So, here we are. All characters involved in sexual behavior are 18 or older. This is a fictionalized story, based partially on personal experience. How much is real and how much is fantasy? I’m not telling! Enjoy.
*****
HARD LESSONS
It was 1984, and my big sister was moving back home!
It had been several years since Nancy and I lived under the same roof. She was four years older than I was, and had moved out of our childhood home immediately after graduating in 1980, having eloped with her high school sweetheart during their senior year.
Her husband John had enlisted in the Army, and after spending several years stationed in Washington state, he’d gotten orders for Germany. He had a choice: he could either spend two years in Germany without his family (they had a daughter by this time), or bring his family with him and do a three-year tour. They opted for him to spend two years overseas by himself.
In the meantime, Nancy and her infant daughter moved back in with our mom. At this time, I was 18, a senior in high school, and just a few months away from graduating. My older sister was seriously my favorite person in the world, and I was thrilled to have her back in my daily life.
Growing up, it was really important to me to stay in my big sister’s good graces. After our parents had divorced, mom worked multiple jobs to make ends meet, and Nancy became the de facto guardian of me and our baby sister when mom was working, and what she said was law.
Of bigger import to me, though, was the fact that Nancy and her friends were all stone-cold foxes! When I was 12, Nancy and her coven of lovelies were freshly 16, and these girls were all more wild than sweet; they were deliciously 18 when I was 14. I would do whatever it took to be included in their gatherings. Being amidst a group of sexy teenage girls was always a turn-on, to say the least, and I didn’t want to ruin it by being the annoying little brother. Though her friends had always treated me as a surrogate ‘kid brother’, I didn’t think of any of them is a sisterly way. I spent many solitary nights doing what teen boys do while fantasizing about each of Nancy’s friends, and, in truth, my big sis herself. My sister was a large part of my fantasies during my developmental years. In fact, my very first orgasm came from a wet dream I’d had about her!
Fear of rejection kept me from making a move on any of my sister’s friends; I thought I’d be seen as the kid brother forever.
An experience when I was 14 that let me see that wouldn’t always be the case. I was in the garage, working out with free weights when Nancy’s friend Kathy showed up. The garage door was up, and we frequently used that door to go in and out.
“Hey, Jim. You know, you’re looking good. Those weights are paying off for you!” Kathy said with a flirty smile as she walked into the garage.
I quickly racked the weights on the bench and sat up. I was shirtless, a sheen of sweat covering my torso. I’d been lifting daily since getting the weight set as a Christmas gift three years earlier, and had developed a toned, muscular body already. Top that with the dark suntan I had, turning my fair skin gold, and yeah, I guess I was looking pretty good. I was absolutely thrilled to hear it from Kathy!
“Hey! Kathy! Thanks! Yeah, and you…. you’re… uhh…you’re looking good, too! Good to see you! How’s it going?” Kathy was without a doubt my sister’s hottest friend, and probably the sexiest chick I’d ever seen in person. If I sounded a little over-eager, it’s because I was! Just being in Kathy’s presence, I tended to get really tongue-tied, and she knew it.
Nancy came into the garage to collect her friend. As they were walking into the house, I heard Kathy fake whisper to Nancy “I swear, if your brother was just a couple years older, I’d be headed to his room now, instead of yours!”
“Ewww! Shut up!” Nancy replied loudly.
“Have you seen your brother lately? He’s turning into a fox! I thought of licking the sweat off his chest just now,” Kathy said, not really whispering anymore. Looking back over her shoulder and seeing that I was eavesdropping, Kathy winked and blew me a kiss, then turned and pushed Nancy forward with a giggle.
“Stop! He’s my brother!” Nancy protested as they moved
“Which is why you shouldn’t be the one to lick his chest,” Kathy laughed. “But look at him sometime as though he’s not your little brother, and then tell me it wouldn’t be ‘drop your knickers’ time! You can’t blame me for grooving on a sexy guy!”
Wow! I couldn’t believe what I’d heard. I knew I’d be imagining Kathy’s wink and kiss later that night. Unfortunately for me, I was still pretty shy, and had no idea how to hit on a girl my own age, let alone the goddess-like best friend of my hot sis.
A couple days later, I was working out in the garage again. I got thirsty and went into the kitchen for a glass of water. Nancy was in the kitchen, getting some dinner ready. She looked at me when I came in, and her gaze etimesgut escort lingered a bit on my shirtless, sweaty form.
