I was just about to do some more unpacking when there was a knock on the door. I was in half a mind to ignore it but then there was another knock, this time much louder. Damn, I wasn’t in the mood for uninvited guests. However when I opened the door I was pleasantly surprised.
“Hi sis, I thought you were coming tomorrow?”
“I was, but I couldn’t wait to see your new place.”
“It’s in a bit of a mess, I haven’t finished unpacking yet.”
Suddenly her smile disappeared, it was replaced with a frown.
“I have a question for you.”
I waited, but she just stared at me.
“OK, what is it?”
The smile came back and then she said “Can I come in?”
I laughed, then I moved aside so that she could enter. As she passed me I muttered “Very funny.”
I liked my new apartment, I was anxious to hear her assessment of it. She can be very critical, and at times quite rude, so I was prepared for the worst.
“I like it, the kitchen could be bigger, but it will do.”
“Thanks, I wasn’t sure if you would approve of it.”
She smiled then said “Why, because I am such an awkward bitch?”
With a straight face I answered her with “You are not awkward.”
Luckily she found that really funny.
We then talked for a while. I offered to make her some lunch but she declined, she was meeting some friends later on and would eat with them. As she was leaving I noticed a slight limp.
“What’s wrong with your leg?”
She turned round to face me then said “It’s nothing serious, just some problem with my right calf muscle. Too much exercise, I think I have been overdoing the running.”
I was concerned, “I think you need to get it checked out.”
She shrugged her shoulders then said “It will get better with time, or if I get a sports massage.” She then continued with “Normally I see a guy who works at the Gym, but he is booked up for the next two weeks.”
“I could do it?”
I had intended it as a joke but she wasn’t laughing, instead I could see she was considering it.
“Are you serious?”
I hesitated, then I said “Yes.”
However as soon as I had said it I wasn’t sure if I could deliver on what I had just agreed to. Lily would expect me to do a proper job. I was just about to tell her I had changed my mind when she spoke.
“OK, but when?”
It was now too late, I would just have to give it my best shot. When was I free to do it?
“How about tonight?”
She was obviously keen. I couldn’t think of a reason to say no, so I agreed. We decided to do it at eight, that would give me time to do more unpacking.
“I need to go, otherwise I will be late meeting up with Carol and Janet. I will see myself out.”
I was deciding what box to tackle next when I heard the front door close, then I heard knocking. What had she forgotten
“Sorry, I should have said before I left. I will bring the massage oil and you provide the towels.” Then she quickly added “I am assuming you have some towels?”
“Very funny, now go and leave me in peace.”
“OK, but I think you should let me have a key.”
I shook my head before saying “No chance.”
As I closed the door I heard her say “It’s a good idea me having a key.” I just ignored her.
I spent the next hour working, most of the kitchen stuff was now done so I decided to take a break. I smiled as I sat on the sofa drinking a mug of coffee, at twenty-three it felt good to have my own place, even if I was only renting. I checked my watch it was just after four, I would stop for fifteen minutes.
At seven I decided to call it a day. I still had a few boxes to unpack but they contained non-essentials, mostly books. I had neatly stacked them in the spare bedroom so they were out of the way. I desperately needed a shower and a change of clothes.
As I showered I thought of Lily and how I would conduct the massage. I have always played a lot of sport and consequently I have had a lot of injuries, mostly minor ones though. If it was a sore or stiff muscle then a massage always helped. What I would do to Lily is to try and copy what has been done to me in the past. That was the theory, we would just have to see how it worked in practice.
“Sorry I am late.” It was eight-thirty.
“No problem, but I was beginning to think you had changed your mind.”
She just smiled then proceeded to check the apartment again.
“You have been busy, I am impressed.”
I beamed, proud of what I had done.
“Let’s get started. Where can I hang my coat up?”
“Sorry, no coat hooks. It’s on my list of things to do.”
She unbuttoned her coat and placed it over the back of a chair. I stared at her. When she turned round she could see the look on my face.
“What?” She then laughed and said “Yes the skirt is a bit short.”
“Short, it’s almost non-existent.”
She laughed again before saying “I don’t wear it in public, it’s just for the massage. I don’t want to get oil on my clothes.”
