A Long Weekend

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His sister's friend needs to relax.
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Ashson
Ashson
8,545 Followers

My sister, Michelle, turned eighteen about a month ago. One of her best friends, Jennifer, has her birthday on the same date. Part of the reason they are friends, I guess. They tend to have joint birthday parties, except the year they turned ten and were not talking to each other.

A month after their joint birthday there was a public holiday, resulting in a long weekend. Both girls managed to get an extra day off, letting them enjoy a rare four day weekend. Michelle invited Jennifer to stay with us for the long weekend and, to no-one's surprise, Jennifer agreed. (My feelings on the matter were neither required nor considered, not that it worried me.) Jennifer rolled up after work on Thursday and just like that she was settled in for the weekend.

Jennifer was quite an attractive girl. Modest, a little shy, quite intelligent, and socially inclined. I'd always got on quite well with her but had tended to consider her as not in my hunting area due to her close friendship with Michelle.

I'd been out late on Thursday and when I got home the house was dark apart from the girl's bedroom. I assumed that my parents were asleep and the girls were still up talking. Strolling past their room I looked in, seeing they'd left the door open, and saw Jennifer was curled up on her bed fiddling with her phone.

She wasn't urgently texting or anything, just flicking through the screens in a desultory manner, indicating a bit of boredom. A glance to the side showed that Michelle was already asleep. It was a warmish night which was probably why Jennifer couldn't drop off. She was wearing a set of baggy cotton pyjamas, and was just lying slumped on the bed. I strongly suspected that she had no idea that those baggy pyjamas had slipped down at the rear, exposing over half her bottom, and a very nice bottom it was.

"You look a trifle bored," I said, wandering in and sitting on the edge of the bed next to her.

"Just restless," she grumbled, "and you shouldn't be in here."

I laughed. "What harm can it do? Michelle's right there. One loud word and she'll be awake and glaring daggers at me for waking her. It won't matter which one of us actually wakes her, I'll still get the blame. Relax a little."

To help her relax I started rubbing Jennifer's back. Just lazy circles from the small of her back to her shoulders and down again. I could feel her relaxing under the gentle massage.

Now as far as I was concerned it was only reasonable that I rub all of her back, and with that much bottom on display it was only fair that I treated it as a continuation of her back. When Jennifer found that my hands were rubbing across her bottom she didn't think it was quite so reasonable.

"What are you doing?" she hissed at me, trying to push my hand away.

"Rule of thumb," I informed her. "If it's on display then you're allowed to touch it."

"My bottom is not on display," she said very firmly, trying to hitch her pyjama trousers up.

"Actually, it is, and a very fine bottom it is."

"Don't do that," I added, stopping her pulling her pyjamas up. "I prefer things the way they are. Stop fussing about it. It's not as though I'm going to seduce you with Michelle in the room. Just relax and enjoy a harmless massage."

She didn't relax immediately but as I continued to just lightly rub her back (and bottom) she did calm down, going with the flow, as it were.

Now they weren't my pyjamas. I couldn't be blamed if they were a bit loose on her. Neither could I be blamed if when I brushed my hand across her bottom any contact with her pyjamas seemed to push them a little further down. I don't think Jennifer fully realised how far down until my hand idly brushed across her pudenda. Then she knew.

She gave a muffled exclamation and hurriedly tried to push my hand away, but I wouldn't be in it.

"Don't be silly. I'm not hurting you, just rubbing a little. And that's all I will be doing, I assure you."

For some reason my words didn't exactly help her relax and she was all tensed up for a while, but when all I did was continue to stroke her and rub her, even if I was rubbing certain sensitive areas, she started to relax, although she did seem to be breathing hard.

We continued like that for a while, me gently massaging, her receiving that massage. At some point her legs seemed to have drifted apart a little further, giving me easier access, although I'm sure she'd have flatly denied that if it had been pointed out.

After a while she was twisting about under my touch, just slowly writhing in place while she tried to keep her mouth shut. I could hear faint whimpering sounds escaping but ignored them, me being a gentleman and all that.

It was a little harder to ignore when she slapped both her hands across her mouth and seemed to throw a fit. She climaxed beautifully, almost heaving herself off the bed. Then she just slumped back down on the bed, totally relaxed.

