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The Older, The Better

Category: Mature
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Some years ago I worked at a small engineering firm. One of the typists there was called Barbara, and she did most of the typing for me. I was about 25 at the time and she was coming up to retirement. She was a small lady, and had put a bit of weight on round the middle. She had quite a large bust which she didn’t try to hide, and usually wore a skirt and blouse. One day we were doing stocktaking and we were in the production office. There was the usual girly calendar on the wall (not allowed nowadays!) which I had a glance at. Barbara came over to me.

“Do you like that,” she said, pointing at the photo, which was a secretary bent over her desk, with her skirt lifted up, showing her stocking tops. She was turning to the camera and her blouse was open exposing her quite large tits, encased in a black bra. I did like it, and I told her so. I was also getting a stiffy, looking at the photo with Barbara being next to me.

“I can see you in that pose,” I said, feeling as though it was safe to flirt a bit. “You’ve certainly got the figure for it.” I looked down at her blouse, which was showing a fair bit of cleavage. “Do you ever wear black stockings,” I asked her. She chuckled sexily, but before she could answer, someone came into the office, so we had to continue with our work, and nothing more was said that day.

The calendar incident was not mentioned again, but from that day, Barbara and I developed a ‘relationship’ in the office, which certainly made it worth while going to work every day. She was a real tease, but never did any more than that. I used to stand by her desk, pretending to check her work, but it was just an excuse to touch her up, which she encouraged, and I’d often feel her tits or press my cock against her. It became a bit of an obsession and I was always popping to the toilet to have a quick wank. Sometimes I used to bring girly mags to work and when it was quiet in the office I’d show them to her. It really turned me on to be able to discuss the models with her. She would delight in passing detailed comment on their ‘assets’. I once showed her a magazine with a picture of Chesty Morgan and she gasped at the size of her tits, wondering how heavy they were. As she said it I came round behind her and cupped both tits in my hands and ‘weighed’ them. I whispered to her “Chesty Barbara”, and she laughed and called me a dirty sod. I often thought about getting my cock out by her desk, but never went for it.

Later that year Barbara retired and left the company and I didn’t see her again till about a year later. She was in town, with her husband, and she invited me to pop up to her house, anytime, for a coffee. About 6 months later I was made redundant and having time on my hands decided to pay Barbara a call. I’d been thinking about her quite a bit and fantasising about what might happen. I decided to take a mucky mag with me, but this time a lot stronger. It had this one set of photos which reminded me of Barbara. There was this oldish woman with a dark suit and blouse etc at the theatre with her chap and she progressively lost her clothes as all these blokes around them were watching. The final set had her being fucked by one bloke and wanked over by four others while her ‘husband’ watched, and the last photo showed her face covered in spunk and it was dribbling out of her mouth. My fantasy was for her to wank me off while we looked at these pictures together.

I’d phoned her a couple of times before and she was still teasing me. She had a very sexy, husky sort of voice. The second time I phoned her I had my cock out and was wanking. She commented that my voice sounded a bit strange but I didn’t tell her what I was doing. Anyway we had arranged a time for me to visit and I arrived at her house at about 2-o-clock. She answered the door and gave me a quick kiss on the cheek, before showing me through to the lounge. She looked very smart, with a dark green jacket and skirt, and an olive-green, silk, high-necked, blouse. I suppose it was a bit old fashioned, but for 61 she looked quiet trim. I commented how smart she looked and asked her if she was going out.

“No, Clive said I ought to dress up for you. Do you like it?” She did a twirl for me. I noticed she was wearing very smart brown court shoes, with a highish heel. I wondered if she was wearing stockings and felt myself getting stiff.

You look great, I said, and then, thinking – go for it – said, “Do your undies match?”

She did the sexy chuckle again and said “Still a randy little sod then? Are you still looking at those dirty mags?”

“Yes,” I said and produced the mag from my jacket.

She took it out of my hand and had a quick flick through. She paused for a moment, looking at a picture of a naked woman lying on a couch. Her head was laid back over the arm and she was sucking the bloke’s cock who was stood behind her. Between her legs on the couch a second bloke was nudging his prick into her cunt. My throat was dry and my own cock was straining against my pants.

