Exploiting an Opportunity Ch. 01

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Her little brother needs a sex tutor.
5.8k words
4.63
192.2k
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Part 1 of the 6 part series

Updated 06/08/2023
Created 10/28/2016
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S3lwyncd0g
S3lwyncd0g
1,752 Followers

These days people talk about men sexually exploiting women. But In my personal experience, it often goes both ways. My Mom is Joann but everyone calls her Jo. She was born in fifty eight and in her senior year of High School, got knocked up. I came along in the next year, 1977. Yeah the same year as Star Wars. So Mom and Dad named me Leia. My brother was born in 1981, guess what they named him? Yeah, Indy. Dad was a drinker and died in an accident while Mom was pregnant with their third child in 1984. Mom got the news and fell down the stairs causing a miscarriage.

Fast forward a bit. Mom got a job as a secretary for a lawyer and made good money for the time. Indy and I grew up alternately playing and fighting like most siblings. I was athletic and pretty, Indy was a bit shorter and more of a nerd. Indy graduated high school early and started taking college courses at 16. He was already in his senior year at State when he turned 18. I had just graduated but hadn't landed a job yet and still lived at home in 1999. I was in the habit of going for a morning swim in our pool before breakfast. Recently I had realized that due to the privacy fence and trees, no one could see the pool and had started swimming topless. I was aroused by the thrill and risk.

As usual for a Tuesday morning, Mom was out the door and well into her commute by seven and Indy never got up before nine or ten so at eight I felt pretty safe. I paused at the pool to do some stretches and pulled off my T-shirt before diving in and starting my laps. Thirty minutes later I climbed out and lay on a chaise to dry in the morning sun.

After a minute or two I realized that there was someone snoring closeby! I jumped up and grabbed my shirt as I looked around, then I saw him. Indy was passed out in the grass behind the roses. I dashed over and saw that he had thrown up, a lot. The reason was clear as well. An empty scotch bottle was still in his hand. He was wearing only a pair of gym shorts and one shoe. I was so angry that I forgot about my shirt and vented my rage on him. Then I got scared when he wouldn't wake up. I checked his airway and then dragged him over to the pool and dunked him in. Oh I wanted to drown him but I felt that that might be taking it a bit far. Indy sputtered and coughed and threw up a little more. Finally he came around and was able to stand on his own.

"What the fuck Leia?"

"What the fuck?" I raged, "What the fuck are you doing? You are passed out drunk at eight thirty in the morning! You're underage! God if Mom knew you'd be grounded for life! Do you wanna die like Dad? You've got some explaining to do so let's hear it! Spit it out! Tell me or I'll tell Mom."

"I dunno, do you wanna explain to Mom why you swim topless every morning and why you have three dildos in your sock drawer? Leave me alone."

"What the hell were you doing in my sock drawer?" I screamed.

"What do you think? Looking for drugs." he replied.

"Wait, what? Drugs? I don't do drugs dipshit."

"Yeah, so I gather. But I wouldn't know how to buy any so I thought there might be a chance you might have some, now that you're not competing anymore."

"You still haven't told me why you want drugs or got drunk." I reminded him.

"And I'm not gonna." he said and tried to climb out of the pool. Pissed I grabbed him and pulled him back in. We fought and flailed until I realized that he was serious and I reached down and grabbed him by the cock and held on.

"OW! Fuck Leia!"

"Then stop fighting me!"

"Okay! Okay!" Shit just let go!"

"Not until you start talking Indy."

"Okay, shit, there are these two girls that I tutor, they're both sophomores, and they've been flirting a bit all along. Yesterday they passed their final and I saw them in the student union and started to talk to them. You know just kinda 'Hi, how'd you do on finals,' and then asked the cuter one if she wanted to go out. And no shit Leia she looked at me and asked me if I was gay. And the second one said that was because if I was gay I could hang out at Zippers and stand a better chance of getting laid. Then they laughed."

"Oh fuck Indy, that's cruel..." I said. I could see the hurt in his eyes.

"And all day long I couldn't stop thinking about it. And the more I thought about it, the more depressed I became. And I just wanted the pain to go away for a while you know? So it was either drugs or booze and booze won."

"Indy, those girls were wrong! They had no right to talk to you like that. What's more, they don't know you like I do, and I think you're okay and I'm sure you will get laid sooner or later."

