tagFirst TimeThe Girl and the Woman

The Girl and the Woman




Thanks for your feedback. Anonymous or not, it's important and appreciated - it's our only reward! But please keep in mind that English is not my first language.


The party was boring... The fact that it was a wedding party with lots of booze and almost no food - for someone that don't drink like me - didn't help, and the table I was in wasn't the best table in the party either: myself, three people I didn't know, and a couple with two daughters where the father was drinking heavily. But what I didn't know was that my luck was about to change...

The couple in question, Maggie and Rupert were the parents of Pam, an acquaintance I had. Her sister, Anna, was only a child the last time I've seen her, but now she was a pretty, innocent looking, lightly chubby 18 year-old, with a perfect makeup that made her really desirable. But as a responsible 40-something, I would never hit on her, especially with her parents and older sister around. So, I tried to concentrate only in the occasional bite the waiters served and distract my mind from the hunger that was growing inside me.

Around midnight, however, things got a little ugly: Rupert was really, really drunk, and started to behave badly and Pam and her mother tried to calm things down, but to no avail. So, they decided the best option was to leave, and called Anna - that was dancing - to get her things. Anna, on the other hand, was not happy: she was having a great time with her friends, and didn't want to leave so early. The debate started and, while both Pam and Maggie tried to convince Anna to leave, she didn't want to, and at some point said openly that "it always happened" and "it wasn't fair". At that point, the other three people on the table were watching the developments as if we were in a reality show, what obviously made things even worse.

At that point, I called Pam to the side and asked her if she wanted me to get Anna home after the party. It was not a problem for me, I said, it would be a pleasure, and would allow them to leave. She thought a little about it but, me being the responsible, no-drinking, middle-aged guy I am, she decided to talk to her mother about it. A minute later, she called Anna - that looked really happy after talking to her - and then both of them came to talk to me.

Now, as I said, I knew Anna from years before, when she was just a kid. She didn't remember me, and I barely could recognize her in her black dress, eyeliner, makeup and red lipstick. She was really something, that innocent face and somewhat childish behavior in a woman's makeup and chubby, delicious body - tits and ass alike - started all sorts of fantasies in me. Looking back, I can say that it was just then that I decided I would try something, that my initially kind gesture of taking her home turned into something a little more depraved. But at the time, I couldn't really know it - my instincts were working, but my brain didn't take notice.

Everything decided, Anna thanked me effusively while Pam made lots of recommendations to her - to obey me, to avoid drinking too much, etc, etc. After that, Anna got back to the dance floor and I agreed with Pam to get her sister back home before 5AM, since the party should end at 4AM tops, and Pam, Maggie and Rupert - or what was left of him after all the booze - left.

The next two hours were again a bore: I talked a little with the other person's in my table, and nothing more. But at 2AM, the lack of food started to take its toll and a lot of people started to leave and in less than half an hour, the party was almost empty. Anna finally got back to the table, looking exhausted after all the dancing.

- You really like to dance, Anna!

- Yes, I like it a lot! But now everyone is leaving...

- Probably because there's no food - I told her, in a playful tone.

- Yes, probably - she said back, smiling in her provocative red lipstick.

Definitely, that mix of woman and girl was going directly to my head - or should I say heads? At that moment I could say I was finally starting to consciously flirt with her and to try to show her my interest. She looked oblivious, tough, the girl showing herself under the woman's skin, too innocent to acknowledge my gestures.

- Well, since everyone is leaving, what about us going as well? I'm starving! And since we still have almost three hours in your curfew, we could get something to eat in the way home. - I told her.

- Yes, I'm hungry too... But I have no money with me, mom forgot to give me some! - She lamented.

- Not a problem! You're my guest of honor. What do you think?

- Oh, I don't know, Carl... I don't want to be a burden...

- A burden??? You really think that you would be a burden? What I know is that everyone at the restaurant will be jealous of me, having dinner with such a beautiful girl. It will be an honor!

