First of several parts recounting a sexual relationship I had with two young sisters. When I was twenty I moved to Chicago because my girlfriend at the time was moving there to attend Northwestern University. I got a job at a coffee shop in Evanston near her campus and although we broke up pretty soon after it was probably for the best, because this coffee shop was an excellent place to meet young women. The cafe was open until 3 am and it was the only place around that was open after 10pm that wasn’t a bar. As a result we got a lot of undergraduates who would hang out and study all night, as well as high school students who really didn’t have anywhere else to go, and who liked having a safe space to brush shoulders with the college kids. The owner knew her target demographic, and the place was a hip, kinda dirty place with dim lighting, loud music, and lots of big comfy couches – all in all a much cooler place to hang out than the Steak and Shake or Starbucks.
I could tell a lot of sexy stories about this time in my life, but one of my favorites concerns the two young sisters, Claire and Rachel, whose father owned a restaurant down the block. This guy often had to be doing paperwork late into the night and so his daughters would accompany him and hang out at my cafe with hot cocoas or milk shakes while he worked. Rachel was a teen punk rocker: she would usually be wearing a rainbow of makeup, heavy boots, a short skirt, and t-shirts carefully torn to reveal glimpses of her well developed young body. Rachel would usually spend her time texting on her phone and listening to Pixies or David Bowie. Her younger sister Claire was slim and boyish in all the ways her sister was curvy. Claire was bookish, she had thick glasses and usually wore her long hair pulled back into a pony tail and rarely bothered to change out of her school’s uniform – a plaid skirt and white blouse. She would spend her time at the cafe getting ahead on her homework or with her nose in a novel decidedly more advanced than her curriculum. I developed quite a liking to these two girls, and when business was slow I would chat with Rachel about music or give her advice about boys, or help Claire with her math homework or recommend her books more challenging than her teachers were allowed to.
Just before Rachel’s birthday her boyfriend broke up with her, and she was really broken up about it, so I decided I would gift her an old t-shirt of mine: a Talking Heads tour shirt I’d gotten years ago at a thrift store, that was getting a little too ragged for me to wear, but that I knew she was really fond of. They came in the next night and I had the present all ready. It was a slow spring night, so I was able to come right over to the couch they were sharing and I sat between them and put my arm around Rachel. “Hey kiddo, happy birthday.” I said and handed her the wrapped shirt. She seemed happy and astonished that I’d gotten her anything at all, and when she pulled apart the newspaper and saw what it was she let out a loud laugh and threw her arms around me and pulled herself onto my lap. “Oh Drew I can’t believe this!” she said against my neck, and the she surprised me by lifting her face to mine and giving me a quick kiss on the lips. I could have perhaps just let all this go as a kind of adolescent overexcitement, but when she pulled her face back she gave me a decidedly adult, sexy smile and added “Well now I have to get you something.” And she kept her eyes on mine as she began to gently grind her butt against my lap.
This had all happened very quickly, and it took me a second to process. At once I became aware that my hand had by reflex moved to her hip when she’d shifted into my lap and the skin of her thigh felt very, very soft through the thin fabric of her skirt. A nanosecond later I realized that there was nothing between her cute little teenage ass and my cock besides the denim of my jeans, and that my cock must have already been aware of this as it was rapidly becoming fully hard. I looked around quickly but the cafe’s only three other patrons were intently playing cards and wouldn’t even have been able to see what was going on, and then I noticed Claire sitting right next to me, giving off an exaggerated air of being involved with her book. I turned my head back to Rachel to say, well I don’t know what, because before I could open my mouth she leaned her head forward so that her lips were right next to my ear and whispered “Meet me in the girl’s bathroom in fifteen minutes,” her breath hot and moist in my ear, and with a last little grind of her tush she slid back over onto the couch and said loudly “Thanks a lot for the shirt Drew!” and put her headphones on. I stared at her for a moment, wanting to try and talk to her but she just smiled at me and closed her eyes and started bopping her head to her music. I turned and looked over at Claire who was still just sitting there with her nose in her book. “Hey Claire… uh..” I started to stammer, but she just pointedly turned away, refusing to acknowledge me.