"Well maybe, but I'd rather it be sooner than later Leia. I'm so frustrated. Only a few guys in high school were laid before graduating, but this is college and there is sex everywhere and with everyone but a few of us losers."

"Hey! Don't talk like that! You're not a loser! You're just younger than everyone but the freshmen! Remember that you started at 16 and tested out of more classes than most and knock down 4.0 everytime! Now it's just been two years and you're a senior!"

"Yeah but I still haven't kissed a girl..." he said dejectedly. "And the only time I've seen tits for real was just now and I don't think it counts if it's your sister."

Shit I had forgotten that I was topless! I started to raise my hands to cover and then realized that it was too late to be modest. Oh well, fuck it.

"Yeah, well, sorry to be a disappointment. You deserve something bigger and better than these to oogle." I said looking away. If he was going to stare I didn't want to make him more uncomfortable.

"What? No Leia, they're, they're nice." He swallowed and closed his eyes for a second then went on. "D-do you think I-I could... maybe ...you know, t-touch them?"

Now to this day I still don't know what possessed me, but at that moment I felt so sorry for Indy and I heard myself say "Sure, why not, after all I grabbed your dick a couple of minutes ago... Fair's fair."

Indy touched me so gently that it surprised me. I honestly expected him to grab, squeeze and paw me roughly. But no, his touch was delicate and soft. He caressed my small breasts and lightly toyed with my erect nipples. In a deep dark part of my brain I didn't want him to stop. But he did.

Indy pulled away and turned around rather suddenly.

"T-thanks Leia... That was nice."

I saw he had both hands in front of his crotch and I knew he had become aroused and embarrassed. I felt so bad.

"Hey, it's okay, grab my towel and go inside. I'm gonna swim some more."

Indy climbed out and wrapped the towel around himself and fled inside. I stayed in the pool a little while longer, my mind in turmoil. At no time had I ever thought of my brother in a sexual way... Until just this moment. Now I wasn't really paying attention at the time, but his dick did feel, well, kinda big despite it being flaccid. I found myself wondering what it looked like, how big it might be erect...

"Dammit Leia! He's your brother!" I thought. "Yeah, but he's hurting. Screwing your brother is incest! Yeah but incest laws are to prevent inbreeding and birth defects, and they are mostly grounded in religious law and we aren't religious. I have no church to tell me what to do or not to do. And I'm on the pill so pregnancy is not a problem. So does this mean I want to fuck my little brother? Well, no, I just want to help him. You know, educate him so that he doesn't fumble and screw up his chances when he does date. But what about Mom? Hell, don't tell her, dipshit. Will Indy go along? Does he want to fuck me? Well don't tell him you're gonna fuck, just tell him you want to teach, no, tutor him. Yeah that's it! You're going to be his sex tutor!"

I stopped swimming and floated on my back. The morning sun felt nice and the water lapping at my breasts was suddenly noticeable... and kinda arousing. Our house had a full deck above the patio and sliding doors gave access from both my room and Indy's. Mom's, the master suite, was on the other side and though the deck wrapped around to it, her room did not have a view of the pool. As I floated I saw Indy watching me from his bedroom. I closed my eyes and pretended to not notice. Let the boy look. Then, after a few minutes I felt that strange stirring in the back of my mind. Something dark and yet erotic. My hands seemed to move on their own and I slipped my bikini bottom off. I swam a few laps nude and then went back to floating. Careful glances revealed that Indy was still watching. Good. Of course at that distance he couldn't see much. Just a naked girl with small tits and a tiny dark triangle between her legs.

After about twenty minutes of this I got out of the pool and, since Indy had taken my towel, I lay on the chaise and let the sun dry me off. The thought of educating my brother was... well, scary. And arousing too. Yes, I knew it was wrong according to society, yet I didn't really care.

After all, this was going to be done in secret and no one would ever know but the two of us. And it would be just temporary, just to get him confident and experienced enough to go on dates and get his own girlfriend, possibly his own lover. Someone he could touch, kiss and screw in the backseat...

It came as a total surprise. The mental image of Indy groping, kissing and then stripping and screwing a girl in the back of Mom's Volvo... It was arousing, erotic. Then the imagined lover changed and altered from some anonymous girl to... my god... ME! I realized with a start that I was masturbating! I glanced at Indy's window. The drapes were closed. Shit! Was that good or bad? Was I relieved that he didn't see this or disappointed? Fuck, what was happening to me? Why had I suddenly become obsessed with this?

