First Time Sex Worker

The man depicted in this story is in an ethically non-monogamous marriage. The woman depicted in this story is divorced. All sex involves over-18 characters.

TAGS: milf, mother, stranger, christmas, oral sex, hairy pussy, open marriage, happily married, car sex, proposition

Six days without porn went by easier than Leary expected. Maybe it was only because it was the first time. Might future fasts turn out to be just as easy but not as surprising? He dismissed the thought.

In the here and now, Leary was cheerful. Besides the dopamine-detox he was undertaking, his sense of possibilities had just been blown wide open as well. He wasn't in any rush to charge off and start seeking fuckbuddies, but it was an option.

Months of communication, trust and sincere commitment to their 30-year marriage had very recently brought Leary and his wife Kel to a new understanding about what "fidelity" was supposed to mean in a sexless relationship with an asexual spouse. The couple hadn't been this happy and secure with each other, and confident in their future together, in a long time.

Driving to the grocery store on a December weekday afternoon, Leary felt easy, open and positive, as if basking in the afterglow of a nice therapeutic massage. He hadn't had any such thing, but his neurotransmitters had really shifted.

Kel wasn't aromantic, and the couple didn't want to stop loving each other. There was just no sex. The expectation, the anticipation, of yet another showdown over sex was now off the table, and it was freeing them both from maintaining the reservations they had employed around each other for years now. Fond embraces, evenings in bed cuddling together, and low-stakes, high-warmth intimacy like this was becoming as frequent as in the earliest days of their relationship. It was delicious to both of them.

Leary didn't think about why he was smiling, breathing easily and deeply, and feeling so un-stressed and so buoyant while he drove. But he did notice. He was liking it. It could have been the dopamine detox. It could have been the oxytocin hits which Kel's new emotional and physical availability was providing. Maybe it was simply the enhanced sense of future which comes when a depressing situation resolves itself positively.

He was in no rush to go out and score as fast as possible. Instead, he felt like the pressure was off, in a way. Knowing that the option, the permission was there eased the feeling of desperation he had endured during the long years of sexual starvation, and during the months of talking and vulnerability as he and Kel were forced to either work things out or not survive as a couple.

Getting out and locking the car, Leary started stepping across the parking lot lanes toward the store. An "excuse-me, sorry-to-bother-you" triggered a reflexive wariness and he kept his eyes forward. He used his peripheral vision to try to sense whether it was coming at him from an ordinary beggar-woman, or maybe one who would become persistent and pushy. The tone was as a matter of fact very lucid and guileless, and he allowed himself to look.

Shanna began her pitch just as soon as she saw she had his attention. It could be rescinded so quickly. She displayed a tidy, low-sided cardboard box containing half a dozen Christmas-themed gift-type bags. "My kids and I put these together. Can you help us buy a Christmas tree?"

Leary's "No, I'm sorry" was just a touch slower than his ordinary auto-response to begging, but he said it and saw Shanna immediately give up on him, scanning the lot for another person to pitch to. Leary kept moving and did his shopping.

He sure was horny, though. His good mood wafted through the store and he noticed reactions from women in there. He had never refrained from unobtrusively checking women out in various places and circumstances, but had his brain previously filtered out any reactions? Or was he being more forward, less subtle about it now, triggering women to notice and respond?

Maybe it had less to do with whether he was observing how pretty certain faces were, how shapely certain outfits made certain women look. Maybe it was more that his good cheer was simply written on his face, and it was contagious. The unconscious little micro-expressions people made seemed more engaging, different, less shielded, more upbeat as they crossed paths with Leary in the store.

As they entered and exited each other's personal space, as happens in a busy market, he felt like he was alive to them. Was there a hormone, a neurotransmitter, which had been turned up when his sadness had lifted, his major problem resolved? When his brain had absorbed the idea that pursuit was now on the table?

