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Tracy and Don Elliott, empty-nesters in their late 40s, supplement their income by offering two unoccupied bedrooms in their home on an internet B&B website. Tracy manages the flow of customers, and it was not a coincidence that the guests who slept in their home were mostly good-looking men.
Chapter 1 - 2020
"The reservation was only for two nights, Mr. Jackson. I have other guests lined up, and I also need time to clean the room between guests."
Tracy Elliott had dealt with flaky bed and breakfast renters before, so she had some experience dealing with unexpected problems like Jackson's. One of the banes of being a B&B host is that guests frequently want to leave early (and pay less), or stay longer (despite the owner's obligations to other guests). Being a host is often a scheduling ordeal.
Jackson's issue – he wanted to stay an extra night - came up all the time. The good part of the stay longer problem is that it gives the owner a chance to gouge some real money, whether or not there's truly another guest on deck.
Tom Jackson had rented her Cleveland, Ohio guestroom through an on-line room-sharing website. Tuesday evening, which was to have been his last, he asked to prolong his stay two more nights. His business had stretched out into another day or two of negotiation. He had already rearranged his return flight; getting the Elliotts' room for the extra nights was his only remaining problem.
Tracy Elliott and her husband, Don were in their mid-forties. Their nest became empty two years ago when their 22-year old son took a job in Denver, near his older sister's home in Boulder.
Money was tight; Don only worked part-time. He earned a decent but irregular income from part-time computer work. He sometimes worked at home, and the convenience was awesome, but they needed an expensive high-speed connection and cutting-edge computer hardware. Both were expensive. One of Don's clients, however, forbade work from private residences due to concerns about intellectual property protection. When Don worked on projects for Trickle, a start-up in Oregon, they required that he work from an office in one of those new hourly shared office buildings downtown.
Tracy's office job at a downtown hotel paid well for the first 40 hours. But she often was made to put in a few extra hours, and because she was "Salaried Admin" she earned no overtime money when she worked late. Don and Tracy found it amusing that they each "ran a hotel." Tracy helped run the real hotel downtown, and Don was home enough to manage the B&B.
But it was Tracy handling Tom Jackson right now. "If you give me $200 cash, off the books, I'll cancel the next booking and let you stay longer."
Tom agreed. "And fifty more gets me a blowjob?" He grinned broadly. He had a killer smile, and he knew women thought him attractive.
Most of her guests knew that sex with Tracy was on the menu. She frequently had sex with a guest, and word gets around on-line. Tom knew that he could have had her pussy for $250, but he didn't think she would be worth it. She was kind of a dumpy-looking middle-age broad, and with time and effort, he could do a lot better.
But he was in a strange city, his time was valuable, and a mouth is a mouth.
She took his hand, led him into the bedroom, and waited for him to undress and sit on the bed. Then Tracy Elliott went to her knees and began to fondle his testicles.
Chapter 2 - 1994
Before her marriage, Tracy sometimes had sex for money. It had started back in Community College when she was 19 years old. The boss at her part-time job in the shopping mall offered her a way to make more money than the pittance he paid her. She would stay late after they closed up the store, and Carl would give her $15 to suck and swallow.
Tracy was happy to comply. She needed money, and she just didn't think sucking a cock for five minutes was a big deal. And the old guy never lasted any longer than that, unlike her first boyfriend who kept her mouth busy for 15 or 20 minutes for free.
She did the math, and $15 for five minutes worked out to almost $200 an hour. Few jobs paid that well for a teenager. Tracy's only regret was that nasty old Carl was one and done. She would have happily sucked more to earn more; college isn't cheap.
She asked him if he had any friends who might want to share her. He proudly bragged to a couple of his fellow shop-owners about Tracy's skills. Soon she was getting home an hour later but $60 richer. The nights she enjoyed the most were the times two or three of the men crammed into her Carl's little office and she blew them in front of each other. There was a kinky vibe that came from introducing competition between the horny old men – who lasts longer, cums harder, or has a bigger penis, stuff like that. Tracy didn't mind sucking at all and rarely minded swallowing a load. Some guys taste better than others, of course, but it was mostly OK for her.
Towards the end of the semester, her boss started to pester her to go all the way. Tracy wasn't a virgin - she once had sexual intercourse, with that boyfriend who soon after dumped her. She hadn't enjoyed the experience. He had been a clumsy, unskilled, and callous lover interested only in his own orgasm. He'd left Tracy with no hymen and no interest in a repeat performance.
On the other hand, Tracy wasn't exactly fending off boys' advances right and left. She learned early back in high school that she wasn't pretty. Boys and girls in high school quickly sort themselves by physical attractiveness. The hot boys pair off with the cheerleaders and the ugly kids are left to date each other. Even among their own genders, rankings are cruel, with the big-dicked boys lording it over the little-dicked boys, the blossoming full-titted girls smirking at the flat-chested or fat girls. Everything flowed from how good-looking you are.
Tracy wasn't ugly, exactly. She had a pleasant but square face, and nice soft brunette hair. But she was kind of built a little wide and low to the ground. She had no curves. Small breasts and a waist the same size as her hips made her look like a boy. Life can be cruel to a young girl who looks like a boy. That one boyfriend she'd had didn't stick around very long after getting her naked once and popping her cherry.
Tracy drove a hard bargain with Carl before letting him get her in the sack, but those homely looks of her meant that she wasn't going to get rich selling herself. Carl gave her $100 dollars one night and took her home to her apartment to consummate their deal. He was underwhelmed by finally seeing her naked, and quickly maneuvered her onto her hands and knees. He would take her from the rear, her square face and floppy little breasts out of sight. Her cunt was the only part of her Carl wanted to look at.
He learned to his surprise that Tracy had the tightest pussy in town and instinctively knew how to use it. How ironic that the least sexy female he knew was the hottest trick around! She was only a two out of ten on the beauty scale, but he'd never had better sex. By the time Carl was finished slamming it to her that first night he was almost in love. Meaning that he was definitely coming back for more of Tracy's hole.
And the dirty old man was punching above his weight, too. That one painful and unrewarding experience with her jerk boyfriend had not prepared Tracy for the possibility that sex might actually feel as good as everyone said it does. Maybe it was the better position, or perhaps being in a bed instead of the back seat of a car, or even the shape of Carl's penis, but Tracy had her first-ever orgasm that night and then had her second. By rolling her hips and clenching her inside muscles, she wrung joy out of Carl's cock.
She kept his $100 that night, but from then on Carl didn't have to pay her again. Hell, he didn't even need to ask her again, she was so eager to fuck him. When he could, her boss started closing up early and spending more time riding Tracy's ass in her bed. Tracy liked it best - and could have multiple orgasms - if Carl leaned all the way over her back, hugged her chest, and pinched and twisted her nipples. There seemed to be a direct circuit between her otherwise unremarkable little A-cup tits and her cunt. She lubricated so much that her juices ran down her legs and soaked the sheets.
Whenever Carl instead kept his torso upright and off of her back, when he held her hips to bang his cock as deep as he could, then Tracy would use first one hand, and then the other to maul her own nipples.
Three weeks later she missed her period.
After two sleepless nights wrestling with her dilemma, Tracy came to work with a plan. She told Carl they were done, and why. Then she seduced her nerd coworker, Donny Elliott. Tuesday gamerboy got a handjob in the back room, oral sex in his car on Wednesday, and Friday night he scored a home run at Tracy's apartment. He wasn't much to look at, and his financial prospects were uncertain, but when Tracy told Don that he had knocked her up, he gallantly offered to marry her.
He was at her side, holding her hand, helping her breathe, when their daughter was born a month earlier than expected. Tracy ruled out naming her after anyone in either of their families and insisted on "Carla." Don didn't much care, so agreed.
Two years later Don was making better money coding software on the side, and they decided to have a second child. There were many months of trying and failing, and it was Don who suggested he should see a doctor and have his sperm tested. Tracy soothed his anxieties, reminded him how pleasant it was to be having sex so frequently while they tried for a baby, and urged just a bit more patience. "Nature has its ways, darling," she consoled him.
Two months later she was pregnant again. Don was thrilled when their son arrived on schedule. The little tyke looked just like Don looked in his baby pictures.
Tracy would never know if it was Don's brother or his father who had done the job. She'd given them each several opportunities, once together, which turned them both on. She was just glad that Don never found out that his low sperm count and poor motility rendered him functionally sterile.
