Meeting Frances

I opened the door to greet him. Standing there with a nice smile and soft face, he wore a long coat and carried a gym bag. Pleased with his appearance, I presented a nervous smile and invited him to come inside.

The unit was small, with just the basics, a bathroom, a comfortable lounge chair, a double bed, a tv,a small kitchenette and a small table with a single chair to sit on.

I'd already setup my laptop to display output through the tv and was looping a series of erotic pictures which I had collected from the internet over the years.

I sat on the bed after our initial greeting.

He said, "Give me a little bit of time and I'll get myself ready for you."

Walking over to the small desk, he picked up the high-backed chair and took it into the bathroom, closing the door behind him.

I sat there on the bed and waited, and I thought about how I got here. Meeting Frances had been such a coincidence. I was on some internet chat site which had dedicated rooms like 'Çhicks with Dicks' and 'Spanking at Home' and 'Men in Lingerie' etc. There was a few people in the chatroom and I had a usertag called 'Home and Hosed' ', which he liked and we started chatting there.

As it turned out, we chatted for hours getting each other excited with common interests. We discussed the things we would dress up in when our partners were out. The type of clothes we'd wear, and fetishes for womens hosiery dominated our dicussions. He said it was unusual to hit it off so clearly with someone you just met in a chat room.

After chatting for a while, I asked where he was from. He said Australia, which of course I was too. Then he told me he was in Brisbane. Straight away my pulse started racing, as I knew I soon had a work-related week long trip to Brisbane coming up. All I could think of was maybe, just maybe we would get together and act out some of those fantasies we chatted about. He said he'd like to get together in a room to dress up and play and maybe touch. Then I told him in that chat room about my work trip. Over the next month we chatted regularly until about a week to my trip and he asked me where I was staying.

This was the point at which all of this online fantasy that I had been carrying on for a number of years was about to get real. This fantasy life I had kept separate from my family, my partner and the opportunity to act on it had finally come around. I honestly never thought I would do this, but here I am sitting here on a bed waiting for him to get ready for me.

I told him the hotel I was staying at. At that point, this event was on.

When we chatted next, he gave me a phone number and said text me when I check in and we can make arrangements.

The night after getting off that chat I started to get extremely nervous and had quite the panic attack. That voice of reason which had so often guided my path through life piped up. "It's ok, he doesn't know your name, where you live, he doesn't know much about you at all, except for where you are staying. You can back out of this."

On the day I went to the hotel, I picked up the key and went to the room and sat on the bed. I picked up my phone to text Frances, but just couldn't do it.

Likewise the next morning before leaving for work, I picked up the phone, but still didn't have the nerve to text him.

But as the days went by, I could not stop thinking about Frances and this opportunity which has presented while I'm a long way from home. Each day I would get into a state of arousal as the thoughts became more frequent about what we could do, what he would look like. We had decided not to share pictures prior, hoping that we would hit it off regardless when we met.

Should I go through with the fantasy that I have held for years? It wasn't until lunchtime after sitting through a course in which I could barely concentrate, that I just decided I am going to go ahead with it. I am going to do this, yes I am!

While I had the bravery to do it, I got out my phone and sent him a text with the room number and told him when I'd be there.

It was now too late to back out. This Was going to happen.

After the course I got back to hotel, got out of my streetwear and took out all of my girly clothes that I had brought. There was so much there, you would think I was dressing for a week! I had a dress, two miniskirts, a variety of underwear, several pairs of hosiery, a range of tops and even a leotard, and some shoes.

After some deliberation I settled on a black torsollette and some black tights. I had a wig on, long blonde hair and some low heel shoes.

So here I am sitting on this bed with Frances in the bathroom getting ready for me.

The bathroom door opens, and I cannot believe what I'm seeing. The man who came in with a babyish face and a dimpled smile wearing a cap on his head is nowhere to be seen. The person looking at me is a stunning brunette with long hair, wearing a tight top with ample cleavage on display. She has a longish miniskirt made our of spandex I think. She has stockings on, although I cannot quite see the tops under the miniskirt. She has ballet flats on, and the makeup. Oh my the makeup is beautiful - bright red lipstick. This woman staring at me is gorgeous. The only sign to tell me she is a man is the bulge being covered by the skirt.

Frances says to me "Come here darling, let me have a look at you."

I make my way across the bed and stand up (nervously I must say). My pulse is racing and she says. "Darling come on into the bathroom and let me help transform you"

She leads me in there and I sit on the chair and face the mirror.

