First time I bottomed

About 20 years ago I was freshly separated from the Marine Corps and was figuring things out. I was kinda strapped for cash but really needed a massage. So I went on Craigslist and found an ad for a free massage by someone going to massage school or something. I messaged the guy and set up a session at his place. I’ve had a handful of experiences with other men but nothing really substantial, just a kid experimenting. I was immediately attracted to the guy but put it out of my mind as we were surrounded by pics of his wife and kids & never got a vibe other than professionalism. Although to be fair I am on the high functioning end of the spectrum and it’s normal for me to be oblivious of social subtexts. For context he was in his late 40’s, white, salt & pepper hair, & a dad bod.

The massage itself was fantastic, he knew what he was doing and he had the right touch of firm but not painful. I had to stop myself from making some very unmasculine sounds as he rubbed me .
It started out very professionally, but slowly he pushed the boundaries. He came out to do the massage and old basketball shorts and a tshirt, but then he took his shirt sayIng that he didn’t want to stain it front the oil. For the same reason, he wore old ratty basketball shorts, ones shorter than I would’ve wore.

He didn’t have a traditional massage table, so I didn’t have one of those face holes to put my face in. Due to that I was eye level with his ** that was very visibly growing in this light gray shorts. so the whole time he was massaging my back and shoulders. I was trying very hard not to stare at his **. Then he moved down lower and started doing my lower back, moving my towel down with his fingertips and catching my ** crack. By the time he finished with my lower back, my towel was more than halfway down my **. That’s when he switched gears and started doing my legs. He started with my thighs with his fingers traveling further and further north until he was brushing against my ** with his ** tips. At this point, I already had a nice chub going, and that quickly escalated to a steel hard **.
He accidentally squirted too much oil on my lowerback ** area, and we had to discard the towel over my **. He offered to rub it in and it felt so good and so shameful at the same time. He primarily focused on my cheeks, but he definitely put some focus on my ** and **. I was so ashamed for enjoying his ** circle my **, I just laid there and silently let him do it. In hindsight it is so obvious that it was on purpose but at the time I was oblivious.

After he worked away the oil, he just kept moving along as if nothing happened. Moving further down my legs, doing my feet in a way I never knew I needed. He then had me flip over fully exposing my **, But he acted like it didn’t exist and started working on my shoulders and chest. This is when I discovered that I do in fact enjoy my ** being played with. It was so surreal having his ** inches away from my face and mine angrily pointing straight to the sky, and neither of us acknowledged either one of them. We continued on this way, with him giving the best massage of my life and the both of us pretending that nothing sexual is going on.

When the massage was over, he moved aback up to my **. Slowly circling in and teasing my ** and shaft with occasional touches. As he did this he brushed his ** up against my hand, and I pushed back. Apparently my direct touch was what he was waiting for, as he pulled his waistband down and put his ** in my hand. It was a little smaller than mine which I was thankful for, as it would’ve been much scarier if he was as big and as thick as I am.

While I touched his ** he stroked me a bit, but with very frustrating light touches. He told me to roll over on my stomach, which I did without thinking. I guess I was in a bit of a trance and just did what I was told. Maybe I was always submissive or maybe it was conditioning left over form boot camp or maybe it’s both. The point is I rolled over and let him push his ** in my mouth without a single word or protest. It was like one minute I was getting a massage and then before I knew it, I had a strangers ** in my mouth. While I contemplated the sensation and taste of a ** in my mouth, he started dipping his ** into my **. My body betrayed me by lifting my hips off the table against his **. I even enjoyed it when he called me a “good boy”. I got a bit anxious when he asked if I was still a virgin.

I distinctly remember making a whining noise when he pulled his ** out of my mouth. Again I said nothing, even as I watched him roll a condom on and get behind me on the table. He rubbed my lower back and told me relax as he pushed in his **. It was uncomfortable but pleasant, and before long his ** were touching mine. I remember him saying “such a good boy, take daddies **” as he started ** me. He was only nice for about a minute, then he applied more lube and truly started to ** me. It was so humiliating and so amazing at the same time. I mean I’m a ** Marine who has deployed twice to war with an infantry battalion and here I was face down ** up enjoying getting my ** **, making girly noises , & calling a stranger daddy as calls me a good little boy.

I cannot believe how much it turned me on to be spanked and ** by this older stranger. He reached around and jerked me off onto the table, which was probably the biggest load I’ve ever shot. Then he bottomed out in my **, calling me a “** **” as he filled the condom with **.

After that the tension died away and I quickly got out of there. Post but clarity quickly became shame. He reached out to me a few times but it was another year or two before I worked up the courage to meet again.