Dorothy out of town

Dorothys fingers continued to tease your now fully erect cock through your shorts.

“It sounds like you’d like to be with two women Evan, and possibly see what they would do together, isn’t that so?” She asks quietly.

“Exactly” you reply

“Well, I’m certainly open to that idea, if you could talk that cute waitress into it”

“How about you asking Paul if that would be possible?” You ask while raising your hand in a “Mayday” gesture. It gets Pauls attention and he makes his way quickly to our table. Dorothy straightens up and sit with her hands clasped together on top of the table (So innocently).

“Paul, another round here please and Dorothy here has a question about the menu” you say with a sly grin.

“yes Ma’am” he asks

Looking up she puts on her best bedroom eyes and says “Does that cute waitress get off at the same time you do?”

“She does”

“Could she join us?”

“Shes already asked” Paul says with a smile
 
Dorothy was definitely open to the idea of having the busty waitress join us. Without a doubt, the notion of seeing the two women kissing and loving on one another turned me on. I mean, what man's fantasies doesn't include two hot, horny women fucking together?

When Paul came back and admitted that the waitress wanted to join us, if my cock hadn't already been hard from Dorothy's eager fondling, it would have gotten that way, having heard that this sexual free-for-all that was shaping up might actually happen.

"So, Paul," I started, "Dorothy's already shown me your note. The two of you want to join us after your shifts end?" I felt Dorothy's fingers get more insistent at my cock when I asked that. I also noticed that she wasn't hiding the fact that she was playing with my cock from our waiter.

"I'd be happy to," Paul answered, his eyes locked on Dorothy's hand and my bulge. "Let me see if April's available after work."

He turned to leave, then as an aside, almost having forgotten the initial reason we'd come: "Your food ought to be coming out any time now."

He then did actually leave, ostensibly to ask the waitress if she was able to come with us and fuck later.
 
As Evan spoke Dorothys mind wandered to her hotel room on the 15th floor with two men and a young woman, her being ravaged on the hotel balcony by all three of them.

Other rooms balconies with people on them watching the action. Dorothy pushed back against the wrought iron railing, her blouse open in the front with a pair of lips on each one of her areolas.

Three pair of groping hands, something warm and wet between her legs.

“Your salad ma’am” a voice behind her said. She sat up abruptly coming out of her fantasy.

“Oh thank you”

“Yours sir”

“Thank you” Evan replies

Is there anything else I could get you right now?” April asks softly

“No I think we are all set” Evan replies “Other than could you make it later on tonight?”

Smiling she says “i think I could find my way clear” her eyes looking Dorothy up and down
 
Dorothy retreated into another of her reveries for a few seconds. I just let her drift when she did this. It never lasted long, and who was I to deny her fantasies?

While Dorothy's mind was elsewhere, April, the busty waitress, came up to our table, carrying a plate and a bowl.

"Your salad, ma'am," she said, startling Dorothy from her reverie. Her head spun toward the voice, and just like with Paul's crotch, it brought Dorothy's gaze pretty much in-line with April's fine tits.

"Oh, thank you," Dorothy gushed. The tone she used indicated an appreciation that wasn't solely for the food.

"Yours sir," she said, placing my plate before me and bending over just a little more than was really necessary, giving me a fine view of her cleavage.

"Thank you," I told her, my eyes not turning toward the food.

"Is there anything else I can get you right now?" April asked huskily, leaving her breasts there for my enjoyment.

The mind boggled. Between the fondling I'd gotten from Dorothy, then this, the food was swiftly dropping lower and lower on my list.

"I think we're all set," I finally managed, my eyes still not having turned toward my plate. I did, however, finally tear my gaze from the ample chest of the young woman to her lovely face. The smile she gave me said she liked the attention she was getting.

As April turned to go back to work, I stopped her with:

"Would you care to meet us after your shift is over?"

The smile she'd worn ticked up a couple shades brighter.

"I think I could find my way clear," she replied, giving Dorothy and me a visual undressing, a wink, then back on her way.

I watched the girl go. Her ass was as spectacular as her tits. She wasn't a thin woman, but her curves perfectly matched the round glory of her chest and butt. The cascade of brunette curls that fell halfway down her back just put the capper on the whole effect.

And I still hadn't looked at my food.

Placing a hand on Dorothy's thigh, I said, "Well, my dear, it would appear we have dates for later this evening."
 
Dorothy watches Evans eyes as April walks away, she smiles “Cute gal” she says as she takes a small bite of her salad. She wanted to say “Nice tits” but that may have been too forward. His warm hand feels good on her thigh.

