I decided to rewrite the story of my first time because of all the grammar mistakes made. Plus i wanted to add some details that i had left out. Hope you enjoy.
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.
Frank continued to gently work the tip of his finger in and out. Pushing a little deeper each time. At first it just felt weird then he pushed his finger about halfway in.
“Ohh” I let out,” That hurts
“Shh, just relax and push out like you’re trying to poop when I push in. I promise it will feel much better.” He said.
Trusting him I did as he said. I felt his finger pushing in, I arched my but up and pushed out and I could feel his finger slid all the way in. It still hurt but not as bad.
Frank keep his finger in place and reached under me and started to rub 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 while pulling it half out and pushing it back in.
As my hole lessened up he started to pump his finger faster. And just like promised it started feeling really good.
Frank then stuck a second finger at my entrance and proceeded to push in. While the second digit went in easier there was still some pain that quickly subsided. Then the pleaser got even more intense.
Frank started pumping his fingers into me faster and harder which caused me to start rocking my hips up to take his fingers in as deep as they could go.
Then Frank leaned over and whispered into my ear, “Can I fuck you in the ass”
Even though I did not know much about sex, I knew exactly what he was wanting to do. Why, I thought to myself? I’m a boy not a girl. And why would he want to put his thing in my Butt.
I finally asked him why.
He replied, “Because your little ass is so hot and because it would make me feel as good as im making you feel. So, what do you say?”
I thought about it for a second. He did have a point. My but did look cute in those panties and he was making me feel really good, so it’s only fair I make him feel good as well.
“OK” I replied.
Frank then removed his fingers (leaving my hole feeling empty) stood up and removed his shorts.
Wow, Franks thing was huge (at least compared to mine). His thing was about six and a half inches and thick. I thought to myself, that will never fit inside of my butt. I was kind of scared because if his fingers hurt as bad as they did, how much pain would that thing cause.
Terrified I wanted to back out, but I was raised by the saying a mans word is his bond and if you make a promise you have to keep it.
Frank leaned over and gave my hole a few more licks then left a big glob of spit at the entrance. He then moved behind me, spit on his hand and rubbed the spit onto his thing. Leaning over I could feel the tip against my crack.
He whispered, “just relax, I promise I will take it slow.
While I trusted him, his words did little to ease the fear.
He placed the tip at my entrance and started to push in.
“oww oww oww, it hurts” I cried out.
Frank stopped and started rubbing his thing up and down my crack. Feeling his large member in between my check as he humped me felt amazing.
After a few minutes of humping Frank lined himself back up with my entrance.
With a new determination to let him stick his thingy in my butt, I reached my hands back and pulled my cheeks apart, raised my hips and just like before pushed out. I could feel his member start to slid in.
Just like with his fingers, Frank would push in a little then pull back out. After a few tries he had the head in, and it was pushing up against something that was keeping it from going further. I latter found out that it is called the anal ring.
Frank continued to gently push in and pull out, pushing a little harder each time tell with a sharp pain his thing finally pushed through.
Oh, it hurt so bad. But I kept my checks spread and my but, in the air, and Frank continued to push deeper into me. Just when I thought I couldn’t take it anymore; I could feel Franks pubs and I knew he was almost in. I clenched my jaw and pushed my butt up while he was pushing in tell I felt his hips firmly against my cheeks.
I have never felt so full. Having his thing inside of me, although it hurt, it almost felt as though it belonged there.
Just like with his fingers Frank held in place letting me get use to the intrusion.
“Let me know when I can go”, he said.
“ok” I replied.
After a few minutes, the pain was pretty well gone. I started to rock my hips up and down a little letting Frank know I was ready.
Frank pulled back almost all the way out. I could feel every contour of his swollen member as he slowly withdrew then he gently pushed all the way back in. He repeated this process a few times and each time my hole would loosen up a little more. Soon he was sliding in and out with easy, pulling almost all the way out and pushing back in as far as he could go.
