Home for the Holidays Pt. 02

Tiff had a lot to think about on her jog through the neighborhood. She had been woken up at dawn by her soon-to-be husband taking an emergency phone call from work. There was an unusual geological event in the Pacific, and he had to leave for the airport immediately. Tiffany was sad to drop him off at the airport, especially as they had only been engaged since the prior evening.

Thinking of her engagement reminded Tiff of something that she had been trying to block out of her mind since late last night. When she was video chatting with her daughter Kenzie and her soon-to-be step-son Matt, showing them her new diamond ring, Matt had dropped his phone into the hot tub while on the video call. Tiffany could swear, that as the phone camera fell into the hot tub, she saw her new step-son Matt was bottomless and fully erect. Tiffany had a hard time believing Matt was the type of boy who would be aroused by his own step-mom, but she knew how college-aged boys were. However, she did not want to make things awkward for their new family. She decided she would look past the indiscretion, and treat Matt just like she would if he were her own biological son.

After returning home from her jog, Tiffany hung up her coat. She figured she he'd better go downstairs to let Matt know, in person, that his father had taken off early in the morning. After a few knocks on his bedroom door, it swung open. Immediately the smell of stale cum flooded Tiffany's nostrils. She was momentarily taken aback by the odor, but did her best to hide it. She told Matt, "While you were sleeping, your father got called in for an emergency work trip, I'm sorry he won't be here for the holidays. But I am here for you if you need anything. I want you to think of me as your own mom."

Matt was taken aback by the news of his father's urgent departure. He was surprised his dad didn't call or text him. That's when memories of last night flooded into his brain. How Kenzie had jerked him off in the hot tub during the video call with her mom. How he dropped his phone. How at the end of the night, Kenzie took his phone from him. In Kenzie's words, "to help cure him of his Oedipus complex."

Damn, Matt thought to himself, I really need Kenzie to give me back my phone. Matt was still deep in thought when Tiffany snapped her fingers, drawing Matt's attention back to the present time.

Matt, literally snapped back to reality, apologized, "Sorry Tiff, I had a long night. Thanks for asking me to think of you as a mom, I guess we really will be family soon. Congratulations again on the engagement, I'm happy you and Kenzie will be here for the holidays." He added, "I'm glad I won't be spending my break alone."

Tiffany thought to herself, this is the sweet Matt I heard so much about and who I met yesterday. Tiffany was glad she had come to have this moment with Matt. As she was leaving she could not help but notice some movement in Matt's boxers. She tried not to let it bother her too much, but his obvious attraction to her was gnawing at her. To be fair to Matt, she thought, my running clothes did not leave much to the imagination, and as long as he keeps his teenaged fantasies to himself, it won't do any harm. I had better call Susan, she raised a couple of boys and I can get some advice from her.

As soon as Tiff got the laundry going, she and her daughter Kenzie headed out to grab some coffee. On the way to the coffee shop, she called her best friend Susan. Susan was the mother of two very well behaved boys, and Tiff needed her advice on how to raise a young man well. It was a bit uncomfortable with Kenzie in the car listening to their conversation, but she thought it best Kenzie was aware of the situation as well. Tiffany was clueless that it was Kenzie who was had been instigating Matt's behavior all along.

It did not take long for Tiff to catch Susan up on the situation and ask her for her thoughts. Susan recommended, "Tiff you are being too soft on the young man, he needs some discipline. The next time he steps out of line, you need to step-up. I would spank my boys on their bare bottoms anytime they were naughty, I know Matt is college-aged but it might still work." Tiff thought this was a bit extreme, but she would keep it in the back of her mind.

While Tiff and Kenzie were on their coffee run, Matt was at home alone. Just like almost every morning, he woke up with an erection. He was even more aroused when his soon to be step-mom had knocked on his door wearing only leggings and a size too small sport bra. Sure he was practically in love with Kenzie, but her mom Tiffany was beautiful in her own more voluptuous, milfy way.

