First (Almost) Anal

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An almost virgin gets well cared for.
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eljayb
eljayb
61 Followers

I was in my late 30's, very happily bi-sexual and really only interested in receiving good blow jobs. Coming home one Saturday afternoon from a meeting somewhere I stopped off at a public toilet where one was as almost guaranteed to get a quick blowjob. The Toilet was underground which meant you could hear someone coming down the steps before they arrived if you were enjoying some pleasurable activity.

There was one man there when I arrived standing at the wall urinal and obviously stroking his cock so, not one to be shy I stepped up beside him, unzipped and did the same. Within seconds his hand was on me and he started stroking me very softly and very nicely. He stooped and gave me a soft, sweet suck and then said, "I just live down the road, would you care to come back home with me? He was good looking, he had a sensitive mouth, he lived close by. What else could I ask for?

I followed him down the hill to his apartment block parked and he led me up to his flat. It turned out he was Russian and was visiting New Zealand working here for a two year contract.

Now I was hoping for a good oral session and, believe me, he was VERY good but he had an ulterior motive. His cock was the largest I have ever seen outside of a porn film It was thick and it was long (actually MASSIVE is the best description) and it fascinated me.

He asked me to let him try to excite me enough to let him put the head into my almost virgin bum.

There was something about this guy, he was just turning me on. He promised to stop at any time and that he would be very slow and very gently and I believed him.

He positioned me kneeling on his bed but down on my haunches while he stood beside the bed and first he softly licked all around my arse, tickling and gently probing with his tongue, That felt sweet, Then he got some lube and just played around the outside of my hole gently stroking and pressing with a finger and then gradually the pressing became a bit firmer but never fast and never hard. Meanwhile he kept asking if I were OK.

Oh Yes, this was all rather neat. His little finger (at least I think it was) gradually inserted itself a little way in my bottom and then came out, more lube and in again until I became totally used to the lovely slidy and filling sensation and then he tried another thicker finger and repeated the exercise, gradually getting me used to the sensations, then two fingers. I couldn't believe this was happening, The sensation of filling was lovely, the slidy sensation was erotic AND THEN HE FOUND MY PROSTATE. Oh heck!!

He probably fooled around for 15 minutes and then said he wanted to try his cock, I could say stop at any time. I thought of this MASSIVE thing and wondered how it could possibly fit but I was so aroused and trusted him at this stage that I said yes.

Again lots of lube and he pressed this warm soft/hard thing against my hole, pressing and releasing, pressing and releasing and I really believe my bottom just opened to receive him. He was incredibly patient once the head was in. He just stood there with it resting inside me and I gradually became used to the sensation of this enormous plug in my bottom. Then he moved it, ever so slightly, forward and then stopped. My arsehole was being stretched beyond anything I thought was possible but it didn't really hurt, He pressed in some more and I yielded to home. Then he withdrew a small bit and pushed again. I could feel him slathering lots of lube around the outside of my bum and presumably on his cock.

He pushed very gently again and more of this monster came in, Then he moved back a bit and pushed in, moved back, pushed and I pushed back toward him and he slid the lot into me. VERY slowly but very purposefully.

You know I am trembling as I write this and yet it happened probably 30 years ago or more

I was experiencing a whole new world of sensation. By all rights I should be screaming in pain with a monster like this in my but in fact it was novel and nice and I wanted to give him pleasure to so I just let him slide slowly in and out and enjoyed feeling his pleasure increase. Finally he said I am coming and I felt his cock swell in my hole and then he was shuddering and releasing. When he had softened he very slowly eased himself out and pressed me to my side on the bed to rest and to relive my cramped legs. He got a warm face cloth (only three of my male partners ever think of that nicety) and wiped me down..

We had a coffee together and I left and never saw him again.

eljayb
eljayb
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AnonymousAnonymousover 4 years ago
loved it....

mhmmmmm i can so imagine this - as though i was there watching you....and encouraging you both.....

eljaybeljaybabout 5 years agoAuthor
Thank you for your remarks

I would love to hear from you

at

eljayb@protonmail.com

AnonymousAnonymousover 5 years ago
Nicely done!

You were so lucky to have met this fellow. By any measure he was a true "gentle-man", so often one has encounters with men with bad breath or other poor hygiene or are pushy in the extreme. I know some enjoy being used, but I personally find much more satisfaction in slow and attentive sex rather than the explosive and brief rapacious fucking one sees on film these days. Your Russian beau sounds like a dream come true! More please, and thanks for the work you do in writing these lovely memories from your long and sexy life!

So regretful that you did not hook up with him again. Well, hopefully he found a winsome lad very like yourself.

Note: I wrote you earlier today and am now working through your stories, enjoying them one by one.

AnonymousAnonymousalmost 7 years ago
First times

Not always the best , but certainly most exciting!!.. mine was when I was 17 , a near neighbour in his 60s ( partly disabled ) whose wife had died 2 years earlier

My stepmom insisted I offer to help with any garden jobs as Phill was unable to reach lots of things , his left leg damaged in the car crash that claimed his wife ..

Presenting myself at his house early on Saturday morning , I agreed to cut the grass and weed the borders on his rear garden .. the work was quite easy and I was finished by 1 pm , but quite sweaty and dirty ...

Phil ( bless him ) told me to go upstairs and get a shower and n the meantime he would rinse my clothes and dry them ... after a longish hot shower I dried myself and looked for my clothes ..

" Still in the dryer " Phil shouted upstairs " there's a dressing gown on the back of my bedroom door you can wear "

Dashing naked across the the hall I found a white silky gown hanging up ( probably Moiras , his late wife )

Thus attired, I went down into the kitchen where Phil sat

" Suits you " he smiled .. as I sat , the gown gaped and my cock was exposed

" Wow .. you're certainly big for your age !!" He gasped

Covering up quickly I blushed

" you got yourself a girlfriend ? " he probed

" Not really into girls - yet " I replied too quickly

" No shame in that .. so it's boys then I suppose ?"

I blushed furiously and almost cried , but Phil quickly moved beside me and put his arm round my shoulders

" Don't worry, I know how you feel " he said soothingly " I am the same "

" But Moira? "

" Marriage of convenience - she knew everything , that's why no kids "

As he spoke his hand slowly opened my gown and dropped into my lap onto my now

Stiff cock , his face on my neck nibbling it

"Tell me to stop if you want " he groaned, pumping my cock

" I-I want you to fuck me " I gasped out loud

" Ever been fucked ? " he whispered

" Nooo.. but I want to now " I groaned

So right there on the kitchen table I got my first fuck .. he was gentle and understanding, kissing away my guilty tears after he had finished

We started a regular thing after that - including me dressing up as Moira and sleeping with him

eljaybeljaybabout 7 years agoAuthor
thanks for your comments

I can only say that I was writing what happened. I don't have the imagination to make a story like that one up.

A one off experience which I shall never, ever forget

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