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First time with an older woman.

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By (user no longer on site) OP     over a year ago

I had just graduated from Uni, had a new job but next to no money, and ended up living in digs, as I wasn't keen on joining a house share. My landlord/lady were decent people in their late 30's. I did fancy my landlady, as she was pretty good looking, but it didn't seem a good idea trying anything on. Much later, something nearly did happen, but we both shied away from going through with it. Their son had a schoolfriend, and they would often go out for a drink with his mum, who was older still by a few years as she'd had her son quite late on. She was quite a looker, blonde with an hour-glass figure. I should say that I was generally very much into the idea of older women - had fancied many of my mum's friends, had a lot of fantasies about them coming on to me but that's all they were - fantasies.

Sometimes I was invited along to the pub with them all, and on one occasion the woman, Lil, was dragging behind a bit with my landlady on the way back afterward, and I heard her talking about the soldier she'd taken up with the previous summer when he was home on leave. Of course, I priced my ears up, because she would be much older than any squaddie, and this interested me. Then I heard her say out loud, that she was lonely in bed and needed someone to cuddle. I couldn't help wondering if she said that for my benefit, but wasn't sure how to find out. Any false move I felt and she would probably tell my landlady about it, and I would never live it down. Also, I was no virgin, but then still relatively inexperienced with girls. I'd had a few girlfriends, but never any who were any more amazing in bed than I was.

But I was intrigued, and felt I had to try and follow it up somehow. One evening when my landlady and her husband had gone out and wouldn't be showing up I went to the pub half an hour or so before last orders in the hope she might be there, and she was. Seeming like I was there almost by chance, I was glad to se she was drinking on her own, and she readilly accepted the offer of a drink. So we chatted about this and that, and as the pub was closing she asked me back for a coffee. My heart was leaping - could this be the fulfilment of a fantasy since adolescence? It wasn't far to her house, as i walked her home, but it was a cold frosty night already, and we both really needed a

hot drink when we got in. As the kettle boiled she showed me round the downstairs and then we had our coffees and chatted about nothing in particular. I hesitated as she made no obvious signs of wanting to seduce me, and I wondered if I was deluding myself she wanted more. I'd never ever gone from zero to a sexual encounter in one evening so felt practically gauche in the seduction stakes. Finally she looked at me and just said, 'would you like to go to bed with me?'

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By (user no longer on site)  over a year ago

More please keep going

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By (user no longer on site)  over a year ago

good start keep going

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By (user no longer on site)  over a year ago

To which you instantly replied 'No' how dare you treat me like a sex object!!! ..... lol. Only joking. More please, it's sounding good.

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By *eereMan  over a year ago

Gloucester

Good so far ?

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By *ood tongue!!!Man  over a year ago

harwich

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By *opman1111Man  over a year ago

belfast

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By *untimes6969Man  over a year ago

Newcastle upon Tyne

Great start!!

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By (user no longer on site) OP     over a year ago

There's more to come - she was hot!

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By *p519Man  over a year ago

Cork

Very good so far

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By *cfc1965Man  over a year ago

horsham

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By (user no longer on site)  over a year ago

More plz

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By (user no longer on site)  over a year ago

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By (user no longer on site) OP     over a year ago

Thanks to all for the supportive comments. I will resume...

So, when she asked me if I'd like to go to bed with her, I was exhilarated inside, my dream of making out with an older woman was finally going to come true. As I said, she was attractive, she dressed much younger than her age, wearing tight short skirts, and often a tightish blouse too, which showed off a bosom that was obviously impressive, and she had fine hips and a waist that gave her a classic hourglass figure. She really looked fantastic at any age, and I would have fancied her whether or not she would have made my fantasy come to life. It took me nanoseconds to say, with a somewhat dry throat, 'yes, I would love that'. She beckoned me over to the sofa that I'd been sitting opposite, made room for me, and as I took my place by her side we started necking.

As we swapped tongues I fondled her, and for the first time got my hands on her amazing boobs. This night they had been hidden to a large extent by a fluffy angora sweater tied with a belt she'd been wearing, but as I parted it my hands strayed to her tits and I was able to appreciate by feel what I handful they were. Her hands were straying over me too, and I could feel her testing out my rock hard erection, which caused her to murmur approvingly. 'Do you want to come upstairs? ', she asked. Then, sensitively, 'your're sure you won't feel awkward?'. I knew it was now or never. I was in unknown territory, but I had to seize the day. She felt good too, I had to do this, and said,' No I'm sure I won't'. So she led the way up the staircase and I followed at a distance where I could look up her skirt.

