A First, My Friend's Sister Ch. 03

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They share each other for the first time.
18.2k words
4.77
330.4k
161

Part 3 of the 6 part series

Updated 09/22/2022
Created 06/28/2012
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Jeanie led me by the hand into the hotel. My heart was racing in anticipation as we crossed through the lobby to the elevator. She led me inside and pressed our floor number. As soon as the doors closed she pulled me into her wordlessly. Our mouths found one another and we kissed passionately, tongues dancing in our excitement. When the doors opened we separated momentarily as we stumbled into the hallway. She fished into her little purse and pulled out the key card for our room.

She gave me a devious look as she slid the card into the lock. "Can you believe this is happening?" she asked coyly.

"I can't believe anything that happened tonight is real," I replied.

The lock clicked and she pulled the handle. I pushed the door open for her. "Disappointed?" she asked, raising her eyebrows.

I shook my head. "Wondering how I could be so fucking lucky, actually," I said.

She smiled seductively as she brushed past me entering the room. I stepped in after her and let the door swing shut behind me. I put the empty champagne bottle down on the desk, and deposited my jacket on the desk chair. No lights were on but the curtains were open and bright moonlight spilled in. Jeanie clicked on a light, but it made everything seem artificial.

"No," I told her, "leave it off."

"Don't you want to see me?" she asked smiling.

"Yes, I want to see you in the moonlight. I want see you the way you looked on Overlook Ridge, when we first kissed."

She clicked the light off and stepped into me, pressing up against me. "That's so romantic, Jim," she said. I ran my right hand along her cheek and returned her smile. I let my hand caress her cheek and the back of her neck, while I ran my left hand up and down her arm, soothing her. I knew this moment had to feel monumental to her; I wanted her to know I was going to treat her kindly. We stared into each other's eyes for several moments.

"Are you scared?" I whispered.

"No," she whispered back, "I'm with you."

I smiled. "Jeanie, I want this to be wonderful for you. If you're not comfortable or if things feel like they're too overwhelming or anything, just tell me."

She nodded slightly, letting me know she appreciated the gesture. But I could hear her breath coming in shorter, quicker gasps. I knew her heart must have been pounding as hard as mine was. We stared at each other. There was nothing left to say. We'd shared an amazing night. I'd done the best I could to make it memorable, an evening she'd always cherish and remember. Now here we were. Everything we'd shared as friends and as admirers had led to this moment.

I pulled her softly into me and kissed her deeply. She met my kiss with fervor, running her hands around my back and pulling me into her. We explored each other's mouths again, as we had so many times that evening. Again I found myself wondering how the hell it had come to this. I had begun the evening telling myself that I wouldn't lay a hand on her. That she was off-limits and that out of respect for her brother I would not let this happen. Now here I was, alone in a hotel with her, kissing her passionately, about to make love to her. I couldn't believe it was happening.

But she was right. I owed it to her to respect her wishes as well. And she had assured me that this was what she wanted, and that I was the right man for her to be here with. When I searched my own feelings, I knew I felt that as well. I did care about her. I wanted nothing but the best for her, and I respected her completely. I knew my intentions were good.

Once I told myself this, I let go of any inhibitions I had left. I felt her soft tongue searching my mouth and it was as though I melted into her. It's ok to want her, I thought. It's ok to want to touch her, to feel her, to explore her. You care about her. Genuinely and deeply. And she cares about you. It's ok to take her. She wants you and she's offering herself to you. Take her.

As soon as these thoughts entered my head, it was like a switch going off. I ran my hands down her back to her sides and lifted her up slightly, so that we were level and our kisses were straight on. She wrapped her arms around my shoulders and moaned, running her tongue in a circle over my lips. I let my hands drift down slightly onto her behind. She responded by wrapping her right leg around me.

I could feel the firm roundness of her ass beneath the dress. My heart skipped a beat as I ground myself gently into her. I thought of the few layers of clothes between us and how easily they could be removed. Her beautiful dress, which she had looked positively gorgeous in all night, was just a thin, delicate piece of fabric. This airy little garment was all that separated me from the heavenly delights of Jeanie's femininity beneath.

I squeezed her tightly to support her weight and began walking her slowly toward the bed. She moaned again when she realized what was happening. I was taking her there. I was taking her to where this evening was going to meet its inevitable climax, to where our destinies were leading us.

