thissideofparadise's Avatar
thissideofparadise Member Since October 19, 2009

Watching Kenzie Masturbate

thissideofparadise on Masturbation Stories

I had never really thought of Kenzie sexually before. I don’t know why, she was definitely a cute girl with a fuckable body. She was pretty tall, probably around 5’10. Her hair was blonde and cut short around her chin, she had a little button nose and rosy cheeks. Her body looked like one that ached for sex, she was a skinny girl but her lower half was definitely on the thick side. She was wide hipped, decent sized thighs, and a big ass. She was my friends-with-benefits’ little sister. She was a few years younger than me, but that has never stopped me before.

I was over at the sisters’ house for the afternoon and was just wrapping up a fuck with her older sister, who was in the shower getti

Read More
ng ready for a date I was taking her on. I was just wandering around the house when I saw Kenzie run through the hall way in what looked like no clothes. Obviously intrigued, I waited a moment and then followed her in the same direction. To my initially disappointment, by the time I reached her room she seemed to be fully dressed. She had a light colour pair of jeans on and an orange shirt. I still couldn’t help but stare through her narrowly open door, which gave me full view of her bed and the mirror where she was looking at herself and playing with her hair. My attention was then completely captured when I saw her drag her hand across her chest and cup her breast.  She started doing it with both hands on both breasts, and then she let her head fall back a little as she slid one hand underneath what must have been a low cut shirt to play with her nipple. I was starting to get hard as I watched her other hand slip from her covered breast down to the front of her pants that she began to unbutton. She paused for a second that lasted just long enough for me to think that she had seen me, so I took my head away from the door for another split second. I took the quick moment of silence to assume that she hadn’t seen me and I peered back in to see her now on her bed continuing to undo her pants. She pulled her t-shirt up over her belly and unzipped her pants all the way. Her next move was wiggling her pants off her hips, down her thighs, beyond her ankles, and onto the floor. Her panties were white, they hugged her hips so tightly and looked to have some sort of flower pattern along the front and sides, the sight of these made my hard-on stiffen even more. Kenzie let her hands fall down toward her flower panties and explore her panty covered pussy. I watched intently as she her fingers pressed into her pussy and circled round and around as the rest of her body wriggled and her eyes shut tight. Her breathing got heavier and her movements more jagged. Her knees bent up and fell back down as her back bent up toward the ceiling and her head shook back and forth. Her hands pulled back for a moment as she paused again and caught her breath; after her brief recess had ended she used her hands to give her panties the same treatment her pants got, the floor treatment. With her pussy now exposed she started by using two hands to do her dirty girl work. This only lasted briefly as she brought her other hand up toward her mouth and began to suck her middle and pointer finger. All the while she sucked her pussy covered fingers, what she did with her other fingers became more furious. She used what looked like 2 fingers to run circles over her clit and deep inside her pussy. Her girlish whimpers were clearly audible to me, outside her room. Her mouth was wide open as she continued to lick her fingers and curl her fingers in and out of her wet, little cunt. The speed of her hand started to become furious and It sounded like she was really being fucked, her hand pulled back longer than before, but did not linger at all as it exploded back into her pussy. I began to touch myself as well, when I saw her spitting on the fingers in her mouth while she rolled slightly to one side and brought her other hand down toward her ass. I could see her struggle slightly as she worked her other fingers into her ass, while she continued to pound her own pussy. The sight of her almost shaking from pleasure with her hands working not only her pussy but her asshole was one of the sexiest things I had ever seen. She started to work the hands in rhythm, with them coming into her at different intervals. I could see her trying to spread her asscheeks with her thumb and pinking to get more room for her finger’s movement and she lifted her right leg a little higher in the air to get more room to work on her sweet little pussy, which I could now see she was using 3 fingers for. I started rubbing my crotch thinking of how badly I wanted to just stroll in and nail her pussy while she fingered her own ass, and then maybe take her ass for a ride while she worked her own pussy. It was all almost enough to make me cum. Then, as her hip started to jolt around a little I could tell I wasn’t the one who was about to cum. She threw herself back so she was lying completely on her back, she took the finger from her ass and started to suck it like before and now pumped her hands furiously into her pussy. The final pumps of her hand came as big as punches, as she stretched out on the bed and her voice hit a new level of high that she followed with a small girlish sigh. She lie still there for a moment before collecting herself and using a towel to mop up her pussy. She was dressed seconds later and I walked away to another part of the house, kicking myself for not getting involved.

So Sweaty at the Coffee Shop

thissideofparadise on Teen Stories

The last 3 years of my high school career I spent with a bit of a crush and a bit of a sexual fascination with girl in my grade, Kiah. For all of those 3 years we had always been with someone else most of the time and never had the opportunity to turn our little crushes for one another into anything more. We made out once when we were 17, but since then had kept our fancy for each other in secrets and in text messages to one another. After we graduated in the spring and were now college bound, a physical payoff to our 3 years of longing seemed inevitable and completely necessary. Though, neither of us had come out and said that just yet.

 

Read More
s New Roman','serif'; mso-bidi-font-family: David">She worked in a little coffee shop a few blocks from my house where I went to visit her for hours almost every day she worked. It was sort of a miserable little place. Probably no more than 5-10 people came in the whole day, which meant little to no distraction for Kiah and I to talk and flirt. She was also always left alone to run the shop, her boss trusted her and you really only need one employee to handle the minimal amount of business they got each day.

 

So, I went to the shop on a Thursday just like usual to see Kiah alone behind the counter working, also as usual the shop was just as empty as any other day. It was the middle of summer so it was scorching hot outside, at about 98 or 99 degrees and inside the shop I could tell Kiah was at her wits end dealing with a broken air conditioner and flimsy fans like she had been doing all summer. The temperature inside the shop was probably in the low or mid-80s. After I got over the initial little shock of the heat inside the shop all that really came to mind, to put it bluntly, was how motherfucking hot Kiah looked that day. She was a gorgeous girl with such a pretty face, dark shoulder length hair, she had a pretty pale complexion but she tended to get hot easily so her cheeks and chest were a little red. She was tall and very trim; she probably stood about 5’8 or 5’9, so she had legs that went to straight to the heavens and perfect round ass atop them. The fact that her legs and ass were always so perfect sort of steered my away from her breasts that were also nothing less perfect. I’m not too versed in the world of cup size, but if I were to make a guess I would say the fell in the range of a small c-cup. They were enough to make the most of a low cut shirt, and on a day like today, perfect a small tank top. She didn’t really wear much to work, and when it was as hot as it was it made perfect sense. Today she wore a pink tank top, with what I could tell was a white bra underneath, judging from the visible strap on her shoulder. She had on the tightest little pair of jean shorts, she wore them all the time and every time I had to contemplate the physics of how hard they must be to get on and off. And in that moment I wanted to know so badly what her panties looked like I could barely stand it.

