I parked in a corner of the bowling alley's lot, an hour early, and set up the privacy screens on the van. I needed to shower off the dirt from my trail ride and get dressed. I'd spent a little time earlier in the week planning my outfit for the date and I was hoping that Gwendolyn would like it. I started off with black lace panties (yes, the thong, I was growing quite used to it at this point, don't judge me) and one of my lacy black bras. Bowling has a bunch of movement, but I still need to look cute, so the sports bra was not going to cut it.
Feeling a bit daring, I had bought myself a pair of almost sheer black thigh-high stockings and pulled those on, a visible black seam running up the back of each leg. I shivered as the lacy fabric brushed against my thighs and I knew it was going to be a long night until Gwendolyn's fingers could help me break this vow of celibacy. A forest green skater dress went over top, it was just the cutest. It had long lacy sleeves, and then a few lace cutouts around the torso and back. I'd thrown a cream-colored cardigan on against the chilly evening and wore some platform-heeled Mary Jane's to give me a little extra height. I'd have to take them off when I went bowling, but I'd take every minute of height that I could.
I'd pulled my hair back into a ponytail, re-using Gwendolyn's panties as my hair tie, hoping she noticed. I'm not desperate, okay? I'm just making practical decisions, so that I had them handy in case she wanted them back. Because she might, you know. Want her panties back. And then I'll have them ready. I'm very thoughtful like that.
I hopped out of the van at 6:58pm, making my way across the parking lot, spotting Gwendolyn already standing around outside, waiting for me. I grinned, happy to see the fiery redhead, and pleased to know that she wasn't late this time around. I might have squealed and ran over and given her a hug. But there's no evidence, so let's assume I didn't just act like that, okay? I played it totally cool, walking over and greeting her with a casual high five and a "how do you do."
"I missed you so much," I gushed into her boobs as she held me close, rubbing my back. "Three days was FOREVER."
"Well, you only have yourself to blame," she teased as she gave me a quick kiss on the lips. "How's work?"
"Blah," I complained, taking a step back and admiring her outfit. She was wearing a pair of black high-top sneakers, fishnet stockings, and a plaid mini-skirt that would have looked at home in any Catholic school. Tucked into that was a long-sleeve cream-colored mockneck and her usual leather bomber jacket. "Let's talk about how good you look instead."
She grinned, pleased by my compliment, and took my elbow, escorting me toward the front door. "Ready to go finger some tight holes?" I choked, stumbled, and she caught me, laughing as she did so. "I'll take that as an enthusiastic yes."
"You have no idea," I grumbled. "Those daily photos of you were pure torture."
"But they were so much fun to make," Gwendolyn countered, "Thinking of you each time I did." I found no way to argue with that, and let her continue walking me into the bowling alley. We rented a lane, socks, and shoes. I don't think either of us wanted to ruin our stockings with bowling shoes, so the totally classy rental socks protected our delicate legs. We sat down on the bench at our lane, pulling on the socks and laughing at each other as we waddled around in the clown shoes.
Now, I used to be pretty good at bowling, once upon a time in high school. I'm not going to brag, but I was ready to show her that I was actually good at more than begging. I walked over to the wall of balls, reaching for my usual 15 pound ball, only to immediately realize that holy shit, that was way too heavy. That wasn't going to work at all. Fumbling around, I finally settled on an 10 pound ball, walking back over to the lane where Gwendolyn was waiting for me.
She had spent the time typing our names into the lane's computer, getting it ready for me to kick us off. Gwendolyn stood at my approach, a smile on her face. "All set?," she asked and I nodded, putting my game face on. "Oooh, you look so fierce right now," she teased. I wasn't going to let the redheaded vixen distract me, I was determined to crush her in bowling, displaying my dominance. I stepped forward, visualizing the path my ball would take towards the pins.
I felt her step behind me, one hand on my torso, the other reaching down my arm that was holding the ball, her breath in my ear. "Now, make sure you put those fingers into the holes nice and tight, okay? Sometimes you might need to wiggle them around, make sure you're in real snug. Sometimes, I even lick my fingers before inserting them, just to make sure that the fit is right." I dropped the ball, nearly crushing my foot. Fuck.
