Riding With Mom
by alwayswantedto
Copyright© 2022 by alwayswantedto
My father had promised me a trip when I finished college. He said it was a good idea to get away from it all to give yourself a chance to reset your mind. I knew my father had traveled in his youth, so I was pretty geared up for where he was going to send me, at his expense. I had visions of hitting all the sunspots, VISA and booze in hand, and girls waiting to take their place.
Ahhh, but not so fast, Roger. The promised land doesn’t always meet your expectations. As it turns out, my trip around the world was an eight day wilderness horseback excursion with Ma and Pa Hamilton. That’s right. After four years of college, straight out of school, my rite of passage was a ride about with mommy and daddy aback some sweaty old nag batting away horseflies. Swell!
My father, on seeing my disappointment, confided that this was my mother’s idea, that she really wanted us to be together on our last family vacation. I was, under no circumstances, to display anything but the greatest enthusiasm, for my mother’s sake. After all, he said, “I think you’ll find it far more rewarding than you think.”
He followed up those prophetic words with a further promise to fund a trip to Europe, if I behaved myself and made Mom happy during the trip. So I resigned myself to another week or so of drudgery. After all, I’d made it through college telling myself I could take anything for four years. What’s another week and a half?
As trip time approached I learned, not surprisingly, that the horseback adventure was really my father’s idea, something he’d always wanted to do. Mom had wanted us all to go to Europe. But my father usually got his way, typically awarding himself brownie points for fulfilling the wishes of others while he was at it.
So it was that we ended up in the foothills of the Rocky mountains on three horses provisioned for ten days of solitude in the wilds. Neither Mom nor I were happy to learn that we were on our own in the wild outdoors without guides. There were rustic cabins along the route equipped with sleeping bags, food, feed for the horses, and other supplies. We carried only our clothes and emergency provisions in our saddle bags.
And so we were off. My father leading the way, full of vigor on his sparky steed followed by his less ecstatic troop aboard their mellow plugs, as befitting their lower equestrian experience. By the afternoon, I did have to admit that the countryside was stunning. Rolling alpine meadows sprinkled with flowers against a backdrop of snowcapped peaks I’d only seen in pictures and movies. Completely alien and wonderful compared to the corn fields of home.
Along the way, we stopped for snacks, laying in the wild fields, once beside a small stream, reveling in the spectacular beauty that surrounded us at every point of the compass. I began to feel that perhaps this trip wouldn’t be that bad, after all. Although we had been late leaving that morning, we easily reached the cabin we were to spend our first night in, set in a hillside within a clump of trees. We sat outside in the primitive wooden chairs drinking wine as the evening fell, gazing at the valley below and the craggy peaks beyond.
It was a very romantic setting, and I offered to set up a tent if Mom and Dad wanted the cabin to themselves. Mom laughed, saying that there’d be no need for that. Dad looked uncomfortable and disgruntled, muttering something and standing up to walk away a distance to take in the vista on his own. Mom quietly said, “Things have changed a little since you went to college, dear. Your father needs to do this. He isn’t the man he used to be.” She went inside without further explanation.
Feeling a little awkward, I checked to see that the horses were secure in the little corral and then headed into the cabin myself. When I entered, Mom was just slipping into her sleeping bag on one of the rustic, hand-hewn bunks. All of the sleeping quarters were in the same room. In the dim lantern light, the shadows played over her bare arms and legs, and the hem of her nightdress pulled high as she slid her feet into her bag. She zipped up the side of the sleeping bag part way, leaving a flap open across her tummy, the pink cotton material resting softly over her breasts as she leaned on her right elbow, facing me.
“Try to make your Dad happy on this trip, Roger. It’s very important to him.”
“I know, Mom. I will.”
She laid back, curling her arm across her forehead, stretching her nightie over her breasts. “Oh, God, I’m stiff,” she said. “I’ll be sore tomorrow.”
So am I, I thought, but not just from the horse. On the excuse of visiting the outside premises, I left, passing Dad on the way out.
“Goodnight, son. Check on the horses, will you?”
“Sure thing, Dad,” I replied, quickly slipping by in the doorway facing away from him to hide the boner that had exploded in my pants so suddenly at the sight of my Mom. My face was red. This had never happened before. Why would I get a hardon seeing my Mom in her nightdress, something I’d seen probably hundreds of times before? It was ridiculous!
