Anson's Search for a Travel Company

Author's Note: This is entirely fictional. Copyright, 2023. If male on male sex is not your thing, please feel free to move on. Everyone is over 18--as should be anyone who is given access to this. Thanks for reading.

Anson Powell had buried his wife of 25 years, after a long six year battle with cancer, about three months ago. For many years prior to her death, she was bed-restricted, tended to by private nurses which were easily affordable on Anson's generous compensation as one of the top litigators in a large San Francisco law firm. Their marriage had been a very good and loving one, and although Anson realized he was bi when they married, he was faithful to the end. They were childless. Neither Anson nor his wife had family, except for Anson's one younger brother who lived in New York. Their parents had passed several years prior. So Anson had pretty much grieved alone for several months, and of course he had been deprived of intimacy for years prior to that. Business and tennis partners had been sympathetic, but there are limits to distance empathy and time limits on friendship tolerance.

Anson was a great litigator. So good that he had attracted the sobriquet, "Honey-Tongued Advocate"--it was said he could charm any verdict from a jury by alternately seducing the women and the men with his mellifluous arguments and his attractive physical presence. For years during his wife's illness, he had buried himself in work, clocking enormous hours and taking on complex cases one after the other. This made him a very wealthy man indeed and capable of getting just about anything he wanted.

Before the marriage, Anson's physical presence, intellect, and deep voice meant that he had been able to honey coat his way into any vagina he fancied--and any ass or mouth, male or female that appealed. In that latter case, his enormous endowment also helped. Anson's partners always claimed that he paid for his "gifts" by advocating repeatedly for LGTBQ+ issues--always successfully in liberal California. But, of late he had pretty much become a loner, sad much of the time, and borderline depressive.

Recently to change the scene, he had decided to remodel their large loft-style condo on the top floor of one of the prestigious mid-rise condos just off of Embarcadero with spectacular views. He wanted to eliminate the French style and most of the walls in favor of an industrial modern look with one super large two story great room, an office/den, and two bedrooms, with a massive spa bath. It would be appropriately furnished with masculine furniture. In short he was starting on an entirely new life. He had hired an architect and ultimately a contractor. Permits were in hand. Work would start the day after he left on an extended trip. Boxes were stacked everywhere and much of the furniture had been wrapped--all destined for auction or charity, starting in about a week and half to permit the work to begin unimpeded on his departure.. The remaining items would be stored and re-delivered when renovations were completed--probably in about two-three months.

Anson had taken a leave of absence "to grieve" and planned to take an extended trip to Asia, only in part because of the inconvenience of the renovations. He wanted a change, new challenges, and new faces in his life. He expected to leave in about a month.

The Proposal

A few weeks after his wife's death, when Anson had decided on the renovation, healso began planning a trip--and soon realized that solo travel was almost as expensive as couples travel. And he really didn't want to be alone, cruising in strange cities--particularly since it had been so long since he had done so. In fact he was a little afraid he had forgotten how. So, he decided he wanted a companion and assistant, and not just any companion, but one with benefits--so no family, of which he had none anyway.

So he cruised a few gay clubs for a few weeks, but soon realized that his situation was special and would require a unique search. Times had changed; techniques and styles had changed. And he was definitely not a "player." Anson was 52, a handsome man, in great shape with a full head of curly black hair, only slightly graying on the sides. He had regular tennis dates and competition and regular workouts with a trainer which kept him defined--and looking like a 40 year old--but in young SF, 40 was very definitely over the crest of the hill. And he was endowed. It shouldn't be an issue to attract a companion, but cruising was not achieving the results he wanted, although he did hook successfully a few times. But one night stands with strangers and finding a suitable companion for a couple of months were very different.

So Anson decided to mount a careful online search, using a new "meet and greet" gay website that had been created by several older Silicon Valley guys--and it was by subscription only, with entrance fees rising with age and anyone under 30 vetted carefully by the two webmasters--which filtered out many of the less desirable elements. The site had advertised (and recruited) in university, medical and young professional circles particularly. So, he joined Sidewindr and prepared and posted his notice:

ISO of Male Travel Companion (with benefits), 8 weeks, Asia, July and August. Expenses paid for suitable person.

