Gilmore Girls 1. Chapter 1

_This is written as though Logan is telling somebody after his time with Rory. I have never done anything like this before and am a little unsure about it so let me know._

The next weekend I drove up to visit her. Rory lived with her mom and grandparents in a modest town home. She went to college full time and worked part time to help pay rent and for a little shopping money. Her mother was saving to buy a new home, as after her divorce neither she nor her ex could afford the payments on their previous house. I felt it was rather sweet of Rory to stay with her mom and help pay rent, but nevertheless hoped it wouldn't interfere with our fun. Rory's place was a pain to locate, since it was nestled within a community with confusing building numbers. Finally with her guidance over the phone I was able to find her place.

I had made really good time driving up to her place. This was somewhat unfortunate because I was earlier than I'd told her I would be. Her mother let me in and informed me Rory had just finished showering. I silently lamented Rory's living situation, because her being wet and fresh out of the shower could have had fun possibilities otherwise.

After she came down she gave me a quick tour. Her room was really nice, and I swear I'm not biased because of what went on in it. I was jealous of her room's own bathroom with full tub and shower, which I hoped we could put to good use later.

Rory looked very cute in a white halter top and low rise jeans that clung to her lovely ass. We decided to go walk around the mall. In the car Rory's seatbelt shifted her top. It was rather light and loose, and I was able to catch a glimpse of her light pink nipple by looking down her shirt. Rory is small chested and had opted against wearing a bra. She didn't appear to notice me peeking, and my appetite was whetted for what was to come.

Wandering around the mall was fun. Neither of us was really in the mood to buy anything. She seemed happy just to spend time with me and preferred to go into the stores I was interested in. The date was fun though not especially remarkable as far as such things go. We talked, laughed and occasionally found excuses to touch each other flirtatiously. After grabbing some lunch we headed back to her complex to lie by the pool and enjoy the weather.

Lying by the pool was nice. Seeing Rory in a bikini was inspiring, and I could tell she enjoyed seeing me in only my trunks. If seeing Rory half dressed was nice, talking to her was truly wonderful. She's amazingly easy to talk to and definitely has many ideas on topics that I had not yet considered. I appreciate it when people are thoughtful and have their beliefs for a reason. We traded off asking each other questions while we soaked up some rays, and then decided to try out the hot tub.

We hopped into the tiny hot tub near the pool, which was semi-private at best. The sun was high in the sky that bright afternoon. We twiddled our thumbs for a few short minutes before the tension got the best of us and our lips met. There was kissing and groping and even some heavy petting though our swimsuits. We paid no mind to the only other person in the pool area, a middle aged man who was lying on the other side of the pool. If he noticed us at all he didn't care, because he was facing away the whole time. Regardless, making out in public with a really cute brunette girl with startling blue eyes is a wonderful experience and had a bit of an exhibitionistic element to it. I certainly took the opportunity to squeeze her ass as she sat on my lap and ground her pussy against my penis, our lips locked together. At one point she even reached under my suit and stroked my dick beneath the swirling water.

When the limits of public displays were reached we wrapped our towels around ourselves and retreated to her room. Luckily no one was around to ask any embarrassing questions. Rory dropped her towel in front of her mirror and began brushing out her hair. Her wet bikini clung to her body in an enticing manner. I dropped my own towel and came up behind her, placing my hands on her hips gently. I slid my own hips forward and pressed my rock hard dick against her lovely ass through our wet swimsuits. Her eyes remained focused on the mirror image of us while I moved my mouth to her neck. I sucked and nibbled her neck as my hands slid up and down, exploring her body, occasionally glancing up to see my counterpart in the mirror doing the exact same thing to his Rory.

When my hands began trying to liberate her top from her body she decided we needed a tad more security. She squirmed away from me over to her door, which she locked. She picked up her remote and turned on the small TV atop her dresser to create background noise. She then turned to me and gave me the sort of look a woman gives the man she wants to be ravished by. I got the message loud and clear.


	2. Chapter 2

I imagined I was quite the sight for her, standing not two feet away, wet and half dressed. Yet she waited for me to make the next move. I did, taking her into my arms and kissing the young beauty. We moved to her bed and soon our hands and mouths were everywhere. I finally took off her top, exposing her hard light pink nipples atop small firm breasts. I fondled her breasts, suckled her nipples. She moaned with appreciative passion, lust overcoming her nerves.

