He is in me! I couldn’t believe it was happening, but he is in me!
A few months before that happened…..
I was almost fifteen and moving to a new city, well, new to me. It’s my dad’s hometown and after lockdown and furlough he had a new job and we were moving back there. Me, my mum and my sister had already moved ahead in a rented home while dad was sorting the old house sale and tying up loose ends. Mum had taken my sister to a sixth form college and as I didn’t know a soul here, I was a bit bored and being shown around a few places by my uncle. He was really cool, and worked as a graphic designer, something I wanted to do myself as I really enjoyed art and drew a lot of anime characters and things in that style. Oh, I should introduce myself, I’m Andrew, but always go by Andi, and with lockdown I started experimenting with my look and while my sister called me a goth, really it was really more goth lite, maybe a bit emo, but even then that’s not quite the whole truth and I will explain that a bit better when I understand it myself. I had been bullied a bit at school so was quite pleased to escape it with lockdowns. I’m skinny and try to project a bit of an androgynous look, because, well, that’s something else I will talk about later. And while I wasn’t allowed to dye my hair black, it is down to my chin now and I would like to dye it a bit darker as I while I like the brunette hair, I would like it be darker, hence why I liked the product.
Anyway, I was with my uncle being shown around and we stopped at a pub to get something to eat, sitting in the garden waiting for our food. I was sipping on a coke while he drank a
Guinness. It was a nice day, but of course I was wearing a hoody, and as I had had run out of any hair styling product I had put it into what I liked to call a man bun, but in reality was two mini messy ponytails as the hair was always sticking up and out, but I liked it.
We chatted a bit about random stuff and he was asking me questions about my art and how I was getting on with Illustrator and so on, when a woman called Sandy came over to say hello to him. I knew he was gay and had guessed from the rainbows this was a gay bar. I don’t have a problem of course, why would I? Sandy said hello to me and my uncle explained why I was here and what we were doing.
“Do you know what school you’re going to be going to?” Sandy asked me.
I said, “Um, yeah, it’s the academy”.
Sandy replied, “Oh that’s good, I have a niece, well, god daughter who goes there. She’s going to be in Year 11, what will you be in?’
My heart sank, I felt like I was being ‘forced’ into meeting her and everyone hoping that I would have a friend before school. My uncle replied for me, telling her I would also be the same year. There was the expected discussion about us meeting up with her and me trying to think up an excuse to avoid it, when Sandy started to change my mind.
“She’s a goth like you, although I think she calls herself a pastel goth or something like that this week anyway, but I suspect you might listen to some of the same music. I know she likes anime and that stuff.”
I was going to say I’m only kind of a goth, but when she mentioned anime I decided to give her a chance. Sandy then said to my uncle that we should talk about it and if I was ok we would go from there and she left. He’s being protective of me, which is nice and he asked me if I did want to meet her and if I was ok with it if I said no, and that he didn’t know this was going to happen.
I thought about it for a second and the thing is, I’m bored. I only sort of know this place and there’s not a huge amount for me to do here. I was nervous about meeting her but agreed to it with a shrug and a smile, and then he went to chat to Sandy and I saw them both texting people. Five minutes later he came back and told me it was agreed, I would be meeting her tomorrow and we would all go ‘somewhere’, wherever somewhere is.
Mum knew about it when I got home, it had all been arranged and the next day I was trying to work out what to wear. I didn’t have a huge amount of clothes in the style I prefer, but I did have a few things I liked. I put on my baggiest black jeans, my Doc Martens, and a black long sleeve top that I love. It has purple cats on it and I love cats but my sister is allergic so we can’t have one. I found it in a charity shop and it didn’t have a label but it was so soft it felt really nice to wear and fitted me tightly, making me look even more androgynous but I had learned to own that, and with my style it made me feel comfortable. As it was so fitting, I put a baggy tee shirt over the top to hide how skinny I was and so on. It was quite new and an Evanescence shirt as I loved the band. Uncle Steve pulled up in his Audi EV with Sandy already sitting in the front so I climbed in the back and off we went. We drove round the corner and stopped, so it seemed she lived close to me. A door opened and out walked a goddess!
She was wearing a full length body hugging dark long green dress with a split that went to mid thigh on one side and what I first thought was a wide belt but was a little corset type thing, knee high New Rocks and a little bag hanging from her arm. Her long red hair was straight and she looked fierce! I was a bit embarrassed as I felt massively underdressed compared to her. She walked to the car and got in, swinging her legs into the car and she gave me a huge smile.
She said, ’Hi Andi, I’m Sarah. Love the top.”
And off we went with me saying hello back. Sandy and Uncle Steve chatted away and did most of the talking until we arrived at a Starbucks on the edge of a park. We went in and had a coffee and slowly I opened up a bit more to her. I found out later she was nervous as well which is why she dressed how she did to give herself a confidence boost. I know I used my look as armour in a way, and she said that she sometimes did the same, such as almost going over the top with her clothes today and giving her mum a heart attack when she did.
Her original outfits skirt really was that short.
After we finished the coffee, they asked us what we wanted to do, and Sarah wanted to see some of my art so we headed to mine so I could get my laptop out as Sandy wouldn’t let her walk home dressed as she was, even though it wasn’t far, so we went to hers instead. I did see Sarah roll her eyes at that and it made me smile as old people just don’t get us really. Sarah’s mum was in and went out to say bye to Sandy, and went up to her room. We had to leave the door open, but closed it most of the way. I had no idea where this was going but went along with her. I showed her my art, what I was working on and the scans of my hand drawings.
She looked at me and said, ”You know, your eyes would look great with some liner.” I told her I knew and was going to wear it today but didn’t feel confident enough. “Right,” she said, “we need to fix that.” And she opened up her make up box. I told her it’s ok, and she kept trying to convince me to do it, but I just smiled at her until she stopped talking. “What? What’s the problem?”
“I have my own make up.” I told her.
She squealed in delight, and told me to go stand in the corner while she got changed. She told me a little about the scene here and that while it wasn’t that big, there was a club that we could go to when they had a goth night once a month that was kinda cool, even though I had told I wasn’t really a goth, more goth adjacent. But the next one was in three weeks and she said we should go, then told me to turn around. She had swapped the dress for skinny jeans and had a long top that was really a dress that was white with some purple shapes on it.
As I walked closer I saw the purple shapes were cats and it was the same as my top, just the colours reversed. I reached out to touch the material and it felt the same as mine and had the same long sleeves, but hers was just longer on her body. She reached out and took hold of the hem of mine and turned it inside out showing it to me. She said, “Your’s has been shortened into a top. Now you know why I like it!” And with that she picked up her bag and I grabbed my laptop and followed her out the door.
Two hours later when my mum and sister came home, I was wearing eyeliner, eyeshadow, and some of Sarah’s blusher, eyebrows pencilled in (and tidied up a little bit), and the same lipstick colour as her. The first thing mum said to me was that I looked very pretty.
Sarah had given my hair a similar style to hers, no parting for a change and flipped it over the top and behind my ear. We had posted some photos on her insta that were pulling in a lots of likes, and were both giggling away at the comments asking ‘who is the other girl?’ We screamed with laughter when some boys were saying how much they were looking forward to seeing the ‘new girl’ at the school. The DM’s were even funnier with a lot of accounts with no profile picture getting blocked right after they had seen our reply rating them.
Outside of porn I don’t think I had ever seen so many erections!
Sarah went home shortly after my sister, Claire, had got home and she helped me clean the make up off with some of mum’s wipes. Neither had any issue with me wearing it, in fact, mum surprised me when she said she had always thought I was a little gender fluid, and that me wanting to look bit androgynous allowed me to experiment. And then my sister agreed with her.
It gave me something to think about and it made me more relaxed about wearing my own eyeliner and some eye shadow in front of them, and maybe, just maybe I could risk telling them that, well, I think I might be gender fluid, or at least a femboy as I while I like looking androgynous, I would prefer a little more femininity in my style.
The next day I put on my own eyeliner and some black shadow as well, trying for a kinda smoky eye look, and then I went round to Sarah’s as planned. We didn’t have any plans to do anything, we were just going to listen to music, some HIM and Evanescence, even some classic stuff like Bon Jovi and Led Zeppelin and so on while we just chatted.
At some point the conversation turned around to fashion as I was moaning about how few options there really were for goth or grunge or emo men, basically, black jeans, tee shirts or hoody’s and Sarah pointed out it wasn’t really that different for women. We ended up pulling out her wardrobe with me counting the variations. With shoes alone she had so many more options than me. I was wearing a pair of ankle rider boots as my mum called them, but Sarah had four different versions of my boot each with a different heel height.
She said, “Look, if it’s such a problem, you can borrow any of mine when ever you want.”
I looked at her New Rocks and said I wanted to try them. I had a pair of my own but knew she would say no, as I would never let anyone wear mine. But she said yes, so I slipped off my boots and put them on, zipping them up. They fit me perfectly and I walked about in them and she said, “See, it’s no big deal.”
I replied, “I know, but I already have a pair of these.”
She rolled her eyes at me, and handed me a pair of dark burgundy shiny platform boots with at least a four inch heel that were in the same rider style as mine.
“Ha ha! Do you think I’m scared to wear them?” I asked.
“No, I think with those skinny jeans they will look great.”
She had a serious look on her face and I was worried I had upset her, so I took them from her pointing out I will look stupid in them, maybe a little scared to put them on in front of here and she said “Man up and be a woman about it!”
Fine! I took the New Rocks off and put them on. It felt weird having my foot forced into being toe down as I had never worn something so high, but we weren't going anywhere and only in her house. Plus, like mum said, she seems to think I might be gender fluid, and they felt comfortable if a little strange at first.
But secretly I was thrilled and tried to hide it.
We stood in front of her mirror and looked and they did make my legs look great and they weren’t as hard to walk in as I expected them to be. It was also funny being a little taller than Sarah now and she didn’t like that so put a pair of boots on herself with a similar height heel. We went downstairs to her kitchen to see what was in the fridge and that was a bit strange as going down the stairs I knew I had to turn slightly to not fall, and then standing at the worktops I was higher than I was used to and that felt really weird. I mentioned it to Sarah and she told me that the first time she wore heels she felt the same but got used to it so I will as well.
We took a sandwich back to her room with some crisps and carried on chatting and listening to music. She said, “The top you wore yesterday, if you liked it so much, why did you hide it under the baggy tee shirt?”
This was the conversation I was dreading, it was part of why I got bullied at my old school. Sarah saw how nervous I was and came over to give me a hug and said, “It’s ok, whatever you want to say will be between us.”
I looked at her wondering just how true that was, but guessed she would find out about it eventually. I got her to promise that she would keep my secret. She got up, picked up her New Rocks and said they were mine if she told anyone.
I looked at her and got my nerves together and said, “So, a couple of years ago I started budding.”