 

“When is someone going to fix your AC dilemma, Kiah?”

 

“Gah! I dunno. It really is about to kill me. My boss would never even know how bad it is since she’s never here!” She said laughingly.

 

We talked a little while longer about how hot and sweaty she was getting, which she seemed embarrassed by but I was all for it. We only got to talk for a minute longer when much to my astonishment someone else actually came. Some older woman came in to order a few drinks for her and the other women her worked at the bookstore across the street. Right before she ordered, Kiah gave me a little wink and I took a seat by the counter and told her I would be back in a second. I watched her work behind the counter and it was starting to drive me crazy. How sexual she looked being so hot in her tight little clothes, all that skin, all those legs. I went into some strange sort of sexual coma and as the woman left her order I without hesitation got up and followed Kiah into the back of the shop where she was going to get something. She turned around to see that I followed her and she seemed a little surprised. She laughed and asked “What are you doing back here?”

 

“Take a break for a minute.” I told her, and then I pulled her into me by her waist.

 

I put my hand on the back of her neck and we started to kiss. She didn’t miss a beat with anything. She put her arms around my shoulders and met my tongue, measure for measure. I ran my arms up and down her back, squeezing her hips and loving the idea that my hands were so close to her ass. I pushed her against the wall and this intensified the whole event. I ran my hands up the back of her tank top as she pressed her hands against my abs and chest beneath my shirt. I could feel how horny she was getting in her breath. The way it danced on my ear as I kissed along her neck and collar bone. She was giving me so much support and so much cause, I felt the only right and proper thing to do would be relieve her off her tank top. It came off like a bottle cap, she didn’t think twice about shedding the little piece covering her perfect frame. I pulled her again closer to me; her hot skin felt like it was melting on mine. Before I could even react she had taken my shirt off as well. Now that were had passed the point of shirts I thought it was the perfect time to feel that ass for the very first time. I grabbed it low and lifted her up onto a counter for dirty plates in the back, with the small amount of demand for plated items at the shop the counter empty and the counter would prove to play a pivotal role in the romp. I continued to kiss along her neck and explore the boundaries of her back. I kissed along her bra-strap. I pulled down her shoulder, leaving it bare. I did on both sides. I looked her in the eyes as fondled with the snap in the back. I felt the release of pressure as her bra fell to the ground. I grabbed her bare breasts and kissed her again. I lowered my head down and took one of her nipples into my mouth. She had been pretty vocal for our entire encounter, but she was now passing vocal all together. I circled her nipples softly, then quickly with my tongue as she moaned for me and told me how much she loved what I was doing. I continued to lick her nipples, then her entire breast; I would switch between them ever so often until my steady flow was stunned as I felt her hand creep along my belt. I kept my cool and squeezed her hips which had been speeding up her breathing the whole afternoon. Now my belt was undone, she worked the front of my pants quickly. My top button was undone and my zipper was down in no time, she stuck her hand down the front of my pants on top of my black boxer-briefs to grab and caress my cock what seemed to be almost furiously, but intensity was driving the whole the thing, so I welcomed it. She got tired struggling for room in the front of my pants so she pulled a sexy little move by pushing pants down with her legs. This drove me crazy and stiffened my already insanely erect cock. She started breathing so quickly as she stroked away at my cloth covered tool, the longer she went on the more and more turned on I became. I broke the kiss that we been holding for minutes now and looked out into the front of the store, seeing that we were still clear from any spoilers I turned back Kiah. As I turned around I could see the sex in her eyes, it was painted all over her face and I couldn’t stand it anymore. I gave her one kiss and pushed her further back on the countertop. I kissed my way down and around her flat, pale stomach before I reached the bottom at the top of her shorts. I pulled it open and unzipped its zipper. She lifted her hips almost immediately to let me pull off her shorts. They hit the floor and sight of her black panties set me spinning. I told her that she was beautiful and I leaned my face toward her panty covered pussy. I rubbed her through her panties where there was already a sizable wet spot from all her excitement. I pressed my finger down and kissed the top of her panty line. I wish I could’ve appreciated how sexy she looked in just her panties a little longer, but I couldn’t contain myself anymore.

 

I ran my hands down her sides and hips, finally catching the sides of her panties and bringing them to the floor. My 3 year wait to see Kiah’s full naked form and finally come to fruition. Her pussy looked perfect to me. She obviously hadn’t planned this whole thing, she must have not shaved for at least 2 days, but that meant nothing to me. Her legs dangled over my shoulders and I again pulled her closer to face using her hips. Her pussy and my tongue met in the middle and it was just the taste I needed. She began to move her hips a little as I ran my tongue around the outside of her pussy and over her clit again and again. I worked a finger inside her pussy and I focused my tongue in on her clit. Her hips moved from side to side, she swayed her pussy back and forth in front me. My tongue continued to glide over clit and plunge deep into her pussy, listening to her moan and take in her breath was driving me wild. I was willing to do anything to this girl at this point, I put my hands on the backs of her knees and pushed her legs back into the air bring her little asshole into the air, I went for this as well, tongue out. I started to drag my tongue from her ass to pussy and back again, this was driving her wild. I finally needed to have my reward. I stood up to remove my underwear. Just as I started she sat up and insisted that she do it, so I took my hands away and she pulled them down, my cock sprang out toward her and as she stroked it up and down, all the way, she could only say, “Oh fuck,” as she continued to stroke and look up at me. She licked her hand once, stroked my cock a final time, and laid back onto the counter. We were finally ready. I held my dick toward her soaking pussy and pushed my hips forward. She let out a little gasp, closed her eyes, and threw her head back. The excitement was all in my head and I began to pump away at her, just as my heart was pumping in my chest. I threw my whole body into her again and again, reaching the very back of her pussy. I watched her mouth fall open again and again, she had nothing to grab onto so she balled her fists and was nearly shrieking at this point. I leaned forward and held onto her hips so that we could see each other’s face. I slowed down to let her open eyes and focus on my face. Our eyes locked onto one another as I kept pushing deeper and deeper into her. I brought my face to hers as we continued grind into each other, and we kissed. She then pushed my chest back and told me she wanted to try something. I stood back a bit as she turned around and slightly bent over the countertop, “come on,” she told me. I couldn’t have rushed to her any faster. I pushed her further down so that her ass faced me even more. I took hold of my cock and guided it between her beautiful thighs and into her perfect pussy yet again. This was bliss. This time we started slow. I held her ass cheeks and wanted her to feel every inch as I pumped deeper. This was her position, obviously. She was talking dirty to me now about loving how I fucked her and how her pussy has never been this wet and never felt so good. I took off after this; I pumped harder and harder as I squeezed her hips. Then suddenly we heard the front door. There was a costumer.

