My Widower Neighbor

In the early 80s I had gotten an under the table job as a busser at a family friend’s diner a few nights a week. I was too young to legally work, but I looked much older, already having D cups, no one ever questioned it. I walked home, usually a little late, sometimes as late as midnight, past a big fancy (yet fixer upper) house that had been empty for a long time, and was finally purchased. The rumor was that it was a widower, a retired contractor who’d bought the house to fix up as a distraction to get over his grief after his wife had died suddenly in a car accident. You could hear construction during the day, but no one ever saw him, so he was kind of a mystery.

But on my late night walks home I would see him on his porch! He usually kept his porch light off, but sometimes I would see his cigarette and know he was there. I started waving, he’d wave back. He looked kind of handsome, even though I could tell he was my grandpa’s age. I decided I was going to meet him.

One night as I was leaving work I stole a bottle of wine from the kitchen and headed to the new neighbor’s house. I walked up his big staircase to his porch and asked if I could join him. He smiled and said he never turned down wine with a pretty girl and got up to get us glasses. I couldn’t help but notice that construction had left him with a great muscular body, he was wearing sweats and it looked like he had something big down the front of his pants, like he was getting hard. I was sure it was just shadow or something, but when he came back out with the glasses it was impossible to not notice he had a big cock. I remember smiling and looking up at him and he was looking at me, smiling right back, like he had seen me look at his cock and hope it was real.

We talked and drank and smoked a few cigarettes. His name was Oliver, the rumors were true, he was a widower, he was planning on flipping the house when he was done, so he’d only be there for a couple years. I told him about the diner, I tried to not say anything that would give away my age, completely forgetting I’d pulled the wine out of a school backpack and was still wearing my uniform. He talked about being in WW2, so I knew he was in his 60s, but he looked younger, and I’d never been with a guy fifty years older than me so I was super curious. The drunker we got the dirtier our conversation got. I told him about the sex I was having with multiple guys at once, he told me he comes out to the porch late at night to stroke his cock. I made a big point to tell him how much I’d love to see, and SWALLOW that!

I got up to use the bathroom, where I took off my bra and panties, unbuttoned my top enough so my boobs almost just flopped out, and touched my pussy to be sure it was dripping wet. When I came back out, sure enough, he was leaning back in his chair, cock out, slowly stroking and rocking. I couldn’t believe how beautiful his cock was, it was maybe 6 inches, and just so thick. My plan had been to sit on his lap, but after seeing his cock I went straight to my knees, brushed his hands away and started trying to get it all in my mouth. He could barely keep it together, he was grunting and saying oh fuck and I could feel his balls tightening. After only about two or three minutes I felt him shudder and press his cock a little deeper in my throat and just EXPLODE. I knelt there for about a minute while I made sure I had gulped it all. He was winded, but I knew he could go again.

I sat on his lap to let him cool down for a minute, making sure to sit my super wet pussy right on his still somewhat hard cock, and started to kiss him. He grabbed my tits as we kissed and touched tongues, his mouth working its way to my tits. He was loving my tits, telling me how big and beautiful and soft they are, I love getting my tits sucked so it was heaven to feel him latch on to my nipple as I rubbed my pussy down on to him. I guided his hand between my legs and upon feeling how wet I was with his hand he grabbed his cock and pushed it up in to me. He kept saying oh fuck and we shouldn’t be doing this but also moaning and grunting and he never stopped sucking my tits or rubbing my clit. I felt my back start to arch and that wonderful tingle start moving up from my clenching toes. “I’m cumming! I’m cumming! Don’t stop! Don’t stop!”, I pleaded in to his ear. As I felt the orgasm take over and my body shudder, I heard him moan so satisfyingly, and as he twitched inside me I knew he’d cum too. We sat for a few minutes, his cock still inside, kissing, rubbing my clit and making me twitch and clench lol, lightly sucking on my now red almost sore nipples.

When I stood up I felt his cum rush out of me and down my legs. “Oh that’s so fucking hot” he said and just looked at my cum drenched pussy and legs for a minute. I buttoned up my blouse and grabbed my backpack, I was going to get my panties and bra from the bathroom, but he told me to leave them so I’d have to come back. He kissed me goodbye and whispered to think of him as my legs rubbed together on my walk home.

It became a regular part of my walk home. Sometimes we’d go inside his house, sometimes he’d eat my pussy, sometimes he’d bend me over the railing of the porch and we’d look out over the street at night while he fucked me from behind. We had a wonderful time while he lived there, and I miss him so much.