Gathering with Frances
I opened the door to let him in. He stood at the entrance, smiling softly and wearing a long coat while holding a gym bag. I was relieved to see him looking good, so I smiled nervously and welcomed him to come inside.
The unit was tiny, but equipped with the essentials such as a bathroom, a comfortable armchair, a double bed, a television, a small kitchenette, and a small table with one chair.
I'd already set up my laptop to broadcast its output on the TV and was cycling through some erotic pictures from the web that I'd been collecting for years.
After our initial greeting, I sat on the bed.
"Give me a few minutes, and I'll be ready for you," he said.
He walked over to the desk and picked up the high-backed chair, carrying it into the bathroom and shutting the door behind him.
I waited on the bed, reflecting on how I got to this point. Connecting with Frances had been pure accident. I was on an online chat site with specific rooms dedicated to 'C divide Hong GO', 'Spanking at Home', and 'Men in Lingerie' amongst others. There were a few people in the chat, and I had the user name 'Home and boarded'. He liked it and we started chatting.
During our conversation, we shared our mutual fascination with cross-dressing, particularly women's hosiery. We discussed the different clothing items we wore when our partners weren't around and the peculiarities of our fetishes. He found our bonding unusual, stating that it was rare to hit it off so well with someone over the internet.
After chatting for a while, I inquired about his location. He disclosed that he was from Australia, the very same country as me. Excitement surged within me, realizing we would potentially have the chance to act out our fantasies in person. He mentioned he was in Brisbane. Impressed, I knew that my upcoming work trip close to Brisbane might be my chance to finally meet him. We discussed having a room where we could dress up and play around, perhaps even touch each other. Upon hearing about my trip, I mentioned the hotel I would be staying at.
This was the moment my online fantasies were about to become reality. A fantasized life separate from my family and partner was finally within reach. I never believed I'd have the courage to act on it, yet here I was, sitting on a bed waiting for him.
We continued chatting for several weeks, eventually bonding over our shared desire to cross-dress. He even gave me his phone number, telling me to send him a text message when I arrived at the hotel.
The night after we started this conversation, fear threatened to overwhelm me. It was normal for reason to provide warnings in my life, but it felt different this time. "It's okay, he doesn't know your real name, where you live, much information about you at all. You can pull out of this." My fears grew as the days drew closer to my trip.
Upon arrival at the hotel, I picked up the key and entered the room. Sitting on the bed, I reached for my phone to text Frances, but couldn't bring myself to do it. The morning before, I picked up my phone again, but still couldn't gather the courage to send the message.
As the days passed, thoughts of Frances consumed my mind. Each day, my arousal increased more and more, and I envisioned what we could potentially do with each other. We agreed not to exchange images of ourselves before meeting.
Finally, during a lunch break from a course, I weighed the risks and decided to move ahead with the fantasy. "I am going to do this; yes, I am!"
Feeling braver, I took my phone and sent him a message with the hotel room number and my anticipated arrival time.
There was no turning back now. This was happening.
After the course, I rushed back to the hotel room, shedding my streetwear and putting on my entire array of feminine clothing. There were so many options, it seemed I was preparing for a week-long stay. I had a dress, two skirts, various kinds of underwear, multiple tights, an assortment of tops, and even a leotard, along with some high heels.
In the end, I decided on a black torsollette and some black tights. I had a wig with long blonde hair and some low heels.
So here I am, on the bed, waiting for him as he gets ready in the bathroom.
As I open the bathroom door, my eyes widen in shock. The person who walked in, adorned with a baby-faced, dimpled smile and donning a cap, is nowhere to be found. In his place is a breath-taking brunette with a captivating appearance. Her hair sweeps past her shoulders, while her outfit features a tight top showcasing her abundant cleavage. She wears a spandex miniskirt, stockings, and ballet flats - all of which complement her body. A coat of bright red lipstick adds the final touch. This woman, who bears the appearance of a man solely due to the bulge hiding beneath her skirt, is beyond gorgeous.
"Come here, my darling. Let me take a good look at you," Frances says as she beckons me closer.
I nervously make my way across the bed and stand up. My heart is thumping madly, and she beams, "Darling, come into the bathroom and allow me to help you transform."