Chapter 3 - 2017
Don and Tracy had a good thing going with the bed and breakfast. Costs were low, the money was good, and the steady stream of men they'd likely never see again eventually became a solution to their cuckold fantasies.
Tracy's deepest secret was of course that Don had always been a cuckold but never knew it. Ten years ago, when their two children were teenagers, Don discovered on-line stories about shared wives, hot wives, swingers, open and half-open marriages, and cuckolding. Soon many of his sexual encounters with Tracy involved him fantasizing that he was a virile bull making some lady's husband a cuck.
When Don mentioned the fetish to his wife, she happily joined him in role-playing. Now that they were both fantasizing, Don sometimes played the role of a movie star making love to Tracy, while her own fantasies tended towards most of the other men in her office. Many an orgasm was had when Don thought he was Brad Pitt while at the same time Tracy's toes were curling as she imagined getting fucked by the Weekend Manager.
Don had no clue, but it's not a great idea to stoke your wife's slut-wife fantasies if she works 40 hours a week at a hotel. There weren't many men who looked at Tracy and wanted to rip her clothes off, but there were a few desperate guys, and Tracy never said no. There was always an empty room handy. When Tracy opened her legs for random men, there was no need for her to pretend she was cuckolding Don. She just wished there were more desperate men.
And then there were.
As soon as their bed and breakfast operation started, both Tracy and Don worked the idea of "the guy in the guest room" into their cuckold fantasies. Nothing much happened for a month or so, but one night after an unsatisfactory experience with each other Tracy went on the prowl.
That night started like most others, with Don and Tracy excusing themselves and retreating to their en suite bedroom sanctuary shortly after supper. They had a small desk, a nice TV, and two lounge chairs for reading. Don had downloaded some filthy cuckold videos onto a thumb drive, and he and Tracy watched a little before having sex with each other.
At least half the time they had sex with each other, Don would ejaculate before Tracy got her orgasm, so she would make him finish her off orally. There was an inescapable D/S aspect to this, and Tracy liked to verbally deride Don as an incompetent lover as she demanded that he "clean up his mess."
Don enjoyed being talked down to in these situations. He liked being humiliated, and once in a while even ejaculated a second time while sucking his first load out of his wife's vagina. In order for this to happen, however, they both had to pretend the first load was another man's. They pretended that Don was licking Tracy clean after she had sex with a fantasy lover. One night the fantasy lover was their overnight guest.
After Don dirtied the bedlinen with his second squirt, Tracy introduced a new element to the game. "Since you loved drinking Roger's jizz so much, I'm going to go ask him to fill me again, Don." She got out of bed, put on a thin bathrobe, and took some clean towels out of the closet. Breaking out of the cuckoldress role, she truthfully said, "I'm only going to see if our guest needs more towels, dear; but you imagine he's making love to me and when I come back you can eat me some more."
And that's all that happened that night: Tracy knocked on Roger's door, made sure he didn't need more towels, and then tiptoed downstairs for 10 minutes. Not knowing for sure what his wife was doing, Don trembled with excitement as he imagined their guest fucking his wife. When Tracy slipped back into their bedroom Don's cock was so hard it was twitching. Tracy rode him cowgirl to a rare mutual orgasm and then sat on his face while he pretended he was sucking two loads, one his, one Roger's, out of her soaking wet crotch. Going down the hall for a make-believe fuck became a routine part of their game.
Chapter 4 - 2018
Until one night, there was a misunderstanding.
Tracy, almost naked in her bathrobe, knocked lightly on Prentis Jorgenson's door. He was lying on the bed, naked, masturbating while watching porn on his iPad. Tracy thought she heard him say "come in," and slowly opened his door.
He was facing away from the door and appeared not to know she had entered his room. In fact, Prentis was quite an exhibitionist and was excited to have this "excuse" to flaunt his dick in front of the proprietor's wife. So he remained motionless, tugging on his erection, pretending he didn't know she was there. The screen of his tablet was reflective enough to be a decent mirror, and he saw Tracy rub her own clit for a few seconds as she stared at his erection. This was an exhibitionist's dream – he had staged a perfect excuse to be displaying himself, what with her entering his room "unexpectedly. His victim had a perfect excuse for seeing his cock, having heard him say "come in", and she would now shriek, run away, and he could finish himself off. Mission accomplished.
Except.
Her guest's long penis was the first dick other than Don's that Tracy had seen in 15 years since she'd stopped fucking Don's brother and father. And none of the three Elliott cocks were anywhere near the size of the one in front of her now. She stammered something like "I'm sorry," but made no move to leave.
Prentis was disappointed at first by her lack of response to his provocation. The whole flasher kink requires the victim's shock, disgust, and embarrassment, seeing his cock. But Tracy didn't look shocked, she looked interested. And she didn't look embarrassed, she looked, well, she looked hungry.
Prentis brazenly waved his cock around and then asked her if she liked what she was seeing. She wasn't much to look at, this frumpy middle-aged lady, but she had a cunt, and she was there with him. And she wasn't running away, was she?
"Come closer. He won't bite. Have a look."
And she did. Tracy shuffled slowly closer to the bed and, when he offered her the shaft, she gently wrapped her fingers around him. Tracy had, of course, heard of big cocks, but to see one for the first time was mesmerizing. As she slowly pulled and stroked it, Prentis sat up on the bed and pushed gently on her shoulders. Tracy sank slowly to the floor and hit that familiar old position from her youth: on her knees, between a man's thighs, sucking cock.
One reason Don had sex so infrequently was that Tracy was, for the most part, not that interested in sex. Her early experiences had been very transactional, sex for a goal: money, marriage, or even pregnancy. Sex had never been bad, never forced, or painful. But other than with Carl those three weeks long ago, neither had it usually been blissful, either. It was mostly just OK. Tonight, for the first time in her life, she really, really craved a cock. And it was in her hands. Then her mouth.
It was all that recent cuckold talk with Don and the cuckold/towel games. Prentis Jorgenson's good fortune was to be a real, hot, naked, hard, ready to fuck penis when Tracy "pretended" to come down the hall for a fucking. He was about to have the honor to be the man to finally dump a real load of cum into the cunt Don would soon be licking clean.
And Prentis wasn't going to waste his one shot on a blowjob. After letting her slather him with saliva, he got up and raised Tracy to her feet. She moved her head, without thinking, to kiss her lover, but he turned her whole body to the bed, shoved her face down onto the mattress, and mounted Tracy like a barnyard animal. He didn't have any interest in hugging, kissing, or even looking at Tracy. All he needed was to fuck a big load way deep into the back of her vagina. And he was thrilled to discover that it was an extraordinary tight vagina, too.
Jesus, that's good," he said to Tracy. "You're tight as a teenager." He slowly slithered his long snake into her greedy hole from the rear. Wanting to degrade her even more than he already had, he told her "Christ, your poor husband. His slut just eyeballs a real cock and bends over for it? You're a cock-needy old bitch and I hope you don't think I'll pay extra for your tired old pussy."
Tracy had not, in fact, had any thought about getting paid. Since the stunning appearance of his magic wand in front of her a few moments before, she hadn't formed any cogent thoughts at all. She was already teetering on the brink of the first of the three orgasms Jorgenson was going to give her. She almost lost it a moment ago with his "tight as a teenager" remark, and she doubled down on her Kegels and squeezed his big shaft as tightly as she could.
But now, with his wonderful strong pole rearranging her plumbing, she realized that offering her body to future guests might kill two birds with one stone. Don would get his wimpy cuckold fantasies in real life, and she'd make even more money as a hostess getting her slot filled with the jizz he wanted to drink.
Between his sadistic words and his generous endowment, Prentis had Tracy wracked in constant orgasms all ten minutes he railed her. Slapping her flabby ass, banging his cock into the back wall of her vagina, he dumped a prodigious load of cum, then slapped her hard one final time, and said: "did you get what you came for?"
She did.
Changing their normal pattern, when she got back to the room she skipped Don's cock and just sat on his face straight away. "Oh my god, Don, he really fucked me. Jorgenson fucked me so good. What a big cock. Can you taste him?"
Unsure what was real and what was role play, Don dove into her crotch face first, and soon figured out that Tracy was telling the truth. Barely able to chew pussy and speak at the same time, he managed to moan how happy he was that Tracy finally made him a real cuckold.
