The Old Dog Teaches Me New Tricks

I have been fortunate to have had a number of liaisons and relationships with older ladies and each of these relationships has been different in its own way.

The following story however represents a new direction in relationships which gave me as much pleasure as all the others and was again a rewarding experience.

I had been invited to the Open Golf at Liverpool in 2006 by one of our funding banks and they had requested that I went up on the Saturday night so as to get an early start on the last day (Sunday). I joined my hosts at an excellent hotel and we had a good dinner and then on the Sunday spent the day at the course and enjoying hospitality.

Most of the guys worked in Manchester so they were leaving on the Sunday night. I was staying for a second night due to the distance I had to travel and the considerable amount of alcohol I had consumed steadily during the day.

In the evening the guys went their various ways and I was left alone in the hotel. I showered and changed and made my way to the bar where I enjoyed a very large Gin and Tonic whilst contemplating what I would have for dinner.

In the lounge of the hotel there was a woman sitting o one of the chairs on the other side of the room. She was in her sixties (as I found out later 67), well dressed and reading a magazine with what looked like a gin and tonic in front of her.

She had immaculately coiffed grey hair which was tied back and she was wearing a calf length skirt, brogue shoes and a white blouse under a blue cardigan.

Our eyes met and she smiled at me which was all the encouragement I needed.

I wandered over and asked "do you mind if I join you?"

"Certainly" came the reply "please sit down"

It transpired that she was divorced, was a keen follower of golf and had also been to the tournament returning earlier as the day had worn her out having travelled up on her own on the Wednesday night and spent all four days at Royal Liverpool.

We swapped stories about the days play and when I asked her if she wanted me to join her for dinner she said she though it would be lovely – we went in together.

We had an excellent meal with (after much persuasion) two bottles of very good wine and a couple of brandies back in the lounge with our coffee.

She was also persuaded to a "nightcap" of a further brandy which we ended at about 10.30.

We had been talking a great deal about manners and common courtesy during dinner and therefore it was no surprise to her when I offered to walk her back to her room. She welcomed the offer and admitted she may be unsteady on her feet.

We stood, she took my arm and we wandered out of the lounge, through the courtyard and into another building and up the stairs to the first floor where her room was situated.

When we got to the door I said I had enjoyed our chat and I kissed her on the cheek. I started to walk away and she asked me if I wanted "one more drink" before going off. I accepted intrigued by her invitation and we found ourselves in her room.

The hotel was of excellent quality and the double bed in the room was very large, complemented by a large settee and two TVs, one by the bed and one in the lounge area.

She opened the mini bar and returned with two brandy miniatures which she handed to me – I found two glasses and filled them and we sat down together on the settee.

We continued to chat and drink and as I was in much closer proximity to her in he room I could smell her heavy perfume – I was hoping that I hadn't misread the signals so I put my glass down and half turned towards her – she looked back at me, glass still in hand.

I put my hand under her chin and leaned in towards her and kissed her very softly on the lips – she responded and we continued to exchange kisses in a very formal way.

I took her glass away and put it on the table and put my arms around her and kissed her quite passionately. She responded and my hand moved round to the front to cup an ample breast which was very heavy and full.

At once she removed my hand and stood up. I must have looked surprised as she smiled and reach out for me to stand up also.

She pulled me into the middle of the room and let my hands go. Then she walked a complete circle around me as if she was looking at me from all angles.

She knelt down and took of my shoes and my socks. Then she stood up again. I made as if to go towards her with my arms out but she pushed me back with my arms at my sides. Al this time she never said a word.

She walked round me again.

Then she lifted my shirt out of my trousers from the back, pushed my arms up in the air and took it off me returning my arms to the downwards position again.

She walked around again this time running her hands over my back and my chest – I took her hand and tried to kiss it but she forced me to stand with my arms by my side.

She arrived back in front of me, undid my belt and pulled it out of the loops in my trousers putting it on top of my neatly folded shirt. She then undid my trousers and unzipped my fly opening them out but not pulling them down – the suspense was becoming unbearable.

She walked across to the other side of the room and took a drink of her brandy. Then she came back and carefully pulled my trousers down opening them at my feet so I could step out of each leg. She folded them and added them to the pile of clothes. I was now standing in my boxers and finding this activity extremely stimulating.

Again the trip around me only this time my legs front and back were rubbed squeezed and given attention.

She kneeled down in front of me and reached her hands up to the waistband of my boxers – slowly, very very slowly she peeled them off me and again opened up the legs so I could step out of them.

She got up and stood back looking at my hard large cock which was swaying like a serpent – she still never said a word.

Round the back again she went this time cupping my buttocks and rubbing them and putting her hands up my back and down my legs over my arse.

She stood in front of me and lent forward her hand extended and she touched my hard cock not a grip but just lightly allowing her palm to slide over it without really gripping. She got to the bottom of the shaft and gently cupped my balls, teasing them in the palm of her hand.

