Howie Returns to PennsylvaniaChapter 3
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How I Became Me free porn video
Being brought up in a household with an absent father, I spent many hours playing with my two elder sisters, Macy and July. I don’t recall ever playing with toy guns, I never played soldiers and I never had an Action Man. But I do remember playing with my sisters’s dolls. We spent many hours making clothes for the dolls and dressing them up and playing with them. And that was my c***dhood.
As we got older my Macy and July grew out of playing with dolls and started playing dress up with our mother’s clothes. When they were all dressed up and practising with their make-up, I wanted to carry on playing with them so I started playing with Mum’s wardrobe too. I didn’t realise it at the time, but when I look back at the family photo album, Mum must have encouraged me to explore my dressing up. I’d forgotten that when I was still at middle school she had let my hair grow beyond shoulder length. With a little help from my sisters and a little make-up I could have passed quite easily as a girl.
And that was how we spent our c***dhood. At school a was teased a little about my hair length, but it didn’t bother me. Since I spent my home life in the company of women, most of my school friends were girls. Once the boys started getting interested in girls, they were keen to make a friend of me so they could get to know the girls better. I had loads of fun playing matchmaker and I loved the school discos we had each term. I’d spend the night dancing with all of the girls whilst the other boys would be desperate to be invited. When the slow tracks came on I’d have plenty of offers from my friends to smooch with them. My only regret was I couldn’t wear a pretty dress to the disco like my girl friends did.
There were so many days I would run home from school, rip of my school uniform and pull one of my July’s pretty dresses over my head. Once in a dress I was more relaxed and felt so comfortable. Mum would get back from work and shrug.
“I see Anna’s home again. If you’re going to spend so much time dressed in your sister’s clothes, perhaps we should get you some of your own.”
“Oh could I Mum. I’d do anything to have my own things.”
Mum was finally accepting that her baby boy had gone past dressing up being a game with his elder sisters. The desire to dress like a little girl was what made him happy.
“Lets do a deal. Every time you help out around the house I’ll treat you to something for your new wardrobe. If you keep your room tidy you’ll get some underwear or a pair of tights or stockings. If you do the hoovering you’ll get a top or skirt. If you do the laundry, a dress. And if you prepare a meal and do all of the washing up, some shoes.”
“Oh Mum, you’re the best!”
I jumped up and gave Mum a big hug and kissed her on the cheek.
“I promise to do my best.”
And that was how I ended up having two wardrobes. The small one contained the boy clothes I had to wear at school and outside the house and the larger contained my dresses, my skirts, my tops and my ever expanding collection of shoes and boots. My socks and pants were moved to the bottom drawer whilst the top drawers were full of pretty knickers and tights. When Mum brought home my first training bra I was a little embarrassed but couldn’t wait to try it on. With a little tissue padding it gave me a hint of cleavage to go beneath a figure hugging dress.
As a special birthday treat Mum took me shopping. I was now 16 and was nearly as tall as Mum.
“Anna, take of that dress and put on a pair of jeans, we’re going to buy you your first pair of heels.”
“Oh, thank you Mum. But how can we do that. Wouldn’t it look strange with a boy trying on women’s shoes?”
“Don’t worry. Our feet our nearly the same size now. I’ll try them on. If they fit me, they should be fine for you.”
At the shopping centre, Mum let me choose the shoes I wanted and then asked the sales assistant to bring her a pair to try on. As I watched Mum slide the shoes on to her feet, I couldn’t wait to get them home and practise walking around the house in them.
“How do they look son?”
“Very sexy Mum.”
“Good,” turning to the assistant, “We’ll take them.”
And I walked out of the shop carrying my first pair of heels.
“Of course when a lady is wearing high heels, to be properly elegant, she shouldn’t be wearing tights, she should be in stockings.”
“But I don’t have any stockings Mum.”
By the time we got home I was carrying my new shoes in one bag and another bag with a lacy, black suspender belt and a silk pink one. We’d also bought three pairs of stockings – a pair of seamed barely black stockings, a pair of 7 denier nude stockings and a pair of white fishnets.
I was so keen to try out my new shoes, I pulled my jeans off and without removing my socks I tried them on. I loved the way they stretched my calf muscles and my butt checks felt firmer than usual.
“Oh Anna! Where are your knickers? I can’t believe you went out shopping with me dressed like that.”
Mum had always been relaxed with nudity around the house. When I was dressed as Anna she had no qualms about me walking in to the bathroom whilst she was in the shower, but it had been a whilst since she had seen how puberty was affecting my body.
“Sorry Mum. So what do you think? Do you like the effect this shoes have on me?”
“Well they certainly make the best of your legs … and it looks like they’ve got you a little excited!”
I looked down and realised what she meant. My cock was poking straight out quite proudly.
“Go upstairs and sort yourself out. We can’t have you walking around like that and put on a pair of knickers. Why don’t you replace those socks with those new stockings? If you need a hand adjusting them, just shout down.”