I waited to see what she would say and for a few seconds she was completely lost, then her eyes went wide.
“But, you’re a boy!”. I then explained a little more and that after a lot of tests it turned out I had an extra X chromosome making me XXY and had developed gynecomastia thanks to a hormone imbalance because of it. So far that was the only symptom and they’ve been waiting to see if my testosterone goes up, but so far I have similar levels of it as a women, but of oestrogen as well. When I turn 15 right before school starts I have to make a decision about what to do, do I go one way or the other. Sarah gave me a big hug, thanking me for trusting her and telling me not to worry about her saying anything unless I wanted her to. She then asked the question I’ve been dreading, the one my parents don’t ask as they said not until the day after my birthday.
“So what are you going to do?”
I confessed I liked where I am right now, sure school is difficult but it won’t go on forever. I wasn’t ready to confess to her about how I see myself, not yet, just saying I quite like looking androgynous at the moment. Sarah was about to ask something, but stopped herself. I think I knew what she wanted to ask, so told her she could ask me anything.
“So, does it work?”
Ok, not the question I was expecting. Seeing that I had just told her I started growing boobs two years ago, telling her that was nothing.
“Yes, it works.”
And we both started to giggle. There were a few more questions about how I hide them and her understanding why I liked tight tops with a baggy tee shirt over it. She looked at me and I still don’t know how I didn’t see what was coming next. “So take the tee shirt off then.”
This was nerve wracking, I felt like I was getting a friend here, but what do I do? She said it will happen anyway at some point so I may as well get over it now, and I slowly started to take it off, but she wouldn't wait and ripped it over my head, leaving me in a tight top that helped to keep them a bit flatter and stop some of the bouncing.
I was trying to fold my arms to hide them, but she got up and faced the wall, took off her shirt, slipped off her bra and put on a tight top and then turned to face me. She said to me, “See, I’m ok with you seeing the shape of my boobs, now let me see the girls!”
I couldn’t help but laugh and slowly lowered my arms, standing up to face her. She looked me up and down and I thought, well, if she can then so can I, so we stood there checking each other out. Finally she went to a drawer and took something out. It was a tape measure and said, “Come on, arms up.”
I had always avoided this, but she explained she was going to do it and what she was going to measure. She did my waist first, then wrote a number down. Then came back and tried to measure my hips, but her face looked unhappy with that, so she measured around my chest, right under my boobs, then right across my nipples.
She looked at me and said this won’t work. I didn’t understand and she said, “You need to take the top off.”
No way! I was not doing that, and told her in lots of different ways I wouldn’t do it. She took a deep breath and sighed, saying to herself ‘I knew this would happen’, and then she lifted her top over her head. There she was, half naked, right in from of me. She put her hands on hips as she waited for me to do the same.
Slowly I started to lift it over my head, and when my face was completely covered I felt them both drop free, not exactly a big drop, but a drop never the less and she gasped. I quickly covered up and she apologised saying she wasn’t expecting to see what she did, please carry on. It took a few seconds to calm down, get my nerve back and I finished taking it off, dropping my top on the side. And there we were, both half naked.
“They’re quite nice, you know.” She told me.
I was blushing everywhere it felt, and finally was able to say her’s were nice too. It’s funny, other than porn this was the first time I had seen boobs that weren’t in the mirror. It didn’t help that she was very attractive. I was attracted to her, but right now this felt more like ‘you show me yours and I’ll show you mine’.
So thankfully the thing that she asked if it works was only paying a little attention right now, my nerves and fear were keeping it from it’s full, but not that impressive glory. Sarah got back to measuring me and writing it down, asking me to lower my jeans so she could get my hips. Obviously my boxers weren’t Calvins, but they were the same style so I didn’t need to drop them for her. Sarah then handed me the measure, turned over the page in her notebook and told me to measure her.
This was horrible for me! She had just touched my boobs, the first time it wasn’t a doctor and my nipples had done that thing they do and gone all puffy. Now I was likely to touch her boobs and couldn’t think how I could keep them under control, let alone the other thing! I decided to start with her hips, so she undid her jeans and lowered them. There was her underwear and I’m thinking I started at the wrong place. I wrote it down. I then did her waist and her chest. She looked at the paper and told me it was called an underbust, not a chest, so I crossed it out and rewrote it, all while trying to think of things than that I had just touched her underboob, and now I needed to go over her nipple!
I got through it, but down there was very awake now, and thankful it was over. She mentioned to sit on her bed and grabbed her notebook and laptop, as she laid the numbers out next to each other. In her mirror I could see us both sitting there topless as if it was nothing at all.
She looked at me and said, “I should really hate you for this!” I looked at them and what we had each written.
Andi
Boobs - 30
Waist - 24
Hips - 34
Sarah
Breast - 32
Underbust - 29
Waist - 26
hips - 34
I asked her, “Why didn’t you put my underbust?”
She told me she just wanted to see how I would react to my boobs being touched, and if I was brave enough to do the same to her. Then she looked me right in the eye, saying, “Plus I wanted to know if you were lying about it working.”
And her eyes flicked down. “You bitch!” I laughed and nudged her away.
“Takes one to know one.”
It was funny, I felt totally relaxed about sitting here like this. My mum has seen them but only at the doctors, my sister has asked to see them but I didn’t want anyone to see them if I could avoid it. But she had just touched mine, I had touched her and it was just two friends comparing sizes.
She said, “I should hate you seeing that you’re a skinny bitch, but you’re cool.”
We chatted a bit more about nothing in particular, just sitting there and all my self conciseness seemed to slowly fade away about it. Sarah got up walked to one of the piles of clothes and pulled something out that looked like a black blouse and told me to pull it on. I stood up and pulled the blouse over my head. It was quite long and when I looked in the mirror realised it was a short dress. The sleeves were short and puffy and it had a square neckline with black embroidery and edges and was elasticated under my boobs. It looked ok on me.
I turned to Sarah and she was smiling. “You know, with your figure I think we could share most of our clothes. Although men’s clothes are boring of course so I don’t expect to borrow much!”
I threw my tee shirt at her, but she just held it up laughing, telling me she wasn’t surprised I threw it away. I left the blouse/dress on and we carried on chatting away and after a bit she asked me a question that really surprised me. “You know, you really need to wear a bra with that dress. I don’t think I still have any in your cup size but I do have some bra fillers that will help if you want?”
I didn’t understand what she meant and must have looked confused. She went on to explain that when I took my top off it looked like I was an A cup, which of course made me cup them and not really know what she was on about. Mum and my sister had been trying to get me to wear one, even a sports bra, but I was happy with the system I had, although it was nice feeling them be a bit more freer and I did like how the material felt against my nipples.
Sarah was opening up one the lower drawers on her dresser, searching in the back until she pulled out a black bra. She held it up and said to me, “Come on, let’s get you in this!” And she threw it as me. I took off the blouse/dress and slipped into the bra, doing it up behind my back. Sarah stood behind me and helped, explaining what I needed to do by adjusting the straps.
She went back to the drawer and stood behind me, pressing against me as she slipped two things in my bra, lifting up my boobs. I had stopped trying to pretend they were my pecs now, as she adjusted the inserts. I could smell her perfume and while I’ve had a girlfriend before (not like we did much and I ended it when the girls became harder to hide), she wasn’t as stunning as Sarah. She walked me to the mirror and I now had a cleavage and two very obvious boobs. She explained that if I had a padded bra they would give me some lift and she kept staying behind me as she moved about my ‘boobs’ to get them sitting int he bra correctly.
I put the blouse/dress back on and knew for sure now it was a dress, it fitted me a lot better and where it was pulled in at my waist made my ‘boobs’ very obvious, especially with the little bit of cleavage now showing. Sarah kept looking at it and as a teenage boy who’s boobs had just been moved about I was glad the dress was flared as I can’t imagine how I could have hidden what was going on down there in skinny jeans. At the end of the day I needed to go home for food so I took the dress and bra off, completely forgetting about the inserts which fell to ground, making us both giggle away again.
I started walking home and about halfway I stopped and went back. When Sarah answered the door she was holding my boots and I stepped inside to change them back as we talked about how comfortable I was wearing her heels. She was coming to mine tomorrow and we were going into town so she could show me some good shops. Today felt really good, I felt comfortable and desperately wanted to share with her what I feel, but there’s always the fear that she will laugh at me. It took a couple of days before it clicked with me that I had worn a bra, a dress and high heeled boots with her so she was unlikely to be offended by it.
The next day Sarah knocked on my door to take me into town to show me around. She was wearing leggings and the boots I wore yesterday, with a shirt and a wide black belt to show off her waist with her hair down. I was in my skinny jeans and a hoody, black of course and my hair was in a ponytail low on my head. She looked me up and down and said this won’t do, I should at least wear some eyeliner! I invited her in and said I liked how her eyeliner was winged and she offered to do the same for me.
She opened her handbag and took out some liquid eyeliner, I had some but hadn’t used it before so I showed her what I had and she showed me how to do it as she talked me through the process. I have to admit, I wasn’t expecting it to the be the same as hers, maybe a bit less but she said it looked good so I tried to copy it on my other eye. It took a few attempts, cleaning it off each time but I finally matched eyes. I must admit, it did look good and certainly gave my face a more feminine look.
She pointed out that with the hoody it now made my eyes look a bit over the top so we detoured to hers for a change of outfit for me. I told her I wasn’t going to wear the dress or bra and she said that’s not what she was thinking. In her room she handed me a vest with spaghetti straps and I put it on, glad it came up much higher on my chest, but of course it meant the ‘girls were clearly on show’ as Sarah pointed out. Then she gave me a black short sleeved shirt that when I put it on and found out it was fitted to my waist and the sleeves were very short, but I did like the look overall, checking myself out in her mirror.
We got the bus into town and the driver asked where ‘you girls’ were going today. It did make us laugh and it’s not like I was trying to look like a girl, I mean, my skinny jeans had a kinda obvious, if small, male shape, but I was a bit thrilled by it. After looking around a few shops and Sarah picking up a delivery for her mum, she said we would go to the only goth shop tomorrow. Back at Sarah’s after we had something to eat, I got changed back into my hoody and we cleaned off the eyeliner.
We were sitting next to each other on her bed resting against the backboard and she leant against me as we chatted. I looked at her and she looked at me, I was hoping she wanted to kiss me, she really is beautiful, and I leant forward a little, just in case I was wrong. She tilted he head and leant towards me and I titled mine.
I’ve no idea how long we kissed for, but I loved every second of it. We knew we had to stop as our hands were going to a lot of places and I don’t think I was quite ready to have sex yet and I had no idea how to make it happen, or have a condom anyway, but we were certainly touching each other a lot.
We stopped as I needed to be going home and we cleaned ourselves up we chatted a bit. She admitted that she liked my androgyny and thought I made a very pretty girl but also a cute boy that she definitely liked kissing. I told her I thought she was beautiful and that I was really worried I was taking her away from her friends. She said, “Oh don’t worry about that, we’re going to meet some of them tomorrow.”
