Diary Excerpt #69… Guest Post
Hi Elliott… a bit of a different one this week. See what you think?
Diary….69 A fitting number for this entry. While I’m watching porn all sorts of fantasies begin to play out in my mind.
For almost all of my life I’d been perfectly straight and I would cringe if ever I saw gay guys kissing.
So it had been surprising to me that more and more while watching porn with girls sucking off guys again and again , that I began to catch myself wishing I was the girl sucking cock in that scene instead of the guy being sucked. I didn’t just want to suck off some hairy guy on the street but when I saw a tranny escort who described herself as pre-op it seemed a good chance to find out if I really could bring myself to be with a male?
After texting I went to a nice expensive looking apartment block in southbank , close to the city. Having to buzz inside then up 7 floors and walking along the long quiet hallway , all the time saying to myself “if I don’t like it I will just say sorry and leave!”
A girl opened the door.
I say girl because she looked so feminine and talked in a soft calming voice that it was hard to imagine she was ever a boy.
Only her height, which matched mine, hinted at a slight difference.
Her breasts were nicely sized and matched with her thin but shapely figure. She had fine features , fake tan flawless skin , full but not heavy make-up , full lips , long flowing hair and was gorgeous.
After a few minutes chatting about the weather and her day job etc she holds my hand and asks , “so what are you after today?”
She was wearing a sheer , see through black shift so my eyes drifted to her body…..”oh besides that lovie” she chuckled.
I found it hard to say ‘I want to see if I can bring myself to suck a cock’ , so I just shrugged instead…
“Well lets get on the bed and see what happens shall we?” , she led the way still holding my hand.
Somehow the way she said..” ..see what happens..” led me to think she gets a lot of guys like me who are curious but not sure what they’re really wanting. It made me a little more determined to stretch my boundries and to experience something I might never do again.
I drop my clothes casually then lay on the large luxurious bed to watch as she undresses and lays beside me demurely covering herself with her hands. I felt in control.
Without a second thought I began kissing and fondling as if she were any other female escort , while looking for boundries. We kissed passionately with tongues! I sucked big brown nipples ontop of perky but soft breasts. Suddenly I realized I had a decision to make…. if I let her suck me first I’ll get hard which will lead to sex ….after I’ve cum all my lust fueled desire for sucking cock will evaporate! So I had to suck first!
I kiss my way down her body till I found her tiny dick and began sucking. It was only about 3inches at most, even fully erect ,which only lasted less than a minute while she repeatedly called it her pussy. “Oh lick my pussy” , ” my pussy wants you” etc.
I had achieved what I wanted even though it hadn’t been as thrilling as I’d hoped for but at least I could cross it off my bucket list.
I went back to kissing and felt myself firming up. She went down for a bare blowjob that soon had me hard for her to put a condom on.
All my thoughts had been on testing my curiosity so I truely hadn’t even considered that anal sex would naturally come next!
I’d only once gone anal which was with karen , 30yrs ago , so I wasn’t prepared for what came next.
The trans girl got a handful of oil and stroked my covered cock then I knelt between her legs in missionary…. she guided me inside… it felt the same , our position was the same,… if not for the little cock between us I would have sworn she had a pussy.
I came while kissing her.
We had a very friendly chat afterwards even though we were from vastly different lives.
Talking openly about why she’s transitioning and how it all works…. the reason for her lacking penis being a result of years of hormone pills that gives her the very feminine appearance.
Her day job is at a ladies fashion shop with other sales girls her age. She’d kept her secret from them for months till the head boss questioned her about using the ladies toilet. Though shocked at first her co-workers agreed to treat her as one of the girls …the pride she had for those ladies who accepted her was huge!
As I walked to my car I was happy I’d seen her yet now I’d checked off sucking cock from my list I didn’t feel the need to try it again.
The bonus was that anal sex had also been crossed off. Though that was something I’d like to try again… especially with a girl!
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Meet Howie… a 54 year old happily married man living in Queensland, Australia. Unfortunately for Howie, his wife is no longer interested in sex. But, Howie still is, and since he loves his wife, and would never be unfaithful, he seeks relief from sex workers. Howie is not a writer, just an ordinary family man who keeps a diary, well hidden I’m sure, here is a page or two.
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9 comments on “Diary Excerpt #69… Guest Post”
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Life of Elliott... 
Well done. Congrats on the bucket list and Thanks for sharing
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Thank you so much for sharing this, Howie! I think it’s wonderful that you did this, but also that you had the chat afterwards. And yay for those girls at work accepting her as one of them. Brilliant and the way it should be 🙂
~ Marie
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Oh Marie I was so glad I asked. I’m getting to be a real softie in my later years so when she teared up while telling me about the acceptance I couldn’t help but shed a few tears along with her. It was an epiphony for me that gender is a fluid thing.
I tried to imagine her as a guy but I doubt he would have fit into any ‘so called normal’ group like that.
I never went back to her but often think of her and hope she’s happy.
Thankyou so much for taking the time to read and comment marie.
It makes my day to read your comments😍
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Experimenter!
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In sex I suppose I am…. but in life?…not so much.
I’m glad you’re reading my little bits and I hope you enjoy them.
💝
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I enjoyed reading this story. You would be surprised how many men are curious about this.
As an aside the biology of the penis and the clitoris are similar. So she was not really incorrect when she called her cock her pussy. Some women actually have clitorises that could be regarded as a small penis.
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Hi gem , thanks for your comment. I would’ve been surprised a few years ago but I’m now on other amature sex shareing sites and I’ve noticed once guys reach late 50s it seems almost all become curious.
Maybe less sex at home adds to the desire? Only a few might take the plunge and experience same sex relations. I met a guy recently from a site like this that had 14guys in a row that didn’t turn up for a meeting with him.
🤔
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It is hardly worth pestering with such questions why and how. Perhaps he himself does not know all the answers. I think so.
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It was a very friendly chat where she was the one who wanted to talk about those personal things.
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