S001: Scott’s Chronicle: Meeting

It is a Friday night.
Scott is thirty-years-old, new in this town where you just started a new job. After a month of working hard at the job with no real recreation, you decide it is time for some.
After a couple of weeks in company housing, you found a condo that is being rented not that far from where you work. But far enough away in a nice suburban neighborhood. It had been a hard week at work. You are getting the hang of the job, but it takes a lot to stay on top as you learn. Tonight, you decide you deserve a night out.
Driving back and forth to work each day you see a corner neighborhood bar about a half-mile from your home. Each night the place looks busy, and it just seems to keep calling you to stop. Tonight would be the night that you answer that call.
First, you go home to shower and shave and change into more casual clothes than the suit from work. By eight you are ready and heads out. You are feeling really good, as you can wear what you like to for the first time all week.
When you walk into the cozy bar, it is moderately busy. There are a few seats at the bar. You take one with empty seats on each side. One seat away, near the bar station in the middle, is sitting a woman around your age. You nod to me as you sit down and I smile back.
The bartender, a woman, gets your order and then goes back to talking to me. The bartender is telling a story of woe to me, who seems to sympathize and offering some suggestions. The old theory that everyone spills out to the bartender seems to be in reverse here. The bartender is the one spilling to the woman. And it is funny, as the bartender looks to be ten to fifteen years older of the two, but she clings to every comment I make.
Now Scott at thirty is still rather fit. Regular exercise, the company does have an on-premise gym; and rounds of golf, finally spring is here. You just found a course nearby to play at and got one round in last weekend. And an invitation to join the company golf league has been extended to you. So, all in all, Scott looks pretty good with your blonde hair, pushing toward six feet if on your tiptoes. Well in your opinion.
The woman, you keep glancing at me as you overhear the conversation, is cute in my own way. I am a bit chubby, but wow what a rack you think. I smile a lot, which makes my face seem to shine, and I frequently laugh, in a unique tone all its own.
You would like to get to know this woman you think. But you do not want to intrude.
Then the opening comes. A couple comes in, and the two seats on each side of you are the only two still opened at the bar. The woman of the couple sits down next to you while the man stands. You offer to move over so he can have a seat too. Yes, now you are sitting next to the laughing woman without seeming too forward.
The bartender is now busy with orders. You introduce yourself and comment that it seems like I know people here pretty well. Before moving over, you watch as three or four men walk by and say hello to me.
I tell you my name is Becky, and that I live in the neighborhood nearby. “I stop here in the evening for years now,” I explain.
We quickly begin chatting. It is a delightful evening. You buy us both another drink as we talk, then another. Then I insist on buying you one.
I even introduce you to the owner of the bar, an old grumpy seeming guy, but who welcomes you to the neighborhood and bar. By the time midnight rolls around, we are laughing and discussing everything about our lives. Several times as I am emphasizing something, my fingers run along your thigh some.
For several reasons, this gives you intense pleasure.
And as midnight passes, and the new day arrives, I tell you I need to call it a night. You agree and walk me to my car. Now sparks have been flying between us for a while this evening.
It has been months since you last were with anyone. Your previous relationship totally ended before you got this job as she got mad that you were applying for something in a different state.
At my car, you can’t help yourself, but lean to me and kiss me. Tentatively at first, but when you feel me respond, we kiss long and deeply. Over and over.
You lift the back of my dress enough, and discretely as I am against my car, rub your hands over my panties. Oh, you love the feel of panties against your fingers. I respond, and my fingers move to your crotch and rub through your pants at your hardening cock.
And then it happened.
What were you thinking? Why did you let things go this far, dressed as you are tonight?
I unzip your pants as you are pressed close to me. No one can see. We are in a dark corner of the lot. My fingers find there way into your pants, and I begin to rub against your underwear. I look you in the eye with a quizzical look on my face as I run my fingers up to the top of what you are wearing. Then slide down to your thigh, and then smile at you.
“I think we need to get in the car right now,” I say to you as I open the back door.
I have you climb in first, and then follow you and close the door. There is dark glass on the window so no one can see in. But the moonlight does shed some light on us in the car.
“Take down your pants; I want to see,” I tell you.
You are blushing so red right now; your hands are shaking some. You have never revealed this to anyone, but I had smiled.
You could have just said good night, zipped your pant and escaped, but you were drawn to climb in the car with me. You knew what was coming.
So, you unbuckle your pants and lower them to the floor.
Your secret is revealed.
You are wearing silk pink women’s panties, low cut, so your glans is peeking out of the top, a pink lace garter belt, and white silk thigh high stockings.
