So, the last thing that I had my girlfriend, Amber, do with me in our month of what-I-say-goes dares was a pleasant bike ride. She and I ride bikes together often, and both of our bikes are mountain bikes meant for off-road trail use, big tires and rotor brakes and all. My girlfriend has a lovely tendency to wear skirts when bike riding, so I gave her a challenge.
Remember the pillow case from the post where we met Mallory? (If not, go back in my post history about three posts I believe!) Well… I dared her to go on a bike ride wearing that. The story begins on the Sunday after Mallory slept over.
Amber and I began our day pretty normally, awakening in the nude together as usual around 10am. She got up to make us coffee and I followed soon after, walking up to her in the kitchen and hugging her from behind, nuzzling the nape of her neck and kissing her shoulder as she worked on the coffee maker. I traced down the side of her stomach, causing goosebumps to appear on her chest, puckering her nipples and sending a chill down her body. “You’re particularly clingy today,” she remarked, smiling and kissing my forehead. In response I clung tighter to her torso, rocking us back and forth between our left and right feet. She hugged my arms as we did our little dance.
“Did you know that I love you?” I said, smiling obviously into her shoulder.
“I had no idea… How brave of you to make such a confession, honey.”
“Did you know that yesterday was the last day of our challenge month?”
She stopped our little rocking dance and turned to face me, my body still clinging to hers. She reached down to the back of my thighs, signaling that she wanted to pick me up, and I instinctively wrapped one leg around her waist, allowing her to lift me up to wrap the other around her waist as well. Now at her slightly higher eye level, with her full bush tickling my labia, she kissed me playfully for a moment before pulling back to talk. “So what you’re about to say is that you want to do one more thing before I’m allowed to say no. Tell me I’m wrong.”
“Nope,” I laughed, “that is exactly where I was going with this.”
She pecked my lips again, looking slowly down to my chest and then back up into my eyes. “Fine,” she said through a soft smile. “As long as it doesn’t involve that stupid fucking pillowcase again.”
“You’re not gonna like this.”
“Oh fuck you babe, come on!” She rolled her eyes and laughed with me at the coincidental nature of where I was going with this.
She leaned her ass against the counter in front of the empty sink, and I let my feet relax down a bit and rest inside of it. I leaned in to kiss her more deeply again, my newfound horniness fueling my bravery to tell her what I was thinking. I nibbled her lip as our eyes opened and we stared into each other’s eyes as I tugged gently on her lip, soon releasing it to speak again. “We love riding bikes, right?”
“Oh no,” she replied, a smirk forming on her face as she leaned her head back, cringing at the thought of where I was going with this. The smell of coffee was thickening in the air and she stood upright again, lowering me to the ground. My feet tapped against the floor, now damp from being in the sink, along with her pubic hair having my lower lips’ saliva all over it. “What a mess,” she said playfully in reference to her pubes. “So what you’re saying is that you want me to try to ride my bike while wearing the stupid-ass pillowcase.”
I nodded, sitting down on a wooden chair of our dining table.
“Well, we’ll make it work,” she said, pouring cups of coffee for herself and me. We talked about the plan some more before I got up, wiped the chair of my little mess that I left on it, and went to get our outfits for the day.
I put on a yellow floral print dress and a matching thong that I love from Shein, and brought down her pillowcase. She (surprisingly) enthusiastically began trying to get into it, and ultimately we decided that it would be necessary to have the ripped part facing backwards so that she wasn’t displaying her pussy to the world. If she stood up, her lower asscrack would be visible, but while she was sitting and riding it would be hidden by the seat and the tear would essentially cause her bare ass to be on the seat the whole time. So to give you a visual, with it on backwards, since there are two horizontal slits that she cut across most of the width of the thing – one on the technical “front” and one higher on the “back” – her lower back was now exposed, and now her underboob was exposed, with the top of the pillowcase half-cut-up into two straps that are meant to be tied together behind the neck like a bikini top. Since the pillowcase is too loose on her, we decided to use some twine to tie the front right. We wrapped it around the center between her boobs, revealing all of her (albeit minimal amount of) cleavage, and tied the two ends of the twine from there to the straps, tightening them over her shoulders and thus supporting the pillowcase to keep it from falling down!
She opted to wear her converse and I wore my running sneakers, and we went out to the shed to retrieve our bikes. I got on mine normally, my thigh-length dress naturally sliding over the back far out of the way of the tire, my bare asscheeks against the seat under my dress with my thong coming between my pussy and the seat. She finagled her way onto her bike without ripping the pillowcase, and I noted that she’ll have to watch out so as not to stand up off of the seat at all because her whole ass is visible due to the rip. We set off, leisurely pedalling up the dirt driveway, her noting that the vibrations coupled with her pussy lips hugging the seat is not doing her any favors in staying subtle about things. She set off in front of me and I followed, now emerging from our long driveway onto the road.
We got a few cheery honks from people driving by from the opposite direction, and I pulled up next to her, looking her up and down. “Your tits are out babe,” I said matter-of-factly.
“Shit! I keep pulling this thing down but the bottom [of the tit-coverage section] is too loose and keeps riding up.”
