Dorothy out of town

I watched Dorothy's mind drift away to the scenario I posed. She was gone a few seconds, but slowly she drifted back. The sight made me smile. It had been a long, long time since I'd seen a woman so intent on getting laid. Dorothy's behavior made me smile.

Placing a hand on hers, I pulled my gaze from her cleavage.

"You're looking for an adventure. I get it. I don't know what your situation is at home, but I can see what you want for this particular trip. I don't know about multiple men, and I didn't approach you to pimp you out or anything, but later on, if you'd like, I wouldn't mind getting to know you better."

About this time, our waiter came to the table to set two glasses of water down. He was a crazy tall young man, maybe pushing seven feet. All I knew for sure was that when he straightened, his crotch was damn near in Dorothy's face.

"Hi, I'm Paul. I'll be your waiter. Can I get you anything other than the water to drink?"
 
“Hi Paul” you reply and order your drink. Dorothy turns and sees she face to face with Pauls crotch, looks up and says “I’ll have a Cosmopolitan Paul”. As Paul walks away Dorothy turns again “Oh and make mine a “stiff one” Paul acknowledges her with a smile and a nod.

Dorothy puts her other hand on yours. “You know Evan I have to be honest with you, about six years ago my husband was in a nasty car accident that left him partially paralyzed.” “And not only that it robbed him of his Libido” “So these last few years I have used my business trips to various cities to make up a little bit of Pauls attention, if you get my meaning”

“Now it isn’t that I have sex with every man I meet, or that I do it every trip, but I’m not going to deprive myself of some innocent pleasures on occasion”

You watch as Dorothys eyes go from sparkling blue to a smoky gray.

“Oh yes, and by the way my mention of multiple partners, that’s really just a fantasy of mine, I haven’t done that since High School and my first year in College.”

Even the slightest movement by Dorothy wobbles her boobs under her blouse, her areolas bristling with the cooler air.
 
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Dorothy eagerly eyed the waiter's crotch. I could tell the guy was used to it. He was working the wrong job if he was going to have a problem.with it. He took it in stride and just smiled and politely too our drink orders without comment then left.

Once Paul was gone, Dorothy confessed her plight at home. It was as I suspected. I felt bad for her, as well as her husband. Life can be really cruel and unfair.

She also admitted she hadn't expected sex on this trip. If it happened, it happened. She and her husband must have some kind of agreement.

She then went on to admit that multiple partners was a fantasy... now, that is. She had apparently enjoyed a gangbang or two earlier in life.

I couldn't help but laugh at her confession. "I bet you had plenty of fun back in the day.

"Unfortunately, I wouldn't know how to recruit anybody else for you. If it's meant to happen, I'm afraid it'll just be me."

By this time, Paul had returned with our drinks. He stood deliberately close to Dorothy when he asked if we wanted appetizers.

"We haven't even looked at the menu," I told him.

"It's no problem. I can come back in a couple minutes if you like. No rush," he said graciously.

"No, it's okay," I said. Opening my menu, I perused the appetizers, taking more time than was really necessary so Dorothy could admire and imagine what laid behind Paul's zipper.

"How about stuffed mushrooms?" I said after a good minute of false deliberation.

"I'll get that right up," he smiled, giving a little extra glow to Dorothy.

When he was out of earshot, I leaned in. "He knows you're looking at his crotch."
 
As Paul set down the drinks Dorothy couldn’t help but get a view of his crotch. She saw a VERY distinct outline of at least a nine to ten inch cock in his pants.

Taking a sip of her drink Dorothy exclaimed “Oh my Goodness Paul, this is a nice stiff one, thank you very much” her eyes travelled the length of the young mans thick member.

He looked down at her, he could see almost her entire left tit under her blouse from his angle. “You’re very welcome ma’am.”

As he leaves she hears you say that he noticed that she was looking at his crotch.

