Fateful Jessica

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An unexpected visit proves revealing.
1.5k words
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Fate knocked at the door, I answered it like some automaton and through the frosted glass panel a long-haired figure foreshadowed coming events. Opening the door, my face cracked a smile when I saw it was my cousin Jessica, who lived nearby.

"Hi! Come in!", and I stood back to let her pass, "Can I get you a coffee?"

"Yes, please. I haven't had a cup yet."

"And it's after lunch?", I cut in.

"Didn't finish work until 6am."

"You need a coffee then. Have you had any sleep?"

"A few hours. Enough to start the weekend."

"Sit down then, and I'll put the kettle on. Do you want some tucker?"

"Had an apple on the walk over, and I thought we might go to the cafe, then do some shopping. If you're not doing anything, that is?"

That sounded just right, "No, my afternoon's free. What shopping did you have in mind?"

"Nothing exciting, only the usual groceries, but your company would be nice.", said Jessica with a coy smile.

"I've grocery shopping to do as well, and a pretty face makes the task much more appealing."

"Well, I don't know about the face but I figured you could do with some female company."

At this remark I paused. Jessica had hit the nail on the head, metaphorically speaking. Six months or so since my marriage failed and the pain was giving way to nostalgic remembrances of intimacy, including shopping. Loneliness can colour memories of even the toughest times. My mind began considering what Jessica was doing here, although not by way of complaint.

I nodded, and didn't move. Jessica cradled me in her arms and held me close while a few tears dribbled down my cheek. It had been too long since the fullness of a female breast had been felt against my chest. Soon I snuffled and withdrew from her embrace.


"I'll make you a coffee, and you can relax while I have a quick shower."

Jessica said "Thanks," with what seemed a smile in her voice. Having excused myself, I went to the bedroom that had been shared with my ex, to select clothes suitable for a hot summer afternoon. Cotton panties, light-blue lace bra, cargo-pants and t-shirt seemed the go.

Wandering into the loungeroom, washed and groomed, I found Jessica bringing a basket of clothes in the back door. "Oh," as I realised what I'd pegged on the line yesterday, "Thanks.", and reached out to collect the basket from her. This was one of those revealing moments and my heart beat slightly faster.

"Took my coffee onto the porch and noticed the clothes. They were dry, so I thought it might help if I brought them in."

"Thanks, I really appreciate that," I said while placing the laundry on a spare chair. I'd forgotten what teamwork with the housekeeping was like, and this felt warm and comfortable, despite my wonderings about Jessica noticing my lingerie.

"Merv," and Jessica paused, "Are you seeing anyone?"

It seems Jessica had noticed and was drawing a reasonable conclusion. Now was the time for revealing.

"No, and I haven't since the split, but you're wondering about..."

"I am curious," said Jessica, smiling.

Hoping for her acceptance, while settling for a lack of rejection, I replied, "They're mine," and her eyebrows rose. "Yes, I'm a closet cross-dresser."

"That's interesting, and also, it seems we wear the same size knickers."

We both grinned at that knowledge, then chuckled, and I had a thought of Jessica in a pair of my panties.

"Come on, I'm hungry," Jessica said, and we collected our 'going out' bits n' bobs before heading for the shops.

Fed, watered and provisioned, we arrived back at my place a few hours later. Jessica was going to prepare a salad for tea since it was too hot for anything else, and we stowed her shopping in appropriate places. The last few hours had been among the best of recent months and Jessica had shown great kindness and thought in coming over.

Ordinary activities, but shared with a friend made them extraordinary. Being a cousin got her in the door, and being a friend kept her there.

Jessica now knew of my cross-dressing and that felt good, that a friend knew, and still wanted to make dinner. We'd both worked up a sweat walking home, although it was weather you'd do that by sitting around, and this gave me an idea.

"Jessica, do you want to change into fresh clothes? That is if I have some that fit..."

"Let's see eh?", was her reply.

We went to the bedroom and had hardly walked in when Jessica reached down and pulled her dress up and over her head.

"That feels better," and she laid it over the back of the chair, giving me time to notice her bra and panties, both a similar blue to her dress. "Go on, don't be shy. Your clothes are just as sweaty as mine, and I want to see your underwear too!"