“Oh well,” I said, laughing as she gave me a humorous middle finger.
We rode for a mile or so before Amber asked to pull over to readjust things. We pulled off the road into a grassy field, and she stood up, revealing a wet mess on the seat. It was *soaked.* She shuffled her titty-coverage section down again, and I got up off of my bike to stand next to her, laying it down in the soft soil. I wiped two fingers across the seat, both coming away sticky and wet with her lovely juice. I held it up in front of her. “You *are* enjoying this. I knew you would.”
“Okay, fine, this is actually turning me on a lot.” She leaned in closer to me as if she didn’t want the grass around us to hear, “the seat keeps going inside me a little bit. It’s literally just the right size.”
“Let it, then,” I said seductively into her ear. She looked up and down the road, which we could see for about a mile in either direction before the dense woods enveloped it in both directions. She bent her knees slightly and leaned carefully into the front of the seat, allowing it to penetrate her wet pussy. She made a funny face of pleasure and surprise as it slowly crept inside her further. I placed my hand around her waist, leaning in to whisper in her ear, “Cum.” It was a demand, and she knew it.
“Here!?”
“Yup.”
“Well you’ve gotta do it too then. I’m not gonna do this on my own.” She was now standing still with the seat fully inside of her vagina. It was a silly pose.
“Say less, baby,” I said, reaching under my dress and pulling off my panties. I hung them off of my handlebars and stood up my bike and sat back down on it, my seat too wide to fit inside my relatively small (compared to Amber’s) hole. I began grinding on the seat, it rubbing against my clit as I worked, not quite hitting the spot right. I watched Amber work on herself. She grinded against the front of the seat, rocking her hips forward and back to more efficiently work with the weird angle of the horizontal seat. Before I knew it, she had pulled her tits out and was pinching and rolling one of her nipples in her hand, clearly enjoying the experience. She reached down and massaged her clit for a moment before I realized that her body was shivering, the seat allowing her to reach a relatively quick and discrete (aside from her hand motions) orgasm, standing up onto her tiptoes suddenly as her hand prolonged the orgasm. The seat was literally dripping wet.
In the meantime of her getting lost in her bicycle fantasy world, I massaged my clit, but was having a hard time getting anywhere close to orgasm. I was horny, and was trying my darnedest, but the seat and my hand were just not getting me anywhere in terms of climax. She looked back at me and said between heavy breaths, “I came on a bike. I just came on my bike. Holy shit, I just came on my bike. Did you just cum on your bike? Please tell me you just came on your bike.”
“No, mine isn’t doing it for me babe, it’s just too wide.”
She stood up violently off of the bike and wheeled it next to mine. “You NEED to try this. Seriously. I got it ready for you, please try this.”
I laughed and switched bikes with her, and she fixed her top half before resting on the seat of my bike. I swung my leg over her seat and lifted my short dress, getting into a similar position that she was in. Backing my pussy into the seat, it seemed to enter me with ease, it’s almost-pointed and Amber-lubed tip finding my entrance and easily sliding between its tight lips. I looked at my girlfriend and replicated the astonished look that she gave me just a couple of minutes prior, just as a car drove by, seeming not to care about what we were doing. I slowly let it penetrate deeper until my pussy lips kissed the cold metal adjustment knob, and I backed off of the seat. “Holy shit,” I said in amazement, “I need to get a thinner seat.” I began fucking the seat slowly, feeling both pleasure and a light amount of stretching pain from it overextending my labia. I pulled off of it after several slides in and out, and described the sensation to my girlfriend, before she and I decided to ride back home. My thong remained on my bike’s handlebars as she rode it.
Making it back to the house, I grabbed a towel to wipe out seats off and we both squatted to pee in the yard, both urgently having had to urinate since we were about halfway home. Perks of not wearing panties!
Amber turned around to lock the shed, and I walked up behind her and grabbed the pillowcase’s ripped section, yanking hard on it to tear it I’m two halves. Her entire asscheeks became visible. “Hey!!” She exclaimed, soon returning to a seductive state as she turned to face me. She surprised me by grabbing me and kissing me, when suddenly she leaned me over to dip me, only for her to then lower me to the ground and straddle on top of me in the grass.
She lifted the front of my dress to reveal my bare pussy. Humorously, she remarked, “ma’am looks like your radiator’s about to get blown.” I had no idea that she was about to lean in and blow me, her tongue finding my clit instantly and flicking it around until we heard a car coming down our driveway. “Shit, who is that!?” She said, suddenly sprinting to the house with my panties in her hand. She ran inside, and I stood up, fixing my dress, when I saw the Amazon van coming down the driveway. I jogged over to the driveway, meeting the driver halfway to retrieve the package, and I went in the house.
No cunnilingus was completed for me that day. But y’all know what that means… It’s my turn in the next story. ;)
I hope that you enjoyed. Spoiler alert: I did get my way the next day, but it may not be how you expect!
Source: reddit.com/r/sexystories/comments/oyc159/an_orgasmic_bike_ride_ff_exh_my_girlfriends_name
Just finished reading all your stories, for sure the best I’ve read in awhile, loved it! Can’t wait for the next one