 

“Hello? Is there anyone here?” The woman said

 

“Uh, yeah, just give me a second,” Kiah told her.

 

“Ok, no problem.” She replied.

 

“Finish first,” Kiah said to me, with the sex still burning in her eyes.

 

“No problem.” I winked and told her.

 

We kissed again as I slid back into her. “Faster, cum in me,” she said. My hips were like horses at the Belmont now. I rammed into her so hard my balls hit off the front of her pussy as she tried to hold in her shrieks. My hands gripped tighter onto hips I reached the final seconds before I finally exploded and a massive load into her pussy. I could see it begin to ooze out already as I stepped back. She frantically gave me a kiss and got her clothes together as quickly as she could to get out to the ordering counter.

 

“Sorry, I have to go. Call me tonight?”

 

“Of course,” I told her. We kissed again and she ran out to the counter.

 

As I walked past the counter I could still see my cum running down the back of her leg, I loved this. We caught eyes one last time before I walked out the doors as she was taking this woman’s order and I dangled the pair of panties she didn’t put on in the back room right before I stepped out. Her face got even redder and I got one last wink.

 

The Curvy Girl From the Movie Theater

thissideofparadise on Teen Stories

I had been out the country for nearly two weeks. And being out of the country puts you away from most entertainment in your own country. So, in this two week absence of mine I had missed the premiere and almost entire theater run of this movie I wanted to see. By the time I had gotten back, all my friends had already seen this movie and it was on its out way of the theater where it was playing. So, I went to what was probably going to be its last showing, it started at 10:35 PM. I showed up to the theater probably 10 minutes prior to the start of the movie. I walked up to the box office and to a pleasant surprise. A girl from my school named Mallorie was selling tickets. She was the only one working, I made som

Read More
e crack about her looking alone behind the counter and she told me I would be alone in the theater too, I was the only one who bought a ticket. I told her she could join me anytime she wanted. She smiled and we parted. As I walked toward the smaller room where the movie I was showing I thought about how badly I wanted to fuck Mallorie, deep down. I think she caught sort of a bad rep at school, because she was one of the girls that always seemed to have her thong hanging out and if that happens too many times everyone starts to rule that girl a slut, but it didn’t bother me at all and I was sure there was a sexy thong waiting underneath her work pants that very second.

Apart from just her thongs turning me on, Mallorie had a lovely, shapely body with great round tits and a massive, beautiful ass that pushed her jeans around like waves to a sand castle. She was blonde, with blue eyes and red cheeks; they all worked in her favor. Even the uniform the movie theater made her wear worked in her favor. The red polo left almost everything to the imagination, but thinking about her tits underneath that shirt was almost half the fun. And the skin tight, black pants she wore were utterly sexy and I knew there was an itty-bitty thong waiting for me underneath them.

So, just as Mallorie had told me, I was the only one in the theater. I sat up toward the corner of the stadium seating, even though I had the whole theater to myself. I was probably 30 minutes into the movie when I saw Mallorie poke her head around the corner. She was just about to pull her head back when I called out to her.

“Hey! Come up here.” I said in a half whisper, half shout.

“Hey, I just got cut, so I thought I’d take you up on the movie offer.”

“Beautiful.”

We sat there for awhile in silence watching the movie, and then we started the little movements that eventually turned into holding hands. Then, our holding hands turned into the arms rest coming up and her resting her head on my shoulder, which then turned into me holding up her chin for a kiss, which quickly turned into us making out; making out that promptly turned to furious kissing. My hand shot between her thighs and hers between mine, I could feel her getting wet through her insanely tight pants and she could no doubt feel how hard I was getting.

“You know, no one is going to come and check on us here. We’re going to be alone until the movie is over.” She told me.

“Well, what would you like to do then, Miss?” I asked.

After hearing this she promptly got on her knees by seat, took off her work shirt, exposing her big, beautiful tits covered by her tiny white bra. “Unbutton your pants.” She told me.

“Gladly,” I said.

And then no sooner had I undone my belt and pants she was pulling them to my ankles, along with my underwear to my ankles. “You’ve got a great dick,” she told me, as she gave it a huge, full tongue lick from the base to the tip. She continued to lap my entire shaft, expelling all of her spit onto my cock so as to lube it up for later. When she seemed to feel it was properly dripping with her spit she worked her way up to the tip and took me into her mouth. Her head fell up on down along my cock like a theme park ride, her warm, wet mouth glided along the whole way fluently. This girl could really suck a cock. She was bringing it to the back of her throat, getting it dripping wet, and never forgot to give my balls a nice swipe with her tongue. I hadn’t gotten head like this in ages and I never wanted it to end, I grabbed the back of her head, which I rarely do and I tugged her down further, so that my cock would take the journey further down her throat, she moaned along with every bob of her head. I was about to explode, but I knew I couldn’t. I knew she wanted to get fucked, and I didn’t want to deny her of that.

“You want to fuck, don’t you?” I asked her, plainly.

“Yeah, real bad.”

“Take off your fucking pants.”

She stood up and undid the front of her pants, and then she paused. “Do you want to see the front, or the back?” She said in her most smolderingly slutty voice.

“Back. Of course,” I told her.

She heard this and turned her back to me, pushing her huge, still pant covered ass in my face. I gave it a little slap. Then, she slowly started to bring her pants down. I could see the top of her tiny white g-string that I had been waiting for, and then before long her entire round, “phat” ass was exposed and it looked lovely right in my face. This time I gave it a big slap and watched it giggle all around her cheeks and near the top of her thighs.

