The Rounds

Bob slept fitfully on the couch in his outer office, and when the sun came through the window with his name and the words “Private Investigator” lettered on it, he got up. He showered in his back room, changing the bandage on his shin as he did so. He put on a pot of coffee, and got dressed in a brown suit, blue oxford shirt, and red tie. No one would ever accuse him of being fashionable, but no one would think him scruffy, either. His bathroom doubled as his darkroom, so as he scraped his face that morning, drinking his coffee, he was surrounded on all sides by images of two men having sex.

The first thing he did when he sat as his desk was call Mrs. Helena Watting, wife of software designer Joseph Watting, he of the assfucking from the previous evening. As he waited for he to come to his office at eleven a.m., he put the file together on Joe’s actions of the past three nights, clubbing, bars, and three different gay partners, all when he was supposed to be in Gargan on a business trip. Helena hadn’t been happy in her marriage to Joe for years, and had sued for divorce. With his allegations against her that he was a faithful and true husband in the face of her rampant promiscuity, she had needed some sort of ironclad refutation of that in court. Well, Bob Randall had put that together quite well for her.

At eleven sharp, the buzzer signaled that Helena was downstairs and wished to be let in. Bob walked down to bring her in the front door of the building.

“Hello, Mr. Randall. You said you have some news for me?” She was understandably anxious and excited.

“Yes, Ma’am, I believe I have what you need for your day in court - I guess it comes as no surprise to you that Joe’s a naughty boy, after all, that’s why you hired me. Please,” He said as they entered his office, “have a seat. Coffee?”

Mrs. Watting sat down in one of the two cloth and chrome chairs on the other side of the desk from Bob, declining his offer of coffee. Bob held up the file on her husband, he said, “I should warn you, this could be quite a shock - I, well, I don’t know what you’re expecting.” Finally, after several anxious seconds, he handed her the file.

She sat, examining the thick file for quite some time. Inside, along with the detailed descriptions of her husband’s movements and activities, were several photos of Joe engaged in various forms of homosexual activity, with men she’d never seen. Here was Joe getting fucked in the ass, here he was sucking a cock, here, licking a man’s anus and jerking him off. There must have been fifty photos. As she looked at them, Bob noticed her getting flushed and angry. She squirmed in her seat, crossing and re-crossing her legs. Finally, she looked up and said, “Do you have a restroom I could use?”

Bob’s restroom was currently hung better than one of Joe’s sex partners, with pictures of her husband all over the place. Luckily, there was a ladies’ restroom just outside his door for the patrons of the nail and hair place in the same building. He directed her to that, and told her to please take her time, do whatever she needed to do. He went back down and sat at his desk, breathing a big sigh of relief, and taking a shot of bourbon. Just as he was screwing the lid back on the flask, Helena’s voice from the doorway asked, “You always drink this early in the morning?”

Caught, Bob made a lame excuse about late nights and the tension of the job. Helena came around the desk and took the flask from his hand, unscrewed the top, and slowly took a long pull of the booze. Standing silhouetted against the window, Bob could see her figure through the thin material of the dress, and decided that the only reason a man would fuck around on a woman like this is if he were gay. Helena caught him again, this time with his eyes lingering on her perfect breasts.

“Joe’s right, you know,” she said.

“About?”

“I am terribly promiscuous. He hasn’t made me happy for a long time, and so I do find happiness elsewhere. A lot of elsewheres. These pictures just make sure that he can’t continue to make it difficult for me to find happiness. Don’t you think a woman should be allowed to find happiness where she can?”

Bob, fixated on her long legs and sculpted buttocks, allowed his gaze to travel past her small waist and to her 36D breasts, up her elegant neck to her lips, and then into those blue, blue eyes, framed by long reddish-blonde hair before realizing he hadn’t answered her. “Oh, yeah, of course.”

“I’d like to pay you for your services.”

“A check or credit card will be fine.”

