“Sleeping” with sister’s friend? Not Really.

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This happened when I was 15 and my sister was 13.  She has a friend, call her Jane, who is a bit naive about things — including sex.  You think 13-year-olds are a bit more sophisticated about things than kids in the past were?  You won’t believe Jane!

So Jane is sleeping over at our house.  I get out of the shower and put a towel around me.  I walk to my room, and the girls both see me.  My sister barely notices or cares, but Jane’s eyes bug out.  I get into my room, but overhear Jane tell my sister, “Your brother is cute!”

So about an hour after I go to bed, I wake up as I feel someone’s presence.  It’s Jane getting into my bed with me.  I ask her what the hell is she doing, and she tells me she wants to sleep with me.  Thirteen is a bit young for me.  I have no interest in girls younger than 14, so I tell her to get out and go back to my sister’s room.  She begs to stay.  I ask her what she means by sleeping with me, and she answers she just wants to cuddle and go to sleep.  She says we can set the alarm early so she can get back to my sister’s room before anyone else in the house wakes up.

So by sleeping with me, Jane actually means sleeping.  It is obvious this is what she considers sex.  I am too tired to argue, and I figure if it goes no further no harm done.  So she gets into my bed and lays her head on my chest commenting how good I smell.  She kind of smells good as well, and her body is soft and warm.  But I put all that out of my head since I still consider her a kid.  We both go to sleep.

Well, I sleep through the alarm, but Jane got up and left the room before anyone else in the house got up.  Suddenly the door opens and in walks my sister with an expression that could kill.  She slams the door behind her and asks, “What the hell did you do to Jane last night?”  I say I did nothing, to which sis replies that Jane said I took her virginity.  I tell sis what really happened and that Jane apparently thinks simply sleeping in the same bed is sex.  That was the embarrassing part — being accused by my sister of taking advantage of her friend, who’s knowledge of sex is on the level of a 6-year-old.  I still felt a little guilty as sis was right.  I should not have given in.  But hearing the truth from me did calm her down a little.

So next my sister had to explain to Jane that she was still a virgin.  This was news that disappointed Jane.  She never came on to me after that.  Jane barely spoke to me.  She always looked kind of embarrassed herself whenever she saw me.

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Playing doctor at 17

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Jenna is my oldest and best friend.  She is not my girlfriend, but a girl who is my friend.  We have never had any romantic interest with each other, but we are close enough to be each other’s best confidant.  I have had girlfriends and she has had boyfriends who were uncomfortable with our closeness.  Tough for them.  You don’t throw off a friendship like ours so easily.

So, when we were both 17, Jenna was in a bad accident.  She got smashed up pretty bad, but after two weeks came home from the hospital.  But both arms were in heavy casts, so she could do next to nothing for herself.  I would go to visit most every day.

This one day she is on her bed wearing her brother’s old pajamas.  The arms of the top are cut off so she can get it on over her casts.  Only her mother was home with us, and she had an errand to run.  She asked me to stay and look after Jenna.  I said sure.

Around lunch time, Jenna was getting hungry and wanted to go down to the kitchen to eat.  She said I would have to spoon-feed her.  Sounded like fun.  Then I added, “Why don’t I serve you lunch in bed.” She laughed and said OK.  She said her mom had some homemade vegetable soup for her and that is what she wanted.  So I warmed up the soup, place some in a bowl, found a tray and brought it up to her.  I still don’t know how I managed to spill the soup all over her.

Fortunately the soup was not that hot, but Jenna was soaked through – both the pajama tops and bottoms.  I apologized and started to try to clean her up.  She told me she would have to change pj’s and I would have to help her.  I said, “But then I will see you. . . .”  Jenna interrupted, “I know.  You will see me naked.  But the jammies are soaked through and it is starting to feel cold.”

Jenna and I have seen each other naked before.  The first time is when we were bathed together at about 3 years old.  The last time was when we played doctor at the age of 6.  I suggested waiting for her mother, but the spilled soup was just too wet and too cold.

I kept apologizing as I unbuttoned the top.  Jenna said not to apologize, and just get it over with.  The top came off as I tried to look the other way.  Now for the bottoms.  Jenna took a deep breath and said to just yank them off.  I did, and tripped over something since I had my eyes closed.  “I know this is embarrassing for both of us,” she said.  “But you just are going to have to watch what you are doing.  Go get a washcloth and wash the soup off me.”

