a pretty high bed, and my dick is pretty much lined up with her head. She keeps playing with my dick as she slowly scooches more off the bed. Eventually her head is completely hanging off the edge of the bed, with my member inches from her cheek. She subtlety lines me up with her mouth, and gently carcasses the tip of my dick with her soft lips. She keeps jerking it slowly as she gives it light little kisses. I'm fighting the strong urge to just shove my cock into her mouth at this point.

She finally opens her mouth, puts her lips around the head, and gives a light suck.

Holy shit.

She spits it out and strokes me a couple more times, then gives the head a few pecks, and starts to take me in her mouth again. She reaches around, grabs my ass, and slowly pulls me into her throat. I don't know if it was all the teasing, but I don't think a bj has ever felt that good. She was using just the slightest bit of suction. I could feel her limp, soft tongue mold to the bottom of my dick as she took me all the way in. Once her nose was touching my balls, she pushed my hips back, and then pulled me deep into her throat again. At this point she's had enough and pushes me off. 2 sucks. Fucking torture.

She says it's shower time. We go into the bathroom and she steps into the shower. She keeps her tunic on though. She lets the water flow over her clothed body, and you could see her skin through the sheer cloth. I grab my phone and she shows off a bit. She finally beckons me in as she's lathering up. I help her take the painted on tunic off, and get to work lathering. She makes a comment about being self conscious about her tummy, she shows me her c-section scar. She has a little extra around the middle but who gives a shit, so do I. As creepy as it sounds, the idea of one of my peers being pulled out of that opening a quarter of a century ago is incredibly hot. Ya know, like after all this time shes still a sexual being. Anyways once were done washing up, she grabs the razor and cream. She actually starts, and gives me the razor after getting most of the sensitive areas. I am super careful, as I gently shave whats left. Its fun watching her bare pussy appear. It makes her look younger (at least down there.) After I'm done she touches up a few spots and rinses off. Boy was she right, I've never wanted to eat a pussy that bad in my life.

I get on my knees and stick my face in for a lick. I halfway expected her to stop me, but she finally let's me touch her. She puts her back against the wall and opens her legs a bit. She mostly tastes like nothing with a faint taste of soap, but as I keep going I start to get tastes of sweetness as her juices start flowing. I'm only down there for maybe a minute before she pulls me up.

I figure she's finally ready and try to turn her around, but she stops me....again. I can't take this shit anymore. I squat down, push her back to the wall, and rub my dick against her pussy, downward into her crotch. I'm practically begging for it, as I rub my shaft against her clit. She kisses me but doesn't stop me, letting me faux fuck her for a second. She finally stops me, and bargains with me saying she won't make me wait any longer once we get out and dry off. So I fall in line.

We get out and help each other dry off. She spends extra time on my crotch area.

"Damn babe, you're so hard." she says sitting down at her desk. That's an understatement. My dick literally kinda hurts it's so hard. She's grinning at me, loving how frustrated I am. She just kind flirts with me and teases me some more for a minute or two. She drops the towel, sits on the desktop, and starts brushing her hair.

I try to pull her toward the bed pleading for her to give it up. Telling her I've never wanted someone so bad, and that if she doesn't give it up soon imma have to tell her son all the bad things his mom has done.

She lights up. You can tell she liked that. "Get over here kiddo." She orders me.

I walk back over to her, and stand in between her legs.

"I want you to fuck me right here on this desk."

It's a pretty small desk, but I obviously have no problem with obliging.

She leans back onto her elbows on top of everything and spreads her legs.

"I have a condom in my pants over there, should I get it?" I ask.

"When's the last time you were tested?" she replies.

I actually had gotten tested a couple weeks ago so I tell her. I mention I haven't gone without a condom in ages. She then explains that she also gets tested regularly, and that she has an insert for birth control. She said she hasn't gone without a rubber in a long time either, and is really craving my flesh.

"Well, you've already rubbed yourself all over me in the shower, but it's your call honey"

I loved how she kept calling me pet names, it made me feel more like I was fucking a friends mom or something. Now I know this is gonna sound stupid as shit, and I'm not sure if it was just the major age difference, but I felt super conformable with her. Like, safe really. I know I shouldn't have, but I wanted her so god damn bad that I rubbed the tip of my rock hard cock against her lips, and slowly pushed in.