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By *orksvoyeurMan  over a year ago

Keighley

I love an older woman well done great story

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By (user no longer on site)  over a year ago

The view up short skirt is all you need to keep you going as you climb the stairs.

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By *ilberryMan  over a year ago

Scarborough

I love the story, and like women older than myself

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By (user no longer on site)  over a year ago

The view up short skirt is all you need to keep you going as you climb the stairs.

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By (user no longer on site) OP     over a year ago

We reached her bedroom, and clinched again standing up. Feeling her beautiful curvy body against mine felt so good, and as I held her close into me she could feel my bulge and keeness pressing against her mound. Though I'm only of average height, she was a good few inches shorter, and her face was looking up into mine as we kissed with passion. I knew she was no shrinking violet and could tell she was as eager as me. By what I'd overheard he saying to my landlady that night a week or so previously coming back from the pub, it was a while since she had seen any action (as it was for me too), and as she massaged my bulge I could tell she was as eager as I was to put that right. We help each other off with our clothes until we were both in our underwear, with me sporting a very impressive bulge, and a cock longing to get free. Only now could I really start to appreciate how impressive her boobs were. I began to fumble behind her to unclip her bra, but she showed me that it could be undone from the front - much more practical for taming those boobies in the morning, and easier for me to free them. And when I did, what a glorious sight! Tits you could get lost in, and I could now see as I'd never been able to appreciate with my former girlfriends how good a tit-wank could be. She had amazing large dark aureolae, her nipples erect at their centres like bullseyes on a target. I cupped each one up in turn and began to suckle her.

At this point it really dawned on me how different all this was to 'first times' with my girlfriends. I'd always been at least a bit in love by the time it came to embarking on a sexual relationship, and that always made things a little sacred and special in a particular kind of way - maybe the start of happy ever after. But here, we both knew we were together for 'just sex' or to satisfy our lust, and I felt this extremely liberating. Of course we liked each other, and felt friendship, but without the 'love' thing, the idea of it being pure lust, as well as the fulfilment of a fantasy felt amazing.

She was still in her panties and I in my underpants, and when she had finally pulled my underpants down freeing my very upstanding cock she wanked me slowly. I then returned the compliment and got her completely naked too after pulling her panties slowly down her lovely thighs kissing the skin where they left, and then, on my knees kissing her very prominent mons, which I loved, and began to finger her pussy which was already dripping wet.

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By (user no longer on site)  over a year ago

More needed x

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By *rodigalMan  over a year ago

sunderland

wow

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By (user no longer on site) OP     over a year ago

As you'll have gathered, Lil was the one to drive things forward. As the older one, I felt easy that she dictate the pace. She soon asked me if I'd like to get into bed with her. She lay back and I climbed between her shapely thighs, which with a little cellulite were about the only thing about her that showed her age. She was wet and ready, and without anymore foreplay we got down to it. I positioned my cock head at the entrance to her pussy and pushed... I sank in easily and as she was so wet, I was pushing my whole length inside her almost immediately. As I thrusted inside her I watched her tits giggling beneath me, and gazed into her eyes which looked back at me, while she murmured gently. I was just getting into a rhythm when she surprised me by asking if I could get off and lie on my back as she would like to go on top. Such was my inexperience that I'd never done that with anyone before, but I readily agreed. I lay back and she straddled me and then arranged my cock back at the entrance to her pussy and eased down on to me. I just loved this, and ever since it has been my favourite position. Somehow I'd never imagined an older lover being so energetic, but she was quite fit and rode me hard, sometimes slowing it and leaning back as far as she could. I am quite well endowed, a good length, but she told me that she wanted the extra penetration that she could get from on top, and it felt so good for me too being so deeply inside her as she moved and gyrated on my cock. As she moved up and down on me, I could see my cock slicked with her juices moving in and out of her lovely labia - proper love-flaps - and with my hands free I could cup her gorgeous tits as she continued to ride me. Though I would meet her movements by thrusting back into her, it was clear that it was her fucking me much more than me fucking her, and I was enjoying every minute of it. The thoughts rushed through my head as to how this was not only the fulfilment of my adolescent dreams, but surpassed them in every way. Even today, this remains my all time best first time. I did not last all that long really - I was just so excited and must have come after only five minutes or so, but though I could feel my cum exploding into her vagina, thankfully I was also so turned on that I remained hard, and could stay so until she finally shuddered with her own orgasm and subsided sweaty and exhausted on top of me. I kissed her tenderly, because you need that afterwards, and also in thanks for a unique experience she had given me.