Frances starts to apply makeup on me and sets about the process of changing my hardened male look into a softer female look. By the time she's finished I'm in awe of the beautiful gurl looking back at me. It doesn't look like me. I mean it looks a bit like me, but its not me.

She brushes my hair and the sneaky little smile which has been threatening to appear is suddenly plastered across my face.

She says warmly "Up you get. Let's go into the bedroom"

We'd previously kind of agreed that we wouldn't take photos of each other, but still she asked me to unlock my phone.

"I'm going to take some photos of you on your phone so you can see how beautiful you are. You can take some photos of me too if you like to keep for yourself. I trust your discretion."

This was the first time I had ever done anything like this. My nervousness was ample evidence. Frances on the other hand appeared to have no nerves at all and seemed comfortable with how things were proceeding. I was pretty sure Frances had done this a few times before.

I unlocked the phone and Frances takes photos of me. Urging me to stand up, look this way, look that way, sit on the bed, raise my legs, do this, do that, stand up, bend over. Soon she has a stack of photos.

She stands up my phone on the bed side table and takes time to position it so that it's lens will capture whatever follows on the bed.

I'm standing at the edge of the bed, and Frances takes up position directly in front of me. I am in awe of this beautiful crossdressed woman and she says "Go ahead and touch me. I know you want to."

The truth is, I do.

I start by putting my hands on her tight shirt, and feeling her breasts. They are not huge, but they are real and bigger that I'd expect on a man her size. I wondered if she had been taking some hormones. I gently caress those breasts, and she has a huge smile. She's loving the newness of me perhaps. I keep going, feeling the sides of her body, up to her shoulder, and then down her arms until I reach her fingers, which I entwine with mine.

We stand there facing each other eye to eye with hands locked together. It's only for a few seconds, but to me it feels like much longer.

I let go and reach up to touch her face. The decision to kiss her is taken out of my hands as she surprises by leaning forward and kissing me.

I am kissing a crossdresser and her tongue is going around the inside of my lips. I am holding her hips while she plays with my mouth. This goes on for a minute or so, which doesn't seem a long time, yet is long enough for me to feel the butterflies of a teenagers first kiss.

She pulls away and then puts her hands on my shoulders and gently pushes me down. This is what we talked about in the chat and now its happening. I'm meeting up with a crossdresser who is going to force me to give her oral sex. I am powerless at this stage. My fantasy is too strong and I have to keep going. I am nearly down on the floor with her hands on my shoulders.

She no longer needs to gently push, as I move of my own accord.

I grab that skirt and roll it up and I can't help looking at that cock, wanting to wrap my lips around it. I've never done it before but its been such a fantasy, and here it is.

Tentatively at first I put my tongue out and lick the head. Its not long before I have more of it in my mouth. Then I just go for it. My technique is probably awful, but the thrill of it is beyond compare.

Back and forward I go bobbing on this cock, back and forth, back and forth. I'm lost in it. I'm so lost in sucking this cock I don't even notice Frances pick up my phone and start taking pictures of me sucking her cock. I hear the click, I don't even flinch, and keep going. We do this for what seems like a long time. Frances doesn't come, and eventually puts her hand gently under my chin.

I take this correctly as a sign to stop and follow her guidance. She asks me to stand up and tells me to kneel on the bed on all fours and face the other direction. Which I do.

Dressed up in my wig, black tights and torsolette, I wait for the next direction. Frances takes another photo, moves around the bed and takes some more. She is documenting this event for me, for my own fantasies, for my own sexual enjoyment.

She puts the phone down.

I feel her kneel on the bed behind me and Frances rips a hole in my tights. I get nervous. What's she going to do now? Is she going to fuck me in the ass?

I heard her bag rustle as she grabs some stuff out.

I hear a lid snap open, then the recognizable sound of gel being squeezed out of the tube to be put on a sex toy.

I can feel the coolness of the dildo pushing against my ass. Frances is slow in how she progresses. Gently circling the dildo around, she pries open my hole.

She pushes further and I feel the pain, only slightly though. Pressure is more like it, not so much pain.

I can feel a serve of my precum leaking onto my tights.

The dildo has edged its way inside me, and Frances slowly pulls it out partially before pushing it back in.

She takes her time doing this for a few minutes, and I find myself thankful that the dildo she has chosen is not very big, and not very thick.

