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Introduction:

This is the true story of my frist time with a man and my frist time wearing womens panties. I hope you enjoy

My awakening
This is the true story of my first time with a boy and my first time wearing women’s panties.
I was raised by my grandma who was a real conservative woman who sheltered us a little to much.
One day while sitting in my room playing video games my grandma came in and said One of my great uncles passed away. He lived in a different state so I never meet him, but since he was her brother she had to go help with funeral arrangements.
No I protested I will miss my ball game. We were one game away from going to the finals.
I already made arrangement for you to go stay with Jennifer and I will be back in a few days she explained.
Jennifer was her friend from work. She has two kids Frank who is also my older brothers best friend and Katie who lives with her dad since there divorce.
Since my brother was off at college it would be just me Frank and Jennifer there. Even though Frank and my brother never really hung out with me he was always nice so I didn’t mind.
I quickly through a few think in a bag and we were off.
We arrived shortly after 7pm and Jenifer had just finished dinner. I sat my stuff in Katie’s room where I would be staying since she wasn’t there this weekend and went and ate.
After dinner Frank and I were watching a wrestling movie and like normal boys we started wrestling.
During our wrestling match I bumped the table and red Kool-Aid spilled all over me.
Jennifer sent me to the bathroom to get cleaned up and changed and that’s when I notice the only thing I packed was my baseball gear. No underwear no sleeping clothes. I called for Jennifer and told her the issue.
I’ll put your clothes in the washer and try to find something that will fit you she said.
Ok
I jump in the shower and wash off then get out while drying off Jennifer comes to the door. I wrap the towel around me then tell her to come in.
I’m sorry Matt but the only thing I could find that might fit you is some of Katie’s underwear that I bought and were too big for her.
What I can’t were girl’s underwear I protested.
Well you can’t run around naked either so you’ll just have to deal with it since you didn’t pack anything to wear. She laid the panties and one of Franks t shirts down on the sink and left the room.
So, there I was standing in my older brother’s friend’s house and basically being forced to wear girl’s panties.
Hurry up I hear her shoot you need to get in bed.
I grab the panties and look at them. They were white with pink floral print and pink bands. I slowly put them on and as I slid them up my legs I noticed how different they felt than my underwear. Once I had them on I was amazed at how great they felt. I started to get hard instantly. I looked at myself in the mirror and noticed how my butt looked. The bikini cut panties covered only about half my cheeks and I couldn’t help but think how my butt looks a lot like my step sisters. (I had seen her in panties numerous times growing up). I put the shirt on which I was happy to find was way too big for me and went down almost to my knees.
I exit the bathroom to find Jennifer waiting.
Hand me your clothes and I will sook them tonight and put them in the wash tomorrow then we will go by your house and get you some clothes.
Do you want to watch a movie with us before bed she asked?
Sure
We go into the living room and Frank Starts the movie. I laid down on the floor facing the tv with my hands propping my head up. Frank and Jennifer was on the coach behind me.
About halfway through the movie Jennifer gets up and says I’m going to bed you boys don’t stay up to late. Then she looks at me and says with a grin you may want to pull your shirt down your panties are showing.
Oh crap I thought, I was so into the movie I forgot I was wearing panties.
I pulled my shirt down and went back to watching the movie.
I must have dosed off because I woke up when I felt something touching me.
When my eyes opened, I saw Frank beside me. He had my shirt pulled up and was staring at by butt while gently rubbing it. He hadn’t noticed that I was awake and his hand felt kind of good rubbing my butt so I just let him keep rubbing me.
Know at this point in my life I knew about sex but had never heard the term gay or that men had sex with men. I was confused as to why Frank was rubbing my butt. I figured it must be because my butt looks like a girl butt in panties. More confusing was why did I like it. I felt my thing getting hard as i enjoyed the feeling of his hand gently rubbing across my butt cheeks and down my crack in-between me slightly parted legs and back up.
As I felt his hand going back down my crack I lifted my butt up and spread my legs a little more. This caused Frank to pause and he noticed that I was awake.
He quickly removed his hand saying sorry.
Why were you rubbing my butt?
I couldn’t help it he explained. Your butt looks so cute in these panties that I just had to know feel it, and your butt felt so good I couldn’t stop.
Please don’t tell he pleaded.
I won’t tell in fact it kind of felt good.
Do you want me to do it some more he asked?
I shook my head yes and he placed his hand back on my butt.
Not being worried with waking me he rubbed a little harder. I spread my legs and lifted my butt up a little and his hand went down in-between my legs and under tell his fingers were on my thingy.
It felt so good I let out a soft moan. Encouraged by my sound he rubbed it a little then moved back to my butt. I found myself starting to rock my hips up and down as he continued rubbing me. As I did I felt his hand going under the leg band of my panties. I didn’t want this good feeling to stop so I just allowed him to. Then he started rubbing my butt under my panties then down to my bare thingy then back up only this time as he was bringing his hand back up his fingers went into my crack and he started rubbing my butt hole.
What are you doing?
Shh just relax we don’t want to wake mom he said.
I lay my head back down as he continues to alternate between rubbing my little hole to rubbing my thingy. I was really starting to enjoy his fingers rubbing my butt when he removed his hand.
Thinking he was done I was feeling a little disappointed then I heard what sounded like him spiting then he placed his hand back in my panties. I felt something warm and wet on my hole as he resumed rubbing. I quickly realized it was his spit. Eww I didn’t want his spit on my but before I could protest I noticed how much better it felt. I relax and lift my butt up a little more really starting to enjoy his fingers rubbing my hole. I started to let out more soft moans. Then I felt his finger start to enter my hole a little. I felt weird but didn’t hurt so I didn’t protest.
