2 comments/ 79052 views/ 4 favorites Classy but Crazy Ch. 01 By: ChelseaBoy 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. Classy but Crazy Ch. 01 Holding her cheeks apart with one hand I ventured a finger forward to her arse crack. There was a little resistance but the tip of my finger slipped in to her quite easily although not too far. She immediately stopped what she was doing and came back up to me and kissed me, still playing with my very hard cock. We rolled over and I was now on top of her. I moved down, bit her nipples, which caused her to moan, and again went down to lick her clit and finger her. I pulled her legs apart and pushed my hard length into her cunt. She moaned and grabbed my arse pulling me harder into her. I thrust and pumped for a couple of minutes until she was quite tired out. I slowed down and gradually stopped but immediately I had done that I pulled out and turned her over on her stomach. She was completely pliable and when I pulled up her hips so her arse was stuck up in the air she was happy for me to do it. I grabbed my cock and slipped it into her cunt from behind. I then reached over and cupped her huge boobs in my hands twisting and pulling the nipples while I plunged into her hearing her huge arse slapping loudly against my stomach. She was calling out "yes – yes darling darling" so I knew she was enjoying it. I adjusted myself so I could get more purchase from a different angle from my legs, and this released one of my arms from "boob duty". I was then able to put my free hand on her arse and rub the crack whilst still fucking her from behind. Gradually I moved my hand so that I could introduce a finger up her arse whilst still fucking her. She resisted at first and even came out with a couple of "no no's" but over about three minutes I had my cock up her and almost all of my index finger up her arse. I slowed down again and gradually as she was on all fours and appeared to be exhausted I pulled my cock out of her and rested for a moment. I started to rub her clit again and she made some more noises like she was enjoying it. I moved my hand up from her clit and gathered up what juice there was in her cunt straight up to her arse. Re-adjusting my position I took my hard cock in my hand used the other to part her cheeks and pushed my prick against the entrance to her arse. There seemed to quite definite resistance for a few seconds and then suddenly it gave way and all of my cock was deep inside. Betty screamed and said "oh no" but then seemed to be resolved to what was happening. I did not want to be rough or hurt her but the feeling of her arse against my cock was so fantastic and tight that I needed to pump away and so I guess she would not have been able to do anything about it anyway. It was so tight and I was so turned on that it did not take long. I felt my cock pulse and pulled out of her arse just in time to spray come all over her arse and her back and her hair. In fact while I was doing it she turned round and a good few spurts landed on her tits and her face. We fell asleep again and when we woke up it was late so I had to go. Betty may be 28 years older than me but I'm 50 now and I still see her at least once a month and we've done lots more together in every location and with other participants. – In praise of older women! Classy but Crazy Ch. 02 The Adventures of Dave – in praise of older women For several days after the episode described in the original story I was in somewhat of a daze. I kept pinching myself and asking if it had really happened. Certainly for the ensuing days I had a number of physical mementoes, which reminded me, not least a very sore cock. After about a week I decided I had to go back. I thought that it would probably result in an embarrassing politeness and a firm "no thanks" but I simply had to find out. It was a Wednesday night about 7.00 p.m. and the sun was just disappearing. The apartment block was the same dull concrete and there was little to uplift me when I pulled up in the car park. I had armed myself with a bottle of brandy to be sociable and, after a short pause to check that there was no one about, I had gone into the entrance doors and found myself two flights up outside her door. The sound of a television could be heard. I knocked... no answer. I knocked again, louder. The television was turned off. The door opened on a chain. "Who is it?" asked Betty, "It's me, David" I replied. "Who?" she asked. "David" I said again, beginning to regret this, "remember, we met last week – I gave you a lift home." She took the chain off the door and opened it a little further. "Hello" she said, "What are you doing back here" "I thought we could have another drink" I said, "I've brought a bottle of brandy" Her eyes widened when she saw the booze and she opened the door and let me in. She was dressed in a fluffy dressing gown and a nightie underneath. "Come in please" she said and led me through to the lounge " sorry I'm in such a state, I wasn't expecting visitors – let me get some glasses" She got two glasses and I opened and poured generous measures. We chinked the glasses and I took a healthy swig, she took a sip. "Sit down please" she said " you must excuse me for a moment, I need to make myself