Dorothy out of town

Joined
Apr 12, 2007
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646
Dorothy
Age-59
Hair-Dirty blond
Bra size-C cups, sometimes D cups depending on her weight
Enjoys dressing up, likes lacy bras, stockings and a polite gentleman in a business suit

Has an out of town meeting with a supplier in Atlanta, the trip was fine, the weather hot in Atlanta as she got out of the cab at the hotel. Pulling her suitcase behind her she walks into the hotel lounge for a drink before checking in.....
 
I wasn't looking for her when she walked in the bar, but when she did appear, I was interested. The fact that she'd entered with her suitcase rather than checking in and getting rid of it first spoke of many possible explanations.

Like I said, I wasn't looking for anyone when I'd arrived, but she was a nice-looking lady. Maybe a little older than me, but let's face it: you reach a certain age and younger women start to view you with suspicion and disdain, if not absolute indifference.

I'm not a pick-up artist. In fact, the last thing on my agenda was to find a hook-up on this trip. Still, she looked like she could use a friend, even if it was only for a few minutes.

Stepping up to her, I said, "Hi. Rough trip?"
 
The trip from Toledo to Detroit was one construction area after another, her husband Dave was not in a great mood having to drive her to Detroit Metro rather than her leaving out of Toledo. The plane ride was uneventful but just seemed long. She did dress comfortably luckily with a light floral dress with a pleated skirt, the scoop neck showed a bit more than she liked for a trip on a plane but she didn’t mind. Along with her wedding rings she completed her ensemble with 2 thing gold necklaces, a few thin silver and gold bracelets along with 2 other small rings and a pair of strappy samples for comfort.

“Rough trip?” She heard from beside her. Turning and seeing a man standing a few feet away she replied
“It’s just been a long day” with a smile
 
When she looked over at me, I noticed her wedding ring. It was okay. If all she cared to do was talk, that was fine with me. It's just nice to have somebody to talk to when you're away from home. I've made some nice - if temporary - friends by just taking the chance and saying something.

"Just been a long day," she smiled wearily.

I laughed lightly. "It sure must have been. You didn't even wait to drop off your bag."

I held out my hand. "I'm Evan. It's nice to meet you."
 
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“Hi Evan, I’m Dorothy, nice to meet you” she says as she shakes your hand and situates herself on the seat at the bar. “I’ll have a cosmopolitan” she says to the bartender. She pulls her bag closer to her as she waits on the drink.
“Are you staying here too” she asks. “I got stuck coming down to visit a vendor having quality issues at the last minute, so I need a drink before I go to my room” she laughs.
 
"Personalized customer service. Don't get a lot of that these days," I said, taking the chance and parking myself beside her.

"I'm here a couple weeks to learn some new software package the company's installing." I then told the bartender I'd pick up the lady's drink.

"I assume you're here till the issue's resolved. Got any idea how long that'll be?"
 
Pondering the question her finger runs the rim of the glass sitting in front of her.
“Well, we’ve had a problem with this supplier before and my boss came down here and he was here for 4 days so, it’s difficult to say really” She picks up the glass and takes a sip, her blue eyes looking at you over the rim of the glass.

“So, tell me about yourself Evan” she says slightly turning to you and crossing her legs.
 
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I watched how Dorothy moved, the looks she gave me. Whether she flirted like this any time she was away from home, I couldn't know. She was flirting now, and was doing a fine job of it.

Since she obviously wanted me to look, I glanced down at her legs and imagined how it would feel to run my hands over them. The cleavage she had on display begged for attention, so attention was paid. Just as I had with her legs, I imagined laying my hard-on between those lush breasts and a vision of seeing them coated with semen as she admired my handiwork popped into my mind's eye.

"Me? I'm pretty boring. Seems like I'm away from the office more than I'm at it. One son, married for two years. Wife and I are separated. When I am at work, I sit at a computer most of the day."

It was a vague but succinct description of my life. I hoped clarification wouldn't be requested. I generally don't like to talk about me.

