Dm and the Dirty 20s
Copyright© 2025 by BreaktheBar
Chapter 72
Fantasy Sex Story: Chapter 72 - Shane has been playing 'The Game' for over two decades with his old college friends - D&D, but with sex. Now he's being asked to run 'a normal campaign' for some college coeds. It couldn't possibly happen again, right?
Caution: This Fantasy Sex Story contains strong sexual content, including Ma/Fa Fa/Fa Mult Consensual Romantic Lesbian Heterosexual Fiction High Fantasy Magic Were animal Sharing Light Bond Rough Spanking Group Sex Harem Polygamy/Polyamory Swinging Interracial White Male White Female Indian Female Anal Sex Analingus Cream Pie Exhibitionism Facial Masturbation Oral Sex Petting Sex Toys Squirting Tit-Fucking Voyeurism Big Breasts Slow Violence
“Can I ask for one thing, while we’re here?” Tori asked, stopping me before we started to get out of my Wrangler.
“Of course,” I said, frowning slightly at the serious look on the beautiful young woman’s face.
Tori had texted me on Friday, asking if I wanted to go cycling with her. It hadn’t come up since the first time the girls had come over to my house and gotten a look in my garage, but I remembered she mentioned she did a lot of biking before college, and she’d sounded a little nostalgic for the activity when she saw my bike. At the time, it had just been a little something to connect over, more of a ‘nod of understanding’ than anything. Now that my relationship with the girls had changed so dramatically, I realised that those were the exact sort of things that I probably needed to circle around to, so that we weren’t just texting, playing D&D and having sex.
Those three things were pretty great, but everything I’d learned over the years with The Game and how things had gone for us all told me that the better, more broadly spread and specifically individual, our connections could be, the better we would be. For each other, at the game table, and in each other’s lives.
So I’d offered something more than just a ride through town, and I’d picked her up that afternoon with my bike loaded up in the back of my Jeep, helped get hers secured as well, and we set off to the city. Well, there was a big hello kiss from her in there too, and one from Elyse as well, as she saw us off, grinning like a fool and waving as we drove away.
Of all the things that Detroit was known for, it wasn’t exactly bike trails that made the top ten lists. But it had a few, and I’d done some Googling to double check that they were still open and available ... and hadn’t been overrun with crack dealers or homeless encampments. Thankfully, there were a few spots that still had good reputations, and it was a solid late-June summer day. I’d picked out the Belle Isle Loop, and we didn’t run into any trouble or particularly bad traffic on the way, so we got to the island in the middle of the Detroit River in good time.
Tori took a breath, still looking at me seriously, and then reached over and grabbed my hand. “Can you treat this like a date?” she asked me. “Like, a serious date. Not just you hanging out with your younger friend. I don’t have any sort of problem with being friends with you, Shane, but we have- I mean, we have really great sex. I don’t have sex with my friends, that’s not the kind of person I am usually. Our game is different, with the girls, but this isn’t game night, so ... Are you OK with it being a date?”
I took a breath, nodding slowly. “Honestly, Tori?” I said after a long moment. “I’m so fucking relieved you’re asking for that, because I don’t know if I could act like it wasn’t. This is a pretty date-like scenario.” She snorted and chuckled in agreement, and I sighed, relaxing a little more as I squeezed her hand. “And, to be clear, I think the sex is fucking great, too. But I know how I would act with a woman I was on a date with, and we were already having great sex. Do you want me to act like that, or like this is our first date?”
“There’s a difference?” she asked, eyebrows raising a little in surprise.
“There’s a difference,” I chuckled. “Mostly in how often I grab your ass or kiss you. And there’s the added element of our age gap here in public. I don’t know-”
She stopped me by leaning over the middle of the car and kissing me, pushing her tongue against my lips for a moment before I let her in. She was quickly making out with me, and I cupped a hand on her jaw lightly as I enjoyed the feel of her lips on mine, and the smell of her perfume and shampoo. Once we were firmly into the kiss, she surprised me further by climbing out of her seat and awkwardly throwing her leg over, crawling and bumping her way to straddling my lap, making out with me even harder. She pressed her body to mine, and I grabbed her ass with my free hand, kneading it lightly through her tight athletic shorts.
When she pulled back from the kiss, she was breathing heavily, looking down at me a little due to her stance on top of me. Then she leaned back a little too far and the car horn let out a bleep! as her ass hit the steering wheel, making us both jump in place and then start laughing.
“If this were a first date,” she said as we started to come down from our chuckles. “I wouldn’t even be kissing you at the end, just to make sure you’d be willing to stick around.”
“And other people seeing us acting like this?” I asked.
“Let ‘em look,” she said. “I know I’m hot, Shane. I work to be hot. I exercise, and diet, and research skin care routines and makeup and hair styles and fashion and all the shit that I need to know and do if I want to be ready if an opportunity comes knocking. Being attractive takes a lot of work for a woman, but you know that. I’m happy to- I want to use my attractiveness on a date with you. You’re hot, too, even if you blush a little when we tell you that. Rhia’s Mom showed us pictures of you when you guys started The Game, and sure, you were a little nerdy and a little gangly back then, but you were always cute. And you matured into a sexy man. If someone wants to stare, they’ll be staring at a hot girl and a hot guy on a cute as fuck date, and they’ll be jealous.”
“OK,” I said, shaking my head as I smirked a little. “Whatever you say.”
“I say,” she grinned, then kissed me lightly again.
Tori’s grin, flashed over her shoulder at me once again as she pulled ahead a little on the trail, told me that she knew exactly what she was doing. She might not have had Elyse’s particularly great ass, but hers was still very nice, and looked great in her shorts as she leaned over the handlebars of her bike a bit.
“Tease,” I chuckled, since there wasn’t anyone nearby us at the moment. The Island was a public park with a bunch of different facilities, so on a summer afternoon, it wasn’t surprising that the Loop had plenty of people biking, jogging, and walking around. The one thing I hadn’t been counting on was the electric and motorised scooters - I had to admit, they looked like fun, but most of the idiots riding them seemed to lack common decency and tended to crowd people off the path.
I almost fell over sideways as I guffawed when, after another quick glance over her shoulder to check for anyone behind us on the path, Tori quickly reached back and yanked down the waist of her shorts, mooning me with one warm brown butt cheek.
“Come here, you,” I laughed, peddling to catch up, and she yanked up her shorts and took off, trying to stay ahead as she giggled like mad.
Tori’s weight against my front as she leaned back against me felt good. She was taller than Elyse, which put the back of her head a bit more at my shoulder height instead of lower on my pecs, and I was in less danger of just grabbing her tits when I hugged her from behind.
Not that I didn’t want to grab her tits, but we were in public, staring up into one of the glowing blue tanks in the public aquarium. Our bikes were locked up out front since we’d already done the full loop once, and I’d suggested we take a walk through the blessedly AC-equipped facility as we ate a couple of Häagen-Dazs bars to cool down.
“Sometimes I feel like a puffer fish,” she said. We’d stopped in front of one of the tanks, and there were a trio of the round little guys swimming around right in front of us.
“What?” I asked softly. “Why is that?”
“Because, like, at work this summer? I feel like people look at me and think they know everything about me,” she said. “That I’m just some cute ornament, and the only reason I’m there is because of my parents. But inside, and if someone pokes me too hard, I’ll blow up and be this big problem. Like I’m hiding all these parts of me when I’m not playing a character who feels more like me than I do, sometimes.”
“Mmm,” I hummed, leaning down a little to give her a kiss on the cheek as we continued to watch the fish. “That sounds really tough,” I said. “I’m sorry you’re feeling so contained.”