A High School Reunion of Sorts [MF]

I was home for college after my first semester, and decided to stop into the local Diner I used to hang out at with my friends in high school. The waitress looked familiar. I couldn’t place her at first until after she recognized me.

Amber was a few years ahead of me in high school. She had always been a bit on the “thick” side, but in the years since I’d last saw her, she had grown a bit chubbier. This is not an insult: she wore the weight well, it suited her. And to be crass, her weight gain suited me too: her ass was wider, her breasts looked maybe a size or two larger. Her hair, naturally auburn brown was now dyed black, curled and shoulder length. I had a bit of a thing for her in high school. She was heavily involved in the Drama Club, and I guess my thing for super-outgoing, curvy brunettes started early.
Her manager had already gone home for the night, and business was slow, so she invited herself to sit at my table. We caught up for maybe an hour. I knew that she had a kid shortly after high school, but other than her son, she seemed to try to avoid questions about her personal life. That should have been a clue. the other clue should have been when she first came over to say high. I saw her put something in her pocket. In hindsight, it was probably a wedding ring.

After we finished our coffee, she told me her shift was over, and she didn’t want to have to walk home so late. Being the perfect gentleman, I offered her a ride.
I didn’t make the first move. Once we were alone in the car, she started telling me how she had caught her husband cheating recently. How angry and sad and small that made her feel. “But now it’s fine,” she smiled sadly. “Because now you don’t have to feel guilty about this.” And she leaned in to kiss me.
I kissed her back, running my hand through her curly hair as I leaned toward her, pulling her close over the console. She groped me over the fabric of my jeans.

“Word on the street in high school was that you’re a big boy,” she teased, as I began to grow aroused. She pulled down my zipper without waiting for me to respond, began to struggle to free my now semi-engorged cock. She leaned over to whisper in my ear, asked me if I remembered how to get to the local park teenagers used as a make out spot. Again, maybe it should have been a redflag that she didn’t ask me back to her place. But you try thinking straight when your high school crush is lightly kissing the head of your dick.

She leaned over me as I drove, slowly stroking me with both hands, admiring me. She took me in her mouth and I whined a bit.

“Sorry about the teeth,” she gasped. “I’m not used to dealing with something this thick.”

Her work was slow and steady, mainly focused on my head. I drove slowly, barely able to focus on the road. She worked the base with her delicate, french-manicured hand as she felated me. Both hand and mouth moved excruciatingly slow until we were maybe five minutes from the park. Then she forced herself down almost to the base, gagging loudly before coming up for air. She began bobbing her head faster and faster, as if gagging had awoken something deep inside of her.

I triple parked in the parks’ lot, barely able to keep my hands steady on the wheel. She told me she had a pack of condoms in her purse. I frowned when I saw they were standard size.

“Yeah, those aren’t going to work, she agreed reluctantly. She forced herself down until she gagged again. She came up for air, giggling. “The least you could do is finger a gal when she’s choking on you”

As she bent over me, I reached back, under her skirt. I traced her over the fabric of her panties. She pulled my cock from her mouth with a pop “Stop teasing” she pleaded. She began to flick her tongue expertly on the underside of my cock’s head as I slipped first one finger, then two inside of her. She gasped between licks. Caressing my balls, she began to kiss and lick the rigid sides of my cock, her jaw clearly sore from my size.

She gripped my base as my fingers moved faster inside of her. Her face growing deeper red. She took me back into her mouth, working her right hand on the base at the same tempo, her left still caressing my jewels. I could tell from her body language that an orgasm was imminent. She began forcing herself deeper and deeper, past the halfway mark where she had been gagging earlier. She tried screaming as she hit climax, my cock deep in her throat muffling most of the sound.

She came up for air, “come for me,” she begged, her puppy dog eyes watery from the work she had been doing. She took me back in her mouth slowly. Savoring every inch. She had almost reached the base this time when I felt myself about to release.

“I’m going to come,” I tried warning her, but the words came out weird. She knew what I meant, and hummed out a clearly supportive sound. I released, wave after wave filling her mouth. She swallowed dutifully, even taking a moment to suck my head to make sure it wall got out.

After she lit a cigarette. She laughed at the way her makeup stained my now soft cock, “so much for smudge proof” she laughed. She then looked at herself in the mirror, her watery eyes making her mascara run. “You put me through the ringer,” she laughed. “You should come by my place in the morning,” she giggled. “i’ll make sure to have proper condoms for you.”

Source: reddit.com/r/gonewildstories/comments/6eijw5/a_high_school_reunion_of_sorts_mf

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