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Hot Wife Hotel - Olivia Gets All of Her Holes Filled (Part Two)

"Steve gets a front row seat to watch Bill use Olivia."

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Author's Notes

"Bill brings his A game, and his very large cock, to fill up Olivia like she's never experienced before, and she quickly becomes his favorite Hot Wife."

After a successful first shift at the Hot Wife Hotel, Olivia decided she deserved to sleep in the next day, so she didn’t bother setting her alarm. She’d had three clients on her first shift, which didn’t seem like a lot, considering some of the other Hot Wives had six or seven. But her husband, Steve, reminded her that she was new.

“Three is probably a good number to start off with Liv, you don’t want to overdo it on your first day,” he’d said.

When she woke up, she realized he was right. She was a little sore, but not terribly so. Still, it was better to work up to more clients over time. She also realized this wasn’t a contest. The whole purpose was to have fun and to fulfill some of their sexual fantasies.

She tossed on a robe and meandered down to the kitchen. Steve was at work already, but he left her a note by the tea kettle.

Liv,

I hope you enjoyed your experience yesterday as much as I did. I love you so much! It was hot to watch you suck and fuck those three guys. I would bet you see all three of them back sometime soon. I know Ray said he wanted more of the redheaded vixen when we were done fucking you in the shower. That was so hot, baby! You know I usually just like to watch, but I’d be game for a threesome with Ray again.

I want you to know that you don’t need to worry about how many clients you have in a shift. I’m happy to see you with one guy a week! Anything else is icing on the cake, baby!

See you after work!

Steve

Olivia made herself some tea and opened her Hot Wife account. All three guys had left her an email, each of them thanking her for a great time. Ray said the same thing about being open to a threesome, like Steve. Olivia laughed. It wasn’t often that her husband wanted to do more than just watch the action. Pretending to struggle as he held her down while Ray was fucking her had made him hot last night. She knew that was also one of his fantasies. She didn’t realize, until last night, that it was one of hers as well.

She checked her schedule yet to see if she had any clients lined up for next week. She was pleased to see she already had two guys booked. Both were new to her but repeat clients. She clicked on the first reservation and read the request.

Hi, my name is Bill and I decided to book an appointment after reading your profile. You sound fun! I am open to pretty much anything, as long as I get to fuck your ass. Thanks!

She smiled and opened the second one.

Hi, I’m Doug and I booked time with you because I have been with all of the other Hot Wives and wanted to try someone new. I just want you to masturbate for me and talk dirty to me. If you get me really hot, I will probably want to jerk off and cum on your tits. Let me know if that’s a problem for you.

Not a problem at all, she mused, but she made a note to check with the other women to see what Doug’s story was all about. She was just about to log off when she got a notification about a third appointment.

Hello, I am Sam. I’ve never done this. I picked you because you look nice. And I like your tits.

Olivia laughed. Sam was clearly a man of few words. She’d make sure he got to enjoy her tits and that he had a good experience so he would come back.

Over the weekend, she and Steve enjoyed some incredibly hot sex while he talked about watching her get used by other men. Reliving the experience made them both so hot and brought them to several amazing climaxes.

The week flew by and it was already Wednesday again. A quick check of her schedule showed Bill at noon, Doug at 1:30, Sam at 3:00, and she now had a fourth appointment, Ray at 4:30. She clicked on Ray to see what his request was for this time.

Hey Olivia, it’s Ray. I had such a great time, I decided to come back for more. I must admit, it was really hot when Steve held you down for me. I wondered if you and Steve would be up for a little role-play. Nothing too weird. I just want him to hold you down again, but this time I would like you to struggle a little more. I won’t hurt you or anything, but I might want to talk dirty if that’s okay. If it’s an issue, just drop me a message. Otherwise, I will assume that you are cool with it. Oh, and I want your pussy clean this time and I would love it if you’d wear something innocently sexy.

Olivia felt her pussy tingle a little at the thought of a little reluctance role-play. She mentioned it to Steve in the car on the way to Hot Wife Hotel.

“So, Ray booked again, and he wants to role-play you holding me down and me acting like I don’t want it. Are you cool with that?” she asked.

Steve felt his cock come to attention. “Sure, baby, whatever you want,” he said, trying to sound nonchalant about it. But truth be told, he was more than happy to play along as the husband who makes the reluctant wife fuck another guy, or even part of a duo who convince a hot babe that she needs their cocks. He thought back to last week, when Liv pretended to try to break free of his grasp. He knew his wife was a lot stronger than that, but it stirred him up when she acted helpless and gave in. He wondered what that said about him, then decided it meant that he and Olivia had great imaginations and a fabulously satisfying sex life.

