It was not a good day. It was the afternoon of Halloween, and just hours earlier my sort of girlfriend, Lisa, had told me that we were over. I should have seen it coming; we didn’t really connect like most couples do. Our relationship was more a matter of convenience, one that meant we wouldn’t be the only two seniors with no significant other to go with to school events and parties. I guess it was just as well, since we didn’t even enjoy hanging out together as friends anymore.

There was supposed to be a big party happening at Michael Chamber’s house that night, and I was hoping to go with Cindy, but that didn’t end up working out. All I had to go back on was hanging out with best friend, Nick, and his little sister, Stephanie. It’s been a tradition that Stephanie and I break away from our respective groups of friends and go trick or treating by ourselves since we were little.

I know it might sound weird, but Stephanie and I are almost better friends than I am with Nick. Stephanie and I share many of the same interests, from simple things like soccer and the latest AAA video game releases, to watching awfully cheesy sci-fi flicks and trying all of those weird foods at county fairs. Stephanie is like a sister to me, which makes what comes next a little awkward.

When Stephanie turned sixteen, there wasn’t some magical transformation in the form of her breasts or anything body related, but she had begun to wear a lot less clothing, in particular around me it seemed. Typically, Steph used to wear comfy clothes like loose fitting tees, sweatpants, or baggy soccer shorts that went down to her knees, but that changed last summer.

Now, Stephanie’s shirts were tight and form fitting, showing off her belly and even some cleavage. Her shorts were also tight, and barely able to cover her butt. Her changes in clothing were also accentuated with makeup and flashy jewelry, as if to say ‘Look at me.’ Even worse was when we were swimming, as it’s common for Nick and Stephanie to hop the fence that separates our property and theirs and use our pool whenever they want.

One day when I came home from soccer practice, I put my uniform in the washing machine and changed into my swimming trunks, ready to cool off after a gruelling afternoon of running drills. Coach had been pushing us really hard lately, so it was common for me to hit the pool after practice. My parents both work until six or seven o’clock, so I had the pool to myself for roughly two hours. That day I did not.

I walked through the kitchen and looked out the sliding glass doors into the backyard and saw Steph hopping the fence. I was about to go out and say hello when she started to pull off the extra-long t-shirt that she was wearing. Below the t-shirt was a hot-pink bikini that showed off her tantalizing teenage curves. At first that might not seem like a big deal, but up until then, Stephanie had only ever worn one-piece suits, so for me it was like seeing my best friend’s sister, who is practically a sister to me as well, in her underwear.

I’m sure you’re probably wondering right now what Stephanie and I look like, so here’s a brief description of the two of us. Stephanie is 5’ 5” with slightly less-than-shoulder length, dirty blonde hair, a slim build, green eyes, the cutest smile you’ve ever seen, and a few freckles scattered all over her body. Her breasts weren’t anything special, probably A’s bordering on B’s, but I kind of liked that for a change from the usual large breasted women I usually look at on porn sites. Her ass was also pretty small, but seeing it then in those bikini bottoms, I could tell that it was tight as hell.

As for me, I’m 6’ 1” with short jet-black hair, an athletic build, and blue eyes. Thanks to soccer, I keep in shape without looking like one of the over-muscled pricks on the football team. With regards to my dick size, well I’ve never actually bothered to measure it, so I’ll leave it up to your imagination. Let’s just say that no girl, or woman, has ever been disappointed with it.

I had an almost instant hard-on, the first one I ever had for Stephanie, and if I went outside to say hello, there was no way that I’d be able to hide it. I decided to go up to my room before Stephanie saw me staring at her from the kitchen. I got up to my room and was going to get dressed and just watch some TV or something until she left, but I couldn’t help but take a look outside my window at her.

From my window there was a perfect view of the pool, and with it a perfect view of Stephanie as well. I couldn’t stop staring at her body, as if I was seeing her for the first time. I guess in a way I kind of was seeing her for the first time, as this was the first day I ever thought of Stephanie of anything more than a friend or a little sister.

For a second, I thought Stephanie might have seen me staring at her, so I ducked away from the window and prayed that she didn’t notice me perving on her. After a few seconds I looked back out the window and saw that Stephanie had exited the pool and gone over to one of the loungers to sunbathe. Since she was going to lay there in the sun with her eyes closed underneath a pair of whit-rimmed sunglasses, I felt like I was safe to do what I was about to do next; I slid my swim trunks off and started to jerk off to the sight of my best friend’s little sister.

