Classy But Crazy Ch 01

A true story!

It had been a good day at work. The deals we had been working on had suddenly materialised and it looked like we would be getting more than £100k in the next two weeks or so. That would keep the main shareholder off our backs.

I had broken the news to Mike and Lawrence at about 11.00 a.m. With a little more work to do the celebratory lunch at the pub for 12.00 was agreed and we all met at our local, a basement bar in the town centre.

We had set up the company some 18 months ago and things were tough initially but the business was now beginning to take off. David (that's me), 36 and the youngster of the bunch. Full of great ideas and well respected in the finance industry.

Mike was 58, very much the patriarch and Lawrence was 45 and great with figures. We all got on very well.

Lunch was always simple – a sandwich and as much Thai or American beer as we could get down us. It always lasted three or four hours when we had something to celebrate.

That day we had something to celebrate. The two girls who ran the bar were a lot of fun. Chat, innuendo and even the real possibility of something happening was always in the air, even with Mike.

The time went by and soon after it was 4.00 and back to the office to check messages.

Nothing too urgent, a couple of phone calls made, check the e-mail and fax and by then it was 5.15 so time to go home.

The drive home was usually half an hour. The town where our office was had a lot of business premises so at 5 o'clock there was guaranteed a jam going out of town and the half hour journey was often 45 minutes or an hour.

Tired and probably a little too boozed to be driving I am slowly creeping along, stopping every 5 yards or so, waiting to join a junction. Radio playing in the car and it's fairly boring.

About 50 yards away I notice a figure on the other side of the road waiting at a bus stop. Even from that distance I can see it is a woman. She's in a white suit with a red collar and is wearing a fairly large red hat. Even from the distance I am, I can see that the skirt is fairly short.

As I approach I can see that she is carrying a small parasol. She doesn't seem to be able to stand still, walking about and swinging the parasol from side to side.

The closer I get the more detail I can take in. She's fairly well built, probably 5 feet 4 or so in height.

When I get about 10 yards away she has her back to me. Just as I draw level she turns round. This is like something from Royal Ascot. Absolutely dressed to the nines in the middle of a small town in England.

Her age - at least 60. Her dress - weird in the extreme. It is evident that the suit is home made, albeit not tremendously well, although it fits.

I begin to wonder where this woman has been and why she has dressed the way she has.

It is then that she catches my eye, looking at me with a broad smile. I smile back and begin to wonder. She waves the parasol and I wave back with my hand. Then the traffic moves again and I'm 20 yards past her.

I look in the mirror and she is still looking straight at my car, now swinging the parasol and standing square on to me.

"Don't be daft – she's old enough to be your mother!" – "I wonder " – I look again in the mirror and even though I'm a little the worse for wear from the booze, calculate how long it will take for me to reach the junction, turn round and come back on her side of the road.

"OK – by the time you get back there the bus will have come and that will be that"

I get to the junction and execute a slick U turn. I'm about half a mile from where she was. "She'll be gone – this is silly"

I'm getting closer now, just round this bend and as I come round it I can see that she's still there! "What do I do? – Drive Past? – Stop? – Come on make a decision"

As if someone else is in control I slow down, pull in to the bus stop and offer her a lift. Down goes the window.

"Hello – I passed you on the other side – are you waiting for a bus?"

She smiles – "yes I am"

"Can I drop you somewhere?"

"Are you sure – you were going the other way"

"That's OK – I have lots of time"

She opens the door and gets in; the short skirt rides up and shows a good deal of white stockinged thigh.

"Where can I take you?"

"Dunheved Road North – do you know it?"

"I think so – you can show me"

We pull back into the traffic and I've done it, I've picked her up, but what now? As she sits next to me I can see that the suit jacket is over a fairly low cut white top and that there is a sizeable cleavage on display. Also the skirt has settled at a level where the stockings are freely on display.

Does she know this? Is it intentional? All of these questions are going through my mind as we go along.

She tells me her name is Betty and she's just been for a job interview. I try and make conversation by asking her about the job but I am conscious of the fact that I am beginning to get a massive hardon as my mind races ahead to the possibilities of this situation.

