A Secret Shared

This is my first attempt at writing anything. It is mostly a true story (well 90% true) about the first time I confessed to anyone about my crossdressing and what happened afterwards. It is rather long-winded and anyone hoping for lots of sex will be disappointed (but don't go away though - I hope to write something for you very soon). The names have been changed and the timing of some of the events have been rearranged slightly, but this is my story that I felt I needed to get off my chest before I tried my hand at pure fiction. I hope some of you manage to get to the end of the story and perhaps even enjoy or empathise with it. Any feedback will be appreciated.

The Meeting

I arrived at the door of her university hall of residence room, full of apprehension, excitement, anticipation, fear and hope. I had not seen her for a whole week, and we had parted in the worst possible circumstances. I really could not wait to see her face, feel her embrace, smell her perfume, taste her lips on mine, feel her soft skin against mine. However, I did not know if I would ever experience any of this ever again. For this late-developing, hormone filled twenty-year-old, the anticipation, excitement and fear was both exhilarating and frustrating. The combination of first love and the subsequent recent discovery of having real sex with a beautiful, caring, intelligent woman, had my pulse racing. The realisation that I may have messed it all up with her, filled me with dread and hesitation. I took a deep breath and knocked quietly on the door.

"Hi Clare. It's Jeff. Can I come in?" I quietly croaked, before clearing my throat and trying again, hopefully sounding calm and in control, unlike how I was really feeling.

The door slowly opened half-way, revealing a room in semi-darkness, the only light coming from the sun breaking through edges of the window, around the ill-fitting curtains. While I strained to see into the room from the bright corridor, I felt the soft skin and gentle caress of a hand as it glided down my forearm and took my own hand,

"Quickly, come in," she implored, before pulling me into the room, the door quickly closing behind me. Her body quickly pressed into my own before I even had the chance to drop my weekend bag onto the floor. I wrapped my arm her waist, feeling the almost perfect way it fitted the curve of her back and rested on her hips. I pulled her tight against me, feeling the outline of her breasts pushing against my chest. Her lips pressed on mine, and I tasted the light oiliness and flavour of her lipstick. Her hand caressed the back of my neck as she pulled me further onto her lips. My lips parted fractionally as I quietly moaned from pleasure and her small, moist tongue slipped between them to dance over the tip of my own tongue.

"Well this has to be a good sign." I thought to myself. "Perhaps, there is still hope for us."

She pulled her lips away from mine, stepped back and taking me by the hand, lead me to the bed, at the side of the room. Sitting next to me, holding my hand with both of hers, squeezing and rubbing it; she seemed uncertain, building up the courage to say her mind. Despite the obvious passion between us a few seconds earlier, she now seemed nervous; as if she was about to tell me something that she was unsure about; something she was finding difficult to say.

Fearing the worst and suddenly also remembering the darkness inside the room, I placed my other hand on hers.

"Are you OK? Are we OK? Why is it so dark in here?" I asked, desperately trying to remain calm. Pleading internally that she would not leave me, or worse.

She squeezed my hands again and whispered, "I have been thinking all week about what you told me last week. I really do not know how to handle this. There is no way I can unhear what you told me, and I am not sure this is something I can deal with. I really don't know where we can go on from here..."

"Oh no!" I thought. "How could I have been so stupid? Why couldn't I have just kept it to myself? Kept it hidden, like I always have? Why did I have to open my stupid mouth? I knew it would ruin things." I was ready to leave in shame; never to return; knowing that I had destroyed the best thing to happen to me in my life so far.

How did we get here?

Last weekend, after a few glasses of wine, I had decided that Clare was my soulmate; the one; the only; my forever; the person I would grow old with. Over the past few months, we seemed to be able to talk about anything and everything, spending hours just sharing our inner-most thoughts and beliefs, into the early hours of many mornings. As such, I assumed it was only right that I bared my soul to her and told her my biggest, deepest, shameful secret.