Confused and incredibly horny I slowly got up and went back behind the counter where my coworker Stephanie was doing her Sociology reading, and apparently hadn’t noticed anything. “Slow night, huh?” She said looking up as I came over. “Uh.. yeah. I guess I’m gonna do some prep for tomorrow” I responded dazedly. “Fuck the morning shift, man. What have they ever done for us?” She said with a smile, and went back to her textbook. I started to clean some of the shelves just so I wasn’t standing there like an idiot, while I tried to wrap my head around what had happened. Did all that really happen? What was going to happen next? I mean, I had certainly noticed that Rachel was a sexy little thing – she had big tits for her small 5’1” frame and she loved to show them off by wearing shirts and tank tops so small that her breasts seemed to strain against the fabric, which she’d also started cutting off to show off her flat midriff and new belly button piercing – and I’d inferred that she was sexually active from hints in the conversations I’d had with her; but maybe because she was always there with her little sister, or that I knew her dad, or just that she was so young, I’d never actually thought about fucking her… but boy was I thinking about it now. I was thinking about the feeling of her sharp hip bone in my palm and the heat of her ass on my cock as I’d held her in my lap, the feeling of her lips against my neck and my ear, that wetness of her lips against mine and that seductive look she’d given me afterward. I hadn’t realized it before, but this little girl was clearly a thirsty little whore. She knew exactly what kind of look to give me and just the right place to put her fat little ass cheeks. I started thinking about her sex life, fucking some jock in the closet at a party, or furtively sucking a boyfriend off in his car. I thought about how from hints she’s dropped she’s clearly bisexual, and I imagined her experimenting with her other little girlfriends, clumsily licking each other’s wet little pussies at a sleepover. My cock now felt like a hot iron rod painfully constricted by my pants, and I realized I’d been scrubbing the same few inches of metal for God knows how long. I looked at my watch and it’d been almost twenty minutes since I’d been sitting with the girls. I looked over at their couch and Claire was there alone looking at me, but when we made eye contact she quickly put her face in her book. Then I stopped thinking. “I’m going to the bathroom.” I said to Stephanie. “Have fun pooping,” she replied without looking up.
The cafe had two bathrooms that were out of the way in back by our storeroom, and each was just a single 8×8 room with a door that bolted. I walked back to the women’s, and softly knocked “Rachel?” I asked quietly. I heard the door bolt release and she opened the door, grabbed my hand and pulled me inside, locking the door behind her. “Look don’t say anything,” She said quickly. “I think your sexy and you’ve always been real nice to me and my sister and I can’t stop thinking about how bad I want you to fuck me.” She was still holding my hand and she pressed it tightly against her breast, my hand cupped it of its own accord and her eyes half closed for a second, her breathing was fast and ragged. “Whenever we’re here I think about what your cock looks like and tastes like and how it would feel inside me and how badly I want to be your little slut.” Her eyes were closed now as my hand continued to knead her breast, I could feel her hard nipple poking into my palm through her bra and tank top, while her other hand had reached under my shirt to touch my stomach and my chest. “When we go home I lie in bed and put my fingers in my pussy and my mouth and my butt and imagine you touching me all over and fucking me however you want to and calling me your dirty little whore and…” she had been talking faster and faster and I’d stopped listening and I moved my hand down her body and under her skirt where her thighs felt so soft and smooth against my rough hands. My other hand cupped her cheek and my thumb brushed against her full lips. She hungrily opened her mouth and sucked on it hard as my fingers followed the curve of her thigh, past the sparse hair on her mound and inside the intense heat and sopping wetness of her little teenage cunt. She let out a low moan around my thumb as I slowly pressed two fingers into her tight little hole, the muscles of her pussy clamping down on them hard. I removed my thumb from her mouth and grabbed her by her short hair and brought her face up to mine. Our tongues mindlessly writhed together as I pressed her against the bathroom wall with my body, her hands wildly scratching my back while one of mine clutched her head tightly and the other kept pressing my fingers deeper and deeper inside her. She began shaking, her breath coming out in hot gasps and she grew increasingly limp until I was basically holding her small body up as she came. I’d finally pushed my fingers as far as I could get them inside of her and the hot wet walls of her puss gripped them tightly in spasms, her cum feeling like it was dripping down from her onto the rest of my hand.
