My Grandma and Jennifer’s Family Connection

My grandma’s words still lingered in my mind as I sat in my room, lost in the virtual world of my video game. “Matt, I have some bad news. Your great uncle John passed away this morning.” I replied with a sympathetic tone, “That’s terrible.” My grandma continued, “I have to go help with the funeral arrangements and will be gone for a few days.” I chimed in, “But my game is tomorrow,” referring to our upcoming baseball game, which would determine if we’d advance to the state finals. My grandma reassured me, “I know, I made arrangements for you to stay with Jennifer while I’m away.” Jennifer was a friend of my grandma’s from work, and her daughter Katie lived with her father, but her son Frank and my brother were close friends. I had never really hung out with them, but Frank would occasionally include me in their park trips or fishing excursions.

I went back to playing my game, but my grandma’s voice interrupted my concentration. “Are you ready yet? I don’t want to miss my flight.” I quickly packed a few essentials and headed out the door. We arrived at Jennifer’s house shortly after 7 pm, and my grandma kissed me goodbye, leaving me in Jennifer’s care. Jennifer led me to Katie’s room, as she was only there every other weekend, and we wouldn’t disturb her. I put my bag on the bed and headed to the kitchen for supper.

Over dinner, Frank and I engaged in some light small talk, discussing my brother’s Army training and my performance in school and baseball. After eating, Frank and I started wrestling around, and in the heat of the moment, we bumped the coffee table, spilling red Kool-Aid all over me. Jennifer intervened, instructing us to clean up the mess before I took a shower to remove the stain. As I showered, I realized I had forgotten to pack any clothes, only my baseball uniform.

“I forgot to pack a change of clothes,” I said to Jennifer, who replied, “Well, go ahead and get in the shower, and I’ll see what I can find for you.” I showered and dried off, still wearing my towel, when Jennifer entered the bathroom. She said, “I’m sorry, Matt, but the only thing that I have that will fit you is some of Katie’s underwear.” I protested, “I can’t wear women’s underwear!” Jennifer firmly said, “You can’t go around naked either, and since you didn’t pack any clothes, you’ll just have to deal with it.” She laid the panties and a t-shirt on the counter and left.

I couldn’t believe my eyes; I was being forced to wear girls’ panties. As I reluctantly put them on, I noticed how different they felt from my usual tighty-whities. The soft fabric was snug around my privates, and the bikini cut only covered part of my cheeks. I looked in the mirror and couldn’t help but notice how girly my butt looked in the pink floral pattern panties.

Jennifer told me to hand over my clothes so she could put them in the laundry, and I went to the living room where Frank was sitting. He asked if I wanted to join them in watching a movie, and I agreed. As we watched, Jennifer reminded me to pull my shirt down, as my panties were showing. I felt embarrassed but tried to ignore it and focus on the movie.

At some point, I must have fallen asleep, because I was jolted awake by Frank’s touch. He was softly rubbing my butt, and I was confused as to why he was doing it. I didn’t know what to make of it, but it felt…good. Frank continued to rub my butt, and I let out a soft moan, lifting my hips up. He asked if it felt good, and I replied, “Yeah.”

Frank’s actions only added to my confusion, and I didn’t know what to expect. He started rubbing his hand between my legs, and I felt a surge of pleasure. I let out soft moans and rocked my hips to meet his hand. Frank whispered in my ear, “Does that feel good?” and I replied, “MMM yeah.” He then pulled his hand out and started rubbing across my panties again, before pushing them down and exposing my bare bottom.

Frank’s fingers returned to my hole, this time wet, and I felt a wave of pleasure. I thought he was rubbing his spit on my butthole, but it felt…good. He asked if it felt good, and I replied, “Gross, but also kind of good.” Frank continued to massage my hole with his fingertip, and I felt myself getting more and more relaxed.

Frank spread my cheeks apart, and I felt the stubble from his facial hair and something big and wet against my hole. He was licking my butthole, and I felt a sudden wave of pleasure. I was moaning, but Frank told me to be quiet, so I wouldn’t wake up his mom. He continued to lick me, and I felt myself getting more and more turned on.

Frank’s finger returned to my now spit-saturated hole, and he started pushing the tip in. I felt a slight pain, but it quickly subsided as he continued to gently work his finger in and out. He asked me to relax and push out like I was trying to poop, and I did as he said. His finger slid all the way in, and it felt…good.

Frank kept his finger in place and started rubbing my thingy while my body got accustomed to the intruding digit. After about a minute, my butt muscles started to relax, and Frank started to wiggle his finger around. He then stuck a second finger at my entrance and proceeded to push in. I felt a slight pain, but it quickly subsided as he continued to pump his fingers into me.

Frank leaned over and whispered in my ear, “Can I fuck you in the ass?” I knew exactly what he was asking, and I thought to myself, “Why would he want to put his thing in my butt?” I asked him why, and he replied, “Because your little ass is so hot, and it would make me feel as good as I’m making you feel.” I thought about it for a second, and he had a point. My butt did look cute in those panties, and he was making me feel really good, so I agreed.

My body still reeled from the events of the previous night as I lay in bed, Frank’s words of praise echoing in my mind. “That was amazing,” he had said. “You have a great little butt.” I couldn’t help but feel a sense of pride, knowing that I had been able to take his thing inside of me and make him cum.

But the morning brought a new reality check. As I woke up to the smell of Jennifer’s cooking, I was reminded that I still had to face the world outside our little bubble. And to make matters worse, Frank’s mom had witnessed our little encounter.

“Good morning,” Jen said, as I walked into the kitchen. “Did you sleep good?”

“Yes,” I replied, trying to brush off the awkwardness.

“So, how’s your little butt this morning?” she asked, a sly grin spreading across her face.

A look of terror spread across both Frank’s and my face as Jennifer continued, “I woke up because I heard a noise last night and imagine my surprise when I look into the living room and see Frank with his fingers in your butt.”

“I can explain,” Frank tried to cut in, but was immediately silenced by his mom.

“I was so filled with shock and rage that I was just about to come in there and beat the hell out of you,” Jennifer said, her voice dripping with amusement. “Then I heard Matt’s moans and stopped, and I got to say Matt, you looked so cute with your panties pulled down rocking pushing your little hips up to meet his hand.”

“What,” I said, shocked by what I had just heard. “Jim put his thingy in your butt too?”

“Yes,” she replied, a hint of a smile on her face. “And it hurt. I think after what you experienced last night, you’re mature enough to say it. And based on what I saw, you loved it as much as I did.”

We finished eating in silence, the tension in the air palpable. Then Jennifer looked at me and said, “You better hurry up and go get ready, little missy, or you’re going to be late for your game.”

I went into the bathroom, my mind reeling with questions. Why had Jennifer called me little missy? Did she know what I was thinking? And then I saw my reflection in the mirror, standing there in just a pair of panties.

I looked like a girl. The lack of a bulge in my panties made me look even more feminine. I reached into my panties and pushed my thing between my legs, feeling a sense of wonder and curiosity.

“Your clothes still haven’t been washed yet, so here’s a clean pair of panties,” Jennifer said, knocking on the bathroom door. “Now hurry up, young lady.”

I took the panties, feeling a sense of unease and uncertainty. Why was Jennifer teasing me? And why did I feel like I was meant to wear these pink panties with white polka dots?