Warm Interlude

My Awakening Rewrite

This is the story of my first-time wearing women’s panties.

I was raised by my grandma. She was a real conservative woman who believed the bible word for word. As a result, I was extremely sheltered from the shows I watched and music I listened too to clothes and even the kinds of friends I could have.

One day I was sitting in my room playing video games when my grandma had come in.

“Matt, she said, I have some bad news. Your great uncle John passed away this morning”.

My great uncle John was my grandma’s brother. I heard a lot about him but because he lived so far away, I had never actually meet him.

“That’s terrible” I replied.

“I have to go help with the funeral arrangements and will be gone for a few days” she said.

I chimed in, “But my game is tomorrow.”

I was on the baseball team and we were one game away from going to the state finals.

“I know”, she replied. “I made arrangements for you to stay with Jennifer while I’m away. So go ahead and get you bags packed, we will be leaving soon.”

Jennifer was my grandma’s friend from work. She also has a son and daughter. Her son Frank is my brothers’ best friend and Katie is her daughter, but she lives with her dad. I never really hung out with either of them, but Frank would on occasion let me tag along when he and my brother would go to the park or fishing.

Like most boys my age I went back to playing my video game instead of packing tell I herd my grandma shout, “are you ready yet? I don’t want to miss my flight.”

I jumped up and quickly through some things in my bag and was out the door.

We arrived at Jennifer’s house shortly after 7pm. My grandma and Jennifer talked for a few minutes the grandma kissed me good by and left.

Jennifer led me to Katies room. Since she was only there every other weekend there wouldn’t be any issue.

I put my bag on the bed then went to the kitchen for supper.

We made small chit chat at the diner table. Frank asked how my brother was doing in the Army. Jennifer asked about school and baseball.

After eating Frank and I started wrestling around. It wasn’t much of a challenge since Frank was 6’1 and muscular and I was 5’4 and 120 pounds, but it was still fun. That is until we bumped the coffee table and red kool-aid spilled all over me.

Jennifer yelled angerly, “You two get that messed cleaned up now! Then you (referring to me) go get in the shower and bring me those clothes so I can try and get the stain out.”

We got the messed cleaned up and I went to my room and that’s when I noticed that the only clothes I packed was my baseball uniform. No underwear, no socks, nothing.

I went to Jennifer and said, “I forgot to pack a change of clothes.”

Jennifer: “Well, go ahead and get in the shower and I will see what I can find for you.

“OK” I replied and headed for the shower.

As I finish my shower and start dying off, I hear a knock on the door. I wrap my towel around me and said, “come in”.

Jennifer comes in and say’s, “I’m sorry Matt, but the only thing that I have that will fit you is some of Katie’s underwear.”

“What, I can’t wear women’s underwear,” I protested.

“Well, you can’t go around naked either and since you didn’t pack any clothes you will just have to deal with it”. She said, then laid the panties and one of Franks t shirts down on the counter and left.

I could not believe it. I am basically being forced to wear girls’ panties. I’m a boy I thought to myself. I can’t wear these.

“Hurry up” came a shoot.

I reluctantly picked up the panties and looked at them. They were white with a pink floral pattern and pink leg bands.

I slowly put them on sand slid them up my legs. I immediately noticed how much different they felt than my whitey tighties and how differently I looked in them. The soft fabric was snug around my privates and the bikini cut only covered part of my cheeks.

As I stand there looking at myself in the mirror, I couldn’t help but notice how girly my butt looks.

Already embarrassed I quickly put-on Frank’s shirt which thankfully went down to my knees.

I exit the bathroom to find Jennifer waiting.

“Hand me your clothes so I can go put them in the laundry”, she said.

I hand them to her and go to the living room ware Frank was sitting.

“Were just fixing to watch a movie, want to join?” he asked.

“Sure,” I replied and went and laid down on the floor facing the tv.

When Jennifer came in Frank started the movie. About midway through the movie Jennifer got up and said, “I’m going to bed. You don’t stay up to late.” Then looking at me she said, “You may want to pull you shirt down. Your panties are showing.” She gave a little grin then left.

I was so caught up in the movie that I had completely forgot about wearing them. I pulled my shirt down and started watching the movie again.

