Cassie
Copyright© 2025 by TheDarkKnight
Chapter 2: Just Horsing Around
Fiction Sex Story: Chapter 2: Just Horsing Around - I come from a family of teachers and educators, so becoming a teacher was what everyone expected of me as I was growing up. However, after I earned my degree and started teaching, I found that being around teens and tweens only fueled my formerly hidden perverse interests. I thought that taking a job as an online tutor might be the answer, then I met my new neighbor, Cassie. Frying pan, meet the fire.
Caution: This Fiction Sex Story contains strong sexual content, including Ma/ft Romantic Heterosexual Fiction First Oral Sex Petting Teacher/Student Slow
Cassie’s fifteenth birthday was a week after our totally inappropriate conversation. That Saturday, Gary took Cassie and some of her friends to a pizza restaurant, then bowling. Gary invited me, but the idea of spending the afternoon with a bunch of teenage girls, tempting as it was, didn’t seem like a good idea.
Cassie came over after they got back and brought me a slice of her birthday cake. “How was your party?” I asked.
“Good,” she said, “you should have come. Dad was kind of overwhelmed. My friends can be sort of ... rowdy.”
“Rowdy? Don’t hear that word much, outside of Texas.”
Cassie sighed. “I think there’s a cowgirl in me just waiting to burst out.”
“Ever ridden a horse?”
“Just a pony at a carnival when I was like five or six. I still have a picture of me in my cowgirl outfit, sitting on that poor pony that wasn’t much bigger than I was. Dad keeps saying he’ll take me to ride a real horse, but it never seems to happen. He’s always too busy.”
“What are you doing next Saturday?”
“Uh, nothing special,” Cassie replied, with a suspicious look. “Why?”
I don’t even know where the idea had come from, and it was still forming in my mind when I told her my plan. “I know where there’s a ranch not too far from here where people can go ride horses. Real horses, not ponies. I could take you there.”
Cassie smiled a lot, but when I told her that, she gave me an extra-special, whole-face smile that warmed my heart. “You’d do that for me?”
“I didn’t get you anything for your birthday, and I’d be doing it for me too. I used to ride when I was younger.” That was a slight lie. I had gone riding once with a college girlfriend. I managed to fall off twice before we both agreed that putting me on a horse had been a bad idea.
So, that was it. I asked Gary for his approval, and then went online to schedule our trip to “Maisie Clark’s Riding Experience.” The only reason I knew about it was from a former coworker who had taken his kids there a few times. It turned out to be a bit expensive for a part-time teacher like me, but there was no way I could disappoint Cassie.
On Saturday morning, I picked Cassie up, and we headed for our adventure. Just before we got there, I told her to get the big white box out of the back seat. She reached around, grabbed it and pulled it over the seat and onto her lap. “Open it,” I told her, as I was pulling into the long drive leading into the “Riding Experience”. When she did, I heard her take a breath and ask, “Is this for me?”
“I don’t think it’ll fit me,” I told her.
She reached into the box and pulled out the genuine cowboy hat, complete with a headband and feather, that I had bought her. She put it on, then looked at herself in the rear-view mirror. “This is amazing!” she said. “Where’s yours?”
I didn’t want to tell her that I had planned on buying one for myself, but the cost of riding and her hat had stretched my budget to the breaking point. “I don’t look good in a hat,” I said, which seemed to be a good enough excuse for her.
I parked in the Visitor Parking area. We were greeted by an older woman who looked remarkably like a real cowgirl, an unusual sight in Florida. “Hi ya’ll,” she said as we got out of the car. “I’m Maisie. You must be Mr. Simpson. And this sweetheart must be your daughter.”
“Oh, I’m not...,” Cassie began, but I cut her off. For some reason, it seemed better to let our host think she was my daughter. I was still dealing with occasional twinges of paranoia, even though there was nothing unusual about a young man taking a teenage girl riding.
“That’s us, ma’am,” I said, trying not to sound too much like a make-believe cowboy.
“Well, come on, let me introduce you to your rides.”
When I called to set up our lessons, Maisie asked about our experience, and when I told her we had almost none, she assured me not to worry, as she had a couple of older, gentle steeds for us to ride. One of her assistants, a leather-skinned oldtimer named Jake, took us to meet our horses. It had been a long time since I had been up close and personal with a horse, so these creatures seemed huge. Cassie looked almost like a little kid next to them, but she didn’t seem to be at all intimidated. She started petting her horse on the nose, which seemed to please the large animal. She was off to a good start, while I was trying to work up enough courage even to stand next to my ride, which I swear I had seen on Game of Thrones.
Jake gave us a quick lesson on how to properly mount, dismount, and guide our rides. I started to tell him that I already knew a few things about dismounting, but decided to keep that story to myself. Callie picked up all the instructions right away, which didn’t surprise me. Before we even got on Mack (my horse) and Sapphire (Callie’s), she was already beaming. Jake gave her a hand up onto her mount, and I noticed he was taking a good look at her cute butt in the almost skin-tight jeans she was wearing. I couldn’t blame him. Being the perv that I am, when I saw her settle into the saddle, I couldn’t resist thinking about how widespread her thighs were. I don’t think I had been jealous of a horse before.
I had expected us to just ride around the corral a few times, maybe a more grown-up version of the pony ride Cassie had taken at the fair when she was a kid, but Jake told us to take a trail that led through a small pine forest behind the ranch. “They know the way,” he told us, “but it helps if you encourage them. Just keep a tight hold on the reins. Sometimes they see a snake and get spooked.” I knew the feeling. Mack stopped a couple of times for no apparent reason, and I had a hard time getting him going again, but Cassie had no problems with Sapphire. She was a natural rider.
When we returned to the stable, Maisie gave us a quick debrief. She was just being a good businesswoman, making sure that we had enjoyed ourselves so we might come back. Cassie asked her a lot of questions: How much does it cost to take care of a horse? Did she have any faster horses? Could she get a job caring for the horses? Maisie was patient enough to answer all of Cassie’s queries, then we said goodbye and headed back to the parking lot.
When we got to my car, I opened the driver’s door, but Cassie didn’t head for the passenger side. Instead, she followed me, then squeezed between me and the car while she tossed her hat into the back seat. I wasn’t sure what she was doing, but when she turned to face me, we were inches apart. She put her arms around my waist and hugged me. “This was maybe the best day of my life,” she said, “at least this year. Thank you.”