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14
I 29[M] spent three nights unlocking the sexuality of a stunning bridesmaid 28[F] - Part 1 - Jack's Adventures #8
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propmasterflex is a male
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This is the eighth story.

This is the story of Stacy.

One of my best friends was getting married, up in the mountains around the Bay Area. I was a groomsman, so I had to fly in on Thursday for wedding party obligations, with the ceremony happening on Saturday. The wedding party would be staying at the venue itself, a resort of log cabins spread over a hillside deep in the woods.

I came from the airport by rental car, driving out of the city and into the low-lying mountains. Before turning up the steep road to the resort, I stopped at a convenience store to buy myself some late-night snacks, Pringles and Twix bars, a bottle of wine. Then I began the precipitous climb up the mountain, the trees growing taller and thicker, the road narrower. A mile up, the driveway for the resort appeared on the left and I turned in.

I followed a one-lane road cut into the hillside, trying to not look down the sharp drop on my left. Eventually a large cabin appeared at the side of the road, a man sitting outside with a clipboard. He checked me in, gave me directions to my cabin and a key, and sent me on my way. I drove even deeper into the woods, along the same narrow road, until a parking area appeared on my right. A trail switchbacked up the mountain away from it, and tiny a-frame cabins sat alongside it, rising in rows. 

I parked, gathered my things, found my cabin. I entered and was standing in a tiny living room, just a table and couch, with a bathroom beyond. The bedroom was lofted above the bathroom, accessed by a wooden ladder. Everything was pine green or timber brown, bathed in just the right amount of natural light, from windows that looked out onto the surrounding woods. It was a perfect place to call home for a weekend like this. I couldn't believe I had it to myself.

The first event was welcome drinks at a brewery back down the mountain. A shuttle would pick everyone up from the main cabin at 5:30. It was currently only 2, so I went for a walk. I didn't get out of the city much and wanted to enjoy the natural world. The absence of sound, the absence of manmade air. Listen to the woods, breathe them in.

I meandered among the other cabins, then wandered down to the main resort. I saw the clearing where the ceremony would be held, the hall where the reception would be. As I climbed the hill back toward my cabin, I saw another car coming down the road. It parked just as I reached my door. I paused with my key in the lock, and the car door opened, and out stepped Stacy.

She was tall, maybe 5'10", with wavy dark brown hair that fell down past her shoulder blades. Right now she was in a t-shirt and jeans, but it couldn't hide her gorgeous figure, skinny but with some meat on her, a good ass and nice breasts. She looked up at the cabins and we made eye contact.

I smiled and waved. She did the same. Her face was heart-shaped, with dark eyebrows and a small mouth. She looked vaguely like Lily Collins. She was fucking beautiful. 

"Jack!" I called.

"Stacy!"

"Bridesmaid?"

"Yeah! Groomsman?"

"Yeah! Nice to meet you! From incredibly far away."

She laughed.

"You too!"

I waved again and then entered my cabin. The weekend had just gotten a hell of a lot more interesting.

At 5:25, I left my cabin and walked toward the shuttle pick-up. It was late summer, the sky still bright, but the sun had fallen behind the mountain and the whole resort was now in shade. The day's warmth was fading, replaced by a light chill. I was in a hoodie and jeans, perfectly comfortable.

I stepped onto the shuttle. The front rows were mostly full of older people, the family of the bride and groom. I greeted the groom's parents, then made my way down the aisle. A couple other groomsmen were just behind them, the groom's high school friends, who I'd met at the bachelor party. We shook hands and chatted briefly. I would've sat with them, but then I saw, alone a couple rows back, Stacy.

We made eye contact, she smiled, and I proceeded down the aisle and swung myself into the seats across from her.

"Stacy?" I said.

"Jack?" she said.

"You got it."

She was wearing a light blue sundress, with a square neck and puff sleeves. The color matched her eyes, and complemented her lightly tanned skin. I tried to not look at her breasts pushing out against the top, c-cups I reckoned, or her legs, which were crossed, the lower hem of the dress riding up above her knees.

"Aren't you cold?" I said.

"Um, currently," she said, trying not to smile but failing, then laughing too. "I figure it'll warm up down the mountain."

"If not, you can borrow my sweater."

"That's very kind of you. If it's scorching hot, you can..." She looked at what she was wearing, then back to me. "I've got nothing for you."