To be honest, Clare was my first love (I was her second). It was embarrassing that we were both nineteen and both so inexperienced when it came to things concerning the opposite sex. She had religion and I was just a very shy, slow developing boy. When all the other boys at school were growing tall, growing hair and getting girlfriends, I seemed to remain as I was when I was 12. I was the shortest boy in my Sixth Form school year and painfully shy when it came to the girlfriend / boyfriend thing. I would stutter, sweat, look at my feet and generally avoid any romantic connections for fear of rejection.

It was not that I could not talk to girls. I did it all the time. In fact, most of my best friends were girls. At school, I always chose the clever girls as class partners (mostly because I needed their help to understand the lessons). Between lessons, I would sit with different groups of girls and chat about music, clothes, who had a crush on whom and other inconsequential topics. My parents did not think there were any problems as I would regularly bring a girl (or several girls) home or go to their houses to watch movies. They assumed I had girlfriends like all the other boys at school.

However, I was never really boyfriend material. The girls generally thought I was 'sweet' or 'cute', but never a boyfriend. To be honest, I was more like one of the girls. I joined the girls at lunchtimes and weekends in town, where I would follow them from shop to shop, and I watched them, seemingly trying on the same clothes, day after day, but never actually buying any. Sometimes, they would ask what I thought about a top or a dress, occasionally jokingly asking me what size I was and whether I would like to try on a skirt. Each time I would look embarrassed, laugh and say it was not my style, or I did not have the legs for it, or I did not have any money.

They enjoyed embarrassing me. However, what they did not know was that I only pretended to be embarrassed while, in fact, I longed to try on the clothes with them (or perhaps they did know and were giving me the chance to confess to them?). I dreamed of joining in with them; putting on a dress, heels and make-up; looking in the full-height shop mirror, with the girls telling me how great I looked; how I should definitely get the outfit. Unbeknown to them, since the age of about fourteen, I had secretly dressed up in my sister's clothes whenever I was alone in the house.

I had always been jealous of the way girls seemed to get all the breaks. They did not have to be charming, witty, or clever to get a date, boys just seemed to throw themselves at them. Boys never turned a girl down if they asked to go on a date. Boys never had to wash their hair or look after their dog. They would drop everything to go out with a girl.

Boys only ever wore jeans and t-shirts with trainers. Girls got to wear so many different styles of clothes and types of shoes. They could change their hair, wear make-up and put on jewellery to look pretty, any day of the week. I wished I could do the same.

One day I decided to see what it would be like to be pretty; how it would feel to put on some pretty panties and a cute little bra; slip into a skirt and feel it caress my thighs; wear a thin-waisted t-shirt or a cropped sweater. So, while I was alone in the house, I nervously went into my older sister's bedroom and tried on some of her feminine clothes.

I soon discovered that not only did they look good, but they also felt amazing. Luckily for me, my sister also had a boyfriend who would buy her sexy lingerie, so I had a wide selection of padded satin bras, silky panties, lacy suspender belts and patterned or fishnet stockings (it was the 1980s) to experience. In addition, there was a wide choice of figure-hugging nightclub dresses, short party dresses, long flowing skirts, and my particular favourite, a short red ruffled Ra Ra skirt and matching woollen cropped top, all smelling of an intoxicating perfume (Lou Lou). It often amused me that the girls had tried to embarrass me with an innocent looking knee length denim skirt and here I was, lay on my sister's bed, wearing a basque, stockings, G-string and skin-tight, thigh-high stretch woollen dress, with red heeled ankle boots (once again, a 1980s thing!).

The dressing up sessions continued on a regular basis, usually about once a week. However, I was becoming increasingly confused about it all. The desire slip into some feminine finery was unstoppable. It became an addiction. However, afterwards came the feelings of revulsion. What was I doing? Why was I doing it? What was wrong with me? Was I the only person in the world like this? This was pre-internet, so my options for finding answers were limited to asking friends or family and that was certainly not going to happen! I soon developed a love-hate relationship to my 'hobby'.

