Stepmom Goes To The Prom free porn video

When Jillian's period came a few weeks after her encounter with the boys she breathed a huge sigh of relief. So far her stepsons had not said anything to their father and she felt this was the last bullet she had to dodge. Despite taking a "morning after" pill she would not believe she was in the clear until she was sure she wasn't pregnant. She had never been so happy to have her period in her life. Her husband had asked during those weeks why she was so nervous, but she kept putting him off with one excuse or another. Now things could truly go back to normal.

Except that things were not exactly the same. Nick's behavior was more an annoyance than a problem, as long as his father did not notice. Nick stopped propositioning her a few days afterward, when she made it clear nothing else would happen between them, but that did not stop him from finding a million excuses to casually touch her, like squeezing by and brushing her ass in the kitchen or even "accidentally" grabbing one of her boobs. It was something she could put up with, she figured it was at least partially her own fault anyway, as long as he did not really push it.

Sam's attitude toward her had clearly changed too, but in keeping with his personality he never said anything or made any of his brother's moves. No, it was more in the way he looked at her now, like she was a woman and not his mom, or stepmom. He looked at her like he wanted her. Anytime she leaned forward he tried to spy a peek down her top and she'd become much more careful about how she dressed around both boys. Again, she could not blame the Sam. He was only eighteen and he was just a ball of raging hormones. The fact that they'd slept together probably clouded his already confused thoughts. Sam also lingered when he hugged her and more than once Jillian thought she could feel him getting aroused.

However, the problem was not just the boys. It was funny that she still thought of them as boys because they had proved to her they were men now. In her unguarded moments, especially in bed alone at night, Jillian found herself thinking about that night with the boys. She loved her husband and their sex life was fantastic. Although he was twelve years older than her, he was just as fit and handsome as ever, if not more so. But work kept him away from home too much these days and there were too many nights when she was alone in bed missing him. They had phone sex pretty frequently, she'd even texted him some racy pictures, but using her vibrator to get off while he was on the phone was not the same thing as him being there, insider her, making love to her. And on those nights when he wasn't available and she was alone with her favorite toy and her thoughts memories of that night with her stepsons came flooding back unbidden. Jillian just could not help it. That night was just so incredible. One of her hottest, darkest fantasies was having a threesome. She never thought she would actually do it, let alone do it with her stepsons. While buzzing her clit with the little Pocket Rocket she flashed back on both boys taking her at the same time, one in her mouth, the other in her pussy, like she was impaled on one giant cock.

Jillian felt guilty when she fantasized about her stepsons, but she told herself they were both of age and that they had seduced her, instead of the other way around. Everyone had a good time so as long as they kept everything in the past everything would be fine, right? The problem was, all those thoughts and lusts could only be buried for so long. If the temptation grew too great, would she be able to resist?

"Hey, bro, why so down?" Nick asked his little brother, who was in the living room playing Xbox.

"Things are over with Emma," replied glumly, not taking his eyes from the big flat screen TV, where he was busy mowing down Nazis in a first-person shooting game.

"That sucks, but you guys have split before. I'm sure you'll be back together in no time." Nick plopped down beside his brother on the couch.

"No, it's permanent this time. I think she was cheating on me because she's already got another date for the prom."

Nick chucked Sam on the arm. "Well, you're too young to be tied down anyway. There are plenty of chicks out there, just pick one and work your magic."

"Thanks, but I don't think I have any magic. I can't even think about other girls right now."

"Dude, Emma's cute, sure, but there's plenty of tail at your school."

"Everyone else already has a date for Prom. I'm not going to get some hot chick to go with me with to Prom with just two weeks." Sam took a head shot and GAME OVER flashed on the screen. He threw the controller on the floor and said, "This sucks."

Nick eyed his brother shrewdly. While he was an operator who had no trouble going from one girl to the next, Sam had always worn his heart on his sleeve. If he weren't such a good looking guy Nick didn't think his brother would ever get laid. They were both large, athletic boys with exotic looks due to their father's Filipino heritage and their mother's Italian background. Looking at his brother, Nick knew this was about more than Emma breaking up with him. Sam hadn't been quite right since they'd banged their stepmother. Nick understood. That had been a mind blowing day for him too. She was only thirty-three and she was a piece of ass. He was twenty and thought she was a cougar any guy his age would be proud to bag.

