Sarah's Sexual Saga Ch. 01

Note: What you are about to read is a true story, the first of several that I would like to share with you. I would like to thank Roftlheory, Jasperspen, and Charlie for the Herculean task of editing my first draft. I hope you enjoy it, and I thank you for reading my story...

I was scared out of my mind, and Troy was loving it. He could be an asshole for sure, but what guy couldn't. Recompense, I suppose, for all of the times I made him beg me for pussy, now he was making me beg him to sleep with me, literally. I didn't care about fucking him, I just didn't want to sleep alone.

I grew up on a cattle ranch a few miles outside of a small, Midwestern town. I was the youngest of four kids and none of my older siblings lived at home by this point, and my parents were out of town for a work associate's wedding. That meant that I had the house all to myself.

It was December 20th, 1996, a Friday night and my boyfriend, Troy's nineteenth birthday. I had turned eighteen the previous May, and as of that day, I was half way through my senior year of highschool. Troy was currently a freshman at our local, private, liberal arts college.

There was a bigger town about 30 minutes from home that had a number of good places to eat and a nice 16-screen theater. For his birthday dinner we went to the Olive Garden and from there to the movies.

Two movies opened that night. The first choice and the one I wanted, was 'One Fine Day', a lovely little RomCom with smoking hot Michelle Pfeiffer and not-hard-on-the-eyes George Clooney, just a win-win for everyone. The other movie was 'Scream'...

The Birthday Boy made his choice... We watched 'Scream'. In the first act (Spoiler alert... I guess, I mean the movie is twenty-four years old at this point, if you haven't watched it by now, I feel like that is on you, not on me), a pretty, popular, blonde, high school senior, in a country home, gets eviscerated by knife wielding psychopaths.

Fast forward two hours and I, a pretty, popular, blonde, high school senior was heading home to an empty house in the country...

"Please Troy, I'm freaking out!"

Troy, failing to suppress a giggle, "Sarah, it's just a movie."

"Yeah, a stupid fucking movie that YOU MADE ME WATCH! I haven't seen it, but I bet there are zero girls I could identify with that get murdered in 'One Fine Day', betcha a fucking dollar!"

"My mom knows we went out tonight. I can't spend the night with you!" he said, fighting back the laughs.

"Dude, you have snuck out a hundred times! I am not fucking you in this car tonight, fuck your birthday! If you want some pussy, you are going to sneak out," I stated, with belligerent authority.

"Okay, but I have always been back in bed in the morning when she wakes me up for breakfast. I can't spend the night with you and be home to wake up for breakfast," Troy explained.

"I can drive you back before she wakes up," I replied.

"You're going to wake up that early? You, Miss-I-had-detention-twice-this semester-for-tardiness, you're going to wake up in time to drive me home before my mom wakes up?" A mixture of sarcasm and scepticism coated each word.

"Mother... Fucker... I don't know if I can sleep tonight, waking up is not an issue here!" I insisted.

Finally, after I begged for the majority of the ride home, he agreed, and we made our plans. We went into his house where his mom, Terri, was waiting for us. She and I sang 'Happy Birthday' to Troy, then she cut us each a slice of cake atop which Troy plopped scoops of vanilla ice cream. As I was about to take my first bite, Terri asked if I wanted a smaller slice of cake or maybe less ice cream. It was at least the twentieth time in the nearly three years since I had started dating her son, in which she took the opportunity to make a not-so-thinly (no pun intended), veiled comment about my ass, diet and/or weight.

I have never been fat save maybe the few years during and after my pregnancies, but I have always been a bigger girl and I have had to work to keep my weight reasonable. I was 5'8" tall (still am), my tits were firm-ish C cups at the time, on their way to the still perky D cups they would peak at. I am, and was, a thickly built girl, and like all the women in my mom's family, I had plenty of junk in my trunk, even as a teenager.

Twenty minutes later I got into my car, drove to the other side of the block and parked. We had agreed to thirty minutes, but I sat in that car hyped-up on sugar and lingering fear, for what felt like hours. I had never realized just how poorly lit the streets of my hometown were until that night. Every bush that blew in the wind was the killer springing out towards me, every distant dog bark was a warning to RUN!

Tap. Tap. Tap.

"FUCK!" I screamed, nearly jumping out of my skin as Troy knocked on the window. I reached over and unlocked the door.

