Going Gay / Tim – Chapters 2 – 4

NOTE TO READERS: Posting my story one chapter at a time is tedious. So… here are the next three chapters, all in one post! I hope this is easier for me to handle, and more enjoyable for you to read. Please let me know what you think: timhobson69@outlook.com.


Las Vegas was every bit the tawdry, suggestive den of iniquity that I remembered. I settled into a penthouse suite on the 35th floor with a view of the Strip, and started enjoying all the freebies that are lavished on a big spender. Only, I didn’t spend one red cent in the casino. Instead, I took in shows, ate in fine restaurants, lounged by the rooftop heated pool, and tried to avoid the attentions of the twenty-something girls who clearly saw a meal ticket in me.

The boys, however, started to get to me. They were so handsome, fit, and overtly sensual that I began to struggle with a desire in myself that I had never acknowledged. Of course, I knew they were after the same thing as the girls, but it became fun to tease them a bit and lead them on. And it was definitely not torture to have them join me for dinner or a show and watch the envy in the eyes of certain men who saw us together. But I always said goodnight with a handshake in the lobby and went up to my room alone, no matter how disappointed my “date” appeared to be.

I had one hard and fast rule. I would treat them to food and entertainment, even take them with me on excursions around Vegas, but as soon as there was the slightest hint that I might help them with a little “loan” or anything else to do with money, I was done with them in a heartbeat.

And it wasn’t that I couldn’t afford it. With Keith guiding my investments, the balance in the bank was actually larger each month, even though I was living the high life.

Yet, despite the fact that I left them physically at my front door, the memory of their hard muscles, the scent of their musky cologne, and the image of their eager bodies haunted my dreams every night.

When we reached the door to my suite, I invited him in, poured us a drink, and suggested we get more comfortable. We sat side-by-side on the balcony, looking out over the lights of the city. Our hands brushed, and then he took mine and gave it a warm squeeze. We turned to face each other and the young man leaned over and kissed me on the lips. I returned the gesture, and he opened his mouth to take in my tongue. Impassioned, we embraced, our hands exploring each other’s bodies.

“Let’s go inside,” I said, and we quickly repaired to the large bed. Undressing each other eagerly, we were soon naked, writhing on the silken sheets. Frantic with desire, I took his hard cock into my mouth as he gasped in pleasure. As he lay on his back, I sucked and teased and deep-throated his perfect prick. In no time, the boy came in my mouth, and I eagerly drank his sex juices.

At that point, I usually woke up with my own cum all over my belly, got out of bed and washed it off. Returning to my bed, I tried to sleep, but the imagined act was never fulfilling.
Unsurprisingly, after a few weeks, Las Vegas lost what little charm it had for me, and I decided to head west. Southwest, to be exact: San Diego.

There, I booked into a thousand-dollar-a-day suite at the Del Coronado, on order to live up to my newfound standards as an old, rich bastard. And I found something else there, too.

One evening, dining alone al fresco on the hotel patio, I noticed a table nearby where there were three men of about my age. They returned my look and smiled, raising their glasses to me. I nodded, returned their salute, and finished my dinner. As I was nearly done, they rose from their table, and one of them walked over to me.

“There’s a beautiful view of the sunset from the rooftop bar, and being’s you’re alone, we thought you might care to join us.”

As I looked up at him in astonishment, he proffered his hand. “Lowry. Martin Lowry.”

With a sly grin, I replied, “Bond. James Bond.” We both guffawed. “Actually, it’s Tim Hobson. Nice to meet you, Lowry.”

“Martin, please. So what do you say, you up for it?”

I agreed, and signaled to my waiter that I would be moving. I followed Martin over to the other two gentlemen.

“I’ll do the honors,” he began. “Tim Hobson, this is Alexander – Allie – Raymond.” We shook hands. “And this is Lord Franciscus Antiochus Worthington Windermere – we call him “Windy,” but only behind his back!” A bit awed, I took his handshake.

