It had all started some years before when I was a teenager. I had stolen into my mother's bedroom one day while she was busy downstairs wih some friends and rummaged through her lingerie drawer.
What delights lay inside! Bras, panties, slips all there for the trying, all mine for the moment and what a moment!
I knew from that moment on that my future lay in wearing women's clothes wherever and whenever I could.
College came and went in a blur, I did well enough, met a few girls and even dated some, but the truth was that I was dating them for appearance sake. Most thought I was only dating them to get into their panties, what the didn't know was that I was - but to wear them!
Then one day I was caught and my life changed forever.
I was in my room, it was my third year at college and I was out of the grounds and in my own bed-sit which allowed me a certain level of privacy and, of course, the chance to dress up as Joanna whever I could.
This day was a quiet one, no lectures, no essays and no dates. I had set aside the whole day to pamper myself. I had bought a new slip, matching bra and panties and a nice summer frock and had waited eagerly for this chance. I even summoned up the courage to go to the makeup department and buy some bits and pieces ("for my girlfriend") and a book on makeup tips.
This was my special day. The first day that Joanna was going to be fully dressed and made up - and that's when the knock came at the door!
Luckily for me I only had on my bra and panties, so I was able to throw on a tee-shirt and some jeans and hide the rest away under the bed while I dealt with whoever it was.
It turned out to be Melissa, a girl I had dated a few times, kissed and cuddled and even managed a little grope with, but no sex, nothing like that at all looked even on the cards.
"Hi Joe!" she chirped as she marched into my room. "I heard you were at a loose end and thought I'd come and help you clear out the cobwebs!"
"Mel?" I asked "What cobwebs?"
"You know, let's spend the day together doing something - anything!" She looked around. "I know I'd be bored staying in here all day so I thought I'd cheer you up!"
I stuttered and stumbled over an excuse (dammit I wanted to be on my own!) but she was having none of it.
"Look you've been far to self-indulgent this month. I've hardly seen you (no shock there, we'd only dated four times in two years!) and I felt like a day out - come on!"
She was insistent and I had no suitable excuse and so, with heavy heart, I said "ok, give me a moment to change".
But she was having none of it. "Come as you are!" she insisted as she grabbed my hand pushed me on the bed and offered me a pair of sports shoes.
I put them on and tried desperately to work out how I was going to survive all day with what I was wearing underneath my clothes but I wasn't thinking straight at all and before I knew it, we were out and on a bus and heading for the town centre...
We went to a local cafe, which was a popular one with the students, cheap food and some quiet corners to study, if required, or hold hands. A light breakfast was my intention and as we sat down in one of the quiet booths and started eating, Mel dropped her bombshell.
"You know that bra doesn't fit you properly at all - why didn't you ask my advice before you went and bougnt one?" she asked, as if she was talking to a long-standing girl friend.
I almost choked on my food as she said it and she had to bang my back hard to dislodge the piece of bread that had stuck in my gullet. "H...how long...?" I began, but she cut me short. "Since today. You're not very good at it are you," she said. "Your bra strap has been showing ever since we got off the bus."
I looked down at my shoulder and sure enough, there was the tell-tale sign that meant - what?
"Are you going to tell anyone?" I asked.
She started at me for a few minutes as if weighing up what to do. "No, silly!" She said suddenly. "That's between you and me!"
It was like a huge weight had suddenly been lifted off my shoulders and I must have sagged visibly because she reached over and held my hand and looked into my eyes. "Everyone has secrets in college. You're no different to anyone else and I think it is very sweet!"
"So," she said after I had composed myselft. "Are you just a dresser, or are you looking to go further?"
"What do you mean?" I asked.
"Well are you happy being a guy, or are you looking to go the full monty and chop it all off?"
I laughed. "I dunno. I've not really thought this out at all yet. It's only been in the past year, that I've decided that I would start dressing up on a regular basis."
She studied me for a moment, as if wanting to say more, but then decided against it. "Well eat up and then, if I were you, I'd sneak into the loo and whip that bra off because it's never going to be covered by the tee-shirt, I promise."
I laughed and sat back relaxed. I began to think about Mel. She was pretty enough and was always outgoing and friendly which made her a hit with most people. I knew she had been out with a few boys, but most said that she was a kiss and grope date, not an all-the-way girl and most used her as a stepping-stone to meet other girls and move on.
She had long hair and, from what I remembered of our one groping session, nice firm breasts, a bit small, but nice...
She outlined her ideas for the rest of the day. "Are you rich?" she enquired. When I assured her that I was ok this month, that pleased her.
"Then let's go shopping," she announced. "I'll help kit you out properly, but on one condition..." I looked at her ("uh-oh, here it comes...") and waitied. "You must model for me when we get back!".
What could I say? I agreed and we set off for a long day's hike around the various shops in town...
Mel was a canny shopper, to give her credit though. For much less than I thought we came back with three outfits and some underwear that I was looking forward to trying on.
All day Mel had been bubbly and cheerful and very supportive. I knew we had become even closer and a bond had formed which I was never going to want to break in a million years.
On the way back, we laughed and joked. Mel was on top form. The only time she got serious was when we discussed my sex life.
"So have you ever - you know - been with a guy?" She asked suddenly.
"No," I replied.
"Why not? Don't you fancy them?"
"Well there's been a couple that I liked," I replied. "But I've never had the courage."
"Well now...this could be interesting," she said cryptically.
We got back to my bed-sit and I threw my bags on the bed. Mel sat down next to them and motioned me to sit next to her.
We kissed. It was the natural thing to do and, after what seemed like an eternity, I broke away and looked at her, waiting.
"Time for you to model for me!" she announced as she reached round and began rummaging through the various bags.
"Now we have three outfits, prissy, proper and slutty. I want you to dress up in that order...off you go!" she said as she pushed me towards to bathroom.
The first outfit was a short summer frock, powder blue with wide straps. I selected a pair of lace frilly panties and a matching bra and as I donned them, I felt warm inside. Mel had kept her promise - the bra fitted like a dream!
"Ready?" I shouted thrugh the door.
"As I'll ever be!" She shouted back.
I opened the door and stepped through. "Ta-da!" I sounded as I made my entrance. Mel wolf-whistled appreciatively and clapped and cheered as I twirled around to show all sides.
"Hubba hubba!" she shouted and then giggled at my clumsy attempt to curtsey. "We'll have to work on that!"
I sat next to her. "You like huh?". She stroked my shoulder. "I love it!" We kissed again. By now I was sporting such a hard-on it was incredible.
Mel took the lead. She pushed me back on the bed and started to kiss my neck and down towards the top of my frock. I was on fire, each kiss sent shudders down my body.
Then she stopped and looked deep into my eyes. "You know you've shared a very special secret with me today a secret I will never reveal unless you want me to. But it works both ways you know."
I looked up at her. "What do you mean?"
"Promise you'll never tell. Promise you'll not be angry," she demanded.
"I promise, I promise," I said urgently, my throbbing hard-on driving my thoughts.
Mel stood up and lifted her top over her head revealing her two perfect breasts. "Ready...?" she asked.
I was ready for almosy anything..."Ready"...except for what happened next.
Down went her slacks and her panties and out popped a dick!
Want part 2? Then click here for more!