Hello you awesome readers! This story does contain some Fetish material which I feel always causes a handful of you to immediately leave a poor rating without even reading the story at all. This always drags my ratings down to the mid 2’s right out of the gates which I believe may lead to fewer total readers. I will say what the Fetish is in the next paragraph, so if you think this could be you, please exit the ride now.

This is a historical account of notable experiences of what I consider to be my first legitimate girlfriend (I was a very late bloomer, I know). I am a very nostalgic person, and having all my stories completely written out is as much for me as it is for you. This story fits the “First Time” category best in my opinion, but fair warning, it does contain some mild (to me) poop and pee Fetish material which is not really central to the main story. If you don’t personally like this Fetish, please just move along to a different author.

I only find solid turds from women who I personally rate at least a 7 erotic. No smearing or eating in any of my submissions. If you have some curiosity about the Fetish I would argue that this could be a good starter story. If it’s not your thing, then hey, we can just part ways right here. No harm no foul. Most of the previous stories I have written go a little more extreme in this department.

This story immediately follows my previous submission “Fast Cars and Freedom” chronologically which would add context to the opening scene of this story. All of my stories to this point are intertwined and largely draw from or are 100% true experiences to my memory, some of which were recorded in very rough and unpolished form just after they happened in a “Masturbation journal” if you will (which originated out of necessity long ago during the dark ages of dial up). This being the case there are gaps in my memory and/or certain details which I found uninteresting to write about which sometimes I just fudge through a little. The following is a series of journal entries written down over the course of about a year which I tried to tie together and polish the best I could. It is not just one cohesive story and I apologize if some parts seem abrupt.

There are references and details sprinkled throughout my previous submissions which I think cumulatively enhance all the stories read in any order. However, my goal is to make each piece erotic and stand alone just by itself.

All characters in this story are over 18. Thank you and enjoy!

*****

It was the night before an away basketball game my senior year of high school and I thought everyone else had left on the bus to go to the store. I sat upright, stiff and motionless on the foot of my bed alone in the hazy dark motel room. I heard a knock at the door and got up to see who it was.

I instantly teleport to the door and open it to see that it was Savannah. She was brightly lit up and had a beaming smile. Savannah was a stunning, athletic, 5’9″ tall dirty blonde with a cute face, beautiful hazel eyes and a fucking nice rack.

She asked to come in and we lay on the bed before she immediately began to touch my stomach through my shirt.

“Mmm, I Love your abs…”

She leaned over and kissed me. Oh my god it was amazing as she alternately nibbled my lower lip and stuck her tongue in my mouth. She put her hand under my shirt and felt up and down my abs and up to my pecs.

Her hand ventured down to my pants. My half erect cock immediately swelled to its full length and became a rock hard pole. I could see it tenting my jeans as Savannah slowly inched her hand down my pants and touched my pubic hair.

I knew she could see that I was hard and I asked, “What do you want?”

Savannah said, “I want you to do whatever you want to do to me…”

I couldn’t think of anything to say other than, “Just keep doing what you’re doing…”

Savannah looked at me with a shy and innocent look as she continued down my pants until she reached my throbbing cock. She grasped it in her hand and moved up and down its length and let out a gasp. Then a look of lust came over her face.

She then began to unbuckle my belt and unbutton my jeans. Savannah leaned forward onto her knees with her Ass in the air. Her jeans slid down to reveal the top of her thong and Ass crack and her shirt opened up as it hung down to show her white bra and reveal her incredible cleavage. Savannah pulled down my pants and then started on my boxers.

My cock got hung up in the waistband of my boxers as she pulled them down until it finally sprung forth and audibly smacked my stomach.

“Mmmm…” She said as she moved her face closer to my thick penis. She grabbed it and lifted it up straight.

“You want me to suck your cock Matthew?” Said Savannah before she tried to swallow me whole. I just moaned as she took my penis into her mouth. She took it as deep as she could go and gagged.

I put my hand on her Ass and pulled down her jeans to reveal more of her Ass crack and big juicy buns.

I flipped her onto her back and put my cock near her face. She opened her mouth and took it in as I pumped a few times as I grabbed on to her breast.

