I [40M] had sexy encounter with new massage therapist 50?[F]

I have been to many massage places (from 4/5 star hotels, spa like places in hotels/spa’s all over the world. I have had probably 50 massages in the past 20 so years for 2 years I went regularly for back issues). All very reputable, never any Thai or Asian massage parlors. I typically go to some massage places that offer monthly subscription and you wouldn’t expect to have sexual encounters. It is a typical afternoon, I check in at the front desk tell them all my aliments, then they lead me back to the sitting room. I am futzing around on my phone when my massage therapist (Jen) [not real name], calls me in and directs me to the room, she was stunning. She was about 5’8, really dark African American, B/C cup, athletic build. She was really good looking, initially I thought she was 20, but later I realized she was older. We go to the room and after a quick talk, I am left alone, I strip naked, go in between the sheets on the table. She comes back in and then begins to massage my back. First sign was that she pulled the sheet really low (at the top of my butt), so she knew I was naked.

I never say a word when I am getting a massage. They are doing their job, I am here for the experience. I am always respectful, and say when pressure is too soft or too hard. She doesn’t talk during the whole thing, I barely do. I am skipping ahead… she is massaging my back when she does one side and lets my arm hang on the side of the table. Her leg brushes my hand… (i am thinking that is weird, usually massage therapists keep their distance). I didn’t get the chance to really do anything, so I wait till she does the other side. And again my other arm is draped over the edge of the table, and i slowly brush my fingers against her leg/calf. I am expecting her to walk away so that I don’t touch her. Again she doesn’t move. So I go bolder, and start softly grabbing her calf. And I match her massage movements with my hand on her calf. In my mind, I never thought that this would ever happen to me. I have read some stories here, but never in a million years would I think this would happen to me. My hand was probably on her calf for like 3 minutes, and she doesn’t move that leg, even though she is continuing to massage my shoulders and back like I am not doing anything. Neither of us has said a word. As she places my arm up on top of the table, she guides my hand all the way up to her inner thigh, just below her crotch. I am breathing heavily. I didn’t want to be a creep and just grab her crotch, so i just squeezed her inner thigh and brushed up against her crotch. Then she places my hand on the table, and I am going wild in my head. She quickly massages my legs, and always brushes up against my inner thighs and testicles. I am super hard at this point, and my dick is underneath my body.

Once she was done with my legs, she tells me to flip over. I am still being covered and going on the typical massage like nothing happened. When she gets to massaging my head, shoulders, and pecs, she slowly massages my arms, and guides them to her ass. So I am softly squeezing her ass while she is massaging my chest. I am not squeezing, but i am enjoying the tightness of her yoga pants, and I feel the outline of her underwear. She stands up and lowers the table, and as she is massaging my abdomen her crotch is right in my face. I pull her butt towards my face and she is grinding her pussy in my nose and chin (I am wearing a mask). Then she climbs up on the table and presses both of her hands on either side of my shaft, the sheet is still covering me, and she is doing vertical rubs from abdomen to legs, touching the sides of my shaft, and we are in a 69 position and I am rubbing my chin on her clit. I try to put my hand in her pants, but with her utility belt and tight form fitting yoga pants, I can’t get very far in my laying down position. So for about a minute or two she isn’t giving me a happy ending, but she is rubbing both sides of my cock while she is grinding her pussy in my face. And rubbing her hands up and down my legs and abdomen, touching the sides of my hard cock in the process. I so wanted to pull her pants down and lick her pussy, but her pants were too tight and getting a hold of them was difficult with her pouch with the massage lotion. So I just enjoyed digging my face in her crotch while she slowly rubbed my body while grazing my hard cock.

She slowly climbs down, as I am out stretched trying to keep my hands on her ass above my head. It was an intense couple of minutes. I was just muttering to myself “oh my god” over and over. Just getting over the fact what just happened. And she just massages my scalp and shoulders. I just keep my hands resting on her ass, in somewhat of an uncomfortable position with my arms and hands above my head. She slowly backs away, and I put my hands back. I don’t say anything, she walks to the door saying time is up and get dressed. She writes her website on a separate envelop where she has her own massaging practice. And then fills out the tip envelope and leaves me to get dressed. Before she goes, I tell her that it was my first time ever doing that, and I really enjoyed the massage she gave me. And I never expected anything like that to happen. I tipped her 40% in cash. And paid my bill out front. I will be seeing her next month for another massage. What should I do the next time I see her?

Source: reddit.com/r/gonewildstories/comments/p66o9s/i_40m_had_sexy_encounter_with_new_massage

1 comment

  1. The fact she has her own practice means what she does in her own space can be more sexual. Next time book privately with her and tell her you’re comfortable without the sheet covering you. Good luck!

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