The dressing up continued up until, at the age of 18, I went to university. This involved moving away from home and away from my source of sexy feminine clothes. Living in a small room, in a hall of residence and having no money, other than for the essentials of food and course books, meant that there were no opportunities for dressing as a girl. I decided that I would finally get back to being 'normal' and leave my dressing days behind me.

My first year at university was also the year that my body started to change. Better late than never! While I did not particularly become very muscular or hairy, I at least got taller. Tall enough that in my second year of university, I found I no longer needed to lift my head upwards to look into the eyes of the girls on my course. I was actually the same height as most of them, sometimes even taller.

Just like I had done at school, I connected with some girls on my course, becoming their lab and study partners, and then working on projects with one particular girl called Clare. Soon this extended to activities outside of coursework, and I found myself regularly playing squash and badminton, cooking and eating with her, and we even started going to concerts and parties together. I was so happy I had found such a great friend. Then, after a few months, the unthinkable happened, following a night out together, we found ourselves back at my room, hugging and then kissing. I had finally found a girlfriend.

During this time, I had not thought about dressing up in feminine clothes. I had plenty of other interesting things to keep me occupied. However, as we began to spend almost all our time together and living out of each other's rooms, I started to notice the way she dressed. The different clothes she would wear. Her underwear. At Christmas and Valentine's day, I would buy her sexy lingerie. Sometimes, when we made out, I would ask her to leave her lingerie on. I could feel her lacy bra pressed against my chest, her silky panties sliding against my crotch, her stocking-clad legs squeezing my thighs. It was not long before long I started to imagine I was wearing the sexy lingerie while were making love.

One night, after seeing a band at a local pub, we went back to her room. We stripped down to our underwear and jumped onto the bed, play fighting over who was going to be on top. I like to think that I let her win, although as I was to find out later, she could have overpowered me if she really wanted to. As she knelt over me, straddling my crotch, and looking down at my smiling face, she unhooked her bra and it fell to my chest. My cock twitched at the sensation of the bra on my nipples. I began to panic that Clare had noticed, my shameful secret had been discovered and she would throw me out in disgust. Worse (or possibly better) was to come as she took the bra and placed the cups over my nipples and started to caress them. By now my erection was its full six inches and there was no way that Clare would not notice. I panicked and started to push the bra away, but she just increased her efforts to overpower me and forced my arms through the straps, so I could not remove it. She then leaned forwards, lay on my bra covered chest and kissed me deeply. I did not know if I was in heaven or hell. It was a dream come true, but my sordid secret was about to be exposed. In desperation, I turned sideways and wriggled from beneath Clare and threw the bra across the room. I think the sudden reaction shocked Clare and certainly spoiled the end of the evening. We ended up just cuddling quietly, while Clare fell asleep in my arms.

However, I could not sleep. The episode had brought back all of my old feelings from the past few years. I had just blown the chance of fulfilling my fantasy of making love to a beautiful woman while dressed in sexy feminine underwear. The exhilaration and excitement; The inevitable subsequent self-loathing of not being a real man. It went round and round my head until the early hours of the morning and I could see the sun rising through the window.

I loved Clare. She was going to be my one and only (I was young, immature and heady from the throws of first love). I could not keep secrets from her. I had to tell her everything. But what would she do? Would she reject me? Would she ridicule me? Would she tell all my friends? Would I have to leave the university in shame and return home without explaining to anyone the reason? Surely Clare was a better person than that. She would understand. She might throw me out and call me a pervert, but surely, she would not tell anyone else? But what if she let something slip, to a girlfriend after a few drinks, or a new lover when regaling tales of past dating disasters? What was I to do? I needed to go to my room to think (and get some sleep).

I looked across to Clare's beautiful sleeping face, kissed her on the forehead and headed quietly across the room, hoping to get dressed and slip back to my room before she woke. However, as I got out of bed, she stirred and looked across to me.

"I am sorry about last night," she whispered. "I didn't mean to upset you with the bra. I thought it was just a bit of fun. I didn't think you react so strongly about it. I have been thinking about it all night. I hardly slept a wink. Are we still OK?"

