Jill

"Nevermind 'why' I'm asking. Just answer the question." Jill firmly demanded.

"I'm still a virgin, if that's what you want to know." Andi said unconvincingly.

Jill paused for a moment, not sure how bad it was going to sound, but decided to say it anyway.

"Anal virgin?" Jill exhaled.

Andi's face went white. How could she know? Did she find the enemas? Were there come stains in her panties? She hadn't always told her mother everything, but she didn't make a habit out of lying to her mother, either. This was big. She couldn't hide this one.

"No." Andi sighed. She explained that she had experimented with anal sex as a way to keep boys interested, when they would have gotten bored with her otherwise. She also admitted to giving blowjobs, which Jill accepted much more easily. "How did you know?"

"Mother's intuition, and then some," Jill answered. "Just be careful, Andi. There are a lot of guys out there that may seem nice. But deep down, they're not. I don't want you to get hurt, okay?" Jill paused for a moment. "Do you enjoy it -- anal sex?"

"Yeah, I mean, not at first." Andi answered. "At first, it hurt really bad. But when you do it a lot, you get used to it, and eventually it starts to feel good." Andi realized she said more than she wanted to. "I don't know if you and dad ever tried it, but you should."

Andi went back to check on Mark, leaving Jill standing motionless in the garage. Mark being in her house triggered more memories of that surreal night. This was literally hitting too close to home. Her daughter recommending that she experiment with anal sex momentarily left her in a catatonic state.

Andi found Mark in the bathroom, naked, washing his cock in the sink.

"Really? What if my mom walked by?" Andi half-joked.

"The more the merrier! Besides, your mom is pretty hot." Mark laughed, stroking his cock to erection. "Wanna finish this?" He didn't have to tell her twice.

Mark had no feelings for Andi, whatsoever. He held more than one part-time job this summer. When he wasn't working at a hardware store, he was working with tools of a different trade. He was one of about a dozen guys recruited by Officer Friendly to star in low-budget porn videos, and occasionally, tasked with finding female "talent" for a variety of positions.

He had met Andi in high school. He had been a year ahead of her, so their paths rarely crossed. He thought she was pretty, but Andi was right; he was not the marrying type. He was going to be a businessman, and he liked to fuck. That about summed up Mark.

He knew Andi wouldn't take a cock in her pussy willingly, but she loved to suck cock. There was work for girls like her. One of the porn "fluff" girls just quit so she could get married. If he worked on her long enough, Andi would be a perfect replacement. She'd get to suck a lot of cocks and get paid well for doing it, although she might be disappointed that she wouldn't get to taste the results of her efforts. Her job would be to blow men back to erection so they could fuck on camera quickly following an orgasm. Andi seemed to get aroused by the mouthfuls of come she had swallowed over the last few months. He'd have to convince her that's why they called it "work."

Jill was startled out of a trance by the clothes dryer buzzer. The wrinkle-free cycle continued, waiting for Jill to stop the machine and empty it's contents. When she pulled the door opened, the machine stopped. The house was quiet. She thought she would hear Andi talking with Mark, but there were no other sounds in the house.

She put the clean clothes in the basket to take to her bedroom for folding.

Jill almost dropped the basket of clothes as Andi and Mark quickly brushed past her.

"Going out for awhile, mom." Andi called out. "Don't wait up."

"Nice to meet you, Miss Jill," Mark added with a smirk. He didn't hide the fact that he was buttoning up his jeans as he walked out.

Jill could only imagine that her daughter was minutes away from getting fucked in the ass again. She began to remember more about that night when Mark and several others had their way with her. His cock was big, but he also knew how to use it. Jill's pussy suddenly became wet, soaking her baggy jogging shorts. She peeled down the shorts and reached under the bed, searching through the recently acquired collection of dildos.

"That looks about right," Jill said as she removed one of the larger toys from its box.

She pulled off her half-shirt, carefully placed her glasses on the nightstand, and lay on the bed. There was no need to lubricate the toy. Her pussy was already dripping wet. She raised her knees and guided the head of the toy to her glistening opening.

Jill could only get half the length inside her, but that was enough. As she thought about Mark's big dick fucking her daughter's ass, the walls of her vagina constricted around the toy. She gasped as the orgasm took her by surprise.

The tiny camera Mark had placed on her husband's dresser captured every detail.