“You’ve got the best ass, Mallorie. Really, genuinely fuckable.”

She giggled and ran her hand all around it, and then reached for her panties as if to pull them down. “No, no, no.” I told her. “Leave them on for a second.”

She giggled again. “Ok,” she said.

I took in a few more seconds of gazing at her ass and licked all the way up one of her cheeks. It tasted just like I wanted it to. I pulled the string of her panties to the side, exposing her pussy and asshole. Another lovely sight. I spread her cheeks and took another long lick upwards, this time getting to taste her wet pussy and her asshole. It was time to fuck. I grabbed hold of my cock and told her to sit back. I held her panties to the side and she spread her own cheeks as she slowly rocked her massive ass down on top of my painfully erect cock. This was the perfect way to get inside of her. Her hot little pussy wrapped around my cock and swallowed every inch until it was like she was sitting on my lap. It was no sooner that she got to the base of my cock that she took matters into her own hands and started to bounce and rock herself up and down on my cock. The shine from the screen silhouetted her curvy frame perfectly and she looked so good getting fucked in the dark. Every time her ass hit my thighs it shook around like a water balloon that wouldn’t pop. Every time she got the full of my cock in her she let out a little gasp and then took in what sounded almost like an angry breath as she went to its tip. We continued to fuck like this until I could tell in her lack of speed that she was getting tired. I took the initiative this time and I told her I was ready to fuck her. We both stood up and she undid her bra as well letting her breasts. “You’ll love how they swing around,” she told me.

“Bend over,” is all I replied with.

She bent one leg and rested it on the seats next us and stood up with the other, I assumed my position behind her and told her that I wanted to see her spread her sexy cheeks for me again. She obliged and opened the passageway to a treasure chest of lust. I grabbed hold of my cock and rammed into her pussy quickly and deliberately, this was no time for soft fucking. I had absorbed all of her energy from our first position’s romp and exploded into her like a train. I slammed into her ass again and again, making her ass shake around like bouncing basketballs. They would separate on impact and then almost wrap themselves around my cock every time I pulled back. She moaned and inhaled sexually, and deeply. I reached my hand around her waist to play with her clit as I pounded into her. Her knees began to buckle and her hips began to go into fits, seemingly. She pushed her ass back toward me every time that I would thrust my hips forward. I abandoned her clit and used both of my hands to squeeze her ass and hips. I told her I was ready to explode in her pussy. She told me no, that she wanted me to cum on her face while she rubbed the cum out of her clit.

“I’m really close, let’s do it now.” She told me. So, I pulled out quickly as she turned around and got on her knees. I let her get her fingers into her pussy before I pushed my cock out toward her face. She used her bare hand to grab hold of my dick while she went back to work on it just like before. It was so wet, so sloppy, and so sexy watching her lips massage my dick. She pulled my dick out for a second to tell me, “Oh, fuck. I’m close, I’m gonna cum.” She rubbed away at her cunt furiously as she jacked me off and licked my balls.

“Me too, Christ. Open wide.” I said.

Just as her face seemed have released some from her own climax it was almost immediately coved in my cum. It splattered across one of her cheeks; it smeared her lips, covered her tongue, and a bit rolled down her chin. She looked like such a slut, it was so sexy. She licked her lips and used a finger to collect the cum from her cheek and chin and swallowed it all. We stared at each other, breathing heavily for a moment until we realized the credits were playing and the lights would soon be up, and we laughed. I was fine with missing the ending.

My Yoga Class Eye-candy

thissideofparadise on Teen Stories

The 2nd semester of a person’s senior year in high school is always sort of a joke. You take classes that mean nothing and that have little to no actual academic merit. I am no exception to this. My 2nd semester senior schedule centered mostly on part B’s of other classes, newspaper, and my personal favorite, beginning yoga. It was a pretty popular class at my high school, for whatever reason. On any given roll of the class, it was always predominantly girls, usually a “guy among the girls,” if you know what I mean, and a few guys from the football team who took it as a joke. I was none of these things, I was obviously not a girl, definitely not gay, and I didn’t play foo
Read More
tball. I saw myself as pretty normal; I did the newspaper, a few plays, and took AP English, so I didn’t fall into much of a demographic.

 

The dynamic of our class was sort of chaotic. It fit the usual description of having about 80-85% girls in the class, which the 3 jock guys who were in the class never stopped chasing around. While I didn’t terrorize the girls as much as they did, we all had the same things in mind, because the girls in this class were out of control hot. And if it wasn’t enough that we already knew how hot all these girls were outside of class, our instructor always told us that the usual PE class uniform wasn’t necessary for yoga. So, the girls came in their itty-bitty shorts and their tightest tank tops to help their flexibility. There were a few girls in the class who fit the general, archetype description of a hot girl. Vicki, Becca, and Jordyn were all girls who had huge tits and just a general sense of slutiness about them. They fed all the attention they were given. But, it was a different girl who drove me wild every day. Her name was Emily, she was a junior. I was friends with her sister who had graduated the year before, but I had never really spoken to Emily at all. You can always call a girl hot, but that isn’t really what she was, she was cute, she was pretty. Her attractiveness was a nice thing, and though I took it all so sexually, I think that’s just me. She was a pretty short girl, maybe 5’3 or 5’4. She was really thin, so her tits weren’t too big, but that didn’t bother me at all. Her ass wasn’t of my usual large preference either, it was small and round, just like a peach, and it drove me crazy. I intentionally set my yoga mat behind hers when we started class so I could watch her body press in and out of the air each day. It was always the highlight of my day. I would stare at her in downward and upward dog, that cute little ass going up and down, her back arching and bending, her ass coming back high into the air. Some of the poses we did were perfect for moving her shorts just enough to give me a little glimpse of her panties. White, pink, yellow, it was so sexy. I fantasized all through the lessons about fucking her in the center mat in front of the entire class. Letting her gasps be the set breathing for everyone.

