Alana, an Epic Tale

It is strange when you first meet the person of your dreams. You do a double take and if hit hard enough, you stop and stare, with mouth slightly open.

My name is Sam and at 23 I had only been working for the big employer in town for a couple of years. I didn't need to work as my parents and brother died in a car crash and I was heavily compensated. My bank balance was VERY healthy, but I would rather have had my family back and been poor.

With thousands of people working for the firm, we regularly came across people we had never seen before. One lunchtime, there I was sitting quietly eating my cheese sandwich when I first spotted Her. She was like a goddess, beautiful and was just over six feet tall, with dark brown hair. The way she walked, you could tell she was athletic and her perfectly formed frame backed up this notion I had of her. I couldn't take my eyes off her. Like a complete idiot, time stood still for me as I just watched her for ages. Then she spotted me. I thought, she must think I was a complete loser gawping at her.

For the next twenty three hours, I couldn't take her out of my mind. Everything revolved around her and at that time, I had no idea even of her name or which department she worked in.

The very next lunchtime, I was sitting at the very same table I sit at every lunchtime, eating another cheese sandwich. I hoped to have another glimpse of her, but that is not what I got.

She came into the room and walked straight over to me with a big smile on her face. She sat next to me and nice as anything started chatting to me as if she had known me for years, all very relaxed.

Soon I knew her name was Alana and she worked in the research department, was 24 and most importantly was single. It was a surreal lunchtime as we even decided to meet up on Friday evening.

One minute I wanted to punch the air in celebration and the next I wondered why someone so beautiful would be interested in a five foot four inch guy, who wasn't particularly athletic or particularly good at anything. My mind flipped between joy and doubt.

Friday evening came about and we had a wonderful evening. Alana had originally come from an Eastern European country. Her home town had one of those names that would score a thousand in scrabble.

Very quickly we were going out most weekends, with me staying over at hers many nights of the week. Whatever doubts I had had, were gone for good and I was on cloud nine. I even was comfortable enough to tell her about the money I had.

As winter approached, we were, for the first time ever, invited as a couple to a Halloween fancy dress party. Well one of Alana's clients invited her plus one. I am no fan of dressing up, but Alana was keen as it was a client, so it was important for me to join in.

We spent literally weeks searching for good costumes, but with Alana being over six foot, there was little for her. Plus with me being five foot four, I was having the opposite problem.

With just a week to go to the party, I saw a twinkle in Alana's eye as she had a suggestion. I looked at her and although we hadn't known each other long, I knew I was not going to like the idea.

Alana took a deep breathe and suggested I go as a witch and she go as a vampire. She pressed and pressed, until I agreed, just this once. She took care of everything, including both our costumes. I had no idea what I was going to wear even as we drove into the hotel carpark.

We checked in and the room was nice and clean. Not five star opulence, but also not back street dive.

Alana got me to shower and remove all my body hair with a cream. After the shower she fitted me with long nails and then painted them with black nail varnish. Once she had done my toe nails as well she was going to head for the shower. It was so weird doing all these things. I found it tough doing even basic things with these silly nails on. How on earth women coped, I would never know.

Before Alana got in the shower herself, she said she needed to do something that I would like. She laid me on the bed, then legs astride of me with her facing my groin. She explained, we couldn't have any accidents like me having an erection, so she got to work pumping my cock. It took no time at all for me to cum with her physique and I felt completely drained.

Once Alana had cleaned up around my cock with wipes, she said she needed to do something else to avoid accidents. I didn't know what she was doing. My cock was back to its shrivelled norm, but she was doing something down there. Then I heard a rather loud click.

Alana said "Great, now you wont have any embarrassing lumps in your dress tonight."

Alana got off and headed to the shower. Looking at my groin, before me was a flat chastity cock cage. The only thing sticking out were my balls. I had a fiddle but it was locked in place. On the front was a wee hole and I could tell there was a small pipe that ran inside my willy.

Coming out of the shower, Alana dried off. She checked my nail varnish and then the chastity. Admiring the look of the little cage on my groin area. She reminded me this party was one of her clients and couldn't be messed up.

