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  • Painfully Shy Ch. 03

Painfully Shy Ch. 03

The idea of being sent up to fuck a man with a large cock excited Emily and Jerry. Emily was going to let Jerry do the leg work and Emily had exclusive say at any time to stop everything. Jerry would have a key to the room and might appear at any time. Both had to feel good about things or cancel out.

With Emily's permission, Jerry put a nude picture of her, face covered, in an ad. It read as follows:

My wife is in search of a gentleman with a large cock to fuck her as long as they both agree. He must be clean, well read, somewhere between 35 and 50 yrs. Please send pics of face and cock. She will give me potential partners and I will vet them.

Emily got very wet when she saw the ad had been published and demanded that Jerry fuck her immediately. He absolutely loved her transformation. She was still quite shy, but as she learned, it contributed to the ecstasy as she got into the moment. There was going to be a certain amount of embarrassment for her. She understood that going in. Jerry was going to find someone that was cognizant of that and would be sensitive to any and all concerns she might express.

The picture of Emily in the ad helped to generate 50 emails a day. They both loved looking at them before Emily would give her selections to her husband. Over the next few weeks they started whittling down the earlier selections, and by the time they felt they were ready, there were 3 different guys that Jerry had to set up interviews with.

Each was told that there were three people in the mix and that even if they weren't selected now, it didn't mean that they might not be called in the near future.

The first guy, Rick, was well groomed and over 6 feet tall. He had gray hair with an engaging smile and manner to him. He seemed perfect for Emily, but he was going to meet them all. As it turned out, Rick's interview won his overwhelming endorsement and Emily agreed.

Jerry called him right away and set up a second meet to square away the dos and don'ts. Jerry told him he'd pay for the room and have a pass key to get himself in and that he might come in at any time. He also told him that he probably wouldn't.

"So tell me more about her."

"As I told you before, she's very shy, but once she gets comfortable she'll fuck you into next week."

"Does she like anal or swallowing?"

The conversation was turning Jerry on as he sat there discussing his wife's sexual preferences. Rick seemed to be hanging on every word which inspired Jerry to lay bare all of Emily's past, how she liked her nipples played with, how she loved the full feeling of a big cock, the ease at which she could be molded, talked into almost anything.

"That's why I look out for her. What's happening with us was not even considered possible a few weeks ago. This is a first step for us, so if all goes well, chances are we'll see you again. She's interested in two men at once too, I think. I'm not going to say anything about the set up except to say it's a big surprise. You'll have to seduce her to keep her from getting cold feet. She knows to call me if she decides to call it off."

"I thank you again, Jerry, for the honor of sharing Emily with me and I'll do my best to make the night memorable for both of you."

The men shook hands and had each others cell number in case a typhoon hit either house. It was set to take place 2 weeks from that night.

Since the whole affair began Jerry and Emily fucked every night at least once, and often, more. They talked dirty to each other about the upcoming event.

"What if he wants to fuck your wife up the ass? What if he wants to lean me against the window and fuck me from behind? Should I be another man's slut? Should I let him cum in my mouth or on my face? Do you want to see cum on my face, baby?"

She egged him on getting great pleasure from being able to turn him on so completely. The more she talked, the faster he fucked her until he stiffened up and collapsed from exhaustion. His desire heated hers directly, and his constant praise made her feel more confident.

As the big night approached they quit fucking each other. He was going to want her several times immediately following her tryst and he wanted her as horny as possible to help ensure her desire to have this happen. He was more than ready, but there was some trepidation on her behalf. She was scared as they entered the hotel bar that night, but she was on fire knowing that the man was sexy and had a very impressive looking cock. The fact that her husband wanted this to happen took away a great deal of her initial skepticism.

As they started consuming alcohol, they began talking more about what was to take place.

"What's going to happen to me up there?"

"Nothing that you don't want to happen. If at any time you feel uncomfortable leave the room and call me. I can tell you this; it's going to be a big surprise for you and I think you're going to love it."

Earlier in the day, Jerry had placed a small fish-eyed camera pointing mostly toward the bed. He was going to record the entire night, but he didn't have time to set up a way for him to watch in real time. He didn't tell Emily about it as he wanted her to feel free to be herself and he would get to see her later on film in an unabashed version.

Jerry received a call from Rick at eight o'clock, right on time.

"I'll meet you in the lobby," he told Rick.

Turning to Emily he said, "Wait right here, baby. I'm going up to let him into the room and then I'll be right back down."

"I'm so nervous and excited!" she said with a wild look in her eye, helped in part by the drinks they'd had over the last hour. "You're sure you want this?"

"Probably more than you do!" he chuckled. He kissed her and said, "I'll be back shortly."

She couldn't believe this was happening. Their lives had changed so dramatically since their threesome. She began to allow herself time to consider what this guy's big cock was going to feel like. It looked to be larger than Jordan's but she didn't fear that part. She had accommodated him without any pain. Her pussy was already wet in anticipation of the coming hours.