Me: In shape 52, bi-widower, financially secure, attorney, long-time SF resident. Weight proportional to height (6-2), in shape (tennis and gym), lightly cut, small love handles, very well-endowed. Dark curly hair, but otherwise shaved. Well-educated and intelligent. Certified clean. Probably a regular top.

You: 22-30, gay or bi, attractive, in shape, clean, masculine (no femboys, cross dressers, twinks, flamers). Must have passport. Respond to Box 2025 Sidewindr with head and full body shots, email and cell phone. PLEASE don't respond if you don't fit. It will waste both of our time. All answers not responsive will be destroyed.

What I Plan: A few will be chosen though exchange of emails and photos and a call, followed by an informal lunch/coffee/cocktail meeting where more will be explained. Then we'll meet a few more times to insure compatibility. Departure scheduled for July 2 from SFO.

With an offer like this, Anson expected dozens of non-conforming responses and he didn't hold out much hope of finding a companion, so he continued to cruise. But, to his surprise, within three days, he had about a dozen answers. Many seemed possible, so he chose four at random and emailed (with his head shot and in tennis whites) and called.

The Initial Phone Calls

Leigh was 22, a recent graduate of USF and planning on grad school in Asian politics. He was possibly mixed Asian with a darker complexion. Claimed to speak Mandarin. He had a local family; he was gay and out; maybe a little intense and nerdy, usually a bottom. His coy photos showed a medium height, smooth high bubble butt, light muscles, but his equipment was in shadow, but he appeared to be completely shaved. Anson set up lunch the next day at a small café near USF.

Lloyd was 25, a biology student. He was headed for a career in medicine, possibly an EMT or in ER. He was tall, perhaps the tallest at 6-3, with a long attractive dick, a sculpted gym-body, on the thin side. He was reserved and unsure about the prospect. He was a veteran (which explained that he was still an undergraduate at 25), but hadn't come out until departure from service. Recent breakup with a partner of 9 months. They had been vers, but Lloyd usually bottomed. He didn't want a dom or a daddy. Probably mixed race with mocha coloring. He was anxious to get out of Dodge--was he on the rebound? Anson set up coffee the next day nearby.

Jessie was 27. He was a software engineer whose employer had just been acquired by Google. He was given six months with compensation to decide whether he wanted to join the team or strike out alone. He claimed some significant savings. Active in SF gay scene for 7 years. Had had several medium term relationships, but wasn't in one now. Gym rat. Blond, clean cut, longish hair, and surfer tan. Definitely a California laid-back boy. His only body photo was in a jock which seemed barely able to hold his manhood, but he had lightly defined muscles. Model quality. He was sexually active--both top and bottom. Lunch was set up in two days.

When Anson called Jorge, the phone was answered by a young girl who quickly called her brother to the phone. He was a Latino, 29, and PA/RN--a physician assistant in the respiratory ward of SF's large public hospital. He was light-skinned, like a good tan, handsome, with dark curls, dark eyes and a smile that would light a room, set in a square-face. He was the shortest at 5-11--broadly muscled and with beer can cock potential. He had a friendly voice, but was probably the least liberally educated although he spoke perfect colloquial American English. He had a large SF extended family, but had been raised without a father. Very little sexual experience, mostly recent and usually as bottom. (Was he perhaps on a Daddy search?) Cocktails at the condo on Thursday afternoon at 4--the only one invited to Anson's home. His voice was a "safe" one.

And then Anson started comparing and contrasting--and spinning back up stories, motives, and qualities. What did he want? A sub who carried bags, received his spunk when he was so inclined, and was otherwise a silent, attractive companion? Or someone with intellectual substance? Maybe just a big dick? Anson would gladly pick up any of these guys as a hook at the club. He couldn't base the decision on a quick lunch or a coffee--it was going to take a full-on experience--in his bed, maybe more than one. So he decided to use the first meeting to measure the vibes and convince all the candidates that this was something they really wanted--so it would be his choice, not theirs.

Finally, he wondered whether he was looking for a travel companion for two months or so or a potential life partner. Either way, the decision was going to be difficult: who did he want to wake up in bed with for two months? The decision was not going to be an analytical one, but that was the way Anson's approached decisions. He would need to be careful to examine the intangible vibes--and consider his own unconscious reactions.

