Trip to the Cabin with my Stepmom

*Author's Note* Those of you who follow my account, and my stories know that my fiancé and I have begun to enjoy watching a little bit of porn together each week. After watching a video recently that used the premise of this story, we got to talking about how hot that type of situation would be, and thus this story was born. As always, ratings and constructive comments/feedback are always appreciated; I hope you enjoy!

Well, this trip wasn't going as we had planned. For the fifth or sixth time, my stepmom Kelly and I were slowing to a stop due to the snow clogging the roads. I groaned, "Seriously people, this isn't that bad."

Kelly looked over at me and chuckled, "Calm down James, we are still making decent time given the weather."

"I know, but I was hoping to get to the cabin before dark, it's easier to get things turned on."

She placed her hand on top of mine on the gear shift of the Jeep, gave me a small smile and said, "I understand. Thank you for coming up and helping me clean it out. I know that this isn't easy for you."

I nodded my head and thought back to a year prior when I got the call from Kelly that my dad had a massive heart attack while out for his evening run. There had been no real warning and since he was only 44 and in what we thought was good health, it came as a shock to all of us. Luckily Dad and Kelly did have a will and based on his investments, savings, and other things, her and I were both set for a long time.

While Kelly was my stepmom, we didn't have the typical stepmom/stepson relationship. Kelly had been in my life for as long as I could really remember. My mother, rest her soul, had died giving birth to me, a massive hemorrhage from what Dad told me. Dad and Mom were young when I was born, she was 21 and he was 22, college sweethearts. According to pictures and Dad, Kelly came into our lives when I was four, they began dating when I was five and were married when I was seven. While she was the mother figure in my life, she tried to be like an older friend or even an older sister more than my mom, my grandmother tried to handle the normal motherly stuff such as keeping me in line. At 24 now, I never really called her mom, simply Kelly or Kell, something that never seemed to phase her.

As I got older, I did what every young man with a beautiful, younger stepmom did, I fantasized about her, nothing I would try to pursue obviously, she was married to my dad, but young fantasies none the less. My friends often commented on her, and I couldn't blame them honestly, Kelly was beautiful, how my dad snagged her, I still don't know. Kelly has blonde hair and stands 5'9, she has always been physically fit and active, hiking, running, yoga and clean eating. While her and my dad never had children, she definitely has that MILF vibe from her body shape; she has a toned ass and wider hips from her physical activity, a narrow waist, and when I was younger and snuck a peak at her bras, I discovered a 34B tag. I have to admit, there were a time or two that I stole her panties out of the laundry and used the lace to get off, before quickly throwing them in with the next load of laundry I did.

We always got along well, even as I went through my "jack-ass teenager," stage, she was able to tolerate me, even when I was insufferable. She was about 5 years younger than dad having just turned 40 right before he passed away, so maybe she was able to see my point of view on things better than he could, I dunno.

I was snapped back to reality when Kelly tapped my hand again, "Hey, traffic is moving a bit."

I shook my head as we began to creep forward, "Sorry, was just thinking."

She squeezed my hand, "I know it's been tough, are you sure you're okay with me selling the cabin?"

"Yeah, it was more your and dad's place. I enjoy it, but I'll be honest, I want to use some of what he left me to get a place up around Kalispell so I can take advantage of fishing and snowboarding."

"Ooo that'll be great for you!"

"Yeah, just wish it was under better circumstances..."

"Me too honey, me too."

We crept along for another hour or so before I noticed people hitting their brakes and starting to ease off onto the shoulder and onto the exit ramp. I next saw flashing lights of a highway patrol pickup and the officer directing people off the highway. We pulled even with him, and I rolled down the window, "What's going on officer?"

"Road's closed up ahead, major wreck. Diverting everyone off here."

I sighed, "We've got a cabin outside of Sedan, can we go up another 2 exits?"

"Sorry son, with the weather and the wreck, I don't think you are getting there tonight."

I groaned and thanked him before joining the stream of cars making our way off the highway. "This is just great, it is almost 7, we aren't going to get to the cabin, and who knows where we stay with everyone getting detoured."

I glanced over and Kelly had her head in her phone, "Already on it."

