We slide into a booth at the rear of a quiet and dark resturant.  It’s very intimate, almost more than I would expect for a first … I guess … date.  Sure, we have been talking for weeks, but this was our first face-to-face.  We were friendly and I knew some of Her other interests, but never felt connected to them.  I saw us as becoming good friends, but after the greeting, She gave me on the street and now this very elegant place to have a quiet lunch it was all a little surprising.

She puts her hand on my thigh and while I was tempted to remove it, it felt really good in a way I haven’t felt in a long time.  I was quite a few years older than Her and didn’t think such feelings could be between us.  Maybe I was just imagining things.  I mean why would someone so young, so vivacious, and even so sexual be interested in me, practically old enough to be Her father – but not quite grandfather.

As we spoke, She took my hand and placed it in Her lap.  I went to pull away, but Her hand held me there and She whispered, “Don’t,” in a slightly authoritative tone.

The server came by and took our drink order.  I was more nervous than I had been in years.  I half expected the server to say something about our arms, but she just carried on.  There was this tiny exchange between the server and Her that didn’t make any sense, but before I could think about it, She slid my hand up almost to Her waist and back down again.  I could feel Her response.  The nerves struck me again.  Many things ran through my mind, “What was I doing?” and “I need to leave now!”, but chief among them was, “Who was this woman and why does She make me feel this way?”

She removed Her hand from mine and I kept rubbing her.  I could feel everything and it should have frightened me even more, but something kept me there.  I’m not sure I understood it, but I knew I didn’t want to leave.  As I kept moving my hand, She whispered very sexily, “Good boy!”  The words were delivered with a hot breath across my ear and neck and I shivered.

A small part of me bristled at the words, but a larger part of me felt something I hadn’t felt before and I was both confused and aroused.  I felt Her hand press down on me and I realized She knew it as well.  I discovered I wasn’t the only one getting excited.  Then the server returned and I stopped moving my hand.  She leaned back and whispered again, “It’s OK, she’s a friend of mine.  Don’t stop, it feels so good.”

I was confused, but when the server stood very close, in effect making sure no one else in the place could see into our booth, I felt both slightly reassured and more nervous than before.  Then my adrenaline jumped again as I felt Her pull up her skirt.  Another whisper, “Would you like to take a small taste?”  As She said it, She started guiding my head down into her lap.  It was too dark to see, but I could feel it as soon as it touched my lips.  Part of me expected it, but another part of me couldn’t believe it was real.  As She pushed me lower, I opened my mouth and felt it.  It felt huge, but I think that was mostly my imagination.  Then She let off any pressure and I surfaced, both literally and figuratively.  An unexpected milestone breached as She again whispered, “Good boy!”

Right then our food showed up and we ate.  It must have been delicious, but I barely tasted anything.  She enjoyed it and kept up Her side of the conversation like nothing unusual had happened.  I paid as an old-fashioned kind of guy that I am not sure I would recognize at the moment.

We strolled down the street, arm in arm.   “I told you we were going to stretch your limits!  You can’t say I didn’t warn you.”  As I gave thought to that, she guided me through a double glass door into a … sex shop.  After that little … interlude in the restaurant, I shouldn’t have been surprised by anything She did, but it still caught me off-guard.

The shop was, in a word, unexpected.  It wasn’t some dark place near the highway, but a bright, open place filled with all sorts of things.  Some of which I could identify, but a few of the things I saw left me a little baffled.  A lovely young lady quickly crossed the floor and greeted us, at least she greeted Her by name and the hug lasted a few seconds longer than expected, which told me the two knew each other well. 

“Hi, Jessie, it’s been a while,” She said to the clerk as they two broke up their hug.  The sight of two such lovely ladies hugging so enthusiastically was certainly attention-getting.  She continued, “How is Wit?”

“Oh, he’s doing well.  We just came back from a vacation up in the mountains.  It was glorious.  We’ll have to get together and get caught up.”

“I would love that.  Today, Jess, we are looking for a few things.”  She then introduced me and when I went to take Jessie’s hand, she pulled me close and kissed me on the cheek.  “Any friend of Hers gets more than a handshake!”  I thought referring to Her with an uppercase letter was just my own brain’s way of categorizing, but I thought I could hear it in Jessie’s words as well.  What was my mind doing to me and who really was this Lady at my side?

Jessie turned and waved across the shop.  “Please, be my guests.  The girls are here to help you with whatever you need.”  On that note, she smiled and went back toward a counter.  As I looked around, I realized there were other people in the place.  Some looked like shopped, but three young ladies I could see must have worked there. 

I guess I should describe the place a bit more.  It was very large, more like a small department store than what you might think of when it comes to a sex shop.  There were also signs directing people to the basement and much more merchandise.  I was surprised at how clean everything was.  There was a large selection against one wall of movies, racks, and racks of what I assume were various toys, and many clothing stands showing off things I really would love to see Her wearing.  I almost tripped when I realized where my mind was going.  I swear I came to meet a friend, at least someone I thought was going to be a good friend.  But I found something so much more and we’ve barely spent two hours with each other and already I am questioning things about myself.

We didn’t wander aimlessly, exactly, but we slowly went toward the stairs leading down.  At the bottom of the stairs was another employee, a very tall woman and one who obviously worked out.  She looked like she could break me in two.  She greeted Her, by kissing her hand, “Jess told me you might be in today.  It’s lovely to see you!”

“Thank you, Susan.  I’m just here looking for a few things to maybe spice things up.” 