“Oh my,” I chuckle. “This is even better than I imagined. I had wondered what that little knobby thing I felt when I caressed your leg earlier. Do you wear these often?”
How I said it was rather kind, and like I was interested in understanding. And while I am asking, my hand slides to rub against your shaft outside your panties.
Ooh! That is the first you have ever felt someone else do that to you when wearing panties. You almost spurt at my touch.
First, you turn and kiss me deeply.
“Becky, I started wearing women’s undies about six years ago. I don’t know what came over me then. I was shopping for a present for my then girlfriend, and feeling the softness of them as I tried to choose the ones to give her as an anniversary gift I couldn’t stop myself from buying two pairs in my size too. They were so pretty.”
“That night, she wasn’t over, I put on my first pair. Feeling the silk against my dick, so close and nice, then rubbing myself I came in minutes. And could not turn back. I only wear them a few times a week. The stocking came a bit later. And the bra I wear at home when relaxing in these after that.”
“No one has ever known about this. That girlfriend and I broke up shortly after, as at first, I wanted to be in them all the time when I was off work, so for a while I did not want anyone else around to interrupt my pleasure. Later I got a handle on it, and dated one or two other women, never letting on what my true pleasure was.”
“Now moving here, and working as hard as I have this last month, as I told you, I haven’t been able to indulge for over a week. And while I decided to go out tonight, I so wanted that special feeling too. So, that is my secret, which I must keep a secret, and I hope you understand.”
I listen to your story, and put my arm around you and let you lean on my shoulder as you are telling it — all the while stroking your stocking covered thigh.
“Scott, is it just wearing the underwear, or do you want to be even more? Have you ever?” I ask you as now my other hand is running my fingers through your thick blonde hair.
“I would like to do more, be dressed up, have makeup and hair done, be a boy/girl,” you confess.
“Would you like me to help you do that?” I ask in the kindest voice.
You look up and gaze in my eyes, seeing that I am serious with what I am offering, and reach and bring your lips to mine and kiss me over and over.
Both breathing heavy now, and you rather hard from all of my caresses, and actually telling someone about this, we pull apart.
“Do you mean it Becky?” you stare at me, hoping I am not joking.
“Well, this is new but rather interesting to me. You do look so cute in these. It does feel so nice rubbing against you through them,” I confess.
“We could see how far we are both comfortable going with this. I mean as long as you don’t become too much a girlfriend and not a boyfriend to me,” I laugh.
You kiss me some more, and say, “I will be the best girlfriend, and boyfriend, to you as possible if we could do this together. I feel like I am dreaming.”
“Well it is getting late now, but…” I say as I lean over your lap and begin to lick up and down your hard shaft pressing against your now tight panties.
The glans, red and sticking out of the top I take into my mouth. Just the glans and suck on it.
“My someone has a big clitty,” I kid you.
And then I suck and lick at it, licking up all the precum and then sucking the tip even harder until you explode.
This whole night has been beyond your wildest imagination, and it all comes to a head rather quickly under my lip care. You start to apologize for cumming so quickly, but I raise my head and kiss you deeply. You taste your cum on my lips.
I then press two fingers against your lip and tell you to “Hush.”
“There is nothing to apologize for, this has been building up in you for a good while I would guess, so the first time it is expected that it comes over you quickly. There will be many more times ahead I am sure.”
We kiss again, and I help you pull up your pants. You take me in your arms and hug and hold me close to you.
We exchange phone numbers, and I tell you we will talk and plan our first play date tomorrow morning.
We climb out of the back seat, you kiss me once more, and help me into my driver seat. Only when you know my car has started, do you go to yours. And it is sweet; I sit there watching until your car starts too.
I pull out, and head in the same direction you are going to. You realize you are following me as we drive home, and you hope that I don’t think you are trying to come to my place now. But then, I pull into the same condo development where you live. And in amazement you see me turn into a drive only a block or so from your unit.
Could we be that close of neighbors?
I watch as you drive on, and getting out of my car; I can see down the block you pulling into your drive.
I smile to myself. This might be a very interesting relationship which might be starting.
You sit in your car for a few minutes when home, your head whirling with all that just happened.
You quickly text me good night and thank you. Closing it with, “your neighbor Scott, it seems.”
I laugh to myself as I read it as I walk to my door. Inside I send a reply, “Until tomorrow. Do you want to come to brunch around noon?”
Your “yes” reply is instantaneous.
You can hardly wait the ten hours until you can see Becky again.