When we arrive, she has me sit in a chair and face the mirror. She starts to apply makeup, gradually changing my rough, masculine appearance into one that's more feminine. The reflection staring back at me is mesmerizing. It's not completely me, but it is a version of me that I've never seen before. The sense of arousal that envelops me feels different compared to my usual experiences. The woman, Frances, is seemingly accustomed with such processes, which is evident from her confidence.
Brushing my hair, she gently smiles, "Up you get. Let's go back to the bedroom."
We had previously discussed not taking photos, but she asks to take pictures with my phone.
"I want to take photos of you, so you can see how stunning you look. If you'd like, you can also take photos of me to keep for yourself. I trust your discretion."
This is a kind of experience I had never encountered before. Nervousness overwhelms me, while Frances appears incredibly comfortable. I'm quite certain she's done this numerous times.
Following her instructions, I unlock my phone. Frances begins taking photos, urging me to perform various positions: standing, sitting, leaning, and so on. Before long, a large stack of images is ready.
She sets up my phone by the bedside table, positioning it to capture what's about to happen.
I'm standing at the edge of the bed, uncertain and slightly terrified. But Frances, the crossdresser, approaches and holds out her hands. "Go ahead and touch me. I know you want to."
Despite my initial apprehension, my hands reach out to her shirt, tracing the shape of her breasts. They're not large but real, much bigger than I expected on a person of her size. It's possible that she's been taking hormones. Gently caressing her chest, she appears delighted. Encouraged, I continue to explore her by running my fingers alongside her body and up her arms until I reach her hands. We stand there, locked arm in arm, gazing into each other's eyes.
After a few seconds, I let go. Following our earlier discussion, Frances positions herself in front of me, and I find myself weakened. She pushes me down, and I eagerly comply. I'm now on the floor, with her hands on my shoulders.
As she guides me, she pulls up her skirt, exposing her masculine attributes. The moment I've longed for is finally at hand. I tentatively extend my tongue and lick the head of her, then proceed to take her into my mouth. My inexperience may have resulted in an awkward technique, but her moans leave no doubt about her satisfaction. Before long, she pulls away, offering her hands, and I gladly interlock them.
We face each other, eye to eye, and our hands clasped, relishing in this moment that lasts what feels like an eternity. Then, she releases my hands and pushes me back on the bed. The reality that this is happening, according to our plans, is overwhelming. I seize the skirt and turn it into a miniskirt, allowing my eyes to focus on her "package." It's much larger than I anticipated, and with this, the intrigue is palpable. As I lean in, Frances whispers, "Just take my cock and lick it." I eagerly comply and execute the act, feeling the colossal sense of fulfillment as I please myself through giving Frances pleasure.
I tentatively lick the head at first, then engage more keenly, and finally go all in. My technique may be horrendous, but the moment is thrilling beyond imagination.
When she finishes, she kisses my forehead and whispers in my ear, "Thank you for helping me."
As she rises and leaves, I am left to reflect on this extraordinary experience.
I sway back and forth, clinging to this penis, back and forth, back and forth. I'm completely lost in it. I'm so lost in sucking this dick that I don't even notice when Frances snatches up my phone and snaps pictures of me sucking her cock. I hear the shutter, but don't even flinch, and keep going. We do this for what seems like a long time. Frances doesn't cum, and eventually lays her hand softly under my chin.
I understand this as a sign to stop and follow her instructions. She tells me to stand up and kneel on the bed, facing the opposite direction. And that's what I do.
Dressed in a wig, black tights, and breastplate, I wait for the next order. Frances takes another photo, moves around the bed, and takes more. She's preserving this experience for me, for my own wanks, for my own sexual pleasure.
She puts the phone down.
I feel her kneel on the bed behind me and tears a hole in my tights. I hesitate. What's she going to do now? Is she going to fuck me in the ass?
I hear the sound of her bag rustling as she grabs some things out.
I hear the sound of a lid snapping open, followed by the familiar sound of gel being squeezed out of a tube and smeared onto a sex toy.
I can feel the coolness of the dildo pushing against my ass. Frances is careful in how she handles the process. She circles the dildo around, slowly opening me up.
She pushes forward and I feel a moderate pain, more like pressure than pain.
I can tell that a small bit of my precum has soaked my tights.
The dildo has worked its way inside me, and Frances slowly extracts it momentarily before pushing it back in.
She takes her time doing this for several minutes, and I'm thankful for the small size of the dildo, given that it's not very large or thick.
She switches to a circular motion, if possible, and I take a moment to enjoy the pleasant feeling of fullness I've never appreciated before.
