Anna’s Diary: A Fantasy Confession

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I did something I know was wrong and I should feel bad about it but truthfully I don’t because it made me happy and I felt the need to get it out my system.

I should probably explain what I did but first I must confess something. Ever since I was a young girl I’ve had a thing for bald guys, I don’t know what it is but there’s just something really sexy about it.

I’d spent countless hours watching clips of guys buzzing their hair off on YouTube and pleasuring myself to them.

I’ve spoken to friends about sex and what they’re into and most of them I would consider kinky or into some sort of fetish but I realised from a young age that my fetish wasn’t common and people might laugh at me if they knew so I kept it to myself whenever my friends would ask me what kinda porn I watched.

As much as I enjoyed the videos it wasn’t enough to keep me fully satisfied. I really wanted to shave a boy, there was one boy in particular. His name was Joe, we had a couple classes together but we never really talked. There was no way Joe knew that I liked him, heck, he thinks I don’t even know his name.

We’re in completely different social circles, I don’t mean to sound egotistical but I’m the pretty, popular girl and Joe is a little bit of a loner. It’s not like I could walk up to him and tell him that I had a crush on him, my friends wouldn’t understand and I couldn’t explain to them.

Truthfully what attracted me to Joe was his hair. I loved the way his hair covered his face, every time I looked at him I couldn’t help but fantasize about taking a pair of clippers to it. It fell well below his shoulders and was a dark brown.

There was just something about a boy with long hair being shaved bald, revealing his handsome face that had been hidden behind his long locks that was a huge turn on for me.


The Invitation

I was sat in English class, talking with a group of friends. We were talking about the party that was happening at mine on the weekend whilst my parents were out of town.

I could see Joe sat at the front of the class, I really wanted to invite him but I didn’t know how. As much as I wanted him to come but I couldn’t invite him normally in front of my friends because I knew they would judge me for it.

I scrunched up a piece of paper and threw it at the back of Joe’s head. “Hey nerd” I shouted. Joe turned around rubbing the back of his head. “What do you guys want?” he asked in an annoyed tone. “How come I’ve never seen you at a party?” I asked, trying to come across as an asshole as not to seem like I’m being weird.

Joe turned back around and didn’t respond. I scrunched up another piece of paper and threw it at the back of his head. “I bet you’re a big virgin. Probably not even tried alcohol before” I said.

I know I was being kinda an asshole but I really wanted him to come and I didn’t know any other way of making that happen and still being seen as cool.  I needed to pressure him and making him feel like a loser and that he needed to fit in. In my friends eyes I was just messing with him so it didn’t seem out of the ordinary.

“Come to my party you loser, or are you a little mommy’s boy that had a bedtime” I said. I could see Joe begin to get frustrated, the whole class was laughing at him. I knew that with enough social pressure he would cave, I know that makes me kind of a bad person but I did it anyway.

“Fine, I’ll come. You guys are assholes” Joe said. All my friends were laughing at him, I sat there in a world of my own, I couldn’t believe I got him to agree to come. I was trying to hold back my smile.


The Party

It was finally Friday night, it was party night. The week felt like it had been dragging, especially so since Joe agreed to come to my party. I didn’t even go into school on Friday, I spent all day sorting everything out for the party.

If I’m being honest, I also wanted to go shopping and get myself a new outfit and I couldn’t do that if I was in school. My dad gave me a credit card for emergencies, I doubt he would even notice if I had used the card for non-emergency purposes. He had a good job, I’m sure with the amount of money he makes he wouldn’t notice the charge on his account anyway.

It was just after 9pm, I was with a group of friends drinking a beer and I noticed Joe walk by. I know he agreed to come but I still couldn’t believe that he actually came.

“So the nerd came” I shouted. My friend Chris grabbed Joe by the shoulder and pushed him towards us. “Drink this nerd” said Chris handing him a beer. Joe looked incredibly uncomfortable “I can’t, I’ve got drive home” said Joe.

People just started chanting “drink” over and over again, pressuring Joe into drinking. I took off as Joe chugged the beer. I just needed to get some fresh air.

The party had been going on for a couple hours now, I hadn’t seen Joe since the chugging incident but I knew he was pretty upset about it. I kinda new that would happen if I called him out but Joe needed to loosen up a bit, I thought the alcohol would help.

I was stood in the lounge, Joe stormed in and unplugged the stereo, stopping the music. Everyone turned towards him confused on why he was so heated “someone here slashed my tyres” he said. He was visibly upset, I could see that he reached his point. People started cussing at him, I wanted to defuse the situation so I approached Joe and grabbed him by the arm and dragged him into the kitchen.

