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It was just after my eighteenth birthday that my parents decided to separate prior to divorcing. They decided that I would be better off if I transferred to a high school closer to my mother’s new residence in Yonkers, N.Y. Of course this yanked me away from all my friends and thrust me into a foreign land, or so it seemed to me.
I knew my parents loved me, but after two kids, they really didn’t have time or energy for a third. Between my home life, my school life, and no sex life, I wasn’t quite suicidal, but I was really fucking depressed. Rebelling at this great injustice, I ran away. Not all that far, after all I only had twenty-seven dollars and thirty-eight cents to my name.
Rebelling was one thing, but I still retained a semblance of common sense and took the train into New York City and then a cab to my sister’s apartment on 87th Street in Manhattan.
My sister—Stephie—was six years older than me and worked at Random House, a famous publishing firm in mid-town. She was at work when I arrived, but I let myself in with a key she’d given me when we first learned of our parents plans to separate. Stephie always thought a couple moves ahead of me and probably always would.
Anyway, as I wandered around her apartment I decided to take advantage of being alone and began rummaging through her dresser drawers, sniffing her panties and bras and other unmentionables. I found a pink vibrator next to the DVD player and in the player itself a porno flick that featured mostly 2 guys doing one girl which I promptly slipped into the DVD player and whipped out my dick in order to jerk off to the early scenes.
You may have guessed that being so young my hormones were working overtime and I was jerking off six or seven times a day.
Now the decision to leave my mother’s and the travel time had cost me masturbatory time, at least two or three chances and I had a stiffy you wouldn’t believe by the time I put Stephie’s bra and panties away—although I kept this one pair of black lace panties to sniff while I whacked off while watching the porn.
I had just finished watching the porn flick and returned it to its proper hiding place when Stephie walked in the door.
“Howie, what are you doing here?”
I had no problem telling her everything that had caused me to leave Yonkers behind. Even before I finished telling her, I realized that my sister was a very attractive woman, with breasts and everything, and that I was alone and in close proximity to her. To my horror and embarrassment, my dick responded, as it was prone to doing. I blushed furiously, and felt like a pervert, but Steph didn’t seem to notice. She ordered Chinese for dinner and we watched a romantic movie, and then out of politeness, I yawned, said it’s been a long day, and she set me up with sheets and a blanket on the couch.
As soon as she left me and went to her bedroom, I jerked off into my dirty t-shirt, with even dirtier images of Steph and her tight black sweater and jeans going through my naughty little head. I felt like a creep doing it, but I was too horny to care.
Stephie kept me busy all day the next day. We went out for breakfast, then came back to the apartment and played video games, then went out for lunch and checked out a couple museums and went for a walk in the park. It was nice out, and Stephie was wearing a light t-shirt that really showed off her perky breasts and a white skirt that I could occasionally almost make out her underwear through. My dick, needless to say, stayed shamelessly hard all afternoon.
Stephie went out for a while in the early evening, leaving me alone in the apartment. I confess that I promptly renewed my snooping and found a twelve pack of condoms with three missing, Woo-Hoo!
I also discovered a couple of dildos and a stash of porno DVD’s, which looked highly intriguing. But before I could slip one into the player and find out more, Stephie came home, and I had to scramble to avoid being caught red-handed.
She asked me what I thought of New York, and I told her that I loved it, and wanted to move there after I graduated. She smiled and said “Yeah, it’s not for everyone, but I think it suits me really well. I think you’d like living here too.”
We ordered a pizza for dinner, and then we went back into Manhattan. A friend of hers was in a band that was playing downtown, and we were going out to hear them play.
I’d never been in a bar before. The band was good, but really loud. I had a beer, which I didn’t like very much, and then Stephie got me a rum and coke, which I liked a lot better. There were lots of hot girls in the bar. I liked the Big Apple, and thanked Stephie for showing me around.
“Youhaven’t seen anything yet, Howie. It’s a really big city with so much to see. We can’t eveven scratch the surface on a weekend.”
Then as we got out of the cab in front of her place, my life changed.
“Can I ask you a question?” Stephie asked.
“Okay,” I said. I was pretty sure I was drunk.
“Do teenage boys really masturbate hardcore porno as much as everyone says they do?”
I turned purple and fell back into the taxi. She pulled me out laughing and paid the cab driver. “I take it that’s a YES then?”
I mumbled something, but even I didn’t understand what I said. Stephie laughed again.
