One Rainy Night

Story Info
A violent attack leads to a new life.
3.6k words
4.39
18.6k
3
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Rikki
Rikki
20 Followers

When I woke up by the side of the road in the pouring rain it took some time for me to remember just what had happened. The moral is never to pick up hitchhikers, even if they look miserable and wet as the pair certainly did. I stopped the car invited them to hop in and the next thing I remember is waking up on some cold, wet ground and my car nowhere in sight.

While it seemed no bones were broken I felt sore all over and my left leg could scarcely take my weight. A quick check revealed my mobile and my wallet were both gone, along with my car. The bastards had even taken my shoes. There was nothing to do, but try to walk to the nearest house.

It was easier said than done as I was out in the countryside, my whole body ached and walking was difficult. I shuffled along for what seemed a long time, but might have only been a few minutes before I saw a light in a window in a large house set far back off the road. By the time I reached the front door I barely had the strength to knock and when it opened I simply fell inside.

'You poor thing! What happened?' I heard a soft voice say and, looking up I saw an attractive face surrounded by brown, shoulder length hair. I think I managed to say something like 'Beaten and robbed' before she began to help me to my feet. I am just twenty and rather slight for my age so she was able to manage to get me up and help me into a warm living room.

Suddenly I couldn't stop shivering. 'You need to get out of those wet clothes while I get you a blanket.' While she was gone I managed to get my shirt and jacket off, but seemed unable to bend down to take off my socks. When she returned I was almost in tears from the effort. She was by my side immediately. 'Don't worry I'll help,' and she knelt down and removed the offending socks. Again I needed help with the trousers. I could get them undone, but she had to pull them down. Then before I could say anything she reached up and removed my underpants, leaving me sitting naked on the sofa. Before I could say a word she retrieved the blanket and gently covered me with it.

It was most likely a delayed reaction to the shock, but suddenly I was shaking and crying as I huddled beneath the blanket. Again she was by my side, putting an arm around me and letting my head rest on her shoulder. The tears soon stopped. 'I'm sorry. It's just that I've never had anything like this happen to me before. You've been so kind and I don't even know your name. Mine's Rob.'

'It's Jane, and it's not a problem.' She looked to be around forty or a bit less and about my height, which is not to say very tall, and quite slender. She must be stronger than she looked because she managed to get me from the doorway to the living room. She was also an attractive woman, dressed in a grey cardigan and black leggings. 'Now tell me what happened.'

When I went through the story, she insisted on calling the police to report the car stolen and then had me contact the bank to cancel my credit cards. The police said they would send someone out the next day to take a statement.

By the time all that was done I was sipping hot chocolate and feeling much better. 'Right, time for bed,' said Jane. 'I've prepared the spare room for you and I'll just go and get something for you to wear.'

A minute later she returned carrying a white, button-through flannel nightgown. When Jane caught me looking at it, she smiled. 'Well you have to wear something and I live here alone, so there are no male clothes in the house and you can't wander around naked.' It was hard to argue with that so I sat up and let her slip my arms through the sleeves. ' Now can you stand while I button you up?' I did and she started fastening the buttons from the neck down. In spite of the circumstances the soft feel of the nightgown had given me an erection. Jane seemed not to notice and as she moved down to my waist she was starting to kneel when it happened. Her woollen-covered wrist happened to touch my cock. The result was an instant orgasm. I had never cum like it in my life. Great gobs of the stuff splattered onto her cardigan. It seemed like it would never stop. 'Goodness!' was Jane's only comment, but she never stepped back or looked disgusted.

I was mortified. 'Oh God! I'm so sorry. I don't know what happened.' It was all too much and I collapsed onto the sofa in tears. She knelt in front of me and took my hands in hers. 'It's okay. I've never had that effect on a man before,' she smiled as she looked down at the cum on her cardigan.

'You've been so kind and this is how I repay you. You must think I'm some kind of pervert.'

'I said it was okay and I meant it. Nothing a good wash of this cardie won't fix. Now let's get you to bed.'

Getting up the stairs was not easy, but with Jane's help I got there. In the spare room was a large bed, turned down and waiting. The last thing I remember was Jane saying good night and telling me she would just be in the next room if I needed anything.

