My best friend Ashley


My best friend Ashley
Ashley Robinson had been my best friend since kindergarten when her family had moved into the house next door. During the almost ten years we did everything together, for example, this morning we decided to go fishing. Living in a small beach town in Florida has its perks, we were far enough from Daytona that we didn’t get all the tourists but close enough that we still had the same white sandy beaches. This morning we had the beach mostly to ourselves.
We joked around and laughed as the warm tropical sun rose above the ocean and although we really weren’t catching anything it was still good to be out fishing. We fished for a couple of hours without much luck then decided to go for a swim. We reeled in our lines and set the poles in the sand with my tackle box. I peeled off my t-shirt while Ashley did the same revealing her new white bikini top. She then dropped her shorts and kicked them onto the growing pile of our clothes.
“You like it”, she asked as she twirled around to show off the new bikini.
I did and I told her so. The bright white fabric stood out against her tanned skin and while it was a fairly modest bikini, there was still a lot of skin showing. Growing up with Ashley I had watched as she began to develop into a young woman. We were best friends and I’d never thought of her in a sexual way, I was still a teenaged boy, so I had noticed as her breasts began to develop. She’d also developed a really nice round butt. I had to admit to myself that my friend was hot.
We ran down to the water and crashed our way through the first line of breakers. The water felt great and the waves weren’t too big, so it was easy to keep our footing as we splashed around. As we did, I noticed an older man standing on the beach watching us, or more likely watching Ashley. The longer he stared the more it was beginning to piss me off. Ashley noticed him too and called him a pervert. Just as I was about to head back to the beach to say something to the old creep he turned and down towards the line of hotels.
“Can you believe that old bastard staring at us like that”, she asked incredulously as she wiped a stray wet brown hair from her eyes.
“He wasn’t staring at us”, I replied, “He was staring at you.”
Ashley looked genuinely surprised at that and asked, “Why just me?”
“Because you’re a beautiful girl and I’m just a skinny k**.”
“You’re not that skinny”, she laughed, “Maybe he’s a queer and into blond guys.”
I laughed at that and we went back to horsing around in the waves. At one point she came up behind me just as a wave came and lifted me up dropping me headfirst into the swell. I came back up spitting the saltwater from my mouth. Two can play at that game, I charged at her and grabbed her around the waist and dumped her into the water. It took us both a second to realize that I’d somehow managed to accidentally pull one cup of her top to the side and her perky little boob was now hanging out. I only got to see it for a couple of seconds but the image of that pale breast with its cone-like pink nipple was burned into my memory and my dick began to fill with blood. “Shit, I’m sorry”, I apologized and turned away as she put her boob away.
“Shit happens”, she laughed then added, “That old pervert should have stuck around for a few more minutes.”
We joked about that for a while before heading back to shore. Thankfully my boner had subsided, that would have been awkward. When we got to our pile of stuff on the beach Ashley shook the sand from her towel and laid down on it to soak up some sun. As she did so I noticed that her nipples were poking through the wet white fabric of the bikini and could suddenly feel my dick begin to swell again. Quickly I snapped my towel in the air to get rid of the sand and sat down beside her before she could notice the situation in my shorts.
After about half an hour we decided to head back home to get cleaned up. It was a short walk, maybe fifteen minutes, to get to our respective homes where we each put away our fishing gear. Neither of our families was home as it was the middle of the week, so I took advantage of that to take a long hot shower and rub one out thinking about Ashley’s boob. I washed the puddle of my seed down the drain and got out to get dressed. With fresh clothes on I walked next door to see if Ashley wanted to hang out and listen to some music. She answered the door wearing a pretty yellow sundress. Damned if she didn’t look beautiful with her shoulder-length brown hair still wet from her shower. “Knock it off”, I silently admonished myself, why the hell was I suddenly looking at her this way?
We decided to hang out at her house, so I followed her back to her room. I’d been in her room many times over the years and was very familiar with the pictures of horses and teen heartthrobs that adorned her walls. It was a typical teen girl’s room, unlike mine which was very spartan in comparison. The radio was already playing the local country station so we sat on her bed and talked about the upcoming school year that would start in about three weeks.
