Sandra, the IT Exhibitionist Pt. 01

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Streaking and flashing have unexpected consequences.
10.3k words
4.68
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Part 1 of the 4 part series

Updated 06/09/2023
Created 01/18/2020
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SANDRA FELL BACK on her hotel bed and let out a gasp of exasperation. This was not a good sign, she thought, to be so irritated just after the pre-conference cocktail party, before the bulk of the participants had even arrived.

"Smell like a brewery, look like a tramp,

"Ain't got a quarter, got a postage stamp

Tom Waits growled out of her cellphone, buried in her purse. It took her a couple seconds and some more lyrics to dig it out.

"Hi, sweetie."

"How's my honey?"

"I'm cranky, and I'm upset that I'm cranky so early in the conference."

"What's the matter? Classes not go well?"

"No, the classes were great. I love these pre-conference classes, because you get people who already know a lot and want to learn more. It's like graduate school. But then they had a pre-conference cocktail party for the speakers, workshop leaders, coordinators, and some of the people there just pissed me off."

"People you've seen before?"

"You've heard me rant about Charlie Matson from Florida. He's done good work, but I think he's riding on his reputation from five, ten years ago. He's a pompous ass, and he's always got a flock of admirers hanging around> He just got under my skin. And Linda Sterling, you've heard me talk about her. She should know better, but she seems to be part of his flock."

"Sounds like they really got to you." Jerry's voice was always so soothing, that she could feel the tension draining out of her body just by being on the phone with him.

"And how about you, sweetheart? How are the girls?"

"They're asleep. obviously. They were a little wired from our face-time with you earlier this evening, but I got them settled. Mara read to Jessi, and I read to Mara, and they went down around 7:30."

"And how about you, love? How are you doing?"

"Just resting. I've got a photo shoot tomorrow after I drop the girls off, and it'll take me till I have to pick them up."

"Anything interesting"?

"A fashion shoot for one of the local department stores."

"Nobody naked?"

"Not this time."

"I'm sorry."

"I'll get over it. How about you? Are you naked yet?"

"Not yet."

"Well, get to it, woman, You need to shoot my bedtime video. What are you wearing?"

"The black dress with the gold belt."

"The one with the big zipper in the back that makes it easy for me to undress you? Take it off."

Sandra curled up on her side, feeling cuddly with her husband on the phone. "I will. First, I have to take off my shoes."

"Kick them off."

"I have to unbuckle them first. Settle down." She chuckled. "I'm putting the phone down, so I may sound muffled."

"Put me on speaker."

"Then you'll sound like you're coming through a shredded tin can. Just be patient." It was a struggle to undo the tiny buckles on the straps of her shoes, but she finally got them undone and kicked the shoes to the floor. "Okay, now I'm undoing the belt . . . and now the zipper." She rolled over a little more, so she could reach both hands around to the top of the dress and start moving the zipper down, then settled back to pull it the rest of the way down. She pulled it off her shoulders and lifted her butt to take it off. She tossed it onto the floor with the shoes.

She picked her phone off the bed. "Okay, dress is off."

"What else do you have on?"

"A black bra, pantihose, and red panties."

"I thought you weren't going to wear panties when you have pantihose on."

"All in good time. I'll do that when I'm a featured speaker, and I'll feel foxy because nobody will know what they're missing. What should I take off next?"

"Pantihose."

She lifted her hips to get them started, then pushed them down her legs and off. She tossed them across the room, where they landed on top of the TV.

"Oh, that feels good. No more elastic around the waist."

"What's left?"

"I'm unhooking my bra. Oops."

"What?"

"I tried to toss it onto the TV, where the pantihose are, but it hit the floor."

"Now the panties?"

"Now the panties. Oh, cool, they landed on a lampshade. I should leave them there, people will think I've had a party."

"Tell me about your room."

"Since I'm a featured speaker - yay - they gave me a suite. I've got a nice big bedroom, separated from a living room with a tiny kitchen, more just a sink with a microwave and refrigerator, and there's a balcony."

"A balcony! That's where you should shoot your video."

"It's cold out there. This is Chicago. Even in spring, there's a wind blowing off the lake."