I breathed heavily, turned on immensely by the fact that I was secretly jerking off to the bikini-clad body of my best friend’s sixteen-year-old sister. I breathed heavily, knowing that no one would be able to hear me. I couldn’t believe what I was doing, but any thought of how wrong it was, I was easily able to overlook, thanks to  the sexy sight in front of me.

As I continued to stroke away, I noticed Stephanie lean up from the lounger, so I retreated slightly from the window while I waited to see what she was going to do. To my shock, she undid the strings of her bikini top and threw it on the ground next to her as she continued to sunbathe, now topless. I couldn’t believe it; it was one thing to see your teenage neighbor wear a bikini, sure, but to see her in your backyard sunbathing topless, that was a whole other level.

My strokes intensified as I stared at the milky white globes of Stephanie’s breasts, her nipples stiff and at attention thanks to the cool water of the pool she had just been in. Like I said earlier, Stephanie’s tits were not that large, but they looked quite perky, and her nipples themselves, stiff as rocks, looked so appetizing.

I was getting ready to cum, but  my strokes stopped dead when I noticed Stephanie slide the fingers of her right hand into her bikini bottoms. Not only was my best friend’s sister suntanning topless in my backyard, she was also masturbating. There was no way this could get any better, and I couldn’t hold out much longer. So luckily for me, Stephanie came pretty quickly, so I was able to come at almost the same time she did.

To some embarrassment, several streams of warm cum flew from my cock and hit the wall under my window, while whatever was left oozed out of the tip of my cock and onto my hand, leaving me with quite a mess. I slowly stroked myself as my cock went limp, watching Stephanie take deep breaths in reaction to her own orgasm.

I hurried to clean the cum off of the wall and on my hands before they made any marks my parents might notice. As I cleaned up, I looked over at Stephanie again, who had put her bikini top back on and re-entered the pool. From that day on, I secretly had a major crush for my best friend’s little sister, someone that up until that afternoon, I thought of almost like a sister of my own. However, on that day, she became the object of all of my fantasies.

Anyway, I’ve gotten a bit off track, let’s get back to the night in question, Halloween.

I walked down my street with Nick, occasionally going up to the houses whose owners we thought might be more likely to give candy to eighteen-year-olds. Nick dressed up like some sort of hip-hop star I didn’t know, and I dressed up like James Bond, wearing the tuxedo I was going to wear to prom while holding a toy gun that I had spray-painted gold. Nick looked ridiculous, but I think I didn’t look half bad in a tux, in fact, a few girls even looked at me and smiled as we walked by.

8:00 pm was approaching, which was the time Nick and I were supposed to meet with a group of people consisting of a combination of our friends from school, as well as Stephanie and her friends. The plan was that we would split up and Nick could hang out with some guys from the swim team, while I walked with Stephanie around the neighborhood and hit up a few houses ourselves. It was a tradition that she and I had been following for quite a few years, and while I was initially hoping to forgo it this year in order to get to Michael Chambers’ party quicker, I was no longer in the mood to party.

Nick and I approached the street corner where we were told to meet up and I began looking through the group of people to find Stephanie, and boy did I find her. I don’t know what she was wearing, but damn did she look sexy. Upon seeing me, Stephanie beamed and ran over to give me a tight hug, which was odd, seeing as how I just saw her a few days ago, yet she was acting like she hadn’t seen me for months.

“I’m so glad you decided to hang out with me again this year, Chase. I knew you were hoping to get to that party at Michael’s place faster, but I’m so glad you’re still hanging out with me tonight.” Her smile disappeared and was replaced by a scowl. “I heard about what happened with Lisa; what a bitch move. She doesn’t deserve a great guy like you.”

Woah! What’s up with that? I thought to myself. I know Stephanie cares about me, but the look of disdain on Steph’s face when she mentioned Lisa was intense.

“Thanks Steph. I’m just glad I can rely on you to cheer me up.”

As I spoke, I looked down at Stephanie’s costume and was perplexed as to just what the hell her costume was.

“That’s a, uh, cute costume Steph, but what is it?” I had to ask, as I had no idea what the it was supposed to be.

Stephanie pulled the edges of the costume’s skirt outward and did a small bow as she crossed her legs.

“Like it? It’s a Poison Apple Princess costume, like a modern-day hipster version of Snow White.”