presentable" She left me and almost immediately I heard the sound of a bath running. I sat down, found an ashtray and poured another very large shot of the brandy. I looked around the room. It was clean if a little worn and there were all sorts of knick-knacks scattered around. The TV in the corner had a VCR underneath and there was a large window. A corner unit had all sorts of exotic looking bottles in it. It had been about 15 minutes when she came back in and I was already half way down the brandy. She had changed into a brightly coloured kaftan with a zip right down the front if it and it was evident from the way her breasts swayed that she was not wearing a bra. My cock stirred. I was sitting on the couch and she picked up her drink and sat across from me on one of the chairs. She started to talk, telling me she had not heard about the job she had been interviewed for when we first met, so she had 'phoned them up and they had said she was unsuccessful. I reassured her, saying that I was sure that she would find something soon. We then exchanged conversations for the best part of an hour during which time I ascertained that she had been divorced for a long time, had a daughter who was married with two children (she showed me the pictures) and she had been living in the apartment for about two years. I filled her in on myself by making up all sorts of stuff, saying I worked in professional golf and travelled a lot and that I had a house nearby where I lived on my own. During this time I regularly topped up our glasses by going over to where she was and filling her glass and then returning to my seat. The brandy was by now all gone and I had just drained my last drops. "We need another drink" she said and got up and went over to the unit from which she produced another bottle of (considerably cheaper) brandy. She gave it to me and I opened it and poured two more generous slugs. Time to make a move, my cock was aching and we had spent nearly an hour and a half talking! "Why don't you come over here?" I asked, patting the couch next to me and moving the small table in front of it with the ashtray, the bottle and my glass. She obliged. We continued to talk and as with the last time I put down my glass, took hers away and leaned forward, putting my arm around her back and kissed her. This time she responded very forcefully, kissing me back and holding me very tight. I slid my hand up from round her waist and cupped a full breast, pinching the nipple, which rose hard and erect under my touch. We continued to kiss. I moved my hand up to the top of her kaftan and started to pull down the zip which came away quite easily, down to her full stomach. I slid my hand inside and grasped her breast again, rubbing the nipple very thoroughly. I opened up the kaftan with one hand exposing both her breasts and I moved my mouth from hers to suck first one tit, then the other, nibbling at her nipples and rubbing them. She started to moan. I kissed her again and, taking her had placed it on my (by now) very hard cock. She gasped and squeezed my cock outside of my trousers, rubbing it and squeezing it repeatedly. I went back to work on her ample breasts and sucked and rubbed them for some time. She arched her back and started to moan as her first orgasm swept over her. I pulled back. "Get up" I said. She stood up and in front of me, facing me. "Take your clothes off." I ordered. She unzipped the kaftan down as far as it would go and slipped out of it, letting it drop on the floor behind her. She was standing in front of me completely naked, and put her arm across her breasts and her hand in front of her cunt in a very defensive posture. I pulled my shirt off and sat back on the couch looking at her nakedness. I removed my shoes and socks. I was only wearing a pair of jeans, having made the decision to go "commando" for this evening, I guess because my imagination had been running away with me. "Put your hands by your sides" I ordered. She obeyed. I was now looking at the body of a sixty plus woman, round and curvy with pendulous hanging breasts, each topped by a beautiful small and very hard pink nipple. Her stomach was round and podgy and her hips were full. Her stomach was not so large that it obscured her pudenda and there, framed between two sizeable thighs was her fully shaved cunt with her outer lips completely on display. I laid back. I was wearing jeans with a button fly and, after undoing the top button I ripped open the fly. As each button popped open, my hard cock sprung out until it was sticking up proudly in front of her. I slipped my jeans off and spread my legs, my huge hard cock pointing up at her. I pulled back my foreskin fully, exposing the helmet, wet with pre cum. I held out my hand, took hers and guided her to a kneeling position between my legs. I put her hand on my cock and she leaned forward and slipped the end of it in her mouth, putting her other hand on my balls. This was heaven! I put my hand on the back of her head and pushed my hips upwards trying to get as much of my hard cock in as I could. She gagged and resumed her sucking action round the helmet. No deep throat for me but she was now fully involved in stimulating my raging cock, pulling back the foreskin and