Stillwater
Copyright© 2021 by Maxicue
Chapter 37
Erotica Sex Story: Chapter 37 - After completing a lengthy prison sentence, Harry finds luck beyond any he could imagine, including with the ladies.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Ma/ft Fa/Fa Mult BiSexual Sharing Anal Sex Oral Sex Prostitution
In Nashville, Marie watched the newest episode of Miss Leo being filmed where more sex was involved than ever, and more glimpses of his cock and balls if one looked close while Leonora rode him reverse cowgirl. In between, the audiences got glimpses of him in action, dramatically, from a scene with him and Marisol from the amateur PI film they’d done during the summer while he discussed his acting career with Leonora.
And speaking of acting, after his reading at the cool independent bookstore in Nashville, he flew to LA for a shoot, a small but pivotal role of an oblivious nice guy fucking a gangster’s moll and getting killed for it. He was thankfully only needed for a couple days shooting and flew to New Orleans to meet up with Leonora and to say a planned goodbye to Marie.
It didn’t turn out that way. Marie found her mother, since she was still living in the apartment Marie grew up in. Her mother had become a junkie and looked very much like an old whore. The worse part was her mother’s supplier, her former pimp, who shacked up with her as partial payment for the dope, the rest of the money Marie didn’t even want to know how her mother got, but almost immediately when the ex-pimp arrived in her mother’s apartment, her mother tried to arrange her fucking him for more payment. Marie immediately ran off.
Comforting a shaken Marie eventually meant Leonora making love to her, and, at Marie’s insistence, Harry joining in. The next morning they headed to Houston.
Being a huge city, there was a lot of escorts. An online chat room for them brought Marie potential partners, both for work and possibly in bed. “I’ll help pay for their time,” Leonora offered.
“Thanks,” Marie smiled.
It amused Harry when he opened the door for the auditioners. “I thought...” they inevitably started, to which he would interrupt with, “Follow me.”
Again they had a suite, an upgrade from what the publisher had Harry in, though they at least put Harry in the fancier hotels so they didn’t have to deal with a different one. Leonora insisted on paying for the upgrade, and in fact arranged it.
His greeting the escort candidates had a purpose, a sort of quick vetting, noticing how difficult they found Harry being there instead of some woman, and how quickly they recovered. The higher vote on Harry’s part he assigned to those who switched all the way over to seductive. Only two did that, and one was especially attractive in a similar way as Heather was attractive, a voluptuous blonde, though even more buxom which Harry wasn’t sure was a good thing. Augmentation seemed likely.
After a couple days of this they conferred, much like a director, casting director and scene partner might do choosing who would be good for callbacks.
“Let me guess,” Leonora smirked. “The blonde bimbo.”
“Depends on how you feel about boob jobs,” Harry said to Marie. “She’s augmented, isn’t she?”
“Not my favorite thing,” Marie nodded.
“Heather wasn’t?” Harry asked.
“She got her shape naturally, which means she has to watch her weight and can’t really be impossibly slim.”
“Because tits are basically fat,” Leonora nodded.
“It’s a balancing act, but I like her softness.”
“I imagine men do too,” Leonora concluded.
“They do,” Marie agreed. “I did like the bimbo.”
“She did seem likable,” Leonora agreed.
“And I liked her idea of me joining her onstage when she strips.”
“She’s a stripper?” Harry asked.
“A prostitute doesn’t really need such tits. Unless it’s just to make her feel more desirable, it’s only for strippers and porn stars.”
“Is she a porn star?” Harry asked.
“She promotes herself as one,” Marie told him.
“And would you do that?”
“I don’t even know if that exists anymore. Maybe porn video star? Maybe shoot movies with her?”
“I don’t think Harry would mind the second audition,” Leonora said.
“I’m with Marie on the fake tits thing, but if you’re still interested, I think she’d be one of the better ones with men.”
“Anyone else, Harry?” Leonora asked.
“The dark brunette with tattoos,” Harry said. “She’s not as pretty as some, but...”
“Really?” Marie asked. “She actually did have a great body, but she seemed pretty butch.”
“She did end up putting on her charm for me.”
“Probably figured out you were part of the approval process,” Leonora guessed.
“Which at least makes her clever,” Marie realized. “I thought she was cool.”
“Me too,” Leonora agreed.
“What about you, Marie?” Harry asked.