Outside, my dick refused to subside, and the picture of my Mom laying back, arm covering her eyes while her tits pressed against her light pink, flannel nightie, seared into my vision in true color HDTV. Walking around to the far side of the little coral, I pulled my dong out of my jeans and quickly jacked off into the grass. It didn’t take long. I was glad it was dark when I returned to the cabin. I made my way to my bunk without turning on a flashlight.
I opened my eyes to the sun filtering in through the window and the open doorway. Mom was cooking breakfast on the cabin’s little propane cook stove. Dad was nowhere in sight, out for a morning walk, I presumed. Mom was still dressed just in her pink nightie. I hadn’t made as sound as I awoke, and I continued to lay still, peering at her as she moved about. The nightie fell to about the middle of her back, lower than in front, and the hem was about mid-thigh level, showing off her well-exercised, tanned legs. Mom was a pretty nice woman for forty-something, pretty nice. There was something basic, almost primordial, being alone in a cabin in the mountains with an attractive woman. My cock started to swell. I turned more onto my stomach, forcing my stiffness against the wooden bunk, closing my eyes as my mother turned to look at me.
When I cautiously opened them just a slit a moment later, she was next to her bunk fishing around in her pack. She pulled out a new pair of panties. Lifting her nightie a little, she sipped her hands underneath and then slid her old panties down her legs, stepping out of them and then pulled the new ones up and into place. I caught a brief glimpse of her bare ass as the change took place. Next, she grabbed her riding pants and pulled them up under the nightie, pulling them up tight.
Glancing over her shoulder in my direction, she then pulled her nightie over her head, stretching her arms far above, providing me with a wonderful view of her smooth back, her narrow waist flaring out to her hips, and a hint of the side of her right breast, sloping down and then bouncing as she brought her arms down and tossed the nightie to the bunk. Picking her bra up from the pack, she slipped her arms through it and pulled it around to the front, squeezing her breasts in. I could clearly hear the snaps click into place, the room was so still. Finally, she picked up her pullover blouse and put it on, pulling it down tight. As she turned back to check on breakfast, I feigned waking, perhaps a little too obvious.
“Oh, there’s my boy. Finally. Come on, up and at ‘em.”
When I balked, looking around, she said, “Don’t be shy, I won’t peek. Anyway, I don’t think there’s going to be much room for privacy on this trip.”
Fortunately, she kept her back to me as I dressed because my dick would not listen to my silent reprimands. As soon as I got my jeans on, I walked stiffly outside, shirt in hand.
“A little sore, I see,” Mom laughed as I limped out the door, attributing my awkward gate to saddle sores.
After breakfast we saddled up and headed out. We expected a five hour ride to reach the next cabin, following a gently climbing trail through grassy meadows and thickets of small pine trees, just like the previous day. The scenery was even more fantastic than the day before, getting better and better as we climbed along the side of the mountains. We didn’t run into anyone. This was by design, as the outfitters only let one group leave every second day. We were pretty much guaranteed a trip with the wilderness all to ourselves.
When we stopped for lunch we dug into our stash of wine again. That is, Mom and I did. Dad couldn’t help but walk around. Mom and I laid back on our blankets, leaning on our elbows sipping wine, chatting and gazing about. It was soul cleansing, that’s for sure. My mind didn’t entertain thoughts beyond what I could see, and when Mom laid back, covering her eyes with her arm, allowing me to freely run mine over her figure, my thoughts remained very close by, indeed.
I couldn’t understand why I was checking my Mom out so much. Why I kept getting boners watching her, as I had on much of the morning ride as I watched her butt swaying in the saddle ahead of me. Was it because she was the only woman around? She hadn’t done anything to encourage me, though she definitely had a figure worth looking at. The stretchy riding breeches clung to her legs up and over her hips, outlining her buttocks in fine detail, and clearly molding the mound in front. The form fitting t-shirt she wore equally displayed her other womanly charms which, while not large, were firm and supple, and clearly hadn’t strayed long from the best days of their youth despite the calendar years of their host.
“It’s gorgeous, isn’t it?”
Startled, I jerked my eyes away from Mom’s breast up to her eyes which were regarding me, shading from the sun by her cupped hand held against her forehead.
“What?”