Pater was a classics scholar,” he said, explaining his high-sounding name. “Nice to meet you, old boy,” Windermere had a Brit accent. “How ya doin’?” from Alexander.

With that, we four boarded the outdoor express elevator to the roof and walked out into the open-air bar.

No sooner did the elevator doors open, than four gorgeous young men stood up and walked toward us.

“What the…?” I exclaimed. The three smiled at my surprise.

“Timmie, allow me to do the honors,” Windermere said grandly. Indicating the first young man, he said, “This is Ty Roper.” The second was introduced as Beau Botham, the next was Jonny Comer, and the fourth was Jimmy Coxx.

“Beg pardon? Those are odd-sounding names,” I said.

Windy explained, “Well, of course they are, old man. They’re noms de porn.”

“Noms de what?”

All three had a good laugh at my expense. “Come on, old boy, you’ll soon be up to speed.”

The eight of us proceeded over to a sort of conversation pit with three couches and two easy chairs, arranged around a stone circle with a gas fire dancing in it. As we sat down, I couldn’t help but notice that each man was seated next to one of the “boys” – as I would call them, given that none of them could have been more than 25.

Windermere finally clued me in. “These young gentlemen are our guests for the night. They are well-known in certain circles.” He raised one eyebrow archly and winked at me. “They are famous, each in his own right, for their performances in shall we say, ‘adult’ videos.”

That’s when it dawned on me. These handsome, sexy young men were porn stars, and they were probably here to entertain the men in an intimate way, most likely for a lot of money.

His Lordship continued, “Ty, for example, is renowned for his scenes of bondage and domination, by women and men. Beau here has an absolutely perfect tushy, if you get my drift, and he knows how to use it to its fullest advantage. Jonny’s forté is only revealed at the end of his scenes, when his, shall we say, ‘output’ is measured in yards and gallons. And Jimmy lives up to his name, having an endowment that is off the charts in terms of size and girth. You don’t want to be on the receiving end of that cattle prod!”

I was speechless for what seemed like minutes. Then I spoke, shakily, “Well, it’s nice to meet all of you, but I’d better be going. This isn’t really my cup of tea.” I rose to leave.

“Now hold on just a fucking minute there, Hobson!” Martin began. “You may be shy, or, hell, you may still be in the goddamn closet, but we’ve all been watching you since you got here. There’s not a hot guy in this joint that you haven’t undressed with your eyes every time he comes into view. You may not know it, but your reaction is just like ours was, the first time we entertained young studs like these. But you’ll get over it damn fast, or I don’t know shit.” With that, all the others laughed loudly.

“But, I’m a married man – or at least I was.”

“That’s never been an impediment, old bean,” Windermere said with a sly grin. “All of us are either married or divorced just now, but all that’s a world away from here.”

For the first time, it dawned on me that he was right. I had been looking longingly at all the nearly-naked young men sporting their golden tans and tight Speedos around the pool. I even had half an erection several times, forcing me to cover my crotch with a book or towel.

“But…” I began.

“But nothing,” Allie broke in. “You’re here to have a good time, damn it! The wife is away… or out of the picture?”

“Deceased.” I interjected.

“My condolences, but it’s apparently been a while for you, because here you are, cavorting around the place, lusting after every hot boy you see. So why not go for it? Take a chance. If you can’t find something to interest you in this little stable of stallions,” he gestured at the four gorgeous young hunks seated with us, “then I know a dozen or more who might do the trick for you… or turn a trick for you!” With that, they all nearly fell out of their seats belly-laughing.

“I don’t know what to say.”

Martin had mercy on me. “Look. it’s plain to see you’re new to this scene. And we don’t want to pressure you into anything. It’s just that we have been keeping a watchful eye over you!”


“Because there’s a certain element around here that is ever on the prowl to find a rich sugar daddy to hook up with and drain his bank account, and we think you’d be a lot happier, a lot more satisfied, and a lot safer if you hang out with us. The quality and caliber of our companions is much to be desired over the alternative.”


