A gay adult story: My Awakeining by pantieboy1985 ,
True Story, Anal, Boy / Boy, First Time, Gay, Young
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.