"There you are," I said cheerfully. "You seem a little more relaxed now. I'll leave you to catch some sleep."

I departed, switching off the light as I went. I'd performed my good deed for the day. I'm quite sure Jennifer didn't mean it when she muttered what sounded like, "You rotten bastard."

I didn't see much of the girls the next day. It was a case of they went their way and I went mine. When I got back home in the evening they'd already retired so I didn't bother them. A little later I was just about ready for bed myself. Heading in that direction I noticed the light showing under the girl's bedroom door so I tapped lightly and stuck my head in when there was no reply.

Jennifer was awake and lying on top of her bed again. When she heard the door open she turned her head to see who it was, spotted me, and hastily lay on her back, making sure her pyjamas were pulled up. She glanced across at Michelle and then mouthed a rude word at seeing her asleep. I'll say this for my sister, she can always go to sleep at the drop of a hat.

"Go away," Jennifer told me as I strolled across to sit next to her.

"Don't be like that," I grumbled. "I'm not going to hurt you or seduce you. Not tonight, anyway."

"Not any time," retorted Jennifer.

"If you say so," I said agreeably, dropping a hand onto her tummy. "No, I just thought a little massage. Slightly different to last night's though."

She glared at me but didn't try to stop me rubbing lazy circles on her tummy. I suspect that she felt it would be useless unless she made enough noise to wake Michelle and she didn't want to do that. After all, I hadn't really done anything reprehensible.

The trouble with rubbing a girl's tummy is that you can't really be sure where the tummy ends and her chest begins. Of course, once your hand starts brushing those lovely upper curves you tend to know it. So does she.

"Shift your hand," Jennifer demanded in a voice that hinted that she meant what she said.

I did so, of course. I'd felt the lower curve of her breasts and knew just where she was coming from. My hand rose over her curves, caressing her lovely breasts, my thumb rotating each nipple as my hand passed across her.

"I didn't mean like that and you know it," gasped Jennifer.

"Oh. Sorry," I murmured, my other hand starting to trace little circles on her tummy.

"Well?" she demanded.

"Well what?" I asked.

"Your hand. Move it lower."

Now there was a surprise. I'd have thought she'd be more concerned about her breasts. The hand on her tummy dipped lower, slipping inside her pyjamas and soothing its way across her mons. Finding some nice warm curves down there I started massaging them.

"Stop that. You're doing that deliberately. You know I meant move the hand on my breasts."

"I am moving it, I assure you," I told her, that hand continuing to wander back and forth across her breasts. Her breasts seemed to have swollen slightly under my touch. Her nipples were certainly paying attention to what I was doing.

For that matter it wasn't only her breasts that were reacting. Those lower curves and shapes were also paying close attention to what was going on. I could almost see her legs drifting slightly further apart.

I ignored Jennifer's muttered protests, continuing to give her a nice little massage, one that I was sure would relax her and help her sleep. A real boy scout was what I was.

Now some people might think I was being inconsiderate ignoring Jennifer's protests but you must remember that Michelle was right there in the room, even if she was asleep. All Jennifer had to do was make a slightly louder protest and Michelle would have been stirring and I would have been going while I remained healthy. No loud protest equalled no protest in this instance and so I felt quite free to stroke some lovely curves and to explore interesting places.

I will admit that there was nearly a very loud protest when I accidentally brushed against Jennifer's clitoris. Fortunately her small scream was muffled by the hand pressed against her mouth. Equally fortunately, so were the next couple.

Disappointing though it was to realise that my work was almost done I set forth to do a final bit of teasing and tempting. Jennifer made a couple of very peculiar noises and then grabbed her pillow and slammed it down over her face.

After that she seemed to throw a fit on the bed, bouncing about and screaming. It turns out that a pillow is an excellent muffler for loud noises.

When Jennifer finished bouncing about I lifted up the front of her pyjamas top, dropped a light kiss on each lovely breast and departed, wishing her a pleasant night as I left.

Saturday passed much the same as Friday. The girls went about their business and I went about mine. For some reason or other our paths just did not seem to cross. That night when I went to bed I found that the girl's door was closed and the light was off. I considered for a moment and then tapped lightly. I waited a moment but there was no answer, so I tapped a second time, not much louder than the first.