I kept my fingers inside of her and lightly kissed her cheek and her neck while she slowly recovered her breath and her balance. When I noticed her breathing return to normal I stepped back, undid my belt, and let my pants drop to the floor. Her eyes cracked open at the sound and then fully widened as she looked at my cock, its length and girth clearly greater than the boys she’d been fucking. “You cum like a good little slut now let me see if you can suck like one.” I told her sternly, seating myself on the toilet. She gaped at me, clearly surprised by how quickly I’d adopted the degrading kind of language she’d fantasized about. She immediately got down on her knees in front of me and tightly gripped my penis, her hand barely able to wrap itself around it. She looked up at me with eyes full of a devouring kind lust and a vast need to please as she lowered her mouth onto my dick, and I gave a low moan as I felt the hot wetness of her mouth envelop my glans. My cock was too big or she was too inexperienced to try deepthroating me, but she used her hand to jerk on the half of my cock she couldn’t fit in her mouth, and her eyes never left mine as she bobbed her head up and down. “That’s a good girl Rachel. I’m so happy to have a little slut as filthy and disgusting as you.” I told her while cupping her cheek, our eyes still locked. She gave out a little moan and I could see her other hand go down between her legs, moving in time with her lips. “I knew you were a little whore baby,” I continued, “I knew you loved to suck cock… that you probably sucked on every boy at school that asked you to… show me what they make you do you little bitch.” She quickly stopped sucking me and took a few deep gasps of air, then licked down my shaft to my balls while slowly jerking and squeezing my cock. I had a feeling where she was heading and gave a light groan as her tongue flicked around my testicles and scooted myself slightly forward and leaned back, raising my foot to the toilet seat giving her access to my ass. She didn’t hesitate and leaned forward, pausing for a second to run her tongue up and down my taint before pushing her face between my cheeks and licking my asshole. I gave a longer groan, unable to believe this hot little teen was such a dirty girl… and that she was so fucking horny for me. As she pressed her tongue directly against my sphincter, forcing it into my butt I gasped, the feeling was just incredibly filthy and utterly erotic. I knew I couldn’t last long with this kind of stimulation so I grabbed her hair and pulled her head away.
We were both gasping for breath now, and when we looked at each other there was no doubt about what was going to happen next. We moved as one, me getting off the toilet and positioning myself between her legs as she lay back on the dirty bathroom floor, wrapping her arms tightly around my shoulders. As soon as my cock found her hot slick little hole I shoved it inside, getting three quarters of its seven and a half inch length into her cunt with that first savage stroke. Rachel let out a gasp and started shaking, and the walls of her pussy began spasming with an intense pressure, squeezing my cock. I could already feel the tension of my own orgasm building in my thighs, and I lost myself in the storm of electricity gathering in my loins, pulling out of her only slightly before ramming my cock the rest of the way in, repeating the motion savagely again and again, pressing her down into the floor as she moaned and gasped and shook beneath me. I was unable to think about anything but the feeling of Rachel’s soft little body under mine, the grip of her teenage cunt on my cock, her hyperventilating gasps in my ear. It only could have lasted a minute or two before I began spurting inside of that little slut, seemingly endless ropes of cum shooting deep into her womb as she writhed beneath me, fingers clawing my back, legs squeezing me tightly to her as the orgasm that had started when I entered her had never seemed to stop, just kept rolling over her in waves as I came in her, until finally I was done and we just lay there, sweating, taking deep breaths, my cock still inside her, exhausted.
We relaxed for a moment like that in the afterglow of our orgasms, before I slid myself out of her and shakily stood up, my legs feeling like jelly. I studied her as I struggled to level my breathing and pulled my pants up: she lay on the bathroom floor, her skirt was up around her waist exposing her plump pussy, its shaved lips shiny with our juices, her eyes closed and her lips were slightly parted in a broad, satisfied smile. She opened her eyes and looked at me, smiling even wider. “Jesus Christ, Drew… I think that was the hardest I’ve cum in my whole fucking life!” I grinned back, “Glad to hear it Rach. I was about to apologize for cumming so fast – I don’t think I’ve cum that fast since my first time!” She giggled, standing up and straightening her skirt, “I’d love to hear about that sometime, maybe while I’m sucking you off?” “Fuck you’re a dirty little bitch.” I said, pulling her to me. She flashed me a wicked smile, then wrapped her arms around me, pressing her body against mine. “I have some cleaning up to do, and I think you better get back to work.” Her makeup was smeared over her face, leftover drool from the blowjob and rimming still clung to her chin, she looked like a little slut who’d been used hard, and I already couldn’t wait to do it again. We kissed, her tongue and mine sliding against one another, my hands running over her smooth curves, before I reluctantly pulled away, gave her another smile, and left the bathroom.