She answered, “I feel as though you went above and beyond, though, Bob, and I want to go above and beyond for you, too.” She put her foot on his chair, with her toes at his crotch. Her toenails were painted red. She leaned forward, proffering his flask. When he went to take it, she pulled his head into hers, their mouths together. Their tongues explored one another’s mouths, and her toes wiggled against his growing cock, and under his balls. His hands rested on her breasts, and he felt her tight nipples through the flimsy fabric - apparently the bra had come off in the restroom. She broke the kiss and stood back, dropping her dress to the ground, revealing her naked body, clad only in red spike heels and earrings. She grabbed him by the tie, and hauled him out of the chair, massaging his cock through his pants.

Once into the back bedroom, she slowly undressed him, lingering at each item of clothing, kissing each part of him that came into view. She took off his tie, and nuzzled her face against his neck, kissing him, and nibbling his earlobe. Unbuttoning his shirt, she sucked lightly on his nipples and worked her way down, kissing his chest and stomach as she unbuttoned. His cufflinks hit the floor, and one rolled under the bed. It's weird, the things you'll make mental note of when the unexpected is happening. Bob stepped out of his shoes as Helena unzipped and unbuttoned his pants. Her earrings were cold against his cock as she kissed and sucked on his balls. Soon he was totally naked, and she stood and kissed him deeply once again. He squeezed her buttocks as she pressed her tits against him, their mouths locked together once again. She slowly pushed him down on the bed, in control, with an obvious idea about how this was to progress.

Once he was lying on the bed, she began to suck his cock, gently, teasing his balls. She looked up at him as she likced and teased him, and soon he lay back and closed his eyes. She stopped for a moment, and when he opened his eyes again, they were 69’d, her ass above his face, her pussy in plain view. It was so wet that a drop of moisture had formed and was slowly travelling down her left thigh, in a kind of sideways motion, making its way to her knee. She brought her sex down to him, and he spread her out and licked her pussy lips, going around in smaller and smaller circles until finally pushing his tongue inside her, tasting her wetness. Pulling out, hee slowly worked his way back around her labia to her clit, and sucked it into his mouth, licking it and sucking on it like a tiny cock. While he did this, he slipped two fingers into her, one straight, and one crooked so as to massage her G-spot. He could feel her mouth on him, and Helena was amazing. Her tongue teased the base of his shaft, and her mouth grew tighter on his cock as she rose up, and then looser as she went down. Her could feel her long hair tickling his balls and thighs. She took the whole of him into her mouth, moaning against him as he ate her pussy from behind. They stayed this way for a while, on the bed in his back office, teasing and sucking, making each other wetter and wetter. Occasionally, her body would tense against him as he stroked her G-spot.

Abruptly, she stopped sucking his dick and sat up, pushing her pussy into his face. He buried his tongue in her, and she squirmed, sitting on his face, his hands now on her cheeks, spreading her out, tasting all of her. She cried out, "Oh god yes, Bob, fuck me with your tongue!" Eager to please, Bob's nimble tongue darted in and out of her, licking her juices, making her crazy, if her fidgeting was any indication. She tasted so good, and he wanted her to cum for him. He put his fingers back inside her, and thrust them against her G-spot as best he could from his somewhat awkward position, all while licking from the opening of her vagina to her anus, and back again. She gasped and began to play with her nipples, massaging her tits, bringing first one then the other up to her mouth to suck on them and bite the nipples. When she came, she was quiet - she lurched forward, grabbed Bob's legs, and a seismic shudder ripped through her body. Her thighs clamped around his face, and her nails dug into his legs. She pushed her pussy so hard against Bob's face, he briefly thought he might suffocate. When she was done, she rolled off of him, her head at his feet, and her red toenails at his eye level. Her hand strayed to his still-throbbing cock.

"Bob," she said, "I want you to fuck me like that man did to Joe."

