- Joined
- Nov 15, 2025
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- 116
We go back to when I was in school, when I discovered the thrill of girls clothes, the knickers, the tights, skirts... Oh I took every opportunity to get dressed up! It was my escape, I didn't have a happy childhood - I mean it wasn't too awful, the physical abuse didn't leave any marks that lasted more than a couple of days, the bullying took its toll mentally, the sexual abuse left a few more mental scars, but lots of people had it much worse. So dressing up was my secret joy.
The more time I spent in a skirt, the happier I was. I would sometimes wear my sisters knickers under my school clothes, not on gym day of course! I'd wear her clothes as much as I could, as often as possible. I always dreamed of getting fully dressed and going out, around town, anywhere, just being a girl.
I did ok at school, I wasn't a super brain, but I was a bit of geek and got reasonable grades. People started to talk about going to university and were asking where I was going to apply to. I had no idea about any of this, my family were very working class, no-one had ever stayed on beyond compulsory school age, much less gone to university! So I asked a few questions, and I could see a glimmer of hope for the future - I could go away, a long way away, to university!
I was only 14 at this point, but I started to plan ahead. I need to make sure I got good enough grades to get a place. I also day dreamed about going to university as a girl, and then my plan was born.
Always a chubby kid, fat if I'm honest, I set about changing things. I just started with smaller meals, healthier choices. I started working hard in PE - we had a new PE teacher, the old one was a nasty guy, if you weren't super sporty he wasn't interested. I was fat and asthmatic, couldn't run 100 metres. When I told the new teacher I wanted to get in shape, he was amazing - he helped coach me with exercises that I could do with asthma - how to train up to the limit of my breathing and not set off an attack. Over time I got fitter, my asthma improved, I got leaner and lighter. I wasn't interested in team sports, or weights, I just discovered a joy in running. I wasn't fast, I wasn't going to suddenly be a sports star or anything like that - it was a revelation, but just for me, nothing amazing for anyone else.
I also let my hair grow out. In addition to being fat, I also had bright ginger hair - might as well have had a target painted on me! But I wanted long hair to help be look more feminine. This was a battle; my parents, particularly my dad, were not happy about this. I was a fan of rock and heavy metal, so it was pretty common for guys to have long hair - but they did not like it.
I stood my ground, and stuck with my other changes too. My weight slowly dropped, my fitness improved, my asthma reduced, my figure became more lean and less pudgy, my hair was longer and down reached halfway down my back. I worked hard on my school work too, my grades increasing a little, solidifying my chance of good A levels, and a good university place. I spent as much time as possible dressed - whenever I had the house to myself, I'd strip naked and get fully dressed in my sisters clothes.
My relationship with my family didn't get any better, the bullying and violence remained the same - cementing my desire to go to university and move far away. I moved on from school to college, meaning no school uniform any more. I was desperate to dress as I wanted, but the risks were too high. I got some lip gloss once, and wore that walking through town after college - but I was so terrified that I would see someone I know and word would get back to my family!
Eventually, it came time to apply to university. This was before the internet, so there was no way to know which university cities might be more LGBT friendly (well, it was just LGB back then). I visited a couple of different university campuses (on my own, my family weren't interested), and I checked out the student union. I saw an advert for the LGB club, which helped me feel at ease. I wasn't too sure what I was - I didn't really know about TV / CD / TG etc. I only know that I was much happier when I was dressed as a girl and that I had thoughts for both men and women.
It was Bristol that took my fancy the most. The Uni was great, the city too and I was able to find a couple of gay clubs when I went for a look. So that was it, I applied and I was off to Bristol!
Part 1 of the plan - get to university - complete. Part 2 was a bit more complex.
I found my accommodation, a shared house near campus. There were three guys, a girl and me signed up to stay there. I met the landlord when I went down to see the property, in normal guy clothes, and sign the lease - I introduced myself as "Nat" and signed the lease with the same name. A month later, it was time to move to Bristol, and enrol at university! I made sure that I arrived several days before the other tenants - I had some work to do!
