In My Room

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A crossdresser has sex (?) with a neighboring couple.
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Here I am in Daytona. I'm staying on the beach at a "resort" along the strip. It's a nice hotel but I'm not sure I'd describe it as a resort. I'm on the fifth floor and the best feature is the ocean view. My room's wide sliding glass doors and balcony look down on the Atlantic to infinity. It's chilly out but that's OK. Don't travel to Daytona Beach in January or February and not expect to be cold.

I'm sitting here in my underwear typing on my iPad. By underwear I mean colorful microfiber bikini panties and sheer-to-waist nude pantyhose. The door is cracked so I can listen to the relentless, rhythmic rush of surf, so I've pulled on a loose-fitting top to combat the chill. I'm seated only a little more than a meter away from the opening, and the ocean air is leaking in. My slender feet are sheathed in a pair of strappy sandal flats. The sandals are open-toed, the wide straps ivory in color. I also packed a red pair, my favorites. Though I prefer to wear them with black stockings.

Although now considered old-fashioned, I love pantyhose. They not only keep my legs—and joints—warm but feel creamy and massaging against my skin, my shaved legs. In addition they're far cheaper than thigh-highs, which also tend to quickly develop runs. It's a bitch to pay fifteen dollars for a pair of lace thigh-highs, have a man over and then only get one wear out of them. Because of my height the pantyhose are a plus-two size. I purchase them online from No Nonsense. My panties are Jockey brand, one of their ever-changing designer styles. This pair features a flower pattern against a purple background. As usual the pattern's colors are somewhat unrealistic, the design rather abstract.

I used to wear Olga's, creamy, sensuous microfiber ones with lace waistbands, but they stopped making them. I switched to Jockeys. I love the variegated patterns and they fit like a dream. And they're VERY cute.

Theoretically my neighbor to the south, one room over, standing on their balcony, which juts out forward of mine by balcony's depth (about five feet), could, if they were standing in its north corner, look back and see me sitting at the end of the desk in my room and comment, "Our neighbor's sitting there wearing nothing but their underwear."

Husband (excitedly): "A woman?"

Wife: "No, a man."

Husband: "A man in women's underwear?"

Wife: "Well, from the waist down."

Husband: "I've got to see this. Move!"

Wife: "Shhh! He'll hear you!"

Husband: "I don't give a shit!" Then: "Holy crap!"

Wife (whispering): "Not so loud! He'll hear you!"

Husband: "Fucking weirdo!"

Later, back in their room, one identical to mine, after both have showered, the wife might suggest to her husband, "Maybe we should invite him over for drinks tonight."

"Who?"

"Our neighbor."

"The faggot?"

"He's a crossdresser. Doesn't necessarily mean he's...gay."

"Of course he is, Karen [or some similar, common name]. And why do you want to invite him over?"

A coy smile: "For kicks. Could be fun."

"How?" the husband asks dubiously. Karen shrugs.

"He could dress for us. We could sit around...have drinks."

"What, like some kind of carnival act? A freak?"

"I didn't mean it like that, George," putting a downward spin on the name. "He's obviously not shy about showing himself. Maybe he'd enjoy being with other people."

"She," George says sarcastically, in correction.

"We promised each other this was going to be a fun trip. Different," Karen reminds him, again with descending emphasis. "I'm sixty now George," this time reminding hubby of the reason for the trip. The flight out of the cold Midwest. The thousands of dollars this vaca on the famous beach was costing them. "I want something different. Once in a lifetime."

"Maybe you should sleep with him," George suggests, the insult darkening his deep voice.

"I doubt he's into that."

"He could pull his pantyhose down and..."

"I was thinking...," that coy smile returning to whatshername's face, still attractive at sixty, still sexy, "...we could have drinks. Then the three of us together."

"Doing what?"

"Whatever happens."

"Me in bed with another man?" George asks incredulously. "Is that what you—"

"I'd be in bed with you too, George. It would be like having two women."

"He's not a woman. He may dress like one, but..."

"You told me once, a long time ago, the biggest thing in those adult films you like to watch was she-males."

"It is."

"Well?"

George clucks his tongue. He's getting dressed, trying to hide from his wife his swelling penis. Its attempt at swelling, anyway. "A she-male IS a woman, Karen. She just has a cock and balls, that's all."

"Oh is that it?" Karen half-laughs.

"That's it," her husband replies definitively.

"Well, who knows, George? He may have a wig? The whole deal? We could ask him if—"

"I'm not asking him anything. I don't want to talk to the creep."

"Well maybe I will."

"Don't even think about it, Karen. Wipe that idea clean from your mind," George says with a sweep of the thick arm.

"What if I can't?" Karen again smiles. "It's my fantasy..."

"It's a fantasy that HE, sitting over there typing on his little thingamajig, put in your mind, Karen. Forget about it."

"Well maybe he'll write it so I go over, later in the day if he's home, and knock on his door."

"That's crazy talk, Karen," swinging another arm. "Just drop it. I thought we were going for a walk on the beach."

"We are," Karen sing-songs, her mind obviously elsewhere.

"So this is some kind of Lesbian thing," George, a spectator at this point, comments. "Zat it?"

Given that both our mouths are occupied at the moment, in the 69 position, with me on top, the forward curl of my blonde wig, a page-boy cut, draping both my powdered cheeks, neither of us answers.