So I went upstairs, sorted out my erection and tried my first pair of stockings to go with the new shoes.
When July and Macy got home they complimented me on my more mature look. They gave me a few tips on walking in heels and took great pleasure on watching my wobbling attempts to walk demurely.
“You need some posture lessons. Perhaps we can teach you a few dance moves?”
July and Macy had been taking dancing lessons and were looking at doing it professionally when they left school. They had started with ballet lessons when we were younger. I had always been jealous when they pulled on their exercise tights and leotards. Since then they’d progressed to modern dance and were in a dance school which had provided plenty of dancers for cruise ships and West End musicals. Their teacher had plenty of contacts and she had put their names forward to various booking friends.
“If you think it’d help.”
For years I had been desperate to join them when they danced around the house and when I had the house to myself, I would turn the music up and repeat what I had seen July and Macy doing, so when they started showing me a few steps, they were amazed how quickly I picked them up. After about half an hour they had taught me a simple routine which we showed Mum.
“Wow, the three of you look fantastic dancing together. If you keep practising, you could do that for money.”
I know that a mother only ever sees the good in their c***dren, but it did put the idea in my head that perhaps we should keep at it. That night over dinner I asked July and Macy if they really thought I was a good dancer.
“Anna, if you came to our dance classes, you’d fit in with the best of them.”
I had a long think over night and the next morning over breakfast I asked Mum if I could join the dance class. Mum put her spoon down and looked me in the eye.
“Anna, do you realise what that would mean? If you want to do it as Anna, you’ll have to present her to the outside world. We love having Anna around the house, but if people find out that things aren’t what they seem, you could be putting yourself in danger. If you really want to do it, I’ll back you all the way. Have a think about it and if you’re sure it’s what you want, we’ll make it happen.”
All day at school, I couldn’t stop thinking about what Mum had said.
“Mum, I really want to do it. I’m more relaxed when I’m wearing a dress and I think I could pass as a young girl.”
“Okay Anna. Well, let’s do it straight away. The girls have a class tonight, lets get dig out some of their old togs and you can join them.”
We went up to July’s room and found an old, pink leotard and matching tights. I put on my training bra which produced just a hint of boobs to show beneath the tight leotard. I looked at myself in the mirror and loved what I saw. Looking back at me was a young girl getting ready for her first dance lesson.
“Come on Anna. Don’t want to be late for your first class do you?”
July and Macy took me to the class with them and said they’d look after me. I was nervous going out for the first time as Anna, but I think I got away with it. Macy told her teacher that I was a cousin from out of town and wanted to try a few lessons. The teacher said that would be fine and made sure that I was between my two sisters and I should follow what they do.
I loved it!
We warmed up with a few stretching exercises and then went straight in to a routine that the class had been working on. I started slowly but by the end of the class I was just about keeping up with Macy and July and was significantly better than some of the other girls. At the end of the class the teacher came up to us.
“Are you sure you’ve not danced before Anna? With a little practise, you’ll soon be as good as your cousins.”
I thanked her and beamed all of the way home. I knew I’d be going back to the class next week.
And I did.
I kept going back to the dance school. Even when July and Macy got dance jobs in London I kept going to the classes. I was soon to be leaving school and I knew what I wanted to do. So far I only went out as Anna when I went to the dance class. Other than my family, no one knew that I wasn’t a girl. But I knew I wanted to become a professional dancer. I’d been to London and seen July and Macy in their show. They were part of the chorus but it all seemed so exotic. Their costumes were amazing, their make-up was stunning and the show was out of this world. I called them to ask if they thought they could get me a job.
“Leave it with me. One of the girls is leaving and there might be a small spot for you. It’s only a small part and it doesn’t take much dancing. Do you remember the scene when we have those fabulous fairy wings as backing dancers for the lead and the girl runs on stage and shakes her butt at him?”
“I do. Reminded me of that time Jarvis did the same to MJ at the Brits.”
“That’s the one. Well, the girl who runs on stage is leaving. It’s not much, but it could be our first step on stardom!”
I just laughed and asked if they could get my an audition. Two weeks later I made my first stage performance.
I was so nervous before hand. I had no dance moves to remember, but running on stage with my sister’s was the most exciting thing I’d ever done in my young life.
After the show July and Macy were so proud of me. It wasn’t a big part, but I had loved it.
The three of us stayed with the show until the run came to its end. We had moved in to a flat together. I still spent most of my days as a young man and only brought Anna out at show time. I had to arrive at the theatre as Anna or the other girls in the changing room would have been shocked. To this day I don’t think they realised that the girl at the next mirror was a boy. The sights I saw in the changing room sometimes made it difficult to keep my manhood hidden. Seeing the dancers doing their quick changes was quite a sight. As I only had a small part in the show, I got in the habit of helping the girls in to and out of their outfits. The number of times I’ve man-handled their breasts in to a tight outfit or helped them out of a skimpy dress was beyond imagination. And some of the girls were very relaxed about their bodies. Every boy should spend a couple of weeks assisting behind the scenes with a chorus troupe!