“There’s a real beauty, here, isn’t there?”
“Yes,” I stuttered as I recovered enough to speak, “yes there is.”
Had she noticed where I was looking? Had I been saved by the sun in her eyes? At that moment, Dad sauntered out of the trees fifty feet away.
“Let’s go, saddle up,” he called out. Mom and I struggled up, stiffly.
“I have to visit nature first,” Mom said and strode off toward the trees.
“You’ll have to catch up then,” Dad responded, then, to me, “Saddle up Mom’s horse and stay with her. I’m going to scout out ahead and give this filly a stretch. Those plugs of yours can plod along behind.”
“Ok, Dad. We’ll tag along.”
Mom emerged from the trees and waved to Dad as he trotted by. She walked up and put something into her saddlebag and then struggled to get on her horse.
“Roger, give me a hand. These old bones can’t do it by themselves.”
I walked to her side, and tried to lift her up by her elbow.
“No, give me a push. Come on, don’t be shy, give my butt a boost.” She stepped into the stirrup and started to lift herself up. I swung my open hand down and pressed it against the bottom of her ass as she started to rise, pushing up until she could swing her leg over the saddle.
“Thank you, sir. I think I might need a little push every time I get on this damned horse,” she laughed as she prodded her nag into a walk.
I quickly swung up onto my hardly more spry steed and nudged it into action, catching up and pulling abreast so we could ride side by side. There was something different about Mom, but I couldn’t quite put my finger on what it was. We rode along in silence, Mom surveying the scenery away from me to the right, but not turning away, sitting square in the saddle. Then I noticed. Her breasts were jouncing up and down, freely, bouncing along with the sway of the horse. A flash of her saddlebag entry shot into my mind. She’d taken off her bra while she was in the trees doing her business! My cock swelled up, throbbing against my jeans. She kept riding along, angled perfectly for me to watch her tits in their erotic dance, and her face turned away. Was she giving me a show? No. Impossible.
“Oh, God, it’s so beautiful, it feels so exhilarating,” she suddenly cried out in a throaty voice as she leaned back, pulling her elbows back to rest on the rear ridge of the saddle behind her, throwing her head back, arching her back and thrusting her tits up, the nipples expressing themselves strongly against the thin material of her shirt. I stared, riding along with my head moving up and down in time with the bounce of her tits. “It makes me feel so good.”
I couldn’t agree more. Despite the chance that she would suddenly look over and catch me staring, I kept my eyes fixed on her. She kept riding on, leaning back even further, almost lying on the horse’s rump. Her t-shirt pulled out of her riding pants, baring her belly with just a hint of fuzzy blondish hair reflecting the sunlight. What a sight. She seemed to be part of the wild scenery as she swung along beside me, until we could hear my Dad riding back toward us. Mom jerked herself up at the first sound of his approaching hooves, tugging her shirt down.
“Come on, you guys. You wouldn’t believe the scenery ahead.” He swung around us and sped off again, quickly leaving us behind.
As Mom watched him disappear, she turned toward me, smiling, “I think you and I will have to amuse ourselves a lot on this trip.” She laughed, a full throaty laugh, and spurred her nag into a trot.
I tried to catch up beside her to continue my observations, but my candidate for the glue factory wasn’t up to the task. Every once in a while, Mom teased me, turning to laugh, “Can’t keep up, young fella?”
We stopped for a snack when we caught up to Dad almost an hour later. He was waiting around a corner which opened to an incredible vista of craggy peaks. Dad waited for us to take it all in. When we got ready to leave, I reached to help mom into the saddle again but she declined, saying briskly, “I can get up myself, thank you. I’m not that old.”
Disappointed, I mounted up and fell in behind Mom, plodding along. The ride was uneventful and not particularly exciting. Beautiful country, to be sure, but I was more interested in living vistas with captivating forms of movement than landscapes. Then, Mom seemed to get tired. She leaned forward over the neck of her horse, with her hands falling to its shoulders and grasping its mane. She seemed to be resting. But the interesting side effect was that, by leaning forward, her butt was prominently displayed, the tan riding breaches pulling tight around her cheeks and clearly outlining her panties. It was as if she was kneeling on all fours, brazenly displaying her ass in tantalizing, repetitive little rocking motions. My eyes stayed glued to her butt all the way to the next hut.