Wheeling his cart out of the store, a twenty-six year old, long-haired blonde attendant was bringing a stack train of eight or ten carts back from the lot. They were on a collision course, and Leary easily made room, swinging his cart wide on one side. The young woman read his intention perfectly and went wide around the other side instantly, and they smiled at each other, sharing the moment of lucidity. Leary spontaneously opened his mouth and briefly joked to the attendant as they passed each other, saying "Do-se-do!" and stepping with his feet in a slightly exaggerated square-dancing type of shuffle as they curved toward each other, now with room to pass.

He was pleased to see the attendant take the joke cheerfully and smile engagingly at him as they passed. It felt like a flirtation to Leary. He thought that she was unlikely to perceive it that way, mostly due to the age difference, but to him it made him think a little about his abilities in that department, for future encounters. This whole situation was so new, still.

It crossed his mind that the woman who needed the tree hadn't looked unappealing to him. She was younger than Leary, maybe forty or forty-five. Her face was pretty in an Anatolian way, healthy dark hair in waves over her neck. He remembered the bosom he had seen under her hooded sweatshirt, and had an idea.

Shanna was unselfconscious about trying to drum up Christmas tree money in a shopping center parking lot. She had done it the previous year, too. The time she had spent on the project with her fourteen-year-old daughter and nine-year-old son had been really nice. They had chosen the goodies, picked out cute bags, and stuffed them with the treats and knick-knacks.

They were rewarded with hot cookies baked from a pre-made refrigerated dough roll. The busy single mother didn't have so much free time as to make them from scratch, but it was still a treat. The tree would be even more so.

Temperatures were chilly but not freezing. The sky was heavily overcast. Shanna hoped she could get enough help from sympathetic and generous grocery shoppers to not have to spend a lot of time doing this. There was no precipitation today but cold rain was forecast for the next days.

Leary put his purchases in his car, closed it and locked it. He looked around the parking lot. He didn't see Shanna but started walking around.

He saw Shanna before long. She was talking to a Boomer-aged woman, looking into the tops of her gift bags and Leary guessed she was listing the goodies inside. The other woman had given her enough time, and hope, to cue up this part of her pitch, but Leary saw the woman shake her head apologetically and edge away. Shanna resignedly let her go and started scanning for her next potential patron.

"Hi again." From four cars away, Leary approached from the middle of the parking lane. Shanna recognized him after a brief look. Ten or fifteen minutes earlier, Leary had declined to stop for her. He had heard her pitch and decided No. Was he changing his mind?

She upnodded back, acknowledging Leary's greeting. He approached closely enough for conversation. "How much is a tree these days? Sixty, eighty bucks?"

To Shanna, this represented a pretty damn nice tree. "About that, yes."

"How much do you need?"

"I haven't sold one bag yet. They have - "

Leary's head was shaking. He wasn't listening to the pitch, didn't care about the goodies in the bags. "Hold on."

He had never done anything like this before, but he was in a mood. He had momentum. He had a six day load in his balls for the first time in decades, and a nervous system full of healthy, rebalanced neurotransmitters. He had cash in his pocket.

On his way into the store, he had not. He normally only carried plastic anywhere. But his credit card had been fraud flagged and closed, and he was waiting for the replacement to arrive, so he had been stuck paying with a debit card in the store. Unconsciously he had elected to get cash back from the transaction.

"Do you want to quit walking the lot and go home with all the money you need for the tree?"

Shanna looked at him, suspecting what he had in mind. Her immediate feeling was to shut this creep down and get rid of him as fast as she could. He was a middle-aged white guy, normal looking, no red flags other than the proposition she was just positive was going to escape his stupid filthy mouth if she didn't figure out how to reject it before it was even asked.

But she was slow. Not frozen, but this was so out-of-the-blue that her mind wouldn't make the necessary connections to lash out and repel the - Predator? Creep? Boor? Whatever you call those guys who have bottomless buckets of unwanted attention for you.

But was he? His manner was cheerful. He didn't seem desperate or predatory. Her instincts tried to sort out the conflicting messages. The alarm system blaring about danger conflicted with her senses which reflected a calm, reasonable-seeming person who hadn't even yet said out loud what he was thinking, regarding the money for her tree. The amygdala wanted to override the social mind, but she held it back just a little. Not ignoring it, but permitting a different stratum of her mind to operate while the alarm system fought for control.