sucking and licking my helmet, while her other hand caressed first one of my balls and then the other. I cupped her breasts, rubbing the nipples and pinching them, feeling their heavy weight, while she sucked harder, making slurping noises and licking all around the top of my cock. I sat back and guided her fully between my legs, so I could place my cock between her breasts. With a thumb on each nipple and with her pendulous breasts squashed around my huge cock I started to masturbate myself using those massive tits, thrusting my hips into her. With each push the head of my cock emerged from her cleavage and she greedily licked or sucked it as it pushed towards her. All of this action made me start to feel the pressure building in my balls and I pulled her up so she was lying on the couch with her legs wide apart. I stood up and put one foot on the couch and grabbed by cock, wanking furiously. Almost immediately I came with a huge jolt, which delivered a spurt of come square in her face. The subsequent spurts landed on her shoulder, her tits, her stomach and her cunt and as I squeezed the last drops off my shrinking cock she moved under me to let them fall on to her face. She got up, went to the bathroom and brought back a flannel, after cleaning herself off. Very attentively she wiped my cock and balls and returned to the bathroom where I could hear the sounds of the flannel being rinsed out. I sat back on the couch. She returned and went to pick up her kaftan and made to put it on. I looked at her and shook my head. She sat down naked on the opposite chair. I lit a cigarette and topped up the brandies, getting up and taking one to her. We carried on a further conversation like we were having a tea party and I found the experience quite bizarre. I finished my drink, topped it up again and got up and went to the bathroom. On my return I stopped by the chair and my cock was stirring slightly. I took her hand and wrapped it round my hardening cock. She pulled it back and forth and started to lick the end of it again. I took her hand and led her to the settee and laid her down on it with one of her feet on the floor and her legs apart. I kneeled down and opened up her lips with my hands. She was very wet and the fact that her cunt was totally bald made my cock rise again with a sudden twitch. I put my head between her legs and started to lick, long strokes from her arsehole all the way up to her clitoris. She shuddered and put her hands on my head, holding me at the top where my tongue could do most good. I felt her clitoris stiffen and introduced a finger to stimulate the G spot behind it. She started to buck, pushing herself against my face and moaning. "I want you inside me – now!" she barked. I rose up and, supporting myself on my hands pointed my cock in the general direction of her cunt. It slid in very easily, finding its own way and I started to fuck her with long slow strokes, which she was evidently enjoying, from the cries of "Darling, Darling, yes! Yes!" which she came out with. I started to speed up, moving faster now and actually pulling completely out of her cunt only to ram back in with the next thrust. She was now totally out of control and was moving in harmony with my thrusts pushing against me when I filled her up with my massive cock and pulling away when I withdrew. She started to make some very curious noises, which grew in intensity and volume, and as she thrashed about it was apparent that she was having an immense orgasm. I continued to keep up the speed of my thrusting and as I felt my balls tighten I pulled out again and this time sprayed cum all over her stomach, tits and cunt. We collapsed together, clinging tightly in a soaking mass of bodies, sticky, sweaty and totally exhausted, breathing heavily from our exertions and the orgasms. Eventually we separated and she again went to the bathroom returning with the flannel to studiously wipe my cock and balls and stomach. I got dressed and she put her kaftan back on. I said I would see her soon and left. As I've already mentioned, this was in 1989 when Betty was 64 and I was 35. She is now 78 and I'm 50 and hardly a week goes by without us getting together. Over the years we have known each other we have had many an adventure and lots of excitement together and with other people and future stories will relate these experiences. I say again and again – In praise of older women! Classy but Crazy Ch. 03 The Adventures of Dave – in praise of older women After the first two frantic encounters with Betty our relationship settled down into one of regular visits. I found out that the apartment she was in had a mix of residents from young married couples staring out on the property ladder. To ladies and gentlemen who were in a similar situation to Betty, living alone due to bereavement or divorce. Their average ages must have been about 64, the same as Betty. In conversation with Betty the subject of her friends often came up and she had remarked that some of them had asked whom I was. She was at a loss because she didn't want to give away the fact that I was calling round for sex and she was seriously beginning to think about putting a stop to my visits. I explained to her that this was not a problem and asked her