Grief Relief

"What...?" I said, wondering what she was up to, knowing there was no time with the kids around for us to do anything if her motive was, as usual, sexual.

I ran my hand over both arse cheeks then brought my fingers together to run them up and down in the crack of her arse ... surprised to feel something very hard at the centre between her cheeks.

"What the hell is that?"

She had a mischievous grin, "Slip your hand up under my skirt and find out."

I ran my hand down over the backs of her thighs until my fingers found the bottom hem of her skirt. Pulling it up, I slipped my fingers onto the bare skin of her thighs, sliding all the way until I felt the smooth lycra of her panties. Into the crease of her arse and there it was, something hard and round. To assist my curiosity, Penny turned away, presenting her back to me and lifting the back of her skirt, holding it up high around her waist and out of the way.

I looked at her arse encased in the panties, saw the bulge of that hard round object. "What is it?" I asked.

"You have to find out for yourself."

I reached up to the elasticised waistband of her panties and pulled them down off her cheeks, spotting an emerald gem at the end of some object that looked to be protruding from the tight confines of her tightly clamped cheeks. I touched it, even pushed on it ... the latter getting a verbal response from the woman who wore it, "Ummm!"

"Is this one of the sex toys you mentioned the other day?"

"I guess it could probably be called a sex toy Bobby. Don't you know what it is?"

"No," I admitted.

"You have led a sheltered sex life, haven't you little brother?" Penny peeped out of the kitchen window again to check that my kids were happily occupied out in the backyard, "Pull on it, Bobby. Take a hold of the emerald stone and pull it out of me."

I took a hold of the emerald and pulled, but initially it wouldn't budge. "You'll have to pull harder than that, but once it starts to release, do it slowly."

I took hold and pulled quite firmly, feeling it begin to dislodge from its secure resting place. "Ooh!" my sister exclaimed and I saw a very narrow bit come into view, followed by a wider section ... while I may not be familiar with this toy, I knew enough to realise that it would have been this wider part passing through her sphincter that caused her to gasp.

I kept pulling on it slowly until her arse at last released it, the remainder of it in the shape of a cone, sliding out easier until I held it in my hand. Looking upon her bare arse, I could see her anal ring distended, opened up by having had that emerald toy inside her.

"That's a butt plug Bobby that you hold in your hand. Now I've given away my little secret, what my special treat for you tonight will be."

"I'd already made a fair guess at it."

"Did you, I guess I talked about it too much, didn't I? I stuck this plug in a couple of hours ago and I'll keep wearing it all afternoon and evening. So by the time you take me to bed tonight, you should find it easier to slip your cock inside my arse. You're going to have anal sex for the first time tonight Bobby, are you excited?"

"Yes I am actually, Wendy and I never talked about it, as far as I know she never even thought about it. I guess I have, buddies have told me how good it is, but they did say never try with an inexperienced woman ... do it with one who has done it before and knows what to expect."

"That's me little brother, I've done it a lot. Richard loved being in my arse, so I had to like it. But fortunately I did, and I will just love having you cum in me tonight."

She straightened up to take another peep out the window. Appearing satisfied that the kids were still occupied outside, she bent forward again, her hands pulling each cheek wider apart to expose her anal ring that was already starting to shrink back to normal size. "We better put it back inside me, can you do that Bobby? Just slip it in at the same pace that you removed it ... that was perfect. Don't be put off if I wince or sound in pain when you push the thick part through my sphincter."

I did as my sister asked, placing the cone tip at her anal ring and gently pushing. I needed to exert a little more pressure as the plug widened and she did gasp quite loudly when I firmly pushed the widest part through her tiny pucker, "Ohh, oh my God." I kept pushing and the narrowest part lodged tightly inside her and I tapped the emerald stone on the end to check it was secure again. I reached down to pull her panties back over her arse cheeks and she dropped her loose skirt. My sister was decent again, she straightened up. "So what do you think?"

"That's great sis, thank you for going to so much trouble to make it special for me tonight. You know, I'm a little sad today, I'm going to miss you being here."

"You're going to miss the sex, that's what you'll miss."