"Come clean, dude. This isn't just about Emma. You don't want any other girls because you want to fuck Jill again," Nick said. He was only ten when she came into their lives and both he and Sam thought of her as their mother since their own had mostly disappeared from their lives.

Sam looked away. "It's not like that. And you shouldn't talk about Mom that way." He was only eight when she came into their lives and both he and Nick thought of her as their mother since their own had mostly disappeared from their lives. Sam still called her Mom as much as he called her Jill. He wasn't exactly lying. Yes, he would love to get his stepmom in bed again, but it wasn't just about sex. It angered him that Nick talked about her like she was just another notch on his belt. Sam loved her. He'd always loved her, of course, she really was like a mother to him, but when they were in bed, especially when they were in bed alone, it was like they made love. It wasn't just fucking to Sam. He knew he could never be with her for so many reasons, but that didn't mean he didn't have feelings.

"Oh, shit. You have feelings for her. Listen up, it can't be anything more than what it was. She is married to our dad. She's not leaving him for his eighteen-year-old son. If anyone even knew what's already happened they would freak."

"I know that. I'm not stupid."

"What you need is to get her out of your system. Maybe if you fucked her again you could move on. Do you think?" Nick understood that feeling. She was phenomenal in bed. That Mother's Day had been the hottest sex he'd ever had in his young life. It should have been weird to share a woman, any woman, with his little brother, but it wasn't. Jillian was just open to everything. He would have loved another shot with her and even tried to get some, but she made it clear it was a one-time only thing and he backed off rather than cause a problem. Besides, it wasn't like he couldn't get other chicks. But still, he'd love another piece.

"Maybe," Sam admitted. Another chance to be with their stepmom would be amazing, but he knew it wasn't going to happen.

"Then we'll have to make that happen. Maybe if you took her to the prom. You know, everyone expects to get laid on prom night."

"I think it would be weird if I took my mother to the prom," Sam scoffed.

"Stepmom," Nick reminded him.

"Mom, stepmom, whatever."

"Jill's hot and she totally looks younger than she is. Our friends know her, but not that well. If she disguised herself somehow you could say she was someone else, like a younger sister, or a cousin."

"That wouldn't be weird?"

"She's not blood and if people thought she was going as more of a friend who cares. Then, at the after party, she's had a few drinks, you get her alone, and pow, make your move."

"You're crazy."

"It could work. Trust your big brother," Nick insisted.

"Even if I said yes, Mom would never do it."

"Leave that to me. Jill loves us, she'd do anything to us. I know we can convince her."

"If you can get her to do it, I'm in, but for the record, I still think you're crazy. Why would you help me get her again anyway? You're not going to be there."

"I just want to help my little bro out. Besides, if it softens her up maybe I will get a shot at her too."

They made their pitch that night over dinner. Their father was out of town once again, so it was just the boys and Jillian. Their small talk through the salad made Sam want to scream. He wondered how long Nick was going to await to bring Prom up. They were just finishing the salmon when Nick got the ball rolling.

"Did Sam tell you he and Emma are broken up again? He says it's for good this time," Nick told Jillian.

"No, honey that's terrible. I'm so sorry. Are you okay?" Jillian asked, putting her hand on Sam's arm.

"I knew this was coming, but it's still pretty tough. It seems like we were together forever." Sam really laid it on, figuring that making her feel bad was their plan's only chance. "We did everything together, y'know?"

"And he means everything," Nick added with a wink.

"Do you always have to be so crude, Nick? Your brother is genuinely upset. I'm sure sex is the last thing on his mind." Clearly, Jillian did not understand the mind of the teenage boy. Even as she leaned forward Sam was trying to peek down the shallow V-neck of her sweater without getting caught and she was so distracted by her feelings that she didn't notice. She knew just how much Sam liked his girlfriend.

