The Tackle

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Jamie was over the moon. It wasn't like I meant to ignore her, but I do have to admit that I had seen a lot less of her since college started. And while I could keep my hoe-ing secret from Mom and Dad, Jamie didn't approve. I explained that I wasn't taking advantage of anyone or lying or cheating, but she'd just narrow her eyes and shake her head. I really didn't like that I might be disappointing her. That was really the first time that my lifestyle haunted me at all. I made the decision that I would start spending more spare time with her, starting with this break. I loved her and she still looked up to me. I didn't want her to start to resent me.

In any case, we still got along fine. She was a senior in high school now, taking college-level courses. We had an hours-long conversation and got each other caught up on our lives. I told her about Irwin's success on the field (she liked him too but in a second big brother kind of way), Trina's research opportunities and painting-shows (Jamie really looked up to her), and my grades, which were actually pretty great.

I was sure to tell her that I still used her study techniques and that the base of knowledge that she helped me establish had made my courses much easier. This seemed to take the sting out of me not being around much last summer due to my, uh, activities.

She told me about her group. Stevie and Greg had hooked up, which I agreed was excellent news. Julian was following in my footsteps and seemed to have the goal of sleeping with every boy and girl in the Art Club. I shook my head disapprovingly but privately cheered him in his quest. They were all still very close friends and played D&D together. A girl named Ellie had joined their crew this year and they had become fast friends. Ellie was also pretty awkward and was a good source of moral support for her with regards to romantic troubles. I noted that Jamie said that she was cute for future reference but even I was a little bit loathe to try to seduce my sisters best friend.

After we got caught up, I took her out to dinner. I decided that I'd spend the money that I usually spent on being a degenerate on Jamie this break, both to assuage my guilt and maybe boost her self-esteem a little. I really did love hanging out with her and showing it more couldn't help. It was more or less a date, sort of. In the back of my mind, I was thinking that if she got used to interacting with men in social situations then she might have more luck. At this point, I was cheering for my sister to find a boy that she liked and have a great first sexual experience but I was conflicted about the idea of anyone, even a generally good person, taking her virginity. I wrote that feeling off as just being a good protective big brother, but I don't think that covered it.

I think it was jealousy.

We went to a local steakhouse, the sort of place that isn't too expensive, but that's still classy enough to turn down the lights at night and light some candles. We didn't dress up or anything, I really wanted this to be casual and relaxed. It was good to be with a girl I felt an emotional connection to, and I wanted to continue the same sort of easy conversation that we had earlier that day. She was smiling when the server seated us.

"Wow. I don't think I've been here without Mom and Dad. It's ...different with you."

"Well," I philosophized, "You can swear as much as you fucking want to. And get me to tell you stories that I'd never talk about in front of the parents. Oh, and I might sneak you some wine if you're good, Tiny."

She laughed, playing along.

"Hmm. I don't know. You have something of a reputation, dear brother. You might just be getting me drunk to take advantage of me. Many of my peers have remarked that my elder sibling was 'totally fuckable, but a complete slut'."

I almost spit out my water. I'd never heard her talk like that before. It was equally shocking and hilarious. I managed to keep it together enough to respond with mock seriousness.

"Please don't slut-shame me. I'm expressing my natural tendencies in an ethical fashion."

She rolled her eyes dramatically, but then her mouth turned down into a small frown. It was the look she had when she was sad but trying not to show it. I paid attention.

"Seriously. Why do you...do that? I mean, go out with so many girls. Or just sleep with them. Are they like challenges to overcome and when you're done with them you put your trophy on the shelf and forget about it?"

I was taken aback by this. I knew men who thought like that. I never did though. I barely thought about consquences at all. Maybe that was the problem. I decided that now was as good a time as any for transparency.

"No. I'd never do that. I've sincerely enjoyed being with every girl that I've dated. I'm friends with most of them. And it's not like I just jump to a new girl's bed every time I get horny. I have, uh, 'regulars'. I guess, to answer your question, I do it because I have needs and desires like anyone else. And..."