“Was it that obvious Evan, I don’t know if you noticed or not but that young man was at least three quarters erect”

You notice that Paul had returned to the waiters station and was having a conversation with another young waiter and a attractive waitress looking back at your table as they chat.
 
"I don’t know if you noticed or not but that young man was at least three quarters erect”

I chuckled. "Can you blame him? You couldn't take your eyes off it. If it'd been me, that much attention would certainly get me hard."

Back at the waiters' station, a conversation was going on. Paul was talking with a couple of his colleagues, and the glances and the smiles kept turning our way.

"I wonder what they're talking about," I mused. "Maybe he's trying to recruit some friends to come over and take care of you."
 
“Maybe, just maybe” Dorothy replied. Within a few minutes Paul was back with our appetizer order. He places it down on the table then a small plate for you and one for Dorothy. A small rolled up slip of paper falls into Dorothys lap. She quickly snaps it up and drops it into her purse.

Paul smiles at both of you, “Anything else right now?” He asks

“We’ll be ready to order in a few” you say

“These are delicious” Dorothy remarks emptying her glass.

After a few of the delicious mushrooms Dorothy excuses herself to the ladies room. You watch as a few of the patrons watch as she makes her way through the outside tables then into the restaurant itself. Once in the ladies room she quickly digs out the slip of paper from her purse and unrolls it.

“I’m available after 11 PM, Paul”

Is swooning still a term, her face flushes upon reading the little note.

She couldn’t believe he actually gave her a note. She tucked it back into her purse, fixed her makeup just a tad and made her way out of the ladies room, winding through the tables once more she spots Evan across the outdoor dining area watching as she approached...
 
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I notice Dorothy fumble for something when Paul handed her her appetizer plate. She didn't say anything, but quickly she was back. It made me wonder what just happened.

When Paul asked if we were ready to order, I told him a couple more minutes and he nodded and left to help his other customers.

Dorothy seemed really flustered and after a couple of the mushrooms, she excused herself to the restroom.

When she returned, she was even more flushed and flustered.

"What's going on?" I asked, hoping nothing was wrong. "Are you okay? If you need to head back, we can leave."
 
Without speaking Dorothy hands you the slip of paper Paul dropped in her lap. You pick it up, open it and read it.

“He wants to fuck me Evan” Dorothy says quietly and almost breathlessly. You watch as she turns to look at the waiters station, Paul is nowhere to be found.

“it appears so from the looks of this little note, do you want to fuck him Dorothy?” Dorothy looks down at her empty plate, “I’m out with you Evan” she looks up at you “and I’m going back with you” she feels a tingling between her legs just imagining the tall young man with his head between them.
 
At my question, Dorothy handed me what looked like a sheet off one of the wait staff's order pads. A glance at it told me why Dorothy looked shocked.

"He wants to fuck me, Evan." She sounded like she didn't believe it. The waiter's station was empty when she looked in that direction. She must have been trying to get confirmation for what the note said. Even though I knew the guy was at work, his lack of presence at that moment sent my mind to a dark place. I didn't like to think such things, but young folks can be cruel. Pushing such thoughts away, I replied:

"It would appear so. Do you want to fuck him?"

Dorothy seemed surprised by my question, but her eyes guiltily dropped to the table.

"I'm out with you, Evan, and I'm going back with you." Her voice was small, the tone embarrassed, but the little squirm she gave said some part of her was definitely interested.

"I appreciate that, and I'm honored, but you didn't answer my question: do you want to fuck him? It's okay to tell me yes."
 
“Well as a matter of fact I would” she tells you “My good friend and I have a saying about young men like Paul, Young dumb and full of cum”.

She begins to tell you about her friend Debbie from work. A tall strawberry blonde gal, divorced, can drink beer like a guy and can “Suck the chrome off a trailer hitch” as shes been told by a few guys in the plant.

“I love Debbie, shes so fun to be around”

You’d like her Evan” she says as she leans toward you across the table and takes your hand, her full tits on top of the table presented like appetizers on a party tray, the tops of them jiggle slightly.