If we wanted to stay in London we knew we’d have to earn some money. Despite the glamour, we weren’t earn much money so we had little in the way of savings. Macy and July were confident that they could find another job with their dancing and they contacts they’d made, but I hadn’t been dancing so I knew I’d have to use my initiative if I wanted to contribute to the rent.
Within days of looking Macy had found a job as a show girl at a cabaret. It wasn’t what she wanted to do and didn’t use much of her dancing skills but with her beauty and charisma, she was a natural. Her outfit consisted of a skimpy white playsuit which was just a step up from a bunny girl. But it showed off her long, dancer’s legs and she got plenty of tips to help with the rent.
July had managed to find herself a job as a hostess at an old fashioned dance hall. Her classic dancing skills were to the fore. She spent her afternoons and evenings teaching and dancing with mature men who wanted a reminder of their younger days when they would go to the local dance and take their young lady around the dance floor. July loved it. She got to wear some lovely cocktail dresses, paid for by her employer, she got to dance for a few hours a day and got to meet plenty of gentlemen who were so pleased to be dancing with such a pretty young lady. Within a few weeks she was the most popular girl at the dance hall. The men would be queuing up to get a dance with her and the tips almost paid our rent on their own. Perhaps not the job she thought she’d be doing when she left for London, but there were worse jobs out there. In fact there were far worse jobs out there.
With my two sisters out of the flat most nights, I had plenty of time to find a way to earn some money. I’m afraid that I made some bad decisions. I found myself spending most evenings surfing the internet. I had no money to spend so this was the only pleasure I could afford. As a young man I spent quite a bit of time exploring porn sites. I signed up for XHamster and started chatting with a few friends. The pointed me in the direction of a few sites where girls would put on a live show and get paid a few tokens for their efforts. I noticed that the site also had a selection of transsexuals and crossdressers who put on a show. Some of them were very good and convincing, some less so.
I spent a few evenings watching them and thought to myself,
“Anna, you can do better than some of these. They seem to earn enough money to live off of it. Why don’t you give it a go?”
So I did.
I got myself dressed up in a little black dress, borrowed some of Macy’s false nails and a pair of July’s hoop ear rings. I sorted out my hair and put on some sultry, come hither make-up. I thought I looked pretty good, but what would the outside world think?
I needed one more thing – a couple of glasses of wine inside me. All of those years dressing up and appearing on stage as a girl, but other than getting to the theatre, I’d rarely interacted with anyone as Anna and here I was about to become a whore – that’s what you call someone who sells sex for money isn’t it?
I started slowly. I lined the camera up and sat there drinking a glass of red wine trying my best to look like someone you might buy a drink. Someone you might want to ravage.
When my first visitor arrived I wasn’t sure what to do. I greeted him and he started complimenting me how sexy I looked. All I could do was thank him. He said that he couldn’t believe I was a guy, would I like to prove it. I had noticed that the number of viewers was going up. The wine was taking over so I proved that I was really a guy by lifting up the dress and pulling aside my panties. Within a few minutes there was little doubt that underneath the dress I was not a girl. The number of viewers was going up quite quickly and the wine started to take effect.
My viewer numbers were shooting up as I opened my legs wider and started to enjoy myself. The comments were getting more and more lewd and were getting me horny. I started the evening pretending to be a lady, now here I was reading comments from guys telling me they’d like to have their lips around my girly cock. Comments telling me I was a whore who should be sucking their cocks. Would I like to be fucked by their huge shafts?
I didn’t have time to respond to the messages. After reading each message I got more excited. Before I knew what was happening I was stroking my cock and knew I was going to cum. I laid back and stroked quicker and harder. Soon my cum was shooting out of my balls and spraying all over my little black dress. Those viewers had turned me in to a sissy slut and I loved it!
When I got my breath back and realised what I had just done, I noticed that I had over five hundred viewers and they’d paid me over a hundred pounds. I was now officially a sissy whore and I knew I’d be putting on another show, very soon. Was this the perfect job? I got to dress up in sexy clothes. I worked from home. I got to cum whilst men did their best to turn me on. And I got paid for it!
When Macy and July returned home that night I told them the good news that I had a job. Of course I didn’t tell them that I was dressing up for strangers on-line, showing them my cock whilst they talked dirty to me. I told them I was working at one of the local take-away restaurants. They knew it wasn’t what I wanted to do but were proud that I’d taken any job I could find to help out.
As they thought I was on minimum wage, I had to hide the extra money I was now making on a nightly basis. I spent some of the money on buying sexier and sluttier clothes which I considered to be an investment – the sluttiest the dressed, the more money I made.