She start to dress me. I couldn't believe I was letting her do this. A padded black bra and knickers were followed by black tights with a spiders web design on them. They slid up my hairless legs really easily and felt better than I thought they should. Looking at my body, Alana was happy there was no bulge in my groin, just all very flat. Then she set about my makeup. Alana had been a beautician in her home country before moving here, so she was pretty good with the makeup pallet. My eyes were dark and evil, as were my lips. A jet black wig followed and a short sparkly black dress. A pair of high heeled shoes that were black and sparkly were next and they had ankle straps.

I was not enjoying this, but Alana clearly was. She was having so much fun creating something special. So I followed instructions as best I could. A black spider encrusted necklace and matching clip on earrings were fitted and to finish off, Alana gave me a black cape, pointy hat and a broom.

She stood back to see all her hard work and I could see she was pleased. I could hardly walk in the damned shoes, but guessed I would learn through the evening how to.

I looked in the mirror and it was not me, but a young lady dressed as a witch. I was confused whether I liked it or not. Alana was happy though and that was the main thing. She seemed to be ready in just a few minutes. She had a black men's suit on and a big cape. We decided to take a few photos of ourselves before the event.

We headed down to the party and had a great time. We seemed to attach to two single ladies, Donna and Tracy that were on the hunt for men. They didn't have any luck so stayed with us the whole evening. We still had a good time, drinking, dancing, drinking, eating, and possibly more drinking.

Returning to our room that night, everything was buzzing. As soon as the door shut Alana grabbed me and we were on the bed snogging. My dress gave me no protection from her hands and soon she was inside my knickers, playing with the cage. I wanted her to take it off, but she refused. Instead she said I deserved a forfeit as apparently I had agreed to meet up with Donna and Tracy the next day and wander through town. That is when Alana decided on a bit of role play.

As I laid there, not sure of what she meant, she pulled down the tights and knickers and got them off me. I was still unsure, as she unzipped her men's trousers to reveal that she had been wearing a strap on all evening! There before my eyes was a good eight inches of erect dildo.

In my state of shock, Alana turned me over, placed a pillow under my hips and without any second thoughts, I felt the tip at my anus. I had never done anything like this before, so when she pushed the head into me, the pain shot up my body. Inch after inch penetrated me.

Alana got into a rhythm thrusting it into me and then back out, literally fucking my ass. As she did it she told me I was stupid for agreeing to meet my new friends Donna and Tracy tomorrow. The thrusts were planted every time she thought of another name for stupid..."silly", "idiot", "crazy", "fool", she went on for ages pumping deep within me.

Something though was happening to me. Obviously I couldn't have an erection, the strong metal cage made sure of that, but I could feel my balls tingle like I was about to cum. Then I let out my tell tale yelp and I came really hard onto the pillow.

Alana stopped and was transfixed by that event. She said "So you enjoyed that then!" Her face lit up with excitement and she proceeded to impale me again with the strap on. Harder and harder she drove deeper within me. You could tell she was fit as for thirty minutes there was no respite in the pounding of my ass. Eventually I came a second time and that satisfied Alana. We undressed, cleaned up and were asleep in minutes.

The next morning my head was bad, really bad, as was my backside. Alana was up and about busying herself. She called me a silly idiot again for arranging to meet the girls and go to the shops. I couldn't think why it was a problem.

Alana then said "one, your friends Donna and Tracy think you are a lady and two I have got to get home and do some project work ready for Monday. Three, you cannot avoid them as they are part of my clients company, so it would be bad form letting them down. AND four those two can be trouble at times. They can be scheming madams, so you need to be very careful!!!" She went on. "I am popping out and will be back in time for us to go to breakfast." With that Alana rushed out the door.

Thirty minutes later Alana returned with a couple of bags. "Right" she said, "Get in the shower."

I asked to have the chastity cage taken off, but Alana responded vaguely saying she thought she had left the key at home and I still needed to have a forfeit.