Leary felt a sense of flow. That state you can achieve when you're carried along by events, acting spontaneously in the moment, without calculated effort to decide each moment's words or expressions. He instinctively didn't wait for Shanna to come up with an answer to his question. He continued and offered, "I'll pay for your tree if you would spend some time with me."

There, it was out. He knew she had to already be putting two and two together, and see where he was going with this. "Do you want to talk about it? It doesn't have to be long. You could be done with all this and get home before you know it."

Shanna's face looked stunned. She had not been wrong. She felt her mouth gape open, and closed it. A part of her shuddered against a slimy feeling his words triggered. She stopped looking at Leary, and her eyes rolled around the parking lot. Nobody was paying any attention to the two. They lifted to regard the heavy clouds. It was dark and cold and she could be here for hours. Last year it had taken three days to sell enough bags and get enough donations to pay for the tree. And it had just been a shitty little one, not one of the tall, full, even and fragrant ones sixty or eighty dollars could procure.

Leary saw her struggle with how to react. She probably was just trying to figure out how to say No. He would of course let it go, if that were her response. But until he heard the word, he felt an imperative to keep pitching this to her. "My car's right there. We could just park it at the empty side of the lot, you could keep me company for a little while." He noticed something in the direction he was pointing. "There are security cameras over there, you'd be fine. I'm not a psycho. I'm just lonely."

That was a magic word. Shanna's eyes found his again, and she picked up the vulnerability behind his confession. It struck a chord, as she had been lonely too. Two years divorced now, there had been nobody but her kids and her sister. She had had no idea how to even consider seeking the attention, time and touch of a man in all that time, and much longer. She was just struggling to hold on, for herself and her kids.

It didn't make her want Leary. An offer to pay for your "company" was not a turn-on at all. She could still hardly believe she was being propositioned like this. Her mind was busy isolating that fact, segmenting it away into a zone of thoughts entirely separated from the sudden hope that surged. Could this relieve her of hours and hours of basically begging in the supermarket parking lot? Could she use the time which she might win back in order to rest, to play with her kids, to give her poor sister a night or two off?

She didn't know what to say. Her mouth was open again, her brow was knotted. She was jarred with conflict, and was surprised by it. She was not processing this quickly enough to reject Leary or to negotiate.

Leary saw her conflict and brought his head just a little lower, and closer. Stooping to her eye level would have been patronizing, but he wanted to get her to focus on him again. Shanna did peripherally notice the inviting position his face had assumed, and her eyes flicked to his.

Leary wasn't thinking of her as a prostitute. He knew she was a mother doing the best she could for her kids, and just trying to do something special to adhere to the tradition. He was interested in what she might become willing to do for him and continued his persuasion. "Here, let's just talk about it. You can sit in my car with the heat on. I'll stay outside, you can crack the window, and let's just talk about it."

He smiled reassuringly. His words flowed persistently, filling in the spaces where she had had the chance to say No but missed taking it. Yet he tried conveying humility, low stakes, and safety. "I won't be mad if you say No, but if it would help you out, do you wanna come think about it?"

Shanna pictured sitting in the stranger's car with the heat on. Keys in it, to run the heat. Leary outside, talking to her through a cracked window. One of the various parts of her mind clambered out of the soup of conflict to reach the surface and direct her mouth to act. She heard the words come out, quietly. "You have eighty dollars? Cash?"

Leary casually took in the parking lot without an obvious 360º scan. Nobody had paid any attention to the pair while they talked. He answered Shanna with a silent nod, and turned. He beckoned, and walked to his car.

Shanna also took an awkward look around the parking lot. As if anyone would have any idea what was going on. Nobody's attention extended beyond their own personal three-foot bubble. She followed Leary, and noted that he was allowing her to keep up with him.

He opened the driver side door, got in, started the car, and turned on the heat. He put eighty dollars on the passenger seat. He got out, closed the door, and opened the other side for Shanna, smiling encouragingly.

Shanna frowned to herself as she saw the bills on the seat, but got in. At first she sat on them, and left them there. Leary lowered the window three inches and swung the door almost closed. He stopped and held it at the last moment, and Shanna pulled it the rest of the way shut.

