I’ve always been shy. I’ve been afraid to try new experiences. And I’m gay, through and through. I knew in middle school when I’d look at the other boys in gym class. I always wished for open showers. I heard some schools had them, but in ours, each shower was a separate stall. When I realized how much I wanted to see the other guys, and didn’t care to see girls naked, I knew.
I came out to my father first. He shocked me when said, “I know.” I guess to him it had been obvious the way I looked at boys vs girls. Then I came out to my mother. she said, “I know.” Geez!
I’ve had a lot of sex with guys, but never have I had a real relationship. I mean, it’s never been like sharing an apartment with a guy. I long for that, but it simply hasn’t happened yet. Or, maybe I don’t long for it. I believe I’m keeping everyone at arms length. I think I value my independence. Anyway…
So by profession I’m a butler. My first client was very kind but very old gentleman who had done well in real estate. I was with him for six years. Our relationship was very ‘correct.’ I was his butler. That’s all. He died. I cried. I had to move on.
It turns out in this day and age, it’s hard to find work as a butler in the traditional sense. I had to expand my horizons and so I started calling myself a ‘personal assistant.’ That’s not really what I want. I like setting tables, setting out clothing, cleaning and polishing, arranging the home – you know, butlery things. A personal assistant is more about setting appointments, buying plane tickets, running errands. Still, that’s what I had to do to find work.
I got a call from the mayor who had known my old client, and had seen me at work. She wanted to interview me. I had never worked for a woman. The thought had never even crossed my mind. Normally, I would not have even considered it, but I was cutting into my savings account. I had to find work soon.
She hired me. As women go, she wasn’t bad-looking. Slim, tanned, short attractive curly hair, outgoing personality, and coincidentally, the same age as me. To my delight, even though she referred to me as her ‘personal assistant,’ I was really more her butler. I lived in a room of her house, and worked the evening hours. I did not follow her to work and have to do office things.
At home, she was the perfect lady, and of course I was the perfect gentleman. I served her well, and she expressed her appreciation, never yelling at me or being a jerk in any way. The only thing that concerned me is that sometimes she got quite personal, asking about my life, telling me about hers, as if we were supposed to be old friends or something.
One evening, she came home with a sore shoulder. It seems she had met an influential business man for tennis that afternoon, and she hasn’t played tennis in a while. I saw her favoring that shoulder, so naturally, I offered to massage it. Immediately regretting the offer. Too personal, especially since she was, well, female.
Unfortunately, she accepted. She told me to unfold the massage table that had been in the closet since before my first day of work. I set it up, and turned around, seeing Marjorie standing there topless, rubbing her shoulder with her opposite hand. Topless! She acted as if it was a normal situation.
One thing butlers do is keep their cool in all situations, so I tried to act as undisturbed as possible. She climbed on the table, and I went to work on her shoulder.
It wasn’t horrible. I kneaded for a while, she said nothing but “Ummm” a couple of times, and that was that.
A week later, the shoulder was hurting her again. The situation repeated itself. I got the table out, she got topless and hopped on. Only this time, when I thought I was about done, she rolled over, asking me whether I could continue the massage from this direction.
I tried not to stare at her tits. I don’t think I found them attractive, but my eyes kept going back to them, especially her large nipples. As I was rubbing her shoulders, both shoulders, and her neck, she said one word, “Lower.” I found myself rubbing the softer tissue at the top of her breasts. She said “Ummm” again.
“Larry, I know this is a lot to ask, but can you go lower? My breasts feel a kind of itch inside, and I think massaging would settle that.”
She was asking me to massage her breasts. Well, another thing butlers are trained to do is to understand their clients will have their own little private eccentricities, and we are supposed to accommodate to a reasonable extent. Was this unreasonable? I decided it wasn’t.
So, I started massaging her breasts. It was the first time I had touched a woman there. I was very delicate. She kept telling me to “really get in there,” to press harder. I mean, I wasn’t pressing very hard, but I had been under the impression breasts are super-sensitive for some reason.
You might wonder if it was doing anything for me. It wasn’t. There was no stirring in my pants or anything.
A week later, her shoulder was fine, but she told me the insides of her breasts were itching again. Somehow I doubted that, but I knew what she wanted. For some reason, I was happy to comply. Maybe it was the naughtiness of the situation.
I set up the table and when I was done, I was totally shocked to see Marjorie was standing there totally naked. Not a stitch on her! I was quite uncomfortable with the situation. As she got on the table, I went to get a sheet or a towel or something to cover her ‘down there.’ As I turned to go, she said, “Larry, don’t bother, I’m fine.”