“What do you think of this set?” I asked. “She reminds of you dressed up for the office.” I showed her the photos in the theatre and held up the page with the woman’s face covered in spunk.

“I’m surprised at you,” she said, putting the magazine onto the nearby table. Oh shit, I thought. I’ve blown it. “You get an invite from an attractive housewife and then want to start looking at magazines. Wouldn’t you prefer the real thing?”

Before I could answer, she moved away from the table and standing by the fire, she removed her jacket. Her blouse was tight and showed off her still ample breasts. I went over by the fire and took my jacket off. I stood next to her and whispered into her ear.

“You know I’ve always fancied you. All those times, touching you, feeling your tits. You must have known how I felt”

“Yes, I’ve felt that a few times”. She said, looking down at me and laughing. Then she took hold of my hand and placed it on her right breast. “Go on have a feel. Enjoy it. Now we’re alone.”

I ran my hands over her tits, revelling in the sensation.

“Why don’t you try and guess what I’m wearing?” She pulled my hands down to her waist, and I felt the straps and further down her stocking tops.

“Oh, Barbara. It’s a corset, and you’re wearing stockings as well”. I pulled her backside towards me and she kissed me full on the lips. We stayed like that for some time. I could taste the cigarettes that she had been smoking before I got here.

She pulled away and looked at me.

“It’s a basque actually. And it does match. What would your wife say if she could see you now?” She leant forward and traced the outline of my cock with her fingers.

“What would Clive say,” I countered, holding her hand against my cock, rubbing it slowly against her.

Barbara laughed out loud. “He’d probably like to watch. He’s a bit of a dirty bugger, just like you.” She pulled away from me again. “I think we both need to cool down for a minute. Shall we have a drink or shall I show you around the house first?”

Without waiting for an answer she ushered me around the downstairs rooms and then out into the corridor.

“I’ll show you upstairs – in case you need the bathroom,” and proceeded to walk up the carpeted steps. I followed behind her, my eyes in line with her legs.

“I like your shoes Barbara, are they new?”

“Yes,” she replied. ” I bought them especially for today. My others are bit frumpy. I don’t often get an excuse to get tarted up.”

At the top of the stairs I said I did need the loo, so went into the bathroom. “I’ll just be outside,” said Barbara.

Once in the bathroom, I dropped my trousers and freed my aching cock. I sat on the toilet and started to toss myself off. Barbara was only a few feet away. I could hear her walking around the landing. I thought I could hear voices and I called out to her.

“Are you alright in there Jimmy” she shouted. “Do you need a hand?”

I stood up and stood by the door with my cock in my hand. I could hardly speak.

“I’ll be on the second floor. Come up. I need your help with something.”

I got dressed again, and followed her up to the next landing. She was standing by a wardrobe door looking through the clothes which were on hangers. She turned to me and held up a white silk blouse.

“Do you remember this”? I used to wear it work. It was one of your favourites.

I walked over to her and felt the thin material. Barbara then held it up against her. I put my hand out and smoothed the white silk down across her full breasts.

“I’d forgotten just how nice it felt”, I said to her, as I pressed harder onto her tits.

“Just think how nice it feels for me. Why don’t you try it? Go on, put it on. Just for me.” She handed the blouse to me.

“What, you want me to wear this,” I stammered.

“Yes, and while you’re at it why not try some other things.” She went to a chest of drawers nearby and produced a black bra.

I stood there while she removed my shirt and fitted the bra on me. It was quite big, with broad straps, but it felt so good. She then produced some black stockings from the drawer.

“I wore these at work as well. They’re a bit worn but they will do to pad out your tits.” She stuffed several stockings into each bra cup till they jutted out, and then put the blouse on and fastened the buttons.

“Now you need a skirt. Black I think. This is one of my old ones from work. And a suspender belt. Oh no, you’ll need a girdle to keep that under control,” she said pointing at my erection which was jutting out from my trousers. Eventually she had a full set of clothes laid out. “Take off your pants Jimmy. Let’s see what all the fuss has been about.”

I unzipped my pants and stepped out of them and then quickly pulled off my briefs. For a moment I felt very vulnerable in front of her. Almost awkward, with my cock sticking out from below the white silk blouse. Barbara moved round behind me and pressed me towards her, cupping both of my ‘breasts’ in her hands.

