Dear Diary: Virginity Lost

More later,

Amber.

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Dear Diary,

This morning is bittersweet. I need to start packing up because John is coming home tonight, which means I won't be staying here, but it also means I can get back to planning away for him to take me and make love to me.

I'm going to finish this entry in a bit. I'm going to try something...

DAMMIT! It didn't work.

I texted John and asked if I should just bring the key by later when he was home. He asked me if I was working tonight, I am, so I had to say yes, and he said he'd come by the restaurant and pick the keys up and pay me on the way home from the airport. This sucks. Now I have no way of being at his house when he's there. Fuck! Sometimes I'm so stupid.

Mad at myself,

Amber.

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Dear Diary,

He dropped by the restaurant tonight, picked up the keys, paid me, and then headed home without even staying to have a drink. I'm sure he was tired from his trip, but it seemed so business-like. Unless he needs a house sitter again, I doubt I'll ever have the chance to be over there alone with him.

It's not like I can say, "Hey John, can I come over and seduce you?"

Oh well. Maybe I should just find someone else.

Good night,

Amber.

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Dear Diary,

There is a God! Oh shit. You will not believe what just happened. I just put down my diary and he texted me and, oh my god, I am totally on cloud 9 and I have to tell you about it now; there is no way I can sleep.

John texted me, and said, "Hey thanks for keeping the place really clean. It looks better than when I left."

I replied, "No problem, I'm hope you had fun on your trip."

He said he did and then asked me if I had fun staying at his place, and I said, "Yes!! It was so nice using the hot tub. I'm really going to miss it."

And, I still can't believe it, maybe I'm dreaming, he told me, "Feel free to come over and use it anytime."

Maybe he's just saying that, but then again maybe not. I'm almost out of breath.

I texted him back, "Sounds good. I will." And then, that was it. I am so wet. I am going to get myself off in a big way right now.

Good night again,

Amber.

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Dear Diary,

A few days have gone by since I've written because I've been kind of dumbfounded about how to figure out a way to invite myself over to John's to use his hot tub. I called Aunt Sandy to update her and see what she thinks, but she was really busy and told me just to be patient and let it happen naturally. It is so hard to be patient, but I guess she's right.

Amber.

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Dear Diary,

Aunt Sandy was right!! Here we go! I am going to write this quick because I need to leave.

I am ON MY WAY TO HEAVEN!!

I worked a huge private party that bought out the restaurant tonight. We were closed to the public, but John came by later and Daniel let him in to have a quick drink at the bar. No one was around and I walked by, and John asked, "How you doing Amber?"

I was so busy with the party I seriously wasn't even thinking anything, and I answered, "I am so tired and my back and legs are killing me from helping serve this party."

He said, "Well, the invitation to relax in my hot tub still stands."

I quickly looked around to see if anyone could hear us and it was safe, so I said, "That would be amazing. Tonight after work?"

"What time are you off?" He asked.

"Pretty late."

"It's Friday. I have nothing to be up for tomorrow. Text me later."

I talked to Daniel into letting me go once the party was all served and now I am home grabbing my bathing suit and heading to John's. I texted him as I left work and he said to come right over. This has got to be it.

The next time I write you, I won't be a virgin anymore.

Amber.

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Dear Diary,

I am really close to becoming a lesbian and not worry about ever making love to a man.

Seriously, I didn't think it would be this hard to seduce a guy like John. I mean, I know he's like twice my age, but come on, I thought he would have jumped at the chance to fuck me tonight.

Here's what happened...

I went over to his house and he greets me at the door in some sweats and a hoodie. He is so cute. I wore some sweats pulled over a sexy, one-piece swimsuit, so the top of my swimsuit was showing. Okay, I don't have big tits, but it is very low cut and I know got his attention.

He tells me to head into the kitchen and make myself at home and get something to drink while he goes and changes. I wasn't sure if he meant alcohol, but I grabbed a wine cooler anyway and poured it into a big red cup.

John comes back out in swim trunks and a t-shirt and we head out to the hot tub. When he peeled off his shirt, I damn near had an orgasm right there. He is so fucking sexy. Anyway, I pull off my sweatpants and make sure he gets a nice look at my ass while I ease into the tub. Okay, the tub feels great, but seriously, I wasn't there to get relaxed.