I fell silent. I looked at each of the older men, then into the faces of the eager young studs. Beau, who was seated next to me, gently put his hand on my knee.

“You don’t ever have to do anything you don’t want to do,” he said, gazing deeply into my eyes with his own perfect blue ones. “Nobody’s trying to force you. We just thought you might enjoy a little diversion.”

I thought again for a while, then said hesitantly, “so what does all this cost?”

There was a stunned silence. I quickly realized that I had fucked up by saying something totally inappropriate.

Then Windermere spoke, harshly, “We never discuss money amongst ourselves. But for your information, there is no cost. All of us enjoy our sex lives, whatever they may be at our age, and often share the experience with willing companions, but there’s never a word about remuneration. These fine young men are not fucking prostitutes! They graciously accept our generosity from time to time, and we show our appreciation in many ways, but there is no tit-for-tat, as it were.”

“Shit. I’m sorry. This is just so new to me. I really don’t know what to say.”

There was a general sigh of relief among them all. Then Allie said, “Well, then, let’s just get on with enjoying a delightful evening. And if it leads any of us to share an intimate moment together, then so be it, but it may or may not happen. Que será, será, as they say!”

With that, we all ordered drinks and began a three-hour bullshit session that wandered from politics to religion to the economy to the history of pornography. I found myself equally at home discussing price-earning ratios and cock sizes. It was so natural and relaxing that I abruptly looked up at the others with what I’m sure was an expression of shock.

“What is it?” Beau asked with concern, putting his hand on my shoulder.

“Oh! I just realized that for the first time in almost two years, I feel completely comfortable and at ease.”

“I don’t mean to pry, but how did your wife pass?” Martin asked quietly.

“Breast cancer, the aggressive kind.”

“Deeply sorry to hear that.” They all fell silent. I immediately regretted throwing a wet blanket over what had been a jolly conversation.

“Look, guys, I’m sorry. Like I said, this is all new to me, and I am still figuring out how the hell to deal with all that has happened, and who the fuck I am now.”

“Perfectly understandable,” Martin began. “And we don’t want to muck with that in any way. You know, Tim, we see something in you that we see in ourselves, and we only hoped to help you engage with it. If things are moving too fast, or if, as you say, this is not your cup of tea, right now or ever, we understand completely. I am sure we all agree that we’ve had a fine time meeting you and sharing the evening with you. And there need be no more to it than that.”

Now I felt like a complete asshole. “I’m really sorry. Can we rewind the last ten minutes? I am having a good time, and like I said, I feel better right now than I have in years. Please excuse my prudishness. And – confession time – I think I’ve always suspected that I would enjoy the company of a younger man. I just never considered it an option while I was married and everything.”

They all looked straight at me. Then Beau extended his arm around my shoulders and lightly kissed my ear. I turned to face him and, surprising myself, leaned in and kissed him right on the lips.

Everyone let out a deep breath. Apparently, a Rubicon had been crossed, and I was now on the same side of it as the rest of them.

With that, Windy stood up, and, taking Ty’s hand, said, “Well, that’s quite enough sentiment for me for one night. Welcome aboard, Hobson. May you enjoy the rest of the evening in the delightful company of this young Adonis,” he said, nodding toward Beau. “I believe we lads shall retire now, I think. I have a few loose ends to tie up.” And the two of them headed for the elevator to the roar of laughter from the group.

“Did he actually say ‘tie up’?” I said, looking at Beau with wonder.

“You bet your ass!” Beau responded, and we both laughed again.

Martin and Allie also got to their feet, Jonny and Jimmy with them. “I think the four of us have some champagne chilling in my suite,” Martin said slyly, winking at me. “I do hope you and Beau won’t miss us too much.”

As the foursome left, I found myself feeling as clumsy as a schoolboy on his first date. Breaking the awkward silence, I turned to Beau and admitted sheepishly, “I’m not sure what to do or say.”

“That’s fine with me. I usually let the others do all the talking anyway. I don’t have the kind of experience that they do.”