“How does that feel,” she whispered. I could feel her own tits pressing into my back. She then moved her right hand down and started to finger my arse. My cock twitched in time to her fingering.

“You like that don’t you? ” Her voice was low and husky. “I knew you would like playing the submissive woman. What you need is a stiff cock in there.” As she said this she pushed one and then two fingers into me. I reached down and got hold of my cock and started pulling at it.

“Now, now,” scolded Barbara. “There’s time for that later. We don’t want you wasting all that lovely spunk, do we?” Barbara moved away and picked up the black corset from the bed. I stepped into it and she slowly pulled it up my body, pressing my cock against my stomach as it was pulled up around my hips. Once in place, my cock was covered up by the black elasticated material and she proceeded to put a pair of black silk stockings on me, fastening the tops to the straps on the corset. Then the old black skirt that she had used to wear.

“Now to finish off you need some shoes. Look what I’ve bought for you from the charity shop.” She produced a pair of white high heels, complete with ankle straps from the wardrobe.

“Size 7, I guessed,” she said. “You look quite the little tart now. Sheer white blouse, with a black bra showing through. Black stockings and white high heels. Perfect. Come and look in the mirror.”

I walked unsteadily toward the mirror. I was shocked and excited by what I saw. The heels looked great and the black bra thrust out darkly against the blouse. I ran my hands over my ‘breasts’ and then down over the skirt feeling my cock tight against the corset.

“Come downstairs now,” said Barbara. “We can have that drink.”

I followed her down the stairs. Walking in the high heels was difficult but the way they thrust my body forward felt really great.

“Sit down Jimmy, or shall we call you Jenny? Yes Jenny, like Jenny from work.” Barbara guided me to the settee, and I sat down. In a few minutes she came out with some coffee and a bottle of brandy.

“Are you ready for your next lesson in being a woman, Jenny?” Barbara said. “Clive,” she shouted, “we’re ready for you now.” I heard a door open upstairs and footsteps coming down the stairs.

“Don’t worry, Jimmy, sorry Jenny. Don’t look so shocked. Clive has been listening to it all. He’s dying to meet you. Aren’t you darling?”

Barbara’s husband had come into the room and stood over by the window.

“What’s this,” he said, holding up the dirty mag, which Barbara had left on the table. “Jenny, come over and here and explain what this is all about.”

Barbara pulled me to my feet and I tottered across to the window on my high heels. Clive had sat down and was looking at the magazine. He called Barbara over.

“Have you seen this. It’s disgusting. Look at the size of this young bloke’s prick. And look at her fanny.” Barbara sat down next to him and started to make comments about the pictures, just like she had done to me at work.

“Now get my cock out,” he ordered Barbara. She leaned over and unzipped him and pulled out his cock. It was quite big, though he was only a small chap, and he had big balls, and as she pulled back the foreskin she looked up at me and smiled.

“Jenny, darling, you hold the magazine for Clive, while I give him a wank.”

I bent down and did as she had asked. This left Clive’s hands free and he put his right hand onto my stockinged leg and ran it up to feel my suspender belt. Then further up to feel my breasts. All this time Barbara was rubbing his large cock backwards and forwards, with long slow strokes. Each time she would pull the foreskin right back and hold his cock erect with the bell end standing proud.

“Now Jenny, it’s time for your turn to be the lady. I’ll hold the mag and you get hold of this big cock.”

I knelt down at the side of her husband and put my hand around his cock, I was surprised how heavy it was. Heavy and hot. I started to wank him off. It felt very good.

“Fucking hell Barbara……..She certainly knows how to handle a cock…….. I wonder how good she is at sucking?” Clive was really into it now and his words came out slowly in between his moans of pleasure.

“Come on then, love,” she said to me. “I’ll show you”. She put down the mag and bent forward, putting her hand over mine. Together we guided his cock into her mouth. As she took it into her mouth she was looking at me, her eyes bright with the excitement of the sex. “Now it’s your turn.”

I shuffled nearer and placed my lips around her husband’s cock. It felt so big and I could hardly breathe as he thrust forward, gagging at the back of my mouth. Barbara pulled me away. “No, you need to bob up and down. Let the knob end slide in and out of your mouth. Like this.” She bent down to him again, her head moving back and forth. “Now you.”