She smiled and then began another series of orgasms even better than the ones she had down the hall. It was like having a seizure, and she twisted her own nipples painfully as she squirmed her hairy wet snatch all over Don's face.
Her stupid fucking husband, she thought, oblivious that he was in fact cuckolded soon after his marriage by his own father and brother, was finally getting his cuckold dream come true. The premature ejaculator who got his little rocks off imagining his wife a whore was drinking the seminal fluid of a better man's prostate, delivered from his darling wife's well-fucked cunt.
Tracy looked down on his hips, wriggling around as she sat on his head, his little pecker throbbing and finally squirting his own watery, worthless load onto his own belly. Things were going be different around here, she thought.
For one thing, she was going to take charge of selecting their guests from now on. And the good-looking ones would get lots and lots of towels.
At breakfast in the morning, Jorgenson behaved completely normal, so Tracy broke the ice. She knew that humiliation by the bull was a part of Don's cuckold fetish, and frankly, her own, too. So she said "Prentis, I want to thank you for the fantastic fucking you gave me last night. Donny, don't you want to thank Mr. Jorgenson for screwing your wife so well?"
Outrageous as it might sound, Don had long desired a humiliating scene like this. He had no trouble replying immediately, "Mr. Jorgenson, Tammy's right. She loved your big cock last night. Thank you for sharing it with her. She needs more than I can give her, and I want her to be happy."
Tracy added, "My wimpy husband really loved cleaning my pussy hole after you filled it up. He told me that your cum is delicious. We hope you can stay again with us next time."
Neither business nor pleasure ever brought Prentis Jorgenson back to Cleveland. But choosing his words carefully, he gave their B&B a positive review on an off-brand website that reviewed short-term accommodations. The salaciously-named FarmersDaughter.com hosted sex tips and recommendations for traveling businessmen. Jorgenson's review was the first for the Elliotts, but their hospitality options soon became more widely known.
Chapter 5 - 2018
Shortly after Jorgenson's review was posted, the Elliotts received a reservation request from an old man planning a visit to the city.
The nationally-known B&B website most people used was rigorously intolerant of direct communications. Their business model depended on maintaining themselves as the intermediary between would be renters and hosts. FarmersDaughter, on the other hand, existed mainly to facilitate direct contact and enable lusty discussions.
Gerald Bates first booked a room using the stuffy website, then canceled it after getting the Elliotts' address and telephone. He then called them directly to book a room, making it clear to Don that he also wanted the $50 special turn-down service. Soon Bates arrived and the Elliotts had their first pre-arranged sexual encounter with a visitor.
Bates was NOT one of those old men about whom it was said that "seventy is the new fifty." He looked every day of his age, a wrinkled, bald old man, tall and skinny as a rail. Tracy got no pleasure out of bringing him fresh towels that night and sucking his half-erect penis, surrounded by a thick, grey bush. In the end, she was pleasantly surprised by the size and tastiness of his ejaculation, but the night was one of the rare times that the subsequent sex with Don was better than the cuckolding encounter itself. But $50 was better than nothing.
Tracy resolved to do a more careful, active screening of future guests. Tracy had Don's consent to let her offer herself to a guest or not. But if the sexual encounter is pre-arranged, it becomes a commitment, and turning a man down would lead to negative reviews and financial harm. So it was important to screen out the pigs and toads. The Elliotts had transitioned into a situation where Tracy pretty much had to suck and fuck her guests, whether or not she felt like it.
Neither did it matter what Don thought. They had reached a point that Tracy would fuck who she wanted, when she wanted, and Don could either enjoy being cuckolded or not. One night Tracy told him that she had screwed several of her coworkers over the years, and might continue to do so if she so chose. Don's first thought was not that Tracy cheated on him, but instead that these men all now knew that he was a cuckold, and he didn't even know who they were. How deliciously exciting and humiliating!
Tracy fiendishly dragged Don to the hotel employees' holiday party, where she held his arm and introduced him to one person after another, all the time whispering "You think I fucked him? Maybe I did, maybe not." She lightly rubbed her hand over the front of his trousers to keep his little cock hard all night.
Don got a thrill out of his abasement. Just before midnight, while they spoke to the Weekend Manager, Tracy said "I told Don that I cheated on him with someone here, but I didn't tell him it was you. Knowing I'm a whore makes his cock stand up. This is your chance to tell my hubby what a good time you had fucking his wife."
There were two other men at the party Tracy had opened her legs for, and she had a similar conversation with each one, all the while clinging to Don's arm. All three men thought it was fun to taunt Tracy's husband, and by the time Tracy declared it time to go home Don was almost trembling with excitement. Just think: he'd spent hours in the company of men who knew what an inadequate husband he was, men who had plowed Tracy's cunt behind his back.
In their car, before pulling out of the garage, Tracy stroked him all the way and laughed at him for "jizzing your pants like a little boy. Too bad all their wives were here, or we could have taken one or two of my office-husbands home with us."
Unfortunately for Don, as their cuckold play took over their sex lives, Tracy found herself less interested in normal sex with Don. His modest cock and his hair-trigger made him a really lousy fuck. His access to Tracy became completely oral for a while until he told her about this "pegging" thing he'd seen on the internet and she got interested.
They started slow, with one or more of Tracy's fingers in Don's hole while she masturbated him to climax. Don became increasingly submissive as night after night Tracy laid him on his back, tugged his cock with the fingers of one hand, and gently inserted fingers from the other hand into his rear end. Using lots of lube, and switching hands often, she literally manipulated his arousal until she wanted him to have release.
Unless she didn't want, and she would say something demeaning like "I give up. Go jerk yourself off in the bathroom. And don't make a mess."
The second step towards Don's emasculation came at the end of one of Tracy's vibrators. Sexually speaking, this was a disappointment for both of them. Tracy got little sexual pleasure from manhandling the vibe in and out of her husband, and the stiff unyielding plastic cylinder didn't do much to stimulate Don either. The idea of being pegged had been more thrilling than the actual event.
It was a little better for both of them when Tracy bought a harness and tried wearing the dildo. Pumping in and out of Don stimulated something primal in Tracy. In almost every sexual encounter in her life, sex had pretty much been something someone was doing to her. Often, she had enjoyed only the getting paid part, not so much the getting laid part. Pegging was obviously something she did, not something done to her.
But real joy eluded her until Tracy pegged Don with a double-ended device that was inserted into her vagina and Don's ass. Her orgasms now were better pegging Don than having regular intercourse with him.
Don liked it best when Tracy mounted him doggy style and humped him vigorously, often while either giving him a reach-around or maybe pinching and twisting the nipples on his man boobs. Tracy could slam his prostate gland on each thrust. They soon learned how to position themselves so that Tracy banged Don's prostate and he experienced hands-free orgasms of his own. Don's best orgasms came whenever Tracy mounted Don's ass and gave him a thorough screwing. Eating creampies was still a treat, but as humiliation, it couldn't hold a candle to letting your slut wife bugger you while calling you names.
Tracy's favorite position, however, was lying down in opposite directions, scissoring each other, crotch to crotch, connected by her double-ended dong. She'd gotten the idea from lesbian videos. The two of them would slither around, humping each other's crotch, and moving the dong in and out of their holes until she orgasmed. This position usually left Don unsatisfied, but increasingly Tracy just didn't give a fuck what Don liked. She'd become a selfish whore, and their sexual adventures were just beginning.
Chapter 6
Don and Tracy frequently talked about sex. They were immersing themselves in sexual fantasies. They discussed what they did with whom, and what they dreamed of doing.
With guests, however, Tracy found silence was usually golden. Few of the men cared about what she did or what she wanted. Some of them didn't want to talk at all, just to dump a load in whichever hole they'd paid for and roll over to sleep.
Patrick Hannover was an exception. From the moment Tracy entered his room he babbled bout the sex they would have and things he'd enjoyed in the past. He asked about her husband and delighted in talking about Don's cuckold fetish and creampie addiction.
Then he did something no other guest had – he offered more money to fuck Tracy in front of Don. He wanted her husband in the corner, watching Tracy be his whore. Tracy was fine with his idea; it just meant more money for her, and if Don didn't enjoy watching, well, too bad. Might even be more fun if he refused; they could tie him up in a chair against his will.