Matt began stroking himself to the thought of Tiffany. He was dreaming about her large, grapefruit shaped breasts, peaking out over the top of her sports bra. It was impossible for him to not notice her large, firm glutes, which gave her leggings-clad ass a nice full, round peach-shape. Most arousing for Matt, was the clear camel-toe he had noticed when she was at his door way. Her pussy lips had looked so puffy and inviting, their outline clearly visible through her tight leggings... Fuck, Matt thought, realizing, Maybe Kenzie is right, maybe I really do have an Oedipus complex. He panicked and remembered Kenzie's instructions, "From now on you only jerk off to me, no more porn and definitely no more thinking of any milfs while you jack-off, and most importantly do not ever think of my mom when you are touching yourself."

Kenzie still had Matt's phone, and she left with her mom, so Matt knew porn was out of the question. He had to find a way to jerk-off without focusing on his step-mom. He tried to get into Kenzie's room to see if he could find his phone or something else helpful, but she had locked her bedroom door. Matt was desperate, he headed up to the laundry room.

He found a pair of lavender colored lace panties in the dryer, he figured a girly color like that must belong to Kenzie. Her panties were exactly what he needed to get himself off, he took them down to his bedroom. The panties were a physical reminder of his step-sister's sexy, co-Ed figure. He thought about how sexy she looked last night in the hot tub, when she was jerking him off, how it felt when they kissed for the first time. How hot she looked in her red bikini. Her thin, youthful frame that accentuated her full, perky breasts. He had an incredible orgasm, thinking about Kenzie the whole time. When he was finished he was proud of himself, he knew he now he had a cure for his Oedipus complex. From now on, whenever he was horny, he would think of Kenzie as he jacked-off, and totally move Tiffany out of his mind. Unfortunately for Matt, In his post-orgasmic brain fog, he threw the dirtied panties back where he found them, into the finished dryer.

When Tiffany and Kenzie returned home they had a lot on their mind after hearing Susan's disciplinarian advice. Tiffany hoped she would never be forced to discipline Matt, let alone spank him. She knew boys would be boys, but as long as he controlled himself around her, there would be no issues. When she grabbed her clothes out of the dryer, she knew she had an issue.

As she was putting her clean, dry clothes into the hamper, her hand grabbed something wet and sticky. It was a pair of her favorite purple panties, slick with fresh cum. Tiffany thought to herself, Matt has gone too far this time. Behavior like this cannot continue, I need to step-up as a step-mom and discipline him.

Matt knew he was in trouble when the normally light-footed Tiffany was stomping down the stairs. As she entered his room he could see the anger on her face. Even worse, she was holding the purple laced thong that he had just jerked off into not even 20 minutes ago. It was still glistening with his spunk as she held it up in front of him with her bare hand. She asked him, "Care to explain, why my panties are sodden with your spunk?"

Matt was bewildered, he had no idea what to say. He knew it would only make things worse if he explained the truth, that he thought he had been jerking off into her daughter's panties and not hers. All he could do was stay silent and hope his new step-mom would ground him or something.

His silence only made Tiffany more upset, she raised her voice, "Jerking off into your step-mother's panties is unacceptable behavior for a young man of your age, it is childish! If you are going to act like a little boy, I am going to treat you like one. You need tough love and that's what you are going to get. Take off your pants, starting now, you're going to be spanked for this type of behavior."

Matt was humiliated. He was too old to be treated like this, but what choice did he have? He stripped naked and waited for instruction. His shame only increased, as his bare cock began to harden in front of his step-mom.

Tiffany noticed Matt's growing cock but did not address it, wanting to focus solely on the punishment. She sat on the edge of the bed and motioned for Matt to lay down bottom-up over her lap. His now hard cock protruded down between her legging clad thighs. His bare ass was exposed to her. She started swatting it as hard as she could. It was clear to her the spanking was working as Matt began to quietly sniffle into the sheets. After only a couple of minutes of punishment, Matt's quiet sobs turned into groans. She wondered if she had gone too far, hit him too hard, or humiliated him too much. But her growing soft-heartedness was soon overcome with disgust. It was surreal to her when Matt's hard cock began to pulsate and then spasm between her thighs. She tried to ignore it, but she could not deny the reality when she felt an abundance of warm goo seep through her leggings. The same cock that had covered her panties in cum earlier, was now shooting its load all over the crotch of her leggings.

Matt had never been more embarrassed in his life. His own step-mom was spanking his bare ass, and he had just involuntarily orgasmed all over her thighs. He was thankful she remained silent as she administered her last few swats.