I didn’t know what to say. I had naively assumed I would just be doing her calves but it looked as if Lily was expecting me to go higher, much higher.
She lay face down on the bed and I placed a towel over her to cover her bottom. I was just about to start when I had a thought.
“Give me a few minutes, I will warm the oil up.”
“OK, but don’t be too long or I might fall asleep.”
I placed the bottle in a bowl of hot water, a couple of minutes should do the trick. As I waited I thought of Lily, my big sister, seven years older than me. She had recently split with her boyfriend so was now living on her own. If they had still been together I guess he would be massaging her now rather than me. It was six months since my last regular girlfriend, now that I had my own apartment I was hoping my luck would change.
I checked the oil, nearly ready.
How long before sis would find a new partner? I wouldn’t say she is a raving beauty but she generally does OK getting men, the problem is in keeping them. She is about five feet three inches tall, quite slim, probably because of all the exercise and sport she does. Her face is average but she has a really nice smile, it’s probably her best feature. On second thoughts no, it must be her tits. They are not massive but are quite big and prominent.
“How long are you going to be?”
I tested the oil before shouting “It’s ready now.”
I started on her right leg, slowly massaging her calf. When I got to the tender part she winced.
“That’s the spot. Do it gently at first then dig deeper into the muscle.”
After five minutes she asked me to stop.
“That was good but I think it’s enough for now. Just do the rest of my legs.”
I did the same to her left calf, but this time for about ten minutes.
“How does that feel?”
“Good, but you need to do my thighs as well.”
I removed the towel, her short skirt was only just covering her knickers. This was going to be awkward. I started massaging her right leg again, but this time just above the knee. As I slowly moved my hands higher I realised that in order for me to continue she would have to spread her legs. Should I ask her to move her legs or was she expecting me to push them apart? I stopped, I wasn’t sure what to do. Lily must have realised why I had stopped because she suddenly parted her legs.
“Are they wide enough?”
I couldn’t speak, my mouth was wide open and I was staring at her white knickers. She then wiggled her bottom and opened her legs even more.
I managed to mutter “Yes.”
My cock had now grown several inches and was straining in my trousers. I quickly adjusted it to make it more comfortable. My gaze returned to her bottom, covered by her tight knickers. I could see the outline of her cunt. I couldn’t be sure but it looked as if she was shaved.
“What are you doing?” She sounded slightly irritated.
“Sorry sis, I was just deciding if I needed to heat the oil up again.”
“There was a quick “No” from her.
As I continued with the massage I smiled to myself. What I should have said to her was ‘I was just admiring the shape of your cunt and imagining how good it would be if I could finger you’.
I was now working on her upper thighs, just below the hem of her skirt, about six inches away from her knickers. She was giving appreciative moans, particularly when I went deep into the muscle. My cock was throbbing but I was trying to ignore it. I was finding it difficult to concentrate, but thankfully we were nearly done.
“Finished, did I do a good job?”
“Yes.” Then she said “But I want you to do a bit more. It’s slightly sore higher up on my left side. I think it’s because when I have been running I have put more strain there to compensate for the problems with my right calf.”
I hesitated, I didn’t feel comfortable massaging any higher. However if it needed doing then I should just get on with it.
“OK, let me know when I hit the spot.”
I started where I had left off, then I slowly moved up.
“Be careful of getting oil on my skirt. It might be better if you lift it up out of the way.”
I was trying to decide how to do that without using my oily hands when she reached behind and did it herself.
Her whole bottom was now clearly visible, just covered by her tight knickers. It looked good, nice and firm, I was resisting the urge to touch it.
When I found the tender spot she groaned. As I worked on it my wrist accidently brushed against her cunt, she groaned again. I stopped for a few seconds, expecting some harsh words from Lily, but she didn’t say anything. However what I did notice was that she moved her leg slightly in, making it more difficult for me to massage her without my wrist doing the same again.
I knew I should end the massage but I continued. This time when I brushed against her I left my hand there longer than I should have, just for a second. It was enough to make her moan. I waited then I did the same again, but this time I kept my wrist against her cunt whilst I massaged her groin.
“Is that good?” Then I quickly added “The massage.”
