The Cupcake
Copyright© 2020 by Emily Trout
Chapter 3
Romantic Sex Story: Chapter 3 - When a young lesbian falls hard for her straight roommate there's bound to be a little pain, humiliation, and guilt. Don't ask me why, some mysteries just aren't meant to be solved, I guess. (codes will update as story progresses)
Caution: This Romantic Sex Story contains strong sexual content, including Fa/Fa Consensual Romantic Lesbian Masturbation Petting Sex Toys Foot Fetish Public Sex Slow
Seventy years ago Dick Burden’s Goldmine had been one of those small neighborhood taverns where the working stiffs could grab a beer on their way home. The place had been built to last with real bricks and mortar, a hardwood floor, and a bar that must have been thirty feet long and weighed six tons. There was real history there; four or five generations had spilled their drinks, dropped their cigarettes, and carved their initials into the oaken countertop. A dozen taps with long brass handles stood proud and polished, and I always thought...
“Don’t those look like a bunch of pricks to you?” Jennelyn wondered. She gestured with her half-empty glass, spilling a dollop of foamy Budweiser onto the bar.
“I dunno,” I shrugged. “Why? Do you think about pricks a lot?”
“I think about you a lot,” she countered. “Does that count?”
“Probably.” I drained my glass and tapped the bottom on the wood. “Get another one, Sandy?”
“Two, please.” Jen downed hers as well with three large gulps.
We were going to get drunk, I hoped, and the sooner the better. Jen and I had dated for almost ten months. I thought we’d make it a year, but we didn’t. Just ten months and now we’d been broken up for two. Sandy, my favorite bartender in the world, didn’t say anything as she refilled our glasses. That’s why I liked her. Not because she didn’t talk too much, but that she didn’t believe in giving her customers a clean glass every time they ordered a refill. I hate those guys. Like, what? I’m gonna catch my own cooties?
“Happy anniversary,” I offered, holding up my glass.
Jennelyn touched it with hers and smiled. “Happy anniversary, Emily.”
We both drank, still smiling. We only ever argued when we were sober, which might be unusual. I’m not sure. On the other hand, if we got a little buzzed, things were usually pretty good between us. Probably because we both tended to get horny as hell and who wants to fight when you can fuck? So all we had to do was get through an hour of relative sobriety, survive the tiny jabs and button pushing that would inevitably occur, and then we could get down to business.
But the best laid plans...
A shadow fell between us and said, “Hey there, Jenny. This bitch bothering you?”
“Shut-up!” Jennelyn laughed. “I thought you were working tonight?”
I tried to be polite. “How are you doing, Nancy?”
“Better than you,” she said, pulling my squealing ex-girlfriend off the barstool and into the older woman’s tight embrace.
Nancy was Jen’s new dyke daddy, and don’t worry, I know how derogatory that sounds to some people. That’s what she was though, and proud of it. Everything about her was a stereotype and perhaps that’s why we’d taken an instant dislike to each other. I mean, how many girls do you know that walk into a gay bar with a strap-on in their pants? It was right there. This big lump of cock-shaped rubber, obvious beneath the faded denim. It stretched from her crotch halfway to her left knee, trapped against her thigh.
And I had to sit there watching as my sweet Jennelyn, a lipstick lesbian if there ever was one, had her ass grabbed in front of a dozen hooting regulars. Linda, hunched over her pool cue twenty feet away, looked up just long enough to holler that they should get a room. Her much younger partner, a ginger with big tits and a cute little beer belly, had a sweet laugh. I hadn’t seen her around before and wondered how Linda would react if I sent the girl a drink.
“Who needs a room when you got a truck?” Nancy yelled back, pulling Jennelyn towards the tavern’s back door.
I had absolutely no doubt that they were going to fuck right outside in the parking lot. Nancy had done it before, and not only with Jen, but with a number of different girls. Exactly how many, who could say? But she was one of the relative old timers, although she couldn’t have been more than thirty-five or so, and people had stories about her. Most of them were pretty funny if you’d been drinking, but some of them not so much.
After almost three years of coming into the Goldmine, I was considered a regular, but still a fresh face, too. Mostly because I was only twenty-two, and that alone made me fair game for women like Nancy and Linda, and even Sandy, who was in her mid-fifties, but still a serious bull. I don’t know how it is in the big cities and their big clubs, but where I lived the lesbian community had its own rules and hierarchy. And anyway, that’s the long way around trying to explain exactly how I knew that Nancy was going to fuck Jennelyn in the back of her old Ford -- Because she’d fucked me back there, too. I suppose that’s the real reason I disliked the woman and to this day I don’t know what bothers me more, that I’d actually let Nancy have me, or that I’d enjoyed it so damn much that I’d come crawling back for more a few days later.