The door opened a crack and Jennifer glared out at me.

"Go away," she said.

"No," I promptly replied. "Let me in."

"You can't come in. If I let you in you'll molest me. I'm not having it."

Molest her, indeed. She could have made me back off at any stage and we both knew it.

"I'll give you a choice," I said softly. "Let me in and I'll just give you a nice back rub and then go away. Alternatively, come with me to my room and I'll give you an all over massage, but you can probably guess how that will finish up. It's been hard walking away the last two nights. If you're in my room I won't have to walk away."

She flushed quite nicely.

"I am not going to your room and I'm not having sex with you." It was a flat statement with no room to argue. Still, it left me the option of giving her a back rub. I pressed lightly against the door and she backed off, muttering to herself. I entered, flicking on the light as I did so.

"Back rub only," she said, looking nervous. "I'm going to be lying on my stomach, I assure you."

"That's OK," I told her. "I wouldn't dream of disconcerting you. Ah, it will be easier if you're naked," I added, almost as an afterthought.

"No way am I getting undressed."

"Why not? I've already seen every lovely inch of you. Tell you what. Seeing you're uncertain we'll wake Michelle and explain about the previous massages and see whether she feels that this one should be dressed or undressed."

"Are you crazy? I'm not waking Michelle."

"In that case. . ." I said softly, letting the sentence trail away as I reached out and tweaked at her pyjama trousers. They were still too loose and baggy and slipped past her hips without a problem, leaving her gasping and grabbing too late. She glared at me but I just smiled and started lifting her top up. Resignedly she let me take it off, casting nervous little glances at Michelle while she did so. Finally naked, she hastened to lie face down on the bed, her face glowing a nice red.

"Why are you doing this?" she demanded to know.

"Because it's fun and you like it," I replied.

"It's not and I don't."

"Then why did you answer the door when I knocked? Very lightly knocked, I might add. Why not just pretend to be asleep."

She threw me a nasty look but didn't say anything. I started to rub her back and she let out a little groan and seemed to just about melt onto the bed. Things went much the same as for the first night. I rubbed her shoulders and back, with my hands slowly moving down over her bottom and finally finished up stroking that happy little area between her legs. I hear another little groan and her legs slowly moved further apart.

I lightly massaged and teased and probed where I probably shouldn't have and Jennifer seemed to be tensing up slightly. I changed the direction of the massage, moving back up over her bottom, along her back and onto her shoulders. My hands moving sideways I found myself rubbing the edges of her breasts where they bulged out either side of her, stroking them, slipping my hand between them and the bed, dragging my hand back, feeling her nipples rubbing against my palms.

Slowly moving back down to her bottom, tracing light circles on it with my fingertips, then dipping down, following the curves, seeking the source of the heat I could feel. Once more some more intimate massaging, feeling her start to tense up again.

"Roll over," I told her, lifting my hands away.

"No," was the immediate reply, but I just waited. With an irritated sigh she rolled over. "You said just my back," she accused.

"So sue me," I murmured, my hand closing over her mound and squeezing slightly. I continued to rub her mound while my mouth reached for, and found, her nipples. I kissed her breasts, tasting them, tasting and teasing her nipples.

I could feel her excitement building so I moved my hands away from her earthy treasures, moving them up to fondle her breasts, giving her excitement and arousal a chance to die down.

By this stage I'd been teasing her for a little while, slightly longer than the earlier sessions. She was getting puzzled and a little frustrated.

"What are you playing at?" she demanded, writhing a little on the bed, wanting me to touch her properly.

I didn't even try to pretend that I didn't know what she was talking about.

"It's called climbing the stairs," I told her. "The idea is to build up your excitement and then stand back for a moment, effectively taking a step down. A bit more excitement each time, but each time I stop there goes that backward step, calming you down. The idea is to see how long I can prolong this. Doing it right I should be able to keep it up for ages."

"You stop it," she said, breathing hard.

"Mm. There's three ways of stopping this. First, I just back way off, letting you finally relax. Second, I increase the pressure, forcing you up and over the edge. I'm in favour of option three, myself."

"What's that?" she demanded. Silly girl.

I stood up and unzipped, my erection standing tall.