I slept for hours and when I finally awoke I felt much better, although every bone in my body still ached. The nightie felt soft against my skin and when Jane opened the door I was able to greet her with a smile. After helping me to the bathroom, and then back to bed she brought in a tray with breakfast. While I ate she sat on the edge of the bed and began to discuss what we were going to do.

I told her I had no family or friends who needed to know and that I was something of a loner, off on a month's leave from work that I intended to spend driving around and camping. 'Well, that's not a problem,' she said. 'You can stay here until you feel better. We can discuss details later. Now have a rest.'

An hour later the police had been and taken my statement. I managed to get the nightie off and slide it under the covers before they came in, but it went back on the instant they left. I was surprised how much I enjoyed the feel of it and how relaxed I felt.

After lunch Jane suggested that I might like to get up and see how it went. 'Okay, well let's get you dressed then.'

'In what? I don't have any clothes.'

'Oh, I'm sure I can find you something of mine to wear. We're the same size.'

'But I can't wear women's clothes.' I could feel my face going red with embarrassment.

'Rob, you're in one of my nighties now. You're already wearing women's clothes. Now no arguments! What do you want -- slacks and a cardigan or a dress?

She had me. I couldn't think of a single thing to say. When I was a boy I had been quite interested in women's clothes and had even tried on some of my mother's things when I was alone in the house, parading around her bedroom with my cock tenting out the front of her cotton panties. I really enjoyed it, but was too scared of being caught to do much. Now someone was offering to dress me up.

I settled for the slacks and cardigan. I would have liked to try a dress, but that might have been going too far too quickly. Jane left the room and returned in a couple of minutes with my clothes. -- a pair of plain white cotton panties, black stretch slacks and round-neck, waist-length brown cardigan.

Jane pulled back the covers, 'Now stand up.' I did as I was told and she unbuttoned the nightie, leaving me standing naked. Almost before I could think she had me step into the panties and pulled them up. The slacks were a little more difficult, but when they were on they were skin tight, with a bulge in the groin that left little to the imagination. Jane also had to help me with the buttons on the cardigan. She was right about us being the same size and her clothes were a perfect fit.

I could move a little more easily, but Jane still put an arm around me and helped me down the stairs. In spite of the situation I found myself getting excited and the bulge in the groin was getting bigger and more uncomfortable. Sitting opposite her on the sofa I folded my hands in my lap to cover my growing erection.

It didn't work. 'You seem to like wearing my clothes,' Jane said with a smile.

I didn't quite know what to say. 'I, er, they feel nice, and soft,' I managed to get out.

'Did you ever try on women's clothes before?'

'Yeah, when I was a kid I did it a few times.'

'Did you enjoy it,' her eyes were sparkling. I nodded. 'Why did you stop?'

'I was scared of being caught. There was only my mom and I knew she wouldn't understand. Since she passed away a couple of years ago I've never had another opportunity.'

'And now you have.'

'What do you mean? Surely this is only until you go and get me something to wear and I go back home.' I wasn't sure what she was getting at.

'Well, not necessarily. You said you have a month's leave. You are welcome to spend it here, with me, and I'd be quite happy for you to wear my clothes the whole time.'

I was amazed at the offer. 'Are you serious? But you hardly know me. I could be a really horrible person.'

She laughed. 'I don't think so. I think you're a very gentle, lonely person and I'm a bit lonely myself. We could help each other and have a good time. What do you think?'

'I don't know what to say. I've never had an offer like this before.'

Jane laughed. 'No, I didn't think so. Anyway, we can play around and you can try different things on. You have quite long hair and with a bit of styling and some make up you would make a very attractive girl. Are you in?'

All I could do was nod, stammer out my thanks and ask if she was sure about this. She was definite, 'Yes, I'm looking forward to it. Now that swelling in your slacks looks painful. Perhaps you should take care of it.'

'What do you mean?'

'Well, you could take it out and play with it and I could watch.'

'Are you sure? I mean last night.'

'Yes, last night was interesting, but maybe I might get a better look today. It's been a long time since I had a chance to watch a man cum. So come on, stand up, come over here and pull down your slacks and panties and let's get started.'