Tiffany was at a loss for words, she pushed Matt off of her lap and left without saying another word. As she walked up the stairs, she saw her daughter Kenzie, waiting for her. Kenzie saw the cum splattered all over the crotch of her mother's leggings and knew exactly what had happened, she had heard the spanking reverberating up the stairway. That did not stop Kenzie from asking her mom to fill her in on every painful detail.

While Tiff recounted the events with disgust, Kenzie found it titillating. By the time her mother had finished her story, Kenzie was struggling to hide her excitement. The moment they were done talking, Kenzie ran down to her bedroom to play with herself. As she imagined both her step-brother and her mother's humiliation, Kenzie worked herself into a fierce orgasm. After climaxing, it dawned on her that she had developed full-blown sadistic fetish, humiliating and embarrassing those closest to her had brought her to a mind-blowing orgasm. Now that she was certain what got her off, she just needed to escalate things further.

Several hours later, Kenzie decided to see how far she could take things. For an early dinner she made everyone oysters, paired with a fine Chablis wine. She had heard that oysters were an aphrodisiac and wanted every advantage she could get. The beginning of the dinner was terribly awkward, Matt could not look Tiff in the eye, Kenzie enjoyed the tension. Eventually though, the wine and aphrodisiac loosened everyone up a little bit. Matt was even able to manage an apology to Tiff for his actions earlier in the day, both for the panties and for the spanking mishap. Hearing her own-step brother confess to cumming while being spanked was almost too much for Kenzie, it was more delightful than any dessert ever could have been. Kenzie slid her chair closer to him, to comfort him as Tiff begrudgingly forgave him. As Tiff poured herself a second glass of wine to get through the awkward exchange, Kenzie began rubbing Matt's thigh under the pretense of consoling him. It did not take long for her rubbing to spread to a wider and wider area, quickly reaching his crotch. She played dumb as she felt his cock harden, hidden from their mother's view by the table. Kenzie knew that with a hard cock, and a glass of wine, Matt would not be able to think clearly. She had also noticed it did not take her mom long to gulp down a third, full glass of the Chablis. Kenzie was coming up with a plan.

The day Kenzie and her mom moved into Matt and his father's very large house, Kenzie was fascinated by the novelty of an almost commercial sized laundry chute. When she was exploring the house, as Matt had not come back from college yet, Kenzie had grown a bit nosey. She had gone into Matt's vacant room and looked around. She wondered if the college boy had ever hidden anything in his laundry chute. Unfortunately, she had to crawl a little bit into the chute to see past the bend in the tube. Although it was easy to get into the tube, pulling herself back out was almost impossible as her breasts got caught against the rim of the chute, and her hands were stuck above her head further into the tunnel, unable to assist. She had been bent forward in compromising position and was embarrassed. Luckily her adrenaline kicked in and she was able to barely slide her thin frame out of the chute. She knew her mother, who had much larger breasts, would be able to fit into the chute, but would never have a chance of extricating herself. Kenzie now knew her plan, but would have to improvise quite a bit to make it happen.

Kenzie started weaving her sadistic plan into fruition by sending Matt out to shovel the sidewalk and driveway, there was not much snow yet, but it was a good excuse to get him out of the house while Kenzie worked on her mom. As soon as Matt's boots were laced, he was out the door. Kenzie knew she had to work fast.

Tiff was in the middle of cleaning the dishes, and her fourth glass of wine, when Kenzie interrupted her, "Mom, I need to talk to you. I think Matt has been acting weird because he is on drugs. I was doing some investigating, and I think he has been hiding them in his laundry chute. I can't see far enough in to know for sure, would you mind taking a look?" Tiff fell for the ploy. The mother and daughter headed down to Matt's bedroom, and Tiff squeezed herself into the laundry chute, flashlight in hand. There were no drugs of course, but by the time Tiff realized there was nothing hidden there, it was too late. She was not able to back out of the tube, her entire upper body was bent forward into the tunnel, and her perky ass was invitingly poking out into Matt's room. Kenzie knew her mom must be shouting out for help, but she could only hear muffled noises through the walls. Her mom's voice would only be intelligible through the upstairs laundry chute opening. Kenzie went up to the laundry room, and talked to her mom through the chute. Kenzie explained she was going to go the garage to find lube to help get her mom out of the laundry chute. Tiff thanked her and told her to hurry up before Matt finished shoveling.