She got off me and laid on her side, and we cuddled some more. She asked if I would stay all night (and it was about 1 am by this time). It was no problem to agree, apart from a niggling worry that it would be embarassing if her teenage son was up when I left as he'd know what had happened. But the bed was warm, and so was she, and I couldn't help hoping that we might get another round in before I left in the morning....

(to be continued)

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By (user no longer on site)  over a year ago

Love the older woman. My first sexual relationship was wit my neighbour when I was in my teens and she was late 40's. Ended up being with her for 7 years

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By (user no longer on site)  over a year ago

Nice, and it's good if you can carry on a couple more times in the morning before you have to leave.

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By (user no longer on site) OP     over a year ago

She turned the light out and we dozed off. Before I knew it, though, perhaps it was barely half an hour after we had shagged each other senseless, I woke to feel her under the covers, taking my limp cock into her mouth. I turned the light on, and lifted the duvet to see her, taking me in her mouth, sucking me back to life. She looked up at me, with a greedy look in her eyes and I knew that she was intent on me fucking her again. It didn't take than much for me to spring back to life, and I knew that I would soon be inside her again. I caressed her face and wound her long blonde hair around my fingers as she sucked me, feeling my cock harden more and more under her attentions, and feeling more and more randy as the thought of another delicious fuck rose in my mind. None of my girlfriends had been eager like this, and I realised that my idea of women as having to be coaxed into sex was all wrong, that there were women like Lil who wanted it just like us men. It was in a way like going up to heaven, a universe constructed in a different way to what you knew. Or that I had struck upon a genuine nympho, that they really existed. As soon as she had me good and hard she straddled me again. By now I knew the score, and as she rode me hard again I just thrusted into her hot warm snatch enjoying every moment. As it was not so long since I had cum the first time , I lasted much longer. i went through all the same sensations as before but had so much longer to linger over every move she made on me, and to respond back as much as I could. I savoured all her curves, moved with her every move, and felt joyous at the way we were satiating our lust for each other. This time it seemed as if the moment lasted forever until I could tell she was near to cumming, and at the same time could feel my spunk rising. I can hardly remember what we said to each other, not all that much, as we were so engrossed in the sheer joy of fucking again. I came just before her this time, but again hung on until she again reached her climax as I penetrated so deep I could feel her cervix, and again we collapsed together in a sweaty heap. Twice in a night was as much as I had ever achieved with anyone, and I thought that that would be that until morning.

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By *outheasthornyguyMan  over a year ago

Guildford

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By *urreyloverMan  over a year ago

Guildford

Well written

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By *oth0712Man  over a year ago

cambridge

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By (user no longer on site) OP     over a year ago

Maybe an hour later, I felt the urge of a call of nature, and got up to find the bathroom. I was still naked, it was cold and I was also anxious not to burst into her son, Kev's room by mistake. The house was a standard semi, and it was fairly easy to work out which door would lead to the bathroom. Being soft after the previous exertions, it was easy to pee, and I got back to Lil's bedroom, shivering, and dived under the cover. She must have been awake, or woken by my getteing back into bed, as she said, 'are you cold? would you like to cuddle up?'. I snuggled up to her, and enjoyed lying against her pillowy bosom - more uses than one (!) - and held her close. She began kissing me, at first chastely, and then as I responded it bacame hotter and in both of us the lust was rising again. Her hand wandered down to my cock and it did not take much massaging to bring it back to hardness. Similarly, I reached to her pussy and bagan to push one then two fingers inside her, and felt she was already wet again. Her very prominent mons fascinated me, and as I worked my fingers inside her I tried to find her g-spot, and she soon began to moan as I worked on her, while she continued to wank me, making me harder still. She whispered in my ear, would I like to spoon her from behind, and as she turned her back on me I positioned myself to plunge my cock slowly between her now gaping pussy lips. As I reached full penetration I held her thighs and rocked with her, and at the same time I could feel the pressure of her hand on her mons while she frigged her clit with her fingers. I kissed her neck and she sighed, 'Oh yes David, I love you being inside me like this'. I loved being inside her too. For all that she had borne two children, she was still nice and tight, and as I moved inside her I could feel how firmly she was gripping me. I brought my hand around to work with her fingers on her clit, and as her breathing got shorter and sharper I started to move more vigorously inside her, plunging in balls deep anticipating her climax. As she started to cum, I went faster, and not long after deposited what little was left in my balls inside her wet cunny. As we caught our breaths she turned back to me and we kissed deeply again as I continued to hold her close. I pulled out and my wet cock emerged, limp as a discloth, much shrunken from its prouder state just moments earlier.