I did as I was told and when my panties were lowered my dick sprang to immediate attention. It wasn't of a great size, but it looked okay. Jane leaned forward in her chair. 'Now start playing with it.' I slowly moved my hand up and down the shaft and as I did I noticed the rapt, intent look as she followed my every move. Then she said, 'Stop! I'm going to give you some encouragement.' As she spoke she removed her top and unclipped her bra, letting her breasts hang free. They looked magnificent.

I soon felt myself building towards a climax. 'Ah! Jane I think I'm cumming and if I do I'm going to make a mess.'

She smiled. 'Don't worry. You can cum on these,' and she lifted her breasts towards me. It was all I needed as I sent jet after jet onto her naked tits. Then we just looked at each other and smiled. While I pulled up my panties and slacks, Jane wiped my cum off her tits and stomach.

When I was sitting down again, she said, 'Well that went well. I actually came while I was watching you. '

'Would you like to cum again?'

'Why Roberta whatever do you have in mind?' she said using the feminine version of my name.

'Well you just take down those slacks and panties and sit back and let me take care of you.' Jane did as I asked and then I knelt down in front of her and put my head between her legs. As my tongue found her slit she began to moan and push my head into her groin. She came almost instantly and kept on and on as one orgasm after another shook her body.

Eventually she calmed down, a contented smile on her face. 'I have never felt like that in my whole life. You were amazing.'

I laughed, 'Glad to be of service. At least I know one way to pay you back for all the kindness you've shown me.' Jane laughed with me, telling me she was sure she had the best end of the deal.

The rest of the day we really got to know each other and that night we snuggled up together in Jane's bed, both wearing our nighties. As strange as it sounds I could not believe how relaxed I was and how much I was enjoying myself. And especially how much I was enjoying wearing Jane's clothes. They seemed so soft and sexy, but they were nothing compared to the lady herself. She was so kind and loving, helping me make a dream come true.

The next morning while lying in each other's arms Jane asked me what I would like to wear today. I decided to really take the plunge. 'Could I wear a dress please?'

'Of course you can my darling. I've got just the thing -- and I think we might do your hair and add some make up as well. Make you a real girl. Well, nearly real,' she said taking hold of my cock and giving it a squeeze. It was a while before we were ready to get out of bed.

After we had enjoyed a long morning shower Jane took me back to the bedroom. I sat on the bed, wrapped in a towel while she busied herself gathering clothes. After dressing in what I had come to understand as her favourite leggings and cardigan, only today she had chosen not to wear a bra. When I pointed this out she said she wanted a bit of freedom.

'Right,' she said, 'now let's get you sorted. I've got a lovely button-through floral dress for you. Now stand up and we'll put your panties on.' I did as I was told and the white cotton panties were slipped on. 'Now for the bra.'

'Hang on a minute. Why do I need a bra? I don't have breasts.'

'Sorry sweetie, but without breasts and a bra the dress won't hang properly.'

'Well how do I get breasts?'

'Easy, I made them for you,' she said, producing what looked like two breast-shaped bean bags. These are the same size as mine and they will fit into your bra perfectly. Anyway, if you are going to look like a girl you need boobs.'

With that said, she slipped my arms through the straps of the white bra and fastened it. Then she slipped the falsies into the cups and adjusted them to give the look of real breasts. 'How do they feel?' she asked.

'Strange,' I answered. 'A bit heavy, but I'm sure I'll get used to them.'

Jane laughed. 'Sounds like you're really getting into this.'

'I guess so. When I was younger it was always something I wanted to do, but the chances were so limited and I was just too scared. My mother had a completely different attitude to you. She was very old-fashioned and would never have understood. If she'd known I would simply have been a pervert and she would have probably thrown me out.'

'Goodness, your childhood sounds a bit grim.'

'It was. She wasn't cruel, but I had no friends and it was pretty lonely.'

She put her arms around me, 'You poor thing. Anyway that's over. Now stand up and we'll get your dress on.' She put the sleeveless dress on me and buttoned it up. 'There, that looks great. It fits you perfectly and the bra makes it hang just right.' She gave me some flat-heeled shoes and then led me to the bathroom where she went to work on my hair and make up.