“You really shouldn’t walk around all the time like that, you know,” she said, seeming strangely uncomfortable to bring up the topic.
“Walk around like what?” I asked, truly confused.
“Well, I mean, would it kill you to put a shirt on?” she asked.
“I’m working out,” I protested. “It’s like 100 degrees in the garage.”
“Well, you’re not in the garage now, are you?” my big sister said, turning away from me, trying to find something to do with her hands.
“Whatever,” I replied, rolling my eyes. And then: “At least Kathy doesn’t seem to mind it!”
Nancy spun toward me, sputtering. “Wh-what do you mean? What about Kathy?”
“I heard her the other day as you two were leaving the garage. Don’t spaz that your friend thinks I’m sexy. I’ve had to put up with the same shit from my friends about you for years!”
With that, I drained my glass and went back to the garage, proud that I’d just left my big sis speechless. That was a first!
*****
Nancy was a seriously cool older sister, even if she wasn’t always the best role model. She taught me to smoke and shoplift – I think I was about 11 or 12 at the time! In her senior year, she got really serious with John, who she eventually married. He tamed her wild ways; he was a jock who was too concerned about his health to drink or smoke, and would definitely never smoke weed, habits Nancy had regularly up until then.
Nancy had never lacked for attention from guys. She was tall and curvy (think old-school voluptuous), with thick, wavy brown hair and gorgeous blue eyes. She and I both get our looks from our father, where our baby sister takes after our mom. Nancy always had a boyfriend or two spending money on her, so she never even had to get a job. I, on the other hand, started work young. I liked having money to spend, and learned early to work for what I wanted. I knew I’d never be given a car, so I started putting money away when I got a paper route when I was 12.
Over a few years, I managed to build a savings account of a couple thousand dollars, which led to my big sister hitting me up for money from time to time.
“Hey, little brother,” she’d cajole. “You got $5 I can borrow?”
“Borrow?” I’d reply. “You understand that ‘borrowing’ means you’d pay it back, right? How would you do that, Miss ‘I don’t need a job’? Your boyfriend going to give you money to give your little brother? I think what you’re really asking for is free money, and there ain’t nothing in this world for free!”
So began an innocent game between us. Truth, I adored my big sister, and would gladly give her what I could afford, but it was also fun to make her earn the money. Typically, I’d make her do a dare, something like eating bizarre combinations of food. A big bowl of yogurt topped with yellow mustard and 5 apple seeds was one of my personal favorites I made her do.
After completing a dare and being given the money, she’d always say the same thing: “I fucking hate you, baby brother!”
To which I’d reply, “Betcha don’t. Not even a little!” Then I’d throw some variation of a line our father was fond of using: “Life is full of hard lessons!”
Though Nancy wouldn’t admit it, I think she enjoyed this little game of ours, too.
***
So, Nancy settled her and her daughter into her old room, which had been my room since she’d moved out, as it was the biggest in the house, aside from mom’s master bedroom. I only grumbled a bit, mostly good-naturedly, about being demoted back to my old room.
Old habits die hard, though, and one day, coming out of the shower with a towel wrapped around my waist, I walked into the wrong bedroom out of habit. I opened the door and was greeted by the sight of my sexy, 22-year-old sister, stark naked on the bed, knees raised and legs spread, one hand between her legs, the other tugging on a very hard nipple! Her eyes closed, she was unaware of my presence until she heard me exclaim “Fuck!”
Nancy’s eyes flew open and she sat up on the bed. “What the hell!?” she exclaimed as she tried to cover her tits and bush. Not an easy task, as my sister has curves for days. Seriously, she is a woman and a half in every direction, and even the very best imaginings of my horny mind never came anywhere close to how gorgeous her nude body actually was.
“Sorry! Sorry!” I said as I backpedaled, pulling her door shut. “Wrong room!” I hollered through the door. “So, so sorry!”
I went to my room, my heart racing in excitement. I was seriously torn. On one hand, I felt bad walking in on her; on the other, I wanted to go back and see more.
“Hey, brother,” I heard Nancy’s voice as she knocked on the door. “You ok?”
“Come on in,” I answered. She stepped in, the short bathrobe wrapped around her leaving most of her thighs exposed, and closed the door behind her.
“I’m really sorry, etimesgut escort bayan Nancy. That’s been my room for so long, it was just force of hab…”
Nancy shushed me. “I should’ve made sure to lock the door. It’s ok, but please don’t tell mom about this, ok? I’d die of embarrassment!”