The ‘Poison Apple Princess’ costume was actually one of those cheap, hoodie-based outfits that had a few features similar to a more elaborate costume, in this case Snow White. Rather than an elaborate Disney styled princess dress, Stephanie’s costume consisted of a blue hoodie with white lace around the hood and pockets, red piping along the zipper section and yellow cuffs around the short sleeves. Below was a really short, yellow pleated skirt, and a pair of glittery, red ballet flats. Besides the skirt being very short, she also had the zipper on the hoodie down just below her breasts, showing off whatever cleavage she had.

How did she convince her mother to let her wear something this skimpy?  Was my first thought. After figuring out that her mother probably didn’t know about it, since she and Mr. Clapper were on vacation that week, I then wondered, WHY would she wear something like this? Stephanie always loved to dress up in elaborate costumes during Halloween, so why was she wearing a lazy, skimpy outfit that I would have expected to see on girls my age?

“So, you ready to get started, or are you just going to stare at my costume all night.”

I realized that I had been staring at Stephanie, and her costume, for almost fifteen or so seconds now, so I awkwardly tried to recover in as cool a fashion as I could.

“Ready? I’m waiting on you, princess!”

Stephanie practically yanked my arm out of its socket as she grabbed my wrist and pulled me towards the first house on the street. Nick managed to yell out to meet him back at the same place in an hour.

Going up to the first house, we had a nice old lady remark on how cute Steph’s costume was and how dashing my tuxedo was. I think going around with a younger girl on Halloween helped me get more candy, since I might be confused for a chaperone or something. The second house had a middle-aged man answer the door.

“Trick or treat?!” Stephanie gleefully squealed out.

“Well, I think you definitely deserve a treat,” the guy said with a more than friendly smile. I could tell that the guy was looking at Stephanie in a way that a man his age shouldn’t have been looking at a teenage girl, so I was glad to get the candy and get out of there as quickly as possible. Unfortunately, as I turned I saw that the guy was watching us as we left, no doubt trying to get a look at Stephanie’s backside as we walked away.

We hit a few more houses and upon visiting our eighteenth house, I told Stephanie to go on to the next house without me while I checked my phone for any texts I may have missed. She said okay and hopped up the stairs to the house. After going up a few steps, some of the candy in Stephanie’s overflowing bag flew out as she skipped towards the house. I heard her say ‘Damn!’ and then bend over to pick up the lost candy. Rather than bend at the knees and squat to pick up the candy, Steph bent over at the waist with her legs remaining straight as she scooped up the scattered confectionary.

Bending over like she did caused the tiny skirt Stephanie was wearing to ride over her ass and expose the yellow underwear below it. I was thankful that no one else was close to this house yet, both for the fact that I didn’t want anyone to see Stephanie in this position, nor did I want them to see me staring at her the way I was. She was wearing yellow bikini-cut panties that matched her skirt, leaving me to question, Why would she wear underwear that matched her costume’s skirt? Was she planning on having someone see under her skirt? And if so, who? Was it for me? Did she spill the candy on purpose so she could bend over and show me her ass?

My train of thought was interrupted as Stephanie finished picking up her lost candy and turned around to smile at me and signal that everything was okay. She finished collecting her candy from the house and came back to me. The rest of our time together was fairly normal, with no more awkward moments like when she had bent over to retrieve her lost candy. We mostly just talked about school and other insignificant stuff, although I did learn that Stephanie did not have a boyfriend yet and was still waiting for the perfect guy.

“You know, Stephanie, you may be disappointed if you’re looking for the 100% perfect guy to come along. It’s pretty hard to find someone that checks off every box on a list of qualities you want in a boyfriend.”

She smiled at me.

“Well, if I can have a friend like you, it might not be impossible for me to find the perfect boyfriend,” she said as she hugged my left arm and rested her head on my shoulder.

I couldn’t help but blush and think again about whether or not she was trying to send me some kind of signal. I know some people might think that she was totally trying to get me to make a move on her, but remember, she’d been my friend for eight years since she was little, and was more like a little sister to me than a friend. Maybe I was reading too much into things, since I had just been dumped and was feeling kind of distracted, but I couldn’t help but wonder, What if she is trying to send me a signal? If so, what do I do about it?

It was two minutes to 9:00 pm, and we arrived back at the meeting place where Nick and the rest of our friends were waiting to go to the party. Since Nick and Stephanie’s parents were on vacation that week, Nick was stuck looking after Stephanie at his place and couldn’t go to Michael’s party tonight, so we just planned to have a few drinks at his place and watch a movie after Steph went to bed.