And let me tell you, it being the first time in over a year that I'd had sex without a condom, it felt fucking fantastic. She was so wet, I just glided in. She tensed up pretty hard as I slid in deeper. She sucks air through her teeth as I stuffed the last bit in.

I slid out slowly and pushed back in, really gripping her hips hard. She was still tense as hell, and it made me realize that she was probably just as worked up as me from all that teasing. I started to pick up the pace, and pumped into her deep but smooth. She was moaning pretty loud.

I've heard plenty of girls moan over the top loudly, because they think that's what they are suppose to do, but she honestly sounded like she was loving it. She'd give me encouragement every once in awhile too. I asked her to keep using pet names, and she was saying things like "come on kiddo, fuck me deeper" or "mmm just like that honey". It sounds kinda creepy now that I am typing it out, but it was hot as hell at the time.

She looks kind of uncomfortable, so I stop pumping and have her get off the desk. I stand her up and have her face the desk. I bend her over, and slide in from the back. I start off fucking her slow and deep. I slowly increase the speed until were fucking at the same pace as we were before. I keep a steady pace taking mind to not pound her as hard as I really want to. I'm loving the loud claps as I smack into her ass.

"Just like that, I'm getting close" she says in between heavy breaths.

I keep the same tempo and smack into her ass steadily. Her moans turn to grunts (sounds kinda like short, loud hums. Almost like the someone getting the wind knocked out of them or something). I reach under and grab her tits as she lays her head and arms against the desk.

"Oh God..." she says quietly as I feel her body start to tense up. Her mouth is wide open and eyes shut tight as she grabs the table runner into her fist. Funny how she'd been pretty vocal up to this point, but was completely silent as she was coming. I slowed the tempo down as she came and pumped nice and slow deeply into her, letting her ride the wave. She eventually puts her hand back on my stomach halting my slow pumps. I give her a minute to recover, just kind of playing around back there.

After a few seconds she asks if I want to go over to the bed to finish. I tell her no, and that I want to finish her on the desk. So she leans back over it, but picks her leg up and puts her knee on the desk. I slide back in and start pumping. I feel like I'm getting even deeper with her leg picked up, not pulling back until my pelvis is pressed against her hard. Another minute goes by and I'm ready to cum. I edge a couple times as I'm not ready to be done, but go a little too far the last time and go past the point of no return. I pick it up and fuck her hard and fast as I feel my balls tense up. I keep pumping until the very last second, then pull my dick out and shoot a rope onto her ass cheek. I jerk it against her ass and shoot another couple shots onto her, with the last of it just dribbling out.

I grab her towel off the floor and we wipe off with it. She tells me I shoulda came inside her. But birth control or not, I don't think I could bring myself to. She immediately starts brushing her hair again as I'm still try to get my bearings. I linger and just kiss her shoulder as she brushes, when she explains she's gonna get dressed and do some running around before picking up her kid from school. She didn't do it in a rude way, but she was pretty much telling me we were done.

So I got dressed and watched her dress a little before getting ready to head out. We both walk toward the door, and she gives me a deep, soft kiss in the entry. We walk out and she locks the door behind us. Honestly I wish I could just tag along and be around her some more, but I understand the arrangement. She tells me how much fun she had and how Imma be her new toy. She apologizes for me skipping out on work.

"It was worth it for sure. But then again I might be out of a job if this continues, I don't think I could tell you no." I respond.

She says to text her when I get those mid day urges, and if she's not busy, She'll take care of me with enough time to get back to work next time.

We say our goodbyes, and she gives me another kiss (albeit a much tamer peck on the cheek).

This was yesterday. I haven't texted her again as I didn't want to smother her, but honestly I can't stop thinking about her. The sex was great, but I really just wanna take her out again, as I had a lot of fun at lunch too. I'm not sure if I should complicate things by trying to have casual meetings with her or just stick to the sex. I guess I'd just be happy to see her again at all though. Updates to come.