When Harriet Met Sallie Ch. 06

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Chapter 6 Sallie Gets Used

The day after was Sallie’s “date” with Mr. Thompson, and she was aflutter with anticipation. As she folded the sleeper couch, Harriet staggered out of the bedroom asking for coffee. With a good night’s sleep, though groggy, she had recovered from the previous day’s adventures and left her room on her own. The couple spent most of the day on Sallie’s prep; she was excited but anxious. Mr. Thompson would pick her up at seven, and she had to be ready. Harriet helped her prepare for the big “date,” did her makeup, helped her into a corset and a miniskirt, and clean her insides. She also tutored her on walking in high heels. It was hard, at first, but Sallie soon took to it like a natural. They even tried walking up and down the stairs. Sallie’s small lithe body made it easy to train even with very high heels she was to wear.

Harriet might have been envious of Sallie getting what she never had with him. Dinner out in public, at a nice restaurant: romance denied her in exchange for total submission; but she wasn’t interested in any of that. Still pleasantly sore from the activities of the previous day, her mind kept drifting to Brandt’s big fat cock and then her impending punishment for her reaction to it. The image popped into her mind repeatedly as the day went on with Sallie’s prep.

At ten to seven, Sallie could wait no more, and was peering down their street looking for his limo. There he was! a few minutes later inside the luxury car, looking dashing and manly, as Sallie stooped in to get in giving him a view of the fake cleavage Mistress helped her create with falsies, a training bra, and makeup. He smiled broadly and chivalrously offered his hand drawing her into the car.

He spoke casually, which he had not done until then. All she had heard from him were insults or careful instructions. He conversed with her charmingly, asked after Xandra, whom he called his sister, and related tales of adventures of their younger days. This went on through dinner at a fancy steakhouse, where the atmospheric dim lighting was amenable to the new-minted sissy. Who, very nervous about exposure, demurred all evening, letting him do most of the talking.

She had become hyper-aware of the masculine tone in her voice, and practiced modulating, but a grating falsetto was the result. That wouldn’t work; so, she said everything in a husky whisper. She couldn’t wait for the surgery to help with this. He recognized the problem and was happy enough to survey her mew look, as he chatted with and interacted with the waitstaff. He ordered for both, choosing a T-bone steak for himself and a plain salad for his companion. “You’ll get your protein later, tee hee,” he leaned over and murmured cheekily.

As much as he had, at first, claimed he would not touch her until her complete transformation, once back in the limo, he couldn’t keep his hands off her. He grabbed the back of her head and pulled her hard toward him and shoved his tongue deep in her mouth. She had practiced cocksucking all afternoon with Mistress, first on a smaller dildo and then on the big one. The tongue in her mouth made her think of nothing else. She gave in to his tongue and tried to follow it around her mouth, but it seemed to be everywhere at once.

As he kissed her, he slipped his hand under her miniskirt and fondled her ass cheeks, closing in on her little hole, a plug buried deep inside, its bejeweled tail poking out. He knocked his fingers against it and tapped at it, sending waves of joy to Sallie’s prostate. She moaned into his mouth like a bitch in heat. This moment was strange for Sallie; it may not have been a long-held dream, but it may have been her whole life. Salvatore could not have named this desire, even as he watched and jerked to sissy hypnos, but Sallie knew this was always the objective.

Now, that she had embraced these desires, her mind was aswirl with expectation, it was thrilling to now get what she thought was weeks, maybe months away. Her tiny clitty was engorged; it embarrassed her to still get hard. She found it incongruent for her superfluous clitty to be hard in front of her Master, disrespectful to him, an abomination. But she was glad her penis had begun to shrink, and only harden occasionally, as her new cage constricted her teeny hard-on. So lost in the sensuousness of the moment, she still was going through kissing motions and wriggling her ass, when he backed off and declared:

“C’mon, sissy, we’re here.”

“Here” was the B-Sides Cabins, a boutique motel, whose schtick was small individual private cabins rather than a strip of side-by-side rooms. It was two exits out of town on the interstate, but set up around a private wooded land. The B-Sides was very popular with patrons interested in short but “ultra-private” stays, and had the money to avoid a seedier venue. Mr. Thompson had booked the most isolated cabin for the whole night. The chauffeur pulled in, came around the passenger door, held it open for Sallie with one hand, and helped her out with the other.

Once in the room, Mr. Thompson pointed toward the big round bed, with an old 45′ Ankara escort record coverlet. This one was a replica of Eric Clapton’s single “Lay Down Sally.” Requested from a list by Mr. Thompson. Sallie smiled at the thoughtfulness and the double-entendre.

