Mary Mary, Quite Contrary

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My sex life begins with an older very petite lady.
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Pipe69
Pipe69
5 Followers

This is a true story, but names have been changed to protect the guilty.

I'm Rob; now aged 57 and I stand at 6'4" tall, brown hair, brown eyes and broad build. I was born and raised in Cornwall in England, and as a teenager I used to play County level rugby until I got a ban for being naughty on the pitch (OK so he didn't need both ears).

As a child in a working class family I grew up respecting work ethics and realised just how hard my parents both worked. I ended up being the first child to go to University from our family and got a bursary from the Town Council to help with my education costs. You could say that like most boys I was bright but lazy.

My nickname was 'Pipe', after one of the other players saw me in the showers after a match. I am as most women would say nicely endowed. I did measure it at nearly 10" when erect, but it was also very thick.

I started part time work in a photography shop and realised very quickly that the Photographer was (a) Gay and (b) developed material others wouldn't. The 'special' developing was always held in a drawer and sealed in a brown envelope. I got curious and took a peek at one set and got a pretty big shock to see the Jeweller's wife nude and being screwed by the dentist. I then opened every packet I saw and learned very quickly that most of the so called respectable people in the town were anything but.

Whilst all this peeking aroused my interest further in sex I kept focused on my studies and by the time I was finishing my Sixth Form doing my A Levels the girls assumed I was gay and tended to be closer to me as a result. I also knew what many of their parents got up to and that always gave me a smile.

It was at this time I finished my job at the Photographers' after he retired and I looked for something that enabled me to use my brain a bit more. This is when Mary entered my life and I definitely entered hers.

Mary was my mum's friend. She was in the same Maternity Ward as my mum and whilst they were very different personalities they stayed firm friends. Her daughter was the same age as me to the day and was to be honest gorgeous, but an absolute bitch. I stayed away as she really annoyed me with her Princes attitude; her mum, however was a different matter. Mary was 5'2" tall, very slim, dark hair to her waist and although determined or hard in her looks she was really good with me and my mum.

My mum asked me to help Mary put together her parties, as she sold kitchenware. She was very good at these and quickly rose in the ranks, but then was asked to organise and attend exhibitions and put up displays. She clearly needed help and my mum volunteered me. Mary paid well, we stayed in nice hotels and B&B's and I was very diligent. When I could drive I ferried her around and shared the driving. I used to look at the guys admiring her and the ones that tried it on with her got short measures, however, I could tell her marriage was on the rocks. Her hubby was weak and spineless and eventually left her (moving in with another man). She was very upset, but threw herself into work.

We were setting up a trade stand at a show in Bristol and got to the hotel late and discovered they had double booked and there was only one room. Mary looked at me and said "Well it looks like we are sharing then"; so that was that. I just went with it. I had decided to do a gap working year before Uni to build up the funds.

The hotel room was ok; you know reasonable size, decent bathroom, but only a double bed. I would be sleeping right up against Mary and with my 'friend' likely to wake up and poke her in the back I was a bit concerned.

Mary went to the bathroom first and came out in a fairly sheer nightey and got into bed, but I generally slept in the nude so I kept my T shirt and underwear on. I could see Mary looking but decided she was just curious. How wrong could I be?

We both snuggled down and after a hard day I was away and asleep, but during the night I woke to find Mary had snuggled into me and my hard-on was poking into her. She appeared to be dreaming and was running her hands over me. It was then that I realised she wasn't asleep and that she had her hand on my cock. She stroked her hand up and down through my underwear and murmured "That's the biggest cock I have ever felt ... Nice". I then felt her slide down the bed remove my underwear and put her mouth over my glans. She couldn't fit it in her mouth so she started to work her hand up and down the shaft and at the same time sucked. This was all too much for me and I instantly shot cum deep in her mouth. The amount of cum was such that although she gulped it down it was going all over her chin and breasts.

Once I had cum she sat up and kissed me. It was not a new experience licking my own cum, but she was now utterly rampant and asked if I had ever given a woman oral sex. I just said "No" and she took her nightey off to reveal amazingly taut breasts, which were just a bit too big for her small frame and topped off with gorgeously small and tight looking dark nipples. Her body seemed unmarked by childbirth and she had a very neatly trimmed mons, with small labia lips. She had an amazing body and definitely was every young guys dream.

