Erection

lost my swimtrunks

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It was 1966.

I was 16 when this happened and the PE lesson was coming to an end. We were practising diving that day. I dived into the pool, the drawstring was not fastened tight enough so off they came off and I didn’t know, then about 40 girls from another school entered the pool area, I swam to the poolside and climbed out of the pool, yes you guessed it, everybody got a good luck at my parts and my butt, I also had a tan line and my butt was pale. I got out of the pool, walked away from the edge of the pool, the rubbed my eyes and pushed back my hair. I spent about 10 seconds looking around to find out what everyone was laughing about, then I looked at the girls in the pool. I put my hands down to pull up my swimwear and realised I had nothing on. It was about 40 seconds from when I came out of the pool till I realised I was naked. I covered my bits immediately and I looked around the pool for my swimwear and when I found nothing I ran to the men’s changing room. One of my mates was sent to retrieve my trunks. The PE master was not best pleased since nudity in front of the opposite sex was not accepted, he thought I had done it on purpose he called me an exhibitionist. I told him it was an accident and tried to explain but he then decide that 6 whacks with the slipper was not enough and gave me 12, ouch it hurt, after the spanking my friend who had retrieved my swim trunks handed them back to me, with a grin on his face, probably because I had started to get an erection, which most of my friends watched. My mates where laughing during my punishment and when they saw me come out of the water naked . Most of the girls were laughing and giggling, as girls do. It was so embarrassing.

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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 😉 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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Sexting with my girlfriend kinda

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So my girlfriend and I are texting each other and she asks me to sen a hot picture of myself and do i take a picture of my erection through my pants (I did indeed have a erection) and then afterwards i sent a picture of a oak tree and it says this is how hard i get when i think of you. And she responds with “lol”. Then i say “are yo going to send me some?” And she replies with sure. The after avout fifteen minutes she sends me this picture of herself in these really hot red and whit striped knee socks (I have a stockings/sock fetish) and then a picture of a waterfall and it says this is how wet i get when i think of you. And i fucking lose it, it is so damn hot my erection started to hurt so i run in the bathroom (cause my door to my bedroom is unhinged) and i start whacking and my little sister knows my girlfriend from school and from times she has been over. And i’m whacking it in the bathroom pretty much silently. Then my sister walks in and she sees the me and says “what are you doing” and i shove my dick back in my pantd and yell “nothing” and the picture is still open on my phone and my little sister sees it and she just says in like a really low voice ”jacking off to your girlfriend” and i just hang my head in shame and say yeah pretty much then she grabs the door handle and just slowly walk out of the bathroom. And so i just stood there for awhile and i could not mastubate because of that experience i was so goddamn embarrassed.

 

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Humiliated in school

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I go to Catholic school where you can get spanked and hit with rulers for begin bad. I got caught cheating on a finals test in one of my classes and the teacher brought me to the front to make an example of me. She paddled me like 6 times on my butt then made me take my pants off, and then even my underwear right in front of everyone. I had to stand with my hands behind my head and get paddled on my naked butt right in front of everyone with my penis on full show. Everyone laughed at my small penis and after 5 minutes of getting spanked on the butt naked my dick started getting hard. Everyone was laughing and pointing and I was so embarrassed I tried to cover up but the teacher would not let me. She made me keep my hands behind my head and kept spanking me with my boner bobbing all around for all to see. The teacher got mad at me for getting a boner while getting punished so ordered me to jerk off and keep jerking off while she paddled me across the butt. Everyone laughed hysterically watching me get spanked while having to jerk off. I wound up squirting cum all over right in front of the whole class as they exploded in laughter at me. It was the most humiliating thing ever

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Lost my virginity to a total jerk

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When I was 14, I had my eye on two guys.

The first was Alex. We grew up together. He was my age. We had been like brother and sister, but now we were looking at each other quite differently. Actually, we were distantly related. We shared the same great-great-grandfather, so we shared some blood but were distant enough to make a relationship OK. Alex also went to the same school as me, and even lived just a block away.

The other guy was Joe. He was a hunk at 16. He had a bad reputation for using girls, and I was warned about him. But with me he always acted like he loved and respected me. He admitted to his past, but told me in a very nice, soft way, that he would give up all other girls and just be with me if I agreed to be his girl.

Joe was also very good with math, which was my worse subject. He had been getting As in college level courses, so when he suggested I come by his house on a Saturday to have him help me with my math homework it seemed like a good idea. Well that Saturday, no one else was home. I went with him up to his room and we worked on my homework for almost two hours. After that I was pretty worn down. He told me to lay on his bed to rest, then he laid next to me.