Susan chuckled and simply said, “If I can do anything, just holler.” And got out of our way as we entered a place I can barely describe.  First, the scent – have you ever been overwhelmed by the scent of leather?  Well, I can now say I have.  The first several rows of clothing were all leather, different colors, different objects and I didn’t see a single leather jacket.  I wasn’t sure how to describe it until I saw a sign that said “Fetishwear”.  As we passed through it, She picked up an item and showed it to me.  It was a black leather collar.  I looked at it for a second.  “What’s the clip for?”

She answered, “I’ll tell you when we get a little further along.”  I mentally stumbled, ‘Further along what?’  I didn’t say it, I think I was still overwhelmed a bit.  She snagged a couple of other things as we kept moving through the goods.

We passed through another section and it seemed all plastic latex.  “Do people really wear this stuff?” 

Susan was closer than I realized, “Oh yes!  Just think how something so tight and sexy would look on Her.”  Aside from hearing the uppercase ‘H’ again, I did think about what that would look like across Her hips and it made me swallow.

We paused near a wall with some wooden structures near it.  She took my wrist and wrapped a leather cuff around it.  When I started to say something, She put a finger to my lips, “Not just yet.”  She did the same to my other wrist.  The cuffs weren’t uncomfortable and they had a chrome ring on them.  She then grabbed a couple of … I’m not sure what to call them, maybe leads?  She clipped them to the cuffs and slowly my arms were pulled apart, not uncomfortable, just firmly.  In a moment I think I looked more like a Leonardo Da Vinci image with my arms outstretched.  Again I went to say something, but then She pressed her body against mine.

“Don’t freak out, nothing bad is going to happen.  This is a reputable business, not a freak show.  You know where some of my own interests lie and I thought you might like to explore a little.  I know seeing you like this is a real turn-on for me.  She stroked me for a minute and then stepped behind me, pressing up against me.  I could feel Her ‘interest’ growing as She pressed tight against my butt.  Then She reached around and started stroking me again. 

Mentally I was all over the place.  I was in a public store, luckily there was only one person downstairs with us and if I thought about it, I would have been surprised she hadn’t said anything.  But this beautiful woman was pressed up against me, I could feel Her excitement as She stroked me, and while my brain was a bit fogged over, my body sure liked it. 

Then She started speaking in a low, very sexy voice, “You knew something like this was going to happen eventually.  From all our talks, including some rather risque and sexual ones.  You knew exactly what I was like and what I liked.  We could dance around with this for days or weeks, but you knew it, whether you wanted to admit it to yourself or not.  I cannot help myself.  When I meet someone I want, I have to take them.”

She stopped stroking me, knowing just how physically turned on I was.  I have no idea how She could know how mentally excited I was getting as well. 

“Push yourself against me!”

I couldn’t stop myself.  I had enough leverage that should could feel me.

“Good boy!  That feels so good!” 

Those words again burned into my brain.  How could two simple words make me feel so strange and so good at the same time?

I felt Her at my neck and realized She was putting that leather collar around it, buckling it. 

“Before we leave, there is one thing we need to do, but for that, I have to unclip you and take you to another room.  If this is really scaring you, you can take off the cuffs and collar and just leave but know you will never see me again.  But if you stay, know that I am going to test all your limits!  You think I don’t know you that well, but just like you know what I like, I have a good idea I know what you need.  I am just the person to fulfill those needs.”

She pressed hard against me and then stepped away.  The sudden change from the heat of Her body to the cool basement air was almost shocking.  “I’m going to go in the other room,  Susan will unclip you and take you back there, if it’s what you want.  The choice is always yours.” And then She was gone, and this large room felt smaller for some reason.

Susan stood in front of me.  There was no reaction, there was no smirking.  She was like a robot unhooking the leads from my cuffs.  I stood there for a second trying to think hard, but I was lost in my own mind again.  She then gestured toward the back of the room.  I assume that was the direction She went.  I rubbed my wrists and neck and tried to decide when my feet did that for me.  I moved in the direction Susan had indicated.

She took me to a door and led me inside.  It was small, almost a closet, but I was confused, She wasn’t there, just a chair near the wall.  Susan gestured for me to sit down, then she took something from the wall and another unthinkable thing happened to me today, she hooked it to the clip on the collar.  That’s when I noticed the hole in the wall.  I couldn’t see through it, it was dark on the other side, and behind me, the door clicked closed as, I guess Susan left. 

To my astonishment, a cock poked through the hole and went right into my mouth which had opened to say something.  For the second time this afternoon, I tasted a cock.  There were no words exchanged, but the command was obvious.  It was hard, and felt enormous, not that I had a lot to compare it to.  Part of me shrugged while the rest of me couldn’t help but do the obvious thing.  I mean I knew from the beginning that She was a trans woman.  And we started talking on Twitter about so many things.  Yes, I confided some fantasies, and She did the same, but never in any dreams did I imagine this scenario.

So, I sucked Her and licked the head and shaft.  I guess she really was excited because it didn’t take long before she was pushing in and out of my mouth.  The clip kept me in position and all I had to do was keep trying to suck on it.  After several minutes I could feel it expanding and then, the only word for it was, that it exploded.  My mouth was filled with a slightly astringent fluid and I had to swallow or I would have been soaked down my front.  I was also out of breath like I had been running.  I pulled off of it and just looked at it.  There was cum on it and it really looked incredible.

A hand reached around and unclipped my collar.  “Good boy!” I heard right in my ear.  I jerked to the voice and She was standing there next to me.  The cock was still poking through the wall, “Who, what?”

She licked some of the cum that had escaped off my cheek and smiled.  “Now you know what being with me will be like.  Oh, you will have me in ways you cannot even imagine, but first, you have to earn that.  If you are brave enough, let’s go pick up a few more things to make tonight more interesting.  And, dear one, know that I will be forever surprising you and testing those limits – all of them!