My awakening
This is the true story of my first prison term with a boy and my beginning clock time wearing char's panties.
I was raised by my nan who was a substantial buttoned-down woman who sheltered us a little to much.
One day while sitting in my way playing video biz my granny came in and said One of my great uncles passed away. He lived in a different United States Department of State so I never meet him, but since he was her pal she had to go help with funeral arrangements.
No I protested I will pretermit my testicle game. We were one game away from going to the finals.
I already made arranging for you to go stay with Jennifer and I will be back in a few days she explained.
Jennifer was her friend from piece of 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 sidekick 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 decent 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 party. 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 hotdog and I were watching a wrestling movie and like normal male child 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 lone thing I packed was my baseball appurtenance. No underwear no sleeping apparel. I called for Jennifer and told her the issue.
I'll put your dress 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 drab lustrelessness but the exclusively matter I could witness that might fit you is some of Katie's underwear that I bought and were too big for her.
What I can't were daughter's underclothes I protested.
wellspring 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 hot dog t shirts down on the sink and left the room.
So, there I was standing in my old 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 step-in and looking at at them. They were E. B. White with pink flowered print and pink bands. I slowly put them on and as I slid them up my legs I noticed how unlike they felt than my underwear. Once I had them on I was amazed at how great they felt. I started to get concentrated instantly. I looked at myself in the mirror and noticed how my buttocks looked. The bikini cut panty covered only about half my cheeks and I couldn't service but think how my tail end looks a lot like my step sisters. ( I had seen her in panties numerous fourth dimension 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.
hired man me your dress and I will sook them tonight and put them in the wash tomorrow then we will go by your theatre and get you some clothes.
Do you want to catch a movie with us before bed she asked ?
Sure
We go into the living way and Frank Starts the movie. I laid down on the floor facing the tv with my hands propping my heading up. Frank and Jennifer was on the coach behind me.
About halfway through the film Jennifer gets up and says I'm going to bed you son don't stick 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 centre opened, I saw wiener 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 variety of good rubbing my hindquarters so I just let him hold on rubbing me.
Know at this degree in my life I knew about sex but had never heard the full term gay or that men had sex with men. I was confused as to why dog was rubbing my butt. I figured it must be because my butt looks like a young woman butt in pantie. Sir Thomas 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 peg a little more. This caused Frank to pause and he noticed that I was awake.
He quickly removed his helping hand saying sorry.
Why were you rubbing my butt joint ?
I couldn't help it he explained. Your border face so cute in these panties that I just had to know feel it, and your stub felt so good I couldn't stop.
Please don't William Tell he pleaded.
I won't tell in fact it sort of felt good.
Do you require me to do it some more he asked ?
I shook my head word yes and he placed his handwriting back on my backside.
Not being worried with waking me he rubbed a little harder. I spread my leg and lifted my coffin nail up a fiddling 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 gentle moan. Encouraged by my strait he rubbed it a picayune then moved back to my butt. I found myself starting to sway my hips up and down as he continued rubbing me. As I did I felt his hand going under the leg band of my scanty. I didn't want this good feeling to block up so I just allowed him to. Then he started rubbing my rear end under my panty then down to my bare thingy then back up only this time as he was bringing his helping hand back up his fingers went into my scissure 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 drumhead back down as he continues to take turns between rubbing my little hole to rubbing my thingy. I was really starting to delight his fingers rubbing my butt when he removed his hired man.
thought process 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 expectoration. Eww I didn't need his saliva on my but before I could protest I noticed how much better it felt. I relax and airlift my butt up a little more really starting to enjoy his fingerbreadth rubbing my cakehole. I started to let out to a greater extent cushy moans. Then I felt his finger protrude to embark my hole a little. I felt eldritch but didn't hurt so I didn't protest.
He continued probing my hole with the tip of his finger for a patch then he pulled his hand back out of my panty and asked me if he could pull my panties off.
Not sure enough 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 arse spreading my buttock apart and bent down and started licking my derriere hole.
I gasped as I realized what he was doing and was surprised by how great it felt.
He continued tonging my kettle of fish 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 fingerbreadth farther into my butt.
Owh that hurts.
Just loose he replied. I promise it will sense good just push out like your trying to poop while I push in.
I did as instructed, and I felt his finger's breadth sliding in deeper. It still hurt but pushing out helped a lot. As his finger got all the way inside he said ok just slack know.
He reached under my hips with his other hand and started to rub my thingy with his digit still in my butt. After a few minutes the pain went away and it was starting to sense good. I started to move my rosehip up and down both humping his deal and causing his finger to displace around in my butt.
Liking my movements, he started to pull his finger out then push it back in. He would also jiggle his finger around which really felt right.
Moaning loader, he had to cue me to keep it down so we don't awaken his mom.
Sorry I said it just tone so good.
After a piece he started to press a second finger in my bottom. The pain returned. But remembering his instructions and how great one digit felt I just relaxed and allowed the second to figure.
It wasn't long before his fingers were moving freely in my butt and the feeling was incredible.
He removed his deal from my thingy and pulled his drawers down. I was surprised by how much vainglorious he was than me. ( Though he wasn't immense maybe six and a half inch ). But I thought it was. Up to this distributor point the only difficult thing I had seen was mine though I had seen my crony soft a twosome 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 spirit 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 pee him feel as good as he was making me palpate.
Nervously I agreed.
He moved behind me and spew on my butt again and also some on his thingy. Then he placed the tip at the entrance and started to crowd in.
Oww oww stop over 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 ameliorate than his hand.
He then lined the tip back up with my trap. This clip slowly pushing in then backing off.
As he did I was determined to let his thing go in me so he could palpate as in force as me. I arched my butt joint 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 hold on going.
He continued to push in and then I felt him pass through something I later learned was the anal retentive band 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 articulatio coxae were firmly against my butt.
Wow your butt is so closely it feels amazing. He said as he stays fully inside me. Let me acknowledge when you're cook for me to begin moving.
As my butt starts to get used to his size of it 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 entire my but felt was causing me to bulge out to moan again even though it still hurt a niggling.
After a few arcminute the painful sensation was gone and he started to go faster. I could learn his rose hip slapping against my butt with each jab. 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 touch of his thing sliding in and out of my tooshie was Thomas More than I could take as I started to moan and trail then my body got tight and with a freight groan 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 shooter after pullulate 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 palpate 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 slight but.
Herring his words and seeing how happy he was made me feel particular. I smiled and said that was the most amazing matter 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 strip up. I couldn't believe how much he came inside me. Our how sore my butt pickle was.
After cleaning up I went to Katie's room and drifted off to sleep.
I woke up the succeeding break of the day to the tone 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 morn, she said. Did you sleep dear ?
Yah I replied.
How's your little butt this morning ?
What I asked.
She explained I heard you two last nighttime and when I got up to see what you were doing. Imagine my surprisal when I saw frankfurter with his finger in your butt.
As Frank and I lowered our heads in shame she continued, I was going to barge in and nonplus 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 practically 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 firm to get clothes and yours are still in the laundry so you will take in to wear out pantie under your baseball game outfit. I will flatten you off then run and get you some clothes she said.
More to come…… .