That wasn't necessary; Don was delighted to comply. Tracy's sex life involved him less and less, and she almost never cared any more when or if he had an orgasm. He sat in a chair in the corner and was soon masturbating while Patrick, energized by his audience, fucked the daylights out of Tracy. The masturbating was also Patrick's idea, not that Don needed his arm twisted. But he might have sat there quietly if Hannover hadn't taunted him to "pull out your sissy dick and beat yourself off."
Performing in front of Don and taunting him had been Patrick's idea, but Tracy loved the new kink and had one of her best-ever orgasms. It was a bigger rush to humiliate Don in front of another man – a bigger, more sexual man - than merely to humiliate him in the privacy of their bedroom. As she lay on the bed next to her guest, enjoying the after-glow, sperm leaking from her banged-up cunt, she had an idea. It, of course, involved both sex and money.
"Patrick? For another $50, I'll let you watch Don eat your creampie."
What followed gave all three of them pleasure. Don had never even imagined anything as humiliating as eating Tracy in front of the man who had fucked her. It was absolutely delightful. As he lay face down on the bed, his face firmly planted between Tracy's sweaty, meaty thighs, he orgasmed, soiling the comforter. Patrick had never felt manlier, more powerful, than fucking a load deep into another man's wife and making him clean it up. Tracy was enjoying herself so much that she had a tremendous cum of her own, her second.
Two days later, in the comfort of his own home, Patrick Hannover left a detailed, glowing 5-star review on FarmersDaughter.com and the phone at the Elliotts' house started ringing all the time. Requests for simple blowjobs or intercourse diminished, and threesomes became a house specialty. They were a bargain at $300.
Chapter 7
The Elliotts really enjoyed many of their FarmersDaughter customers, but the "regular" B&B guests using the national B&B webpage still came frequently, too. In the autumn B&Bs in college towns get busy. High school seniors across the country start selecting colleges to be applied to, and a campus visit is almost a necessity.
B&Bs with two guest rooms, like Don and Tracy's, get booked by families, with the parents in one room and the student in the other. When demand is high rates rise, too, and an October booking by a family pays more than an offseason "single with a blowjob".
The Andrews family booked two rooms for two nights so that Todd, their 18-year-old son, could visit two campuses in one long day. They arrived mid-day on a Sunday, planned the campus expeditions for Monday, and would leave town Tuesday. Two rooms for two nights would keep Tracy and Don busy in the kitchen, but they loved the money a booking like this provided
Wendell, Nancy and Todd Andrews arrived around Noon on Sunday. The husband was over six feet tall and carried some extra weight on his broad-shouldered body. He appeared neither fat nor fit, just bulky. Nancy was a tiny woman in comparison, about five foot four, and slim. It wasn't obvious the way she was dressed, but she was lean and toned. Their son was a very handsome combination of the two parents, tall like his dad but lean and fit, like his mother. His arms were solid muscle, and Tracy kept noticing them as Todd flexed and motioned.
An attractive couple in their forties, Mr. and Mrs. Andrews wanted to do some sightseeing Sunday and then visit a well-reviewed restaurant. When their son begged off, they left Todd in his room to study a little, to prepare for his interviews the next day, and to relax. Planning to be alone for three or four hours, instead of doing anything productive Todd opened the bedroom window as much as he could and fired up some marijuana. He was very relaxed indeed when Tracy caught a whiff while walking down the hall.
If you work in a hotel there are some smells you become familiar with. Regular cigarettes, of course, are number one. I mean, what part of "No Smoking Room" do those idiots not understand? Sperm, surprisingly, is smell number two. Who are the pervs who whack off all over the bed comforters? Guests sometimes leave a room fragrant of beer, vomit, or an unflushed toilet.
And marijuana. Tracy knew what she smelled in her house right away. Smoking anything was not allowed in their house. It wasn't so much that Don and Tracy cared about morality, but residual smoke odors of any kind could ruin the stay of the next guest. Tracy knocked on Todd's door and, not waiting for an answer, went right in.
He was sitting in the room's only chair, next to the open window, stretched out backward as if the chair was a recliner. It looked uncomfortable, but he seemed relaxed. He slowly raised his head but made no move to get up. He was so tall, well over six feet, that his athletic body stuck way out of both the top and the bottom of the chair. His brain wasn't firing on all cylinders – he was really baked – and he just turned his head and stared at the middle-aged lady shooting daggers at him with her eyes. Holding a cigarette in his right hand, his left on his crotch seemed to be idly stroking an erection inside his sweatpants.
It took a second before he connected his brain cells and remembered that she was the landlady. As he stared at her, ogled her, really, he ran his eyes up and down her body. Her hair was cut in a style suitable to an older woman, with touches of gray. Some wrinkles around her eyes and her neck. Her blouse didn't show any curves, so Todd knew her boobs were small. He noticed she had no waist at all and her torso was all straight up-and-down like a tree trunk. Chunky thighs with surprisingly trim, shapely calves. The lady wasn't ugly, but she was far from beautiful. A lot of hard miles on this broad, he thought. Not a woman to be fucked with, he bet.
Her best feature, at least as she appeared to Todd, was her eyes. When her mouth smiled, her eyes just twinkled. Todd locked on her eyes and reached inside his waistband to grab his erection unencumbered. He was too stoned to wonder why she didn't care about his jerking off, and at the same time was too befuddled to have any particular plan to continue, or to stop. His dick was sending pleasure signals to his brain, and he kept stroking. Tracy kept staring.
"I just came to see if you were comfortable in your room, Mr. Andrews."
Todd's dick jerked in his hands when she called him that.
"There's no smoking permitted in my house. I thought you knew that."
He just continued his vacant, drug befuddled stare.
"I don't think I've ever seen someone look more comfortable than you do right now, Mr. Andrews." Her eyes watched his hand manipulate his hard cock, still inside his pants. Tracy knew that, brain all fucked up by the grass, Todd wasn't going to be much of a conversationalist. She idly wondered if he had any money.
"I mean, I stopped in to see if you need anything to make yourself more at home." As she continued speaking softly to Todd, she approached the chair.
"Is there anything you need, Mr. Andrews? Anything at all to make you happy here?"
Todd just stared at her and stroked his dick inside his sweats. Tracy knew that if Todd was fucked up enough, he might never utter a complete sentence, so she took some initiative and reached in his pants to take over the job of whacking him off.
He groaned and stiffened in the chair. His hand, slathered with his own pre-come, fell out of his pants and dangled next to the chair. Once Tracy leaned forward, his hand slowly went to her thighs, and then up under her dress. Todd was gently rubbing the older woman's meaty ass as she lowered his pants.
"Mr. Andrews," she said, and felt his erection twitch, "you have a really nice cock. I hope you don't mind if I play with it for you, do you? I like my guests to feel right at home here."
After deciding that Todd was not going to object to anything, she tugged his sweat pants completely off of his body and fell to her knees between his muscular thighs. Tracy Elliott had blown so many men in her life that she couldn't count. But the first five inches of Todd Andrews's teenage hard-on were the best she could remember. That left several more inches exposed, but Tracy's mouth could only take just so much dick before choking. She gave it her best, being sure to clinch her lips tight just behind the large head on the end of his teenage erection.
Todd stared down at the older woman's face. He took another pull on his cannabis cigarette. His dick looked terrific between her lips. His brain slid sideways, and he wondered whether it was a pretty mouth or a pretty cock. He didn't finish the thought. He wasn't finishing any of his thoughts.
Tracy's hands were tugging and squeezing his big balls. She began to whimper, and Todd's brain was so clouded that he feared he might be hurting her. His first complete sentence in several minutes was "Am I too big for you? Most girls say I'm too big."
"You're perfect, Mr. Andrews." Another dick twitch. Several more twitches of cock and clenching of scrotum. He kept smoking, getting more wasted. She kept sucking, and occasionally touching herself. Her underpants were soaking wet.
He loved being called Mr. Andrews for some reason. Tracy decided to go with it. "I love your dick, Mr. Andrews. It's just the right size for a horny old woman like me." Actually, Tracy thought, he really might be too big. She'd never taken a cock his size before and wondered if it would be too much for her vagina. It would be fun to find out. He was definitely going to get fresh towels late tonight.
Tracy was beginning to think Todd enjoyed being called Mr. Andrews as much as he enjoyed her slobbering blow-job. "Your hard cock looks perfect to me, Mr. Andrews." Tug and rub. "What silly girl said you were too big, Mr. Andrews?"