It was my turn to laugh. 

But she ended up being right. The shuttle descended the mountain, then circled its base, and we were blasted by the sun again. The shuttle warmed up, and I unzipped my hoodie and took it off. I looked over at Stacy, who was looking at me from the corner of her eye, trying not to grin.

"You can say it," I said.

"I told you so?" she said.

"Yeah. That."

She laughed, gave me a playful push on the shoulder.

"Do you know the other groomsmen?" she asked.

"Sorta. I met them at the bachelor party."

"I don't know the other bridesmaids at all. I didn't get to go to the bachelorette weekend."

"Well, at least you know one groomsman."

She smiled. "At least that."

The brewery was a large space, filled with locals, and we'd reserved a back couple tables. There was an open tab, and we all milled about, meeting the rest of the wedding party, making small talk. At a certain point the father of the bride made a toast, but everything else was generally casual and unplanned. After making the rounds of meeting everyone, I saw Stacy standing off to the side. We made eye contact, and I approached her.

"Did you meet the other bridesmaids?" I asked.

"Yes," she said, looking around for them. "They've got, like, seven hundred inside jokes. That I am not inside of."

"When'd you meet the bride?" I asked.

"In high school," she said. "We played volleyball."

My desire to see her naked increased tenfold. I was such a sucker for leggy athletic girls.

"When'd you meet the groom?" she asked.

"A couple minutes ago. Nice guy."

She laughed, looking at the floor. Then her eyes traveled up to me, she tucked a strand of hair behind her ear, and I saw a glint of sexual interest.

We stood there and chatted for the next half hour, our eyes generally fixed on each other, the distance between us gradually evaporating. She was 28 years old, single, lived in Austin, was in graduate school getting a psychology degree. My Los Angeles life, unpredictable and stressful as it was to me, sounded like a dream to her, the stuff of fairy tales.

Around nine the wedding party announced the shuttle was heading back to the resort, and that the bride and groom were hosting an afterparty at their cabin.

Stacy and I were attached at the hip now. We sat next to each other on the shuttle back, and at the afterparty, in a much bigger cabin than mine, we were constantly by each other's side, only breaking off to get quality time in with the bride and groom. 

When people started to head off to bed, I turned to her.

"Are you done for the night?" I asked.

"I'm not sure," she said. "Are you?"

"I've got a bottle of wine in my cabin."

"Yeah?" she said.

"And Pringles."

"Pringles? Well, in that case..."

"Nightcap?" 

She nodded. "Sure."

We said our goodbyes, and wandered up the trail toward my cabin, casually bumping shoulders as we strolled. The night air was chilly. I noticed Stacy crossing her arms, shivering.

"Well, well, well!" I said. "Who's cold now?"

"I maybe didn't plan this far out," she said.

I took off my hoodie and wrapped it around her shoulders. 

"Thank you," she said, looking up at me.

She held the eye contact. Our feet stopped. The woods were quiet around us save for the night trill of crickets.

I leaned in and kissed her. Lightly. Softly. 

She returned it.

Then I pulled away. She smiled.

"Well," she said.

"Well," I said.

We continued up to my cabin. I let us in.

"Bigger or smaller than yours?" I asked, shutting the door.

She looked around.

"Much smaller," she said. "They must hate you."

I laughed.

"I'm kidding," she said, "it's exactly the same."

She sat on the couch, taking off the hoodie while I grabbed the wine and Pringles. There were two plastic cups on the counter of the bathroom. I spread the wine between them, handed her one, and sat next to her. 

We sat in silence, looking at each other, taking sips of wine. I put an arm around her and she scooted her side against mine. I played with the ends of her hair. Her eyes were a startling pale blue, framed under her dark eyebrows.

I drained my cup, she did as well, and I tilted my head toward her slowly, going halfway. She rose the rest of the way and we kissed. Her lipgloss was minty, flecked with red wine. Our lips pushed softly against each other. I reached back and put my cup on the arm of the couch. I found her wine hand and took her cup from her, and put it next to mine.

Her hand came up to my cheek, her fingers softly caressing it. I put my free hand down across her stomach and held the far side of her waist. Her belly felt firm under the fabric of her dress. She lifted her far hip slightly toward me, and I slid my hand under her, placing it on her butt. I squeezed a cheek gently, feeling its weight, its firmness. 