"What the Fuck Troy?! We said thirty minutes not three hours!" I yelled at him.

Troy put his hands out signaling that I was being too loud. "It has barely been an hour," he corrected, "I waited until I heard her snoring before I left."

"Wait... Terri snores?" I said, smiling, as I started the engine and began our five-mile drive to my house.

"Yeah, why is that funny to you?" he asked.

"Because she is always so... perfect and critical," I said, loving this revelation.

Sadly, a little over a decade later, Terri died from complications from her undiagnosed sleep apnea, which ever since has filled me with guilt for getting such a kick out of her snoring. Even in death my high school boyfriend's mom continues to fuck with me.

"What are you talking about?" Troy asked, incredulously.

"Troy, I know you heard her back there, (in a mocking Terri voice) 'Oh Sarah, are you sure you want ice cream with that or maybe a little smaller piece of cake' after she cut the slices," I pointed out.

"Yeah, that was a little weird, I don't know what that was about," Troy said.

"Troy, you're not this dumb, you've heard her say shit like that all the time... On my birthday she offered to take me shopping, which was her way of saying she doesn't like the way I dress, and then asked me if I was able to buy bottoms off the rack (again mockingly impersonating Terri) 'due to, you know' and then she held her hands out to the sides of her hips to mime that I have like a sixty-inch ass."

"Well, it is sixty sexy inches," he quipped.

"Fuck you!" I replied.

"You have to remember, she's a baby boomer, her generation, sure they had the whole hippy free-love thing, but they didn't have the wisdom of Sir Mixalot... She's from a time when little butts were the thing... 'My anaconda don't want none unless you got buns hun'," Troy flirted sophomoriclly.

"Whatever," I laughed.

"You know the football team voted you 'best ass in the school', right?" he asked.

"Yeah, I saw the list you pigs made about us, it's my crowning achievement that 30 pervs on the football team like my ass," I said, with no small hint of sarcasm. "But I didn't say 'whatever' about my prize-winning ass, I said 'whatever' about your (I took my hands off the wheel of the car just long enough to make air quotes) 'anaconda'," I teased.

"I see how it is... You know, I'm starting to rethink this whole sleepover thing."

"Oh, grow up, your mom has made dozens of comments about me, you can handle one joke about your dick!" I interrupted.

In truth his cock was perfectly fine. During my twenty-plus years of swinging, I have had cocks of all sizes and colors, and I have enjoyed every one of them; for me, Troy's was a champion.

We pulled into my driveway. It was pitch-black, and the 'Scream' viewing induced fear came back in force.

I parked my car significantly closer to the house than I normally did, my dad would have thrown a fit. Though I am sure he would have been more upset about the guy I was bringing home to fuck.

We both screamed when our family dog, jumped up on the driver's side door, excited to see me.

"Buster's here, that makes me feel better." I admitted.

Buster was a Bull Mastiff, and honestly if he had to face a pair of knife-wielding psychos, he would have slaughtered them with expedient and abject brutality. The thought of it made me kind of hope there were killers waiting for us inside, just to see the massacre.

I got the keys out and ready. My hands shook slightly, and it took me a couple of seconds to get the key into the lock.

Reaching inside, I flipped on the light in our mudroom. Troy led the way through the house with me clutching onto his left arm with both of mine. We went room to room turning on every light in house. We looked under beds and inside closets. My bedroom was the last we checked; I knew Troy would pick it last so that we could start making out as soon as his sweep was complete.

"So, have we rested your fears of the Scream killers waiting in your house," he laughed.

"I knew there weren't... but maybe we should get my dad's gun just to be, you know... safe," I suggested.

"Yeah," Tory replied, like a jerk, "adding guns increases the safety of every situation."

"Tell you what, you go get the gun out of my dad's nightstand and I'll get a little more comfortable," I promised.

Troy, always one for getting pussy sooner rather than later, jumped off my bed and swiftly made his way to my parents' bedroom.

True to my word, I began to undress. I had gotten my top and bra off when...

"NICE!" I heard from down the hallway.

Now there is a part of me that knew who yelled 'nice', but I was still a little on edge. I took off running, tits slapping, with buster right behind me, down the hall and into my parents' bedroom.