We talk about the job and whilst for the life of me I cannot image why a 60 (64 as it turned out) year old woman would go to a job interview dressed like that.

She directs me to a turning and I pull into a car park in front of a fairly shabby block.

"This is it" she says – "thank you very much"

"My pleasure" I blurt out, thinking OK that's it.

She stays seated in the car and I then realise that she is expecting me to get out and open the door for her!

I open my door and walk round the back of the car, hastily arranging the folds of my suit jacket to hopefully cover the large lump in my trousers.

On opening the door she swings her legs out and I see the white of lace underwear at the tops of her legs framed in the stocking tops. Is this intentional?

I close the car door and she turns to me and says' "you have been so kind – I don't know how long that bus would have taken – I did not have a timetable"

I reply that it was not a problem and I was happy to do it. My prick is now straining and I can feel the damp of pre-come in my shorts.

"I wonder – would you like to come in for a coffee?"

"I'd love to" – she walks – I follow.

Through the main doors we go, and up two flights of stairs. She gets a key and opens a door to a one bedroomed studio apartment.

"I'll put the coffee on" she says " go through"

The lounge is small and the furniture shabby. I'm now a little nervous – is this what I think it may be? Probably not. She may be outrageously dressed but she is an old lady. I take my jacket off. My prick is still straining at my shorts. I try and adjust it and suddenly think: what if this is just coffee? Relax – you will know if and when it happens. I feel better and sit down.

She returns with a bottle of cheap sparkling wine and two dirty glasses. "I though better of coffee – let's celebrate my job interview and that should bring me luck"

THIS IS IT! SHE'S GOT TO BE WANTING MORE THAN A DRINK OR A COFFEE – ISN'T SHE?

I open the wine and pour it into the glasses. We chink and I say "lots of luck" Then we sit in silence.

Something else is said and then more silence.

What happens now? Do I make a move? I look at her and she's looking back. She must want something to happen. OK let's think this through. Another piece of meaningless conversation. If I try and kiss her and she doesn't want me to then all I will do is apologise make my goodbyes.

I pick up the bottle and refill the glasses. More conversation and she's still looking at me.

And then the idea. I put my glass down on the coffee table. A pause. I look round at her and she's just taken a drink. OK here goes. I reach out and take her glass away from her and put it on the coffee table next to mine.

She hasn't said anything she's still looking at me – maybe I am right. I lean forward and put my arm around her shoulder and put my face close up. She still looks straight at me. Here goes – I kiss her on the lips, softly at first but as my grip on her tightens the kiss becomes more intense.

She's kissing back now and my tongue begins to explore the mouth of this 64-year-old woman!

As the kissing continues I slide my left hand from her shoulder and into the front of her suit jacket. The white top is stretched by the fact that she is sitting up and I run my hand over her breast. They feel full and heavy and I can just detect her nipple beginning to rise slightly.

She continues to kiss me.

Encouraged, I slide my hand down over her lap to the top of her leg and from then on down to the hem of the short skirt. I begin to move up, feeling the nylon of the stockings and eventually the cool of her thigh above.

She is sitting with her legs together so I can only get to her panties by gently pushing my hand between her thighs. She seems to get the hint and opens her legs slightly.

Now I'm touching her outside her panties and I can feel that it is damp. Using my finger I move the panties slightly to one side and push into her. She shudders.

I stop and move my hand back up to her shoulder. She seems happy to continue kissing but it is now evident that she wants more than that.

Her right hand is round my waist and, still kissing her I take it and put it on my raging hard cock outside of my trousers. I squeeze her hand on to my cock so she can feel how hard it is. She gives out the longest sigh and because of it we stop kissing.

I try to kiss her again but she looks at me and says "come to the other room"

I stand up and follow her into a small bedroom with a single bed in one corner. She turns round and kisses me again this time she's doing all the kissing. I start to unbutton my shirt.

She stops kissing me and puts both her hands on my arms and stops me undoing my shirt. She puts my hands by my side and reaches up to undo my tie. Once off she undoes all the buttons on my shirt and the cuffs. She pulls the shirt out of my trousers and takes it off me. She runs her hands over my chest and round my back still not saying a word.