She blushed, for the first time acknowledging my interest. I thought that I had gone too fast and that she would not accept the dinner idea, but after a few seconds she opened the prettiest smile and said:

- OK then! It will be fun!

In the way to the car, I could see that she was a little drunk herself - not wasted, but a little light-headed. Another thing I could see is that she was really my type: a plump, curvy ass, generous tits, black, curly hair and that young face full of make-up. I was in heaven - or at least hoping to be in my way to heaven at that point.

I didn't try anything more ambitious, though. In our way to the restaurant, we started to talk about the party, and she started to complain about things at home. I believe it was the booze speaking, since we didn't have the intimacy to that type of talk, but she told me how difficult it was with her dad drinking. He was not the violent type nor caused any real problems at home, but he was a really absent father in her life, and there was the economic burden of his bad habit. I tried to comfort her, but to no avail.

At the restaurant, her mood improved a little, and as we ate we talked a lot about lots of things, with her laughing openly. At some point, however, the lady in the table adjacent to ours let her purse fall to the floor, and Anna got it to her. The lady thanked her and said to me:

- You raised a very polite young lady!

I didn't think in an answer at the time, since she got me by surprise, but Anna answered her in a serious tone:

- Thank you! But he didn't raise me, that was my father. He is my boyfriend! - and made a face as if she was offended.

While I looked surprised, the lady started to apologize profusely. Anna made a stern face, told her it was OK and got my hands in hers, turning back to me with a really funny face, trying not to laugh. I almost laughed out loud, too, but tried my best to stay serious while the poor lady turned back to her husband visibly uncomfortable. But, when we left, we laughed all the way to my car like two teenagers.

I confess that, at that point, I was hooked. The girl was fantastic: funny, pretty, young-looking and sensual at the same time. And that ass... Anyway, we got into my car and I drove the short distance that separated the restaurant from her house, arriving almost at 5AM as agreed.

- Well, princess, this is your castle. Dream with the angels. - I said, courteous.

- Thank you, my prince - she said, jokingly, and blushed lightly.

- It was a really pleasant night, Anna. I mean it. You saved me from that party with your charm and beauty - I blurted out, unable to contain my words.

Looking embarrassed by my compliment, she looked down but answered anyway:

- Yes, it was a really good night for me, too. Thank you for everything, Carl. The lift, the dinner... And the company.

She started to open the door to leave, when I asked:

- So, not a kiss for your "boyfriend"? - I said, half-joking, half-trying.

She stopped for a moment, as if she was thinking about it. Then, she turned back rapidly, gave me a small peck on the lips, turned back and left running for her door. The girl was back in her body, the woman now absent... I felt like a teenager, too, with a pathetic smile on my face.

I couldn't sleep that night without releasing my... tension. And, obviously, it was her in my mind while I masturbated. With the same makeup, but without any clothes, beautifully chubby on my bed, moaning... I came almost instantly, and as the sun was starting to appear, I fell asleep.

The next day, as soon as I woke up, I was again thinking about the night before. For some time, I couldn't get her out of my mind. Anna had an effect on me... Her innocent smile and sometimes childish manners coupled with the sexy young woman she has become were like fire on my mind... But, on the other hand, I didn't want to risk being seen as the creepy middle-aged man that was hitting on an 18 year-old girl.. So, even with the small kiss and the princess/prince talk from the night before, I decided not to try to contact her, reasoning that it could be only the booze from the party plus the wine she had on the restaurant doing their thing.

A week passed with no developments, and I confess that I was starting to lose hope, although she was still in my solitary pleasure moments... Then, out of the blue, she sent me a "friend request" on a social network.

When I received the request, I felt like a teenager: do I answer it now, or do I wait a little? Do I contact her after accepting, or just accept and wait? But in less than a minute I had accepted and sent her a private message:

- Hello, princess!

- Hi, Carl... Can we talk?

- Yes, sure!

- Well... Not here. I want to talk with you in person. Can we meet somewhere?

Well, that was more than I could hope for...

- Yes, yes, absolutely. When?

- Could it be tomorrow, around 1PM?

