I'm almost too embarrassed to admit it but I almost slept myself to death. When I woke up in the middle of the afternoon and stepped out of bed I was ankle deep in water. I know it had been pouring for days and last night there were flood warnings, but you never expect it to really happen. When I look out of the window all I see is water in the streets, and what's more concerning, there's nobody out there. Suddenly I get in a hurry, I need to get out of here. I run to the garage where the car is wheel deep in water. I throw some dry clothes in the back and find $200 that was left from when I bought my big screen tv, and I got it on sale due to an error in the flyer. Oh, my beautiful new TV, the reason why I woke up so late anyway as I had been watching movies until daylight started. No way was I going to leave that behind and get destroyed. It took me an hour to get it dismounted from the wall. Luckily I still had the box and I managed to get it in the back of the car without getting wet. I was exhausted by now as last week a friend helped me carry it and mount it.
I grabbed some food from the fridge and the pantry and got going. Or so I thought. The power was out and the garage door would not open. Normally you pull a handle to release the chain from the motor or something but since that handle would bang my windshield every time I drove the car in I had it taken off. Now I had to climb on top of the car to mount it back in place while the light coming through the glass panels was already getting less as the evening was approaching. Another twenty minutes later I had the door finally open and I was on my way. Thank goodness I have a Jeep and it's fairly high on its wheels. But where is the road? There were a few mailboxes still standing and I sort of aimed at the middle between them. I had to get to the closest bridge.
You see, the little town where I was living is in a valley between a decent size mountain range. On both sides there is a river, joining together a couple of miles downstream. But to get to higher grounds you have to cross a bridge across one of the two rivers. It normally takes me five minutes to reach the closest, but now it took another half hour. And when I reached the bridge I gasped. The water level almost reached the bottom and looking across I could see the end of the bridge also in water. No road was visible there either. I had to hurry, it was getting darker and I needed to reach dry land before I couldn't see anything anymore. So I carefully crossed the bridge that was shaking in the force of the fast moving water.
At the end I dipped back in the water but there were no homes around so no mailboxes. From memory I know it's fairly straight towards the slope of the mountain and I could see dry land ahead of me and maybe a piece of the road there, so that's what I aimed at. The water got deeper, perhaps I had driven off the road, and within minutes even my Jeep gave up. But it didn't stop moving, I was slowly pulled to the high speed water of the river. At that moment I started realizing for the first time my life was in danger. I have to get out of this car and try to walk through the water to dry land. And for the first time I got lucky. A big tree was down and in the path of my floating car. For a moment the car stopped moving but then it started to slide along the tree and in minutes it would go around it. I managed to get out and with a last glance at my TV I saw my car slide away while I held on to the tree.
Now I can tell you one thing, wading through water waist deep is not easy and even less when the water is moving fast and continually tries to sweep your legs from under you. If it wasn't for the tree I would have drowned right there but now I managed to get closer to dry land, step by step. When I was almost there I thought I run the last few yards but I stepped in a hole and broke my ankle. Or sprained it, I don't know, all I know is the tremendous pain and the water slamming me into the tree. I managed to hold on and dragged myself to the dry land, with just one foot to help me. When I finally reached I was exhausted, soaked and most of my clothes torn. But I knew I had to move on, the rain had started again and the water level would only rise more.
I crawled as good as I could on two hands and one knee, dragging my bad leg along. It didn't go fast but I got away from the water. Everything was muddy and I slipped many times on my face but I slowly moved higher up. And then I saw it, a light, maybe a mile away. There must be a home up there. I had a goal now but it took me more than two hours before I finally reached the light which was indeed connected to a home. My whole body was in pain now, I was bleeding heavily from multiple wounds and there was no way I could reach the doorbell on the front door. I slammed my fist into to door or so I thought, because the knock hardly made a sound. But two minutes later the door slowly opened. With my face lying on the floor I saw heels and part of a skirt and all I managed to say was "Please help" and then everything went black.