 

We spoke a little bit in class, but never enough I thought, to talk to her about how I was feeling about her. My little hour long, daily crush went on for probably the first 6 weeks of the class until we started to catch eyes during the lessons, and make what seemed like longing for one another eye contact in the halls. She had me wrapped around her little finger with just a look. A few weeks later fate would throw me a bone and put us at the same party together after my friends and I had put on the final performance of our spring drama production. We came into an in-progress party where some kids were already drunk, the beer pong was in full effect, and people were starting to make their moves for the late-evening-pair-offs. I spotted Emily on a couch with two of her friends almost as soon as I walked in. I gave her the eyes that we usually gave each other in the halls expecting the same eyes back and then nothing else. Instead, her eyes lit up and she almost jumped off the couch to come talk to me. She could’ve probably seen how surprised I looked but I think I played off. She came to tell how well she thought I did in the play, we talked about yoga class, and her sister off at college. We kept talking and we both started drinking a little. This went on for probably more than a half an hour, before I could tell how drunk she was getting. Her little body had given her a small tolerance, obviously. She started to be a little flirtier and touch my legs. I told her we should go upstairs.

 

“That took you way too long!” She told me.

 

I took her hand and we went toward the stairs. I let her walk in front of me so that I could watch that cute little ass go up the stairs in her nice tight blue jeans; I could see her bra through the meshy back of her read top as well. She turned around to me as we reached the top.

 

“I can’t fucking wait for this,” she said.

 

She was being so sexy I couldn’t help but play along.

 

“Oh, yeah? What are you excited for?” I asked her.

 

“Well, first I want to suck your cock.” She grabbed the top of my jeans and pulled me forward.

 

All of a sudden we were in a dark room that must have been the parent’s room.

 

“Perfect. A big bed is just what I wanted. Turn the lights on though, I want to see.” She told me.

 

“Of course.”

 

“Now, come here.” She said.

 

I walked forward to her sitting with her legs spread at the end of the bed. She went right to work at the front of my pants and my belt was undone, with my pants by my knees in no time. She ran her hand across the front of my grey boxer-briefs for a moment before pulling them down as well. My cock wasn’t fully erect at this point, but it was so damn close. I looked down and saw her tiny hands running all over it and then it turned to stone.

 

“God, I knew that you would have a big cock. I think about it all the time in yoga class.” She said to me.

 

“You have no idea how much I think about you in that class,” I said as she started to daintily lick my shaft and balls.

 

“Oh, I know how much you do. That’s why I was so excited to see you. I know you’re going to fuck me hard.”

 

I couldn’t believe all of this was happening. Hearing that and seeing her work around on my cock. All of her tiny features made my already 7 inch long cock look even bigger. Her tiny fingers wrapped around the base of my shaft and her little tongue followed it up and down.

 

“You’re right. I am.” I assured her.

 

She gave out a sexy little moan and then finally took my cock into her mouth. She nursed the tip so well; her mouth was so warm and wet. The more she stayed toward the tip; little bits of her saliva would run down my whole shaft, it was driving me crazy. And I started to run my cock in and out of her mouth a little. The friction of her little tongue was just what I needed. I could hear her little muffled giggles behind my cock, she was so proud of herself, but I was nowhere near cumming.

 

“Are you going to fuck me now?” She asked me.

 

“I will, but I want to taste your sweet little pussy first.” I told her.

 

“Deal, let’s 69,” she said.

 

“Deal,” I winked and told her.

 

We both took our shirts off, which left me now completely naked, as she then got to work on her pants. She pulled her jeans down and she had a pair of tiny, white bikini-style panties on, that I could swear I had seen under her shorts before in class. As she started to take them off I told her to leave them on, she smiled at this and then swung her leg over my chest putting her perfect little panty covered ass and pussy right in my face. She wasted no time getting back to work on my cock. This angle helped her a little and she started to get it deeper and deeper down her throat. I couldn’t hold back my excitement anymore and pulled her panties to the side, exposing her perfectly, freshly shaved pussy and asshole. I dug straight in. I buried my nose toward her ass and started flicking her clit with my tongue, then zigzagging it back up toward her asshole which I didn’t think twice about before licking as well. She moaned in agreement with every location my tongue found. I ran my hands over her back and would push her hips back toward my face to get her pussy even closer. I ran my hands over her back more and got to her bra that I unhooked to give her perfect little breasts some air. We continued to lick, suck, kiss, and nibble each other for nearly 5 minutes before we both could no longer stand it. She abruptly got off of me and threw her panties across the room. She pressed her hands down on my chest so that I would stay laid down and she took hold my cock and brought it between her thighs to her small, smooth prize. We were both dripping with one another’s spit, but her pussy was proving that it may be too small for me to fit. She kept working my cock with her pussy trying to wedge it in, and then I finally took control. I used one hand to hold onto her ass and the other to maneuver my cock around, I told her to use her fingers to spread herself and she did. Then like that my cock slid into her slowly. She said that she could feel her little cunt opening for me and with every inch her voice cock higher and higher. Once she had finally reached the bottom and I was all the way inside her I pulled her face to mine to kiss her as I slowly started to sway my hips at hers. She tried to kiss me, but she couldn’t keep her mouth closed from her gasps and sobs of pleasure. I moved my hands to fondle and spread her little ass as I started to pick up speed. She started to let out small, near phrases which she couldn’t seem to complete. She grabbed her own breasts and played with her nipples as I continued to rock into her hard now like a high-tide to the shore. I rocked into her and we slammed into the bed’s backboard again and again. She was in ecstasy and I was in control, her little body was nearing collapse as she told me, “I might cum,” I could feel her pussy getting wetter and wetter around my hard cock. Then in a rush sexual charge I pushed her onto her back and started to let her have. I slammed into her harder now than I ever had before. I was driving deep into her pussy now. She shrieked and shrieked, there is no way the rest of the party couldn’t hear her. My balls smacked against her ass as she finally reached her end. Her fingers dug into my back and I could feel her cumming. This drove me wild. My hips turned to a train’s pistons and I continued to pump and pump until I finally unleashed in her. Our cum ran together and out of her pussy, she told me she could feel like drip down her ass, this bed was a wet mess, no doubt. I came in then for a kiss and we continued to make out as our climaxes ran out of her sweet cunt.

 

From then on we would tease each other every day in our yoga class. She would wiggle her little ass about in the hair and I would accidently bump into her with my big cock when she wasn’t watching. Then, after school we would go take out our sexual frustration on each other.