“Tell mom? Oh, yeah. I’d love that conversation ‘Hey, mom, I got an unexpected hard-on today. You wanna know why?'” I laughed.
Nancy’s jaw dropped. “You did NOT just say that!” she laughed with me.
“I mean, I always knew there was a reason you’re my favorite sister, but damn!” I teased her. “I guess I’ll just have to tell Brian and Bill they were right about you being a fox all along…”
“I fucking hate you, baby brother,” Nancy was laughing hard now, tears in her eyes.
“Betcha don’t. Not even a little,” I replied with a smirk. “Besides, what was that you were doing in there, anywhere? I’m not familiar with what that might’ve been.”
“Knock it off. You know damn well. Everybody does it. I mean, you do too… right?” Nancy looked as though she wasn’t sure if I was serious or not.
“Me? Do such a thing as that? Especially growing up around you and your tribe of wet dreams on legs? I have no idea what you must mean.”
“Ewww,” Nancy said. “I don’t want to hear about you beating your meat to my friends!”
“Oh, so you only want to hear about me beating my meat to you? OK, I’ll be sure to let you know the next time I do. Might not be too long, either. You still smell like sex, you know! It’s kind of getting to me.”
Nancy grabbed my pillow from my bed and swung it at my head.
“Growing up to be quite the pervert, aren’t you?”
“You know, I’ve always aspired to grow up to be a dirty old man!” I said, trying and failing to cock one eyebrow.
Nancy threw the pillow. I caught it and threw it at her back as she slipped from the room, looking back with a small, secretive smile before pulling the door closed.
It was good to have my big sis back. Kind of different, too, in a very interesting way.
*****
Later that night, I had an incredible orgasm, stroking my cock as I replayed the vision of my big sister rubbing her pussy and fondling her tit. In my mind, the scenario played out differently….
“Fuck!” Nancy’s eyes flew open and she sat up on the bed. “What the hell!?” she exclaimed, not trying to cover herself, staring right at me as I stared at her, lust written all over my face.
“Getting a good eyeful?” I imagined Nancy saying. “Well, you may as well get closer so you can see all my goodies.” Her eyes went to my crotch, and she could see the outline of my hard cock through my shorts. “And get those pants off. If you’re going to watch me, I want to watch you, too!”
And there my sexy older sister and I were, she laying back on her bed, me standing between her spread legs, each of us pleasuring ourselves as we gazed intently into each other’s eyes….
I squeezed hard around the base of my cock, trying to hold off my orgasm so long that when I came, the first jet shot over my stomach and chest, hitting me squarely in the face. I resumed stroking myself hard and fast, my cock continuing to spasm and shoot, leaving me covered from cockhead to lips in thick ropes of hot, sticky cum. I lay back, sated and happy, not thinking too much about the taboo nature of the fantasy that had brought me such ecstasy. I mean, I couldn’t be held responsible for what I see when my eyes are closed, right?
*****
My days were pretty busy. Though I only had a half-day of school (I only needed two classes to graduate, but the school required a minimum enrollment of 4 hours a day), I also worked at least 30 hours a week, getting off work usually around 10 pm. I’d then go to the 24-hour Nautilus gym where I had a membership, and would work out until midnight before going home for some sleep. Add to that my steady girl, a beautiful blonde exchange student from Finland named Katariina, and yeah… I was usually on the run.
*****
One night, Nancy was in the living room, the TV on low so as not to disturb anyone sleeping.
“Hey, little brother,” I heard the singsong tone she used when she needed money.
“Hey, big sis, how’s it going?”
“Not bad. But can I maybe borrow $25? John sent us a check, but the mail takes forever, and it’s not here yet.”
“Borrow?” I started, but Nancy cut me off.
“I do have money coming, and I’ll totally pay you back, but I need to get diapers and some other things.”
“Oh, that’s too bad,” I said, “because I just realized how much I miss making you do dares.”
“Well, that would work, too,” Nancy said. “Honestly, money is tighter than we thought, with us not living together. I looked into getting a job, but the child care for an infant would cost more than it’s worth.”
“That’s a shame,” I started. My mind was turning with possibility. “I can help you with the money, but that’s kind of a lot. I’d need escort etimesgut to come up with a really good dare.”
“I haven’t eaten anything gross in a long time,” Nancy giggled. “It might be fun.”
“Oh, that? That was kid stuff, sis. We’re beyond that now, what with being grown up. That just wouldn’t be entertaining enough for me, I’m afraid.”
Nancy’s eyes narrowed. “What exactly is it you want me to do?”