“What do you mean?”

“Hell, I’m just a farm boy from Iowa. I don’t know shit from Shinola in this town.”

“How did you get here, if you don’t mind my asking?”

“Pretty typical. After high school I went to community college. I soon learned that it had been a total fucking waste of time and money. There weren’t any jobs in my town for someone with my kind of education, so I bummed around a while, doing odd jobs – waiter, Uber driver, construction.

“Then one day a dude I knew showed me a business card. It was from a guy who was hiring dancers for a ‘gentlemen’s club.’ As soon as I walked in, I could see that it was a gay strip club, and I was scared shitless, but I auditioned anyway and got the job. I guess I was good at stripping, ‘cause I made a shitload of money.”

Gauging my reaction, Beau went on, “at first, I only stripped on the stage. Then customers started asking for a ‘private show,’ and before I knew it, I was letting them blow me, and pretty soon I got into fucking them.”

We sat silently for a moment, while I tried to take it all in.

Beau continued, “After about a year, one of my buddies at the club told me we could make a lot more money in porn, and he said he was about to leave for L.A. to see someone he knew there. I went with him, and that also turned out to be a good move.”

As he paused for breath, I considered all he had said, “do you feel like you were taken advantage of?”

“Fuck, no. Everything I did, I did because I wanted to. Nobody forced me to do a goddamn thing, and I could’ve kept on like I was, working shit jobs here and there. But the money was good, and I also found out that I liked doing it.”

“So you like having sex with men?”

“Getting personal, are we?” He raised an eyebrow as he looked at me.

“Oh, I’m sorry. I didn’t mean to pry,” I said, hanging my head and blushing a bit.

He laughed, “I’m just jerking your chain, Tim. I’ve been ‘addicted’ to sex ever since I was fourteen, when I learned how to jack off. I fucked lots of girls through high school and college and while I was working around. It was fun and easy, but it was just physical. I never connected with any of them or ‘fell in love’.”

He took a sip of his beer and continued, “The first time I fucked a guy, it was a whole new world. And the first time I let a man fuck me, I knew I was right where I oughta be. In fact, I’m told I’m pretty good at it – bottoming, I mean – you oughta check out some of my videos when you get a chance. You can decide for yourself whether I’m enjoying myself or not.”

We sat in silence as I tried to take it all in. Then Beau looked at me with those amazing blue eyes. “What about you?”

I hesitated, wondering how to answer him.

“I guess I’m still at the point where I’m trying to discover or perhaps reinvent who and what I am, now that my whole life has changed. I’m afraid I don’t have any answers for you.”

“Well, who the fuck says you have to?” He grinned at me. “So, are we going to visit your room, or do I have to go back to mine and beat off three or four times?”

“That many?” I asked with a twinkle in my eye.

“That’s how sexy you are,” he said, and I thought he was at least being kind, if not completely honest.

We stood and made our way to the elevator. The bar was nearly empty. It occurred to me that it had been full of older and younger men an hour ago, but apparently they all had some place they’d rather be by now.

As the elevator doors closed silently, Beau turned to face me. “If this makes you uncomfortable, I can get off at my floor, and you can have a quiet night…”

“What, you want to leave me to jack off three or four times… or maybe once, if I’m lucky?”

After we both had a good laugh, I went on, “I’m surprised to say it, but it feels really right, being here with you.”

We rode in silence for moment. Then Beau turned toward me again, pulled me into his arms, and kissed me on the mouth. His tongue gently prized my lips open and began to explore inside. My initial reaction was to stiffen, but his loving touch quickly put me at ease and I hugged him tightly and returned the kiss.

We were in that position when the elevator doors opened, and I thanked my lucky stars that there was no one on the landing waiting for the elevator. I quickly took Beau’s hand and led him to my door. The key went in, the door opened, closed, and we were back in a loving embrace, all in under 60 seconds.


