As I’ve gotten older (I just turned 60) not only has my sex drive increased but so has my sexual attraction to men. My first same-sex experiences were as an adolescent, experimenting with cousins and friends. I chalked this up to innocence and youth and while fun, they did not go far and never resulted in ejaculation. The first experience I’d consider “sex” with another guy was the partner I was randomly paired up with in a water safety instructor course my freshman year in college. We spent a lot of time grappling in the water as part of the course and ended up making out and jacking each other off after running into each other at a bar one night. We met a few times after that and actually swapped blowjobs a few times in the locker room after class (potentially a future story). Shortly after college, I met my wife and maintained a committed sexual relationship with her for several decades. Throughout my marriage, guys still captured my attention and I occasionally fantasized about guys I had seen in various stages of undress at the gym, but never acted on it.
As I reached my 40’s I had begun reading Craigslist personals and found myself fantasizing about responding to an ad, often working myself up sexually (and relieving it with my wife). I traveled a fair amount for work and there were certain times that I felt if I pursued it, I could have had a sexual encounter with a co-worker or another guy staying at the hotel, but I never pursued it. In fact, one time, I was sitting in a hotel bar watching some sporting event and despite multiple open seats, an attractive guy I had seen in the hotel gym that morning sat right next to me and started up a conversation. My spidey-sense led me to believe this guy was looking for more than someone to chat and watch the game with at the bar. But fear and commitment kept the conversation from getting personal or encouraging with him. I eventually excused myself to go to bed.
As I got into my 50’s, the desire and intensity for sexual intimacy with a guy increased while I found my inhibitions beginning to decrease. I was discovering all the new technologies creating so many more ways to pursue and find a sex partner and while I found myself reading them with increasing seriousness, I still never took any action. The idea of an anonymous encounter was incredibly stimulating (and the source of many loads of cum) but the rational side of my brain along with post ejaculation clarity always took over and prevented any actual pursuit. Then I stumbled upon the escort websites. While I was of course familiar with “the oldest profession” I was pretty naive about the process of hiring a sex worker and quite frankly, was never interested enough to run the risk and public humiliation of getting arrested for it. It was the Tiger Woods escort story in the 2010’s where I learned that Escorts bypass the law by entering agreement for their time and what you did with the time was up to each consenting adult. Even then, I only associated escorting with women, never considering that there were male escorts for men were a thing . My impression was that male for male sex worker trade was more tawdry, consisting of street hustlers who were potentially dangerous and vulnerable to transmittable diseases. As I write this, I deeply regret that I held such a prejudiced belief stemming from my naivety and provincial beliefs about sex with men.
Looking through the online listings of male escorts opened me up to a new world I had no idea existed. The range of types of men was the first thing that opened my eyes. I would have assumed that most escorts were 25-30, 6’, perfect bodies and big dicks. But that quickly changed as I read through descriptions in the listings of their services and expertise, their physical stats. Listings ranged from guys who were barely 18 to senior citizens, a range of sizes, ethnicities and types of interactions, not to mention the rabbit holes I went down learning about all of the kinks that could be satisfied. I was truly oblivious to this world but the more I learned about it the more I knew I was not alone in my feelings and fantasies and that there was an economy that existed to support the fulfillment of them. I looked through these ads for months, each time bringing myself to various stages of arousal. There were sites where men submitted listings and profiles with varying degrees of detail on what they were willing to do (boyfriend experience, top/bottom/versatile…). These seemed more like an escort service. There were other sites with listings of men offering an array of massage styles often categorized as therapeutic, sensual and erotic for men. It felt like there was some code that I was not aware of as the ads seemed purposefully vague about what the experience entails so it took a bit of detective work between the masseur’s listing and the reviews from past clients for me to get a good sense for what the experience would entail and what defined the line between sensual and sexual. I was looking for a connection with a man that led to a sexual experience. While I was not seeking a specific sex act, my fantasies were much more about the physical connection than they were about getting off (I could do that on my own). I hungered to be naked and vulnerable with another man, to have him touch me with purpose in a way I imagined was more raw and less delicate than the touch of a woman. I wanted someone to take charge in an area where I lacked experience like a coach, a guide or a trainer. I was even excited by the idea of being more submissive.
After living for over five decades, I’ve embraced that life evolves in cycles and I was at a point where recent personal and professional events left me especially vulnerable and feeling sorry for myself. I never found drugs or alcohol to be an effective way to decompress but I did find sexual fantasy – especially those that felt forbidden – to provide an effective escape and path to helping me center myself. It was during this recent down cycle that I began binging on these erotic masseur sites, attracted to the experience of having another man’s hands on my naked body for an hour+. My vulnerable mental state, my built up curiosity and the freedom to explore brought on a new sense of courage to take the next step of actually booking an appointment.
