Lolita Revisited
A Short Story
By Maryanne Peters

I never thought that this kind of thing happened for real, but there are strange people out there.

I suppose my mother was strange too. She always had a hankering to see me dressed as a girl. She told me that she did it when I was a baby, dressing me in pink just because she liked to hear people say: “What a pretty little girl”. Any chance to put me in a dress for Halloween or fancy dress she always said: “Go as a princess. Let me get you the outfit.”

She always encouraged me to wear my hair long, and she would like to brush it when I was doing my homework. Sometimes she would lift it up at the back and twist it around – just playing with it as if it was girl’s hair.

You might think that being treated like this would turn me into some kind of sissy, but I never was like that. I wasn’t a jock either, but I found my place with a good bunch of guys, mainly Paul and Rocco, and we did fun things together. Everybody understood that my Mom was a bit wacky, especially when I turned up to a Halloween thing in the princess get-up.

“Don’t tell me. This was your Mom’s idea”. Same thing every time. I just shrugged my shoulders and checked my lipstick.

My mother loved to take photos of me dressed as a girl. She would say: “Strike a pose. Look like a princess longing for her prince.” Embarrassing stuff like that. It was her thing. It seemed harmless. How could I refuse?

Well I did refuse, eventually. It was Halloween 2014. She had the princess thing all laid out. I just said no. I was going as a zombie and that was all there was to it. I have to say that she lost it, and she1 started talking about all the photos she had of me dressed up as a girl and loving it. Did I really want all those images out there? My own mother … blackmailing me!

“Look Mom, everyone knows. All my friends have seen me in girl’s clothes. And they all know that it is because of you and some perverted need to pretend I am your daughter for one night a year. But I am 14 now Mom, so this bullshit is over.”

She was mad at me. Hell, she was just mad, in both senses of the word as it turns out.

I knew that my Mom was a failure in business. I guess she was a failure in relationships too. She only had me, and as it turns out, she was happy to trade me to get out of debt. As far as she was concerned that fight meant that I was no longer a child and she no longer owed me a thing. Rather, she figured that I owed her.

I didn’t know it, but she had been posting pictures of me dressed as a girl on the internet, or some of those dark places where people are interested in such stuff. She ended up in deep correspondence with a guy called Victor.

I didn’t learn details of the deal until much later, but Victor was looking for a sissy boy to have what he called: “A lasting relationship, or maybe even marriage”. It must have been that he couldn’t find one – a sissy I mean. To be honest I had no idea that guys wanting other guys dressed as girls was even a thing. Why would I?

Mom had financial problems, - I knew that. But I had no idea how serious they had become. She had borrowed from the wrong people. She was desperate to pay it back. She said that she even thought about selling a kidney. She would never sell me, she told me, but she did.

This guy Victor said that he would clear her debts, if I could be his. What does that mean? It sounds to me like being sold for cash.

Mom said it wasn’t. She would be going with me to his home. I was underage. We would just live with him. I would live dressed as a girl and have my own room. Mom would have her room next to mine. Victor would have his own room. He just craved the joy of having a young sissy living in his house. He could not lay a finger on me until I was of age, and even after I was, he could only go further with my consent.

It was weird. Plus I would be moving to a strange town and away from my friends. She just told me that I could stay in touch through social media.

It was just that Mom was in trouble. Of course I did not want her hurt or killed. Of course I wanted her to be free of the burden of debt that made her suffer so much. We had our differences, but she was still my Mom. I agreed, but I said that if it got any more weird, I was out of there.

I never found out what price had been agreed upon to promote this deal. I tried not to think of it as me being sold and bought, but it seemed like that sometimes, that is exactly what it was. She had not really got out of debt, just swapped lenders, but she was free of her past and he had agreed to forgive her over time. She said that we would both be free within a few years.

Then one day a moving truck arrived, and plane tickets and a taxi to the airport. I said goodbye to my friends and told them that I would stay in touch and when I was 18 or earlier if I could, we would be back together.