What's it going to feel like when she pushes her dick into me?
My tights are soaked with precum now.
She reverts to the in and out routine with the dildo, preparing me for the main event.
Without warning, she suddenly grasps my soaked cock with her hand. Almost cumming from the touch.
Here I am dressed up in this hotel room with a hand on my cock and a dildo up my ass. I'm in the midst of my fantasy.
Frances lets go of my cock. The elastic on my tights snaps back against my skin.
She withdraws the dildo gradually from within me.
There's been barely any dialogue since Frances exited the bathroom, and any noises generated in this room have been from me expressing my pleasure.
I hear the dildo placed on a nearby table, and then Frances reaches for the lube.
She lubes up her dick with it and I can hear the lube squishing as she pumps her cock in her hand to distribute the lube.
In a quiet, girlish tone, she says, "This might sting a bit, dear, but I'll be gentle."
And she is, as she begins to insert me from behind.
She pushes against my ass, sliding into me slowly. I take a deep breath, as the girth is slightly larger than the dildo. She fills me up completely.
She follows the same procedure as with the dildo, slowly in and out.
This combination of intense pleasure and slight discomfort feels amazing.
It's been quite a while since I've noticed her hands are on my hips. When did she put them there?
She tightens her grip on my hips as she uses more of her weight to thrust harder into me.
She's as deep in me as the dildo used to be, and I'm not sure how much bigger she is than the toy.
With her cock stretching my tight ass, Frances spends a moment exploring my nyloned legs with her hands. She starts with my ankles, caressing the areas she can reach, ensuring she stays inside me. She continues to touch the front of my nyloned legs before taking up her previous position on my hips again.
Oh my! Frances starts fucking me with incredible strength and intensity. She's no longer being so gentle, now humping my ass with considerable vigor.
I ejaculate. I have cum all over my tights in thick ropes.
"I've cum. Oh my God Frances, I'm sorry."
She doesn't respond, doesn't change her rhythm at all - just keeps ramming me harder and harder, and I keep cumming like I've never cum before.
It's so intense and fast.
I can feel her cum, and it feels fantastic. She withdraws and I collapse onto the bed.
I'm lying on the bed with Frances stalking me, snapping pictures with my phone. I don't know when she started taking the pictures - probably the whole time.
Afterward, we just sit on the bed. Two dressed-up crossdressers.
We didn't feel uncomfortable since we had talked online before.
I had my saved Internet images playing on the TV, and was beginning to get turned on again.
I was seated there, still in my wet tights after coming, when Frances jumped up and moved in front of me. Looking right at me with a grin, Frances bent forward and started sucking my hard cock through the wet tights. She licked me softly, swallowing up the cum from the material, which made me even harder.
Licking me tenderly, sucking and cleaning, Frances said, "Untie your tights, sweetie."
I obliged, pulling them down just enough for her to continue sucking my firm cock.
Here I was, debating between watching my porn on the TV and watching Frances sucking me.
I grabbed my phone and began snapping pictures of this scenario. My fantasy had come true, and now I had photographs to appreciate it time and again. I took pictures of the room, Frances grinning at me.
This was the moment that caused me to climax again.
Frances took it all. She swallowed and swallowed, and just minutes later, she sat up and simply stated, "I need to leave now."
Her abrupt departure surprised me.
"Did I do something wrong?"
"No honey, This has been equally enjoyable for me as well. But this is all the time I have."
I could only say, "Okay."
Frances got off the bed, went to the bathroom, and soon I heard the shower running.
The idea of joining her in the shower momentarily crossed my mind, but it didn't excite me at all. The thought of showering with a man, who was that beautiful, enjoyable woman with me, did not entice me in any way.
I felt just a bit awkward and grabbed a hotel gown to wear over the top of my female disguise.
When the bathroom door opened, there was no hint of Frances. Instead, the same man with the boyish, somewhat femme face in street clothes with sneakers and his gym bag appeared.
Frances said goodbye, without much emotion.
I said, "Bye Frances, I'll chat with you later."
To which there was no answer as he left and closed the door.
I sat on the bed, contemplating that while Frances was a fantasized part of my dreams, possibly I was a part of hers as well.
Read also:
- Exploring the Springs: Part 2
- Harry Herrick's "Summertime Without Clothes" Part 1
- Woman in Fitwilliam Lineage: Instruction
- The Leader and the Scholar
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