Out of the blue Ashley asked me if I liked seeing her boob. How the hell was I supposed to answer that one? I figured that honesty was usually the best policy, so I told her that it was a nice boob. It was as far as I was concerned, not that I’d seen a boob in real life before. Of course, talking about her boobs made me drop my eyes down to the subject of our conversation. The dress that she was wearing was strapless and had an elastic-like top that conformed to her breasts so I could tell that she wasn’t wearing a bra.
She caught my gaze and laughed, “eyes up here!”
Embarrassed that I’d been caught looking I looked back up at her smiling face. “Sorry.”
She laughed again and sheepishly asked, “Do you want to see them again?” She didn’t wait for me to answer as she gripped the top of the stretchy material of her top and pulled it down.
I was speechless as I stared at my best friend’s perky boobs. They were maybe a b-cup with big puffy nipples. I was glad that we were sitting because my dick immediately began to swell in my shorts. It became even harder when she asked if I wanted to touch them. Of course, I did! It was a bit strange to be reaching up to cup her soft yet firm breast. The pale globe felt great in my hand as I softly squeezed the pliable flesh. When I ran my thumb across her rubbery nipple she sighed. I switched and played with her other boob for a while before building up the courage to lean in and suck one into my mouth.
“Wow”, she cooed as I gently suckled on her breast like a hungry baby, “That feels really nice.”
By now my dick was rock hard and uncomfortably twisted in my underwear so I tried to discretely adjust it. Evidently, I wasn’t discrete enough because just as I got it into a better position she asked if I had a boner. I admitted that I did but then laughed that it was her fault.
“Can I see it”, she asked with big puppy dog eyes.
This was getting interesting. I laid back on the bed and unbuttoned my shorts. I’ll admit that I was a little nervous as I lifted my ass and slid both my shorts and underwear down past my ass. My hardon caught up in the elastic waistband of my Fruit of the Looms and when it got free it audibly slapped back against my belly.
“It’s cute”, she giggled as I slid my pants the rest of the way off.
“Cute”, I thought to myself, no guy wants to hear his dick described as cute, massive would have been better even though I knew I was really quite average down there. I sat back up and figured that I might as well remove my shirt as well, so I did.
“Can I touch it”, she asked while reaching into my lap before I could answer. It’s not like I was going to say no. I nodded and laid back on my elbows. For the first time, another person’s hands touched my dick and it was amazing. Her hands were so soft as she wrapped her petite fingers around my shaft. “Am I doing it right”, she asked as she stroked my throbbing dick.
“Oh my God yes”, I gasped.
With one finger from her left hand, she smeared the precum that was oozing from my piss hole around the head of my prick. “What’s this”, she asked.
“I think it makes it easier to get into a woman’s vagina”, I guessed, but really wasn’t sure.
“Oh, kinda like how my pussy gets wet when I play with it.”
I really hadn’t thought about it that way, but it made sense. “Yeah, I suppose.” I really hadn’t thought about my friend playing with her pussy before, but that made sense too. After all, I enjoyed playing with my dick, it goes without saying that girls did it too. “What’s it like when you play with your pussy”, I asked, angling for a demonstration.
“It’s the most amazing feeling ever”, she replied, “How is it for you?”
“It’s great”, I answered truthfully. I loved jacking off, in fact, I sometimes did it so often that my dick would hurt and once it even bled near the bottom of the head. “But it feels even better with you doing it.”
Her eyes lit up at that and suddenly she released my dick and stood up next to the bed. Speechless I watched as she took the hem of her sundress and pulled it up over her head revealing her modest pink panties. She grabbed the waistband of her underwear and pushed them towards the floor. For the first time since we were six, I saw my best friend naked, a lot had changed in nine years. Her pussy was covered with a mat of dark brown hair, yet I could still make out the shape of her sex at the junction of her toned thighs. She looked like an angel. “What”, she asked when she noticed me staring.
“You, you, you’re beautiful”, I stammered.