I told Jenna that I really was not enjoying this, as I cleaned the soup from her chest.  “Just what a girl wants to hear when a guy is looking at her boobs,” she joked giving a forced laugh.  “Sorry, bad joke.  I thought making light of this will make it go easier.”

I cleaned off her belly and then stopped.  “You got a little on my legs and. . . .”  I offered to look away, but Jenna was afraid I might poke her in a sensitive area.  “I’ll make this up to you,” I nervously offered.  “If that means you are going to let me see you naked,” she replied seriously, “please don’t.”

Jenna mentioned it could have been worse.  “I could have needed to go to the bathroom,” she joked.  Then she added, “It just got worse.  I really have to pee.”  “Can’t you hold it in?”  “I have been holding it in for the past hour.”  “You need my help?”  “Just to clean me off when I’m done.”  “I don’t’ think I can do that.”  “I don’t think I can either since I can’t move my arms.  I will tell you what to do.”  Sure, that makes it easy.

So Jenna runs to the toilet naked except for her arm casts, because it would take too long to put on new pajamas and she is about to explode.  After a long pee, she asks me to come in, take a piece of toilet paper. . . .   You know.

So she goes back to bed while I wash up.  She tells me to take a pair of blue pajamas and to help her dress.  Noticing how I am walking she asks, “Have you got a boner?”  I admit I did and apologized as I unfolded the clean pajamas.  “At least you get to cover your parts,” she says.

Within two minutes it is over.  But this time we are both beet red.  “If you tell me you are just as embarrassed as I am, I’ll kill you,” she said.  We both laughed, but we knew it would take a while to get over this experience.

I was spoon-feeding Jenna her soup in the kitchen when her mom came home.  “Did you change your pajamas?,” she asked?  Jenna told her what happened.   Her mom looked at me and said, “You lucky guy.”

Jenna soon got her casts removed.  We went out to celebrate with my girlfriend girlfriend and her boyfriend boyfriend, telling the story.  I told my girlfriend I wish she would have been there to spare us the embarrassment.  She replied, “If I was there I would have just sat back and watched the fun.”  Jenna’s boyfriend stated, “Dude, you helped her on the john?  Ewww! I wouldn’t even do that!”

All is good now.

3

THE MOST EMBARRASSING THING HAPPENED…GIRL PERIOD

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Okay so there’s this guy who is a FWB but we didn’t see each other for a couple of months before this accident happened. The other night i went over his house, we hung out and as usual we just talked and cuddled, got high and eventually passed out. I could tell he wanted to hook up but I didn’t want to and ignored the moves that guys do when they want sex lol. During the night i woke up and realized my period started. my underwear wasn’t stained or my pants so i knew it didn’t get on his sheets YET. I did the necessities and went back to bed, morning comes along, I touched my pants and noticed that my period had gotten on them and freaked out! he was already awake so I didn’t know what to do and played it off, then saw a small stain on his grey sheets. I WANTED TO DIE! Like how the hell do you handle this sort of things?! I wasn’t suppose to get it for another week so I had no idea I was getting it! I was so embarrassed that I tried to play it off and pretended I was unaware. before I left i sort of covered it so he wouldn’t see it right at that moment cause I was just so petrified and embarrassed and grossed out that I didn’t know how to deal with it. Anyways, Im pretty sure by this time he saw the stain, although it wasn’t a lot, I know he probably did. It’s been 2 days and he hasn’t hit me up :(

ps – Our FWB rship is weird though, like we def act like we’re a couple when we hang out and had gone out on dates. I met his friends, and he talks to me about everything. Family, friends, he even plans things and invites me to them. We’re good friends but don’t text too often or see each other a lot. Idk it’s weird…BUT lets just say we’re at the stage where we feel comfortable around each other so idk if he’s gonna be weirded out by it or ignore it and move on from it…ughh FML

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Caught naked by little sister and her friends — again!

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I previously posted a story where my sister, then 9-years-old, outsmarted me and got me naked in front of her friends at a slumber party.  I was 13 then.  A year later I thought I was a year smarter.  Sis was having another slumber party.  This time I was staying out of the shower so I would not be put in an embarrassing situation again.  Not good enough!

I stayed in my room the entire evening.  Around midnight I decided to go to sleep.  In the summer I always sleep on top of the covers wearing only underpants — something my sister knew.  The next morning my underpants where no where to be seen.  I got dressed, went outside my room and then saw my underpants hanging on the door handle to my sister’s room.

