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Hot Wife Hotel - Olivia Takes Vinnie's Virginity (Part Twenty-Three)

"Olivia has a lot on her plate, but manages to find time to help out a guy looking to lose his virginity."

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Author's Notes

"For those of you who haven't read any of the other parts of this series, you can still enjoy this part! But most people who start with the most current episode have a tendency to go back and read the other adventures of Olivia, a wild, sexy redhead who works at Hot Wife Hotel."

Olivia put on a flowery dress that didn’t show too much cleavage and headed to church. She caught Pastor Jesse's eye when she slipped into the pew as the service was about to start. Though the look on his face was sheer terror, he meandered over to say hello in a smooth, calm voice.

“Well, hello, Olivia. It’s nice to see you again.”

Liv smiled. She knew that an innocent bystander would think he meant here in church. But she knew by the bulge in his pants that he was thinking about how he’d whipped her ass till it turned crimson just over a week ago.

“Likewise,” she all but purred.

“Are you thinking of joining our congregation?”

“No, I’m meeting someone here.”

Jesse went pale. He leaned down and quietly said, “Olivia, you can’t conduct your business here. What if someone finds out what you and I have done?”

“Relax, Pastor Jesse. I won’t do anything to embarrass you. But I want you to meet my friend when the service ends.”

Jesse nodded, but his expression was wary.

As the service began, a sexy little blonde scooted into the pew next to Olivia. Jesse was grateful that he was behind the pulpit so his rock-hard erection wasn’t in plain view. It took all of his energy to keep his train of thought going while he preached the good word.

Fortunately, talking about loving God and following in his ways was enough to help Jesse’s cock soften. So, by the end of the service, he was back in control of his man parts.

Still, he had promised Olivia he would meet her friend. He just hoped the sassy redhead wouldn’t say or do anything to cause a scene.

He walked up to her smoothly and said, “Well, now, Olivia, who might your friend be?”

Liv smiled. “Why, Pastor Jesse, this is my sweet young friend, Cindy. She’s looking for a new church. One where she can find the discipline she craves.”

Cindy smiled sweetly at Pastor Jesse. “Hello, Pastor. I am hoping that some one-on-one sessions might be just the thing I need to get on the right path.”

Jesse willed himself to look behind these two beauties and focus on old Mrs. Blonsky, the dear octogenarian who still came to service every Sunday. Her wrinkles had wrinkles, and it helped keep his penis flaccid while he finished his conversation.

Olivia handed Jesse a handwritten note and suggested he read it.

Dear Pastor Jesse,

Cindy is a nineteen-year-old girl who needs a good spanking now and then. The priest at her Catholic church sent her away when she asked him to spank her. I told her there wasn’t anything wrong with her; she just needed a new church.

Since you need to swat a sexy bottom like most men need to breathe, and she needs to feel the sting of whatever suits your fancy, I figured the two of you would make a good match.

She doesn’t work at Hot Wife Hotel, so you don’t have to worry about being seen coming and going from that heathenish den of iniquity. You just have to work out a schedule for some steamy bible thumping.

Say thank you if you want what Miss Cindy is offering.

Pastor Jesse looked up at Olivia and smiled. “Thank you. You’re too kind. I’m happy to help your young friend find what she is seeking.”

And with that, Olivia gave Cindy a quick hug and whispered in her ear, “He will spank the living daylights out of your ass and make you cum like a faucet. Enjoy!”

Cindy thanked Liv and turned to take a walk with her new Pastor.

Olivia mentally checked helping Cindy off her to-do list as she headed to her car.

The next day, Liv met with Marilyn to review the lengthy waitlist of women who had applied to work at Hot Wife Hotel.

“Why didn’t Darko mention this list to me? It would have saved me a lot of time. He might be the original owner, but now that I'm a partner, it would be nice for him to communicate better with me."

Marilyn shrugged. “I don’t know, but I’m sure you’ll find some great candidates among this group.”

Olivia glanced at the applications and chose six to invite in for interviews.

“Let’s set these ladies up to meet with us first. Then we can see what Darko thinks.”