Stephanie saw a small group of her girlfriends close by and decided to go talk to them for a bit. She thanked me for the evening, gave me a peck on the check, not out of the norm for her, and gave me a strong hug. I had gotten hugs from Stephanie all the time, since we were pretty close, but this time the hug went on for a little while longer than usual, and I could have sworn that she was non-intentionally, or perhaps intentionally, lightly grinding herself against me. With a goodbye she rejoined her friends and I went to speak to Nick.

“Hey, Nick. Let’s get back to your place, I could really use a drink.”

Nick’s face twisted a bit, like he was either having bad gas, or he was about to ask me for something he knew I wouldn’t want to do, something I had become used to him doing when he had that look.

“Well, actually, I was kind of hoping that you could do me a solid and spend the night at my place, with Steph, while I go to Michael’s party.”

I couldn’t believe it; Nick wanted me to babysit his little sister while he went off to a party.

“So what are you saying, Nick? You want me to babysit your sister while you go and party all night?”

“DUDE! Come on! We both know you have zero interest in going to the party tonight, and I have a really good chance to get in that chick, Harper’s pants tonight. I could be an asshole and just leave Stephanie home alone, but I’m not, I’m asking you to do me this favor. You really like spending time with my sister anyways, so this shouldn’t be too big of a deal, bro. What do you say, man? For me?” He turned and gestured at Stephanie. “For Stephanie?”

As annoyed as I was to have one of my friends use me by trying to get me to watch his sister while he attempted to get laid, I didn’t really feel like doing much tonight anyways since Lisa had just dumped me. Actually, getting to spend more time with Stephanie was a bonus, but I didn’t want to let Nick know, or else he’d use me as a babysitter whenever he wanted to get out of having to watch her.

I looked over at Stephanie and her group of friends and she smiled when she saw me looking over at her. It was in that moment that any hesitation on my part to help Nick out faded away. I faked a sigh.

“Okay, man. For you, I will do this favor. You’re lucky I like your sister and she’s not a big brat like most little sisters are.”

“Oh dude, THANK YOU!” I thought Nick was going to break out into a happy dance.

“Yeah, yeah, okay, just calm down. Get the hell outta here before I change my mind.”

Nick gave me one last thank you and bolted away from me to talk to his sister. I may have been seeing things, once again, but from where I was, it looked like Stephanie was beaming with more delight than she had shown all evening at the prospect of us spending the night alone at her place.

We walked back down the street towards Stephanie and Nick’s house while comparing the different kinds of candy each of us got. I figured Steph would get more on account of the fact that she wasn’t an eighteen-year-old like me trying to squeeze out one last year of trick or treating before giving up the practice for life. Still, I couldn’t help but think to myself, With a costume like that, I bet a lot of the guys who answered the door to her gave her extra candy. The thought of that middle-aged guy perving on Stephanie actually made me angry, even though I was older than her myself and had also been perving on her that night. I guess I was just, well, jealous.

We arrived at Stephanie’s house and she unlocked the door and let us in. She immediately re-locked the door, and out of nowhere, she pushed me against the wall. Normally a petite, sixteen-year-old girl would never have been able to push me like that, but I was so caught off guard by her shove that I stumbled backwards into the hallway wall. Even more surprising was what Stephanie did after she pushed me; she got up on her tip toes and pushed her lips against mine.

I gently pushed Stephanie away.

“Stephanie, what are you doing?”

“I want you, Chase.”

She tried to re-initiate the kiss, but again I gently pushed her away.

“What has gotten into you tonight, Steph?”

“I’ve been trying to get your attention all night, but you haven’t made a move yet. I’ve been throwing hints at you and trying to show you that I want to have sex with you, but you haven’t done anything yet.” She ran her hands along my chest. “When Nick told me that we would be alone tonight, I thought I might as well try the direct approach, since the odds of us ever having the house completely to ourselves for a whole night again anytime soon is probably almost non-existent.”

“But Steph, why me? You’ve never tried anything like this before.”

“I thought you might try first, but you never did. I mean, ever since I noticed you looking at me that time I snuck into your backyard to go for a swim a few months ago, I was hoping you might put the moves on me.”

My face drained of color.

“You saw me that day?” I felt like such a perv, and even though Stephanie seemed to be okay with it, I still felt like such a creep.

“I did, and I really liked it. I know you were masturbating to me, that’s why I took off my top and started masturbating too. In fact,” her smile widened ever so slightly. “I was thinking of you when I did it.” Even with what was happening, Stephanie’s smile still seemed so sweet, so innocent. “You’re the first boy I really like to take an interest in me. I’ve never been with a boy before, and I really want you to be my first, Chase.”