I was relieved to see there wasn’t a line of girls waiting to use the restroom when I stepped out – it had all happened so fast that I was only now wrapping my head around the fact that I’d just fucked a teenager, in a public place, in the coffee shop I worked in no less. Someone could have seen me walk into the wrong restroom, and I really wasn’t sure how loud we’d been since I’d been so wrapped up in the moment so I was feeling pretty scared. There was a second when I walked back out onto the floor where I fully expected someone to be glowering at me, or angrily striding towards me, but a scan of the room revealed that everyone appeared to be where I left them: three regulars playing cards in the corner, Stephanie reading her textbook at the bar, and when I looked over at Claire her face was completely buried in her book. With a relieved sigh I walked over and stood next to Stephanie, “Slow night, huh?” I said lamely. She glanced up at me, “Not for your bowels though, right? You missed six teenie boppers who all ordered milk shakes.” She gave me a toothy smile, and added “I think they would’ve much rather had you make them, you big stud.” I laughed as I went back to my sidework – this was the usual banter between Steph and I. I’d gotten away with it after all.
A few minutes later Rachel came out of the bathroom and rejoined her sister looking like nothing had ever happened. The next half hour went normally, making coffee drinks and milkshakes, doing dishes. When I checked in on Rachel and Claire, Rachel just said “Thanks again for the shirt Drew, it was really sweet.” and Claire seemed even quieter than normal curled up in the corner, but I noticed she was watching me closely with her big green eyes. They left shortly after. Instead of giving them a bill I’d just dropped off a little doodle I’d drawn in the down time with a lame “happy birthday!” written on it, and when I was bussing the table I noticed that at the bottom Rachel had written her phone number with a few x’s and o’s. I smiled and put it in my pocket, unable to keep visions of her kneeling on the bathroom floor, my fat dick in her little mouth, from entering my head. Just thinking about it immediately got me hard again.
Fortunately this wasn’t a problem for long as business quickly picked up, and soon my thoughts were completely wrapped up in the mundane mechanical tasks of working a busy night at a cafe: steaming milk, waiting tables, flirting with customers, talking shit with employees, and drinking tons of coffee. After we’d closed I was hanging out at a booth, smoking a cigarette and counting down the drawer when I pulled out my phone and Rachel’s number and sent her a brief, but very dirty, text. A few minutes later, so soon that I hadn’t even finished the cigarette, I got a text back. It said “The shirt looks great on me! ;)” and was accompanied by a pic Rachel had taken of herself in the mirror wearing my shirt… and nothing else. She was sitting on the edge of her bed, the large shirt pulled up over her hips, her legs spread exposing her young pussy completely to the lens, and it looked like she’d been masturbating as her shaved lips were swollen and wet, parting slightly around her protruding little clit. I gaped for a second before quickly coming to my senses and shoving my phone into my pocket, glad the booth’s table was hiding my body’s reaction.
For the next hour or so I hung out with a few of my coworkers for the nightly ritual of gossip, flirting, and smoking in the closed cafe before everyone started trickling out, calling it a night. When I got into my car I pulled out my phone and brought Rachel’s picture back up and took my cock out and began slowly stroking myself in the deserted parking lot, thinking about the slutty things she’d said to me, the way her mouth felt on my cock, how ready and wet her cunt looked in the picture. It was then that I got another text, from a new number. Confused about who’d be texting me at four in the morning I pulled it up. The text said “I think it looks way better on me :(“ and it was accompanied by a picture of little Claire, wearing nothing but the shirt I’d given Rachel, in the almost the exact same position her sister had been, except that her feet were up on the bed and she had two fingers inside her bare little cunt, the lust and pleasure in her expression looking startingly, erotically, incongruous with her young face. I just stared at the picture for a minute taking in all the details, wrapping my head around what I was seeing, until I realized that my hand was still wrapped around my cock, and it felt as hard as a steel beam. I started stroking myself again, staring at her face, her skinny frame, and finally her little pussy, tightly wrapped around her small fingers, muttering, without thinking about the words “Fuck Claire you hot little bitch… I’m going to shove my cock into your tight little pussy… I’m gonna make you scream you little brat… ohhh Fuuuuuuuck” as I came, sending spurts of cum onto the floor of my car. I sat there, catching my breath, my cock and my hand covered in cum, my eyes unable to leave my phone, and started thinking about what I was going to do.