“Tough luck, kiddo,” Sandy said, wiping up the beer that Jen had spilled and collecting her glass.
I shrugged and we shared a look. Both of us had been watching Jennelyn’s ass move beneath the plaid skirt she’d worn. She had the white knee high socks, too, and a pair of black Eastland loafers that had once been mine. It seemed like I was always giving away my shoes for some reason. And, of course, if Jen was playing naughty schoolgirl she had to wear a pink angora sweater over her cotton blouse. Christ. My ex-girlfriend was a total femme and while I knew we would never, ever get back together, it still hurt to watch her leave with someone else.
She hadn’t even said goodbye. Or thanks for the drinks. Or fuck off, Emily. I would have settled for that.
“Am I really this pathetic?” I asked, reaching for my wallet.
“The world turns,” Sandy offered. “You want some peanuts?”
“Nah...” That made me laugh for some reason. “I just want to be happy,” I said, but not out loud.
I had a man’s wallet. I had a couple women’s wallets, too, but they’re too big. I had a few purses at home to carry them in, but I preferred my genuine cowhide wallet. I liked the way it felt under my ass when I was sitting at the bar, not that I really noticed, but if you’ve ever sat on a purse you know what I mean.
Men have great wallets. A billfold. What a cool word. I opened it up and pulled out a twenty for Sandy. Since Jen would probably be sucking Nancy’s fat clit for the next couple hours, there wasn’t much point in getting drunk. Well, actually that doesn’t make any sense. It would be the perfect reason to get drunk, if Jen was still my girlfriend. Fuck. Was I drunk?
No, I was just looking at a picture of Jennelyn and myself that I’d kept in my wallet since our first date. We’d been walking along the boardwalk, such as it was, and passing an arcade, we’d found one of those two minute photo-booths. When the pictures came out of the machine, a strip of five 2x2 color photos, Jen had ripped the top one away and given it to me.
“One for you,” she said, “and four for me!”
I’d said something like, “Oh, so that’s how it’s gonna be?”
She’d stared right into my eyes. “You have no idea, Emily.”
It could be that I’m just attracted to that sort of women. The kind that just use up a girl until there’s nothing left but ragged, half-forgotten memories. But seeing that photo and reliving that moment from almost exactly one year ago ... Something inside me snapped. I wasn’t going to mope around feeling sorry for myself the rest of the night. Heck, it was still early. I could definitely screw something else up if I really put some effort into it.
Emily Effort, that was me! Actually, that was me back when I was about ten years old. I was at YWCA summer camp and we had to come up with our super-hero alter-ego selves for a big party, and ... never mind. I should have been Effortless Emily, but that sucked, too.
She picked up on the very first ring, as if she’d been sitting there in the dark, just waiting for me to call.
“Emily? Hi! What’s up?”
“Hi, Lindsey.”
Shoot. I hadn’t thought this far ahead. I must have been drunk, but I’d only had two beers. There followed a pregnant pause and when I didn’t say anything...
“Yeah. Hi there!” She laughed. “Did I call you?”
“No! Uh-uh ... I called you, I was just ... What are you doing?”
“Packing up some stuff for Goodwill,” she replied. “Dishes and stuff I won’t need.”
“Oh.”
“I mean, I don’t need to keep it, right?”
“Nah, I have plenty of dishes,” I agreed. “Glasses, too. And cups.”
“What are you doing? Are you at a party?”
“Uhhh...” I looked around.
The jukebox was going, naturally, and getting on towards nine o’clock at night, more customers were arriving. The Goldmine never really got packed, with the exception of Saint Patty’s Day and New Years, when everyplace got busy. But, you get a couple dozen women all drinking in one place and it does get surprisingly loud. Especially if you’re trying to talk over the phone with someone that you’re still getting to know. Lindsey wasn’t moving in for another ten days, and I’d only known her a couple weeks, so...
I should invite her to a gay bar? Okay.
“I’m in a bar, to tell the truth,” I said, “and I was wondering if you wanted to get out for a little bit. You know, come down and have a drink with me?”
“Is it a gay bar?” she asked, sounding so coy that I could easily imagine her sweet smile.
“Uhhh ... Kinda. Yeah. Pretty gay,” I admitted. “We can go somewhere else if you want. I mean, we probably should, actually, so...”
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