I used to be so shy but not any more and I love the way I am now.
Part 1
I grew up with very prudish parents. When I left my bedroom to go to the bathroom I always had to wear a dressing gown over my nightie and I had to be fully dressed to go downstairs. My parents also sent me to a catholic, girls only school. Even the college that they sent me to was all girls catholic. At the college the other girls idea of fun was play chess.
So, when I left college and got my first job I was the dowdy, quiet girl whose skirts were always below my knees and my blouses buttoned to my neck and I couldn't even join the conversations with the other girls about boys because at twenty one I had never even had a boyfriend and was starting to think that I would live for whatever years and die a virgin.
The only thing that gave me a bit of hope was that the job that I have is in a city about one hundred miles from my parents so they got me this one bedroom apartment. For a few months I settled into both my job, my little apartment and my dreary life.
Now is probably a good time to describe myself, I'm a skinny girl, my mother having only ever given me small portions of healthy foods and I was never allowed to have any confectionery. Would you believe that at twenty one I had never even been inside a McDonalds or a KFC. This upbringing got me into the healthy eating habit and that never changed when I went to college, nor when I started living on my own.
My name is Claire and I am only one hundred and fifty centimetres tall and weigh forty one kilograms. Fortunately my breasts never grew more than a 'A' cup so I never have to worry about unwieldy breasts even though my mother always insisted, and got me into the habit of wearing sturdy bras. I wear glasses and have long, blonde hair, my mother only letting me get it cut when it got half way down my back.
.
When I started my job things started to change, although it took one of my co-workers to tell me before I realised that one of my bosses had started to spend more time than necessary at my desk talking to me. Ethan is only a couple of years older than me and when I first met him my heart gave a little flutter for the handsome young man.
I started thinking about why Ethan came to my desk so often and realised that most of the occasions were unnecessary and I just couldn't understand why he came. I could never imaging that he would have any interest in the dowdy me but he was definitely flirting with me but I was enjoying his visits and our little chats.
I assumed that he was just using me to practice chatting to girls and some of the things that he said embarrassed me and some I didn't really understand because I was a very naive and lacked even basic relationship experience.
Then one day Ethan asked me if I'd like to go for a drink with him. At first I thought that he was joking and I said so. When he said that he was serious I asked him,
"Why would you want to go for a drink with me, there are lots of girls here that are more beautiful than me and I'm sure that they would love to go for a drink with you."
"Because underneath that long skirt (knee length), that heavy blouse and those glasses I believe that there is a very attractive young woman."
That really made me blush and I replied,
"Stop it Ethan, you're just trying to embarrass me and you are succeeding. You don't really want to go for a drink with me, you're just winding me up."
Ethan picked up one of my hands and held it with both of his and said,
"Claire, I am deadly serious, I really want to go for a drink with you. I want to get to know every bit of you a lot more than is possible in the office."
"You're serious Ethan, you really want to got for a drink with me?"
"Yes Claire I do."
"But I don't drink, I've never touched any alcohol."
"That doesn't matter Claire, believe it or not, pubs do sell none alcoholic drinks. Please say that you'll come."
"Okay, I will, but I warn you that I don't have any nice clothes."
"Claire, you could turn up totally naked and I wouldn't mind, I just want to get to know you better. Having said that if you did turn up totally naked it would certainly help me to get to know you better."
"Stop it Ethan, I'm a good catholic girl, I could never be naked in front of one man, never mind a whole pub full of them."
"Well that might change but for now I would be very happy if you turned up dressed like you are now."
I was still a bit embarrassed, but also excited at the prospect of my first ever date when I replied,
"Okay, what time and where?"
We fixed up a time and a place and we got on with our work although it was an excited me that happily got on with my work.
As I walked to the pub I was both nervous and excited. I was wearing what I considered to be my nicest dress, knee length, buttoned to my neck and with long sleeves. I'd been thinking about getting some new clothes that were more like those that other girls in the office wear, and after listening to quite a few girl's conversations I was coming to the conclusion that my upbringing was holding me back but I hadn't decided on how I would go about changing myself to be more like the other girls. I wondered if going on a date, or possibly more that one date with Ethan would help me change.
I had never been inside a pub before and didn't really know what to expect and I was very happy when I saw Ethan waiting outside the pub for me. I was also very happy when he took my hand and led me in. After getting us both a drink we went to a table in a quiet corner and talked, and talked and talked.
When Ethan went and got us a second drink he suggested that I get a cocktail. I told him that I'd never drunk any alcohol before he suggested one that only had a little alcohol in it. I didn't get drunk, not that I really knew what being drunk was like, but I did feel a little less reserved after I'd drunk it and I did reveal some of my desires, in particular that I wanted to be more like the other girls in the office.