I then pulled her shirt up and my god did she have a nice set of titties. I expertly unhooked her bra in an instant and her big thick tits just bounced Free out in the open. I jiggled and bean dipped one boob as I took an erect nipple in my mouth and sucked. I then unbuttoned her pants and quickly pulled them and her white thong off.

I had Savannah naked on my motel bed with my cock out and she spread her legs for me. Her Pussy was soaking wet and I bored my cock straight into her tight entrance.

I fucked Savannah hard, in and out, thrusting my hips as she groaned. I was on the verge, but just before I came I pulled her up and told her to get up against the wall.

I smacked Savannah’s jiggling Ass as she walked and I got up behind her. She rubbed her big round Ass on my cock as I stared at her sexy butt crack. I grabbed my cock and penetrated her Pussy as I mounted her from behind on the wall and pounded her hard.

I looked down as my cock went in and out of Savannah’s Pussy, but from my angle it just looked like it was going in and out of her fine Ass crack.

God she had a fucking nice Ass. Her firm, plump, huge cheeks bounced and shook as I smashed myself into her. I spanked her and watched her fat Ass cheeks jiggle. Just a big fat round Hot Ass Savannah had.

She moaned in pleasure before turning around. Savannah pushed me onto the bed and jumped on top of me. Her huge hanging D cup tits swung and knocked together as she mounted me on her knees. Savannah hovered her Pussy over my cock and rammed herself onto my dick.

She ground herself back and forth several times before she moved to get into a crouched position. Savannah then slammed herself down repeatedly on my cock causing loud wet smacks. I leaned forward with my powerful core and flexed my abs as I grabbed her Ass and began ramming my hips up into her hard and fast.

Savannah then stood up and turned around so her Ass faced me and then ground her Pussy into my pelvis again. I was just staring at that honky-tonk badonkadonk as it jiggled wondrously while she fucked herself on me.

I told her “I’m gonna fucking cum…” and she immediately got off and led me to the bathroom. Savannah squated down on the bathroom floor, “Put your cock in my mouth Matthew…”

I didn’t argue with her and I simply stuffed my cock into her mouth and she started giving head.

As Savannah blew me she started peeing. Savannah pissed all over the floor as she continued blowing me. As Savannah’s piss stream came to an end she let out a loud sexy fart.

Savannah took me out of her mouth and stroked me with her hand as she said, “You wanna watch me take a shit?”

I just about came right there, but I just gritted my teeth and nodded. Savannah stood up and grabbed my head to angle it up as she pushed me down onto my hands and knees. She turned around so her Ass was about a foot away from my face and bent forward slightly to lean up against the wall. Savannah turned her head to look back at me as she let out another nice fart and then sighed as a big poop began to slowly emerge from her asshole…

It continued to come out slow and steady until roughly 7 inches hung from her Ass. Savannah then squatted down and continued to push. Her shit became even longer, 12 inches perhaps, and she stopped again to look back at me.

She gave me a cute little smile and then glanced down towards her Ass as she pushed again. Finally her log hit the floor and began to curl.

“You like watching me dump a big long fat poop baby? Cum for me… cum all over my huge shit…” Savannah said as her thick log continued growing longer and longer…

“Cum for me…”

“Cum for me…”

“Cum for me…”

BEEP! BEEP! BEEP! BEEP! BEEP! BEEP! Smack.

I awaken to my belly and boxers soaking in gooey sticky jizz. My mostly erect morning wood is glued to my boxers and I uncomfortably tear them apart from one another.

Despite finally figuring out what the hell was happening to my penis at night, and subsequently regularly masturbating before I went to sleep now instead, I still got the occasional wet dream.

Today was a special day as the school was providing bus transportation all the way out to the mountain for the seniors to go skiing or snowboarding over a long weekend during Christmas break.

I had tried skiing one time before and got to where I could get down the mountain without falling, but I wanted to try snowboarding lessons this time.

I have “Thunderstruck” blaring with the windows down and unnecessarily rev my throaty V8 just a little on the downshift as I pull into a parking spot before turning off the engine.

