First Time I Bottomed

About 20 years ago I was freshly separated from the Marine Corps and was figuring things out. I was 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 him 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 suppose he was an attractive guy and he had pics of his wife and kids all over. He was middle-aged, white, Dad bod.

The massage itself was fantastic, he knew what he was doing and he had the right touch. 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 did the massage in old basketball shorts and a tshirt, but then he took his shirt saying that he didn’t want to stain it from 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 erection 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 erection. He did a fantastic job doing my back,

He accidentally squirted too much oil on my lowerback butt area, and we had to discard the towel over my butt. 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 balls and butthole. I was so ashamed for enjoying his finger circle my butthole, 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 down my legs, doing my feet in a way I never knew I needed. He then had me flip over fully exposing my erection, 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 nipples being played with. It was so surreal having his erection 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 cock. Slowly circling in and teasing my balls and shaft with occasional touches. As he did this he brushed his cock 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 cock 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 cock 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 cock 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 cock in my mouth. While I contemplated the sensation and taste of a cock in my mouth, he started dipping his finger into my butthole. My body betrayed me by lifting my hips off the table against his finger. 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 dick 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 cock. It was uncomfortable but pleasant, and before long his balls were touching mine. I remember him saying “such a good boy, take daddies cock” as he started fucking me. He was only nice for about a minute, then he applied more lube and truly started to fuck me. It was so humiliating and so amazing at the same time. I mean I’m a fucking Marine who has deployed twice to war with an infantry battalion and here I was face down ass up enjoying getting my ass fucked, 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 fucked 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 ass, calling me a “faggot slut” as he filled the condom with cum.

We eventually met again once I came to terms with what happened.