Victor lived in a huge house, and it was very tidy. I mean he was one of those people who liked everything organized. He liked to control people, and by that I mean us. He even planned our diets. He had me taking vitamins – or that is what he said they were. He decided on the clothes that he would like me and Mom to wear around the house, and when we went out.

He had Mom dress as a maid in a grey uniform. She did not have to do any maid stuff. He had a housekeeper who did that and who cooked our meals. He just wanted Mom to know what her place was. She was a servant. He had paid off her debts and now she owed him, so both Mom and I needed to do things the way he wanted.

What he wanted for me was that I wear ridiculous frilly girly outfits around the house. These are the kind of dresses that a 5 year old girl might wear to a wedding, but in my size and with room for tits in the front. I just laughed about it, and went along, but soon I started to notice that the space in the front left for breasts was filling up.

Mom knew what it was, but I didn’t. What guy knows about female hormones? Why would I?

He wanted my hair to be even longer and Mom agreed. She had me washing my hair with some miracle growth promoting stuff. She loved playing with it, and arranging it, and I guess that after a while I learned to like that too.

Victor only wanted to have me around. He said that I could call him “Daddy”, so I did. He liked to see me in the morning, and he liked me talking about girly things. Then he went to work. He liked me to dress up for him and sometimes do a little dance or sing him a song in the girly voice that I had been practising. I could see that it made him happy.

It seemed like that was all there was to it. I had no idea about the hidden cameras in my room and my private bathroom. I guess people like Victor need to see me naked some time. What is the sense in having a boy dressed as a girl if you cannot check that he really is a boy under all the clothes.

I say that because there were times when I had doubts, especially as the titties grew and my pecker shrunk.

One morning I danced into the conservatory to have breakfast with Daddy and I had put rags in my hair the night before to get girly ringlets

“I want to go to high school like everybody else,” I said. “I don’t mind going as a girl. I just miss school.”

He looked a bit worried. He said something about girls growing up too fast.

I said: “I though that you liked the grown up me!” I pushed out my chest so he could see what had happened to me. It looked like his head was about to explode. I pleaded with him as a little girl does: “Pleeease Daddy, Pleeease.”

Victor was a creepy guy, and I did not know just how creepy, but when it comes down to it, he was not evil. He had kept his promise and not laid a hand on me, but sometimes I think eyes feel worse on you body than hands. He agreed that I could go to school at the local high school, using the name Josephine or Josie, and with his surname.

He also agreed that I could have a phone, so that he could know where I was. That gave me the chance to reopen social media and get back in touch with Paul and Rocco so far away.

I felt that I needed to stay grounded with those guys, because now I had another life in another city – a life in another gender. It was agreed that I did not need to wear silly frilly clothes to school so long as I changed when I got home, but I had to wear dresses or super-feminine blouse and sandal if I was wearing pants. I found a style which worked for me. It did not make me look weird, but it marked me as an individual proud to be feminine. There were other girls like that at school, so I bonded with them. But underneath I was still me and that was the guy who messaged Paul and Rocco almost daily. I could take images of my new school and new friends, but never myself.

“The one on the right is super hot – are you going with her?” She was just a friend, but the thing that worried me was that she was hot, and I had barely noticed. Maybe because she was not nearly as pretty as I was.

Time went by, as they say. At school I had become popular with the girls, and I had guys hitting on me, but I told them that my father was very strict so there would be no dating. That was getting hard for me, as I wanted to do what everybody else was doing, but I knew messing with a guy could be dangerous. Was I attracted to boys? I was in a way. When I felt like that, I would pull out my phone and send a male mail, and that would put me straight.

And time affected my body with the drugs I was being fed. There was no denying what it was by then. I researched it. The effects are reversable – at least in most cases. The blockers had made my nuts and pecker tiny, and the female hormones had made my breasts as big as most girls at school. But this could all be put right once Victor was done with us. One day we could be out of this – Mom and me, or maybe just me. It seemed that Victor was becoming dependent on Mom for little things.