I started laughing too. I realized I was drunk and laughed even harder.
Stephie pulled me up the stoop to her front door and fumbled for her house keys. “So how many times a day does that add up to?”
“What?” I said already wondering why I was laughing so much.
“So how many times a day do you masturbate?”
“Two or three times a day, usually.” I managed to mumble.
“That’s not so much.” Stephie replied as she got the door open and led me up the stairs to her apartment. “When I was your age, that’s about how often I diddled myself; and sometimes even more. And that was–before–I discovered pornography!”
She dropped her keys and then recovered them, letting us into the apartment and closing the door behind her. About that point I realized that she was drunk too.
“So let me ask you something else… Do you stare at the tits of every girl you hang out with; or do you actually think I have nice breasts?”
I turned purple again. I hadn’t realized I’d been staring. Or at least I thought I’d been discreet when I was checking her out. But Stephie thought I was going to be sick and rushed me into the bathroom and introduced me to the toilet.
“Don’t miss the bowel. It’s a big target. Get sick and you’ll feel better. I’ll give you some aspirin and coffee and that will help too.”
I knelt by the toilet but nothing happened. I thought about what my sister had just said. Not about not missing the bowl; about her masturbating several times a day. I remembered the vibrator and the dildos I’d found and knew she still masturbated several times a day. Maybe she was addicted to it! Maybe she wanted to know my habits in order to save me from becoming an addict too!
l was still kneeling in front of the toilet when Stephie returned and helped me to my feet. “Maybe you’re not that far gone, Howie.”
“I guess I’m addicted sis,” I said with a rush as I staggered into the living room.
“Addicted? You mean you take drugs? What kind? How often?”
“What?” I stammered as I sank down onto the couch.
“Come on Howie, this is serious. What kind of drugs are you on? Are you stealing them from Mom? Is that why you ran away?
“I—I—I’m not stealing any drugs from Mom!”
“Where are you getting them? Oh that’s a stupid question. You can get them on any street corner.”
“Steph … I AM NOT TAKING ANY DAMN DRUGS!”
“But—but you said you were addicted!”
“You just told me you were addicted, Howie. What else could that mean?”
“Addicted?” And then almost to myself, “Addicted?” It hit me like a fist to the jaw. “Oh …”
“Well?” Stephie said and waited.
I was already dying of embarrassment, and in spite of myself I had a treacherous erection that Stephie might not have seen yet, but would as soon as I opened my mouth again.
“Come on, Howie, out with it. What are you addicted too?”
“What?” As understanding overtook my half-inebriated sister, her eyes dropped to my lap, and almost in sync with hers my eyes dropped to the bulge in my pants.
Damned if my pet monster didn’t twitch to make certain she saw him. There was a long moment of silence between us. I remember hearing the grandfather clock ticking in the quiet.
“I’m sorry,” Stephie whispered, “I didn’t mean to stare…”
“I can’t … I can’t help it Stephie!” I said as my voice cracked. “I’m cursed!”
“Aw Kiddo,” Stephie said, flopping down next to me on the couch, “You’re not cursed. Someday some girl is going to die of pleasure when you introduce that … thing to her. I was kind of teasing you about masturbation. Everyone does it. Really! Some more than others, but everyone does it. It’s part of growing up.
“You mean it?” I groaned unhappily.
Stephie gave me a squeeze. “You know what I said about my breasts … I guess I was always insecure about them growing up. I take your staring as a compliment. And if you must know, I appreciate the attention.”
I swallowed. “I think they’re… really nice.”
She laughed. “Thanks! I guess I haven’t gotten too many complaints. Have you ever actually seen a pair of boobies in real life? Of course not, I forget, you’re only 18. Do you wanna have a look? I mean, up close and personal?”
I managed to nod “Yes”
Stephie grinned real big and pulled her t-shirt off over her head. Her breasts were contained in a flimsy lacey white bra. I couldn’t believe this was actually happening. This HAD to be a dream. She reached behind her back and unsnapped her bra, letting it fall into her lap, and setting her beautiful breasts free.
“God… Stephie… They’re beautiful!” I blurted out.
“Well hd porno thank you!” she replied, wiggling her torso slightly and making her boobs jiggle and dance. They reminded me of a couple of ripe pears. The nipples were pink and erect and pointed slightly up and out. “I’m glad you like them!” She seemed genuinely pleased that I liked her tits. “Would you like to touch one?”