Anyone who has looked at these listings in a major city certainly knows that there is a large number to choose from. On my first pass, I ruled out anybody around my kid's age or younger. It not only felt weird but it was hard for me to imagine I’d be able to find the emotional connection I hungered for with someone in their 20’s. After overthinking the options I let my cock lead the way and sorted to guys over 30, under 6’ (to be closer to my 5’7”), with body hair, offered incalls and that I could tell (often from reviews) that the masseur would also be naked during the massage. Many of the descriptions of what they offer were starting to sound similar. But there was one that I kept coming back to which seemed a bit different from the rest. It was for a Thai massage, which I had experienced once before. Typical Thai massages are done on a special woven mat on the floor with no massage oils and at least in my case, fully clothed and in the open gym (vs a private room). I loved the experience as it involved all the masseur’s body parts (including feet) and really stretched my muscles in new ways, reducing muscle and joint stiffness and enhancing mobility. There is also a deeper level of intimacy involved as the masseur is right at your level, even laying on top of you with most body parts touching each other. Seeing Jack’s listing on the site made me recall my previous experience and the thought of that type of massage in a private and with both of us naked definitely registered with the brain south of my waist.
I reached out to Jack via the site to inquire about his availability, rates. I also wanted to confirm that we would both indeed be nude. He responded quickly and with very little back and forth, we set a time for the upcoming Sunday. With the appointment set, my paranoid mind started to go through all of the worst case scenarios but my raging libido prevailed and overcame any hesitations I may have had about keeping the appointment. I fantasized several times over the ensuing days leading up to it, imagining what it would be like and what types of sexual situations I might get into. Despite getting incredibly aroused, I chose to abstain from masturbating in the days leading up to my appointment knowing that arousal = courage.
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I’m actually in much better physical shape now than when I was 40. Less body fat and more muscle on my 5’7” body. I have a 32” waist and spend a lot of time building my quads, glutes and hamstrings which is evident when I wear anything that clings to my body. I keep my graying hair short and in style. I’m hairy, but trimmed - nothing too short or shaved, except my balls. Call me old school, but I love a full bush of pubes and the way mine surrounds my slightly below average-sized cut cock. Sunday arrived and as I do nearly every day, I got up and went to the gym. I definitely needed the activity and a tension release and a freshly pumped body always filled me with some nice endorphins. I grabbed some lunch and a few hours before my late afternoon appointment, I took a long shower and decided to douche out my ass. I’d never done this before but if the opportunity arose for any anal or prostate massage, I wanted to be confidently clean. Using a makeshift device from a water bottle, that was both a process and a learning experience in and of itself. After drying off, I slipped into clean clothes that were comfortable and easy to remove. I chose a pair of lightweight joggers, on top of tight, 3” boxer briefs, a t-shirt and a quarter zip pullover. After confirming the appointment with Jack, he texted over the exact address. I left with plenty of time and arrived about :15 early to the area where his apartment was located. It was an older neighborhood, closer to the city and it took a bit to find some street parking. Once I parked, I texted again to say that I was walking toward his building and received further instructions to get buzzed into the building and to his specific unit. Once up there, I knocked just once before the door opened. Unlike other masseuses, Jack’s listing included only a few pictures, the most revealing being his hairy chest. Typically that would have been a red flag, but his numerous reviews provided the assurance that Jack was clean, fit and attractive. They were absolutely correct – Jack is a beautiful human being. Not effusive, but warm and welcoming which immediately put me at ease. He too was wearing joggers, a well-fitting t-shirt and a baseball cap over his shaved head and he was barefoot. Understatedly sexy.