She moaned very softly into my mouth. I tightened the arm around her shoulder, increased my grip on her ass. Our kissing grew more feverish, the lust intensifying. 

I took my hand off her butt and pulled it over her far leg and let it rest on her knee. She lowered her hands, shifted her weight, and pulled the hem of her dress up until it slid out from under my hand and my fingers were touching her bare skin. I moved my hand up slightly, started moving my finger in slow circles against her inner thigh. She shivered very gently, and I felt goosebumps on her skin under my finger.

"Is this okay?" I said.

"Yes," she said.

I laid more of my hand against her thigh and gripped it gently, massaging it. Her legs pushed together, pinning my hand between them, and her hips started to softly gyrate. Her thighs were meaty, her legs strong. I could feel her athleticism, the former volleyball player.

One of her hands now moved to my chest, rubbing over one of my pecs. I turned more of my body toward her, we kissed harder, suddenly desiring more of each other, more than it was possible to have. 

My cock was swelling in my jeans, starting to grow painful against the denim. My hand was still clenched between her thighs, and I gently pushed it upward, wondering if she would let me get closer. She did, her thighs spreading, and I moved deeper between her legs, the fabric of her dress bunching around my wrist. I decided to go all the way, the warmth inviting me further, and I softly planted my hand over her crotch, the base of my palm beneath her belly button, my fingers down over the crotch of her panties. I could feel wetness through the fabric.

She pulled her lips away from mine.

"You okay?" I asked.

"Yeah," she said, "it's just...been a while."

She looked up at me, trying to seem composed, but begging my understanding. I smiled gently, reassuringly.

"Then we'll take it slow and easy," I said. "However you want it, whatever you're comfortable with."

She smiled, nodded, and leaned up and kissed me again. I kissed back, my hand moving to the back of her head, holding her to me. The hand up her dress started to move in slow circles, exerting a soft pressure. She moaned into my mouth. I then reached my fingers up and put them under the hem of her underwear, pulled it gently away, and slid my whole hand under it.

She moaned again and, as my hand felt its way through a small patch of pubic hair and cupped her vulva, I felt something in her body give way. A deep yearning to be touched like this, that worked its way through her muscles and eliminated all tension. Her body rose further toward me. She reached up with a hand, pulled her dress off her shoulders, everything falling and revealing a bra the same dove egg blue as her dress and her eyes. I looked down at her breasts, yep, c-cups, heaving over the top edges of the bra, and my cock pushed harder against my leg.

I started to move my hand in small circles over her labia. Wetness grew on my palm. I pushed my finger between her pussy lips and found her clit. She made a soft animal noise and broke off from kissing me. She pushed herself into the couch, her eyes closed, her breathing soft, her head angled down toward where my hand was working her pussy.

I looked at her furrowed eyebrows, her pursed lips, and I sped up. I moved my finger in concentrated circles over her clit, letting my other fingers play across the other parts of her pussy. I watched her face the whole time, enjoying what I was doing to her, making sure I was never going too far. After a minute, I felt I could explore further, and moved my finger down off her clit and inserted it in her pussy.

Her eyes opened wide and her face swung up to me.

"That okay?" I asked.

She stared at me for a second, and then nodded wordlessly.

She kept her eyes on me now as I started to finger her, one finger moving in and out of her hole, my hand wrapped fully around her vulva, the top of my palm stimulating her clit. I curled the finger inside her and rubbed it up against the top of her pussy. She looked down at my crotch, to where my cock visibly strained against my jeans. She moved her hand to my fly, unzipped it and reached through, bending her wrist to get her hand down around my dick. Her fingers were strong, feeling around its girth, and then she wrapped them around it and pulled it out through my fly. She smiled softly at the sight of it, and her hand started to work it gently, her head relaxing back against the couch, her eyes moving back to me.

Neither of us was making a sound, and I was suddenly aware of the silence of the woods outside the cabin, the lack of city noise. It was like we were the only two beings in the vast universe, and the whole point of existence was to be in this cabin on this couch, getting each other off.

I decided it was time to make her come, so I sped up the motion of my finger inside her pussy. Her mouth opened, her hand continuing to tug on my cock. She was very wet now, and my finger started to make suction noises as it ran in and out of her. I then pulled my finger out, and with a few fingers started rubbing her clit in fast circles, everything slick with her juices.