I kissed her again as I left and passed her mum on the way home who said she was pleased that I had found a friend after moving here, reminding me we had to leave the door open. I laughed and told her she had nothing to worry about as we’re just friends.
The next day I arrived at Sarah’s early and it was already a hot. Once again in skinny jeans but also in a tight long sleeved top and a baggy tee shirt with my hair down for a change to try and stay cool. Sarah was in shorts, wide fishnet tights and a vest top, also with her hair down. We had some time, so we had a can of coke each before we left. She asked if I had my own shorts and I admitted I only had swimming trunks I haven’t worn in years so doubt if they fit me anymore, reminding her of our conversation about men’s fashion.
She looked at me for a couple of seconds and said to follow her. She rushed ahead to her room and when I got there she was pulling things out of drawers and her wardrobe. She turned to me and said, ‘strip’. I took my tee shirt off and picked up the vest she had laid out in the same style as I had worn yesterday but shorter, and started to put it on. She told me to stop, she had more to do. I waited till she finally looked round and she said I need to lose the jeans as she handed me a pair of jeans shorts.
“Really? I can’t wear these!” I told her and she told me to put them on as she walked to the corner of the room to face away from me. I stripped off my jeans and pulled the shorts on. The felt really weird, what with me wearing boxers under them that were poking out of the legs.
She said, “Mmmmm, I thought so.”
And she went to one of her drawers and pulled out a packet of something. She opened them and handed me what I realised was a pair of brand new underwear. “They are boyshorts, brand new. Go to the bathroom and put them on, and then the shorts.”
I took them with me out the door, wondering what was going on. She told me to hurry up. In there I stripped my boxers of and pulled up the black cotton boyshorts, wondering if they would fit as the seemed so small. They stretched to fit and obviously weren't made for a boy, and I debated whether to tuck or not, but just pulled the shorts up and headed back. She looked me up and down and then handed me her iPad. I looked at the screen and it was a page saying ‘how to tuck’. I was confused and looked at her and she pointed to the bulge in my shorts. Ok, back to the bathroom taking the iPad so it at least looked like I was going to follow the instructions, and three minutes later I returned with a very smooth front on the shorts, which I swear were only a little bit bigger than daisy dukes!
She smiled at me saying how much better it looked, but was worried it was painful or uncomfortable but I reassured that wasn’t the case at all.
‘Ok,” she said, “now I need you to take the shorts off so you can put these on.” And she held up something that once I took them from her realised it was a pair of very wide hole fishnets like the ones she was wearing. I told her I wasn’t sure about this, which wasn’t really true as I kinda wanted to try her look after yesterday, plus I did like how my boobs felt supported in the bra yesterday, so I decided to go with this. It would be fun to dress like her and maybe it was the excuse I was looking for. She gave me a smile and said, “Go on, I know you want to really.”
I unbuttoned the shorts and lowered them and she stopped to look at me down there. I wondered what was going on, but she was looking closely at my tuck to see how I looked. Her hand reached out to have a feel but I stopped her. “Please don’t, I’m worried that if you do it will get, well, you know, and be painful where it’s tucked.”
She pulled her hand back and I sat down to pretend to work out how to put the tights on and she talked me through it. Finally I pulled them up, then stepped back into the shorts. I was about to head to the full length mirror but she stopped me, and handed me the black bra. I slipped it on and got it hooked up at the back then put the inserts in and adjusting the fit to give me a cleavage. I was about to put the vest on, but Sarah opened up her make up case and together we finished making up my face, lipstick the works. I then put the black vest top on, picked up a pair of boots similar to what I wore two days ago but in black and put them on.
I looked at myself in the mirror, but the look just felt wrong. Somehow on me the wide fishnets tights just didn’t feel right. I was already super self conscious and they felt like a step too far, and I told Sarah, so off came the shorts again, then the tights and the shorts back on. Like this I couldn’t pull off the whole androgynous look, I was very much looking like a girl, and while I was excited about that, I was a bit scared too, and decided to tone down the make up around my eyes until I felt a little bit more invisible.
We stood in front of the mirror together and I grabbed my phone as we started taking loads of selfies, selecting the ones we liked the best before Sarah posted them.
I was looking at the ones in my phone and wondering if I should post them to my account but I wasn’t quite sure, so maybe I need to think about that for the future. Plus my sister followed me and might tell our parents. What about the others from my old school? What if they see it? I’ll save that decision for another day. Sarah grabbed a handbag and asked for what was in my jeans pockets. It took a second to understand what she meant so I got my keys, phone and they went into the bag while she emptied my wallet into a purse.
While I was admiring myself in the mirror, I picked up a shirt she had left out, and pulled it on, feeling a bit more covered up and maybe a bit less visible. Sarah went downstairs for something, and when she came back she had a carrier bag and put my clothes in. “Come on,” she said, “let’s go.”
I followed her out blindly and it was only when she opened the front door I realised what was about to happen. We were going into town today and my clothes in the bag were going back to mine before we went out. I was dressed like this and I froze. She walked back and took my hand, “It’s ok, you can do this. I can tell you want to.” She told me.
She gave me a big hug and I nodded. I think I can do this, I like looking feminine, and I’ve been wanting to do this for a long time, but never had an excuse to do it. At least I can say we were messing around and I wanted to try to look more fluid in the feminine direction rather than just androgynous. I took a deep breath and holding Sarah’s hand I walked out the door with her.
I was very aware today, more than the other day, that the boots with the high heels were making me walk like a girl, but I wasn’t trying to act like a girl, I was just being me. We dropped my bag at home and headed to the bus stop. No one stopped and pointed, although a lot of people were looking at the two girls waiting at the bus stop in tight shorts that showed a little bum cheek and I kept trying to fish the wedgie out until Sarah told me to not worry about it, the shorts are meant to do that.
When we got into town, the first thing Sarah did was take me to a shop to get a bra fitting to find out my right size. It was kinda awful to be honest, having to take the inserts out in front of a woman, then her measuring me. Turns out I was an A cup and not long before I’ll be a B cup the woman said, while Sarah was very much a B cup.
So that’s the story of how I brought my first bra, well, Sarah picked it out, a simple black tee shirt bra and I wore it out the shop with the inserts in my handbag, and Sarah’s old bra in the bin. We headed towards a different part of town, not far from the main shopping area and went straight to a boutique shop for alternative fashion called The Stop. Sarah knew the people in there and introduced me, and we looked around, tried a few things on and I even tried on a very short tartan dress, and borrowed a belt that pulled it in at the waist. It was really short and I was very aware that bending even a little would mean my boyshorts would be on display.
I did like it though, and knew Sarah had one so I could always borrow her’s. Wait, did I just say I would borrow a dress? I need to slow down a bit. Anyway, I took a few photos of it in the mirror, along with everything else I tried on before changing back. There was a corset top that hooked up at the front and I really loved it and almost brought it, but just had to stop myself as I wondered how I would explain it to my parents.
After chatting to the staff in there, we left and headed to the shopping mall to meet her friends. I suddenly felt a bit nervous and asked about Sarah about it. Sarah had already told them after seeing us on insta and no one seemed to mind about me at all. She told me they were surprised I had shaved under my arms as well as my legs. I admitted I did that after the first day together when I tried on some clothes with her, but I hardly needed to as there wasn’t a lot of growth anyway.
Sarah said, “I thought so, I wanted to ask after you took you jeans off as I couldn't see any hair down there.”
I told her I had shaved that as well, turning very red, but she told me not to worry, she does as well. I became very uncomfortable in my shorts at that point for a little while.
We walked into the mall and Sarah said she needed to go to the loo and was I coming with her? I was really confused at this point, what do I do? Yes I need to go, but do I go in there. Sarah made my mind up for me as she walked towards it holding my hand and I knew I needed to and couldn't go into the gents dressed like this. We went in, I sat down to go, wiped, joined Sarah at the sinks and washed my hands before we touched up our make up. While it wasn’t super busy in there, we weren’t alone and no one took any notice of me. Well, other than what I was wearing of course, but now my clothes felt like armour, like they made one part of me invisible and it was only my clothes that people saw. It was freeing.
Besides, I felt good about how I looked, no longer feeling like I’m hiding.
We headed to the food court and Sarah waved at a group of girls who very much were not dressed like us. We got a drink and went to join them and after being introduced, I realised they knew who I was; in that I was a boy. They didn’t really seem to care that much, but I was honest when asked about it, that yes the cleavage was all me. I explained that I was experimenting due to my condition and that while I liked the androgynous look, my mum thought I was probably gender fluid, but right now this is fun so I’m choosing to enjoy and embrace it today.
We chatted together for about an hour and they told me a little about the school and which teachers were nice, who wasn’t and so on. And then a boy walked over to us, looking at me. At first I thought he knew about me, but the girls knew him and he was friendly enough when he said hello. He was in the same class as them all and his mum was buying a new school uniform for him, so he was trying to get away for a bit but had to go back soon for the shoes! He pulled up a chair and sat between Sarah and me, and Sarah and the girls exchanged looks so I guess he is interested in her.
He looks at me and says, “Hi I’m Dave and you must be the new girl then?”
I blushed and felt my whole body go hot. I looked down and could see that even my boobs had gone red. Oh god, I thought, this is horrible! My school life flashed in front of my eyes and no matter what I said now, I would probably end up being bullied at my new school when everyone knew.
I opted for truth, just get it out the way and accept it. “Not exactly,” I told him, “I am going to be new at the school, but I’m not a girl or a boy, I’m gender fluid, I think, but a boy under here.”
I didn’t even know if that was true yet, but it was easier to just say it,
“Oh, well that’s ok, I’m sure everyone will accept you.” He told me.
I gave him a look and he smiled and said, “Ok, maybe not everyone but I’m sure it won’t be as bad as it could be. I mean, this is the 21st century.”
I smiled and said I hope so. We chatted a bit and talked about the school, music, film, streaming, and just general stuff until he was called away by his mum. He said bye to everyone, gave me a wave and walked off. I watched him go and turned back to the girls who were all looking at me with big smiles. I looked at Sarah and said to the girls, “What?”
And they started to laugh until Sarah took my hand and whispered in my ear, “So I guess I have some competition with boys then?” And she gave me a kiss on my neck and I melted for her as the girls went ‘ahhhh’.
We seemed to chat for ages and look round some shops where I was able to get some more makeup and a couple of bras as I now knew I needed them and my mum was right before we headed back.
I realised that my clothes were already at home so no matter what I was walking indoors dressed as I was, but as Sarah said, at least now I have a full set of make up so I won’t need to borrow some of hers anymore.
