RIDING LESSONS

 

RIDING LESSONS

Growing up, my best friend and I shared two things, a birthday, and the agreement that the 

hottest woman on the planet was my Mom. It didn’t hurt that the older we got, the more open 

Mom got when it came to talking to us about sex. In fact, she was so open and honest with us, 

that when we were 17, my buddy confessed, on both of our behalves (to my HORROR), that we 

were both, at the very least, in LUST with her. Thankfully, Mom just laughed it off. She then 

informed him that, while he was very sweet, she didn’t touch anyone under the age of 18. 

Now… that was interesting phrasing, and it alone would have been enough to fill our every 

waking thought for the following year. But that wasn’t all, because every chance she got, for the 

next solid year, Mom was relentless in her teasing and flirting. Anytime she got us alone, she 

turned it all the way up. She even took to walking around the house braless, and later, in just 

panties and a t-shirt. That said, we did NOT complain. 

When we turned 18, I thought for sure that my buddy would confess his love/lust again; but when 

my Mom, very suggestively, asked him what she could do for him for his 18th birthday, he 

replied, “riding lessons”. Now, my Mom was great with horses, and her rich friend had this little 

beach-side house with a stable that Mom would often vacation at when no one was using it. But 

still... Recognize an opportunity bro! 

Still, a week after he turned 18, Mom took just the two of us to the resort, and I had to admit, 

seeing how naughty Mom’s flirting was going to get when she had days with just the 3 of us was 

something I was very much looking forward to! 

Then the first morning rolled around, and Mom greeted us with breakfast. Of course, she did so 

wearing a tiny half shirt that managed to be so small that if she were to yawn and stretch her 

large breasts would surely have been on display, and yet so large that the straps could not seem 

to stay on her shoulders. The material gave the impression of being too plentiful to stay in place, 

and too scarce to cover what it should. She was also wearing a tiny black skirt, a black thong, 

and knee high riding boots. I knew about the thong because when Mom bent over to grab her 

saddle off of the hallway floor (she brought her own), we both got a real clear view of just how 

short Mom’s skirt really was. 

Then she told us that it was time for my buddy’s lesson, and they left together. Honestly? I have 

never been so jealous. 

I was down at the beach, just hanging out, many, many hours later; when Mom rode up and 

trotted her horse into the water some. She did that after a good run sometimes, but, that wasn’t 

what was interesting to me. In fact, it wasn’t even the splash of water that I saw hit the front of 

Mom’s shirt, even though I knew she wasn’t wearing a bra. No, it wasn’t that, but after a second, 

Mom caught me staring, and gave me the most flirtatious and wicked grin I’ve seen. In a sexy 

purr she asked, “What is it sweetie?” But her innocence was barely feigned, and I was pretty 

damn sure she knew full well what I was looking at. 

For the record, I was looking at my Mother’s pussy. Because, even though she still wore her 

flimsy shirt, and her knee-high riding boots; that was now ALL that she was wearing. Her skin 

was glistening in the light, as little beads of sweat and seawater sparkled all over her body. Her 

firm ass was raised up by her spot on the horse, and from my angle, the full lips of her swollen 

pussy were naked to my eyes. I even thought, for just a second, that I might have been looking at 

creampie… at cum, leaking out of my Mom’s pussy lips. 

With a sudden heat in my brain like I’d never felt before, I managed to ask, “What um… What did 

you do today Mom?” Then she rode a little closer, still wearing that smile that was all sex and 

control, and she replied, in the sweetest tone; “Why… your best friend of course.” Right at that 

moment, my brain almost melted. I don’t think I could have possibly replied. Thankfully, Mom saw 

my plight, and did all the talking. “Like you, little (then she said my best friend's name), turned 18 

recently. Then, when I asked him what he wanted, he said he wanted to see me riding him.” She 

saw my confusion, but just smiled reassuringly, and continued; a silent promise that all would be 

explained. “Well, I told him that he was certainly old enough, but that I thought he should have to 

say so in front of you if he was serious. Well, later that day when I asked him in front of you, you 

heard his response… honestly, it was just cute enough, clever enough, and bold enough to get a 

passing grade from me. So, we set up this little trip, I took him to a nice secluded spot, laid him 

out on a blanket, and I fucked his brains out.” 

Mom was dismounting then, and walking up to me as she continued talking with a sexy sway to 

her hips that was magnitudes more powerful, now that she wasn’t wearing a skirt or panties. 

“Then,” she continued in a sultry purr, as she walked up to me, and draped her arms over my 

shoulders. “We had a little picnic, talked for a bit, and after awhile… I rode him again.” She was 

so close to me her breasts, through her wet shirt, were pressing firmly into my chest. Then she 

leaned in, and whispered into my ear. “Am I still your fantasy girl sweetie? Is that hot for you? 

Picturing your friend’s cock slamming up into Mommy’s tight little pussy… Me moaning for it? 

Hmmm?” Then she reached down, turned her hand, and gently cupped my balls while sliding her 

hand gently up the outline of my hard-on through my clothes. “Well?” 

I nodded so hard I thought I heard my brain rattle, but it was suddenly so hot inside my head, and 

I was finding it increasingly harder to breathe. It felt like being on the brink of orgasm while 

knowing that I was nowhere near it. 

“MMM…” Mom half-moaned into my ear. “That’s what I thought.” Then she said, “Tell you what 

honey. It’s your Birthday, so, just this once, how about if Mommy skips the teasing and just tells 

you exactly how this is going to play out? Would you like that?” Again, I tried to find words, but her 

hand moved again, and all I could do was breathe in sharply through my teeth and nod. “Okay 

slugger, here is what’s going to happen. I’m going to head back in, take good care of my friend's 

horse, and grab a shower. But, when I get out of that shower,  well, let me ask you a question; 

and, be honest… Have you ever pictured me going down on you while you were masturbating?” 

The moment she asked, she gripped my cock firmly in her delicate hand, and I couldn’t have 

admitted to it any faster. But she clearly didn’t mind. Because in response, she simply smiled 

and asked, “When I get out of the shower, would you like to see that for real?” I started to answer, 

but she wasn’t really asking anymore. She was just telling me what was definitely going to 

happen, and letting me play along. “That’s good honey. Because after tonight, you are never 

going to wonder what that looks like again. You are going to see your own sweet Mother’s face 

getting stuffed full of cock. You're going to hear Mommy moaning, and slurping, and when I’m 

done, you are going to get to see what your Mom looks like with her face slathered in hot cum… 

sound good?” She teased. 

But this time, when I answered, she released my cock and stepped away from me. Honestly, I 

didn’t want it to ever stop, but at the same time, I felt like I’d been holding my breath for an hour. I 

was struggling to breathe and all she’d done so far was touch me through my clothes. Then 

Mom got back on her horse, and shot me a wink. But before she left, she added, “Oh, and 

sweetie… We are out here for almost a week, just the three of us, so maybe start thinking about 

all the other things that you want to see you and your friend do to your Mom. Maybe make me a 

little list okay? After all, you boys are only 18 once, and I am just…” and then Mom gave a little 

shudder of pleasure, her eyes looking at me while filled with lust. “...SO ready for you two to 

make Mommy do all the things you want me to for your birthdays”.