Gilmore Girls: Educating Rory
Featuring Lorelai Gilmore (Lauren Graham) and Rory Gilmore (Alexis Bledel)
By The Pornographer
(MF, blowjob, reluc)

This FICTIONAL story contains graphic sexual situations, if you are easily offended STOP READING! Feel free to send any comment or suggestions

My name is Jack, and I’d like to share with you about how it came to pass that for the past six months I’ve been sleeping with two extraordinary women – Lorelai and Rory Gilmore. I’m 27-years-old, and 5’10. So how you ask, how did I ever become so fortunately to be blessed with enjoying both mother and daughter? Let me explain.

It all started one cold winter morning when I arrived into the sleepy town of Stars Hollow. New in town I was out grocery shopping when I bumped into this incredibly attractive woman by the name of Lorelai Gilmore. From the moment we met there was an undeniable attraction between us. Chatting over coffee, I later walked her back to her place which was just around the corner and by the time we reached her front porch we both knew we had to have each other.

Making out passionately, Lorelai then pulled me inside and proceeded to blow my cock, and my mind. I couldn’t believe a woman of her calibre was available. So over the next few weeks we started to date, despite the fact that Lorelai was almost 5 years my senior! Regardless, Lorelai and I continued to see each other on a daily basis, and due to the scandal regarding our ages no one knew about our relationship – no one except of course Lorelai’s 17-year-old daughter, Rory.

Spending a lot of time at the house to our amusement everyone in the town just assumed I was helping out seeing as I was a part time handyman. Then at one point when the girls and I went out to dinner someone assumed and asked if I was Rory’s new boyfriend, and of course to Rory’s dismay Lorelai jumped right in and announced that in fact Rory and I were together. Despite the fact that we couldn’t tell anyone, Lorelai really got a kick out of that – secretly dating someone who was young and attractive enough to be with her teenage daughter.

But eventually spending so much time together word soon spread around town, and feeling pressured Lorelai openly acknowledged our indecent relationship. I suppose it didn’t help that on any given afternoon pedestrians would just stop and gawk at the Gilmore house seeing as anyone who was in ear shot could clearly hear her moaning and shrieking out my name in ecstasy. The woman was insatiable.

If I thought I was the luckiest man alive to have found such a sexy, willing, and open minded partner, I soon thought all my Christmas’ had come at once as her sweet, bright, and shy daughter Rory and I began to flirt and exchange knowing glances at each other. It all began innocently enough as a few weeks earlier when anytime someone would stop by the house, Lorelai would make Rory and I pretend to be a couple, and a very happy one at that.

At one stage Rory and I even pecked each other on the lips – putting on a show and trying to convince Sookie that we were together. That day in particular was quite entertaining as the moment Sookie left the house Lorelai playfully yanked me out of her daughter’s arms and smiled, “Hey, don’t get any funny ideas about my daughter Jack, you’re my stud!” and with that kissed me hard on the lips while squeezing my butt.

Clearly disgusted by her mother’s behaviour Rory protested, “Mom! Can’t you control yourself? Why don’t you get a room!!”

“Good idea!” Lorelai exclaimed, and we rushed upstairs to fuck.

From that afternoon I began to notice a certain way Rory would look at me. At first I thought I was just imagining it but soon it was obvious she indeed had a crush on me, and truth be told I was beginning to have a thing for her as well. But with Lorelai pretty much fulfilling my all and every desires, I was just happy to play along and continue to harmlessly swap glances with her from a far.

So now Lorelai and I had been publicly dating for just over 3 months when Rory’s eagerly anticipated 18th Birthday rolled around. Standing around in the kitchen and celebrating her big day we all cheered as she blew out the candles. Organizing a sleep over with her friends, Lane and Paris, I had convinced Lorelai to allow the girls to have a few drinks, and in their excitement they all kissed me on the cheek before disappearing into Rory’s bedroom where there they drank themselves drunk in celebration.