honestly if she could simply stop seeing me. She readily admitted that this would be a major problem. I for my part had got quite attached to this "crazy" old lady so I didn't want to suddenly stop my visits. We had known each other now for about six months and it had become apparent to me that Betty was quite suggestible. An idea came to me. "Why don't you tell your friends that I am a fully qualified masseur?" I suggested "Then they will know why I am round here. You could say that the doctor recommended me and that I am giving you a course of treatment" Betty thought that this was a brilliant idea. Our meetings went on for some more months and the problem of nosey neighbours seemed to have been solved. It had been almost a year. Work was gong well and I was able to practically take off what time I wanted. The result of this was more visits to Betty and more of them during the day. It was high summer. During one visit Betty asked me if I would like to meet her friend Elizabeth who lived in a flat on the other side of the building. I was curious as to date the concept of me being "shown off" was not one, which I had understood Betty wanted to subscribe to. Elizabeth was 66, widowed for 16 years and was a very good friend to Betty, bringing her plants and joining her regularly for coffee and shopping. Betty had told Elizabeth that I was a masseur and did admit to her that I was making her feel a lot better with my "treatments", although she assured me that she had not said anything of the stuff which Betty and I got up to. Elizabeth had asked how much I charged for treatment and Betty had told her it was £50. Elizabeth seemed quire happy with this and so Betty had said she would ask me if I was available for her. Betty and I had a long discussion during which I was unable to find out just what Elizabeth's angle was, whether she had cottoned on to what Betty and I were up to or whether she genuinely believed that I was a masseur and would give her a massage. After the conversation I really thought that Betty did not know. What was I to do? I asked Betty how she would feel if Elizabeth really wanted sex and the two of us got on and it happened. She simply said that she would be pleased if Elizabeth could be made as happy as she was at the moment, but she stressed that all of this had to be confidential as she did not want people talking. Betty 'phoned Elizabeth and it was agreed that I would visit her the following afternoon. Betty made me promise to visit her immediately afterwards. The next day was very hot, 80 degrees and sunny but with a cooling breeze. Elizabeth lived in a top floor corner flat, which was bigger than Betty's and at 1.45 in the afternoon I found myself outside her front door. In order to add realism to the "masseur" front I had purchased some aromatherapy oils and other lotions and had them in a small case with two hand towels on top. I had also dressed in a sports shirt and shorts with trainers to create (as I thought) the right impression. I rang the doorbell. A small woman with dark hair answered the door. She was reasonably attractive in a print dress and sandals. "Good afternoon" I smiled, "I'm David, Betty arranged for me to visit." "Come in" she said and I followed her through into a very well kept lounge with modern furniture. I put my case down and took a seat. Elizabeth went to the kitchen and brought back a tray with a cafetiere and some biscuits. We sat and chatted and she asked me about massage and how she had heard that Betty was feeling much better after my visits. She said that her right shoulder and left leg were her problem and asked if there was anything I could do for her. I said I was sure there was but I would need to take a look. She became a little embarrassed and eventually asked just what was involved. I reassured her and said that to effectively ascertain and treat the problem I would have to be able to manipulate her on a table or a high bed. She took me into the bedroom and there was a sizeable bed there, which would have been OK but was a little low. We had passed a dining room on the way in and there was a very sturdy dining table in the middle of it about six feet by three. I mentioned that this was ideal and if she could find a blanket to put on it then it would be almost the same as my normal treatment table. She wandered off and five minutes later the table was set up. I moved my case into the room and took out some bottles. I waited. Elizabeth came into the room wrapped in a large white towel. I asked her if she needed any help getting up on the table but she assured me that she did not. I looked out of the window while she was doing it and turned round when I heard her say "ready." She was lying face down on the table with the blanket draped over her shoulders. I asked her to relax as much as possible and slowly removed the towel from her shoulders folding it back over her waist, just past the top of her white panties. She was naked from the waist up. I started to feel her back and shoulders and although it seemed fairly tight and knotty, I really did not have a clue what I was doing. I asked her where the pain was and she directed my hands to the appropriate area. I said I thought I could feel something and after a small