We kissed each other on the cheek as we said goodbye outside my house as she walked on and I went in. I was a bit surprised that my mum and sister were home early but maybe not as surprised as they were in what I was wearing, so I explained about the day and the new bra (to which my sister said ‘well that explains the magnificent puppies you have now then’), meeting more kids from the school and then my sister looked in my little shopping bag with my makeup and asked if she could borrow my mascara.
My mum told her in no uncertain terms that ‘it’s bad to borrow makeup, I keep telling you that.’ And then I got an even bigger surprise as the front door opened and dad walked in. He looked at me and said, “Hi Andi, you look pretty. I saw you say goodbye to your new girlfriend is it? Anyway, you can tell me about it later as I hope you ladies are all ready?” And with that I learned we were going out to eat as dad was visiting for a couple of days before going back to the old house.
Walking out the house with my family and wearing a lot less clothes than they’ve seen me in for years felt a bit weird, but they just accepted me. I think I have a great family.
He looked at me and said, “Hi Andi, you look pretty. I saw you say goodbye to your new girlfriend is it? Anyway, you can tell me about it later as I hope you ladies are all ready?” And with that I learned we were going out to eat as dad was visiting for a couple of days before going back to the old house.
Walking out the house with my family and wearing a lot less clothes than they’ve seen me in for years felt a bit weird, but they just accepted me. I think I have a great family.
The meal was fun and it was great to see dad again. My sister talked me into taking the shirt off so I was just sitting there in shorts and the vest, but no one had an issue. When we got home my sister made it very clear she wanted to speak to me, so we went to her room.
She wanted to know about the last few days and I told her everything. I showed her the photos of me in the tartan mini dress and the other items I tried on, and as she was flipping through the pics on my phone, she stopped and looked up at me, then showed me the pic. I had taken a topless pic in the changing room mirror just wearing a pair of pink hot pants. My faced burned and I tried to grab the phone from her, but she said only if she gets to see what I’ve been hiding from everyone for months. I finally let her see my boobs and she was surprised at how developed they were.
The next day I went shopping with my sister, wearing the same underwear and a pair of skinny jeans, but my sister leant me one of her fitted tee shirts. It was red, which I was against at first, but I have to admit I did like the way it fitted me. Turns out the ‘rents gave her money to help me (and I suspect to find out more), but I was ok. I didn’t want to hide anything from them, it felt unfair, so I knew I would have a long chat with mum soon. I ended up buying quite a few packets of underwear, got a few tops from Primark, two sets of sleepwear (the shorts and vest kind). My sister got a couple of tee shirt dresses, then told me the next place would be a treat. We went to a posh shop and I got three matching sets of really nice lingerie, one in black, red and pink, and a lacy teddy in green which I have to admit I loved. On the way home my sis said how excited she was to be able to go shopping for sexy lingerie with me as it was horrible doing it with mum.
Once home I unpacked everything and it turns out the two dresses she bought were for me, then she gave me a few pairs of her shoes she didn’t wear anymore. These included a pair of knee high suede boots with a three inch heel and a pair of high heeled platforms court shoes, pumps as some call them but I couldn’t think of when I would ever wear them. With the platform they must have been five inches high, and she told me I would like how they make my legs look.
I touched up my makeup to head round to Sarah’s and for the first time in my life I really had to decide what to wear. I knew I wanted to wear the sexy red set of lingerie, not worrying about the suspender belt as I didn’t have stockings anyway. I knew they would hold my tuck, so I wasn’t overly worried and was going to wear the shorts I wore yesterday, but I kept looking at the tee shirt dresses, Should I?
It’s a big step to make, what would Sarah think? Screw it, in for a penny, in for a pound. It was a polo style tee shirt dress and came down to about mid thigh in baby blue. It was a lot of flesh to show, but technically less than the shorts. I picked up my handbag and headed for the door. Sis saw me and tried to say something, but I kept walking saying, “Don’t say anything or I will change my mind!” I opened the door and walked around the corner. Sarah loved the look and told me to keep what I wore yesterday, but she did want the boots back, and as I was wearing them today we went to buy a pair for me when I also picked up some tights, two pairs of stockings and a pair of hold up stockings.
I’d mentioned that I wanted to say thanks to my family and Sarah knew a shop with some great cards. My sister got one with a hot naked man on it, but with a towel hiding the good bits, my dad a classic car as he likes watching car shows, and mum one with some flowers on it.
The shop also had lots of little gifts like clocks, ornaments and so on, and some things called ‘massagers’ which were very obviously vibrators and next to them some dildos.
I looked at Sarah and she laughed saying, “Well where do you think I got mine?”
My mouth dropped open and I asked if she really did have one? “Yeah, don’t you have one?” I gave her a look and she said, “Come on, you must have tried something?”
As she picked one up at random just looking at it, I said, “Well, I do have a favourite hairbrush.”
She squealed in delight, and said I needed something better, so we looked and tried to work out what would be best for me. We weren’t sure if a vibrator would work for me, but we did know hairbrushes did, so I picked something up, looked at her and asked what she thought? She thought it might be big, but I pointed out she hadn't seen my hairbrush!
Five minutes later we were heading back to hers, me with a gift bag including five and half inches of insertable length dildo with ‘realistic’ balls and a suction base. Oh, and some cards.
I thought they would ask for some ID, but as they weren't technically a sex shop, they never asked so I didn't say anything. Sarah got a little gift for me as well, I knew she got something but didn't realise what it was, but now I also had a douche to use. We collapsed on the bed together, laughing and comparing our toys and it wasn’t long before we started making out again. It was a lot of fun having hands up each others skirts and it didn’t take long for us to end up with fingers inside each others pants.
Feeling my tuck be undone by someone I liked, she stroked me gently and pulled me out through the leg hole. It was standing upright and it would hold up the skirt of my dress with it, but to be fair I didn’t care as my fingers explored her vulva, her clit and then slipped into her vagina. As we masturbated each other, two thoughts crossed my mind, why did I think the guy on the card was hot, and why did I chose something that looked like a penis and bigger than me own penis?
We were interrupted by her front door closing, and footsteps on her stairs. We both jumped up and tried to get covered up, but I still had a problem that I couldn't tuck. Her bedroom door opened and I sat on the bed, hoping I could hide it. Sarah’s mum looked in and asked if she was ok, and then looked at me. “Andi? Is that you? What are you making him do?”
So I quickly had to explain my medical situation and said if she calls my mum she can explain it all. She looked a bit suspicious and repeated that the door needs to stay open. If we hadn’t done that I dread to think what she would have seen as we wouldn't have heard her come in. Ten minutes later, thanks to Sarah’s helping hand, I was tucked and on way home.
The next two weeks I seemed to be spending all my time dressed in shorts or the tee shirt dresses, but the day finally came that we would go to the alternative club. It was really just a normal bar that was rented out and not that big, but had a downstairs dance area. Sarah really wanted me to go all out to look good and we chatted a lot about what to wear.
In the end I wore my knee high boots with he three inch heel, along with a black pleated skirt and a white crop top vest. Under that I had my first ever tee shirt bra as I really liked it, and a new discovery in underwear, a thong. Thankfully they would hold me in place and I felt quite comfortable and enjoyed feeling the skirt move against my bum as I walked. I had got my sister onside for the outfit in case my parents tried to stop me, but I shouted a ‘see you later’ and they told me when I had to be home and out I went for the short walk to Sarah’s. She came out the moment I rang the bell, wearing the tartan mini dress I had my eye on, with a wide belt and ankle boots. We walked to bus stop to get there, intending to get a cab back.
The bus dropped us a short walk from the club and when we got there they asked us for ID and put a red stamp on our wrist meaning we wouldn’t be able to buy alcohol, but I was ok with that. She introduced me to some of the people behind forming the club, then we got two cokes with straws and sat down to chat. After about ten minutes two guys sat at the table next to us, and before long one started chatting to Sarah and I realised he was chatting her up, and flirting with her, and she was flirting back. I felt a bit jealous, but then his friend moved to our table and started chatting to me.
I felt really nervous, they were both older than us and what would they say if they knew I was really a boy? Ok, a boy with boobs, but still very much a boy in my thong. They went to get us a drink and Sarah said we should go to the ladies. I was nervous but she gave me a hug and told me not to worry, this is just a bit of harmless flirting.
When we got back to the table the two guys came back and I was suddenly worried they may have put something in our drinks, but Aaron whispered in my ear that it was ok, there was nothing in it as after they saw the stamps on our wrists they looked after them for us. Chatting to him I decided to let him know that I was almost 15 in case he got any ideas and he admitted he wasn't even 18 yet himself. I told him a bit about how I had just moved here and so on, he told me he was joining the navy soon.
I felt really comfortable with him, and Sarah seemed to be getting on well with his friend. On our next trip to the ladies, she told me that her guy had suggested we go to the bar a few doors along to play a game of pool for a bit, but wanted to know how I felt about it. I agreed, it might be fun, so the four of us went next door and Aaron’s friend went to that bar while he sorted out the pool table and we sat there looking at him.
Sarah asked me if I thought he was cute, and I admitted I did and she told me she liked her guy. We agreed we would just let whatever happens happen, and Sarah said to me, “now your fem side is coming out, maybe you need to see what it’s like for us girls.”
I had to think about it, but after the game started, I told her, ‘yes, but can we keep what we have as well?’ She gave me a hug and said definitely.
Aaron stood behind me when I was playing and Steve stood behind Sarah. It was only when I could see her behind I realised what they were both doing, they were checking out our bums!
Ok, it’s like that is it. When I next bent over the table I stuck mine right back, bending at the waist to make sure he could see. After the game we sat at a table and just chatted till we finished out drinks and went back the club. On the short walk I felt Aaron slip his hand into mine and I really liked it, looking up at him and smiling.
Sarah suddenly stopped, looked at her guy put her arms around his neck and they kissed. I was watching my girlfriend kiss another man right in front of me. Wait, am I really a man? I’m kinda between both, but holding Aaron’s hand I’m not sure I could be called a man.
Anyway, he slowed down and I slowed down with him. I think he stopped first, but we were both standing there, looking at each other while holding hands. He leant forward and down slightly as he was taller than me. I looked up and lifted myself up on my tip toes. I leant into him and our lips touched lightly and my eyes closed. I was kissing him. I felt his mouth open and his tongue touched my lips and I opened them to let him in. I stood there kissing him on the street feeling his erection grow against my stomach as one of his hands slides up my body to cup my right boob.
I liked it.
In the club we made out a bit more, and Sarah and her guy went to dance, and I looked at Aaron. “I need to tell you something and I hope you don’t hate me for it.”
He put a finger under my chin and lifted my face up to see him. He was smiling at me. “It’s ok,” he said, “you can tell me.”
So I checked no one else could hear me and I told him the truth about me. He moved a hand to my leg, gently stroking me with his thumb. He said, “Thank you for trusting me.”
He leant in and kissed me again.