"No really, I'll miss having you around, it's been so good bonding with you again. You've been an enormous help to me." I paused, "...and you're right, I will miss the sex too."

She turned and came forward to give me a warm hug, "Oh Bobby, I will too. I know I said we wouldn't do it anymore, but I'm already thinking that I might have to come and stay over one night a week. This has been so good this week that I can't just stop now. We might have to wean ourselves off each other."

The look on her face told me she wanted to be kissed so I did. It was intense, lips apart from the moment ours touched. A lot of twisting tongues and grinding lips, hands roaming over arses, bodies in front pressed tightly together so she would feel my growing erection against her belly.

At last we separated, "Oh God, I wish you could bend me over the kitchen table and take me now. Damn, I don't want to wait until tonight."

"Neither do I sis, but we have to. We can't take any chances with the kids around."

"Yes I know, you're right. A clean break ok, step apart and keep our hands to ourselves."

I stepped away, then walked away, my head full of anticipation about tonight after seeing and touching her butt plug. I was amazed as I thought about the things that my sister had told me about her sex life with Richard. I never had any idea what went on in her marriage behind closed doors.

If we thought there had been a lot of sexual tension in the air around us these past three nights, then it was nothing compared to how we both felt this Sunday evening as we attempted to busy ourselves, firstly with dinner, then cleaning up, giving the kids our time to ensure they went to bed as happy as we could possibly make them given the circumstances.

By 9.30, I sat in front of the TV, waiting for Penny to reappear after putting my kids to bed, my body tingling with anticipation. She seemed to take ages, but at last she came into the living room wearing her long fluffy dressing gown. She walked right up to the sofa where I sat and stood in front of me. She looked much taller and I looked down to see that she was wearing very high heels. It looked odd for her to be wearing stilettos with her dressing gown.

"Are you ready for this?" she asked and I stared curiously at my sister without an answer. Her hands pulled the knot out of her belt and reached up to pull the two sides of her gown apart. The vision exposed took my breath away in a rush. My sister stood before me in a black push-up bra, the half-cups making the mounds of her smooth breast flesh even more round and pronounced, the lacey material of the cups failing to conceal her magnificent nipples. At her waist, a black garter belt from which long thin suspenders hung tautly down to attach to black stockings that rose to just above mid thigh, leaving an expanse of bare skin on upper thighs and even part of her hips. Her black lace panties were high cut at the sides ... see, I do know some things about women -- sexy women, I know what high-cut panties are. The high stilettos that she wore accentuated her long legs beyond belief, causing the roundness of her arse to become even more prominent.

What a vision before me. I had discovered how beautiful and sexy my sister is these past few days, but tonight I was seeing an even more appealing image of her. "What is this, where did all of this come from?" I asked, certain that she hadn't brought it in her luggage when she first arrived or surely I would have seen it all by now.

She dropped the gown to the floor and pirouetted on her high heels until she was facing away from me. She was close enough that I was able to reach out and run my fingers caressingly over the large expanse of butt flesh revealed by the high cut of the panties. "That will all be yours shortly, my darling brother."

I brought my fingers around to the cleavage of her arse and followed the lacey material down into the crack, finding the hard shape of her butt plug still in place. Continuing over it, my fingers traced a line down between her thighs, causing Penny's feet to quickly shuffle apart to grant access to my wandering fingers. My fingers touched the crotch piece of her panties at where her vaginal entrance would be, concealed by the material that I found to be sopping wet ... saturated already by her flowing juices.

"You know that I said I was going out shopping this afternoon..." she began to explain.

"Don't tell me you went to the shops to buy all of this?"

"No Bobby, I lied, I didn't go to the shops. I drove home and rummaged through my lingerie drawer, looking for the finest pieces that I used to wear regularly for Richard. He bought me heaps of sexy underwear over the years, he loved to see me dress in my finest lingerie when we had special nights."

"No wonder," I told her, "so do I ... sis, you look a million bucks. But tell me, what were special nights?"

"Oh, that's when he'd have us do some of our kinkiest things. We used to send the twins to mum's so we could have the run of the whole house for whatever he'd have us get up to."

"What kind of things sis?"