One day I was wondering what I could do with the money and I had a life changing brain wave. If I invested some of the money on me I could make even more money, so I looked on the internet and found myself a plastic surgeon who would work on enhancing by breasts. On almost every show I would get a comment about how much better I would look with real breasts in my bras. So, why not? Who was I harming?
A few weeks later I went to the surgeon and returned with a cleavage to be proud of. I had told July and Macy I was going away for a few days to visit a friend from school who was studying in Exeter. It was a white lie as that was where the surgeon was and I did see an old school friend. As I walked through the door in a low cut dress, my sisters were both speechless.
“Well do you like them?”
“What the fuck have you done?”
“I treated myself to a little present. Nice aren’t they?”
I popped them out of the top of my dress for them to get a good look at. They both stood up and squeezed a boob each.
“Not so hard. They’re still a little tender.”
“Well Anna, I guess you’ll not be going back to being our baby brother now. I’m so glad you’ve finally made the transition. We wondered if you’d ever become what you should always have been. I guess you’ll make even more money on-line now!”
I was shocked.
“How did you know?”
“Well you never smelt of greasy oil when we got home, we’d noticed all of the new dresses in your wardrobe and we’d seen how much more confident you’ve become. Besides, you left yourself logged on to the PC and we saw your profile. Your shows are pretty hot! If you ever want to put on a show with a couple of real girls to play with …”
That night my visitors got a very special show. Not only to they have the big revealing of my new breasts they got to see two sexy girls playing with them. A brunette sucking my right breast and a blonde on my left. Each had a hand wrapped around my sissy cock and took pleasure and getting me as hard as possible. I just laid back and let them have their pleasure. When I told them I couldn’t hold back any longer they left my erect nipples covered with their lipstick and fought over my cock. They both wanted to receive my first load of cum with my new boobs. Macy took the first load and July the second. They swapped it between each other and then moved up my body and kissed me, dripping my own cum in to my mouth. I’d done many things on-line, but had never tasted my own cum. I knew that I’d be adding it to my show on a regular basis.
The tips I received that night were more than for any other show. I didn’t tell my tippers that these two sexy goddesses were my sisters, but I promised that they would be regular visitors from now on. With the money from that one show I treated my sister’s to a good night out and bought myself a new dress to show off my new assets.
As my life took a path I’d never expected I found myself getting further and further in to the amateur porn industry. I had set up my own website and was selling self-made videos. I was making enough money for the three of us to move to a bigger flat. Macy had found herself a job back in the theatre and July soon followed her. Everything was going well for all of us. Some of the favourite photo shoots were when I dressed up in rubber. I loved my skimpy blue rubber dress, but the pink sleeveless catsuit should off my new boobs to perfection. It appears in a few of my shoots and a coupl eof videos that July helped me to shoot. Perhaps you’ve seen some of them or perhaps even stroked your cock whilst looking at them?
We were never happier than when one or both of them joined me on-line for a show. Having one of your sisters helping you to cum in front of a bunch of randy strangers is exciting beyond belief. Having her stroke your cock whilst suckling your boobs and then wrap her lips around your cock and taking all you have to offer is what families are for. And then when you taste your cum on her lips, well, if you get the chance, give it a try!
We’d been doing shows together for quite a while when one day July said,
“So Anna, when are you going to fuck me?”
I was a little stunned.
“Well, erm … I didn’t think you’d let your little brother screw you.”
“ Despite what you do for a living, I know that you’re still a virgin. Kind of ironic isn’t it? All of those strangers who have seen you cum so often and yet you’ve still never had your girly cock inside a pussy.”
I didn’t know what to say.
“Would you like me to fuck you July? Wouldn’t it seem strange?”
“Being fucked by your brother is strange. But watching your brother grow up to be a pretty dancing girl and then have breasts bigger than you is also pretty strange. Knowing that he’s got a bigger fan club on the internet than some pop stars is pretty strange. But watching his videos every night whilst wanking myself off with my pink vibator, wishing he’d take the hint and join me in bed to fuck me, that’s reality. Laying in bed knowing that you’re on the other side of the wall and wondering if you’ll ever offer to make love to your sister, it’s been tough s*s.”
That night we put on the best show so far. July got me harder than ever as we both knew how this was going to play out. As she lowered herself on to my erection all I could hear was the tip jar getting fuller and fuller … but I didn’t care. Here I was on my back looking over my breasts looking up at my pretty sister as she bounced up and down on my cock. Her cunt muscles were working my cock so much I couldn’t hold back any longer. As I was about to cum I looked over her shoulder and saw Macy standing naked behind her. She was squeexing her nipples with one hand whilst shoving a rather large vibrator in and out of her leaking pussy. I beckoned her over as I wanted to feel her lips on my bullet like nipples.
As I felt her lips around my nipple and July started to grind herself against me I shut my eyes and enjoyed the full body stimulation it was receiving. My eyes opened as another pair of lips started sucking on my other nipple. I had assumed July was leaning forward and suckling me as she rode my cock.