The Candidate Interviews

The first coffee was with Leigh, the youngest, who was probably Chinese American. He was on time, dressed appropriately in chinos and polo, trying hard to be college preppy. He was good with words, charming, on the make, and a take charge guy--although he was deferential to Anson's age. Almost immediately Anson decided it would be like traveling with his grandson. (He didn't have a grandson.) But it would be a grandson with an attractive, probably receptive body and possibly useful language skills. Perhaps he wanted a sub after all. Leigh was immature, perhaps a bit too practiced, too much on the make. He had probably mastered the club protocols--and would be able to to walk off with a stud most nights. Anson decided he might be an interesting lay and a definite candidate for the trip--if he decided on a young sub, so he set up cocktails for Friday night at the condo at six. Did he want a toy or a companion? Leigh clearly understood that cocktails were foreplay.

Three hours later, Anson met Lloyd at a Starbucks. Lloyd was a knockout specimen of manhood. Heads turned when he entered in his scrubs, (for which he apologized--"I'm just coming off duty.")--looking for all the world like a young muscled underwear model (not the metro-sexual, but the square jawed, dusky hunk kind). Lloyd sat and Anson got up to get their drinks. His lazy voice seemed to mimic the honey tones that Anson used with a jury. He had no family left in California and wasn't really active in the bar scene--choosing instead to find partners in several LGTBQ charity projects. He seemed genuinely sincere, was very deferential and a little quiet, but responsive to Anson's interrogation. "Can you afford to take off the summer? Have you traveled much?" "Yes to both, I'm not doing summer classes this year. Most of my travel was while I was in the military." Anson spent a few minutes talking about himself, then asked the question, "Could you live with me for a couple of months? Am I your type? Do you usually bottom?" Yes to all three questions. "You're a good looking man, Mr. Powell. I could do it--and I think I could really enjoy it, and I think I could make it very good for you as well. Give me a chance to prove it." "Okay, here's my address; can you do a light dinner at my place on Saturday?" "I'll be there." Later Anson realized that Lloyd was the only one who actually asked for the job on the first interview. It would definitely be a pleasure to be in this young man's company for a couple of months. Anson's lust was aroused. He'd have to be careful that his dickhead didn't make his decision for him.

Lunch with Jessie was set on the terrace of the tennis club where casual was the rule at lunch. He fit right in--tall, blond, definitely multi-generational Californian. His chest muscles stretched his white polo to its limits. Jessie was a computer nerd--everything (except boarding which he did every week, often more than once) revolved around tech--in fact he took and sent several txts during lunch. Anson wondered if he answered his phone while fucking. But, he was good looking and Anson wanted a shot at his ass and he definitely wanted to see the dick without jock interference. Both guys were athletes and lunch conversation turned on the progress of several SF franchises. Jessie knew what he was talking about, often citing obscure statistics. Jessie seemed very mature for his age and would be a good companion. So Anson, not wanting to burn any bridges, invited him for drinks on Sunday at the condo. But, Anson thought Jessie was probably a long shot--interested for a hook, but perhaps not a keeper for a long vacation.

Jorge was a no-show, but later txted that a family emergency had kept him from the cocktails. He was still at the ER. Anson replied that he understood and would be in touch. But, first he had three guys to consider--and it was definitely time for the "no swimsuit audition" in this contest.

Before Friday came, Anson had six more responses. This was definitely getting interesting. Why hadn't he considered this before--even as a scam? Sidewindr was definitely paying off his investment.