Bob rose from being prone on the bed into a kneeling position at its foot. Helena spread her gorgeous, firm legs for him, and he licked her pussy a bit more, teasing her clit and her lips, kissing her on her vaginal opening. She moaned quietly. Bob worked the moisture, which ran down Helena's pussy to her asscheeks, into and around her anus with his tongue. He slowly slid a finger into her ass, and she gave an involuntary sigh, pushing all the air from her lungs, as he did so. He eventually worked another finger into Helena's tight little asshole, trying and remembering the sequence of events from the bedroom last night. He moved them back and forth, feeling her grip him from the inside, and also becoming aware of a prolific amount of lubrication seeping from Helena's snatch. He bent forward and lapped this up, spreading it with his tongue all around her ass. Finally, he felt she was open and wet enough, and he didn't think he could take anymore of this, anyway.

He knelt on the bed, and put her legs on his shoulders, emulating the position of the two men from the night before. He placed a hand beneath each of her firm but oh-so-soft asscheeks, and spread them apart, gently, giving each a squeeze. She gave another sharp gasp as he slid his prick inside her, and began to slowly thrust back and forth, giving her a little more of it each time, until he was buried up to the hilt in her warm and anxious ass. She relaxed and opened for him, and welcomed him insider her. He gripped her thighs tightly, leaving little red fingerprints, as he solidly thrust into her each time. Helena lay back on the bed, her ass filled with Bob's cock, pinching her nipples and licking her lips. Bob got a mental image of Mel's ass from the previous evening, clenching and unclenching as he fucked his partner, and he thought he must look like that from behind. The thought caused him to involuntarily check the doorway as he pumped into Helena, even though he knew he had locked his outer door. He turned back to Helena, whose eyes were closed tightly, and whose breathing was shallow and rapid. Her ass felt so good, wrapped around his cock, so hot and responsive, flexing around his cock as if to milk his balls dry. Bob felt his orgasm before it hit him, and gave a short "I'm cumming!" warning before shooting his hot load into Helena's asshole in a series of spasmodic jerks. When she felt this, Helena began rubbing her already engorged and stimulated clit furiously, and she came again, just a few seconds after Bob.

His legs shaking, he slowly pulled himself free of her gripping anus with a soft pop. Her ass oozed his cum onto the bedsheets, and as he lay next to her, he could feel her wetness drying on his cock and on his legs. She was lying quietly next to him, looking up at the ceiling in a daze. Bob leaned back on the pillows at the top of the bed. The whole room smelled like sex. Bob reached for his smokes, a pack of Gauloises, and lit two, handing her one. She took it from him and took a deep pull from the French tobacco.

"So that's what Joe was looking for, I suppose. I'd never had anal sex before."

"Really?" Bob was incredulous. "I'd never have known that."

"I'm going to choose to take that as a compliment," Helena glanced sideways at him. "Why do you suppose men stray, rather than try to work it out? I only started cheating on Joe after it was clear that he had no interest in even trying to figure out what our problems were. If it was just a new sensation he was looking for, I could have tried toys, or even swinging, but this deception makes me just want him out of my life for good."

"Maybe he's gay, and just realizing it himself," Bob asserted. "After all, I would imagine that it's a whole different experience with another guy. Also, some guys have that Madonna/whore hang-up when it comes to doing some kinds of things with their own wives." Bob regarded her sweaty, sexy body next to him in the bed. "I'm going to go with him being gay, though." He tickled her trimmed bush with his fingers.

"Hmmmm, I just don't know."

After a few moments of quiet contemplation and smoking, Helena rolled over, leaned across Bob and crushed her cigarette out in the University Club ashtray next to the bed. Her arm draped across Bob, she kissed his nipple on the right side, and her hand strayed down and began to slowly stroke his spent cock. After only a few moments of this, he began to get hard again. She moved her mouth down around his dick, and he thought to himself, " Well, maybe I can get some work done tomorrow."