They say once you hit thirty your life will take a downturn. I definitely experienced that, although for a while I didn't see it myself. I was perfectly happy being a bachelor although I did have a few girlfriends along the way.

Drinking with my buddies typically started Friday nights, well into Sunday nights, with all sports an excuse for betting and drinking more. It all ended one Saturday night, after an exciting college game, our favorite team winning, then driving back home from the pub.

I got my first DUI, but that was still better than two of my buddies, who drove together, and got into an accident. One died, the other lost an arm and a leg, literally.

It made me really think about my life, my drinking, my health, and where I was heading. I decided to lay off the alcohol and lose some weight. 230 pounds on a 5 ft 8 frame really didn't look that good.

The judge had pity on me. I explained how sorry I was and my plans to improve my life. She explained that she could easily send me to jail for a couple of months, even though it was my first offense. But she chose an alternative. I was to lose 60 pounds in the next 6 months, and not drink any alcohol.

If I failed, two months of jail time were waiting for me. If I succeeded, my records were cleared. I vowed I was not going to fail. The judge was very clear though, it had to be a sustainable weight loss. Not just take a few pills for a quick loss, no, I had to keep a diary of what I was doing each day. Food, exercise, sleep, everything I did for the next six months, had to be turned over to the court.

It seemed a bit harsh, for a first offense. But it was in line with what I had planned already, to get my life on track again. Maybe a bit more to lose in a shorter time than I had in mind, but this should be possible.

I bought a exercise bike and was on it three times per week for half an hour. And in the first month I lost the ten pounds I needed. Hindsight, it was probably the effect of no longer drinking for a month, but that didn't work in the second month, as I dropped less than one pound. It was probably time to panic.

Going back through my diary it was clear that I still was taking in a lot of calories. Going out for lunch as well as dinner did not help. And I knew I hadn't written down any of the chocolates and candy that some of my colleagues put out in the office, but which I took plenty of.

I needed help. That much was clear. It wouldn't come from my old buddies though, who still kept calling to come out with them again. They felt sorry for me, but they were just happy it wasn't them. And watching games without them wasn't funny either. I didn't drink but I did eat a bowl of potato chips.

The first one to help me was one of the suits at work, unexpectedly. I was joking how he managed to just walk by the bowl with chocolates on someone's desk, and he told me he was wearing a compression shirt under his suit. It limited his intake, he said. And that's what I needed, I realized.

It was a bit tricky to find the right size. Do you buy what you are, or what you want to be? I opted for something in the middle and boy, was it tight. I managed to get it on once but I couldn't breath or move or anything. So I exchanged it for something better fitting. It was still tight, but it did help a bit with pushing my belly in, and I ate less.

How annoying was the bottom of the shirt though. No matter what I did, the material started rolling up, and no longer covering my belly, whereas the rolled up material was tight around me and clearly visible through my clothes. I needed something better.

There wasn't much available that would be the same tight material, but would go between your legs to the back, effectively stopping any of the rolling. Unless you were a woman. They had plenty of leotards to chose from and many in the compression material that I needed. And when I saw one with what they called an open crotch, and a sizing chart that showed it could fit me, I clicked the purchase button.

Two days later it arrived. No frills, thank God, but I hadn't realized it had slight cups and my man breasts fit right in. Other than that it was perfect, it really compressed my belly, and my manhood easily stuck out from the open crotch. There was even a hole so I could sit on the toilet for a number two. It was a set though, together with some shorts in the same material, but that was uncomfortable in the crotch area, as I was not flat like a woman.

So I used my own boxers, and with my regular clothes over it you couldn't see a thing. The effect was almost immediate though. With meals I had only room for small portions, and when I would normally eat a snack at night, I couldn't handle more than a quart of what I normally would take. And in the office I picked up maybe one chocolate but not more.

I bought a second set right away, so I could switch them out and clean them each day. I slept in them as well and essentially during my shower was the only time without compression. That was the only time I could see how my body reacted and the first thing I noticed was how unpleasant it was on my skin. I had little bumps all over and if I scratched them it was a little pocket with a hair in it.

It took me some googling but I realized it had to be a reaction to the stretchy part of the leotard. The solution was to get rid of the hair, not with a razor but with special cream. The relief was immediate, my skin was smooth and stayed smooth, as long as I treated it regularly. The reaction spread though, to my neck, my legs and arms, and even my private areas, and I had to use the cream all over.

Food wise the first few weeks were the hardest, as I felt the urge to eat, and I couldn't handle enough to take the hungry feeling away. But my body was adapting and required less. By the third month I had lost an additional twelve pounds. Still behind on my schedule.

The good thing was that I needed new leotards in a smaller size, and to force myself I skipped one size. It was tight but when I got used to it, the portions I could handle were smaller again. An awkward side effect of the smaller leotard size was that more of my fat was pushed around, making my man boobs and my butt a bit fuller.