She looked up through the window with her dark eyes. Leary looked back. He was glad she was pretty. He thought he wouldn't be doing this otherwise. Shanna didn't think about how Leary looked, in terms of attractiveness. She simply paid attention to whether he seemed honest and non-violent.

Leary re-initiated his patter. He said through the gap in the window, "Yeah. I'm lonely. My wife doesn't have sex with me. But she lets me do this." He stopped talking about himself. "Your kids must love you a lot. You're very pretty."

He stopped there. His cards were all on the table, there was nothing else to say. He needed Shanna to start thinking and talking about what she would consider doing for this money with this man.

She didn't quite know where to start. "What do you want me to do?"

Leary didn't have this explicitly figured out, so he thought out loud. "How about, a blow job? And feel your tits? Would you kiss me too?"

"I won't kiss you. Come on, let's go over there, then." She pointed where Leary had indicated, the far side of the lot where the spaces were mostly unoccupied. Then she lifted her butt up and retrieved the four twenty-dollar bills from the seat. She stuffed them into one of her gift bags and Leary got in the car.

Shanna rolled up the window as he drove and parked by a light pole with a security camera and a blue panic-station light on it. He shut the car off and described his thinking to her. The camera could see the car and its surroundings but not past its roof or into its windows.

She nodded, getting it. "Good thinking. All right, I guess. Let's do it." She wrestled the box of goodie bags between the seats and into the back of the car.

Leary said, "Thanks." He twisted in his seat, facing Shanna. "Can I touch you?"

She nodded, and he reached for her far shoulder. With his hand pressure, he invited her to stay turned toward him as well, as she was coming back from putting the bags in the back. He smiled at her, she grudgingly quirked the corner of her mouth and looked down. He cupped the side of her neck and felt under her scalp with his fingers.

Shanna was uncomfortable with the familiarity of this. Ironically, it would be better if he would just go for her boobs. That was easy to compartmentalize. She took his hand from her head and neck, and put it on her chest.

"I want to go under your clothes." He felt her through her hooded sweatshirt and a couple of layers underneath that. Then he moved his hand down to the hems at her hips, and used both his hands to lift her layers until he could get his hand to her bare waist.

Shanna allowed it. She looked about through the windows. Nobody was nearby. The windows were starting to fog slightly. She helped with the lifting, and Leary's hands skimmed up her flanks and ribs and found her bra.

Leary was feeling the hormones and juices begin to pump through his body. The bra-covered tits in his hands caused a surge of desire. He breathed out a quiet moan, and rounded his lips in a silent "Ooh" at Shanna. His eyebrows pulled together in the middle. She looked at his sex-hungry expression and kept her own face straight. One shouldn't laugh at the one paying.

He liked looking in her eyes as he felt her. He watched an expression that said, "All right, whatever," cross her face, and she undid her bra in back and lifted it over her tits.

They were bare now, under her layers, and Leary's hands explored them eagerly. "My God, I love them," he promised Shanna.

She almost rolled her eyes, but allowed herself to smile. It was a compliment, after all. And he was being honest. When he tried pinching her nipples, it was too much, and she covered his hands with her own through her layers and made them go still, holding her breasts.

Leary's jeans were very uncomfortable, an erection having risen in them with no attempt to arrange things to accommodate. He got his hands from under her top and sat facing forward. He let the seat roll all the way back and pinched the front of his jeans inside his curled fingers and palm, pulling the snug fabric away from his groin and making room for the stiff boner to live within.

"Take them off," Shanna said.

Leary cooperated and undid his belt and fly. He didn't take them off, but he tilted the seat-back, laid back into it, and pulled the jeans and undershorts past his hips. He pulled the front of his flannel shirt and sheepskin-lined jacket away from his belly, draping them down his sides. His sex was fully exposed and he brought a hand to his balls, lifting them from between his thighs to rest on top of them.

Shanna looked around through the windows again. It was starting to seem a little darker outside, but still nobody was nearby. She leaned down into Leary's lap and took him in her hand.