She giggled and sat back down next to me and took my hand. She bit her lower lip cutely as she guided my fingers between her tanned thighs. Her pussy seemed to radiate heat as I got closer. She let go of my hand, I guess she figured that I had the idea, which I did. I ran my fingers through the soft brown hair on her mound and then over the lips of her sex. I let one finger slip between them and into the steamy gash. She was already starting to get wet and I used her fluids to lubricate my finger as I rubbed it up and down her slit. “Mmm, it does feel better to have someone else do it”, she cooed.
It took a minute of awkward fumbling to figure out a comfortable position when we could both masturbate the other, but we figured it out. Soon we were laying on the bed with her stroking my cock while I massaged her clit. She began to softly roll her hips while squeezing my hand between her thighs. The rocking gradually became more urgent and her moans became louder until finally, she let go of my dick as her whole body seemed to spasm and she screamed out that she was cumming. She thrashed on the bed as she climaxed crushing my hand with her thighs until she eventually lay back, spent. After she caught her breath, she went back to stroking my dick, “That was the best!”
Having just made a girl cum for the first time I wasn’t going to be far behind. She turned on the bed and laid her head on my chest as she pumped my shaft. I could feel my sack beginning to draw up and gasped that I was going to cum. She fisted my shaft a little faster and that was all it took. My back arched up off the bed as the first thick rope of my seed soared high into the air above us. It splashed down across her cheek just as the second spurt was reaching the top of its trajectory, it too landed partially on her face and onto my belly. The next couple pooled on my stomach before the last of my seed dribbled down her hand.
“Wow, that was a lot”, she giggled looking up at me. She looked so hot with my dick still in her hand and one big glob of my creamy cum dripping from the end of her nose. “Be right back”, she said as she got up and ran into the other room. She came back a minute later with a washcloth and cleaned up the cum from my stomach and dick.
“You wanna see something crazy”, she asked with a wild look in her eyes.
I reached up and tweaked one of her nipples, “Is it going to be better than I can see right now?”
“I don’t know about that”, she blushed but come on. I let her pull me by the hand off the bed and into the hall. The way her sexy ass swung back and forth; I would have followed her anywhere. I did not expect anywhere to mean her parents’ bedroom. She let go of my hand and opened the top drawer on the taller of the two dressers. From the men’s underwear that I could see, it was her fathers, I didn’t want to see her dad’s fruit of the looms. She reached way into the back and took out a small key and walked over to his gun cabinet.
“We shouldn’t be messing with his guns”, I warned cautiously. Being a cop and an avid hunter, Ashley’s dad had a pretty formidable arsenal in the case.
“Not his guns silly”, she giggled as she unlocked the case. At the bottom were two drawers and she pulled the lower one open. She dug behind what appeared to be enough ammunition for a small army and pulled out two VHS tapes. “These”, she declared triumphantly as she held them up.
I was confused, why was her father apparently hiding videotapes in his gun cabinet? How did Ashley know about them?
With the tapes in hand, she led me out to the living room. VCR’s were still pretty expensive back then so if a family had one it was usually in the family or living room where everyone could enjoy watching movies. She sat me on the couch before firing up the TV and VCR although honestly, I was paying more attention to her perfect little ass than what she was doing with the entertainment center.
She sat down next to me as the tape started, “This is going to blow your mind!”
So far everything that had happened to this point already had my mind blown.
The tape started with the usual static and then an out of focus view of her parent’s bedroom. The picture cleared up just as Asley’s mother Linda walked into view wearing just her bra and panties. Her father entered the view, also in his underwear. Holy shit, Ashley had found a tape of her parents having sex! Sure enough, her mother laid back on the bed and her father walked up to the side beside her head and fished his dick out of his briefs. The camera zoomed in as Mrs. Robinson took her husband’s limp cock into her mouth, that was very sexy, but it dawned on me that there had to be someone else in the room to work the camera. The camera stayed focused on the half-naked woman sucking lovingly on her husband’s prick as he grew harder by the moment in her mouth.