amount of kneading of the area asked if that was better – she answered that it was. I asked her if she could turn over so I could look properly at her leg and I held the towel while looking away so she could do so. As she turned I noticed out of the corner of my eye that she had medium sized breasts which seemed to be very well preserved for a lady of 66, but each breast was topped with enormous brown nipples with huge aureola which seemed to cover almost 25% of the front of the breast's surface. The sight of this made my cock twitch and start to rise. Elizabeth was now lying on her back, with a towel covering her and I moved round to the other side of the table to examine the troublesome leg. To do this I had to push the towel up her thighs and on doing so I noticed that there was a sizeable amount of black hair protruding from the side of her large white panties. I clasped her leg above the knee and gently squeezed from each side. Slowly I moved up her thigh alternately squeezing one side then the other as if I knew what I was doing. Once I had worked my way all the way up I had one hand on the outside of her thigh and one between her legs, hard up against her cunt, covered only by the thin white panties and the copious black bush of hair. I moved down the thigh and then up again, each time making sure my hand pushed quite firmly against her cunt. My cock was rock hard. "OK" I said, " you have a muscle problem with the leg and the shoulder is related to the lower back. I can help all of that with some massage. Turn over please" Whatever I was doing it must have convinced Elizabeth that I was genuine and she could be totally relaxed around me. This time she didn't even bother with the towel, sitting up immediately and then turning over, giving me a full view of the huge brown nipples on her beautiful tits. As she turned over, she took the towel and let it fall to the side of the table. She was now lying on her stomach in just her panties. I opened a bottle of lavender oil and started to massage her back from the shoulders down to the small of her back. She moaned gently with each sweeping stroke. "Feeling relaxed?" I asked "Mmmmm yes" she replied. "We'll soon get you sorted," I said. I felt bolder and so rolled down the waistband of her panties so I could massage the top of her buttocks. All this time my cock was making a huge lump in my shorts and I was lucky that she had her head turned away from me. I moved down to her legs and started on the one I had been working on earlier. Again I moved upwards from the knee and worked my way up to the side of her panties with the back of my hand hard against her panty clad cunt, rubbing as I massaged her inner thigh. I worked the other leg as well and did the same movements, ending up with a hand against her cunt, between her legs, which seemed to be opening a little wider from this activity. I moved round to the other side and returned to her back, concentrating on first her shoulder and then her lower back. I felt Elizabeth lift herself up on her hands. Her breasts swung slightly as she steadied herself. "What's that?" she asked. She was staring at my shorts where my cock was sticking out hard against the material like a tent pole, with a small dark stain around the end. "I'm so sorry" I replied, frantically trying to think of something to say, "This doesn't normally happen" "Why are you like that?" Elizabeth asked. "I don't know." I replied, " I think you are very attractive" "I'm old enough to be your mother" she said, "That's not right" "Sorry" I said, "I'll go" Elizabeth raised herself on one elbow. Those breasts were great and for a woman her age they held up really well. "I want to see it," She announced. I walked back towards her. It was still pressing hard against the shorts. Slowly I pulled them down and stood up with my cock right in front of her face. She looked scared. "You can touch it if you want to" I said, emboldened by her request. She stretched out a manicured finger and prodded my cock. It swayed. She ventured a hand and wrapped her fingers around it. "It's throbbing!" she exclaimed. I leaned forward and kissed her. She had very soft lips. There was no response so I moved my hand to her breast and squeezed it gently. She still had her hand on my cock. Her nipple rose and I rubbed it. "No. Stop" she said and let go of my cock. "What's the matter" I asked "I'm too old for this" she said "It's almost 20 years since I was close to something like that. I don't know, I really don't know" I kissed her again. "Is that nice?" I asked. "Yes" she replied, "but I'm scared" "I wont hurt you, and I'll stop if you want me to" I reassured her. "Just hold me," she asked. We went to the bedroom and she turned back the bed. We got in together and cuddled, her still in her panties. I moved my hand down again to her breast and probed her nipple, causing it to rise and harden. Each time she started to say something I kissed her and soon she was kissing me back. With every kiss she seemed to relax more and more. I slid my hand down the front of her panties. She stiffened and her legs closed together. I left my hand there and kissed her again and gradually she relaxed more. She stopped and pulled away, sitting upright. "I can't. I want to