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Girlfriends Younger Sister

Categories Fiction, Boy, Cheating, First Time

Authror: thehobbesian

Published: 31 May 2018

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I got nowhere with girls at school. Literally nowhere. Being academically accomplished in a non-academic school in Glasgow was not going to get any hearts racing. Especially in the late 80s and early 90s. Maybe now when being a geek or a nerd has a certain cache, but not then. And I imagine not now. So, I was surrounded by hot young girls, with a near permanent hardon, and only my hand for outlet.

Until 5th Year. By then most of the morons had cleared out, and the people that were left were the more academically minded. I discovered I could flirt and, I felt, reasonably well. Certainly, started getting on better with a few of the girls in my year. And the result? Nothing. Except for my right hand of course.

Thank fuck for University. Fresh start, even though I stayed at home for uni, and an environment that was much better suited to me. It took about a week.

There was this girl, Joanne or Joanna, I could never get it right even then. I spotted her in my philosophy class. Long dark hair, quite pretty but not stunning, and probably she didn’t think she was pretty at all. But what stood out, literally stood out. This girl was stacked. The first time I saw her she was wearing a tight pink sweater, and there they were, standing large firm and proud. Utterly magnificent.

Being me, I sat in the row behind her, and to one side. Close enough for a fantastic view, but not close enough to actually talk to her. Still no confidence. But when I saw her sitting outside the politics lecture hall, reading Thomas Hobbes’ Leviathan, I decided I had to make an attempt. Sitting down opposite, I waited a few moments before commenting on the book she was reading. Although Hobbes was a political writer, this was actually the text for the philosophy class and we quickly got to talking about the class and the text. She was shy, a little, but was happy to chat. More comfortable talking about the text, her shyness was more obvious when I moved the conversation on to more general topics, but she was clearly warming to me. And then her friend arrived and joined us. Gerladine. 5’ 5”, short mousy hair, blue eyes and a stunning smile. Slim, but not skinny, small breasts, especially compared to Joanne, great legs that were well developed from the exercise that generally comes from a private school education. And much more confident than her friend. She immediately joined in the conversation until a few minutes later when we all trooped into class.

I was trying to decide whether I should sit between the two girls, or if I should let Joanne sit in the middle so she could talk to her friend and I could talk to her. Geraldine settled the issue by letting me go first and then squeezing past her friend to sit next to me. Done deal. I finally had a girlfriend, and within a week we were fucking. I could have made this story about our first time, it was hers as well as mine, but to be honest it wasn’t worth writing about. I did, however, get better.

Geraldine also stayed at home, so opportunities to fuck didn’t come easily. My mum was pretty easy going, but not to that extent. Her parents were also great, and really welcomed me into their home, but again, there are limits. So, we had to manage when we could, an afternoon screw, a quicky (and quietly) when she was at mine and, in the case of extreme horn and no other option, a quick fuck outside my tutor’s office while I was waiting to go over an essay I had written.

But then, we caught a break. Her parents were going away for the weekend. Geraldine was going to be home alone for a couple of nights. Well, not exactly alone. Her 13-year-old sister Caroline was also going to be there. That, however, presented no problem for any of us. Caroline and I got on fine, she was mature for her age, tall at 5’9” so not much shorter than me, and all leg. The word coltish could not have a better object. But what she had in leg, she lacked in breasts. Small, but cute. And I had always been a breast man.

So, there I was. Friday evening in Geraldine’s house, looking forward to a couple of days of pretty solid sex. The only thing that stopped it being non-stop was that Geraldine had a weekend job in a local restaurant. She left at 7pm and didn’t get back until almost 2am. Still, Friday went great. Quick fuck before she went to work. Caroline left shortly after Geraldine to go stay over at a friend’s and I just hung out, watching TV and reading until Geraldine got back in the early morning. A more relaxed session before going to sleep, woke up hard and ready for more on the Saturday. And Saturday was pretty much non-stop. Even the return of her sister in the late morning didn’t make any noticeable difference. Nor did the couple of sarcastic comments she made about how much noise we were making. Sucks to be you kid.

I was all set for a repeat on Saturday night as Geraldine set off work. But this time, Caroline was not going to be staying with a friend. She was out playing tennis at the local club, but was due to be back shortly. Company for me I guess, while I waited for Geraldine to get back.

In truth, I had been very aware of Caroline from the moment I first saw her. Not my usual type, physically, but something about her caught my attention. I had tried not to show it, not around Geraldine, and certainly not around her parents. But a week or so earlier there had been a small incident that could so easily have gotten me into trouble.