When I woke up the first thing I noticed was that I wasn't wet anymore, I wasn't cold anymore and the pain in my body was bearable. I opened my eyes and I saw the most beautiful face I've ever seen in my life. An angel, I thought, but at the same time I knew I hadn't died. "Welcome back" she said. Her voice was like music and her smile made me warm. "Where am I?" I managed to stutter, my throat hoarse. "You're safe" she said, "you managed to knock my door before you passed out. I cleaned you, my god, you probably had ten pounds of mud on you. I took care of your wounds and I stabilized your sprained ankle. You slept for almost 24 hours."
24 hours? And I hadn't really eaten anything before I left my home. No wonder I felt so hungry. But my angel had soup for me, she put an extra pillow in my back and fed me the most delicious soup I've ever had. I gulped the food in, ready immediately for the next spoon. It had chicken, beef, veggies and potatoes in a thick broth. When the plate was done I thanked her for the best meal I'd ever had. She smiled, saying that cooking was her favorite hobby.
I suddenly became very aware of my own helplessness in front of this beauty who had been spoon feeding me. She must have seen the look in my face and said "Don't worry, I'm a nurse at the clinic downtown. I know how to take care of people in need". And with that she handed me a bed pan to do my business, and she moved away to give me some privacy. When I pulled my underwear down I realized it wasn't mine. "What the .. ?" She looked back at my sudden outburst. "Oh, I'm sorry", she said, "I should have mentioned that. Your clothes were all shredded, I couldn't save any of it. And I have no male clothing in my home, so I ehh... I found something that was left by an old girlfriend which fit you. I hope you're okay with it."
"Of course", I replied, "better than nothing, right?" But I wasn't sure about that myself. I did my thing and handed her the pan. "You better get some more rest", she said, "tomorrow we need to talk." She was right, I put my head back down and was gone in sixty seconds.
The next morning I woke up to the smell of coffee and bacon. She didn't feed me this time but she stayed close and helped me to sit comfortably. After breakfast she opened the curtains and when I looked out I saw water below us. Where there should have been two rivers with a town in between there was one big lake with the tops of a few buildings sticking out. I could not see the bridge that I had used a few days ago. "It's still raining upstream", she said, "and with the funnel effect downstream the water level has been rising. There's nothing left of the town or the rest of the valley. There's still no power or cellphone service. I have my own generator and gas tank and the freezer is reasonably full but in another two to three weeks we need help. I haven't seen anybody come down this low on the mountain yet. Unfortunately my car was in service when this all happened so at some point we have to start walking up the road to find help. We have to get your ankle in good shape before then." She pulled the blanket away from my legs and my one leg was zipped up in a leather boot, clearly female. She smiled, "it's a little trick, I put a compress on it and used the boot to stabilize it. As long as we don't take it off you can probably walk on it." I don't know, I looked at the wedged heel that was at least two inch high. "You'll have to wear the other one as well of course." And she started pulling up the second boot on my good leg.
By now I didn't care anymore, I wanted to get out of bed, heels or not. I slowly started putting weight on my feet and I didn't feel any pain. She helped me stand and the slight wobble I had was due to the heels, not because of my ankle. I looked proudly at her and said "Thanks, from the bottom of my heart." She just nodded. I finally got a better look at her, so far all that I had seen her in was an apron. But under that she was wearing a black dress made from what looked like leather. I suddenly became very aware of my own fetish thoughts, how many nights have I been browsing the internet looking at women in leather skirts and dresses. And my beautiful savior, my angel, would have been a perfect fit in that sexy group. And I couldn't hide my excitement in my flimsy panties. "Knock it off sailor", she said jokingly, "I'm only attracted to girls. So if you want to stay here for the next weeks, you better get that thing under control." But in my mind one strong thought remained, she's single and she wants a girl...