Later my sister explained everything.  She had promised her six guests they would get to see me naked.  Around 2 AM, they quietly snuck into my room.  I am a heavy sleeper anyway, but it was easy to remove my underpants revealing all.  Each girl took turns lightly tickling my penis.  It was not enough to wake me up, but it was enough for me to get a fairly good erection.  So six 10-year-old girls, plus my sister, got a good look at my fully erect member.  She then showed me pictures she took of me laying there with my penis pointing straight up.

For the next few months, whenever her friends came over I had to hide out of shame.  The girls always would look my way and grin.  After six years, sis still has the pictures saved and password protected on her computer.  She only shares them within her circle of friends, and still views them from time to time.

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shopping with my mom

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When i was about 5 or 6 i was shopping with my mom and got lost, then i thought i found her and went to go grab her hand
once i grabbed the hand she turned around and gave me the death stare… this wasnt my mom :s

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my summer uniform

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when in summer in an outside class my summer uniform fell down and my mothers vest I was wearing was revealed. OH My God! I just realized right now someone must have undone the zip! its the only way it could have happened. Even the teacher was laughing. I just ran for the girls changing rooms.. oh Kids are Mean

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Caught naked by little sister and her friends

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This took place when I was a boy of 13 and my sister was 9.  She was having a slumber party with 5 of her friends over.  I did my best to stay out of the way.  I decided to shower before bedtime, and our bathroom door does not lock.

OK, so I finish my shower and notice all the towels were gone.  I did not hear the girls enter and with the blue shower curtain did not see them.  I figured they were all just outside the door waiting to catch me naked.  I opened the door a crack and saw no one.  The door to my sister’s room was slightly open with a light shining out.  I could hear the music playing and figured that is where they all were.  I could run to my room before they knew I was out of the shower.

So I run to my room, open the door, go inside and shut the door.  I am safe!  I turn on the lights and I am looking straight into the faces of a half dozen grinning 9-year-0ld girls.  My sister had the biggest grin of all — not to mention her new digital camera.  I was so shocked, I could not move.  I couldn’t even think enough to cover myself.  My genitals were there for all to see.

“This is so cool,” said my sister as she took a few shots with her camera.  The girls began to skip out of the room, each one pausing a moment to get a closer look at my cock or to look at my butt.  I was so embarrassed, I did not leave my room until all the guests went home.  I then confronted my sister about the photos she took.

She said she was only going to share them with her friends who were at the party — sort of a souvenir.  No one else would see them.  The next week I passed her room.  She was on the computer with some friends telling them, “Let me show you some naked pictures of my brother.”

I did not tell my parents.  What 13-year-old would admit to being outwitted by his 9-year-old sister?

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I was 19 and hungry

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I was 19 and hungry, I got desperate and drove down to 6th Avenue here in Des Moines one night. I picked up a hooker and took what I thought was a “she” to a roadside Motel. We started making out and as I started to stick my hand down “her” panties I discovered a pair of balls.

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embarrassing moment in public

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Did not have many of those,but recall one,as I was very shy,you knew me you knew this,this girl,she pulled my towel off me when went to shower after gym,she regretted doing so as well,My best friend kicked her *** as well My Mother got her suspended for doing so as well. I was just so embarrassed she yanked it off me as I was walking to the shower,because I was given permission to use the single shower in gym, My Mother did this,because I would get so embarrassed to shower with all these people,and did this so did not have to shower with all the rest,this ticked her off,so she did this to me. I sincerely,almost died,really did. Jealous *** she was. None liked her after that.

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Gym punishment

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One day i was in the gym and me and my friend told the teacher to fuck off so he told us to stay after school during 10th period so we did he told us to run down and back and we did.then he told us to take off our shows and socks and run down and back. so we did. after that he told us to take off our shirts and we did but after we ran down and back he told us to take off our pants and underwear and run down to the end of the gyme and do 20 jumping jacks. we protested and he said he would give us detention for a week if we didnt do it and we did and when we where doing the jumping jacks he took our close and said we would get them back after the school day was over and told us to walk around the school. it was so embarrasing since i was still in puberty i had hair down there but i got erections if anything was the less bt erotic. so i had an erection the whohl time and i even leaked precum when the real popular guys where teasing us and makng fun of me for being hard. it was thw worst day of my life

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