I slid up her body and kissed her once more, grinding my erection against her pussy through our clothes. Despite my lustful state I took my time, savoring each new shared experience, treasuring the whole experience.

Finally I took off her bottoms and got to see her fully naked for the first time. It was worth the wait. Her pussy was beautiful with a lovely haircut of a small strip above her clit and shaved lips. Her lips and clit were of balanced size, and she truly had one of the prettiest pussies I've seen.

In our conversations we had discussed spanking as a sexual activity, one which she had a lot of curiosity about and no experience with. I had spanked women playfully, but never beyond playfulness or a random lustful swat during a heated moment. This would be spanking as foreplay. Rory's firm ass demanded to be spanked if one ever did.

"Roll over," I said to her, tenderly yet with force. She looked at me for a moment, her face showing a mix of lust and nervousness. I had my own nervousness about executing our shared desire satisfactorily.

I admired Rory's bare ass for only a moment before placing my hand on her buttock and squeezing it gently. "Tell me if it is too hard or not hard enough," I said, then lifted my hand and brought it down gently, cupping her ass with only a slight impact.

Rory giggled and spoke only "Harder."

I was happy to comply, lifting my hand once more and bringing it down upon her lovely ass, somewhat harder than the last. It made a satisfactory smacking sound as it connected with her flesh. She gave a slight shiver from the sensation and confidently stated "Harder. Please."

She didn't see my huge grin as I lifted my hand and once again brought it to her ass, this time with the level of force one might use to punish a small child. Once again I left my hand on her bottom and cupped it rather than striking it. She gasped slightly at the impact this time. I felt a rush of power and a certain animalistic glee. I was thrilled when she let out a low pitched, "A little harder. Spank me."

She didn't have to ask twice, and I brought my hand down twice more in quick succession. The first was a repetition of the previous spanking with a little more force. The second was of similar power but was more of a striking blow across her bare flesh. At that Rory gasped once more before letting out a guttural moan.

"Gosh. You really know what you're doing!"

I leaned forward and kissed her between the shoulder blades, my right hand still cupping her ass. "I'm glad that you like. It's a learning experience for me, but I've done some reading," I told her.

I delighted in giving her right buttock a few more swats before switching to her left cheek and giving it similar attention. We both were aroused before our foray into spanking, but as I finished we both were overwhelmed with lust.

I grabbed her hips and rolled her over, taking a moment to refresh my memory of her luscious body before trailing kisses across her tummy all the way up to her mouth. Our mouths intermingled once again, this time with her rubbing her bare sex up against my dick through my trunks. I forced myself off of her and positioned myself at her side. She started to protest, but I shushed her and slid my hand down her stomach, through her pubic strip, and across her swollen labia. She jumped slightly at my touch. I looked her in the eyes as I teased the outside of her pussy with my fingertips. She closed her eyes and bit down on her lower lip. In that moment she was truly a vision of aroused beauty.

I gently parted her lower lips and slid a finger inside her. Though the outside of her pussy was not damp, inside she was a soaking wet furnace. I adore women's physical signs of arousal, and this was further affirmation that she'd enjoyed me spanking her.

I took my time fingering her, hooking my fingers slightly and sliding them halfway within her wetness. I pressed my palm down as I moved my fingers back and forth to simultaneously stimulate her clit. My mouth nibbled on her nipples, collar bone, and every inch of her I could reach while maintaining my gentle, yet steady, stimulation of her pussy. She opened her eyes and looked at me longingly, whispering out "Please, more!"

I was happy to give her what she wanted and began rubbing her faster and firmer. Her body responded marvelously. She began bucking her hips and panting, her chest rising and falling rapidly. At last she sucked in her breath, her pussy tightened around my fingers, and her whole body tensed up. I felt her climax, watching her face with great interest. As she came down from her peak she opened her eyes and looked at me adoringly. I held her tight. I could see she was savoring her post-orgasmic bliss.

"Our clothing situation is a bit unfair," I said, and took off my swim trunks to let her see me fully naked, and fully hard.


	3. Chapter 3

It was not a surprise to her, but she said to me "Wow. It may be cliché, but let me say it is even more impressive in person." I lay on my back and she pressed her naked body against my side. "I've got to get my hand around that gorgeous penis!"

