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Straight Pleasures

"Theo craves straight married men…"

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Theo had no desire to be a woman and did not think of himself as a transvestite or crossdresser in any way or form. He was very happy being gay and although he was rather feminine and quite camp, he enjoyed being a man. There were a few things about him that bordered on the ‘girlie’ side, however. Firstly, he loved wearing ladies stockings and G-strings. Secondly, his hair was shoulder length, which he constantly tucked behind his ears (when not at home), to give himself a more masculine appearance. Thirdly, the shirts he wore after hours were slightly on the ‘flouncy’ side.

Theo was petite. He weighed around one hundred pounds and stood five-foot-four-inches tall. He was practically hairless and the few sprigs under his arms were barely worth mentioning. He did, nevertheless, shave his armpits, lower legs, and genitals, because the stockings and G-strings he favoured simply worked better without that unnecessary hair. It also fascinated him how the stockings and G-stings seemed to put the straight men that he fancied, at ease. He supposed that to these guys, half a woman was infinitely preferable to having to admit to one’s homosexual propensities.

Theo did not like gay bars or clubs and the men in those places were not to his liking. Butch gay men always seemed like ‘pretenders’ to him. Theo, therefore, only hung out in straight cocktails bars in upmarket hotels. Married men were like an aphrodisiac to him and Theo had a rather successful record in these places. He was always very upfront about being a guy, when the men mistook him for a woman, and loved the bewilderment that this caused. Most men simply apologized for their blunder and moved off very quickly. But being as pretty as Theo was, there were enough guys who simply couldn’t get past their intrigue. Their additional consumption of alcohol, of course, invariably stimulated further fascination.

Theo wasn’t looking for romance and all he wanted was sexual gratification, and a quick fuck suited him perfectly. Most guys were happy to get their rocks off and see him leave as soon as possible. Very occasionally, a guy would ask him to spend the night. Naturally, if this suited him he would comply, but most times, Theo would make an excuse and be on his way shortly after the encounter. He was a fussy boy and mediocrity was definitely not to his liking. This was another reason why he frequented swanky venues. Second-rate motels definitely didn’t do it for him.

One Friday evening, as Theo arrived at one of his favourite venues he was delighted when he saw a notice at the front door, welcoming a farmer’s convention. This excited him enormously. After making his way to the bar he ordered a glass of wine. There were two straight couples seated at tables behind him, whom he naturally paid no mind to.

Thirty minutes later, however, things took a very distinct upturn when a very hunky guy entered and sat at the counter, one stool away from him. ‘Hunky’ was dressed in chinos and wore a toned-down cowboy shirt. He was ruggedly handsome and ticked every box in Theo’s partiality for men. Hunky ordered bourbon and was soon sipping his drink. In a friendly, country boy manner, Hunky soon turned to Theo and introduced himself as Shooter, explaining that this was actually a nickname given to him because he was the best marksman in the area he came from.

“Pleased to meet you, Shooter, my name is Theo,” he answered.

“Is that short for Theodora?” Shooter inquired, with a typical straight boy, ‘I’m available,’ shitfaced grin.

“No”, It’s simply Theo because… I’m a man,” Theo replied. The usual bewilderment that Theo had become accustomed to then occurred.

“Fuck… I’m sorry,” Shooter spluttered. “I hope I haven’t offended you?”

“Not at all,” Theo assured him with a laugh. “Many guys make the mistake you’ve just made.”

“It’s just that you are so pr… handsome,” Shooter replied, uncomfortably correcting his error.

Theo immediately let out an elegant laugh and then smiling, said, “Please relax, I really am not offended.”

After a brief silence, Shooter resumed, “You’ve got to forgive us country-folk… we’re not as… sophisticated as you city people.”

After another brief lull, Theo asked his normal rhetorical question, eyeing the wedding ring on Shooter’s left hand. “So, you’re married?”

“Yip,” Shooter replied, “Got a wife and two daughters.”

Shooter then began to fumble in his wallet for a photo of his family. Finally, he produced a dog-eared picture of his family. His wife was a large motherly type and his two girls were very sweet and pretty.

“Trying to get my missus to produce a boy,” he stated, “But she’s not keen on another child,” he said, with caricature sadness in his eyes. “I need a male heir,” he stated, with conviction.

As Theo handed the photo back after a complimentary gushing, he asked, “What’s your real name, Shooter?”

“Reggie… actually Reginald,” Shooter replied.

“Do you mind if I call you Reggie?” Theo inquired.

“Nah… suit ye’self, my family call me Reggie.” Shooter concluded.

There was a momentary silence in conversation before Reggie awkwardly broke the impasse by asking, “Are you married?”

“No, I’m not involved either, in fact, I’m gay,” Theo replied, laying his cards on the table.

Reggie was somewhat taken aback by Theo’s candour.

“Is this a homosexual,” and then quickly correcting himself, resumed “I mean… gay place?”

“No, not at all,” Theo answered, as he observed Reggie quickly slugging down the rest of his bourbon.

“So why do you come here?” Reggie asked, with a dumbfounded look on his face as he ordered more bourbon.

“Well, I like the atmosphere. Secondly, I usually hook-up with the kind of men I like and have a good evening.” Theo casually replied.

“You mean married guys?” Reggie questioned, in disbelief.

“Yes. Many guys simply move off when they realize I’m a guy. But then there are those who don’t,” Theo concluded, mysteriously.

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After a thoughtful pause, Reggie straightforwardly asked, “Do you charge for sex?”

