Stuck in August

Nis 23, 2024 // By:analsex // No Comment

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(Note to readers: The characters in this story have flaws. If you don’t like that, or interracial male-female-male group sex, with anal, or a male character with a bisexual history, you might want to read something else. All sex acts in this story are entered consensually, among characters who are all at least 18 years old. Thanks to vanmyers86 for beta-reading the first draft.)

When you met Hannah Robertson for the first time, you’d probably find her to be pleasant company. Let’s say you waited on her table at a restaurant, or visited her real estate office: She’d be as friendly as necessary for the encounter.

When you met her a few more times, you might see that you weren’t getting any closer.

Hannah didn’t talk about herself. She’d ask “How are you?” and maybe a question about something you had divulged about yourself earlier. If you answered that question, she’d stay with you on the topic until you paused. Then she would steer the discussion back to the reason for your meeting with her.

She wasn’t insincere. There were simply times when she had to make an effort to relate to people. When she didn’t have to make the effort, she wouldn’t, and kept to herself.

She had a sex life, but it was on her terms. Definitely NSA, because she didn’t want strings to be attached, but not FWB, because she sought benefits without close friendships.

This didn’t mean that she banged total strangers. She sought familiarity with her lovers, so she’d feel safe with them.

Familiarity, however, did not tell her everything.


She had been on her own for several days. Her mind was therefore tranquil, but her body was getting antsy. On this day, because she hadn’t lately worn her nerves raw dealing with anyone in her personal life, it was easy for her to be a nice and encouraging boss to the other five people in the office. She even chuckled at one of Darrell’s lame jokes.

But the day’s events soured her mood. A scheduled property inspection didn’t happen. Three of the open house yard signs used last weekend weren’t there when the others were picked up. Worst of all, the headquarters of the nationally-advertised realty firm connected to her operation sent a dour e-mail, with metrics purporting to show underperformance in Hannah’s office. By the time she closed up, she could no longer sustain her nice act.

As she drove home she wondered, Why the hell would somebody swipe an open house sign?

This failed to deflect her awareness of her streak of being alone. Her body wanted more than what she could do for herself, even as her mind insisted that the body still wouldn’t be satisfied fully on a date, when she may also have to put in an effort to get the guy’s rocks off.

At home, she checked messages and social media. Nobody was sniffing around in her direction.

Chiding herself for being desperate, she posted that she had an open calendar.

This got her no companionship for that night. A man named Brendan, with whom she had shared only some light chatting online, responded with a dinner-and-movie offer the night after tomorrow. She accepted, with a message she believed was light and upbeat. Then she got offline, resigned to addressing her own immediate needs.

She stripped, trying not to notice everything she considered wrong with her physical self. A life of desk-sitting, which she considered an advantage in her 20s and 30s, left her at age 46 low in energy and prone to muscle pains.

As she had done more times than she could count, she wondered if there existed a man whom she would welcome as a companion. Someone who’d be there when she needed him, but leave her alone the rest of the time. When, exactly, would she need him? And for what? She wasn’t happy, but had never seen evidence that she’d be happier with a guy in her life. What was happiness, anyway? If there was some condition, in adulthood, that was an improvement over the absence of annoyance, anxiety, pain, and dread, she hadn’t yet chanced upon it.

At 5′ 8″ and fairly big-boned, Hannah had excess weight that wasn’t obvious when she was fully dressed. Her ample bosom drew most men’s attention, and made excess elsewhere even less obvious. There was no fat yet in her face, but she was plain-featured. As for when she was undressed…

Any guy who wants it, she thought as she lubed a narrow-gauge dildo, is going to have to get it in the dark. She often resolved this, but never enforced it. In her experience, sex in total darkness was clumsy and disturbing.

She set pillows under her thighs so she could elevate them and bend her knees while on her back, and limit sciatic strain. She held up one jiggly breast, and set her other arm along her side as she carefully inserted the rounded cylinder in her cleft, and thus kept both boobs out of her armpits.