“MUM!”
And my cock emptied itself deep inside July’s convulsing pussy.
As we got older my Macy and July grew out of playing with dolls and started playing dress up with our mother’s clothes. When they were all dressed up and practising with their make-up, I wanted to carry on playing with them so I started playing with Mum’s wardrobe too. I didn’t realise it at the time, but when I look back at the family photo album, Mum must have encouraged me to explore my dressing up. I’d forgotten that when I was still at middle school she had let my hair grow beyond shoulder length. With a little help from my sisters and a little make-up I could have passed quite easily as a girl.
And that was how we spent our c***dhood. At school a was teased a little about my hair length, but it didn’t bother me. Since I spent my home life in the company of women, most of my school friends were girls. Once the boys started getting interested in girls, they were keen to make a friend of me so they could get to know the girls better. I had loads of fun playing matchmaker and I loved the school discos we had each term. I’d spend the night dancing with all of the girls whilst the other boys would be desperate to be invited. When the slow tracks came on I’d have plenty of offers from my friends to smooch with them. My only regret was I couldn’t wear a pretty dress to the disco like my girl friends did.
There were so many days I would run home from school, rip of my school uniform and pull one of my July’s pretty dresses over my head. Once in a dress I was more relaxed and felt so comfortable. Mum would get back from work and shrug.
“I see Anna’s home again. If you’re going to spend so much time dressed in your sister’s clothes, perhaps we should get you some of your own.”
“Oh could I Mum. I’d do anything to have my own things.”
Mum was finally accepting that her baby boy had gone past dressing up being a game with his elder sisters. The desire to dress like a little girl was what made him happy.
“Lets do a deal. Every time you help out around the house I’ll treat you to something for your new wardrobe. If you keep your room tidy you’ll get some underwear or a pair of tights or stockings. If you do the hoovering you’ll get a top or skirt. If you do the laundry, a dress. And if you prepare a meal and do all of the washing up, some shoes.”
“Oh Mum, you’re the best!”
I jumped up and gave Mum a big hug and kissed her on the cheek.
“I promise to do my best.”
And that was how I ended up having two wardrobes. The small one contained the boy clothes I had to wear at school and outside the house and the larger contained my dresses, my skirts, my tops and my ever expanding collection of shoes and boots. My socks and pants were moved to the bottom drawer whilst the top drawers were full of pretty knickers and tights. When Mum brought home my first training bra I was a little embarrassed but couldn’t wait to try it on. With a little tissue padding it gave me a hint of cleavage to go beneath a figure hugging dress.
As a special birthday treat Mum took me shopping. I was now 16 and was nearly as tall as Mum.
“Anna, take of that dress and put on a pair of jeans, we’re going to buy you your first pair of heels.”
“Oh, thank you Mum. But how can we do that. Wouldn’t it look strange with a boy trying on women’s shoes?”
“Don’t worry. Our feet our nearly the same size now. I’ll try them on. If they fit me, they should be fine for you.”
At the shopping centre, Mum let me choose the shoes I wanted and then asked the sales assistant to bring her a pair to try on. As I watched Mum slide the shoes on to her feet, I couldn’t wait to get them home and practise walking around the house in them.
“How do they look son?”
“Very sexy Mum.”
“Good,” turning to the assistant, “We’ll take them.”
And I walked out of the shop carrying my first pair of heels.
“Of course when a lady is wearing high heels, to be properly elegant, she shouldn’t be wearing tights, she should be in stockings.”
“But I don’t have any stockings Mum.”
By the time we got home I was carrying my new shoes in one bag and another bag with a lacy, black suspender belt and a silk pink one. We’d also bought three pairs of stockings – a pair of seamed barely black stockings, a pair of 7 denier nude stockings and a pair of white fishnets.
I was so keen to try out my new shoes, I pulled my jeans off and without removing my socks I tried them on. I loved the way they stretched my calf muscles and my butt checks felt firmer than usual.
“Oh Anna! Where are your knickers? I can’t believe you went out shopping with me dressed like that.”
Mum had always been relaxed with nudity around the house. When I was dressed as Anna she had no qualms about me walking in to the bathroom whilst she was in the shower, but it had been a whilst since she had seen how puberty was affecting my body.
“Sorry Mum. So what do you think? Do you like the effect this shoes have on me?”
“Well they certainly make the best of your legs … and it looks like they’ve got you a little excited!”
I looked down and realised what she meant. My cock was poking straight out quite proudly.
“Go upstairs and sort yourself out. We can’t have you walking around like that and put on a pair of knickers. Why don’t you replace those socks with those new stockings? If you need a hand adjusting them, just shout down.”
So I went upstairs, sorted out my erection and tried my first pair of stockings to go with the new shoes.
