I have been teaching high school in California for thirty-five years. I am happy to say that this is my last. I’ll turn sixty in March and max out my retirement benefit based on the “Age & Years” schedule. After thirty-five years, my pension will be well over $100,000 per year.

It was the first week of August, and teachers returned to campus on Monday. After everyone checked in and settled into their classrooms, we had the first staff meeting of the year mid-morning in the cafeteria. Our principal, Mr. Douglas, is very laid-back and casual, so we knew this would be a simple one-hour meeting, with the main function being to introduce the new teachers on campus, and any major announcements.

I have a strict rule that is often hard to follow, but the rule is to not date or have sex with any of the women who work at my school. Or my student's mothers. This is a lot harder than you might think—especially the divorced women, who have been ignored in the bedroom. Or the young teachers who see me as a fatherly type but fall victim to my charm and large bulge in my pants.

As I walked into the cafeteria, I searched for the group of guys that I always sit with at staff meetings. Seeing them in our usual location, the back corner, I walked toward them and looked around the crowd, acknowledging some of my co-workers.

“Adam! Hey, Adam!” I heard.

I turned to my left and saw a woman whom I had gone on three dates with three summers ago. At the time, she was teaching middle school English, and while we had a lot in common, we didn’t have that magic spark of chemistry.

Deb was several years younger than me. She’s a big woman, as in six-foot-tall, wide shoulders and thick, but not overweight. She has a tall, large frame and is very proportionate. Some might call this cute woman with brown eyes and long brown hair an “Amazon woman.” I stopped and took a few steps toward her. She stood and gave me an unsuspecting hug. “So nice to see you! How have you been,” she said.

“I’m good. Let’s catch up later in the day, I told her. “I’m in Four West. Where is your classroom?” Deb replied Seven East.

Vineyard High School was only five years old and was designed with a middle area of the school offices, library, and cafeteria, as well as four two-story buildings with twenty classrooms in each. Each building also had a copy and supply room, break room, teacher restrooms, and two small conference rooms, all located in the center of each floor.

When I sat with my group, one guy asked who the woman I talked to was, so I explained that we had gone out on three dates about three years ago. Gregg looked around our table and said, “I’m predicting Adam will get laid this week.” The rest of the guys laughed, and I told them that Deb and I hadn’t even kissed on those three dates.

My male co-workers enjoyed hearing my stories of hot, horny, middle-aged women I met on dating sites. And I was having a lot of fun, or should I say sex. I was in far better shape for a man approaching my sixtieth birthday than the average guy. I was still going to the gym every day after school, lifting weights, stretching, spinning classes, etc. I had recently given up jogging on the advice of my physician due to my thick frame and the constant pounding. Standing six-foot-two and weighing two hundred pounds, I had strong, wide shoulders with large biceps. My chest measured forty-eight inches, and my waist thirty-six inches. My dark brown hairline had receded some but matched my brown eyes.

Deb and I texted a few times on Monday and had lunch together the following day in the cafeteria. Living in the Oak Valley wine region of California, many of the wineries have musical groups and food trucks on Friday nights, and Saturday and Sunday afternoons. On Thursday I asked Deb if she was interested in going out on Friday for wine, music, and to catch up. She agreed.

***

“I’ll get the next bottle,” Deb said as she stood and headed to the tasting room.

We had just finished a bottle of the winery’s Rose’ Zinfandel and split a wood-fired pizza when Deb said she was getting us more wine. The band was a three-piece group playing covers of seventies and eighties pop songs.

When Deb returned with a bottle of vino, she was in a bit of a giggly mood. She told me, “I’m getting a little buzzed. I had a rough week at school with a ton of technology issues. Please, Adam, don’t let me get too drunk.”

I laughed and told her, “Then you should have got us a glass of wine each, not a bottle.”

The first bottle went down quickly with our pizza. It didn’t help that it was a warm evening with cloudy skies, making it a bit humid. It was now only six o’clock, and people were still arriving, including a younger couple I know from town.