Todd had a far-away stare in his eyes as he slowly formulated a reply. "Mom says it's too big. Way bigger than Dad. It hurts her sometimes if I'm not careful. Then Dad gets mad at me."
Tracy was both shocked and inflamed by Todd's careless confession. Lewd images of the tiny Nancy Andrews being impaled on the giant dick of her muscular teenage son flashed through her horny mind. Tracy sucked harder and faster on Todd's long shaft and used her hands to maul his scrotum. "Your cock is perfect for me, Mr. Andrews. Would you like to cum in my mouth for me, please?"
His brain was messed up by the drug, the feelings on his cock and the incestuous fever in his brain. He remembered the last time he and his father had DP'd his mother and suddenly orgasmed without warning into Tracy's throat.
Tracy Elliott had swallowed a lot of cumshots in her life, but Todd Andrews's marijuana and incest-fueled load was the most she'd ever swallowed. When she first went to her knees in front of him she'd planned to charge him money for her service. But when she later left his room, she hadn't given money another thought.
Chapter 8
Late Sunday afternoon Mr. and Mrs. Andrews were out on their "date night" while their son Todd was watching porn on his laptop in his room. Don and Tracy often took a few quiet moments before dinner, sharing some cocktails or wine. Tracy told Don everything about her afternoon with Todd. He was fascinated by her description of his athletic, ripped body and the length of Todd's erect penis. Like Tracy, Don was feverishly stimulated by the incest story. They discussed several possible ways to approach the husband and wife, but every scenario had flaws.
In the end, Don went upstairs and invited Todd to join them for supper. B&B guests usually did not have dinner with the hosts, but then again guests didn't usually leave their teenage kid alone, either. Todd was ravenous - and brazen enough - to have dinner with a man he had just cuckolded.
Todd found the situation kind of titillating, sitting between Don and Tracy for a meal knowing she had his sperm in her stomach. The Elliotts did, also, and Tracy decided on the spur of the moment to just jump into the deep end. Dinner could wait.
"Todd, I mean Mr. Andrews, I told my husband all about how I sucked your big cock this afternoon." Before the young man could respond, she gave him a big smile and continued, "We always tell each other everything, Mr. Andrews, and my dear Don doesn't mind other men giving me sex when I need it."
Todd swiveled his head to look at Don, who silently nodded. The pot had worn off and his brain was working again, but this shit was crazy and he had no idea what to say to either of them.
"Don was disappointed in one thing, Mr. Andrews. My husband isn't a real man, you see. He has a cute little dick that just isn't big enough for the pussy of a grown woman. He likes to play with himself while he watches me have sex. He's really bummed that he didn't get to see you feed me my appetizer before."
Don jumped in, "Tracy is right, Mr. Andrews. I would have enjoyed watching you pleasure my wife with your big penis. Would you have let me? You're not too shy, are you?"
"I can go again. Do we have time?"
"A penis like yours? I'll always have time for a man like you, Mr. Andrews. Tracy got out of her chair and went to Todd's side. As she began rubbing the front of his pants, she said, "Sure we do." Then she took Todd's hand and led him upstairs to his room. Don was hot on their heels.
This time Tracy asked "Mr. Andrews" to get naked and lay on his bed. She lay between his legs, her face over his groin. He was so tall that his lower legs hung off the end of the bed. As Tracy slurped on his dick, she took several opportunities to boss Don around, ordering him to sit in the chair, or to play with himself.
Eventually, as Todd neared his climax while she licked his furry ball sack, she ordered Don to hold the base of Todd's cock while she sucked the head.
Don grabbed the hot shaft without a moment's hesitation, although he had never touched any other man's cock before. It was harder than his own erections and felt warmer. Don squeezed and relaxed his grip, and slid a little bit up and down. For all the hundreds of hours Donald Elliott had spent with his own cute little weenie in his hand, he'd never experienced the passion he now felt. He was hanging on tightly to the end of a big man's big dick, and he felt as if Todd's sexual power was passing into him through his hands.
Then, deciding to take a chance, Don's wife ordered her wimpy husband to hold Todd's cock straight up while she climbed on for a fuck. Riding Todd cowgirl style would allow her to control his penetration in case he was, indeed, too much for her insides to handle. Her natural lubricants slathered his dick with oils and juices from deep inside her. As experienced as her pussy was, it had never before been stretched this wide, and the sensation was exquisite.
For the first few minutes, each time Tracy descended on Todd's erection she took one more half-inch of his cock. Slowly more and more of his penis glistened in the light with her juices. There was a tense, strained look on her face as she controlled each dip down onto his dick.
All this time, Don hung onto Todd and was amazed by the boy's power. Keeping his grip, his face stayed near the site of their coupling, and he smelled his wife's arousal and the sweaty smell of Todd's saliva-soaked balls.
Tracy looked down triumphantly as her sissy husband jerked her lover's dick. "Fondle his balls, Donny. Help Mr. Andrews get off. Take his balls in one of your hands."
Don tried and switched his left hand from clutching the widest end of Todd's root to cupping his oversized, overheated, testicles.
Tracy continued to watch and to humiliate her husband. "Lick Mr. Andrews' balls, Donny. Lick him for me."
Todd was in heaven. He'd poked his dick into other women's cunts before, and Tracy was the tightest. Her vagina, even so thoroughly juicy, felt like it was compressing his shaft, squeezing it thinner. Tracy calling him by his father's name, and Don now using his mouth, licking and sucking at his penis and his scrotum, was driving him crazy.
Tracy surrendered first, orgasming with only most, but not all, of Todd's shaft inside her. He'd gone as deep into her as any other man ever had, and with his extra girth, he had stretched her to her limits. She cried out and moaned as her orgasm took control of her body. Drooling from her mouth and convulsing in her vagina, her hips jerked forward and back and then she fell sideways into a heap.
Don had been hypnotized by Tracy's herky-jerky climax, but suddenly she was gone and he had sole possession of Todd's long, thick manhood. As he turned his head to look at Todd, he continued to knead the cock meat and lick the ball sack of the masterful teenager. Todd's eyes locked with Don's and they stared silently at each other across the expanse of Todd's firm, cut abs. A primal coded message was transmitted silently, and Don slowly raised his mouth from Todd's testicles to take the head of the dick into his mouth.
It was now Todd's turn to use his hands to hold something tight – Don's head. With his open palms on Don's ears, Todd forced the cuckold husband's face up and down the length of his cock. Don's mouth could only handle half as much dick as Tracy's pussy had managed, but the way Don instinctively knew how to give pleasure with his mouth made up for it. Don's lips tightened just behind the cock head, and Don's tongue swirled around and worshiped the slit where the cum would soon shoot out. Nibbling, sucking, almost chewing on his first dominant male erection, Don lost contact with his surroundings.
Tracy had turned her head and now stared silently at the man she married, the impotent wimp who fathered neither of her children, the sissy who loved creampies. She saw him trying to swallow a God-like cock. She would have a hard time ever considering him a man in the future.
And still, Don stared into Todd's eyes.
Todd felt like the most powerful man in the world. It was always a rush to fuck his mother, but men and women are supposed to fuck. Maybe that was how boys were supposed to become men, by taking their mothers away from their fathers.
But this? What Todd was now experiencing seemed so perverted that he couldn't hold his orgasm back even another minute. And he saw the knowledge in Don's eyes. The husband knew he was losing his manhood on the end of Todd's perfect penis while his wife sneered at him.
Don whimpered like a puppy as he felt Todd's balls first lift up high into his scrotum, then felt the tube of flesh in his mouth pulse and jerk. Finally, his mouth filled with Todd Andrews' delicious sperm and Don's own little dick gave up its load, too.
And in the open doorway of the bedroom, Wendell and Nancy Andrews stood unnoticed, until they both began a slow clap for their pride and joy.
Chapter 9
Monday went fantastically well for the Andrews family. Todd did exceptionally well in his college interviews, and the two campus tours gave the family confidence that Todd would excel at either school.
That night, to celebrate, Wendell and Nancy treated to an elaborate take-out dinner and the two families had a pleasant evening together around the Elliotts' dining room table. Nancy proposed a toast: "to our new friends" and Tracy toasted back "To Todd, who will always be welcome here while he's in college."