"How about you, Dorothy? What should I know about the lovely lady who suddenly and all-too-briefly has dropped into my life?" I followed this up with another glance at her tits and legs.
 
Dorothy pushes her glass to the inside edge of the bar with a well manicured hand then tapping the rim lightly to indicate she wanted a refill, the bartender gives her a quick nod.
“Ive been married for 30 years to my second husband and we have 4 boys, two from his previous marriage and two from mine”
“And I don’t have to tell you Evan that raising four kids from young boys to young men can be a challenge”
You notice a wistful look come over her face as she speaks “and sometimes very... how should I say it..well, erotic”
She takes a long sip of her drink.
“But I digress....”

“Do you have any children Evan?”
 
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I was a little surprised at Dorothy's description of what it's like to live in a house full of men. I thought mothers - even steps - weren't supposed to harbor such thoughts about the offspring that live with them. Then again, if I'd had a daughter instead of a son, would I have been able to look at her platonically at all times, and not let the woman she would have grown into affect me on some level, whether I'd act on it or not? I'd never know. Apparently having all those cocks around her - whether she could see them.or not - got Dorothy's imaginitive libido pumping.

"I've just got the one son. He graduated college a few years ago, got married and is now living a few hours from home. He's got a good job and he married a smart, pretty girl he met his junior year of college. They're waiting a few years to try for kids. They both want to get their careers going and some money saved first."

The nosy, improper part of me wanted to ask Dorothy about her "erotic" comment, but sitting at the bar didn't feel like the place for such conversation.

"Would you like to move this conversation to a table or something?" The bartender had brought Dorothy's second drink by now, and she'd already taken a couple pulls from the glass. "Or maybe you'd like to get your bag to your room and take it easy for a bit. I'm not going anywhere for a while. I'll probably be around when you've had a chance to relax somewhere a little more... peaceful than the bar.

"I'm not looking for an excuse to get rid of you, trust me. After a couple drinks, I'm usually ready to kick back for a while. I wouldn't be offended if you needed to take off."
 
“Actually Evan that is a good idea, I need to get freshened up and change into something more comfortable”
“Let me check into my room, freshen up and I’ll be back, perhaps we could have a quiet dinner?”
You agree
Dorothy empties her glass, pushes her bag away from under the bar and stands up. She teeters a bit and you catch her by her elbow to steady her.
“Wow those are pretty potent aren’t they” she says with a laugh
“I’l be back in a bit” she says as she turns to the exit and into the lobby area.

Checking in was a breeze, the hotel was quite efficient. Her room was nothing to get excited about, two double beds with a small balcony off the sliding doors.
Slipping out of her dress she tosses it on the bed, the straps of her bra pushed down her upper arms, the bra itself spun around and unhooked.Her large heavy breasts sag as the cups release them. She looks at herself in the large mirror.
“Not too bad for an old woman” she thinks to herself.
She warms the shower and gets in quickly soaping up her boobs and soft belly. Her hands slide down between her legs to wash between them.
“I’m glad I shaved last night I don’t have time tonight” she thinks

Drying off she moves to her bag finding a nice thin blouse and a medium length black skirt.
“Bra or no bra?” She asks herself......
 
At the suggestion of dinner. I readily agreed.

Dorothy then emptied the rest of her drink in a single gulp, and started to rise from her seat. Her little wobble told me either she wasn't very used to drinking, or what she'd had was pretty strong.

As I reached out to steady her, Dorothy giggled, "Wow, those are pretty potent, aren't they?"

I smiled lopsidedly. "I didn't think to mention that you get what you pay for in the alcohol department with this guy," I said, giving a nod in the bartender's direction. "You gonna be okay?"

Dorothy placed a hand on my arm. "Be back in a bit." She then picked up her suitcase and used it to steady her as she left the bar.

I took this as an opportunity to get cleaned up a little, myself. Asking the bartender to let Dorothy know I'd return, if she reappeared before I did, I headed back to my room.

