A Trip to her Childhood Home
The next day was a trail ride with friends from her past. By lunch, I notice the same problem coming on. I was numb; even worse, I seemed to be withdrawing from the numbness. Imagine having to whisper in your wife’s ear that you can’t pee in the woods during a stop because you can’t get your dick to poke out. She died laughing, told me to squat like a girl, definitely loud enough for her friends to hear, and walked off. So I did. I squat I’m the woods, wiped the leftover pee off, and was going to pull my pants up when my wife’s ex walked up. Not a proud moment.
He said, “Sorry, I didn’t see anything, don’t worry. Hey, your wife mentioned you’re having trouble getting the correct position in the saddle. She asked me to help.”
I replied, “Yeah,” wondering if she had explained the situation, not sure if that mattered given what he walked up to.
“The first problem is these jeans aren’t the right cut,” he said. “See how mine is fitted?”
Of course, I could, given his junk was pronounced pressing against them. Damn, how’s that possible after riding? Then he showed me how to sit in the saddle. I thought like a guy needs to. Instead, he showed me how a girl should ride. This was embarrassing two-fold. First, I would find out later it made my problem worse, and second, the group, including my wife, spent the rest of the day snickering behind my back for ‘riding like a girl.’
Of course, that evening was a worse repeat of the last, with my wife mocking my ‘clitty,’ not wanting to grow while she got on top and ‘rode me like a girl.’ I don’t know what set me off, but when she said, “Ride you like a girl,” I came despite never being hard.
She giggled and threw me a t-shirt (I thought) to sleep in. In the morning, I would realize it was a nighty. I figured it was a mistake in the dark, laughed it off, and changed on my way to breakfast.
At breakfast, she asked if her ex had any tips for riding today. I blushed. She asked, “What happened?”
I explained how he walked up while I was wiping after squatting to pee.
She giggled before saying, “Oh my God, babe. I didn’t mean to do that. So what advice did he have?”
“He just told me my jeans weren’t the right cut for riding. I don’t even know what that means.”
My wife says, “I do.”
So we swing by the local clothing store. She explains how she knows exactly what jeans her ex wears. We buy a pair, and I change into them before the ride.
I was definitely taking a beating still in the new pair and told my wife as much. She dropped back and told her ex the update. We stopped for a break shortly after that, and they caught up with me. I swear I hadn’t seen them for a while, so I was glad they weren’t lost. As I get off, her ex says, “Hey, let me see the new pants. Your wife said you were still having trouble.”
I said, “Yeah, she bought whatever pair you usually wear.”
He said to my wife, “Well, there’s your problem. I said you need better-fitting jeans, not mine. I wear these because they cradle my package, which prevents all the pressure. I knew from looking at you that your jeans had too much room in the crotch.”
That made my wife snicker. I told them I couldn’t keep riding in this much discomfort. My wife said, “With where we are, it’s the same distance to go back as to finish, but I have a solution.”
She dragged me into the woods as the others whooped, assuming I was getting some sex. She dropped her jeans and panties. I asked, “Are we really gonna do this out here,” while taking my pants off.
She laughed and said, “Yeah, right, as if you could even get it up.”
She grabbed my crotch. Her hand felt incredible. It felt even better when she twisted my nipple while she flicked my mostly inverted dick like a clit. I moaned, and she laughed, so I dropped to my knees to go down on her before I came too soon. After I got her off, I realized I’d gotten an erection. So did my wife as she pushed me down to mount. I entered her without any resistance, which was weird. She was so loose (from being turned on?) I couldn’t feel her. She couldn’t feel me either reaching down to see what was up. She only said, “Oh, here, this seemed to work the other night just as well.”
She pulled me out and began to grind her clit on my dick. I came after maybe two strokes this way. She used my boxers to clean up and threw them into the woods.
I said, “I guess your solution doesn’t involve underwear. Not sure that’s gonna help.”
She said, “No, we’re gonna swap pants. I don’t need my package to be cradled, so the baggy crotch is no big deal.”
I was beside myself and said, “I’m not wearing your pants. They’re for women, plus tight jeans directly against my package is not gonna feel good.”
She giggled and said, “I know. That’s why you’ll need to wear my panties too,” holding up her silky, lace, black thong. “That’s why we had sex. I thought you’d fit better with your balls recently emptied. I know how your little balls draw up into your body after sex, and your little clitty dick has already gone back to internally pointing at me.”
She was right. I looked ridiculous.
She said, “Listen, everyone will get a kick out of this, and I bet it helps. Just do it.”
So I grabbed the panties and started sliding them on. Of course, I looked just like a woman in my compact state in the front. I mean, next to no bulge.
That, of course, is when her ex walked up to check on us. “Holy shit,” he said. “Why didn’t you say your spouse is a woman? We’re not that backward here.”
My wife says, “He’s not a woman. He’s just smaller than you.”
Her ex replies (while I remain frozen in embarrassment), “It couldn’t be small enough to look like that in panties. Plus, you told me you missed sex with a cock when we did it back there.”
My wife replied (not realizing she was admitting to cheating on me), “No, I said I missed sex with a real cock. Look, he’s a man…”
She then reached over and yanked mine (I mean her) panties down, revealing me in all my glory. He seemed genuinely shocked before finally saying, “I’m sorry, dude. I didn’t even know that was possible.” He turned and walked away.
My wife said, “Alright, pull your panties back up and get those jeans on before anyone else wants a show.”
To no one’s shock, my wife’s jeans fit me well. Even in the crotch. My final blow was my wife’s comment on the way home.
She said, ‘We might need to ride horses more. I think I prefer your clitty small enough to fit in panties and women’s jeans. Just looks right for you.”
*This story has been edited to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story was submitted directly to this website.