He continued probing my hole with the tip of his finger for a while then he pulled his hand back out of my panties and asked me if he could pull my panties off.
Not sure why I just shrugged my shoulders.
He grabbed the hem of my panties and slowly pulled them down. Then he placed both hands on my butt spreading my cheeks apart and bent down and started licking my butt hole.
I gasped as I realized what he was doing and was surprised by how great it felt.
He continued tonging my hole for a few minutes stopping only to ask if I liked it.
Yes I replied.
Then I felt him spit on my hole then started rubbing it again with his fingers. Only this time as he was probing my hole he started to push his finger farther into my butt.
Owh that hurts.
Just relax he replied. I promise it will feel good just push out like your trying to poop while I push in.
I did as instructed, and I felt his finger sliding in deeper. It still hurt but pushing out helped a lot. As his finger got all the way inside he said ok just relax know.
He reached under my hips with his other hand and started to rub my thingy with his finger still in my butt. After a few minutes the pain went away and it was starting to feel good. I started to move my hips up and down both humping his hand and causing his finger to move around in my butt.
Liking my movements, he started to pull his finger out then push it back in. He would also wiggle his finger around which really felt good.
Moaning loader, he had to remind me to keep it down so we don’t wake his mom.
Sorry I said it just feels so good.
After a while he started to push a second finger in my butt. The pain returned. But remembering his instructions and how great one finger felt I just relaxed and allowed the second to enter.
It wasn’t long before his fingers were moving freely in my butt and the feeling was incredible.
He removed his hand from my thingy and pulled his boxers down. I was surprised by how much bigger he was than me. (Though he wasn’t huge maybe six and a half inches). But I thought it was. Up to this point the only hard thing I had seen was mine though I had seen my brothers soft a couple of times.
He started to rub his thing. As he did he started moving his fingers in and out of my but really fast.
Oww god I cried that feels good.
He stops and pulls his fingers out and leans over and askes can I put my dick in your butt.
What? Why would you want to do that?
He said because it would make him feel as good as he was making me feel.
Nervously I agreed.
He moved behind me and spit on my butt again and also some on his thingy. Then he placed the tip at the entrance and started to push in.
Oww oww stop it hurts.
He apologized and started to just rub his thing up and down my crack.
I don’t know why but having his thing rubbing in between my cheeks felt so much better than his hand.
He then lined the tip back up with my hole. This time slowly pushing in then backing off.
As he did I was determined to let his thing go in me so he could feel as good as me. I arched my butt up, reached back with my hands to spread my check apart and pushed out. I felt his thing slowly starting to slid in. It hurt so bad I was starting to cry.
Do you want me to stop?
No keep going.
He continued to push in and then I felt him pass through something I later learned was the anal ring and his thing started to go in easier but still with pain. Then I felt the hairs around his thing touching my butt and knew he was almost fully in. And then his hips were firmly against my butt.
Wow your butt is so tight it feels amazing. He said as he stays fully inside me. Let me know when you’re ready for me to start moving.
As my butt starts to get used to his size I till him its ok just be easy.
He slowly pulls back and pushes in. The feeling of his thing sliding in and out and how full my but felt was causing me to start to moan again even though it still hurt a little.
After a few minutes the pain was gone and he started to go faster. I could hear his hips slapping against my butt with each thrust. I arched my but up more to try and take him deeper and who it felt so good as I felt his tip going in so deep.
The feeling of his thing sliding in and out of my butt was more than I could take as I started to moan and shack then my body got tight and with a load moan I came. As I was coming down from the most incredible feeling ever I felt his tense up he pushed in as hard as he could then I felt his thing moving on its own as he pumped his seed into me. The feeling of his cum going inside me was amazing as shot after shot went into me.
Then he sort of laid on top of me not putting all his weight on me but keeping his hips firmly against my butt. After a few moments, I could feel his thing getting smaller and then slid out of my butt. He rolled over and said WOW that was incredible. You have such a great little but.
Herring his words and seeing how happy he was made me feel special. I smiled and said that was the most amazing thing I have ever felt.
We better get cleaned up and get in bed he said.
I agreed and pulled up my panties and went to the bathroom to clean up. I couldn’t believe how much he came inside me. Our how sore my butt hole was.
After cleaning up I went to Katie’s room and drifted off to sleep.
I woke up the next morning to the smell of Jennifer’s cooking.
I got up and went into the kitchen.
Frank was already at the table and smiled when he seen me.
Good morning, she said. Did you sleep good?
Yah I replied.
How’s your little butt this morning?
What I asked.
She explained I heard you two last night and when I got up to see what you were doing. Imagine my surprise when I saw Frank with his finger in your butt.
As Frank and I lowered our heads in shame she continued, I was going to barge in and beat the hell out of him but then I heard you starting to moan.
I can explain Frank cut in but was immediately hushed.
As I watched I thought you looked so cute with your panties pulled down and lifting your butt and moaning up while he fingered you that I decided to just watch.
You watched us?
Yep I sure did she said. As my head sunk down in shame. And it looks like you like taking it up the but as much as I do.
WHAT? You do that to.
Yep Franks dad use to stick it in my butt all the time. Though he wasn’t near as gentle with me as Frank was with you.
Now hurry up and eat. We don’t have time to go by your house to get clothes and yours are still in the wash so you will have to wear panties under your baseball outfit. I will Drop you off then run and get you some clothes she said.
More to come…….

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