Julia, the Hot as fuck blonde MILF school secretary is loading some items into the low outside compartment on the side of the bus. I would guess she was probably around 32 to 35 maybe? She is in tight blue jeans and squatting down on her haunches showing off a good 3 inches of luscious Ass crack and I don’t see any indication that there are any panties on…

I stroll slowly, faking a stretch to lengthen my viewing time, but I don’t risk staring for too long as there are quite a few people around and I get on the bus. Though the boys could no longer sit next to the girls on the bus for basketball games, (my bad) the sensible rule is not enforced on this particular bus today.

I sit towards the back on the driver side of the aisle seat next to a cute 5’1″ tall, 100 pound asian foreign exchange student named Jade who I was extremely slow playing. We had been flirting in class for a few months by now I would guess.

During the ride we talked for probably an hour or so and listened to songs on my new Ipod with one earphone each. I could tell that Jade liked me, and with my recent experience (and by that I mean complete failure) with Savannah, I decided to be bold. My heart raced at just the thought as I prepared my maneuver.

Jade didn’t object when I put my arm around her waist. I slowly inched my arm lower and lower. After a few minutes I moved my hand down so my finger tips rode just under Jade’s waist band. Then I started playing with her thong. My heart was beating out of my chest as I finally moved my hand to the center of her lower back and reached down her jeans and under her thong as far as I could go. My middle finger went right in between her Ass cheeks.

For the remainder of the bus ride my hand remained down Jade’s pants as I caressed her and dipped my fingers in and out of her sexy butt crack.

We finally got to the mountain and I took snowboarding lessons the first day and got to where I could get down the mountain without falling.

We stayed one night in the lodge and on the second day of snowboarding I decided to try to go down the slope as fast as I could. I am goofy and started going really fast. I tried to make a gradual left turn and lost my balance. I then overcorrected and rocketed backwards onto my back, smacking my head onto the hard snowpack. This caused my black santa hat and goggles to fly off as I continued to slide uncontrollably down the mountain. I continued to slide probably about 50 yards down from my gear and had to walk back up to get it. I didn’t try to go fast again after that, and I still don’t to this day.

I really didn’t see Jade at all at the mountain until we got back onto the bus. Perhaps not interacting for awhile made her want me more, but I don’t know for sure.

This time we sat on the passenger side of the bus in the back with nobody on the opposite side of us. I sat next to the window.

I put my hand down Jade’s pants again causing my cock to strain against my baggy basketball shorts. It felt so Hot when I eventually changed position to display my erection to Jade. My heart was racing as my cock stood straight up long and hard, tenting my shorts. Jade definitely noticed the blatantly obvious bulge, but didn’t make a move for at least 10 minutes.

Then she puts her hand on my leg and my heart rate shoots up again. My cock is throbbing at this point and it noticeably starts twitching involuntarily under the fabric.

Jade slowly inches her arm towards me. The back of her hand brushes up against me and she applies pressure to the base of my shaft and begins making caressing motions. This was the very first time in my life that a girl touched my penis with her hand. It felt amazing and I wanted that feeling to last forever…

To my disappointment the bus ride came to an inevitable end. That incredible high of a first time can never be reproduced.

Flirting in class with Jade continued for a few more months. I’m telling you that back then I was glacially slow and terrified of rejection. My rule was that I had to be 99.9% sure a girl was into me before making a move, and even then I was still too shy to make a move. I honestly don’t know what the hell got into me on the bus on the ski trip, but I knew I was wanting more.

I remember a group of us putting up Valentine’s day decorations in the hallway at school. Jade was squatting down in front of me while working on something and when I thought nobody was looking I stuck a yard stick down the back of her low rise jeans into her exposed butt crack. However, Julia just happened to be walking down the hall towards us from behind me and saw me do it.

As Julia strutted by swaying her mature, womanly, child bearing hips and shapely plump round Ass she just said, “That’s not very appropriate Matthew…”

I was smirking with a treat in my hand just above the cookie jar as Julia caught my eye. She smiles and winks at me while tugging at the front of her jeans as she struts her fine Ass into the bathroom… 10 feet away from where I stood.

Mmm, what I wouldn’t give to just walk right in there and open the stall door with my dick exposed and just stroke it in front of Julia while she pisses and takes a nice big poop as she lets me watch…

She then gets up to stand behind me and grabs my penis. “You need to piss baby?” she says, “Go ahead and piss all over my big turd.”

