I cut across the square and walked into the bar after work. I usually only come here at lunchtimes, the fish always being fresh and the salad light. I can come in here, have a quick lunch and be back at my desk within an hour easily.
In the evenings there’s a lot of people in from out of town, there being a large hotel next door. And there’s a fair crop of locals too. It’s quite busy after six. It’s surprising how crowded this lonely city can be when all the commuters go home.
I don’t think I’d seen this one before. Maybe I had but it didn’t matter anyway. It’s not like I go out looking for romance. But he looked interesting. He told me a name, and I just let him freestyle his way into my evening.
He bought me a few drinks, and started to get a little touchy feely. Well, it was ok. The bar was closing soon anyway.
I decided I’d walk home with him, his place wasn’t far from mine, and we’d part and he’d never know how different I am.
But that’s not quite how it went down. Sometimes it doesn’t. Sometimes it just gets more interesting.
We decided stopping at my place for a nightcap might be ok. Why not? He leaned close as I fumbled for my keys, his breath heavy against my cheek. By the time I found my keys he was running his hands inside my jacket searching for my breasts
We climbed the narrow stairs, upstairs above the two students on the second floor, all the way to my loft apartment in the roof. As I prepared the coffee I could see him poking around my bookshelves, as though he were interested in my reading habits.
By the time I returned he was a little more sober, and his advances more manageable. How would he respond, I wondered, to finding out that I was not quite as he imagined. My tiny cock, reduced in stature from years of hormone treatment, would still be an issue. Like so many, this one liked the wrapping paper, but had no idea what this particular parcel contained. Would he be angry?
That’s how some people respond. Realising that they are quite literally getting more than they bargained for is sometimes too much for them.
“Does this mean I’m gay? Did you turn me gay?” That’s a common one. As if I could ‘turn someone gay’!
I’ve heard it all over the years.
And so now I handle things just a little differently. The routine is something I’ve practiced, and as a result it’s polished. Sure a kiss and a cuddle is great. I don’t mind, and I like kissing. It’s intimate and I do get a kick out of the fact that at that stage my partner has no clue what they’ve got ahead of them. It’s exciting for me.
Second date, I’m already geared up. Yes, a pair of tights, panties and usually jeans by then, topped with fishnet tights and heels. It’s looks interesting, but is secure. They’re not getting anywhere near the goods. But I might give them a blow. Why not?
I might let them cop a feel of my breasts too. And I can get pretty creative around how I play with them. You’d be surprised what you can do with hands, feet and breasts.
The third date I may get kinky with them. Sure, they can suck and kiss all they like, on my mouth and my breasts. I might even let them rub themselves between my breasts. The feeling of warm cum on my tits is something I adore, so I’ll go there. I may even tease them, getting them naked and see how they respond if I put on a strap-on over my jeans. It depends just how far they wish to go. They’re not getting inside the jeans though.
I figure if I’m going to see them a fourth time, though, they might as well get to know what they’re really dealing with. It’s what you might think of as the big ‘reveal’. And it can be quite shocking.
I usually have a chastity device on. It makes them feel better – less threatened. Of course, I have the key and can release it at any time. I may spin them a story though. It all adds mystery.
As I drop my jeans, their hands inevitably reach between my legs. I brush them away. I know how to do this, and it’s a practiced motion. I usually have them on their back by this stage, and I straddle them, allowing them to slide lightly against my buttocks. They are so sensitive there. Sometimes they’re on the point of cumming, just by my rubbing them against my tights.
By now they are desperate. I’ll say something like, “Are you sure you want this?” and they look at me like I’m an alien.
Yes, they want this. Even though they have no idea what they are getting.
As I ease my tights down, they feel my buttocks warm through the fabric of my panties. And I let them rest against me. They can’t really see much. All I need do is lean forward to completely obscure their view. And I usually do. It makes my ass more accessible.
They always start pushing against me, and slowly I remove the last barrier between them and my body. The hot flesh is almost electric now.
I reach beneath that particular cushion where I know the lube is, and slowly coat my palm in it.
“You’ll love this,” I say as I reach behind me and massage lube generously over them. It amuses me that if I wanted I could simply slide down on them and they’d have no control now. They couldn’t help themselves. And still they don’t know.
“Really, Jeff? Are you sure you want this?” I ask again. Jeff, or John or whoever. It really doesn’t matter to me.
“Oh god, yes!”
My hand massages the lube into them and coats between my buttocks and I take them and bring them to the point of entry. I feel how they lurch forward trying to penetrate me, and I pretend to hold them back, still leaning forward. They can’t feel the warm steel of the chastity device, thinking only of sliding deeply into me.
“And you really want me,” I say as I feel them begin to move deeper.
They always affirm their desire vocally. I want them to. I need them to. Because in a few minutes they will realise the bridge they’ve crossed, and so often they have second thoughts. Their words will ring in their ears. Their lust clouds their thinking.
I sometimes wonder what they’d tell their brother and sisters, or their mothers and their fathers, if they were here to witness their headlong dash into an indulgence so repelled by much of society. And yet, here they are practically begging for it.
Their straining and heaving, all passion made flesh, and their gasping thrust and release… Afterwards I ease myself from them and that’s usually when they notice the steel chastity device. The tiny penis. And they usually recoil.
They go quiet.
It’s not me, of course, they say. It’s them. They didn’t realise.
Of course they didn’t. And the dribbling semen still drips from them.
For them this is the first time and for me the fiftieth? The hundredth? I don’t know. I don’t keep score. But it’s something I’ve seen plenty of times, even if it is their first.
Sure, they’ll call me in the morning.