I remember everything clearly. He gently ran his finger across my cheek saying how beautiful I was. He told me he wanted me and if I agreed then I would be the only girl in his life. He gently kissed me on the lips and put his arm around me. All my thinking went out the door. I told him yes, so he began to undress me.

Soon I was totally naked. I reminded Joe I was still a virgin, and he needed to be careful. Dont worry about it, he said. I then asked if he had a condom. He said no, but would pull out before he came. I knew from health class this is not the best means of protection, but I agreed to let him have me.

It was terrible. He lowered his pants and his shorts. I could see he already had an erection, and it was huge. Without any foreplay, he spread my legs and then my pussy lips, and then shoved himself inside of me. I screamed from the pain, but he continued to bang me harder and harder. I screamed at him to please stop, but he continued. I said he was hurting me, and he said it was because it was my first time and not to worry about it. Then I felt a different sort of jerking inside of me. I may have been a virgin, but I could tell that he came inside me. As he pulled out, I could see I was bleeding. He just told me to go clean myself up in the bathroom.

I showered and then came back wrapped in a towel. I let the towel drop, not caring if he saw me or not, and quickly got dressed. I was afraid since he came inside me that I would get pregnant. He told me he couldnt help it, and if I did get pregnant that I could get an abortion.

Next Monday at school, I tried to talk to Joe, but he ignored me. It was like that for the rest of the week. I woke up Friday morning to see a little blood on my panties. I knew I was having my period, and I was relived I wasnt pregnant. I sought out Joe at school and told him. He really didnt care. But what he did tell me hit me like a punch in the stomach. He said, Will you piss off already? All I wanted was to bust your cherry. I did that. Now go away.

I felt like shit. I felt like dirt. I had been used like some thing, and it hurt. After school, I decided to go over to Alex house. I wasnt going to tell him what happened. I just needed to be with someone who actually did like me. But when Alex opened the door, he told me he heard about me and Joe. Joe had been bragging all over school about what he did to me. Alex said he was really disappointed in me. I started crying and told him I was sorry. I had made a big mistake. But Alex wasnt interested. He was too hurt as well.

Now everyone in school knew that Joe had fucked me. That was embarrassing and humiliating. I suddenly realized that all that week people had been pointing at me and laughing. I didnt think anything of it at the time. It was obvious the next week at school. Boys had labeled me an easy lay, and were asking me out obviously for that purpose. Girls who hated me called me a whore and a slut, even though most of them had been fucking guys long before I did. The only sympathy, if that is what you call it, came from girls who said I was an idiot. This kept up for week, but lessened after Joe started bragging about another girl he fucked. The incident was not totally forgotten until the beginning of the next school year.

Alex and I made up enough to become friends again, but there would be no chance of any romance between us. He soon started up with Amy, another girl in my school. Shes a nice person and I like her. Im glad for Alex.

I didnt get a real boyfriend until my senior year. He had transferred from another school. He also had a bad first time. Thats another story, but Ill just say he unintentionally hurt a girl he liked due to his own immaturity. They later became friends, but he still feels badly. I told him about Joe. My boyfriend’s name is John, and we are still together. Six months into our relationship we began sleeping with each other. Sex with John is great. I just wish that he or Alex would have been my first rather than that dirtbag Joe. I have never forgiven Joe.

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My Wet Dream

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I didn’t reach puberty until I hit 13, and then it hit me with everything it had.  I began waking up in the mornings, about three times a week, with a boner sticking out from my pajama bottoms and my pj bottoms soaked with cum.  It was my dark, embarrassing secret.  I did my best to hide it from my family.  Before anyone could catch me, I would go to the bathroom, take off my pajamas and put them in the hamper.  Then I would wash myself off.  It never occurred to me that my  Mom could figure things out from my stained pajamas, but she never said anything.

Then one day my secret was discovered.  I was late waking up, and Mom told my 10-year-old little sister to wake me up.  She came in, pulled off the bed covers, and got a clear view of my erection sticking out of my cum stained pajamas.  Not knowing what it was, she screamed.  My parents came running in, and when they saw the situation, Mom took my sister out of the room.  Dad sat down next to me and explained what was happening.  I had a wet dream.  It was nothing to be ashamed of.  It was only my body trying to get used to the changes I was going through.  It was normal for a boy my age, and eventually they would take place less often and then practically stop.  I felt a lot better.  After that I was not ashamed to the point where I felt I had to hide anything.  I even would tell my mom that due to last night I needed a freshly laundried pair of pajamas.