Dorothy picks at her food as she watches Evan across the table thankful for meeting him at the hotel. An attractive man with good manners is difficult to find these days she thinks to herself.

They both are eating quietly when a voice behind her says “How is everything so far?” It was Paul.

Almost in unison they say “Just perfect”

“Good, good” Paul replies just as he turns to leave he says “Excuse me Ma’am it seems you have gotten a bit of salad dressing on your blouse”

“Let me get that for you” he says while producing a damp kitchen towel from behind him. Placing his left hand on Dorothys shoulder he squeezes gently as he blots up the dressing from the blouse with his right. Dorothy feels him blotting on her mature breast.

“Almost done” he says as he begins to brush at the spot making her boob wobble underneath his hand.

“There, I think I got it all, it would be a shame to ruin a pretty blouse like that, don’t you think?” As he stands up next to her.

“An absolute shame” she replies

Dorothy actually somewhat taken aback by the waiters move to clearly “Cop a feel”.
 
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With the possibilities of a body like April's dancing through my mind, I finally looked down at what she'd brought me. It looked good, and with a smile to Dorothy, we began eating.

Little conversation went on as we enjoyed our meals and watched the press of humanity march by.

After a few minutes, Paul's voice rang out, "Everything okay so far?"

Without practice, Dorothy and I were almost in unison responding: "Just perfect."

He nodded with a grin then started to leave, but stopped. He mentioned something about a spill on Dorothy's blouse, then proceeded wipe it away for her. He lingered far longer than would otherwise have been necessary, and came damn close to just cupping his hand over her breast. When he was finished, he stood, a confident look of proud accomplishment on his face, then went back to work.

Dorothy seemed a little nonplussed by this, though why, I couldn't quite understand.

"You okay? You look kind of surprised. Just remember, you were practically jerking him off in front of the whole place a little while ago. I think he just wanted to get a little, too. Besides, in a little while, he and that sexy April are going to be playing with us. Think of it as foreplay."
 
That familiar warm feeling began radiating from between Dorothys legs out into her upper thighs as she heard Evan say that Paul and April will be playing with us. Imagining the extremely tall young man and the shorter busty brunette groping her body excited her.

As they ate she began to feel just a bit guilty as she started the evening with Evan and now her thoughts were consumed with the two young wait staff of the small Bistro. She had plans for the younger man seated across from her after dinner and now she was making plans with those two.

She had brought a number of sexy outfits that she thought she would model for Evan later up in the room if he wanted her too still. She liked the idea of teasing other men that she has come in contact with and Evan seemed like the type that would enjoy that.

Or would that just be a foolish thing to think of at her age, although she thought that she could still “Pull it off”

“Ya know Evan” Dorothy said between her last bites of salad. “ I am looking forward to meeting Paul and April “up close and personal” she says using air quotes. “But we began our date with just you and I and I was kinda hoping that we would be able to spend at least a little bit of time together alone, maybe before they arrive”

“Am I being too forward?”
 
I couldn't help but chuckle at Dorothy's sudden fear that her talk was moving things too quickly.

"No need to be afraid of my being put off by your candor. Yes, we'll be here for a few days, but we don't really have time for games that take a long time to play out, do we? While innuendo is fine, I get that there comes a time when you just have to say what you need to say.

"I approached you with the hope that we might get some time together. If we happen to be in the middle of that when our young friends arrive, I'm hoping they'll just join right in."
 
Just as we finish our dinner Paul shows up with the check. You quickly snatch it up, insert a tip along with a number at the Bottom “1517” Dorothys room number. Paul returns a few minutes later takes it back to the waiters station.
He says thank you very much upon returning placing your card and receipt on the table. Checking the receipt prior to putting it in your pocket you see he has put a number of his own on it “11:15”
You make out way out from the little Bistro your arm around Dorothys waist feeling her softness through the thin material once again. It has gotten quite dark since you first arrived, even the lighting from the small street lamps was dim.
Dorothys heels clicked lightly on the faux cobblestone street as you make your way back to the hotel.

Suddenly you feel her hand on yours pulling you toward a small dark abandoned shop entrance.
 
Paul eventually brought us the check. I saw Dorothy write a number on it. It didn't look anything like the total or payment with tip, so I guessed it was her room number. That solved whose room we'd be having our play in.

When he returned, he gave back a receipt, and on it was written a time. That must have been when he and April were finished with work. That still gave Dorothy and me some time to explore whatever our brief relationship was going to amount to on our own.

Paul and April saw us out as we left, and I found myself greatly anticipating seeing both of them nude.

We started wandering back toward the hotel. Suddenly, I felt Dorothy pull on my hand. I didn't resist, and next thing I knew, I was against an alley wall, with Dorothy pressed against my rising cock.