Marilyn frowned. “This last one lists herself as a vampire. Do we really want to go there?”

“If you read her bio on the back side, it says she’s into vampire role-play. As long as she understands we don’t allow blood play, she might fill a need for some of our kinkier customers.”

“Good point,” Marilyn shrugged. “She’s pretty sexy looking, anyway.”

“If we can find some hot wives who are into more fetish-type sex, then the gals who prefer your standard fuck and suck won’t have to be pushed so far out of their comfort zones. As it is, we are down to only one hot wife who likes piss play and has clients on waiting lists.”

“We add some variety with new hires, which will help widen our customer base.”

“Exactly!”

Liv left Marilyn with the task of contacting the potential candidates and sent a text to Steve.

I’m finishing some paperwork here, and then I’ll be home.

Steve responded quickly.

How would you feel about contacting Master Julian for a session soon?

Liv felt a rush of desire. Master Julian had been the ridiculously wealthy man who won her at the recent auction. He’d expressed interest in seeing – and using – her again.

I’d be interested in a session, but I’d like you to set it up. That way, it will feel like my owner is sharing me with another Master.

Steve’s cock twitched at the thought of watching Master Julian spanking and fucking his hot, redheaded wife.

I’ll make it happen. Soon, you’ll spread your legs, offer your body to him, and beg him to do anything he wants with you.

She felt her panties dampen. Oh, yes. She’d beg.

When Olivia was getting ready to leave, Marilyn poked her head into the office. “Hey, there’s a guy who had a session booked with Holly, and she went home with the flu. Any chance you could stick around and take him on?”

“What’s his deal?”

“He’s a twenty-six-year-old man who wants to lose his virginity.”

“Oh boy, a fumbler. Well, hell. Sure, why not?”

“Thanks, Liv! I appreciate not having to reschedule him. He sounded so sweet on the phone.”

Olivia sent a quick text to her hubby.

If you want to witness me taking some guy’s cherry, head to Hot Wife Hotel. Holly’s sick, and Marilyn asked me to fill in.

I’ll be right there.

Olivia headed to her penthouse room and freshened up. Wearing only her black robe, she pondered how to approach this session. Perhaps she should play Mistress Liv? But without knowing more about the client, she decided to play it by ear.

Steve arrived just in time to take his spot in the observation room. A voyeuristic wank was just what he needed after talking to Master Julian on the phone. Julian had gone into detail about what he wanted to do with Olivia, and Steve’s cock had been aching ever since. Watching her fuck a virgin sounded like just the thing to help relieve his full, heavy balls.

When the client knocked on the door, Liv answered with her robe open, exposing her naked body.

“Hello, I’m Olivia. Won’t you come in?”

“Um, sure, yes. I’m, um, I’m Vinnie. I thought I was supposed to be with Holly today,” the man said nervously.

“I’m sorry, sweetie, Holly went home sick today. But I promise to take good care of you,” Liv purred.

The man nodded. His hands were damp, and his heart was racing. It was finally going to happen. His first time. He was about to finally lose his virginity to this gorgeous redhead.

“I want you to know that I, um, well, I masturbated this morning so that I wouldn’t shoot my load the minute you touched me down there.”

“That was a smart idea,” Liv said, trying to make Vinnie feel less awkward.

“But if you cum quickly, no worries, okay? I’ll be sure to get you hard again for a second round.”

“Oh, well, whatever you think is best.”

Olivia could tell that Vinnie was too nervous to just jump in bed. “Would you like a beer or a glass of wine?” she asked, trying to help him settle.

“Wine would be great.”

“White or red?”

“Whatever you’re having.”

Olivia poured two glasses of Pinot Grigio and motioned for Vinnie to join her on the couch.

“So, you’re a handsome guy. Why are you here with me instead of out with a pretty girlfriend?”

“I’m not good at talking to girls. I always get so nervous. It’s just easier not to even try. But my therapist said part of my issue is that I’m afraid my first time will be a train wreck, and that is holding me back.”

Liv felt compassion for this self-conscious man. Thoughts of pulling out her Dominatrix persona flew out the window as she realized he needed a girlfriend experience.