'You are a lot better than my soldier friend,' she said, though I never asked why, but this seemed a huge compliment as I'd rather thought a 9st10 comparative weakling would hardly match up to a fit squaddie, as I'd assumed him to be. Perhaps it was my ability to last, and to make sure I satisfied her was what counted. My experience that night was way beyong what I'd ever dreamed of in fantasy, she was a true sex machine, and I'd never encountered any girl or woman who relished sex so much. I caressed her cheek and said thank you for being so amazing, and we lay back and went back to sleep.

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By (user no longer on site)  over a year ago

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By (user no longer on site)  over a year ago

Cracking read!

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By (user no longer on site) OP     over a year ago

Thanks for all the great comments!

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By (user no longer on site)  over a year ago

Great story

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By (user no longer on site) OP     over a year ago

And it happened again... she was under the covers and had started licking and sucking my limp cock. It was still pretty dark, but I was not sure how long I'd slept since our last bout. I was beginning to think of Lil as something of a nympho, it seemed that she could not get enough cock. I'd never been with someone like that, and the times when I'd had multiple goes it had usually been me pushing for more. I didn't feel my male pride dented however, but felt a bit nervous that I might be found wanting. I turned a light on and raised the duvet cover so I could see her working on my cock, and as she looked up at me smiling I smiled back and wound my fingers in her long blonde hair, gently encouraging her. I was pleased to feel faint stirrings at the thought of more fun with this amazing older woman.

Then she moved, and straddled me in reverse, leaning over and with her lovely big arse waving in my face, so I could return the favour and enjoy 69 with her. As her mouth moved down again on my cock, her pussy moved closer to my face and I began to run my tongue over her gaping pussy lips. She gave me instructions on where to lick, and murmured approval of where my tongue went, though increasingly all I could her was her sluring as she took my slowly stiffeniing and lengthening member deeper and deeper into her mouth. I plcaed my hnds on her hips to steady her and kept licking for all I was worth. I felt her wanking my cock harder and harder as her mouth and tongue concentrated on my bell end. This was deleicious, and I felt like I could maybe endure that forever, even if my tongue might soon wear out, and her juices were dripping onto my chest. She wanted me good and hard, not just semi-hard and when she was satisfied she turned around again, facing me, straddling me still and positioned herself so my cock was close to her pussy again. It was now living a life of its own, jerking up and down off my chest raring to go. I saw and felt her grab it purposefully in her hand and rub my cockhead along her pussy lips repeatedly, teasing me and herself. Then finally, fixing me with her eyes, she found the spot and angle for it to penetrate into her pink hole, and lowered herself once more on me. I watched as her pussy swallowed me till only my balls were left showing, and rode me like a jockey, her legs so surprisingly powerful and energetic as I'd never imagined an older woman could be. She was incredibly wet, and I could see how my cock was slicked with her juices every time she rose off me. I met her movements thrusting upwards as she came down, to penetrate her as deeply as I could, and we were moving so vigorously that sometimes on the upstroke I came out, but she quickly reached back and slid me easily back in. She leaned back and gyrated and I could feel my rock hard cock being bent backwards in an almost painful ecstasy. Her magnifcent breasts sawed again above me. Her nipples were standing proud like bullets in the middle of her large oval aureolae. I played with them, rubbing my thumbs over them, seeing her smiling above me, lost almost in a reverie or trance as she continued to ride me. I kept thinking about how I wanted to fuck her deep cleavage, how my slicked cock would slde so nicely between those magificent tits, but my cock was gripped tighltly inside her hot pussy, and she was in the zone. We both knew that we needed to finish each other off and she rode me harder and faster, and I thrust more urgently until I could feel my spunk rising and I told her I was going to cum. At that she started frigging herself hard, trying to bring on her own orgasm. Her breathing turned sharper, shorter and faster and it was becoming harder and harder now for me to hold off. I had reached th point of no return, and called out, 'oh fuck, Lil, I'm cumming'. 'Yes, cum in me, cum in me now', she said and she collapsed on my chest as I hammered my cock into her pussy for all I was worth until the wave of orgasm ran through me. I had already spunked so much into her that night, that it felt different, as I was less aware of the spunk spewing forth as the orgasmic brain waves that ran through my head. I felt well and truly shagged and just lay there as her blonde hair tumbled over and around my face, and she kissed me softly.