"No dropping balls!," came the yell from a bored teenager by the front desk.
"Sorry," yelled Gwendolyn back. "She's new! Won't happen again."
"I am not new at this," I hissed at her. "I'll have you know that I'm actually very good at bowling." I snatched the ball off the ground, visualizing its path down the lane again. "You'll be singing a different story when I win!"
"Hmm, is that so?" Gwendolyn paused, posing with her hand on one plaid-covered hip, cocking her head to the side. "In that case, how about a wager before we begin?"
"I'm in, whatever the stakes are," I said, ego writing checks my body couldn't cash. "You're going down."
She looked thoughtful for a second, then nodded. "Agreed. If I win, you're going down on me. And if you win, I'll go down on you." I dropped the ball. Again.
"No dropping balls!"
"Sorry!," Gwendolyn and I yelled back in unison. She smirked at me. SMIRKED. If you can believe it. I snarled at her, showing my teeth. I was fierce. Small but feisty. I could tell she was afraid, it showed in the way she laughed. With me, not at me. Before she could distract me again, I grabbed the ball off the ground, visualized my path down the lane toward the pins, and let it fly. I didn't bother to look, turning as it left my fingers, a smug smile on my face as I sauntered back to Gwendolyn.
"Nailed it," I bragged. She doubled over, howling with laughter, and pointed down the lane behind me. I glanced over my shoulder and - what the FUCK? The ball rolled straight into the gutter like it was personally offended by my existence. Fucking traitor, I thought you were on my side. Didn't I just finger you, stupid sphere? "Look, I'm just warming up. That one was just to give you a chance." I bowled again, figuring that the first one was a mulligan. I, uh got another gutter ball. IT WAS ON PURPOSE, OKAY? TO GIVE HER A FALSE SENSE OF CONFIDENCE BEFORE I DESTROY HER! Really. It was.
She patted me soothingly on the head as she grabbed her own ball, making sure to lean over very seductively, the plaid miniskirt riding up, almost flashing me and the rest of the bowling alley. My mouth was dry and I had trouble breathing. I couldn't wait to destroy her in bowling. I'd have her eating out of the palm of my hand.
That frustrating redhead bowled a spare, blowing pretend smoke from finger guns as she walked back to me, smacking my ass as I went to take my turn. I scored a measly three points that time up, my hand shaking so badly that I had trouble fitting my fingers in the ball. She bowled a strike, then another. The game went about like that for the full ten frames, ending 47 to 189. And, uh, I didn't have the 189. Just in case you were curious.
Gwendolyn sat me on her lap, claiming a kiss from my lips before giggling. "Double or nothing?"
"You're on," I said defiantly as I stood from her lap, adjusting my dress and trying not to show how flushed I was feeling. "You'll be begging for mercy."
Gwendolyn tilted her head, her red hair spilling across her shoulders like a curtain, and gave me a slow smile that made my stomach feel all kinds of funny. "Aww, listen to the little puppy barking so fiercely," she cooed, voice pitched high and syrupy sweet. She reached out two fingers and booped me on the nose. BOOPED ME ON THE NOSE. Like I was a pet. "Rawr rawr, I'm Tiffany, I'm going to win, rawr!" Her voice the most condescending baby-talk imaginable and I could feel my anger building.
Dropping her tone back to normal, she turned, "Yes, cutie. I hear you. I'm quaking in my fishnets in terror that you might actually knock a few pins over this game." She put a finger under my chin and raised my face to look at her, her head close to mine. "Keep pouting, baby. Every time you stomp that pretty little foot and throw a temper tantrum is another minute until I let you cum." She ruffled my hair like I was a five-year-old, and sauntered over to the computer with a wink over her shoulder that challenged me: Your move, Tiffany.
I, ah, had no moves. I stood there, dumbstruck, mouth open and pussy throbbing as my dignity joined the bowling balls in the gutter, watching as she punched the second game into the computer. When she finished, she walked back over, giving me a slow kiss and then whispering in my ear. "If I win, you're eating me out in the parking lot. Windows down so everyone knows how much fun I'm having. No mercy."
She did not, in fact, beg for mercy. I did. And so did my panties. I lost by even more the second game.