Geraldine and I had been pretty tactile right from the beginning, and I had discovered that massaging her thighs, high up on her thighs, had a very obvious impact on her. Looking back on it now, it seems obvious that it would, but at the time I thought it strange that she would be so turned on by me touching somewhere other than the obvious areas. In truth, I could bring her close to orgasm, just by massaging the top of her thighs. I loved it, but was genuinely surprised by it. We were discussing it one evening in her home, with me saying I still didn’t believe it could have that effect. Caroline had walked into the room in the middle of the conversation and, sitting down on the sofa next to me, asked what we were talking about. Without thinking, I told her that Geraldine got turned on by me massaging her thighs and then asked, again without thinking, does this do anything for you? At which point I quite firmly squeezed both of her thighs, through her jeans.

The response was instant. From both sisters. Geraldine had shouted “Danny, WTF?!” I protested that I meant nothing by it, the truth, and I was only trying to prove a point, to which she replied: “I think you have proven the point”, and I had. The contact with Caroline had been momentary, but it had caused her to tense and shiver, and even thirty seconds or so later she was obviously affected by it. And seeing this, I was affected too. Thankfully, I don’t think Geraldine could see how hard I was, or all my protestations of an innocent mistake would have been useless.

That moment had changed how I looked at Caroline. Although I hadn’t seen her much over the following week, I had found myself thinking about her more and more. She had gone from being someone I had simply noticed, to be the centre of most of my fantasies. I don’t know what turned me on more, the idea of fucking my girlfriend’s sister, or the idea of fucking an underage girl. But both combined had me hooked.

And now here she was, walking around her home doing random shit, wearing a short white tennis skirt that was just perfect for her legs and a white t-shirt that clung to her and emphasised her small breasts. I could see her bra through it, and as small as her breasts were, they fascinated me. Add to that the sheen of exercise, not sweat, just a healthy glow, that she still carried with her. As she walked around the living room she would occasionally grimace and reach over with her right hand to rub her left shoulder. Clearly, she was in some distress.

“Are you alright?” I asked.

“I’m fine. I just pulled something, or tweaked something, but it’s fine.” She sat down on the sofa next to me. Interesting choice, I thought. There were plenty of other places she could have sat. Not that I was complaining. I could feel the warmth from her body, could smell her. And I couldn’t help but look at her amazing legs as they emerged from her little pleated skirt. Just looking at her thighs reminded me of that moment a week earlier and, just like that, I was hard.

She was obviously still in some pain, flexing her shoulder, trying to get a little relief. When she pushed both her shoulders back, her little breasts pushed forward and all I could think about was taking one of them in my mouth. She reached back again with her right hand to massage the shoulder and this time grunted a little in pain.

“Look. You are obviously in some pain. Would you like me to try to help?”

She stopped working her shoulder and looked at me. I don’t think I had ever noticed how pretty her eyes were, but now she was looking straight at me I was struck by how soft they were.

“What do you mean?”

“Well, it would probably be easier for me to massage your shoulder than for you to do it yourself.” I replied. Then smiled cheekily. “Besides, you know I’m good with my hands.”

The reminder of the earlier contact made her laugh, blush and then bite her lip a little shyly. But I also saw her pupils widen slightly and I thought I noticed her breathing quicken momentarily. Still she hesitated.

“I’m teasing Caroline,” I said gently. “But seriously, maybe I can help with your shoulder. What harm can it do?”

With a slight nod she turned in the sofa to face away from me, her head bowed very slightly. I reached up and moved her hair out of the way, exposing the left-hand side of her neck. Had she always had such a long slender neck? Stupid bloody thought, of course she had, but as I reached both hands up to begin my massage I couldn’t think I had ever noticed before.

Pressing both thumbs quite firmly into her left shoulder, just where it met the neck, I was rewarded with a sudden groan.

“That’s exactly the spot, right there Danny.”

Satisfied I hadn’t hurt her I began to work at her neck with both hands, working my thumbs from her neck down her shoulder blade and back again. Increasing the pressure on her body, she grunted and sighed and then leant slightly back into me. Pushing her forward slightly to create more space for me to work in, she slid back slightly on the sofa so that she was now bent over slightly with her backside brushing against my crotch. I wondered if she was aware of that. The touch was featherlight and fleeting, but I was as hard as I had ever been, and she was so close to me.

By now I was working both shoulders, my fingers pressing down onto the top of her shoulder, my thumbs working up the curve of her shoulder blade.