Finally I was allowed to look into the mirror. I couldn't believe it. Looking back at me was an attractive young girl. I would have found it hard to recognise myself. 'There, what do you think?'

'Amazing. I really look like a girl.'

She gave me a white cardigan in case I got cold in the sleeveless dress. We spent the rest of the day with Jane teaching he how to walk and sit and even talk like a lady. I found controlling my voice the most difficult, but by the end of the day it was improving. Jane gave her verdict, 'You've done well. You couldn't pass just yet, but you're getting better and within a week or two no one will be able to spot you and when that happens we can go out.' Jane noticed my startled look. 'Trust me, when the time comes you'll be fine.'

She looked at me. 'Now will you do something for me?'

'Anything you want. I don't think I could ever repay you for all you've done for me. What is it?'

'Well you had your fantasy of dressing as a woman and some people would think that is pretty kinky. Well I have a fantasy of making love to a woman wearing a dress, just like the one you have on, and being screwed by her cock.' She giggled, 'Now you'll think I'm really weird.'

I looked into her eyes. 'Jane I'm not only grateful for all you've done for me, I'm in love with you. There is nothing you can ask that I would not try to do. One person's weird is another one's fun. Come on.' I reached out and took her hand and led her up the stairs to the bedroom. 'Now what do you want me to do?'

She thought for a moment, 'I would like to be on top so can you lay on the bed for me.' I slipped my shoes off and did as she asked. While I was doing this she took off her own shoes and slid down her leggings and panties so she was naked from the waist down. Then she climbed onto the bed and sat astride me. She unbuttoned my dress from the waist down and asked me to lift my bottom so she could remove my panties. 'I see there's no problem with getting you interested,' she said as she looked at my erection.

Without another word she grasped the base of my cock and lowered herself onto it. I swear she came instantly as she started moving up and down on my shaft. At the same time she began to squeeze her woollen-covered breasts. 'Unbutton your cardie,' I said, 'so I can see your tits.' In between gasps she managed to get the task done, giving me a view of her breasts framed by the sides of her cardigan hanging open. 'Now squeeze them.' Again she complied, grabbing her tits and holding on for all she was worth. She must have cum a few more times before I eventually began to build towards my own climax. 'Jane, I'm going to cum.'

'Yes! Yes! Give it to me! Give it to me!'

I did and I think it was the most amazing orgasm I had ever had. It just seemed to go on and on. Eventually it ended and Jane collapsed on top of me. It was some time before we could speak. 'Thank you,' she said. ' You know that you're not the only one in love. This is going to be a fun month.'

And so it was. By the end of it there were some major decisions made. I wasn't going back home. I'd be staying with Jane, or at least Roberta would be and there would be no need to change back. Rob made one appearance to go and quit his job and then clean out his flat -- not that there was much to take -- and then he vanished.

Jane had her own computer website design business. She was very successful and made lots of money. Roberta became her personal live-in assistant. The locals thought we were a couple of lesbians, but the truth would have shocked them even more. But it's our life and we will live it the way we want. The police never caught the guys who robbed and bashed me, but that no longer matters, in fact I think I should really thank them because what they did that rainy night led me to Jane and a new life as Roberta.

Rikki
Rikki
20 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
fireguy365fireguy365over 11 years ago
One problem

The story was a pleasure to read but I would have changed one thing... the panties. Cotton are okay but if they had been soft nylon panties it would have made it much better for me. Regardless, a nice story that had a happy ending.

PepperpuppyPepperpuppyalmost 13 years ago
I liked it

A nice little story. It may have been able to be catagorised as a transexual crossdresser story, but it was enjoyable either way.

I rate it 3 fingers, and my partner...... well he didn't rate it, he screwed me silly after reading it! ...... THANK YOU!

Share this Story

Similar Stories

A Harmless Favor A young wife assists her young husband to become a sissy.in Transgender & Crossdressers
My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
Transformations Joey goes to bed as a boy, wakes up as a girl.in Transgender & Crossdressers
Mr. Wallace and Me Pt. 01-05 My fat, ugly boss makes me dress like a girl.in Transgender & Crossdressers
Curiosity Paying the consequences of being caught dressed.in NonConsent/Reluctance
More Stories