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. What he didn’t like was that she had allowed the man to ‘bareback’ her anally. The silly girl would have to be more careful, and he made a mental note to insist on her having a complete check-up at his expense the day before they met. And he intended to wear a condom for anal sex.
Contacting her was simplicity itself. There are not many Salts on Facebook! He sent a PM to her, explaining what he wanted, and within a short time, she had replied, telling him that she was presently at home in her province but would be returning to Manila the following week and would be able to meet him then. She was happy to have the check-up. She had a clinic she had used before for the same reason, and the cost was minimal. She would pay for the tests, and Bob agreed to reimburse her when they met.
The wait until the day of their meeting was agonising. Bob refrained from masturbation or sex in the week before and so was very horny come the day of their assignation. He had a lot of backed-up sperm to give her!
Then the day arrived. She had agreed to meet him at a no-tell motel in Makati. Bob arrived thirty minutes before the scheduled time to ensure everything was in order. He expected that she would be late. Filipinas in Manila are always late and have a ready-made excuse in the form of the horrendous traffic. It is no good to scold them for it or tell them to set off earlier, as they inherently have little concept of time management. It is just something that you live with and not get stressed about. Life is always easier in the Philippines if you go with the flow and not sweat the minutiae.
So Bob was surprised when he got a call from Reception telling him that Miss Salt had arrived and was to come to his room? She was on time! He assented, and five minutes later, there was a knock at the door, and he let Salt in.
Bob’s first impression was very positive. Salt was well dressed in fashionable leg-hugging jeans that showed her great ass to perfection. She wore a tight-fitting shirt tied under her shapely breasts.
Her attractive, if not beautiful, face was pleasant enough, and she had pushed a pair of Nike sunglasses atop her head. She was very feminine and could no doubt fool those asked to guess her gender.
They kissed, and Bob was a little taken aback. She kissed just like a woman. Of course she does, he thought. What did you expect? An unshaven hairy chin. He mentally told himself to behave. She was, in every respect except one, a woman. And he had better get with it.
They undressed, and he asked her to join him in the shower, which she did. Her figure was astonishing with hips and breasts, which many real women would envy. The only difference was the cock between her legs.
As they caressed underneath the warm flow of water from the shower, he took hold of and gently massaged her circumcised penis. This would be, he thought, the first time that he had ever held a male cock except his own in his life. He felt it twitch slightly in his hand. He had heard that some ladyboys have difficulty getting and maintaining an erection and are unable to produce sperm and, therefore, ejaculate only seminal fluid. He wondered if this was the case with Salt.
He asked Salt if she wanted him to piss on her, and, in her husky voice, she said yes, but only on her body and not her face. He had a partial erection but thought he would be able to manage it, so he turned off the shower, and she knelt in front of him. It took a little while for his urethra to relax sufficiently for him to urinate, but after a few moments, his stream began, and he directed the flow over her breasts. Another first for him. He had played water sports with women before, but this was the first time with a ladyboy. He thought that today, there would be many firsts.
Once she had hosed off the urine, Salt joined Bob on the bed, and the real fun began. Bob’s cock was as hard as a rock, and he desperately needed it sucked off. The uniqueness of the occasion had made him hornier than he had been in a very long time, and he was sure that when he came, it would be a meaningful event for him.
As she slid his cock into her mouth and she wrapped her slippery tongue around his super-sensitive frenulum, he trembled with the undiluted pleasure it gave him. She surely knew how to suck a cock, but that was to be expected as she knew what pleases her would likely please a man. This line of thought brought Bob to the conclusion of whether he should return the favour and blow her. He had decided before the meeting that this was a step beyond the pale, but now he was with her and was able to see what a pleasing little cock she had; he was undecided.
However, first things first. Bob could feel himself getting close to critical mass and didn’t think he could last much longer. He linked his hands behind Salt’s head and forced her down until she had most of his seven-inch cock in her mouth. She did not resist, and apart from a couple of small choking sounds at which he temporarily withdrew so she could catch her breath, she remained silent and did as he bade. He warned her that he wanted to come in her mouth, and she nodded assent.
Bob began to face fuck Salt in earnest. She had told him that he liked it rough, so he didn’t hold back and rammed his dick deeper and harder into her throat. She took it well, and it was one of her specialities as now that she had recovered from initial discomfort, she took his cock deep in her throat without a murmur. This spurred him to thrust harder. Shit, he was so close now and could feel tremendous joy in his entire being as he rammed himself hard into her mouth for one last time. His cock began spurting large gobs of cum into her throat.