As he grew harder the camera zoomed back out and the camera operator joined in on the fun. I instantly recognized the curly brown hair of the woman as she sauntered naked into the camera’s view. Long before the woman turned to smile at the camera and showing a profile of her big tits, I knew that it was my mom and damned if she didn’t look sexy. She reached the bed and tugged down at our neighbor’s panties until she pulled them free and dropped them on the floor. It was hard to make out any details of her newly exposed pussy given the distance and a large amount of hair that covered her sex. I watched in amazement as my mother apparently licked and kissed her way up Mrs. Robinson’s body until they locked lips on either side of Ashley’s father’s dick.
They took turns sucking on his bulbous knob and licking his shaft for several minutes before he backed away from the two women. He walked closer to the camera and then out of view. A few seconds later the camera zoomed in again on the two women as they embraced and kissed as only lovers do. My mom seemed to break the kiss and begin to work her mouth down her friend’s neck and onto her heaving chest. She seemed to reach behind the other woman’s back and suddenly her bra was being pulled from her shoulders to join her discarded panties on the floor. I knew Ashley’s mom had big tit’s, so seeing them set free was shocking but, it wasn’t as shocking as seeing my mother suckling on them like a baby.
Ashley’s hand found its way onto my lap and began to softly stroke my cock which was already rock hard and oozing from the tip. I wrapped my arm around her slim shoulders and played with her titties as we watched the action unfolding on the screen. Ashley moved her head lower onto my belly, only inched from my hardon. Her dad moved the camera to get a closer view and then walked back into the picture. My mom was now obviously licking her friend’s pussy and Mr. Robinson stood beside the bed and fed his rather large cock into his wife’s open mouth. As she sucked on it, I felt Ashley’s hot breath blow across my own throbbing member. “Oh fuck”, I groaned as her soft lips wrapped around the head of my prick. She bobbed her head up and down my shaft doing her best to emulate what her parents were doing on the TV. Words could not describe the feeling of her hot wet mouth sliding along my shaft.
Neither of us was really paying attention to the TV at this point so I nearly missed Ashley’s father pull his cock from his wife’s mouth and move behind the upturned ass of my mom. From the way he grabbed her hips and rolled his own, it was obvious he was fucking her. I wanted to do that with his daughter! Having obviously seen the tape before, my best friend allowed me to roll her onto her knees on the couch. I looked down at her perfect round ass and aimed my dick at her hole. I pushed against her, but her hairy pussy was still too dry and tight for me to get into her, so I spit on my fingers and spread it around her entrance. I lined up again and this time I was able to push inside of her tight canal. I only got a little more than an inch inside of her when she clenched her hands around the cushions and seemed to cry into the bright red throw pillow. I stopped pushing out of fear that I had hurt her but after a moment she began to push back against me, drawing more of my cock inside of her. Slowly, I pushed all of my six inches into her and began to fuck her with a lot slower pace than her father was doing to my mom on the TV. Her mouth had been amazing, but the feeling of my cock in her virgin pussy was mind-blowing. I looked down to view my hard cock pumping in and out of her pussy and noticed a bit of pink-streaked wetness along my shaft, blood from her torn hymen.
“Oh, God that feels so good”, she whimpered as I pushed into her tight hole. “I’ve wanted you to do this for a long time and now I don’t want you to ever stop!”
Feeling my best friend’s pussy gripping my cock in its hot wet embrace, I didn’t want it to ever stop either. I grabbed the soft flesh of her hips and began to fuck her a little harder, and then harder still until the sound of my belly slapping against her firm ass echoed through the house. Yeah, I wanted to do this forever, but I could already feel my balls filling and knew that wasn’t going to happen. I looked over at the TV hoping for a distraction but saw that our parents had switched positions. Ashley’s parents were now fucking in the missionary position while my mother straddled her friend’s face. Seeing this certainly didn’t help stem the rising flood building in my sack.
Not wanting to cum just yet and being a bit curious after seeing my mom eat Linda’s hairy snatch and now being tongue fucked by her, I pulled out of Ashley’s pussy and urged her to roll onto her back. When she did, I leaned over her and kissed my best friend for the first time. Her lips tasted like strawberries as our tongues explored each other’s mouths.
“Did you shoot already”, she asked breaking our kiss.
“No”, I assured her, “I was getting close though.”