"Option three, I finish things properly," I said calmly. "Are you going with option three?"

"No!" she exclaimed. "You promised."

I hadn't really, but if she took it that way what could I say?

"Then why don't you defend yourself by holding me while I go ahead with option two?"

I placed her hand on my cock and her fingers closed around it. She was looking appalled at find herself holding a cock but she wasn't going to let it go and have it attack her. I settled onto the bed beside her, my head bending, seeking my target, and it wasn't her breasts I was looking for this time.

My mouth closed over her pudenda, my tongue starting its dangerous work, darting inside her and moving around quite freely. I could feel the increase in her excitement by the increased strength of her grasp upon my cock. I poked and prodded and generally teased her. It wasn't going to take much effort as I'd already had her close to climaxing a couple of times already.

One last poke in the wrong place, or the right place, depending on your attitude, and Jennifer climaxed again. She was using the pillow again, I noticed, which was fortunate or it could have been quite noisy. She sagged back down onto the bed, totally wasted. I carefully pried my cock loose from her grip. She'd apparently decided to keep it.

I stood up and looked down at Jennifer. She was looking up at me with a slightly dazed expression. Oh, my error. She was looking at my cock with that slightly dazed expression. I was about to drop a kiss on her and leave when a voice spoke up.

"Geez, put it away, man. Have you been fucking my best friend?"

I glanced over to see Michelle awake and watching us.

"Not guilty," I said quickly. One does not want to irritate little sisters. They can be murder. "She was just feeling restless and I gave her a little massage. Ah, she was curious about what my erection looked like. She'd noticed that I'd had one. If you'd been watching you'd have seen for yourself."

"I was watching and that wasn't what I saw," came the pointed reply. "Why didn't you take the cock option, Jennifer? You can see it wants you."

"I couldn't do that. He's your brother."

"Exactly. I couldn't do that because he's my brother. He's not your brother so there's nothing to stop you."

"But, but, won't you mind?"

"Not if I get to see it happen. I'm just as curious as you about things like this. I thought for a moment I was actually going to see you get popped."

"You still can as far as I'm concerned," I pointed out, trying to sound totally casual.

"Oh god, I'm still a virgin, you know."

"You won't be after that thing sinks in," Michelle said. "Think of it as getting an education and helping me to learn more about sexual intimacy."

"Do you really expect me to have sex with your brother while you lie there and watch?"

"Uh, yes."

"I couldn't. I'm sure I couldn't."

"Actually, you won't have to do anything to start with," I told her. "Just lie there and I'll start things off for you. You don't even have to agree. Just stay silent and I'll take your agreement as a given."

I moved back towards the bed, dropping my trousers as I did so. Jennifer's eyes seemed to widen slightly as she watched me but she didn't protest, just lay there, watching.

Sinking onto the bed next to her I took hold of an ankle and moved her leg well to the side, pleased to see her automatically doing the same with her other leg, leaving her completely available to me. A slight shift of position and I was kneeling between her thighs, my cock standing out firmly, hovering slightly above her. Jennifer's eyes were now firmly fastened on that weapon of intimidation but somehow she failed to look intimidated.

What with the earlier foreplay and climax she was well and truly ready to receive me, just not knowing it. I stoked the head of my cock back and forth along her slit, getting it wet with her juices and encouraging her lips to purse a little more. Finally settling into position I eased the head of my cock forward, first pressing against her soft lips, and then moving past them as they happily yielded.

Michelle, to my amusement, had also moved over to the bed and was sitting on it. Seeing and feeling my cock making its move Jennifer gasped and gripped hold of Michelle's hand. I have to admit that Michelle seemed dead keen on watching what happened.

Leaning into Jennifer a little I went slightly deeper and now my cock was pressing against her hymen. She made a nervous squeak and I paused, ready to pull back if she panicked and said no. She didn't. She just held her breath, clutched Michelle's hand, and watched to see what happened next.

I didn't try to just bull my way through. It might be effective but it could also be painful. I pulled back a little and returned. Not really thrusting into her but going through the motions, letting her arousal build slightly. Then with one of those little motions I pushed a little harder, Jennifer squeaked again, and my cock started its journey down her passage.

Ashson
Ashson
8,545 Followers
12