There was more wine, and instead of a marijuana cigarette Nancy broke out their stash of edibles. As the evening went on, the four adults had a great time telling each other about their regular lives and their sex lives. Don and Tracy had of course never previously talked openly to others about cuckolding, or pegging. The Andrews likewise enjoyed the opportunity to have their first-ever conversation about incest. Wendell asked Don how it felt to watch total strangers fuck his wife, and Tracy asked Nancy what it was like to invite a son to take his father's place in her bed.
Todd mostly sat in the corner, soaking it all in. Yes, he was a naturally talented cocksman, but he was, on the other hand, only 18 years old. He had never before had the opportunity to hear adults talking about sex. He could afford to be smug: he was the one person in the room who had fucked both wives and been blown by both husbands. At one point, he said so.
The two couples laughed at his braggadocio and said the cocky young man "needed to be brought down a peg." That pun sparked more laughter and soon the five new friends agreed to move the fun to the master bedroom for a pegging demonstration. Once they were there, and comfortably sitting or lying around in their underwear, Tracy took out her double dildo for everyone's enjoyment.
Don was embarrassed to be the butt of all the jokes, and he quickly agreed to show the others what he loved his wife to do for him. But Tracy threw him the first of what would be a series of curve-balls when she said to Nancy, "Come over here and let me teach you how to fuck my husband's ass."
Tracy first placed Nancy on the bed and ordered Don to lick her pussy to prepare her for the dildo. Nancy was able then to insert her half into her own vagina and got up on her feet next to the bed.
Tracy then ordered Don to fellate the end that would go into his ass. After that mostly symbolic act of submission, Don slathered KY on the phallus and handed the tube to Nancy as he lay face down on the bed.
Using first one finger, then more, Nancy greased up Don's anus for the imminent insertion. This small task was by itself deeply thrilling. Nancy had never touched anyone's anus before, and she felt suddenly very powerful as a grown man wiggled around in delight on the end of her oily finger. The smallest part of her body was sexually dominating all of his body. She began to get carried away and was soon pounding his ass with her hand and its extended fingers.
Tracy offered her expert advice and got Don to lay face down at a 45-degree angle on the bottom corner of the mattress. His thighs naturally opened as his legs went down the two sides of the bed.
Nancy stepped around to the corner of the bed and gently started to pump the dildo into Don's well-practiced sphincter. Her small height allowed her crotch to be at just the right height to line up with Don's greasy cock socket sagging off the end of the bed.
As she stroked in and out of her host again and again, at first gently, the dildo penetrated both of them until both her cunt and his ass were happily stuffed with cock. They both began to moan and it wasn't obvious at first glance which one was enjoying this more.
Probably it was Nancy, for whom this was a personal first. Don was vigorously pumping his hips up and down into the mattress, obviously enjoying Nancy's dick in his rectum. But Don had been fucked before, and Nancy had never felt the thrill of inserting herself into another human being. A girl could get used to this, she thought, and resolved on the spot that the next man she fucked would be her own husband. She held that thought quietly for a minute or two, but when she lost control of her pelvis and found herself slam fucking Don as deep as she could, teetering on the brink of her orgasm, she groaned out loud "Oh, Christ Wendell, I'm definitely buying one of these to use on you when we get home."
Wendell and his son sat naked nearby, each stroking their cock as the watched Don bottom for their wife and mother. Todd's monster was almost twice as long as his Dad's perfectly adequate but very average-sized erection. When Nancy glanced over and saw her two men jerking off, she felt another ripple of pleasure. "Wendell," she ordered, "get over here and stuff my ass, please. Sorry, Toddy, but we know you're too big to play in my little backyard."
"I'll take care of Todd," Tracy said, and knelt between his knees to once again suck the teen's iron-hard cock. Just like the day before, she was only able to get the front half of his fat dick into her mouth.
Wendell used the KY and quietly plowed his six-inch penis into Nancy's bottom. This was familiar for both of them, including when Todd played the front nine and they drove Nancy insane double-fucking her in their big bed back home.
With Tracy's dong in Nancy's pussy and her husband in her ass, Nancy twitched her hips back and forth as if she was being electrocuted. She exploded into orgasm from the joy of once again being penetrated front and rear. Sweat was dripping off her face and her entire body seemed flushed and pink. She cried out loudly, her cunt muscles squeezed the unyielding dildo, and her anus tried to bite her husband's cock in half. And then she just deflated, like a stuck balloon. She collapsed onto the bed next to the men, moaning words that didn't quite make sentences, "So good. Never before. Fucked him good. Hungry ass. Next time."
As Nancy became more collected, she took a deep breath and gave her husband, whose cock was now waving around aimlessly, a devilish grin. She also leered at the abandoned dong, still half-inserted into Don's bowels. "Finish him, Dear. Stuff your little cock up Donny's ass and finish both of you off."
Tracy exclaimed, "Yes, do it, Wendell. He's still a virgin. You'll be the first man to take his ass."
Now it was Don's turn to whimper as Wendell slowly withdrew the half-cock from his butt and tossed it aside. Taking the smaller man's hips into his big hands, he lined up his dick and slowly slid his erection into his host. He began to thrust gently back and forth, never quite mastering the skill of getting that final inch of penetration. But as clumsy a fuck as it was, both men soon emptied their prostates and laid quietly next to Nancy on the big bed.
"I want to see something now, Nancy," Tracy muttered, her mouth still half impaled on Todd's monster cock.
"Todd, your mother and your father have fucked my husband. They owe me this. I want to watch you fuck your Mom."
Nancy moaned, delighted at the prospect of having a cheering audience for the first time as she let her boy once again make a woman out of her.
Todd smirked broadly as he walked slowly to the bed, gently tugging on his spit-soaked erection. He loved the thought that when he had sex with his mother, he was somehow "taking her away" from his father. He also got very aroused by the entire "return to the womb" thing. He forcefully reached for Nancy's ankles and dragged her exhausted body down towards where he stood at the foot of the bed. Still holding her ankles, he opened his arms to spread wide the grown woman's soaking wet crotch. Then he leaned over her and aligned that big dick at the mouth of her reddened labia.
"Ready, Mommy?" he sneered down at her.
"The KY, Todd, please use some lube. You stretch me so much, baby. You're too big for me. Please use the jelly."
Inflamed by all of the things he'd never seen before today, cuckolding, pegging, the whoring landlady and her sissy husband, his dad butt-fucking another man, Todd's senses overloaded and fried, Todd went off-script.
"No jelly for you, slut."
Then he leaned over his mother's crotch, licked her two or three times, and spit on her pussy three times. The first time there wasn't much saliva, but Nancy gasped from the shock of it. The second time, she reached up for him and begged him to fuck her. Todd said, "Get ready, Mommy, your baby boy is coming back in again." Then he spat on her clitoris the third time and stabbed half of his horse-cock straight into her vagina. Nancy squealed in delight as his cock stretched her labia wide open and slammed into the back wall of her cunt.
Turning to Don and Wendell, still on the bed, Don's asshole and Wendell's soft dick messy and slimy, covered in cum and lube, Todd said firmly, "Watch this, you two fags. Watch a real man fuck a real woman."
Nancy moaned endearments as her legs wrapped around her young son's hips and her arms went around his neck. He was so tall that, even though he was bent forward over his mother on the mattress, his chest did not rest on hers. He hovered over her as their genitals slammed into one another. Nancy clung to him. When her arms and legs tightened, she lifted herself off of the mattress into his sweaty embrace. Todd had the strength to stand up, Nancy still clinging tightly to him, and he performed the athletic feat of fucking Nancy Andrews in mid-air as she screamed her excitement and wriggled all over the front of his body.
Tracy watched, enthralled, as Todd's muscles rippled and flexed. She gaped as he almost effortlessly tossed the 115-pound cock socket around in the air and made her moan and wriggle in his embrace. Todd stood fully upright, planted his strong legs slightly apart, and then remained almost motionless.
Don, Tracy, and Wendell watched in awe as Nancy did all the work to fuck herself.
She pulled her arms light around Todd's neck to lift her pussy to the end of that great cock. Her dainty ass cheeks were tightly cupped in her son's strong hands and he curled his arm muscles to aid her ascent. Then they both relaxed their arms while she tensed her legs, and her soaking wet pussy slid back down his shaft, almost to the bottom now. Up she pulled, down she slid, babbling senselessly and drooling all over Todd's shoulders.