She then took two hands and wrapping them around my shaft just below the tip slowly pulled back my foreskin all the way until the huge helmet was fully exposed. A small drop of pre-cum had formed and she touched it with her finger and pulled it away watching it stretch until it snapped back to the tip of my cock.

The first words were spoken then for almost 15 minutes –

"Your turn" she said

She stepped back from me and stood with her hands by her sides. This was unbearable but at the same time a real turn on – I was naked in a hotel room with a fully dressed 67 year old woman and now she wanted me to do to her what she had been doing to me!

I stood back and walked around her, got to the front and knelt down slipping off her brogues – I noticed that she was wearing stockings.

I removed her cardigan and neatly folded it – then undid her blouse all the way down the front and eased it out of the waistband of her skirt – she was wearing a petticoat slip underneath – the blouse was again neatly folded.

I walked round the back and looked at her broad shoulders, came round to look at the large breasts covered with the slip and the underclothes.

I unzipped her skirt and slipped it down the silk petticoat round her ample hips and behind, again opening it up on the floor so she could step out of it.

After another inspection I gathered the base of the petticoat and after lifting her arms up removed it by lifting it over her head.

With all these clothes removed I could see that she was wearing what could only be described as a foundation garment, a one piece white combination of bra and corset which had suspenders built into it and over this she was wearing a sizeable pair of white lace knickers.

I ran my hand over her back feeling the smoothness of the nylon material and walked around the front where I did the same to her ample breasts and stomach.

I again knelt and this time slid the lace panties down getting a brief glimpse of a copiously hairy bush. Around the back two buttocks freed from the lace panties showed at the base of the foundation garment and I ran my hands over them and between her legs briefly – still no sound from her.

I undid the suspenders and slid the stockings from her legs.

The contraption was secured by a number of hooks and eyes and one by one I managed to release them from the middle of her back to the top of her buttocks, each release enabling more and more flesh to be shown. Having undone all of the hooks I then moved round to the front.

I released her arms from the shoulder straps and gently but firmly began to pull the foundation garment off her. With each pull her breasts became more and more exposed until finally the garment was down to her stomach.

Her breasts were huge and droopy; each topped with a very large brown aureole and very big erect nipples.

I was now on my knees and slowly pulling the garment over her hips and thighs – her stomach rolled out as the garment released it and having to move round to the rear to continue pulling down the garment I was also able to see an absolutely huge bottom.

At last the resistance gave and the garment now relieved of its stretchy duty was compressed and could be removed by her lifting her feet.

I stood up and folded it on the rest of the clothes.

I walked towards her and looked at her old fat body still showing marks of where the foundation had been. I touched her breast, lifting its weight with one hand and watching where it spilled out of my large hand. I rubbed my thumb over the dark brown fiercely erect nipple and watched it spring back to attention – my cock stirred, throbbing.

I grasped a breast in each hand rubbing her nipples and watching them intently. My hands moved up to her broad shoulders, and then down again to slide over her distended belly.

Walking around her I put my hands on her shoulders at the back and slowly slid them down over her shoulder blades to the small of her back and on to her buttocks. Her arse was huge!

I parted her buttocks and looked with interest at her arsehole, small and puckered deep in between the cheeks. Holding her cheeks apart I probed her arsehole gently with my finger. She shivered.

I came back around to the front and knelt down – I parted her copious pussy lips and looked at a huge clitoris nestling in a forest of grey hair. I rubbed it gently at first with my thumb then applied a little pressure in regular probing movements. She squirmed visibly, her pussy became moist and a musky scent emanated from it.

I stood up and looked her – she was old, fat naked and I was standing naked opposite her with a huge and very hard erection. Still no conversation.

She wandered over to the pile of clothes and retrieved the foundation garment – I thought that this was it she had enjoyed her thrill and it was over. I could not have been more wrong!

She held the garment open inviting me to step into it. I had never cross dressed or attempted anything like this in my life but suddenly the thought of wearing this thing, still warm from her and still smelling of her perfume was the greatest turn on imaginable.

I stepped into the garment and she pulled it up my legs and over my hips, taking great care to make sure that my rampant cock was steered appropriately. With practised skill she pushed my arms through the straps and one by one did up the hooks until I was firmly encased in the nylon. She then lifted my legs one by one and put her stockings on me stretching them so as to enable the suspenders to be done up.

She stood back as if admiring her handiwork looking at me in a white all in one foundation garment with stockings tightly fastened in all the right places and pulled up far enough at the front to allow my cock to stand up hard. The feeling of the garment and its constriction and smoothness was a real turn on.

She walked towards me and wrapped her hand around my hard cock – I reached out and cupped her breasts – I pulled her towards me and kissed her hard my hands grabbing at her breasts and buttocks and sliding round to her hairy wet cunt.

