My twenty-second birthday will definitely go down as the most memorable birthday that I, or probably any guy, has ever had. But the buildup to that birthday night is a bit of a whirlwind. How I went from sitting at my desk, my hand down my pants, watching porn, to spending a night with the most amazing cougar I could dream of still seems pretty surreal to me, but damn if it isn’t the best type of surreal.
I already kind of gave up where the story starts off, but like most guys in their early twenties, I often spend my evenings in my room, my web browser navigated to some porn site or another, and my hand wrapped around my dick. I can’t help it, but as long as I can remember, I’ve had a thing for older women. It’s not that girls my own age don’t turn me on. I mean, I’ve been with a handful and always enjoy myself, but there’s just something about a cougar, a sexy older woman, that really turns me on.
So on that night, about a week before my birthday, I had the house to myself. I pulled up a video that looked like I would enjoy it: this one with two women in their 40s or 50s having a three way with a guy about my age. They weren’t the typical porn star type. Rather, they looked like they could be any one of the women who live in my neighborhood. Sexy but real. The guy was a normal, average guy, with a way-above-average member. There wasn’t the normal stupid lead-in plot that most porn movies have. They were just in a bed room and got right to it. Wishing I was in that young dude’s position, I pulled my dick out and started stroking.
Now, here it helps to understand the layout of my room and my street. I’m on the top floor of the house, my computer across the room from one of the two windows in the room. The houses on my street are pretty close together for a suburban street. Not conjoined like rowhouses, but pretty damn close. As I was getting into the scene, I had a quick realization and turned toward the window, realizing that I didn’t close my blinds like I normally do. As I spun around in the chair, not thinking about the consequences of my actions, I locked eyes with Bev.
When I saw those women in the video, Bev was one of the neighborhood MILFs that I thought of. Slim but curvy with shoulder-length blonde hair and an amazingly tight body for anyone, let alone a woman in her late forties, my friends and I have spent countless hours discussing the filthy thoughts we have about her. As soon as I spun around and locked eyes with her, I knew I was in for an awkward encounter. Not knowing what to do, I just froze, not even trying to cover my now-rock-hard boner. Bev, seemingly equally shocked, didn’t do much either. Dropping the t-shirt that she was folding out of her hand, she opened her mouth slightly as if to say something, but realized the windows were both closed, and didn’t. Instead of turning away, like I thought she would, she took a step or two closer to the window, unlocked the latch, and slid the window up.
Absolutely shocked, I jumped out of my chair and quickly pulled my shorts up. I moved toward my wind after she beckoned me to do so.
“Hey Jon! This is a bit awkward, but I’m sorry about that. I didn’t mean to spy on you or interrupt,” Bev said pretty nonchalantly. Not knowing quite what to say, and still a bit hard, I kind of just stammered a half-assed response.
“Jon, are you alright?” Bev followed up.
“Oh, yeah, um…I’m really sorry. I should have closed the blinds, I should have turned away quicker.” I quickly apologized for everything I thought I did wrong.
“No need to apologize, sweetie,” she laughed. “I should have realized what you were doing when I caught that glimpse of your computer screen and closed my blinds. Why don’t you get back to what you were doing before everyone else gets home,” she smiled and closed her blinds. Absolutely shocked at how cool she was about it, I closed my blinds, sat back down in my chair, and tried to get back into my video.
A few moments later, I’m back enjoying my video when my phone starts to buzz on my desk. At first, I try to ignore it, choosing instead to focus on the sexy MILFs on my computer screen. But when I looked down and saw the Facebook message from Bev, my curiosity got the best of me. I picked up my phone and saw two messages.
“Hey Jon! I’m sorry again. I hope you are having fun in there.” The first message caught me off guard, but the second one really got me thinking.
“I shouldn’t say this, but seeing you got me more excited than I have been in a long time. Would you open up your window again?” I couldn’t believe it. I didn’t know if she was kidding, if she was trying to trap me into something, or if she was serious. I’ve known Bev for a long time and she was always the sweetest, so I figured I should take her words at face value. I got up out of my chair, went back to my window and drew open the blinds. She had pulled a chair up to her window and had taken her shirt off, leaving her in her jeans and a white bra. She looked a bit nervous, but definitely relieved, a smile on her face when I opened the window.
