Dear Diary Virginity Lost

(Everyone involved in sexual activity in this story is a consenting adult over the age of 18. Any similarities between this story and real life are purely coincidental.)

Author's Note: This story has elements of Incest/Taboo sex, First Time sex, and certainly Erotic Couplings. Since I couldn't list it in multiple categories, I decided that someone losing their virginity is the most prominent aspect of the story, so here it is in the "First Time" category. I really hope you like it.

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Dear Diary,

I am sitting here on my bed on the night of my 18th birthday. I grew up picturing a much different 18th birthday and the "real thing" has been a disappointment. All my close friends are away at college. A few of my cousins came over for dinner with my parents, but that wasn't what I had in mind. Where is all the wild partying to celebrate me becoming a woman. Hell, I'm still a virgin and I don't even have a boyfriend to shower me with love and gifts on this, a girls biggest birthday in some ways.

I think I'm going to eat another cupcake from downstairs and then cry myself to sleep. I didn't expect to be this lonely. I didn't expect to be so sad. This was supposed to be a BIG day for me. And I'm not sure how many people even know.

Goodnight,

Amber.

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Dear Diary,

I remember when I was a little girl, before I wrote in a diary, I would have a bad day and my mom would say, "tomorrow will be much better." When I would ask why she said that, she would say, "because tonight, an angel will sprinkle you with dust while you sleep and you'll wake up all better."

You know, I think she might be right. I woke up this morning, read over what I wrote last night and decided, it's my responsibility to be happy. It's up to me if my 18th year on this earth will be one to be remembered.

So, starting this morning, I am going to be excited to be an adult and live a little; starting with the whole virginity thing. I need to find someone worthy of taking my virginity. I know it sounds shallow to focus on that, but for now, it's what I want. I'm getting tired of pleasuring myself.

I'll write more later,

Amber.

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Dear Diary,

I can't believe it has been a week since I have picked this up and written to you. I think I found the guy. Mario. He's the cousin of a good friend of mine and I met him at her birthday party a few months ago. He's a year older, but he's in my history class at college. I noticed him the other day and re-introduced myself after class. We've hung out a few times, in between classes at the student center, and I think my flirting is having an affect on him. I hope he asks me out soon.

More later,

Amber.

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Dear Diary,

Oh my god! I'm so excited. My flirting worked. He asked me out. Well, honestly, I had to help. We were sitting in the student center and I asked him what he was up to this weekend and when he said, "nothing really", I asked him if he wanted to hangout and he agreed.

He is supposed to text me later this evening and figure it out. I can't wait to write more to you about what happens. Maybe he'll be the one.

Excited,

Amber.

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Dear Diary,

Mario is definitely the one. He's so cute. He's so fun. Okay, okay, here's what happened.

He picked me up about 6 and we went to a movie, I barely even remember the movie. After we went to pizza he suggested we go somewhere to "talk". I knew what he meant.

I had on some tight ass jeans, I knew they'd drive him crazy, and I wore a flannel shirt and a sexy, lacy bra underneath. I picked it so he could get into it easily. Listen to me talking like a little slut.

Anyway, we went and parked in this dark lot at the soccer fields. We were talking and laughing a lot and then he put his hand on my leg and started rubbing my thigh. It got really quiet and then he leaned over and kissed me and we started making out. He's a good kisser. A really good kisser.

I let him unbutton my shirt a little bit and he felt my tits. He was so sweet, he even said he really likes tiny tits better than big ones. While we kissed, I rubbed his dick through his jeans. He got really hard. He started to unbutton my pants, but I stopped him and told him that had to wait until our next date.

Another car came into the parking lot and I got kind of scared, so I told him to take me to ice cream. We had so much fun at ice cream and then he took me home and kissed me goodnight. I'll go further on our next date.

It was so much fun. He just texted me goodnight and sweet dreams.

Not a virgin for much longer,

Amber.

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Dear Diary,

Mario texted me this morning and wants to go out again tonight. He said his parents are going out late and I should come over and watch TV. Yes! Yes! Yes!

Later,

Amber.

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Dear Diary,

Why can't anything go right for me? Tonight got totally fucked up. I don't know if he'll ever call me again. Fuck! It was so lame.