I trailed off, unsure about going deeper.

"And?" she said, suddenly very interested.

I sighed.

"And, I don't feel anything for them beyond friendship. What I do feel is real, and some of them are among the people I trust the most, but there's nothing deeper. I tried to date women without that spark but I end up feeling a lot worse than if we kept it light and fun because I would be deceiving at least them and maybe myself. And it ends badly."

At that point, the server came back and broke up the heavy mood. Thank god. I ordered the ribeye and she got the prime rib. I raised my eyebrows but didn't complain. She smirked at me afterward. Was this revenge for what she saw as my bad behavior? What she said next made me think that it was. Well, it just made me think in general.

She looked away, face getting a bit melancholy.

"I know you aren't vain or full of yourself, but maybe it might help if you weren't so humble. Have you ever considered that girls...women too I guess, might see you as something other than a one night stand? That they see a very kind, generous, loving person who also happens to be hot? And maybe you aren't lying, but some of them go out with you thinking or hoping that maybe they will be the one that you'll feel something for? I know you aren't really to blame but...I can't help but think you have some responsibility. I know you've broken some hearts. Once I had a drunk blonde girl yell at me at a party. I had no idea who she was but apparently she didn't even warrant a second booty call. I yelled back at her until she burst into tears. Then I ended up talking her down outside. She just kept asking me what was wrong with her that you didn't love her. It was so sad."

Holy shit. I've never claimed to be a smart person. I'm proud of the grades I get in my program because it's difficult, but I get there through work, not naturally. It had honestly never even occurred to me that the girls that I slept with might see me as something more than I see them as. I was honest, right? I never lied or cheated. I always behaved ethically.

Then why did I feel so awful? Dammit.

"The girl was Amy. I remember that she looked a little like you, but not as pretty. I got some drunken calls and texts from her that were...pretty emotional. I just wrote her off as being crazy. I never meant to hurt her. I'm sorry."

I don't know who I was apologizing to. Amy? Jamie? Both of them at the same time? And wait, did I just admit that Amy looked like my sister but not as attractive? Amy was, for the record, extremely hot. Fuck. Well, hopefully, she'd forget about that.

Jamie reached out and took my hand, her eyes understanding.

"I'm not trying to make you feel bad, I swear. I just know you is all. If one of your partners did something extreme to hurt themselves you'd never forgive yourself. Hell, if Amy walked in here and shot you then you'd feel guilty that she went to jail. That's who you are."

I laughed at the image, as dark as it was. Jamie laughed too. I took this as an opportunity to lighten things up a little as well.

"Ok. Well, here is my proposal. Tonight will be a learning experience. For both of us. This is now officially a date."

Her eyes got huge and I tried not to laugh. I continued.

"What I mean is, we'll do some roleplaying. We'll pretend to be on a first date. I'll be on my best behavior, trying to get to know you as a person rather than just try to jump in the sack with you. I'll make conversation and won't be slutty. And you can practice being out with a man and flirting. You always worry about making mistakes but you know I don't judge so you can be yourself and relax. Win-win."

She reached over, grabbed my wine and took a big sip, then set it down.

"All right," she said softly, "but you have to really act like you're my date. And tell me how I did at the end of the night. And be honest."

"Agreed," I said, not even remotely considering the implications of any part of what Jamie had just said.

She squeezed my hand. I suddenly realized that we had been holding hands for a few minutes now. It just seemed right and natural. After what I'd just said I squeezed back. Had to keep up appearances, and this seemed romantic without being overtly sexual in nature. That's what I told myself, anyway.

The dinner passed. The food was good, the company better. She was flirtatious in a way that I'd never seen before. She was witty, of course, so she could complement and double-entendre as well as anyone, and she found excuses to touch me with her hand or rub her foot against my leg. Every now and then I said something challenging. Nothing major. I'd be very direct with a question or flirt right back at her. These were things that I knew from experience made her freeze up, or feel awkward. She did a pretty good job. Sometimes she would get a look like a deer in headlights for a moment and then steal some of my wine before answering.