"Let's not go there now, I've told you a few little bits these past few days so let's leave that in the past now."

"Did you like doing them?"

"Most of them, those I was unsure of at the start I mostly learned to like. Come on Bobby, I don't want to go there now, I only want to concentrate on you."

She spun back around to face me and leaned forward to place her hands on my knees, the two huge mounds of breast flesh inches from my face, my lips. "Are you up yet?" she asked as she moved a hand to test the obvious bulge in my trousers, "Oh God yes, you're huge Bobby."

"Natural reaction sis, all the anticipation all night, and now this. There's no way I could keep it down."

"Oh baby, we are going to have such a good night. You know we won't get any sleep tonight, I'm going to work you until I drain all of the sperm from you."

Her words reminded me of the question I kept meaning to ask these past five days, "That reminds me Penny, I trust that you're still taking contraceptives? I mean, you surely didn't stop once you lost Richard?"

"Yes I am Bobby. No, I didn't stop ... I did think about it at first. You know, as you are now discovering, when you lose your life partner, you go through this feeling that your sex life is over. But before I made a decision to stop taking the tablets, common sense had begun to kick in. I realised that my sex life had been so active with Richard that I would just have to find a man with comparable needs and wants. And see, temporarily I've found you. While I could be content for us to do it with each other for the rest of our lives, I know that can't happen. But my darling brother, even though you don't think so now, in time you will find another woman who will look after you as well as Wendy did."

"I sure hope so."

"Oh God, let's not get too maudlin around here." She bent over to retrieve her gown from the floor and put it back on, "Bobby, we have been so careful around the kids these past few days, each night giving ourselves a buffer zone of one hour to ensure they are asleep. I'm not about to take the risk and ignore that this last night, so my darling brother, I'm covering all of this up for another..." she glanced across at the clock, "...55 minutes, and counting."

She sat down and nestled her head into the crook of my neck and we both watched TV for the best part of the next hour. I don't know how much of the show Penny took in ... I can tell you I had no idea who any of the characters were or anything to do with the plot. My mind was racing, reflecting on the vision I had seen when my sister took off her gown, thought about how good her body looked in all of that sexy black lingerie. She lay here up close to me, only her gown preventing me from seeing and touching. I thought too about the guarantee that tonight my erection - now straining within my trousers, the tight skin of it feeling like it may burst from the hard intensity of it - would soon slide up inside my sister's arse. What would it feel like? I'd been told by buddies how tight it gets inside a woman's anus.

That must have been the longest 55 minutes either of us had endured. When the clock at last ticked over, Penny lifted her head and turned to look at me, "It's time little brother, are you ready?"

I nodded but when she stood up, instead of us heading off to bed together, she told me, "You go to your room ... our room darling ... I just want to make sure the kids are asleep. I'll join you in a tick."

So I made my way down the hall on my own, entering my bedroom, heading for the bed, my head a mix of sad and happy. So full of anticipation that my sister was about to introduce me to something new sexually but my joy there was tinged with regret that this was to be our last night together. We had brought each other such immense pleasure at a time of such intense grief ... my grief probably more so than Penny's because it was so recent and I was still pained by losing Wendy.

I turned on the bedside lamp and began taking off my clothes. I had got down to only underpants by the time the incredible vision of my sister appeared in my room, her arrival signalled when I heard the click of the bedroom door as she closed it behind her. I looked up to see that she had already discarded the dressing gown, probably back in the bedroom she has been using.

She slowly walked toward me, all of her bodily parts accentuated by the up-thrust that those high heels provided to her legs and arse. My eyes took in the two mounds of breast flesh pushed up to extreme twin globes by that special bra, the sexiness of the garter belt and those long, long suspender straps that secured her stockings, the high-cut panties that exposed so much bare skin of her hips. A vision in black lingerie and all mine to make love to.

By the time she came from the door to reach me, I had let my last garment drop to the floor, pooling at my feet. I stepped out of my underpants and greeted my sister totally naked, my erection completely horizontal to my body, straining to be inside her wonderful body.