So, while losing weight, I didn't feel much healthier. I figured that three times per week on a bike wasn't enough and I decided to jog every day before work. The very first time was not a good experience. The open crotch was smaller in size as well and my scrotum barely fit through it, causing my manhood to be pushed forward. During normal movement I could keep it pushed down, but while jogging, in my roomy boxers, it was swinging like crazy.

The solution turned out fairly simple. The shorts that had come with my first sets were now perfect. The tightness pushed my testicles up into my body, and my manhood could easily bend back now between my legs. I still put my regular shorts on, but my girl shorts were longer and showing under it. I didn't care too much about that, and just for fun I turned my man bun into a girly ponytail.

With the temperatures quite warm I didn't put an extra tshirt on, and when I looked in the mirror before I started I looked a bit female with my smooth legs and arms and a decent chest size. And not to forget my buttocks, with the new shorts all remaining fat was pushed into my rear.

I really enjoyed the jog now despite a few whistles by some guys, and just to spite them, after a few days I even left my man shorts home. That's when I met Jenny.

It was mutual attraction. I jogged behind her for awhile, enjoying how her ass swayed. She had to stop however to tie her shoelaces, and soon was coming up behind me, enjoying apparently my own looks. When I slowed down to take a breather, she stopped with me and we started chatting.

I made it clear right away that I was a guy, and she was pretty amazed. Of course I had to tell her what had happened, and I explained my whole ordeal. We were walking by now, and when I said that although I was losing weight, it didn't feel much healthier. That's when she questioned me about nutritions. She was what I would have called just months ago a health freak. Now however, she was an expert. And clearly someone that I needed.

I was totally eating wrong, missing out on multiple food groups. I needed a drastic change and she offered her help. And just like that I had my new buddy. She promised she'd get me ready before my court appearance. I had to promise to do everything she advised.

She wanted to know where I worked and where I had my lunches and dinners. It wasn't too far from where she lived, so from now on I had to eat at her place and she would teach me how to live healthy.

We'd jog every morning together and she showed me how interval training was more effective than just a standard run. She was a personal trainer, and she made me come to her workout place each night as well. The only problem there was, it was for women only, and that's how I became Paula, at least any time I was with Jenny, which turned out quite a bit this way.

I learned a lot. Nutrition wise, health wise, exercise wise, and woman wise. At first Jenny helped me with some makeup and a bit of padding in the chest area with some silicone inserts. She styled my hair better and then realized I had a some growth still on my chin. She had a friend that could treat it with a laser and before I knew it my whole body was done, so I didn't have to use the hair cream anymore. We did quite some shopping as well, so I had more outfits to wear in her gym, and also while jogging as the weather got colder. Being Paula came easier and easier to me.

I think it was the healthy salads and protein shakes, plus fruit as snacks rather than chips, combined with continuous training each day, but I was truly losing weight now. More importantly, I felt stronger, had more confidence and definitely more energy. Plus I got some friends. Women from the gym with whom we went out afterwards. They had no clue I was really a guy, so I had to bring new outfits to wear, and I learned to walk in heels.

I changed to smaller sizes a few times, and wore the shorts now at all times with the leotard. My work outfits were more difficult as my hips were relatively large compared to my waist, and that's just not how male pants are cut. You can't keep on tightening your belt and eventually I borrowed a pair of jeans from Jenny. We had become lovers by now, sleeping often together, and I was a girl with a dick, her perfect companion.

I really had to remember in the morning to take any leftover makeup from my face, or removing my inserts, actually missing the weight on my chest. And as Paula I had a collection of earrings, but as Mike I could only wear some studs. And with my longer hair it was harder to maintain a man bun.

Things went wrong when I was pulled into a meeting with a client in China. Which was late at night. Jenny and I had just come home from a get-together with some of the girls from the gym, and we were kissing on the sofa, when a video call came in. I thought it was Allison, one of the girls we went out with, but it turned out to be my boss, Mr Addison, from his private number, and with the client on the line as well.

I saw the shock in his face when I answered in full girl mode. Mr Addison recovered quick enough and introduced me as Miss Forrester to the client, and I managed to answer all questions. The next day however they let me go.

It seemed just the natural thing to do to move in with Jenny and I became Paula full time. She convinced me to add a few pounds back to my body, so that I wouldn't need the inserts anymore. As a matter of fact, I didn't need the leotards either anymore, as my body had shaped into a permanent female form by now. She found a very expensive pair of panties, that would hide my manhood completely and give me my own pussy. And soon I became Paula Forrester officially, which allowed me to become a personal trainer myself in the gym.

When my six months were over I stood again in front of the judge, having lost 70 pounds, in a beautiful business suit and high heels. She was actually quite proud of me and cleared my records of any wrongdoing. Three months later she officiated my marriage with Jenny and another year later we named our first daughter after the judge, who changed my life forever.