”What’s wrong with you dude, you could’ve gotten your ass kicked” I said.

“Someone slashed my tyres and I can’t get home and my parents are going to kill me, I knew this was a bad idea” he said in a panicked tone.

“Look, I’m sorry about your tyres but you can’t be sure that someone slashed them” I replied.

”Yeah I can, you guys only invited me here to make fun of me” Joe replied.

”I can’t fix your tyres but look if you wait around I’ll give you a lift home once everyone’s gone. I’ve only had one beer” I responded, trying to calm Joe.

“I’m not waiting around with these assholes” he responded.

“If I let you wait it out in my room, promise not to touch my stuff please?” I said, just trying to find a workable situation.

Joe agreed, thankfully I defused the situation. The music began playing again and the party resumed. The rest of the night was pretty uneventful, a couple people got wasted but at least nothing got broken. My parents would’ve killed me if someone had broken something.

I didn’t exactly tell them about the party, but in my head it’s their fault for going away for the weekend leaving a high school senior home alone. What else did they expect?


Truth or Dare

Everyone had pretty much left, the last few people were leaving, it was getting close to 3am. I headed up to my room to see if Joe was ready to leave. I opened my bedroom door and Joe was looking at my trophies on the dresser.

“I thought I told you not to touch my things” I said, Joe was startled.

“I’m sorry, I was just looking at your trophies. I didn’t realise you played Magic: The Gathering. You’ve won a lot of regional tournaments, I wouldn’t have expected that from a girl like you” he said.

“I know, I like to keep it on the down-low. You know what it’s like in high school with all the pressures to fit in” I replied.

Joe and I got caught up in conversation and the time flew by, the ride home had been completely forgotten about. We sat on my bedroom floor and we were playing spin the wheel.

Joe was kinda boring not gonna lie, he took the truth instead of the dare every time but it did allow me to find out some useful information about Joe, like how he was a virgin and that he had a crush on someone in our English class.

The crush had to be me, surely I thought to myself. Not to sound arrogant but I’m by far the prettiest girl in the class. It had to be me, at least I really hoped that it was me.

“Hey, can you grab me a beer out of the fridge? I’m just gonna head to the bathroom” I said to Joe.

“Sure” he responded.

Joe wasn’t gone more than two minutes, I could hear him approaching my room. The floorboards creak getting louder as he got closer.

“Is Corona fine” Joe said, stood in my doorway with the beer in hand.

“Yeah, that’s cool. Come sit back down and play” I said, patting the floor as to signal him.

He handed me my beer and a took I sip “So I have an idea, no more truths, only dares” I said.

“I dunno” Joe responded.

“You can come up with the first dare if you like” I said, trying to convince him to continue playing.

”Okay, if it lands on you, you gotta down that entire beer” he said. It was pretty tame for my liking but at least he was going along.

Spinning the arrow it landed on Joe “drink up” I said. Joe grabbed the beer and downed the entire thing in a couple seconds.

“Okay, my turn. If it lands on you, the other person gets to send a random text from the losers phone to anyone in their contacts list”

I spun the arrow and it landed on Joe again.
“Hand over the phone” I said. Joe handed it over reluctantly.

“You’ve not many contacts in your phone” I said.

“Well I don’t have many friends” he responded.

I clicked on his Dad’s number and began to text him, the text read “Hi Dad, I’m a huge virgin. I seen you fucking Mom last night and I wacked one out watching you. You guys were great. Love you, Dad”

Joe was so embarrassed, he knew his Dad would probably be really pissed at him when he got home. I thought it was funny, I thought of it more as playful flirting.

“It’s your turn” I said to Joe.

“I can’t think of one” Joe replied.

“Okay, I have an idea. Let’s step this up a notch. Loser has to shave their head” I said.

“No way. I’m not doing that, that’s too far” Joe asserted.

“Come on Joe, don’t be a pussy. There’s no way this lands on you three times in a row” I said.

Sure enough, it landed on Joe three times in a row. “No, I’m not doing it” Joe said, trying desperately to back out.

“Come on Joe, don’t be chicken” I replied.

”I’ll do it tomorrow” he said, just trying to get out of it.

“My Dad has a pair of clippers in the bathroom, I can do it for you” I said.

“I’m fine, thanks” Joe said.

”Come on, fairs fair. I would’ve done it if it had landed on me” I said trying to pressure Joe into it.

“You know how long it took me to grow my hair out this long?” he asked.