We got to the bed and I sat her down gently. We broke our kiss and looked into one another's eyes. I felt like I should say something reassuring.

"Jeanie..." I began, but she cut me off.

"Jim, I want you." She said it quickly and authoritatively, dispelling anything I may have felt compelled to say. I put both hands on her face and just looked at her for a moment. Then I slowly and seductively ran them down onto her shoulders, slipping my fingers under the straps of her dress. I let my hands run lower onto her chest, moving agonizingly slowly. Her shoulders heaved with the depth of her breathing, anticipating my touch on her sensitive flesh.

I ran my hands down under her dress onto her bare breasts, giving the tiny little handfuls a gentle squeeze. Her head dipped back, as though her neck suddenly became soft, and she exhaled deeply. I cupped both tits gently and squeezed them firmly. I let my thumbs trace little circles around her nipples, and I felt the sensitive flesh of her areolas begin to tighten and harden as the blood rushed into them. I was dying to see them, to slip the dress off her and see her beautiful breasts in all their glory. To pinch the nipples until they were engorged, to lick them, suck them, bite them. I could feel my eagerness boiling up inside me.

I ran my thumbs over her nipples repeatedly. They had hardened to fullness and I tweaked them softly. Jeanie moaned deeply, and I pushed my mouth into hers. I gave her a little push and she fell weakly backward onto the bed, breaking our kiss. My hands slipped out from under her dress and I stood above her, gazing down at her lying on the bed.

She met my gaze for a moment, then broke eye contact, letting her eyes drift down to my crotch. My cock had hardened in my pants and I felt it twinge involuntarily as she stared at it. She looked back up at me and grinned deviously seeing my cock twitch. She grabbed me by my belt and pulled me down onto her. I let myself fall on top of her into a deep kiss. I pushed my tongue immediately past her lips and into her mouth, simulating exactly what I was absolutely dying to do to her. She accepted it willingly, curling her own tongue around it and sucking it gently with her soft, fleshy lips.

She ran both of her hands down my back onto my ass and squeezed hard. I groaned into her mouth and thrust my hips into her. She tilted her head back and broke our kiss, letting her tongue lick my teeth and lips erotically on its way out. "Mmmmmmm, you don't even know how long I've wanted to grab this ass," she growled, fixing her gaze in my eyes, her jaw hanging open hungrily.

"Really?" I asked seductively, raising my eyebrows.

"Hell yes," she groaned, "you have the cutest little ass." She squeezed me again harder, her nails digging into my cheeks through my pants.

I ground into her and turned her just slightly onto her side. "Oh I don't even want to hear about cute little asses, girl," I responded, running my right hand down the small of her back onto her behind, pressing the heel of my palm into her crack and curling my fingers up, pressing the fabric of her dress between her cheeks. "I've had to look at this perfect little butt for years knowing I could never touch it."

She smiled again. "You really looked at it?" she asked.

"God yes," I replied heatedly. "I had to pretend I didn't notice how amazing you look in your jeans, how perfectly your tight, little sweatpants fit, how you'd wear those little short-shorts in the summer. You drive me so crazy with this cute little butt." I ran my hand under one of her cheeks and pulled it upward, squeezing it tightly.

Jeanie laughed and ground herself into me, swatting my ass with her hand. "You lie!" she laughed. "You never checked out my ass."

"Oh yes I did, sweetheart," I assured her. "I wanted to do this so badly it almost drove me insane." As I said this I gave her ass cheek a slap like she did mine and squeezed it again.

"Did I really drive you crazy, baby?" she asked, smiling and biting her lower lip seductively and grinding into me again.

"God yes, you have no idea," I panted.

"Oh I think I have an idea," she said, renewing her own grip on my ass and squeezing harder. "Is this what you wanted, huh?" she asked, nipping my lips with hers. "Did you want to grab my ass?"

"God yes, sweetie."

"Did you want to squeeze it?"

"So badly."

"Do you really want to feel it, huh?"

"You know I do; I have for so long."

"Really? You wanna feel it like this? Is this what you want?" As she said this she ran her hand behind her and in one deft motion pulled the back of her dress up so that my hand could fondle her bare ass. She held my gaze with hers as she did it to heighten the naughtiness of the moment. I knew she wasn't wearing panties; she'd told me so earlier in the night. So in the split-second it took for her to slip her dress up, I went from having a handful of her dress to having a handful of her bare flesh.

