The Older, The Better

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.