Not was I was expecting

Bill is a trainer at the local, independent gym I had been going to for several years. Being both in our early 50’s in a gym full of millennials and gen Z-ers, we were friendly, often striking up casual “hey, how’s it going” kind of conversations. Sometimes he’d give me a few pointers on my form even though I did not train with him. While I’m strong and well-proportioned, I was not as disciplined about my nutrition which gave me a bit of a dad bod compared to Bill.

I had been single a few years after a long marriage and used working out as my therapy. Being a bit older and trying to keep up with my fellow gym goers, I pushed myself pretty hard and found myself moving too slowly the days after working out. I’d visited a chiropractor who had provided some relief but said what I really needed was massage. I have a had a few massages here and there over the years but more for relaxation vs. for therapeutic reasons. My chiro made a strong case, convincing me it was worth considering and so I asked if he had any recommendations for masseuses in the area. He gave me a list of three that I shoved in my pocket as I was heading out the door.

The next morning, I woke up to hamstrings that were so tight I had to shuffle my feet to get myself to the bathroom. While a hot shower restored some of the mobility, the stiffness was incentive-enough to fish the list of masseuses out of the pants I was wearing the day before. The first two names were women and the third was a guy named Bill Benjamin which I quickly recognized as the trainer from the gym. That made the decision easy as I was planning on hitting the gym later in the day (for back and arms – no legs!). After I finished my workout and saw that he was not with a client, I approached him saying “Hi Bill. When he looked up, he looked directly into my eyes and immediately smiled. I’m not sure what it was, but his look hit me differently than our other interactions. Perhaps it was I noticed the deep color of his eyes or maybe it was a warmer, friendlier smile – I’m not sure, but it was different, and it gave me a calm, welcoming reassurance. I told him about the recommendation from the chiropractor and the issues I had been experiencing and he assured me he could help. So, I went ahead and set up an appointment with him for the next day at his studio which was at the back of the gym. I figured that I would work out then head right into the massage.

After finishing up my workout, I took a hot shower, slipped on a clean pair of boxer briefs and headed over to the massage room with the towel wrapped around my waist. Bill opened up the room, asked me to get under the sheets, face down on the table and he would be back in a few minutes. I have to admit, as I was laying there, I looked forward to both the attention and the muscle relief.

When Bill entered, he was low-key in a Zen kind of way. A little small talk, but mostly asked a lot of questions about what areas were bothering me, how I may have gotten injured, and what my workout routine was. He also asked a bunch of lifestyle questions about nutrition, hydration, medications, amout of sleep as well as depression, anxiety and loneliness. I answered his questions openly and honestly and as I was doing so; he moved the sheets and started running his fingers across by back, stopping and pressing in certain areas moving to my arms, legs, feet and glutes. Very quickly and intuitively, Bill found the source of my pain – some from the spot where it hurt and some from what he called “referral pain” – an injury in one spot that was creating pain in another. Between a combo of deep tissue pressure and a variety of stretching he worked hard to alleviate the issues and the symptoms. His touch was strong and confident – like him but at the right times gentle and soothing, which is actually sums up him – he is about 6 feet tall, shaved head, full beard with a solid, well-proportioned frame. He’s not stocky, but has thick thighs, butt, arms and chest. While his massage provided relief from the pain, I found his touch throughout unexpectedly pleasurable.

I knew in my teens that I was on the sexuality spectrum – not straight, not gay yet never really identified with being bisexual either. I never indulged any of my gay tendencies and went on to live an exclusively hetero lifestyle yet would fantasize from time to about some random guy I’d seen at places like work, a store or at the gym. Again, while I accepted these feelings for what they were, I always held back acting on them. However, the longer I was unpartnered, the less inclined I became to suppress these feelings. In fact, if a guy hit on me, I now would probably respond or at least acknowledge whereas previously I would have imply brushed it off or ignored it. I’m still not at the point of ever proactively hitting on a guy.

I felt so much pain relief from Bill’s first massage that I went ahead and scheduled regular appointments with him. Because I was feeling better, I found myself training and pushing myself much harder with exercise and starting to see continued improvement on my results. I still have a dad bod – but less dad, more bod. While Bill was always warm and friendly, as time went on our discussions got deeper and I felt we were become friends beyond the client/masseur relationship. While not baring my soul, discussions also had gotten more personal, like what I was feeling, what was frustrating me, family and work challenges. I found myself really looking forward to the massages not just for the relaxation and pain management, but the connection I was having with another human being and a more spiritual connection. And while not ready to admit it to myself, I was getting hot for Bill. Like when I first inquired about setting a massage appointment, I would continue to notice little things about him during each appointment that gave me a feeling that transcended a friendship. One time the sight of his perfectly shaped masculine hands and fingers got me, another time it was seeing his nipples poke out of his shirt and once when I was face down, I saw his strong, hairy feet nicely manicured (but not polished or buffed). Other times it was his voice or the way he breathed when he applied pressure to tight muscles. While I increasingly gazed at his crotch and ass, he never really wore clothes that revealed what was beneath. After about the 3rd or 4th massage, Bill started to make his way into my jackoff fantasies, but I would never dream of acting on them.

After about 2 months of appointments, Bill decided to mix things up a bit and we started on a massage chair instead of the table. Seated in a kneeling position, (shirtless and in my boxer briefs) Bill stood above me, giving him good leverage to dig his fingers and elbows into my shoulders which felt great. The positioning of my body on the chair and his standing above me also provided more opportunities for more parts of his body to touch more parts of mine throughout the session. Several times I clearly felt his cock press against my arm and back – not hard, but substantial enough to be felt. During this session, Bill definitely started to take his questions down a more personal path. He asked more questions about my emotional well-being – what I did for recreation, friendships, relationship satisfaction. As he moved his hands from my shoulders to massaging my scalp, he said he sensed that I was “hungry for connection and touch” based on my response to massage. He said it somewhat matter-of-factly and it just hung in the air. He did not follow-up and I did not respond.