"Can't wait?" I asked with a sly grin.
 
Dorothys hot mouth presses against yours, her wet tongue penetrates and probes. She feels your arms embrace her then your hands sliding down her waist to the tops of her hips.

“Can’t Wait?” She hears you ask

Without a reply her body presses against yours, her full boobs against your chest.

Your hands slip farther down on her skirt feeling the telltale bumps of her garter and the tops of her stockings. Your fingers grip her skirt curling in it and tugging the material upward, her tongue exploring, searching.

Her hands sliding upward under your shirt onto the bare skin of your sides then up to your chest.

“Mmmm” she coos softly
 
I don't intend on going too far, here in an alley where just anybody - including the cops - could find us. I'm pretty sure Dorothy's plans didn't include a stay in a holding cell for indecent exposure and lewd and lascivious. That'd put a crimp in everybody's plans, including the companies that sent us here.

Nevertheless, we could get naughty, as long as we kept our heads about it. Dorothy seemed to really love my hard-on, because she pressed hard against it, I'm sure wanting to haul it out and see what kind of milky, gooey prize she could coax from it.

My cock surged when I reached to her hips and discovered the garter belt she wore. I love garter belts. It's possibly my favorite form of lingerie. I could hardly wait to see what it looked like in person.

I ran my hands over the sexy undies and started bunching Dorothy's skirt in my hands, making the hem rise inch by inch and exposing her ass to anyone who might poke their head into the dark where we stood.

Eventually, there was no more skirt to gather. Dorothy had to be feeling a breeze by this time. I pushed my hands down over the exposed skin, getting a good feel of her bare ass. I wasn't sure what - if anything - Dorothy might be wearing for underwear, but I liked the feel of her ass in my hands.

All this time, we kissed like a couple horny teenagers in the house with the folks not home. If we weren't careful, we might let caution abandon us and start doing something truly dangerous...
 
Dorothys tongue probes and darts in and out of your mouth as her hands move around to your upper back, her full braless mature globes press against your chest. Her finger nails slowly rake down along your shoulder blades then the small of your back until her fingertips find the waist of your shorts.

Her fingertips on both hands run between the waist band and your skin until they meet in the front. She leans back and away from you as her fingers deftly unbuckle your belt and unsnap the snap.
Looking down you see the smooth skin between her tits.

She tugs down the small tab easing the pressure on your erection. Her eyes cast down as she does. Your shorts fall to the ground the metal buckle clanks as it hits the ground.

Lowering her self down in front of you she hears you say “Dorothy, I don’t think…..”

She interrupts “You don’t think what Evan?” as her fingers tug down the waist band of your undershorts allowing your thick tool to escape. It dangles in front of her until her warm wet mouth engulfs the swollen head. “mmmm Hmmmm” she coos……..
 
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When Dorothy started unzipping my pants, there was no doubt she didn't care about getting caught. When she lowered herself to her knees, there was no doubt what she intended to do.

'Okay, we're going to do this,' I thought to myself. My cock was hard as hell, so there were at least two here who weren't afraid of potential consequences. I knew what consequence Dorothy was thinking about.

At my warning, Dorothy looked up at me, her hands fondling my hard-on to the point where conscious thought was way in the background.

"You don't think what, Evan?" she cooed as she wasted no time gulping me down her throat.

Oh god, it was amazing! I'd never done anything like this in so public a place before. Then again, practically everything that had happened in the last hour or so had been a "first" for me.

I don't know how long Dorothy had been expertly sucking my cock, but I opened my eyes and saw two forms in the entry of the alley we were in. One was obviously male, the other female. They simply stood there, whether stunned by the sight or turned on, I wasn't sure. The possibility was good that they had turned down this alley to do pretty much the same thing Dorothy and I were.

Gathering my wits, I held up a hand and beckoned them closer. I saw the silhouettes turn to one another, then start coming closer. No, it wasn't Paul and April. They wouldn't be getting off-shift for at least another hour or two, and those forms would have been really easy to discern, even in the low light. These were two strangers.

As they came closer, it was a little easier to see their features. They were a young couple, probably late teens, early twenties, and it was pretty obvious they liked what they were watching.

They stood there a little while. Eventually, one of the girl's hands went to her tits, the other sliding under her skirt, while her date's hand rubbed his bulge for a few seconds before he unzipped himself and hauled out an impressive erection, which he started to slowly stroke.

Dorothy didn't miss a beat. She looked over at our young friends and gave them a smile around my cock, never once stopping what she was doing. One of her hands reached for the nearest of our two voyeurs, which happened to be the young lady. Dorothy's hand landed on the girl's thigh, but couldn't reach much higher than the bottom of the hem of her skirt...
 
