This true account first appeared as a Sexy Letter in Pip Caligulone’s Houseboat magazine. To read more about that singular publication, click here.
Dear Houseboat, I never thought this would happen to me…
I didn’t go to Thanksgiving dinner at my girlfriend’s house to fuck her mom, but I also certainly didn’t go to watch football.
Let’s back up. I met Katy at a Halloween party. We hit it off immediately because we were the only people who weren’t in a costume. Both of us had said “Oh fuck!” upon walking in to see a roomful of Slender Man and Eleven and a certain candidate’s toupee. Apparently we were invited by the one housemate who just didn’t get the memo. I mean, it was a week before Halloween—should we wear costumes all week?
Anyway, she and I landed on a couch together, like the losers we were, and soon we were engaged in that very special kind of drunken flirting where your hand casually brushes this body part or that one and then just stays there. I had my hand up her dress as the lights got dim and I expertly/drunkenly jilled her off right in front of a sad little group of Charmanders who were never going to evolve into Charizards.
And this wasn’t a one-night stand. We sheepishly called each other the next day and admitted we liked each other and even wanted to do non-sexual things, like go to farmers’ markets and get coffee. Of course, when we did those things, we were never too far from one of our places, where we’d return and fuck the autumn day away.
It was one of those relationships that starts with sex that means something, that makes you think, “You know, sex on the first date is a really good idea. It erases all the inhibitions so you can really get to know each other.” So it was in that spirit that, once she’d blown me on the toilet, she asked me, through a mouth of my own come, if I wanted to have Thanksgiving dinner with her family.
What I wanted to say was: “This is a red flag.”
What I said instead was: “I would love to meet your family.”
Katy’s family consisted of her mom, Miranda, and her older brother, Paul. Paul was one of those Failure to Launch guys and it was clear that Miranda had made him squeeze into his one good shirt for the occasion. Miranda, on the other hand, was just—just something else. Yes, she looked like Katy, and yes, no one would confuse them for sisters, but Miranda had this Sadder But Wiser thing going on and she wore these faded, hip-hugging jeans under a black velvet top that just made you want to slap her ass in spite of yourself.
Things were kinda low-down at Miranda’s house. She was the still-hot single mom of a son who wouldn’t leave and a daughter who, come to think of it, blew people on toilets and tried to talk with come in her mouth. From the conversation the two women were having during the stuffing and cranberries and green beans course, I got the feeling that the two of them shared a lot of secrets.
“So I hear you played Pokemon Come on Halloween,” Miranda said at one point.
“Mom!” Paul said. I was uncomfortable.
After dinner we all repaired to the TV room where Paul and Katy put on a football game.
“Come sit with me!” Katy pouted, and I sat with her while she draped her legs over me and pawed at me. I was uncomfortable with this show of affection in front of her family, so when Miranda asked me to help her with a pitcher of margaritas (now we’re talking), I respectfully patted Katy’s tasty thighs and joined Miranda in the kitchen.
“I can’t stand football,” Miranda said.
“Neither can I,” I said. “I watch the Super Bowl and I’m pretty much good for the year.”
Miranda poured me a strong margarita in a heavy glass. Not a Thanksgiving drink, but this family didn’t really stand on tradition.
“So Katy says you have a big fucking cock,” she said, and before I could pick my chin from the floor, Miranda spilled her drink on her blouse. Ice cubes clattered on the floor.
“Fuck!” she said.
“Everything OK, Mom?” Katy called from the next room.
“I just need to make another pitcher,” she said. “I fucking dropped this one. I’ve got more tequila in the garage. Hold on.”
Miranda flipped her blouse over her head to reveal an amazing set of firm, frank, heavy, pink-tipped breasts. I grabbed them instinctively. I had a very strong feeling that if Katy walked in, she wouldn’t be surprised, and neither would Paul.
The slickness and confidence with which she disrobed, quickly unzipping her jeans and pushing them down, made my cock hard. As she probably knew it would. She undid my belt quickly and freed my cock. I’d been freeballing that evening because I knew I’d have some drunk sex with Katy before the tryptophan wore off, but here I was with her mother instead.
I kind of admire guys who can just take a blowjob—I really have to trust someone before I let her do all the work. It was that way with Katy. I just felt comfortable with her. And Miranda was the same way. I leaned against the counter, while I heard the game going on in the next room and the various shouts of her adult children, and let this 48-year-old divorcee goddess suck me off, squatting with her jeans pushed below her knees.
I think I could have let her finish me off that way, but I was in for a penny, in for a pound, and I pulled her up by her hair, gently pushed her to the opposite counter, and forced her ankles apart as far as they’d go with her jeans pooled around them. I didn’t have a condom but I was absolutely not thinking straight at that point. Her pussy was dripping and slicked the edge of the dirty counter where the remains of the turkey sat on a plate. I pushed the head of my cock slowly past the puffy, meaty folds of my girlfriend’s mom and stroked her once for every year of her life, feeling her erupt somewhere around 30, and then at 45, and by 48 I sent the warm gravy into this hot, hot mess.
Yeah, we’d done something scandalous, but we didn’t make a peep. I kissed Miranda warmly, excused myself to clean up in the bathroom, and heard her making a new pitcher of margaritas in the pantry. I returned to the couch with Katy, drinks in hand, and watched the end of the football game. It was really strange to have warm, sweet Katy’s head resting on my lap as my cock still felt the receding pulses of having fucked her mom. But I gave thanks anyway.
—Gobbled in Redmond, WA
Previously on Porn Valley Observed: Labor Day in Porn Valley
See also: International Workers’ Day—Working on the Houseboat
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