There I saw Troy with a goofy, shit-eating grin holding a dildo in his hand.

"Troy! That's my mom's side of the bed!" I told him, irritably.

"Yeah, I hope so... Man, this is way cooler than finding a handgun," he said.

He tossed the fake phallus onto the mattress and dug back into my mom's drawer.

It was then that I first noticed the winter chill on my exposed breasts causing my nipples to harden.

Troy was now flipping through the pages of a small, paper-back book titled 'Guide to a Life Time of Incredible Sex'. "You know if this was in the school libraries, the national literacy rate would be way better than it is," he said, tossing the book on the mattress next to the dildo.

"Oh, boom shakalaka!" he said, holding up the next sex guide he found titled, 'The Beginner's Guide to Anal Sex'. "God, your parents are the coolest old people I know."

In the half a year since I had turned eighteen, I had discovered my mom's sex guides and read them more than once; this one was new. Also during that time, due having two older brothers and a dad, combined with my preternatural snooping skills, I had surreptitiously viewed a considerable amount of pornography. As a result I had discovered a multitude of sexual acts that, for whatever reason, captured my imagination, not the lease of which was anal sex.

To this day I don't know why I found it so enthralling from the first time I saw it way back then. I suppose there is something undeniably slutty about a girl that takes it up the ass. On a few masturbatory occasions, I had experimentally penetrated my asshole with my fingers, I loved it, but was too afraid to try the dildo (yes, I had stolen my mom's sex toy a few times for personal use).

A sudden playful tweaking of my nipple from Troy made me realize that I had been staring at the book. "Someone's a little excited by this... Little miss high-beams," Tory said, still smiling like a dufus.

"Oh, fuck you! It is like fifty degrees in here; we forgot to turn the heat up when we were searching the place," I said, maybe too defensively.

Realizing I may have betrayed my interests, I quickly walked down the hall to the thermostat and turned it up to eighty degrees.

When I came back into my parents' room, there was a tube of gel sitting on the nightstand. Troy was holding the booklet open with one hand and a small box in the other, his head swiveling between the two.

"What now?" I asked, trying to sound annoyed instead of intrigued.

He looked up at me smiling for a long silent moment before speaking. "Well, if this book is to be believed, these are dildos... for your butt," he said, raising an eyebrow at me.

"No way," I said, honestly not believing him.

"Come look for yourself then," Troy said, with confidence.

I walked over to him. We sat on the bed, and I started looking through the book. I noticed the box clearly said, 'Butt Plugs -- 5 sizes included'.

I opened the box and looked at the plugs inside. The smallest was only slightly bigger than my thumb, the middle one was probably just slightly smaller than the average cock, and the largest one was, I could only assume, for someone that was preparing to take a doorknob up the ass.

I lay down on my side and began reading the guide from the beginning. Troy lay down next to me in the big spoon position. He reached around my side and started rubbing my nipples and playing with my tits in general.

His sporadic comments about various bits of the content showed me that he too was reading every word. At one point he jumped off of the bed, and took the lube into my parents' bathroom, where he placed the tube of gel in the sink, and then filled it with warm water. I gave him a confused and questioning look.

"Like you said, it was only fifty degrees when we came in. We want it about body temperature when we, you know, put it inside you," he said.

"Oh, thank you!" I said, surprised by my own words.

I suppose that the uncharacteristic thoughtfulness caught me off guard to the point that I totally missed the fact that he had already assumed we were doing this... and I missed the window of opportunity to, even if only in pretence, challenge that assumption.

By the time we had finished reading, midnight had come and gone. We had both had a long, last day of school and a date, but we were both wide awake. We lay there in silence, and I realized neither of us knew exactly how to proceed, so I made the first move.

"So, you're going to leave me here alone if I don't let you do this?" I asked, knowing it was a flimsy cover. 'I drove him here, how's he going to leave now?' I thought to myself.

I don't know if he was playing along with me trying to frame this as something he was "making me do" or if, in his I'm-about-to-get-laid, lizard brain, he didn't realize he couldn't leave anyway. Whichever it was, he simply said, 'Yep'.

"And you can NEVER tell any-"

"I won't," he interrupted, "I... Won't... tell anyone... I swear." (he later told like, everyone).

The first step to Anal sex is hygienically prepping. Due to the not-so-sexy aspects of this, I will skip the specifics to these vitally important steps...

