I've been thinking about sharing this for a while. I've never told anyone this.
I was in my mid 20's, and had never gotten a full body massage before. One day at work they had a massage therapist come into the office to do free 20 minute shoulder massages. Of course, she passed out her business card. So eventually I called, made an appointment, and started seeing her periodically.
The first massage I left my underwear on, since I really didn't know how the draping worked. I was still kinda young and awkward, and actually kinda innocent in a way. After seeing how that I was always covered, I went naked from that point on.
She must have been in her mid 30's. She was a bit on the heavy/big boned side, and not what I would consider that attractive. But she was very friendly and I felt very comfortable with her. And she was a lesbian whose girlfriend I would sometimes see coming or going.
She was a very good and strong massage therapist. I always had huge knots in my neck and shoulders from all the work on the computer, and she would absolutely pound them out. She worked out of her apartment which was fairly close to the downtown area. I got to be pretty good friends with her, and we would talk about a lot of different stuff (at least during the times I was awake). She was very professional. Until the last massage.
She was moving away. I think it was to Seattle, but I don't remember. So I had one last massage with her. Everything started off normal, and I dozed off a few times as usual. Roughly half way through she has me turn over, puts a little blindfold thing to cover my eyes, and does my front (chest, arms, thighs, and neck/head area). Then she whispers to me "hey, since this is the last time, I'm going to try something a little different, ok? It's called a ------ massage. If you want me to stop, let me know."
I don't remember exactly what kind of massage it was that she said, but in retrospect, she might have said lingam massage. Or maybe she said tantric. Of course, I said "ok" while in my half-asleep relaxed stupor.
So she goes back to my feet, and works her way up my legs, and the next thing I know her hand brushes against my penis, and I gasp. As she began to massage my shaft and testicles, she whispers something like "is this okay?" to which I simply mutter "uh-huh". As she kept working it, I was trying my hardest not to moan or yell, because I was afraid somebody outside would hear. She reminded me to keep breathing. As I felt the climax coming (which seemed like an eternity), she told me to hold it as long as I could, and when I was about to explode (which again, seemed like an eternity), she told me it was okay to "let it out", which I did.
As I was lying there, she whispers to me "You're my last tonight. There's no one else coming. So take as long as you need to. Seriously." I then fell asleep for what might have been half and hour. I woke up covered with the sheet, and cleaned up (no semen or anything). I dressed and came out of the room, where she was sitting with a glass of water. We talked a little about what had just happened, and she said that she really liked me as both a friend and a customer, and hoped that she didn't freak me out. Which she didn't. Well she did, a little, I guess. I did ask her if that was a "legit" massage style and she said it was, as opposed to a handjob. Not that I would have been able to tell the difference.
She later moved away, and I never saw her again. This was in the early days of the internet so there was no exchange of e-mail addresses or anything.
And that's my story. Although I've had massages over the years, I've never had anything like this happen to me again. Well, my girlfriend became a massage therapist while we were dating, but that's doesn't really count, because that was always an automatic happy ending.
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