Humiliation

Rigged spin the bottle game

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So about 5 years ago when I was 15, I had a nice gig babysitting around the neighborhood.

One time I was doing one of the most expensive jobs I’ve taken, since I had to babysit one 12 year old girl called Jamie with three of her friends, and all the parents were paying me to sit this one night, so it was four times the pay.

The girls were gathered around Jamie’s new iPad, it had been out for about a year at that point, and they were all gathered around it and fiddling with it, I was pretty okay with that, since that meant I could just ignore everyone and relax with my own phone.

suddenly I heard Jamie

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Blackmailed by Step Sister

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Word of advice, if you’re gonna listen to something while you jerk off, make sure you have complete privacy, or things could get real bad like they did to me.

It was a while back when I was 15, and I didn’t have a computer of my own back then, and it was really hard to find masturbation material that was easy to hide for me, plus I was still kinda young so I didn’t know all the ins and outs.

I tried to find inconspicuous things to jerk off to, like small clips I could fit in my phone, or pictures in magazines or catalogs.

I had gotten suggestions from a friend in school to use audio materials, and he gave me a clip of a girl dirty talking and making suggestive noises, and so on.

In hindsight, I really should’ve probably locked the door, but I got naked and tried to close my eyes and “enjoy myself”, and I was actually getting into it when I heard a laugh.

I opened my eyes and saw my older step-sister, about 17 years old, with her shiny expensive camera phone (it was a while back, and she got a job to buy the thing), I instantly figured she got a picture or video of me jerking off.

I panicked, and begged her to not tell anyone or show anyone, she laughed and said that I would have to do whatever she wanted from now on.

I know I couldn’t say no to her, and it didn’t occur to me to tell my parents, so I agreed to essentially do whatever she wanted.

To make sure I was going to listen, she told me to finish jerking off, and so I stood there beating off and jizzing into my hands while my own step-sister laughed at me.

From then on, whenever my parents weren’t looking, she would make me do all her chores and treat her nicely and essentially act like her manservant, but that wasn’t the end of it.

One time when my parents were out, she invited a couple of her friends, including a younger sister of one of her own friends, who was around 13 at the time, I guess.

They made me stand in the living room and strip naked while they sat and watched, and then proceeded to play with me and pose me and make me do and say all sorts of embarrassing things, they finally let the younger sister jerk me off until I came before making me fetch them food and drinks from the kitchen.

And this continued until she finally graduated and moved away to college a year or so later, and I was more or less released.

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Strip Poker Loser

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So this one time when I was 17 I went to my girlfriend’s place to have fun with her and her best friend, who also brought her boyfriend.

We had stolen some beer from the fridge and were kinda buzzed, when my girlfriend suggested we play strip poker, everyone seemed okay with it, I was still kinda worried, but they kept insisting and I finally went with it.

we played until one person was naked, sadly, that was me, I was completely naked with my cock showing (six inches), the other boyfriend was in his pants, my girlfriend was in her underwear and her friend was only in her panties (she had pretty great tits, so I was kinda stiff).

The other boyfriend took his girl away to have a quickie I guess, leaving me with my girlfriend who started making out with me.

Soon we were interrupted by the happy couple again who were now dressed, the boyfriend said he had to jet and left almost immediately, I looked around for my own clothes but couldn’t find them anywhere, the friend told me she hid them away, and while I was distracted, my girlfriend put her clothes back on and I was the only one left naked.

She told me to go home, and when I asked for my clothes she told me she’d keep them and that I had to streak home (she drove me here).

When I said no way she told me that the only other option was for me to put on a show for them, they took out their phones and started making a video, they forced me to say out loud that I lost strip poker to two girls and I had to pay the price, then they told me to jerk it.

I started beating off and came very quickly (Quicker than I wanted) all while they filmed me and giggled and made fun of me, I remember jizzing on a glass coffee table they had.

She finally took me home naked, I never got my clothes back and I found out later that she did this with all of her other boyfriends, they usually said nothing because it was humiliating, and so she wouldn’t let the videos out.

ofc we broke up soon after.

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My first night as a girl. Forced feminization. Trick or treat!