So, not only was the girl I had known for nearly a decade, and was the sister of my best friend, hitting on me, but she also wanted me to take her virginity. I was torn down the centre between thinking that this was so wrong, and so, so, SO fucking hot.

“Stephanie, you’re sixteen, I’m eighteen, your first time should be with someone special, someone closer to your age, and most importantly, someone who isn’t your brother’s best friend. We can’t do this.”

“But I really like you, Chase. You said my first time should be with someone special, and that’s you. You’re not just some boy at school hoping to get lucky and then toss me aside afterwards. I know you, and I know you wouldn’t do that to me. I know we’re different ages, and that you’re my brother’s best friend, but I just feel like this is the right thing to do, and that my first time couldn’t be more special with anyone other than you.”

I didn’t know what to say. She did sound like she’d thought this through and wasn’t making the decision on a whim. I really did like her, not just as a friend, or a sister, or as a girl to just have sex with, but someone whom I really cared for and lusted for in more ways than just the physical sense; I wanted to make her happy and give her what she wanted. I thought about it for a second and made my decision.

I  gently took hold of the back of Stephanie’s head and pushed her lips to mine. She Immediately returned the kiss and wrapped her arms around me. I had dreamed of kissing Stephanie for so long, but I always feared what her reaction might be, and even with her teasing me all night, I still couldn’t stop thinking of what the consequences might be for us going through with this. But in that one moment when her tongue started grappling with mine, all of those concerns vanished and the lust within me threatened to overtake me and cause me to push Stephanie against the front door of her house and take her right then and there.

As we kissed, I undid the zipper on her costume and exposed her young, soft breasts; she wasn’t even wearing a bra. I gently massaged each one, really enjoying that I was able to fully grasp each one in my hand, something I couldn’t do with a big breasted girl or woman. Our tongues danced around with one another, exploring each other’s like we were both so desperate for water that we were trying to suck the saliva out of each other’s mouth.

Eventually, it hit me that there were still people trick or treating, and even though the lights were off out front, someone might still come up to the front door anyway.

“You know, if we want to continue this, we should really head on up to your room.”

“Agreed. We wouldn’t want someone to ruin my first time, would we?”

I kissed Stephanie once more before picking her up and holding her by her back and knees, causing her to give a cute little “Ooh!” as I carried her up to her bedroom.

Once in Stephanie’s room, I gently placed her on her bed and switched on a small lamp next to her bed before returning to her. I knelt next to the bed and started kissing her again as she laid there. This time our kiss was less sloppy and lustful, and instead slow and passionate. It was as if we weren’t sure before if we were going to keep going and needed to get everything we wanted from each other right then and there; but now that were knew we could enjoy this for the rest of the night, we could take all the time that we needed to do things right.

After a minute, I broke our kiss and offered Stephanie a proposition. “I’ve heard that giving a girl a little oral sex can loosen her up a bit before actually doing it. You wanna try?” I quickly got a smile and a giggle.

“Sure, I’ve never had a boy eat me out before.”

“Well then, you better take off your underwear so I can loosen you up before the main event.”

“You got it, Chase.”

Stephanie got up and walked a few feet away while looking at me seductively over her shoulder. Slowly, she bent over and started to slide her yellow panties down her legs and remained bent over at the waist until the yellow fabric hit the floor. I was pleased to see that Stephanie had a little golden blonde hair covering her pubic area, not a full-on bush, just a little ‘fuzz.’ It was refreshing to see a girl with some hair downstairs; too many people were buying into the whole shaved pussy thing. A little bit of hair on Stephanie highlighted how she was growing up.

I told Stephanie to lay down on the edge of the bed and spread her legs. It was so hot that she kept her costume on too; besides removing her panties and me unzipping her top, the costume was pretty much intact, including her short yellow skirt. Having sex with a girl still wearing a few articles of clothing always turned me on for some reason.

It was finally time that Stephanie got to see a little bit of me too, so while she was getting comfortable at the edge of her bed, I decided to remove a few articles of my own clothing. I started with my bowtie, followed by my tuxedo jacket, until I got to my white dress shirt, which I proceeded to unbutton slowly to make things more interesting for Stephanie.

I left my pants on for later and proceeded to move a hand between Stephanie's legs. I wanted to slowly tease her in order to make her first time as long and memorable as possible. As my hand reached her warm pussy lips, I used two fingers to gently massage the folds of it. She was so wet that I couldn’t believe it was possible. No girl I’d ever been with before had gotten this wet from foreplay alone.