“I liked the redhead. She was beautiful and her body reminded me of Heather’s. She could lose some weight though.”
“She seemed the most disappointed when she saw me,” Harry said.
“Even more reason to test her,” Marie decided. “What about you, Leo?”
“The raven haired vixen,” Leonora told her.
“Because she looked the most like you?” Marie laughed.
“Maybe her body, but...”
“She could be your sister with darker hair and a more Roman nose.”
“I’m not that much of a narcissist, am I Harry?”
Harry shrugged.
“Asshole,” Leonora grumbled, but ended up laughing with the others.
It ended up being an interesting and expensive couple of days, hiring four fairly elite escorts for two hour sessions, the first for sex with Harry involved and the second for conversation. Leonora became the greeter at the door, and remained outside the larger bedroom. Harry would join her in bed during the second hour, and Leonora would bring him into the second bedroom a couple times because hearing the sex had made her horny.
That first hour, Marie pretty much did her bit like she had with Heather, giving a show for the john, Harry, encouraging her partner to be vocal about her pleasure the way she did, not too over the top, but convincingly, then beckoning Harry over to join them. If Harry hadn’t cum as voyeur, which he didn’t, she’d have the potential partner choose whatever method she wanted to make him cum, keeping a hand towel handy for whatever they chose: hand job or blowjob, presuming the woman wouldn’t swallow. Once he came, Marie offered her mouth to get him hard again while he caressed the other woman, or in Harry’s case, licked her mostly. She gloved him up, took the sixty-nine position with the potential partner on top and Harry fucked the woman from behind.
Harry proved spot on with his choices, the redhead revealed herself to be much too reluctant about him joining them, at least at the beginning with the hand job. She tried to feign indifference, which still wasn’t the best choice. The raven haired beauty, ironically, proved to be a bit narcissistic, like she was queen of her realm. She gave a rudimentary blow job and Harry purposely failed to warn her when he came, and she immediately pulled off and spit his first ejaculate into the hand towel before drying off the spend on her body when he shot onto her chest.
The blonde proved not at all convincing with her vocalizing, made all the more obvious when she actually did cum when Harry fucked her. She did give a great blowjob, doing the porno thing with her mouth wide and his cum hitting her face as much as her mouth. She discreetly spit what he did manage to send into her mouth, the discreetness helping her cause.
The butch brunette ended up being remarkably different than the others. For one, she completely took things over from the beginning, essentially making love to Marie including kissing her. And once done sucking an orgasm out of Marie’s quim, she beckoned Harry over when Marie returned the favor, after a lengthy kiss, once her mouth became free. She had Harry kneel beside her head and she suckled his glans when she wasn’t fisting him. “You better warn me,” she demanded.
When he did, she ended up swallowing. He kissed her afterwards, his choice not hers. You don’t demand a john to kiss a spermy mouth even if you tend towards dominance. While she got him hard again, mostly with her fist, she paused to express the intense orgasm Marie brought her. The woman showed real truth in her sounds. The only time she gave up control of things was when Marie shifted to sixty-nine with her on top so that Harry could fuck her from behind, and again the two orgasms he gave her sounded honest, the last harmonizing with his own moaning grunt.
The post-mortem happened after the disappointing raven-haired queen, sent packing fairly early though paid the full two hours. Marie entered the second bedroom watching Leonora post on his cock, and once Leonora became sated, she remained there, slowly continuing the fuck, just to keep Harry hard and her excited.
“So?” Leonora asked.
Marie wanted to wait for the last applicant to be finished, in part to mull things over, and in part to give every lady a chance.
“Definitely Freddy,” Marie decided, meaning the butch woman. “She’s hot, fun, and knows her way around a cunt.”
“A cock too,” Harry added. “She said she’s interested in a partnership?”
“She loves the idea. She said it was like filling in a missing piece for her. She’s done doubles before because she looks the part, but never got together with the girls like I did with Heather. They seemed to think it was a lark or something. She also brings stap-ons just in case, and had used them, including a narrower dildo for double penetration with the john. She actually brought them along,” Marie giggled.
“What do you think about that?” Leonora asked.
“I think it would be kind of hot,” Marie admitted. “She showed me the anal dildo, and it’s slim enough that it wouldn’t hurt.”
“Have you done that?” Harry asked.
“That’s always been Heather’s thing, mostly for more tips, but it just seems a lot less scary with a slimmer dildo, and she says it makes things tighter and more sensitive.
