Massaged by a Man for the First Time Ch. 02

It will make sense for you to read the first part of this series. In part-1, I had my first massage from another man. It blew my mind, and my cock.

I went home after that initial massage, and felt quite at unease. A little shamed perhaps, but I remember when I went to bed, I couldn't help get it out of my mind. I found myself masturbating again, thinking of what had happened, and wondering what else I could explore.

During the week, I masturbated a number of times, and couldn't wait for the week to finish so I could make another appointment. I phoned up, and made an appointment for the Saturday.

It seemed to crawl along, but the appointed time came, and I rocked up to my appointment.

Michael greeted me warmly. As I was getting undressed he stayed in the room. He was chatting away, asking if I was happy with everything last time, alluding to the handjob he gave me. Taking off my underpants, my erect penis was in sync with my answer of 'yes, for sure'. At this stage, he too undressed, and he too was rock-hard. Again, I was impressed with his cock. Definitely over 7 inches and thick.

I lay down again on my stomach, and again he started with a lovely massage of my shoulders and back. Before too long, he moved down to my bottom, and gave it an exquisite rub. Nothing was rushed.

He then moved to my left calf, rubbing that before moving up to my thigh, and upper thigh, gently caressing my scrotum and inside of my buttocks. A light graze of my anus, and then a circling of it. He then retreated back down my thigh, and lifted my ankle up, having my heel touch my buttock, before placing it back down, in the corner of the table. He repeated the process with the other leg. Now my legs were spread wide apart.

He climbed up onto the table and placed himself between my legs which were spread wide apart. I could only imagine what view he had.

I could feel his hands on my bottom, one on each cheek, and he spread them even further apart. Then, something I was totally shocked by, I could feel his warm tongue on my anus. I very nearly ejaculated there and then. I couldn't help it - I moaned loudly. Initially I clenched my bum, but then relaxed, and enjoyed the experience. He was good at it -swirling his tongue, around, and in and out.

He then stopped and I could feel the edge of his arms, next to my upper rib cage. I then felt his rock-hard penis moving up and down my crack, and over my anus. I wanted to go the next level. I said "If you have a condom..."

He said, "are you sure". I said "yes absolutely".

He told me that he would "get me ready" so that it doesn't hurt too much.

He got up and got some lube, different to his massage oil, and put some on his finger, and entered me. When he hit my prostate, I was in heaven, though he was really focused on loosening me up. "Okay, I"m going to use 2 fingers now, just relax". A couple of deep breaths and he had 2 fingers in me.

He then went and got his packet of condoms, and stood near my head. He was only semi-hard at this stage, having spent the last 10 minutes or so opening me up. With the cock right near me - it was available for me to suck on. I licked and sucked and seemed to be doing the right thing, because he was fully erect in only a couple of minutes. It seemed so big in my mouth.

He put the condom on, and plenty of lube on. He got me to get off the table, and stand facing it, with one knee up on the table and to lean forward. He had a mirror facing the table, so I could look back, and see my bottom open and facing him. I could see his hard cock ready to fuck me.

He put some lube in my anus, and eased his cock head in. He told me to relax and that he would just put the head in, and we would take it from there. I breathed out, and he put in - it did hurt, and he asked how I was. I said it was pretty sore.

He took it back out, and after a minute, I said let's give it another go. This time, it went it much easier, and after the first 30 seconds or so, started to feel good. He then started to gently fuck me, and after a couple of minutes it started to feel really good. He was hitting my prostate and it felt like a continual high.

I could feel him getting close to orgasm, and to be honest I had been close to coming since early on in the massage. As he was getting close he grabbed my cock, and as he was climaxing, his gentle strokes also sent me over the edge. He withdrew, and then got a small wet towel, and wiped us both down.

He got me back onto the table again, face up this time, and gave me a beautiful head massage, stomach and thighs. He then slowly and exquisitely masturbated me again, and I had an incredible second orgasm.

I went back many times, with many variances on this. Sometimes he fucked me with my bottom at the edge of the table and legs over his shoulders. Sometimes he lay on the floor on his back, and I lowered myself onto him. Sometimes we would put a pillow or two under my hips, which would really open me up, and he would enter me that way.

After about 2 years, and probably 20 trips, the sessions took a new turn, a disciplinary turn. Happy to talk about that more in part 3 if there is interest...