It was soft and yielding and warm to the touch. I moaned with the sexiness of the moment and kissed her aggressively. She used her hand to press into mine and encourage me to really squeeze her ass. I grabbed a full handful of her ample flesh and curled my fingers into her crack. Then she broke the kiss off suddenly.

"Ohhh yes," she moaned. "Do you like that? Is that what you wanted?"

"Fuck yes, Jeanie, it's better than I even imagined."

"Is it? You really like it?" As she said this she pushed my hand further onto her ass, forcing it down deeper into her crack. I obliged and pulled her ass cheek open, then ran my fingers up into her crack and found the little soft spot in her crevice. I didn't push deep into her, but just let my fingertips gently caress her delicate area. She groaned and her head lolled backward onto the bed.

I could feel tiny little prickly hairs around her little ring of muscle, and below it my fingertips just barely grazed the slick velvet of her sex. It was warm and moist, and I was overcome with the desire to dive into it. Instead I buried my face into her exposed neck and licked from her chest to her earlobe.

My cock was now rigid in my pants and I ground it into her again. In the heat of that passionate moment, Jeanie moaned and almost shuddered, then spread her legs widely so I could press between them. I felt her secret place open wide with my fingers, and I was dying to be inside it, but I didn't want to rush things. I slipped my hand out from under her dress and ran it up over her breast again.

I simultaneously kissed my way down her neck to her chest. There I met my hand which was under her dress squeezing her tit, my palm pressing against her nipple, swirling it around brazenly. My fingertips were slick with her nectar and I licked the sweetness off each finger.

"Oh my god," Jeanie whispered. She was watching me. Her hair had come out of its perfect set-up and curly tendrils were hanging tantalizingly down in her face. She looked so incredibly sexy I could barely even breathe. I couldn't believe I entered this evening thinking I could possibly not lay a finger on this girl. She was unbelievably beautiful in that moment.

I met her gaze for a second, then I slowly and seductively wrapped the shoulder strap of her dress around one finger of the hand I had on her breast. Her lips curled into a grin. I returned her grin then very slowly pulled down on the strap until the dress slipped down off her breast. I backed my hand away slowly and stared at her exposed tit.

It was gorgeous. It wasn't big, but she certainly wasn't flat-chested either. It was a delightfully perky little handful, and she looked indescribably sexy laying there with her dress half pulled down, and one breast hanging out. Her nipple was taut and erect, pointing slightly upward. It was dark brown, with a puckered areola encircling it. The flesh of her breast was slightly lighter than the dark, olive-colored skin surrounding it. Even though it was only May, she'd obviously already gotten some bikini time in the sun.

I looked back up into her eyes. She was still smiling sweetly, but now her breathing was heavy. I held her gaze for a moment, then without warning I descended greedily on her nipple, pulling it into my mouth and sucking it eagerly.

"Ahhhhhhh," Jeanie moaned, and arched her back to meet my suction. I ran circular licks around her areola, then flicked her nipple vigorously with quick back and forth strokes. Then I pulled it gently between my teeth and sucked it hard. Under my ministrations, Jeanie began to grind her hips into me. I remembered our earlier session of dry-humping and realized almost immediately I wouldn't be able to do that for long without cumming in my pants.

I re-positioned myself so that I was kneeling over her. I broke off my suction on her tit, and pulled her other shoulder strap down, revealing her other breast. "Holy shit, Jim," she moaned.

I just smiled at her and descended on her other breast. I gave it the same treatment I'd given the other, sucking it long and hard. I started gently, just caressing and massaging it with my tongue to make it stiffen. But soon I was pulling it with my lips and nibbling it between my teeth. The entire time Jeanie's head was rolling back and forth on the bed, moaning my name and squeaking softly.

After several minutes I lifted my head again, breaking my suction on her breast. Jeanie put her hands on my chest. "I'm so turned on, Jim," she whispered hungrily.

"Come here, sweetie," I said, taking her hands in mine. I stood up off the bed and helped her scooch to the edge and stand next to me. The straps still hung limply off her shoulders, but the dress fell back into place covering her breasts.

I looked her in the eyes, still holding her hands. "Can I take your dress off, Giana?" I asked softly. I used her more formal name because I knew this was a point of no return. I wanted her to know that I was still that guy that she trusted enough to use that name.