I took his cock into my mouth again, but this time just gently licking and sucking at the first inch or so. Clive’s breathing was getting heavy now and he was urging me on to make him come.

“This will make you shoot your load darling,” said Barbara. “Watch Clive.” She pulled my head away from his cock and then towards her face. She kissed me deeply, our tongues exchanging the salty pre-cum from Clive’s cock.

“You dirty bitch,” he moaned as he grabbed hold of his cock and pulled it just a few times before shooting a hot stream of sperm onto the table and over the magazine. His cock jerked out further short bursts of cum and he slumped back in the chair.

“Now Jenny, rub the spunk all over him,” said Barbara. I reached down and smeared the sticky white cum over Clive’s balls and then further down, pushing one spermy finger into his arse. His cock jerked, and as I slowly finger fucked him, with Barbara whispering words of encouragement, his cock grew hard again.

“Right, you two, now it’s my turn,” said Barbara, and she took me by the hand and led me back upstairs. Clive followed close behind us. We went into the main bedroom and Barbara told Clive to sit on the bed..

“Jenny darling,” said Barbara, “come and help me with these clothes. I want you to take off my blouse and skirt.” I stood in front of her and slowly undid the buttons on her blouse. As I was doing this, Clive had his left hand up my skirt and was rubbing my cock through the material of the corset. I had no panties under the corset and with his other hand he was fingering my arse. Under her blouse Barbara was wearing a brown and cream basque, which thrust her breasts forward. I pulled the blouse from her shoulders and ran my hands over the cups of the basque, squeezing her tits together. Clive was behind me now and as he continued to rub my cock I could feel his own, pressing into me through the material of my black skirt. I was near to coming and Barbara, sensing this, told Clive to sit back on the bed.

I then unzipped her skirt and it fell to the floor. Under the basque she was wearing brown stockings which were held up by suspender straps, and a matching pair of lace pants completed her outfit.

“Now, Jenny, I think you need a slight change of clothes. It really is unfair of us to keep you locked up in that corset. Clive, go and get Jenny a nice matching bra and suspender belt from upstairs.”

When he had gone Barbara pulled me towards her and kissed me again. It seemed a bit odd actually. Here we were wanking and sucking etc, but the kissing seemed the most shocking thing to do. Despite the difference in our ages, I found myself enjoying this strange intimacy and I wanted it never to end. I pulled away from her and then kissed her again. Our mouths were wet and slipped noisily together and apart. I had a raging hard on and just wanted to make to love to her there and then.

Clive came back into the bedroom. He really was a dirty sod – he had the underwear wrapped around his cock and was wanking himself. He stood at the side of us and they both started to undress me. It was wonderful to feel my cock spring free from the tight constraints of the corset. The end was wet and leaking pre-cum. I gasped as Clive reached down and started to wank me. “Come on Clive darling, help her on with the undies first,” she scolded, holding up the bra. Clive put the bra on me and padded it out with the old stockings. Then he fastened the suspender belt around my middle, and reached down for the stockings, which had slipped down to my shoes. He expertly pulled up the black stockings and fastened them tightly in place in the suspender straps.

“Come and have a look in the mirror,” said Barbara. I walked over, unsteady on the high-heeled shoes. The combination of stockings, heels and stiff cock was really sexy. “What do you think Clive?” she asked. Clive kneeled down in front of me and got hold of my cock and pulled it towards his face. “Go on then darling, suck our lady-boy.” His tongue flicked up and down my cock and then he started to suck and wank me. It looked great in the mirror. This seemed to really turn Barbara on. She was breathing quite heavily and encouraging Clive. “I think you really want to fuck our lady-boy don’t you darling? Go on suck him. Fuck him. Oh, God…”

“Jenny,” she whispered quickly, “help me out of these pants”. I turned to her and she leaned forward and kissed me again. Clive’s movement on my cock increased. It was incredible to be kissing Barbara while her husband was sucking me off. “Now Clive, leave her alone for a minute,” she said, taking his hand away from me. I dropped to my knees and slowly eased off her frilly pants and pulled them to the floor. Her wet fanny was now just in front of me. Her cunt lips were quite big and brown and she was very hairy. I put my hands behind her, feeling the taut suspender straps and the tops of her stockings and pulled her towards me, burying my nose and tongue into her old cunt. She smelled and tasted quite strong but I loved it.