That evening was a repeat of the night before. We sat outside in the pleasant, waning sun as darkness fell over us. Dad got up and went to bed, leaving the lantern on but turned down low. Mom stayed behind until we could hear Dad snoring softly. She didn’t talk, and neither did I. I felt tense, but didn’t know if she did. I was confused about the day’s events and didn’t know what to make of them. So I did nothing.
Finally, Mom got up and said, “Let’s go to bed, honey. Come on.”
I had been waiting for her to go in and get into her sleeping bag first, but I did as she asked, following her in. Dad was sleeping facing the wall with his gear strewn around him on their bunk. There was no room for Mom to put her sleeping bag unless she woke him to move his stuff out of the way. Mom walked over to the other double bunk against the far wall, “I guess we’re here, tiger,” she whispered.
She spread her sleeping bag out on the edge, whispering back to me over her shoulder, “I like the outside.” Then she sat on the bunk and motioned for me to pull her riding boots off. I pulled both boots off but she kept both feet up, so I pulled her socks off and threw them to the floor as well. Still, she kept her legs up, holding them together. With a soft smile on her face, she whispered so quietly I could hardly hear her, “I need help to get these off too, and Dad’s out of commission.” She looked down at her riding breaches and slid her right hand up to unbutton the top.
I grabbed the bottom of each leg and pulled, tugging several times, almost pulling her off the bed. She giggled as I yanked on her pants, ever harder, trying to pull them off. Resistance ended as her breeches cleared her hips and they suddenly slid quickly down her legs, up toward me, baring her legs right up to the bottom of her t-shirt. The breeches bunched around her ankles, her bare feet resting on my thighs. She slowly pulled her left foot out of her pants, lifting her knee, which opened her legs sufficiently for me to see under her t-shirt to her panties between her legs. She placed her left foot on the floor, leaving her right foot on my leg. She looked up at me, cocking her head slightly to the side, and said, “Hand me my pants, sweetie.”
I lifted her foot from my thigh and pulled her pants off, then stood there dumbly, looking down at her with her pants in one hand and her foot in the other. Despite the fact that I knew she was looking at me, I couldn’t help looking at her panties. I even moved her foot out to my side, without thinking, to open her legs to reveal more. I was having a hard time breathing. I pushed her leg out and her knee back toward her, opening her legs and stretching her panties tighter against her. She let me do it. I stood frozen, my eyes locked on the crevice faintly showing on the front of her panties, my cock swelling hard against my jeans. Her voice startled me, partly because it jolted me back to reality, and partly because it wasn’t angry.
“I need my foot if I’m going to get into bed, honey.”
I looked up to her face, she was smiling. Woodenly, I let her foot go and she swung her legs over to push her feet into the sleeping bag, bending them at the knees to do so. Although she didn’t need to, she opened her legs wide, pushing her t-shirt up to her hips and exposing her brief pink panties completely. As she slowly pushed her legs into the bag, they gradually closed but the shirt didn’t again cover her panties, and she didn’t pull the sleeping bag up to cover herself. “You’ll have to get undressed yourself,” she laughed in that throaty laugh again, one I hadn’t heard until today. “Don’t forget to turn off the light.”
I turned the lantern off but the cabin was still lit by moonlight. I quickly doffed my shirt, boots, socks and jeans, turning away to hide my swollen prick since she lay on her side, watching me. I found my sleeping bag and stretched it out behind Mom, having no choice but to lean over her to do so. I desperately hoped the dim light would hide the hardon bulging against my under shorts. Mom didn’t say anything. I clambered over her and awkwardly got into my bag, nestling in and laying on my side facing her back. Within a few minutes, she sat up, facing her feet. “I’m too hot,” she said. Crossing her arms to opposite sides at her waist, she grabbed the bottom of her t-shirt and pulled it up and over her head, her hair falling down over her shoulders as she tossed it on to the floor. She hadn’t turned away. I stared at her tits as they slowly bounced to a standstill, the nipples jutting out in the moonlight.
Mom sat there for several moments. Then, she stretched her arms behind her, bracing her hands against the bed and arching her back, like she’d done on the horses rump that afternoon. “I feel so alive out here,” she whispered.