“Sit, for a moment, Sissy,” which she nervously did.

He continued his conversational, even affectionate, tone. She had no idea what to do with herself while sitting idle, how should she sit, or where. She finally opted to cross her legs at her ankles and keep her hands on her sides, trying to affect the look of a proper young lady. Her obscenely high heels letting her feet touch the floor rather than dangling above it.

“Sissy, I’m not going to mark you, tonight, like I did your wife the other night. We’ll wait for when you are more femmed up. I heard from Xandra how nicely your little hole opened for her, and just had to get a little taste of my own. Are you happy, my little cuck sissy bitch? Do you mind that you had to give up your wife and… haha… being a man?”

“Oh, Sir. I am so happy! I don’t think I have ever been happier in my life. Thank you, Sir!”

“Aww, that’s really sweet, faggot… you mind when I call you faggot; I guess you’re not really a faggot anymore, cause you’re not really a man, huh?”

“No, Sir! But I don’t mind what you call me. And… I love my wife, but I’m honored that you have chosen her to be your subslut. I know I was never really a man and never deserved to ever fuck her… yes, haha, I guess I’m not a faggot after all, but I’m so happy to be yours, Sir. I want to be such a good sissy bitch for you, Sir. I’m such a pathetic sissy bitch, I deserve and want to be degraded by a big beautiful alpha male, with such incredible cock. I want to be dominated by you, Master. I want to be emasculated by your big black cock deep in my hole… Daddy?!!”

She uttered the last word nervously, but alluringly. She had heard it a lot in her sissy videos. Salvatore’s parents divorced early in his life and his father was not in the picture; the mother never remarried. He had never called anyone “Daddy.” She loved the sound of it, but wasn’t yet sure if he would approve. He nodded and smiled at her, reaching her chin with his huge hand.

“That’s okay, sissy, but don’t say it in front of your wife, okay?”

“Yes! Thank you, Daddy. Daddy…?!”

“Yes, sissy!”

“I want to be punished. Please…? for letting Xandra take my virginity instead of you.”

She sincerely felt this way, though he set up the whole thing himself. He didn’t really care about it. He never meant for Sallie to be used exclusively. But he was delighted by the request and the gesture. She was going to be a special sissy bitch; he smiled to himself. But he had no time to punish her just now. He would use it to help build up Sallie’s expectation.

“I’m glad you thought of that. Though I okayed it, Xandra told me you didn’t resist giving her my hole for a minute. I will be happy to punish you properly, whore, when I get back from my trip… Sooo, I have some news that you are going to like and some I’m not yet sure how you will take.”

“Yes, Sir. What’s the good news?”

“I am going to fuck your sweet little hole tonight, sissy bitch.”

“Oh, thank you, Sir. I have been looking forward to that. The other news, Master?”

“You’re going to spend the night getting fucked, sissy… but not by me. I only have time to get a little taste of that sweet hole before I must fly out to the West coast. But fear not, my little faggot sissy bitch, the cavalry is on its way. I have some very good friends, who will be along shortly. I think you will be happy with their… ahem… equipment. What do you say, sissy?”

“Oh, thank you, Daddy!” That’s what she said, but what she thought was: “I could have skipped dinner, I would much rather have spent the time here getting fucked by my Daddy.”

“I’m going to prep you for them, my sissy whore.”

He approached the anxious Sallie sitting on the bed, and led her to her feet. He twirled her round like part of a dance. She looked super cute in her five-inch-high heels and super short Catholic schoolgirl skirt with white mid-thigh stockings with a lacy design. The corset gave her a somewhat waspish waist that gave her slim hips slight curves. Harriet had done a great job on the makeup, letting her be sexy, but not trashy, helping to soften her less feminine features.

If one didn’t know what she was, she might pass at a glance. On closer inspection, you might notice the Adam’s apple or the male forehead her bangs tried to hide. The top was a magic trick. She had no breasts yet, but clever use of a bustier and bra insert, gave the impression of cleavage. Harriet drew shadows and contours with makeup on her chest, making it look like B cups. Mr. Thompson gallantly helped her remove the light jacket that did more to highlight than hide the lacy red bustier, then had her slip out of the teeny skirt, which was a bit of struggle with the heels. She slunk off the thong that drove her crazy, teasing her little hole. She had the big plug all day to distend Escort Ankara her anal ring to better please his big cock.