Jerry came back after 15 minutes to find Emily being talked to by three well-dressed black men and she looked to be blushing. He actually saw this as a good sign knowing that her juices were going to be running overtime. They were looking her over, fairly certain that she was wearing nothing beneath the skin-tight black dress, the same one she'd worn at the party. He hung back a bit watching these men lust over her. His cock was becoming very hard.

He watched for about five minutes before finally walking over to her.

"Hey, baby."

"Jerry, this is Matt, Kevin and, I'm sorry, I don't remember your name.

"No problem. Hello Jerry," he said extending his hand like the two before him. "I'm Darryl."

"Pleased to meet you all. I hate to be a kill joy, but my wife and I have plans so we'll have to be going."

"That is a shame," Matt said. "Your wife is a sweet gal and beyond beautiful. I hope you know you're a lucky man."

"I'm reminded of that every day," Jerry said with pride as they both then made their way toward the elevator, the three men's eyes watching Emily's every move.

"Wow, it didn't take long for the wolves to move in, did it?"

"I know," she said. "They were surrounding me before I even knew it. Do you think they wanted to fuck your wife?" She was slipping into her role for him and loved his lust filled eyes.

"I know for a fact they wanted to fuck that delicious pussy of yours, just like Rick's going to do." They kissed passionately until the elevator door opened. "Room 815, baby. Have a great time and I'll see you in a few hours ready to continue our night together."

"I love you, Jerry."

"I love you too, sweetheart."They shared a short peck on the lips as the door began to close.

Jerry decided to avoid any explanations to the three guys that Emily had been talking to. He left the hotel and walked across the street to a pub with a view of the hotel bar. He watched them drinking and high-fiving for the next hour until they finally headed for the elevators after one of them had received a call on his cell. He then walked back over to the bar and began his wait there for the next couple of hours for Emily's call.

Emily got off at the eighth floor and walked toward room 815. She stopped just short of it, reached into her hand bag and pulled out three bar napkins. Looking up and down the hall, she put the napkins between her legs to wipe off her inner thigh as her pussy began to run. Returning them to her bag, she approached the front of the door and knocked lightly.

He must have been just inside the door as it opened almost immediately, startling her. "Hi, Emily. Please come in."

"Thank you," she said as the door closed behind her.

"My God, your pictures don't do you justice. You are breath-takingly beautiful."

"She began to blush and her pussy started its oozing down her leg again. " Thank you."

"Please, come in and sit with me. Your husband left us a bottle of bubbly. Could I get you a glass?"

"Yes, please, I'd like one."

They sat on the sofa together, but not too close at first. They turned toward each other and began to unwind. His eyes kept scanning her. It both excited and embarrassed her.

"Are you nervous?" he asked.

"Doesn't it show?"

He gave an easy laugh. "Yes, I guess it does. Well, if it's any consolation, so am I. But I also have to admit that your beauty is helping to chase that away. I feel both lucky and honored to be able to share time with you."

Rick was saying all the right things if you asked her pussy. It was running non-stop and caused her to move about involuntarily. She downed her drink quickly and he was quick to give her a refill.

"This is our first time doing this," she told him.

"That's what your husband said." He looked at her for a bit before asking. "Would you mind kissing me very much? It might go a long way toward calming us down."

She looked at him meekly and said, "Okay."

He moved closer to her before slowly moving his mouth onto hers and kissing her softly. She was starting to relax and began returning the kiss. He gently put his hand to the side of her neck and face as the kiss became more passionate. His tongue began to caress her lips before entering her mouth completely. They finally broke the kiss but their faces remained close.

Looking into her eyes he said, "You are a great kisser, Emily!"

"Mmm," she moaned, "so are you."

He began kissing her again as it lasted much longer. Emily was beginning to heat up. She felt his hand slowly drop from her neck until it was softly caressing and cupping her tits, their mouths never parting. She put one arm around his neck and was breathing heavily through her nose as the kiss and touching became more urgent. He broke the kiss and began talking to her.

"Your husband tells me you're very shy." He started kissing her again before she could answer.

On the next break she said, "Uh huh."

"It excites you, doesn't it?" as he again kissed her between questions.

"Yes," she hissed. His hands continued rubbing her tits and lightly pinching her nipples through her dress. She was on fire.

"Do you want to be my slut tonight, Emily?"

She answered by kissing him more aggressively. She was flushed and more turned on that at any time in her life. She desired to be everything to this man she'd met literally moments before.

Rick broke off the kiss and said, "Emily, I want you to stand up and remove your dress. It's the hardest thing for a normally shy person to do."

She was scared, but this feeling of wanting to be all things to him compelled her to a standing position. She reached behind her and began pulling down the zipper, never breaking eye contact until her dress fell in a puddle around her feet. The redness began in her chest and continued to her face as she stood there, completely naked, in front of this clothed stranger.