“Oh god, that is so good. I had no idea how much I needed this.” She practically moaned her approval, and while it wasn’t intended to be sexual it certainly hit me in that way. I edged forward slightly to make sure there was contact between us, and I am certain when she felt that she pushed back. Just a little. I was so aware of how hard I was, I thought it must be impossible for her not to be.

Slowly, I started to work my way down her back, still working through her T-shirt, applying steady pressure to either side of her vertebrae with my thumbs and massaging her sides with my fingers. When I reached the small of her back I stayed there, working her back and sides and receiving a series of satisfied little groans as a reward. As I slowly worked my way back up her back she arched slightly, and although I couldn’t see them I knew her small breasts were pushed out and all I wanted to do was to reach round, cup them, squeeze them hard.

This was now, clearly, a sexual act for me. I was getting more and more turned on as I used my hands to please my girlfriend’s sister. Her 13-year-old sister. But I didn’t think it was for her. Clearly, she was enjoying my attentions, but I don’t think she was aware of how much of an effect it was having on me. I had worked my way back down her back again, but this time when I started to work my way up, I slipped my hands under her t-shirt and began to massage her flesh directly.

She felt amazing. Soft skinned, still radiating warmth from her recent exertions at the tennis club, firmly muscled. Her breathing was noticeably quicker now, not quite panting but she was clearly being affected by this. Her intentions may not have been sexual, but the effect on her was starting to be. As I passed her bra I allowed my fingers to reach round a little further, brushing very slightly against the underside of her breasts. She shuddered and straightened suddenly, pushing back into me and it was all I could do not to grab both of her breasts in my hands. Instead I went back to massaging her and she quickly relaxed, resuming her slightly bent over position.

Geraldine had always loved me massaging her. She said I had a great touch and just seemed to know where and how hard to press. But she always complained that I got bored too quickly. I told her my fingers just got sore, which was true, but in either case when I did this for her it maybe lasted 5 minutes or so. But with Caroline I completely lost sense of time. Even if I had been aware of it, I wouldn’t have wanted to stop. I wanted this girl. I needed her. And I wasn’t going to stop unless I had to.

Eventually the massage faded, and I was now simply caressing her body. Her wonderful, tight, toned, smooth body. She felt amazing. Soft little moans of pleasure were coming from her. Still not sexual, just content. She had straightened up and was leaning back against me slightly as I stroked her. Allowing my hands to slip around her, I softly stroked her stomach. Tracing little circles on her abdomen, from the undersides of her breasts to the top of her skirt, I was so close to where I wanted to be. Where I needed to be. Caroline pushed back slightly against me, she must be able to feel how hard I was, and as she squirmed gently against me she seemed to like it. But still, I didn’t know if she was actually aware of this. As I ran my hands up her sides very lightly, I allowed both of my hands to caress the outer sides of her breasts. She shivered and leaned back more. My hands were back to her stomach, just moving back and forth lazily, enjoying the feeling of her and the reaction it created. I needed more.

Clearing my throat, I was still a little hoarse when I said. “This isn’t really a massage any more, is it?”

She stiffened very slightly, my voice obviously pulling her slightly out of her contented distraction. “No. I guess it isn’t.” She spoke really softly, almost reluctantly.

For a few minutes I just continued to stroke her, giving her the chance to say something, to ask me to stop. But she just settled back into her contented purring against me. But I needed to do more.

“Do you want me to stop?”

Her breathing quickened, I could feel it as her stomach moved under my hands. I could feel her little breasts moving just above my hands, easily within reach.

“No.” She whispered.

It is strange that the question you ask isn’t always the question the other person hears. When I asked Caroline if she wanted me to stop and she said no, she meant she wanted me to keep doing what I was doing. But I was on a journey, and when I asked her if she wanted me to stop and she said no, I took that to mean she wanted me to keep going. To take the next step.

She stiffened suddenly, broken out of her semi-sleep as my left hand moved up to cup her right breast, and my right hand moved down under the band of her skirt, inside her underwear and began to fondle her pussy. She was on fire. Wet, but almost burning with heat. And need. Startled she looked over her shoulder and began to say my name, but instead I leaned forward and kissed her. As she felt my tongue in her mouth she stiffened even more, I was certain she was about to pull away, and then she started to kiss me back. Passionately. Hungrily. She was trying to devour me as the sexual tension that had been building began to find expression.