Barbara pulled me to my feet and kissed me, savouring the taste of her own cunt juices. My hand went down to her fanny and I started to frig her, gently at first and then more urgently, with finally three fingers pushing into her. She, in turn, took hold of my cock and was pulling it backwards and forwards. We stopped kissing so that I could have a look at what I was doing. I stood back to admire the sight of my fingers slipping in and out of her wet cunt. Barbara was staring at me, her face contorted with lust. “Jenny, please….slower, slower. Please. I want you to kiss me again, down there. Make me come. Quick, lie on the bed”

I lay down and Barbara climbed across the bed and sat astride me. She shuffled up the bed and then lowered her smelly wet cunt onto my face. I tried to lick and suck her but she was in control, rubbing herself across my face. She was shouting out. Suddenly I felt a hand on my cock. Clive was wanking me off with his right hand. Then I felt him fingering my arse. “Now Clive,” said Barbara, “I want to watch. We can come together.” She lifted herself off me, but only in order to turn around to face Clive. She pushed her cunt back down into my face. “Now, lick me, Jenny. Make me come.”

My mouth, nose and eyes were blocked with Barbara’s cunt and arse. I was trying to concentrate on licking her but my attention was taken by Clive who had been fingering my arse. He had slapped some KY jelly on it and the sensation of his fingers slipping in and out was incredible. Barbara had now taken hold of my cock and she was wanking me furiously. I was near to coming, when I suddenly felt Clive lifting up my legs. Barbara helped him, and then released my cock so she could hold my legs up by her shoulders. “Now Clive, I want to see you fucking Jenny. Go on, slide it in to her cunt.” I gasped as I felt his cock press against my arse. He pushed gently in and then out, just the first inch or two. It felt so good. I could feel my orgasm building. Barbara was shouting “Fuck, fuck, fuck….”

Clive took hold of my cock and started to wank me off. With each movement of my prick, his prick was forced against my arse. “Oh my God Clive, now. Do it now,” Barbara screamed. Clive thrust forward and I felt his cock push tightly into me. The sensation was incredible and as he held his cock deep inside me I felt it pulse and jerk with a hot flood of sperm. I came immediately, my body racked with flow after flow of orgasm, my groans drowned out by Barbara as she came again and again, her cunt juice dripping down onto my face.

After a few minutes resting, Barbara lifted herself off me and lay back on the bed. I still felt really horny, and my arse was twitching. Clive’s spunk was seeping out, and the sensation made me start to get stiff again. Clive had sat back in the chair, and he was trying to encourage his wilted cock to grow again. Barbara said we should go into the bathroom to clean up so we all went in there. I was still wearing Barbara’s clothes and still had my heels on and the sensation of walking in the heels had me fully hard again. Barbara chuckled, got hold of my cock and led me over to the sink. She ran some warm water and then soaped and washed my cock.

Then Clive joined in. It was an amazing sensation as they both slowly wanked me with their soapy hands. Barbara then took a hand mirror from the bathroom cupboard and told me to watch. She rinsed her hands and then put the mirror underneath, between my legs. With one hand balanced on the basin Clive lifted my right leg up, still with my black stockings on, so that my shoe was on the toilet seat. I watched in the mirror as Barbara gently pushed a finger into my arse, opening it up, and a thin stream of Clive’s cum dribbled out onto her hand. Seeing this, Clive pushed against me again. Barbara soaped his cock, which was erect again but not as hard as it was before and as he tried to fuck me his prick kept slipping out, but watching it in the mirror was amazing. Before this I had never had sex with a man and here I was being fucked for the second time, and loving it. Eventually Barbara whispered to me that we should swop round, as Clive couldn’t manage to stay erect.