“Well, then, consider this a date,” she said as she closed her robe just enough to allow her cleavage to draw Vinnie’s eye. “Are you hungry at all?”

“Only for you,” he said sheepishly.

Olivia smiled warmly at him. “That’s excellent because I’m hungry for you too.”

Vinnie blushed, but he started to relax a little. He sipped his wine and smiled when the gorgeous redhead patted the spot next to her on the couch, inviting him to join her.

“You’re very handsome,” Liv murmured as she nibbled on his earlobe. It wasn’t just words to make him feel better; he was attractive enough. “I’ve been waiting a long time for this, but I don’t want to rush you. We can take it slow, baby.”

He sighed and relaxed a bit more. “You’re so beautiful. You have a pretty smile and the bluest eyes I’ve ever seen.”

Feeling brave, he brushed his lips against hers and felt the heat of desire wash over him. In a move he considered bold, he took her in his arms and deepened the kiss. As their tongues danced, he felt his manhood grow. At least he could check that worry off his list. Earlier today, he panicked about his ability to get and stay hard for a woman he’d never met. But she was so sensual that he was more than aroused.

Liv moved her hands down Vinnie’s body. “May I take off your shirt? I want to see more of you.”

“Yes, please.”

Liv carefully unbuttoned the blue oxford shirt and moved it off his shoulders. “Very nice. Of course, it’s only fair to show you my chest too.”

Vinnie shot her a goofy grin as he untied her robe and pushed it open, exposing her large, firm breasts. “These are the most beautiful tits I’ve ever seen. I watch a lot of porn, but nothing I’ve seen holds a candle to yours.”

“Thank you. Next time with a girl, don’t share the part about watching porn,” she laughed softly.

“Oh! Right!”

Olivia ran her hands down Vinnie’s chest and looked at him seductively. “Would you like to step out of those jeans?”

“Yes.”

He stripped down to his boxers as Olivia flung her robe across a nearby chair. She stood naked with her red curls spilling over her shoulders and reached out to him. “Come to bed with me. It will be more memorable for your first time.”

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It would also give Steve a better view of his wife being fucked by another man. And that was the whole reason behind working here at Hot Wife Hotel.

Olivia knew that all the effort she was putting into making Vinnie’s first time a sweet, romantic experience would pay off later when her husband reclaimed her body.

“I’m going to start with some oral play, okay baby?”

“Oral play?” he asked, confused.

“I’m going to suck your cock as foreplay.”

“Ohhh! Yes, that sounds wonderful.”

“Ever have a blow job before?”

“No, I tried once, but I came before my date could even get me out of my pants. It was so embarrassing.”

Not wanting to kill the mood, she said, “Well, that doesn’t seem to be a problem this time, does it? You’re naked and about to enjoy an experienced mouth.”

Liv leaned in and kissed the tip of his rigid shaft, eliciting moans of pleasure from him. She took it slow, licking him from base to tip before guiding him into her mouth, an inch at a time. He had a decently sized cock. Not exceptionally long, but nice and thick.

She continued to work him in slowly until her nose was against his belly. She allowed drool to run down his sac and then licked it up with her tongue, all the while still sucking on his cock.

She cupped his balls and moved her mouth up and down on his pole while his hips rocked.

“Oh, God, I’m gonna cum!” he shouted.

Knowing she could get him hard again, she picked up the pace as he thrust himself into her throat. His balls tightened and let go, shooting his load in her mouth.

He seemed annoyed until she opened her mouth and let his seed spill out erotically onto her breasts.

“Holy crap, that’s hot!”

Olivia used a finger to scoop up the sticky white substance and licked it clean. “Not all girls like to swallow,” she said as she moved to lie beside him. “So, letting me know you were about to cum was a good thing. It gave me time to decide if I wanted to let you cum in my mouth or not.”

Vinnie nodded. “That was amazing, but technically I’m still a virgin.”

Olivia pointed to the clock on the wall. “Good thing you still have half of the session left, then. Have you ever gone down on a woman?”

“No, but how is that going to help?”

“Eating my pussy always makes my lovers hard.”