”It’ll grow back. I think it’ll suit you anyway. Plus how many guys get to say they got their hair cut by a pretty girl like me?” I said.

Joe reluctantly agreed after I kept pressuring him. I may have used my sexuality a little bit but I was doing him a favour even if he didn’t see it that way.



I searched through the bathroom cabinets frantically looking for my Dad’s clippers. I couldn’t believe I convinced Joe to let me shave his pretty, long locks. To say I was excited was a bit of an understatement. I had fantasized about shaving his head a lot and here I was about to do it. 

“I’ve got them” I shouted, emerging from bathroom.

Joe was still sat in the same spot that I left him. I removed the guard from the clippers “I’m not gonna need that” I told Joe, just trying to torture him.

As I flicked the clippers on I could see the dread in his face. He really didn’t want to lose his long locks. “Maybe that girl in English will like you with a shaved head” I said to him, trying to make sure he didn’t back out.

I faced him, I wanted to see his face as the first glide of the clippers went across his head. I went straight down the middle, his hair fell so perfectly. It was almost like he was supposed to be shaved.

“Oh my gosh, everyone is gonna make fun of me” he said.

“It looks good, don’t worry” I replied, just trying to calm him.

Seeing the long bald strip down the middle of his head, being able to see the contrast between his long locks and the stubble was a huge turn on for me.

Joe sat there silently with his face in his hands, I couldn’t help but wonder what was going through his head. I knew he wasn’t enjoying his shearing but I sure was.

I couldn’t help but giggle, I was really enjoying shaving him. He looked adorable hiding his face as his hair fell around him. It was only minutes before his shoulder length locks was replaced by a short buzzcut 

“I can’t believe I let you do this” Joe said, taking his head out of his hands. It was the first time I had ever seen Joe with short hair and I couldn’t believe how handsome he was.

I really wanted to compliment him but I held my tongue. Seeing him sat there with nothing more than a little bit of stubble left on his head, knowing what I had just done to him was a huge turn on.

Joe stood up, scratching at his neck “I need to go rinse off” he said

”I’m not finished yet” I replied.

“How are you not finished?” he responded, it was obvious that he was annoyed.

“I’ve got to go over to your head with a razor” I replied.

“I didn’t agree to that” he responded.

”Come on, you’ll like it. It’ll be relaxing, I shave myself all the time” I said, trying to convince him.

I really wanted to see Joe completely shaven down to the scalp. Every time I had imagined shaving Joe, I had always imagined leaving him completely bald. To get this close to fulfilling something I had dreamt about over and over again and not doing it, I wasn’t going to let Joe get out of this.

“Just sit back down, we’ve gotten this far you might as well let me. It’ll grow back to this length in a couple days anyway” I said, trying to pressure him.

I had gotten my way a lot with Joe up until this point. Pretty girls like me always get their way with guys and I knew how to use my sexuality to get what I wanted.

Joe finally agreed, when he said I could do it to him I got the biggest butterflies. My stomach felt like it was in knots. I could feel my heart beating, it felt like it was going to burst out of my chest.

I headed back in to the bathroom to grab the stuff to shave his head. I looked at myself in the mirror and smiled from ear to ear. This was the first time I could let my excitement show, I mean I didn’t want Joe to know that I was really into this. This was my little secret.

Razor Shave

I knelt down behind Joe, lathering his head up with shaving cream until it was completely covered. I wiped my hands down on a towel that I had put on the floor next to a jug of water that I’d use to clean off the shaving cream from the razor.

I placed my fingers on the back of his head to make sure I could shave him properly. I wouldn’t say that I was an expert but I had seen so many videos of boys getting their heads shaved that I felt like I knew what I was doing.

“That feels strange, I don’t like it” Joe said as the razor moved across his head. I don’t know what it was but Joe’s hesitancy to embrace his headshave and his nervousness was arousing to me.

It was the rough, scratchy sound of the razor working against the growth of the hair too. Seeing his bald head emerge from underneath the shaving cream with each motion of the razor. His head shape was perfect, it really suited being bald.

I couldn’t believe how hot I felt, it must’ve been from the increased heart rate from all the excitement. Honestly, I was so excited I couldn’t even keep my hands still. I’m shocked I didn’t cut him just from how much I was shaking.

”You’re all done” I said to him.

His hand reached towards the back of his head “oh wow” he said feeling what his bald head felt like.

We both stood up “let’s go look in the bathroom mirror” I said to him. I wanted to see his reaction to seeing himself bald for the first time.

I walked into the bathroom behind him, as he walked in I heard him say “oh my god” in a shocked voice, he honestly sounded a little upset but I found his reaction cute.