I stood up straight again and Barbara sat on the toilet. The lid was now up. Her right hand was pushing down into her fanny as she motioned to Clive to lean across her. “Now Jimmy, I think it’s time for you to play the man again, seeing as Clive can’t manage”. Barbara’s voice had got lower and sexier. She now had both hands in her cunt, her right one pushing deep inside her and her left rubbing on her clit. Clive lay down across her knees as though she was going to spank him. She told me to take my underwear off and I removed the bra and suspender belt and stepped down out of the shoes, removing the black stockings which by now were stained with spunk.

“Now Clive I want you to suck Jimmy’s cock”. I knelt down by the side of her and Clive started to suck me off. Go on Jimmy, grab his head and fuck his mouth. I did as she asked and found that he could take nearly all my cock in his mouth. “Now Jimmy use the stockings to cover his mouth. No wait” she said, “give them here”. She took them from me and pushed them into her cunt so they were smeared with her cum juice and then we proceeded to gag him with the stockings.

“Now, Jimmy come round here and look at this.” Her husband’s arse was wide open and it seemed to me that he was used to being fucked. I’d never done this with a man before but I wanted to see what it was like and after fingering him for a few minutes I placed my cock against him and just pushed. It went in easily and I was surprised how loose it was. It felt nice though and I started to really bang into him. I was right up him and going for it. It was quite warm in the bathroom and my sweat was dripping down onto Barbara’s face. She was loving every minute of it and mouthing off “Fuck him. Fuck him really hard”. She shouted out loud and then came again, her fingers deep inside her cunt, her wetness dripping into the toilet. Seeing her body shake underneath me, her tits wobbling in the basque, I suddenly wanted to fuck her, and pulled out of Clive. I helped her to her feet and into the bedroom.

She lay back on the bed. I knelt between her legs. Clive had followed from the bathroom. I noticed that amazingly he was hard again. I asked him to help me, and as I lifted her legs he held them up in the air. I looked down at her. Her cunt was dripping wet and wide apart, the lips hanging down. I ran my hands down her stockinged legs, and then placing the tip of my cock against her slit, pushed gently into her. I held my cock there for a while as her cunt twitched around it. I could feel her cunt muscles pressing and releasing. I leant forward and kissed her and then leant back and gently pulled my cock out. It was smeared with her cum. I did this quite a few times. Slowly in and out. Barbara was squirming, wanting me to fuck her but I kept her waiting. Then I quickly thrust hard into her making her scream out. I held my cock in there and then just as quickly pulled out. She gasped and shouted “bastard”. I got off the bed and told Clive to put her legs down.

“Now Clive, lets do her together,” I said to him. “Can you bring the mag from downstairs, there’s something I want to do. I lay on top of her and entered her cunt again. I felt Clive behind me and I stopped my fucking whilst he got himself comfortable. Again I felt that slippiness as he edged into me and then the tightness as he pushed further. It was a bit odd at first but we soon got it sorted. I had got her to bring her legs together so my cock was pushing down into her cunt, which increased the tightness and the sensation. My legs were at the side of hers which meant that Clive could penetrate me more easily from behind. The easiest was for me just to stay deep inside Barbara and as he pushed his cock into me his movement pushed me deeper into Barbara. I reached across for the magazine and opened it at my favourite page. I put the mag across Barbara’s face, so as I fucked her I could look at the photos. Barbara was calling out all sorts of names, but Clive and I ignored her as we talked loudly about what was going on in the photos. I could feel my second orgasm nearing and from Clive’s muffled groans could sense that he was near. Barbara was breathing very heavily and moaning.

“I’m nearly there Clive, shall we come on her face like in the magazine?” I had it open at my favourite photos. We both stopped and Clive slipped out of me and I pulled away from Barbara. Her face was still covered with the mag. I picked it up and asked Clive to pass me the stockings. He pulled them from his face and handed them to me. I then wound them round one end of the mag and pushed it into Barbara’s cunt. She took hold of it and pushed it in and out. The sight of her frigging herself like this sent me over the edge and I jetted a long stream of spunk across her basque. I fell forward and aimed the second spurt onto her face. Clive then pushed his cock into her mouth and tensed as he too dumped another thick stream of cum. I leaned back on the bed and looked down at her. She was smiling and the spunk was bubbling between her lips. I laid beside her on the bed and she kissed me. The smell and taste of the spunk was really strong and I could feel myself getting hard again. It was going to be a long night!

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