Cisco and Lupe are a young Hispanic couple I met at a craft beer and wine tasting room in downtown Oak Valley. He had on a shirt from a brewery that I had never heard of in the Bay Area, so I struck up a conversation. The next weekend, I saw them at another spot in town. We talked, and we’ve been friends ever since.

“Adam,” said Lupe as she walked toward me and waved.

“Mamacita! Hermosa mujer!” I said in my horrible Spanish accent. Lupe is only thirty-five, five-seven tall, with long black hair that she curls a bit at the ends. She is one of the prettiest young ladies I know.

Laughing, Cisco said, “Stop hitting on my wife.”

When I looked across the table at Deb I could see the puzzled look on her face. “I take it you know them,” she whispered. I nodded “yes.”

“Deb, these are my friends Lupe and Cisco,” I said. I made the introductions, how we met, etc, and got Deb up to speed on the younger couple.

They said they love this winery and come out often for the Friday Night Live music events. Lupe said they were meeting her cousin and his wife, who were already sitting at a nearby table.

Over the next hour, Deb and I enjoyed the band, danced a little, and sipped slowly on the second bottle of wine, hoping to make it last until the band stopped playing. Between two songs, the lead singer announced, “The weather forecast is saying we should get rain here in about fifteen minutes.

Before the rain arrived, Cisco and Lupe stopped at our table and told us they were heading to the craft beer spot “Kegs & Corks” due to the forecast. Lupe showed us a weather Doppler app, and it looked like the rain would start any minute now.

I asked Deb what she wanted to do, and she said that she did not want to get caught in the rain. “This thin summer dress is so thin I’m afraid everyone will see my nipples if it gets wet.”

Sarcastically, I said, “Let it rain!”

“Oh, you’d like that, wouldn’t you?” she said.

After giving her a look, I replied, “I never would have asked you out three years ago if I didn’t think you were attractive. Hell, yes, I’d love to see your big boobs.”

As mentioned, Deb is a big woman. She went to college on a basketball scholarship at a university in a power conference, where she was all-conference her last two years as a power forward. Her breasts are large, yet due to her size, they are very proportionate. I “guesstimated” her tits to be 38DD’s.

When we got into my car, it started to sprinkle. I looked at Deb, “Damn, I wanted to see your wet boobs.”

“Here you go!” she said. Deb pushed her spaghetti straps off her shoulders and pulled down the top of her dress, exposing her big, beautiful breasts. “Go ahead, touch them. Lick’em too.”

I knew then that Deb was a bit drunk. I figured going downtown and drinking more was not a promising idea, so I decided I’d take her back to my house. But, first, I softly squeezed both tits and gave each nipple a long, slow lick.

“Ohhh, that feels so good. Suck on my tits,” she moaned.

“The sexual tension has been building all week. Would you like to go back to my house?” I asked.

“Absolutely,” Deb said. “I want to get naked with you and have some fun. No strings attached, though. Nothing serious. Is that, ok?”

“That sounds perfect,” I said as I drove out of the winery parking lot.

Not twenty seconds later, Deb’s hand found my crotch and was rubbing my growing erection over my khaki shorts. Then she leaned over and kissed up my neck, nibbled on my earlobe, and tongued my ear.

“Oh, fuuuck!” I whispered.

She smiled, “You liked that?”

“Yes. But if you do that again, you’re going to have to give me a blowjob because I’ll be ready to bust my nut,” I joked.

Deb pushed her hand up my right leg and under my shorts. She was now rubbing my cock over my boxer briefs. “Why don’t you pull over somewhere,” she said. “I want to suck your cock right now.”

I knew there was a short dead-end road nearby that was surrounded by vineyards, so I pulled down Free Road about a hundred yards. As soon as the engine was off, and we took off our seatbelts, Deb and I were all over each other.

After a few sensual kisses, my mouth locked onto her left boob, and I suckled on her large soft milk melon. Her hand was fumbling with my belt, so I quickly slipped my shorts and briefs down to my ankles. Deb took hold of my manhood and slowly stroked my growing woody.

“You are such a tease! You better swallow my big load,” I told her sternly.