but I can't." she whispered, " It's been so long." She started crying. I took her in my arms and cuddled her I said that everything was OK, we could forget this if she was unhappy, or we could take our time and she could control everything. We lay together for over an hour and she told me she had been happily married but that her husband was no great shakes between the sheets and that she had never expected to have another opportunity. They had no children and all during their married life she had felt unsatisfied but was too afraid to query anything or to do anything about it. I asked her if she trusted me having only just met me. She said she knew that I was a good friend of Betty's and that was good enough for her. She made me promise that I would not tell Betty what she had told me or that we had done what we had done. I said we had not done anything yet but that I wanted to help her if I could. She agreed. I switched the bedside light on. The room was very warm. I rolled back the covers so we were lying on the bedsheet. Elizabeth was on her back. I moved down to her feet and slowly pulled down her panties, discarding them on the floor. I moved up to her head and kissed her softly. She kissed me back. I worked down her neck planting soft kisses on her old body. I reached her breasts and gently sucked one nipple, whilst slowly rubbing the other. She stiffened a little. After some time I moved down again, gently kissing her stomach, which was a little distended and finally reaching a dark mass of black pubic hair. I sat up and placed my hand on her mons, gently touching her and slowly moving her legs apart. I inserted the tip of one finger. It was damp but not wet. I took hold of her legs and parted them, pausing only to return briefly to her head where I kissed her again gently on the lips. I nuzzled into the hair and darted inside with my tongue. I had to use one hand to part her lips so I could lick her. She moaned soft and low. I increased my attention, concentrating on her clitoris. I pushed a finger in, slowly, slowly. It was very very tight. Gradually I managed to get enough lubrication to be able to push my one finger in and work up a rythmn. Her head was rolling from side to side. I climbed between her legs. Using one hand I parted her outer lips and guided the head of my cock to the entrance to her cunt. I pushed gently and her lips parted ever so slightly. Getting a bit more purchase I managed to push my cock in a little further. This was the tightest cunt I had ever been in and it was on a 66-year-old woman! She opened her legs as far as they would go. Bit by bit my cock filled her up. I had never been in such a tight soft pussy. Eventually I was fully in and supporting my weight on my hands. I started to pull out slowly and worked up a gradual beat with no speed at all. I was slow fucking this woman and it was fantastic. She wrapped her legs around my waist and joined in with the thrusting, still at a very slow pace. The totally erotic nature of what was happening and the slow and steady pace of my thrusting got me very excited but I resisted the urge which was running through my body to fuck her senseless. Then it happened. My balls tightened and I felt wave after wave of cum gush out of me, filling her up for what seemed like an age. We lay together for a while. She looked at me, smiled and said thank you. We got dressed and before I went she tried to give me £50. I refused. When I went to Betty's I said that Elizabeth had wanted and had got a massage. In subsequent visits Elizabeth got a great deal more and I was enjoying myself as much as I did with Betty. Betty never knew what Elizabeth and I got up to and I respected her confidence. The following three years were a wonderful time and then Elizabeth suddenly died, aged 69 years. I know I made her last years wonderful and taught her to enjoy something she could have been enjoying for the preceding 40 years. Everyone wondered who the youngish, smartly dressed man was at her funeral. Everyone wondered even more when she left him £10,000 in her will. I will always remember Elizabeth. She was wonderful and sexy and funny and educated and demure. All in one package. In praise of older women indeed! Classy but Crazy Ch. 04 As the months and years went by I had established a relationship with Betty, which to any man who is attracted to older women would have been ideal. I was a regular visitor and she was always glad to see me. She had introduced me to a fellow resident and as far as she was concerned (at Elizabeth's request) all I was doing was visiting her once or twice a week to give a massage, which had been Betty's excuse for my regular presence anyway! So it was great to be able to visit two elderly ladies in turn, and make love to them in all sorts of ways and pursue a "no strings" relationship with each of them. From time to time I questioned what I was doing. At least once a week I would visit one of them and we would fuck for an hour or two. Whenever my doubts were raised I only had to look at either of them or listen to them when I was performing. These were feelings and activities they both thought they had left behind years ago and they were very grateful and in their own ways loved me for it. They could