Dorothys head bobs slowly taking in more and more of the fat shaft, her soft lips caressing it.

“Oh yeah” you groan softly

The young man moves a bit closer “”Oh wow, look at that” he says slowly stroking a very impressive tool as he watches Dorothys mouth.

Dorothys Emerald and Diamond encrusted wedding ring sparkles in the dim light as her fingers tug gently on the young ladies skirt, she moves closer, her eyes glued to Dorothys mouth as well as the thick member she working on.

“I have to say that your wife has a very nice set of tits” the young man says “along with the obvious” his hand moving slowly up and down.

Dorothy tugs at the young ladies skirt hem urging her to join her in front of you. She lowers herself down.

“Would you mind if I got them out?” He asks softly

“Please do” you grunt as Dorothy takes in your entire shaft
 
Next thing I knew, the young lady was kneeling next to Dorothy and the young man was asking permission to bare Dorothy's breasts.

The situation was spiraling away past the point of no return, so I told the guy to go ahead, just as his date was leaning in to join Dorothy in working on my cock.

I'd never had a double blowjob before, so this was going to be a treat. And while I'd seen Dorothy's tits beneath the thin blouse she wore, having them out in the open was even better. The young guy was a tit man for sure, because he wasted no time kneading and squeezing, pinching her nipples and making Dorothy moan around my cock, while her blowjob partner sucked my balls.
 
Dorothys head bobs up and down on the thick tool as the young man moves behind her. She feels his hands on her shoulders massaging them gently. “Mmmmmm” she moans softly around your shaft. The young woman slips your shorts down to your ankles as she gets a good angle with her full lips on your balls.

“Oh yeah” she hears you groan.

The young mans hands move to the front of Dorothys blouse and spread it open in the front exposing her large mature melons. Quickly they move downward cupping, squeezing and groping at the big set of tits.

“Oh fuck yeah baby” he grunts “Nice set of tits”

You glance down at the sight of the two women, Dorothys lips around your shaft as the young woman (Who can’t be any older than 18 years old now that your eyes have had time to adjust) has her lips on your swollen balls. Your hands move to the sides of each of their faces, caressing them.

“Good girls” you whisper as you get a nice view of Dorothys tits being groped and fondled.
 
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Before long, both ladies are going at my cock like it's their favorite toy and candy. As I said: I've never had a double blowjob before. I must admit: I like it. Between the sight of both women's faces at my genitals, the sensations they were causing, and the vision of seeing Dorothy's tits exposed and getting mauled by this young man, it was a dessert far better than anything we could have gotten at any restaurant.

Suddenly, an idea came to me. Finding a voice amid the sexual sounds I was making, I asked our new friends:

"You guys want to join us back at our room?" I didn't figure Paul and April would mind more company when they arrived.
 
Your hard cock was sliding in and out of Dorothys mouth with ease as she let it slip from her lips with an audible “pop” the thick shaft bobs up and down seductively.
“Give it a try” she says breathlessly to the young gal as the young man continues to grope and feel up her mature tits. You watch as she takes the head between her lips and begins to emulate Dorothys movements.

Reaching behind her, Dorothy finds the young mans fully erect penis and tugs him next to you facing her.
She looks at the thick tool “Mmmmmmm” she coos just before taking it into her mouth.

“Oh Fuck yes” he grunts as she finds her rhythm matching the young girl next to her. Both of their heads bobbing in unison. Dorothy feels the young mans hand caressing the top and back of her head encouraging her.

Somewhat out of breath he hears you “You guys want to join us back at our room?”

“Oh man” he says haltingly “This chick is old enough to be my Grandmother, but hell yes”
 
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The problem with my suggestion, and our new young friends' agreememt to it, was that it was going to be necessary to bring a halt to what we were doing to change venues. The plus side would be that it'd be a hell of a lot more comfortable, even if my cock was going to hate the ladies' cessation of attention it was currently receiving.

"Whenever you're ready," I told the young man, who couldn't seem to get enough of Dorothy's big tits.
 
“Hold on for just a minute” he croaks as Dorothys mouth begins to move up and down on his thick cock.

He turns to look at you “Man where’d you find this one?”

“Ohhh fuck” he groans as Dorothys lips and tongue work over his shaft.

Just as you are going to answer the young lady in front of you takes your entire shaft into her mouth.

The young man pushes Dorothy away “As much as I hate to do this, lets get back to your guys room. He says. Dorothy stands up the area around her lips and her chin wet with saliva. She buttons up her blouse covering up most of the big tits that were just on display.