But I was the object of his lust. He started talking to me about my 16th birthday and marriage. That was the legal age in the state we lived in, despite the age of consent for sex being 17. But there was another problem – no marriage between males in the state, and consent for surgery was 18.

“I always want you to be a little girl,” he said. “I want you to be my little girl, with a little tinkle between your legs. 18 seems so old.”

Like I said, Victor was a creepy guy. Marriage was just a way to get into my panties, and even if he expected to be able to get there when I was 17, it seemed that by 18 he would be done with me, and maybe move onto somebody else.

I knew that I had to get out, but I needed time. I told him that I would not consider any relationship until I had reached the age of consent. He offered to move to a neighboring state where you only had to be 16. I could see how keen he was. I asked whether I could have a 16th birthday party, but I said that my 17th birthday would just be for him and me to share alone.

I think that he almost fainted, or maybe that was him coming in his pants. I had found a way to push his buttons by then. Although I was not small, I would sit on his knee if I wanted something, and play with his beard. I was disgusted of course, but I could hide that. I could be his little girl, if that was what he wanted to call me, but on his lap, I could feel that erection growing. It was sickening. He was a sick man.

He agreed to the party and said that we could have it at our house. He said that I had to dress as he liked, so I told all the girls at school that the theme was “Lolita” and we all needed to dress like that, with the boys in suits.

You will know the term maybe, but perhaps not the book. It is the story of a young girl, I guess like me but a bit younger, and her stepfather Humbert Humbert, who is obsessed by girls of certain age – he calls them “nymphets”. I read the book at school so Victor would not know. Some people call it a classic, but it was in the restricted area. It described Victor completely. In the story he runs away with his nymphet but she is stolen away from him, and at the end of the story he is on trial for the murder of her abductor.

I had an idea that I would use the plot of the book to win my freedom.

There was a boy at school who was interested in me. In fact many were, but Jake in particular seemed to be seriously fixated on me. I wanted to be taken away by Jake. I figured that if it came down to a fight that Jake would get the better of Victor.

I invited Jake to the party. There were a few other guys who were friendly with some of my girlfriends, but I invited Jake for myself. But I spent most of the party beside Victor. I would cast him longing looks but when he approached, I would wave him away. I engineered a couple of incidents where I was pulling away from Victor, and I was staring towards him with a pleading look. It was all me, but it did not look that way to him. I knew that it had gone well.

As he left, I took him aside and said: “I am sorry, but the situation here is complicated. It is just like the book, the book ‘Lolita’. I am Victor’s Lolita.”

The party ended, and he left looking confused.

He was not up to reading the book, but he was able to find the movie. The more recent one. He told me about it when he saw me at school. We went to the music room for privacy.

“I have to get you away from him,” Jake said.

“I’m afraid Jake,” I said. “Hold me.”

I have to say that I felt that I was just playing him up to that moment, but when he put his arms around me it felt so good. My mother was great at hugging. Victor loved to hug me, but any time he did I just felt uncomfortable. But Jake’s embrace just felt good. I felt all floppy in his arms – like, passive.

I felt that I needed to send a male mail. I sent a message to Paul and Rocco, but I may have been a bit flushed or something. It was not quite as male as it should be. It said: “Things are shit here at the moment. I just need to escape but I feel helpless.” The second sentence read girly, like me. But it was gone. So what do you do?

The message came back: “Hold on. We will be there Saturday”.

It just made matters worse. I was living in the same house as a paedophile, I was leading on a boy from school who thought I was a girl, and my two pals were coming to town expecting to see me as a guy. I looked at myself in the mirror in the hall. I just looked so wonderfully pretty. There was no way that I was cutting my hair, and my titties looked huge.

I sent a message back: “Please don’t come. It will make things more complicated”.

I got no reply.

The following day Jake wanted to meet me privately again. He said that it would be difficult to run away, but that he had relatives leaving town that week and he was checking on their house, so that was a place I could stay for a bit. I started to wonder if maybe that was an answer, just in case my pals turned up. I could just disappear for a while.

