It all starts, innocently enough, when Joanna's looking for a dresser. On one hand, she can just go to a big box furniture retailer and get an inexpensive, functional one that looks decent (and build it, of course). Or, she can browse around online and find a new or used one with a more elegant pedigree.

Joanna, by the way, is a very practical, elementary schoolteacher of medium height, 30ish with boyfriend, a rather buxom blond with fairly generous hips, attractive lips and a pleasant but always curious demeanor. She wears her hair long, likes pencil skirts and tasteful makeup.

She thinks she's typed "dresser" into her browser, but what pops up and what she innocently clicks on is a photo-sharing page titled "cdannette" and then a series of photos of mostly attractive women taking selfies. So Joanna keeps scrolling and then there's a photo of a woman with what appears to be a penis! Or is it a strap-on dildo? Upon a VERY close examination, Joanna decides the erect organ is definitely a penis, and a large one at that. Certainly larger than her boyfriend Richard's.

Joanna starts to piece things together, and being the avid crossword puzzle maven she is, quickly realizes that "cdannette" is short for crossdresser Annette. Certainly Joanna has seen crossdressers before - several times in real life, but more often in movies. But never with an exposed tool.

She scrolls down and finds another photo of an even more attractive woman. Joanna is fascinated, first by her beautiful Hispanic face and lips and saucy attitude and nicely formed bosom, but also by a well-formed, erect penis. Its upward arc is near-perfect.

Rather turned on by the image, but not exactly familiar with the photo-sharing site, Joanna finds she can click on the link next to the photo and go to "marisamartina." This leads to more photos of this rather sexy woman, Marisa, sometimes displaying her dick, but always looking flirtatious and inviting. And then Joanna sees photos of Marisa with ... what must be Martina.

Martina doesn't exhibit any vestiges of maleness (like, no penis) and she's also good-looking. So, what's between them, Joanna wonders. Are they just friends, and maybe Martina helps Marisa with her female look, or are they lovers, or?

Then, OMG, there's a little .gif video of them doing it, except it's not crossdresser Marisa doing Martina, it's Martina with a big black strap-on dong doing Marisa in Marisa's little arsehole. Martina looks pretty athletic and is humping Marisa with great vigor, and Marisa is practically swooning with pleasure. Still, Joanna isn't shocked, but rather, fascinated, thinking, "... of all the wonders of nature, I have come upon this little corner of the world."

Joanna goes to bed that night with some blankets tucked between her legs, as is usually her habit, but as she lays there a new, almost forbidden thought creeps into her head ... of a woman in bed with her - maybe Marisa - and this woman is hugging her, and their breasts rest gently against each other, and then this woman, a little like her boyfriend Richard does, deftly inserts her hard penis into her, and slides inside, and fills her. And the penis is alive like a fish inside her. This vision so turns Joanna on that she soon finds her clit and rides the crescendo of an orgasm to its rollicking conclusion. Her peak is all-consuming, more powerful than some she's had with Richard (with Richard, she's always so concerned about him being satisfied).

She speaks to Richard maybe every other day, but she doesn't talk about women with dicks.

So, the next night she's back in front of her laptop, wearing a comfortable nightie, and she goes to marisamartina again. After a day relating to children, their parents and other teachers, she's very ready to explore the World Wide Web of wo-men once again. Now she impatiently scrolls past the photos and video she saw before, and sees photos of the lithesome Marisa and Martina out on the town and at parties, looking like two totally happy friends, all dolled up and beautiful. And then there's another video of, this time, Marisa fucking Martina - her nicely formed rod entering Martina's cute shaved pussy.

Joanna is amazed that people post such personal and intimate things on the Internet. But as she feels some wetness from excitement down between her legs, she's glad they do.

How does Martina feel, Joanna wonders, being balled by a person who totally looks and acts like a woman but with a man's warm rod? And then Joanna wonders - does Marisa live all the time as a woman, or is "Marisa" a once-in-a-while creation? Maybe Marisa is Mario, a car salesman? Funny.

As Joanna continues to scroll to new pictures, she finds even more excitement. There's a .gif of Martina giving Marisa, OMG, a blow job, so erotically done, with Marisa's eyes closed and obviously in heaven. Joanna wonders if anyone else was in the room taking the video, but sees no camera movement, so it's most likely just the two of them.