She stopped stroking me, we made eye contact, and she said, “I always swallow.”

Deb sensually licked my shaft and twirled her tongue around my mushroom helmet. She then took my large head in her mouth and started softly sucking as she made eye contact with me.

She licked, sucked, kissed, stroked, and deep-throated me for about ten more minutes before I felt the lava boiling in my balls. “I’m going to erupt soon,” I whispered.

Deb started to bob on my upper shaft and head, making sure to tease me with her tongue. With her left hand, she was fondling my shaved balls, giving them a squeeze every few seconds.

She had to know I was about to climax as my legs shook and my hips began thrusting, forcing my cock down her throat. When I finally exploded, I had several ropes of jizz into her mouth and throat. Deb gagged, trying to swallow the first few loads. My jizz continued to flood her mouth as I emptied my balls.

When I was finished, my cock began to shrink, and she opened her mouth. Deb showed the pool of baby batter in her mouth and then swallowed a second shot of spunk.

“Your cum tastes good. It’s a bit sweet and sour. I taste grapefruit,” she said.

Suddenly, we were shocked back to reality by the lights of a big SUV driving by us on the narrow country road. The suburban honked thrice as it drove by, then turned left down a secluded driveway.

Ten minutes later I was pulling into my garage and walking Deb through the mudroom into the kitchen. I took her hand and led her down the hallway to my bedroom. We were soon naked on my bed in an enthusiastic kissing session.

My hand went south and spread her legs apart, which allowed my fingers to softly rub her puffy camel toe. While I wanted to finger her, I also wanted to lick and suck on her labia, clit, and probe her vagina. I chose the latter.

I moved quickly and ended up on top in the sixty-nine position. I kissed down her swollen labia, softly spread her lips, and allowed my tongue to taste her sweet nectar. She was bubble gum pink and glistening in the bright lights of the bedroom.

Deb’s hands were caressing my outer thighs and ass when I felt her take my cock into her warm wet mouth. She lightly sucked on my head before licking my shaft. I tried to concentrate on pleasuring her, but it was so difficult.

“Let’s switch,” I told her. “Prop up some pillows and spread your legs.”

I was now on my stomach, my arms under her upper thighs and hips, holding her tightly. I looked her in the eyes as I took one long slow lick from her rosebud north until I found her engorged clit. I teased her tic-tac with soft licks, rapid flicks, and a Hoover-esque suck.

“Oh, fuck! Yes! Suck my clit again. That was amazing,” Deb moaned.

As my lips surrounded her clit and I began sucking at various levels, I inserted two fingers into her box. They slid in easily as Deb was super wet. I buried my digits and went in search of her G-spot. When I found the soft pad, I applied medium pressure as I rubbed back and forth.

She was rocking her hips in sync with my finger fucking her. I looked up and saw she had one hand playing with her breasts and pinching her nipples. It sounded like there was a moaning soundtrack as I continued to bang her box.

I released her clit from my lip lock and went to town on her cunt, pounding her pussy with my hand and fingers. I was now on my knees and started sucking on Deb’s left boob. That set off a chain reaction.

She began bucking her hips, with her fists holding on tight to my bed comforter. Her moans changed to a panting sound, similar to “Uh! Uh! Uh!” And her legs were bent at the knees and raised.

“I’m cumming!” she screamed.

As she yelled, “Uh!” a blast of pussy fluid sprayed my hand. “Oh my God! She’s a squirter!” I thought.

Deb yelled two more times, accompanied by two more gushers of fluid. She then pleaded with me, “Stop! Stop!”

I removed my fingers from her snatch and estimated there was about one cup of fluid soaking into my navy blue duvet cover. The dark color made it easy to see the large wet spot on my bed.

After she caught her breath, she said, “I’ve never done that before. I had no idea I could do that.”

I was honest with her, “I’ve never experienced a squirter before. It shocked me at first until I realized what it was,” I told her.

Deb sat up, looked at me, and said, “That was the best orgasm of my life. Thank you.”

The End – Chapter One