My First Love

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The first time of a DILF and the boy next door.
791 words
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His first licks were tentative, like a kitten lapping at milk. I arched further, bending my waist so that more of my ass was within his reach. I could feel his mouth smile against my ass meat as I did. "Your hole's so delicious," he murmured, sliding a finger across my anal opening. I smiled and looked up at the mirror. There he was, his handsome face smothered in my milky goodness: his huge arms holding my thighs apart, down to his magnificent dad-bod still in his prime. My vision continued further down to where his own huge thighs met, at the downy root of his humongous cock, which was dripping precum resolutely onto his abs. I reached for my phone and took a photo, just as he was swiping a large swathe of his tongue across my perineum. I hissed, shuddering in warm, wet delight.

He was a difficult one to break. He was my closest friend's dad, and was all in all a happily married straight guy with a propensity for dad jokes, but it all changed when my friend confided in me that he heard his dad and his mom fight - of all possible things - about sex. Being eighteen changed me into a veritable walking erection so I asked him what the problem was. "Apparently dad was... er, too big down there," my hapless friend told me.

That was a major turning point in all of our relationships. Up until then I was the innocent kid from two houses over who came to his house for games and snack and the pool and shit. I saw his dad in a new light. A new, sexy light. I also noted his furtive glances at my nubile eighteen-year-old ass when he thought I wasn't looking. See, I had been told by the boys my ass was my best feature, could have turned a straight man should I want to. And apparently, they were right on the money.

I picked a time when I know my friend and his mom was away for the weekend. It was all innocent at first. I asked him, a carpenter by trade, about a hands-on wood project I have to submit for midterms. He knew about it because his son had to submit the very same project. We spent thirty minutes in the shed tinkering away, where I made sure to brush at any opportunity at the fearsome bulge in his shorts. Soon the bulge was a veritable hill, and he was lightly panting as I bent down to fetch a fallen nail or a hammer.

Then it was all or nothing. I gathered my wits and grabbed at his swollen crotch, which led me to two conclusions. First, he was hard as iron tacks. Second, and more importantly, he was hung like a horse. He groaned aloud and looked into my baby blues. That was when I know I wasn't in trouble and soon I would have a very thick cock up my delectable ass.

I took another picture, this time facing the sun so that my blue eyes looked almost radiant as his face was buried between my ass cheeks. I contemplated against taking a video - too risky - and threw my phone down the bed - his kid, my best friend's bed - as I twerked my ass onto his face. He laughed, a deep belly laugh that sounded so masculine and resounded in his abs, which made my carriage throttle, the echoes vibrating across my flat tummy, where his cock laid, so ready for sex. "I need you to fuck me, daddy," I moaned throatily.

"Thought you'd never ask."

Later, I was watching the clouds ran in the sky from the tall window - the news had been adamant that it was going to rain later in the afternoon - when I felt him shudder quietly and came past my prostate. We had been fucking loudly for forty minutes when he suddenly got rather quiet but reached an intensity in the force of his butt thrusts that signified his coming orgasm. He had called me every name in the book: slut, whore, man-bait; but as he came up my ass he was all awhimper. I turned back and watched his face; he was crying from the force of his climax. "I thought I'd never have another orgasm again inside someone."

I felt his cock's aftershocks deep inside me, where he was lodged against my pussy button. His tears ran down his cheeks. I wiped them and licked them from his close-cropped beard. He gave me a deep searching kiss. His cum ran down my abused taint, warm, electric.

That was perhaps when I fell in love with him.

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7 Comments
AnonymousAnonymousover 1 year ago

Sexy scenario, but not enough description of the actual sex! More please

AnonymousAnonymousover 1 year ago

This was so hot. I’d love a future installment of the neighborhood teen boy and his friend’s married dad continue their secret affair. The married guy should pick the teen over his family and they should get married.

AnonymousAnonymousalmost 2 years ago

I definitely want more of their affair!! Very steamy, but also a bit sweet. I want the dad to fall for the friend.

dnsontndnsontnalmost 2 years ago

That was kinda tender. Great, hot, short story!

AnonymousAnonymousalmost 2 years ago

It was ok.

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