She reached down to grasp my penis gently, feeling its girth with her hand. She stroked it somewhat tentatively. This virgin had given a hand job or two in her life, and I was happy to allow her a chance to pleasure me with her hand. Her eyes were intensely fixated on her hand pumping up and down my thick shaft.

The whole scenario had excited me immensely. Kissing in the hot tub in public, making out, sucking her tits, seeing her naked, spanking her ass and making her cum with my fingers had all combined to push me close to the limit of arousal. As her hand slid up and down my long shaft I could feel that my own climax was imminent, and given the long build-up I knew it would be a big one.

"Do you want to make me come?" I asked her.

"Yes," She replied eagerly.

"Where do you want it? Where do you want me to come?" I asked her with some urgency.

"You choose" she said, perhaps with a mixture of desire to please me and indecision.

"I want to shoot all over your stomach." I told the nineteen year old virgin who was stroking my rock hard dick. She rolled onto her back, not releasing my dick from her grasp. I nestled my body next to her, aiming my swollen weapon at her navel. She stroked me faster and I began to thrust with my hips.

"So you want me to come?" I asked her almost demandingly.

"Yes." She said with conviction.

"Tell me. Ask me to come on you" I said, allowing my dominant side to show through in that moment of passion. I could feel the beginnings of my climax.

"Come on me. Come on my stomach!" she spoke out clearly. I love hearing a woman ask for my cum. Her words set me off, and I erupted onto her flat stomach. Her hand immediately slowed. The first blast or two shot up all the way to the middle of her chest, while the rest of my significant load pooled itself in and around her small belly button. She purred appreciatively.

"That is some load," she said, using her free hand to scoop up a dollop of my warm seed. She brought her finger to her lips and tasted it tentatively. She then slid her finger into her mouth and sucked it clean before sending it back for seconds. I watched as she cleaned off the majority of my load from her skin, sending it down to her tummy.

"You like?" I asked.

"Yeah. Honestly you're the best tasting guy I've ever been with. It's salty, yet sweet. Nice and warm too. Next time I think I want it in my mouth." My still hard penis jumped at the mention of my penis in her mouth. We hadn't explored oral sex yet, but I expected it would happen soon.

After some relaxing and pillow talk we took a shower together. It naturally entailed more kissing and groping. At one point, I pinned her right arm to the wall while I was fingering my pussy and she just about lost it. She loved it when I would take control, and told me she experienced a feeling of pure heat within her as she felt herself surrender a bit of herself to me. Eventually the shower got too hot for us and we dried off and somewhat reluctantly dressed. We cuddled together on her bed, simply enjoying the company. Part of me wanted to play with Rory more, but unfortunately my hunger got in the way. Rory was famished as well.

We passed Rory's mother on our way out and informed her of our plans. I have to imagine that Rory's mom had some idea of what we were up to in her room with the door closed. But, I also suppose that the mother of a shy 19 year old is accepting and perhaps somewhat happy when her daughter brings a polite young man home. I've known plenty of mothers who happily ignore the evidence of their children's sexuality.


	4. Chapter 4

We got together again the very next weekend. Rory hopped a commuter train to San Diego and I met her at the station. She looked lovely in shorts and a small t-shirt, and I greeted her with a kiss.

I greeted her with "Hey beautiful."

She blushed adorably and responded "Hey stud. How are you?"

"I was good earlier, now I'm great." We had gotten into my car and begun driving towards my house. "What do you want to do first?"

"I'm open for anything really. I mostly just want to hang out," she replied. Her hand stroked my thigh suggesting the true meaning of 'hang out'.

I really just longed to take her home and ravish her young body, but I figured a short wait would only whet our appetites. "Are you hungry?" I asked. She nodded. "How about we eat first, so we don't have to worry about it later?"

She nodded at my suggestion. "Yes, I would hate to have to interrupt our activities to eat," she said in a suggestive tone. We stopped for some fish tacos and soon arrived at my apartment.

Rory all but marched straight to my bedroom and I quickly followed. I shut the door behind me and she threw herself into my arms. Our hands were everywhere as we settled ourselves down onto my queen sized bed.