It's already midnight when Joanna forces herself to close down the computer - how time flies when one's being stimulated! Being quite aroused after an hour of looking at marisamartina, (with photos of other chicks with dicks too) she slides into bed, and wastes no time putting blankets between her thighs and finding her pleasure nubbin again. Now, she almost guiltily imagines lying on her side in bed with Martina spooning her from behind and fucking her with her strap-on, and Marisa in front of her, inserting her penis into her mouth, and tasting it, and cradling Marisa's balls gently with her fingers. With all the imagined stimulation from both ends, a swelling of the most beautiful music fills Joanna as she rides the most extreme orgasm of her entire life. It's so good it's scary.

Before she goes to sleep, she wonders if this new level of excitement will ruin sex with Richard. Poor guy. He tries so hard to be the perfect boyfriend while she tries to be the perfect girlfriend.

On her next sleepover with Richard, she again doesn't mention her new fascination, but eventually asks him to try on some of her panties, "just to see how you'd look ... ." But Richard, who always wears boxer shorts, quickly squelches that idea. "Then let me put some lipstick on you, just to see how it'd feel to kiss lipstick." Richard actually looks a little scared and shocked that Joanna would seek this detour away from their usual sexual track, and she gives up, but hopes she's planted a seed that might grow in his mind.

When Joanna reaches climax with him later, in bed, with her eyes closed, it's because she's strongly fantasizing that he's Marisa; the girl with the dick.

So, brimming with interest and fascination, Joanna continues to browse the Web around the subject of chicks with dicks. One evening she remembers that at her previous Catholic school of employment, she'd heard that one of the male teachers, Kenneth, was rumored to be into crossdressing. Her fellow teachers there had comments like, "Didn't you see that trace of mascara around his eyes?" and "I saw him shopping for lingerie at Macy's." Nonetheless, none of this resulted in any parent or school administration difficulties. He was, overall, one of the more popular teachers.

And then there was the fact that Kenneth was married ... with no children.

Joanna's never one to be shy, so she emails Kenneth on the pretext of catching up on news at his school. He responds promptly, telling her at length about the latest gossip, and all about their new principal. Then he in turn politely asks about her working in a public school.

Eventually, after a couple exchanges, Joanna asks about his wife.

"Oh, I should've mentioned it; I forgot. We separated eight months ago. We're going through an amicable divorce."

Joanna: "Oh, I feel so sorry for you. I always thought you were beautiful together."

Kenneth: "Nothing awful; it was just one of those things. She was promoted, but had to move across the country for her new job. She'd be making a lot more money than me, and expected me to move with her, but I love this town and school too much."

Joanna: "So, are you seeing anyone?"

"Not at the moment. But soon, I think."

On the pretext of helping him feel comfortable with going out again, Joanna meets Kenneth (he never liked being called Ken) at a trendy crepes restaurant for breakfast one warm Saturday morning. They eat outside under lovely trees. She's wearing a long, white camisole top which extends a ways down over her gray-and-blue patterned leggings. It nicely cradles her breasts. She's let her hair fall down around her shoulders and her elaborate earrings. She wants to put herself out there without seeming cheap.

She wonders if Kenneth has aged. After a hug and greet, and some early patter, and placing their orders, she sees just a couple gray hairs in his generous hank of dark hair. He's wearing khaki shorts and a somewhat tight long-armed T-shirt with his college alma mater emblazoned across it. Underneath, his nipples show through. She scans his face: no trace of mascara today! No leftover lipstick around his mouth. But - aha! - he's sporting tiny stud earrings in his pierced ears.

"So nice to see you again, Joanna. You look great, you really do." From time to time, his eyes settle on her bosom. He seems relaxed and reflective.

They enjoy sparkling mimosas along with crepes and are soon feeling like old friends.

Finishing up, Joanna prods him along by asking if he still lives nearby.

"Yeah, I'm still using our old apartment over on Third. I have a roommate to share the rent."

"Someone I might know?"

"No. Guy named Francis."

"So, I suppose that now with just two guys, it's not quite as neat as a pin as before?" Joanna remembers visiting it once when he was married.

"We do OK with it. Francis is a bit fastidious, in his 40s."

"Sounds like the Odd Couple," Joanna laughs.

Finally, Kenneth takes the hint. "Like to come over for a glass of wine?"

She pretends to be surprised. "Ah, sure, why not?"