His back arched as the orgasm hit him hard, and he had to withdraw his now super-sensitive cock, still spurting sperm, from her mouth. The cum dripped down her chin in large gobs. He rubbed the cum into her skin and bade her lick his fingers, which she did without dissent. Only after she had cleaned his tool with her tongue, licking up any stray droplets which had fallen onto his body, did she get up and go to the bathroom to clean up.
He felt energised and ready to go again almost immediately, and when Salt returned from the bathroom, he asked her to lie on the bed, where he stroked her body for a little while before reaching down and taking her penis in his hand. He shuffled down the bed until her cock was inches from his face and examined him closely. It had been expertly circumcised, and the bulbous head of her penis and the skin of her glans were contrasting pink and brown.
He thought, ‘What the hell,’ and took Salt’s cock into his mouth and began sucking her off. She had shown him the clinic’s ‘all clear’ letter, so he was reassured of that score. He found that the taste and smooth feel of her cock was not unpleasant, so he upped the tempo. Salt moaned softly and reached down to try and pull Bob’s head away. She was obviously about to come and didn’t want to do so in his mouth, but Bob was enjoying himself and let Salt ejaculate into his mouth. He felt the warm cum on his tongue, an experience that he had given to many women, but the first time that he had experienced it. The semen tasted sweet and slightly salty, reminding Bob of pineapple juice. He went to the bathroom to spit and clean his teeth.
Bob was ready for some seriously rough fucking, and Salt looked momentarily scared as she saw him approach the bed with his enormous erect tool, hard and glistening with the lubricant that he had applied in the bathroom. Bob lay on the bed and instructed the seemingly always-willing Salt that he wanted her to rim him. He opened and lifted his legs and forced them as far back as his creaky joints would permit. This allowed Salt access to his asshole, and she licked and teased him, sliding an adventurous tongue and then a finger into his bumhole. Bob loved the sensation, which was incredibly erotic, and his cock got even harder, if that was possible.
He urgently needed to fuck her now, and lifted her back onto the bed and ordered her to lay on her back. He pulled on a condom. He then roughly opened her legs and pushed them back as far as they would go until they were almost behind her neck. Luckily, Salt was much more flexible than he was, and she seemed very bendy. Bob climbed on top of her and slowly but relentlessly pushed his cock against her sphincter until he felt the muscle relax, and he was up her.
He began a rhythmic stroke, slowly at first and then picking up in speed until he was pounding her for all he was worth. She gasped in pleasure or pain (he didn’t know which) as his cock thrust in and out of her ass. Bob was feeling great. This was the best sex that he had enjoyed for quite some time, and he wanted to savour every moment.
He pulled his cock out of her ass and manoeuvred Salt into the doggy position with her fine ass as high in the air as it could go. He slapped her butt a couple of times and then quickly reentered her. This time his cock slid inside her back cunt as if it was designed for the task, and he quickly built up the pace until the regular slapping sound of his groin against her bum cheeks signified that he was balls deep up her ass. He pounded as hard as he could for a few more strokes but could feel himself weakening.
He wasn’t young anymore, and the exertions were taking their toll. He was exhausted and would have to call it a day. But not without the coup de grâce. He withdrew his cock from Salt’s ass, removed the condom and then flipped her onto her back. He then straddled her and, using a combination of her mouth and hand and finally his hand, he brought himself off on her face. Yet again, she scooped up the cum and put it in her mouth.
‘You are a dirty little bitch, and there is no doubt about it,’ he murmured under his breath. Salt smiled sweetly at him before cleaning up and dressing in the bathroom. Bob was glad he had the foresight to take the room for six hours. He could recharge his exhausted batteries with a bit of sleep before he had to return home.
Salt emerged from the bathroom, looking just as cool and smart as she had when she had just arrived. It was hard to believe that she had been a sweaty, hard-fucked mess just fifteen minutes earlier.
He kissed her on the cheek and slipped the agreed-upon fee into her hand: three thousand pesos plus a five hundred pesos tip for her efforts above and beyond the call of duty and an extra thousand to cover the cost of her tests. She smiled and kissed his cheek in return.
He let her out into the humid air of Manila late afternoon. They had agreed to meet again, but he was one for the ladies, and although he was to enjoy the company of more ladyboys in the future, they were a treat for when he felt tired and ready for a change from pussy. So he never met her again after that momentous afternoon.