I had a three month fling with the milf of a wrestling team teammate as a young lad and enjoyed it immensely. However, in the intervening years I never was able to hook up with another milf until a pool party the beginning of July.
I was invited to a birthday party at the house of a woman's mother, the woman being someone I'd had a hot and heavy fuckfest going until we moved on, but we stayed friends having many common friends in our circles. I didn't know it was a pool party when I showed up in regular shorts and shirt and bringing a gift of a bottle of wine. This was the first time I met the milf, who turned out to be a gorgeous, voluptuous brunette that turned every male's head, and I'm sure inspired partly engorged dicks all over the place. I gave her the bottle, wished her a happy birthday, and got a kiss that was a bit more on the mouth and a bit longer than usual, but I enjoyed it and thought no more. She asked if I bought my bathing suit, to which I said no, I didn't know it was a pool party. She said she still had some suits of her ex's she kept as spares and she'd get me one. She returned with trunks and said I could use the master bedroom to change. I thanked her, went there and started undressing.
I was down to my undies about to remove them when she startled me by coming in the room, came over and wrapped herself around me and started kissing me. Part of me was, "Shit, this is Linda's mom, I can't do and part of me responded with lust, than part being my engorging dick. She put her hands in my briefs, grabbed my dick and said "Linda always talked about how big you are and I see she wasn't exaggerating. I so want to get filled and streched like you did her".
The "you shouldn't do this" part of my brain was immediately drowned out by a chorus of "gotta fuck gotta fuck gotta fuck" and I promptly had my briefs off and had her on the bed pulling off her suit and then sucking, licking and massaging her clit. She moaned and arched her back, clamping her legs around my shoulders. Her long hair was splayed out like a crown around her head and she then kissed me as I climbed all the way on top, my now rigid cum-dripping shaft stroking her slit, then with one swift thrust I entered her wet swollen pussy and slowly drove in, almost my whole length before hitting bottom. I paused, soaking inside her feeling her grip me then started with long slow thrusts which made her gasp and shudder. I sped up, her writhing and cries increasing with it, her big breasts rolling up and down and her mouth on mine seeking to devour me when with a shriek and clamping of her legs, she orgasmed. It was only a few moments when I felt my cock swell, my nuts tighten and almost with a bang started pumping a load deep into her.
We collapsed and laid there momentarily and she went "Don't stop, I want to feel you stretch me and cum in me more". Who am I to say no? So I pushed up and started thrusting again and it was, at most, a couple minutes when she went " Oh my god!" and I felt my crotch get gushed wet by her squirting, then her orgasm which made me immediately cum another load into her. This time I didn't pause but kept going after finishing and after another few more minutes we both came again, her first and me following. At that point I had to take a pause and she went "I think I should get back to the party plus I'm starting to hurt a bit from your thickness", so I pulled out, rolled on my back with my pussy juice soaked shaft lying on my stomach and watched her dress then leave, smiling.
I then put on the trunks after my cock had gone down so I wasn't sporting a tent. Going out to the party, I got a beer, socialized a bit and then sat on a lounge with some other guys talking. My milf sauntered by with every guys' eyes on her, and I will admit I felt a bit of a visceral thrill and internal male ego stroking knowing she was walking around with three loads of my seed swimming around inside her.
The guy next to me said after she passed "The guy who gets to tap that has to be a god in my mind". I almost invited him to worship me 😄 but instead just agreed.
I've seen her daughter Linda a couple times after, I don't think mom shared anything, and I haven't gotten a booty call. Every time I think of her under me getting filled I get a chub. Maybe I should call her...
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