During this palpable silence (at least it felt palpable to me) and still standing behind me, he started to lightly run both sets of fingertips down the back of head, slowly down my neck, out to my shoulders and down the sides of my back. Just below my armpit, he slowly and still just with his fingertips his hands went to my chest and very lightly circled my nipples several times. My internal sensation was electrifying while externally it generated goosebumps at which point Bill simply said, “point made.” He alternated between light touches on my chest and firmly massaging my pecs, still from behind and in the position of a hug from rear. I was clearly breathing heavier and starting to sweat a bit more and it was at this point, that he asked if I’d be uncomfortable if he removed his shirt. Without really waiting for an answer, he removed it, brought his hands back to my chest and slowly moved them to my abs where he dug individual fingers to release my ab muscles. In doing this his chest pressed more tightly into my back – I could feel his chest hair and nipples press and brush across my back. Between the feel of his chest and the change in his breathing I was clearly getting turned on. At this point however, I was still confused as to whether his intentions were anything more than professional. His hands continued down to my quads where he pressed deep as his hands were heading toward my knees (and his chest more tightly pressing against my back) than lightly coming back up the inside of my thighs and back again. He repeated this about six times, creating a back-and-forth rhythm, with each stroke getting closer to where my briefs met my leg.

During this whole sequence the only sound was our breathing until he huskily whispered in my ear that “this feels really good.” At that point he wrapped his hands around my waist, gave me a tighter hug and very lightly began running his fingers over the outline of my penis which was the hardest it had been in a very long time. He did this emitting subtle “mm’s” for what seemed like :15 but actually 2 or 3. At one point he began to cup my balls with one hand and stroke the outline of my cock with the other. These simple movements were giving me an out of body experience. His hands migrated to the top waist band of briefs and slowly went underneath them moving throughout my pretty dense bush of dark pubes. With one hand still circling my bush, the other started circling my short but fat cock, I learned that my pre-cum days were actually not behind me as he swirled his index around the tip of my cut cock, making the entire head of it slightly lubed. His other hand moved from my pubes to my balls – gently squeezing and cupping them – down to my taint where is finger stopped to give a gentle massage. While I was in this increasingly intense, blissful state I realized the position had to be uncomfortable for him, so I said “let’s get more comfortable” as I flipped around and moved into a seated position on the massage chair. Keep in mind, the whole time I was in the chair, my face was in the cushion in the chair and Bill was behind me, so I saw very little – including inability to see Bill without his shirt. I was literally breathless when I first laid eyes on his semi-undressed body. I never thought something that I’d seen thousands of times at the beach, pools, or the gym seem so hot, but the fact that he was there, and it was potentially mine to feel and play with made it sexiest thing I’d ever seen.

At that point, I lifted my ass off the seat and took the bold step (for me) of taking off my dark blue briefs with a rather large wet spot on the front, making myself fully open and vulnerable to Bill. Before he could make a move, I tugged at the waistband of his gym shorts, and he proceeded to pull them down and step out of them. He was a hairier guy than me with a furry chest, stomach, pubes and legs. I leaned in reached around with both hands to grasp his ass and buried my face in his stomach. While not fully erect, Bill’s dick was hard and the perfect size to fit in my mouth. I examined it for a while and asked him to turn around because what I was feeling in my hands was spectacular – two hairy, perfectly shaped firm mounds of man ass. While in his fifties, he had the ass of a 25-year-old. I ran my hands all over it and up and down the crack. He bent over slightly (an invitation?) at which point I saw my first asshole up close and personal and while I never wanted to lick my ex-wife’s, my first instinct was to stick my face in his crack and bury my tongue in his hole. Just as instinct was ready to take over, Bill turned around, got on his knees and immediately went for my cock with his mouth. His hands went up to my chest where he pinched both my nipples while his mouth easily went to the root of my cock, and I could feel the breath from his nose on my pubic hair. He stayed down there for a long time, swirling his tongue around my cock head and going up and down the shaft. I gently caressed his head and ears while he did this. I was literally light-headed from the feeling and told him I didn’t think I could hold back and was really close to which I expected him to take a break or step off my dick, but he double downed and inched his finger to the rim of my ass, circling it a few times before apply pressure at the hole. That was the point of no return for me, and I let loose at least 8 volleys of cum into Bill’s mouth. The sensation of him continue to suck me while I was coming was truly indescribable. His mouth stayed on my penis until it softened in his mouth at which time, he lifted his head up to mine. We passionately kissed while he still had a mouthful of cum (and that we passed it back and forth) despite swearing he’d swallowed. That was a first for me and I found it both hot and intimate.

After our kiss we looked at each other, smiled and I asked if I could return the favor. I admitted that I was not confident in my cocksucking skills, so he talked me through how to do it (which got me hard again) but when he got close to climax, he asked me to finish him off with my hand. I squeezed his furry balls with one hand and aggressively jacked with the other watching him shoot his cum impressively high in the air. I had never seen another guy’s ejaculation up close and personal. I played and sucked on his cock, licking the sperm that continued to drip down his shaft until it started to shrink back to its natural state. Bill got us a washcloth from his bathroom, we wiped up and got dressed, recounting what had just happened. Bill swears he never gets intimate with clients -- especially in his studio. I could tell that after the fact he had concerns about letting himself get carried away.

The next night we met for dinner, and I learned a lot more about Bill that I will save for another story.