“Okay, I feel comfortable with that as long as you do,” she said. “I wouldn’t want to be forced for real, but pretending was pretty hot last week. So was the bonus time in the shower. Hopefully, no one else books a time slot after him.”

At 11:58, she heard a soft knock at the door. She was ready, so she answered the door.

It was policy for her to answer the door in a robe and heels unless the client requested something else. Bill had not asked for anything special, so she donned the robe, tying the sash loosely, and a pair of red, four-inch heels.

Bill was a nice-looking older man, with silver mixed in with his dark hair. He had brown eyes and a really sexy smile. She decided to be a little playful and she pulled the sash seductively, letting the robe open to tease Bill.

“Mm, baby, you’ve got a rocking body!” Bill said. “I want to put my hands all over it, I mean you, sorry.”

Olivia pulled him inside the room and reassured him that putting his hands all over her was absolutely wonderful. She also reminded him that her husband was in the next room watching through the glass.

Once the door was closed, he took her into an embrace and slid the robe down off her shoulders, letting it drop to the floor. He lowered his head to take a nipple into his mouth, sucking and nibbling on it. Bill wasted no time as he slid a finger into her pussy to see if she was wet. She was, of course, drenched.

“Mm, your pussy is so wet and warm. I’m gonna start there. You get on the bed while I take my clothes off,” Bill said.

He undressed quickly and joined her on the bed. “Lift your legs up for me and hold them back,” he directed, as he spit on his hand and rubbed his saliva all over his hard shaft. Liv realized, as the head entered her, that he was much thicker than most of the guys she’d fucked. She shot a glance in Steve’s direction and he grinned, knowing she was going to be filled up good.

Bill saw the glance and said, “Is that where your husband is watching from? He’s welcome to come in the room and move a chair next to the bed if he wants a closer look at my thick meat invading your tight little pussy.”

Steve saw Liv nodding and decided he wouldn’t mind a better view. He stepped into view and nodded at Bill. He pulled the chair closer and sat down. Bill nodded back and then directed his attention back to Olivia. Seeing her on her back with her legs spread wide open and pulled back for him was so erotic. Her delightfully bare cunt with its puffy labia, waiting for him to penetrate her, stirred the lust in his loins something fierce! He wanted to just plow into her cunt, but he knew he needed to ease himself into her. He wanted her to enjoy the feeling of being filled up by his girth.

If all he wanted to do was fuck hard, he had a fleshlight for that. Sex was a hell of a lot more fun for him when he knew he was making his partner feel good. Pleasing a woman made him feel more like a man. So, he would take his time and use lots of lube to help her accommodate his large size. He’d have a better chance of convincing her to let him in her tight little back door if he gave her a great experience in her pussy.

Steve watched as the thick head of Bill’s cock disappeared into Olivia’s wet hole. He was glad Bill had invited him to watch from such an amazing vantage point. He waited a half a beat for the sound he knew meant pleasure. And when the long, drawn-out moan escaped her lips as Bill worked his shaft into her, Steve’s own cock became fully rigid. He loved hearing the sounds of her delight and seeing the look of it on her face. He instinctively rubbed his raging hard-on through his jeans and ached to see Bill move in and out of his wife’s glistening pink folds.

Olivia moaned again and said, “God, baby, I’m so filled up!”

Steve wasn’t sure if she was talking to him or to Bill, but it didn’t matter. Her beautiful pussy was being pleasured and that made them both happy. His own hard-on was begging for some attention, but he felt awkward stroking his cock while sitting this close to a man he’d never had a conversation with. Besides, a little self-denial would make him that much more turned on while he watched his wife be used all day. It suddenly dawned on him that his wife was basically a whore, letting men fuck her any way they wanted. And this little red-haired whore belonged to him. Others could use her and enjoy her body, but her heart, mind, and soul belonged to him. God, he loved her!

Olivia’s hips began grinding and Bill saw this as a cue to speed up his thrusts. He started to fuck her harder and faster, and realized he was going to cum in her pussy. He knew she was close too, so he started rubbing her clit while he pushed into her again and again. He felt the little nub grow hard under his touch and figured a little dirty talk might push her over the edge so he could explode inside her. He was determined to wait until she came before shooting his load.