“Then why did you stop?”
“Because I wanted to do this”, I said with a smile and moved down until my face was only inches from her amazing pussy. Without a second thought I spread her hairy lips and ran my tongue all the way up her glistening slit. I’ll admit that I was a little nervous about how it would taste, would it taste like fish like they say in all the jokes, or maybe like piss? It didn’t taste like either, instead it was delicious.
“Oh yeah”, Ashley sighed as I began to lick her in earnest.
I thought back to how she reacted when I rubbed her clit earlier and focused my tongue on her clit which instantly made her roll her hips and grind her pussy on my face. As I continued to lick her tasty snatch her little moans and cries of pleasure grew louder as her body writhed on the sofa. I looked up from between her thighs and watched as the first waves of her orgasm washed over her face. It was a look of pure ecstasy as she cried out unintelligibly and clamped my head between her strong thighs. Her whole body seemed to shake as I lapped up the addictive creamy nectar that flowed from her.
Eventually she came down from her climax and with her juices cooling on my face I climbed back up onto the sofa and between her silky-smooth thighs. She reached down between us and guided my cock back inside her steamy cunt. It slid in easily and soon I was back to fucking my best friend, or was it girlfriend now? It may not seem like a big deal, but when you’re still in your teens it’s an important distinction. Either way, I kissed her like she was my girlfriend as I pumped my cock into her wet pussy with long slow strokes. I loved the way she moaned into my mouth each time I sank into her tight cunt and my heavy balls slapped her asshole.
As we made love, she wrapped her legs around my ass and urged me to fuck her harder, which I naturally did. Soon enough, the sounds and scent of our coupling again filled the room. The scenes of our parents on the TV were all but forgotten as my senses were completely locked on the beautiful girl below me. She rolled her hips, fucking me back in perfect rhythm until finally I could feel her beginning to cum again. The velvety walls of her canal gripped my shaft seemingly trying to milk the seed from my balls. I fought to hold off my own climax as she thrashed on the couch below me, but it was a futile effort.
“I’m gonna cum”, I warned her and tried to pull out.
“Don’t stop”, she cried and tightened the grip her legs had around my ass.
“Ashley, I can’t hold back any longer”, I grunted as I desperately tried stem the growing eruption.
“Then don’t”, she exclaimed, “Shoot it inside me.”
That was the final straw, with one last mighty thrust I buried my cock inside of her and held her tight as the first shot of my seed exploded into her. It was like getting shocked with electricity each time my cock twitched and sent another load of cum deep into her pussy until finally there was no more to shoot, and I collapsed breathless on top of her sweaty body. We lay there for a while, catching our breaths and kissing. My dick softened a little, but not enough to be squeezed from her sloppy hole and soon she began rolling her hips against mine again. Ah, the wonders of a teenage boy’s stamina, I was quickly back to being totally hard and fucking her as if I hadn’t just cum. We fucked for another half hour before I shot a second load of my seed into her young womb.
By the time we finished with round two the tape had finished, not that we’d been paying much attention to the last half of it. I sat back on the couch, tired and sweaty as she got up to rewind the tape. When she bent over to hit the rewind button, we didn’t have remote controls back then, I could see the cum oozing from the swollen lips of her sex and beginning to run down her sexy leg. Damned if I wasn’t a bit worried about becoming a father while still in school myself.
While the tape rewound, we took a quick shower which was pretty cool since the last time we’d showered together we were both only six. That time we’d been more interested in the toys that we’d snuck into the bathroom with us, this time we spent almost the whole time playing with each other. After we got out of the shower and reluctantly got dressed Ashley put the tape back in the gun cabinet. We kissed for a little bit more before I had to head home before our parents got home.
Dinner with my mom was a little awkward knowing that she was having sex with the neighbors. It was hard to look at her the same way, I’d never really thought of her as a sexual being before, she was just mom. Now all I could think about was the images of her eating Linda’s pussy and getting fucked by Ashley’s dad. By the time that I went to bed that night I was beginning to wonder what I could do with this new information. I fell asleep with a sock full of cum next to the bed and a smile on my face.

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