I didn’t know if she was speaking to me, or if she thought I was facing against the wall. I stayed as still as I could, hoping for nothing to change, for the world to stay just as it was. I couldn’t believe how the slope of her tits, the curve of their undersides, the jut of her nipples, was so much more beautiful than all the incredible nature I’d observed that day. I could have gazed at them forever, and can still replay every minute movement in my mind, even now. Suddenly, she turned to face me, reaching out with her right hand to gently tousle my hair. “It is gorgeous, isn’t it, honey? Are you glad you came?”
I nodded, too numb to speak.
“So am I, darling.” She leaned over to kiss my forehead, her tits pushing on either side of my cheeks, her nipples brushing against my nose and lips as she pulled back at bit. “Give me a couple of bumps if you need to wake me,” she said, “you know, if you need to get up.” She snuggled down into her bag. Turning to face away from me, she pushed back until her rump was pressed against me. “Keep me warm tonight, baby.”
I snuggled closer to her, but kept my errant hardon pulled back. I couldn’t sleep for a long time, thinking about her body, clad only in little pink panties, pressed against me between our sleeping bags. I kept my arm around her until I fell asleep, keeping her pressed in against me.
I awoke during the night, reasserting my hold and pulling her in to me. My cock had somehow released itself from the confines of my shorts. If she hadn’t been sleeping, she would have had to feel it, but she didn’t move. Cautiously, I pushed it a little harder against her ass. When she still didn’t respond, I pushed again, a little more firmly. No reaction. I repeated the action several more times, slowly so as not to wake her, but more firmly each time, and stayed pushed against her for longer as well. I could always claim I was trying to wake her, I thought, as per her suggestion. Why had she provided me with such a convenient excuse? I lost this train of thought as I softly thrust and slowly ground my cock into my mother’s ass through the material of the sleeping bags. I kept grinding and holding my cock against her until I came, spurting all over the inside liner of my bag.
Only after the final spurt did I come to my senses. She hadn’t moved or responded in any way, thank God, but she hadn’t been breathing like she was sleeping either. She was just very, very still. I fell back, and eventually fell asleep, in my own mess.
When I awoke, Dad was gone again, and Mom was making breakfast. She was wearing a new t-shirt, a long one that stretched down below her bum. I think that’s all she had on, as the material was thin white cotton and I couldn’t see the line of any panties underneath, and she clearly wasn’t wearing a bra. Her tits sloped down in a slight sag, standing out from her belly against her shirt, her nipples jutting out like craggy little peaks. Mom’s legs were muscular. I could see the muscles tensing along the outside of her thigh and the tightening of her calf muscles as she moved about in her bare feet. Finally, she turned and saw that I was awake. She padded over to me, leant down and gave me a big kiss on my forehead, and then, to my shock, directly on my mouth.
But she acted as if nothing was out of order. “Hey, sleepyhead, it’s about time. Dad’s been up for hours. He couldn’t wait so I told him to go on ahead. Get up and eat while I saddle the horses.”
Mom grabbed her boots and put them on, then strode out the front door. I got up, pulled my jeans on and ate. Just as I finished, she came back in, grabbed a riding skirt out of her pack and pulled it on over her boots, tucking the t-shirt into it. She rolled her sleeping bag up, grabbed her pack and told me to hurry up. Then she laughed and said, “There’s clean sleeping bag liners in the cupboard over there.”
Shocked and embarrassed, I nonetheless did as she said and then rushed out after her. She must have known what I was up to last night. She couldn’t have been sleeping. But she’d let it happen. Holy shit!
Mom was already down the trail. I got on my horse and took off after her. We rode for several hours before Dad came up behind us. He’d gone on a little adventure on a side trail loop. About half an hour later we stopped for a short lunch. Dad was eager to get going because he wanted us to take another side trail loop because the one he’d just done had been so cool. And so we did. It was a longer loop with an overnight stay at a more remote cabin halfway around the loop. An hour after lunch, Mom’s horse came up lame.
Dad looked at the horse, picking her foot up, examining its hoof, and so on. “Well, we can’t do anything here,” he said. “You two will have to double up. You have to take things in stride out here,” he said, “You can’t whine about things, you just have to handle them.” He seemed almost happy at the opportunity to ‘rise to the challenge’.