Stripping down, I wondered what might happen with this woman I'd just befriended. I ran a razor over my face quickly, then down over my balls - the only other place I shave: been doing it for years - then jumped in the shower and cleaned up, my cock semi-hard the whole while.

A quick brush of the teeth and I turned to clothing. If it was up to me, I'd rather run around nude, but the rest of society has no sense of humor about such things. I hadn't brought any dress pants, only jeans. This trip didn't require being real dressy.

Slipping on a pair of clean jeans (no underwear - been going commando for almost as long as I've been shaving my balls) I then put on a black T-shirt and topped it off with the jacket I'd brought to make things "business casual". Shoes back on and I was ready to go.

Back in the bar, I grabbed a glass of water, took a seat at one of the tables and waited...
 
Slipping on the blouse Dorothy buttoned it up and looked at herself in the mirror. She gave her upper torso a little shake as well. Her full mature boobs only jiggled a bit under the thin material. “This will be fine” she thinks. “It will feel good to go the evening braless” she slips her garter on along with her black stockings lifting each leg onto the bed to secure them to the garter. A pair of 3 inch black heels completes her ensemble. She gives her make up a quick touch up, maybe making it darker than it should be, her hair a quick brush and off she goes to the lounge. Standing at the entrance to the lounge she scans the room for Evan..Oh there he is, she sees him waving to her. She makes her way to him......
 
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I was scanning the room, just doing some discreet people watching, when I saw movement at the entrance to the lounge. Curiosity turned my head in that direction and what I saw astounded me.

It was my new friend, Dorothy, and she'd had a chance to get cleaned up and changed. However, what she'd changed into was most surprising.

Now, I'd seen pictures of women in see-through clothing before, but I never thought I'd meet one in real life. The top Dorothy wore left nothing at all to the imagination. Heads turned as she moved through the bar and Dorothy owned it like a woman half her age. There was no embarrassment evident in her posture: in fact, she seemed prouder, dressed this way than she had when I'd first met her.

Uncertainty swept through me, but I got her attention before any of the wolves I saw ogling her could have a chance to make their moves. Although, with the comment about her family, I got the impression she'd take on however many men wanted to. I couldn't know if she acted this way at home - I suspected not - but it would appear my friend Dorothy liked to cut loose when away from her normal circumstances.

As she approached, I saw that her high beams were on, if you get what I mean.

"Wow," I gushed appreciatively. "You clean up nice.

"You want to grab a bite here at the hotel, or would you like to take this to the streets? There are some very good restaurants in the area."
 
Dorothy blushed at the compliment. “Why thank you Evan, I want to to be comfortable this evening, tomorrow will be a long day”
“Take it to the streets, that sounds like a great idea..get out of this place” she says looking around noticing a few of the men in the lounge looking her up and down. Never even sitting down you get a nice side view of her, her full breast silhouetted against the well lit bar area, the hard nipple obvious.

She was a bit taller than when you had first met as her heels added the 2-3 inches, making the calves of her legs that much more shapely as well.

You stand up and move to her placing your hand in the small of her back to guide her out of the lounge. Her light perfume hits your nose, “You smell nice” you say discreetly. She turns to you her blue eyes sparkle “Thank you” she says with a smile.

One of the men close to you both notices the small telltale bumps under her skirt. “Mmmmm, nice, garter straps” he thinks to himself.
 
My mind reeled at her "comfortable" comment. If this was her idea of comfortable... bring it on!

Along with her see-through top, she'd put on heels, which brought her up a little closer to my height, but I still was at least a head taller. They were a nice addition to the show she was putting on. With what she was wearing, it made me wonder if she had panties on...

When Dorothy agreed to go out, I stood and began to lead her from the room, aware of the looks she was getting.

My hand on her back detected the definite feel of a garter belt under her skirt, and it made me wonder even more whether there were panties underneath.