“I really don’t know what I’m doing, though. I don’t want to disappoint you.”

“The only way you could disappoint me, Vinnie, is by not trying.”

He smiled weakly and moved between her legs. He’d watched porn vids where guys licked pussy, and figured he’d try to emulate what he’d seen. Before he did, he inhaled her scent and felt a twinge in his dick. Maybe she was right.

His tongue glided along the pink folds of her pussy. She tasted sweet, which surprised him. He looked up at her and saw her eyes flutter, so he must be doing something right. He circled her clit before sucking on it a little.

“Mmm,” Liv moaned.

Encouraged by the sounds, he tried alternating nibbling with sucking and was rewarded with a flood of nectar in his mouth.

“I didn’t know that women came too!”

“Not all women squirt their juices as I do, but it’s always polite to swallow if they do.”

Might as well train him right!

“My dick is hard again. Can we fuck now before we run out of time?” he asked anxiously.

“No worries. I don’t have any other clients today. I’m not letting you leave here a virgin. If we run over, the extra time is my treat. Okay?”

He nodded. But I could tell he had reached the point of needing to stick his hard peg in my soft hole. Who could blame him? Most of his friends have been fucking for at least ten years. He’d waited long enough.

“What position would you like?”

Vinnie suddenly had that deer in the headlights look, so she said, “Do you want to be on top or bottom? Or, perhaps, fuck me from behind, like a dog?”

She could almost hear his dick get harder as his eyes bugged out a little.

“That last one,” he blurted out. “I want to fuck you like an animal.”

Wasting no time, Liv rolled onto her hands and knees and put her ass and pussy in the air.

Vinnie moved behind her and was about to enter when she said, “Get your cock wet with my juices. It will slide in easier then.”

Following her instructions, he stuck two fingers into her drenched pussy and rubbed her sweet nectar over his dick. Then he guided himself to her hole, grabbed her hips, and pushed his cock into her pussy.

“Oh, fucking, Christ! You’re so tight! Your pussy is gripping my dick!”

“Move it in and out of me, just like in the porn vids,” she suggested.

He moved slowly at first, but soon he pumped into Olivia like there was no tomorrow.

“Oh, fuck! Your cunt feels so fucking good on my cock!”

Olivia grinned as the shy virgin was no more. He’d gotten bold enough to talk dirty, although she made a mental note to tell him most women don’t like the word cunt.

She met his every thrust as he jackhammered into her pussy.

“I’m gonna cum. Can I cum inside you?”

“Cum, baby! Cum hard, deep inside my pussy.”

She reached between her legs and rubbed her clit so she could cum with him. And when he flooded her pussy with his seed, she enjoyed the throbbing sensations from her own orgasm.

Vinnie slid out and collapsed on the bed. “That was incredible!”

Olivia smiled and checked the clock. “You still have time left; what else would you like to experience?”

“Can I suck on your tits?” he asked. “And finger your pussy while I do that?”

“Of course,” she said. He might still need some lessons on how to talk to women, but he had the basics down pretty well for a man who’d never had sex before this afternoon.

He took a nipple into his mouth while two fingers slid inside her. The sucking motion was incredible, and Liv was about to compliment him when he started to bite.

“Not so hard,” Liv said. “Save hard biting for BDSM sessions. Nibble gently, like you did earlier with my clit.”

“Oh, okay, sorry.”

He did precisely as she directed, and soon, he had her bucking wildly on the bed.

“Add another finger!” she cried out.

With three fingers, he fucked her hard while he sucked and nibbled the other nipple.

“Oh, God! Yes!” she screamed as her body exploded in an intense orgasm.

As she was catching her breath, Vinnie grinned at her. “My dick is hard again. Can I put it in your ass?”

“Why not,” Olivia chuckled. So much for the shy virgin now. He was going for the hat trick, and she was happy to oblige him. “But we’re going to need lube for that.”

She grabbed a bottle of Analease from the drawer and handed it to him. “Spread copious amounts of lube in and around my anus.”

He followed her directions to the tee and then pressed the tip of his dick against her puckered star.

“My ass is very tight,” Liv explained. “You have to push harder to get in.”