I’m not sure when Sarah got back, but suddenly she seemed to be there smiling at me, and I realised I had a hand up my skirt and on my hip. I sneaked a look at the time and saw I still had two hours to curfew, and Sarah told me that Aaron has a car and they’ve offered to take us home later, making me smile.
I’m not sure who suggested it, but we ended up going for a walk. There was a park nearby and we were all walking through it. Sarah and her guy stopped at a bench and we walked to the next one. Obviously we were going to be having a make out session with them and this was just somewhere a bit more private to do it.
I was both nervous and excited at the same time.
Sitting there kissing Aaron his hands were on my legs, my boobs and up my skirt again and I felt my hand on his cock, feeling the hardness there.
He was so much bigger than me. I think it was just the heat of the moment, but I ended up giving him a handjob in the park, then he whispered in my ear, ‘I’m going to cum’ and I didn’t know what to do, but I felt myself willingly leaning forward and I took him my mouth, using my hand and tongue to finish what I had started.
He flooded my mouth and I swallowed as fast as I could, only a little ran down his cock but I licked it up eagerly, wondering what had happened to me to be enjoying this so much. I sat up and smiled at him, then looked across to see Sarah on her knees sucking away herself.
Aaron hugged me to him and lifted me onto his lap with my legs astride him. He started rubbing me down there and I was squirming on his lap. I felt him lift me a bit to encourage me to stand up and then he pulled my thong down.
I tried to stop him but he was gentle and reassuring and I think to be honest I wanted it. He helped me step out of them and pulled me back onto his lap. I was fully erect and tenting my skirt in public.
Ok it was getting dark and no one was around, but still, I was fully erect and tenting my skirt in public!
He kissed my neck and stroked my legs, teasing me, getting closer each time until finally he brushed against my erection but kept his hand moving away from it. I pushed myself down on him, I wanted this badly. Finally he touched it and wrapped his hand around me, slowly stroking me.
I felt like I was on fire. With Sarah it was erotic but this was off the scale! He was kissing my neck and stroking me and I told him I was going to cum. I lifted the front of my skirt and he kept going, shooting my cum out in front of us. As I came down from my high I looked across to Sarah and she gave me a thumbs up while still sucking away. Aaron took a tissue from his pocket and cleaned me up as I deflated in his hand, squeezing out the last drops and covering me with my skirt. I finally put my legs together as I turned to face him and we kissed. We heard Sarah finally get her guy off but we just sat together and waited.
Someone must have suggested we go back to the club before they take us home and I realised I wasn’t wearing any underwear and looked for it. Aaron whispered it’s ok, he has them and will give them back to me in the club.
I was scared silly at this point as we started walking, trying to hold my skirt down in case there was a gust of wind with one hand while holding his hand with my other. There was no wind at all and feeling myself swing down there as we walked felt weird and wrong. I begged him for them back but he just gave me a kiss and a smile and told me he liked knowing I wasn’t wearing anything.
Sarah was suddenly next to me, she sensed something was wrong so we walked ahead of the guys and she asked me if I was ok with what happened? I told her that was fine, good in fact, it’s just that he’s not giving me my thong back! Sarah gave me a hug and out of sight of the boys put her hand under my skirt, felt me up a bit and her eyes went wide.
She gave Aaron a dirty look and was about to have a go at him, but I told her what he said and she giggled. She said, “Ok, that is funny. You better not get excited.”
And she walked back to her guy and Aaron came back and took my hand. How could she be so mean to me! Aaron stopped, pulled me close and gave me a kiss, stroking my bum and boobs and then I felt his erection against my stomach and then I felt myself twitch below.
He must have felt it too as he increased the intensity, kissing my neck and trying to turn me on, slipping a hand under my skirt and stroking me a little. When I was fully hard he broke the kiss and said, “Come on, let’s go back. Guide the way for me.”
And he smiled a smile that really didn't help me at all! I’m not that big, only about four inches when fully hard, but I looked down and even with the pleats of the skirt it looked obvious as he held my hand as we walked. I tried to put my handbag in front of me but the strap wasn’t long enough and now I could see the club, in fact I was pointing towards it and at the sky too!
I tried to crouch over to hide it as we walked but I could feel myself holding the skirt down at the front and lifting it at the back. I looked at Aaron and he was smiling and his eyes flicked down so I looked. I wasn’t tenting anymore, I was holding it up with the head poking out from under and very much on display.
I flipped my skirt to cover it and then we were out of the park and crossing the road. Why didn’t it occur to me to just stop and demand them back? Why was I letting myself be led along like this?
Ok, on some level I was quite liking it, I know that now, I know why I didn’t demand them, Sarah knew it too and knowing it turned them on was, well, fun.
We walked into the club, showing them our wrist stamps and no one seemed to notice what I had going on. The boys took us to the bar and got us a couple of soda’s and Aaron was doing just enough to stop me from going down, and still no one noticed. Sarah was trying not to laugh and her guy had no idea.
Finally we walked to a table and sat downed I put my bag on my lap as the tent was going to lift up the front of my skirt while Aaron stroked my leg out of sight of everyone. Finally he put his hand in his pocket and handed my thong to me in his fist. I jammed them into my bag as quick as I could, grabbed Sarah’s hand and pulled her towards the toilets.
As we walked past people, I was keeping myself covered, but several times I had to squeeze past and it touched them. This was awful and not helping me at all! We both went into a cubicle and I started to put my thong on, but now faced another problem, how was I going to tuck?
Well, five minutes later we both went back to the guys and thankfully Sarah had lent me a helping hand again and although it was still tough to tuck and I had a bit of a bulge, under the skirt it wasn’t obvious and I felt very relieved. I did get to sort the tuck properly before the boys drove us home and I managed to get to my room before my mum saw my smeared lipstick from a very intense goodnight kiss. Turns out despite everything that happened I’d agreed to see him in a couple of days and we swapped numbers.
The following morning, Sarah came round and dragged me to my bedroom. Inside she asked me one question, “How brave do you feel today?” I had no idea what she was talking about and she pulled a bikini out of her bag. She didn't say it to me last night, but the girls we met at the mall were going to the beach and she wanted to know if I wanted to go as well. I really wasn’t sure but she suggested I try it first, so I made her leave the room and I looked at it. It wasn’t super revealing but it was a bikini. Did I really want to do this?
It would be nice to go to the beach, but I’m not a great swimmer. I took my tee shirt off and looked at the top, it was easy to put on and tied at the back which was a bit difficult but I managed it. I looked at the bottoms and slipped out of my joggers and pulled my pants down. Stepping into them I could feel them stretch and thought ok, this might work as well. I did my tuck and pulled them all the way up. They seemed to hold me ok, and I did a few lunges and bends to see how they felt and if they were secure enough, sitting down, squats and so on. I looked at myself in the mirror and yeah, I looked ok.
I opened the door to let Sarah back in and in rushed my sister as well. Sarah explained she had told her and she wanted to see as well, and the first thing she said is I need to do something better with my hair. I then ended up sitting there and them both playing with my hair and insisting I go to a hairdresser at some point before school.
Once they seemed happy I started to put some makeup on and my sister left for a bit, coming back with a pair of shorter shorts than I already had and a white skimpy crop top that tied at the front, so I put them on and now I looked beach ready. Sis handed me a bigger bag and put a towel in, telling me to put some clean underwear in as well, so in went a thong as well as these shorts are really short.
I went downstairs and just before I got to the door mum said, “Stop right there young lady, you're not going out like that!”
I was really hoping she wouldn't see me, it didn’t even bother me that she called me a young lady. Mum walked over and said, “Sunscreen, you need sunscreen if you’re going to wear that outfit.”
And she sprayed my arms and as I wiped it in, she sprayed my legs, then put it in my bag and told me to have a nice time and off we went.
The beach was so much fun, just sunbathing and chatting with the girls. Yes I told them about Aaron and Sarah told them I was seeing him again and they shared stories with me of other boys they had dated and things they’ve done, even giving each others sex tips.
They thought it was funny what he did, but were also empathetic for me for the fear I must have felt. One of them had a boy steal her favourite panties and she was still mad at him as she had to walk home in a very short dress that barely covered her as she was afraid to get the bus knowing she would be on show.
About one o’clock we packed everything in our bags to go and eat and there I was, walking along in a bikini with a group of girls, with boys and some creepy old men checking us out, but we hit a shop and picked up some water and crisps and as we turned to head back, bumped into Dave and one of his friends. He did a double take when he saw me and I blushed, especially as the girls looked at me and him, and then each other with a giggle.
I just wanted to tell them to grow up, but Dave was checking me out and I realised I told him I was a boy and here I am in a bikini with very obvious boobs and nothing obvious below. I’m not sure how it happened but they ended up walking back with us, but as neither of them had swimming stuff with them they were unlikely to stay for long. When we picked a new spot and laid out our towels and they both sat down with us, his friend paired off with Jodie and chatted away, while Dave sat down with me and Sarah.
He was fun to talk too, the three of us shared some of the same interests and he seemed nice. Sarah excused herself to go to the toilets and walked off with Jane and suddenly I’m sitting there with him while Jodie chats to his friend and the other girls laid on their backs to work on their tan. Dave leant towards me to say something, saying, “Can I ask you a question?”
I nodded a yes as it was obvious what was coming. “I thought you were a boy?”
I told a little bit more about the extra X, why I have boobs and that yes, I am a boy, but if I wanted to go to the beach it’s easier this way. His eyes flicked down and before he could ask I told him about tucking but could see he wasn’t quite sure if I was telling the truth. I looked him in the eye and said, “Ok, if you promise to say nothing about these,” and I pointed to my boobs, “then I will prove it.”
And I pulled the front of my bikini bottoms down a bit and he could see the base of my tucked dick where a vulva should be. His eyes went wide but I could see he finally believed me. I said, “You’re not weirded out by that are you?”
He said no, he was just so surprised as he’s never seen me looking anything other than a girl. “Well, normally I would be more androgynous and it would be easier to believe me. But this is actually much easier and I haven’t been to the beach in two years or even thought about getting a tan. Speaking of which,” I tuned and laid down on my stomach and handed him the sunscreen. “Would you mind?”
As he opened the bottle I untied the bikini top and moved the straps out of his way as he very nervously starting spraying it on me. And that’s how Sarah found us. I told him to make sure he covered my legs as well, and it felt really nice, like a mini massage. He did my back and I asked him to make sure he got all the exposed skin, so yes, he did go inside and outside of my thighs, getting as close he would dare to go. He definitely touched me down there, just for a fraction of a second and it felt nice, but he stayed well away after that.
Sarah decided to get in on the teasing and asked him to do hers as well, so the poor boy was really suffering. The other girls thought it hilarious and tried to hide their giggles, but his friend was clearly jealous and wanted to ask Jodie if he could do the same. I snuck a look at Dave and it might just have been his shorts gathering fabric, but it could also have been something else.