Jill gasped as Brian shot his come in her pussy for a third time. She loved the sensation, the warmth inside of her. He rarely lasted for more than ten minutes at a time, but he could keep her going with his mouth while he recovered.

It had been two weeks since that terrible night. The bruises on her body were gone, and her pussy and asshole both felt normal again. She had only seen Mark, her daughter's friend, at her home twice, and was hoping she wouldn't have to see him again. Both times he was at the house, she felt like he was up to no good. For now, though, Mark was a distant memory.

Jill's pussy gushed as she rode the waves of her fifth orgasm.

"Brian, stop!" Jill panted. "Give me a break. What's gotten into you?"

"I've been away three weeks, I'm horny, and you shaved your pussy again." Brian said as he turned her onto her stomach. "What can I say?"

Jill crossed her arms under her head as Brian spread her legs. Jill playfully curved her back, raising her ass and causing her pussy to open. Brian's tongue, thrusting deep into her asshole, was the last thing she expected.

"Oh fuck!" Jill cried.

Brian's tongue swirled inside her asshole several times before he withdrew and kissed her ass cheeks. He gently kissed the crease where her legs met her ass, and then proceeded kissing her up and down her legs. Jill's hips gyrated as her right hand found her clit.

Brian kissed the bottom of Jill's feet, licked and sucked on her toes, and then licked, kissed, and occasionally nibbled on her calves and thighs.

Jill's ass was raised in the air as Brian's semen coated the fingers in her pussy. Again, Brian swirled his tongue around her anus. He could tell Jill was enjoying this, and leaned forward.

Jill felt his stiff cock pressing against her folds as he whispered in her ear.

"Do you want it in your ass?"

"If you want." Jill whispered back.

"No, I want to hear you ask for it." Brian rubbed his cock harder against her hand and pussy.

Jill paused for a moment. Her handed rubbed her clit faster.

"Yes. I want you to fuck me in the ass." Jill confided.

Brian positioned himself above and behind her, squatting as he lowered the tip of his cock to her slick anus. He was very careful. Previous attempts at anal sex with Jill had been pleasurable, but he knew the initial penetration was especially painful for her. This time, though, he was able to sink his dick into her ass much easier.

Jill barely moved as he lowered half his shaft into her. Instead of signalling him to wait, she arched her back further, as if taunting him to push himself in just a little more.

Brian could feel Jill's fingers inside her pussy. She was finger-fucking herself hard. He thrust inside her ass deeper and faster until his rhythm matched hers.

Jill had a flashback to that night a few weeks ago. It was the first time she had ever experienced a cock in her pussy and a cock in her ass simultaneously. The first time hurt like hell and she couldn't help but feel she had to shit throughout the whole event. But by the fifth or sixth time, she was able to position her body in such a way as to enjoy the double-fuck.

How she wished a fat cock were pounding her pussy right now.

Brian had held out as long as he could. He deposited his come in Jill's ass in three long spasms, before unceremoniously pulling out his deflated cock. He collapsed on the bed next to her while Jill continued to finger her pussy. Seconds later, Jill's stomach tightened and come bubbled out from between her fingers. She held her breath for a few seconds and then fell flat on her stomach, slowly bringer her hand to her face.

"What's gotten into YOU?" Brian asked.

"You were gone for three weeks, I was horny, and I just shaved my pussy." Jill smiled.

She paused for a minute. She knew he was going to ask why it was so much easier to penetrate her ass this time. Telling her husband that her dildo scavenger hunt for a bachelorette party caused her to end up on the wrong side of town, AND that she was accused of whoring in the process, AND a twisted cop had her service him and at least a half dozen other men with her mouth, pussy, and ass for almost five hours straight as part of her "community service" punishment... was not an option.

"Remember that scavenger hunt I was on -- for the bachelorette party?" Jill asked.

"Yeah, I remember." Brian answered disapprovingly.

Jill leaned over the edge of the bed and reached underneath for one of the toys. She picked one still in its large box and pulled it onto the bed.

"Don't be angry, and don't tell anyone." Jill said shyly. "I decided to experiment."

"Really?" Brian's eyes widened. "With this!?!" It was one of the largest dildos in Jill's collection.

Jill looked at it closely. "No, maybe not this one."

She reached under the bed again, this time pulling out a toy similar in size to her husband's slightly-above-averaged-sized cock. "This one."