When July and Macy got home they complimented me on my more mature look. They gave me a few tips on walking in heels and took great pleasure on watching my wobbling attempts to walk demurely.
“You need some posture lessons. Perhaps we can teach you a few dance moves?”
July and Macy had been taking dancing lessons and were looking at doing it professionally when they left school. They had started with ballet lessons when we were younger. I had always been jealous when they pulled on their exercise tights and leotards. Since then they’d progressed to modern dance and were in a dance school which had provided plenty of dancers for cruise ships and West End musicals. Their teacher had plenty of contacts and she had put their names forward to various booking friends.
“If you think it’d help.”
For years I had been desperate to join them when they danced around the house and when I had the house to myself, I would turn the music up and repeat what I had seen July and Macy doing, so when they started showing me a few steps, they were amazed how quickly I picked them up. After about half an hour they had taught me a simple routine which we showed Mum.
“Wow, the three of you look fantastic dancing together. If you keep practising, you could do that for money.”
I know that a mother only ever sees the good in their c***dren, but it did put the idea in my head that perhaps we should keep at it. That night over dinner I asked July and Macy if they really thought I was a good dancer.
“Anna, if you came to our dance classes, you’d fit in with the best of them.”
I had a long think over night and the next morning over breakfast I asked Mum if I could join the dance class. Mum put her spoon down and looked me in the eye.
“Anna, do you realise what that would mean? If you want to do it as Anna, you’ll have to present her to the outside world. We love having Anna around the house, but if people find out that things aren’t what they seem, you could be putting yourself in danger. If you really want to do it, I’ll back you all the way. Have a think about it and if you’re sure it’s what you want, we’ll make it happen.”
All day at school, I couldn’t stop thinking about what Mum had said.
“Mum, I really want to do it. I’m more relaxed when I’m wearing a dress and I think I could pass as a young girl.”
“Okay Anna. Well, let’s do it straight away. The girls have a class tonight, lets get dig out some of their old togs and you can join them.”
We went up to July’s room and found an old, pink leotard and matching tights. I put on my training bra which produced just a hint of boobs to show beneath the tight leotard. I looked at myself in the mirror and loved what I saw. Looking back at me was a young girl getting ready for her first dance lesson.
“Come on Anna. Don’t want to be late for your first class do you?”
July and Macy took me to the class with them and said they’d look after me. I was nervous going out for the first time as Anna, but I think I got away with it. Macy told her teacher that I was a cousin from out of town and wanted to try a few lessons. The teacher said that would be fine and made sure that I was between my two sisters and I should follow what they do.
I loved it!
We warmed up with a few stretching exercises and then went straight in to a routine that the class had been working on. I started slowly but by the end of the class I was just about keeping up with Macy and July and was significantly better than some of the other girls. At the end of the class the teacher came up to us.
“Are you sure you’ve not danced before Anna? With a little practise, you’ll soon be as good as your cousins.”
I thanked her and beamed all of the way home. I knew I’d be going back to the class next week.
And I did.
I kept going back to the dance school. Even when July and Macy got dance jobs in London I kept going to the classes. I was soon to be leaving school and I knew what I wanted to do. So far I only went out as Anna when I went to the dance class. Other than my family, no one knew that I wasn’t a girl. But I knew I wanted to become a professional dancer. I’d been to London and seen July and Macy in their show. They were part of the chorus but it all seemed so exotic. Their costumes were amazing, their make-up was stunning and the show was out of this world. I called them to ask if they thought they could get me a job.
“Leave it with me. One of the girls is leaving and there might be a small spot for you. It’s only a small part and it doesn’t take much dancing. Do you remember the scene when we have those fabulous fairy wings as backing dancers for the lead and the girl runs on stage and shakes her butt at him?”
“I do. Reminded me of that time Jarvis did the same to MJ at the Brits.”
“That’s the one. Well, the girl who runs on stage is leaving. It’s not much, but it could be our first step on stardom!”
I just laughed and asked if they could get my an audition. Two weeks later I made my first stage performance.
I was so nervous before hand. I had no dance moves to remember, but running on stage with my sister’s was the most exciting thing I’d ever done in my young life.
After the show July and Macy were so proud of me. It wasn’t a big part, but I had loved it.
The three of us stayed with the show until the run came to its end. We had moved in to a flat together. I still spent most of my days as a young man and only brought Anna out at show time. I had to arrive at the theatre as Anna or the other girls in the changing room would have been shocked. To this day I don’t think they realised that the girl at the next mirror was a boy. The sights I saw in the changing room sometimes made it difficult to keep my manhood hidden. Seeing the dancers doing their quick changes was quite a sight. As I only had a small part in the show, I got in the habit of helping the girls in to and out of their outfits. The number of times I’ve man-handled their breasts in to a tight outfit or helped them out of a skimpy dress was beyond imagination. And some of the girls were very relaxed about their bodies. Every boy should spend a couple of weeks assisting behind the scenes with a chorus troupe!
