My Russell Hustle Pt. 01

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The play's the thing with two crossdressers.
1.7k words
4.56
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Part 1 of the 6 part series

Updated 06/12/2023
Created 06/30/2022
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ValoryG
ValoryG
287 Followers

(This is a work of fiction. Any similarity to persons living or dead is purely coincidental.)

This was our third get-together. As before, I drove an hour and a half to his place because, for some reason, he was afraid to come to my town. Russell, a.k.a. Rene, was as usual dressed in his/her usual "wench" look: long, dark hair; bountiful, shapely boobs; pencil skirt; nylons of course; and tasteful two-inch heels.

Oh yes, about me: Jessica, 15 years older than her (Rene is 20), but highly practiced in the art of crossdressing. This time I'm wearing a soft but tight sheath dress (knee-length), lavender in color, long sleeved, so nicely fitted to my boobs. To this I've added leather sandals and a nice, brown, shoulder-length wig. I really maxed out my makeup for this trip (driving on a freeway is so much fun when I'm thoroughly, completely "Jessica").

After our soulful hug as I entered her apartment (Rene is quite a shy one) we engaged in some small talk as she went about preparing a most wonderful dinner -- the aromas captivated me just as she herself had captivated me from day one. Rene works for a food photography studio, helping to prep dishes for the photographer. Along the way, she learned a lot about cooking. In that role in the studio, though, she's Russell.

They pay her well, and that's enabled her to build a wonderful -- thoroughly "Rene" -- wardrobe along with quite a variety of makeup bottles, jewelry, and whatnot. More than I have, in fact.

The first time I came to visit (after we'd met at a crossdressing gathering) I dressed at her place alongside her. But since then, we've met already rigged out as Rene and Jessica, leaving our maleness behind.

"How have you been doing?" I ventured as Rene skillfully handled fry pans and a cutting board. I always have to break the ice with her.

"Oh, just fine, I guess. I was really looking forward to your visit. I couldn't quite decide what to wear."

"Well, you may not believe it, Rene, but you really do have such a style sense. I know you've never gone out in public as Rene, but you could pass so easily."

"Oh, but my voice would give me away. My big feet."

"You're too self-conscious, dear. I think you're so attractive. Don't you sometimes wish you could just flip a switch some days, and just become a genuine woman for a day or two? And then return to maleness? Or maybe you'd like to totally become a woman? You've never said."

Rene was taking a casserole out of the oven using hot pads. As she bent over, I got a nice rear view of her wonderful derriere.

"Oh, I don't know," Rene chirped. "Right now I'm happy just being Rene at home. I guess that meeting you was a next step for me. Socializing more."

The meal was exquisite. So good that I promised to take Rene to an expensive restaurant some time (because I'm a poor cook). That is, when she felt comfortable enough to go public.

To be quite honest, ever since I met Rene, I've been sexually attracted to her. I never want to see her as Russell again -- to me she is only "Rene," a woman with a prick.

My current state of affairs: I'm a divorcee, with no kids, living alone (usually as "Jessica"). I work in commercial real estate. I socialize a lot, mostly in my male role.

On my last (and second) visit, I had come very close to kissing Rene fully (I think she'd wanted it too), but I only got as far as hugging her, and kissing her lightly on her cheek as I left. Since then, I've had fantasies of a full kiss, and coiling our bodies together. Even though I'm 35, I too can be a bit shy. But not as shy as Rene.

Rene served some dark, excellent Zinfandel wine during dinner and that loosened us up a bit.

We talked about TV shows we'd seen; about politics; about how the prices of women's apparel, makeup and so on are going up too fast; and about a crossdressing event coming up.

I've concluded that Rene really is a woman inside, and over the meal I was drawn even more to her looks and innocence. There really isn't a crafty or devious bone in her body.

Afterwards, in her living room, she found a way to stream that old and zany movie "Some Like it Hot," with Jack Lemon and Tony Curtis in drag, and of course, Marilyn Monroe. It had been years and years since I'd seen it.

We were sitting, two broads, side by side on her plush sofa, still nursing our refilled glasses of wine. Laughing, making comments about the performances.

At some point -- I don't think it was deliberate -- our bodies touched -- and we didn't pull away. Then our thighs touched. But we just sat there, not acknowledging this at all. Disregarding the electricity between us.

We did this all through the movie, and when the credits began to roll, I did this nutty thing of imitating a wedding couple, where they link arms and drink their glasses of champagne through each other's arms (too bad one of us wasn't dressed as a bride!).