That was a definite invite and I wasn't needing a second one. Off came the t-shirt and pants, and we stood facing each other in only our underwear, and smiles. A few years ago, the sight of a near-naked woman, particularly with Jessica's firm size 14's and well-rounded body, would have sent my cock pointing skyward, but these days it took a little more effort. However, the intimacy of this tableau was a balm to my bruised emotions, and its unexpectedness, a cool shower on this sweltering afternoon.

Jessica moved toward me and enfolded me in her arms. We gazed, kind of awkwardly, for a moment into each other's eyes, then our lips met for the first time. Now my cock stirred as our sweaty bodies pressed together, with only two thin layers of fabric between our naked selves. Lips parted to allow tongues to dance together, before we lay down on the bed.

Still in our lingerie, I reached out to feel the smoothe fabric of Jessica's bra, filled with the warm fullness of her breast. Firm, yet yielding to delicate touch, as I spread my fingers to grasp the contours of this flesh a moan escaped my lips. Jessica lay on her back and my fingers, from starvation, tried to be everywhere at once as they feasted on her bounty.

Across Jessica's stomach my fingers lightly ran, with each lap eliciting a contented sigh from her. My cock strained against its cotton panties, begging with clenched muscle to be released. Gently I kissed each nipple, where it made a tiny tent in the nylon-elastane cups, and Jessica said breathily, "I want you inside me, now!"

We removed our own panties, and kept our brassierre's on. My cock stood at attention; Jessica spread her legs a little wider apart; I knelt between them and supported by my right hand, used my left to lay my cock in the nest of her pubes. The room was hot and our bodies glistened with sweat. Our bra's were damp. With the sigh of a thirsty man receiving a glass of water, I pushed slightly and slipped inside.

Natural rthymns from deep inside our bodies, took over, slow and easy, building steadily, a crescendo of tension, till waves of semen splashed onto Jessica's shore.

All I could do afterwards was say a heartfelt "Thank you.", as we gazed into each other's eyes, before my body, both spent and refreshed, succumbed to rest. It was the classic scenario of the man falling asleep on the woman. When consciousness returned, I wandered out of the bedroom, slightly embarrassed at falling asleep, to find Jessica sipping tea and wearing my favourite pink ankle-length skirt, and a pink bra – no top.

A warm smile greeted me, and I said, quite sincerely, "They look better on you than on me!" It was wonderful seeing my clothes on a real woman, and with this sharing of clothes another log was placed on the fire that we'd kindled this afternoon.

"Had a good sleep?", Jessica replied, still smiling.

"Sorry about falling asleep on you."

"That's okay. I took it as a compliment."

"Huh?"

"That I was good enough to tire you out."

"You were VERY good."

"Do you want a coffee?"

I did, but felt I needed to give this vision of loveliness a break. Jessica had been reading some of my rail magazines, from the pile on the shelf, and that too was a delight to see. She worked as a customer service attendant, what had previously been called a station assistant.

I'd stuck at teaching, finally persevering after a rough first few years, but kept an eye on the railways – my first choice of career. Seeing Jessica in my skirt and bra, sipping tea and reading railway magazines, in the afterglow of our earlier intimacies, was almost a dream, unimagined when I crawled from beneath the sheet this morning.

"You stay there. I'll make it, and join you."

We sipped our drinks as the sun moved toward the west, bringing in its wake the shades of evening and some relief from the day's heat. After we ate dinner, Jessica headed home, sayinig she'd call tomorrow.

Jessica did call, and I headed to her place for afternoon tea. That began a pattern which grew and sent forth a fragrant blossom – our son, Mervyn Junior.

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AnonymousAnonymousover 15 years ago
Wonderful! Is there any more?

As a closeted cross dresser myself I can only dream of such an exciting experience as you have shared with us. You must have more to share with us as your life with Jessica and your son has continued. Please give us an update.

AnonymousAnonymousover 15 years ago
Wonderful! Is there any more?

As a closeted cross dresser myself I can only dream of such an exciting experience as you have shared with us. You must have more to share with us as your life with Jessica and your son has continued. Please give us an update.

AnonymousAnonymousabout 17 years ago
Sooooo glad you wrote this story

Being a long time closet cross dresser, and having had sex with my lingerie on (with both women and men) I can appreciate sooo much your story. It is gentle, sexy and inviting to more stories like this. Am sooo glad you are now writing about our passion, keep it up, plizzzzz

Di

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