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One Halloween while I was living with 4 college-aged girls (I was 30) when one of them got the idea that my costume for the night should be to be made up as a girl. I protested at first, but eventually gave in to their badgering and cajoling, to their delight. So they all got to work on various aspects of getting me dressed and made up, gathering this and that, making preparations, checking for sizing, etc. Hair, tweezed brows, nails, makeup, panties, bra, skirt, stockings (with freshly smooth legs, of course), a proper garter belt, stiletto heels, jewelry, the works. All the while they were getting more and more excited, and giggling like crazy, buzzing around from room to room.

Finally I was done, and that’s when the real kicker came (for all of us) when they stepped back and gathered around after the last bit of makeup was applied, completing my “outfit” and transformation.

Now, all along one or two had been in the room, with others coming and going, getting this or that, staring in wide-eyed curiosity and wonder, or just poking fun at their new girlfriend housemate, but about the time my makeover was done the one doing it shouted for everyone to come see, that they HAD to SEE. They all came in and were virtually transfixed. Each of them looking me up and down slowly, taking it all in approvingly, and squirming at the same time. I myself was more embarrassed than words can ever do justice to, but they were all STUNNED, I mean seriously stunned, some with their mouths agape in shock, but ALL now looking at me with these eyes of astonishment or adoration.

Now, I’m an attractive man, so I’m told, but this was a whole other order of magnitude altogether. You could tell that they had no idea I would be so gorgeous, so feminine, and apparently so attractive. This was when I had only medium length long blonde hair, I might add. Nowadays, I have much longer mid-back length hair, so wonder what they might have done or thought about me now, with it all coiffed up properly! Probably would have been sensory overload for all of us, and we would never have even left the house for Halloween festivities. More on that in a minute. But getting back, I was at once confused by their shock, admiring/approving eyes, giggles, etc. As well as by the face of the girl now looking back at me in the mirror. I had to admit to myself that I liked it, and all the attention/help getting there, as I hadn’t told them I had always loved wearing panties, stockings, and being hairless. For me, there’s something very erotic and exciting about standing there as a girl in a man’s body, in panties, stockings, a short skirt and all. Along with the makeup that really brings out one’s eyes.

Eventually they got around to asking me what I thought. I was nearly tongue tied, but then one of them noticed I was fully erect and said “hey look, he LIKES IT, he REALLY likes it!!” The giggling taking on a different tone and intensity. She then came up to me, reached under my skirt, and boldly felt my shaft through the thin fabric of my panties, which instantly throbbed deeply in her hand as she squeezed it firmly, while also pulling up the skirt so all the others could plainly see it (and my subsequent humiliation and embarrassment). I went beet red, and tried to stammer some protest, but my body told the truth, that I did secretly like it. In fact, I LOVED it and was awash in all these intense feelings. There I was, with my hair done up in pig tails and ribbons, eyeliner and mascara over enough foundation to hide my facial hair, wearing earrings, with bright red pouty lips, a neck choker to help obscure and hide my Adam’s Apple, a cute little white school-girl-type blouse (through which you could clearly see my padded black lace bra and underbust corset, which helped give me a little cleavage and a girlish waist), a short black skirt, with freshly shaven legs swathed in sheer thigh nylon stocking, wearing a black lace garter belt, and 5″ black patent heels with a dainty little ankle straps.

It was then that a camera flash went off, as one of them began snapping pics of my tormented, erect state. And I was in torment, with my cock throbbing hard. Painfully even. Alexandra, the one with camera then said, “these pics were just to insure that others get to see our hot new housemate tonight, one way or the other. Whether you join us in going to our parties, or if we have to post them online for all to see how you clearly enjoy being a girl, to help convince you”. Ugh.

Eventually we were all ready to go out to a few parties they had been invited to, even if I was still a bit wobbly like a baby in my heels. Part of me excited, part of me dreading what might be ahead. And out we went into the cool Santa Barbara night.

Arriving at the first party we made our way inside with more than a few stares directed at me since I appeared to be the only one out of costume, mostly from males who shocked me with their stares and unmistakable lust for what appeared to be a hot girl, but as we approached the front door and their friend the host, my destiny for the night became very clear, as anytime I walked, or really even moved, the caress and exquisite feel of the sheer stockings and silky pink panties would give me an immediate erection. This, along with the coolness of having my silk covered butt and privates out in brisk October air was a massive turn on, no matter how I tried to not think sexual thoughts. Add to this that as I walked I just got harder and harder from all the stimulation and the fact that I was the center of a LOT of attention, and you had a recipe for my hard on to be noticed if I moved the right, or should I say wrong way.