Mom also had explained it to my sister, who now had a new game.  She tried to get up before me every morning, come into my room, and pull back the covers to wake me up – and hopefully catch my hard cock and cold, sticky pajamas.  Several times she did.  Eventually I didn’t mind.  No harm done.

Well, sometime later my sister’s health class was learning about puberty.  They learned about the changes and new experiences for both boys and girls.  No, she didn’t mention to the whole class that I was having wet dreams.  But she did confide in Janie, her best friend.  Janie apparently wanted to see for herself, although she did not tell that to my sister.  Janie managed to wrangle an invitation to sleep over one Saturday night, hoping to catch me the next morning.  And she did.

Janie snuck into my room before my sister or I awoke.  She had her cell phone camera ready.  I woke up as she pulled back my covers.  Janie struck pay dirt.  There was my hard cock and this time I had shot off a super load in my sleep.  I gained consciousness after she got a few shots off with her camera.  I jumped at her to get the camera, but she ran out of the room.  I yelled for her to give me the camera, chasing her out into the hallway.  My hard dick was still sticking out and my pj’s were cold, damp and sticky.  The noise woke up my sister, who came out of her room and saw what was going on.  She told Janie either to give her the camera, or delete the photos herself.  Out came my mom who saw my condition and told me to cover up.  This distracted Janie just long enough for my sister to grab the camera.

My sister began deleting the pictures saying, “He’s my brother!  Only I get to see his dick!”

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REVERSE: My mom embarrassed me instead!

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I’m seventeen and my thirty five year old mom and I were getting ready to walk to the swimming pool in our swimming suits which was half a block away. I was wearing my trunks and she was wearing a bikini. As we stepped out of our house, I decided to do something funny while she was locking the door. I reached to her back and untied her bikini top and then took it off her. There weren’t any people outside in the street, but it was the daylight hours of midmorning, so there was a chance that someone could come out, or possibly just look out their window. My mom turned around and yelled for me to give back her bikini top while covering her exposed top, but I stood there and danced around with it in front of her. Since she could see I was playful, she reached a couple of times for the bikini top, but I kept moving the dangling top out of her reach as a keep away. I wanted to get her away from the door and then pinch her nipples, and then I would give it back to her. She then had to decide whether she would come after me, or go in the house, or do something else. She then dove towards my waist and ended up pulling my own swimming trunks off and then with them in her hand, she ran towards the house door and unlocked it and ran in, but I pushed myself in before she was able to close the door. So we both ended up in the house, her with her top off, but me, with nothing on.

Now that we were inside we got to see each other’s position a little more clearly. My mom doesn’t have big breasts. I would say she’s a small B, and now that we were inside, she said, that I had given her a good idea and that she might go topless like guys do in the house from now on since she almost had a guy’s chest, so she didn’t get embarrassed at all by my prank except for the initial reaction due to us being outside even though her breasts were small. She had turned the situation into something positive for her. On the other hand, since we had showered before leaving for the pool, I was small and flaccid down there, although we could both see that I was starting to get aroused from her being topless, even though she was my mother! She said that it looked like my little thing was getting excited, and then told me to give her the bikini top and I wouldn’t get in trouble and that I should give her the top first since I had taken it off her first. I got embarrassed by the comment about my arousing little thing, but tried to laugh it off as I handed her the bikini top. She then said, she wanted to see if I would get aroused before she would give me my bottom and even though I had given her the bikini top, she didn’t put it on yet, but held it in her hand with my trunks. I felt mortified by this, but she said I should have thought about that before I took her top off. She then used the finger of her other hand and stroked it across my chest and we both saw that I got fully stiff, she then said that was fast and now we were both going to sit down and see how long it took me to get down without any stimulation of it by either me or her. She put her top back on and we silently waited for an hour until I began to go back down. I truly learned what the term “blue balls” meant by this, because it was aching the whole time and for a long time afterwards, but when it did go down she gave me back my trunks with a smirk and said that she might occasionally walk around the house topless and I’d have to get used to having no release from it and that my “blue balls” would be a reminder of all of this since we both knew that she could arouse me very quickly. I never did get to pinch her nipples though and over the next few days she did walk around topless, which left me in a continual aroused position, but unable to do anything to release it.

2

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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Staring at girl punishment

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A year when I was 14(boy) I was home alone with my older sister(19). It was in the afternoon and my sister had her friend over to come swimming in our pool. My sisters friend name was Heather and she was More

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Worst Embarassing punishment

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I’m a fifteen year old boy and I’m dating a girl from my grade. The school year was almost over and it was really hot out. One day after school, my girlfriend (Katie) planned to go swimming at her house. More

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