If we wanted to stay in London we knew we’d have to earn some money. Despite the glamour, we weren’t earn much money so we had little in the way of savings. Macy and July were confident that they could find another job with their dancing and they contacts they’d made, but I hadn’t been dancing so I knew I’d have to use my initiative if I wanted to contribute to the rent.
Within days of looking Macy had found a job as a show girl at a cabaret. It wasn’t what she wanted to do and didn’t use much of her dancing skills but with her beauty and charisma, she was a natural. Her outfit consisted of a skimpy white playsuit which was just a step up from a bunny girl. But it showed off her long, dancer’s legs and she got plenty of tips to help with the rent.
July had managed to find herself a job as a hostess at an old fashioned dance hall. Her classic dancing skills were to the fore. She spent her afternoons and evenings teaching and dancing with mature men who wanted a reminder of their younger days when they would go to the local dance and take their young lady around the dance floor. July loved it. She got to wear some lovely cocktail dresses, paid for by her employer, she got to dance for a few hours a day and got to meet plenty of gentlemen who were so pleased to be dancing with such a pretty young lady. Within a few weeks she was the most popular girl at the dance hall. The men would be queuing up to get a dance with her and the tips almost paid our rent on their own. Perhaps not the job she thought she’d be doing when she left for London, but there were worse jobs out there. In fact there were far worse jobs out there.
With my two sisters out of the flat most nights, I had plenty of time to find a way to earn some money. I’m afraid that I made some bad decisions. I found myself spending most evenings surfing the internet. I had no money to spend so this was the only pleasure I could afford. As a young man I spent quite a bit of time exploring porn sites. I signed up for XHamster and started chatting with a few friends. The pointed me in the direction of a few sites where girls would put on a live show and get paid a few tokens for their efforts. I noticed that the site also had a selection of transsexuals and crossdressers who put on a show. Some of them were very good and convincing, some less so.
I spent a few evenings watching them and thought to myself,
“Anna, you can do better than some of these. They seem to earn enough money to live off of it. Why don’t you give it a go?”
So I did.
I got myself dressed up in a little black dress, borrowed some of Macy’s false nails and a pair of July’s hoop ear rings. I sorted out my hair and put on some sultry, come hither make-up. I thought I looked pretty good, but what would the outside world think?
I needed one more thing – a couple of glasses of wine inside me. All of those years dressing up and appearing on stage as a girl, but other than getting to the theatre, I’d rarely interacted with anyone as Anna and here I was about to become a whore – that’s what you call someone who sells sex for money isn’t it?
I started slowly. I lined the camera up and sat there drinking a glass of red wine trying my best to look like someone you might buy a drink. Someone you might want to ravage.
When my first visitor arrived I wasn’t sure what to do. I greeted him and he started complimenting me how sexy I looked. All I could do was thank him. He said that he couldn’t believe I was a guy, would I like to prove it. I had noticed that the number of viewers was going up. The wine was taking over so I proved that I was really a guy by lifting up the dress and pulling aside my panties. Within a few minutes there was little doubt that underneath the dress I was not a girl. The number of viewers was going up quite quickly and the wine started to take effect.
My viewer numbers were shooting up as I opened my legs wider and started to enjoy myself. The comments were getting more and more lewd and were getting me horny. I started the evening pretending to be a lady, now here I was reading comments from guys telling me they’d like to have their lips around my girly cock. Comments telling me I was a whore who should be sucking their cocks. Would I like to be fucked by their huge shafts?
I didn’t have time to respond to the messages. After reading each message I got more excited. Before I knew what was happening I was stroking my cock and knew I was going to cum. I laid back and stroked quicker and harder. Soon my cum was shooting out of my balls and spraying all over my little black dress. Those viewers had turned me in to a sissy slut and I loved it!
When I got my breath back and realised what I had just done, I noticed that I had over five hundred viewers and they’d paid me over a hundred pounds. I was now officially a sissy whore and I knew I’d be putting on another show, very soon. Was this the perfect job? I got to dress up in sexy clothes. I worked from home. I got to cum whilst men did their best to turn me on. And I got paid for it!
When Macy and July returned home that night I told them the good news that I had a job. Of course I didn’t tell them that I was dressing up for strangers on-line, showing them my cock whilst they talked dirty to me. I told them I was working at one of the local take-away restaurants. They knew it wasn’t what I wanted to do but were proud that I’d taken any job I could find to help out.
As they thought I was on minimum wage, I had to hide the extra money I was now making on a nightly basis. I spent some of the money on buying sexier and sluttier clothes which I considered to be an investment – the sluttiest the dressed, the more money I made.
One day I was wondering what I could do with the money and I had a life changing brain wave. If I invested some of the money on me I could make even more money, so I looked on the internet and found myself a plastic surgeon who would work on enhancing by breasts. On almost every show I would get a comment about how much better I would look with real breasts in my bras. So, why not? Who was I harming?