She licked her nipple, while she slid the dildo in and out. This hastened her arousal, fikirtepe escort but hurt her neck. She let her head drop back and moved her hand to her crotch. After the usual fruitless search for her G spot, she settled for rapid clit rubbing with the dildo held at full insertion. The orgasm was brief, but at least the spasms didn’t hurt her back and thighs.


Hannah’s father had been the boss, and he hired her after she got a business degree. From the words and actions of people in general, Hannah concluded that a local real estate office was considered okay as a family business, and the operation would have to be much larger before there would be grumblings of nepotism. Hannah nonetheless worked hard and smart, both to maintain the family’s prosperity and to uphold her self-respect.

Together, Hannah and her father had survived the mortgage debacle of 2008-9, working up to 80 hours a week and making the right moves at the right times. For a while this brought them closer, but eventually it wore them out, and they snapped at each other.

Her father was gleeful when he retired to Florida in 2011. The office was still in fragile condition, but the departure of her parents gave Hannah what she wanted from her close relatives: Less closeness. Her brother, who had moved out west, had three children, so Hannah was under no pressure from her mother to pair-bond and breed. The economy recovered and raised real estate values, so Hannah was under no pressure from her father to run the office differently. And Hannah got cheap winter vacations by crashing with her folks, each year enduring two weeks of closeness.

So now, the only person who had influence over Hannah Robertson’s life was Hannah Robertson. What she did with that influence was…nothing much.

Sometimes she challenged herself over her acceptance of the status quo. Shouldn’t she do more than go to work, get some no-strings sex once in a while, and live by herself? Yet this was her comfort zone, and she didn’t stray from it.

Hannah had never been in love. With no experience of it, she couldn’t even guess what that was like. She questioned whether she had the sort of emotions that other people had (or claimed to have), the sort that could make her give up her preferred isolation.


She and Brendan had agreed that he’d pick her up. She decided against insisting on them meeting at the restaurant, with two cars in use and each person able to depart alone if something bad happened between them in a public place. She chastised herself silently as she put on earrings, for behaving like a pushover. At least she hadn’t seen any red flags when she had looked into Brendan’s background.

She brushed her light brown hair as she waited. Many women her age basically gave up and got short, low-maintenance cuts. Because she had no gray yet, Hannah let the hair reach almost shoulder length. The hair spread in waves, and might be her best feature, apart from what swelled out from her rib cage.

Her phone chimed with an e-mail. One of her known quantities, Chet Guatreaux, gave her one of his flowery invitations to meet him, at her convenience. Deciding that it was too late to ditch Brendan, she sent back that she was free Saturday. Her feelings were on the down side of mixed, because she considered asking Chet for a favor that had nothing to do with hooking up.

When Brendan arrived, Hannah saw that he was fleshier and thinner-haired than he was in his profile pic. She wasn’t surprised, but was still brought down a bit.

Like most of the available straight guys her age, Brendan was divorced. Also like most of them, Brendan seemed to want someone to share remembrance of Gen-X stuff to which she had paid little attention. As a kid she had watched MTV, and for a while liked Michael Jackson, but gave that up when she decided he was starting to look inhuman. In her 20s and thereafter, she mostly let pop culture roll on without her, spending some of her leisure time on mystery novels, and not really getting a big charge out of them, either.

Brendan said he didn’t read much. He mentioned that he played self-help audio books in the car. Hannah was relieved that he didn’t elaborate, or share.

The food was nothing special. Neither was the movie. The sex completed the evening’s trifecta of meh.

She blew him only for foreplay, and she could see he made an effort not to be disappointed. He licked her pussy the same way, and didn’t seem to check if she was disappointed. The fuck was a one-and-done missionary, and he kept slobbering on her tits after he spewed, giving her time to finger her clit to a mildly pleasant tension release. His attention to her breasts helped, and she even told him that. She didn’t say that his weight on her caused some back pain, or that the most provocative thing that happened inside her was his withdrawal, as the condom wrinkled.

Despite her gebze escort admission, and his grinning response to it, neither made an effort to pursue a relationship. There was a kiss at the door, and the next day an exchange of private messages, with each saying that work was about to become really time-consuming.