I nodded dumbly and held out my hand, cupping her left breast. It felt wonderful in my hand, heavier than I had expected and amazingly soft.
She laughed as my hand traversed the flash of her boob, and then said, “What?”
I wondered if she could read my mind, decided she couldn’t and said what I was thinking. “You could take off your skirt, I wouldn’t mind.”
I couldn’t believe my boldness, but Stephie just nodded and got up and wiggled out of her white skirt, leaving it in a pile on the floor. She was wearing high-cut turquoise panties, the ones that had been just on the edge of being visible in certain kinds of light all day. Her ass wiggled delightfully in them, and I could see a few stray strands of dark pubic hair.
“Okay Mister,” Stephie said. She was standing three-quarters naked in front of the futon couch. “Now I wanna see your goodies. Drop those pants, little brother!”
I was dying of embarrassment and boiling-over horniness. My hands shook, making it difficult to unsnap my jeans. Stephie giggled and moved her shoulders so that her boobs shook even more. “Let me tell you a little secret, Bro. It’s not how big it is that matters, just how you use it,” she said knowingly.
I lifted up my butt and scootched my jeans and Jockey shorts down around my ankles, letting my long-confined dick spring out like a jack-in-the-box.
“Oooh Kiddo! You’re looking mighty grown-up there!” Stephie flopped back down onto the futon. I jumped as her naked thigh pressed against mine.
“My, my, you’re not my little brother anymore! Not with a dick like that! And Howie if you know how to use it … oh man, look out world!”
I didn’t know what to say. Clear pre-come was leaking copiously out of the end of my rigid dick. I was sobering up more every minute. I doubt the same was true of Stephie. And she proved it with her next words.
“Okay” Stephie said. “This is sooo outrageous I know, but—but I’d love to watch you jerk off for me. I mean, you obviously need some release. I can’t bear seeing you go to bed like that!”
“Are you serious, Sis?”
“Yeah—yeah I’m serious, but then we go to bed. Um, I mean in our own separate beds. But Howie …You can cum on my boobs you want.” she added.
So I got up on my knees, straddling her lap with my dick just inches from my sisters’ gorgeous tits and started stroking myself, while she watched hungrily.
It was a good thing I’d already masturbated once that day, because I was able to last for more than four strokes.
“Oh that’s nice, Howie … nice … yeah … soooo nice!” Stephie intoned as I thought to rub my cock all over her boobs, lightly slapping each nipple in homage to the first pair of tits I’d ever encountered.
I didn’t last long at all. My body went rigid and my toes curled and my balls clenched and I squirted all over Stephie’s boobs. It was an incredibly intense climax, and it seemed to go on forever and ever. When I could think again, the first thing that occurred to me was the copious amount of semen I’d released. It was all over both her breasts, and all the way up onto her neck. For some reason I was afraid that Stephie would be mad at me; but she just grinned and slowly used my T-shirt to wipe the residue off of her breasts.
Then, as if nothing unusual had happened between us, she chirped, “Bedtime, Kiddo! Sweet dreams. And don’t forget to brush your teeth.” And with that, she sauntered into her bedroom and closed the door behind her.
When I woke up the following morning, a Sunday morning, Stephie was already out. This time I successfully managed to resist the urge to snoop in her room and check out the pornos. Stephie came home soon enough, and made me waffles for breakfast.
“Last night was a little weird, huh?” she asked me over the kitchen table.
“Sorry,” she said sheepishly, “I guess horny and drunk are kind of a bad combination. I’m sorry, Howie.”
“Actually,” I said quickly, “I enjoyed it.”
Stephie smiled and seemed to relax a bit. “I did too. But it was still weird. That’s not the kind of stuff brothers and sisters are supposed to do. But ….”
She left the ‘but’ hanging. My curiosity got the better of me and I asked, “But what, Steph?”
If you’re really horny, I’ve got a friend I can hook you up with.”
“Are you serious?”
“Heck yeah I’m serious Kiddo! Her name’s Candy, and she’s my age and she hasn’t had a boyfriend in six months. And she’s a serious pervert. There’s just one condition, okay?”
“I get to watch.”
While I thought that strange, even perverted, I agreed, for I wanted nothing more than to latina fuck tour porno get laid and shed my virginity. It didn’t really settle into my brain what Stephie’s request entailed. I just knew that what I’d heard was the best news I’d ever heard about anything.