I was self-employed and doing very well, so I could easily clear my afternoon, even it being a Monday... Especially for Anna. So, I answered yes, and she told me to wait in a specific square, a few miles from where I live.

The next day, after 24 hours of painful wait and wet dreams, I was parking my car near the place we have agreed. A minute later, looking ahead, I saw something that both chocked and aroused me: Anna was coming directly from her school and, as such, she was still dressed in her middle-school clothes: a blue skirt, white blouse, sneakers and a backpack. As I would find out later, she had lost two years of study due to problems at home with her dad, as she had to change schools and had a difficult time keeping up with everything. She was now a senior, in her last year of high-school, despite already being an 18 year-old.

Anyway, she walked directly to my car and entered, barely saying hello before asking me to go.

- Go where? - I asked, confused.

- Anywhere. But please let's go, otherwise a friend could see me with you, talk to someone, and my parents could find out, and I prefer they don't.

I didn't question why, and just drove off. And then, when I thought things couldn't be weirder, she started to cry.

To make things shorter, I will not transcribe the entire dialogue. But the fact is that Anna was tired of things at home - the financial problems and the daily fights because of her father's drinking - and, after that night we spent together, she started to think of me as someone with whom she could share what she haven't shared before. "Her friends couldn't understand" - her words - "as they were too young". Poor thing.

I parked near the beach but in a secluded place, and we talked a lot. I couldn't offer a solution, but I tried to offer comfort, and it worked. Her mood improved little by little, and after a couple hours she was starting to smile and relax. Then, to my surprise, she asked, out of the blue:

- Carl, do you have a girlfriend?

- I... No, I haven't.


- Why are you asking me this, Anna?

- I... Never mind.

- Oh, no, young lady. You can't ask me something like this and then give me a "never mind". - I said, amusingly.

She laughed, but then looked to her feet and blushed in the same childish, extremely charming way she did at the wedding night right before kissing me. Then, after some time, she blurted:

- I loved the dinner we had...

- Yes, my princess... I loved that too... - I said, my heart melting.

- And... And I wanted to know if... Maybe... If we could do that again some time...

She was... Asking me out? Me, the middle-aged, regular-looking guy? Again, I felt like I was 18 again, my heart pumping in my chest, my hands sweating.

- Oh, Anna... I would love it very, very much!

Finally, she turned, and not being able to hold myself anymore, I embraced her and slowly kissed her mouth. I could feel her trembling, her breasts pressing my chest, her hands touching my face, and that delicious mouth dry of excitement and tension starting to open to let my tongue have its way...

I can't say for how long we kissed, Initially in a purely romantic way, later, passionately. She was completely mine that day, I could do anything I wanted to her... And things started to get hotter and hotter, my hands travelling through her body, she moaning... But no, I couldn't. And I broke our kiss.

- Anna...

- Yes, Carl? What's wrong? Did... Did I do something wrong?

- No, no, not at all, my princess... I... I just want to ask you something... Please, please don't be offended...

- I... I think I know what you want to ask... Yes, I am 18... 18 and a half.

- No, not that... I know you are, I've seen the pictures from your party in Pam's social network page. But... But I want to ask you if you are...

The silence was so heavy that someone could cut it with a knife. But after some time, she understood my question, looked me in the eyes - the woman was back - and told me:

- Yes, I am a virgin. But I want you to be my first.

I could feel the electricity running through my spine, the excitement of these words making me almost cum right there. But I was already hooked... If a week ago she was a pretty, young girl with a fantastic ass and marvelous tits, now she was something else, she was someone that I cared about and that - as out of my mind it could sound - I really wanted to have a full relationship with. And fuck the looks we would get, fuck what her parents and my friends would think!

But exactly because of this, I didn't want things to be that way. Not in a car, in the middle of the street... She deserved better, she deserved a castle, on par with the princess she was.

- Anna... God knows how much I want the same thing... But...

- Please, don't start with the "you're too young for me"! - she said, upset, behaving like a spoilt child.

- No, not that my princess... I just don't want it to be like this... You deserve much better... I want it to be perfect.