At first, I was rather clumsy and Rene didn't understand. Then she did, and we managed to pull it off with giggles. I looked at her sexy eyes and downed the remainder of my wine.

Then, just as clumsily, I slowly approached with a kiss. She looked like a scared rabbit. I stopped inches short of her lips (to which she had artfully applied lipstick after dinner). She was about to turn her head away to decline, then stopped and looked at me soulfully.

"Jessica," she said almost in a whisper, "I don't know about this. Couldn't we just be friends and bosom buddies?"

I took a chance, saying quite quietly, "When I left last time and gave you a peck on your cheek, I really felt that you very much wanted a real kiss. Yes?"

"Well, maybe."

"Here we are, enjoying each other. It would seem such a shame if we didn't do what we want to do, deep inside."

"I don't know."

With that, my lips did approach hers, and I lightly brushed them.

That's all it took. We were soon engaged in a very full kiss -- her lipstick against mine, and soon the tips of our tongues touched. Our arms wrapped around each other, and I loved feeling her tits against mine.

"We really kissed," she said. "I enjoyed that."

So we kissed again, longer this time.

Now, I really wanted to reach down and touch her boi clit, but I held back. The kiss had been enough.

Soon, it was time again for our usual show and tell. I brought a few photos of me wearing some new outfits I'd bought. She took me to her bedroom to take hangers of new outfits out of her closet to display. Then she reached into some drawers to show off her new lingerie purchases -- panties, bras, a nightgown or two. Even a sexy half slip.

"Rene, you have such taste. We kinda like the same things. Lacey, mostly white, with a risqué black confection here and there."

Then I gambled again. "And what panties are you wearing now?"

I guess the wine and kissing had gotten to her, because after a moment's hesitation, she hiked up her skirt just high enough to provide a glimpse of some lace-fringed, slightly tan-colored panties under pantyhose.

"I love it, dear, but can't you show me more? Girls share, you know."

We both laughed.

After hesitation, and with a half-serious demeanor, she had me unzip the back of her skirt (quite a sexy operation!). As it slipped onto the floor, I urged her to remove her expensive and sexy pantyhose, which she accomplished like a practiced pro. Finally, feeling a little liberated, she wiggled her hips sensuously so I could fully appreciate her panties.

She was completely devoid of body hair, which helped preserve the illusion of her

woman-ness.

Now -- she seemed as surprised as me -- her cock came alive and pushed against the stretch fabric of her panties.

I couldn't keep my eyes off it. I wanted to reach out to pet it, but something held me back. Meanwhile, I felt my own cock pressing against my panties.

"Don't be embarrassed, Rene. Tell the truth, I really like to look at pictures of crossdressers with big erections under their panties. What a turn-on."

Looking aside, she managed a "Me too."

To move on from her embarrassment, I said, "Well, since you've been so kind as to show me your panty, would you show me your bra too?"

She was beginning to enjoy this show. Maybe she had fantasized about doing it, I don't know. But off came her thin cashmere sweater. Underneath was the sexiest, light-blue embroidered bra, not showing a trace of breast forms underneath. It helped that her figure was close to that of a woman, except for slimmer hips.

I whistled in appreciation.

Rene came to sit on the bed in her attire, and then lay down, with her head and shoulders propped up by an elbow.

Rene's cute (or is a better word, "powerful"?) erection still raised her panties into a tent. Her eyes and small smile said it all. I knew exactly what she and I both wanted.

I reached out with my full hand to touch the top of her prick, now quite wet. She stiffened briefly and sighed. I looked again into her sexy eyes, which had closed for a moment.

Then I pulled my fingers down a bit, pulling the panty fabric tightly against the head of her penis. I totally loved to see it like that. My own erection was getting stiffer. I pulled my fingers down further.

Her hair-trigger pelvic muscles made her cock twitch several times. I wondered if she was going to explode on me! So I took my hand away, and went to explore the contours of her bra. The straps. The embroidery.

She was breathing deeply, and seemed so completely pretty and passive at that moment. I had the feeling that I could, at this point, do anything I wanted, within reason. I had seduced her.

ValoryG
ValoryG
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2 Comments
JDonna1996JDonna1996almost 2 years ago

Really looking forward to seeing where this story goes next!

JasmineHeartJasmineHeartalmost 2 years ago

Mmm. Slow silky seduction, and her first kiss too. She is lucky to have such a wonderful friend. I hope she finds her bliss.

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