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By *cfc1965Man  over a year ago

horsham

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By (user no longer on site)  over a year ago

Phew!!! Wonderful. So hot.

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By *ichaelxx11Man  over a year ago

Gloucester

Nice. Really nice

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By (user no longer on site) OP     over a year ago

Must have gone fast asleep after that, and I woke to see chinks of light through the curtains. I looked at the alarm clock next to the bed, and saw that it was nearly 7am. I felt I needed to go, as I didn't want to bumo into Kev, her 15 yo son on the way out. As I began to move, Lil strirred. ' What are you doing?', she asked. I told her I needed to be going, how much I'd enjoyed the night. She leaned over and kissed me sweetly, and said she'd enjoyed it too, how it hade been so long since she'd had anyone. 'Could we do it just once more before you go?', she asked me. I had morning wood, and could hardly deny that I couldn't get it up. She had put a nightie on since we'd last fucked, but as she sat up and opened the front and I saw her tits bared to me, I found her just irresistable, I sat back on the bed and we started to nog again, my hands roaming on my tits and her small hand around my cock wanking me to another full erection. I fingered her pussy and found her wet again so pushed her back and mounted her. She didn't insist on going on top this time, maybe as I was being more forecful, but as I positioned my cock ready to plough her love hole, she placed her legs around my back and drew me in. I went in in one go and started to fuck her like crazy. As I hammered into her, her huge tits jigged back and forth in time. "yes, fuck me David', she cried. 'Dont stop'. I kept fucking hard and roughly, hearing her whimper beneath me. Again I heard her breathing shorten, she seemed to go almost into a trance, her pussy that must have had a fair number of lovers before me still tight, hot and gripping me. 'Keep going, don't stop', she repeated, and I just kept fucking her forall I was worth. I ground my pubic bone against her mons. "mmmm oh yes,' she cried, and then long strokes, almost coming out but slamming back deep. She was now moaning, and then I began to feel her pussy begin to convulse beneath me, and with one final thrust I fel my balls tightne and then empty themsleves inside her. I flopped on top of her, gained my breath and then closed my mouth over hers as we exchanged tongues again savouring the moment. I pulled out and laid beside her, my cock now well and truly limp. She placed her hand on it and gave it a gentle squeeze.

I said, I really must go....and she said, 'Ok, but will you promise you'll come and see me again?' I promised, why wouldn't I want to make out with her again. (Not tonight though, I said to myself, as I'd find myself shagged to nothing). If next time was to be anything like the same, I'd need to get my strength up.

I dressed and she accompanied me downstairs in her nightie and a fluffy dressing gown. Fortunately, no Kev in sight. As she let me out of the front door I leant down to kiss her and she hugged me close, and again made me promise to see her again soon. I walked donw her garden path and turned to see he still looking, and blew her a kiss to wave goodbye before walking the half mile to my digs and trying to let myself in quietly as if my landlady saw me it would be obvious I'd been out for a night on the tiles, and I didn't want to have to answer any embarrasing questions. I was too tired to go to work so when it got to 8.00 I phoned in and said I seemed to have a cold, and then slept the rest of the morning.

(To be continued)

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By (user no longer on site)  over a year ago

Wow!! Amazing story mate

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By *cfc1965Man  over a year ago

horsham

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By (user no longer on site)  over a year ago

Well and truly shagged out... mmmmmm.

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By *aseyjones7Man  over a year ago

leicestershire

Great story . I wanna hear more.

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