Brian breathed a sigh of relief until Jill pulled out another toy from under the bed.

"And this one." Jill winked at him.

"Isn't tomorrow night the bachelorette party?" Brian asked. "What are you going to do when you don't have any more toys?"

"Well, I was going to ask you..." Jill started. "Would you be okay with me keeping one or two?"

"If it makes you happy -- and if you continue to fuck me like you did just now -- I'm all for it." Brian smiled. Jill hadn't fucked him that hard since their honeymoon. Jill kissed him deeply as she stroked his cock back to erection.

"Are you sure your mom got all the dildos on the list?" the bride-to-be asked Andi.

"Yeah, she got them all." Andi smiled. "Aunt Margaret is going to freak!"

"I bet she'll take it all in stride. You know some of these women probably haven't seen a dick bigger than five inches. Heck, I bet some of them haven't seen a dick in twenty years, period."

"Is the banquet okay with the strippers?" Andi asked.

"The banquet hall is owned by a woman. I invited her, too. What do you think?" the bride-to-be smiled. "Oh, I almost forgot! Your friend, Mark, even volunteered to dance and strip at the party, too."

Andi smiled uneasily. She wasn't the jealous type. That wasn't what concerned her. She was afraid Mark would turn her on so much; she'd want to suck his cock in front of everyone. She let out a deep sigh as a wet spot formed in the crotch of her jeans.

Jill stood outside her car for a moment before walking into the banquet hall. In less than a month, she had experienced so much... all because of this stupid bachelorette party.

She wasn't sure why she hadn't worn her contact lenses. She knew she needed her glasses to drive, so rather than lose them; she left her glasses in the car, just to be safe.

Jill had given her sack full of party favors to Tammy, the maid-of-honor, and Tammy wrote Jill a check for the full amount.

"What's this?" Jill asked, looking at the check.

"We didn't expect you to spend a thousand dollars of your own money on a sack full of dildos and vibrators, Miss Jill." Tammy smiled. "You just had to do the dirty work of getting them. I'm impressed. You found every one on the list! I hope it wasn't too much trouble."

"It wasn't what I expected, I can tell you that." Jill answered.

Tammy knew exactly what Jill meant. She had seen the video of Jill be fucked in every possible position by a half-dozen men. Some of those men would be at the party performing as strippers, and she wondered if Jill was going to let loose and provide an encore.

The women attending ranged in age from 18 to 68 years old. Jill took comfort in knowing that the dildos were kept secret, as not everyone was going to get one. Instead, most of the evening was spent with the forty women in attendance sharing stories with the bride-to-be on every topic revolving around a good marriage. The food was excellent. The dessert was classy. The drinks were free. Jill wondered how in the world a 20 year-old could afford to throw a party, as the bride-to-be insisted on paying for everything herself.

After about three hours, Tammy and some of the banquet hall staff carted in a few serving tables with party favor and gift bags. None of them were big enough to conceal some of the toys she had acquired. Jill peaked inside one of the bags and found condoms, male porn magazines, lubricant, and coupons to an upscale day spa.

A few of the women seemed to know there was more planned for the evening, but didn't say anything. Most of the older women and a few of the younger ones took the opportunity to take their gifts, say their goodbyes, and make it an early night.

The rest of the women, including Jill, took seats close to the dance floor.

The banquet hall staff cleared off the tables, but kept the bar open. Jill looked around and counted just over a dozen women remaining, including Andi and the other bridesmaids.

Tammy had the staff dim the lights and turn on a disco ball over the dance floor.

"Okay, ladies. We all know that if the guys can have girls at their bachelor parties, they'll want them to be strippers." Tammy said as she walked to the center of the dance floor. "Some guys will want them to do more than strip, and I think that's okay -- as long as they don't mind if we want the same."

The bride-to-be stood up and next to her maid-of-honor. "I want you to have fun tonight. But whatever you see here, stays with you. Okay?" All of the women nodded, not knowing exactly what she meant. Jill knew they were about to find out when Tammy held up a green wristband.

"If you see a green wristband, the guy is recently-tested and disease-free." Tammy said sternly. "If you don't see one of these, lick, suck, and fuck at your own risk."