"So you'll get goosebumps, and your nipples will be hard."

"And the hotel has another wing, where people could see me."

"Don't you always say what's the point of being an exhibitionist if nobody sees you?"

"I said it once. You're the one who turned it into a daily mantra."

"That doesn't make it less true. So, do I get my video of you on the balcony?"

"Yes, my sweetheart, you'll get it. As soon as we hang up, I'll head out to brave the cold and watchful eyes, and give you your bedtime video kiss."

"And no rushing things."

"No rushing. Goodnight, sweetheart, I'll talk to you tomorrow."

"By the way, have you opened your care package yet?"

"Of course not. I don't do that till Friday night, that was our deal."

"Well, you've had a rough day. You could open it tonight if you'd like. It might do you some good."

"All right, sweetheart. I'll go make the video first. I love you."

"I love you, honey. Sleep well."

The call ended, and she lay there for a moment, thinking about him and feeling her body relax from the release of tight clothing. She put her hands on her cheeks and slid them down her neck, massaged her breasts and stomach, then down between her legs where she massaged the tightness in joints. "Better not get carried away," she said to the empty room. "I promised him a video."

She turned on the overhead light in the living room. It filled the room with light and spilled out onto the balcony. She looked out over the city and across to the other wing of the hotel, where there were balconies in sight of hers. She didn't see anybody out there, so she slid the door open and stepped outside.

The spring breeze off the lake felt like a blast of winter air, and she had goose bumps almost immediately. She looked around again at the other balconies, then turns and leaned against the railing.

"Good evening, dear husband," she said when she turned on the phone's video camera. "I'm out here on the balcony, and it's just as cold as I thought it would be. You can see here that my arm already has goosebumps on it, and oh, look,my nipples are getting hard." She scanned the camera slowly across her breasts, then moved down to her stomach, where she lingered over her belly button. "Sorry you're not here to pour some wine in here and lick it out. That's one thing I can't do myself."

She pulled the camera out away from her body, so he could get a broader view, then moved down toward her pussy. She slowly squatted down to open her legs and give him a better view. "What did that book about tantric sex call this? The gateway to paradise? That was a nice visit you made there last night before I Ieft. You must come back again soon.

She got up slowly and turned around, so the light would fall on her butt. "And here's my other gateway," she said, spreading one cheek with her spare hand so she could get a view of her butthole. "It's much nicer in person, I assure you." She kept moving slowly as she stood up and brought the camera back around to her face. "That's the end of your private tour, my love. I hope it helps you get off to a nice sleep. I love you."

She stopped recording and sent the video. She hugged her arms against herself and turned back inside to get out of the cold. She stopped at the desk to check on her notes for tomorrow's class. After a few minutes, she sat down to make some more notes, then began reviewing her major presentation for Saturday afternoon. An hour later, she yawned and realized that it was getting close to eleven, or what would be midnight for her, since she'd traveled from the east coast.

On her way to bed, she spotted the care package that Jerry had slipped into her suitcase before she left. She opened the box and saw two packages. First came a soft package with a card that read, "I know this hotel has a pool." Inside was a micro-bikini that seemed more strings than anything else. The triangles for her breasts and crotch were very soft and would probably highlight as much as conceal her delicate parts. She would have to be careful in choosing the time to use this one.

The other package turned out to be a new dildo, a thin blue plastic one that had a few ridges and shapes. She smiled. The last one he had bought for a care package had been too big, and it was not as much fun as she would have liked. This one looked to be about the right size.

"I think we'll check this one out in the morning or some time tomorrow. Right now, honey, I'm ready for sleep." She kissed the tip of the dildo and gave it a lick, then stuck it under her pillow.

ROOM SERVICE KNOCKED right at 6:00 the next morning and woke her up. She grabbed a short dressing gown, still tying the belt as she opened the door. She signed the receipt after he set up and gave him a cash tip. She grabbed a piece of toast and some coffee, then went into the bathroom to shower and get ready.

Breakfast was lukewarm when she got to it, but she took her time to eat it and get ready for the morning. She gathered her notes and her rolling briefcase full of give-aways and headed out. She wanted to make sure she was there first.