“I need another drink, don’t you? She asks with a gleam in her eye
 
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The fact that I still was willing to play perked Dorothy up. She grinned and admitted: “Well as a matter of fact I would. My good friend and I have a saying about young men like Paul, Young dumb and full of cum.”

She then told me about her friend, the "good time who was had by all." From the way Dorothy talked about her, it sounded like this Debbie was kind of an inspiration for her fantasies.

"It sounds like I would like Debbie. Maybe I could get the two of you to show me a good time. Two women has always been a fantasy of mine." I half spoke to the tits Dorothy had laid on the table in front of me. Dorothy was having fun being a flirt, and I couldn't deny I was enjoying it, too.

After grinning at my "two women" line, Dorothy said, "I need another drink. Don't you?"

Grinning back, I asked, "What, are you going to ask Paul for a sip directly from the tap?" If she was still up to playing, I was willing to go along.
 
As Paul approaches the table to take out order Dorothy notices that all the male wait staff is wearing loose fitting cargo shorts. He stands next to her and asks “Are we ready to order?” As she peruses the menu Dorothys right hand slips below the table and onto the back of Pauls bare knee.

“Let me see whats looks good here” she says as her hand now slides up under the leg of Pauls shorts.
Moving around to the inside of his thigh the smooth skin feels good on her palm. Her hand moves up higher...she feels something soft and warm on the back of it, her eyes widen.
Pauls going commando under his work shorts! She feels the warm soft hairless skin of his scrotum on the back of her hand.

“Mmmm” the large chefs salad sounds good” she says looking over at you, her palm flips over and is generously filled with a large set of meaty balls. Her manicured nails reaching upwards then raking down gently over them. As you order Dorothy gently rakes her nails over his scrotum over and over slowly, her palm caresses and cradles the heavy balls as she does.

Her eyes never leave yours
 
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I don't know if it was intentional, but when Paul came back to take our food orders, he stood particularly (or sould I say: peculiarly) close to Dorothy.

She wasted no time and next thing I knew, she had her hand up his leg and into his shorts. Dorothy must have found something she liked, because she got a huge, pleased grin on her face and her hand stayed up the leg of his shorts while she pretended to look over the menu.

Paul appeared to be having a good time, too, if the blissful look on his face was any indication. I could only imagine what Dorothy had found under those cargo shorts, but I have a pretty good imagination.

A glance over to the waiters' station revealed Paul's co-workers were watching the treatment he was getting, and they were silently rooting him on, even the ladies.

When I looked back to what Dorothy was doing to our waiter, I noticed it was having the effect I'm sure she was aiming for.

"Dorothy, I think you're going to have to let Paul get our orders in. You're going to make him have to wait his tables with a raging hard-on if you keep it up. You probably wouldn't mind, but it might be at least a little embarrassing for him."

I couldn't tell if Paul really gave a damn if he sported a huge woody here at work, at least not at the moment, but if he was going to get our orders taken, he'd need to be free to do so.

I hated to curtail Dorothy's play - and Paul's, for that matter - but this WAS a public place and the last thing any of us really needed was for the wrong person to notice...
 
Dorothys expert fingers find the base of Pauls thick tool and using her thumb and index finger give it a good squeeze coaxing a low grunt from the tall waiter before hearing you mention that she ought to let Paul get back to work.

She slips her hand from the leg of his shorts letting her nails drag down the inside of his thigh as she does. Paul after taking your order turns slightly toward Dorothy letting her get a good view of the size of the erection she had given him. As Paul walks away his coworkers get a good chuckle at how obvious his erection is.

“I’m sorry Evan, here let me show you a photo of my friend Debbie” Dorothy slides her chair around the table next to you then begins rummaging around in her purse.

She pulls out a photo of a woman standing next to a bicycle. “We were on a bike riding day at the park in this one.