She began to bite him now, and claw at his back. Having an audience for her lust made it all even more electrifying for Nancy. She began to draw blood with her sharp nails and her teeth. Todd didn't even flinch. This was without a doubt the best sexual experience Nancy had ever had. She was losing her mind as Todd's long dick banged into the mouth of her cervix and pounded the walls of her pussy, deeper than ever before.
Tracy was no longer able to sit by. She ordered Nancy's husband off of the bed and into the chair, and then ordered her husband to clean Wendell's cock with his mouth. Tracy then shoved Don aside, took Wendell into her arms, and dragged him down onto the floor for a fuck. Nancy's husband was already rigid and erect from watching the performance of his wife and son.
Don watched, alone now, as Wendell made love to Tracy on the floor and Todd banged Nancy against the wall nearby. He didn't mind sitting it out at this point; his anus was still sore from getting pounded first by Nancy's dildo, then by Wendell's real dick. The other man's cumload was still trickling out of Don's hole, soaking his ball sack as it dribbled out. As Don watched his wife orgasm in Wendell Andrews' arms, he idly thought about the two creampies he would soon enjoy from the fucked-out wives. Don also thought that it was pretty cool that he and Tracy were getting paid money for participating in the best sex of their lives.
Three months later Tracy got a cute note from Todd telling her he was sad to announce he'd be going to a college on the east coast, so would not likely get the chance to see the Elliotts again. "It's a great school," Todd wrote, "but I was kind of looking forward to being in your city for four years."
Chapter 10 - 2020
Tom Jackson, who paid the extra $200 for the unplanned extra night, and fifty more for a blowjob by his hostess, was having his testicles fondled. Not all the guests at Don and Tracy's had sex with her, but enough did to constitute a lucrative side business. Tom was one of those rare men who often preferred getting blown to fucking. It was less work, less messy, carried far less risk for him of disease, and no risk of pregnancy. He was discovering that Tracy was an artist with her mouth.
Tracy loved sucking cock, especially the ones that were short enough not to choke her. The problem was that Don got left out, and of course, she made a lot less money. Maybe if her husband was with them she could snowball him or something. They sometimes made extra money when, after Tracy fucked a guest, Don performed by eating her creampie. Tracy was sometimes surprised how much kinky shit she had learned the last 2 years from Don's porn.
She tugged on her nipples as she sucked, and Tracy wondered once again if maybe Don would suck a guest's cock all by himself? He'd enjoyed fellating that Todd Andrews boy a few months ago. And then sucking the boy's father, too, while Todd railed his mother.
The next morning, after breakfast, with Tracy at work and no guest in the house, Don turned from the regular computer and popped open his personal laptop. After more than a decade in the software business, Don wouldn't even think about running business and personal tasks on one machine.
Especially not pornography, and Donald Elliott breathed, ate, and dreamt of pornography. Like most men, his first exposure to porn came from magazines with photos of naked women. Then he started buying videotapes and DVDs of people having sex. It was here he started noticing that he got just as aroused by the naked male erections as he did from the naked women. The directors of porn movies aided and abetted Don's cock-watching habit; straight porn has an obsession with "the money shot", which is kind of gay when you think about it. Don didn't think about it.
The first year of his marriage Don was busy enough with real sex that his porn consumption dwindled close to zero. Tracy seemed an adventurous lover, and the couple had a high degree of sexual compatibility. She made a point of initiating sex with her new husband often, at least once a month. The little minx was wearing Don out!
Nowadays the few DVDs and then internet pages Don still made time for featured men crossdressing, transsexual males with breasts, and interracial gay movies. After all, any time he might want to see tits and pussy, he could leer at his wife. Porn is famously boring, and many men soon start watching a broad array of deviant activities such as bondage, lesbians, group sex, and so on.
Like most porn-addicted men, his real-world life was mostly unaffected. In their marriage, sex had usually been something Tracy initiated, and Don always responded eagerly. Don had never thought about it but letting his wife green-light their intimacy had the benefit that she never had to turn him down when she wasn't in the mood. Sex for Tracy was rarely great, but it was always good because she never had to deal with sex if she didn't feel romantic. The words "not tonight dear..." never passed her lips.
After the birth of their second child, when Tracy's sexual initiatives became too infrequent for Don's own inclinations, he could just crank one out in his study watching porn. As sexual satisfaction goes, Don was in the sweet spot: once in a while his wife craved dick, and he saddled up. Any other time the spirit moved him, he had his chicks with dicks, sissy cuckold, or men in drag videos to help him pound one out.
Tracy didn't want much sex, and her needs were more than satisfied by her prostitution when she fucked or sucked a paying guest. It only happened sometimes, but she always loved the money and sometimes liked the sex.
For his part, Don got a thrill out of his otherwise meek wife "forcing" him to eat her dirty pussy after she cuckolded him under his own roof. Don particularly enjoyed the kinky breakfast banter the next morning, when Tracy let the stud know that Don was a submissive willing participant in his own cuckolding.
Some of the guests got so aroused by this reveal at breakfast, learning Don had eaten their cream pie the night before, that they wanted another romp with the opportunity this time to watch Don clean up.
Funny thing was, Tracy was never horny in the morning and didn't enjoy these encounters at all. She soldiered through for the money. Frankly, most of these customers didn't care at all if Tracy orgasmed – they just wanted to load her cunt and then watch Don suck out their ejaculate.
Don realized that his porn fantasies were narrowing on the kinkiest kinds of sex. But they were only fantasies. He could not imagine himself ever doing any of these things he found so theoretically. It's not like he would ever actually go to a glory hole, or submit to breast augmentation, or go out in a dress.
One day Don realized that he didn't need to "go out" in a dress. His wife went out, and he was home alone, except for the occasional B & B guest, and they were always out all day.
Maybe not a dress, he bargained with his demon. Maybe he could wear panties in the privacy of his house. And it wouldn't hurt anyone if he wore a matching bra, would it? He could borrow his wife's things or, better yet, buy his own, on-line. He could have them delivered to the nearest UPS Store and fetch them when he knew Tracy wouldn't be home.
Soon Don was spending hours in front of his computers – it didn't matter which one – dressed partially or completely in feminine lingerie. Don had three or four matching sets of bras, panties, and nightgowns. When he worked, he worked, laptop closed, happy in silkies but mentally focused on his software projects. And when it was time for a break, he'd turn towards the laptop and stroke a load right into his very frequently laundered ladies' panties.
Tracy had no idea her husband spent hours every day in drag, pretending to be a woman.
Don knew that if his wife or his guest arrived unexpectedly, he would hear the front door opening chime. His study door was also locked. Some days he dressed more than others, and many days he never got around to masturbating at all. But his study was his castle, and he wore what he felt like whenever he felt like it, with no worry about being interrupted.
What Don didn't know is that Tom Jackson had never left the house that morning. His meetings had been canceled, and he slept in.
Shortly after Tracy left for work, Don fired up his laptop and resumed browsing PornoTube. Soon he was watching his favorite content, "chicks with dicks," while stroking his erection with a pair of Tracy's dirty panties. Every few strokes, Don liked to pause a second or two to sniff the musty crotch, then resume stroking. He wore gym clothes, a loose-fitting absorbent T-shirt and athletic shorts. Under the shorts, his favorite robin's egg blue bikini pants.
He sat that morning gently stroking his very hard cock. He kind of liked edging himself – 5 minutes on the laptop every half-hour or so, then 20 minutes of porn-free, clearheaded computer debugging. He thought he'd go an hour or so, and then dump his prostate around 10:00 a.m.
Tom didn't waken until 9:00. He decided to get himself a cup of coffee from the kitchen before he jumped into the shower, so in a bathrobe and slippers, he went downstairs, where he thought he heard the sounds of sex from behind the door to Don's study. It clearly sounded like porn, not real people, and Tom smiled at the thought of Dirty Don rubbing one out while his cock-sucking wife was out.
Standing in the kitchen, sipping his coffee, Tom could hear the laptop a little bit more clearly now. Not really well, but better than from the foyer. And it all sounded a little gay.
Now Tom really got curious. Tracy had assured him the night before that Don knew about and encouraged her sex with guests. He wondered what other kinky shit Don got involved in. Maybe Don swung both ways, like he did?