I picked up my bikini, shirt, and the empty scotch bottle and went into the kitchen, dropping the bottle into the trash. I poured myself a glass of juice and saw that Mom had left some biscuits and sausage on the stove. I grabbed some and stood at the counter looking outside, but not really seeing anything. My mind was far away. I was about 90% committed to this plan but the 10% of doubt and fear still argued that I should quit before it was too late.

Okay so I've always been a bit of an extrovert and now that collegiate athletics was over, maybe I had been missing that. Maybe that was why I had been swimming topless and why this whole thing with Indy was such a weird turn on... Maybe. But why did I suddenly think of him in a sexual way? Why did I want him? And yes I had to admit, I did want him. I wanted sex. And I had no boyfriend at the moment that I would be willing to screw. And even though I was curious, I had not yet had a girlfriend as a lover. Lesbianism was kinda arousing but as yet unexplored. My dildos helped take the edge off when I was really needy but I truly wanted a man. I was no virgin, I had made love with three different guys over the last five years, but none of them were stellar performers. They all thought that they knew how to please a woman and of course none of them really did. Oh the sex was fun and enjoyable but not the awesome orgasmic experience I craved and fantasized about.

I set my glass on the counter and saw a reflection in the window of the oven. Indy was in the kitchen behind me.

"Want some juice?" I asked.

"N-no. What are you doing Leia?"

"Thinking... and eating. Why?" I didn't turn around. I was afraid of scaring him off.

"But you're naked."

"Uhm-hm."

"But..."

"So what? Mom's gone, we're alone, we're adults, and it's called an ass. Big deal. Everybody has one. Do you want to touch it?"

There was no reply. In a moment I heard him running upstairs. Damn.

I tossed my bikini and shirt into the laundry and walked into the living room. I lay on the sofa and idly channel surfed as I tried to develop a plan. Sure I could go into his room right now and tell him I was going to teach him to fuck. I doubted if that would work because he was still too weirded out by the incest stigma. I could continue to flash him for the next few days until he was ready to be teased and finally convince him to fuck me. But that would take days, maybe weeks and I wanted it sooner. So, I needed to get him both comfortable and aroused, okay.

I heard the postman dropping the mailbox lid on the front porch. I got up and walked to the window and watched as he walked away, then went and opened the door to get the mail. The feeling of excitement was surprisingly strong and... arousing. Standing in the open doorway naked. Cars drove past but no one slowed or crashed. Hell, from the street no one could see me well enough to tell I was nude. Closing the door I sorted the mail, tossing the junk into the wastebasket, the bills onto the hall table and took Indy's mail up to his room. I paused outside and considered just walking in and giving him the mail and a full frontal nude. Nah, that might be too much, too soon. Instead I knocked.

"Indy? Here's your mail."

When he opened the door I kept my body turned away from him.

"Thanks."

"You're welcome." I replied and went down the hall. I reached my room and closed the door. Only then did I hear him close his. So he had been watching me...

I had a plan. Now I assessed the risks. If we went out it had to be away from school where we were known. And then as the lessons progressed I would need to be certain we wouldn't get caught. We could do most of it at home while Mom was at work. Her steady 8 to 5 Monday through Friday job almost guaranteed we would have the house to ourselves. Wait, Mom had said something about taking some vacation time! When was that? I went back down to the kitchen to check the calendar. Nothing. Her computer! I ran back upstairs and went into her room. She kept her personal computer on a desk in the huge master bedroom. I turned it on and opened her calendar. There it was, good it was three weeks away. I had plenty of time.

As I closed the calendar I noticed a file on the desktop labeled "pics". Curious I clicked to open and it requested a password. Now I was intrigued. Why would Mom have a password protected file of pics? I tried her name, our address and several others without success. Then I tried Dad's name, Hamilton. The file opened and I got a shock. It was full of nudes. Not just porn, you know, nudes of unknown people, but this was nudes of people I knew and in many cases was related to! Fuck!

There were pics of Mom, her sister Shelly, Uncle Pete, Mrs. Bishop (Mom's best friend), and a few I didn't recognize.

As the shock wore off I realized that my family was probably full of incestuous relationships. Cool. that meant that I wasn't crazy or sick for wanting my brother. Mom probably used these pics to masturbate to. Other than Mrs. Bishop, everyone I recognized lived out of state. And since Mr. Bishop's picture wasn't included, I assumed he wasn't involved. There were some subfolders here that were numbered rather than named and they too were password protected. This would take too long to try to guess them now.. A problem for another day. I closed the file and turned off her PC before going into my room. Holy shit. What a morning! And it was only ten o'clock!