Stephanie’s soft moans were so intoxicating that I had to force myself to let up a bit on her, or else she would cum far too soon. I knelt down in front of Stephanie and began to suck on her left nipple as my free hand came up to gently knead her right breast. As her moaning continued to intensify, I tried to slide my two fingers slowly into her, but she was so damn tight that it was going to be a miracle if I managed to fit even half of my dick into her.

"Stephanie, you have to try to relax. There’s no way I’m going to be able to enter you if you’re so tense. Just breathe and try to relax your muscles, try to think about the pleasurable part of this, not the pain."

"Okay, Chase, I'll try."

After getting her warmed up, I decided it was time for Stephanie’s first oral. I removed my fingers from her pussy and my mouth from her nipple and proceeded to kiss my way down her body. My lips finally made it to her pussy and I gave it a small kiss, causing her to give a sharp gasp at the new feeling. My tongue replaced my lips and began to slide up and down the juicy walls of her cunt

“Oh my God! Oh my God, Chase, that feels… that feels perfect.”

The praise caused me to smile as I continued to lick at her sweet folds. Just as I moved my tongue to tease her clit, I heard Stephanie cry out as she came all of a sudden, leaving me scrambling to lap up whatever sweet juices I could from her. I didn’t even get a chance to truly explore her before she came, which was usually when I was able to shine and introduce my fingers back into the mix. Next time perhaps…

"Oh, Chase. That was the best orgasm I’ve ever had. I’m glad that you were the first boy to make me cum.”

The more praise I received from Stephanie, the harder and more aching my cock became, and I decided it was time to do something about it. I got up from my knees and undid my belt before unzipping my pants and letting them fall to the floor. My cock was left straining against my boxer briefs, the outline of it clearly visible. Stephanie’s eyes lit up at the sight and she got up from her bed.

“You know, you’ve been pretty good to me so far…” She leaned against me and began running her fingers up and down my chest. “It’s only right that I do something for you in return…” Her hand reached down and slid back and forth over the thin material that separated my cock from her fingers.

I Smiled and lowered my head down to kiss her. The kiss was short, and no tongues were used, as I was too eager to get to the next event. I sat on the edge of the bed that Stephanie formerly occupied and slid my underwear off, leaving my cock free to spring out and practically stand straight up into the air.

Stephanie lowered herself to her knees in front of me and just sort of looked at my cock for a while. Eventually I asked her if anything was wrong?

She sheepishly replied, "No, it’s just that, this is the first time I’ve seen a real dick up close. I didn’t think that my first one was going to be as big as yours is."

I smiled at Stephanie and slowly stroked her cheek. “Don’t worry, Steph. We’ll take it slow when the time comes, and I’ll do my best to make sure it hurts as little as possible, I promise.”

She returned a smile of her own and I could tell that she was comfortable moving forward.

Stephanie brought her hand up and gave my cock a few jerks. I let out a series of involuntary moans that Stephanie picked up on, causing her to smile. After a few more pumps, she lowered her head to my cock. She stuck her tongue out and gave the head of my cock a small lick, causing her to giggle nervously.

“Hmm, that’s actually better than I expected. It’s not great tasting, but it’s not totally disgusting, either."

Stephanie lowered her head down again and slowly let the tip enter her mouth, her lips sliding over it and creating a truly magical sensation. Her mouth was so warm and soft that I exhaled slowly for several experiences as I enjoyed the feeling that I had dreamed of experiencing for so long. She continued to slowly push herself down my shaft, inch by painfully pleasurable inch as my breathing picked up and I stroked her beautiful, silky hair with my right hand.

A little over halfway, Stephanie reached the maximum amount she could handle, letting out a small gagging noise as my cock reached her throat. Having had no experience before this, her mouth and throat likely needed time to loosen up and get used to having something like a cock shoved into them.

After a few bobs of Stephanie’s head, I winced in slight pain. She was definitely an amateur when it came to both receiving, and giving, oral sex. She couldn't find an acceptable rhythm, and her teeth painfully scrapped against my shaft, and even worse, the head of my cock. I gently used a hand to lift her chin up and pull her mouth away from my dick.

A pained look came across Stephanie’s face. “What’s wrong, Chase? Was I really that bad?"

"No, of course not, Steph. I just want to make sure that I don’t cum before we get around to the best part."