Without any further help I walked slowly through the room. I actually think the heels helped in setting my foot in the right angle. But when I looked in a mirror I knew there was another problem. I really needed more clothes. She saw me look and said, "I have nothing male, I tried to put you in some of my scrubs when you were out, but it didn't fit. You can try my apron?" It sounded more like a question than a suggestion and I shook my head, it wouldn't do much to hide my erection. "Well", she said, "I may have something else, if you can move beyond gender issues." And she stepped in a different room and came back with a dress, also in black leather. But I saw immediately why it could work, it didn't have a zipper but laces in the back, so it could fit my bigger frame, and I could step in it without having to take my boots off. My fetish mind screamed to try this, to feel what such a garment would feel like on the inside. And so I nodded and she helped me step into the dress, the leather wrapping around my hips, as she started tying the laces. She made me stretch with my arms high up against the wall and tightened it, more than I expected. I had to gasp but she said I would get used to it. I also realized there was no way I could get out of this without her help, but somehow this made the experience more attractive. Looking down at my crotch area the leather was perfectly hiding my added excitement.
When I looked in the mirror again it was much better, the skirt part was fairly loose from my hips down and with my tight waist I actually had a slight hourglass figure and it was not unattractive. I was very aware of the sexy material on my naked skin and I started feeling myself, rubbing the outside and feeling the material warm up both on the outside as on the inside. It was a very erotic experience. My angel looked at me, clearly satisfied with my looks and my reaction to the leather material. And suddenly it hits me, "I don't even know your name", I blurted out. She laughed out loud, "it's Olivia!" "A beautiful name, very fitting", I replied, "my name is ...". She stopped me before I could tell her my name and said, "listen, you're wearing a dress, high heeled boots and panties. I feel much more comfortable with a woman in the house than a man. Why don't you think of a female name that you like to be called for as long as you're my guest here, no one else in the world has to know." I thought about it for a second, I understood where she was going with this, but it also gave me a chance to experience more of this feeling. I liked it and I wanted more. "Deanna", I blurted out, "like the woman in the Star Trek series, I had a serious crush on her." "Me too", she said and I saw her blushing.
So Deanna it was, at least for the next few weeks. It was suddenly much easier to talk, like a barrier was removed. I told her my story, how I could have died if it wasn't for that tree, and how her porch light was the one thing that kept me going. She hugged me and she cried for me. It was sisterly but it felt good. For the first time I felt the leather on her skin and her warm hands on me and both felt even better than touching myself. And I suddenly realized that perhaps the same thing was true for her, as she kept rubbing my back. In the days that followed there was a lot of touching going on and we both enjoyed it. We cooked together and I learned a lot of things from her, but my food never tasted as good as hers. She taught me how to clean the leather clothing, she had her own dry clean area. She had found another dress in her extensive collection that fit me, as did some of her larger size underwear. My ankle was doing great, even after we took the boot off. But I liked the feeling of having them on so I kept wearing them.
Olivia asked me if I dared to go a bit further, maybe getting rid of some hair, and try a bit of makeup. I could tell the thought excited her and I wondered myself what I would look like. So the next thing I know, she was using a spray on me, all over my body including my face and crotch area. When it started burning I took a shower and when I came out I was as smooth as a baby. Or as a woman... I allowed her to apply some makeup on my now smooth face and she had some sort of a wig that she weaved into my own hair. When I looked in the mirror I could only think that I was pretty, as in girl pretty. She seemed very happy with the result herself and asked for one more favor. I could not refuse her but when she brought back a box containing two very realistic breast forms I knew we were crossing a line. When I looked in her eyes it was simple. She wanted me to cross that line and become a woman that she could love. And by now I was so in love with her that I was okay with becoming that woman. So I simply nodded and an hour later I had to borrow one of her bra's to help me carry the weight of my own breasts. When I wore my dress again no one would ever think I was not a woman.