"She already has another date to Prom. I couldn't believe it," Sam said.

"Do you think she was cheating on you?" Jillian asked with concern.

"Maybe. It seems like she moved on pretty fast."

"Yeah, she left my boy high and dry. She's still going to Prom while he sits at home with his dick in his hand," Nick said.

"Nick, please." She shot the older boy a look and then turned back to Sam. "I am sure there is a girl at your school who would be happy to go with you."

"I don't know any." Sam was trying to look at pathetic as possible.

"That can't be true."

The only girls that don't have dates two weeks before Prom are the scabs. Do you want Sam to show up at Prom with some skeevy girl while Emma shows up with some stud on her arm?" Nick said.

"Her date is on the soccer team," Sam added.

"Looks aren't everything, but I guess you have a point." Jillian remembered what it was like to be a teenager. She was sure Sam wanted to take some hot girl to make Emma jealous. That's what she would have done. But she'd seen some very pretty girls hanging around with Sam and saw the way they looked at him. She was sure they were just waiting for their chance. "What about one of your friends? I know it's not the same as taking a real date, but you'd still have fun."

"Whitney and Sarah and Becky all already have dates. I think I'm sunk." Sam stared down at the table.

"I'm sure if we put our heads together we can think of something. One of the women I work with has a daughter about your age."

"Why don't you go with him?" Nick said casually. Jillian looked at him like he'd suggested she run naked down Main Street and he struggled not to laugh.

"I'm sure the last thing your brother wants to do is take his stepmother to the prom. That would be really cool."

"Well, you are a hot chick," Nick said.

"Stop it," Jillian said dismissively.

"I guess it might be okay. I mean, if that's the only way I could go," Sam said as if he was thinking about it for the first time. He watched Jillian carefully as she looked between him and his brother. Seeing the look on her face he thought, This is never going to work.

"Sam, you do not want to take your stepmother to the prom. Think about it. What would your friends think?"

"You could go in disguise," Nick said helpfully. "Our friends don't hang out here much. They don't know you that well."

"We've had barbeques here with your friends. They know me well enough. Do you think if I ran out ad got a cheap wig they wouldn't know me?"

"Well, maybe a nice wig," Nick chuckled.

"I'm in my thirties. My prom was like fifteen years ago. Surely I would look out of place," Jillian laughed. She did not take the suggestion seriously at all.

"You're really pretty, Mom. You could easily pass as younger."

"Thank you, Sam." His compliment touched her. He's such a sweet boy, she thought. But then she noticed where his eyes were and wondered, Is he looking down my sweater again? She took her hand away from his arm and sat up, disturbed that he was checking her out, but feeling a tingle down below because he wanted to.

"Yeah, I think with a wig and some make-up you could easily claim to be a younger sister or something like that. You could totally do it," Nick said.

"You guys are sweet, I think, but this idea is nuts." She was flattered that the boys seemed to think she could pull it off, but the joke was over. She got up to clear the plates and noticed both boys were just staring at her. It dawned on her that they were serious. They really thought she should be Sam's date for the prom. "You guys aren't kidding, are you?" Jillian said slowly.

"It will work. I'm telling you," Nick insisted.

"It's nuts and besides, Sam never actually said he wanted me to take him to the prom. This is all something you made up."

"Actually, it would be cool if you did it. I mean, I don't want to make you do anything you don't want, but I am stuck and you would be a totally hot date and I think it could work." Sam was trying to hide his excitement because he noticed that in all her protests about what a crazy idea it was she had never actually said no she wouldn't do it.

"Sam, I am flattered that you think I could pass for some hot college student, but I don't think that's true and I don't think this idea would ever work. Your friends would recognize me and then everything would get weird. And besides, I would never do anything like this without talking to your father first and I am sure he would never go for it." Jillian was exasperated. She was going to have to check the boys' rooms for drugs because they had to be smoking something.