Mario and I were at his house. We ordered some Chinese food for delivery and then we were sitting on the couch watching TV and started making out again. I wore jeans again and a tube top under a sweatshirt. He put on some loose basketball shorts and I reached up them and felt his dick. He got hard really fast and said he was going to get something from his room.

While he was gone, I stripped down and was laying back on the couch wearing only my black panties. I was right! He came back with a condom. He climbed on top of me and his bare cock was rubbing against my panties a lot while we kissed. He pulled my panties off while I kept stroking his hard on. He started to fumble with the condom wrapper and told me not to stroke him anymore, but did I listen? No!

"Oh shit. Oh fuck," he yelled. And then, before he could put the condom on, he started shooting cum onto my stomach. It was all over the place and just kept going. I had no idea how sticky it would be.

"I told you to stop," he said in a really angry voice. He got up, trying to keep from dripping everywhere, and ran to the bathroom to clean up.

I almost started to cry. There I was, completely naked and still a virgin when he came back. I tried to apologize, but he threw my clothes at me and told me to get dressed so he could take me home before his parents came back.

I got dressed and we barely talked at all on the way home and he didn't kiss me goodnight.

I suck at this. I'll be a virgin until I'm like 50. I swear.

Amber.

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Dear Diary,

Well, I was right. It's over with Mario. I texted him and he said some shit about it was better if we just stayed friends. Fuck him!

I went and talked to my Aunt Sandy at her hair salon. She's really cool and won't tell my mom I'm trying to have sex. She called Mario a "little boy" and said I needed a more experienced guy. She said it was his weak dick that made him not be able to hold it and that more experienced guys wouldn't do that.

Back to looking,

Amber.

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Dear Diary,

I thought it would be really awkward seeing Mario in class today, but we both just smiled and said "hello" and it wasn't that bad. I saw him chatting up some other girl in the parking lot. I felt like warning her about his weak dick. Oh well.

I need to go to work, so I'll write more later.

Amber.

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Dear Diary,

I better lock this up even tighter after I write what I am about to tell you. I am so bad. If my mom ever read this, she'd ship me off to a convent.

There's this group of men that hang out at the bar at the restaurant I'm a hostess at. None of them even know I exist, let alone my name. Except this one guy. John. He's like 40! But he always says "hello" and he always asks me how school is going and stuff.

Anyway, tonight, he left the bar and came up to me at the hostess stand when no one was there and handed me a little card. I asked him what it was for and he said, "You just had a birthday, right? It's just a little gift since you never get tipped."

I went to the restroom later and opened it. It was a sweet little birthday card and $50! What the hell? He is so nice. And he's fucking hot. He is definitely more experienced. Oh shit. I shouldn't even think like that.

Can you imagine? I may think about him tonight as I go to bed. Wink, wink.

Wet with excitement,

Amber.

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Dear Diary,

John was drinking at the bar again when I went to work tonight. I swear he checks out my ass when I walk by him. Okay, maybe I just want him to, but I swear he does.

He's so sexy. He's like 6 feet tall and very well built and seems to always be golfing or something like that. He has short, blonde hair and a cute goatee.

Last night, I totally thought about him while I fingered myself to orgasm. Wouldn't that be something if he was the one? He doesn't wear a ring, but there's no way he'd do anything with me. I think I'm going to touch myself again tonight and imagine him taking my virginity.

Sweet dreams to myself,

Amber.

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Dear Diary,

I haven't written for a few days because I've been totally consumed with John. I can't stop thinking about him. He hasn't been into the restaurant for a few days. I can't sound creepy and ask the bartender about him, so I just have to hope he comes back soon. What's wrong with me? I'm obsessing over a guy who is probably like twice my age. It's so wrong.

I need to get a life,

Amber.

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Dear Diary,

He's back! He was so sexy tonight. And, I talked to him more than normal. I walked by him at the bar and, when he said, "hello", I asked him how he was doing.

"Happy to be home," he said. I stood there, staring at him of course, while he told me he had been away on business for a few days. I couldn't believe it, but I told him it was good to see him again and that I missed seeing him. What the fuck? I probably sounded like such an idiot. But, he did tell me that he always looks forward to seeing me there.