Jake wanted to kiss me. I let him. It was actually quite nice. I thought that it would be yuck to share saliva with another guy, but it was Okay. I could do it. He loved it. He was starting to love me. It was another complication I did not need but he had a hideaway.

The rest of the week seemed to go slowly. I sent more messages to Paul and Rocco saying things like: “Everything is cool now. No worries over here. We can catch up later, but just not now”. But still no replies.

Jake showed me the house after his relatives had gone on Thursday. He wanted for us to use the bed right then and there. I said no. We could kiss and cuddle, but I was brought up properly, and I was not yet 17, although he was.

I needed any excuse to keep the contents of my panties well away from him. He was bigger than me, which is what I wanted. He was bigger than Victor. But if he found out that he had had been licking a guy’s tonsils he could easily break me in half. I started to wonder if I had made a huge mistake in tempting him the way I had. I just felt that if it came down to a fight I needed a big guy in my corner.

I sort of avoided Jake at school on Friday. And then, when school was coming out, I saw Paul and Rocco standing by the gate. They were watching everybody leave school. They were looking for me. They were looking for the guy they knew. Everybody was walking past them. I stalled for a minute, but I would have to go out this way.

The exit crowd was thinning out. I just needed to get past. I pulled the band out of my ponytail to let a screen of glossy hair pass down the side of my face as I walked through the gate. I was only just through when My phone buzzed and I looked at the screen. It read: “We are outside your school. Where RU?”

I was holding it in my hand, right out in front of me, and the screen was bright. And then there was somebody standing behind me. Two people – one on each shoulder.

“That’s not your phone.” I heard Rocco’s voice.

“Where is he?” said Paul.

What could I do? It was like that slow motion car crash that they talk about. I turned around and pushed my hair away from my face.

“Well fuck me,” one said it. They may both have. They just stared at me open mouthed.

“I can explain.” My girly voice came out. It seemed like the only voice I had now.

“Don’t tell me. This was your Mom’s idea”. It was Paul, saying what he used to say.

It was then that I started to cry. I am pretty sure it was the hormones they had been giving me. Sometimes I could feel them having an effect on me like that – emotionally. My two old friends just looked at me at first, as guys do when confronted with a girl in distress. Then I felt Rocco’s arm around me, and Paul’s hand on my shoulder. It felt good.

“Let’s find somewhere to sit down and talk,” Paul said.

They walked either side of me and that made me realize just how different I was. They were two guys escorting a girl to the diner. I was that girl.

“It has all got very complicated,” I explained, when we were seated. “My mother has basically sold me to that old creep Victor, and he wants to marry me, I think. He wants me to be his nymphet, but with a pecker.”

“What’s a nymphet?” said Rocco.

“It’s for sex. He wants to ass-fuck me.”

“You have to get away from this place,” said Paul.

“I want to. Jake wants to help. But I think he wants to fuck me too.”

“Who’s Jake?”

“He’s my boyfriend.”

“You have a boyfriend?!”

“It is not like that. Look at me, guys; I need protection.” I was starting to get upset. I was looking for understanding. I was the one in difficulties. “Jake looks after me. He calls me Josie. He doesn’t ask much. He likes to play with my titties.”

“You have titties?” Rocco exclaimed. “Can I see them?”

“I am not going to pull off my sweater in here,” I whispered. “But here they are. You can touch them if you like.” It was a V neck and I pulled it down so they could see them nestled in my bra. They both reached out and I wished that I had never invited them.

I saw the looks on their faces. It was just like the way Jake looks at my chest when I wear something revealing. I know what is going on. It is a boy thing, and it was not the way I was anymore. I liked to look at my breasts in the mirror, but not that way. After overcoming the horror of the changes in my body, I had learned to love my breasts.