I entered through a short hallway, off which was a bathroom and bedroom to the right and a living room to the left. After removing my shoes and pullover, Jack led me into the living room where his Thai massage mat had been laid out on the floor. The room was dark, cozy, smelled good and was overall very inviting. Some east asian-ish music was playing very softly in the background. Jack proceeded to ask where on my body I was having issues and where he would like me to focus. After explaining the usual neck, shoulder, back and hamstrings he said “got it” and asked if I needed the restroom before we started (which I did to unload all of the water I had been nervously drinking up to that point.) The bathroom was a little steamy, which indicated to me that Jack was freshly showered. My pee sounded heavy as it hit the water and seemed to flow forever. I had that charged up feeling of nervous excitement. I was grateful to be past the initially hard part of facing any apprehensions I had about scheduling the appointment and what the masseuse would be like. I gave my still nervously soft and short penis a vigorous shake, pulled up my joggers, flushed and washed my hands before stepping back into the living room. Jack had placed a pillow on the mat and instructed me to remove my clothes, place them on the chair and lie on the mat (it was covered in a sheet) face down with my arms above my head and the pillow underneath my chest and armpits. He said while I was doing this, he was going to get himself ready. With trembling excitement, I slipped out of my joggers, underwear and t-shirt, neatly folding and placing them on the chair and got myself positioned on the mat as instructed. While I was uncovered, the temperature felt really comfortable. What was likely just a minute or two, I layed there on the mat in a heightened state of arousal but still feeling vulnerable. I’m in a stranger’s house, bare assed, on the floor still uncertain about what was going to happen next. While a bit anxious, I was at peace and made a conscious effort to let go and let my body feel for the next 90 minutes. The click of the bathroom lightswitch signaled that Jack was on his way out. He walked out of the bathroom into the dimly lit hall and padded quietly into the living room, completely nude except for a backward ball cap. He has the build that always gets my attention – about 5’8” or 9”, athletic frame, thick trunk, nicely defined and a chest full of light brown hair, decent sized shoulders and biceps proportionate to his muscly trunk. His penis was soft and average sized, cut and deliciously nestled in a nice bush, with his balls hanging slightly below. I did not get a glimpse of his ass as he entered, but given the size of his trunk, I imagined it to be nicely built also just as I like.
As described, the entire experience was deeply intimate. Jack’s body was within inches of mine right from the beginning and throughout. His approach to Thai massage included a combination of stretching, pulling and muscle manipulation, putting my body in specific positions only possible on a hard surface and when both the masseuse and client were on the same level at the leverage afforded by that. Unlike my previous Thai massage in addition to the nudity, Jack also at times used oil when he was applying deeper pressure. As he worked various parts of my body, his hairy chest would brush and rub against my face, back and legs and I could feel his hanging cock and balls occasionally come in contact with parts of my body. Some of his movements were big and with deep pressure, others were small and more nuanced but all combined to create an experience that was as therapeutic as it was sublime. I was so into the sensuousness and intimacy that was able to form between us, my trust grew and I relaxed which only enhanced the sensations as he methodically pushed the boundaries back and forth between sensual and erotic. The electric touch of his soft but heavy cock was just the start. Eventually, his hands subtly brushed against the back of my balls which evolved to rubbing his oiled hand down the hairy crack of my ass, using his slick fingers to circle my anus and gently plunge a finger in and out of my rectum. This continued with increasing levels of pressure and eroticism until Jack laid his entire body on top of mine. It was not a nuru experience where I was massaged by the back and forth of his slicked-up body but rather the pleasure of shifting pressure along the entire back of my body from his. With his head slowly behind mine, he also started to softly kiss my back while making slight moans as he kissed his way up to the back of my neck to check my ear. Ultimately I turned my face to meet his lips. Kisses turned to full on making out with our tongues literally fucking each other’s mouths. After a few minutes, Jack lifted up, looked directly into my eyes, asked how I was doing as he gently pulled at my shoulders saying it was time to flip on to my back. As I flipped, Jack shimmed down my body, resting on his knees between my spread legs which gave him better access to my chest, arms, abs and quads. He leaned over my body, reaching his arms to the front of my shoulder and neck and began to massage them while his mouth was working my nipples. Kissing and light licking evolved into full-on sucking. At one point, he was sucking them like he was trying to nurse my tits and I went into a trance from the ecstatic feeling. He raised up and continued to use his oiled up hands and fingers to deeply massage down my biceps, pecs and abdominals, continuing to ensure my nipples maintained their erect and engorged state, poking through my lush salt and pepper chest of hair.
Jack then slowly worked his way down my right leg, applying deep pressure with his fingers along the way, hands casually bumping into my balls and cock which while not erect, was much larger from all the blood flow. This tease continued as he moved and did the same thing to my left leg. Things started to heat up toward the boiling point as Jack stretched my legs, bending my right knee and pushing it against my body. When he did this, our cocks touched for the first time. As he pressed my bent knee deeper into my chest to stretch it further, his dick ground into mine. The stretch went on for a few minutes as he rocked it back and forth along with his dick, still pressed into mine. This pressure and direct stimulation brought me to full erection and I could definitely feel the size and firmness of Jack’s cock increase as well. That alone was worth the entire massage it was so fucking stimulating. After repeating the same thing on the left side and rock hard at this point, Jack spread and positioned my legs in a butterfly position providing full exposure and access to my groin. After doing deep work on the sides and top of my quads with deep pressure from his fingers, he moved to my cock and began to stroke it with his well oiled hand. He went between full strokes and what felt like oiling my ballsack, adding his other hand and moving his oiled fingers below my balls back to my asshole which he gently darted in and out of. He was very well on his way to working me up into a sexual frenzy for which there was no return.