There was a “Yes” from her. Then she continued in a dreamy voice with “It’s made me so tired I think I am falling asleep. Just continue with what you have been doing. Wake me up when you have finished with me.”
My head was spinning. She had just given me permission to continue, but still making it look like an innocent massage. Logic said stop now but my cock said continue. I gave a low sigh, I knew I was weak.
In a low voice I said “Are you asleep?”
Nothing. I doubted that she was but I went along with the pretence.
I could see the outline of her lips through her knickers, that’s where I put my fingers. I rubbed against them, pushing in I searched for her clit. Now that I had felt her on the outside I desperately wanted to finger her. I managed to squeeze two fingers into the side of her knickers, her skin was smooth, she was shaved. I wanted to push them deep into her cunt but it was difficult, I had to make do with just the tips going in. That wasn’t going to work, so I took them out and put them on her clit.
Whilst I was playing with her I had managed, one-handed, to unzip myself. If I am honest I would say my cock was no better than average, six inches on a good day. This was definitely a good day. As I firmly rubbed her swollen clit, I stroked myself. She was now moaning continuously, and at times gasping for breath. I was ready to come and from the sounds she was making Lily was as well.
I reached it first, with a loud gasp I climaxed. As I watched it pour out onto the towel on the bed, and some onto Lily’s leg, I furiously rubbed her clit, my fingers were a blur. However it took her another thirty seconds before she reached it. Her body jerked and she closed her legs, trapping my hand. Eventually she relaxed and I got my hand out.
Whilst waiting for her to recover I pushed my limp cock back into my trousers and zipped myself up. I wiped Lily’s leg, then I threw the stained towel onto the floor.
She gave a loud yawn then said “I must have dozed off. That was a nice sleep, have we finished?”
“Yes, I think you should have a shower now.”
As she walked past me I gave her a big smile, she smiled back. After she had showered we had a coffee. We talked about all sorts of things but no mention, or even a hint, of what had just happened.
“I need to go. Thanks again you do a good massage. One of the best.”
I wasn’t sure if she was complementing me on my massaging skills or my fingering skills, I hoped it was both.
I was just about to close the door on her when she turned back and gave me a quizzical look. I waited.
“Two questions for you.”
“OK, what are they?”
“Can I have a key?”
I laughed then said “No, but what’s the other one?”
“When are you going to give me another massage?”
I was surprised, but not disappointed. I had assumed it was just a one-off.
“Don’t you want to?”
“Yes, it’s just I thought you only needed me to do it once.”
She made eye contact with me, then holding it she slowly said “I think this injury may take some time to heal.”
I smiled then said “Yes, how about tomorrow at the same time?”
She hesitated then said “That’s too soon, I need time to recover. Make it the day after, Wednesday.”
“OK, at eight.”
When she had gone I pondered over what she had said. Did she need time to recover from the massage or from her climax? I was keen to see her tomorrow but I would just have to wait an extra day.
The next two days seemed to pass very slowly, I was marking time until Lily returned. On Wednesday morning there was a three hour management meeting at work. I found it difficult to concentrate, I kept thinking about what had happened before and what might happen again tonight. In the middle of the meeting the boss asked me a question, he didn’t look happy when I had to ask him to repeat it. Fortunately I gave a good answer and, to my relief, he seemed pleased with me.
Just after eight there was a knock on the door, please let it be Lily.
“Hi Henry.”
“Hi Lily, come in. Go into the bedroom and I will go to the kitchen and warm the oil.”
She nodded, and then walked passed me.
When I entered the bedroom I was surprised to see her lying on her back, I had assumed she would be on her front as before. She was wearing the same short skirt, but her legs were closed so I couldn’t see her knickers. I just hoped this time she had on a different pair, ones that were easier to get into.
“I thought it might be better this way.”
“OK, can I start?”
She hesitated then said “Not yet, just pass me that small hand towel.”
I was curious, but I did what she asked without saying anything.
“Close your eyes.”
I stood there, eyes closed, wondering what was going on. I could hear her moving on the bed.
“Keep them closed. I made a mistake of wearing an expensive pair, I don’t want you to accidently get any oil on them.”
She was taking her knickers off.
“You can open them now.”
I could see the towel draped between her legs. I was now getting excited imagining what was under it, her naked cunt. On the floor were the discarded knickers, red ones this time.