After the shower, Alana set about tidying me up. First she got me wearing a pink bra and knicker set. She said it was all the charity shop down the road had. The bra was far too big, cup wise, but it had padding so although the cups were empty, I would look like I had boobs. She then pulled out a floral dress that flared out at the waist, a bit like skater dresses. It had proper shoulders and sleeves rather than just straps. The hem didn't get anywhere near my knees. To finish off she handed me a pair of low heeled shoes and a small shoulder bag.

With ten minutes of makeup time and a new wig, we went down to breakfast. As Alana had said, Donna and Tracy were there waiting for us. To be honest they were good company, but I really felt nervous about the whole thing. But it had been my fault for offering to meet up the next day.

Rather than my usual full english breakfast, I ended up just having some fruit, cereal and juice. I felt it was the ladylike thing to have. Alana on the other hand went for the full fat breakfast. I looked at her plate and wished I had gone for that as well.

After breakfast, Alana headed back to our room to pack our things, put them in the car and drive home. I was to catch a train that evening. Before leaving Alana gave me one last thing she had got in the charity shop, a little jacket.

As Donna, Tracy and I left the hotel to have a wander around town, I could tell it was winter coming. MY bare legs and short dress hardly kept me warm. Looking at what the others were wearing, both had jeans, warm tops and big coats.

We had a good morning pottering around the clothes shops looking at the fashions. Over lunch the girls had an in joke that they didn't want to share with me.

I am not sure what happened, but as the lunch progressed I felt funny, sort of drunk and sort of "out of body" experience.

In this weird feeling I was having, Donna and Tracy took me to a beauticians. In there I was shown to a private room at the back. I was almost asleep as my jacket was removed and dress undone.

When I woke up, the girls were looking at me smiling. They talked about doing me a massive favour, well two massive favours. I didn't have a clue what they were talking about. Then as I tried to stand up, I realised I had far more weight on my chest. It was then that I realised my breasts now filled the cups of the bra.

They had tricked me and I needed to just get out of there. I said I wasn't feeling well so made my apologies and left there sharpish, getting the next train home.

As I sat on the train, I suddenly realised I would have to explain to Alana what had happened, plus would she believe me. How would she react?

Walking in the door at home, Alana looked at me in shock. She could tell straight away my chest had changed.

Alana made me undress to show her my problem. It was only then that I saw how big the problems were. There I was with 36D breasts.

Alana went off on one "I told you to be careful with those girls. And I cannot complain as they are a client." She bent my ear for nearly an hour. "You are meant to be in work Monday, how you going to do that with those things?"

Once she had calmed down, we organised a game plan. It must have been done with saline, so eventually the substance will dissipate around my body. I would have five days off sick, self certificating. Then hopefully the breasts will have reduced enough for me to return to work.

Friday came about, the breasts hadn't reduced at all. Alana carefully measured them and they still were 36D and they wouldn't be much different by Monday. We talked about going to a doctor, but we knew they could do nothing. I suggested going private to have them removed, but Alana was adamant for me not to, as she had had a bad experience with a private doctor.

Eventually we decided that Alana was earning enough and I would resign and stay at home until the boobs reduced down. That left the problem with how I would live. It didn't matter what male clothing I tried, nothing seemed to work. It was then that Alana carefully suggested I stay dressed as a female for the time being, only temporarily. I had managed to for a whole weekend. Why not for a few weeks at most until things got back to normal.

The problem with that decision was that I didn't have any clothes to speak of, so we spent whole weekends and evenings going round the various shops finding me things.

What was concerning though was that I didn't really get to choose the clothes. Alana's reason was that in a few weeks I would be back in men's clothes, so lets have some fun. Her idea of fun though was short dresses and mini skirts. Blouses that were either tight, cropped or see through. Every pair of shoes had big stiletto heels. Alana said it was to help raise me up to her level, but I really found four inch heels difficult to walk in.

There wasn't enough space in the wardrobes, so one evening Alana got all my male clothes, filled black sacks with them, and put them up in the attic. I really had no choice now.