And when somebody admires something about you that is beautiful, it makes you feel good. Surely that applies to boys as well as girls? I like the way Jake looks at my breasts. But Paul and Rocco were my friends. And when they both took their eyes of my chest and looked me in the face, I could see that things had changed.

But I guess I had changed too. What I should have said is – ‘hey, I am still me’, but instead I gave a little smile and tossed my hair back. Who does that? A girl – a girl does that.

Paul said – “We need to get you away from this place, Josie. We can stay overnight. You need to pack up your stuff”.

He did not call me Joe. That sealed it for me. The two guys sitting across from me were no longer friends, they were boyfriends, or boyfriends in waiting. The only difference between them and Jake were that I had not kissed them yet, and they knew that I was not really a girl. But it seemed that did not matter.

If only this was a Nabakov novel, but it was so much more complicated.

There was Mom to think about too. It was not like I could just up and leave. And where would I go? Back to my old home town? I could be a boy again there, but somehow it seemed that I did not want to go back there. It was like I had moved on. But moved on to where? Or who?

I asked the guys to stay in town while I packed some stuff, but the idea of leaving was still a problem for me, I just could not explain why.

And then that night everything changed. Victor had a stroke.

Victor was watching Mom brush my hair as he liked to, sitting at the table so we could not see his naked cock in his hand, when suddenly he just groaned and his eyes rolled back in his head. We both went to him, but I would have happily watched him die. Mom, however seemed genuinely concerned.

Victor treated Mom like his maid, but I never quite understood what they had going on. I was the object of his desires, but he seemed to feel comfortable just having Mom around. I guess she felt the same way. She called 911 and the paramedics came around and took him away, and Mom went with him.

It was just me in the house. I thought about calling Jake, but instead I sent a message to Paul and Rocco and asked them to come around

“I can’t go with you guys,” I said. “I need to see where things are going with Victor. If he dies, then my problems may be over.”

“Would you go back to being Joe, then?” asked Rocco. He seemed to be dismayed at the thought.

That really put me on a spot. I mean the obvious answer was yes, if Victor was dead, or reduced to a vegetable. But I did not want to give that answer.

“Maybe,” I said, only because that is not an answer at all.

“You really look good as a girl,” said Paul. “I mean you don’t look like a guy at all, even without trying. And those titties are just beautiful.”

I suppose I realized that Paul was not looking at them with lust, but more with envy.

“Being a girl does have its pluses,” I said to him.

Rocco was looking at Paul, and then at me, and shaking his head. It was a WTF moment, I guess. He looked confused.

“What hormones are you taking?” asked Paul, ignoring Rocco’s stare. What guy knows about female hormones? I didn’t. I just took them because that is what Mom and Victor wanted.

“Do you want me to get you some? Would you like me to call you Pauline, or Paulette?”

Rocco was having real trouble. One of his old pals was now a girl, and the other was heading in that direction. When you think about it, he handled it pretty well.

I think it was because I was there to help him through it. I mean, Rocco and I go back further than me and Jake, as I had to explain to him. But Jake was a neat guy, and so I introduced him to Paulette.

Victor came home and was cared for by my mother. He hardly ever looked at me again. The stroke must have affected his sex drive. After the stroke he only had eyes for Mom, which was fair because she was caring for him no questions asked.

He had ongoing health problems as a result of the stroke, but he recovered enough to propose marriage to my Mom and to marry her in his wheelchair. When he died he left plenty and enabled me to have my surgery, and to help Paulette with hers.

Just like in the book, the creep dies at the end, but somehow I can’t feel too bitter about Victor. It turns out that for whatever reason, my mother was quite attached to the guy, and all said and done I have a lot to be grateful to him for.

The End

© Maryanne Peters 2020

My original caption based short on Fictionmania was called “Sold Off and Wed” but it was a much less likely story than this one – the old “family sells the son to become transwife of the local weirdo” tale. But I had so many review calls to make it longer, including Nikky, Jennifer and RH Music. It started to get so similar to the classic novel that I had to include it, rename the story and take it in a different direction.