The last class always featured student presentations on a scenario she had outlined at the end of the previous session: a security problem with the information system of a large organization. The challenge to them was to outline a correction to the problem and other necessary steps. Each student had five minutes to present, followed by ten minutes of discussion and questions. With eight participants in the class, the session ran less than three hours, giving everybody some time off before the main part of the conference started at noon.

Most of the presentations were fairly standard: suggested changes in the technology to make the system more secure. One woman, older and more elegantly dressed than the others, had a somewhat different take on the challenge, not relying solely on the technology, but including some steps for changing people's behaviors. The discussion after her presentation was more intense than most, and Sandra sensed that some of the participants were feeling challenged by the unfamiliar.

After a break following the last presentation, Sandra handed out certificates and trinkets in thanks for everybody's participation. Then she closed things out with some comments of her own.

"Each of your solutions to the challenge has some value and would definitely improve the particular situation. In a way, though, I wish Kathy had been last with her idea, because it touched on one of the points that I like to make. Technical solutions are essential, of course. At the same time, though, I think we in IT need to pay more attention to the culture of the organizations we work for. Just sending out memos about what not to do under certain circumstances is not enough. We need to help shift the culture, and this work is not something we should leave to HR, which is where it usually rests."

As always, these remarks puzzled some people and excited others. There was some lively back-and-forth with the class, then she wrapped things up with plenty of time for a break before lunch.

Back in her room, she changed from the shirt and slacks she had worn for class to a camisole and light flowered blouse with a mid-thigh skirt and pantihose. She checked herself in the mirror, to make sure the outfit met her criteria for professional, yet sociable. Satisfied, she grabbed her shoulder purse and headed downstairs.

By now, most of the participants had arrived, checked in, and gathered in the lunch room for the opening activities. Sandra, of course, had a seat reserved at one of the tables for presenters, but she spent time working the crowd, talking to her students, chatting with people who remembered her from previous conferences, even a couple who recognized her name from articles she had written.

She spotted Charlie Matson in one corner of the room, surrounded by his acolytes, with Linda Sterling off to the side. She turned away and almost bumped into Kathy, the older student from her training sessions.

"I was just coming over to thank you for your classes," Kathy said. "And thanks for commenting on my work."

"You had some good ideas, and very few IT people think about organizational culture. I think it's important, as I said."

"Are you going to any of the workshops this afternoon?"

"I'm going to take a break after lunch," Sandra said. "Most of the early workshops are fairly general in scope and don't do much for me. I may take a trip around some stores. But I'll be back for the 4:00 p.m. speaker. I'll want him to show up for my talk, so I should be at his."

The lunch bell rang, and everybody headed to their tables. Sandra had seen most of the people at her table at other conferences, so it was somewhat of a reunion. The food came quickly and was fairly good. The opening remarks started on time, and the speaker was mercifully brief. At the end of the remarks, the organizers invited all the participants to the rear of the room for some ice-breaking get-acquainted exercises, and Sandra and other speakers slipped out the side door.

Back in her room, she stripped off all her clothes, then put the blouse back on without the camisole. She stepped into a beige tube mini-skirt and folded the waist down a couple of inches, so it sat below her navel and above the middle of her thighs. She stepped into a pair of flat, soft-soled shoes, suitable for brisk walking, grabbed her small purse, and put on a floppy hat and sunglasses.

She was grateful to have the elevator to herself. She got off on the second floor and walked down the hall to the side stairs, which took her out behind the lobby and away from the registration and vendor table. She stepped out through the revolving door and was on the street, heading toward the river.

The spring breeze stiffened her nipples and tickled her bare pussy under the tight skirt. As she walked, she unbuttoned two buttons on the bottom of her blouse, so her navel was exposed when the breeze lifted the tail of the shirt.

After getting a couple more blocks away from the hotel, she undid two more buttons from the top of the blouse, giving the wind more of an opportunity to expose her cleavage. Her breasts were small enough that they did not bounce all that much as she walked, so she liked to provide opportunities for passers-by to get some quick glimpses. Her nipples were dark enough to show through the thin material, though they blended with the rosebud design. As she got closer to the river and out from between the tall buildings, she knew that the sun would shine right through the blouse and give anybody walking along beside her a clear view of the shape of her breasts.

