This happened last month while traveling on business.
If you've ever heard of a 'massage with a happy ending' it's usually a sensual massage where the woman gives you a hand job at the end. For me it's the perfect combination of relaxation and safe sex because there's no intercourse.
I had searched an online site and found an attractive blonde in Chicago (where my business meeting would be) who made it clear that her sessions are sensual with a happy ending, nothing more. Through a couple of emails we established an evening to meet at my downtown Chicago hotel. I told her I would order wine and we'd chat in my room before the massage.
I was pretty aroused that evening. She called to say she was in the lobby and on her way up, my heart pounding, cock twitching. The hotel is so large, she actually got lost on my floor and had to call one more time so I opened my door to wave to her. She was a stunning tall blonde with long legs and a great smile.
We drank our wine and made small talk. I'm 46 and I am guessing she was in her late 20s. This was going to be interesting, I kept thinking. I wasn't expecting a girl to be so innocent. I finally suggested we start the massage and she went to the bathroom to change while I turned down the covers of the bed. I remained dressed not sure if I was supposed to strip down (again, I have done much of this) and when she came out of the bathroom, she was topless with a g-string. What a cute Goddess. OMG, I was in heaven staring at a topless angel.
She smiled and said, 'Oh you're still in your clothes..' but I removed my shirt and jeans quick enough. My cock semi-hard.
I laid face down for a great massage with warming gels. She took her time caressing my back, butt and legs. At times I wanted her to finger my ass (something I sometimes do while masturbating) so I arched my butt while her hand glided through my crack, what a tease! She eventually asked me to turn over and I laid back as she sat on the bed with me and carefully studied my cock.
She lifted it gently, appreciating it's full hardness, applying warming gel and slowly stroking it. Knowing she must do a lot of massages I asked her opinion. 'What do you think of this cock?' Smiling she said, 'It's definately big and thick. Are you always this hard?' I said usually I am.
The handjob went on for as long as I could hold on without cumming. I rode the waves of pleasure while I watched her. She was in no hurry. I asked if I could touch her breasts and she agreed. I borrowed some of her warming gel and rubbed her perky tits wanting badly to suck them, but I sensed that would not be allowed.
A few times I took the pre-cum from my cock and licked it. This amazed her and she laughed, 'Oh, that's kinky!' She was young and didn't know that some men like me get turned on by our own cum.
I asked her to add warming gel to my anus while she stroked by cock. Again, she was surprised. (There's so much I could teach her about men and masturbation.) She did it lightly but didn't finger me...which was fine and I licked more of my pre-cum wanting so badly to explode.
She asked if I was a big cummer. She said some men shoot large amounts while others only had small spurts of cum. For me this varies by how much edging I do and when my last orgasm had been. I told her that it would probably be a big load because we were taking our time and that I was obviously aroused by her technique.
I then laid back and told her, 'I want to cum now.' And she brought more focused attention to her stroking. What a lovely sight to have this Goddess with flowing blonde locks of hair and perky tits, stroking me.
Her eyes went from my cock to my eyes. She was reading my pleasure and anticipating my orgasm. I could tell she was trying to figure out if fast or slow was my preference, faster was my request and I suddenly burst two good shots of cum out of my cockhead down to my balls.
It wasn't my biggest load, but a satisfying one for sure. I caught my breath and she asked if I wanted a warm towel to clean up. I said I was in no hurry. I liked seeing my cum dripping down my legs and the feel of it on my balls. I wanted to admire the fruits of her great work.
I then grabbed a small hand towel and slowly cleaned my cock. We chatted as we got dressed and I thanked her for a very sensual evening. I said I would contact her again on a future trip and she said she'd look forward to it.
As I mentioned earlier, I've done this only a few times. I've never done a repeat session because I either travel too much or that maybe variety is half the thrill. However, I would probably repeat with this lovely young lady because of her casual pace (no rush) and her curiosity toward my cock.
That night, while lying in bed with the smell of her warming gels on my sheets I stroked my cock and came hard onto my chest and slowly licked my cum off the tips of my fingers and then fell asleep.