She pulled away and led me to the bed by my cock – she laid me backwards on it and lifted my legs spreading them as wide as the garment would allow. I had not noticed before but her hair having been tied up was quite long – she undid the clips and it fell over her shoulders shiny and full and very grey. She walked to the end of the big bed and started to climb on to it coming towards me on hands and knees her pendulous breasts swaying as she focused her eyes on my straining cock.

She got level with my cock and then turned her head from side to side so that her hair was swishing along the tip of my cock – the feeling was indescribable.

She spoke for the first time in ages "you like?" she said – "I love it" I replied my breathing getting heavier.

She moved further up and allowed her breasts to drag across my balls and cock – they were warm and I could feel the hardness of her nipple against my sensitive helmet.

She lay down between my legs " I'm going to wank you until you cum" she said and she proceeded to rhythmically pull my foreskin up and down whilst cupping my balls very slowly with a strong slow beat.

After a few moments I felt my balls tighten and I arched my back as seven or eight spurts of hot cum flew through the air as she pulled and squeezed me with each successive spurt. Each time I shot she exclaimed "yes!", and "yes!" and "that's my good boy!"

When I had stopped she pushed my foreskin back up and kissed the end of my cock.

I had never been so turned on in my life.

She got up and went back to the mini bar and poured another brandy – watching her bend over my cock began to rise again and the garment I was wearing was squeezing my hips and thighs and making me even more turned on. I got up and walked over to her, took her in my arms and kissed her – she kissed back.

"Come over to the bed" I whispered

She stood back and looked at me – "don't ask me to do things – just do things to me – please?"

This was weird!

I cupped her breasts and rubbed the nipples hard again – this time I lifted each breast and sucked hungrily and hard on the nipples biting and licking each one in turn. She whimpered.

My hand went to the back of her neck and I led her by the hair to the bed – she made as if to get on it from the bottom but I stopped her.

I took her hands and put each one on the footboard of the bed about four feet apart so she ended up leaning forward with her hands on the footboard

I ran my hand over her buttocks and slipped my finger between the cheeks stroking her from the top of her arse down to her cunt – she was soaking.

I opened up her cheeks and I could see her puckered arsehole and the lips of her cunt – I bent my knees and positioned my cock just at the entrance to her cunt – slowly I pushed in and felt the hood of her cunt lips wrap around my shaft drawing me into her. I started to thrust into her slowly at first and then building up to a strong rhythm. The wardrobe mirror pictured her, bent over her huge breasts swaying and flapping about with my thrusts her belly wobbling and hanging down.

Again the small sounds "yes! yes! Mmmmmmmmm, oh God! oh Christ! oh Fuck! Yes! Yes!" she moaned -she was almost whispering them.

I was completely pulling out of her with each thrust and plunging my hard sore throbbing cock back into her cunt. I slowed down and reduced the pace still pushing in and pulling out as she whimpered after her orgasm.

I probed the entrance to her arsehole – it was wet from the sweat and the pucker gave as my finger entered a little way.

"don't ask me to do things – just do things to me – please?" the memory of that statement ten minutes previously was still in my mind.

I grasped my cock and pulled the foreskin all the way back and positioned the tip against her arsehole. It looked impossible – my huge helmet looked far too big to get into there – she tensed.

Firmly and slowly I pushed it seemed to give a little but still not enough – I backed away, reached down to her pussy and slipped my hand along its length upwards transferring some of her own wet slimy juices up to the small puckered arsehole. I tried again – it gave a bit more – she moaned.

I pulled her cheeks as far apart as I could and also got her to hold them by moving her hands away from the bed I grasped my cock firmly and slowly bit by bit entered her arsehole. Once my helmet was in the pucker closed around it and I felt like she was clamped on to me. I put her hands back on the bed and holding her hips pushed harder.

Bit by bit inch by inch my whole cock was going inside her. Tight! I have never felt anything like it – she was moaning and crying and I thought she was upset – I tried to pull out but she would not let me – so I went for it and I started to build up again in and out of her arse until I was thrusting harder and harder – she was by now openly moaning and it seemed like crying but she met my thrusts into her by pushing back hard onto my cock – I could not hold out and I pulled out of her arse and came all over her back and hair and arse cheeks.

We fell together on the bed and the activity and the alcohol made me sleep almost immediately.

I woke up in the middle of the night and the garment had been removed from me evidently when I was asleep. The hotel notepaper had a simple message on it:

Thank you for a wonderful night xx

I went back to my room and showered and slept and checked out the next morning – I asked about my companion of the night before but was told she had checked out early.

I never saw her again and although the night was weird it still remains one of the most intense experiences I have ever had with any woman let alone a 67 year old – I would certainly love to try it again! In Praise of Older Women Indeed!