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“You’re such a dirty little slut!” Bill said through gritted teeth. “Your pussy was meant for fucking, it’s so tight. I can’t wait to feel how much tighter your ass is when I fuck that too!”

Steve grinned. He knew she was turned on by his words and that her orgasm was just seconds away. He wanted to whip out his own dick and stroke it over her tits, but he was just the observer here.

Olivia was panting and moaning, her pussy ached for release! She was so close and felt that Bill was close too. She cried out, “Fuck my pussy harder baby, use me for your pleasure! Cum deep in my cunt and then I will suck you hard again so you can pound into my ass!”

That’s all he needed to hear! He picked up the pace, thrusting faster and harder. He felt his balls tighten and said, “I’m gonna cum, baby! I’m gonna fill you with my seed!”

Olivia came hard, with Bill’s dick pulsing inside her. She arched her body and screamed out, “God, yes, fill me with your cum!” She felt wave after wave of pleasure and was in heaven.

The contractions of her climax milked his cock and they both collapsed on the bed, out of breath. Steve wondered if Bill still meant to take Olivia’s ass. He didn’t have to wonder for long.

Bill sat up and then climbed over Olivia, so he was straddling her face. “Suck my cock, you little whore! Make it hard for me so I can enjoy the ass I need to fuck!”

Olivia opened her mouth obediently, letting him fill it with his prick. She cleaned it of her own juices and felt it grow harder again. He pushed at the back of her throat, trying to get in deep, but it was too thick, and she gagged a little. He eased back and then tried again and again until, finally, the tip of his cock was in her throat, blocking her air. Steve wasn’t worried. He knew Olivia enjoyed that style of breath play. He watched her hips rocking and knew she was more than a little aroused.

When Bill realized that Olivia was turned on by him pushing into her throat, he continued to do so, each time waiting a little longer before letting her get air. He gave one final thrust into her throat and said, “Get ready, because your ass is mine now.”

Steve could no longer ignore his own cock’s need to come out and play. He unzipped his jeans and pulled his rock-hard dick out. He willed himself to wait until he looked up and saw Bill lubing up Olivia’s asshole. He doubted very much that she would be able to take that thick of a cock up her rear end, but he wanted to watch the effort.

Bill told Olivia to stay on her back, “I want to see the look on your face as I take your tight ass. I want to be able to gauge how slow I need to proceed. Just know, I intend to get my whole cock inside your ass and then fuck it hard. But not until I can see the pleasure on your face. Fucking isn’t fun unless it's fun for both of us, baby.”

“God yes, baby, I want you to take my ass hard,” Olivia said, completely revved. Steve knew that she wasn’t just putting on a show for Bill. He knew she enjoyed anal and wasn’t surprised that she encouraged him to take her hard. He hoped she wouldn’t be disappointed when it didn’t fit.

But, to Steve’s amazement, Bill managed to get Olivia’s little puckered hole to open for him as he slid just the tip in gently. Both men looked at her face to see her reaction. Both were surprised when she took a deep breath, let it out slowly, and said, “More, please, I need it, all of it, in my ass.”

Bill pushed in as if he were moving in slow motion, easing his thickness into the tightest hole he’d ever fucked. He’d never been able to get a woman to even let him try accommodating him like this, let alone succeed. But here he was, buried to the hilt in her tight ass. Fuck, it was like nothing else he ever experienced. Her pussy had been incredible, but this was beyond words.

“God, your ass is so tight! Are you sure I’m not hurting you?” Bill asked, wanting to be sure that she was really okay.

Olivia smiled, “It hurt at first, but now it feels so amazing to have my ass filled like this!”

Bill grinned and shot a glance over to Steve, “Dude, I hope you realize that your wife is the best Hot Wife here. I’ve been with all of them, and not one of them has been able to please me like this.”

With that, Bill started to move in and out of Olivia’s ass, gradually picking up the pace until he was driving into her like a jack hammer. He felt lust consuming him as his balls slammed against her with every thrust.

“I’m gonna cum in your tight ass, you little slut. No one’s ever made my cock feel this good,” Bill said, panting wildly.

Steve found himself stroking at the same pace and was close to his own orgasm when Bill shouted, “I wanna see you cum on her tits while I cum in her ass!”

Steve stood up and jacked off over Olivia and shot rope after rope of white, sticky cum all over her beautiful breasts. Liv cried out, “Fuck, yes!” and came hard while Bill exploded in her ass.