I told him that I wanted to dress more like them and I told him that I'd got the impression that all of them were having sex and really enjoying it.
"So what's stopping you from changing Claire?" Ethan asked.
"Well I don't have much money but the main obstacle is my upbringing."
"Don't tell me Claire, you are a catholic and your mother told you that you must always wear dreary clothes and never let a man see your body until you get married."
"How did you know?"
"It's a common thing. I bet that a few of the girls at work were the same."
"So are you saying that my mother was wrong?"
"Your mother just passed on what her mother told her, it's not her fault that she isn't changing with the times, when you've been brainwashed it's difficult to snap out of it, especially when you are not too young."
"So are you saying that I should wear clothes like the other girls at work and have sex with men as often as they say they do Ethan?"
"That's not up to me to decide for you Claire, only you can make that decision, but I'll tell you now that it will not be easy, you'll have to work hard at it and get out of your comfort zone quite often. But the first obstacle that you have to overcome is you have to want to change. Do you want to change Claire?"
I thought for a couple of seconds then replied,
"Yes I do, those girls appear to be having a lot more fun than I do. And I want some of it but I don't know how to change."
"Well you've just solved the first obstacle, the next one is to force yourself into situations that are outside your comfort zone."
"Like what, how?"
"Baby steps Claire. How about getting some new clothes, ones more like those that the girls at work wear?"
"You mean shorter skirts?"
"Well yes, and low cut blouses. I'm sure that you have a really nice pair of legs under that skirt Claire."
"The first problem with that is that I only have small breasts. I could never display a cleavage like some of the girls."
"Not having big breasts isn't a problem look at Jenny Smith, she only has tiny breasts but that doesn't stop her showing most of her sternum most days. Besides, I don't like big breasts."
"The other problem is that I don't have much money, but I guess that I could shorten some of the ones that I've got. That's one good thing that my mother taught me, sewing, she even let me bring her old sewing machine with me."
"That would be a great start Claire, but maybe one new skirt or dress just to make you feel good because feeling good is half the battle. Maybe I could come with you to help you choose something."
"You'd do that for me Ethan?"
"Of course I would, it will be an excuse to see you again, outside work that is."
"I'd like that Ethan but you don't need an excuse to see me outside work again Ethan, I'd like to see you again." I was silent for a couple of seconds then I continued, "would you kiss me please Ethan?"
"That will be my pleasure Claire."
Ethan bent over and we kissed. At first it was just on the lips, but that alone was magic for me, I'd never had a proper kiss on my lips before and these strange feelings were starting in both my nipples and my pussy.
Then I felt Ethan's tongue trying to open mine so I relaxed and let them open. When I felt his tongue exploring my mouth I was a bit stunned. What was he doing? Does he expect me to do the same? I didn't have a chance to decide what he wanted or expected because my tongue had a mind of its own and the two tongues explored the other.
The strange feelings got stronger.
When Ethan finally broke the kiss I just sat there not really knowing what to say or what to do. After a couple of seconds Ethan said,
"What was that like Claire?"
"I, I, I don't know what to say, I've never experienced anything like that before."
"But was it nice?"
"No, it was awesome, it stated strange feeling in my, my lady parts."
"You mean your nipples and your pussy?"
"Yes." I quietly replied.
"You can say those words Claire, say them again."
"Nipples." I replied.
"And?"
"Pussy." I replied.
"Again Claire."
"Nipples, pussy."
"Again Claire."
"Nipples, pussy."
"Again Claire."
"Nipples, pussy."
"Good, well done Claire, now tell me what the feeling was in your pussy."
"What, no, I can't do that, it's embarrassing."
"Claire, what did you say you wanted to do?"
"Change. Okay, my pussy tingles and it feels wet."
"Good, that's two more baby step achieved, well done Claire."
There was silence for a minute or so then I said,
"Thank you Ethan."
"You don't have to keep thanking me Claire."
"But you're helping me and I'm grateful."
"If you're going to be my girlfriend you don't need to keep thanking me Claire."
"You want me to be your girlfriend Ethan?"
"I do, but to you want me to be your boyfriend Claire?"
"I do Ethan. Will you kiss me again please?"
"You don't have to ask me Claire."
So I got brave and lent over and kissed Ethan on the lips again and it was just as good as the first time. Ethan put one of his hands on my knee over my dress. I tensed up for a second then relaxed and enjoyed the tongue wrestling.
When the kiss broke Ethan asked me if I'd like another drink. I asked for another cocktail and when he came back he sat closer to me and started asking me about my hobbies. I laughed and replied,
"What hobbies, I haven't got any."
"Okay, what nice places do you like going to Claire?"