I want to fuck him. Okay, at least I want to kiss him.

Amber.

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Dear Diary,

Tonight was amazing! I am literally sitting here on my bed pinching myself to see if I am alive or if I died and went to heaven. Here's what happened. I can't believe it.

I was polishing some wine glasses near the bar and staring at John of course. He was talking to the general manager, Daniel, and telling him about some big trip he has coming up and how he hated to be gone from home that long, but it was some kind of a really awesome opportunity. I couldn't help but eavesdrop.

Daniel suggested he get someone to house sit for him. John agreed and asked Daniel if he knew anyone and, holy shit, I still can't believe it, Daniel turns to me and says, "Amber, do you do house sitting?"

I probably sounded like a mumbling idiot, but apparently I said some form of "yes" because the next thing I knew, John was inviting me to come over to his house to see if I would be willing to do it. We exchanged phone numbers and he said he would text me to find a time to come by.

I must have got an extra dusting of angel dust last night because my dream is coming true. I am going to be alone with John at his house.

I'm in heaven,

Amber.

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Dear Diary,

Now I know exactly where I want to lose my virginity to John. Wow! What a nice house. It's way up on the side of a hill. The house is so awesome inside. It has a sunken living room that is totally set up like a home theater with these really cool recliners, but the best part is the patio and the view.

He has a big back patio with a view of the whole city and a big built-in grilling area and bar and a hot tub. That is where I want to lose my virginity. In his hot tub. I'm going to slowly peel off my bathing suit and then sit down on his erect cock and just fuck away with my chest in his face.

I may have to stop writing soon. I'm getting really wet thinking about it and I'm going to need to do something about it.

Anyway, he is going away on golf trip and wants me to stay the whole week. He said I could have my boyfriend over and when I said I didn't have a boyfriend, he replied, "Really? How does someone as cute as you stay single?"

In a moment of brilliance, I replied, "The same way someone as handsome as you stays single, right?"

He didn't reply at all, but I swear he smiled really big and winked at me. I know he's single. I know he is. He's probably a player, but who cares. I just want to get fucked by him.

And, oh my god, he totally noticed how good looking I am. I knew he was looking at me. I wore some tight, striped jeans that make my ass look really bubbly and I know he loved it.

Now I just need to find a way to be alone with him at his house and then I can seduce him. He'll never be able to resist.

Off to make myself happy,

Amber.

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Dear Diary,

John is leaving in a couple days and today he is supposed to come by the restaurant and give me the key to his house and some other information. I can't wait to see him. I'm useless these days at school and around the house. My mom even asked me why I was so giddy lately. I wish I could tell her straight up that I found a much older man to take my virginity. She'd fucking freak out.

More later,

Amber.

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Dear Diary,

I could not drive home fast enough tonight to write to you about what happened. There is no way I can possibly go to sleep tonight. I'm so excited.

I got into work and John was sitting with some other regular at the end of the bar. I stopped by and he gave me the key and a note that lists when to put the garbage cans out, how to use the hot tub, and all that crap. I took the key and told him he didn't have to worry and then I headed to the kitchen area to get ready for the night.

As I got out of sight from the bar, the other guy asked John, "What was that all about? Is there something going on you want to tell me about?"

No one was around, so I stopped to hear what John said back. At first, he replied, "Nothing. She's house sitting for me while I go on a golf trip for a week."

Then his friend keeps going, "She's cute as hell. You should let her house sit when you're home sometime, if you know what I mean?"

John replies, "She is fucking hot and legal, too. Hell, if I thought I could get away with it I'd let her babysit me for a while."

Just then, Daniel came around the corner, so I had to get back to work.

Okay, he's probably just "guy talking", but seriously, I want him so bad and I think he'd do it.

I can't wait to stay at his house and dream about him.

Amber.

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Dear Diary,

I forgot my diary at home, so I was finally able to go back and get it. I have been at John's house for a couple days now. Some of the fun has kind of worn off, but not before I was able to snoop around and have some fun.

He wears boxers and even has a few pair of silk ones. Oh god, I would love to see his cute butt in some silk boxers. I might steal a pair and take them home. I wonder if he'd notice them missing.