As we approached the door the host welcomed us, and I was introduced as Tori. My male name is Troy, btw, so it was easy for me to remember to respond to “Tori” all night long. I tried to keep my voice as feminine as possible, which apparently made it soft, husky, and sexual sounding. This would be a huge turn on for any men within earshot, as it turned out, to my distress, as it made even more men rivet me with their eyes. I could FEEL them looking me over, head to toe. Double ugh, since though I AM bisexual, I was not ready to add THAT to the mix this night! This being the center of much male, AND female attention, would be the norm for the whole night. It’s really amazing how many women were drawn to me, almost without exception, for some reason. It’s almost as if a part of them could see or sense the maleness, yet not.

Finally towards the end of the night we were all a little tipsy, which helped me relax considerably, when one male got up the courage to approach our group, and me in particular. As he came past behind me in the crowd I clearly felt his hard cock rub over my butt through my skirt, till he paused, feigning like we were in a crowded subway or elevator, pausing to rub his harness right between my cheeks! Though part of me was in shock and tensed, another part nearly swooned at the headiness of it all (no pun intended;), the whole of me feeling so sexual, so desired. I pushed back against him, wiggling my butt just a little, to tease him, then up and down ever so slightly so no one would notice but us. As I did I felt his right hand gently come up under my skirt to feel my buttock through the soft silkiness of my panty, and stroked me for just that split second. I nearly went weak in the knees and fell forward. Ever sharp Alexandra saw this and smiled at me big time, and quickly came to my side of the circle to intercept him before he said anything or moved on past us. She stopped him, winked at him, took his hand and brought him and it around in front of me as she raised my skirt and place his hand on my crotch. I felt the jolt of shock hit him, and can remember it like it was yesterday, though he instantly softened and relaxed. Seeing as how it was very dark where we were, this all went unnoticed by even those right next to us and our group. Only the three of knew of this little exchange thankfully, since my cock instantly began throbbing at being touched. He paused long enough to stroke it a little and I began to pulse even more. I could feel a bead of precum forming at the tip of my head, and so did HE! He then leaned in and with a whisper of “you are SO beautiful, honey” placed a light kiss just below my right ear. I nearly passed out, it was so dizzying for me. Alexa, seeing this, smiled a wicked and knowing smile as she caught my arm just to be safe, steadying me. Apparently this was one of her little desires for me and this night. That is, to tease and be teased, like a true girl. She called it “an initiation”, bringing me more fully to know my inner feminine side. And right she was, as I instinctively swiveled my ass towards his crotch, pressed back against him, and gave him a little milking motion in kind.

It may sound like it took place over a minute or minutes, but it was all over in seconds, with him smiling at Alexa and I as he moved away. Which made part of me relieved, and another part to ache like a woman to be taken somewhere where I could help satisfy him, and possibly even be penetrated by him, or bred like his girlfriend.

The only other incidents were when a couple guys really began coming on to me, and who clearly hadn’t a clue I was male. Alexa, each time interjected herself again like a Mistress/Dominatrix and quickly and discreetly lifted the front of my skirt so they could get an eyeful of my cock and panties, with each time ending in winks, knowing looks of recognition, and broad smiles rather than some ugly homophobic slur. So that made the evening a LOT easier to endure and navigate.

By the time we got home my balls were aching terribly, after having had so much stimulation all night long, and I was simply going to head up to my apartment. I said goodnights and many thanks all around, with lots of giggles, stories being relayed back to me of social exchanges at the parties, of various looks and admirers who I hadn’t seen, but which the various girls had, and began to head to bed when Kiana, one of my housemates, asked if I would care to join her for a nightcap. I couldn’t refuse. Plus it gave me another few minutes to relax in my female attire, fully made up still, which was still a very heady experience, and an incredibly exciting one once I calmed down.

Alexa took me aside real quick to let the lugnut in me know that Kiana REALLY liked me, since I sometimes miss women’s signals. This news kind of jolted me, but was still very welcome.