Then she takes my hands and pulls me towards the bed. She sits down and her face is now at the level of my crotch, staring at the huge bulge in my trousers. I slip my loafers off.

Almost as some kind of ritual she undoes my belt and my trousers and unzips my fly. She stops for a moment and then pulls down my trousers, helping me to get out of them and take off my socks.

I am now standing in front of this 64-year-old woman with a huge prick straining at my shorts and pointing right in her face. She has a look on her face, which I can only describe as frightened anticipation. I would love to know how long it has been for her.

Slowly she pulls down my shorts and because the waistband slides down over my cock it pulls it downwards when the shorts get down so far my huge cock leaps out and actually catches her in the face. I step out of the shorts and stand before her.

She reaches out her hand and touches it, wrapping her fingers around the shaft. I am not circumcised and she pulls the foreskin back to fully expose the throbbing helmet. I am very close to her face and she opens her mouth and puts the end of my cock in, closing her lips around it. As blowjobs go this is not great but I am so carried away with the whole fascination of what is happening that I am spellbound. She sucks the end of my cock with no movement making little slurping sounds.

I take her hand gently and try to move it up and down the shaft to get a little more of my cock inside her mouth. She gags a little so I stop.

She lies back on the bed and reaches out her hand to me to lie with her.

Now it's my turn. I take her hand but instead of joining her I gently pull her so she's standing upright.

She looks at me a little quizzically. "Now it's my turn," I say.

I slide the jacket off her shoulders and put it on the nearby chair. She is wearing a sleeveless top and by the way it clings to her I can now see that it's one of those one-piece items that does up under her crotch. So – my lady is dressing like someone 40 years younger than her?

I continue to kiss her and whilst doing so I release the catch at the back of her skirt and unzip it. It slides to the floor (with a little help from me – she's not small!) and I help her to step out of it.

Now she's standing in front of me with a tight white top on, underwear underneath, white stockings and suspenders and lacy panties. – Nice.

I kiss her again. My hand slides down her back and over her arse – need to get this top off. Two poppers are already undone and the last one shows little resistance. I pull the top up from the bottom and she obligingly raises her arms so I can get it over her shoulders and head.

She is now standing in front of me in a lovely lacy bra and panties, with a suspender belt holding up white stockings and she still has her white stiletto shoes on!

64 or not, this is well packaged and I am now determined (my boozy haze having been enhanced by the cheap wine) to enjoy this.

I kiss her again and take her hand and put it on my cock. She goes immediately on to her knees and takes me in her mouth. Still there's not too much of me inside her so I take her head and try to push more of my cock into her mouth. She takes a bit and gags again so I quickly take it out and pull her back to standing upright.

I reach behind her and undo the straps on her bra. The shoulder straps are pulled from her and I take the bra off and discard it. As the bra is removed her heavy breasts fall on to her stomach. I touch one. It feels full and the nipple starts to rise as I brush it with my thumb.

I use my hand to lift her other breast and lift it up, lowering my head to meet it and sucking hungrily on the nipple. Her nipples are small with beautiful pink areola and as I suck I can feel the tiny nipple hardening and becoming bigger.

My cock is still ragingly hard and as I am close to her it bangs against her stomach and her arse as I walk round.

I now sit down on the bed and she is standing in front of me. I reach my hands up and cup her breasts. They are huge but not saggy although they have obviously seen some years.

I lie back on the bed, pulling her on top of me. As she was standing up she naturally slides down to her knees and this leaves me with her kneeling in front of me sat on the bed. My cock is at her chest level. It seems somehow to fit perfectly between those pendulous boobs and my hands on either side close them over my cock and bollocks with just the tip of my helmet, poking out at the top.

I start to move the huge breasts up and down, masturbating my cock with the tip alternatively disappearing and appearing from the very large cleavage. She seems to get the idea and every time my tip appears she either licks it or, if enough pops out she wraps her lips around it. This is wonderful.