At this point, I was so in the moment that I had no idea how much time had elapsed. I had essentially surrendered my body to Jack and he had masterfully brought me close to the point of unleashing the six day load brewing in my balls and prostate. I’d actually thought that this was his final lead up to what would have been a magnificent happy ending. But not wanting to come just yet, I motioned to Jack to back off which he did immediately, sitting back on his knees looking at me with a smoldering grin. He moved himself back, guided my legs out of the butterfly positioning and gently lifting my ass to lay on me on my left side. Once settled, Jack did the same, placing us in a 69 position. He laid his bottom leg flat along the ground and bent his top leg up, placing his foot flat on the floor and giving me unencumbered access to his balls and penis, which was sticking straight out from his perfectly furry groin. It took a few seconds to finally examine this prize but I could not resist the gravitational pull of my lips to its moist tip. It was beautifully shaped, cut and its ample head was nicely proportioned to the shaft. The entire package fit perfectly in my mouth as I quickly engulfed it until I could feel his soft, wiry pubes under my nose. My mouth was open wide as Jack gently pushed his cock into the back of my throat. I truly loved his cock and it was by far the most favorite I’d had in my mouth. While this was going on, Jack was alternating between using his mouth and hands on my cock and balls. He found my spot of ecstacy under the tip and I could feel him lathering up my frenulum with his spit and going to town up and down the underside of my cock with his wet tongue. Once again, I had to grab his wrist to hold off my ejaculation. At that point my mouth had not left Jack’s cock, so I let up to get some air and shifted slightly to explore his ass for the first time. With a hand on each mound of fur, I worked my tongue from his balls all the way up to his hole, getting it really wet and darting my tongue in and out. How I would love to fall asleep with my hands grabbing onto Jack’s firm, fuzzy ass. To do this, I’d been craning my neck so I went back to his dick to give my freshly stretched neck a little rest. Slobbering all over the tip, I dove down on Jack’s cock again, eliciting gentle moans from him each time his tip hit the back of my throat. All the while, he continued with his hands and mouth on m penis, alternating between easily engulfing the length while he expertly tongued the head. For a third time, I had to ask him to back off but we both knew I could not last much longer. I was definitely a guy in heat.
Jack sat up and I followed his lead. I moved my head up his belly, kissing up him and lingering around his erect nipple then burying my face in the fur that covered his chest. As I inhaled, I could smell the clean soap from his shower but as my head inched closer to his armpit, I got a musky whiff that I was tempted to extend my tongue to taste - up until this moment, that not something I would have considered a turn on but in the moment it was instinctual. It was probably from the sweat induced by the bodywork he was doing on me. He gently leaned me on my back, lifted my ass onto his lap and started to massage my still stiff dick, gently but tightly jacking it while looking into my eyes, again with that sexy smoulder. That look is what took me to that point of no return, giving into the ejaculation that had been trying to work its way out my cock for a while. Even if he had stopped jacking me, I would have exploded at that point, but he continued stroking up and down. My lower body began to shudder as the first volley was working its way through my urethra. One, two, three, four, five six volley’s of hot cum shot out the tip of my dick, landing between my neck and belly button. Between the 6 day load and the edging, the volume was much greater than I had produced in a while. Jack continued to stroke through all the final spasms, squeezing out the sperm that remained in the head my dick. Feeling a slight burn in my prostate from the ejaculate force, I stayed in the position for a bit, savoring the feeling until I could regain my composure and speak. The first words were heaps of praise for his masterful work. He gently shifted my hips and ass off his lap, leaned over and we made out. I’ll never forget the feeling of our chests pressing together with a thick layer of cum between them. It felt so good and so right. As Jack got up and walked out of the room to grab some towels to clean up, I got my first good look at his perfectly shaped, muscly mounds shifting in lock step as he walked toward the kitchen. That was my last image as he emerged from the kitchen minutes later with some warm towels but now clothed in a tshirt and gym shorts. He proceeded to swab my puddled body with the warm towels while I continued to lay there naked, still coming down from the high of the experience and the contractions of my orgasm. We talked, but I have no recollection of what we said to each other. It was lovely.
As I dressed, he asked how I felt and I shared both the improvements in my physical and emotional state. He said “goal achieved” and we hugged. I gave him a kiss on the lips and went on my way. I have a lot of respect for Jack and I felt that respect was reciprocated. I’m grateful for skilled men like him who provide a valuable, healing service and hope that the experience provided him with some satisfaction as well.