I guess at some point I feel asleep because I woke up to the feel of some one touching me. As I came to I realized that it was Frank. He had pushed my shirt up and was softly rubbing my butt. Frank wasn’t aware that I had woke up and I just laid there quite and confused as he gently ran his hand from the small of my back down over my butt to the back of my legs then I could feel his fingers tracing then leg band of my panties then back up.

Now at this point in my life although I knew about sex my knowledge was very limited. I had heard the term gay but didn’t know what it meant or that boy’s can have sex with each other. So I was very confused as to why he was rubbing my butt. I guess its because it looks so girly, but why did it feel so good?

The questions and confusion keep swirling around in my head as I felt Franks hand at the top of my butt. He turned his hand so that the palm was at the top and his fingers were going in between my checks. He gently rubbed his hand down following the curve of my butt until his fingers were ware my legs connected. I don’t know why but for some reason I let out a soft moan and lifted my butt up.

This action startled Frank who was now well aware that I was awake.

“I’m sorry Matt, I didn’t mean to, I mean” he said stuttering his words.

“Why were you rubbing my butt?” I asked.

Continuing to stutter his words he replied, “ I didn’t mean to its just that, your butt looks so good in those panties. It looks just like a girls but. I just wanted to feel it. I’m so sorry. Please don’t tell, my mom would kill me.”

“I’m not going to tell”, I replied, “ it actually felt kind of good.

“It did?” he asked

“Yes” I replied.

“Do you want me to keep doing it?” he asked

I nodded my head yes and laid back down. That was all the invitation Frank needed. He placed his hand back on my butt and this time with out the fear of waking me rubbed me a little more firmly.

His large hands basically covered my entire backside as I lay there enjoying all the new feelings running through my body. He gently cups and squeezes my butt then continues rubbing up and down pushing his fingers into the crack of my panties covered hind end. His large fingers gently squeezing and rubbing me caused my thingy to get hard only adding to my confusion.

Why am I getting hard from having my butt rubbed? I thought to myself. It just didn’t make ant sense. But it felt so good.

Frank then added to my confusion when I felt his hand go in between my legs.

Instinctively I lifted my hips and allowed him access as he started to rub my hard thing then he would go back to my butt. He kept rubbing back and forth for a few minutes then I felt his hand go on to the small of my back and his fingers start to work there way under my panties.

What are you doing?” I asked

“Shhh, just relax.” he whispered as he continued working his hand into my panties.

I could feel his fingers making there way down my crack to my hole. When his fingertip rubbed against my hole a shiver ran through my whole body. I had never felt anything like that before.

Emboldened by my reaction he continued rubbing his finger against my hole, gently circling the hole with his fingertips then rubbing firmly across the opening.

Started to let out soft moans and rock my hips to meet his hand.

Frank leaned over and whispered in my ear, “dose that feel good?”

“MMM yeah” was all I could reply.

Frank then pulled his hand out and started rubbing across my panties again. Then with his hand back at the small of my back he started to push down my panties slowly.

Although I was still confused, I made no objection.

He pushed my panties down just below my cheeks then started rubbing my bare bottom and down under may panties to my bare thingy and back up.

He done this a few times then I heard something that sounded like him spiting. Then I felt his fingers return to my hole only this time they were wet.

Oh my god, I thought he is rubbing his spit on my butthole.

“How’s that feel?” he asked

“Gross” I replied, “but also kind of good”

He continued massaging my hole with his fingertip and it started feeling really good.

Frank then took both hands and spread my checks apart. Then I felt the stubble from is facial hair and something big and wet against my hole.

He’s not, Oh my god he is. He is licking my butthole.

But before I could even wrap my mind around what he was doing I felt this sudden wave of pleasure rush through my body. Lifting my hips up to allow better access, I was overwhelmed with the feeling of his tongue. I could feel it going around the rim then push into my hole and back around the rim.

With this new wave of pleasure, I was really startling to moan

“Shh” Frank said, “You’re going to wake up my mom.”

Trying not to moan so load with all the pleasure I was experiencing proved to be quite the challenge.

Then I felt Franks finger return to my now spit saturated hole. Only this time he wasn’t rubbing my hole, he was pushing the tip in.

“What are you doing?” I asked

“Just relax” He replied, “I promise it will feel good.

While still uneasy about it I let Frank continue. I didn’t know how it could feel good especially compared to his tongue, but I decided to trust him.