To be honest, she stole a lot of my wine. As the evening went on she got bolder. Nothing too serious but by the time I paid the check her hand was on my knee more often than not and she was giving me looks that I could only describe as 'bedroom eyes'. I realized that she had slipped into the role of the pursuer and because I was trying not to be overly forward I had become 'hard to get'. It was an interesting role reversal and I found it enticing.

Maybe enticing isn't the right word. Maybe arousing is.

Driving her home was an adventure. I began to get actively worried that she was going to try...something. I wasn't sure exactly what but I knew that I couldn't let this go too far, especially after just making a big deal about trying not to sleep around. And that's beside the whole point of her being my little sister.

How was it an adventure, you ask? Well, her hand didn't leave my knee the whole way home. I moved it off, shifted around, but all that happened was that it moved up to my thigh. I was worried if I resisted any more she would end up giving me a hand job. And the looks she was shooting me were smoldering. If I would have been with someone else there would have been no doubt whatsoever that we would be fucking later.

When we got home I opened her door for her, and thankfully, things defused a bit when she released her loud, delightfully nerdy laugh.

"Oh my god that was so much fun. I didn't freak you out too much, did I? I...I just got really into it. It was so fun just being sexy and...and watching a man react to it how I wanted him to. And you were trying so hard to be on your best behavior so you were a little nervous and that made me feel better about feeling nervous."

It all rushed out of her and I felt relieved. She was just really into the whole scenario, so my idea was as much a success for her as it was good practice for me being a little more restrained. Great. But she went on.

"So," she said more hesitantly, "How did I do? You promised to tell me, remember? Be honest, even if it hurts a little. I...I know that you care about me and just want me to do well so criticism is ok."

Well, this I could do. I was glad I could be both honest and positive.

"Uh, you were amazing. I was struggling to be on my best behavior. You were, without a doubt, the most seductive girl that I've ever been on a date with. The way you were talking and touching me drove me wild. I was honestly worried about what would happen when we got home. I only have so much willpower."

Her face and changed, going from light to serious. I could tell, however, that it was because she was touched by my words rather than offended or depressed by them. I paused for a moment, then had another thought. Any sensible person would have kept it to themselves. I guess I had a lot of wine too.

"Oh, and of course neither of us really dressed up for a date. But your body in jeans and a sweatshirt is way more hot than any other girl I've been with in the skimpiest slinky dress."

Her face got even more serious and took on an odd cast like she had just seen something surprising. I realized immediately that I had gone too far by commenting on how amazing her body was, but I couldn't take it back. Not without hurting her or lying.

So I've been avoiding talking about this because it forces me to examine what I've repressed for years. Jamie...had changed.

Hey, we all do. Puberty, right? It turns out that Jamie was a late bloomer. I told you earlier that she was a hottie in her sophomore year. And she was, just petite and slender. She was still petite, but no-one who looked at her would think "slender" anymore.

The phrase that they would use, the one that I had overheard other men use, would be "extremely fuckable". A nicer way to say it would be voluptuous. She was about the same height but she'd let her hair grow longer. Her glasses were new but just as fashionable. Her makeup skills were even better. While it was simple that night she could easily go from anywhere between "perfect contour" to "sexy goth". But the stuff out of her control was what had really changed.

Her hips had widened out and her ass had grown a little and taken on the shape of a perfect upside-down heart. It wasn't flat, either, but flared out into something round that would fit into the hand nicely. Her waist had not grown, giving her an amazing hourglass. And to top it off (literally) her bust had increased. Significantly. I'm sure it was "only" a C-cup, but on her petite frame her firm breasts pushed at any material and it was clear that there was no sag, either.

I didn't just feel bad because I had quite obviously said that my little sister was hot as fuck, but also because she was still getting used to being so. She didn't like showing off her body in part because of how creepier older men had treated her. I didn't want to be added to the list of men she felt that she couldn't trust, nor did I want her to think that was the only way that I saw her.