not have been more different. Elizabeth was a real lady, initially nervous about what was happening but subsequently so happy with the sex and the company that she was obviously telling herself that she deserved this and was going to thoroughly enjoy it! Betty was (and I choose my words carefully) a dirty cow! Sex had obviously been extremely important to her for a large part of her life and here it was, back again, with a much younger man and she was determined that it would last. She started to give me small presents, aftershave, cufflinks and always made sure there was brandy in the flat when I called. She also acquired a number of "toys" notably some vibrators, a Polaroid camera and when she found out I owned a video camera she almost begged me to bring it to film or sessions. I was asked about videos quite early on and when I brought some porn, the sex was amazing! It was one summer after about a year of our relationship that an episode took place, which is very worthy of recall. It was a very warm day and I had finished a business meeting about 11.30 a.m. so I called Betty and asked her if I could come round. As always, she replied "of course" and I found myself about 1.00 p.m. outside her door with two bottles of chilled white wine from the off-licence. She answered the door – "Come in," she said with a smile. I gave her the wine and she opened one bottle and brought two glasses The TV was on and the Open Championship was being shown, the first round I think. We watched TV for a while and she got up and went into the bedroom. I continued to watch the golf. About fifteen minutes later she came back in and stood in front of me in a light beige trench coat, a very nice ladies' one. She was wearing white stiletto heeled shoes. "You look nice" I said, wondering what she had been up to "Thank you" she replied, "want to see some more?" "Of course" I answered, wondering what she was up to. Slowly she undid the buttons of the trench coat from the top and pulled the top half of the coat open. She was wearing a lacy white bra, low cut and it showed off her enormous breasts perfectly. The lace was so thin that her hard pink nipples could be seen clearly. "Lovely," I commented. My cock was beginning to get hard, so I unzipped my fly and got it out. She undid the rest of the buttons, and pulled the coat wide open. She had on the skimpiest transparent lace thong on showing her cunt lips and her shaved mons. She was also wearing a suspender belt in matching white lace and white nylon stockings. She looked a picture – mid sixties and dressed to fuck! She made as if to take the coat off. "Leave it on" I told her. She knelt down, undid my belt and trouser button and slipped my trousers and pants down to my ankles. She grasped my hard cock and pulled the foreskin back. Slowly she licked the end of my cock and cupped my balls with one hand whilst masturbating me with the other. Keeping her bra on she pushed my cock underneath it so it was between her tits. As she masturbated me with her lovely large breasts I pinched her nipples through the lace. Soon she was pulling and sucking the end of my cock very hard and I felt her finger slip round to my arse. She reached behind me to a shelf and took the smallest vibrator she had. Slowly and quite expertly she inched it in to my anus until with a final shove she had fully inserted about four inches of it. This was too much for me and I started to cum, first in her mouth then into her face and hair and all over her tits. I lay back, the vibrator still up my arse and she left, returning with a wet flannel to clean us both off. "Let's go to bed," she suggested "No" I replied, " I've got a much better idea" I stood up and got dressed, having removed her stimulating vibrator. "Let's go out" I said, " It's a lovely day." "OK," she replied, " give me five minutes to get dressed." I picked up the trench coat "put this on and you are dressed" I said "I can't do that," she said "Why not? I asked, " you're with me – you'll be quite safe" I offered her the coat and she put it on. "Bring the camera," I said We left in my car and drove about ten miles to a country park. The area had a lake, open spaces and woodland as well as a play area and a café/bar. I parked the car and we walked down to the lake. There were a few people about, not many. To all intents and purposes we could have been a mother and son dressed up for a visit to the park, me in my suit and her in a nice rain coat, suitable wear for a warm day. We walked around for a while and from time to time I undid one or two buttons on the coat just to give a glimpse of stocking top or lacy cleavage. It was turning me on and evidently one or two of the men sitting reading or fishing in the lake. We walked round the lake to a wooded area behind it and a path that threaded through the woods and came out on the other side. Half way along the path I took Betty's hand and led her into the trees. I found a small clearing in the wood where a tree had fallen. "Stand over there by the fallen tree" I ordered. She did so. "Lean back against it" I said, "now start to unbutton the coat from the top" Betty leant back against the tree and undid the coat. Inch by inch her body was exposed, her huge breasts encased in the