So Mom got up ahead of me and we tied a lead for her horse to follow behind. Dad led the way. Doubling up soon became uncomfortable for me. Mom’s ass was right against my dick, moving back against it with each swaying step of the horse. I couldn’t help but get an enormous hardon. After a while, she leaned forward over the horse’s neck, grasping its mane to steady her self, as she had done the day before. This raised her ass allowing me to fit even tighter under her, closer to her pussy.
Soon, unable to stop myself, I started rocking my crotch forward into her, thinking I could blame it on the horse’s movement. Mom didn’t call me to task, so I became bolder until I was rocking into her hard enough to shove her forward a little along the horse’s neck. She turned her head to look back at me. Oh, oh, I thought, I’m going to get it now. But she only said, “‘Grab hold of me so I don’t fall off.”
I put my hands loosely around her waist to steady her but she put her hands over my wrists and pulled them forward, higher up above her waist until my hands were grasping the sides of her chest, right beside the swell of her breasts. Mom turned her head back down onto the horse’s neck and grasped its mane in her hands again. I slipped my hands further in and slid my fingers around the front of her breasts, splaying my fingers on either side of the nipple of each tit. I pushed my cock into her. She squeezed her legs on the horse’s shoulders and lifted her ass higher, providing even greater access for my bulging jeans. The lump there matched up with the rear of her pussy, and I pushed it in hard to make contact. I stood in the stirrups and started pushing against her, rocking her forward. There was no question about horse movements now, I was dry humping my Mom and she was letting me do it. I leaned forward, resting my head on her back, increasing the tempo of my thrusts, grasping her tits in my hands. Panting wildly, I finally came, pulling her back hard on my jean-covered cock.
I pulled back. Dad was further ahead. As far as I know, he never looked back. Mom lay as she was, still grasping the horse’s mane, breathing heavily. She hadn’t come, I’d left her hanging.
Dad stayed with us for a while longer but soon quickened his pace, pulling ever farther ahead. I looked down at Mom, leaning ahead, still breathing heavily. I grabbed the back of her riding skirt and pulled on it until it came free from under her. I lifted it up and looked down at her ass, at the line of her panty as it disappeared into the crack of her ass. The saddle below was slippery with her juice. I slid my right hand down, cupping it and pushing it up against her ass, slipping forward with my fingers along the bottom of her pussy.
“No, oh no!” She tried to get up but I kept her down with my left hand pressing into her back.
“No, Roger, don’t!” I ignored her, sliding my fingers back and forth from her asshole to her pussy, pushing ever further forward until soon I was rutting right through the crevice between her lips up to her clit. Back and forth I rubbed, back and forth, ending when my thumb pressed between her cheeks onto her little rosebud. I grasped her hair and tugged her back. She clenched her knees and pushed her ass higher up, giving me more room to savage her pussy with my hand, I stopped moving, holding my finger on her clit and mashing the bridge of my palm against her cunt lips, moving in a very small circle but pushing firmly against her. She was grunting. She started to fuck my hand. “oh, oh, oh, unngghhhh, unngghhhh, unnnggghhhhh, unngghhhh” until she was constantly moaning.
She got so wild, I thought she was going to throw herself off the horse. Christ, Dad must not have fucked her for ages. I knew he was older than her but had he stopped doing her altogether? How long for her to be this horny?
Finally, she came. She clutched my hand tightly, squeezing it in random, involuntary pulses, while she continued little fuck moves, slowly subsiding until she was still. She tried to get up but I stopped her. Leaning over, I whispered into her ear, “You’re beautiful, you’re so beautiful.”
I pulled back and tugged her up with me. I leaned back in the saddle, pulling her with me, my arm around her waist. Her head fell back against my shoulder, turning off to the side.
“Isn’t it gorgeous, Mom? Don’t you just love it out here?”
She was quiet for a moment, then she answered me, “Yes, I do, I do love it.”
Up ahead I could see Dad had dismounted for our afternoon break. Mounting. Dismounting. The words echoed in my head. I had some ideas for tonight.
Mom showed no discomfort or embarrassment during our afternoon snack. Her face was flushed, making her seem more beautiful than ever. Dad mentioned that the outdoor air was really seeming to agree with her. She laughed, a genuine, throaty burst of humor. “Maybe,” she said, “I think I’m just enjoying being alone with my men,” she laughed again, getting up and dancing away toward the trees.
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