It was an ordinary night when I received a text from my brother-in-law, Martin. He lives down the street and we’re close enough that our interactions are more like friends than family members. We often share messages throughout the day about things happening in our lives, but this night was different.
“Hey, what you up to tonight?” he asked.
“Oh, just watching some TV,” I replied, not thinking much of his message. “What about you?”
“Same. Just chilling at home. What show you watching?”
We started discussing our favorite shows for a bit and then he sent me a text that changed the entire tone of our conversation.
“I’m just imagining you sitting there in your PJs, watching TV,” he wrote.
I was surprised by his message but responded with, “I’m just wearing my usual sweatpants and tank top.”
He sent back a winking face emoji and I couldn’t help but laugh at the playful tone of our conversation.
“So what have you been up to today?” I asked, trying to change the subject.
“Not much. Just worked on some stuff around the house,” he replied. “What about you? Do anything fun?”
“Nope, just hung out with my kids and did some laundry.”
As our conversation continued, it took a slow but steady turn towards the sexual. Martin started asking me more personal questions, like what kind of underwear I wear or if I sleep in a bra. At first, I was taken aback by his questions, but then I realized I was enjoying this little game we were playing.
“You know, I’m really tired tonight,” he texted. “I might just go to bed early.”
“Oh yeah?” I asked, hoping for more information about his plans.
“I can barely keep my eyes open,” he replied.
“Wow, you must be really tired then considering it’s only 9:30,” I teased back.
He sent a laughing face emoji and then things got explicit.
“I don’t know how you do it with your kids always keeping you up,” he wrote. “But I guess that means you must have some good stamina.”
“Ha! Yeah, I guess so,” I responded, feeling my heart race a bit at his comment.
The back and forth continued like this for a while, each message getting more flirtatious than the last. At one point, he sent me a photo of himself in bed, looking relaxed and slightly disheveled.
“This is where I’ll be for the rest of the night,” he captioned the photo. “Hopefully without any interruptions.”
I couldn’t help but think about how nice it would be to crawl into that bed with him, feeling his arms wrapped around me as we drifted off to sleep together. But instead, I responded with a simple “Lucky you.”
“So what are you wearing now?” he asked after a few more messages back and forth.
I hesitated for a moment, unsure if I should continue playing this game with him. But then I thought about how much I was enjoying it and decided to go along with it.
“Still just my sweatpants and tank top,” I wrote back, copying his earlier message almost word-for-word. “What are you wearing?”
He sent me another photo, this time of him holding up a pair of boxer briefs.
“This is what I’m planning on wearing to bed,” he captioned the photo. “But who knows if that will actually happen.”
I couldn’t help but laugh at his message and decided to take things even further.
“Well, you better get those put on then,” I wrote back, feeling my face flush with excitement.
He sent me another winking face emoji and then our conversation took an even more explicit turn.
“So are you going to sleep in just your underwear?” I asked, hoping for a more detailed response this time.
“Oh no, definitely not,” he replied. “I’ll at least wear a t-shirt too.”
“What about me? What do you think I should wear to bed tonight?” I wrote back, feeling bold and daring in my sexting game.
He sent back three fire emojis and then we continued our flirtatious banter, each message growing more explicit than the last. Eventually, he even sent me a photo that allowed me to subtly see his slightly erect bulge coming up from his boxer shorts.
I took a screenshot of the photo and saved it to my phone before it expired and disappeared forever, knowing that I would probably never get another chance to see him like this again. Then I sent back a simple “I like what I see,” along with a few naughty emojis to match his tone.
As our conversation wound down for the night, we both agreed that we had crossed a line and should probably stop sexting each other before things got too out of hand. But despite our promise not to take things any further, I couldn’t help but feel a strange mix of excitement and guilt over what had just transpired between us.
As I drifted off to sleep that night, all I could think about was Martin lying in his bed down the street, probably with one hand on his cock while he looked at our naughty sexting messages, imagining all the dirty things we might do together if given the chance. And as much as I knew I should feel guilty for engaging in such a taboo conversation with my brother-in-law, I couldn’t help but wonder if maybe there was something more to this unexpected connection between us after all.