I kept driving north and Kelly made a phone call, "Good Evening! My stepson and I got detoured because of the wreck on 191, I was just wondering if you had any rooms available? Just one, okay, we will take it."

Kelly dug her wallet out of her purse and proceeded to read her credit card number over the phone and thanked them before hanging up. She reached over and grabbed my phone out of the small nook between our cups and after asking for my passcode, began to enter an address, "Follow these directions, I got us the last room for a ways I figure."

"Alright, thanks for handling that."

She reached over and squeezed my leg, "Anything for my boy."

"Boy, I'm a man now."

She laughed, "I know you are, I'm just messing with you." She turned a bit more serious and continued, "You've really grown into a successful and handsome young man. I'm really sorry that Mandy didn't see that."

Mandy was my ex that I had broken up with about three months after my dad passed away, after she complained that I wasn't fun anymore and was becoming a homebody. I scoffed, "Yeah, her loss, dumb bitch."

Kelly feigned shock, "James, language!"

We both laughed as we began to pick up a little speed as the traffic thinned out as people began to make their ways into small towns looking for rooms as it began to get later. Finally, around 9, we pulled into the town of Gallatin and made our ways to the parking lot of the Gallatin Gateway Inn.

We found a parking spot and jumped out of the Jeep, grabbing Kelly's suitcase and my duffel bag before making our way into the lobby. Kelly walked up to the desk, giving her name and began to discuss things with the clerk as I looked around. I heard her remark, "The room only has a queen size bed?"

"Yes ma'am, it is the only one we had left."

"Oh, is there a recliner or could we get a roll away?"

I glanced over as the clerk shook his head, "Normally we could get a roll away, but with the storm, we are all out."

Kelly sighed, "Okay, it is just for one night, thank you."

She walked towards me with a key, "So did you hear that?"

"Yeah...we will track down some extra blankets and I'll sleep on the floor."

"You don't have to do that, it's a queen size bed, and as long as you don't sleep naked, we will be fine."

I laughed as we walked down the hall and as we reached the door, I replied, "Nope I sleep in gym shorts, should I be worried about you?"

Kelly smirked, "You wish." As she opened the door, I was speechless and just stood there. Kelly turned and looked at me, then winked, "You gonna make it?"

"I, Uh, ummm..."

She burst out laughing, "I'm just screwing with you, I sleep in gym shorts and a sports bra usually. You've seen that plenty, now get out of the hall."

I followed her into the room, unsure of what to think of her comment. She had always picked on me playfully, but never with comments like she had just made. I quickly tried to clear my head, silently scolding myself, "Cut it out you moron. God, you need to get laid." Since Mandy had broken up with me, I buried myself in my work and wrapping up Dad's affairs with Kelly and hadn't had time to get back to the dating scene.

Setting our bags down, I observed a very basic, if not dated hotel room. Right when you walked in the bathroom was to your left. Once you entered the room, there was a classic style dresser with a TV on top; across from it there was a queen size bed with small end tables on either side of it.

Kelly broke the silence, "Home sweet home for the night. Mind if I go ahead and use the bathroom then shower?"

"Sounds good to me, I'm going to track down some vending machines."

"Perfect! Can you get me a bottle of water and a bag of chips?"

"Will do!"

As she began to rifle through her suitcase, I couldn't help but try and sneak a peak at her clothes, seeing her typical jeans, hoodies, leggings, t-shirts, but then a plain black bra, a sports bra, and multiple pairs of panties. As she set things aside that she would need, I quickly turned away and headed out of the room making my way down the hall towards the front desk to find vending machines.

It took about 15 minutes to make my way to the front desk, find the vending machines, and then double check that everything was out of sight in the Jeep before making my way back into the hotel, then back to our room. When I unlocked the door, the bathroom door was open, and I found Kelly sitting on the bed rubbing lotion on her legs. As she had said before I left, she was wearing a black sports bra and a pair of black high waisted yoga shorts that showed off her toned legs and thighs.

"Got us some drinks and snacks."

She looked up and smiled as I set the stuff on the dresser, "Thanks!"

I moved to my duffle bag and found and began to dig out my toiletries bag and a pair of shorts, "You done in the bathroom?"