"So talk to Dad and see what he says," Nick said. He wasn't so sure his father would reject the idea out of hand. His father was a pretty loose, fun guy and he would probably get a kick out of Jillian dressing all up and going to a prom, as long as he got to see pictures, of course. He knew his dad still thought Jillian was as hot as his sons did and on a few drunken occasions he'd let slip just how hot she was in bed. That was when Nick first got the idea that if he ever had a chance to find out for himself he would. And this past Mother's Day had been a happy surprise. He hoped his dad stayed away even longer on business because maybe Jillian would get so horny again that she couldn't help herself.

"Your dad is going to think I'm crazy if I go to him with something like this!"

"Please, just ask," Sam said.

"It can't hurt to ask," Nick chimed in.

"I never even said I was willing to do it."

"You never said you weren't," Sam pointed out.

"I ... I... " Jillian sputtered. She had to admit, deep down, that it sounded fun. She had a great time at her own prom and wanted Sam to have just as memorable a night. Well, maybe not just as memorable. She'd done some things in the limo and later back at the hotel after party that she would not want her stepsons knowing about. But she did want Sam to have a good time and if this was something he really wanted could she tell him no. What would be the harm, really? And maybe, she could admit, their flattery had worked on her. She was starting to think that maybe with the right look she could pull it off.

"Listen, guys. I am not making any promises, but when I talk to your father tonight I will talk to him about it. But don't be disappointed if he says no."

"Okay, no promises," Sam said, trying not to burst. He couldn't believe it. Jill actually agreed! Now they just had to get their dad to go along.

Later that night, after the boys had gone upstairs, Nick told Sam, "Don't worry, Dad never tells you no for anything. You're in, my man." Sam didn't quite believe him and went back down later to talk to Jill. Her bedroom door was closed at the end of the hallway and before he could knock he heard she was still on the phone and paused.

"Oh, you would just love to see me dressed up like some little high school tart, wouldn't you?" Jill laughed. Silence, and then, "I don't think the boys should see me like that." If only Dad knew what we've seen, Sam thought.

"Are you sure it's okay?" A pause. "Really? Sure, you can help pick my dress. I can't wait for you to get home, baby. You have no idea how much I miss you. You want to know how much?"

Sam couldn't hear what she was saying after that, but then there was the unmistakable buzz of a vibrator, joined shortly by the soft sounds of Jill moaning. Oh shit, Sam thought. Mom's having phone sex and masturbating! His cock was at full staff. He couldn't believe what he was hearing! The pitch of the buzzing changed, like she was moving it around and her moans grew louder. God, he wished he had X-ray vision. He couldn't help it and pull his own thick shaft out and stroked it, imagining he could see her in there, on her back and naked, while she worked a big vibrator between her legs. He could just see her pumping her hips up at it while she plunged it in and out.

"Oh, baby, that sounds so good. You know I love that," Jill cooed. Sam wanted to know what she loved! Jillian's moans got louder and louder until she finally gave a sharp cry and there was silence, except for the buzzing of the vibrator.

"Oh, Jill! Oh, Mom!" Sam moaned quietly before shooting his load all over his t-shirt. When he realized he'd spoken allowed, he panicked and retreated down the hallway and back this room with his heart pound. What if Jill heard him listening in?

Sam need not have worried. Jillian was so swept up in her orgasm that he could have been in the room with her and she wouldn't have noticed. Her husband was telling her how he would strip her out of her prom dress and what he would do to her next. He was so good at spinning fantasies for her and she climaxed hard. If only he'd been there for real! He was away almost three weeks at a time these days and she could hardly stand it. They used to have sex almost every day and now she had to try and pack all that sexual frustration into a few days at a time. got the new division in Texas up and running. But in the meantime she had other things to worry about. Amazingly, he had said that yes, he thought she should go to Sam's prom with him. Now she was going to have to go through with it!