When he finished he sat down and tried to ignore us, so it definitely wasn't something else.
After about ten minutes, he said he would see us all later and him and his friend left, clearly recovering. Sarah and I jumped up to talk to the girls, holding our tops in place with our hands as we all talked at once. They thought he liked me, but I pointed out I’m a boy so he probably likes Sarah more. Anyway, after half an hour of talking about them, me, Sarah and Jodie went into the sea while the other two girls looked after our stuff.
We just splashed about for a bit, but I was too nervous to go too far out. Jodie and Sarah were great swimmers, but after a while it was time to go so we headed back. We dried ourselves off, then headed to a nearby ladies to change out of our swimwear, taking it in turns in a cubicle. When I changed I realised I hadn’t brought a bra with me, so I just put the top back on and I was very worried about the bow I had tied, and very aware of my nipples and the thin material of the top. They were standing out as always but when I walked out and looked in the mirror I could even kinda make out the aureoles.
The girls all told me I looked fine, but getting the bus home I felt like everyone was looking. Still, at least I didn’t need to worry about them thinking I was a boy. Me and Sarah didn’t talk much on the bus and I found myself thinking about my day in a bikini, how nice it felt when Dave was touching me and wondering what I would wear for my date tomorrow with Aaron.
Jodie and Sarah both pointed out it was clear that he liked me even though he knew I was really boy and that if I want to I should have sex with him, making me gasp in surprise. They both said if I’m happy using my dildo most days, then I will be really happy with how a real one feels inside me.
Two days later, I was sitting in a Starbucks on a double date with Sarah. Aaron looked hot and I even thought his friend looked good, although I purposefully kept getting his name wrong as he is going to be with Sarah. I was in my baby blue tee shirt dress and the knee high boots, Sarah was in a summer dress that came to mid thigh but with her New Rocks on.
The date was fun, but also felt a little awkward in a way, I guess the fun of the other night was on our minds and now we were dating in reverse, but slowly things got easier. At some point we left and walked through town and the shopping precinct, which was weird it being so empty of shoppers, but also kinda felt romantic strangely.
I stopped to kiss Aaron every now and then, while Sarah did the same with her guy. I loved feeling Aaron hard against me, and even undid his flies and put my hand in there to hold him and walking along like that. Sarah later told me I was sending him some pretty big messages but to be honest, I wanted that to happen and had prepared before we left.
I half guided him to a little alleyway next to a shop and he half guided me there as well. Soon we were out of the bright lights kissing intensely and both his hands were up my dress up my hips and I was very much on display, but by then I had already got Aaron out into the air as well, tasting him between kisses. I turned my back towards him and felt him lift up one of my legs, his erection rubbing on my groin and pressing lightly as he instinctively tried to enter me.
I opened my bag and quickly put some lube on him as he pulled my thong to the side and slipped in easily. As he slowly fucked me I leant back to kiss him and there I was, looking out at a shop with a cock inside me and a hand up my dress caressing my boobs as we kissed. It was wonderful, it felt right and then I noticed that Sarah was getting similar treatment from her guy in the alleyway, with a condom wrapper at his feet.
I thought, ‘oh well, at least I can’t get pregnant’. It really felt good, so much better than my dildo or hairbrush, better than anything I have ever felt in my life. He was hitting something inside me that felt amazing and sending pleasure through every part of my body it seemed. I wanted this to last but he didn’t quite get me there. I could feel the desire to cum building in me and if only he had lasted a minute longer I think it may have happened. He thrust himself deep into me as we kissed and I could feel him twitching and pulsing in me as he filled me with his cum. He slowed down and held me, inside me still and kissed me gently on the neck. We both watched Sarah and his friend for a bit then he whispered in my ear, “Do you want to cum?”
I nodded and he wrapped his hand around my own little erection, I must have slipped out when we fucked and was just pointing out, but it soon disappeared into his fist as he slowly stroked me. My lust was still high and feeling him in me still just added to the erotic nature of my first time.
It didn’t take long for me to start shooting my own cum, shooting much further than it had before. Aaron whispered in my ear again how great that felt for him as I squeezed him inside me, and he would make sure I was always first, just to feel that again as he slowly pulled out of me.
God, he felt great in me.
I sorted myself out, using a tissue to wipe away the little cum that dribbled out of me, tucked and dressed myself again. Sarah’s guy looked close to finishing but he was watching me all the time he was having sex with her, so he saw my thing, so while sorting out my bra that had been pushed up, I flashed my boobs at him before I pulled my dress down and joined Aaron to wait outside the alley.
After fixing our make up we went into a Costa this time for a coffee. I felt kinda slutty sitting there with a man’s cum inside me and in the toilets me and Sarah almost screamed in excitement at what had just happened. I had lost my virginity and Sarah got something she needed that I couldn't really give her.
Yes I have a penis but it’s not that big and I know that, my condition means it will never be big unless I decide to pick the male option, so until the day I pick that I’m ok with her having someone if it means I get to enjoy feeling what I feel inside me right now.
And I got a cum top up later that evening before we were dropped off at home. He wanted to see me on Saturday but that day I had to keep free as I was finally turning 15 and spending the whole day with my family.
Over the next week I saw Aaron twice, but between me and Sarah things cooled down a bit, not surprising really. She very much likes her guy, and to be honest I don’t blame her. We did talk about it in a bit of detail and she admitted she thinks she’s a little bi and she found herself attracted to me, but is very aware that she prefers, well, men. Which is where the conversation turned to me and what I liked admitting that yes, I think I am a little bi and enjoyed our make out sessions, but when I kissed Aaron for the first time, well, something clicked inside me.
Not that, get your mind out of the gutter, although, yes, that as well once it happened. It’s like it confirmed for me what I’ve known for a while.
I like guys.
But apart from that, during the week I was flipping between being a boy and a girl depending on my mood. Sometimes I felt more fem than others and I lent into that side of me, sometimes less so and went back to my more androgynous self. I bumped into Dave on one of those days and we hung out for a couple of hours in town. The only interesting thing to report is when he needed to loo, I went with him into the mens and stood one urinal away while I peed.
At least that fully confirmed I am a boy down there at least to him.
When I woke up on Saturday it there were two things I couldn't miss; my sister shouting happy birthday as she opened the curtains and how bright it was! While having some cereal the ‘rents said it was going to be a hot day today but wouldn't tell me anything about what was planned. I still felt a bit nervous to be around dad dressed as a girl, I mean, I know he says he’s ok with it but I am a boy, so I picked out a pair of skinny jeans, baggy tea shirt and converse.
Of course, when I walked downstairs they were waiting for me and all dressed for a really hot day, so my dad just asked my sister if she has something she could lend me so I wouldn’t bake all day, with mum suggesting a summer dress, so back upstairs I go with her and after changing my underwear to something more suitable along, I came back down in an above the knee summer dress with a handbag and light make up, and now wearing white converse instead of black ones.
Turns out the plan was to get me some more clothes as I was spending more and more time as a girl, but I didn’t mind, it was so much fun. At some point me and my sister Claire decided to dump our bra’s in our bags as the day was already getting hot. Mum noticed of course but said nothing.
After picking up a couple of outfits and some shoes, we stopped for some food before heading out to a zoo of all places. I can’t remember the last time I went to one and we spent a very happy day as a family, even if my sister did dare me to walk around for an hour without any underwear on. I made her do it as well and the deal was we had to look after each other to make sure there was no cheating.
I wanted to tell her that it’s not like I haven't done this before, although at least this time there was nothing to make me ‘stand up’.
I was very aware of a couple of cute guys there and giggling about them with Claire and how we were going commando. It was really nice not feeling anything restricting me, but I did miss feeling smooth so I guess it’s a swings and roundabouts thing. Anyway, we put them back on before heading home and had a family movie night, eating pizza and popcorn till we felt like we would explode. I really do feel like this is the perfect summer before school starts in just over a week.
The last week before school obviously involved mum insisting I make sure I’m ready for my last year and reminding me how important my GCSEs are, but I did get to see Aaron twice and hung out with Sarah a lot. We didn’t do a lot, it was just moaning about the summer being over, but when we were out we bumped into Dave.
I could tell he wanted to talk to me, and I wasn’t the only one. Sarah was being really annoying and kept talking and after a couple of minutes I started to get it. Dave had admitted that while he knew Sarah, the whole goth thing really intimidated him a bit. But then Sarah said, “Oh, stay here I’ll be back in a second I need to say hello to someone.”
We watched her walk off, and Dave turned back to me. I of course could see her over his shoulder and she just stood there watching us with a smile on her face.
“Hi Dave.”
He looked really nervous and I think I could guess that he wanted to ask me out, which is a surprise as today I definitely wasn’t dressed or presenting as a girl, no make up, he knows I’m a boy really. Ok, a boy with boobs, but he knows this. He knows nothing about me and Aaron, no idea what my sexuality is, and here he is looking nervous like he’s about to ask me out.
Should I help him out?
He said, “So Andi, I wondered if you wanted to go and see a film?”
Not what I expected, so I said, “What, I go to yours or you come to mine to watch Netflix?”
He blushed, and said, “No, no. I mean, that would be ok too, but I was thinking of going to the cinema, maybe?”
Ok, he does look cute when embarrassed.
“Yeah, that will be nice. But you do know I’m actually a boy, right?”
He blushed again, answering, “Yeah, of course. I was just thinking it would be nice to hang out before school starts.”
I stood there and looked at him, thinking over what I would say. I knew I was going to say yes, but I maybe needed to make some things a bit clearer.
“Yes, and I know you’ve seen me in a bikini, but when we go to school I will be there as a boy all the time, you know that, right?”
He answered so quickly I was wondering if he was trying to hide something about himself. “Yes, of course, it’s just two mates going to the cinema, nothing else. Is that ok with you?”
I nodded and Sarah saw that as her queue to come back, and the three of us hung out for a couple of hours. She of course was desperate to know what we talked about, but there were no chats in the girls toilets today so she had to wait. When I told her not he bus she was actually excited and told me just how nice Dave is and that we would make a lovely couple.
So we went to the cinema together the next day and with school about to start I was probably the most manly I had looked for a long time. No make up, I was wearing jeans and kept my boobs as hidden as possible, but I was still directed to the ladies by someone. Anyway, we watched the film and as walked home we held hands a couple of times, but it was just a sweet little thing. I mean, I like him, I think he is sweet but I’m not sure if I want to date him. Maybe once Aaron has left in a week or so I would feel differently as I think discovering sex has maybe confused some of my feelings, plus I have no idea how things will be in school if I was openly dating a boy.
Anyway, who knows.