When I arrived, I unpacked a few things, but left most of my clothes in my suitcase - pushed under the bed. I took the bus into town and went shopping. I began with a few basic sets of underwear, black knickers with some lace trim and a matching A cup bra. Some tights, a simple skirt and blouse. Some basic make up. Then I took myself off to the disabled toilet (the only gender neutral facility) and got changed. I hadn't had a chance to practice with make up before, so just did the very basics (I'd been studying the tutorials in my sister's magazines). I was confident that I was passable - the bra showed some small breasts, which was enough on my slender frame.
Then I took to some serious shopping! I didn't have a lot of money, so needed to shop carefully - things that could mix and match to make multiple outfits. Now that I was fully dressed, I was able to use the changing rooms to check that clothes would fit, and looked good. Some careful selection of clothes and judicious use of my budget gave me a good enough wardrobe to get going.
I took the bus back to my new home, made a cup of tea and sat in the lounge relaxing - just happy to be me; "Nat" an 18 year old girl starting out at university.
My next hurdle was to be able to attend university as a girl... That was a job for the next day. I went to bed that night in my bra and knickers, lay there in my girly underwear my hands wandering, running over my skin, across my bra. It's a real turn on, and very soon, there is a significant lack of space in my knickers. I start to imagine someone else is there with me, this starts to take the form of a girl - I imagine she is kissing me, pulling my bra down just a little, enough to expose my nipple so that she can kiss and nibble it. She is naked, and I am stoking her breasts. My other hand caresses her buttocks, and we kiss. her hand moves down to my kickers, and frees my aching cock. It's quite small when it's soft, but a good 8 inches when it's hard. She straddles me, and slowly lowers her tight pussy on to me. I am stroking my cock as I continue to fantasise about this, duvet thrown back legs spread and a thick hard cock sticking out of my knickers. In my fantasy she is grinding her pussy on me, hot, tight and clenching. It's not long before she reaches a climax, and me with her - shooting a torrent of cum up in the air - landing all over my chest and face, some landing in my mouth, which I immediately swallow and lick my lips. I am soon fast asleep, cum drying on me.
Today is my challenge - can I register as a female student? I get out of bed and go for a shower, washing off the dried cum from my adventures the previous night, and throwing my cum stained underwear in a pile. I come out clean and fresh, with a towel wrapped around my chest and another around my hair - girl style.
I dress nicely, another simple skirt, skater style this time, and a vest top. I spend a bit more time on my make up, nothing fancy, just keeping it simple as I practice. It takes a few goes to get what I'm after, but eventually a bit of eyeliner, mascara, some foundation and lip gloss are adorning my face. I keep comparing my results with some magazine pictures, I'm no expert, but it's ok. I slip on my shoes, grab my backpack and keys - I head out. Walking to campus doesn't take long, and I find the registration area for new students. There are lots of desks set out, with signs to break people up by the initial of their surname. It's pretty empty, I shouldn't be surprised, I suppose, it's still early on the first day of registration - we had a week to register. I head to the A - H section and find a smiling middle aged lady waiting for me.
"Hi, I've come to register." I tell her. Of course I have, it's registration, I'm nervous and prattling.
"Ok, love. Have you got your letter?" She asks me.
I hand her my letter, which just gives my 1st initial. She taps my details into her terminal. I'm sweating with nerves.
She frowns.
"Hmmm. That's not right."
I'm struggling to control my breathing.
"Is there a problem?" I manage to squeak out.
"Nat? Is it?"
"Yes."
"Are you Natalie, or just Nat?"
"I go by Nat." I tell her, not entirely honestly but not a total lie.
"Then there's definitely a mistake! It's listing you as Nathan!" She exclaims with a laugh, but no problem, I can change that."
I don't correct her.
"Oh!" I force a laugh. "Thank you."
She taps a few more keys, and the printer lurches into life. The clack clack of the dot matrix printer. She tears off my enrolment sheet, and directs me to the next section for my photo to be taken.
One photo later, I have my student ID listing me as a female student called Natalie. I'm nearly in tears. Happy, joyous tears. I take my student ID to the Student's Union and get my NUS card - vital for a student in the early 90s!