Jillian checked herself out in the mirror, turning all the way around to make sure the dress was fitted properly in all the right places. She had to admit, it was fun to go out and try on all those gowns and she was proud to still be a size four so many years after her own prom, but she couldn't pick a dress on her own. It was amazing how much prom gowns had changed since her day. So many of them were so short and they were all revealing. She didn't think she would be wearing something like that around Sam, especially considering recent events, so she snapped pictures of herself in the dresses and texted them to her husband and let him decide on the dress. Jillian was shocked when he chose one of the sexiest dresses! Even with his not knowing she'd slept with his sons she was surprised he'd picked that dress. It was a black cherry color and low cut and had sparkly straps that crisscrossed in the back, leaving the prom gown virtually backless. There was no bra she could wear with that! And if that wasn't bad enough, the long gown had a slit that came all the way up to mid-thigh. She did look sexy in the dress, but she was surprised her husband would send her out on even a mock date with his son in it. Satisfied the dress was covering her in all the right places, though just barely, she stepped into her four inch heels and went to make a last check on her hair and make-up. Of course her husband was once again out of town and would not be there to see them off. She hoped he thought about her in the sexy dress and had to jerk off.

Jillian did try a wig, as the boys suggested, but she did not look right as a blonde and the red wig just did not look real. In the end she dyed her naturally auburn hair a much deeper red and added extensions so that it fell all the way down her back. With the hair and wearing more make-up than usual, she had to admit, she did look like a different person. The cover story was that she was her own distant cousin, a college student, who was in town visiting. Can I really pull this off? Are any of Sam's friends going to buy I'm some twenty-three-year-old college student? She still out her doubts, but she had no choice now but to try and pull it off.

Sam was pacing in the living room and fussing with his tux as he waited for Jill to come out of her bedroom. He couldn't believe it was really happening. He was actually going out with Jill and he might have a chance to be with her again. It was the only thing he'd been able to think about for the last couple weeks. He couldn't wait to see what she looked like as she refused to let him see her dress ahead of time. Jill had been shuttered in her bedroom since she came home from the hairdressers while he was upstairs earlier.

"You're going to wear a hole in the floor, chill out," Nick said. He was lounging on the couch and trying to watch the TV Sam kept pacing in front of.

"The limo's going to be here any minute and Mom's not out here yet. We're the first stop so everyone will be late if we're not ready," Sam replied, adjusting his cummerbund for the hundredth time. He was wearing a classic black tuxedo. His short, black hair had been trimmed at the barber earlier. He was ready for his big date.

"She will be out any minute. And don't forget her name tonight is Jenna."

"Right, Jenna."

Right on cue, Jill emerged from the bedroom and both boys' jaws dropped. Neither of them could believe the stunning girl standing before them was their stepmom. Obviously they both thought Jill was sexy, but they had never seen her wear anything like that prom gown and with the make-up and the hair she looked like sex in a dress! Sam's mouth worked, but no words came out. Her hair was partially gathered on her head, but then tumbled down her back like a cascade of flame. She looked so hot as a redhead! Her make-up was done perfectly and when she moved he realized she was wearing a touch of body glitter. The dark red dress dipped low to show off plenty of cleavage and hugged her lithe body and Sam did not miss the sliver of thigh exposed by the high slit as she walked. His cock was rock hard staring at her and he knew that if he did not get to bed Jill again tonight he was going to have the world's worst case of blue balls.

"Wow, Jill," Sam finally said.

"Holy crap you look hot. Goddam, why didn't I take you to my prom?" Nick marveled. He was pretty hard too and then he saw it only got better when she came into the living room and he was the gown was basically backless.

"Thank you, boys. I'm glad you approve. Do I really look good enough?"

"Are you kidding? I think every other girl there is going to hate you," Nick said. He jumped off the couch and took Jill's hand and twirled and then dipped her, using the chance to cop a quick feel. When she felt his hand on her tit Jill tried to pull herself up, but not before he got a good handful. Damn, he missed those titties.

"Thanks, Nick. I think. Actually, your dad picked this dress out. I was surprised."

Thank you, Dad, Sam thought. "You do look amazing. This is so cool."

Jillian saw his excitement and almost blushed. Both boys looked like they wanted to rip the dress right off her body and while it was so inappropriate it did feel good. She hadn't made love to her husband in almost two weeks and seeing two strong young men who wanted her did have an effect.