“But, Marjorie…”
“No, it’s OK, really. As my butler, you’re bound to see me naked at times.”
That was interesting. For the first time, she had referred to me as ‘her butler,’ not her PA. That was pleasing to me. I hated being called a personal assistant, and loved being a butler.
Frankly, I didn’t like seeing her naked. It wasn’t right. But what could I do? And, was it really weird, after all? Maybe I was making too much of it.
So, I massaged her ‘itchy’ breasts. Then she asked whether I could massage her feet and her legs. I did so reluctantly. I really didn’t like touching female feet and legs.
A couple of times my eyes wandered to her crotch. I could barely make out the slit among her hair down there. I found it interesting, but not sexy in any way. After a while, she rolled over, and I massaged the back of her legs. On my own, without her asking, I started rubbing her ass cheeks. I don’t know why, but I figured she’d enjoy that. I tried to imagine that it was the ass of a small, smooth young man. I was rewarded with a big “Ummmm,” so I kept going. At one point, my hands spread her ass cheeks apart a little bit, and I got a glimpse of her puckered asshole. It seemed smaller than a man’s and more clearly defined.
That evening in bed, I jerked off as I usually do, but couldn’t get the vision of her anus out of my mind. I came quickly and big time. Weird, eh?
Over the course of a few months, the massages changed in nature. Now, she had an ‘itch’ in her vagina itself. Since I had gone too far already, I complied, learning to finger a woman’s vagina and even massaged inside her anus. And, every night I jerked off, remembering the images and feelings of fingering Marjorie to orgasm. Sometimes, I notice the remaining sweet odor on my fingers, and it would send me over the edge almost immediately.
I had the wrong idea about vaginas. I thought they were big bloody messes. Sorry, but that’s the way I felt. And, I thought that down inside they were very tight little holes. I didn’t even know that inner labia existed. I’ve learned a lot. When I saw Marjorie’s peehole for the first time, I was fascinated. It never occurred to me there might be a specific opening for that.
She didn’t cum every time. But when she did, her legs would go all jittery, she’d start moaning and she’d end up shivering all over. I have to admit that I loved that. To give that gift to another human being, male or female, is a delight for the giver as much as the getter.
When I had been doing that for about a year, she started hinting that she wanted me to be naked when I gave the massages. At first, I hinted just as strongly that there was no way I’d do that. But something inside me was rather excited. Oh hell, more than ‘rather.’ I was very excited at the idea. Still, I resisted for a month. Finally, the evening happened. At the appointed time, I came out of my room, not wearing a stitch, and feeling very funny, maybe what you’d call embarrassed about the situation. I wanted to run back into my room and put all my clothes back on. I didn’t. And I did set up the table. She gasped, looking at me with a wry smile, evidently quite pleased with what she saw. I do keep myself in shape. I was surprisingly proud of myself.
The massage started as usual. When it came to the point where I slowly introduce my finger into her anus, I was quite surprised to see I was becoming erect. I ignored my penis, and completed her massage. No doubt she saw my erection, but said nothing.
Not long after that, she wrapped her hand around my hard penis during the massage one evening. It was electrifying. I had no idea that could happen with a woman. I was thinking she might stroke my penis, and actually secretly hoping she would, but she didn’t.
On my birthday last year, she surprised me at the end of her massage by demanding I get on the table. I laid face down, scrunching my erection under my stomach. She massaged my shoulders, my arms, my legs, and finally my butt. It was delicious. Then she had me roll over. My erection was sticking straight up. I was no longer ashamed of it, or weirded out by being erect around Marjorie. It had become natural. She ignored my erection as she worked on the front of my legs, my arms and even my forehead. I have to tell you, the massage was delicious. Then, ever so gently, she started rubbing her fingertips over my nipples. I couldn’t help it, sperm just started squirting out of my penis, shooting a good foot in the air. Some even hit my chin.
It seemed wrong, and I started to apologize, but Marjorie stopped me with a big smile, saying, “I’ve wanted that to happen for a long time, Larry.”
Things have evolved. She massages me as much as I do her, yet, I’m the one getting paid. What a job! I wouldn’t trade my position for anything. And now, her treatments are always happy-ending massages, with good testicle massage thrown in. I had no idea about testicle massage. No man had ever done that for me.
So, I’ve been with her three years now and I have to say I get a real delight out of our massages. Oh, I’m still gay, and I still haven’t had a full-on, live-in relationship with a guy, but it’ll happen someday. I haven’t actually been with a guy at all, even for a bit of a blowjob or anything for over a year, and oddly I don’t really miss it.