A few weeks later I went to the surgeon and returned with a cleavage to be proud of. I had told July and Macy I was going away for a few days to visit a friend from school who was studying in Exeter. It was a white lie as that was where the surgeon was and I did see an old school friend. As I walked through the door in a low cut dress, my sisters were both speechless.
“Well do you like them?”
“What the fuck have you done?”
“I treated myself to a little present. Nice aren’t they?”
I popped them out of the top of my dress for them to get a good look at. They both stood up and squeezed a boob each.
“Not so hard. They’re still a little tender.”
“Well Anna, I guess you’ll not be going back to being our baby brother now. I’m so glad you’ve finally made the transition. We wondered if you’d ever become what you should always have been. I guess you’ll make even more money on-line now!”
I was shocked.
“How did you know?”
“Well you never smelt of greasy oil when we got home, we’d noticed all of the new dresses in your wardrobe and we’d seen how much more confident you’ve become. Besides, you left yourself logged on to the PC and we saw your profile. Your shows are pretty hot! If you ever want to put on a show with a couple of real girls to play with …”
That night my visitors got a very special show. Not only to they have the big revealing of my new breasts they got to see two sexy girls playing with them. A brunette sucking my right breast and a blonde on my left. Each had a hand wrapped around my sissy cock and took pleasure and getting me as hard as possible. I just laid back and let them have their pleasure. When I told them I couldn’t hold back any longer they left my erect nipples covered with their lipstick and fought over my cock. They both wanted to receive my first load of cum with my new boobs. Macy took the first load and July the second. They swapped it between each other and then moved up my body and kissed me, dripping my own cum in to my mouth. I’d done many things on-line, but had never tasted my own cum. I knew that I’d be adding it to my show on a regular basis.
The tips I received that night were more than for any other show. I didn’t tell my tippers that these two sexy goddesses were my sisters, but I promised that they would be regular visitors from now on. With the money from that one show I treated my sister’s to a good night out and bought myself a new dress to show off my new assets.
As my life took a path I’d never expected I found myself getting further and further in to the amateur porn industry. I had set up my own website and was selling self-made videos. I was making enough money for the three of us to move to a bigger flat. Macy had found herself a job back in the theatre and July soon followed her. Everything was going well for all of us. Some of the favourite photo shoots were when I dressed up in rubber. I loved my skimpy blue rubber dress, but the pink sleeveless catsuit should off my new boobs to perfection. It appears in a few of my shoots and a coupl eof videos that July helped me to shoot. Perhaps you’ve seen some of them or perhaps even stroked your cock whilst looking at them?
We were never happier than when one or both of them joined me on-line for a show. Having one of your sisters helping you to cum in front of a bunch of randy strangers is exciting beyond belief. Having her stroke your cock whilst suckling your boobs and then wrap her lips around your cock and taking all you have to offer is what families are for. And then when you taste your cum on her lips, well, if you get the chance, give it a try!
We’d been doing shows together for quite a while when one day July said,
“So Anna, when are you going to fuck me?”
I was a little stunned.
“Well, erm … I didn’t think you’d let your little brother screw you.”
“ Despite what you do for a living, I know that you’re still a virgin. Kind of ironic isn’t it? All of those strangers who have seen you cum so often and yet you’ve still never had your girly cock inside a pussy.”
I didn’t know what to say.
“Would you like me to fuck you July? Wouldn’t it seem strange?”
“Being fucked by your brother is strange. But watching your brother grow up to be a pretty dancing girl and then have breasts bigger than you is also pretty strange. Knowing that he’s got a bigger fan club on the internet than some pop stars is pretty strange. But watching his videos every night whilst wanking myself off with my pink vibator, wishing he’d take the hint and join me in bed to fuck me, that’s reality. Laying in bed knowing that you’re on the other side of the wall and wondering if you’ll ever offer to make love to your sister, it’s been tough s*s.”
That night we put on the best show so far. July got me harder than ever as we both knew how this was going to play out. As she lowered herself on to my erection all I could hear was the tip jar getting fuller and fuller … but I didn’t care. Here I was on my back looking over my breasts looking up at my pretty sister as she bounced up and down on my cock. Her cunt muscles were working my cock so much I couldn’t hold back any longer. As I was about to cum I looked over her shoulder and saw Macy standing naked behind her. She was squeexing her nipples with one hand whilst shoving a rather large vibrator in and out of her leaking pussy. I beckoned her over as I wanted to feel her lips on my bullet like nipples.
As I felt her lips around my nipple and July started to grind herself against me I shut my eyes and enjoyed the full body stimulation it was receiving. My eyes opened as another pair of lips started sucking on my other nipple. I had assumed July was leaning forward and suckling me as she rode my cock.
“MUM!”
And my cock emptied itself deep inside July’s convulsing pussy.
Fawn
- 27.03.2020
- 17
- 0