Now her moans were sexual. How could they not be with her tit being roughly massaged in one hand, and her 13-year-old pussy being stimulated by the other. Her teeth bit down on my lower lip, hard. The pain was sudden, but I smiled around it and felt her smile back at me. Breaking our kiss to an audible moan from her, I began instead to kiss her neck. The moan became a soft squeal. She reached around her back to rub the bulge in my jeans, and then tried to unbutton them. The angle was impossible for her, however, and I could sense the frustration in her.

“I want you Caroline.” I breathed into her neck. “So much.”

“God, Danny! I want you too. Please…”

Kissing her forcefully, I pulled my hands away from their prizes and quickly unbuttoned and unzipped my jeans. Still facing away from me, her hand shot into the newly created opening, into my boxers and closed unerringly around my rock-hard cock.

“Oh god! You’re huge!”

I’m not by the way. I think I’m probably slightly longer than average and have been told I am thicker than most, but certainly not huge. But this was the first time she had had her hands on a cock, and I was as hard as I have ever been.

My left hand fisted in her hair, pulling her head round and her lips back onto mine. And we resumed our mutual devouring. My right hand went back to her pussy, but this time I reached round under her skirt and into the top of her panties, giving me more room for manoeuvre. She cried out into my mouth as my middle finger sank fully into her. Seconds later it was joined by a second finger. She was soaking wet, and so hot. And so tight she gripped my two fingers more firmly than I had thought possible. But she was also incredibly soft and yielding.

Again, I broke our kiss and at the same time released my hold on her hair. Her head fell forward slightly, exposing her neck to me and immediately my teeth clamped around it. I bit into her, hard enough to make her cry out over her moans of pleasure. I desperately wanted to mark her, to leave MY mark on her, but enough sense remained to me to know that would only cause a lot of problems. So, I contented myself with nipping at her neck, hinting at what I wanted to do. By now my left hand was back on her right breast, but this time inside the cup of her bra. Her tiny little breast was fully in my handle, soft and pliant. I was going to have to suck these later, but for now I just pulled sharply on her nipple. At the same time, I bit down a bit harder on her neck and pushed my two fingers as hard and as deep into her as I could.

“Oh god Danny!! That’s too much! It’s too much! Please!”

Ignoring her plea, I continued to finger fuck her while pulling at her nipple and biting her neck. If anything, her pained pleading urged me on to be more forceful. After a few seconds, she was still pleading with me, but now for something completely different.”

“Oh Danny! That’s amazing! Please don’t stop! I need more!”

Someone really needs to teach teenage girls how to give hand jobs. That would be a useful part of sex education, because they all seem to have the same bad technique. Caroline’s fingers were lightly curled around my cock, as if she was afraid she would hurt me; and she was moving her hand back forth extremely rapidly, but with a very shallow oscillation. What they need to do is imagine how tight their virgin pussies would feel or, better, their asses, and grip at least twice as tight as that. Then they need to imagine how hard and deep men want to fuck them and try to match that.

Still it’s the thought that counts. Right? Not hardly. My raging hardon needed release, her hands weren’t giving it, I doubted her mouth could, it needed to be the tight little hole that was currently clamped around my two fingers. I pushed her away from me a little, and abruptly pulled my fingers from her.

“What?! No! Why?” She asked, then her mouth fell open as I smiled at her and sucked both my fingers deep into my mouth, tasting her for the first time. And for the first time she was being tasted.

I smiled again, kissed her gently on the lips then turned her around. I ran my hands up the outside of her t-shirt, gently fondling her breasts, and lifted her arms above her head. Reaching down I lifted the bottom of her t-shirt and pulled it over her head. Dropping it to the floor I immediately undid her bra, freeing her perfect little tits. Immediately cupping them in both hands, I kissed her again, passionately but more gently than before. My need was about to be met and I no longer felt it necessary to express it in other ways.

Gently pushing her forward she put both hands on the arm of the sofa, bent over fully for me now. I pushed her legs slightly apart and lifted her tennis skirt up over her back. I smiled at the sight of her white cotton panties. Absolutely perfect. But then, if you are going to be playing tennis and there is the chance of an inadvertent flash, perhaps they are the ideal choice. Not willing to take any more time, I slipped them gently down her wonderful thighs to her knees. Positioning my left knee on the sofa behind her, and adjusting my standing foot on the right I lined myself up with her glistening pussy.