In fact, he enjoyed being blown by a man more than a woman. For one thing, men swallowed. They always swallowed, and you couldn't say that about broads. At some point, every guy on the planet tastes his own cum, and many find it delightful, if not the first time they try it, maybe the tenth. (Funny thing how many guys go "yech" the first time but then continue to do it every time thereafter, until one day they admit to themselves that in fact they kind of like it.) Most men who taste cum once do it often, and most men wish they had more cum to swallow. A mouthful of some other dude's cum scared very few men.
Tom quietly opened the door to the back deck and leaned around over the railing.
Don was facing away from the wall, sideways to the window. Curtains had been pulled together, but not quite all the way. A roll-up blind had been pulled down as well, but again, not quite all the way. Tom had a good view of Don and his busy penis, but couldn't see what was on the screen.
Which was fine. Tom knew what was on the screen because the audio was even clearer now. Don was watching a porn wife order her porn husband to suck some porn stud's dick. Tom quietly went back into the kitchen, retrieved his phone, and went back to capture Don playing with his erection in Tracy's dirty panties. Don continued edging himself, beating a little hubby meat, then sniffing a little wifey crotch.
Tom decided to go for it. Back in the house, he knocked on the door of Don's study quite a bit louder than strictly necessary. His plan was to knock Don off-guard right away. There was the expected "just a minute," and some shuffling of chairs and desk drawers. Don opened the door a little bit and said "Mr. Jackson, what is it? Is there a problem? I thought you were out."
Tom just bulled his way into the room and started pretending to be outraged. "A sex pervert? You're renting rooms to the public and you're a sexual deviant?"
Don just spluttered and Tom went on. "Disgusting gay pornography? Playing with women's underwear?" He then strode boldly to the window and rolled up the shade. "Masturbating in front of a window where anyone can see you?"
Don tried to utter some sort of rebuttal about his privacy and an invasion thereof, and Tom cut him short with a raised palm and went for the goal line.
"I have it all on camera, you sick fairy. Does your wife know what you do here every day? Shall I show Tracy this video of you," Tom paused dramatically, "of her dear husband, smelling the crotch of her panties and indecently exposing himself while drooling over pornographic pictures of hard cocks?"
Don crumpled into his chair. He looked stricken, pale. He leaned forward to put his head in his hands, and his shoulders shook as he began to cry and hyperventilate. While he was open with Tracy for two years now about his – their – cuckold fantasies, he carefully kept from her his interest in transsexuals and cross-dressing.
Tom lowered his voice. Soothingly, he went on, "It's OK, Don. Don, I'm sorry. Get a grip on yourself, buddy. All men are a little curious. That's all it is, right? You're a little curious?" He gently placed a hand on Don's quivering shoulder. "Tracy doesn't have to see this camera, Don. Why upset your wife?"
He reached with his camera hand and opened his bathrobe.
"It's just a little curiosity, right?"
Tom now drew his very erect penis through the fly front of his pajama pants. Don stared at it like a drowning man who thinks maybe he sees a ship approaching to save him.
"Just curiosity, Don. Me too. I'm like you, Don. I'm so curious. I wonder what it's like, you know, for a man to please another man. Maybe we can help each other." And with that, Tom gently stroked his hot cock against Don's cheeks, and lips. As Don yielded, he saw no point in telling Tom that this wasn't Don's first blow-job.
"Let's both be curious, Don. Let's explore, all right? You and me. It's not fair that Tracy gets to suck cocks and you can't. What do I taste like? Open just a little and kiss my cock, Don. My cock is hard for you. You made me so hard. Harder than Tracy did."
Don stopped shaking and pulled himself together. Tom now had his hands on both sides of Don's head, holding it gently in front of his erect penis. Don tentatively, very slowly, licked the head of Tom's cock and then drew just the head of it into his mouth
"What do I taste like, Don? Is it as good as you always dreamed it would be? You've been dreaming of this for years, am I right? Years. Wasted years, Don. Just a taste, for curiosity, OK? Our secret."
For a long time, quite a long time, he just suckled on the large round head at the end of Tom's cock. Don's lips nibbled Tom's glans and his tongue swirled around the head and across the slit. With each passing minute, Don became more relaxed and tranquil as Tom came closer and closer to his impending climax. This was a first for Don; not the first blow-job, but the first sex he had without Tracy since they married decades before. As much sex as the two of them had shared, this was a kind of coming-out party for Don.
Filming again with his camera, Tom held his jizz back as long as he could. He knew Don needed to settle down and do this for a while, unhurried, exploring both the cock and his own heart. Tom restrained himself from too much motion. No thrusting, no stabbing his cock into Don's throat. Tom was unconsciously aware that while he was fucking Don's face, his throbbing cock was healing something in Don. Something that had always been broken inside. Tracy sucked dick for money, but Don was sucking cock because he just needed to.
When, ten minutes later, Don swallowed Tom's ejaculation, it was like finally getting the right medicine to put him on the path to the happiness that had always eluded him. Soon Tom spoke to Don while still stroking his head: "Let's go rest for a while." Tom took Don's hand and led him upstairs to the guest room. "We need a few minutes to talk. You'll be back at work in no time. But we need to talk about us."
They lay side by side on Tom's bed and talked a little bit about fear, and curiosity, and bisexuality. Tom drew Don out, offering a few facts, or maybe fictions, about himself, and eliciting secrets from Don. Tom learned how the Elliotts stumbled into prostitution while they were chasing Don's cuckold fantasies. Tom spoke about his own first time being blown, in college. Don talked about the time he masturbated a stranger in a movie theater downtown. When Tom took Don's ass half an hour later, Don was ready, even eager, to offer it to him. Tom was persuasive, and Don was still curious. Well-lubed and curious.
Tom was experienced at anal sex, and did all of the right things: used lots of lube, and one finger at a time. He knew that for a beginner the easiest position in which to open his anus was face down on the mattress, so Tom started Don there. Don chewed the pillow a bit before Tom finally slid the final inch up into his rectum.
Then, when Don was ready, Tom lifted him up on his hands and knees and mounted Don like a dog. This was always Tom's favorite position for taking another man because he could reach around and either torture his bitch's nipples or give him a reach-around. For Don, Tom worked his inexperienced tits. No reach-around for the new guy, not this time.
Finally, Don's body completely surrendered the fight and stopped trying to resist entry to Tom's dick. Soon after that, Tom was happy to see that Don was rocking back up onto the cock unaided, horny for more penetration. After a few minutes savoring Don's submission, Tom rolled Don over on his back and introduced him to the intimacy of the missionary position.
Tom knew that while it was humiliating for a man to be fucked from behind, it completely transformed a new bottom to take another man's cock between his splayed legs, face-to-face, like a woman. There's nothing quite as humbling as staring into a better man's eyes as his hips heave back and forth between your thighs and his hard shaft plumbs the depths of your ass, hopefully banging your prostate from the inside on each stroke.
Don wrapped his legs around Tom's hips and tried to hang on tight as Tom's hips thrust forward and back, drilling for satisfaction. Don's sphincter was spasming uncontrollably, pinching and chewing Tom's dick as it thrust in and out. Once every three or four strokes Tom withdrew completely, and Don's asshole closed all the way with relief. But then Don's empty rectum complained, and his anus willingly reopened as Tom came sliding up inside again.
It can't be explained why so many straight men fantasize about cock but shudder in disgust at the thought of being kissed by another man. It just isn't rational. It makes no sense to think a cock in your mouth will be merely an adventure, but male lips against your own would be an unspeakable, disgusting horror. But rational or not, it is universally true, as Tom knew from experience when he attacked the very last shred of Don's masculinity by French-kissing him.
Don firmly resisted at first, holding his lips tightly together and trying to turn his head away from Tom's mouth. But Tom persisted and held their lips together despite Don's efforts. Don finally accepted who he was and let that last shred go when he finally sucked Tom's tongue into his own mouth and then ejaculated all over his own stomach. No reach-around had been necessary; Don was a natural, and Tom just simply fucked the cum out of him. Don would never quite feel like a man again.
Sound asleep, exhausted, they heard nothing when Tracy came home early and found them together, Tom naked, Don wearing a brassiere and a nightie, his battered shit hole still leaking cum, the bedroom door half-open. To be honest, she'd always had her suspicions about her husband. She quietly closed the door and left the boys as she found them.
Downstairs she smiled and thought that now their B and B could really make some money. She opened the web browser and logged on to LGBTQBandB.com.