He was looking in the mirror, touching his bald head “Everyone at school is going to laugh at me” he said.

He looked devastated, the longer he looked the more upset he seemed to get. As he turned around to leave the bathroom I just burst, I couldn’t hold it in anymore and I kissed him on the lips.

It was nothing more than a peck, but I couldn’t believe I just did that. Just seeing him with his bald head, knowing I did that to him and seeing his reaction to seeing himself bald had just aroused me so much that I couldn’t help myself.

I felt the regret the moment my lips left his, he must’ve knew at that point that I had a crush on him. I felt panicked, just trying to get out of the situation I just put myself in “I just wanted to boost your confidence, it didn’t mean anything” I said frantically.

He looked pretty shocked, I mean sure he was. There’s no way he could’ve known before tonight that I liked him. I had pretended I hadn’t even known his name and acted like a jerk towards him throughout high school.

It was going to be my word against his, there’s no way anyone would believe that I kissed him. I could’ve had any guy in school that I wanted, no one was gonna believe that I kissed the quiet nerdy kid. I didn’t want this ruining my popularity.

“You can take a shower if you like to get the hair off you, I’ll drop you home in the morning” I said, desperately trying to change the subject.

“urm okay, but where am I going to sleep?” he replied.

“There’s a spare bedroom, if you go out into the hall it’s two doors down” I responded.

”I’m gonna head to bed, I’m really tired. Towels are in the cupboard. Try not to make too much noise” I continued.

Honestly I wasn’t tired, my heart was racing, I felt more awake than I ever had but I just wanted to avoid the awkward situation I just put myself in.



As I laid in bed, I couldn’t stop thinking about Joe. I felt so aroused thinking about his bald head, I kept replaying that kiss in my head over and over again. The thought of his lips pressed against mine.

I just wanted to go for it, the last fulfilment of my fantasy had always been to have sex after I had shaved him bald but there were thoughts I was having that were holding me back.

I guess this is why I’m writing this in my diary, I can’t sleep. It doesn’t matter how many times I play with myself I just can’t seem to get him off my mind. It’s already 10am, I haven’t been able to sleep at all. I just want to go into the other room and do it but I’m afraid.

I have a confession, I have a couple actually. I’m a virgin, I know it’s kind of shocking, the most popular girl in school is a virgin. It’s not that it couldn’t have happened, I just never wanted it to happen until this moment.

I’ve had a crush on Joe since freshman year. I know my crush mostly stemmed from my fetish but I had admired him from afar for so long I feel like I’m in love with him. I’ve not so much as looked at another guy so that’s why I’m a virgin.

All of my friends have lost their virginity, they would talk about it. I was the only one in my circle that was still a virgin and there’s no way I could let that get out.

I wanted to lose it, I wanted to lose it to Joe but I was afraid. When my friends talked about it they said it hurt the first time and I was a bit of a baby when it came to pain.

There’s another thing, I mean I don’t feel horrible about it but I feel bad enough to write it down. None of last night was a coincidence

Some random person at the party didn’t slash Joe’s tires, it was me. I used the distraction of my friends to sneak out and pop them. I planned this whole thing in my head from the moment I knew I was having a party.

I knew Joe wouldn’t be able to get home, I’d stalked his Facebook enough to know he lived about a half hour drive away. I wanted him to stick around long enough for us to get time to be alone together.

I knew he would react like that, I planned on him going to wait in my room. Those trophies in my room were usually kept in a box in my closet but I put them on my dressing table on purpose knowing that Joe was also into Magic: The Gathering. I knew that would give us something to bond over.

The wheel didn’t stop on Joe three times by coincidence when we were playing truth or dare. I didn’t head to the bathroom when he went and got me a beer, it was all in my plan to get him out the room so I could rig the game so it would always stop on him.

I manipulated him by letting him go first at picking the dare, I knew I had to make him feel comfortable. I didn’t want to go straight to shaving your head because that would’ve freaked him out.

I used my sexuality and I pressured him into letting me shave him. I know he hated his bald head but I got so much pleasure out of doing that to him.  I’d been planning this whole thing for weeks. I know I should feel like I’m a horrible person but I don’t truthfully.

I felt like I needed to get this out of my system. I don’t feel bad about manipulating him into letting me shave him, but it feels like a different thing entirely to use that manipulation to have sex with him.

I don’t feel like I can be fully satisfied without going into that room and having sex with him. If I did go in there I don’t want it getting out either that we had sex. I just don’t know what to do.

*knock, knock, knock


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