Mary took one of the pillows and put it under her bum and opened her thighs to expose a very small pussy with very neat lips and leaking profusely already. Her clit seemed large for her body and looked like a small cock as it stuck out from her body. I really wanted to taste a woman for the first time and Mary pulled her lips apart and I could see deep inside her wet hole. She then started to show me what to do. I was instructed to slide a crooked finger inside her and to locate her G spot. This made her leak even more profusely and she shook as her first orgasm hit her. She then pushed my head down and told me to lick her clit and slide another finger inside her. This made her go all stiff and arch her back as she came again. She seemed quite fixated on cumming as much as possible and it was my job to help her achieve that.

After about twenty minutes she pushed me away and fell back on the bed utterly exhausted. She noticed that I was already erect and said she wanted to be fucked. I was instructed that under no circumstances was I too cum until she let me. It was at this point I realised that she was very much in control.

She didn't use contraception as she said she had been told she couldn't have more children so wanted me to fuck her bareback. So my first fuck was not with a condom, but deep inside a petite gorgeous mature woman which as I found out had the most amazingly tight wet pussy I still have ever experienced.

I positioned myself with my cock pushed up against her labia and she dragged it up and down her clit making herself wetter and wetter, until she asked me to slide into her. This took some doing as I watched her lips stretch around my huge glans and I gradually eased into her. I managed to get about half way in before she asked me to stop. As I slid into her I could actually see my cock pushing her stomach muscles out and watch its progress as her tummy bulged. I told her I had as much to go as was already inside her and she said she wasn't sure she could take all of me. I have to say that I wasn't sure either but she then pushed me on my back and started to slide up and down. My shaft looked magnificent against her tiny frame and much to my surprise she finally managed to get all of me embedded inside her. This triggered a massive orgasm and I could feel her internal muscles ripple along my shaft. She said afterwards it was the most intense orgasm she had ever had.

Being inexperienced I would have probably cum earlier if I hadn't offloaded in her mouth previously, but I was still having trouble not cumming. She could feel this and sat down hard on my cock to prevent me blowing my load. She just said I had a lot to learn and not to cum until she said. I could see she meant it.

She continued to ride me with my cock wedged against her cervix and having orgasm after orgasm. The bed and my crotch area was soaked in her juices. The room smelled of sex but I was lost in watching and hearing her own self enjoyment. She would rise until the very tip of my cock was inside her then crash back down squeezing my shaft with her muscles and sending her into another wet orgasm. This must have continued for at least thirty minutes until she rolled off me utterly spent.

I was still hard and desperate to cum. She grabbed my cock and began to wank me until she gave me permission to cum. I just let loose and pumped so much cum out it went in her face and hair and dripped down her breasts. She just said I'd make an excellent lover with her tuition and so our long term affair started.

If you want the next installment say so?

Pipe69
Pipe69
5 Followers
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  • COMMENTS
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7 Comments
oldwayneoldwaynealmost 4 years ago
Enough...

but thanks. Five Stars!

Pipe69Pipe69over 4 years agoAuthor
Thanks

Thank you for the feedback. It's my first effort.

I wont please everyone and don't aim to.

I never have commented on others stories as I didn't feel I should unless I too have contributed; therefore the negative comment I shall ignore as I declare them to have no real voice.

kjohns2001kjohns2001over 4 years ago
Brings back memories

Brings back memories of my losing my virginity with an older woman. She taught me well and I still remember her fondly nearly fifty years later. I think that there are far more younger men who are taught how to love a woman by an older woman than most would believe. In any case I enjoyed your story, and yes I would like to read more about you and your first lover. Thank you for sharing it with us.

chytownchytownover 4 years ago
No***

Borderline boring it's the same oh storyline boy has ten in dick women has a clit that as big as a small penis and the hotel overbooked and they have to share a bed. Give me a break!!!!!!!!!! Sorry !!! Thanks for writing.

AnonymousAnonymousover 4 years ago
Mary !

SO !

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