I go to the student union cafe, wandering around a bit lost and bemused, the ladies behind the counter smiling towards the clueless fresher. I decide to get a coffee and sit down for a little while. I'm joyous, interacting with the cafe staff just like a 'normal' girl. No-one is pointing and laughing, no-one is chasing me out of town. Everything is going the way that I didn't even dare to hope.
I've been sitting there sipping my coffee for a few minutes, and I notice someone else coming in. A cute girl, also looking a bit lost, so I guess she's a fresher too. She grabs a can of Coke, pays and walks over to the tables. Our eyes meet and I smile at her, in what I hope is a friendly way. She smiles back, and walks towards me. I gulp. Suddenly nervous. This will be my first interaction with someone of my own age as Nat.
"Hey, it's really crowded in here, mind if I share your table?" She asks, joking, since we're the only ones in there.
"Sure, please do." I excitedly / nervously blurt out.
"You a fresher?" "Are you new?" we both speak together. I think about what she said "are you new?" I smile.
"Yes, I'm brand new. You?" Inwardly thrilled by the double meaning.
"Yes, came down a few days ago. Just registered and came here."
We chatted for a while, I told her I was Nat, and she told me she was Amy. She was from Nottingham, and studying English. I was from near Sheffield, and doing Biology. We finished our drinks, and she asked if I wanted to explore campus a bit. We walked and walked, I think we must have covered every square foot of campus! And we talked, well, Amy talked mostly. I was still a bit hesitant. Second guessing how convincing my voice was, making sure I didn't accidentally talk about any boy specific things that might give me away. We exchanged phone numbers for our house phones, no mobiles back then, and arranged to meet up for a drink in a few days.
I walked home via the doctor's surgery, I needed to register with a doctor here. I was going to need some help. The surgery was only a few streets away from my house, I walked in and walked up to the reception counter. Before I could open my mouth to speak, the receptionist did:
"New student, need to register?"
I opened my mouth to say yes, but before I did she thrust a form at me.
"Fill this in."
"Thank you" I squeaked out, feeling intimidated, taking the form.
This wasn't easy to fill in. It asked for my name, and they would need my old records, so they would need my real old name. But I didn't want to register with that name. This was before easy networked computers, I mean, the internet existed, but it really wasn't used much. There certainly wasn't any easy way for them to look up my name. I decided I would speak with the doctor and explain. So I filled out the form as Natalie, same date of birth and previous GP. I took the form up to the desk and asked if I could make an appointment.
"What for?" She demanded.
I definitely didn't want to give her that information. So I did the best I could think of:
"Hormones"
She pulled a face, and looked at the appointment book. "You're in luck. Dr Higgins had a cancellation, he can see you now."
I smile, "thank you". She points me to the corridor.
I walk down, heart thumping, sweating, on the edge of a panic attack.
I take a deep breath, on the verge of tears, and knock on the door.
"Come in!"
I go in, and hand him my new patient form. He asks me to sit, and what the problem is.
I blush.
"Don't worry, whatever it is, I will have heard it before."
I open my mouth to speak, but can't find the words.
"Are you pregnant?" He asks.
I burst out laughing.
"Sorry," I say, as I get myself under control. "But you've just paid me a compliment by asking that." He looks at me quizzically. "I have a hormone issue, I need some oestrogen. I'm not making enough."
He raises an eyebrow, and opens his mouth, but now I've started talking, it all comes out.
"I was born a boy."
He sits back in his chair. Somewhat flummoxed.
"Well." He says, blowing his cheeks out. "I haven't heard that one before! But ok, let's chat about that."
He asked me all sorts, how long have I been feeling this way, dressing, what to I want to achieve etc. Then we reach the physical examination. I take off my top and bra, and one eyebrow raises when he sees my puffy little tits. I've been taking my mum's HRT and old birth control tablets. I don't know how much I should have taken, but for the last year, since I found them stuck at the back of the bathroom cupboard, dusty, I've been taking them.
Of course, he asks how I have started growing breasts. So, of course I have to tell him. He sternly tells me that I must stop taking them.
"If you give me a prescription, sure."
He's surprised by my response.
"I need this." I tell him, with real desperation in my voice. "If you will help me, I'll do whatever you tell me, if you won't help me, I'll find another way."