After a bit, I climb up and sit on the edge of the tub facing John and spread my legs wide. He couldn't help staring straight into my crotch at my pussy.

We were chatting about his trip and funny people that come into the restaurant and stuff. I was trying to figure out a way to take my seduction to the next level when, all of a sudden, he announces, "I'm done. I'm turning into a cooked prune, but feel free to hang out." Next thing I know, he's out of the tub and drying off.

The only bonus is that I swear when he got out, I think he was getting a woody and it was starting to push out his shorts. I stayed a few more minutes in the hot tub and then got out.

I didn't have a good plan after that. I didn't bring a change of clothes, so once I dried off a little and put my sweatpants back on I couldn't really sit anywhere, so I headed home. He did tell me to come back anytime. Whatever. I don't know if this is going to work out.

I'm about ready to give up.

Amber.

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Dear Diary,

It has been like two weeks and John hasn't even been into the restaurant. I thought about texting him, but I don't really have a reason to and I don't want to act weird. I wonder if he felt weird about the hot tub and is too embarrassed to come in and face me.

It's Friday night, my parents are gone this whole weekend, I don't have a date because I'm obsessed with a much older man. Sounds like a weekend of junk food and binge watching TV.

Depressed,

Amber.

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Dear Diary,

Well, it is Sunday night at 10 o'clock. I just pulled out my diary to write when my mom, who just got home a few minutes ago, popped her head into my room and said hello. She asked if I had a good weekend and I must have blurted out "YES" really loud because she asked why I was in such a good mood for a Sunday night.

"Oh, I don't know mom, I guess it was just really fun to lay around a do nothing all weekend and binge watch TV for a change," I answered.

"Sometimes that is a great way to spend a weekend. I'm glad you had fun. Goodnight."

What I couldn't tell my mom, is that I am euphoric right now because, not only did I lose my virginity this weekend, but I may never have this kind of weekend again in my life.

I may run out of ink before I finish telling you, but here goes...

As you know, I was totally depressed Friday night. I put on a dingy flannel shirt, some old cut-off jeans, and headed out to grab some groceries. I didn't even do my hair or make up or anything.

I scored some junk food for the weekend and got out to my car and realized I had locked my fucking keys in the car. I slumped against my car and was sobbing. I don't think I was only crying about the keys, I mean I could always call our auto club 800 number, but I think I had just had it and I just started bawling. All of a sudden, I heard a man say, "Amber?"

I looked up and John was standing there. Shit. No make up, I look like a hick, my hair is a rats nest, and I am crying my brains out and partly about him. He asks me what is going on and I can't really say, so I say, "I locked my keys in my car. My mom and dad aren't home. And just everything is going wrong."

"Can you get into your house and get a spare car key if I took you there?" He asks in a sweet voice.

"Um, yes. I can open the garage door with a code," I answer.

So, he takes me to my house, but I am so mortified at how I look that I can barely stand looking at him the whole way. I was so embarrassed.

Anyway, I get the key and on the way back to my car, John asks, "Any big plans for the weekend?"

"No," I replied. "Just hanging out alone at home binge watching TV and eating junk food."

"Sounds like fun," he laughed.

Then, almost like an out of body experience, I heard myself ask him, "Want to join me?"

"Well, I wouldn't mind watching a movie and eating some junk food. Shall I follow you home?"

I lost my breath for a minute when I realized what he had just asked. "Um, uh, yeah. Sure. Okay," I burst out.

He dropped me off at my car and I quickly hopped in and sped for my house with John following. It is only about a 10 minute drive to my parents, but I swear it seemed like an hour as time stood still. I couldn't believe that the man of my dreams was on his way, with me, to my parents' house.

After we went inside, I quickly left him in the kitchen and told him to figure out some snacks and I ran to my room to make myself look somewhat presentable and not like a mess. I knew this was my chance, so I put on ONLY a long, button-up, night shirt that was made of really thin material. I knew for sure my nipples would poke through it.

When I came back, he joked about whether it was bedtime or not and I just laughed and said I wanted to be comfy. I got a bottle of my dad's wine, knowing he'd never miss it, and opened it for us while he made some popcorn and other snacks.

My parents have this huge, L-shaped sectional sofa, and the one long part is the best seat for laying back and watching TV. I told him to sit there and he insisted I sit there and then I said no way, he was the guest, and then, holy shit, it happened.