Once again I took my time, but it became clear that Rory was eager to resume where we'd left off. Nevertheless, I undressed her patiently and deliberately, kissing her skin and admiring her pretty red bra and panties before removing them. Rory helped me out of my shirt and pants in similar fashion, leaving me in just my boxers.

I admired the beauty of Rory's young body once more. Her pale blue eyes looked at me lustfully as I licked her nipples, swirling my tongue down her tummy, past her navel, to her brief pubic stripe. She moaned appreciatively as I bypassed her vulva and kissed my way down her left inner thigh before slowly kissing my way back up her right thigh, approaching my final destination.

At last my tongue made contact with her smooth pussy lips for the first time. She tasted natural and clean with just a hint of sweat. My tongue slid up and down her outer lips for the first time, and she definitely enjoyed the attention I was giving her.

Gently I dipped my tongue into her pussy, tasting the wetness within. Rory cooed appreciatively as I darted my tongue in and out of her, then licked up and down her pussy slowly. She closed her eyes and clenched my sheets in her hands. As I continued licking her I no longer noticed her taste, focusing only on bringing pleasure to the beautiful naked girl before me.

All too soon she whispered "wait." I paused and looked up at her. She placed her hands on my head and pulled me up slightly. I didn't want to stop licking her, but granted her wish, stopping only to place a couple kisses on her body on my way up. Our mouths reunited, and I knew she could taste herself on my lips.

"That was lovely," she said, just above a whisper. "I've never had a guy go down on me. Not like that." I would have gone down on her for hours in exchange for the beautiful smile she gave me. "Your turn," she said with a grin, and I allowed her to roll me over.

"Let's see what we can find," she said, almost to herself as she brushed her hands softly against my chest. She straddled my thighs, sitting just below my erection and giving me a great view of her pussy. Her hands darted down to the large bulge in my boxers. "Hmmm, now this is interesting!" she exclaimed. "I wonder what this is."

She lifted herself off my legs to hook her fingers and tug my boxers downward. I lifted my hips and helped her free my erection from my shorts without inflicting injury. Once she removed them from both my legs she tossed the shorts aside, returning her attention to my penis.

"Wow. It still amazes me every time I see it." I opened my thighs and she positioned her small body in between them. Her face was just inches from my penis, and she took it in her hand and began stroking it gently. "You like that?"

"Oh yes. I like it a lot." I responded.

"Mmmm, do you want me to put your big dick in my mouth?" Rory asked teasingly.

"Yes!" I exclaimed.

"Tell me what you want. I've never had such a big penis in my mouth and I'm not sure how to handle it." I knew there was a mix of truth and game playing in her statement. Although she'd sucked a dick before I knew mine was bigger. I also knew that Rory enjoyed being told what to do and probably wouldn't mind a pointer or two.

"Keep holding it like you are. Good. Now lower your head and lick it. Oh yes!" I jumped as her pink tongue touched the head of my member for the first time. "Yes, lick the head. Mmmm, now work your way to the little ridge around it. Oooh, yes, that's very sensitive. Lick it Rory." Rory followed my orders perfectly. "You're doing great. Now lick your way down the bottom side. Good. Stay there for a second and lick right there." I instructed as her tongue stopped at a lovely spot between my balls. Now back up the side. Good. Now lick the topside a bit. Mmmm, you look so sexy licking my big dick." Rory smiled at me and giggled before licking the often neglected topside of my shaft.

"Ok sweetie, now I want you to suck on me." Rory positioned her mouth at the tip of my penis. I watched as my thick shaft slowly penetrated her lips for the first time. "Slowly there's no rush. You look lovely with your lips wrapped around my penis." Rory moaned lustfully, muffled by her mouth full of penis.

"Now up and down. Mmmm yes, suck me. Can I put my hands on your head?" Rory nodded. She released my penis for a moment and sucked in a deep breath.

"I'd love it if you guided me with your hands" she replied and replaced her lips on my shaft. I ran my fingers through her hair; guiding her speed and depth but mostly letting her do her own thing.

Abruptly she pulled away and slid up my body. Still holding my dick, she looked me in the eyes and asked clearly "What do I have to do or say to get you to fuck me with this thing?"


	5. Chapter 5

I had given little serious thought to being Rory's first. Although things had moved quickly thus far, I tended to view virginity as something that people lost after long months of dating. My penis certainly liked the idea of penetrating her.

