I have a regular massage client. We'll call her Sarah. She is in her late 40's and is sexually frustrated in her marriage. Over the years, she has become quite comfortable, confiding in me her deepest sexual curiosities. She really likes for me to rub her ass around the area where her anus and pussy meet and gets quite a bit of stimulation that way. One day she asked, "Have you ever had anal sex?" "No," I said, "I'm not really into that." She went on to say that she hadn't either, but always wondered what it felt like. I could tell by the way she was talking that she was propositioning me. I know her pretty well. I just said, "Well, you know, I'm a massage … and I get paid for my time." Then she said she'd be willing to pay a little extra. She looked at me with desire and her pussy was beyond wet. If I said no, I might lose a client. So I said plainly, "If you want me to do that to you, I won't charge you extra THIS TIME, but you're going to have to suck my dick." "With pleasure!", she said. She got off the table, got on her knees and went to town, giving me a very sloppy BJ with a lot of suction. I felt myself getting sensitive and had her get back on the table. Her ass was a little oily already from the massage oil, but I put another thick coat on my hands giving her more stimulation and lubing her asshole and my cock. As I went inside, she said, "Ouch! Go slow!" I gave her long slow strokes, pulling completely out every few seconds and rubbing her clit. "I feel close to cumming", I said. "Fuck me harder!" I went all the way in deep and put a lot of muscle in it, stroking until I was at climax. Then I pulled out and came all over her pussy and ass. "How was it?", I asked. "It was great! A little painful though." "Well, I'm glad I was able to help you with your fantasy. Next time tell me in advance if that's what you want because you'll have to pay double." "What if I suck your cock?" "Well, we can probably work something out." 😉

Two weeks after our first appointment, she booked again. Based on our previous session, I knew that she might need a little extra attention. She was pretty hot and bothered the time before, so I wanted to make sure she left satisfied this time. Our appointment began as before and we had a much more free flowing conversation this time, and it seemed she was more open. I said, "If there is any part of your body that needs special attention, let me know and don't be shy. As she lied on her stomach and I gently stroked her back with oil, and inched my way down to her ass and thighs, ever so slightly opening her legs and pussy. When it was time for her to turn over, I spent extra time rubbing her breasts and nipples. As I made my way down her belly, I said, "If anything makes you uncomfortable let me know." I could tell she was getting wet, so I rubbed her inner thighs, making sure to passively stroke her pussy here and there to tease it. This time I noticed she was shaved, so I just went for her clit, gently massaging in a circular motion. She was getting wetter and wetter, and her pussy was hot to the touch and I watched as she made some pretty intense faces. Then something like an inner scream came forth, her leg was shaking and she was cumming hard. I gently wiped her to clean up the mess, finished my massage, thanked her. After she left, I went back in to tidy the room and noticed she had left a big tip.

She had booked a massage online. We had never met, but she was referred to me by a friend. I showed her to the massage room and left so she could get undressed. She was in her mid-30's, short brown hair. She seemed very self conscious but had a cute, shy smile. I came back in, struck up a conversation to make her comfortable and proceeded to stroke her back. As I made my way to her thighs she tensed up and quivered. "Is everything okay", I asked. She assured me it was, but her quiver turned into a squirm. Lying on her belly she spread her legs and I began to smell her sweet wet hairy pussy. She seemed to be inviting me to rub it. I inched closer to her snatch from behind rubbing her ass and thighs. She began to moan. "Turn over please", I said as a patted her ass. She turned over without saying a word, but she looked at me almost in desperation. I spent some time rubbing her breasts and made my way to her stomach. She opened her legs again. I brushed over her bush ever so slightly and by this time even her pubes were wet. "Time's up", I said. The hour was over, and I couldn't expect to get her off before my next appointment, and we hadn't agreed on that. I could tell she was disappointed, but she knows how to get in touch with me. Maybe next time I will leave her satisfied.