And so, yes, Kenneth's apartment is in decent shape, and Francis is nowhere to be seen. They enjoy some $25-a-bottle red wine from Chile, along with a couple croissants. The sun illuminates the wide-windowed living room as Joanna leans over to gently kiss him. Her breasts lightly contact his chest. Her hair falls around his.

"Ah, Joanna, whose lips taste of wine." Kenneth is very delighted, especially since he isn't the type to make the first move.

"Can't have you wither on the vine, now can we?"

Joanna runs her hand up his shirt and over his erect nipples. "Maybe it's time to jump on a bed somewhere?"

Kenneth is a bit taken aback by her forwardness, but is obviously worked up. "Joanna, give me just a second or two to straighten up."

After an energetic making out and fucking, with lots of heavy kissing and entwining of bodies, and satisfying ohs and ahs, Joanna is very pleased with herself, helping to bring him back into the world of the living. She excuses herself to pretty up in his bathroom, where she puts her rather sexy bra and panties back on - and has a chance to check out his laundry hamper. There, amid Kenneth's male briefs (sexy) she also finds panties, a bra, several pair of pantyhose, and a dress. Yes!

Inserting her arm into one of the legs of hose, she emerges, quipping, "Dear me, looks like someone else has been helping you recover as well ... ."

Kenneth's face goes through two shades of red. "What can I say, I mean ... ."

Joanna sits next to him on the bed - he's totally naked - and runs her nyloned hand lightly along his face. He instantly has the most ardent, vertical erection.

"My, my. What have we here? I'd swear you're into lingerie."

"Well, aren't most men turned on by these things?" he squeakily manages to ask.

"Oh, look, Kenneth. I have to come clean. Look, I kinda already suspected you were into crossdressing. I saw you shopping for lingerie once. Spying on your hamper confirmed that, yeah. But I'm not going to make fun of you."

With that, Joanna takes Kenneth's hand and places it over her bra's cup. Kenneth's cock shows a renewed vigor. "In fact, I like that about you."


Joanna notices Kenneth's eyes getting watery. "Yes, really, I'm not putting you on. I'm not making this up."

"OK, it wasn't OK with my ex. I had to do it when she was away."

"Well, I'll bet you look nice. You're slim and your face isn't too rugged and your voice not deep. Can you show me some photos of yourself dressed up?"

Kenneth, it happily turns out, is quite an accomplished crossdresser. With the same intelligence he needs as a teacher, he also applies to his feminine arts. He once arranged to have a professional photographer known to the crossdressing community do a photo shoot, and the results are quite sexy.

Kenneth also shows Joanna his wardrobe, greatly enhanced since his split. His taste is spot on, and even Joanna is somewhat jealous of his collection.

Finally Kenneth reveals his femme name: Audrey. So, Joanna figures, here I am with an Audrey. A real chick with a dick. I am so, so lucky. I am sneaky, but yay when my plotting yields results!

Joanna: "Audrey, might I stop by sometime when you are enjoying, shall I say, your alter ego? Because I think I might find that very exciting."

Kenneth looks like he's died and gone to heaven. He manages an excited "yes."

Joanna: "Believe it or not, this is all because of an dresser I was looking to buy. But I'll tell you about that some other time. - Oh, by the way, what does your roommate feel about all of this?"

"I chose him carefully. His femme name is Frankie."

"Oh, dear me, is there anything between the two of you?"

"Just that we're often dressed around each other. In fact, almost always when we're here together we're enjoying our female incarnations. But we have this hard and fast pact: because I'm a teacher at a Catholic school, we never leave the apartment dressed. Have to be so careful, you know. ... Once Frankie and I went, believe it or not, on a cruise just for crossdressers and their friends, or spouses or whatever. A real Love Boat. ... But no, Frankie and I, yeah, we're not lovers, if that's what you're thinking. But the trip was such a GAS!"

"When to get together again, Audrey? What size panties do you wear?"

She doesn't buy him just one pair of panties, but three. What wonderful fun to dress a man with sexy stuff. Trying to figure out what might look good over his tool, over his butt, around his hips ...

On Saturday, after both have had time to recover from a long teaching week, she arrives for a promised dinner - just as Francis is leaving. Francis is plump, and Joanna quickly imagines how he would look female, as he already has long flowing hair. He's introduced as an advertising graphics person. His large-frame eyeglasses seem quasi-female.