lacy bra and the thing pulled up tight into the crack of her arse and showing her cunt lips beautifully exposed through the flimsy white. I took picture after picture creating a "striptease" as the coat buttons were undone and the coat was opened up to reveal her plump and pink body underneath. "Now take the coat off and put it on the tree trunk behind you" I said Betty hesitated but did as she was told. "Undo the bra, slowly, slowly and hold it at the front cupping your tits" I asked. She performed the maneouvre perfectly, slowly removing the garment and discarding it at her feet and then stretching her arms behind her head, which made her huge breasts, jut out, the nipples hard and erect. Betty had now got the idea and turned away from me revealing her huge arse with the thong fully wedged into her crack. She started to pull the thong down slowly. "Stop" I said. I put the camera down and came over to her. I put her hands on the top of my trousers and she undid them sliding them down over my hips. She slid her hand inside my shorts and felt my hard throbbing prick. She fell to her knees and pulled down my shorts, hungrily licking and sucking my cock. I raised her up again, and, leaning her back against her coat on the fallen tree lifted one of her legs. In one movement I had pulled the thong to one side and my hard prick filled her up. I started to thrust; slowly at first but as the momentum increased I was fully driving my cock home. She lay back on the coat, her breasts wobbling with every thrust. I pinched her nipples and leaning forward bit and sucked both one and then the other. Before too long I felt myself about to come and pulled out. I sprayed her stomach and tits and pulled her down to lick the last drops from my wilting penis. She lay back, exhausted. I slipped the thong off her and used it, and the bra to wipe the cum off her tits and stomach. I pushed my finger inside her cunt and played with her G spot causing her to get wetter and wetter and my cock to rise again. I folded up the underwear and carefully put each item in one of the larger pockets of the trench coat. I slipped her stockings off each leg and carefully folded them up with the tiny suspender belt, putting them in my suit pocket. I replaced her stiletto shoes. I held the coat for her to put on. We rejoined the path and walked back to the park leaving the woods and coming into the parkland area. Before leaving the woods I had made sure that only the middle two buttons of the trench coat were done up. Despite Betty's protests she had agreed when I told her she would be safe with me. We walked up the hill towards the café/bar. Halfway up there were two benches opposite each other. An elderly man had stopped (presumably for a breather) and was reading a newspaper. Betty and I sat on the bench opposite. Because of the way the coat was done up, when she sat down it pulled apart at the bottom. The man opposite could view her legs all the way up to her bald cunt. Because of our earlier activity, her cunt lips were protruding and her moist slit was on full display. She looked at me, frightened. I smiled back. The man glanced up from his paper, then back down, then up again and repeated the exercise about five times. He looked at me. I smiled back and reached over to Betty. I popped one of the remaining two buttons on her coat. I looked back at the man. His legs had parted and it was evident from the bulge in his trousers that he was excited. I popped the second button and looked at him again. Betty was focused on the bulge in his trousers. I slipped my hand into the coat and tweaked and pinched Betty's nipple. She squirmed and her cunt lips were opened up to this stranger's view. The main raised his paper and from the activity behind it there was no doubt that he had his cock out. I looked around and there was no one in sight. I motioned to him to lower the paper and he did. He was wanking himself slowly looking a Betty naked except for a coat. I reached down and parted her legs and pulled her cunt lips wide apart. He started to pump harder. I pushed my finger into Betty's cunt and then inserted another and another. With three fingers I worked Betty and as she got wetter the noise of her cunt slurping was quite loud. I pulled my fingers out and pushed them into Betty's open mouth. She licked and sucked on her own juices. Suddenly the man's back arched and he started to come. I did up the buttons; Betty and I arose and walked back to the car. We got in to the car and started back. I made Betty take off the coat and she continued the 10-mile journey home naked, curled up on the leather of the front seat. My cock was hard and she released it, playing with it and occasionally sucking it as we drove along. I for my part played with her tits, pinching the nipples, pushing fingers into her cunt and up her arse. When we arrived back at the flat we were both naked and fucking each other by the time we got through the front door. I fucked her arse and drenched her with cum in a two hour-long session, which wore us both out. After that we both got into the bath and cleaned ourselves up. I left in the evening with a very sore cock and a promise of more excursions to come! I say again and again – In praise of older women!