In as calm a voice as I could manage I said “I am going to start with your calves.”
She closed her eyes. For the first ten minutes I did exactly that, then I slowly moved higher. When I got to her inner thigh my cock started to grow. I cursed myself, I should have worn something looser, my running shorts would have been a lot better. I checked she still had her eyes closed then I adjusted myself as best I could.
I was now as high up as I could get, any further would mean going under the towel, or removing it. I stopped, not sure what to do.
“Your massage is so good, it’s making me sleepy again. If I do fall asleep you must carry on.”
I smiled, very soon my hand would be under the towel. However before I could do that Lily spoke again.
“If the towel is in the way of the massage you can move it to the side.”
Even better. I continued with the massage for a couple of minutes then in a low voice I said “Lily?”
No reply. I looked at her for a few seconds, she was still, as if she was asleep. I slowly removed the towel, then I gently pushed her knees up before parting her legs as wide as I could. For the next thirty seconds I just stared at her cunt. I liked what I saw, nice size lips, a prominent clit and an opening that already looked juicy. How many fingers could she take? I didn’t know, but I would soon find out.
With one finger I toyed with her opening. I put it in just enough to get it sticky, then after a few seconds I slowly pushed it all the way in, up to the knuckle. I heard a low moan from Lily. I pulled it out then I did the same again, but this time with two fingers. It felt tight, but room enough for three. I was right, three felt good for me and, judging from the noise she made when I put them in, it felt good for her.
I was now finger fucking her, I was also stoking my cock. Getting it out had been a nightmare, at one point I thought I would have to take me fingers out of Lily, but eventually I managed it with just my free hand.
We continued like this for several minutes. I was close to coming but Lily seemed to be struggling, she needed something extra to move her towards a climax. Last time rubbing her clit had worked but this time I wanted to do something different. I took my hand off my cock and, whilst I continued fingering her, I positioned two fingers on her puckered anus. My fingers were sticky with my pre-come so when I pushed they slipped in easily. There was a loud gasp from Lily. I don’t know if anybody has ever done that to her before, but it did the trick.
I left all my finger in until I felt her start to relax. As soon as my right hand was free I worked my cock. It didn’t take me long to climax. Unfortunately almost all of it went on Lily, most of it on her stomach, but some near her cunt. I quickly put the towel between her legs to absorb it.
When she eventually opened her eyes I was decent. My cock was back in my trousers and I was zipped up. There was an obvious stain on my crotch that she couldn’t help but see, but nothing was said.
“That was better than last time.” Then she paused before saying “Yes, a much better sleep.”
I smiled. I was happy she was satisfied, I certainly was. This time there was no question of us stopping. The only thing to decide was when we would do it again.
“That was nice shower. I feel completely relaxed.”
“Good, I left your coffee in the kitchen. I only made it a couple of minutes ago so it will still be hot.”
When she returned with it she looked at me and said “When?”
I feigned ignorance, “What do you mean?”
She placed her hands on her hips then said in a firm voice “When are you going to massage me again?”
I laughed, “Sorry sis, just teasing, but it will have to be the weekend. I have to work late the rest of the week.”
We settled on Saturday at three. As she left she asked again if she could have a key, I told her no chance of that happening. However I am sure she will keep mentioning it, just to irritate me.
On Saturday morning I got a call from Lily, could we change it to Sunday? I was disappointed but I tried not to let it show. I said yes, but we changed the time to one. We chatted for another five minutes, when the call ended I swore a few times.
It was one-thirty, Lily was late. I was going to call her when there was a knock on the door. When I opened it she was just about to speak, but I got there first.
“No you can’t have a key.”
She gave me a wry smile, “Very funny.”
We then followed our routine, me in the kitchen heating the oil up, Lily getting herself ready.
As I entered the bedroom I stopped, she was sitting on the bed. She looked as if she was about to say something, so I just waited.
“I have been thinking.”
I had a feeling I wasn’t going to like what she was about to say.
“I think.” She then hesitated before saying “I should take all my clothes off.”
I was wrong, I did like it.
“Last time you got some oil on my skirt. Also I have managed to strain a muscle under my ribs when I played tennis yesterday, so you will have to massage me there as well.”