The short story of which is that her and I quickly fell into bed together as she told me of turned on she was by me, and that the seeing “Tori” ratcheted that up off the chart. Ha! Who knew!?! Gotta love that. Anyway, it wasn’t long before she had her hands inside my blouse pinching my nipples, and then up under my skirt feeling my cock through my panties, and the growing wet spot of precum. With a flick of her wrist they were around my ankles, as she pushed up the waist of my skirt so she could better help me gain relief for my poor aching testicles. It didn’t take long with all the night’s “foreplay” through walking and simply moving, and almost no sooner than she wrapped her lips around me and began stroking the head of my shaft with the small of her throat I was unleashing stream after stream of cum deep down her throat in a torrent. I had been so full of cum that even when I pulled back to let her have some to taste (she loves and needs that) in her mouth a veritable stream continued to pump out of me and onto her lips, chin and chest. No wonder I had been aching so much. I had never seen so much semen come out of me.

Getting back to being dressed as a girl, or should I say gurl. It still makes me hard as a rock to think of it. And it always had. Even before that night.

See, I had always LOVED wearing panties, stockings, g-strings, slinky dresses or skirts, corsets, the occasional pantyhose, or anything very feminine or sensual. I had found this little truth out when I was just 10 years old, having found my older sister’s panty drawer, and getting my first erection after I quickly and without hesitation slipped on the sexiest, silkiest pair.

I had dabbled in wearing panties and other stuff over the years, on rare occasions, or when the urge struck me. And it always did. No matter how I tried to deny it. I guess it fulfilled a deep need in me, or felt familiar and welcome, as if perhaps a hangover from a past life as a girl. Who knows. What I do know is that I’ve read enough on that subject to know that it seems that the human soul generally prefers one gender over the other, regardless of which one you might presently be (it seems we change back and forth as we reincarnate). But enough esoteric-type talk. All that really matters is that we enjoy and be ourselves in this life, today, as much as possible.

What I realize now, looking back on that night, is that I was and had lived the dream of many transsexual or transgender/pan-gender men, or even just closeted panty lovers who occasionally might be drawn to wear perhaps more, in that I had a bunch of giddy and enthusiastic girls actually urge and force me into it all! Seems that’s a HUGE fantasy of a LOT of men and boys.

In recent months I have decided to more fully embrace all of who, what, and how I am on much more permanent basis. Which in this life is both masculine and feminine, sensitive and tough, strong yet gentle, but with a decidedly girly aspect ūüėČ Part of which finds me writing this in, and daily wearing skimpy panties and g-strings, even out in public under my clothes, like many men. More than most women know.

Call me a sissy, if you like. I can own that.

troy

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Stripped by senior girls

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It was my first day of high school after skipping the eight grade because the school believed that I had enough knowledge to skip right to grade nine. I was thirteen years old, probably the youngest in the high school, and I was quite scared, nervous and intimidated. When the bell rang for lunch time, I really had to pee so I went towards the bathrooms. But I was so nervous that I accidentally walked into the ladies’ room, and I saw for older girls talking to each other. When I showed myself they quickly looked at me. “I’m sorry!” I told them as I turned around to leave as fast as I can. But one of them got me by my arm and pulled me into their group, putting me up against the wall with the four senior girls looking down at me. “My, why are you here kid? You look a bit too young.” One of them said. I explained to them the whole grade skipping situation and that I was just nervous and walked in on them accidentally. But I got WAY too nervous with them all looking at me, because I couldn’t hold myself in and I peed my pants. It was so obvious with my grey pants getting darker in that area. “Aw you peed yourself?” One of them asked. They looked at each other with a wide grin, and that’s when the hell started.

Two of the girls pinned me against the wall and the other two started to strip me: Unbuttoning my shirt, taking off my shoes and pants, leaving me in my wet undies. “Let’s see how big your cock is.” That’s what the one girl said when she, in one quick action, pulled down my undies, exposing my penis to all of them. I still don’t know why, but my penis had gotten stimulated during that time, and I have no clue why, because if anything I was frightened, not pleased at all. The girls started to exchange comments like “It’s bigger than I thought it would be.” and “It’s bigger than my boyfriend’s!” I didn’t have any idea what size meant big or small for the penis, but I was frozen with fear and humiliation. Even if I wanted to try and break free, I couldn’t bring it in me to move.