She aims me down and I start unleashing a thick stream all over her fat 9 inch long log. After about 30 seconds Julia says, “Damn baby that’s a lot of piss…” as she maneuvers herself into a squatting position to my side.

She opens her mouth and takes me in mid stream drinking intermittent gulps as piss splashes all over. Julia takes my piss in her mouth for about 15 seconds until it spurts and slows to a drip.

Immediately she starts tugging me down hard and stroking me fast from the base to the head.

“Cum for me Matthew… cum all over my huge shit…”

I hear a flush and then a hand wash before Julia walks back out to the front area and stands with her back towards me as she leans over a nearby counter. Julia’s big pear shaped Ass just popped. Her jeans are so fucking tight and form fitting I can see the crack of her Ass and the shape of her taught round buns of steel. Julia spreads her legs out and supports her upper body on her elbows as she remains bent over the counter…

“Damn.” I say under my breath.

“Wha o ou wa fo val en ines ay ath ew… watthew?”

“Earth to Matthew…”

“Huh? What?” I say as I’m abruptly jarred out of my trance.

“I said what do you want for Valentine’s day?” Jade asks.

“Hmm,” I had to stall a little while to appear that I was just now thinking about this for the first time, “I guess your thong.”

Jade just giggles.

I never met Jade’s parents as they lived overseas. Jade stayed with a lady who didn’t usually get home from work until around 4:30 pm and one time Jade snuck me over to her house after school because she wanted to show me something.

The lady Jade stayed with had a special book. I’ve tried to find this book but the name escapes me and I have no idea who it was by. By my recollection the pages were maybe 18×14 inches and the title may have been something along the lines of “Monsters and Maidens” but I don’t think that was it. It may have had some words too, but I don’t recall for sure as I was only interested in the pictures.

In general, I remember medieval inspired settings with various monsters and demonic creatures with big cocks in sexual situations with very attractive young women who had unrealistically perfect bodies.

One image that sticks out in my mind in particular was an ugly, fat, short creature (a satyr perhaps?) with short horns pictured from a side profile standing up and getting its cock stroked and angled towards the mouth of a naked young woman who was propped up on one arm on her side with her perfectly shaped Ass sticking out. I have actually published a pencil sketch on this site entitled, “Monster and Maiden” I drew a long time ago which was inspired by said book in the erotic art section if you want to check it out.

Anyway, my point is if anybody knows what the name of this book is and the illustrator or whoever it was by it would be awesome if you left a comment so I could buy it.

I’m honestly not exactly sure why I had such a hard time making the first move to ask a girl out. I felt awkward and didn’t want to come across as creepy and always just chalked it up to fear of rejection. However, I knew that I had desirable qualities and I knew that I had the green light months ago with Jade. I sometimes cited fear of getting a girl pregnant which could be valid as I really did not want a child to ruin my dreams and aspirations at a young age. Perhaps I just wanted the privacy of my own place first because I really wanted to get soaked…

Just me being shy is probably the real answer.

One day Jade and I walked together to golf practice (I’m pretty sure she joined just because I played because she was terrible) and I opened the door for her into the gymnasium. Somehow we are completely alone and as we walked across the center of the court Jade grabs my Ass and pulls me towards her for our first kiss…

It is relatively quick and very exciting due to the environmental circumstances, perhaps only 5 seconds or so, but my heart is beating hard and continues fluttering for minutes afterward. I would say we officially became an item after that point.

Fast forward to spring break and Jade is sitting on my lap in a maroon, super comfortable passenger seat salvaged out of an old Eldorado. We are making out in a little shed in my backyard and she begins playing with my jeans. Jade slides her hand down the front of my pants and I thankfully was able to keep my mouth shut this time around.

Jade quickly reaches my cock and she lets out a gasping moan combination as she grips the shaft in her tiny hand. Her thumb and forefingers aren’t even close to being able to completely close around my girth as she strokes up and down the entire length. Jade looks me in the eyes as she unzips my fly, undoes my belt buckle and unbuttons my jeans. She yanks my pants down a little and reaches in to pull out my throbbing cock. “Wow… it’s so long and fucking thick…” Jade says in her sexy accent as she admires its size and heft in her hand for awhile.