Steve stepped into the bathroom to clean himself up. He couldn’t help but smile when he overheard Bill, “Damn, Olivia, you’re so sexy and fun! I’ve never had anal sex before. Women take one look at my dick and say, ‘No fucking way!’ I am so grateful for such an amazing experience!”

After Bill left, Olivia took a shower and got herself ready for the next appointment. True to his word, all Doug wanted to do was watch Liv use her fingers to play with her pussy while he jerked his cock so hard, she thought he might pull it off. When he said he was ready to cum, she expected her tits to be covered, as they had been when Steve had exploded on them earlier. But for all Doug’s efforts, she was rewarded with a mere dribble of semen on her stomach. Nevertheless, Doug left happy, and Liv’s clean-up was quick and easy.

Sam, the man of few words, arrived ten minutes late for his appointment and seemed extremely uncomfortable. Liv did manage to get him to put his hands on the tits he said looked nice. But he couldn’t get hard for her and left, thanking her for letting him pinch her nipples, and promising he would try again some time.

Steve came out from his viewing area and said, “Wow, after such an exciting session with Bill, those last two were kind of a bummer. I guess it never occurred to me that you might run into some duds.”

Olivia laughed. “Speak for yourself. Doug came, even if it was only a few drops, and Sam got brave enough to make my nipples a little tender. Besides, we have Ray’s visit to look forward to.”

While Liv freshened up, she checked her Hot Wife messages and found there were two:

Hey, Olivia! One of the other Hot Wives called in sick. I’ve been able to reschedule all but one of her appointments. Would you be willing to cover her 8:00? His name is Don and he’s into spanking. I realize you’re done by 6:00, so this would leave a bit of a break in between, but it would be nice to not cancel if we can help it. Let me know ASAP please! ~Marilyn

Hey Liv, it’s Ray. If it’s not too much trouble, put on some panties for me. C u soon!

“Hey, Steve, Marilyn is asking me to cover a client at 8:00. Is that okay with you?” Olivia asked Steve while she put on a sexy pair of panties for Ray.

“It’s more than okay, baby. I know Doug and Sam left happy, but you know I love to see your holes get penetrated,” Steve answered.

“Well, you’ll have the added treat of seeing me get spanked. Marilyn said he was into that,” Olivia said as she pulled her long red hair into a ponytail.

Steve grinned. “I like when you wear your hair like that.”

“Of course, you do,” Liv joked. “It’s easier to grab onto my hair that way!”

“You know me so well,” Steve said as he gave her a playful swat on the butt. “And I can’t wait to see this sweet round ass of yours get spanked later. I gotta say, that’s got me revved a little.”

“You’re so cute,” she said, while she sent a message to Marilyn, agreeing to take the 8:00 spanker. “I’m glad this is working out. I mean, yes, it didn’t occur to me that this would be hit or miss. But I’ve had some great hits so far, and the misses weren’t horrible.”

“I actually thought Doug was going to pull his dick right off of his body, he was jacking it so hard,” Steve said.

Olivia giggled, “I just felt so bad for him. All that work and literally only two little spurts of cum dripped on me. But the noise he made when he came sounded like it was a powerful orgasm for him. I’m just glad I could help him get off. I know that, for you, this is about enhancing our sex life. But I’ve started to realize that this is a real service to men. I mean, take Sam. He could barely look at me when he walked into the room. But he got to squeeze some real titties today!”

“Honey, you were probably the highlight of his week! I am so lucky to have you as my wife. And fortunate that I get to squeeze those gorgeous globes whenever I want to!” Steve gloated.

“I’m lucky to have you as my husband. I know that you enjoy seeing me with other men, but I don’t think you meant five in one day. So, thanks for this!” she said, kissing him softly on the lips.

“I really don’t mind five in one day, my sexy little slut! In fact, I think it might be fun some time to watch you with five all at once. But we can talk about that another time. Are you ready for Ray? He’s going to be here soon,” Steve reminded her.

“Oh, I’m ready,” Olivia said seductively. “I just hope the two of you are ready too!”

Steve grinned wickedly, “Go lay on the bed and look vulnerable and helpless. I’ll answer the door when he gets here so he can tell me how he envisions this role-play happening. And Liv? Try to look a little less devious and a little more defenseless.”

She laid on the bed in nothing but her lacy red panties and waited for Ray.

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Written by techgoddess
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