I went and showered in the large bathroom Indy and I shared, shaved my legs and labia for good measure and dried my hair. I am a brunette and at the time wore my hair rather short. A drop of perfume and some deodorant, then I stepped across the hall to my bedroom. I selected a pair of light blue bikini panties, no bra (hell at 32 A, I needed no support, I only wore bras to keep my nipples from printing) and a simple sundress also in a pale blue. I stepped into some flats and walked over to Indy's door and knocked.

"Indy? You got a second?"

"Sure, come in."

Indy was at his desk playing some computer game. He'd showered ahead of me and was dressed in his typical jeans, loafers and T-shirt.

"How do I look?" I asked and did a little spin.

"Uh, you look great Leia. Why?"

"Oh I'm going to brunch with a really cute guy and I wanted to look special for him because he is a special guy."

"Wow, he's a lucky guy Leia."

"Yeah, I hope he's not gonna keep me waiting. I'm starving!" I stepped forward and grabbed his arm. "So come on already!"

We managed to get a table at a nice little place Mom and I loved, Cicero's, on the canal. Indy was happy to put this morning behind us and we actually had a good time. We talked more than we had in years, well, if you don't count all the screaming we used to do. We talked about school and movies and music. And we laughed. God how we laughed! Indy was so funny! How had I missed that? Time passed without us noticing until I heard a familiar voice.

"Leia? Indy! What are you kids doing here?" Mom picked today to eat lunch at this place too!

"I'm..." and my brain froze. Was I dressed to sexy? Would she guess what I was up to? How could she?

"She got stood up by a friend and I came by on my way to Game Shoppe and saw her." Indy said saving the day.

"Wow, okay. Well may I join you? I was just going to get mine to-go but this will be nice."

Mom did join us and it was nice even if it kind of messed with my plans. Also I kept thinking about and glancing at Mom's boobs. After this morning, I was feeling a bit self conscious about my small breasts. See, Mom was a 36 D, and it was a warm day so she took off the cardigan she wore in the office and revealed her spaghetti strap shell top. Damn she looked good. No, she looked awesome. As I had from time to time, I found myself again wishing I had more of a busty shape. Of course that would have interfered with my athletics.

As we talked I caught Indy watching her boobs and trying to be discrete. Fortunately Mom never seemed to notice. After we finished, Mom headed back to her office and I took Indy for a stroll along the canal.

"You need to be careful ogling Mom like that Indy. What if she'd noticed?"

"Shit, sorry Leia. I -"

"Doesn't matter, just be careful. I'm not saying stop, just don't get caught. I don't blame you, she looked nice. Now do you know why I wanted to drag you out like this?" I asked.

"Because you feel sorry for me?"

"Well, I would be lying if I said I didn't feel sorry for you, but that's not why we are out today. I am about to make you an offer, little brother. And it's an offer you are going to accept."

"What if I don't like the offer?" he asked.

"Tough luck. Refusal will result in Mom learning about you getting blind drunk last night. And don't think Mom is unaware of my dildos, she gave me my first one a long time ago. My take on the situation is this, my little brother lacks experience with girls. A lack of experience often leads to blunders and mistakes. With girls, the mistakes you make can be critical ones. Relationship ending. Under no circumstances will I allow that to happen."

Then in my best Godfather Italian accent, "It would bring shame upon the family, this, we cannot allow."

Indy laughed. Good, get him relaxed before telling him the extent of my plan. We walked on.

"Now I speak from experience Indy. I've had some pretty bad dates and none of my true relationships have been successful. I may not be a guy, but I know what girls want. But we get bad info or rumor and hearsay and somehow accept it as truth. Mostly because we're all still young and awkward and just learning about our bodies and the opposite sex. Therefor I will undertake to educate you for your midterms and finals on The Female Body and Healthy Sexual Relationships."

Indy froze in mid step.

"Yes, I am going to be your tutor."

I walked over to the railing and leaned back against it. "Come here." Indy came over to stand beside me but I pulled him into an embrace. "Kiss me."

"What? Here?"

"Relax, no one knows we are related. We're just a guy and his girl. Now kiss me."

S3lwyncd0g
S3lwyncd0g
1,752 Followers
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