She sticks the dildo in and changes to a circular motion (as much is possible), and I take a moment to appreciate the feeling of fullness that I have never appreciated before.

What's it going to be like when she sticks that cock in me?

My tights are soaked with precum now.

She goes back to the in and out routine with the dildo as she opens me up, preparing me for the main event.

Without warning, she reaches around in front of me and grabs hold of my soaking cock. I almost cum with the touch. It takes massive restraint to hold on.

Here I am dressed up in this hotel room with a hand on my cock and a dildo up my ass. I am in the middle of my fantasy.

Frances lets go of my cock. The elastic on my tights snaps back against my skin.

She takes out the dildo slowly.

There has hardly been a word said between us since Frances came out of the bathroom, and any sounds in this room have been from me expressing my pleasure.

I hear the dildo placed onto a side table, and then Frances picks up the lube.

She coats her cock with it and I hear it squish as she pumps her cock with her hand once or twice to spread the lube.

She says in a quiet, feminine voice "This might hurt a bit sweetie, but I'll be gentle."

And gentle she is, as she proceeds to take me from behind.

She pushes against my ass and slides herself in me slowly. I take in a large breath, as the girth is a little wider than the dildo. She fills me so.

She follows the same process as with the dildo, slowly in and out.

It is intense pleasure with a slight sting of pain.

It's taken me this long to notice her hands are on my hips. How long have they been there?

I feel her grip tighten as she uses more of her weight to push harder into me.

She is inside me as far as the dildo was previously, and I wonder how much bigger she is than the toy.

With her cock plugging up my tight ass, Frances takes a moment to run her hands over my nyloned legs. Starting with my ankles, she caresses the parts which she can reach, ensuring she stays inside me. After feeling up the front of my nyloned legs, she retakes the position gripping my hips tightly.

Oh my!. She starts fucking me with vigour. No longer being so gentle, she is now seriously riding my ass so hard I can feel her balls banging on my ass with each thrust.

I feel myself cum. I have cum all over my tights with thick ropes.

"I've cum., Oh my God Frances, I'm sorry."

She doesn't respond, doesn't change her rhythm even slightly - just keeps pounding me harder and harder, and I keep coming like I never have before.

Its so fucking hard and fast.

I can feel her come, oh I can feel it filling my ass. mmmmm, it feels so good.

She takes her cock out and I collapse on the bed.

I'm lying on the bed as Frances quickly grabs my phones and takes more pictures. She could have been taking photos all along, I have no idea.

After that, we just sat on the bed.

An hour later we were both sitting on the bed, two dressed up crossdressers.

It wasn't really awkward, as we had chatted previously online.

I had all of my saved internet pictures cycling on the tv, and was starting to get aroused again.

I was sitting there watching, still in my cum soaked tights when Frances jumped up and positioned herself in front of me. Looking directly at me with a smile, Frances puts her head down and starts sucking my cock through my cum soaked tights. She laps up the cum from the material which gets me harder still.

Licking me softly, sucking and cleaning "Pull down your tights sweetie."

I duly do, just enough so for her to go to work sucking my hard cock.

Here I am tossing up between watching my porn on tv and watching Frances sucking me.

I grab my phone and start taking pics of this scene. My fantasy has come to life and I now have all the pictures to prove it, and re-live it over and over. I take pictures of the room, She looks up and I take a photo of her smiling at me.

This is the action that makes me cum again.

Frances takes it all. She swallows and swallows, and minutes later she sits up and simply says."I've got to go now."

The abruptness takes me by surprise.

"Did I do something wrong?"

"Oh no honey, This has been awesome fun for me too. But this is all the time I have.

I'll just have a shower if you don't mind."

All I can say is, "Of course."

Frances hops of the bed, goes to the bathroom, and soon I hear the shower running.

The thought of joining her in the shower briefly surfaces, but I don't find it at all arousing. The thought of showering with a man, who was this beautiful, fun woman with me, does not entice me at all.

I find myself strangely embarrassed all of the sudden, and go to grab a hotel gown to put on over the top of my female facade.

When the bathroom door opens, there is no trace of Frances. Coming out is the same man who came in the front door with the boyish somewhat femme face in street clothes with runners and his gym bag.

Frances says goodbye, not with any real intensity. Just says goodbye as if we had been casually chatting.

I say "Bye Frances, I'll catch you in chat."

To which there is no reply as he exits and the door shuts.

I sit there on the bed, thinking that as much as Frances was part of my fantasy, perhaps I was a part of her fantasy too.