As Beau pressed my back against the now firmly-bolted door to my suite, our tongues and lips battled each other as our hands wandered everywhere. I ran my fingers through his golden blond hair, toyed with his ears, slid my hands down his back, then up to his armpits.

Beau responded with a passionate touch. Clearly, I was experiencing this for the first time in my life, while he was intimately familiar with the process. He reached under my shirt and lightly pinched my nipples. I was electrified by this new sensation. Then he ran his hands down my back and kept going, below my belt, inside my slacks. He gently squeezed my ass cheeks and pulled my crotch into his, revealing that we were both hard. Noticing my surprise, Beau firmly pressed his prick against mine and said, “Mmm!”

It felt awkward at first, hugging and kissing another man. But it also felt exciting and, in a way, just what I needed, what I had been dreaming of doing for weeks.

Beau didn’t rush things. Our embraces went from passionate to gentle, to exploring, to loving, and back again and again. Finally, we leaned apart a little and took a deep breath.

“You sure you’ve never done this before?” Beau asked with a sly grin.

“I wish I had, but no.” I thought a moment. “Well, of course with my wife and a few other women before I was married, but never with a…” I paused, searching for the word.

“A man?” “A boy?” “A hustler?” Beau offered.

“No, no, of course not a hustler, if that means what I think it does. I’m just so new to this, I don’t know what words to use.”

“Well, we both have cocks and balls, and I assume hair on them, so wouldn’t that make us both men?”

“Men with 50 years’ difference in age!”

“Oh, now, you’re not going to get ‘ageist’ on me, are you, Tim?” Beau said this with that sly grin of his.

“I hope to hell not, but you’re going to have to guide me, and especially correct me whenever I say something stupid or insulting, which will probably be rather often.”

“Not to worry. I have a thick skin, including on the end of my cock!” We both burst out laughing and resumed kissing eagerly.

Breaking the embrace, I gestured into the suite and said, “How about we get more comfortable?”

“Now you’re talking!”

We moved into the spacious sitting area and settled comfortably on the soft leather couch. A gas fireplace softly illuminated the room, which was tastefully (and expensively) decorated. Through the balcony windows, I saw moonlight shimmering on the dark waters of the Pacific Ocean.

Beau sat sideways, his knees pointed at me, and I leaned back, thinking how monumentally my life had just changed. I had actually kissed a boy. Well, I guess I’d better say “a man,” so that I don’t get in trouble with the cops. And I had definitely enjoyed it, as my now-aching erection attested.

Beau put one hand on my leg and gently stroked it. I turned to look at him. Those beautiful deep-blue eyes were like powerful magnets, irresistibly pulling me deeper and deeper into his world of man-sex.

“What do we do next?” I wondered aloud.

“Well, that depends on how far you want to go. It is our ‘first date’ after all!” We both laughed at that thought.

“What do you like to do?” I said, looking him straight in the eye.

“Oh, whatever. I always try to go with the flow of the guy I’m with.”

“How many men have you been with?”

Beau fell silent, his face clouded. “Does that make a difference?” he asked meekly.

Horrified that I had offended him, I quickly said, “No, not at all, and I know it’s none of my damn business, so please forget I asked.” In response, he leaned in to me and began another deep kiss.

This time we were in a more open position, and soon I felt his hand sliding up my leg, moving almost imperceptibly. Somehow Beau sensed how well I could acclimate myself to what we were doing. He finally brushed his knuckles against my rigid dick through my slacks. I jolted and took a quick breath, and he smiled and made that pleased ‘Mmm’ sound again.

“You like that?” he asked.

I wasn’t sure if it was a question or an observation, but I replied, “Very nice. Please don’t stop.”

With that, he slid over closer to me on the couch. Our hips and knees were pressed against each other. Gingerly, he unbuckled my belt, pulled down the fly, and gently slipped his hand inside.

His warm hand quickly surrounded my swollen member. “You’re big,” he observed.

“Too big?” I asked with a sly grin.

“In your dreams!” We both laughed at his riposte.