She gritted her teeth and lifted her head and looked down to where my wrist disappeared up her dress. I wrapped my free hand around the back of her neck and gripped it tightly, and then plunged not one but two fingers back into her. She gasped, my fingers stretching the walls of her pussy, and I curled them up and started blasting her g-spot. Between the hand on her neck and the hand up her pussy I had her under my complete control. Her body was shaking, her tits vibrating under her bra. The hand on my cock had stopped moving, now just held it loosely.

She looked up at me, her eyes wide and wild.

"I'm sorry," she said, "I'm gonna come."

I held her neck more firmly, leaned in close to her face.

"Good," I said.

And I kept fucking her with my fingers, the suction noises now one continuous sound, and her torso arched outward and she came, squirting, a small bit shooting from under her dress onto the floor of the cabin. She looked to the ceiling as her body spasmed, me continuing to finger her, her expression wild, her pussy drenched. When her shaking slowed, I pulled my fingers out of her with a squelch. Her orgasm done, her eyes refocused and her body relaxed back into the couch.

I expected her to be sheepish, embarrassed by her wetness, but it was as if her orgasm had awoken something in her, something long dormant. She turned to me, looked down to where her hand was still wrapped around my cock, bit her lip and smiled up at me. Then she took her hands off of me and reached behind her back, undid her bra and threw it aside. Her tits bounced free, beautiful c-cups, paler than the rest of her chest, her nipples pale too, verging on ghostlike.

She leaned toward me, putting one arm back around me, wrapping her other hand back around my dick, and kissed me once. She pulled back slightly and looked into my eyes as her hand started to move up and down on my cock. Her fingers were strong, her motion assured, a firm but gentle twisting motion. I looked down at her breasts, pushing against each other softly with each motion of her hand, my cock hard and thick.

"Can I?" I asked, raising a hand toward her breasts.

She nodded.

I put a hand under one breast, lifting it gently, feeling its weight. I massaged it up, pressing it into her chest, my hand running up her underboob and over her nipple. She made a soft satisfied sound and her hand gripped my cock harder. I let the breast fall and then massaged it up again, held it here now, moved it around in small circles.

Her hand sped up on my dick, working my shaft up to my head. Her form was great, controlled. Handjobs can be a hit or miss proposition, but when they hit, and the woman is gorgeous, not to mention topless, almost nothing is sexier.

I pinched her nipple, pulled on it, watching her boob stretch, then let it go. She let go of my cock, put her hand up her dress between her legs, moved it around, and pulled it out again. Her fingers glistened wet, juices strung between them. She wrapped them back around my penis and twisted lightly, spreading the wetness around, and then started jacking me off again.

The sensation was incredible, her hand now moving slickly up and down. She started going faster, and my cock started tingling. I pushed my hips up, tightening everything, amplifying the pleasure. I placed a hand sideways on her tit, pushing it up her chest at a diagonal.

She took her hand off again, gathered more juices from her pussy, and now focused on just the head, running her hand in circles around it. I moaned, everything feeling incredible.

"I'm close," I said.

She moved to jerking off my entire shaft. I looked into her eyes, down to where my hand kneaded her tit, the other breast bouncing free. Her hand ran up and down my cock one more time, and I orgasmed.

"Fuck!" I said.

I grabbed my empty wine cup, stood up, and came into it. I looked over at Stacy, at her tits, and my orgasm stretched further. When I was empty, and the cup full, I put it down and collapsed on the couch, my cock hanging wet over my slacks.

I put my hands to my face.

"That was so good," I said.

I looked over at her. She was smiling.

"That was really fun," she said.

I leaned in and kissed her, and she kissed back. When we broke apart, she said:

"Can we leave it at that for tonight?"

"Sure."

"We've got a couple more days still."

"I know."

"After the rehearsal dinner, maybe we could..."

"Definitely."

We both smiled.

A few minutes later she left, us sharing a lingering kiss at the door. I watched her up the trail until she entered her own cabin.

Tomorrow night couldn't come fast enough.

Part 2

---

Thanks for reading! If you want more stories like it, plus NSFW AI-generated images of Stacy and the other girls I write about, please consider subscribing to the Jack's Adventures Patreon.

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