All too soon it was the start of the school year and in my new uniform with the strangely itchy trousers I waited for Sarah to come round as my mum was driving us both to school and she was going to be my designated ‘guide’ for the day. I wore no makeup as I didn’t want my fem side to be on show and kept my hair tied back in a ponytail per the dress code. I did check that out online as I didn’t want to cut my hair and the code wasn’t gender specific I noticed so I could either wear it down if I wanted or the suggested ponytail I went for.
After the stuff mum had to do I was given a timetable and Sarah showed me to my homeroom, she was in a different one to me but a lot of our lessons were the same and she said where we would meet, so I walked in the room.
Of course people looked at me as the new kid and I looked for somewhere to sit and I saw Dave, he smiled at me and called me over and I sat down with him, saying hello’s and so on. After that the day was just another school day and me trying to work out the layout of the school.
I did meet up with Aaron that evening, and the sex was good as always but he seemed less willing to talk, we just seemed to get down to things very quickly. But once he had cum in me and got his breathe back, he told me he was leaving next week and had known the date for a while now, but kept it from me.
I wasn’t upset, I like him and enjoy having sex with him, but he’s my first, not my first love and not my first boyfriend. Even Sarah told me that was really obvious in how we both behaved towards each other as it was based purely on attraction and nothing else. Still, we had sex again and hoped to meet up right before he leaves.
Anyway, as one chapter of your life closes, a whole new one opens up, I just wish it hadn't happened the way it did.
The next day I walked to school with Sarah but I was a bit more worried about today as we had a swimming lesson. Mum had told me not to worry, I wouldn't have to do it, just tell them I have a medical condition and that should be it but if there’s a problem she will write a letter. Sarah didn’t think that would be enough, and when I texted Dave about it, he didn’t either.
Apparently a few years ago a kid at the school drowned so they were really strict on making sure that everyone could swim and everyone had at least one term where we were taught and it was now our turn.
At lunchtime I went to see the PE teachers and explained I have a medical condition so couldn't swim. There were two teachers, one old and gruff, the type that likes to bully kids a bit if they can’t climb the rope if you know what I mean. The other one, well, he was a lot younger, maybe even not that much older than me and he wasn’t even wearing a proper teachers ID.
He was kinda good looking really and when I talked about why I couldn’t swim he seemed quite open about it and listened to me. But the older one told me that unless I have a letter from the doctor, I have to swim. I told him I didn't have any shorts so couldn't and he said not to worry, they have something I can wear, but that ‘in this school everyone swims.’
Outside I called my mum to explain it to her, but as she didn’t answer I guessed she must have been in a meeting at work and dad didn’t answer either (he forgot his charger and was out of battery). I was panicking a lot the rest of the day, spoke to the reception staff, but everyone was really firm on this, swimming is important.
Sarah, Dave and Jane were really supportive, but at the end of the day we all walked across to PE for the guided group walk to the swimming pool next door to the school. I tried again with the teachers and the gruff old teacher showed me the lost property box and where I could find a towel or have a month of detention and he walked off to organise the rest of the boys.
I looked in the box and the shorts in there were way too big for me, same as the speedo’s, but I kept looking and then lower down in the box were bikini bottoms and I knew they would fit me. I grabbed two that looked like they could be speedos and a pair of shorts, hoping I would at least be able to wear a tee shirt as well. I stuffed them in my bag along with an old towel and joined the class on the short walk.
I hadn’t heard of wet tee shirt competitions at that point otherwise I wouldn’t have even thought about wearing tee shirt.
Dave was waiting for me and we started walking then Sarah and Jane joined us as well while I explained about the swimwear and I would keep my tee shirt on, but they all said no even the girls weren’t allowed to do that.
Sarah stopped me and said, “Look, if you’re being forced to do this, you may as well just do it properly. You’re a boy so no one can complain when you’re not wearing a shirt, and if bikini bottoms are the only thing that will fit, then wear them how they are meant to fit.”
She squeezed my hand and nodded, with her eyes telling me I could do this.
But could I?
I took a deep breath to try and control my fear, nodded back at her and tried to stop myself crying. She told me later she realised I was about to start crying and she had to make me be in control of my own narrative.
Walking into the changing rooms I was the last boy in and the only cubicle was right at the other end, by the entrance to the pool. The gruff teacher told me to hurry up or I would slow everyone down and put on whatever I found that fits me. Well, I was still small so even though I had the boys stuff I think I knew what would happen. I tried them all on and they all fell down or were so loose they would fall off in the pool, so I looked at the bikini bottoms.
The first was a bit too big and I tried to wear them as speedos but of course there was a big gap around the leg holes with my bulge. I looked at the one I was avoiding, pink and very clearly the right size for me, slipping them up my legs. I looked in the mirror and they looked stupid with a bulge, so I slipped them down and tucked, looking again and thinking how much better they looked.
I even found myself seeing how I looked in the mirror, turning around and so on. The other boys were running past my cubicle and the gruff teacher was telling everyone to hurry up, banging on doors and so on. I slipped off my shirt and stood there in my vest, the one I use to try and stop my boobs bouncing too much, again, checking myself in the mirror and thinking this will do, I will wear this. Then I heard the gruff teacher shout at a boy to take his tee shirt off, it will only weigh him down and ‘until we know you can swim it could make you drown’.
I slipped off the vest and stood looking at myself.
This is going to be a horrible moment, everyone will see me. Then the gruff teacher banged on my door telling me I was the last and to get out there now.
I opened the door and stepped out slowly, no one was there and I turned to the pool exit, taking the hairband off and throwing it on my clothes. I started walking and kept my arms folded at first, but realised that’s a plan that isn’t going to cut it. I lowered my arms and stood there, taking a deep breath and getting myself mentally ready for this.
I look down at myself and I was exposed, in public. My ears were burning and my face must have been bright red.
I decided if I was going to do this I was going to do it right, just because I haven’t been to a pool in years doesn't mean I don’t know you should stand under the shower first, so I did that then stepped out seeing the boys at the shallow end on our side and the girls the same on theirs.
I walked down the length of the pool, focusing on the gruff teacher. If he was going to embarrass me them I was going to return the compliment. I walked to him, feeling my little boobs bounce and slowly it got quiet as everyone was stopping talking to look at me.
The gruff teacher turned to look at me then did an actual double take. If I hadn’t been burning with embarrassment I was trying to hide, I would have laughed. I stopped in front of him and pointed to my boobs saying, “This is my medical condition.” And then I pointed at the bikini bottoms and said, “And this is a tuck.”
His mouth dropped open and of course he looked at me then looked away before focusing intently on my eyes and only my eyes, saying, “Join the other, er, boys.” And I walked down the line of them to stand with Dave near the other end.
Of course everyone was looking at me, but I resisted the urge to fold my arms and cover myself up. If I’m being forced to out myself like this, then I’m not the one who should feel any shame.
We were split into three groups, the great swimmers, the ok swimmers and the non swimmers, which I joined with Dave. Sarah was in the great swimmers and they were going to be taught life saving stuff, but for us, they just wanted to make sure we could swim. We had to duck our heads under, stand at the edge of the pool and practice kicks and swim a little if we wanted to try.
I was partnered with Dave, although I think it may have been that some of the other boys wanted to stay away from me, but at least the girls smiled at me and some looked at me and mouthed ‘are you ok?’ Quite a bit, so I just nodded and smiled back.
Practising swimming with Dave was funny as until this moment he was the only boy at the school who knew about my girls, but I caught him looking a few times. He was really struggling to support my weight as he didn't know where to put his hands and with both on my stomach I kept tipping forward and my head went under. In the end I did it for him, taking a hand and putting it on one of the boobs so he could feel it, but more importantly I no longer felt like I was going to drown.
After that he would kinda feel them when he wanted to, and it was funny really, mostly it was while helping me, but he also kept hold of them for longer than he needed to. I was enjoying it to be fair, he was very gentle and the water made me slippery which seemed to add it.
If I do see Aaron before he leaves I will try and get into the shower with him.
Anyway, as Dave was feeling me a lot, which I thought to myself, ‘ok, fairs fair’, so when I next supported him, I slipped a hand down his stomach slowly and held him there.
He was rock hard, not surprising really, but he was like really rock hard. When no one was close enough to hear us, I said, “You need to stop touching me or everyone will see him when we get out and everyone would know I had caused it.”
“I can’t help it.”
“I know, but you need to think of something else quickly.”
We had a different exercise to do, pushing off the wall of the pool and try to swim four metres, so I tried to swim to him, he tried to swim to me. But I could tell he was still hard.
We were given a five minute break and the whole group either stood by the wall or in little groups in the shallow end, and me and Dave leant on the side. I asked him, “Still?”
He nodded. Great. Here’s me with boobs and my only male friend at school - who also has a little crush on me - has an erection and we can’t be here much longer now.
So I did what any friend would do, and in the pool surrounded by people I gave him a hand job and he felt my boobs till he came, stifling any noise he wanted to make. I told him it was our secret and after that he kept his hands well away from me.
When the lesson was over we climbed out the pool and all stood in a line and of course the other boys were all trying to look at my boobs and there was no point in me trying to hide them anymore. In fact, I felt quite powerful standing there in my pink bikini bottoms. The teachers talked about how important it is to be able to swim but we were just getting cold now being out of the water so they said we could get changed.
As I walked past the younger PE teacher, Mr Howard he stopped me and asked me to hold back a second and one of the women PE teachers came over to talk to me.
She told me how sorry she was I had to go through with this, Sarah and Jane had explained about me and that she will make sure the school rules are changed. She also suggested I start wearing a bra and if I do decide to keep up with the swimming lesson to borrow a swimsuit.
I thanked her and walked back to the boys changing room, some of them were already out and dressed. I walked past Mr Howard and he apologised as well for the gruff teacher, saying that he had good intentions, but is just a bit old fashioned.
Mr Howard said, “I’m currently training to be a PE teacher, only just in my second year and doing a work placement as part of my training. I can tell you that how he behaves is not what we are taught. He’s the past.
I looked at Mr Howard and thought, wow, he’s not even a proper teacher yet and still at university. Suddenly I was looking at him a bit differently and realised he’s about the same age as Aaron.
And cute too.
I walked in to my cubicle but kept the door open as I talked to him, telling him it’s ok really as I wrapped my hair in the towel.
Ok, I was flirting with him a little, pushing my boobs out a bit, hoping he would look and trying to work out if I caught him or not.
Without even thinking I slipped my bikini bottoms down and told him it was ok, I understand and appreciate his concern but really I just did what every other boy did when you think about it. I took the towel of my head to start drying myself and Mr Howard was looking at me, or I should say he was looking at what wasn’t tucked anymore.
I said, “See, I am a boy.”
And because the tuck was released and having my boobs caressed earlier and giving a hand job I was already beyond a semi and now getting harder. I sat down and of course it poked up, but I decided to pretend it was nothing and said, “I really appreciate you asking the girls teacher to speak to me. She suggested I get a bra to wear to school and borrow a swimsuit from my sister for next week’s lesson. Do you think that will be a problem, me wearing a swimsuit?”