"Okay, let's get some pictures. I'm sure Dad will want to see," Nick said, grabbing the camera. He snapped several shots of the couple by the fireplace and then took a few of each of them alone. He had fun posing Jill, making sure the slit in her dress was open or trying to get a down blouse shot. Jill kept posing until she realized what he was up to. Nick played innocent and was saved by the honk of the limo's horn.

The limo was a stretch SUV and Jillian flashed a lot of thigh stepping up into it, which she saw Sam did not miss. Even the limo driver was leering at her. The limo was huge inside, especially with just the two of them inside. Ropes of LED lighting ran around the perimeter of the ceiling and there was a flat screen TV over the bar, which was locked. The parent in her was relieved the limo company was being responsible, but looking around the plush limo she couldn't believe how spoiled kids were these days. Despite all the room, Sam sat very close to her on the back seat.

"Listen, Sam. We need to set some ground rules. I know I am your date tonight and I will do what I can to convince your friends, but you need to remember that I am your stepmother and we need to keep some boundaries. I understand that might seem weird, given what happened between us before, but we can't go back there. What we did wasn't right."

"But it felt right," Sam said, taking her hand. "It was so good, wasn't it?"

"It was good. It was great, but it wasn't right. I really do feel like a mother to you boys and it wasn't right to do something like that to your dad anyway. I cheated on your father." Oddly, it was the first time they'd really talked about what happened on Mother's Day.

"I think of you like my mom, too, but I have to be honest, I always thought you were pretty, even when I was little. And then when I got older I noticed you were kinda hot too."

"Only kinda hot?" Jillian teased, trying to ease the tension.

"You know what I mean. It's just when that happened between us I couldn't believe it. It was just so cool to be with you and wow, it was intense." Sam blushed as he spoke about it. "I mean, girls my age aren't like that. Being with Emma was never like that."

It was Jillian's turn to blush. She supposed she did know more about sex than a teenage girl. She knew a lot more about sex and pleasing a man than she did in high school. Did I blow their minds? Jillian wondered.

"Thank you, Sam. That really does mean a lot to me, but you do understand why nothing like that can happen tonight. Like I said, we'll convince your friends that I am your date and not your stepmom, but nothing will go further than that." She really did want him to have a good time. In fact, she promised his father that she would do whatever she needed to for Sam to have a great prom, but she was sure her husband did not mean for her to go above and beyond. Tonight would not be like her prom night.

"I understand," Sam replied half-heartedly. Jill sounded so serious he started to doubt that he would be able to get her into bed, but then he checked her out again and thought, I just have to do it.

The limo picked up six other couples and it became crowded inside, forcing Jillian and Sam closer together. He slipped his arm around her and lightly caressed her bare shoulder, which felt nice. She was also pressed closely to his friend Buck, a big, beefy boy who was a lineman on the football team, though she thought there was enough room in limo for Buck to give her some space. But Buck had barely taken his eyes off her since he got into the limo with his date, Ashleigh. Sam introduced Jillian as "Jenna," an old family friend from out of town and everyone seemed to buy it so far. Nick proved to be prescient as all of the boys in the limo were checking her out and none of their dates seemed to like it very much. Jillian just kept her hand folded her lap and her mouth shut.

Jillian felt silly when they stood for their official prom portrait. It was so stiff and formal and she wondered if she would cringe looking at it years later, like she did when she looked at her own prom photo. She did try to sex this picture up by standing to make sure the slit in her dress showed off her legs and the expensive, spike heeled shoes she'd bought to match her dress.

The prom took place in a nicely decorated catering hall with several large, round tables placed around the parameter of a huge dance floor. A DJ spun tunes on a stage at the front of the room and there was a bar with two bartenders serving soft drinks, juices and energy drinks. When they arrived Sam and his friend staked out a table the girls put down their purses before dispersing to see their friends while the guys went up to the bar for drinks. It left Jillian on her own for a moment at the table and looking around the room she felt very out of place. She needn't have worried about her gown because so many of the young women's dresses were even skimpier and sexier than hers, although she thought she wore her gown with a confidence most of those girls just didn't have yet. Really, she couldn't believe some of those girls' parents let them out of the house dressed that way. She could imagine quite a number of fathers almost had heart attacks.