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"THe Roleplay Was More Than She Expected."

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Jen and her husband Bill had been married for five years. They had dated for three and had gotten married. They were both twenty eight years old. About a year ago they had started trying to have children but nothing yet. One of their married friends said that her and her husband had the same problem a few years ago and they tried roleplaying in the bedroom and she got pregnant the first time they did it.

Her friend said, “I don't know if it was because of the roleplaying that I got pregnant, but we got really hot and heavy the first time we did. We pretended we were having sex with a stranger and had no inhibitions.”

Jen talked to Bill about it and he told her, “Sure, it's worth a try.”

Three days later on a Saturday night they decided to try it. Bill was at a buddies house helping him do something and they were going to try their roleplay that night. At about seven pm, Jen called Bill on his cellphone just as she was about to go out the door to go to the bar they had decided on. When he answered his phone, she asked him, “Hey, sweety. So, are we still on for tonight?”

Bill told her, “Sure, babe. I'll meet you at the bar in about a half hour, ok.”

Jen said, “Ok, I can hardly wait.”

After she hung up she checked herself again in the full length mirror in the hallway, she was dressed to the nines. She had on a red top, Bill's favorite color, with so many buttons undone you could almost see her nipples because she wasn't wearing a bra. A black mini skirt with black fishnet stockings, and no panties. She looked like someone who should be standing on a street corner trying to pick up guys instead of heading out on a roleplay date to meet a stranger, who her husband was pretending to be. She grabbed her purse and hurried out the door.

It was a ten minute drive to the bar. When she went inside she sat at the bar. She didn't order a drink right away. The first five minutes she was there three men came up to her and offered to buy her a drink. She politely told them no, and they walked away. 

Another five minutes went by, and she heard in a familiar voice behind her, “Hey pretty lady, can I buy you a drink?”

Jen recognized the voice as her husband Bill's, but when she turned around, she couldn't believe what she saw. He looked somewhat like Bill, but he looked somewhat different. He had on glasses, which she knew he didn't need, and his hair was jet-black instead of blonde. She just figured he was dressed this way to get into the stranger role.

She gave him a big smile and said, “Please, have a seat.”

The bartender came up and asked what he would like to drink. He told him, “Two white wines.”

Jen asked, “You always buy women that you just meet, wine?”

He smiled and said, “No, just the beautiful ones.”

Jen could tell she was blushing. It had been a long time since Bill had called her beautiful. So long that she couldn't remember the last time. He touched her face with the back of his hand and said, “Hey, why the red face? I bet you have lots of guys telling you how beautiful you look everyday.”

She didn't answer. By this time the bartender had come over with their glasses of wine and sat them down in front of them. Bill picked them both up and handed one to Jen. He clinked the glasses together and said, “Here's to the most beautiful girl in the world, and the pleasures she may experience tonight.”

Jen said, “My name's Jennifer, but my friends call me Jen.”

Bill said, “My name's Jack. But you can call me anything you want.

Jen thought, Bill is really getting into this roleplay. I should have chosen a different name. But it's too late now.

Jen was only planning on taking a sip of the wine. She wasn't a big drinker, and the last and only time she'd had wine was at her wedding. Instead of a little sip, in her excitement she gulped down half the glass. She started to choke and sat the glass back on the bar. Bill gently patted her on the back and said, “Go down the wrong pipe, did it?”

Coughing, she said, “I haven't had wine since our…um, I mean my wedding.”

Jen was trying to get into the roleplay and she almost messed up by saying our wedding instead of my wedding. They made small talk until their glass of wine was gone and Bill said, “Why don't we go somewhere more private and intimate, so we can get to know each other better? I have a motel room just around the corner. We could go there.”

Jen was ready to leave and said, ”Why don't we go back to my place. We'll be much more comfortable there.”

Bill said, “Are you sure? I mean, what if your husband comes home unexpectedly and catches us?”

Jen laughed and said, “Oh, I'm sure my husband won't come home unexpectedly and catch us.”

They both walked outside and Jen asked, “Whose car do you want to take, yours or mine?

Bill said, "How about I just follow you?”

