Straight Pleasures

by Caliban

6 Mar 2022 12843 readers Score 8.9 (474 votes) PDF Mobi ePub Txt


Theo had no desire to be a woman and did not think of himself as a transvestite. He was very happy being gay, and although he was rather feminine and quite camp bordering on the ‘girlie’ side and enjoyed being a man. Theo loved wearing woman stockings and G-strings. Additionally, his hair was shoulder-length, which he constantly tucked behind his ears (when not at home), to give himself a more masculine appearance. Next, the shirts he wore after hours were slightly flouncy.

Theo was petite. He weighed around one hundred pounds and stood five-foot-four inches tall. Theo was practically hairless, and the few sprigs under his arms were barely worth mentioning. He did shave his armpits, lower legs, and genitals because the stockings and G-strings Theo favored worked better without hair. It also fascinated him how these accoutrements seemed to put the straight men at ease. He supposed that to these guys that being 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 ‘lust-worthy.’ 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 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 this caused. Most men generally apologized for their blunder and moved off very quickly, but being as pretty as Theo was, there were enough guys who couldn’t get past their intrigue. Their additional consumption of alcohol invariably stimulated any latent bisexual allure.

Theo wasn’t looking for romance and 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. Occasionally, a man would ask him to spend the night, and 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 not to his liking. That was another reason why he frequented swanky venues. Second-rate motels did not do it for him.

On a Friday evening, once 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 prospect excited him enormously. In his usual manner, his attire was elegant ‘transgender.’ After making his way to the bar, he ordered a glass of wine. He paid no mind to the two straight couples seated at tables behind him.

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 a 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 a nickname given to him because he was the best sharpshooter in the area where he lived.

“Pleased to meet you, Shooter. I’m Theo,” he answered.

“Is that short for Theodora?” Shooter inquired, with a 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 this mistake.”

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

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

After a brief silence, Shooter stutteringly 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 usual rhetorical question, eyeing the wedding ring on Shooter’s left hand. “So, you’re married?”

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

Then Shooter 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 motherly type, and his two girls were 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… Reginald, actually,” 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. 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 bar?”

“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 move off when they realize I’m a guy. But then, some don’t,” Theo concluded mysteriously.

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 a 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 got requested. It also amused Theo to observe the wedding ring on Reggie’s finger spinning 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?”

Wistfully, Reggie turned his head toward Theo very slowly and answered, “No. I think my wife prefers being a mother rather than a lover.” There was sadness in his eyes before he concluded, “All I get nowadays is ‘Sunday sex,’ he concluded ruefully. 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 is when I sometimes get sex. It does not last too long, 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… Oh well,” he concluded with a shrug.

Theo then served the coup de grace. “You see, Reggie, that the great thing about casual sex with another man is there are no strings attached. Straight men generally do not feel like they are cheating on their wives, and for gay guys like me, there is no pressure, simply gratification.

As a wave of confusion flushed over Reggie’s face, he spoke, “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 straight guy is interested, what happens next?” Reggie gingerly inquired.

“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 left with apprehension on his face.

There was something 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 their 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 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.”

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

After Theo unbuttoned the shirt, Reggie was bristling with nervousness.

When Reggie had stripped to his underwear, 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 then suggested that Reggie lie back on the bed with his legs hanging over the edge. Theo was a blowjob specialist, and when he commenced sucking Reggie’s cock, Reggie immediately began to grunt his approval. Theo’s tongue and Reggie’s dick were like two snakes intertwined in a mating ritual.  

Using his skill, Theo ardently worshipped Reggie’s wonderful phallus. Apart from the gasps and grunts from Reggie that pleased Theo enormously as he kept accelerating his oral onslaught, the unsullied odour of natural masculinity delighted Theo. When Reggie’s body started to shudder, Theo knew that Reggie’s cream would follow shortly. As it did, Theo was overjoyed with by 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, Reggie surprised him by asking, “Do you have to go?”

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

“Please stay. I want you to stay tonight,” 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 bedroom, Reggie sensually removed Theo’s G-string.  Next, as Theo lay on his back, Reggie began intensely pummelling Theo’s backside. Their sustained session was glorious and Theo ejaculated rapturously without even touching his dick.

As they 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 happy on his own and just smiled politely. Not long after, they happily drifted off to sleep.

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

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 and felt like lovemaking. After they exchanged telephone numbers, Theo knew began counting the days until Reggie’s next visit.

by Caliban

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