That night for the first time we shared her bed together. We kept our leather on and I spooned her tight while rubbing her skin through her skirt. She started telling about the few girlfriends she had had. They did not share her fetish for leather, instead they wanted to get naked as quickly as possible. It was fun while it lasted but never for long. I confessed about my own leather fetish and collecting pictures on my phone and masturbating at their beauty. She understood it so well, and also the fact that I'd never had a stable relationship, just because it never felt right. She turned around in my arms and looked me in the eyes and said "Make love to me Deanna. As a woman..." By now you know I've had limited experience and zero in lovemaking as a woman. But the one thing I have wanted to do from the first moment I saw her was sucking her breast. Her top was tight, her breasts in cups, no way to free them, so I put my mouth on the leather where her nipple was causing a small protrusion. She gasped when I sucked hard and then using my tongue to lick around her mound. The taste was intoxicating and I couldn't get enough. I alternated between both breasts, sucking on one while kneading the other in my hand.
She was moaning softly so I knew I was doing something right. I finally moved my tongue down to the skin between her top and skirt and I basically licked up every drop of sweat on her skin. I moved lower even, warming her hips with my hands on the tight fabric. I slowly pulled her skirt up until I could move my head under it, then I moved back up towards my price. I can't tell what smelled more, the leather which taste I had already in my mouth and nose, or her glistening pussy, soaking all her skin around. I took my time to clean it all, while her movements became more urgent for me to go further. Then, with both my hands under her leather covered butt, I moved in, sticking my tongue deep in her eager sex. She cried out now, enjoying the intruder. I started lapping on all the moist, which started almost streaming from her, while I pushed my nose onto her bare clit, pulling her butt into me, grinding us together. My tongue was so deep into her I could hardly breath or even swallow. But she had clearly reached the point of no return as her whole body started shaking and her legs started trashing. I could hear her cry out loud and then in an enormous tense move she came, shooting her fluids straight into my throat, almost causing me to drown for the second time in just a week. But this was bliss, I pulled out slightly so I could swallow her nectar, while rubbing my face in her wet crotch.
Finally she came down from her heights and I started pulling away. I took a deep breath once I freed myself from her skirt as she started pulling my face toward hers. She licked all moist from it and then stuck her tongue in my mouth trying to capture some of her own fluids from my mouth. Our kiss lasted at least five minutes, sharing moist and twisting our tongues, I never wanted it to stop. But when we finally pulled away she had tears in her eyes. She explained in a whisper, "I have chosen to be a lesbian because I strongly believe that only women can provide the intimate gentle touch that I long for. Only to find out that the best sexual experience I've ever felt was given to me by a man." "But I'm a woman now", I replied, "your woman!"
We laid down together, our heartbeats slowly coming down again. I felt extremely satisfied although I had not orgasmed myself. My lover's reaction gave me such a high that I didn't need an orgasm. Maybe this is the secret between female lovers, where giving is just as important as receiving. As a man everything is oriented at cumming quick and hard with not a lot of regards for our partner. But as Deanna my only goal was to provide as much intimacy and love that I could pass on to my lover, her happiness above everything else. I know I crossed a line here, again, realizing I may never return to being a man. And Olivia must have thought a similar thing as she whispered "Thanks Deanna, I will love you forever!"
We must have fallen asleep, or at least I did. But at some point I woke up from a tremendous pleasure. Olivia's head was now under my skirt, bobbing up and down on my member that was growing rapidly. But something inside me was vibrating, quickly driving me over the edge. My balls were on fire from the vibration, warming up fast. But it was her fingers, caressing the inside of my thighs and then slowly pushing the vibration deeper in my anus, giving me a huge jolt. I couldn't even give a warning grunt, I just started cumming, filling her mouth quickly. She swallowed eagerly for a lesbian, but I didn't care. A week of spending time with my lover without any sexual release caused a buildup I've not experienced before. We kissed again and I tasted some of myself which was really not as bad as I thought it would be. And then we finally both fell asleep.
I woke up first, freeing myself from her as she was wrapped around me. I got up quietly, and started making breakfast and coffee. The smell got her out of bed in no time and she sat down at the table, waiting to be served. We ate silently, enjoying my best attempt at breakfast thus far, until finally she spoke. "Thanks for last night. When you sucked my breast through the leather it was perhaps the happiest moment in my life. I have been eaten out many times before and even had my breasts sucked and licked, but always naked, never with my dress on. You made one of my strongest fantasies come true!"