- But you are here, and this is what counts... - she answered, pouting.

- Yes, I know, sweetheart... But patience pays. Let's do the following: do you think you could escape this weekend?

- What do you mean escape? The entire weekend? - she answered, excited.

- Yes, I mean, from Saturday around noon to Sunday around 5PM at least.

- I can try... I can ask a friend to say I'll go with her to her parent's house in the mountains, as she is going anyway this weekend. My mom will not be happy, she is very protective, but I think I can manage.

- OK, then. If you can do that, I promise you I can make it up to you... My princess.

She gave me the most beautiful smile I've ever seen, and then started to kiss me again, what only made my task of avoiding fucking her right there more difficult...

The week passed slowly... We talked every day through the computer and on the phone, to the point that I heard her mother complaining with her that she was passing too much time in her bedroom. It was clear to me that she was really sad about her father and that, in some way, I was being a substitute for the older man figure she never had. On the other hand, it wasn't everything or I would back away, as I would never take advantage of a vulnerable girl. In fact, we discussed this openly, and she agreed that she missed the fatherly figured, but stressed that it was not what made her like me. I was funny, and smart, and charming, and all her friends would envy her - all of this her own words - and I was not her father, but her boyfriend, as she said in the restaurant. And I believed her - not that I was that much, but at least that I was that much for her.

Anyway, the days finally passed and Saturday arrived. The day before, Anna told me to wait for her two streets after her home, and that I shouldn't call her so we would not raise any suspicions from her mother. I waited and waited and waited, and was almost giving up when finally, about two hours after I got to the place we agreed, she appeared, almost running, and entered the car. She was stunning, with a light dress, perfect make-up and that young girl looking I was starting to get used to. I almost pinched myself to make sure I was not dreaming...

- Let's go, my prince!

- Oops... Not a kiss?

- Not here, silly! Let's go before someone sees us! I should be in a bus to the mountains now, mom put me inside one but I got out as soon as the bus left the stop.

- You are something else - I said, starting the car and laughing.

Anna stayed nervous until we finally left the city and got to the highway, when she finally relaxed. She then asked me to stop in the first gas station, and I thought she would need to go to the bathroom. But as soon as I stopped, she let her safety belt go and embraced me, kissing me passionately for some time and saying:

- Now I can kiss you as much as I want. You're really my boyfriend. I can't believe it...

And she embraced me again, a tender, strong hug like she would never let me go, and if we didn't have to keep driving I would not want to either.

Once we got to our destination on the beach, we have gone to check into the hotel. The guy in the reception asked to see her ID (and paid real attention to make sure it wasn't a fake), while she made a face. When he confirmed she was really eighteen, he gave it back to her and looked at me with a funny face, that I've read as a compliment. Finally, he gave me the keys.

As soon as we entered the room, she was ecstatic, running around like a teenager, deliciously amazed with everything. Obviously, I didn't save a penny when searching for the perfect place: we were in the best room of the hotel, the immense sea in front of the glass that served as a wall to that entire side of the room; the bed was enormous and beautifully made, and the room itself was very spacious. I sat on the couch, laughing, while she checked every corner of the room, until she finally found a special arrangement I had with the manager when I called to book the room: a small gift box with her name on it. She looked confused, then surprised, and when she finally opened the box to find the matching golden earrings, chain and ring, she just stood there, speechless.

- There's a card, too. - I said.

She opened the card and read out loud:

- "A princess needs its jewels. Please accept this humble gift from your prince. Carl."

She just stood there, looking to the card and the jewels. After some time, she finally looked at me, crying softly, and suddenly she came at me and started to kiss me everywhere: on the lips, face, eyes, cheeks, saying "thank you, thank you" repeatedly.

I've waited until she calmed down, looked her in the eyes, and said:

- Thank you for making me feel more alive than I felt my entire life.

And we kissed passionately and - I was starting to see it - completely in love with each other. I didn't want to rush things, though. So, after some time I managed to compose myself and break the kiss, telling her:

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