As you can tell things were changing quite a bit. Alana went back to her routine of gym twice a week and I kept the home tidy and made the meals. On Fridays she would have drinks with her work colleagues and come home late quite often. Sex was now me orally pleasuring her or her giving me anal with a strap on. What confused me greatly was that every time, I would cum quite heavily. Did I enjoy it? Mentally, I was is such a strange place of extreme doubt either way.

A number of times I asked Alana again about the cock cage and she said she couldn't remember where the key was or lost her temper. It didn't matter how I asked she ended up getting really annoyed and as she was the one bringing home the salary, I didn't want to upset her too much. So I ended up just accepting the situation.

Slowly but surely I got used to wearing short dresses, even in winter. I built a routine about the shopping trips. I had to walk to the local shops as Alana persuaded me I couldn't afford a car any more. So most days I needed to pop out for something.

As Alana was concerned about my health, I now took pills every day she called vitamins, and she made sure I got enough exercise....mostly in the bedroom. Months passed and still the breasts remained 36D, I was getting really quite sad, as would I ever return to being a male? MY voice was changing and getting softer. The hair got longer and now Alana insisted I go to the local salon for proper styling, colour and cuts. Although Alana assured me I didn't need too much makeup, she trained me in what to wear and when.

As spring came, Alana suggested we go on holiday to her home country. She had been working very hard and needed a break and missed her family. So I agreed and we started to arrange everything. The one sticking point was my passport. How would I get through immigration control sporting these boobs and dressed as a female. Plus how would Alana's family take me? Alana told me not to worry and to concentrate on what I wanted to take.

All too quickly the date of our flight arrived and I was frantic packing everything. As guided by Alana, I was to wear my salmon pink skater mini dress and white lace bra and knicker set. It was then that Alana showed me she had arranged a new passport for me. It seemed they now accept regular photos and she had selected a good photo of me very feminine.

The flight was pretty uneventful, apart from Alana grabbing my bum and boobs a number of times. She seemed to enjoy flicking and twisting my nipples.

Meeting her dad at the airport, he was well over six foot tall, so even with my high heels, I was a good foot shorter. He was a little stern but I wondered if that was just their way in this country as he was pleasant enough.

Alana's family when we arrived came out to meet us. Not only was it still weird wearing female clothes, but to be introduced to the family like it. They didn't have a clue about how I really looked as a man.

Alana had two older brothers, both of which were over six feet tall and Alana's mum was a plump lady in her fifties a little shorter than me. The brothers were all hugs to the point of almost a bit perverted. They literally couldn't take their hands off me. The mum gave me a very little hug and that was it, she grumbled the rest of the time in the local language. I didn't understand a word of it. Thankfully the brothers and dad spoke a little English and they were interested in everything from the UK.

The house from the outside was big but looked a little run down, but going inside it was a palace. In the main family room there was sixty inch TV with all the satellite channels. The kitchen was modern. The only thing missing was a dish washer. In Alana's bedroom there was a large double bed and a whole line of wardrobes.

When there was a lull in the family chatting and greetings, I slipped off to the bedroom and unpacked everything to reduce the creases.

That evening we had a lovely home cooked meal, although I didn't have a clue what it was, but it tasted great. As we sipped a coffee at the kitchen table after the meal, Alana took my hand and rested it on her leg. Straight away I could feel she had something inside her trousers. I ran my hand up to her groin and then down and it kept going. It nearly reached her knee. I looked at her wide eyed. Se smiled and then excused us both from the family and taking my hand I was taken to bed.

Once I had washed and changed into what Alana wanted which was a satin night dress, she suddenly got quite aggressive and got me on the bed, then almost tore off her trousers to reveal a twelve inch strap on. It was massive, not just in length but in width. I just laid there frozen as she proceeded to put a cream on the tip of the large dildo.

She leaned towards me on the bed and positioned the tip close to my anal cavity. I was seriously concerned. Alana lifted my legs up high and then once she felt it was located right, she pressed, gently at first and then with increasing force.