The night before her date with Chet, Hannah’s other known quantity emerged from the woodwork. Treymont McKendrick sent her one of his heavily urban come-ons, full of what she assumed were samples of rap lyrics. Rather than mock him, and point out that he was a techie nerd from an unbroken home, she sent back a neutral response and a promise to get specific with him in a couple days. These trysts, with the two men she had lately bedded more than once, gave her hope that at least one of them would get her pleasure centers to stop complaining about how hungry they were.

Chet took her to his country club. Hannah, in a nice-enough dress with summery frills, saw no sign that the members and employees found anything untoward in a married man having lunch with a woman half his wife’s age. The rich are different, she thought, but they close ranks in support of their kind, just like the rest of us.

“Phoebe had one of her good days yesterday,” Chet said brightly, maintaining his fiction that Hannah cared. Hannah had never met his 90-year-old wife, nor would she. “She definitely enjoyed herself.” Chet showed her his phone, with a selfie taken at an exclusive nursing home. He looked quite dapper, next to the wheelchair-bound heiress who had something of a smile but unfocused eyes. Hannah gathered that the pic had gone also to social media, to show Phoebe’s relatives that Chet hadn’t abandoned his wife.

After lunch he took Hannah on a stroll through the club’s large and meticulously tended garden. At 73, he showed no physical limitations. He strode at a rate adjusted to a companion who was six inches shorter. He swung jauntily an ornate, silver-chased cane that he didn’t need, and he held his panama-hatted head high, relishing the breeze in his wide white mustache. Hannah was still mildly amused by his act, but envious of the garden. She sometimes thought she might enjoy gardening, but this bright floral display triggered thoughts of Why bother? and I am not worthy!

Chet had been attentive to her all along, but now turned to a topic he knew she wouldn’t want to discuss with others listening: “How is your work, Dear?”

She shrugged. “It’s what it usually is.” After a moment she added, “Corporate is grumbling about us. The office needs more activity.”

He glanced her way. “What would that entail?”

She looked up at him, taking a few seconds to choose words and not sound pathetic. “There doesn’t have to be a sudden flurry of buying and selling. But, if we were to get some new properties listed, maybe exclusives…”

He smiled, perhaps looking too sly because of the mustache. “I have friends who put second- and third-homes on the market sometimes, just to see if anyone bites on a huge asking price.”

“Nobody has to sell if they don’t want to,” she said quickly. “There’d be a listing fee, and some continuations, but no penalty if the seller drops the listing after three months.” She took a breath, then added, “Corporate likes big-ticket listings.”

His look was tender. “I think it’s terrible that you have to go through this. Bean-counters shouldn’t rule your life.” He unhooked his non-cane hand from her arm, pulled a wallet from his inner blazer pocket, and flipped it open to show that he still had the business card she had given him last year. “I’ll spread the word.”

She smiled in relief. “Thanks. And now, to prove you’re not my sugar daddy, I should go home alone.”

With the wallet returned to the pocket, he slid the free hand around her back. Leaning down, he whispered, “Whereas I intend to prove I’m not, with my prowess.”

Continuing their moment of fun, she said, “Okay, I’ll give you a chance.”


Chet maintained a suite at a nearby high-end hotel. Neither of them had ever broached the subject of screwing at the estate built by Phoebe Schrader’s long-deceased first husband. A chain of younger lovers, starting with trophy Phoebe, extended through Chet, to Hannah.

Hannah got a mild rush from undressing Chet, imagining what he’d been before. He was 6′ 2″ now, and bone/joint compression may have cost him an inch or two from his prime. He wasn’t stooped, and his carriage was silky. She suspected that he could move quickly if he had to. He had sent her his composite photos from when he was a sometime-working dancer, and links to two ’80s music videos in which he’d spun and jumped behind female pop stars.

She interpolated how he would have looked 25 years ago. Maybe a silver fox. Maybe not yet affecting the mustache. Hannah didn’t look that much better then, but at 21 she was more energetic, içerenköy escort and free of pain. Hannah wondered if banging him in 1995 would have distracted Chet from his project at the time, keeping his new bride Phoebe happy and gaining her power of attorney.