"Believe me", I replied, "it was all my pleasure. And I hope to do this many more times." She nodded her head, smiling from ear to ear. "One thing though", I continued, "what would it take for me to feel the same thing, your fantasy is my fantasy now. I want to experience the real thing, not these fake ones." And I cupped both my breasts, pointing the nipples in her direction.
She was thinking for some time. "There are a few possibilities. Taking female hormones, getting breast implants, or both. Just be aware that once you start on hormones more of your body will change. And that thing down there will not be so easy to please anymore. You can't easily go back. If you don't mind about that then you could even consider castration. Definitely no going back from that. It will stop your male hormones and favor female characteristics. Eventually you can transition into becoming a woman with surgery taking your penis away and forming a vagina.
We have to be very careful here though. This type of sexual changes are typically only used by true women who were born in a male body. They would do anything to match their physical gender to how they identify mentally. If your desire is driven by being with me, wanting to be my lesbian lover, then maybe you're underestimating the enormity of these decisions. If you would lose me would you want to be a man again?"
I started to understand what she was saying. I loved to identify as a woman, be her lover, share her fetish. But a week ago or so I was perfectly happy as a man, although if I'm truly honest looking at pictures of women in leather often made me wonder what it would feel like to be such a beauty. That thought made it real easy to get satisfaction while masturbating. "Maybe it has been in me even before I met you, though I never realized it. One thing is for sure, I don't want to give up on wearing these dresses or making love to you like we have. But I will do anything as long as we can stay together. Start with the breast implants and we'll take it from there."
She smiled, not unhappy with my answer. "Okay, so will be it. But I set the rules. I have a doctor friend who can do the implants. But I want that thing down there under control. I will give you a blowjob every now and then, I will decide when. At all other times you will wear a special prosthetic that will make it look like you have a vagina. You will even have to sit to pee. And who knows, maybe you'll find a guy that you like better than me." She winked when she said the last part, I knew that was never going to happen. I smiled back, our future was bright.
But first we had to deal with reality. Power and cellphone service were restored. The water was slowly receding and it was clear that a big part of the town was wiped out. My home was nowhere to be found, but since I had been renting my loss was not that bad. The insurance paid out some money for my lost possessions. And my car was found miles downstream, dry on the inside and not even a scratch on it. My money, my cellphone and even more important my big screen TV were all there still, unharmed. Olivia was okay with me mounting the TV in her home, our home now. Her car was declared a total loss, under water for more than a week after the garage building had collapsed on it. She got some money for it, but not enough to replace it with a similar model. She did receive payment from the government for rescuing me though and offering me a safe place throughout this ordeal.
The clinic was still standing and one of the first buildings to be cleaned and restored so it could be used again. So Olivia had her job still, unlike me. There was nothing for me to go back to and I'm not sure if I would have gone back, I don't think they would understand my female appearance. I did get a small paycheck from a disaster fund, so at least I didn't fully depend on Olivia. She took our car to work, while I cooked and cleaned. I found a new hobby in fixing or adjusting some of the leather garments. My proudest work was a zipper less wrap dress that I adjusted so it could also fit me. Olivia would wear it with a wide belt but I used a waist cincher on all my outfits, slowly reducing my waist size. I took a course in clothing design and specialized in leather of course. The first dress I designed and sew together sold within an hour after I put it for sale online. I modeled it myself. Soon I was taking orders and requests and I made more money than I ever had as a man.
I had my breast implant surgery and it was worth every penny. Olivia loved to suck on them, with and without leather covering. She had ordered my vaginal prosthetics and I loved wearing them. Our sex life got better and better without me feeling the need to get male relief. She was fine with that and she was very happy how I embraced womanhood. She knew how to make me cum as a woman and to me that felt even more wonderful. By now I started believing that maybe I was always meant to be a woman.