Kenzie did not go looking for lube to help out her mom. She immediately went outside to Matt, right as he had finished his shoveling. She had already gotten him hard during dinner, so she knew he was going to be easily manipulated. She told him she needed to talk to him in the garage quick. When they were in the warmth, she began to manipulate him, "Matt, I am so sorry to hear about what happened between you and my mom earlier today. It sounds like your Oedipus complex has not gone away yet. I saw how much cum you sprayed on her leggings earlier today and it looked like a lot, I don't think you shot that much cum for me last night. Maybe tonight you can make it up to me." Kenzie was now stroking his cock through his snow pants, "My mom is in bed now. And it is just the two of us for the rest of the night. I am going to go down to your room and wait for you, I have a fun surprise for us. When you are done putting the snow stuff away, come downstairs and play with me. Oh yeah, be sure to grab some olive oil out of the kitchen, we're going to need some lube."

After Kenzie disappeared back into the house, Matt put away his snow stuff in record time. While he threw his snow pants and sweatshirt into the laundry room, he could have sworn he heard a voice through the laundry chute, but he chalked it up to the wine and his horniness. As he grabbed the olive oil out of the kitchen, he wondered just how far Kenzie was going to let him go tonight, he was hoping all the way. He was delighted when he opened his bedroom door and saw a woman, who he presumed to be Kenzie, bent over in his closet, waiting for him. Matt had been hoping his first time would be more intimate, but he was not going to refuse Kenzie her wish for some kinky sex. It looked like she was pretending to be caught in the laundry chute. He had seen plenty of porn to know what was expected of him.

He was already hard from Kenzie's teasing earlier, and now he was excited to see if Kenzie was equally wet. He slowly pulled down her leggings, revealing her purple lace panties. He thought it was odd that Kenzie, would wear panties so similar to her mother's, but he figured it was just an odd coincidence or maybe they bought their clothes at the same store. As he pushed the thong to the side and inserted his pointer finger into her pussy, she jerked a bit away from him. She must be playing hard to get, Matt thought to himself, she really is kinky. Matt then used both hands to hold her hips steady, immobilizing her, as he lined his cock up to her entrance. He could hear her whore-like moans through the wall as his the fat tip of his cock touched the fold of her pussy lips. He was finally about to lose his virginity, to the hottest young woman he knew, his own step-sister.

Tiff was horrified. She was stuck in the damned laundry chute, and it was taking Kenzie forever to find lube out in the garage. She had now completely lost her voice from crying out to Kenzie up through the tube. Then it happened, she felt a pair of hands grasp the waistband of her leggings and slowly pull them down, if this was Kenzie playing a trick she had gone too far. When Tiff felt her panties get pulled to the side, and a finger begin to prod her womanhood, she pulled away. Now she knew this was not Kenzie playing tricks. Tiff felt sheer terror when she felt two masculine hands hold her waist steady, she knew what was coming next. She cried out for him to stop, but knew her voice would be too muffled by the walls for him to hear anything. She felt Matt line his cock up with her now exposed pussy, he tried to push through her lips but thankfully she was not wet, and he was not able to enter.

Unfortunately a few seconds later, she felt his large hands slather her pussy with what, judging by the viscosity, must have been a copious amount of olive oil. No more than a moment later, she felt the unexpectedly fat head of his cock press into her, meeting much less resistance now that lube had been applied. Fuck, Tiffany thought to herself, he is not even wearing a condom, is my own step-son trying to get me pregnant? Her worries about pregnancy were quickly replaced by a growing sense of pleasure as his thick cock slowly forced itself further and further into her. She could feel her pussy growing wetter and wetter as he continued to fuck in and out of her. She did not know why she was getting so turned on, his cock was certainly large enough, but he had no skill with it. His cock slid completely out of her a few times, not because he was small, but clearly because he was inexperienced. Tiffany wondered to herself, Is Matt a virgin? Is my own step-son losing his virginity to me right now? Oh my gosh, Matt probably thinks I am Kenzie! Have those two been messing around with each other down here, has she been teasing him? I told Tom we should not have let them sleep in bedrooms right next to each other. I am going to kill Kenzie when I get out of here.