One of the girls then asked the group: “How about we bring him in the hallways?” And there’s when I felt like dying. The girls took me from my arms and legs, lift me up and brought me into the busy school hallways. I was crying while the other people looking were laughing. One of my four kidnappers was rubbing my penis all the while, and it felt so weird. As a lot of students gathered in a half-circle around the four girls in I who were against a wall, one of them yelled that anyone who wanted to play with my penis could step right up and do it. A few other senior girls came closer and started to touch my penis without my consent. I felt an intense feeling in my penis and that’s when I let out a white liquid without warning and without want: My first ever ejaculation, and it was in front of so many people at school.

More people started to rub my privates and it only started to hurt and humiliate me more and more. After a while the other students left, still laughing, and the four senior girls dropped me and left me where I was. I heard one of them say “At least he has a good penis” faintly, but that was not something I was proud of. I felt as if I couldn’t move, so I just curled up into a ball and cried. That’s when three girls from my earlier math class approached me. They looked worried but I hid my face right in my knees after seeing them. “Are you okay?” One of them asked me. I shook my head still in my knees. “What those girls did to you… that was awful…” Another one of them said. “Come on let’s get you to the principal’s office.” The last one said as I felt her cold hand on my wrist. I looked up to see two blond girls and a dark haired girl. They were all pretty, which is what intimidated me and made me try to get them away from me. “Look, we just want to help you! Come on.” After a few minutes of trying to get me up, and some glances from other seemingly worried and puzzled students, I followed them, with one of the girls letting me borrow her hoodie to cover myself as I walked to the principal’s office with them.

The girls told the principal what happened and he immediately gave me some spare clothing and called my mother for her to pick me up and bring me home. He told me to take my time recuperation and that he’d definitely punish the girls that had stripped me. I didn’t go to school for the rest of the week, but I felt better the next school day so I went. The three girls that had helped me out became my closest friends even to this day, but it’s still embarrassing to think that they met me after I was stripped naked and publicly was ejaculated by senior girls…

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Pinned down by a woman

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The office I work at were having a picnic in the park and one of the woman, around 5’11 and on the heavy side, started joking around and taunting me that she could kick my ass. Very nervously I replied “Well I’m not so sure”, the next thing I Know she tackled me to the ground and was sitting on my chest in no time, she felt really heavy on me, and I made a few frantic attempts to escape, but after tiring myself out, I just lay there exhausted and defeated. She slapped me in the face a bit and taunted and humiliated me verbally for about an hour, before finally letting me go with a promise that she would get me again soon. Thankfully it hasn’t happened again , but i know it’s coming. I’ve been trying to avoid her as much as possible at work, but Every so often I’ll run into her and she gives me this look and says “don’t forget my promise, I’ll get you again someday”. Every day I go into work feeling nervous and thinking today might be the day. I feel like I’m back in school all over again.

2

The not so secret masturbation…

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After staying at school to help with a few things and being very tired… I finally went to the girls locker room to change myself up. When I got naked, I looked outside. It was sunset already… and that gave me a though. I started to rub my breasts a bit… it felt nice… ran my fingers around my pussy… felt REALLY nice… I sat down and started to masturbate! I moaned loudly and passionately at my own masturbation! No one would hear… but it was still risky, doing this in school… Then I started to moan out the name of my crush for that extra turn on effect… I closed my eyes and thought of him touching me. “OH JASON! JASON!” I screamed out of my lungs. Then I looked at the window again. I saw three guys, one with a camera, looking at me and recording all of my actions! The window was half open too, so they probably heard me yelled Jason’s name! I ran towards the window and the boys ran away. “DON’T YOU KNOW HOW TO GIVE A WOMEN SOME PRIVACY!?” I told the sixteen year old boys in my grade who were still running away with the video footage of my masturbating… They saw me from the front too, it was completely humiliating!