Even at this age, his prick maintained a good erection. It took time to develop, and wasn’t steel-rigid, but Hannah liked its surface flexibility, and didn’t mind his licking and fondling of her breasts, which produced the erection.

He treated her like a ravishing young mistress, and she admitted to herself that she relished her role. Never mind that she was probably his most worry-free option. She knew from their conversations that younger, prettier women he dated turned out to be golddiggers. Hannah’s silent commentary on this was: Takes one to know one.

His skilled cunnilingus took her most of the way to orgasm. She needed only about ten seconds of clit rubbing to finish herself. Chet had offered to do the rubbing, but she said he didn’t have to, while thinking that he wouldn’t do it properly.

She then fellated him for foreplay. They took turns because neither Hannah’s back nor Chet’s allowed them to stay in a sixty-nine for very long. The ensuing fuck was okay (he came, she didn’t), with Chet fingering her anus as he swiveled his putz in her pussy. A couple times before, she had let him in her rear end. His condomed prick had felt pretty good in her ass, but she’d still needed clit fingering to get herself off.

After today’s fuck, Chet wheedled her for more oral attention. She gave in, since he had eaten her out so diligently. But she expected to suck for a while and then finish him with her hands.

When she unmouthed his putz, he asked for more. And he did again, after more licking. He got whiny. Between his spread legs, she propped up on her elbows to make eye contact. She had never had to let him gunk her mouth before, and her back was getting achy.

“Does it matter that much?” she asked, sighing.

“Certainly! It’s always better inside!”

She offered, “How about between the tits?” She disliked the taste of semen, and the substance. Bad enough that she already had some of the fuck’s leftovers in her mouth. She swallowed just to get rid of them.

“That’s good, but it’s not a mouth!”

She lashed out, “So your meal ticket never blew you?”

He glared. “You leave Phoebe out of this!”

“Like she left you out of her throat?”

“Pleeeeeze!” he wailed. “The last mouth I came in was a man’s!”

She jerked back. A chill raced along her spine. She never thought she was homophobic, but maybe she hadn’t been in touch with her lizard brain. Her mind zoomed through consequences, likely or not. He’s alive and healthy, he must not have anything, oh no I swallowed!

She yanked her hand away. Semi-erect, the penis waved around above his belly.

She lurched to her feet, setting off back pain. She hurried to the bathroom.

On her way out she screamed about what a lover should reveal to a lover before exchanging fluids. He screamed back, but she didn’t process that as strings of words.


Whatever opinion she might have of gay men, she had to concede that her apparently-somewhat-gay man took forthright action. Before the end of the day Chet sent her a link and an access code to his own current test results, showing that he was clean of STIs and anything that could instigate them. He also sent her a pre-paid voucher to a reputable, confidential clinic in case she wanted to get tested, and a cash code to cover her cab fare when she’d bolted from the hotel. His attached text was terse, with no blubbering.

She sent this back:


She was too upset to contact Treymont, let alone set up a date.


The next day, Hannah had calmed to the point where she could put her incident with Chet in perspective. He had never been dishonest or evasive on anything else. While they were still e-chatting, before their first meetup, he told her that he was married, and that his wife was in severe dementia with no prospect of recovery. On that basis, Hannah decided to start dating him. Chet had also not promised, nor even hinted, that he would marry Hannah once Phoebe died, and Hannah had never pursued (or wanted) that.

Conversely, he had never said anything about having a history of sex with men. Hannah honestly didn’t know how she would have responded if he had divulged that. Maybe if he’d mentioned it before they were intimate, she would have dealt with it (while insisting on no fluid contact, except maybe between her breasts). In the abstract, she thought she had nothing against bisexuality, although her immediate reaction suggested otherwise.

However upstanding he’d been in most of their dealings, Hannah knew that Chet was undeniably a gigolo who had cashed in. Maybe, thirty years ago, he and the still-alert Phoebe agreed, in full, open sincerity, on how their marriage would work. Maybe he provided companionship and some amount of sex, and she let him inherit her wealth and sleep around. Hannah, however, knew nothing about that, and didn’t expect to learn such details.

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