"Oh, and one more thing," Tammy added. "Put these on and leave them on until you step out of the building." Tammy held up a mask similar to those worn at Mardi Gras. On one of the tables behind Jill, there was a pile of more masks, each varying slightly from the other, but whose purpose was identical: a very feeble attempt at anonymity.

Tammy dragged a chair to the center of the dance floor, cueing the banquet hall staff to start the music. The bride-to-be quickly took her seat as the first three male strippers strutted onto the dance floor. She put on her mask and jokingly licked her lips while rubbing her breasts and pussy through her blouse and skirt.

The music was loud, but not deafening. The strippers weren't much for dancing, as they mainly strutted in time with the music and allowed their groins to sway in an exaggerated manner. They also wore masks, which covered their foreheads, eyes, nose, but left their chins and most of their mouths exposed. The G-strings they wore left nothing to the imagination, barely covering half the length of their half-erect cocks. All three of the men had shaved their chest and pubic hair, and lathered their bodies with suntan lotion or baby oil. The obligatory bow tie and cuff links completed the ensemble.

Tammy grabbed a microphone. "We all know the bride-to-be worked in the film industry." Two of the strippers took hold of either side of the chair and carefully lifted the chair and turned the bride-to-be so her back was to the other women. The strippers stepped away from the chair and closer to the women in the audience. As they gyrated their hips, one of the strippers allowed his cock to come unsheathed. He made no effort to tuck it back into its hammock.

Jill couldn't be sure without her glasses, but the stripper with the free-hanging dick looked like Wayne, one of Andi and Mark's friends. The other strippers then stepped out of their G-strings, exposing thick, half-erect examples of the male anatomy.

"I've always wondered what it'd be like to be fucked by a dick that big," Mrs. Paladino whispered to Jill. Jill was taken by surprise at the 55 year-old woman's comment.

"Our bride-to-be would like to thank you all for your advice on how to pleasure a man," Tammy continued. "But I think you'll see, she's already a pro in that area."

The three strippers stood in front of the bride-to-be, shoulder-to-shoulder. The women in the audience watched as she leaned forward and took the first stripper's cock in her mouth. She sucked hard, then let it pop out of her mouth so she could lick the shaft, then his balls, and then took half his length down her throat. He became instantly erect and stepped aside.

She took the next stripper's cock in her mouth and eased his full length down her throat and kept it there for a few seconds. As she backed away, she reached up and massaged his balls, and then took his length down her throat again. Within seconds, the stripper's tool was pointing toward the ceiling.

The third stripper's cock was much thicker than the previous two. The bride-to-be could barely get her mouth over the head of his flaccid member. She used both hands to stroke him rather roughly, then pulled his thickening tool from her mouth and rubbed its saliva-covered head on her lips, nose, and forehead. The dick seemed to double in girth almost immediately.

"Ladies, our bride-to-be is a recently retired fluff girl." Tammy said, unbuttoning her blouse. "She's probably sucked more dicks than all of you put together. But she's never been allowed to take them all the way to orgasm -- until tonight!"

Tammy stepped off the dance floor, picked up a long box, and then stepped back under the disco ball. "Don't worry. She doesn't get to have all the fun. If any of you can suck a dick as good as her -- or can make our strippers come in any other way -- you can win one of these little numbers." Tammy pulled one of the large dildos from its box. Mrs. Paladino leaned towards Jill. "I want one of those."

"Ladies, allow me to bring out the rest of the entertainment. Have a good time!" Tammy guided a half-dozen more men in line in front of the bride-to-be. One-by-one, she brought them to erection. The first three strippers walked up to the three closest women and swayed their erect cocks inches from their faces. Two of the women just smiled toward each other and laughed, but the 18 year-old reached out and pulled one of the strippers by his dick toward her. The stripper grimaced in pain as the inexperienced girl dug into his foreskin with her teeth. He withdrew his cock from her mouth, smiling uncomfortably, and stepped aside to another girl.

Jill knew the next girl was her daughter, Andi.

Andi took half the stripper's length down her throat before bobbing her head up and down, and tilting her head left and right with each bob.

"Oh my god, Andi." Jill said under her breath.

The stripper opened his mouth as his legs began to shake. He held his hands on his hips, ensuring that whatever this girl was doing was completely voluntary. Andi engulfed two-thirds of his long tool down her throat and locked her lips around his shaft. He came quickly. The stripper waived at Tammy.