"Turn slowly for me, cunt."

Hearing this new word made her swoon as her pussy was running down both legs. She turned ever so slowly as he checked her out calmly from the couch. When she was again facing him he said, "Walk over to the cart and fix yourself another drink, and then come back to me." She did as she was told. She was highly embarrassed but her desire trumped all.

As she stood next to him he said, "Here, let me sweeten that drink for you," as a clear drop of liquid was released from the eye-dropper he held over her glass.

"Drink your drink, cunt."

A part of her didn't want to, but her arm raised the glass and she drank it.

"Now go over to the drapes and open them wide and remain standing in front of the window."

She knew she couldn't do that as her body continued to be defiant and obeyed him, opening the drapes and standing there, stark naked, looking out at the city lights and the people below.

Rick began setting up the camera and tripod he'd stashed behind the ice machine on the second floor. He'd gone to retrieve it as soon as Jerry left leaving the door blocked open. He beat Emily back easily.Once it was set up and running, he turned to Emily, still standing at the window as he had told her to do.

"Come lay on the bed, cunt. Now spread your legs for me."

Tears were running down the side of her face as her body begged to be touched.

"Your pussy is glistening in the light, cunt."

"I know," she said desperately, "I need to be fucked so badly! Please fuck me Rick!"

"Oh, I'm going to cunt, you can count on that!" He then picked up his cell phone. "Room 815."

========

Jerry asked the bartender about closing time and was told two a.m. He was beside himself. He was burning with jealousy and lust. It was a tug-of-war going on inside him as he again looked at his watch. Four and a half hours had gone by since he'd sent her up in the elevator and he'd figured it would be three hours at the most. He found he couldn't wait any longer as he headed to the elevator.

Arriving at the room, first he listened. Hearing nothing, he slid in the key card and quietly opened the door. He saw her dress on the floor and a dim light coming from the bedroom. He wasn't prepared for what met his eyes.

Emily was lying in the middle of the bed, fucking herself with a big fleshy dildo and covered from face to crotch in thick heavy cum. There was no sign of Rick. She opened her left eye and saw her husband.

"Oh God, Jerry, come fuck me! I need you! Please!

Jerry continued to take in the sight; Emily covered in bite marks, hickies and cum. "My God, Emily! What happened to you, baby?"

"I was a slut for them, just like we wanted. You need to fuck me now!"

Jerry was still rooted to the same spot on the floor. "Them?"

"Time to fuck me now. I'll tell you about it later, but you need to fuck me now!" as she kept on jamming the dildo into her cunt.

To his surprise, his cock had never been harder as he abandoned himself to the desires of his wife, undressed and crawled on top of her cum-soaked body. His confusion and shock kept him from cumming right away as he slipped his cock into her impossibly stretched and lubricated cunt. As he fucked her, his eyes saw the cum matting the hair to her face and the puddle of cum in her right eye, causing it to remain shut.

"Do you want to fuck your slut wife in the ass like they did?"

"Like who did, baby?"

"I'll tell you later. Right now you need to fuck me and bite my nipples. I can't seem to get enough. Hey, why don't you call Jordan and see if he wants some more of your wife's hot pussy. Maybe that kid, Brandon, might want some of this ass."

She was well over the edge and her foul rantings caused his cock to shoot one more load of cum into her overflowing cunt.

As the dumping of his cum into Emily subsided, he pulled out of her and watched as she replaced his cock with the one she'd been fucking herself with when he arrived. The room smelled heavily of cum, pussy and sweat. His mind couldn't comprehend what went on here, but Emily wasn't acting like this because of a transformation.

Quickly, he grabbed his camera gear and put it by the door. He then went to Emily who had started slowing down with the dildo, coming to a complete stop and staring up at the ceiling with glassy eyes.

He helped her up and into the shower where they spent the next 45 minutes. He cleaned her up as best he could before helping her put her dress back on. She was groggy and tired but started coming around enough to be able to help with their departure from the hotel.

She slept the entire way home as Jerry's mind raced. She was obviously fucked by more than Rick, and it seemed as if she enjoyed it immensely.

They got home and he woke her up and helped her into the house, up the stairs and into bed. She was out when her head hit the pillow. He had to know what happened to his wife.

He ran out to the car and retrieved his camera and hooked it to the TV in the basement then sat back to get the answers Emily wasn't able to give him.

There was over 5 hours of recording to view and questions to be answered about the lack of wisdom in jumping so fast into a world they were both naïve about. It was going to be a long, but no less, erotic night. The morning might be something altogether different.

He turned on the video.

To be continued...

*****

Thank you to everyone for your largely positive feedback. If you send me your ideas, I'll pick something and write a story to it sometime. Again, thank you so very much. Please keep them coming as they are the fuel to an author's imagination.

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