Penny took hold of my hard-on and her palm and fingers stroked its length gently. I eyed off her bountiful breasts, so roundly presented ... unable to resist an urge to suckle them, I reached out to pull her warm body to me and lowered my head. My lips latched on to a nipple, blatantly exposed, unable to be contained in the tiny half-cups of her bra. I licked and sucked and grazed with my teeth the taut nub of her nipple, but before I felt I had done that one justice, my sister demandingly used her hands to pull my lips over to its twin and orally, I got busy, lavishing pleasure on her second nipple.

I made a decision to release her wonderful breasts from their pushed-up state, I wanted them to move easily as my lips and tongue roamed over the smooth abundant surface. I reached my hands around to unclasp the bra in back, freeing them, her breasts bouncing against my cheeks. Meanwhile, in the tight press of our bodies, my erection had become squashed between two bodies that craved the tight press of close embrace. "Oh, I could have you do that all night," my sister proclaimed, "but you'll have to wait until later little brother. I want to get to the good stuff now, I want to feel your cock inside me."

"Where inside you?" I asked, checking to see if her anal intentions were still as keen as they obviously were earlier in the day.

"Everywhere my darling brother, I want to warm you up in my cunt, and then have you cum in my arse." Once more, my sister's choice of words stunned me ... on our first long night together like this, I heard her say the word fuck for the first time in describing what she wanted and now on our last night she has adopted the crudest word to describe her vagina.

I reluctantly tore my lips away from lavishing love on her nipples. "Come on Bobby, I want us in bed." She broke out of our embrace and turned to clamber onto the bed, once again presenting me with that alluring sight from behind, seeing that bum as she crawled to the middle of the bed. Only this time, she was still wearing panties and I spotted the shape of the butt plug, still inside her anus to loosen that entrance for me.

By the time I joined her on the bed, she had rolled onto her back and was waiting eagerly for me to join my body with hers. I hadn't expected her to want straight missionary sex first, anticipating that after all her planning we would go straight to my introduction to anal sex.

I attempted to lavish more lips and tongue on her breasts and nipples, but she wanted none of that. Instead, her hands were forcing my head lower, indicating quickly where she wanted to next feel my lips and tongue. I had no preferences, I was just happy having found this kind of connection with Penny. I went with her hand's guidance only to find her panties still concealing her pussy. I took a firm hold and eased them off her, then applied my lips to her emerging clitoris, sucking and licking with great affection.

My guess was that my sister was at a peak of sexual craving this night. She didn't take long to cum from my lips and tongue stirring her clitoris to a pounding climax. Having given her the first orgasm for the night, I brought my head back up to hers so I could kiss her once more, particularly with her juices still lingering on my lips, tongue and chin.

She was eager for me to be inside her now and one hand got busy pulling me to her vaginal entrance. Once fitted there, her hands grasped an arse cheek each and pulled, urging me to fill her. I slid through her tight passage easily, her juices flowing so liberally to ease my way in. I was prepared to pause and enjoy, reflect on the remarkably good feelings that her tight inner lining gave to my hard shaft. But again, her pursuit of pleasure was single-minded, conveying quickly her need for me to be thrusting.

I accommodated her demands and soon had her whole body humming as another orgasm consumed her. Ever conscious of where I had expected to be encased in her body by now, I ceased all movement while she enjoyed her pleasure peak, wondering when I would get my chance to experience my first anal.

Having now cum from my tongue and my cock in the preliminaries, Penny must have considered that the time was now right to move us on to the main event. "Pull out Bobby, I want to give you your special treat now," she promised, her eyes gleaming with eager excitement and anticipation. "I picked up some lube from home this afternoon, it's on the bedside table. Spread a lot on, you'll need plenty and then you can do me too."

I withdrew as she requested, thinking how unusual it was to pull out of a warm vagina without having cum myself. As soon as we were uncoupled, I on my knees above her, my sister rolled over face down, spreading her legs wide and invitingly, the emerald tipped butt plug glinted in the light from the bedside lamp. "You'll need to remove my plug, but lube your cock up first. Even though I've worn the plug for about ten hours now, once you take it out, my hole will start shrinking back to normal size. So for the best result, leave it in until you're ready, then when you take it out, get the lube on and in me quickly and then slide in while I'm still stretched open for you."