“Come to the garage,” I instruct. I extend my hand to help her up. Nancy takes my hand and stands, and we walk to the garage, neither of us letting go of the other.
“You know tomorrow’s trash day,” I begin, “and I haven’t taken the cans to the curb yet.”
“I could do that,” Nancy said eagerly. Did she think doing my chores would score her the cash? Silly girl. I’m not paying her an allowance.
“Yeah, but that’s not very entertaining, unless….”
“Unless what?” she asked suspiciously.
“Unless you did it wearing only your bra and panties,” I answered.
“You fucking pervert!” Nancy exclaimed, her eyes wide and mouth open in surprise.
“Maybe so, but I’m a pervert who doesn’t need extra cash,” I responded with a shrug. “I mean, it’s three trash cans. I can get them to the street myself in under 2 minutes, and I’ll still have money to spend on dates this weekend. It’s ok if you don’t want the money.”
I stood there silently, watching Nancy as she weighed her options. “Just my bra and panties? No tricks? Take the cans to the curb and that’s it?”
“That’s it. It’s almost 1 a.m. and it looks like the entire neighborhood is asleep. All the houses are dark. No one will ever know about it.”
“You’ll know,” she said accusingly.
“Well, of course I’ll know. If I didn’t know, it wouldn’t be entertaining for me, now, would it?” I said innocently.
“And you’ll tell all your friends about it, too. I’m not stupid, baby brother.”
“You really think I want anybody knowing I’d do something like this? If you do the dare, it’s strictly between us, sis.”
“Well, like…. are you going to watch me?” Nancy asked.
“Oh, big sis, you can count on it! In fact, I’m looking forward to it. I don’t know why I didn’t think of this years ago!”
Nancy shook her head in disbelief. “You really are a little pervert,” but she didn’t really look put out about it.
She was wearing a t-shirt which, while not really tight, did cling deliciously to her full breasts. I swear, no one would ever loan my sister a sweater for fear she’d stretch it out too much in the chest. Up and off, she peeled the shirt over her head and laid it on my weight bench, exposing a lacy pink half bra that barely contained her full breasts. Then quickly, she unsnapped and unzipped her jeans shorts and pulled them down to her ankles before quickly stepping out of them. She bent to pick the shorts up, inadvertently giving me a beautiful view of her tits, almost spilling out of her bra as she was bent over.
Damn, she had a dynamite body. Without a word, Nancy went around the corner of the garage. I heard galvanized metal scraping on the concrete as she grabbed the first can.
It was maybe 60 feet from the cans to the curb, and Nancy moved quickly, maybe afraid that someone would see her, maybe just not wanting me to have the chance to ogle her for too long.
Quick or not, seeing my sexy sister outdoors in her underwear affected me immediately. My cock was stirring in my athletic shorts, and I couldn’t resist giving it a quick rub as her back was turned. I watched Nancy every step of the way to the curb. Her pink panties tightly hugged her heart-shaped ass, which jiggled just a bit, but swayed beautifully as she lugged the trash can.
She placed the can on on the street, then turned to come back for the next. Her breasts bounced…. oh my fricking god, I could look at my sister’s tits for days and not get bored… and I’d probably stay hard the entire time, too!
She got the next can, but seemed to not be in as big a hurry this time. She lifted it easily, and turned to watch me watch her at her task. I smiled and stared pointedly at her tits until she passed me, then watched her shake her ass for me the rest of the way to the street.
“You’re unbelievable, you know that?” she asked as she passed me to pick up the last can. “Watching your own sister do your chores in her underwear. You’re a total pervert!”
“I guess I am. More than I even knew,” I answered honestly. “I really am enjoying this, you know. Your are absolutely gorgeous, Nancy. Totally worth the money.”
She placed the last can on the curb, turned to me and said, “I’m glad I’m not a pervert like you” as she reached around behind her back and undid her bra. Sliding it off her shoulders, she stood topless, facing me, then turned in a 360-degree circle, arms overhead in the ‘Victory’ pose, before walking casually back to the garage. I could see her nipples were hard. I didn’t know if that was their normal state, or if she was simply aroused. My sister had just flashed her tits to me and anyone else who might be up at this hour!
Back in the garage, Nancy slipped her bra back on, much to my dismay, then put on her shorts and shirt again. “Well, enough of that. Dare completed,” she said.
“I may be a pervert, but I’m also a man of my word,” I told Nancy. “I hope you can respect that, at least.”