She had a strange smile on her face. I'd never seen it before, which naturally worried me. Then she bit her lip, and I got really worried. I was too slow to prevent what happened next, or I just didn't want to. She reached up and put her hand on the side of my face. And then she leaned in and kissed me.

It wasn't chaste. It wasn't a sister kissing her brother. As soon as it started, I responded, and as soon as I did, I felt her tongue dart into my mouth. I instinctively reached out to hold her, thank god I grabbed her shoulders. Unfortunately, that seemed to remind her that she, too, had hands, and they weren't all that busy. Suddenly both of her hands were running through my hair, along my back, even pulling at my shirt to get underneath and touch my skin. This was something that was one of my personal turn-ons. Feeling a woman's hands on me when she clearly wants me drives me wild, even if she isn't touching anything particularly sensitive.

At this point, we were making out heavily, the kind of kissing where you aren't breathing enough and will have to stop soon to catch your breath before you go back in and escalate further. Jamie didn't wait for that. Suddenly, I felt her small hand grasping my now-hard cock right through my jeans. I stopped kissing her instinctively and said her name, like a moan. Like a lover.

"Jaimie, god..."

That seemed to wake her up. She released my cock, much to my disappointment, and stepped back. Her hand was on her mouth. She was clearly in shock. Oh fuck, I'd done it now...I was sure of it. But I wasn't really thinking clearly about the sequence of events.

"I...I'm sorry," she said, "I, uh, need to go..."

And then she turned and ran inside the house. I couldn't see her anymore but I knew that she ran up the stairs to her room and that I would find the door closed when I went after her.

Well, shit.

---

Irwin's Story

---

I didn't bother Jamie that night. I knew it would make things worse. The following morning I ran into her in the hall and tried to talk to her. I opened my mouth but she spoke over me, talking fast and clearly wanting to be nowhere near me.

"I can't right now please leave me alone ok I love you."

It was the way she spoke when she was anxious or feeling really low. Mom and Dad noticed the way she was and exchanged a look but they didn't say anything. The truth was that she was, in fact, smarter than all of us. I know that all of us worried about her but none of us wanted to make anything worse by pushing. She would, normally, eventually open up to someone. Most often me. I doubted she would be talking to anyone about this.

I felt that I'd triggered this so I couldn't do nothing. I had to save my sister. This was worse than Bryan, in that I couldn't just tackle it head on and hope for victory. I needed help, so I went to the person I knew who gave the best advice.

"Irwin dude, I know you were planning on leaving this afternoon but I need your help."

"Whoa, calm down, dude. I got time for you. The girl will understand if we have to leave a little later. What do you need?"

I stopped and thought about somewhere we could talk without family or friends.

"Hey, the college library will be empty, meet me there in a half hour. Oh, and, uh, come alone. Its kind of sensitive," I said kind of sheepishly. Irwin trusted Trina implicitly and I did for the most part, too. I was more worried about judgment than my secrets getting out.

We met and took the elevator up to the seventh floor, which was the sociology and psychology section. It was usually pretty quiet when class was in session but during the break it was dead. Irwin and I were the only ones there. We sat at one of the old wooden desks. Despite knowing we were alone, I talked low, almost a whisper. I was ashamed, but I knew that Irwin would, at least, know what to say to make me look at this rationally. I explained everything, watching his eyebrows rise in shock. I finished explaining the chain of events.

I stopped talking. Irwin sat back. I gave him time. I knew that he was thinking. He only thought fast on the field, otherwise, he took his time, considering things from all angles. It was reassuring to watch.

"Ok, bro. I think I know what you gotta do, but you're gonna need to listen to me really closely. Maybe you'll like it, probably not. I can't and won't tell you what the right path is, but maybe I can help you figure it out."

I took a deep breath.

"All right. I'm listening."

"Cool. You're gonna need to settle in because I have a story for you. The problem here is that you're thinking conventionally, and only from your perspective. Once I explain things to you I think you'll understand a little better. Oh, and no-one can know about what I'm going to tell you."

That surprised me. I thought I was doing all the shameful admissions today. Irwin began to speak and I didn't interrupt him. He was doing me a favor, after all.