You admire the woman in the photo, but you see another photo under the one of Debbie of 2 gals, one brunette and one blonde.

“Who are those girls?” You ask as you feel Dorothys knee on yours.

“Oh gosh, that’s my daughter Erika and her friend Emily, Erika is the blonde one”

You lean in closer to get a better look, your face just inches away from Dorothys, she turns her face to yours, you turn to hers.

Dorothys world gets smaller, just you and her are in it at the moment, her lips take in yours.
 
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Reluctantly, Dorothy pulled her hand out of the waiter's shorts. A pretty impressive bulge was clearly evident in Paul's pants from her attention, and the grins back at the waiters' station said they were both amused as well as happy for him.

Dorothy watched Paul until he disappeared from view, then turned back to me.

"Want to see a picture of my friend Debbie?" she asked brightly, her mood bouyed by feeling up our waiter.

"Sure," I told her. Why wouldn't I want to see what her friend, the slut, looked like?

Dorothy smiled and grabbed her purse, moving her chair around the table closer to me. After a minute or so of digging through the ephemera in her purse, she pulled out a wallet and began paging through until she found the picture she wanted.

"This is my friend Debbie. Debbie the slut, and I love her. We were on a bike ride in the park.

The woman in the picture was the same degree of attractive that Dorothy was, so I placed her in the "fuckable" category in my mind.

As my horny brain was formulating a scenario where I was having fun with both these sexy mature ladies, the way Dorothy was holding the folio allowed me to see some of the picture just behind the one she was showing.

"Who are these girls?" I asked, flipping the pic of Debbie over and revealing the one beneath of two much younger women

Dorothy had scooted in close to show me the picture of her friend, and I became aware of her closeness when I felt her leg against mine.

"That's my daughter, Erika and her friend, Emily," Dorothy said with pride. As I moved in for a closer look, I saw the resemblance just as she told me, "Erika's the blond."

I leaned in just a little more and was suddenly aware how close I'd gotten to Dorothy. My head turned in her direction at the same hers turned to me.

Soon after, our lips met.

It wasn't a long kiss. Even as sexually charged as this tease session was, we both backed away simultaneously.

"I'm sorry, Dorothy, I didn't mean to..." I wasn't sure where to go. I wasn't exactly embarrassed at having kissed her, but we'd only known each other a couple hours. Was that moving too fast?

Then again, she'd just felt up our waiter after knowing him only a few minutes, so maybe I was reading too much into the situation.
 
Smiling Dorothy looked into your eyes, then hers close slowly as her soft warm lips take in yours once more. Her wet tongue quickly darts in and out between your lips, they press against yours.

You hear and feel the soft ”Mmmmm” from her throat.

Her tongue explores, probes deeper and deeper her soft unrestrained breast presses against your upper arm.
Finally she pulls back almost breathless. “No need to apologize Evan” her lips once more touch yours but in a lighter fashion, just a peck this time grazing sensually, softly across yours.
 
Instead of being embarrassed or angry, Dorothy just smiled slightly and leaned back in and kissed me again.

I just let it happen. Dorothy was being the aggressor here, and I was content to let her do that. This whole deal was kind of her fantasy, so if she wanted to dictate where it went for a while, I was good with it. I could be her boy-toy if she wanted me to be. She could do what she wanted while I was around. If she wanted me to recruit Paul and his buddies for an evening of cock, cock and more cock, I'd sure as hell try to do that for her. If she wanted to feel me up like she had the aforementioned Paul, I'd gladly submit.

I wasn't going to be completely passive, though. After Dorothy backed away long enough to tell me I didn't have to apologize for anything, she leaned back in for yet another kiss. This time, I placed a hand on her bare thigh and let it ride up and under her skirt, even if I couldn't reach all the way up...
 