He walked her to her car and she saw him get into the car beside hers when she went to drive off. It wasn't his car, she would have to make sure to ask him which friend let him drive their car.

Driving home, Jen could tell she was wet. She wanted to reach down and finger herself to orgasm. But she was afraid she might have an accident. Plus she wanted Bill deep inside her before she came.

They both parked in front of the house and she waited for him to come over to her car and then they went inside. The front door opened into the kitchen and once they got inside and Bill shut the door behind him, before she even had a chance to react Bill was bending her over the kitchen table. Laying face down on the kitchen table, she wasn’t all that tall and her feet didn’t reach the floor, so there she was, her feet dangling in the air in 6 inch heels. Bill slid her skirt up around her waist and noticed she didn’t have any panties on.

When he saw she had no panties on he gave her bare ass a hard slap with his hand. Jen let out a little yelp and then she heard him undo his belt and unzip his pants. He then slapped her ass with is cock and asked her, “What hole do you want me to put this in first, baby?”

She replied back, “Put it in my cunt.”

He wasn’t gentle at all. She was so wet he just plunged his cock into her pussy balls deep in one hard thrust. This was unlike Bill. He was never this rough before. Not that she didn’t like it. It was just different. She wasn't sure but it felt like Bill's cock was bigger than the last time they fucked. She just figured it was because of the roleplay, he was just more aroused. She sure was. Bill was very aggressive; he started roughly pounding her pussy as hard and as fast as he could non-stop, he only lasted a few seconds before he filled her cunt. Jen decided that she loved this role play and wished that they had decided to try it before now.

She could hear Bill kick his shoes off and take his pants completely off. Then he grabbed a handful of hair on the back of her head and pulled her off the table and back into him. He ripped her top open, exposing her tits. He reached up with both hands and squeezed them hard, pinching her nipples. He whispered in her ear, “Do you have a tight asshole, baby?”

Jen thought, Oh, my God! He wants to fuck my ass! Bill and Jen had never had anal sex before. They had talked about early on in their relationship and she said she wasn't interested. But again, she wanted to get into the roleplay. And if it meant doing something she didn't want to do…

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She whispered back, “I'm still an anal virgin.”

He kissed her earlobe and said, “Well, we can fix that. I just love fucking a tight asshole.”

Jen thought, Who the hell's ass has he been fucking? But then she just figured, he was getting into the roleplay. Bill then told her, “Let's go to your room so I can be the first guy to fuck that sweet ass of yours.”

She never dreamed that Bill would act like this even in roleplay. He was always so, wham bam, thank you ma'am. When they got to the bedroom, Bill said, “Ok, up on the bed.”

Instead of getting up on the bed like Bill told her, Jen asked, “Do you want me to undress?”

Bill said, “No, I like fucking a woman doggystyle in heels and stockings. Now just get up on the bed on all fours, baby.”

Jen did as Bill told her, although she wasn't really sure she was going to enjoy it. But she decided, whatever Bill wants, Bill is going to get. So she was now up on the bed on all fours, waiting for her husband to take her anal virginity. Bill quickly undressed so he was completely naked. He then got in the bed behind her and spit in her asshole and slid a finger in.

Jen gasped but she didn't tell him to stop.  As he slowly fucked her asshole with a single finger, Bill told her, “Yeah, baby! You might be the tightest ass I have ever fucked!”

Jen still couldn't nderstand why he would say stuff like that. As far as she knew, she was the only woman he had ever been with, and she was sure he would never cheat on her. She figured he was saying it for the roleplay. After all, they were supposed to be strangers. She decided to spice things up a bit and asked, “So, are you going fuck my tight ass, fast and deep, baby?”

She looked back at him and smiled when she asked. He smiled back and said, “You better believe it, baby.”

He then gave Jen's ass a hard slap with his hand and said, “Stay right there. Don't move.”

He then walked over to her closet and opened it and found the belt to her bathrobe, got on the bed behind her and roughly pulled her hands behind her and tied them with the belt. They had never done bondage before, but hey, she wasn't going to complain. 

With her hands tied behind her, Jen's face and upper body was now laying flat on the bed, her ass sticking up in the air. She begged him, “Please, use lube when you fuck my ass!”