Kelly had stood up and was putting her things back in her suitcase, I couldn't help but notice she had bent over to do so, and her ass was perfectly framed in the shorts. Without turning around she said, "Yep, all yours!" I felt my cock begin to subtly rise, so I grabbed my things and slipped past her, slightly grazing her ass with my pelvis. She laughed "Say excuse me young man!"

"Sorry...". I made my way into the bathroom and shut the door, quickly turning the water on and leaning over the sink. I said softly aloud noticing my growing cock, "Dude, get your shit together. You have to share a bed with her, you can't have a fucking hard on!" I grunted and turned the water on, stripping my clothes off, and as suspected, my cock bounced free in a state of half erection. I climbed in the shower and willed myself to calm down; I thought about rubbing one out, but I knew that it would take another 10 minutes after that for my erection to completely subside, damn not having sex in nine months.

I showered and tried to think of everything I could but sharing a bed with Kelly, but I had little luck. I eventually gave up and finished up my shower, drying off and then slipping into my gym shorts that I planned to sleep in. Luckily, they were baggier basketball style shorts and my half-erection wasn't really noticeable. I gathered my things and exited the bathroom to find Kelly sitting in bad with the blankets pulled to her waist. She had taken her contacts out and had switched to her glasses as she read on her iPad. She looked up and smiled at me, "Feel better?"

"Much, I'm ready to conk out, the driving wore me out."

She set her iPad down, laying her glasses on top of them, "Understandable, 3 hours of driving in the snow is always tiring."

"For sure, any news on the roads?"

"Yeah, looks like the accident will be cleaned up tonight and we will be good to go tomorrow morning. Weather is supposed to improve too. Still cold, but clearing off."

I moved towards my duffle, placing my clothes on the floor beside it and said, "Cool, what time is check out?"

"Ten, I figure when we get up and rolling, we can head out. Breakfast on the road on the road or whatever pastries they set out?"

"Sounds good to me, let me brush my teeth and then I'm heading to bed." She nodded and picked up her phone as I headed back to the bathroom to brush my teeth, once I was finished, I came back out and told her it was all hers.

She made her way past me, once again brushing against me in the tight space between the bed and the dresser. As I climbed into bed, I heard the toilet flush, then the sink run and a few moments later, Kelly came back out, "You good for me to turn the overhead light off?"

"Go for it." I turned my flashlight on so she could see as she moved through the darkness after turning the light off. As she climbed into bed, I shut the light off and lay my phone on my table and settled in.

I felt the bed shift and she lay down beside me. We lay in silence for a few minutes before Kelly spoke, "Thanks again for coming up with me, it really means a lot."

I reached over and gently squeezed her shoulder in a hugging manner, "You're welcome. Just because dad is gone, doesn't mean you're getting rid of me."

She laughed, "I appreciate that. Your grandparents told me I am always welcome for the holidays, which means a lot."

"Well good, because if they didn't, I was going to make sure you were invited to family things by me."

She rolled to her side, so we were facing one another, "Thanks, that really means a lot, I guess in the way of family, we are all we've got other than them." She sat up and kissed me softly on the cheek, which while unexpected given we were in bed together, wasn't different from when I used to leave home during college or after I graduated. But feeling her kiss and knowing she was half naked and touching me, sent a different signal to my genitals. "Goodnight James."

"Night Kelly." With goodnights said, I rolled over to my side of the bed and she rolled to hers and I quickly drifted off to sleep.

I woke up a little while later; the first thing I realized was that I was hot, the second thing I realized was that I was on my side and spooning Kelly. I woke up completely and then realized three other things, (1) my right arm was draped over Kelly's midsection and my hand was tucked up under her left breast, (2) my erection from earlier had returned, but much stronger, and (3) Kelly was softly gyrating her ass against my cock.

I'm sure my eyes opened as wide as possible, and my surprise was further compounded when I heard her let out a soft moan, and gently push back against me more. I was frozen in shock, but her movements were having an impact on me as I felt my cock getting harder. As she let out another soft moan, my hips involuntarily pushed into her, causing her to stop and let out a slightly louder groan. We lay there, pressing into each other before Kelly broke the silence, she softly said, "James...are you awake?"