Feeling your soft hand on her thigh she let her legs spread just a bit to allow more access, her lips brushing yours lightly.
The tip of her warm wet tongue lightly grazes your lips as well. Her hand slipping under the table and placing it on yours, encouraging its wandering.
As her tongue glides over your lips she whispers softly “I want this to be the most exciting evening you’ve ever had Evan, is that possible?”
 
“I want this to be the most exciting evening you’ve ever had, Evan. Is that possible?”

I looked at Dorothy a second and felt her hand rest on my thigh. I wasn't wearing loose shorts like our waiter was, so I wasn't going to get a fondling like he had, but taking this to the next level was definitely not out of the question.

"I don't know," I said, changing position in my seat so I could reach under Dorothy's skirt a bit farther. "But I'm willing to do the same for you, if I possibly can."
 
Her lips lightly touching yours as you speak her hand slightly squeezes the inside of your thigh.
“I think that is highly possible Evan”
Glancing to the side quickly then back so her lips are brushing yours she says
“What do you think about that young waitress, I don’t miss much dear” Her hand sliding slowly up the inside of your thigh.
 
Dorothy then pointed out one of the waitresses, a little heavier girl, but with a rack and ass to die for. She had on shorts like the guys did, but hers were a hell of a lot tighter, and her top was strained to bursting from the impressive size and shape of her bust.

"Any of these waitresses would be a hell of a lot of fun, I'm sure. How about you, Dorothy, do these young ladies do anything for you, or are you strictly a cock girl?"
 
Dorothy leans forward, her full melons hanging freely under her blouse, her lips lightly touching yours, her legs spreading even more for you.
“I’m up for whatever you have in mind Evan” she says, her lips grazing over yours ever so lightly as her hand slides farther up the inside of your thigh. As it does her thumb feels a lump through the material. She allows it to gently glide back and forth over the lump as she softly whispers to you.
“I want it to be a fun week for us” she softly kisses your lips.
“Would you like to see us together Evan” she whispers with another soft kiss, her thumb follows the lump as it grows down the inside of your shorts.
She turns her head to get a look at the waitress once again then back, her lips brush against yours lightly.

“I could see myself sucking on those big boobs of hers, could you imagine that Evan? she whispers as her finger traces the outline of the head of your cock through the thin material her lips brushing yours.
 
Dorothy was truly ready for an adventure, considering her answer to my question. While she caressed and rubbed the head of my cock in my pants, I imagined her and the waitress doing the girl/girl bit for me.

"Dorothy, that would be hot as hell, to see you sucking that girl's big tits. I'd love to have the two of you at the same time, one riding my cock, the other my face."
 
Whispering again Dorothy says “Do you think you could make it happen for us Evan?” Her thumb still tracing around the head of your cock.
The lump has gotten so much bigger Dorothy thinks to herself “This guy is certainly endowed” she scoots closer to you, her fingers trace the length of the thick tool now as she speaks, her breath becoming somewhat erratic as her fingers continue up the thickening shaft.

The girth of the meaty pole has Dorothy becoming flush and her nipples harden as her fingers gently squeeze it.

“Remember, we have all week together..don’t we Evan?” She says kissing your lips lightly

As darkness begins to fall, the lights start coming on through the street area and Dorothys fingers now travel up and down the stiff meat in Evans shorts.

She kisses your lips lightly. “It seems you may be ready for a little show?”
 
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"Do you think you could make it happen?" Dorothy asked in response to my comment regarding having two women at once
If Dorothy wasn't already playing with my cock, her asking such a question would have certainly gotten my cock hard.

"I'm not sure," I started, "but I think we know somebody who might be able to help if you want to try. He's already made an offer, you know. Hell, maybe he wants to fuck that rack, too."

I wasn't sure if Dorothy was serious or if she was just continuing the teasing play, but if she really wanted to have an adventure, I was more than willing to take part in it.

As it got darker and lights came on around us, Dorothy began to slowly jack my cock as best she could while it remaimed encased in my shorts.

When Dorothy said, "It seems you might be ready for a little show," I wondered what she meant and asked her just that.
 
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