I could see she was waiting for me to agree with her, that taking her clothes of was a sensible idea.
I put on my best serious face, then I just said “Yes.”
She looked relieved, as if she had been expecting me to say no. That was never going to happen. As I left the room to give her time to undress I smiled to myself, imagining what her big tits would feel like.
I started the massage as before, on her calves, but this time I moved quickly up to her thighs. The small towel between her legs was now getting in the way. I desperately wanted to remove it but I needed to wait, she would let me know when I could go further. It was another five frustrating minutes before that happened.
“I am so tired.” She then gave a small yawn before continuing with “I think It’s best if you work on that strain under my ribs first before finishing my legs off.”
So she wanted me to play with her tits first before I fingered her. I wasn’t going to say no to that. I was now itching to get to her tits, so I only waited a few seconds before saying “Lily?”
Without bothering to wait I immediately removed the large bath towel that was covering her upper body.
I groaned when I saw her big tits, they were even better than I had imagined. Her nipples were a lot darker than the rest of her skin. What I liked best about them was their size, long and thick. It didn’t look as if they were swollen yet, so how big would they get when I sucked them?
I didn’t even pretend to massage her, instead I just when straight for them, I couldn’t wait. However I did manage to keep away from her nipples for a couple of minutes in order to build up the anticipation.
When I did eventually get to her nipples I was in heaven. I sucked long and hard, then I switched to the other one. For the next few minutes I changed from one to the other, giving both her swollen nipples equal attention.
I now wanted more. I finished on her tits with as hard a suck as I could manage, Lily gasped. I then quickly removed the towel that was covering her cunt. Should I fuck her? I wasn’t sure if that was what she wanted, it might be a line she wasn’t prepared to cross. I wondered if I should just ask her, but I decided not to, instead I put my head between her legs.
I had enjoyed her tits, but her cunt was even better. I loved the taste of it. I licked her lips then I pushed my tongue in as far as it would go, but the best bit was when I found her clit.
I was now concentrating on licking it as hard, and as fast, as I could. Lily was responding by murmuring ‘Don’t stop, don’t stop’ almost continuously. The volume was increasing, she must be getting near to climaxing. This time I had worn my running shorts, but I hadn’t taken my cock out, her cunt needed my full attention.
Ramming three fingers deep into her took her over the edge. Her cunt exploded. As she writhed about I lifted my head, I didn’t want to get it trapped between her thighs.
My cock was now out of my shorts, but it looked as if I wasn’t going to get enough time to finish.
“Lily must be tired. I think she will be asleep for at least another five minutes.”
I had said it as if I was just talking to myself, I just hoped Lily would understand that I wanted her to pretend to be asleep for a little while longer.
As I worked my cock I looked at Lily, her eyes were still closed but her lips were slightly open. Should I? I hesitated, then I went for it. I gently pushed the tip of my cock against her lips, they opened wider, then she moved her head slightly so that my cock could go into her mouth.
She was good, very good. I am not hung like a horse but even so she managed to take it all in. After a couple of minutes I could feel it building up, would she swallow? I was about to find out. As I was reaching it I gave a low moan, Lily then took all of my cock in, right up to my balls. She gagged as I poured it down her throat, but she kept it in until I had finished.
Would she swallow? Of course she would, every last drop.
When she opened her eyes I was still putting my cock back into my shorts, but she didn’t seem to notice. Before saying anything she reached for the towel and casually draped it over herself.
“Your bed must be really comfortable. Every time you massage me I always fall into a deep sleep.”
I smiled at her, but then I noticed she was now thinking about something, what was on her mind? Was she regretting what we had just done, and what had happened previously?
“I was just thinking. The massage you give me is very good, but I think you could make it even better.”
I was puzzled, not sure what she was getting at.
“Next time I want you to go deep into me.” She paused before continuing with “Into the muscle.”
Now I understood, next time she wanted me to fuck her. However to be sure I wanted her to say more.
“I can do that, but it will need a different technique. I will have to do something I haven’t done before.”
“Yes, that’s what I want.”
I had already fingered her, licked her and come in her mouth. Without actually saying it she had made it perfectly clear that she wanted to be fucked.