"Are you sure?" I asked, with genuine concern. "I think you're great but I'm not sure where this is heading."

"I know." She replied. "Don't worry about that. Please trust me; this is what I want to do." I silently nodded, accepting her decision.

I rolled to the side of my bed and fetched a condom from the drawer. She watched attentively as I rolled the protective latex down my member. Taking her in my arms once more I kissed her, tenderly then passionately. My hand slid between her legs. She was tense and dry. I continued kissing her as I massaged her clit gently, hoping to relax the young beauty who had offered herself to me.

I moved on top of her and positioned my penis just above her pussy. With gentle purpose I rubbed my shaft against her opening as I continued staring into her sky-blue eyes. I felt her body relax a little, though I knew she was still tense. My penis began slipping across her pussy with greater ease as a result of her natural lubrication. I moved my hips downward, pressing the tip of my penis against her.

"Ready?" I asked.

"Yes. Please, I'm ready." She replied.

I supported my weight on my hands as I pushed myself into her as gently as possible. She was wet and ready. Her pussy clung to me, but I felt no resistance as I eased more of myself into her. She closed her eyes and bit her lower lip, her hands clinging to my hips. At last my penis was fully inside her. Rory was no longer a virgin.

I sat motionless for a moment, letting her adjust to the feeling of having a man inside her. She ran her hands up and down my back, and opened her eyes. "Wow," she whispered. "That is nice."

I could have accused her of making a gross understatement. Instead I began slowly rocking my hips back and forth, stimulating her pussy with small movements. They had the intended effect.

I wanted to give her the fuck of a lifetime, a long fuck culminating with massive simultaneous orgasms. However my penis had other ideas. She'd given some good head, and I was terribly excited to be fucking her for the first time. I knew I couldn't thrust very much without losing control and coming.

"God. You're so sexy. I'm really close," I exhaled.

She smiled at me and suggested, "Let's just sit for a moment. I really like how you feel inside me." We sat together, my penis deep within her, listening to each other's breath.

"Ok" she spoke after a moment. "Please come inside me."

I almost came instantly as the words escaped her lips. My dick definitely throbbed within her, a fact that didn't escape my young lover. I began to thrust into her, slowly at first, but using the full length of my shaft. Her eyes lit up in amazement.

"Oh!" she exclaimed as I slid all the way out and back in again. Sitting still had allowed me to settle a bit. I knew my orgasm was still impending, but I also knew I could give us both a good minute of thrusting before it happened.

I began thrusting faster and harder. Rory seemed to slip into her own little world as I fucked her for the first time. I pressed my body against her as I plunged deep within her, getting lost in my own sensation. At last my climax came. I let out a loud moan, and I'm sure Rory could feel my penis throbbing within her tight pussy. I collapsed on top of her.

"Wow. That was everything I hoped for and more. Thank you." She told me. I couldn't help but chuckle. This beautiful girl was thanking me for fucking her? I kissed her gently.

"I should be thanking you," was my reply.

We enjoyed laying together until our heart rates returned to normal. I lifted my body off hers, the sweat dripping off our heated bodies. As gently as possible I slid my still mostly hard penis out of her pussy. I could tell she would have preferred that my penis stay inside her permanently.

Rory didn't move as I removed the condom and cleaned myself off. I crawled back into bed with her and we arranged ourselves so I was spooning her. We sat quietly for a good while.

Later I became hard again and she decided to have a try at riding my penis. She looked amazing bouncing up and down on top of me. I especially enjoyed gripping her firm ass as she slid up and down my dick. She rode me for a good twenty minutes before telling me she wanted to feel me cum. I was happy to oblige.

She didn't climax from the intercourse either time, which is pretty typical for a couple's first time together, virgin or not. It often takes time and experience to get to know what really works for each other and to achieve a sufficient level of comfort. I was able to help her achieve a lovely climax afterwards by rubbing her pussy while sucking her nipples and telling her the story of how I'd fucked her with my big penis.

After the weekend at my place unfortunately we didn't really see much of each other we talked or rather typed regularly but after a while we just drifted apart and the emails slowed and eventually stopped.

The times I spent with Rory were some of the best times of my life and I am gratefully that I got to spend time with her even the with the unfortunate ending I still have never regretted it and my hope is that she didn't either

THE END


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Gilmore Girls, Angst, Romance