A single, forceful thrust and I pushed every millimetre of myself inside her. It’s impossible to describe how tight she felt, how amazing. I knew she was a virgin, I don’t know how I knew I just knew, and even though there had been no blood from my rough fingering of her, I still had no doubts. Perhaps she had taken care of that herself. But this was the first time she had a cock in her, and it was as far in her as it was possible to go. The fire in her pussy immediately engulfed my cock, threatening for a moment to tip me right over the edge. The tightness of her pulled my foreskin right back, but she continued to clamp down on me. So tight it should have been painful, but so soft it was just the greatest pleasure ever. How could something be so hot, so tight and so soft at the same time? Who cares? The feeling was all that mattered.

“OH MY GOD!!! Oh my god!!! Oh, fuck Danny, oh fuck!!! Oh God! Oh god, that’s just…that’s, OH MY FUCKING GOD!!”

“Oh, fuck Caroline, you feel amazing! I’ve never felt anything like this! You’re perfect!

I don’t think she could hear me. She was still calling out to god, but her hand had found her clit and was starting to work on it. She was taking care of her needs, time for me to take care of mine.

Geraldine had never wanted to fuck in this position, she said it was to impersonal, thought it was even slightly degrading for the girl, but now for the first time in my life I had a girl on all fours in front of me in doggy, with my cock fully lodged in her pussy. My girlfriend’s sister’s pussy. Always with Geraldine, she had insisted on using condoms. Fair enough, neither of us wanted her to get pregnant; but now for the first time my cock was engulfed in pussy without protection, and for the first time I was going to cum inside someone’s pussy. Not just someone’s pussy. My girlfriend’s sister’s pussy. Her 13-year-old sister’s pussy.

Both hands around her waist to give me balance and control, I started to fuck her. Hard and deep, pulling back as far as I could without risking coming out of her, then thrusting forward and pulling her back by her hips until I slammed into her ass, this was all about me. Our pleasure might have been mutual, she was moaning and crying my name out as I fucked her, but my intentions and desire were entirely selfish. If she had asked me to slow down, I would have ignored her; if she had asked to change position, I would have ignored her; if she had asked me to use protection, I would have ignored her. If she had asked me to stop, I would have ignored her. I was going to cum inside her, because that’s what I wanted. What I needed. She really didn’t matter anymore. But fortunately, she was getting exactly what she wanted. The fire in her pussy got hotter, the walls closing in even tighter on me. She was no longer using words, just screaming incoherently. The sound of our fucking was a harmony of her screams, the slapping of my pelvis against her ass and the wet squelching of her pussy trying to hold onto my cock as I pulled back. With a sudden scream her arms gave way under her and she was face down on the sofa, panting and saying my name over and over, with the occasional “Oh god” in between. She had beaten me to it, but I was not far behind her.

Shifting my balance slightly, to compensate for her slight change in position, I continued to fuck her as hard as I could. Fewer strokes, slower, but forced home as hard as I could manage, aiming more down now than before. Holding myself against the wall of her pussy for a second or so before pulling back sharply, and forcing myself in again. Her moans now sounded exhausted, but until I was finished neither was she. But I could feel it building, rapidly, and with the sudden realisation of what I was doing, and with whom, it erupted out of me. I came hard, and deep inside her. And I kept coming. As I emptied myself inside her, she stirred slightly.

“Oh, Jesus Danny! I can feel that! Oh…Wow!”

My heart was racing. I was gulping in breath like I’d just sprinted a mile. My legs suddenly seemed to lose all their strength and I thought I was about to collapse on top of her, but I wanted to stay inside her as long as possible. My cock was still twitching slightly, loosing smaller amounts of cum as she clung on to me. Nothing previously had felt this good, and I had no idea if it was the lack of condom, who she was, her age, or just some perfect match between the two of us. I just knew I would be doing this to her again tonight, and many more times in the months to come.

As my heart and breathing returned to normal, Caroline pushed herself back up onto her arms. It seemed to take some effort. She looked over at me, eyes wide and opened her mouth to say something. But she had no words. I just looked at her and shook my head, smiling slightly. I didn’t know what to say either. A small look of resignation came over her face and, to my surprise and disappointment she pulled herself off me. Her pussy seemed as reluctant as I was, as it seemed to try to cling onto my slowly softening cock.

Making a strange face, she reached down suddenly and cupped her pussy with her right hand. I guess my sudden withdrawal had been the breaking of a dam, and she didn’t want to get any on the sofa. Before I could say anything, she looked at me and kissed me, gently, tenderly. And that was enough for me to start to harden again. Taking my right hand in her left she broke the kiss and said sweetly.

“Come with me.” Holding my cum inside her with one hand, she led me by the other up the stairs to her bedroom.

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