The Auditions

Promptly Friday at six, the concierge called to say that Leigh was in the lobby--and he was sent up, alighting from the elevator directly into the full floor penthouse foyer. Leigh's eyes opened wide when he entered. He had hit the jackpot. This was a prize condo. Anson must be loaded--and probably with well-connected old money. Anson offered G/T's and Leigh accepted. They walked past boxes to the bar and then to the long leather sofa facing the view. Anson explained the impending reno, but gave no further details. Nevertheless, Leigh was impressed. He waited for Anson to sit and then sat next to him--not at the other end of the sofa. They talked for a few minutes. Leigh was voluble, and his face was animated as he slowly moved into Anson's personal space. Then Anson placed his drink on the cocktail table and reached over to pull Leigh into an embrace. Leigh opened and wrapped his arms around Anson's back, dropped his head to Anson's shoulder, but didn't move to a kiss. Soon Anson pushed him back on the sofa noticing the hard tube in his crotch. "With your permission...." He murmured as he began to unbutton and unzip Leigh's slacks. Leigh was commando and his excited dick popped up immediately. He was average-sized, uncut and completely shaved. Anson pulled the chinos completely off. Leigh had not attempted to reciprocate.

After a few minutes of attention, Anson rose. "Let's take this to the bedroom where we can be more comfortable." As he moved toward the bedroom, Anson watched Leigh's bubble bounce nicely. He pulled his shirt from his slacks and began undoing the belt. Soon both guys were nude. Leigh stood there, smooth, hairless, erect and proud. He looked over at Anson, "Wow, when you said well-endowed, I didn't know you meant a Harvard-sized endowment. You must be 12 inches. You're going to tear me up. I'll never walk again." "Thanks, flattery will get you far, but you exaggerate--I'm probably about 10 and a half. And I went to Stanford. Let's see how we fit together."

Leigh reached out and pulled Anson's massive dick into his mouth, sucking hard on the top half, then licked the shaft while he cupped Anson's balls and teased his taint. He was definitely skilled. Anson pushed Leigh down and covered him, so they could move together. They rolled, wrestled, penetrated with fingers, bit on nips, squeezed ass cheeks, while raising the temperature in the room. Leigh was responsive, but a little reserved, definitely a bottom.

Then Anson rose, pushed Leigh back on his chest, pushed a bolster under his gut, and after rubbing his cock along the crevice, lubed and began his finger preparation of the anal cavity. He expected that Leigh would require a good deal of opening--and Anson planned on using four. Leigh made all the right sounds--and all the right moves, pushing his ass up toward Anson, stretching out his legs, and encouraging with language. He might be young, but he was not an amateur. Finally, Anson wrapped, lubed himself, placed his hard plum-shaped head at the entrance and began to pressure. Leigh pushed back and the head popped in. Leigh's eyes went wide as he was stretched to the limit by Anson's massive erect dick. Anson pushed a little farther and found the prostate and started the massage which soon brought Leigh to orgasm, even before Anson had dipped in with half his manhood. In orgasm, Leigh used his talented anal muscles to return the favor and Anson was soon filling his magnum. And then it was over. Anson realized he had not fully penetrated, which was not very satisfactory. Perhaps with practice.

But he had saved the tough questions: "Can you get a ckeab certificate within a few weeks? If we are going to be together for two months, I want to do this bareback and much deeper. Does that worry you? Are you prepared to commit to exclusivity during the trip? Are you still interested in traveling with an old man? Can you top if I want it?" Leigh responded quietly and carefully, obviously still on a carnal high from the intense fucking he had just received from a big dick. But, he was not sure he could take that cock for two months--if indeed he could take it at all. He'd be ruined for any normal male. "I'll be back to you within a week. But, I must say that next time you're taking all of me or this won't work. So maybe you should practice a bit." A week...so Leigh would have time to consider his decision.

Anson's next one-on-one was with Lloyd for dinner. He arrived on time and in a sport coat. "You need to lose that." "Yes, sir," he answered. Was Anson dealing with a confirmed sub or was it residual military training? "Does this whole idea bother you? I think maybe it does." "I've never been in a situation like this before--where I'm interviewing to be your paid whore for the next two months. That is not my style. I've never been paid. Maybe I'm on the rebound. Maybe this is a mistake. But you are a really attractive guy. I think I could get into you." "Actually it's me who is going to get into you," Anson joked.

Anson offered him a drink--scotch/rocks--and got one for himself. "We both know why we are here tonight. I like the way you look and carry yourself. And you are definitely not my whore--or my bitch. So you can forget that. You'd be a travel companion and assistant. I'm hoping we can both cum to enjoy this. Dinner can wait. Let's take this to my room."