Meanwhile, Lorelai and I got cosy on the sofa downstairs where there we shared a bottle of wine and a movie together. It was then just after midnight that the movie finished and Lorelai flashed me that cheeky grin of hers. Squeezing my cock through my pants we proceeded to make out and fooled around when she then stopped half way through and suggested we retire back to her bedroom. Upstairs, we then proceeded to fuck the shit out of each other for the rest of the night, and after 4 rounds of love making we finally fell asleep in exhaustion.

As most people suspected, especially all the men in the town, Lorelai was an absolute wildcat in bed, and was pretty much up for anything. No matter what the situation Lorelai could never get enough. Sex with her was fantastic, and I couldn’t ask for anything more, or so I thought. Later that night while Lorelai lay snoring beside me, I awoke after hearing a noise in the hallway. Glancing at the clock I could see it was just after 4am.

Listening intently I then realized that it was most probably the girls across the hallway, who unbeknown to Lorelai had not only spent the night drinking to their hearts content, but had also snuck in some weed and were experimenting. Hearing the footsteps move around the house I carefully snuck out of bed to see who it was. Carefully opening the door I glanced out to catch sight of Rory drunkenly stagger down the hall and towards the bathroom.

Clad in just some short shorts and a tight little tee, she disappeared into the bathroom and a moment later I heard the shower start. Suddenly intrigued I decided to snoop around and see where the others were. Quietly stepping into the hallway I carefully opened Rory’s bedroom door and found the girls for all intensive purposes knocked out on the floor in their sleeping bags. Snoring softly, I laughed as I spotted Paris desperately clutched an empty bottle of Southern Comfort.

Grinning to myself I then closed the door and was about to head back to my room when for reasons I can’t explain I turned and quietly tip toeing down the hallway. Suddenly, the mere thought of catching sight of Rory drunk and in the shower was just too good of an opportunity to pass up. As I debated if what I was about to do was wrong, I had already arrived to the door and was already turning the doorknob carefully.

Turning it slowly I then suddenly jumped with fright as I heard her cough and clear her thought from inside. Holding my breath I then carefully leaned on the door and ever so gently opened it and peered inside. There to my delight I found Rory standing in front of the mirror examining herself. As the small tiled room began to fill with mist I watched as she looked at her sorry state in the mirror and then began to drunkenly unbutton and unzip her shorts.

Washing her face, a second later Rory then pulled down her shorts and yanking her panties along with them. While I grinned with glee at the sight of her perfectly formed tight little butt, I then watched her turn around and slip her tee over her head, giving me the very first uninterrupted view of her 18-year-old teenage snatch. I almost gasped out loud in sheer delight. Her body was GLORIOUS to say the least. To my amazement her pussy was shaved clean and utterly hairless - which totally took me by surprise and shocked me completely.

Glancing at herself in the mirror again, I then watched as she ran her hand over her breast and caressed her skin, admiring the way her small thick nipples jutted out firmly. I was literally speechless as my cock was now throbbing so hard I thought I was going to pass out. Giving out a low sigh she then stopped what she was doing and reached out to gauge the temperature of the shower. Then to my disappointment, just as her tight little ass wiggled into the open cubicle, the mist had completely filled the small space and totally obscured my view.

Frustrated and upset, I then glanced down at her discarded clothes on the floor and without thinking quickly reached inside and picked up her shorts and panties. Disguarding her shorts almost immediately, without thinking I brought her used panties up to my face and inhaled her scent. I was happy to find them still warm from her body and her 18-year-old nookie. And taking one last look at her silhouette in the shower I shut the door behind me and rushed downstairs.

Getting comfortable on the sofa downstairs I stroked my cock to her used panties in the dimly lit room when a few minutes later unbeknown to me, Rory had exited the bathroom and just clad in a towel head downstairs to grab an aspirin and glass of water. Halfway down the stairs to my dismay she then suddenly spotted me and appalled, watched as I stroked my cock with her underwear. Finally finding the power of speech Rory stormed over and confronted me.