"What am I supposed t'do?" George asks, his sixty-year-old erection, a surprisingly big one, in hand. "Jack off?"

Karen lowers her head, and turns it, her frown, left, and says, "Just be quiet, George. You had your chance."

"My chance to do what? This has been about you two the whole time. All the chit-chat. Kissing on the couch—necking. You groping him in his little," George's tone turning denigrating here, nasty, "girly panties. You prefer his cock to mine? His little balls?"

"Maybe I needed a change of pace after twenty-five years, George."

"Change of pace...," her husband mutters, with a shake of the head.

Despite the cold Karen, a little earlier, put on her one-piece and took a dip in the ocean, the waves. Not a long one—just enough for her to emerge, and to remain now, tasting like the ocean: salty but pure, integral with it, delicious. Like fresh sea urchin on a sushi board. I lick and suck her eagerly, each of my hands under her meaty, pocked thighs. She also smells of nylon, wet nylon.

Afraid I'll cum, prematurely, as is my wont, down Karen's throat, I pull away—abruptly.

Karen frowns, head having fallen again to the double stack of pillows: "What's wrong?"

"No," I reply rather breathlessly. "No, nothing. It's just..."

My panties, my pantyhose, are down around my knees in a figure-8 twist. I stare at them wondering: Should I pull them up?

A disappointed-sounding Karen says, "George, if you want me now's the time..."

"And it's about time," he responds, climbing on the bed even as I awkwardly slide off, a wad of descended nylon and microfiber in hand.

As Karen's thickish legs rise and her husband, on his knees, advances between them, and penetrates her, she says, "Maybe our new friend here can lick me after you cum in me, George. How 'bout that?"

"Ugh!" groans the husband. "You guys do that and I'm outta here. That's disgusting!"

"Well you won't have to be here then, George, will you?" her husband beginning his crude, bucking-bronco motion. "It'll be him and me."

"Good! I'll be long gone!"

But not, it will turn out, long in the saddle.

"Forgive my husband," Karen will say, up on her elbows now watching me eat her. Watching me lap up the fresh cream as it leaks out. She giggles: "Your wig! It tickles!"

I raise up, take a break, my face, the lower half, a mess. Wet with semen, juices, red lipstick smeared long ago. I must, to Karen, look like The Joker. "Sorry," I say, before diving back in. I push the forward curls back, but...

"So how long have you been dressing up? Mind if I ask?"

"A long time now," I swallow. "Nine...ten years? Since my divorce."

"You were married?"

I nod, wipe my face, my chin. "Yes."

"Did your wife know you...?"

"No. It started before the divorce, but..." I paused before explaining, "Once we split up I started in...earnest."

"We'll you're very sexy, dressed, hon."

"Thanks."

"Great legs."

"Thank you."

"I know a lot of women who'd kill for 'em."

"My ex used to say...," I began to tell Karen, to brag, "...with my legs I should've been a girl model."

"You should've been," Karen agrees, with a giggle.

"Well..."

"You just about done?"

Another nod.

"You like to suck cock?" Karen surprises me by asking.

"Yes," I reluctantly admit. "I love to."

"You should've sucked George's cock before he put it in me."

Warily, I reply, "I don't think your husband would've gone for that."

Rising up into the sitting position, Karen's post-middle-aged torso thick, and a little saggy, her breasts, her belly, she counters, "Oh he talks big—big macho guy—but down deep he'd love to have another guy suck his cock. He has a big one."

"I saw," I say, stating the obvious.

"How long are you here for?"

"Till Tuesday."

"So are we!" Karen says jubilantly. "Tomorrow when you come back, if you come back...Would you like to?"

"Love to."

"I would too.

"Tomorrow when you come back...," Karen continues, "after you eat me the first time I want you to suck Georgie's cock. Before he puts it in. In ME, that is," Karen smiles, as if at a private joke. "He'll complain but just ignore him, and go to town. But don't make him cum. Leave that for me, OK?"

"OK," I agree, with a nod. My panties and pantyhose are back up, in place, and my unrequited erection slants off to one side under both sheer nude nylon and colorful microfiber, constrained by thin waistbands.

Noticing it—how could she not?—Karen kindly asks, "Want me to take care of that for you?"

"No, that's OK."

"Sure?"

"I'm sure."

"You don't like to cum?"

"It's not very, you know, fem. Besides..."

"Besides what?"

"I lose interest afterwards."

"Suit yourself," Karen sighs. Knees up, she wraps her arms around them and says, "So anyway. About next time. Tomorrow. Think you could write that into your story? You sucking Georgie's cock before he...?"

"Sure."

"You'll do that?" Karen asks hopefully.

"I'll do it as soon as I get back to my room."

"But that's just it, love," a nonexistent Karen points out. "You never LEFT your room."

Somewhere, down under (I can't tell if it's at beach level, five stories below, or coming from the room directly underneath), a dog barks. Yaps. Presumably at the surfers riding, or attempting to, the waves. This "resort" allows pets.

I think about shushing the little shitter, as it's affecting my concentration. I think about calling the front desk and complaining.

But, finally, at last, the yapping stops and I'm left with the relentless crash of the waves, the sound of it through the open door.

The sun is shining, though clouding over, thinly, white. The water: blue-green. Infinite.


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Private4BrendaPrivate4Brendaabout 3 years ago

Wow! Thanks for sharing this. I can soooo relate to this story, it's something close to what I've done in the past ;)

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