He tells me to remove my skirt, I put the bra and top back on, then remove the skirt; I wasn't ready to be fully naked in front of someone yet.
"Please lower your knickers. I need to examine your genitals now."
I drop my knickers, and stand there. He examines my testicles, my penis. I swell a little. I'm desperate not to get hard.
He asks if I can still get erect and ejaculate. I tell him yes, I can. He tells me to turn and lean forward.
"I'm going to check your prostate now." His finger slips into my ass, I can't quite supress a small moan and am immediately hard. He's not in there long before he's satisfied. "Ok, you can get dressed again now."
I pull up my knickers and put my skirt on - there is a very obvious tent from my cock. I look at the doctor, "Sorry" I mumble, embarrassed.
"Don't worry, it's perfectly normal. Take a seat"
He asks if I'm sexually active, and I tell him no, I've never had intimate relations with anyone. That examination was the most consensual contact with someone else I've ever had, but I don't tell him that part!
He tells me he's reluctant to prescribe anything unless he has blood test results to see what my levels are, but knows that if he doesn't I'll keep guessing for myself. So as long as I promise to stop taking what I have, he'll give me a starter prescription. Then when the results are back, he'll be able to give me the specific prescription I need. He also tells me that I will need to talk to a psychologist and that I'll get a letter with a referral.
I lunge at him and give him a huge hug. Now he's the embarrassed one.
He gives me three injections, and prescription for tablets. I walk out of there feeling like Wonder Woman. I go straight to the pharmacy down the street to get my tablets!
I walk home and as I walk into the house I'm face to face with three semi-naked blokes.
Chapter 2
"Oh hi!" One of them exclaims, "are you Nat or Jo?"
"Um, I'm Nat. I guess you're my housemates? I wasn't expecting you for a couple more days."
"Oh, no. Well, yes. Er. Yes, you see, I'm your housemate, but no, these others aren't - I decided to come up early, and I met up with these blokes in the pub. We just managed to get beer all over each other. Hence the not quite being dressed thing."
"Right... Ok. Well, I'm going to head up to my room for a bit."
"You can join us if you like, we've got plenty of beer! Oh and I'm John."
"Thanks John, I appreciate the offer, but not this time - had a busy day and I just need a bit of quiet."
"Ok, laters!"
I wasn't too sure what to make of this. I didn't want a party house, but at the same time, I was hoping to be sociable and join in with some fun myself. I decided to reserve judgement and see what happens.
I walk up to my room - making sure to lock the door. My cock hasn't quite gone soft since Dr Higgins fingered me. I drop my bag, kick off my shoes and pull off my top. I run my hands over myself, feeling my long hair, my soft skin, my hands over my budding breasts, over my hips, pushing my skirt down past my hips. I pinch my nipples through my bra, I gasp. My hands slip up under the bra, exposing my little titties. The air feels great on them, my fingers brush my nipples, causing pleasure shocks to run down to my groin. One hand slides downwards, and cups my mound. I can feel the heat from my cock, and the dampness in my knickers from all the pre-cum I've been leaking.
I take off my bra and knickers, leaving me naked. I lay back on my bed and stroke my cock with one hand, playing with my breasts and nipples with the other. Wishing Dr Higgins was there with his finger. Or his cock. Or a dildo. At least something in my ass! I knew I was going to have to buy a sex toy!
Remember the feel of that wide finger in my ass, I stroke my cock, thinking about being bent over by a strong guy, their hands holding my hips firmly, big cock pistoning into me. My orgasm builds quickly, my familiar fantasy taking me where I need to go. I slip my other hand behind me, my fingers pressing against my asshole, I shudder, I clench, everything goes tense and I erupt. fountaining my cum into the air, landing across my belly and face.
I relax sighing with pleasure. I quickly drift off to sleep for an afternoon nap.
____________________
I wake to a light tapping on my door, I'm still mostly naked, bra pushed up, knickers around one ankle. So I grab my robe and quickly put that on. I open my door a little, it's John.
"Oh, sorry, did I wake you?"
"It's ok, I was just having a little nap. It's about time I was up." I glance at the clock, I've been asleep for an hour.