 

The Backstage Incident

thissideofparadise on Anal Stories

All through high school I was involved with my school’s drama department. And the kid’s in our school’s drama department were sort of notorious for having sex and fooling around backstage during plays, during practice, or during any point in the school day really. I’m no exception to that little perversion. I’ve gotten blowjobs behind the curtains, fucked girls in the costume loft, and fingered the makeup girl while she did my makeup. The best experience I ever had backstage though came during my senior year, during the second play of the year. At our school we always tried to do sort of a new aged play 1st and then a classic play the next, the 3 years prior to that we had done Oedi
Read More
pus the King, The Crucible, and Romeo and Juliet, this year the play was to be the classic Cyrano de Bergerac. I was playing the character Christian who is in love the character Roxane, who was played by this girl named Carmel. Now, while I wasn’t in love with Carmel the same way my character was, I still wanted a piece of her, badly. Carmel was a tall and gorgeous girl. When I say tall, I really mean it. She was 6’1, which is good for me, I’m 6’4. She was tall and trim, she wasn’t a toothpick she carried around quite the ass and strong thighs, and they definitely weren’t fat. Her waist was very thin and her tits were actually relatively small considering the rest of her. She had a very pretty face, with shoulder length wavy brown hair.

 

She was the sort of girl that I loved to flirt with, I could get dirty with her and she would play along, and I could always tell when she wasn’t playing. I wanted to fuck Carmel badly, and I knew she wanted to fuck me too. I had heard she was a pretty dirty girl, and that she masturbated chronically because she was so horny, I wanted to give her a solution to that problem.

 

During the final week of dress rehearsals before we put on the show, I had really stepped up my flirting with her. And that day during practice I was getting handsy, putting my hand all over that big ass and touching her back, and she followed me step for step. We weren’t in full costumes yet, I only had medieval shirt and pair of brown pants on and Carmel was wearing a long, heavy skirt with a somewhat renaissance looking top on, she looked hot even though she was totally covered up. And it was a few scenes in that I decided to make my move.

 

She and I were both going to be off stage for awhile, while another character gave a monologue about the two of us. She and I were standing alone watching the scene behind a curtain where no one else was. I decided to make my move quickly and quietly. While she watched the scene I came up behind her, placing my hands on her waist I pulled her closer to me and pushed her hair to the side so I could kiss her neck. She put her hands on top of mine and seem not care at all that I was kissing her ear. In fact, she told me exactly what she wanted.

 

“Kiss my ear.” So, I nibbled along her ear, then kissing the very back part of her neck, then back to her ears. She was moaning a little and I started to get hard. As soon as I knew I had a hard I pulled her closer to me. Then with my hard cock against her ass, I kept kissing at her ear, and started to rub her pussy through her skirt.

 

“Are you sure we can do this here?” She asked.

 

“Oh, yeah we’ll be fine. I’m not done yet.” I told her.

 

I started using one hand to massage her pussy through her skirt and I then took my other hand up her shirt, and much to my surprise found her little tits uncovered.

 

“Oh, no bra?” I asked her between planting kisses on her neck. She only laughed in return and began to massage her nipples in time with the treatment I was giving her cunt. I started to get more liberal with the work on her pussy and tried to pull her panties to the side, over her skirt. I started to feel how wet she was getting and my cock got harder and harder against her big ass. I was too turned on to wait any longer at this point. I took my hand off her breast and used it to pull down my pants and boxers, exposing my cock. Then, I used it to lift up her skirt. She had on a pair of full bottom, baby blue panties that shaped her big ass perfectly. There was still a little ass that couldn’t quite fit all the way in them, and it was beautiful.

 

“Look at this ass.” I said.

 

“You want it, don’t you?” She asked.

 

“Oh, of course, let me see it”

 

She then reached back and pulled down her own panties to about her knees. I started caressing her perfect, smooth ass. “Beautiful,” I told her. “Now, bend over more and let me see that pussy.” She bent her knees and her head went down a bit pushing her ass toward me. I could barely see her pussy, but any sight of it was enough. I spread her cheeks and ran my hand up her bare cunt and asshole. I asked her if she was ready and she only replied with a little head nod. So, I spit into my hand and lubed up my cock as best I could and started pushing it into her wet, horny pussy. She tried to suppress her moans as all 7 inches slid into her deeper and deeper. She let out what seemed like a whimper when I finally penetrated her as deeply as I could. She told me to go slow and I did just that. I made her feel every inch of me as I held on firmly to her hips and rocked my hips into her softly, like a boat beating against a dock. I ran my hands up her back to bend her over further, and I started to thrust harder. My cock pushed the boundaries of the walls of her cunt and ran along her clit with every push. She held onto the stage curtains in front of her with one hand and even brought her other hand back to spread her ass.

 

“Oh, god. Oh, my god.” She said. I squeezed tightly on her ass as I picked up speed again. I started to knock into her hard enough that my balls started to swing forward and hit her clit. She didn’t fail to mention this to me, word for word. Every so often her knees would buckle, which every time earned her a harder and harder smack across her big, tall ass. I reached my hand forward on her chest and pulled her into me, so that her ear was close to my mouth. I continued to hump her gently as I asked her, “Have you ever been fucked in the ass before?”

 

“Oh, no. Never,” she said.

 

“Want to try it?” She waited a minute before she responded. “Yeah, I do.”

 

So, I returned my hand to her back and pushed her forward. Her ass pushed toward me again, and my cock lined up directly with her asscheeks, it rested perfectly against her pussy and asshole as I squeezed her cheeks together and spanked them. Her ass was getting red from all of this attention, it wasn’t half the attention her cute little asshole was about to get. I sucked my finger to lube it up some and I worked it up her ass. She trembled as I did this and let out another one of her little whimpers.

 

“You like it, don’t you?” I asked.

 

“Mhm.”

 

So, following this I spit out twice more. Once, onto my hands to rub into her asshole and the other to again lubricate my hard cock. And then I started for her ass. It gave much more resistance than her pussy, but the friction made it even sexier. She still held her hands back to spread her cheeks for me, and she made no effort to suppress her moan as I pushed deeper into her ass. My cock buried into her and she had already begun buckling at the knees. She used her free hand to play with her pussy and steadily rocked my hips and cock toward her nice ass. I pumped and pumped and we were now singing in a harmony of pleasure. Our moans matched one another as we both seemed to be pumping toward our brims. I knew she liked it rough, so I continued to spank her and squeezed her ass as I tore it apart. She plunged her pussy and was breathing deeper than the ocean.