She begins to work her way onto the bed and soon we are lying side by side with her pulling my foreskin back and forth and me playing with her tits and biting her nipples.

I slide my hand down from her tits to the tiny lace panties she is wearing and slip my hand in the top. She is totally shaved and I am so amazed that a woman of this age is bald that I start back and contact between us is broken. She asks me if everything is OK and I assure her that it is. But this is now different.

I don't return to what we were doing but I get myself to the bottom of the bed and pull her legs apart so I am looking up at her, lying in front of me. Slowly I take her panties on either side and pull them down over her thighs and her legs, taking them off each ankle in turn. I am now looking at a 64-year-old naked woman who is totally shaved and I cannot believe it.

Slowly I part her legs so that they are wide apart and I slide each hand up her thighs. I lower my head between her legs and extend my tongue to meet the lips that I can see in front of me. The taste is initially of piss and I have to steel myself to get through that reaction. Now both my thumbs are parting her outer lips and I can see the opening within. My tongue darts forward and I feel a strong smell of musk as I lick and lick and lick.

Suddenly she takes hold of my hair and starts to buck, forcing her very wet cunt into my face. It is all I can do to hold on as she thrusts her pelvis into me and I have to reach round and grab her arse to try and exercise some control. She cries out "Darling, darling, darling" and falls away again.

I take a breath and then go back to my tongue work, licking and biting and nibbling at this old and very wet clitoris.

She pulls my hair and jerks my head up – "I want you inside me now" she says

I get up and pull her towards me by grabbing her arse. My hard cock slaps against her cunt and I take hold of it and easily push it inside her. This is like throwing a sausage down a motorway. Not tight and not too much fun. However I am aware that she is enjoying it and even more aware that the efforts I am making are causing her to come in waves and that this is making entry to her cunt even more of a problem because it is so wet.

At one stage I pull out and grab a handful of tissues from the bedside table, wiping her and then trying to get back in. It only proved to be a temporary respite as the flood of her come continued to run out. The good news was that she was enjoying it and it was all I could do to remain in control with her wild bucking and nails scraping down my back.

Eventually all the activity caused me to react and I came inside her with lots of thrashing and (what felt like) gallons of liquid.

With all that had happened and the booze, I quickly fell asleep, feeling pretty good and somewhat drunk.

It must have been an hour or so later when I woke up. It was dark and there were no lights on. I was cuddled up to a naked 64-year-old woman wearing just stockings and suspenders and the smell of sex was everywhere.

I reached over and switched on the bedside light. She stirred. It was not the first time I looked at her but certainly the first time I looked at her sober. She was old and not particularly attractive. She smiled and kissed me. I kissed her back, all the time thinking how do I get myself out of this?

She said, "you OK?" – I said, "yes fine"

She slid herself down the bed and wrapped her hand round my flaccid cock. She pulled the foreskin back and forward. This was not supposed to be happening! I needed to have a nice kiss and say thank you and goodnight.

I tried to move her hand away but she pushed me back on the bed and moved over so that she was now facing my feet and we were almost in the classic "69" position, although her legs were not straddling my shoulders as she was still to one side.

She lowered her mouth on the end of my cock and I felt it stiffen. No, no not now don't give me away. But she was pulling it and sucking it and with a mind of its own it was soon hard and throbbing under her tender care.

I was lying back, a little hung over, wondering what on earth I had just done and there was my cock ready and eager for more!

I looked up at the huge arse hovering just to one side of my head. Believe it or not it made me feel horny and only added to the pressure in the area down below.

I reached out and lifted Betty's left leg and placed it on my other side. I was now staring at a wet, red and very sore looking cunt, which I had known from past experience, was cavernous. A large gob of my cum was just seeping out of the inner lips.

There was nothing else to do. I lowered her on to my face and plunged my tongue into the deep wet cavern that was her cunt. As I slurped around I reached up to steady what was an arse that was about to asphyxiate me I realised that the whole of this lady was wet with sweat, her come, my come and god knows what else.

I pushed her cheeks apart and looked straight at a lovely pink arse, which was glistening and very very moist.