He gave each of her ass cheeks a hard slap with his hand and said, “Ohhh, no. Every woman's first time getting fucked in the ass should be raw and bareback. But hey, I promise, if you are a good girl I'll be gentle.”

Jen couldn't believe what had come over Bill. They had talked about anal once before, but she told him that she wasn't interested. He had said he was ok with it, and he wouldn't bring it up again. She felt him place a kiss on each of her ass cheeks. She loved the feel of his lips on her ass. She then felt him move up behind her and felt him slap her ass with his cock.

Bill said he'd be gentle. But after the way he was acting tonight, she didn't know what to expect. He again slid his finger in her asshole and slowly fucked her. His finger didn't feel too bad, but his cock was a lot bigger than his finger. He pushed his finger deep, and she moaned. Everytime he pushed his finger in deep she would moan. After about a half dozen times, he said, “Ok, I think you're ready. Are you ready?”

When Jen just moaned, he said, “Yeah, you're ready.”

She felt the head of his cock at her virgin hole. Bill was gentle. He pushed the head of his cock into her, then he reached up and put his hands on her shoulders and gently and slowly pushed himself in until he was balls deep. The pain was more intense than anything Jen had ever felt. It took everything she had not to cry out and beg him to stop.

He must have been able to tell she was in a lot of pain, because once he was in he stopped and planted kisses on her back and whispered, “Ok, baby. The worst is over.”

Bill started to back out but Jen said, “W-wait…p-please…n-n-not…y-yet…”

Bill told her, “Ok, ok. I'll give you a minute.”

He waited and then said, “Man, I'm glad your hubby didn't fuck your ass. Or it wouldn't be tight for me. And I looove fucking a tight ass.”

Without asking her if she was ready for him to start fucking her, he slowly pulled his cock from her ass. Leaving just the head in before shoving it back in her. It didn't hurt as bad the second time, but it still hurt. This time he didn't wait before pulling out. Almost as soon as she felt his balls on her ass he pulled out again, faster than the first time. He didn't wait before shoving it back in. As soon as just the head of his cock was in her ass he shoved it back in, harder and faster.

He did this over and over again. After about the sixth time there was hardly any pain. It actually started feeling good for Jen and she started moaning and pushing back on his cock when he pulled out. When she started doing that he stopped pushing into her and told her, “Yeah, baby! Use that ass of yours. Fuck my cock! Make me come, baby!”

She did like he told her and started fucking his cock with her ass. They were both moaning loud now. Everytime Jen would pull her ass off his cock he would give her ass a hard slap with his hand and tell her, “Faster, deeper, baby!”

She did as he told her and soon he was filling her ass with his cum. When he came he reached up and put his hands on her shoulders and shoved his cock as hard and as deep in her ass as he could, holding his cock balls deep until he emptied them.

Jen couldn't believe how intense her anal orgasm was. After both their orgasms had subsided Bill helped her roll over on her back and moved up by her head, put his cock in her face and told her, “Suck it and lick it clean.”

Jen smiled and started sucking his cock and licking it clean. She licked the length of his cock to get all the cum off it and then sucked on his balls one at a time cleaning them. It would have been a lot easier if her hands weren't tied behind her, but she wasn't going to complain.

Once she was done sucking and cleaning his cock he untied her hands and layed down behind her and slid his cock back into her cum filled pussy. As he kissed her back and played with her tits Jen told him, “We will have to do this more often.”

Bill didn't answer her, but she didn't care. He slowly fucked her again until they both came, then they fell asleep. Jen didn't hear him leave but he did leave a note.

It said, Thanks for the good time sweety. But I figure I better get going before your hubby comes home. He signed it, Jack.

Jen looked at her phone to check the time and noticed she had a missed call. It was from Bill. It said the time he called and it was the same time that she was being fucked in the ass.

She checked her voicemail and there was a message from Bill at the time she got the missed call. He said he was sorry but he couldn't make their date, something came up and maybe they could do it next week.

Jen looked at the note again. She hadn't realized it the first time she read it, but it wasn't Bill's handwriting. She gasped and dropped the note.

THE END.

Published 
Written by LIL1LOOKIN
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