By age 20, I hadnt done anything too adventurous. I was no stranger to sex, but stuck with the basics up until then. Had my share of cute girls, lotta fun, but was feeling the boredom I know now that Im quite prone to.
Id browsed the casual encounters section of craigslist for a while just to check out photos and posts and fantasize about doing something crazy Id never really do. One thing that really caught my interest was sensual massages. It felt like a cool way to ease into some stranger sexual territory. People get massages all the time. This just happened to have a bit more fun at the end.
I decided I was gonna answer one of the massage posts. I found one from a woman that seemed to be more on the spiritual hippie side rather than the raunchy dirty side, if that makes sense. From her post it seemed like she was really into the tantric aspect of erotic massages rather than just saying come get a massage. Ill jerk you off after! Which I appreciated in a weird way.
So I answered the ad and set a time to go see her. I parked a block away from her apartment and sat in the car for a few minutes, getting my head right. I didnt realize how nervous Id be. I was almost shivering from excitement and nervousness and some dumb paranoia that someone I knew would find out what I was doing.
She answered the door and said Hi! warmly and gave me a hug, which was nice. She made an effort to minimize awkwardness. Id put her in her mid to late 40s. She was very fit and though still very pretty, clearly was a knockout in her younger years. Nice dark curly hair and beautiful eyes. She gave me a nice view of her fit ass as I followed her a few flights up to her apartment.
We got in and she offered me water and made some small talk. Cant stress how nice of a person she was. I wasnt there to meet nice people, but any experience in life is enhanced when its with someone cool. Finally she said, well, we ready?
I followed her through her bedroom, into the next room where she had a massage table set up and she told me to take my clothes off. Like a dork, even though I knew the answer, I said um so, everything? I think you just always wanna make 100% sure youre SUPPOSED to have your dick out in any situation. Its better than whipping it out and having her say oh uhh...not yet. Anyway, I took off my shoes, socks, shirt, jeans, and then took a quick pause when I was down to my boxers. I watched as she undressed down to just a thong, revealing her tight, gorgeous body, probably the result of lots of yoga and whatnot.
I pushed down my boxers and was completely naked. This alone turned me on like I never expected. The feeling of being naked in a total strangers house got me semi hard. Its to this day one of the hottest things Ive experienced. I laid face down on the table as she put on some psychedelic sounding chill sitar music, got some organic (probably) massage cream and went to work on me. Sexual stuff aside, she was a great masseuse. Gentle but firm hands, took her time on each part of my body. Id never gotten a professional massage before. I was loving it.
I got turned on again when her hands would slide over my ass. Then, she got up on the table and sort of laid down on top of me and slid her tits down my back. What an amazing feeling that was. If a girl asked me randomly hey want me to slide my tits down your back? Id say no thanks Im good. For some reason though, its incredibly hot, at least during a massage. She went up and down my body like this a few times and then got back up. As she walked back around to my upper back, I slowly ran my hand up her thigh and even more slowly, palmed her ass. I wanted to make sure it was cool with her, and it was. I caressed it and squeezed it. Im powerless against a nice ass, and this was a great ass for a woman of any age. Finally she said very gently ok, turn over.
She worked on my upper body and legs as I continued to play with her firm ass. Now that I was on my back and my dick had some breathing room, I got rock hard immediately. She ran her hands close to my dick over and over, getting close but never touching it. She knew how to build anticipation. I, who live with it every day, was even impressed with how nice my dick looked. It was the hardest its ever been.
After what felt like an eternity of waiting, she gently wrapped her fist around my insanely hard cock. I almost came just from the release of her touching it after her teasing it for so long. It was an amazing feeling. She slowly jerked it up and down, taking her time, and massaging my balls with her other hand as she looked adoringly at it. It didnt seem like work to her. She genuinely seemed to enjoy it. That couldve just been her being very good at her work. Didnt matter to me.
As I played with her ass, I got braver and slid my hand around to massage her pussy. She immediately shot me a look, not angry, just a sort of youre bad smile. I replied with a is this ok? look and she just went right back to staring at my cock and gripped it a little tighter. I took that as a green light and gently rubbed her pussy through her thong. She let out a sigh of enjoyment, closed her eyes, and tilted her head back. Again, that almost made me cum. To see her getting turned on while giving me the best handjob Ive ever had was so fucking sexy I could hardly believe it was real.
We continued like that for a while. She jerked me off and I massaged her pussy as I felt her panties getting wetter. Suddenly, she moved a little closer, took her hand off my dick momentarily and looked me seductively in the eye, and pulled her panties down. Oh my god. This was not happening. But it was.
She laid down opposite me on the table so that our heads were at opposite ends, and went back to jerking me off as I played with her clit and fingered her. She was quiet, but that made it all the more hot when she let out little moans here and there.
We kept going and getting more into it. I knew she was close when she grabbed my arm tight and stopped jerking me off. She came, moaning a little louder and looking up at the ceiling. She took my hand and put it on her chest. I massaged her tits as she came. She quickly got back to business. She stood back up and jerked me off with even more love this time. It didnt take long then. I came, probably about, 30 seconds after she did, and shot harder than I ever have, easily reaching past my own chest.
It was so fucking amazing and blissful I had to just lie there for a few seconds closing my eyes and catching my breath. She got me some wet towels and said that was fun.
Id love to tell you I fucked her, because I certainly wanted to, but this is a 100% true story. To this day, one of the best sexual experiences of my life. I walked back to my car, weak at the knees, feeling a bit like a weirdo on the drive home. It was the first out of the ordinary sexual thing Ive done, and Ive done more since then. And maybe I am a bit strange, but it beats the shit out of being bored.
shhot