I snuck a look at him. Hmm, is that the outline of something I can see there?
As he answered me I stood up and made no effort to hide my boobs or little erection as I dried my hair.
He said, “No, I think it makes sense, you have as much to cover as any girl and no one will complain. But you should speak to your parents about it.”
I stood there looking at him and I was completely rock hard and I needed to deal with my own problem and wasn’t even listening to him as he talked about maybe not needing to swim in future. I stood right by the open door, naked and hard and said that’s ok, these don’t stop me swimming, and I brushed my fingers over them and down across my stomach, copying something I had seen in a film, trying to be sexy.
I said to him, “I do need to take care of this though, I will be quick, I promise.”
And I wrapped my hand around my cock, stroking it slowly as I slowly pushed the door closed. He never once stopped looking me in the eye, and I didn’t close the door completely, and he stood outside all the time, telling boys to hurry up, we don’t have all day. I like to think he was encouraging me to finish, and it really didn’t take long before I came, opening the door a little and looking at him and mouthing the word ‘finished’.
I never told anyone about that, I really didn't want him to get in trouble and I really didn’t want to get in trouble myself. Still, it was kinda hot!
Outside the changing room Sarah and Jane were eating for me with a couple of the other girls, who all asked loads of questions but now I hadn’t bothered to put the vest back on my boobs were a lot more obvious. I told them about what the teachers had said to me after and the need to wear a bra to school and borrow a swimsuit in future, which lead to a long conversation about different styles.
At home though, mum and dad were very unhappy when I told them about it, and I begged them not to do anything. I found out a lot later they did speak to the school and the school and had a meeting with the gruff teacher and this encouraged him to take retirement at the end of this school year, not that it mattered to me.
My sister Claire thought it was hilarious and had already heard about how I ‘strutted out like a supermodel at the beach’, which really isn't true at all, Sarah told me I looked as scared a rabbit but got more confidence as I walked towards everyone. Claire is going to sort out a swimsuit or something for to wear next week, but really wanted to know what bra I should wear, I had too many to pick from.
So the next morning I picked up Sarah on the way to school and she noticed immediately, I was in one of my pink bras as the dress code allowed it, but I was wearing a bit ore than that. I was wearing the full matching set and one of Claire’s old fitted school shirts, and a pair of her trousers which she said are pretty close to the dress code so I should be ok. I was still wearing my boy school shoes, but with my uniform blazer on my boobs looked more obvious and that’s where everyone will look anyway.
Just like Dave said when we first met in the mall, everyone was really accepting of me, I was asked to talk about it in homeroom and everyone was completely ok, well, there were still the whispers and looks, but no one was outwardly horrible to the boy with boobs. I was a lot more accepted by the girls than the boys, but I was never into sports the way they are. The girls PE teacher who suggested I wear a bra spoke to me when we bumped into each other, she did notice my trousers and said not to push the dress code any further.
I had hoped to go out with Aaron that evening, but he had to do something with his parents so I needed up inviting Dave over after school and streamed a movie. We hadn’t talked about what happened in the pool and I wasn’t going to bring it up, but I probably shouldn't have forgotten what I was wearing and changed in front of him.
Honestly, it never occurred to me as we were technically two boys together. I had slipped off my bra and my panties halfway down my legs when I realised he had stopped talking. I looked at him and just stepped out of them, went to get a pair of cotton ones to put on and of course he finally saw in very close detail that I am a boy.
He quietly watched me as I slipped the clean panties on and tucked, then grabbed a pair of leggings and a loose tee shirt, putting them on. I sat next to him again and told him he has no idea how much more comfortable this is, and at least now he knows I am a boy under this. I asked if he was ok about that, and that next time he will need to find a way to control it or take care of it himself.
The rest of week at school was just another week at school, I did start to wear a little make up and was definitely more on the girl side of life than the boys - bras do that to me - but I did have to go to PE again and I tried to keep as much of my body hidden from everyone as possible in the changing room. I also wasn’t dumb enough to wear something so pick or lacy.
At the weekend I hung out with Sarah in between getting throughly fucked by Aaron before he left to join the army. I was sad, but I knew he would leave and he was only a fuck buddy really. A really good fuck, but a fuck buddy!
Monday after school though, I arranged a date with Dave, and I do mean a date. I knew I needed to find out a bit more about this side of me and we were going to get a pizza. We walked to mine first and he waited downstairs while got changed into a skirt and top and put some make up on. I walked into the kitchen with my handbag over my shoulder, took his hand and we walked to his so he could get change and a short walk to Starbucks before going to a pizza place around the corner from his.
To anyone who was looking at us they could see we were on a date, but we had never discussed it being a date. I thought of it as a date, but I did wonder what Dave was thinking about it. I think he might have thought it was a date as when we left he took my hand and he walked me home.
We didn’t say much at this point, just walked together. When we got to my street, he stopped a few doors from my house and told me how much he enjoyed our date. So he did think it was a date as well, and he has seen me naked, he has felt my boobs and I have given him a handjob, so maybe this isn’t so much a date as the start of a relationship?
I’m not sure I want that with him, but I do like him, so when he leant forward to kiss my cheek, I turned my face to kiss him. I think he was surprised as he pulled back. I just looked him in the eye and then he gave me the most toe curling kiss I have ever had. With Aaron it was about lust, but this felt like something different, maybe not passion, but different to lust and maybe more like what I did with Sarah. Maybe he is going to be the boy version of Sarah for me? A friend that is more than a friend and help me be more like myself?
Anyway, we finally broke the kiss and I walked to my door. Dad was cool about me having a date with a boy, mum wanted all the details and Claire was watching me through the window so she knew all about it, but I said I had homework to do.
In the morning though, I seemed to be running late trying to get everything I needed for school, and Claire sorted my swimming gear for me, stuffing it in my bag. Once again I was wearing a pink set of lacy lingerie under my clothes and really I was wearing all girls clothes despite going into the boys changing area at the pool. That I thought was quite funny, and walking in with Dave after our date was just as funny.
It seemed everyone goes to the same cubicles so once again I was right at the end. I stripped off and got out the swimsuit and saw that Claire was being a typical sister and messing with me.
There was a bright pink bikini, the type you wear to the beach not a swimming pool. There was also a swimsuit, but not one for swimming in, it was the type of thing you would wear on a boat party in Ibiza! I slipped it on and it barely covered anything, I was showing a lot of side boob with a deep cleavage that stopped below my belly button and only just had enough material to cover my tuck. I looked at myself in the mirror and almost had a panic attack.
I opened the door a little bit and could see Mr Howard and I called him over, saying my sister played a joke on me and I showed him what I was wearing. His eyes went wide and before I could say anything I told him she also packed a bikini for me, showing him that. I knew bikinis were not in the dress code, but the swimsuit was literally indecent and he agreed it was the best option so I closed the door and changed again. By now of course everyone was in the pool area and I would be the last one out, but at least this time there’s a lot less to be scared off as everyone saw everything last time.
I stepped under the shower and once again made an entrance in my body glow pink bikini that was giving my boobs quite a lift and the bright colour making me more eye catching than ever. Walking out of course everyone looked and I saw Sarah and Jane giving me the thumbs up, so I decided to work it, swinging my hips and rather than being a boy with boobs, be the girl I’ve been all summer as I joined Dave and the other non-swimmers.
This lesson was fun, I felt a lot less exposed which is hardly surprising really, but this time I enjoyed it and was paired with another girl to help each other. Wait, did I just say another girl. Whatever. I explained about my sister setting me up with this, and she told me I should have worn that swimsuit anyway as everyone here has seen my boobs. We then talked about boys and how the girls hate that swimming in mixed classes and that I must know what it feels like to be stared at by now like. But really, I hadn’t noticed it as I’ve not grown up with it and normally just try to hide my body.
At the end of the lesson I was one of the last again to walk back as I’d had another talking to about what I was wearing and only just managed to avoid a detention, promising to get a more suitable swimsuit for next time. I started to walk back to the boys changing room, but this time there was a pool attendant standing by the entrance who was mopping the floor and he stopped me.
He said, “You can’t go in there.”
I tried to explain but he made it very clear I needed to go back to my changing room, not even prepared to go and get a teacher for me, so I walked as fast as I could around the pool and called out to the teacher in the girls changing area. I explained what the attendant said and she looked me up and down telling me she could understand and to follow her but not try anything funny and keep my eyes on the ground.
And into the girls changing area I walked, past the girls in their own cubicles, mostly with doors shut but some open as they dried their hair. Of course Sarah and Jane saw me and and as I explained what’s going on they both said I may as well use the girls in future as we’ve all changed together before, making the teacher raise an eyebrow as she looked at me.
I just shrugged at her.
We walked out into the public area and across to the mens changing rooms and she called out to Mr Howard, then saying to me I looked very pretty last night in the pizza place. I almost died. I thought to myself, so what? I’m in a bikini so it’s not like she isn’t aware of me. Mr Howard collected me and I walked past all the boys, all finished getting ready and all looking at me. It was like that scene in Grease when Rizzo tells someone she’s pregnant and the message gets passed along. Ok, maybe not like that but it felt like every boy knew I had walked through the girls changing area. I stepped into my cubicle, thanking Mr Howard and slipped off the bikini top, gave him a smile and closed the door.
Ok, he’s quite hunky, and yes, I kinda flashed him.
Sarah and Jane were waiting for me but Dave was nowhere to be seen this time so I will text him later anyway, but they both said they were going to speak to the teachers and make them let me use the girls for swimming in future, but I told them not to worry, I just need a proper swimsuit and we agreed to go shopping for one after school the next day.
After I had done my homework I called my sister Claire into my room. She was smirking and I knew she thought I was about to talk about the bikini and I gave them both back to her saying, “The teacher thought the suit was a bit too much for the boys to handle, but the bikini worked ok, thank you.”
I wasn’t going to give her the pleasure of knowing how terrified I was when I first tried it on. I could see was a bit miffed that I was acting as if it didn’t bother me, and if the girls hadn’t been ok with me in their changing area, I maybe would be. But right now I was more concerned about some new school uniform stuff that had appeared in my wardrobe.
Mum had been out and picked up some new things for me. There were four skirts in there, two short pencil ones and two of the short pleated ones (whoever decides these things must like seeing school girls legs). Anyway, she brushed it off saying mum had picked them up for me in case I want to wear them and the school doesn’t have a gender uniform policy so they won’t complain. I opened my sock drawer and there were two packs of five opaque black tights, uniform approved and held them up to show my sister who was holding up a pair of shoes, Mary Janes in my size with a one and a half inch block heel. I sat down on the bed in surprise.
The next day I knocked on Sarah’s door and she squealed in delight when she saw me in the short pencil skirt. She checked my face closely and said I could wear some lip gloss as they allow that as well so I put some on and us girls walked to school.