The next day at school was even worst… apparently they had showed the video to a LOT of the boys and some of the girls… EVEN JASON! When he came to me, he started to talk. I was so nervous and embarrassed… “So you yelled my name, huh?” He said. I left him. I didn’t want him to humiliated or embarrass me with that story. Some of the girls thought came to me and tried to cheer me up and told me that I was just in the heat of the moment and that doing it like that was passionate and really nice. It still didn’t cheer me up.. all of the boys in the school would see my naked body and see me touching it in ways they only wish they could, moaning out the name of my dream man while doing so…

GOSH IT WAS EMBARRASSING!

3

Boyfriend caught me naked

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Iím a girl who has always been shy around boys.† The reason why I think is obvious.† I grew up in an all female household.† There was my mom and my two sisters, one three years older than me and one two years younger.† Our dad left when I was 4.

Still when I was 14 I had my first boyfriend, Alan.† He was willing to put up with my shy quirks.† He didnít pressure me for sex.† He really liked me a lot.† He would often come by our house just to hang out with me.

So this one Saturday, I was home and Alan stopped by.† The only other person home was my older sister.† She let Allan in and told him I was in my room and that he could go up.† What she did not know is I just took a shower and was naked.† So I hear a knock on my door.† I figured it had to be my sister, so I told her to come in.† I may be shy around Alan, but I have no problems being naked in front of my mom and sisters.

So my back is to the door, so I do not see who is there.† Alan enters to get a full view of my naked backside.† I wonder why my sister is not saying anything, so I turn around to see Alan.† He is frozen with surprise.† His mouth is wide open in shock.† I also freeze, now giving Alan the full frontal view of everything.† I finally realize what is happening, so I scream and try to cover myself with my arms.† I could have easily grabbed a pillow off the bed to hold over myself, but I wasnít thinking.† Alan suddenly wakes up and starts saying ďIím sorry.† Iím sorry,Ē over and over again.† He leaves my room and hides behind the outside wall so he would not see me.† Iím crying and screaming.

My sister hears the screaming and runs up the stairs.† She can figure out what happened.† She tries to calm me down saying it was her fault because she did not know I was nude.† I keep yelling for Alan to get out of here and I did not want to see him again.† I was too embarrassed and angry.† My sister tells Alan heíd better go home because I was too upset just then.† Alan calls later that night to apologize, but I refuse to talk to him.† He comes by the next morning, but I tell my mom to tell him to go away.† My mom and little sister know what happened.† Mom said I was being silly.

The whole next week I try to avoid Alan as he tries to talk to me.† I know he feels badly about seeing me nude, but I donít care.† I am just too embarrassed.† He also calls my home to talk to my mom and sisters asking them to help him patch things up.

So itís the next Saturday.† I am in my room listening to music when Mom comes in.† She tells me Alan is here again.† I tell her I donít want to see him.† Mom says, ďThis has gone on long enough.† Heís really sorry about what happened, even if it is not his fault.† He wants to apologize so the least you can do is give him the courtesy of listening.† This has got to end one way or another.† Tell him you forgive him or break it off.Ē

So I follow my mom downstairs to the living room.† I donít see Alan, but my two sisters are there on the couch with big grins on their faces.† My mom calls out for Alan to come into the room.† Alan walks around into the room from the kitchen.† He is totally naked!† There is not a stich of clothing on him!

I am shocked.† My mouth drops open and my hand covers my mouth as I get a full frontal view of Alan.† My sisters are giggling.† Mom leans over to me and says, ďAny boy who is willing to go through this sort of humiliation just to get a girl back may be worth hanging on to.Ē† Alan tells me that he is sorry about seeing me naked, and that he figures the best way to make things even was to let me see him naked.† He asks for my forgiveness.

I tell Alan I should ask for his forgiveness.† I realize his seeing me nude was an accident and I reacted like a spoiled bitch.† I tell him I want him back and I give him a hug.† Then I tell him to put his pants on.† I donít like my mom and sisters looking at my boyfriendís dick.

 

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Humiliated by a 6 year old

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It was humiliating. I was 11, and playing at the park with a bunch of my friends. Lots of kids were around, younger and older then me. Well out of the blue, this girl I didn’t really even know, who was More

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halloween humiliation

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i was in the second grade one halloween at my school in my halloween costume for a boo walk around my school .I decided to go commando under my costume which was a kind of cloak thing . we start the walk More

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