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.
