Disclaimer

If you have no stomach for a male on male encounter, please leave now.

Preface

I'm sure you'd all like to ask the big question.

“Flexi, WTF were you thinking?”

Unlike you young lads, punters of my age are forced to face the truth, that our punting career is in the final quarter and the legs are getting weary. As we await the singing of the fat lady, we reflect on the many a happy time shared with many a lovely young lady. We also contemplate. Will I die wondering? Have I ticked off the bucket list? Will I rue the day I procrastinated?

Having had sex with more than 50 trannies, many of whom were little more than guys in a shallow disguise (and enjoying it mind you), I started thinking about this final frontier. Probably about the only area of sexual activity left completely unexplored. This was too much of a challenge to let it go. Well guess what lads; I'm not one to die wondering.

Source

www.rentboyaustralia.com

Michael

I narrowed the short-list down to three but from the outset Michael was the easiest to deal with. I don't find men attractive so my criteria on looks were easy, fit, not bald and not hairy. A number of telephone convos over the course of a few days and we had a plan for a one hour booking on a Wednesday at noon.

Meeting

I don't mind admitting I was cacking myself. We shared a drink of water infused with mint and lime. We drank as we continued talking. I don't know what I was expecting but it was not what I got. I suppose I'd just assumed we were talking clean shaven and smooth but nope, he was sporting a three day growth.

The Sex

I was still shitting myself as we started what was to be a long shower together. Michael massaged me all over with some scratchy (exfoliating) gloves he had with him. It actually felt pretty good once I got used to it. As he stood behind me, he reached around my body and massaged the front and I could feel his tool rubbing against my arse.

After the massage he turned me around, I felt so out of my comfort zone I didn't even have a boner. As we rubbed each other, he pulled me to him and without any real warning planted a passionate kiss which turned almost immediately, into a probing tongue kiss. He was a very good kisser actually and his breath was nice. Can’t believe his lips could be so soft and his bristles so damn hard. I told him I'd never kissed a guy before and I'm not sure I like all the stubble. He apologised and offered to do a quick shave so I thanked him and accepted. It was still scratchy but least it felt like I may have had some skin left on my face when I got back to work. I don't know how the girls can stand it.

We spent a long time standing under the shower rose with our mouths locked. Firstly he'd push his large tongue into my mouth which is more normal for me as I'm more of a passive kisser. In this case though, I felt we were on solid terms so I'd take my turn to reciprocate by pushing my tongue into his mouth and running it around his teeth. Occasionally our tongues would meet in a stalemate and caress each other in neutral territory outside our mouths. Our penises were both beginning to show a hint of interest, massaging each other to erection as we lightly ground our groins together.

After the shower we went back to the bedroom. Michael put on a DVD on his iPod which was displaying gay porn. I felt a little weird and just gazed at the carpet instead.

He started to give me a very thorough massage and he was quite an accomplished masseur. After the massage he presented himself for more kissing. As I said, he was good at it but I had to close my eyes and pretend I was kissing a girl, albeit a girl with whiskers, lol. I had to psych into it all over again. After about ten minutes he sat up and said do you want to fuck me now. I said I'd rather give you a blow job if you don't mind. He looked a bit shocked but I had been very clear on this point during the initial contact, several times in fact. We started with some mutual oral but he was a little bit rough which surprised me. Soon after I moved my position and it morphed into me kneeling on the bottom of the bed between his legs. His penis was not much different to my own, perhaps a little thicker and circumcised. His balls were quite large and puffy with short hair. I licked them and took then into my mouth one at a time. Trannies often have super-sensitive balls and often don't welcome the attention so it was good to be able to have a nice long play without complaint. I thought with big puffy balls like that he may later unleash quite a load.

After a thorough ball bath, I started to lap at his cock. It's is a fascinating organ, so hard yet so soft. The head of his penis felt awesome against my lips. I took him in my mouth again and started to do what I know feels good for me, assuming it was the same for him. He seemed to enjoy it with his sound effects and the fact that he stayed nice and hard. I particularly like it when you feel a cock pulse in your mouth signalling a level of enjoyment. I used a tension at the base of the penis with my right hand as I gently squeezed his balls with my left. My lips were working only a downward motion on each thrust as my tongue kept pressure on the underside.

I kept my lips gently resting on the penis head as I used my own saliva as lube for the motion of my right hand up and down his shaft. Then all the way down to his groin as his penis push into the back of my throat.

Sometimes, I'd stop everything and just enjoy looking at it and feeling its softness on my closed lips. It took him about ten more minutes before he signalled his intention to cum. It was a thoughtful warning which I disregarded, lol. I was a bit surprised how gentle his explosion was, instead of spraying the roof of the mouth, I was virtually unable to feel it at all. Even without the squirt there is the unique ammonia-like taste that can be felt in the mouth as well as tasted on the ridge of the tongue. I dribbled his load onto his lower belly so that I could play with it with my tongue and prolong the enjoyment. I little bit of play before collecting it up again. Mission accomplished.

It was then my turn to cum which I did with a hand job as I enjoyed the lingering feeling of his softening cock in my mouth.

Michael charged $200 for a generous hour and said if I wanted to be a monthly of fortnightly reg he'd do it for $150.

The fact that I didn't really enjoy it is not a reflection on Michael. I thought I would have been more into it but I just couldn't get very excited about the intimate stuff. I think hence forth I'll stick with trannies for variety in the toy box.