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40 [M4F] #SanFrancisco - [Success] - Erotic [m]assage and more for the pillow princess - Part 1
Author Summary
captjack510 is a male age 40 looking for a female in SUCCESS
Post Body

In recounting a recent experience, I realized I wrote a novel. If you want to get to the massage, fast forward to below. If you want to get to the sex, go straight to part 2.

She had a great experience and is willing to be a referral in lieu of a 5-star Yelp review.

-------------------------------

We had messaged back and forth a few times. Her, naturally cautious of responding to a random online ad. Me, trying to prove I'm not a psycho murder but also trying to determine whether I was being catfished or not.

She was going through a good amount of stress in her life and was looking for a massage. But she also wanted to be a "pillow princess." This would give her the release she wanted.

The reality is that she had vaginismus and she was deprived in her relationship. The full story is incredibly complex but the story is a common one: sexual unfulfillment, resentment and a desire to live out a fantasy.

We talked about visiting a spa together, one that had private rooms. One of her erotic fantasies was for someone to go down on her in a sauna. That also was a desire of mine. We decided that it might be best to meet for coffee first to do a vibe check. I just thought it might be odd to jump straight into a naked spa meeting someone for the first time.

Soon after, things came to a head and she wanted to meet at a hotel for a legit massage and more if I found her attractive. She just wanted release. We had exchanged pics earlier and found mutual attraction. But the reality of people is always a bit different than their pictures.

I picked a hotel in between, but closer to her. I trekked over with a bit of nervous energy that goes into first time, potentially intimate meets. I tried to listen to some music in the car to distract me. My mind wandered -- first into exciting thoughts but then into farfetched thoughts. What if this was some ploy to rob me? Even as a man, one has to be careful. You see sketch ads all the time on Reddit.

I pulled into the hotel. It certainly wasn't the best hotel I've stayed it. Options were limited in the cities between us and those that had daytime use. From the outside, it would certainly do for a few-hours tryst.

Checking in felt like it took ages. I wondered what people checked into day-use hotels -- I'm guessing people like me. I wondered if it was written all over my face why I needed a hotel for just the afternoon. The front desk people made friendly chatter and, after an eternity, I got my key cards.

I entered the room and despite the nondescript exterior, the interior was new, clean and more fashionable, at least compared to the exterior. It wasn't the Fairmont but it would do the job.

I came prepared. Water, music, massage oil. Check. Spotify playlist, check. As I started going over everything she messaged me that was there. Already?! She had just messaged me that she was on her way. Go time.

I came out to the lobby to meet her for that moment where everyone's holding their breath, just in the slightest. I leaned in, peeked over and gave an awkward grin and a wave. She wore a mask -- she mentioned that she might wear a mask. I joked on whether she was going to come in a full-on face mask like the one from scream or a Guy Faux mask. And in that split second I wondered if I was not going to see half her face during this whole encounter. But as soon as she got up and took off the mask, I was relieved to see a nervous smile that went along with her beautiful eyes and face. She wore baggy black clothes -- a black hoodie and loose pants.

I walked her to the room and we sat on opposite queen beds facing each other. Since we didn't have that introductory coffee, I thought we should at least start with a bit of idle chatter just to let the nerves settle and get a feel for each other in face-to-face conversation. All green lights from here. We talked a little bit about what was stressing her and work -- enough to break the ice. But I didn't want the stressful topics to make their way back into this sanctuary so I gently moved things forward.

********************* MASSAGE STARTS HERE *******************\*

She went to shower while I prepped the room. Dark blinds closed, soft lights on, pillow for her head and a thin sheet to provide some modesty, at least to start. I put on a relaxing playlist, and changed into something more comfortable so that I could work her body (soft cotton shorts, tank top).

She came out with her hair up and a towel around her. We both acted as if this were a professional massage as she quickly surveyed the small changes I had made to the room and nodded in approval. I guided her to the bed and she awkwardly tried to lay down on her stomach while undoing her towel and pulling the sheet over her. I helped her by draping the sheet over her first and then pulling the towel away.

I should say some more specifics about how she looked. She stood at 5'5", asian, medium length hair, big beautiful eyes, nice smile and a face that could be both cute and sexy depending on her mood. She's in her early 30's with a medium build with a sexy hourglass figure, small upper torso and beautiful-shaped lower torso.

Even though we had spoken naughty things to each other over chat, there's a certain amount of modesty that comes with seeing someone naked for the first time. It's so revealing and vulnerable.

I put some massage oil on my hands and made long strides down her back. She began to settle into comfort, remarking at the pleasant scent of lavender. With each stroke down her back, she seemed to ease more and more into calm. She laid there, eyes closed, a small smile forming at the ends of her mouth.

I had made sure to focus on her shoulders and upper back where she said she was the most tense, using my hands first, then fists and forearm. I had remembered a joke she made in our chat about how she had met another guy for a massage previously and how she disliked his hairy arms. Thankfully, my forearms are pretty bare.

I made sure to spend ample time giving her a real massage where she needed it most. I eased into more pressure and she had made a previous remark on wanting deeper work. She laid with her head at the end of the bed so I could use my weight on her. I asked her how she was doing and she said she felt great. At times we made a little friendly banter here and there but I kept the conversation short as I could feel that she really just wanted to experience the moment.

As I worked my way down, I moved the sheet down and my hands had reached her lower back and waist. As the sheets ruffled, I wondered what kinds of panties she had worn for me. She had previously joked that she had nothing cute and had on basic black panties with a bit of lace. It still was nice to see on her, peeking out behind the sheet.

I adjusted the sheet so I could work on her legs and she could maintain a bit of coverage on her upper torso and behind. Although we both knew where we wanted to go, I was content with taking my time and giving her a full body massage, first and foremost.

She had legs that clearly had seen the gym. I made long, strokes working her muscles starting with her thighs and making my way down to her calves. I worked both sides. All the while the bottom edge of her luscious ass peeking out from the edge of the sheet, cupped by her black panties.

Read part 2

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Profile updated: 5 days ago
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SanFrancisco

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a male
Age
40
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a female
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Posted
9 months ago