“No. I’m not a rent-boy,” Theo answered.

“Help me here, bro, what’s a rent-boy?” Reggie asked, confused.

“It’s the usual term for male prostitute.” Theo countered, before concluding, “I simply like having sex with married guys, simple as that.”

Reggie bourbon disappeared in an instant before another one was ordered. It also amused Theo to observe the wedding ring on Reggie’s finger being spun around in an agitated manner.

“Wow, you learn new things every day,” Reggie finally uttered, before he attacked his next glass of bourbon.

Subtlety, Theo decided to test the water by asking, “Do you have a good love life?”

With a wistful frown, Reggie turned his head toward Theo very slowly and then answered, “No. I think my wife prefers being a mother, rather than a lover.” There was a real sadness in his eyes before he concluded, “All I get nowadays is ‘Sunday sex,’ he concluded, wistfully. Theo decided to remain quiet and allow Reggie to expound in his own time.

“After going to church we have our traditional Sunday lunch. Afterward, our girls spend the afternoon with my folks. That’s when I sometimes get sex. It doesn’t last a long time and I always get the impression that Beulah, my wife, would like it to end as quickly as possible. She was a lot more spirited a few years ago, before the kids, but nowadays… ah well,” he concluded in a mournful manner.

“Barman, I’ll have a last one for the road,” Reggie then pronounced before looking at Theo and asking, “Can I get you another glass of wine?”

“No, I’m good, thank you,” Theo replied, with a half glass of wine still before him.

“So, if a guy is interested and ‘qualifies,’ what happens next?” Reggie inquired, very gingerly.

“Then we go to his room. Generally, I follow a few minutes later because it’s just more discreet,” Theo informed him.

“Do I pass the test?” Reggie questioned, apprehensively.

“Definitely,” Theo answered, with a warm smile.

Again the wedding ring on Reggie’s finger got twirled nervously. Next, Reggie slugged back his drink before saying, “I’m in room 807, and I hope to see you shortly.” Reggie then got up left with an anxious expression.

There was something very unique about Reggie. Not only was he hotter than most guys that Theo had ever encountered in this manner, but there was a delightful naivety to his demeanour. As Theo slowly made his way to Reggie’s room he wondered how the tryst would unfold.

When Reggie opened the door of his room Theo was pleased to observe, that Reggie seemed a little less agitated. It also shortly became clear that Theo would have to take the initiative because Reggie appeared to be stranded in anticipation. Moving toward the sumptuous bed in the room, Theo expressed his approval.

“I normally stay at a modest motel,” Reggie admitted, before continuing, “But the organizers of the convention arranged a special rate for us, so what the hell.”

As he moved before Theo, Theo lifted his hands and commenced unbuttoning Reggie’s shirt, before suggesting, “Why don’t you remove your boots and trousers.”

As Reggie stripped, Theo followed suit but did not remove his stockings and G-string. Theo was pleased when he observed the look of approval on Reggie’s face.

Once naked, Reggie had a great body and a very substantial knob. Theo now suggested that Reggie lie back on the bed with his legs hanging over the edge. If there was one thing that Theo was extremely accomplished at, it was giving blowjobs. When he commenced sucking Reggie’s cock, Reggie immediately began to groan his approval. Theo’s tongue and Reggie’s dick were like two snakes intertwined in a mating ritual.

Using his skill to the fullest, Theo worshipped Reggie’s wonderful phallus ardently. The gasps and grunts from Reggie pleased Theo enormously, and he kept accelerating his oral onslaught. When Reggie’s body started to shudder, Theo knew that Reggie’s cream would follow shortly. It did, and Theo was overjoyed with the abundance of spunk that coated his mouth.

Afterward, Theo pondered what the next step would be. Most straight men suffered from post homosexual distress once they had ejaculated, and on most occasions, Theo would shortly be on his way.

As Theo began to dress, however, Reggie surprised him by asking, “Do you really have to go?”

“Well, you’ve cum,” Theo stated matter-of-factly, in anticipation of the usual response.

“Please stay the night, I really want you to stay,” Reggie earnestly pleaded.

Although taken off-guard, Theo was delighted by this request.

“Sure, I mean, are you sure?” Theo asked, almost disbelievingly.

“Yes, yes,” Reggie sincerely replied.

After pouring them each a drink Reggie asked if he could contact Theo on future visits to the city. Naturally, Theo answered in the affirmative.

When they returned to the bed, Reggie removed Theo’s G-string and commenced pummelling his backside as Theo lay on his stomach. The session was gloriously sustained and Theo ejaculated rapturously without even touching his dick.

As the lay side by side afterward, Reggie said, “Fuck, if you were a woman I would fucking divorce my wife and marry you in a heartbeat.”

Theo didn’t have the heart to tell Reggie that he was actually very happy being a man, and so just smiled politely. Not long after, they happily drifted off to sleep.

In the early hours of the following morning, Reggie awoke and once more mounted Theo’s body, with Theo’s legs over his shoulders. To Theo totally delight, Reggie kissed him passionately for the very first time. This session was a complete mind-fuck for Theo who had very seldom experienced this level of intimacy with straight men.

As Reggie moved his torso up and down, Theo was more gratified than he had been in a very long while. This wasn’t the normal fucking that he was used to, it was lovemaking. Theo was elated that they had exchanged telephone numbers and knew that he would be counting the days till Reggie’s next visit.

Published 
Written by Tuppie
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