Between the feeling of the fullness, his thing sliding in and out and what ever he was hitting in there it started to feel really good.
Frank continued trusting into me as I started to rock my hips to meet his thrust. A warm feeling of pleaser coursing through my body each time he bottomed out into my quivering hole.
Frank had to constantly reminded me to keep it down, but it was no use. As the rush of pleaser coursed through me, I felt like what can only be described as an explosion inside of me. I recognized this feeling from when I would play with myself, but this was far more intense.
My body started shacking, my muscles tightened up and started convulsing.
The convulsing inside my butt put Frank over the edge and with one final push as hard and as deep as he could go, Frank started Cumming.
The way Frank was pushing into me and squeezing my hips and the feeling of his of his thing jumping around inside of me while he unleashed his seed just prolonged my orgasm.
I collapsed onto the floor, with Frank laying on top of me, lightheaded, exhausted and in a state of absolute bliss.
We lay there for a minute breathing hard, neither of us saying anything.
I could feel his thing going soft inside of me until it finally slipped out. I felt a strange sense of disappointment that it was over. I wanted him to stay inside of me. I wanted this feeling to last forever.
Frank rolled off to the side of me, placed his hand on my butt and rubbed a little, then said, “That was amazing. You have a great little butt.”
I couldn’t help but feel a sense of pride as I replied, “yes it was”
Frank then said, “we better go get in bed before we get caught”
He then kissed the top of my head and pulled my panties back up over my butt, then gave it a little squeeze.
I got up and went to go to the bathroom. It felt like my legs were jello. My insides seemed vacant and hollow and it was at that time that I noticed my panties were completely soaked with cum.
I went to Katie’s room and grabbed a clean pair and hid the cum soaked ones. My new pair of panties were white with a purple floral pattern.
I went to the bathroom and got cleaned up. I could not believe how much cum Frank had shot inside of me.
I finished cleaning up and went to bed. The days events running through my head. I could help but feel a strange sense of satisfaction and pride about how I was able to take his thing inside of me and make him cum just like a girl.
The next morning, I woke up to the smell of Jennifer’s cooking. I got up; my butt was still a little swore reminding me that last night was not a dream. I walk into the kitchen and sit down at the table.
Frank was already at the table and smiled when I walked in.
“Good morning,” Jen said, “Did you sleep good?”
“Yes,” I replied
“So, how’s your little butt this morning?” she asked
A look of terror spread of Frank’s and my face as Jennifer explained,
“I woke up because I herd 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.
She continued, “I was so filled with shock and rage that I was just about to come in there and beat the hell out of you. Then I herd 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. It honestly reminded me of the first time Jim (Franks dad) fucked me in the ass.”
“What”, I said shocked by what I had just herd. Jim put his thingy in your butt too?”
“Yes” she replied, “and it cock. I think after what you experienced last night your mature enough to say it. And based on what I saw, you loved it as much as I did. All though Jim was not as gentle with me as Frank was with you.
We finished eating with very few words said. 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 and started to undress when I realized, she had called me little missy.
Why would she call me that? She knows I’m not a girl. Was she just teasing me? I looked into the mirror and I did look kind of like a girl standing there in just a pair of panties. I’ve always been short and thin and not just in the height category. The lack of a bulge in my panties made me look even more feminine. Then I started wondering what I would look like without the
bulge. I reached into my panties and pushed my thing between my legs. Wow I really do look like a girl now.
As all these thoughts were running through my head, then I here a knock on the bathroom door,” Your clothes still haven’t been washed yet, so hers you a clean pair of panties. Now hurry up young lady,” Jennifer said as she closed the door.
Why was she teasing me I asked myself as I climbed out of the shower. I looked down at the panties Jennifer had brought in and they were pink with white polka dots.
With all the questions swirling around in my head for some reason putting these panties on made everything seem alright, like I was meant to wear them.
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