“I’m afraid I’m going to hurt you.”

“You won’t hurt me, I promise.”

He sighed reluctantly but pushed harder until the head was inside her.

“You’ll need to move more slowly when you fuck a girl’s ass. Give her time to get used to your size before you start thrusting.”

“How will I know when she’s ready?”

“Most women will make a comment about it feeling good when they’ve adjusted to the feeling of pressure. That’s usually the sign that it’s okay to start moving.”

“Oh, my God, your ass is really tight!” Vinnie moaned. “It makes me want to fuck hard and fast.”

“Soon enough, but ease into that pace, okay? Yeah, just like that. Feels good.”

Vinnie decided that was his cue to pick up the pace. He grabbed hold of Olivia’s hips and began thrusting.

Steve watched with lust in the observation room as this man violated his wife’s ass. He would typically stroke himself at this point, but he didn’t want to miss a single moment of the show.

Vinnie pumped into Olivia’s ass until his balls tightened, and he screamed. “Fuck yeah, I’m cumming!”

Steve noticed Liv hadn’t cum during this last portion of the session, but he’d make sure she was pleased when he reclaimed her.

Back on the bed, Vinnie pulled out and grinned. “That was awesome!”

Olivia smiled. “There are a few things I want you to remember. First, not all women like anal, but if you suggest it, you must be suave in your approach.”

“I guess asking if I can put my dick in a girl’s ass doesn’t sound very sophisticated,” he admitted.

“Nope, not even a little bit. But that’s okay; you’re learning. Second, it’s nice to ensure your partner is stimulated while you are fucking her. Not all women can have an orgasm just by fucking. You can stimulate her by playing with her clit.”

“Got it. Anything else?”

“I’ve taken many dicks up my ass, but chances are any woman you date won’t be experienced that way. So, you’ll need to go much slower if it’s her first time.”

“Yeah, I knew I was probably going too fast and hard.”

“Which was great for me but won’t win you any points with a girl who is an anal virgin.”

“I can’t thank you enough,” Vinnie said as he reached for his boxers. “Not only for taking my virginity, but also for coaching me how to do things.”

“Was it everything you hoped it would be?” Olivia asked, slipping her robe back on and tying the sash.

Vinnie blushed. “Better, actually. I was expecting to fuck a pussy, but I got a mouth and an ass as well. I know that’s not what typically happens on a date, but I appreciate having experienced all three holes, so I won’t be so nervous when I finally get up the nerve to ask a girl out.”

Olivia decided to bolster his confidence a bit. “You have a nice, thick cock. Women prefer girth over length. I have great faith that you’ll be able to please any girl you date. Plus, you have decent oral skills.”

“Thank you for everything,” Vinnie said as he hugged Olivia goodbye.

“My pleasure, sweetie.”

When Vinnie was gone, Steve came into the room. “Strip for me, slut. Time for me to take back what’s mine.”

Olivia was delighted that Steve wanted to reclaim her immediately. “Yes, Sir.”

She let the robe fall to the floor and waited for the next instruction.

Steve could tell his sexy little wife was in the mood to be submissive. So, he unzipped his fly and said, “Pull out my cock and suck it, you dirty little slut.”

Within seconds, Liv was on her knees with his engorged prick in her mouth. He grabbed her head and fucked her face. “Yes, suck it like the good little cock sucking whore you are!”

With his dick lodged in her throat, he continued to pump wildly. “You gave your mouth to that virginal boy; now take your man’s seed like a good girl. Here it comes, baby. Swallow!”

The obscene noises as he pushed into her throat repeatedly set him off, and he shot his first load nice and deep. She nearly choked on the amount of cum, but she swallowed it all as he demanded.

They spent the next few hours with Steve reclaiming his hot wife’s pussy and ass. When he was done with her, she was exhausted. He drew a bath for her and helped her slide into the hot water to soak for a bit.

“Oh, by the way,” Steve said casually while he sipped his wine. “We have a session booked with Master Julian in the playroom this Saturday.”

Olivia felt giddy. She couldn’t wait for the weekend!

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Written by techgoddess
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