Once she got to the park, away from the tall buildings, the sun enveloped her and warmed her up. There was still a breeze, lifting the tails of her blouse and opening the top, but she relaxed and let it play about her. She strolled through the trees lining the pathway and finally got to an open space with an overlook facing the river.

She sat on a bench and pulled out her phone to take some pictures. She leaned forward enough to give herself a clear view of her bare breast and let her legs drift open. She did not want to strain to get a picture under her skirt, but she hoped for the possibility that somebody else might get a glimpse. She even hiked the skirt up an inch or so.

She was getting restless after a few minutes, then noticed a couple walking along the river, hand in hand. She settled back and surreptitiously propped her phone at such an angle that she would be able to get some pictures of them if they looked.

They were apparently involved in a serious conversation and stopped not far from her to continue. The woman did most of the talking, and the man was listening, but looking around. He glanced over toward Sandra for a moment, then suddenly shifted his head, as though to look more closely. He must have spotted her, she thought, and she started to record the scene on her phone.

At one point, the woman tapped him on the arm, as though he had not responded to something she said. He responded, then she kept talking. His eyes drifted back toward Sandra, and the woman tapped him again. Finally, after a third time, she turned around, looked at Sandra, hit the guy on the arm, and walked away. He went chasing after her.

Sandra chuckled and sent the video to Jerry with the message, "You might like this one."

She strolled along the park for a while, then headed back into town to seek out some stores where she might get other pictures. She tried a few clothing stores, then found a bookstore with lots of shelves and corners. She took several pictures of herself leaning over or squatting down, all intended for Jerry. She finally found her way into a corner, surrounded by tall stacks and no sign of a security camera. She undid all the buttons of her blouse and pulled the skirt all the way up, so she could take several pictures of herself virtually nude.

Suddenly she jumped up and pulled her skirt down when she heard footsteps on the other side of the stack. She got a bit dizzy from standing up so fast and was fumbling with the buttons when the footsteps rounded the corner.

"Oh, sorry," a voice said. It sounded familiar, and Sandra was struggling to place it when the woman said, "Are you OK?"

"I just got a little dizzy from standing up so fast." She looked up, still fumbling with her buttons and saw that it was Kathy, the woman from her class and the conference. They stood there for a moment, embarrassment in the air, and Sandra finally said, "I guess you caught me."

"I'm sorry," Kathy stammered, "I'll just . . . "

"No, don't go." Sandra finished buttoning enough of her blouse to be somewhat covered. "I told myself that, if anybody ever caught me at this, I should be honest about it."

"You don't . . . ".

"Unless you're embarrassed and don't really want. . . . " She took a breath. "I'm an exhibitionist. I get a kick out of displaying myself, taking risks to let people see me sort of naked, and I send the pictures and videos to my husband."

She got this out quietly and all in one breath. She started feeling a little dizzy again.

Kathy was nodding. "That's kind of cool," she said. "Back in college — so that's about thirty years ago — I went streaking a few times with some friends, all on kind of a dare. I was naked in an experimental play off campus — that was kind of a rush — and I posed nude for a couple friends who were a photographer and a painter. So, yeah, I get it."

"I wouldn't want you to think . . . "

"You want me to take a full-length picture of you, like you were when I barged in?"

Sandra smiled, but hesitated, not sure whether she should jump at the invitation when she was supposed to be a teacher and an authority figure in a professional field. "I'm sure your husband would appreciate it," Kathy said. "I won't tell, I promise."

Sandra handed her phone over to Kathy. "Let's do a video," she said and started recording. "Hi, honey," she said to the camera. "I have somebody to help me, so I think you'll really like this one." She stepped back into the corner of the stacks and slowly unbuttoned her blouse, then shrugged it off her shoulders. It fell to the floor. Her breathing got shallow as she felt a rush of excitement course through her body as she stood topless in front of a virtual stranger. Then, on a whim, she hooked her thumbs into the waistband of her skirt and pushed it all the way down. She stood up naked and looked directly at Kathy, whose eyes had gone wide.