I could see a tear in her eye. I couldn't believe what a shit I had been. She had spent all night worrying about the bad thing she thought she had done to me when it was really all my stupid fault. I knew then that I had to tell he the truth.

"Let me make us a cup of tea. I have a lot to tell you and then you can tell me if we are still OK." I said, turning to fill the kettle, hiding the tears in my eyes.

The Confession

For the next couple of hours, over several cups of tea and many more tears, I told her everything. My dressing up. The feelings I felt while doing it. The opposite feeling I felt afterwards. My growing desires to restart dressing. My dream to dress with someone else, someone special, my girlfriend. She asked the inevitable questions.

"Are you gay?"

"No. At least not how you think. I want to feel like a woman with another woman. It's hard to explain, but sometimes I want to be a lesbian."

"Do you want to have a sex change?"

"No. Is that even possible? No. I only want to be a woman sometimes and a man at other times."

"Does anyone else know?"

"I don't think so. I certainly want it to remain a secret between the two of us."

"Do you want to go outside dressed as a girl?"

"Hell no! I don't want anyone else to know. Telling you is the most frightening thing in my whole life."

"What is your female name?"

"Oh! I don't know. I have never thought about that!"

"Will you still want to be with me if I don't want you to dress up ever again?"

"Of course I will still want to be with you. I love you. You are part of me. I would never do anything that would stop us being together. I cannot guarantee that I will not think about it and wish it would happen, but you are more important."

I looked at Clare, hoping for acceptance. She still looked worried, but possibly not as much as before. She certainly looked tired despite the copious amounts of tea we had consumed.

"I really need some sleep." she sighed. "I also need to think about this some more. I really was not expecting this. Look, you are going off to London for your course work this week. How about we have a little break while I get my head together and then we can get together at the end of the week and see how things stand. I know it is really bad leaving this for so long, but it will give me time to think. Come round on Saturday night, 7pm and we can talk more."

My heart sank. Not seeing her for a week and not being able to talk to her about any of this could only mean one thing. She was going to leave me. At least she was going to let me down gently. Give me a week to get used to the idea before she made it official. I stood up, gave her a long hug, and kissed her on the cheek.

"OK." I stammered. "I don't know how I am going to concentrate this week. I will miss you so much."

Did I mean over the week ahead or forever?

I walked across the room and opened the door, vowing not to turn around and look at her face for the last time.

"Wait a moment," Clare said in a shaky voice. She pressed something into my jacket pocket. "Don't look until you are in your room. It's something so you won't miss me quite so much this week."

I walked down the corridor. Not looking back. Never looking back. Not wanting to make this the last time I saw Clare's beautiful face.

I walked all the way to my Hall in a daze. Arriving at my door, I searched for my keys in my pocket. I felt something soft, smooth and cool. Remembering Clare's last words, I pulled my hands out to inspect what she had put there. In my hand was the pair of silky black briefs and a satin padded bra she had worn the night before. I stared at them in disbelief. Perhaps there was hope for us after all, but how could I wait for a whole week before finding out.

Where are we going from here?

So there I was, after a week of sleepless nights, going through everything I had said the last time we were together, feeling like a defendant waiting for the jury to announce their verdict. A week of going through all the possible scenarios of what might happen next. Most involved, exposure, humiliation and losing the love of my life. None of them seemed to have a happy outcome. The only ray of light in my thoughts lay in the lingerie that Clare had given me as we parted. The lingerie currently in my jacket pocket.

She squeezed my hands again and whispered, "Bear with me. I have been trying to work out how to say this for the past few days. It may not come out too coherently, but please let me finish before you say anything. I need you to understand how I feel inside."

She paused, all the time, looking at our hands. Unable to look into my eyes. Her hands trembling. My heart sank. This did not look good. Finally, she resumed her prepared speech.

"I have been thinking all week about what you told me last week. I really do not know how to handle this. It would be so easy if we could go back a week and stop you telling me, but there is no way I can unhear what you told me, and I am not sure this is something I can deal with. I don't know how we can go on from here..."