She smiled sheepishly. Clearly, she knew that she had hurt me a bit, but she appeared happy that I didn’t criticize her for it. I didn’t want to hurt Stephanie’s feelings, especially since she was doing the best she could for her first time. I would happily help her to learn some more later, but if I did that night, my dick just might have been throbbing out of pain rather than pleasure, and I didn’t want to let her down on her hopes of losing her virginity that night because of a sore penis.

I stood up and pulled my wallet out of my pants. I retrieved the condom that I always carried in my wallet for situations where sex might occur, although I never knew taking the virginity of my best friend’s sister would be one of them. In a hurry to get inside of Stephanie, I ripped the packet too fast and ruined the condom in the process. I was about to swear, when Stephanie reassured me.

“Don’t worry, Chase. I didn’t know when we might be doing this, so I’ve been prepared and had a package of condoms under my bed for over a month.”

Stephanie was definitely more prepared for tonight than I was.  This time I managed to successfully remove the condom from its package and roll it onto my cock as I looked down at Stephanie. Sweat glistened on the small, rising and falling mounds of her breasts in the moonlight coming through her window. The tiny lamp in the corner of the room hardly offered anything other than minor illumination. Rather, it was the moon that lip up Stephanie’s amazing features, which made the situation even more perfect than it already was as I placed my cock at the opening of Stephanie’s waiting pussy.

It had been so long since I had sex with a virgin. The only virgin I had sex with was the one I lost my virginity to, and that was a couple years ago. Since I was sure that virgins react to their first time differently, I had no idea what to expect. Stephanie was biting her lip because she was so nervous. I bent her down and kissed her and her hesitation melted away into a sweet little smile.

“I’m ready for you, Chase.” And I was ready for her.

I began rubbing the tip of my cock up and down the moist lips of Stephanie’s pussy, both as a method of teasing her and to gently probe how tight her opening was, and it sure was tight. After a little teasing, I very slowly, almost excruciatingly slowly, pushed the tip of my cock into Stephanie. She winced in pain as I entered her, but I kept slowly pushing myself in so she could get past the pain as quickly as possible. She gripped the sheets even more tightly than when I ate her out, causing her knuckles to turn white at the intensity of her grip.

After almost a full minute of carefully pushing my cock deeper inside of Stephanie, I reached the end of her vaginal canal, which meant that about two thirds of my shaft managed to make it inside of her before I reached as far as I could go; trying to push my full length into her would be far too painful, but one day it might make it if she loosens up a bit. The grip that her pussy had on my cock felt otherworldly. No girl I’d ever been with had a pussy this tight, no doubt due to the fact that Stephanie was a virgin, at least until that night.

"OWW! Oh, God, it hurts so much!" She practically screamed.

“Don't think about the pain, think about something else. Try to think about how much you liked it when I was eating you out. Once you get used to me thrusting in and out of you, the feeling will be even better than my tongue, I promise. Just hold on a little longer.”

Stephanie nodded her head and looked at me through slightly teary eyes. As great as her tight pussy felt wrapped around my cock, I found myself worry so much about the pain she was in that I was worried I would lose my erection. The pained look on Stephanie’s face threatened to ruin any pleasure I was having , and by extension the night would have been over, leaving her last thought of the evening being about how much pain she was in during her first time without the feeling the pleasure that really came with having sex.

We took it super slow at the start. I slid myself in and out of Stephanie as slow as I could to minimize the pain of being penetrated the first time. After a few minutes, she no longer winced in pain as I thrusted into her, and she also breathed with her mouth slightly open instead of wide with her teeth clenched. Her breathing became steady and moans of pleasure began to replace her grunts of pain.

Luckily for the both of us, about three to four minutes passed and I was able to visibly see Stephanie loosen up.

"Oh, oh, Chase. This feels… this feels incredible."

I couldn’t help but smile.

“I told you, it just takes a little getting used to. Eventually whenever you have sex, there won’t be any pain, just pleasure.”

“Would it be okay if I got on top of you?”

“Of course, Steph.”

I pulled myself out of her and stood back to admire the beautiful sight before me; Stephanie had let herself go limp just as I finished pulling out of her, and her chest heaved up and down as her lungs tried to replenish their air supply. A small, giggly smile made its way to her face as she tried to get up. Realizing that she may be feeling a bit weak, even still pained by my thrusting, I gently pulled her up and gave her a quick kiss on the lips before lying down on the bed and letting her climb on top of me.

