Note: This was an old post I never got to finish so chronologically speaking it’s out of order, but the memories aren’t
This one was handed on a platter. I was late coming from work on a Friday and my cousin, who was staying with me a few days, let my boys in before I got there. He said my neighbour had come by earlier to see what I was up to tonight. Funny thing is I’d met this milf only a couple of times before at a bar near by. I found her pretty attractive – she looked like she took care of herself but wasn’t afraid to trade a martini for a beer- but she never seemed too friendly. While I was talking to the boys about this whole thing, she came by and knocked at the door. A few minutes later we were all chatting and talking like old friends.
The two Wings eventually took their leave (they knew I didn’t need to come out anymore) and I was left on the couch with the neighbour and my cousin. He went off to the bedroom
In the words of my man, Cleveland Brown, “is it just me, or it’s rainin bitches!”. (note: at that period of time I’d had the co-ed, the intern, and a gaggle of other regulars who seemed to really love gettin the good news with the sharp end of my cocksicle)
We talked about all kinds of boring shit until we got on the topic of the apartment. Specifically I got on the topic of apartments because I was hoping she’d ask me to come along and see hers. Yes indeed, do come and see my place, she suggested. Now, this doesnt have anything to do with sex, but I was kinda pissed to find out that she paid less for a way nicer place than mine. It looked in better shape (building was like 80yrs old to begin with), and it was bigger with a way more friendly layout. Apparently she helped out the Super lady a lot, so maybe she got some sort of deal, anyway I was kinda jealous, what can I say.
We’d brought the drinks I made at my place and we chilled on her couch drinking and chatting. She put on a Nina Simone album when I told her how much I liked classics like that and next thing you know, we’re making out and coppin feels. I took her top off and started sucking on her tits, rolling them in my hands. For sure at some point she’d had a tight body, and even though she was still in good shape, her ass and tits were soft, not firm as they once must’ve been.
I unzipped my pants and took my cock out, first time encounters always give me raging hard ons even if after I’m done the complete opposite may happen. She was laying on her back and I straddled her chest a bit, first tapping the head over nipples and then on her waiting tongue. I put it in and took it out again as she moved her head witht he motion, trying to grab it in her mouth again. After doing that a few times, I let her do it herself and she used a hand to grab me right at the base, making the head swell further. She was only getting about 1/2 way and her pants were still on which was somewhat annoying because I wanted to play with her pussy. “Let’s go to the room” I said and helped her up off the couch.
While she went to the bathroom I lay on her bed jerking off, I didn’t want to lose my erection and wanted to remain in the euphoric mood I was in. She came back in the room and went right back to sucking from a doggy position. I started playing with her pussy with one hand and held her hair with the other to get a good look at what she was doing. Sometimes, a girl looks prettiest with a dick in her mouth, and there was definitely something sexy about the way she made my dick glisten with her saliva.
She had a bunch of assorted condoms in her drawer and asked me to make sure to check the expiry date, but those things last forever and I strapped one on that had a good couple of years before expiry.
She got on top and slowly worked her pussy on my shaft until I was buried to the hilt. She then started to move back and forth, and I could feel her pubes rubbing on mine. It’s things like that that ruin the mood as naturally I started imagining a fire starting from the friction. It’s all good to have a vivid imagination, but sometimes it can be distracting…I pulled her down on top of me so I could do the pumping. I had her hair in one hand, pulling her hair back and with the other I grabbed an ass cheek and pumped away, making her moan things like “Oww, you’re fucking me too hard…keep going…keep going”. A confusing message to be sure but telling me I’m fucking her too hard was all the encouragement I needed to keep going anyway.
If that wasn’t weird though, what happened when we fucked doggystyle was. I flipped her over and put it in but instead of pushing her ass further up to take the dick she was leaning forward and it was almost like my dick had to chase her pussy. I’d put it in and pump a few times then she’d do that again. When I started holding her in place she started saying she felt like a whore. Not because we were fucking, but particularly because it was doggystyle. So she was 38, but come on, this wasn’t 1938!
“No, come on, what are you talking about, of course you’re not a whore!”
“I feel like one in this position.”
“If you don’t like it, I’ll stop then.” Notice I said “like”
“Ohh, no, I do like it, it’s so good…”
So I stuck it and grabbed her hips with my hands.
“I know, isn’t it, and you look so sexy like this too”. She moaned and kept her head down on the pillow as I slowly slid in and out. She was enjoying it, I could tell so I started going a bit faster and harder, but then she started with the whore thing again. What the fuck, I just ignored it, but then she started leaning forward and I was stradling her doggystyle now, still pumping like a jackhammer. She moaned really loudly and then almost bucked me off, it was good I was holding her by the shoulder.
I thought, ok fuck it, no use spoiling it, so we went back to missionary like nothing happened. Who knows what kinda daddy or mommy issues she had. I told her I wanted to cum on her and she said anywhere was good but her face, naturally I chose the tits, hoping a wad would end up facializing her a bit, that’s always a pretty image too. It wasn’t too be, the cum came out thick and reached as far as her neck, so I focused on letting the rest of it shoot out on her tits. She helped out by squeezing my cock between them which made it all last a bit longer.
We’d agreed that I didn’t want anything serious and she already had “a lover” so that was as 1 night standish as it gets. I only saw her again once. We said hi and that was that…I doubt she ever learned to love doggystyle though.