She looked up into my eyes, nodded gently, and whispered, "Yes." I ran my hands up her arms to comfort her, then I stepped to her side. I kissed her softly on her shoulder, and ran a trail of tender kisses along her neckline as I maneuvered slowly behind her. She let her head loll to the side as I kissed her neck, until I was standing directly behind her. I let my fingertips just barely graze the skin on her shoulder blades as I ran a line of kisses down her back. She shrugged her shoulders seductively as a little shiver ran through her. Soon I reached the top of her dress with my kisses, and the little zipper lay hidden there.

I slipped my fingers in and slid the zipper painstakingly slowly down her back until I reached the top of her behind. The flaps of the dress swung open and in the moonlight I could barely see the downy little hairs growing from the small of her back down to the top of her crack. I bent down and made a meandering little trail of kisses all the way down her back to where the dress still hung. As I did so, Jeanie let a long, little moan escape her lips.

"Mmmmmm, oh Jim," she whispered. I stood up behind her and she turned around slowly. The dress hung limply off her, held on by just the spaghetti shoulder straps hooked on her arms. I looked her in the eyes, then hooked my fingers into the straps on her arms. I pulled them gently toward me to free them from her, and she dropped her arms slowly. Once I slipped them off her arms, only I had the weight of the dress in my hands.

I let it fall forward, and her breasts fell free. Then I let it drop to her waist where it hung for a split second on her hips, and slipped away. I dropped the straps and the dress billowed to the floor, revealing Jeanie naked before me for the first time.

Her breath came in shallow, ragged little gasps. My own heart pounded in my chest. Our eyes were locked for a moment in utter ecstasy. "I'm naked, Jim," she whispered.

"I know, sweetie," I whispered back, letting my eyes drop slowly down to her exquisite body lit seductively in the moonlight. I drank in the heavenly sight. Her perky little breasts heaved slightly with her breaths, the dark brown nipples standing taut and erect. Her tummy was soft and just slightly swelled in the middle. It wasn't fat by any means; she was clearly fit and in good shape. But it had just the slightest, pleasant little roundness to it, swelling gently up around her navel.

And below her little tummy was an absolute vision to behold. Once again her tan lines were obvious as the skin just below her waist was a little lighter than the dark olive skin around her midriff. Her pussy grew in a tight, curly little patch on her womanly mound. The patch was not large, but it grew thick and dense in a little triangle that narrowed as it approached the sweet chasm between her thighs. The hairs themselves were not long, but instead were tightly curled and grew thickly together in her patch. She had shaved the areas just to the side of her sex where her mound tapered down to her crotch and lips, but her little hairs grew to her clitoral hood, and down onto her outer labia. The sight of her beautiful womanhood made my heart skip a beat. So this was the alluring little mystery she'd left uncovered by underwear for me, I thought to myself. It was gorgeous.

I stared at her sex for a moment, my mouth hanging agape. Then I looked into her eyes again. "You're so beautiful, Francesca," I said breathlessly. I was having trouble breathing normally with my heart racing in my chest.

"Am I?" she asked.

"God yes, you're gorgeous. So gorgeous."

"You're the first, Jim. You're the first to see me."

"Oh honey, I'm so lucky. You're amazing."

"I want to look beautiful for you."

"You do, sweetie, you did all night." I took her by the arms and pulled her toward me. "You are absolutely breathtaking." I ran my hands down her arms then onto her back. Her skin was warm and soft and I let my hands roam down to the small of her back, holding her close to me.

Wordlessly she began unbuttoning my shirt. It was already untucked from our intense makeout session in the limo, and she was unfastening the buttons slowly but easily. She looked into my eyes.

"Can I undress you?" she asked.

I nodded eagerly. The moment was becoming real. No longer was our lovemaking some sort of distant, elusive fantasy in my head. Now it was becoming tangible. She was naked before me, unbuttoning my shirt. Soon I'd have to reveal myself to her. I hoped I wouldn't disappoint her. I hoped I would be as remarkable to behold as she had been to me.

Soon she had my shirt unbuttoned, and she slipped it off my shoulders, letting it fall to the floor. She ran her fingers down my chest, letting her nails dig into my nipples as they raked past. Then she grabbed the bottom of my undershirt and pulled it upward. I put my arms up to allow her to slip it over my head, then helped her free it from my arms and tossed it to the floor. She stared at my chest and exhaled sharply.