 

“I’m going to cum in your ass.”

 

“Do it, fucking do it,” she encouraged me. So, I turned up the speed significantly as I rammed into her ass, she started to shriek. “Shhh, shhh. Here it comes.”

 

And my load erupted into her like I had struck oil. We instantly fell to our knees together as I continued to let out drops into her ass. She turned her head around to me and we began to kiss as my now limp cock fell out of her, uncorking her cum-filled champagne glass of an ass. Drops of my cum fell out of her onto the floor as she worked the last bits of her own cum out of her pussy.

 

“We should try this again sometime. Somewhere where I can be loud.” She giggled as she said the last bit.

 

“Oh, anytime.” I told her.

 

It was only seconds later that we needed to be dressed and on stage. Our little episode backstage definitely helped our chemistry on stage, we later realized.

 

My Friend's Little Sister (Always a Classic)

thissideofparadise on Teen Stories

My friend Will and his family moved into town about 3 years ago. Since then he and I have become really great friends, I even gotten onto pretty good terms with his family, his parents are both funny people and they always seem happy to see me, but it’s his sister that I’m really a fan of.

Katie was a walking, talking apparition of sex and lust. She was a few years younger than us, but that never mattered to me. She was tanned to such a perfect colour of bronze; her skin looked like honey to me. She was a gorgeous girl. She was probably 5’5 with a pair of long, long legs. She was about as thin as she could get without looking unhealthy. Her tits and ass came out from her body like a perfect set o

Read More
f peaches and apples. The combination of her thin legs and waist, her round breasts and ass, her thick, luscious lips and beautiful face, were enough to leave me feeling stunned. I always flirted with Katie and made no secret that I had an eye for her, that’s why I’m sure it was no surprise to Will when he found out what happened between her and I.

The day that it happened I was over at their house pretty early in the morning. I was over to pick Will up so we could go golfing with some other guys and as I was waiting in his living room for him to get his clubs Katie walked out of her room. She was clinging to a towel like it was holding her body together, and that was all she had on. Her hair and skin were still wet from her shower. Her lips grew like a bell into a perfect smile and her eyes opened wide.

“Hey,” she said as nonchalantly as she could, I’m sure.

I gave her a little hi and smile back and she continued right through the house as Will came out, ready to leave. We were gone through almost the whole afternoon and got back to Will’s at around 5 o’clock. It seemed like no one was home when we got there. Will’s parent’s owned a restaurant and were almost always there into the late evenings and Katie was nowhere to be seen. We hung around the house for a minute and really did nothing. Will got a call a few minutes later from his mom reminding him to run a check out to the restaurant, which was about 15-20 minutes away. He said I could hang around his house if I wanted to and wait for him to get back. I had no interest in taking the drive out to the restaurant, so I told him I would take a shower while he was out. He left and I took off immediately for Katie’s room. In all the years I had been coming over to this house I had never really been in Katie’s room for more than a couple minutes, and now I had it all to myself. I opened the door and took in the scent that was without a doubt, all her. He wandered into her room in what was almost like a trance. I stared at the walls and messed around with all of the little things on her dresser and desk, and then I was finally staring at the top drawer. I pulled it back and gazed down at the marvelous treasure chest that was her panty-drawer. She had little thongs, g-strings, boy shorts, and bras of every colour. There was lace, silk, and cotton, everything that I imagined hugging close on her thighs, around her waist, and over that perfect ass. I picked up a few pairs to fully examine. First a ruffle-y, pink thong with a heart cut-out above the ass. Next, it was a pair of lacey, blue, full bottom panties that I’m sure fit the shape of her ass perfectly. And just as I was about to pick up a little, white cotton thong I heard her.

“Looking at my panties, huh? What do you think?” She laughed a little and rested against her bedroom door.

“Oh, it was, I was just only…” I trailed off.

“Where did Will go?”

“To the restaurant, he left 2 minutes ago probably,” I tried to straighten myself up.

“Good, so we have a minute.”

I couldn’t believe what I just heard, I laughed a little. “What?” She took a few steps toward her bed and egged me on again. “Come over here.” Her eyes caught me like a lasso and her direction was the only direction I knew.  I walked closer to her and she put her arms around my neck as we our lips fell together perfectly. We continued kissing as I ran my hands up and down her sides. She wore a pair of jeans that could have only been painted on, they squeezed her hips and thighs better than her own skin and a black halter top dangled down over them. She pulled back from our kiss for just a second.

“How bad do you want me?” She asked me.

“More than you even know.”

“Show me”.

After she said that I was just off to the races. I picked her up by her ass and laid her out on the bed. My mouth moved from her lips down to her neck, back up to her ear, back to her mouth, and then across her chest. As I was kissing her chest I could feel her start to wriggle in anticipation, and I didn’t feel like being one to make her wait. The halter top she was wearing had single loop that went around her neck in the back, which left her shoulders unoccupied, and her breasts easily accessible. I pulled down the sides of her top to expose her breasts, she wasn’t wearing a bra, and this drove me wild. I left my tongue fall out on top of her small nipples as I drug them along her perfect chest, and brought her nipples an erect state of arousal. As I continued to circle her nipples and suck them lightly, I let my hand fall between her legs. I could feel the button of her jeans on my wrist as my fingers flexed over her jean & panty covered pussy. I flexed them hardly, then gently as I could feel her pussy already starting to moisten. She let out tiny whimpers of pleasure between to attention to her nipples and her pussy. This went on until I could feel the erection in my pants getting harder than I had ever felt before, Katie must have had some sort of intuition to this as she glided her hand over my jeans, and giving me an audible smile as she grabbed hold of my jean covered cock. We continued to stroke each other until the jeans we both had on seemed so unnecessary, my worked at my belt as I unsnapped and unzipped her jeans. We crept around on the bed as we removed all our denim, revealing me in my black and white boxer briefs, and Katie, looking nothing less than perfect in her little thong. It was a yellow mesh thong, with pink bits of lace across the front and the sides and a little ribbon above the ass in the back. She stood up on her knees in front of my as we took off our shirts as well. She looked phenomenal there in nothing other than her outrageously sexy panties. I put hands on the small of her back and the back of her neck as I brought her in for another kiss. My hands then fell down her back, grabbing hold of the uncovered parts of her ass. She was so smooth, she was such a dream. I handled her ass as we handled one another’s tongues. I brought my hands around from her ass to touch her panty covered pussy, she was now soaking and I started to stroke her harder. And with this, her little whimpers of pleasure turned to definite moans. I wanted to give her as much as I could give her; I kissed her then whispered for her to lay on her back. As she fell back on the bed I positioned myself between those beautiful, long legs.  I put my hands on her hips by her panties; I stalled for just a second and said.