When she left we hadn’t fixed a time for the next ‘massage’, Lily needed to check her diary. The next day she called me at work.
“Hi, I need to make this quick, I am running late.” Then she continued with “I’ll be at your place just after seven tomorrow, make sure the heating is on, last time it was a bit cold.”
Before I could say anything she ended the call, leaving me staring at the phone. I was supposed to be meeting Andy at eight tomorrow, I would have to call him and rearrange. He was a good friend and I enjoyed his company, but not as much as I would enjoy fucking my sister.
She was late again, this time by forty minutes.
“Sorry, I got stuck in traffic.”
I didn’t reply, I was just glad that she was now here, I had thought she was going to ring and say she couldn’t make it.
There was very little oil left, not worth heating up. I waited in the kitchen for a few minutes to give her time to undress. My cock was already stiff, I was eager to fuck her.
When I entered the bedroom she was face down, naked. I had left a towel so that she could cover herself, but she hadn’t used it, it was now on the floor.
As I sat on the bed she spread her legs, just enough so that I could see her cunt. It was as if she was inviting me to fuck her. I stared at it, trying to imagine what it was going to feel like when I eventually pushed my cock deep into her. Time to find out, but I wanted to get her into a better position.
“Lift yourself up, get onto all fours.”
There was a slight delay then she did as I asked.
i quickly removed my shorts. The only thing that was stopping me now was the fear of getting her pregnant. Was she on the pill? I didn’t know, it wasn’t something she had ever mentioned to me before. I had brought a condom with me but I really wanted to fuck her without. Reluctantly I tore open the packet, better to be safe than sorry.
“What are you doing?”
That startled me. She must have heard me opening it
“I am just.” Then I stopped, not sure what I should say next.
In a firm voice she said “If you are messing about with that oil, then don’t.” In a softer voice she continued with “You can do me without.”
So she did know what I had opened.
“Are you sure?”
She answered with a clipped “Yes.”
I was going to get my wish. Holding my cock firmly I rubbed the tip against her cunt lips, she gasped. I teased her like that for several minutes. She kept wriggling her bottom to get my cock into her, but I kept it out.
When I sensed the teasing was getting too much for her I held her hips and pushed in, as deep as I could go. She gave a long groan that seemed as if it would never end. When it did eventually stop she murmured something, it was too low for me to make out what she had said. She then said something else, this time louder.
“Fuck me, fuck me hard.”
I was now doing what she wanted, long deep strokes. There was a lot of noise from her, a mixture of moans and groans, and some grunting. I was surprised how long she was lasting. I was in danger of reaching it without her being satisfied, that would spoil it for her, and it would also take away some of my pleasure.
I was now very close, but I didn’t think she was. In frustration I muttered “Is her cunt never going to come?”
It wasn’t meant for her to hear, but I must have said it too loud.
“Yes if you fuck me harder.” Then she said “I am a cunt, a dirty cunt. Fuck me hard little brother.”
I did, and she climaxed. As she collapsed onto the bed I poured everything I had into her, there was a lot.
When I had recovered I declared “That was some massage.”
She giggled then said “Yes.” It was quickly followed by “Remember it was JUST a massage.”
We both showered, Lily first, then we sat in the kitchen sipping our coffee. As I was enjoying the moment, thinking back on what had just happened, she dropped a bombshell.
“Dave at work had asked me out.”
She looked guilty, and I guess I looked shocked. There was an awkward silence for a few seconds.
“I like him, but it will mean the end of.”
She didn’t need to say anymore, I knew what she meant. So there it was, but at least it had ended on a high.
She must have seen the disappointment on my face because she said “Cheer up, if it doesn’t work out with Dave I might need your expert help again.”
I gave a weak smile, I was trying not to be childish about it. I guess on the positive side it was a win-win situation. If she and Dave had a long relationship then I would genuinely be happy for her, if not then I would probably get to fuck her again.
As I was closing the door on her she turned back and held my hand.
“Thanks for being so understanding.” I smiled, this time a genuine one, before saying “I hope it works out between you and Dave.”
From behind the closed door I heard her parting shot.”And I hope you are going to give me a key!”
Tell me at [email protected] how’s the story, you can also reach me for some naughty talking, I am very easy to talk.
Added by Aryan Sharma