I couldn't help myself and I laid on his bed one night and fantasized my way to a massive orgasm thinking about him. His bed is a big, four-poster bed that is way up off the ground and would be the perfect place to get fucked, but I still like the hot tub idea.

Tomorrow night, my Aunt Sandy is going to come over. I told her about John and she thinks I should go for it. She's so fucking cool. She wants to check his place out. I just need to make sure she never meets John. She's a wild one and really good looking and he'd go for her way before me.

More tomorrow,

Amber.

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Dear Diary,

What a night I just had. I don't even know where to start. I am still very buzzed and I might feel different in the morning. My Aunt Sandy is asleep on the couch where she passed out, but I had to write and tell you about it.

Aunt Sandy is like the coolest aunt a girl could ever have. She has never been married because she says she could never be with only one man.

She came over and I took her on a tour of John's house. We checked out his boxers and I found some pictures of him laying around so she could see how sexy he is. She totally wants me to lose my virginity to him.

Anyway, we ordered some pizza and were drinking some champagne she brought over and we got pretty buzzed and were laughing and screwing around. We went out on the patio to smoke some weed she brought along. We rolled up our pants legs and were dangling our feet in the hot tub because I forgot to tell her to bring a swimsuit.

Next thing I know, Aunt Sandy stands up alongside the tub, pulls off her shirt, unhooks her bra, and starts unbuttoning her pants, and says to me, "Come on. Let's skinny dip."

I have a very open relationship with my Aunt, hell, she's the one that told me how to play with myself, but I have never really seen her totally naked, and I certainly haven't been naked in front of her, but my inhibitions were way down, so I got naked with her.

Holy shit. Okay, so my perky little, barely B-cup, tits are like mosquito bites compared to her huge breasts. And damn, her nipples are huge and dark. My vagina has a small bit of hair and Sandy's is totally shaved smooth.

After soaking in the tub for a bit, I sat up on the edge of the hot tub with my legs still in the water while Aunt Sandy was asking me about what I'd do with John and giving me tips on doing it for the first time. I was starting to feel really horny and she noticed me slide my hand down between my legs and tickle my clit.

Out of nowhere, she said, "Have you ever let another woman pleasure you?"

I was so buzzed it didn't even phase me, and I replied, "No. It sounds fun. Have you?"

She replied, "Your Aunt Sandy is no church girl. There isn't much I haven't done."

Before I could slow down the conversation, I heard myself say, "Is it fun?"

Next thing I knew, she waded through the water toward me, got down on her knees, spread my legs gently, and ran her tongue from the bottom of my pussy to the top. Oh fuck. It was the best feeling I'd ever felt. She didn't even hesitate to start giving me oral sex; licking me, sucking my clit, and even fingering me in between. I couldn't help it and I started pinching my nipples while she went down on me.

After about 5 minutes, I couldn't take it anymore and started to squirm and shake and finally burst into a wild orgasm. My aunt just sat back and watched me climax and slowly slide into the water.

"I hope that was okay," she said, as I came out of my orgasm induced trance.

"Oh god. That was amazing. I hope John is that good."

"If he's not," she laughed, "Maybe you can think about sticking with women."

"What do you like better?"

"I like whichever happens to be with me at the time. Sometimes both."

We finally got out of the hot tub and went in the house with just our towels. We poured more champagne, even though we probably didn't need it, and sat on the couch and kept chatting. She started rubbing my neck and shoulders and then asked me how I felt about returning the oral sex. I have never given oral sex to anyone, let alone a woman, and let alone my aunt, but it sure sounded like fun.

She was so sweet about guiding me through it and it wasn't long before she was soaking wet and screaming with an orgasm. We kissed and touched a little and it was so incredibly sweet.

Anyway, she's still snoring away on the couch where I left her. I think I'm going to sleep in John's bed tonight. I need to get used to it.

Goodnight,

Amber.

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Dear Diary,

My morning with Aunt Sandy was natural and wonderful. We showered together and agreed to get together from time to time, but for now, my focus was on finding a way to have John be the man that deflowers me.

He'll be home in a few days, so I need to start thinking of a way to make it happen.