“She’s also a dominatrix,” Marie continued. “I actually like the way she took control.”
“Is there S and M involved?” Harry asked.
“She’s got johns where it’s a thing, but just one really likes the pain to be real. If we get together, which I hope we do, she’ll try things out with me, see how it works for me.”
“If she already has johns...?” Leonora pointed out.
“She said there’d be three choices depending on what the john wanted. She could do a show for him where I’m the submissive. I could be another Dom. Or I’d just be there as a sort of protector, watching her back.”
“It’s up to you,” Leonora said, “but it sounds like new territory for you.”
“I know, but like I said, I like the way she takes control. With Heather it was like I had to be the more responsible one. Even if she was older, I was the more mature. It’s like I feel like I can relax with Freddy. Anyway, she invited me to stay with her, and she said if I needed my own space, she’s friends with the super.”
“Friends as in...?”
“She fucks her. The woman’s supposedly the cliché version of a butch dyke, big and tough, wearing overalls and a tool belt,” Marie laughed. “Freddy said I didn’t have to fuck her, but the woman’s very appreciative of a hot young girl, and gives great head.”
“When would you move in?” Harry asked.
“I told her I’d let her know tonight and move in tomorrow because she said whenever I want and you guys are heading west.”
“After my reading...”
“You’ll be getting up early the next day. This way you can help me move in before the reading.”
“Makes sense.”
“Yeah, so, Candy’s not completely out of the picture.” Candy being the augmented blonde. “The partnering thing wouldn’t work out because...”
“She sounds like canned porno,” Harry filled in.
“I’d get her to tone down. But I’m really not all that into her. Still, the stripper bit sounds kind of fun, and I’m thinking about doing some porno with her, just to try it out. I don’t know what Freddy will say, and I’m sure that will be important, but...”
“You really are opening yourself up to new things,” Leonora commented.
“It’s like I been trapped and just got sprung.”
“I can relate to that,” Harry chuckled.
“True,” Marie laughed. “So you guys have fun while I make some calls.”
After she left, Leonora said, “I’m going to miss her.”
“Me too,” said Harry.
Leonora lowered her torso, bringing her lips to his while slowly increasing speed for the fuck. “Turn me over,” she said after the kiss.
“You sure?” Harry asked, knowing Leonora preferred, and was most comfortable in the dominant position, with doggy her second favorite.
“I want you to fuck me Harry.”
“As you wish, beautiful.”
In the missionary position it resembled making love more than fucking the way they gazed at each other between kisses. It took a while, but when pleasure took over, Leonora demanded Harry to fuck her hard, and her hands on his butt as well as the legs wrapped around his thighs further encouraged him, and he ended up cumming after she did by nearly a minute, though she seemed to get a second wind on her orgasm.
They ended up saying goodbye to Marie after Harry’s reading which Freddy insisted on attending, even having Harry sign his book for her. They had a late supper after at a casual bar/restaurant sitting in a Naugahyde booth. Freddy surprised them by ordering tonic water, sans booze. Marie followed her lead ordering the same thing. “Order what you want,” Freddy insisted, so Harry had a beer and Leonora ordered a white wine spritzer.
“I’m an alcoholic,” Freddy told them. “One year sober.”
“Congratulations,” Harry said.
“I don’t know if I am,” Marie explained. “I think Heather was the more compulsive and altered and I really hope she gets into AA or something. I’m not going to drink for Freddy’s sake and see how it goes.”
“I appreciate that,” Freddy smiled and kissed her.
They all enjoyed the fried chicken and thick fries and coleslaw and corn bread, then headed to Freddy’s apartment.
“Strip Mare!” Freddy demanded immediately. “And get on the bed!”
“Yes, Mistress,” Marie replied quietly. The bed took center stage in the apartment. There were two other bedrooms, private spaces, but the bed was central. Once on, Freddy shackled her wrists above her head and her ankles making her spread eagle.
“You two should probably strip, too,” Freddy advised. “And you can do your thing, Harry, to get my little Mare ready.
Harry understood and leaned down at the end of the bed and brought his mouth between Marie’s wide spread legs and began sucking her pussy. Leonora decided to sit on Marie’s face, knees sliding under Marie’s arms, facing away from Harry.