He began gently stroking my cock through my underwear. I decided that it was time for me to take some action in response to his. I raised my ass and slid my pants down to my ankles. Beau removed his hand and bent down, removed my shoes, took my pants completely off, and also slid my socks off.

I sat there in just my polo shirt and tighty-whities. I glanced down and there was no doubt that my pecker was as solid as the Rock of Gibraltar. I expected him to continue stimulating me with his hand, but instead, Beau leaned down and began to kiss my hard-on through my jockey shorts. Each touch of his mouth sent a delightful shiver of excitement up and down my spine, and his soft blond hair tickled my stomach as his head brushed against it.

Then he stuck out his tongue and began licking the length of my dick through the cloth, pulling the knob into his mouth and sucking on it hungrily. I moaned again and pressed it up into his face.

He sat back up and gave me a sunny smile. “I’d better catch up with you.”

With that, he started to pull his muscle shirt up over his head. “Wait! Let me do that!” I quickly said.

He relaxed and smiled again. “That would be nice.”

I leaned closer to him and lifted his shirt from the bottom. As I slid it up his chest, my heart started pounding. I was undressing the sexiest young man I had ever seen, and he was actually enjoying it!

The rising shirt revealed a line of soft hair leading down from his navel and disappearing into his cargo shorts. Then it revealed solid six-pack abs, followed by brown nipples adorned by a few tiny hairs. He raised his arms to allow me get the garment over his head, revealing thick, dark hair in his armpits. The only smell from them was the light scent of some masculine cologne or deodorant. I was pleased to note that he had no visible tattoos or piercings.

The shirt dealt with, I went right for his belt and zipper. Rather than reaching inside as he had done, I tucked both thumbs into his waistband and slid his shorts down. I inadvertently gasped in surprise as I saw that he was not wearing underwear.

Smiling at my reaction, Beau simply said, “Commando.” I smiled back at him for a moment, then continued on my mission of undressing him.

As I wriggled his shorts downs his legs, a delicate bush of soft brown pubic hair appeared. It occurred to me that he must keep it trimmed. Later, I would learn that it was called ‘man-scaped’ but I was still innocent of such things! A moment later, I saw his erection, first pushed over to the right by the shorts, and then, released, bursting out with abandon and sticking straight up, practically in my face.

His penis was as perfect as the rest of his body. It was a lot bigger than what I thought must be ‘average,’ with a foreskin concealing most of the head. It was throbbing and bobbing up and down with his heartbeat. I stopped, breathless.

“You like it?”

My voice trembling, I replied, “It’s beautiful,” giving it just the softest of kisses. As I did so, Beau let out a deep sigh.

“You’re not bad yourself!” As Beau said it, I realized that, while I was unveiling his manhood, he had slipped my underpants down, freeing my own pulsing prick.

He pulled my face toward him, and we kissed deeply again. Then we moved apart and Beau stood up and removed his shoes, socks, and shorts. Seeing him totally naked in front of me, I knew why Windermere had referred to him as an Adonis.

Michelangelo’s David had nothing on the magnificent young man baring all for my viewing pleasure. His blond hair was perfectly styled, but a little mussed from my pulling his shirt off over his head. His face was softly tanned, so his bright blue eyes glowed like diamonds. His lips, which had already become intimately acquainted with mine, were just perfect. His neck and shoulders were strong but not overly muscular. His chest was firm and his rippled abdomen looked like he must get a lot of exercise.

His hard dick was perpendicular to the floor, sticking straight at me with all of its length. His hips and legs were more muscular than his arms, and his feet were rather large, which I have been told goes with a big dick. Once again, I was grateful that he had no tattoos or piercings on his perfect body.

I happened to glance past him and saw in the mirror on the wall that his buttocks were well-developed and powerful. Knowing as I did that he used them for sex, I felt a thrill, as I imagined what it would feel like to press my rod between them. Fully aware that I was taking such a lingering look at him, and liking what I saw, he responded with a wide grin and a wink of his eye.

With that, I also rose and kicked my underwear off.