“What the hell?” She howled, “What the fuck are you doing!?!”

Startled, I tried to explain but Rory wouldn’t have any of it.

“Shut the hell up, you... you dirty bastard!”

“Just keep your voice down Rory, please!” I told her.

“You’re sick Jack! Wait till I tell Mom about this!!”

Seeing how upset she was I tried to calm her down but I knew she wouldn’t understand.

“Look Rory honey, lets talk about this please! Come here, sit down,”

“What! No way!” she protested.

“Come on Rory please, just sit down and let me explain myself. You can at least let me explain...”

Rory stood there thinking for a moment until she finally, tentatively, stepped forward and sat on the edge of the sofa beside me. As she sat down I noticed that her eyes didn’t leave my cock which in all the commotion I had forgotten to cover up.

“Look, it’s just some harmless fun... that’s all,”

Almost immediately Rory retorted, “Yeah right, how could you do that... to Mom... and to me!”

“Hey, I’ve never laid a hand on you Rory, even thought you’re incredibly beautiful and a total babe...” I replied.

Rory suddenly perked up and I knew it was the comment I had made about her being attractive.

Smirking she replied, “Really?”

“Yes really. I care about you and would never hurt you... or you’re Mom for that matter,”

Rory thought for a moment before replying, “I guess...”

“I’m just letting off a little steam, that’s all,”

Staring at my raging hard-on again Rory then took me by surprise when she bit her bottom lip and nervously spoke, “Well... can I watch?”

Shocked, I didn’t answer and simply reached down to gently stroke my cock again. Rory’s eyes widened as she watched my cock grown and twitch with excitement. Sitting back and getting more comfortable I could see that Rory was sincerely fascinated. With one hand resting on the inside of her leg I watched as she squirmed and fidgeted about and without thinking began to run her fingers up the length of her thighs.

Watched me intently for a minute Rory then noticed me sniffing her panties again and spoke, “What’s it like?”

I smiled and handed her underwear to her. Taking them in her hand she slowly brought them up to her face and inhaled. Shrugging her shoulders she wondered what all the fuss was about. Watching her towel hike up a little and expose her creamy white thighs I gulped with anticipation while Rory caught me staring and grinned mischievously. Placing her hands on the hem of the towel she then covered her legs up.

“Hey, don’t do that...” I said.

To my surprise Rory actually had this sly grin on her face and I think she was actually getting off on seeing me squirm.

Slowly lifting the towel she teased, “Is this what you want Jack? Is this what you want to see?”

I could only nod as my hand pumped vigorously over my tool. Seeing this reaction Rory now figured that the more she teased the more I grew, hence the more she enjoyed the sight of seeing me throb over her.

“Yeah that’s it, that’s what I want to see... what I want to smell...”

Lifting her towel a tad too much she then inadvertently flashed me her pussy for a moment and in turn I let out a groan.

“Oh hell yes, show me that pussy Rory,”

To my amusement Rory actually blushed and smiled shyly. Teasing me she then began to flash me her hairless crotch, making me squirm and gasp with delight every time she flaunted me her bare slit.

“Oh god damn Rory,” I breathed, causing her to giggle, “that pussy of yours looks amazing...”

Rory giggled, “So I guess I shouldn’t do this then...” and with that she ran her index finger over her tight moist slit.

Deep down it seemed that Rory was in fact an exhibitionist and loved to tease.

“Oh god yes... more, show me more baby,”

Rory smirked and then reached to the side of her towel to untie the knot – letting it fall off her body and leave her totally naked. At this point I was so worked up I didn’t know what to look at first, her beautiful natural breasts or her incredible pussy. Biting her bottom lips she then proceeded to play with her perfect cunt as she watched me stroke my stiff prick. Running her fingertips the full length of her thin pink lips, Rory continued to stare keenly at my hard-on when suddenly she spoke.