Freddy came out of one of the bedrooms wearing a tight leather boustier that propped her naked tits, leather boots that went up to her knees, all in black. Projecting from her groin was a narrow strap-on dildo. “Please fuck her mouth, Harry,” Freddy ordered. He took Leonora’s place. “I’ll need you later, Leo,” Marie promised.
She knelt and pulled out a box at the end of the bed. The KY from it she used to lube the dildo. She also placed an unopen condom on the bed before bringing out a crop which she used to gently slap across Marie’s nipples and down across her abdomen to her clit. Marie’s moans were stifled by Harry’s cock, the head of which was sliding in and out of her mouth. The crop nudged at the clit and even tugged at with the strap before Freddie replaced it with a leather cat-o-nine-tails. Just the tits and abdomen got whipped, still somewhat gently, because she’d slid the dildo into Marie’s pussy, fucking high inside her at a medium pace.
“Undo her wrists, Harry,” Freddy ordered, reaching over and undoing Marie’s ankles. “Turn over, Mare. Roll the condom on Harry and slide beneath her. Sit on his face, Leo, and make sure Mare’s giving you some licks as well.” After giving Marie some harder whips, Freddy guided Harry’s cock into her cunt. “Fuck him, Mare!” she ordered. Not long after Harry had fully entered Marie’s cunt, Freddy climbed behind her, tossing aside the KY after applying it to the dildo and Marie’s anus, and shoving the dildo in.
“Mmph,” Marie reacted, again muffled, this time by Leonora’s clit.
Grabbing the crop, Freddy slapped the side of Marie’s ass. “Giddy-up Mare,” she insisted.
Harry decided to help out Marie, pressing a finger against her clit and tugging at her nipples. It definitely assisted her cumming intensely, and when she stilled and shivered, he fucked up into her. The groan of her climax vibrating against Leonora’s clit must have sent the beautiful brunette over as well, and while she left her position atop Harry’s mouth, Marie began to move again. At the time her next orgasm hit her, Harry thrusted up into her pussy, his own orgasm approaching. Both undulated against each other while Freddy withdrew the dildo, hopped off the bed, and left them.
Marie shifted forward and kissed Harry, Harry quickly making sure the condom remained on his penis. “That her way of letting us know you’re being taken care of?” Harry asked.
“Yes,” Marie grinned.
“And?”
“It was intense!” Marie reported.
“Good,” Harry chuckled and kissed her again.
She slid off the table and Harry followed. “I’m going to check on Freddy,” she told them.
A couple minutes later they emerged from the bathroom hand in hand, Freddy as naked as Marie.
“I guess we should go,” Leonora said reluctantly, already dressed, Harry just finishing up.
Each got a hug and kiss from Marie and a handshake from Freddy. “I’ll keep her safe and happy,” Freddy insisted.
Harry nodded his agreement and he and Leonora left.
During the trip to the hotel, Harry pointed out, “When you eventually head home, you’re going to be driving alone.”
“What are you suggesting?” Leonora asked.
“Marie hasn’t set up shop yet here.”
“You’re saying...”
“And the farther north we get, snow’s going to be a factor. I’m not trying to get rid of you, but...”
“Maybe after Austin I head back, picking up Marie to keep me company.”
“It does make sense.”
“I’ll call her.”
Marie agreed.
“I guess I’ll need to let the publisher know I’ll need those plane rides again,” Harry realized. “I really am being practical.”
“But maybe some alone time wouldn’t be so bad either.”
“I suppose,” Harry admitted.
“One last episode I guess,” Leonora sighed.
“I guess,” said Harry.
In the hotel room, Leonora waved off getting fucked since she’d missed out on that at Freddy’s, but, not unusually for her changing her mind, she ended up joining him naked in the shower. “Fuck it,” she said, grabbing his penis.
Once cleaned and dried, a sixty-nine followed and her riding him after for a slow, intimate fuck that lasted awhile. When she turned around for reverse cowgirl, he understood she wanted something else and shifted things into doggy style where, when he quickened the fuck, she climaxed, climaxing again after a bit about the same time he did.
Austin became a casual, laid back weekend, helped in part by a laid back coed from UT who seemed to latch herself to Harry at his reading. An Indian/Scotch/Irish mix, she had skin that was naturally tanned and had blood that went way back before Texas became an American state or an independent country. A true native Texan, she reminded Harry of Joan Baez, or actually, at least in Harry’s opinion, her more beautiful sister Mimi Farina. She was also a singer/songwriter, furthering the comparison.
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