Diary Excerpt #75… Guest Post
Page #75… I’m ticking off most of my box’s now by going to a variety of ladies yet one thing I’m not satisfied that I’ve explored enough is if I would ever be able to enjoy being with a guy. Apart from 1 day as a young boy I’d never even considered being with men yet in the last few years an urge has grown in me for sucking cocks. I’m aware by now from many chat’s online with guys my age that it’s something lots of guys are curious about but few have the chance to explore. I still wasn’t sure about all the hairy hard bodies and just how far I’d go in real life. After my first visit with a tranny many months ago had left me feeling like my questions weren’t really answered because he/she looked so much like a girl ,and her dick was so tiny , I wanted to try again. So after yet another session of stroking my cock over video’s of guys having their cocks sucked by girls I book another tranny who looked older and less feminine than the last.
His add said he was my age so that too was going to be interesting. I book 45min and turn up at an older home that had been converted into 4 smaller units so my instructions were to knock on the rear door. The door opened and a guy in a wig said “hi” in a deep manly voice. There was no mistaking this was a guy! He had a fake looking blonde wig , heavy make-up and lipstick , a big firm belly and man boobs! I stepped in as he closed the door. We stood face to face close together in the hallway. Pressed up together in the tight space. It seemed we were both wondering how far each of us was going to go. I find out later he is never really sure if guys like me are going to stay or run away.
I wanted to make sure I didn’t waste this opportunity to test my boundries in case this was the last time I do this sort of thing so I plunge all in. I kiss him fully and passionately.
Tasting his lipstick and twirling his tongue as my hands grope his manboobs and body while telling myself this was what I wanted.
He wore a black satin nightie with matching , loose fitting , panties. His bony thin legs didn’t match his large belly but I was all over him. He matched my enthusiasm yet when I slid my hand down to feel for his penis I got a much better handfull than he did of mine because I was still in my jeans.
“Mmm come this way sweetie” he said as he tried to wiggle his almost flat bum while walking in front of me.
My mind was swirling! For decades I’d been disgusted by any vision of men kissing yet there I was pashing him fully and getting turned on by it! Even when I felt the tiny prickles of his beard!
The real test was going to be when I touch his cock though , it already seemed bigger than mine.
I quickly undress in case my thoughts change and I no longer have the courage to push forward with this experiment.
He’s not ready so I go to him and we kiss as I finish undressing him. He lays on the bed and I crawl ontop as if I really was the man in this scenario. It feels exactly like being with an overweight , older , less attractive female escort but it was very obvious he wasn’t female.
I’m assuming he’d been on a slight hormone supplement considering the un-natural size of his manboobs.
All bodyhair had been removed but the firmness of his body really surprised me. I’d figured a huge belly like his would feel soft and wobbly but it felt like a rock!
I was determined to push on so I work my way down till I had his erection in my hand , without hesitation I suck him.
I called on all those thousands of hours watching porn to instruct my action which seemed work resulting in a very firm dick of around 7″ which was about 1/2 an inch longer than mine. He motioned for me to flip so he could return the favour. I felt myself stiffen and grow in his mouth but became too distracted to continue pleasuring him.
When he asked “do you want to fuck me?” I wasn’t 100% sure as I’d only thought as far as testing my limits for sucking , which it seemed that I had none , I hadn’t thought that I’d get stiff. Once my erection was up then all reservations seem to vanish however they all flood back in just 1 second after climax so although I may regret it afterwards I went for it.
The sensation felt strangely similar to the many times I’d fucked escorts in the past , if not a bit better than some because it was tighter.
He’d offered to turn over so I could imagine he was a woman but I always prefer to see the face of the person as I probe them so he lifts his thin legs for sex which had the added benefit of watching his erection wagging like a dogs tail in rhythm with me.
I came , he cleaned me up, then we lay naked beside each other. As I’d ejaculated all my confidence , my conviction , my desire had vanished too! We’d used up all my allotted time yet he coyly asked ,” so what more do you want to do hmmm?”
My years of church lessons and family values came flooding back as it hit me what I’d done.
I felt a bit numb , like I’d cheated everyone I knew. I think the guy wanted to spend the rest of the day in bed with me but I made a hasty exit and drove home. By the time I’d reached home I’d bounced back a bit so I was able to appreciate how it had felt fairly normal to be with a warm body and how for some I can now understand why gender doesn’t matter.
By the next day all my pent up desires for sex in any form returns. I’ll always prefer a female but now at least I knew what it is like to be with a guy.
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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. E H
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8 comments on “Diary Excerpt #75… Guest Post”
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Life of Elliott... 
As I read the first lines of this story a thought crossed my mind that you would meet this man and he would be someone you knew from your past!.
THAT would have been a twist.
I am impressed that you are following your fantasies.
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Wow true! I hadn’t thought of that😮 So many guys online talk about wanting to experiment but it seems few fullfill those desires so I’m happy that I explored the fantasy. My guess is that men just want to be with someone who wants sex as much as we do. That’s why so many older married men are talking sex on line to other men.👄❤
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Or perhaps having sex with someone of the same gender is just a natural thing to do and not the unholy evil we have been told it is for the last couple of thousand years.
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nicely done.. i tend to be vey oral and bi. so i find this very exciting. glad you had the experience.
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I share your love of oral Sindee. Kissing , sex or sucking. I just like to please others 👅👄❤
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I want to echo what Gemmi has said: I am impressed that you followed through. Thank you for sharing this with us 🙂
~ Marie
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I was worried people would be put off by such a full on man on man story. You wouldn’t believe how terrified I was before I got there but the instant he opened the door I relaxed. It just struck me that just because some people have dicks and others have vagina’s they are all people wanting to love , laugh and be hugged just like everyone else.
Probably won’t do it again but glad I did.🤔😊
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I think and believe what Gemmi said is true ‘ …. having sex with someone of the same gender is just a natural thing to do and not the unholy evil we have been told… “”
Maybe if Cyndi Lauper sang Boys just wanna have fun now instead.
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