Outside, the cool evening air made Dorothy's already prominent nipples stand out even higher. Part of me decided to walk her around a while and let her show off what she obviously wanted everyone to see.

I turned us toward the flashing lights on the next block. The street is blocked off and has been turned into a pedestrian mall, so it's the natural congregation spot. Besides, there are plenty of good shops and restaurants along it, so we were bound to find a good place to sit, eat and for Dorothy to show herself off.
 
“Oh my, would you look at all this” she remarked, her eyes moving from shop to shop. Her heels clicked on the concrete walk as you both strolled along. Her hand moving to the top of her blouse a few times, then the last time a button was unbuttoned.

Her full mature boobs wobbled sensually under the thin blouse. She feels your hand on her lower back and moves a bit closer. Your hand sliding over around her waist.

“Are you seeing a good place to eat?” She asks with a smile her hip bumping yours playfully as you stroll, her arm moves around your waist.

The street is filled with people of all ages, and not just a few of them notice your date.

“I love these outdoor little bistros don’t you?” She asks.

She stops suddenly and turns to you, looking up into your eyes, “I have to say Evan, I feel quite comfortable with you” she says with a smile and turns to walk again.
 
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Dorothy seemed fascinated by all the activity around her. The passers-by seemed to notice her, too. Yes, there were other women showing what they had, but not quite in the same way Dorothy was. The cool night breeze, as well as the way her tits moved, unfettered beneath her sheer shirt, had her nipples as hard as I believed they could get, and she seemed completely unfazed by the display.

I was stealing yet another look at her gorgeous tits when she turned from her marveling perusal of the collection of people around her, asking innocently:

"Do you see a good place to eat?"

I couldn't help my inner response, I think I'm looking at it, but I managed to keep that inside.

"Ladies' choice," I responded. Any of them would be a great dinner. I hadn't tried them all, but from the look of things, they were all popular. The smells wafting out onto the street promised a dining experience par excellence.

Then, out of nowhere, Dorothy stopped and turned to me. I couldn't help but notice the way her tits bounced and bounded as she moved. With big, innocent eyes and a grateful smile, she said, "“I have to say Evan, I feel quite comfortable with you," before she led me to the kiosk with the shortest wait line.

I gave a name to the girl at the kiosk and we moved out of the way to wait for a table to open.

"I'm glad you like me, Dorothy," I told her. "I just know how lonely these kinds of trips can get. Besides, if you're anything like me, you're always in the mood to make a new friend."
 
Twilight had begun, a few shops had turned their lights on. Dorothy snuggles into you as the evening air turns a bit chilly, her left breast pushing against your side her left hand around your waist and her right hand moves to your belly and rests just above your belt buckle. A group of three young college aged boys are walking up the sidewalk talking and laughing amongst themselves approaching the shops area.

“Oh absolutely Evan, even with all the people that I deal with on these vendor trips it seems so lonely”

She turns her head and lifts her face to you

“And sometimes you want more than just a friend”

She turns her head and lowers her face

“I’m sorry, I shouldn’t have said that” her eyes on the three boys walking past.
 
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As we casually walked, keeping within earshot for our table to be called, Dorothy leaned into me and placed a hand on me with an intimacy that belied our brief relationship. I didn't mind. The feel of her breast against me made me want to feel them both in a more intimate fashion, and the hand she rested over my belt made me wish she'd move it lower...

Just maybe not in this particular venue.

When Dorothy agreed with my comment about making new friends on these trips, she followed it immediately with:

"...Sometimes, you want more than just a friend."

She then realized what she'd said using her outside voice and bowed her head in embarrassment.

"I'm sorry, I shouldn't have said that," she apologized. Her hands left my body and she stood up straight once more.

Taking her arm, I turned her to face me.

"Don't be embarrassed. You have nothing to be ashamed of. You think I didn't have a hopeful ulterior motive in approaching you in the first place? Yes, there was some altruism in that, for real. I get tired of being alone on these trips. Hanging out with the guys I've come to see, all they want to do is talk shop. Fucking boring, and the last thing I want to do for two weeks away from work is talk about work, even if I'm away training for it.

