I was in my early thirties when I had my first prostate exam. A visit to a new doctor and she (yes, she) told me that it was something men should do regularly once they reached my age.
My friends and I had joked about prostate exams, as you do, and I was expecting the worst. But here's the thing. I didn't hate it.
The doctor pulled on a rubber glove, covered it in lubricant and had me bend over the examination table. There was pressure and she told me to relax. I managed to do so and felt her finger enter my anus. She moved it around and told me that everything felt normal. I had to laugh. Nothing felt normal about what was happening. Anyway, it was over in a few seconds.
In the following days, I couldn't help but think about the exam. The whole idea of having something up ones ass had always been unappealing, but now I wasn't so sure.
I thought about trying it again. I'd watched bisexual porn before, and been quite excited as an observer. Those guys seemed to enjoy it, right?
I was between girlfriends at the time, so masturbation was a regular hobby. Sometimes, instead of actual porn, I read the Craigslist Casual Encounters page and fantasized about answering ads.
One evening while I was jerking off, I remembered my recent prostate exam and was tempted by its memory. I reached down with my non-stroking hand and began to tickle my anus.
It felt very nice. I decided to try a little more. But I had no lube and there was no way I could go deeper without hurting myself.
I probably would have left it there but, as chance would have it, a few days later I saw an ad from a woman looking for a man.
"Thirty-something female, not lesbian but with tomboy tendencies. Seeks man who is willing to explore role-reversal. I'm okay looking. I work out. I am not crazy. Just looking for a straight guy who wants to be penetrated by a strong woman."
I debated with myself. I'd never answered these ads, they were just wanking-fodder. But this one seemed like a perfect opportunity coming along at the right moment. I sent her a message.
We traded a couple of e-mails, names (she is Megan, I am Rob) and face pictures before arranging to meet in the flesh.
Knowing that we may end up having the kind of sex that had brought us together, I prepared myself carefully. Shaved my face, trimmed my pubic hair and, most importantly, gave myself an enema.
We met at a mutually convenient coffee shop and it went well.
Outwardly, we were age- and looks-appropriate. I think I was probably getting the better of the deal. Her hair was cut short and there were several rings in each of her ears. She was wearing a leather motorcycle jacket, under which her ample bust was barely covered by a low-cut t-shirt. I knew I was going to have trouble keeping my eyes on hers while we chatted.
Later, allowing myself another admiring glance, I noticed that she was not wearing a bra and I could clearly see the outline of a nipple piercing. I tried not to stare, but she caught me and just laughed.
She was self-conscious about only one thing: her height.
At just over six feet, she is taller than I am. I'd never been with a girl even close to my height, but it was fine. Intriguing, even.
We had some similar interests and she had a good sense of humor. I liked her and she clearly liked me. She told me this wasn't the first time she had placed an ad, but that I was the first - apparently - sane man to reply.
Our conversation didn't dry up, but our coffee was finished. I felt that the next move was hers, so decided be patient and not lead her. By then, I knew what my answer would be. When she invited me to her apartment, I readily accepted.
She lived nearby and we arrived at her place within minutes. She kicked off her shoes at the door and asked me to do the same. When she slipped off her jacket, I saw for the first time two full-sleeve tattoos. I've always found girls with tattoos to be very arousing. The whole circumstance was arousing, really. I was standing in a strange apartment, barefoot and facing a sexy, pierced and tattooed woman who was towering over me. Well, it seemed that way. She had me by an inch or so, but that was almost a foot adjustment from the last girl I had dated.
"So, this is my place."
I looked around. She had some nice art on the walls and a view of downtown Seattle across the water.
"It's cool. Great view and plenty of light. And so convenient!"
"Well, not really. I have a long commute."
"Yes, but I'm only two blocks away."
It was a groaner, but I made her laugh, which has always been my most successful approach to gaining a woman's approval.
She invited me to sit and we took opposite ends of the love-seat in her living room.
We were already comfortable with each other and made small-talk, discussing local bars and restaurants. We danced around it but I was very aware, and I could tell she was too, that we hadn't yet talked about the elephant in the room.
Eventually, there was a lull in the conversation. A pregnant pause. We looked at each other.
"So," she said, eventually.
"So," I coyly replied.
"Do you want to do this?"
"Right now?"
"No time like the present."
She took my arm and pulled me over and onto her. My legs straddled her thighs. Then she reached up and forcefully pulled my face close to hers and started kissing me. It was hard and fast. She definitely took the lead. I felt her tongue enter my mouth and she explored. Hard, darting movements, all around.
My hand came up and caressed her cheek. I ran my fingers into her short black hair as I kissed her. Then I slipped one hand down and touched her breast through the thin material of her shirt. I wanted to feel her nipple piercing. The little bar that I had seen the outline of earlier.
As I did that, she reached down and started fondling my ass. Her hands on my buttocks squeezed and kneaded. She lifted her hips, pulled my groin to hers and ground herself against me. I was already erect. She felt it and gently pushed me off her.
"If you're a good boy, I'll take care of that later. But first, you do what I want. Why not take off your clothes."
I stood in front of where she was sitting and slowly tugged off my shirt.
"Come on! I didn't ask for a fucking striptease. Just get it all off!"
There was laughter in her voice, but it was she who was directing the action for now. I quickly peeled off the rest of my clothes and stood naked for her appraisal.
She told me to take my hand away from where I was vainly attempting to cover my cock-stand. She said it was a nice size, much to my relief. I stroked it for her when she told me to. I turned around, when she asked. Bent over for her. Spread my cheeks.
The control she was exerting was arousing her. I was excited too, and my heightened anticipation was ratcheted up even further when she took my wrist and led me to her bedroom.
She made be bend over on the end of the bed. "Are you ready for this? I don't want you to chicken out."
"I think so."
"Well maybe I should make sure."
I heard a clinking sound behind me.
"Reach out your arms."
I reached towards the head of the bed and she swiftly snapped on a pair of padded handcuffs. Then she tied them to one of the rails in the frame. I waited, patiently, while she found a couple of lengths of silky rope which she used to tie each of my ankles to a bed leg. I was immobilized. My bare ass was bent over the end of the bed. My legs were wide apart. Although I was now at the mercy of a woman I knew very little about, I was intensely aroused. My cock, trapped beneath me, was like iron. But it was pointing backwards between my legs. I wriggled around, trying to get it into a more comfortable position.
She misinterpreted my movements.
"Oh, you are keen, aren't you?" she asked, mockingly.
Even though my movements had been for another reason, I was keen. Very keen. I wanted it. But I didn't want to admit aloud quite how aroused I was by the prospect. I played it as cool as a man in my position might.
"Well, it's why we're here, isn't it?"
"It is indeed. I want to fuck a guy, and you want a girl to fuck you. We're a perfect match."
I heard her stripping out of her jeans behind me. Out of my sight. Then some other sounds. She was stepping into a harness.
"I've had this for a while. A girl friend bought it for me. Not a girlfriend, just a friend who happened to be a girl. At least, that's what I thought," she chuckled, ruefully.