A second announcement followed: It had much less significance to me but was important all the same. Steph had called our mother and told her my whereabouts, and what her plans for me were. No, not those plans, but one that our mother would find satisfactory and not put out a missing persons report for me.
And when I found out that Candy would be coming over for lunch and games my erection went to full throttle and stayed there much to Stephie’s amusement. In fact she asked me if I needed to ease my anxiety a little, I understood that to mean ‘Did I want to jerk off?’ I shook my head ‘No.’
We didn’t have lunch at Stephie’s apartment, but at a met up at a Vietnamese restaurant a couple blocks away. I had never had Vietnamese food before; whenever I’d gone out with Mom and Dad, it was to a Chinese restaurant or to the local diner.
While waiting for Candy to arrive, my sister announced blandly, “I told her you were my little brother, and I told her you’re a virgin,”
I started to protest. She quickly overrode me with, “Well its TRUE isn’t it? Anyway she’s never had a virgin, and the idea is a big turn-on for her. I didn’t tell her how old you are. If she asks just tell her you’re over eighteen. She might even believe you.”
Just about then, Candy walked up to our table. She was a slightly overweight redhead with frizzy hair and glasses. She had a tiny little nose ring, a “Daddy’s Little Girl” tattooed on one arm and a “Wouldn’t you like too?” on the other, and she had these really big boobs that were threatening to spill out the front of her skull-and-crossbones t-shirt. She was wearing a really tight black skirt that ended halfway up her thick thighs, and she had a big smile on her round face, and freckles.
“I’m so glad you came!” Stephie said, “I hope you’re hungry!”
“Oh I am,” Candy said, positively leering at me. When Steph introduced us, Candy gave me a big hug that squashed her big boobs against my chest. I already had an erection, and I was pretty sure she could feel it through her skirt, which made me both more self-conscious and hornier than I already was.
Stephie ordered something for me with noodles and beef and spices in it, and it was delicious, but I had a very hard time concentrating on the food because Candy had her hand on my thigh for the whole meal, and I thought my dick might actually bust the zipper of my pants. I don’t remember much of the conversation; it was mostly just girl-talk between Steph and Candy.
After we were all done with our soups, Steph turned to Candy and asked if she wanted to come back to our apartment for a while to ‘hang out’.
“Oh boy, do I ever!” was Candy’s response. So we walked back to Stephie’s place, me with a girl—actually a woman—on each arm, almost tripping over my own erection as we hurried back to the apartment.
“Do you know what I’m wearing under my skirt?” Candy asked me conversationally as we walked down the street.
Stephie giggled. I shook my head ‘No’.
“Why don’t you find out then?” She said taking my hand and guiding it up under her skirt; right there on the busy streets of Manhattan I cupped her ass. There were no panties under there, just warm, soft skin, acres of it. I must have gasped out loud because both the girls burst out laughing.
We made it up to Stephie’s apartment, and then Candy was all over me, kissing me with tongue, pushing me down onto the futon and straddling me, pulling my t-shirt off over my head. She stripped her own t-shirt off, and the tight black jogging bra that was holding her grapefruit-sized breasts in check. They popped out of their confines, jiggling and shaking with her every movement. The big pink nipples were pierced with thick steel rings.
“So do you want to see my pussy?” she asked me, dragging herself up and down the lump in the front of my pants.
“Um … yeah!”
“Have you ever seen a pussy before?” she asked me. I looked over at Stephie, who was watching us intently.
“No,” I replied, “I mean I’ve seen porn before. But not in real life.”
“Well then I’ll show you mine,” Candy said, “But you have to promise to kiss it for me.”
That was an easy one. “Ok” I said, “I promise.”
Candy hiked up her skirt around her waist, and then shrugged and eased it back down. I almost died right then thinking she’d changed her mind. I had gotten a glimpse of her totally shaven pussy.
“C’mon, get naked for me!” Candy chirped, and I did, with amazing speed. There was a moment of silence, with only the sound of the refrigerator in the kitchen to break the silence as both of them started at my erection.
Not to brag, because I’m not the biggest guy in school, but I do measure up at eight and a quarter inches, and am fairly thick. Joey Catrillo has me by at least two inches, but word is he’s a freak.
After starting at it for a long moment, Candy blinked twice and quickly removed her skirt then saw my expression and said, “Aw I wasn’t thinking. You figured I wasn’t going to let you kiss my puss didn’t ya?”
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