He took in her new sexy visage and it turned him on. He loved feminizing little sissy boys. He now recognized this one would be spectacular. Though he instantly recognized what Sallie was, he hadn’t seen this much potential. He expected at best a serviceable not-quite-passable sissy. Ty wasn’t as hung up on sexual preference as he projected; he had many different relationships with his cuckolds. Some he had no sexual interaction with; they watched, humiliated, while he destroyed their wives. Others would blow him as men wearing wigs and lipstick. But gazing at his sexy new recruit, he was afraid—as with the wife—he would wear her out too fast. He felt another twinge of regret at the evening he planned for his new gurl. But he had to keep his troops happy; they did much of the “grunt” work to keep his Dom empire going.

His group was a cosmopolitan mix of fellow travelers. Two he knew from his college football days. It was so easy for them to get women; they would push boundaries getting rougher and rougher with girls that were into it. After college, Ty became more devoted to his dominant proclivities, he found enough women interested to form a club, of sorts, with his old pals. But as some got involved with “real lives” (wives, kids, career, etc.) or moved away, he had brought in others, always with careful vetting before bringing them into the fold.

Tyrone Thompson was never interested in the domesticity of marriage. Now twenty years later, he pursued the same sexual interests. Those that joined the club later were random: a guy he played b-ball with at the gym, one had worked for a Fraugger’s supplier, and others he found serendipitously. They didn’t all have massive cocks like Tyrone, but they were all above average. That was an important point for him, no little-dick Doms allowed in his club.

In all, there were nine direct members of this exclusive group and quite a few others associated but not true members. Tyrone Thompson was their undisputed, though informal leader (it wasn’t like they followed Robert’s Rules, or anything). Guys would swap in and out, but he liked to keep the number right around ten. Big enough to scrounge up a decent gangbang at a moment’s notice, but not so many that he had to struggle to keep them “fed.”

Johnnie, his deputy, made porn videos, including the personalized sissy hypnos he sent Sallie. They also did brisk business filming cuckold scenes with men who wanted to watch and record their wives getting gangbanged; he and others ran a website for the purpose. They turned down more scenes than they accepted; most one-offs, but sometimes they recruited wives and cucks for their crew from the website. Their main rule was that they would share their subs, eventually. But it was loosely kept and functioned within the confines of the “honor system.”

Tyrone Thompson had come upon deliberate cuckolding by accident: he was sleeping with a submissive married woman. One night, she was tied up and he was fucking her up the ass, when her husband appeared at the bedroom door. Ty reared up expecting violence, but the cuckold just began sobbing.

“Not again, honey! Wh… why? [sniff, sniff].”

“Because you are a tiny-dicked nutless wimp, faggot! Just sit there, crying like the little bitch you are, while a real man with real cock fucks your wife’s nasty hungry asshole?”

“But, honey, sniff, sniff, snivel, ugh guguguh!”

“What did I say? Take off your clothes and show my big black bull why you’re a cuckold!”

Shaking anxiously, he took off his clothes. When the cuck removed his lacy panties, the revelation shocked the younger Tyrone. The cuck had tiny button for a penis, which extended out no more than a bump, and hanging below it a sad little empty sack. He was hairless; if one looked quickly, one might think it was just a big clit and the deflated sack, saggy pussy lips.

“You see why I have to get a real man to fuck me?!”

“Fuuuucckkk! That’s the smallest I have ever seen; but what happened to the rest?”

“Tell him, what happened to your little peas, cuckboy faggot!”

“Uhm… erhm, uhh… Well, her last Dom had them cut out.” He was weeping openly, now.

“Why, faggot?” she bellowed.

“Mistress, because… I did not learn my place. I tried to put my teeny peenie into Mistress while she slept, Sir, when I knew I wasn’t allowed.”

“Holy Shit! Hahaha! That seems harsh.”

“Turn around, faggot, show him!”

He turned around, bent over at the waist, and opened his asscheeks to the stranger whose cock still lodged in his wife’s asshole. Where we’d expect to see a rosebud, there was the round bejeweled end of what turned out be a massive glass butt plug. Tattooed around his hole was the phrase: “If you can read this, you can fuck my wife.”

Tyrone chortled loudly. “Oh, fuck! Dude! That’s fucked up.”

“Okay, faggot! Put the plug back in and go sit in your corner, like a good little cuckold bitch.”

“So, he doesn’t mind me fucking his wife?” Escort Bayan Ty asked the slut wife.

