A completely true story
I was then about 30, was working for a large corporation, had some back and neck tension common to office workers. I had never had a massage and was intrigued by the thought of getting one from a masseuse in the privacy of her apartment. I avoided Asian massage spas because from what I'd heard they were only in business to provide handjobs. I had nothing against handjobs as I was single and masturbated frequently (still do) but I needed some genuine therapy. I phoned up some ads from masseuses posted in health stores, legitimate professionals who offered therapeutic treatment.
The several masseuses I saw gave a good treatment but were clinical. One masseuse wanted me to keep my briefs on but I insisted on taking them off. She kept a towel over me while I slipped them off. For the record I'm of average looks, light build, uncircumcised so my penis looks even smaller soft but am a respectable six inches hard. The towel stayed on during her massage. If I had been 17 or so I would have popped a boner but as I got older my penis needed a few strokes to become erect although I had no trouble getting hard. I masturbated on getting home.
Typically the masseuse would leave me alone to undress and then slip under a sheet before entering the room. She would massage me exposing only the body part she worked on, always keeping me draped with a towel over my waist. I liked the feeling of being naked under the towel and wished they would dispense with it. I had no intention of doing anything inappropriate, masturbating, but the idea of being naked while the masseuse worked on me had an erotic appeal and I thought a massage professional should be comfortable with nudity.
I called an ad I found in a New Age newspaper and made an appointment for a massage from Regan who did Swedish massage. She buzzed me in to the small studio apartment located downtown that she used for her business. Regan was slender, about 28 or so with an angular face and shoulder length mousy brown hair, no makeup, dressed down in flannel shirt and jeans. She was very polite and told me I could get undressed for my massage. There was no privacy screen for her clients to undress behind so I stripped off in front of Regan who stood facing me a few feet away. Regan maintained a professional attitude and avoided looking directly at my penis. I got on to her table and she proceeded without draping me.
Unlike the masseuses I'd visited Regan first massaged my front then had me turn over so she could do my back. As her massage was therapuetic without being sensual I remained soft throughout. She avoided massaging my butt. Toward the end, as we were getting along I indicated that I wouldn't mind if she paid some attention to my penis. She frowned, replied that she didn't do that kind of massage and I let it go.
The next time I saw Regan the routine was the same and I lay naked on her table throughout. Her medicinal massage lulled me without provoking an erection and I was hoping she would massage my butt which would have instantly done the trick. While she was friendly enough her demeanor was always very correct.
I went back again as I liked her and of course enjoyed the fact that she was ok with nudity. I was getting an erotic buzz being naked in her presence but my penis behaved itself. I didn't want to do anything like manipulating myself to erection as she might have reacted badly as she had not been so happy about my suggesting that she give me a handjob. As she worked on me we chatted as usual about nothing in particular. She was a shy girl which I thought an unlikely personality trait for someone who did massage especially as her clients were naked on her table.
As usual Regan worked my front and then had me turn over. I zoned out as I felt her supple hands knead me till she reached my lower back, then her fingers slipped into my butt crack which was never until now part of her routine. I felt an erotic charge go through me waking up my penis. I parted my thighs so my balls hung loose. I was rewarded with the delicious sensation of Regan's hand cupping my ballsack so I tilted my hips to give her access signaling that she had a green light down there. Regan's hand went up under my balls and grasped my penis which was now a raging boner crammed against my stomach. She murmured was this ok, did I want her to continue? I said yes to both questions. My penis felt like a rocket about to take off as Regan's fingers encircled the shaft. I swiveled around to sit on the edge of the table with my legs apart so she could get a good look.
Now I was flaunting my six inch turgid tower with Regan perched on a chair between my legs. As handjobs weren't part of her program I gave Regan a lesson in how to give one. I told her not to be afraid to fondle my balls, showed her how to effectively stroke the shaft, manipulate the foreskin around the glans, squeeze under the head till it looked like a purple walnut. As she was a pro at handling flesh she quickly got the hang of it caressing my hot rod, tugging my ballsack. Regan applied herself and I erupted in a geyser of milky cum over my stomach. She then went into the bathroom and returned with a warm wet hand towel and cleaned me up. She told me that she never gave this treatment to anyone else and I believed her. I said I appreciated that and made another appointment.
The next time I showed up Regan said nothing to indicate that her handjob had been a one time thing. I stripped off, told her how great it was to be naked with her after a long day at work and directed her attention to my flaccid penis. She didn't hesitate to get her hands on it. I had to urinate so I asked her to accompany me to her bathroom. I showed her how to hold back my foreskin and point my penis like a hose while I pissed which she did. I was really enjoying being a sex object for her.
After our bathroom session I stood in front of Regan and told her how I had masturbated every night thinking of her hands on me. I told her I felt lucky to be intact as a foreskin was a masturbation aid, that I didn't need any lotion like a cut guy would for a jackoff session. I stroked myself to erection as I did this and began to masturbate showing her how an uncircumcised guy does it. I held my balls with my left hand and stroked my penis with the other, pulling the foreskin as far as it would go over the head oozing precum. Regan was all eyes. I didn't go to finish as I wanted her to do that. She had seen a lot of penises as she didn't drape her clients but no doubt I was the first one to give her a masturbation demonstration.
I got on to her table and gave myself over to her firm fingers. Regan gave me the usual therapuetic massage and my penis went soft but now I was anticipating an erotic finish. She didn't disappoint and when I turned over on to my stomach she switched to her sensual routine massaging my butt, my balls, bringing me to erection. She was only too happy to practice her newly acquired skill at giving a handjob. I sat on the edge of her table flaunting my penile pole while Regan went to work. She balked when I suggested oral sex or giving me a massage with herself naked saying that she couldn't trust herself to go any further. I surmised that I had connected with Regan in some way that let her indulge in erotic activity. Regan was undoubtedly a virgin as it was fairly obvious that she had little experience if any in handling a penis. She was really wound tight.
I couldn't get Regan to open up with any sexual revelations. The only time she got visibly upset was when I asked her did she masturbate as I thought by then we had broken the ice, sexually speaking. I apologized saying I hadn't meant to pry. She had confided that she lived outside the city, hung out with her family on weekends. She was obviously no city girl.
When I called her a week later to make another appointment Regan's line was turned off. I never found out why she had suddenly closed up. I wonder where she is today, if she masturbates to the memory of our sessions?