“You know, I really love looking at these. It’s sort of a shame to take them off.”

“Well, you can have them.” She said and winked.

I trembled at everything she was saying and doing. Then I gazed ahead of me at her panty covered pussy and gave it one last kiss before I slid them off and went to work on her bare pussy. She was shaved perfectly like it had never even seen hair. And she was so wet at this point that my tongue slid all over her clit and around pussy. I worked at her tiny cunt with marked intensity. I lapped up every bit of juice she had to give me and tickled her clit with the tip of my tongue. I started to run one finger in and out her as slowly as I could and still focus my attention in on her swelling clit. We were both getting insanely involved with this. I put my hands under tiny ass and lifted her whole lower body. I spread her little ass cheeks with my thumbs and started to run my tongue over her ass and back to her clit. I never really thought she would be the type of girl who love getting ass licked, but she really was. I liked nothing better than the feeling of having a girl squirm and buckle while I used my tongue to do her; this was making my cock want to explode.

“I need you in me.” She told me.

Before her sentence had even ended I was peeling off my boxer-briefs and bringing the head of my long cock toward the opening of her now drenched with spit and pussy juice slit. She brought her hand down to direct my cock straight in and she put her other hand on the back of my neck as she pulled both hands in closer. My cock plunged deep into her pussy and I went for a kiss that went unfulfilled, because she wasn’t able to close her mouth as my cock pushed into her. Her pussy was as wet as I’ve ever felt one and she was as tight as my own skin, I wondered if this was her first time. Just thinking about that made me ram her harder and harder, as her definite moans now turned to erotic shrieks.

“God, your cock is so big. Fuck me, good God, fuck me, baby.”

She sounded like such a slut, it couldn’t be any better. Our hips smacked and our bodies slammed together. I held onto her hips and she brought her legs around my waist. The sounds of her moans and our skin slapping blended into a perfect harmony and we were in bliss. The longer we went on the more and more intense I got not letting up a bit, I once more put my hands under ass and picked her up. I had her whole lower body off the bed which gave me the leverage to drive deeper and deeper into her.

“Oh fuck! That’s it. Right there, that’s it,” she started in a scream, but then tapered off into a little moan. Her noise level worked like a boomerang in that moment. She screamed “Oh fuck!” then got quieter as he told me “that’s it,” like she was falling into a coma. Then it all came back like a wave.

“I’m cumming! Oh God, baby! Fuuckk, yessss!” She shrieked and rumbled and shook, as felt her pussy clench around my cock and then release, 3 times over. Her body fell almost lifeless back to the bed as she fell off of my cock. She laid on the bed for a moment silent as her body continued to tremble. She then reached her out toward my cock and opened her eyes as she grabbed. I looked down as well to see it still dripping with her juices, as well as little bits of her blood. It was her first time.

“Look at all of my cum all over your cock.” She giggled a little bit. I laughed back a little bit between breaths.  “Yeah, I guess.”

“I want you to cum on me.” She told me.

“You know, I would just love that.” We told each other this all between kisses.

“Where do you want your cum, baby?”

“All of your ass, Katie. It’s so perfect and I have nice big load waiting for it.”

“Perfect.”

She crawled out from underneath me and assumed the position on all fours in front of me. She pushed her head down onto the pillows at the top of her bed and put her hands back to spread her ass for me. I walked up and spanked her ass lightly as I grabbed my cock and rested it between her cheeks, with it pointing toward the ceiling.

“You’ll love this.” I told her. She could only giggle and moan in return.  With my cock and her cunt both still soaking from all our foreplay and our romp before hand, I needed no extra spit and my cock worked its own way in. If I thought that her pussy was tight originally taking her now from the back was even tighter. And if I thought I had been deep in her before, I was again happily mistaken. I loved taking girls from the back. It’s so sexy watching their asses giggles from the contact with my hips, hearing an entirely different moan from them based on this different point of entry, watching their backs arch up as they build up their little cums and climaxes, even just the sound our slapping bodies made was enough to drive me wild. And Katie was better than all girls. It was like she was throwing her own ass and pussy back toward my cock. Her ass was perched up and poked out so high above the rest of her body, she looked like a pin-up model. Her moans were muffled by her pillows, but were almost just as audible as they were before. I watched as my cock sank into her inch by inch, I loved being in control of her like this. And following suit with that idea I took both of her hands and held them on the small of her back like she was hogtied as I used to the other hand to hold onto her hips. I was completely carried away by my own sexual prowess, at this point.

“God, Katie you fucking slut. You’re so fucking sexy. I’m going to cum all over you. You know that, right?”

“Cum on me baby, do it. I’m your slutty little cunt, fuck me!”

It was this that triggered the last few pumps on her little ass that sounded like a tackle in the NFL. Then, it was the release. I pulled out and exploded all over her. The initial shot traveled all the way toward the middle of her back, and the rest trailed in little globs all over both of ass cheeks, down her asshole and the backs of her legs. It was massive.

“Mmmm, God yes” She said as I ran my now cock over her ass, mixing up all of my cum. She took her own hand and rubbed it all over her ass to collect the cum then brought it to her mouth to taste it.

“Oh, yum,” after saying this she turned around and told me she wanted to clean me off. She took my now almost limp cock and spit all of the cum in her mouth onto it and proceeded to suck it all back off of my cock. She looked up at me with her big, brown eyes and cum covered lips.

“You taste real good.”

“Yeah?”

“Oh, definitely.”

As she continued to lick along my cock her door shot open, it was Will.

“Man, what the fuck?!” he said, sounding a little distressed. “I knew you’d try this.”

“Sorry, man, I….” He left before I could finish.

Katie looked at me and laughed. “Don’t worry, I doubt he really cares. Now, I think these are yours now?”

She handed me her yellow thong and we kissed one last time before getting dressed.