"I'd have been fine with it if all you wanted to do was be friends. I saw your ring and came over anyway. Then, you came down in what you're wearing and I knew you were looking for an adventure.

"I've seen how you've been looking at these other men while we've been out here. It doesn't take a lot of imagination to work out that you'd like to lay back on one of those bistro tables and let any man who wanted have his turn, am I right?"

I wasn't angry. I wasn't disappointed. Dorothy laid it all out on the counter from the outset. She wanted an adventure. I had no way of knowing what her sex life was like back home. In fact, it was none of my business. That she was obviously willing... no, eager, to get fucked on this trip told me one of two things: either she and her husband were swingers and she got a free pass when she went on these outings, or hubby was uninterested and she was desperate for some male intimacy.
 
Evans voice trailed off as Dorothys imagination took hold. Evan was leading her across the street to a group of small bistro tables where she was swept up by Evan and another man and placed on one. She could hear many voices but none of them were clear, just noise in the background as her legs were being spread apart.

“Just as I suspected” she heard Evans voice “No panties” as her leg was being held by another Evan moved between them. Her arms being held back by another two men, Evan slides his cock into her.

“Mmmm nice and juicy aren’t you?” He grunts as she hears another voice “Lets get a look at those tits” her blouse being ripped open in the front her full mature boobs hanging off either side of her chest. As Evan finds a nice rhythm multiple hands are feeling, groping at her tits. Her head lays back farther and farther off the small table. A pair of hands turn her head to the side where she comes face to face with a thick uncircumcised penis just a few inches from her mouth. Her lips part accepting the thick tool.

Man after man ravage her between her legs and in her mouth, over and over again......each one ejaculating in their desired location.

“One eighty seven”......”ONE EIGHTY SEVEN”

“Dorothy they’re calling our dinner number” Evan says snapping her out of her fantasy.....
 
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After a while, I realized Dorothy wasn't listening to me.
No, she was off somewhere in her own mind. From the look on her face, I had an idea where she'd gone. Instead of being offended by the things I was saying. I think she'd gone there. It was okay, I could work with that.

Just then I heard our number called, so I had to pull Dorothy put of her reverie.

"Dorothy, that's us." I guided her back to the girl at the kiosk amd we were seated. The place was open air, so we still had a view of the majority of the mass of humanity out on the mall.

As we perused our menus, I asked, without looking up, "So, nice fantasy back there, was it?"
 
Dorothy snickers at your comment, a bit surprised you knew what she had been thinking. “Yeah, as a matter of fact you were in it” she says still looking at the menu.

“Did it have to do with the Bistro table right across the street there?” You ask motioning toward the bistro across the street.

“As a matter of fact it did” she says looking into your eyes now. “And you weren’t alone” she says as her eyes turn back to the menu.

“I wasn’t alone, wow, you certainly have quite an imagination”

“Do you want to be alone?” She asks looking into your eyes once again.....as she licks her lips seductively.
 
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After hearing Dorothy's brief fantasy had been of more men than me, I decided to play along.

"So," I pointed out the three young toughs we'd passed earlier. They were standing across the street, smoking and laughing at each other's jokes. "You'd like to have me bring that young man over here, the one with the tattoos down his arms and the sides of his head shaven, and tell him you want to suck his cock, is that it?"
 
Nonchalantly Dorothy reaches up and unbuttons another 2 buttons on her blouse as she looks in the direction you are pointing. So in addition to her blouse being sheer it now offers a view of her cleavage.

The images run through her mind like a slideshow. The young man coming to their table and unzipping his pants, the customers sitting all around them watching. He reaches in and tugs out a long limp thick cock and steps towards her. “Could you take the wrinkles out of this Ma’am” he asks. Some of the customers gasp as others are wide eyed seeing what the next move was going to be.

She snaps back to coherency

She turns to you “Very well”
 
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