The young lady stands up as well, says nothing as she looks Dorothy up and down, moves to her and puts her hands on the sides of Dorothys hanging mature tits through her blouse, she smiles at the older woman.
 
While I hated to bring the festivities to a close, there are far more comfortable places to do such things. Besides, even though there's a thrill in the possibility of being caught, not every person who might stumble upon us would likely be as accommodating as our new young friends.

I noticed the young man hung close to Dorothy, and he kept shooting glances at her tits, which bobbed and swayed as we walked. His lady friend's breasts didn't move as much, but they weren't quite as big as Dorothy's, and besides, she was probably at least twenty years younger. Nevertheless, I couldn't wait to see them in the flesh.

As the elevator doors of our hotel slid closed, I asked our new friends their names, to which I was told Tyler and Marie. I then asked if they minded more company than just Dorothy and me. The response I got was: "If they're as hot as you guys, I can hardly wait. We've never been in an orgy before. It'll be fun."
 
Dorothy was having a hard time believing what she had done in an alley in Atlanta. She had gotten herself so worked up that she had sucked two strange men’s cocks. It’s not like she had never sucked strange men while on a business trip, she had done that numerous times over the years, but in an alley?

And now Evan was was talking about having four more people in a room with us.

Her pussy was soaking wet.

She felt Tyler move behind her just as the elevator doors close. His arms moved around her waist, then onto her soft belly, he kissed her neck gently. “You smell good” he whispers in her ear as his hands quickly cup her melons through the thin blouse.

“Ding”

Dorothy notes it the fifteenth floor..her floor, as they all exit the cramped elevator.

“Whats your room number?” You ask

“1517” Dorothy replies

“Great that’s the side with the nice view of the city” you say

Tyler watches Dorothys globes wobble as the group walks down the hallway to the room.

“Hand me your key card” you say

Dorothy rummages through her purse, finds it and hands it to you.

You slide the card into the slot, knowing that won’t be the last thing you slide into Dorothys slot.

The door swings open to a large suite with large sliding glass doors to a balcony.
 
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The elevator ride seems to take an inordinate amount of time, what with the erotic tension in the air. If it had broken down before we got to our destination, I'm pretty sure we'd have just decided to fuck right there in the cramped little space. It kept going, though, and eventually the doors opened on floor 15.

Hands seemed to be everywhere as we made our way to Dorothy's room, but finally we were inside and the door clicked quietly closed.

While my cock wanted to get right back to what we'd been doing in the alley, I thought of our other guests, who wouldn't be arriving for a little bit yet.

A glance around the room yielded little with which to prop the door, so I slid off a shoe and wedged it into the jamb. Paul and April would be able to enter without anyone having to take a break from any action to let them in.


When I turned around, I saw that Tyler had wasted no time opening Dorothy's blouse, and he already had a nipple in his mouth and kneaded her other breast with one hand. The other was trying to eagerly get at her pussy from under her clothes.

Marie didn't seem.put out by all the attention her boyfriend was showing another woman. On the contrary, she looked aroused as hell.

"You want to play, or you want to watch?" I asked her.

After a couple of mesmerized beats, the pretty young thing looked up at me. A couple more beats and she murmured, "God, that's so hot."

She didn't seem inclined to answer my question, so I sidled in behind her and cupped her firm, young breasts in my hands.

"You watch and I'll play, how about that?"
 
Dorothy takes Tylers hand and leads him to the balcony. She opens the French doors and walks out Tyler’s hand in hers. She leans her back up against the railing, Tyler begins kissing her, pressing her against it, his hands pushing her blouse over her shoulders and down onto her upper arms.

Dorothy sighs as his head moves down her bare shoulder kissing all the way along the top of her tit until his lips find her stiff nipple.

He lifts the mature tit as he kisses all around the dark areola. Dorothys hand moves up his back and into his thick head of hair, guiding him, letting him explore her, he sucks the fat tit greedily, noisily.

“Mmmmmm” Dorothy coos loving the attention the young man is giving her.

The cool night air and the slight breeze keep her nipples stiff as he moves his lips from one to the other as his thumbs find the waistband of her skirt. Hooking them in it, he pushes the tight skirt down off her hips just low enough to expose her garter.

Lowering himself he kisses under both of the mature globes then slowly down her white creamy soft belly as his fingers tug down the tight skirt. Using her left hand Dorothy assists, unzipping the skirt.

It slides off easily crumpling at her feet leaving her with a garter, stockings and heels. A few people on close balconies take it the sight. His greedy lips move lower past the garter and onto her smooth meaty mound
 
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