Unfortunately, Stephanie lost her footing while she was trying to place her knees on either side of me and and dropped all the way down onto my cock in one fast motion instead of slowly easing it in. Even though I managed to get pretty deep before, I didn’t fit all of me into her, and considering she fell onto me pretty fast and pretty hard, it came as no surprise when she let out a painful cry at suddenly having my dick jab at the very end of her vaginal canal.

“Steph, Steph, it’s okay, look at me.” She did, but with a horrific pained expression on her face. “Just ease yourself up slowly, don’t try to get off of me too fast, or else it’s going to hurt a lot more. Take it slow, and breathe in and out slowly, don’t start gasping wildly, it won’t help the pain, okay?

“Yeah, yeah, okay,” she panted as she struggled to breathe slowly and not freak out from the pain.

Slowly, very slowly, Steph settled her knees on either side of me before slowly raising herself up and off my cock. Just before my tip was about to pop out of her, Stephanie began slowly lowering herself back down my shaft, and eventually going up and down at a fairly reasonable clip.

“Ah, oh, ohhh. It’s starting to feel really good again, Chase,” Stephanie said with her voice calm and slow, but her eyes still squeezed shut.

“Like I said, it gets easier, and eventually, the pain will drift away until all that’s left is pleasure.”

Without adding anything, Stephanie started bouncing up and down on my cock with slowly increasing speed. I couldn’t believe how quickly she was adapting to the feeling of my cock being inside of her. I had only ever had sex with a virgin once before, and it seemed like she would never get used to the feeling of having sex. Stephanie, on the other hand, was adapting quite well, and it wasn’t long before the pained looks on her face were replaced with smiles and looks of absolute enjoyment.

“Oooh. Oh, oh, Chase. That feels perfect, it doesn’t hurt at all anymore.”

“I’d never lie to you, Stephanie,” I said with a smile, happy that Steph was now fully enjoying having sex.

As she picked up speed as she slid herself up and down my cock, I felt comfortable doing things like gently squeezing her breasts, teasing her clit with my fingers, and so forth. Eventually I felt like Stephanie was ready for me to exert a little more force, so I motioned for her to put her chest onto mine and rest her head on my left shoulder. I took hold of her butt cheeks and used them to push her up and down my cock while also moving my hips and thrusting myself in and out of her, letting her relax a bit, and allowing me to push faster and deeper into Steph’s pussy.

This time, there were no cries of pain from Stephanie, no tears, or looks of fear in her eyes, just the begging of more and the cries of a girl, or should I say young woman, who was experiencing just how great sex could be.

“YES, oh, God, yes! Please don’t stop! Oh, Oh, Chase, you’re so… so… aaahhh!” Stephanie never managed to finish whatever she was going to say, likely the result of another orgasm.

After another two thrusts, I couldn’t hold back anymore and let out a loud grunt as I blew my load into the condom. After taking a second to get ahold of herself after her second orgasm, Stephanie raised herself off of me and collapsed next to me. As she took deep breaths and recompose herself, I just laid there and stared at the beautiful girl lying next to me. Something as simple as her breathing was one of the best things I had ever seen in my life.

“So, was you first time as good as you’d hoped it would be?”

She smiled brighter than ever before.

“Actually, it was much better. Thanks for being my first, Chase.”

“My pleasure, and thank you for trusting me with such an important thing like taking your virginity.” I moved my mouth to hers and kissed her for what seemed like five whole minutes before she broke the kiss and cuddled up to me. Eventually we fell asleep, holding each other in our arms.

The sun came up at round 6:30ish and rays of light poured in through the room’s window, slowly wrestling me from my sleep. As I began to rub my eyes, and stretch my eyes I exhaled through a groggy haze. My hands reached to my side where Stephanie should have been, but she wasn’t there.

Was it all just some insanely detailed dream? Too bad, it would have been a dream come true.

As I began to roll towards the side of the bed where my alarm clock was, I was immediately struck with the realization that I was not in my own bed; I was in the bed of my best friend’s sister. I rolled over to see Stephanie curled up next to me, still asleep with her hands underneath her head as she dozed with a cute smile on her face that made me smile too.

"Steph, wake up," I whispered as I gently stroked one of her soft forearms. With a small moan, her eyes slowly lifted themselves open and focused on me, causing her smile to widen a bit more.

“Mmmm, morning.”

“So, still no regrets about last night?”

Her smile intensified.

“None whatsoever. I’ve wanted to do this with you for a long time. I-“ Stephanie hesitated. “I love you, Chase.”

With no hesitation on my part, I replied, “I love you too, Stephanie.”