My brain immediately told me to lie so she would continue, but I eventually squeaked out, "Yeah...". I expected her to pull away and act as nothing happened but once again, I was in for another surprise.

"You feel good..."

"...You do too." We lay in silence for a moment until Kelly began to subtly move her ass while pressed firmly against me. This time we both made noise, me a groan as I pressed tighter to her, and her a moan from the movement and increase in pressure. Taking a chance, I moved my hand from under her breast, cupping it firmly and feeling it give under my touch, which caused another moan to escape her lips.

I kneaded her breast through her sports bar as she ground her ass against me, our noises each increasing with the stimulation when suddenly she stopped moving. I stopped my attention on her breast as she shifted and moved to a sitting position until she was looking at me and I rolled to my back. She looked down at me and said, "James, what I want to do is not okay."

"I want to do it too."

"You realize this is a line we can't ever cross back?"

I nodded my head and she looked at me, her face was one that I had seen many times as she thought things over, but this time was something much different than anything before. I gently reached my hand out, placing it on her knee and slowing sliding it upwards. "If you want to stop, I understand."

She continued to look at me, but as my hand reached the hem of her shorts, I paused, not wanting to go too far or pressure her. As my fingertips fiddled with the tight hem, I noticed Kelly bite her lip and then her hands started to move. I expected them to stop my hand and tell me that we should go to sleep, but instead they grabbed the hem of her sports bra and quickly pulled it over her head. I assume she threw it over on the floor because that's where it was the next morning, but I was too busy staring as her breasts settled without support. As I said before I knew Kelly bra size, and on her frame, they were a perfect size. Her areolas were the size of a half dollar with small nipples hardening and protruding outwards.

"Now we are evenly dressed."

I slid my hand over her shorts, bringing it to the juncture of her leg and pelvis before gently squeezing; she took a breath and closed her eyes. I moved my hand off her leg, shifted to my side and propped my head up, putting my eyes just below her breasts. I reached out and pulled her closer to me; I adjusted so my head was basically in her lap and lifted my head to her breasts, and softly took her nipple into my mouth, sucking on and gently nipping at it, eliciting another moan from her.

I felt her hands cradle my head, pulling me into her chest as she said, "That feels so good."

I let her nipple fall from my mouth, looked up at her sand said, "I'm glad." Scooting a bit further, I was able to take her other nipple into my mouth and repeated what I had done to the other one, causing her to moan once again. I continued alternating between each breast, paying attention to her nipples and surround flesh; as I did, she began to wiggle her hips in pleasure as she continued to coo and moan. I felt her grip loosen on my head and then felt her hand on my side, where it began to fiddle with the waist of my shorts.

I gave her nipple one more good nip, then pulled my head from her chest, "Are they in your way?"

"Just a little bit, I want to see what I felt earlier." She gently pushed my shoulder, causing me to fall onto my back. "Mind if I turn a light on?"

There had been some residual light from the window, but not a ton so wanting to take her in completely I said, "Of course."

She reached over me and turned bedside light on, as she did, I ran down her bare sides to her ass, giving it a squeeze, relishing in the fact that it was a firm as it looked. She squealed and sat up, then moved in front of me and as she reached out said, "Lift." As I did what she said, she pulled my shorts down, depositing them behind her. He eyes got a bit bigger and she began to stroke my erection, "Wow, you have a beautiful cock."

I blushed because I am slightly above average at a little over 7" and thanked her. She scooted between my legs and licked her palm and resumed stroking my cock slowly; with her other hand she began to cup my balls in her hand, causing me to groan. When I opened my eyes, I saw her focused on me and my face, maintaining what she was doing as I continued to groan and began to squirm under her touch.

She kept this up for a minute or two before she grinned and said, "Do you want me to stop?"

"Not unless you're going to take you shorts off."

She smirked and let go of my cock, "I think that can be arranged. She raised up straight and slipped her fingers into the waist of her shorts and began working them down her thighs. Once they were almost to her knees, she sat back and keeping her legs shut so I couldn't see anything, slipped them the rest of the way off, dropping them on the floor. Returning to her knees I noticed a well-trimmed bush above her slit, but what appeared to be a bare slit.