Adventures Of Bob - Part Four - Bob Loses His Ladyboy Cherry In Manila - Sex Stories

Adventures Of Bob - Part Four - Bob Loses His Ladyboy Cherry In Manila

Bob was never really homophobic, even though brought up in a time when homosexuality was not just frowned upon by the so-called polite society but a criminal offence which could result in prison time. Heterosexuals of his generation, whether admitted or not, were uncomfortable with the idea of same-sex relationships and never really came to terms with it. Additionally, Bob had spent many years in the military, where 'queers' were then still incarcerated in a military correctional facility for several months of hard training followed by a dishonourable discharge. It was a brutal world for gays.

Despite this, Bob had always been secretly fascinated by the gay culture, although he harboured not the slightest physical attraction to men, and he found the mere thought of having sex with a man repulsive. But, his visits to Pattaya, which began in the eighties and were to become a regular event, introduced a new concept into the mix - the ladyboy.

Often termed the third gender, these intriguing creatures walked, talked, and looked like women, and Bob couldn't fail to notice that died-in-the-wool heterosexuals were falling for their charms and taking them as their partners instead of the usual real bar girls. Some were quite stunningly beautiful, and he felt confused by his feelings regarding them. Physically, despite their extra appendage, he found them attractive, but it was hard to overcome old prejudices.

However, as he aged, he found that his mindset changed radically, ...

... and things that formerly were out of the question became possible. He decided to experience as many things as possible before he became too old and frail to appreciate them. So fucking a ladyboy shot to the top of his 'bucket' list.

She had to meet specific parameters before he went ahead. Firstly, the 'girl' had to look physically attractive and be feminine. And she should be a submissive and 'bottom'. The last thing that he wanted was some hairy-assed man in a dress wanting to fuck him up the arse or for Bob to blow his cock. That would be horrendous. Secondly, she had to have a smaller cock than him. Bob didn't want to engage in a pissing competition with a ladyboy as to who had the biggest cock!

He had his eye on the perfect date for himself, one who passed all his prerequisites with flying colours. Her name was Salt, and she lived in Manila, which, as luck would have it, was where he lived at the time. Although her face was perhaps only a six on a scale of ten, it was not masculine. And, if the photos he saw of her on Facebook were to be believed, her body was very feminine. And she was a submissive. She liked to have a guy treat her rough and to piss on her.

He found all of this out from a Pattaya ladyboy site. Salt had visited Pattaya a few months before and received rave reviews from the guy who had published a report and photos of his time with her. The pictures were hardcore to the extreme, and he was impressed by the 'girls' ability to take a hard fucking. ...