As Francis exits, Joanna appraises Kenneth, or rather, Audrey. Audrey exceeds her expectations and then some. "She" has obviously gone the whole route. First, Joanna's eyes go to Audrey's face and hair - so sexy! Tasteful yet beguiling eye treatment, some facial makeup (no beard trace, of course), and a lighter-red lipstick color Joanna might've chosen for herself ...

And her hair looks so natural - long, light-brown - maybe it's a natural-hair wig. It has just the right amount of shine ...

"My, Miss Audrey. You have outdone yourself."

"Thank you. I wanted to impress," says Audrey softly, smiling, having dropped her Kenneth voice.

Joanna stands back to take in the whole girl. Audrey's wearing a soft-fabric designer dress, a bold-patterned, Mondrian-ish, half-black, half white creation that nicely emphasizes her boobs, waist and hips. Funny, Joanna had never noticed Kenneth/Audrey's hips before. Are these really his/her hips? Completing the picture are black textured nylons and three-inch black heels. And underneath, down there somewhere, yes, is Audrey's male thingee. Now, it's Joanna who feels she's died and gone to heaven.

There's even the subtle hint of perfume in the air.

Joanna is quite outclassed in the clothing department. She's only wearing a deep violet tunic with leggings underneath, a multi-strand Hawaiian necklace and lazy leather sandals, along with a subtle lipstick. But underneath - her sexiest, matching balconette bra and thong.

Audrey loves the gift panties.

Beyond bringing forth her female self, Audrey brings forth a three-course dinner, all made from scratch, along with more good wine.

Sated, and a little sleepy after eating too much, Joanna thinks to herself she could be happy enough just being in Audrey's presence, taking her in, being around her. But eventually, she can't help herself - knowing that Audrey is never the one to make a move.

"Audrey, how did you get to be such a great cook? Some lucky girl will marry you, and be thoroughly happy letting you do all the cooking."

"Well, I'd be happy if she would accommodate me being Audrey, so I wouldn't need to be closeted. I mean, I'd be happy to cook for her, as Audrey."

"Tell me something, dear - what is it about being Audrey that you like so much? I mean, do you figure on getting to the point where you want to transition to a woman, completely?"

Audrey fidgeted. "I don't know. I haven't thought a lot about it. I've been dressing in secret, off and on, since I left high school. Yeah. At first it was more an erotic thing; you know, when you get so instantly aroused and your hormones take over. And - such a gas to look like a girl, and imagine being one! Wearing a bra. And then, over time, the turnon is still there, but then a maturity kicks in, like my mind becomes smoother and happier when I'm dressed, and I so enjoy picking out what to wear, and figuring out how to make myself the most attractive wench possible. Oh hell, I'm talking on and on now."

"I think women have so much more freedom dressing than men," says Joanna. "If a woman wants to wear a business suit, and tie, and short hair, nobody seems to give a damn! ... But I must tell you, that I find your Audrey quite a turn-on, not that I'm a lesbian or anything, but ..."

"That's nice," admits Audrey.

"I mean, I really do see you as a woman. A woman with a little extra."

They both laugh. And with that, Joanna rises, walks around their dinner table, and begins kissing Audrey on the nape of her neck. Oddly enough, Joanna finds herself fantasizing that she has a dick and an erection, and that some male part of her is coming out. Good God.

She puts her hands under Audrey's tits, curious as to how they feel. A little more firm than real ones, but one can always imagine. They must be silicone, like breast implants, she thinks. Nice.

Now, she playfully bites Audrey's earlobe a little, and with that, Audrey shivers a little. And stands up. They fully embrace, hips to hips, breasts to breasts, just a little awkwardly, and then, kiss - ever so gently at first, just teasingly brushing lips and noses.

Joanna inserts her leg between Audrey's, and pushes. And Audrey pushes back.

Joanna kisses Audrey's neck, and then finds her way back to her lips. There's more urgency now, and both women seal and fuse their lips together, with tongues meeting too.

In bed, under covers, in a darkened bedroom, Audrey has stripped to bra and panties, while Joanna's down to her thong. There's the excitement of slightly sweaty skin meeting skin, a hint of perfume, and the taste of each other's lipsticks. Audrey reaches down to run her fingers lightly over Joanna's hairless cunt and begins to suck one of her nipples, making Joanna breathe deeply.

Joanna really feels she's next to a woman, even though the body next to her isn't quite as soft and smooth-curved as she might wish. "I so love this. I could go on all night," thinks Joanna.

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byValoryG© 5 comments/ 13736 views/ 14 favorites

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