Once the hygiene prep was complete, I exited the bathroom for the last time that evening. Troy had gotten naked and his rock-hard, cock curved up in front of him. We weren't virgins but I had never been as nervous about sex as was at that moment.

I turned on the bed-side lamp and Troy turned out the overhead light. We both took a moment to view each other in the soft dim light. We were beautiful and we knew it, and we were in love in the linear and doomed way only the young can be, and we knew that too, I think.

I lay down on the bedspread and Troy followed suit from across the room, his stiff prick swaying in front of him as he moved to me. As he climbed onto the bed I reached out and stroked his cock, it was glorious. Plenty big enough for any of my needs, with the distal third curving slightly upwards. My fingers felt the veins depress as I moved my hand across it. I could feel the heaving of my chest with each breath.

As he lay down next to me, our mouths met. Looking back on it, he was only a so-so kisser, although I think at that time, so was I. What we lacked in technical proficiency, we made up for in passion. I closed my eyes focusing on the pressure on my lips. The probing of our tongues, the sounds of our obscene smacking, and our excited breathing, set an erotic stage for us to perform on.

I rolled over on top of him and began kissing my way down his body until I was staring directly at his magnificent organ. I took him into my mouth, and he let out a the quietest of groans. I went slow, occasionally gagging, as I worked as much of his cock into my throat as I could.

I cannot deep throat. I have tried more times than I can count, but it is probably the weakest part of my game. I have however always given sloppy, drooling, gagging, eye-watering, blowjobs and honestly, no one has ever complained, and there were no complaints coming this night either.

"Fuck you're good at that Sare-bear," Troy complimented.

I said back 'I know I am', but with a hard cock in my mouth, it came out as "AWE WA AWE AHH."

A few minutes in Troy pulled me off of his cock. "Hey baby, its my turn," he said, as he directed us into exchanging positions on the bed.

He pushed my legs wide, tickling the insides of my thighs as he did.

Troy began eating me out. Again, with the benefit of many years more experience, he wasn't technically that good at it. He, like everyone from my generation, learned how to eat pussy from watching porn, so it wasn't his fault.

He was something of a performer though. Long broad tongue strokes from the top of my taint to the tip of my clit and tugging my labia with his lips. He was good at finding my clit and almost always gave it the lion's share of attention.

This night he added a new twist to his oral routine. Straight out of the booklet, he took his thumb and made circles gently pressing down and out on the outer edge of my asshole, occasionally switching between clockwise and counter-clockwise orbits. Too much pressure and it kind of hurt, too little and it kind of tickled, but somewhere in between the two there was a Goldilocks sensation that was just right.

I closed my eyes and tried to relax. Not an easy task when you are being anally stimulated by someone else for the first time.

A few minutes in Troy asked, "What size should we start with, I say go big or go home."

"If either of the bigger two come anywhere near my butthole, I promise, you will die tonight," I said, as mellowly as I could muster, not wanting to clench up.

With that I felt it push through my sphincter, there was mixture of moderate discomfort and a tickling flutter in my belly button.

Troy climbed up between my legs and aimed his cock at my pussy. He fingered me a few times, rubbing the copious amounts of my vaginal secretions, nature's lube, onto his cock. Laying on my back, I put my hands behind my knees, hoisting my legs up and apart.

To this day it usually takes several strokes before I open up all the way. This night, despite being even wetter than normal, was no exception. He slid into my pussy, it was just the tip, but my pussy held its ground like an entrenched army attempting to fend off an invading force. I was more than ready for the invading army to conquer.

I groaned as he slowly inched his way in. I could feel the walls of my pussy clamping down on him with each thrust in, and my labia gripped him greedily with every out stroke.

"Oh my GOD that is sooo good baby." I said, looking into his beautiful brown eyes.

"Yeah?"

"I have missed your buddy down there," I half giggled, and half moaned.

"Well, we've been missing that monkey."

I have a fairly meaty vulva with thick labia. One of the first times we had sex, I was lying on my side with my legs bent. Troy remarked that from behind my pussy looked like monkey lips. From that day forward he would as often as not refer to it as my "Monkey". The nickname pissed me off at first, but I have to admit that it grew on me over time, to the point that I begrudgingly came to love and use it myself to this day.