I was traveling back to what I used to call home for a reunion of sorts with the guys I played sports with in my 20’s and 30’s. Here I was on a cool, rainy Sunday night before returning home, tired but still with lots of vim and vigor – so as an average middle ages white man, I was horny as hell.

I wandered over to the computer after working out in the hotel gym in t-shirt and loose fitting shorts. I thought I would place an ad on Craigslist to see if I might meet up with someone that night – or possibly to my favorite web-site a bit later for some good material to get myself off – assuming I would receive no positive responses. For an older man I was still in fairly good shape – late 40’s with toned legs but certainly not the toned athlete of years past. I placed my ad for providing a free massage for a woman hoping someone might be interested in receiving some TLC from my learned hands and perhaps allow me to please her orally. If I was truly lucky she’d let me massage myself to orgasm in front of her (I have a fantasy for that humiliation which I rarely get the opportunity to participate in).

After a couple hours off and on browsing posted ads myself I found one that seemed a bit interesting to respond to – a woman looking for someone to play with her nipples and to please her – not looking to reciprocate. Just a simple ad with no age, etc, just mentioning playing with her nipples and not being able to host. I wrote a simple response back describing myself with a g-rated picture, offering my “services” to massage her back, body and certainly her nipples. I explained that I had placed an ad earlier for a free massage from PG to a sensual X rated massage including her nipples and pussy until she was fully relaxed and pleased. I offered oral as well, if she wanted and sent a copy of my ad. This included noting that I would like to please myself in front of a lady as well.

Surprisingly, since there are dozens or hundreds of guys who probably answer ads like this, I received a nice reply back. She told me she was a nice, curvy woman who enjoys being pleased but rarely has had anyone take the time to spend time on her needs. She also mentioned that she’d love to watch a guy do himself. Although she hadn’t seen it before it was one of her things she’s thought about in the past, especially if the guy would cum on her breasts. She also included a picture of her, topless. She had some wonderfully large and firm looking breasts with small, pert nipples. I was hard immediately and quickly fumbled with the mouse and keyboard to supply a response.

I wrote back that I’d really enjoy giving her a show and I’d love to cum on her breasts. I’d never had the chance to do that before, although one time I did cum on a girlfriends hairy bush after pulling out – it looked so good that I even wanted to taste it (since I love giving oral sex more than anything). I mentioned it was part of my “bi-sexual” / fantasy side – along with taking a strap-on, etc.

Although about 30 minutes – her reply seemed like an eternity. Not only did that turn her on even more she wanted to know if I’d really cum on her breasts, rub it all over her breasts and still lick it up. She even noted she had a toy or two she’d like to share with a guy – assuming she found someone adventurous enough to play with in this manner. Before I knew it she asked where I was and could we meet tonight still (it was getting very late).

Before I knew it she told me she was on my way and would meet me in the hotel lobby in an hour. I rapidly took another shower as I’d been rubbing myself for well over an hour and knew it could probably use it.

I knew her when she entered the lobby, although cold and damp out and she was wearing an overcoat her look was between apprehension and desire. She was much taller than I thought – about 5 inches shorter than my 5’11” frame, black lightly wavy hair damp from the shower and like me, thinking we are average but that’s more our feeling about ourselves than how we are actually perceived.