“C-Can I try... can I do that?”

“Would you like to touch it?”

“Yes,” she replied softly.

With that Rory tentatively nudged closer and ever so gently gripped my tool.

Grinning in delight she mumbled, “It’s so warm... thick...”

“Just give it a few nice strokes baby, and watch it grow harder, thicker...”

Flashing me a cheeky grin Rory then began to stroke me steadily. Licking her lips with fascination, she then leaned over to take a closer look and I gently placed my hand on the back of her slender neck and proceeded to massage her and play with her long brown hair – which was still wet from the shower. She smelt incredible. Leaning ever closer and closer, Rory’s face was now just a few inches away from my cock and to my delight I watched as her lips suddenly parted and her tongue darted out of her mouth.

“Ohh yessss, show me that tongue again...” I told her, and she smiled sweetly.

I then told her, “Kiss it...”

For a moment Rory instinctively pulled away, shocked at just the mere thought of it. But suddenly watching it twitch and grow in her hand with anticipation Rory’s curious 18-year-old libido took over and without saying a single word she slowly leaned forward and placed her luscious lips on the tip of my bell-head. Hearing me groan with delight Rory then smirked to herself before she then placing a soft sweet kiss on the side of my cock head.

“Oh yesss, that’s it... do that again,” I groaned.

Rory simply smiled and looked amazed as the contact from her mouth really started to rile me up. I was now as hard as I could be as Rory proceeded to lay soft kisses all over my cock. Gripping her hair I then held her close to my rod and told her to kiss the entire length. Doing as she was told, suddenly, Rory caused me to give out a low moan when without being instructed she stuck out her long wet tongue and began to slowly slither it up and down the length of my throbbing shaft!

“Ohh fuuuuck...” I let out.

Taking her time Rory then worked her way up to the tip and then without warning parted her lips and took a considerable length into her hot mouth. Wasting little time she then proceeded to give me a slow and meticulous blow job. Bobbing her head up and down for a few minutes I was so hard and aroused I could almost scream. Instead I just leaned back and enjoyed every second of this incredibly beautiful teenager giving me the longest, slowest, sweetest blowjob ever.

Rory would bob up and down with just the head of my cock resting between her sweet lips, before sliding it in and out of her warm mouth and taking me deep until I could feel the end of my tool press against the back of her throat. That especially blew my mind as Rory would hold me there in that position for a moment longer and would only let go after she began to cough and gag a little. I tell you, she was a natural, and really knew how to give great head.

I don't know how long we were there, but it was a very, very, long time. If I had to guess I would have to say over and hour. Each time she would sense that I might cum, she’d back off and do something else, like lick my balls or lay her head on my stomach and lightly blow over the tip of my member. Her cock sucking skills didn’t just stop with her mouth as well, as she’d then run her fingernails up and down my stomach and look up at me with those big, blue eyes to see if my imminent orgasm had subsided.

Then, I would nod and she would go back to some serious cock pleasing. Finally, I was close to climaxing, and I grabbed Rory’s head and held it firmly as I humped her hot, pretty mouth. Anxious and excited at receiving her very first cumshot, Rory proceeded to make this low whimpering noise as I vigorously fucked her gorgeous face - which in itself was a utter and total turn on. Finally, I erupted right inside her warm mouth like a fire hose, and Rory gagged terribly for a moment before I finally pulled out, to spray her.

But just like her mother, the younger Gilmore was no quitter, and she frantically licked and rubbed my spewing cock head around her face as I came and came all over her beautiful face, coating her chin, cheeks, and mouth. Still gushing my seed Rory opened her mouth and took more cum till I filled her mouth. Then she looked up at me and her face grimaced as she forced herself to swallow the biggest load I think she had ever had.

Taking a deep breath Rory exhaled and laid her head on my lap and whispered, “Thank you.”

Stroking her hair I smirked, “Happy birthday baby, happy birthday...”