“Nah! he fuckin’ hates it; he’s going to cry his bitch ass to sleep tonight in his cuck-cage, but he don’t get a fuckin’ a vote here, the useless cunt.”

She nodded toward the corner of the room where the cuck was now headed. There, stood a dog crate, outfitted with ties and straps. The cuck opened the crate and climbed in, with the practiced efficiency of habit. He positioned himself on his knees his back stooped and his head low, put a gag on himself, then locked his head into an opening on the side of the cage, for the purpose. Slipped his hands through handcuffs on the roof of the cage and faced the action. He sobbed and groaned audibly even through the gag, as the wife screamed:

“Now, fuck my ass with that huge delicious cock, please, Sir!”

The scene had both startled and enchanted the younger Tyrone. Up that point, he had slept with many married women and even practiced some bondage and S/M with them, but he had always done his best to avoid meeting the man he was cuckolding. He spent no more time with this couple—it was weird, though he kind of got off on the groaning cuck, as he ripped into the wife’s holes. She would moan loudly and bellowed humiliations at her cuckold.

That was his first experience, but the idea didn’t leave his mind, and one day he met a hot white girl at a party, whose diminutive husband followed like a lap dog. She blatantly flirted with Ty right in front of the husband, while he smiled and nodded. Soon, they revealed that they were “cuck-curious” and she always fantasized about big black cock. This was his first cuck conversion; after this, he began to understand how to set the parameters of these situations.

It had not gone well with that couple. He had done what he now feared might happen with Harriet and Sallie. Just like them, the two were overeager and willing, and he was then inexperienced and overconfident. The cuck’s small size and delicate features gave him the idea of feminizing, which turned out okay—not as well as he now expected of Sallie. But he used them up; drove them too hard and too fast, until he couldn’t stand the sight of either.

He whipped the wife, until he couldn’t find her appealing, and the sissy was never as satisfying as he expected. So, he “released them.” He was concerned a similar thing might happen with his latest acquisitions. He continued to have second thoughts about the evening’s plan, but it was too late. He had to be on a plane to California in just a few hours, and his boys were on their way, horned up by his description of his new sissy. He had sent them Xandra’s pics.

He had very different plans for Harriet and Sallie. He wanted them needy, but from different causes. Harriet, he wanted on edge, chaste and ready to do anything for sexual release; Sallie, not only shift her primary sexual organ, but turn her into an insatiable slut. But suddenly, what he most wanted to do was fuck the sissy slow and sensually first, savoring her sweet hole, then a few whacks for punishment and fuck her hard and rough all night. Given what her night would be like, he decided to reward the sissy and give her the first half of the plan. But he had no time to do slow and sensual so he settled on what, for him, would be a tender and romantic tone.

“Alright, my little sissy bitch, on your knees right here.”

“Ooooh, yes, Daddy!” She nearly melted from the heat of her desire.

She got on her knees by a small leatherette banquette at the foot of the bed. Sallie’s mouth already agape anticipating her Master’s cock in her tiny mouth. He leaned way down and kissed her passionately, roughly pulling her head back. He broke their kiss and leaned back just a bit.

“Keep your mouth open, pussy bitch.” He spat a gob of saliva into her mouth, undid and lowered his pants to his ankles, exposing that magnificent member, now burned into Sallie’s consciousness. “You want to suck my cock, bitch?”

“Yesss! Yes, Sir! I’d love to suck your cock, Daddy, please, may I?”

He nodded and nudged her head over to it. Normally, he would have made her earn it; Sallie wished he had, craving that kind of attention, but Ty felt magnanimous. She had earned it: in less than a week, she went from pathetic loser “male,” to a delicious cute sissy, willing to do anything for his cock. She had also gone a long way toward shifting her sexual focus from her tiny useless penis to her asshole and prostate. He kissed her hard again then alternated kissing and slapping her face hard. She found it comforting and loved him giving her what she wanted.

“Kiss it sissy! Worship my cock as your God. Bitch!”

She did! She practiced the night before and during the day, trying to get over her gag-reflex, but she still had trouble getting the big head of the dildo into her mouth. But, when she began sucking the real thing, she was pleased to notice it was more malleable than the replica, and easier to fit in her delicate mouth, stretched to its utmost. She couldn’t wait for the surgery to let her fit his big cock in her mouth more comfortably. She managed to her throat, but the gag-reflex wouldn’t let her relax enough to let it in. He thought about gagging her until she retched, but didn’t want the mess. When she gagged, he pulled out, let her suckle the head and lick his big balls, and turned to her sweet little hole.

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