Bdsm Sex Stories

by Olga Menson

  Every now and then over the next two years she'd come and ask me a similar question, or about why a given boy didn't like her the way she liked him. She had some seriously bad luck in that she'd fall for boys who were unavailable for a variety of reasons, but even when I told her that a boy probably did like her, she'd be too nervous to approach him or even respond if he started talking to her.

  I ended up holding her a lot while she cried when these boys she liked broke her heart by accident by going out with other girls. I felt bad for her, but I also knew that her situation wasn't that unusual, really. I told her what I thought was the truth: High School would end. College would be better. Wait, you'll see.

  I mean, it was true for me so it would have to be true for her, right?`

  ---

  Two Years Later

  ---

  Time passed. Irwin and I graduated. He got a football scholarship to the local city college. I walked on as safety again, but I was mostly a backup. We were in college. The professors mostly treated us like adults, the classes were more interesting, the girls were exponentially hotter, and things were generally looking up.

  Irwin surprised everyone and went pre-law, although he confessed that the humanities interested him more, his major kept his dad off of his back. I pursued being an athletic trainer for college sports, which in and of itself was no joke and would require a master's degree if I wanted to get anywhere with it. Trina followed Irwin, but the college also had solid biology and art programs, which was what she wanted to pursue. They were also getting more serious, which I think surprised both of them.

  Irwin and Trina lived on campus, but I needed to save money so I lived at home. It was kind of a pain but was common, and my parents gave me plenty of privacy and never bothered me when I came home stoned at 4 am. I got a job doing all kinds of stuff at the university gym, and the money I saved by not needing to pay rent allowed me to go on trips with a variety of attractive women for pretty much the entire summer after freshman year. Oh yeah, I was even more successful in college, where my laid-back attitude and complete lack of aggressive masculinity played well with mature young women who were tired of being treated like objects or something you put nice behavior in and expected sex out of.

  In fact, Trina had started calling me a slut and while Irwin defended me (as a good bestie should) he privately asked me if I was ever going to actually date anyone. Well, I'd tell him, it's not like I'm lying to these girls. I'd always explain exactly what kind of relationship we'd have: it would be fun, we'd go to interesting places, we'd have sex and she'd have orgasms. Besides, I didn't really have any emotional connection with any of them beyond friendship.

  My entire first year was a bit of a blur, being busy or getting busy most of the time. The summer was also pretty busy. I was either working for cash or spending that cash on trips with various girls. At the start of my sophomore year in college I was starting to tire out a bit. Constantly being out late, playing football (even as a second stringer) and working was running me ragged. I finally decided I had to quit football. I was doing it for fun and it wasn't anymore, plus I had a minor ankle injury that I was worried might impact other areas of my life. Fall break found me doing something that I rarely did: staying at home and resting.

  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.