She raised her hand, beckoning me to go on. Standing facing the window, I looked down and slowly started to stroke myself again. The smile on her face got wider, and she slid a hand in the cup of her bra, caressing her breast as I steadily increased the speed of my stroking. Her other hand was down in her lap, and even though I couldn’t see because of the angle of the chair and the level of the windowsill, I could tell she was starting to rub herself in much the same way that I was. I could tell that her window was open, so I moved to open mine up too. The air was unseasonably warm, so I didn’t mind the fresh air coming into the room.
She got up and came over to the window, confirming my suspicion that her hands were between her legs, as she was wearing just a matching pair of white panties.
“Jon, I’m so glad you opened the window for me,” she said in a bit of a whisper, just loud enough for me to hear, but quiet enough that a passer by wouldn’t. “I’m sorry if I crossed a line.”
“Well Bev, you probably did, but I’m willing to jump across with you,” I said, a bit nervous about how corny that would sound. Bev laughed, half out of how ridiculous the situation was, half out of how naughty it was.
“If that’s the case then, why don’ you finish yourself off for me,” she asked with the seductive tone of one of the porn videos I would watch. I got as close to the windowsill as I could get as Bev moved her chair closer to hers. She raised the level of her chair and brought her whole body up into my line of sight. She unclasped her bra, revealing a set of tits better than any I’ve ever seen. Her abs, which I had seen several times at various pool parties or trips to the beach or whatever, were perfectly toned and clenched as she put her legs up on the window.
My eyes were glued to her tits, her nipples nice and hard. I wanted nothing more than to jump through that window, climb up through hers, and suck on them as she stroked my cock. But she told me to finish myself off, so that’s what I was going to do. I reached over to my nightstand and grabbed my lube, squeezing a dime-sized dollop out onto my hand before applying it to my boner.
“Oooh Jon, you are really prepared,” Bev said with a chuckle. She slid a hand into her panties and started to rub herself. I was torn between being rock hard at watching her do that and wishing that she would tear those panties off and give me the same show I was giving her. My dick now slick from a mixture of lube and precum, I started to speed up my strokes. I never turned off the video from my computer, so the screams and moans of the exaggerated MILF orgasms from my porn were making me even harder. As I stroked, I could see Bev lean back and close her eyes, playing with her pussy with one hand and massaging her right breast with the other. Watching her get into it, I could feel the cum building up in my balls.
Taking a moment off from rubbing herself, Bev quickly and skillfully removed her and sat up in her chair. She leaned forward, out the window, and tossed them to me.
“See how wet you have me, honey,” she asked. I had heard her call me “honey” thousands of times before. That’s just how she talks. But this time, something about the way she said it affected me like never before. I put her panties up to my face, the thin lace soaked in her juices. I could smell her, taste her, and longed to bury my face between her legs.
By this point, she had resumed her position in her chair, her legs spread wide and her feet planted up on the window. I wrapped her panties around my cock, resumed my stroking with her soaked panties.
“Oh Bev, I don’t know if you can imagine how many times I’ve fantasized about this very thing,” I gasped through an increasingly labored breath as I edged near orgasm.
“I suspected as much Jon. This wasn’t the first time I saw you jerking off, and I see how you always hide your bulge whenever I show even a little bit of skin.” I just smiled and continued stroking, about ready to blow.
“I’m gonna cum, Bev,” I moaned. She pinched her nipple with her right hand as she sped up her fingering with her left.
“I wish you could cover my face baby,” she moaned. With that, I exploded, shooting a rope of thick, warm cum into the crotch of Bev’s white panties. Immediately after, another rope followed as my hips buckled and my balls shot forth the most powerful orgasm I had ever felt. Rope after rope of cum flowed out into her panties, all the while Bev was convulsing in her chair, experiencing what I can only hope was as strong as an orgasm as mine.
“Fuuuck,” I moaned after I finished. Bev was still rubbing her clit, but the strongest part of her orgasm had passed. “That was the best orgasm I’ve ever had,” I told her, thinking she would appreciate that.
“The best orgasm you’ve ever had, so far,” she added with a wink. “You have a birthday coming up, don’t you?” She added mischievously.
“Um, yeah I do!” I smiled.
“Well, give me back my panties and don’t you dare think about ignoring me the next time I send you a message. I have a birthday gift for you.” I through her panties back over to her, which she immediately put on, my cum still covering them.
“I would never think of ignoring you, Bev,” I said with a smile. She winked, closed her window, and left me mesmerized.
Source: reddit.com/r/sexystories/comments/khtabt/the_sexy_milf_nextdoor_mf_mast_exh_milf
Can’t wait for the rest