He said, "It looks like there is enough room for both of us. Why don't I sit there and you lean back into me?"

I don't even know how I answered, given the fact that I started to melt, but the next thing I remember it was dark, except for the light of the TV, and I was leaning back into the chest of my heartthrob watching a movie. I could feel him breathing. I could smell his scent. I was getting really turned on and starting to get wet. I got a chill, but I'll be damned if I was getting up to get a blanket because my nipples were poking through my nightshirt and I knew he could see them.

I shifted my body weight a little and for sure I felt a bulge in his pants pushing on my back. I could not miss this chance. Every few minutes I moved a little bit, rubbing against his bulge, hoping he would know I was doing it on purpose. He got even harder and was lightly thrusting himself into my back.

A few minutes later, he stretched his arms up and then draped them around my neck, and asked, "Is this okay?" All I could do was sigh and mumble a sound that meant yes.

He started playing with the top button on my night shirt. And then, he very purposely unbuttoned the top button. I think he was waiting to see my reaction because he just left his hand there completely still. The second and third button came back to back, and then he eased a couple fingers inside my shirt and rubbed very lightly on my upper chest. I sighed with pleasure to let him know the door was wide open.

He left his hand there, not moving down any further, but started running his other fingers through my hair and tickling my neck. Oh my god. If he had kept it up, I was going to cum right then.

I scooted up a bit on his chest and his hand naturally went down my shirt and rested right at the top of my cleavage. He kept gently tickling the very top of my breast area with his fingers. I eased my head to one side a little bit, and whispered, "I like that." He leaned forward, kissed me on the forehead, and pushed his hand down my shirt and right on top of my left tit. He was officially feeling me out. There was no going back.

My nipple was as hard as it ever has been and he gently pinched it and rolled it back and forth between his fingers. I moaned a little and looked back up at him. This time, he kissed me on the lips. It wasn't a passionate french kiss, but he held his lips on mine long enough that I was desperate for more. Instinctively, I reached back, touched his face and we started kissing some more.

As we broke off an extended, french kiss, he asked, "Are you sure you're okay with this?"

"You have no idea how long I've wanted this," I answered.

"Oh really. I'm flattered," he said, as his hand was now all over my chest and our kissing resumed.

While we made out, I ran my hand down between my legs and I could feel how wet my vagina was getting. I couldn't help it, my moaning increased as I touched myself. Not wanting to bring myself to orgasm, I eased forward and stood up. I think it surprised him for a second and he had the look of wondering whether I was closing the door. When I turned and faced him and started slowly unbuttoning the rest of my nightshirt, he smiled really big, knowing there was more to come.

As I stripped in front of him, I could see the huge bulge in his pants. Totally naked, I straddled him a bit, with one foot across his legs and on the couch, giving him a clear view of my perky tits and neat tuft of dark hair on my pussy.

I leaned over and grabbed his shirt and tugged up on it, signaling it was his turn to undress. He kissed one of my tits, sucking lightly on it, before pulling his shirt off. His belt easily unbuckled, down went his zipper, and I stepped back to allow him to slip off his pants. He was wearing boxers and his hard dick popped through the opening.

In the heat of the moment, I was surprised how rational I was, when I told John, "I need to let you know. I'm a virgin."

"Okay...," he started to say.

I interrupted him, "And I have been wanting you to be the first."

"Wow. Really? If you're sure this is what you want, I'd be honored. And I'll be very gentle."

I remembered the feeling I had when Aunt Sandy licked my clit, so I had John lay down and I moved into position over his mouth. My aunt was right about experienced men, he took right over. He held me in place by my ass as he pushed his tongue into me and started giving me the most amazing oral sex you can imagine. He kissed me and licked me and then sucked on my clit until I squealed loudly. To make it easier, he laid me back on the couch and buried his face in my pussy and increased the pace of his tongue on my wetness. It didn't take long after that. I tensed up, thrust my vagina hard into his face, and burst with an orgasm that lasted for longer than any I had ever achieved on my own.

It was so beautiful. He laid down next to me, caressed my body, and let me taste myself on his lips and tongue as he kissed me while I came down from the highest level of ecstasy I may ever know. I reached down and started stroking his dick. It was huge. The passion helped curb my anxiety a bit, but I couldn't help but wonder how much it would hurt to have him inside me.

I started thinking about how much I had wanted my first time to be in his hot tub, but there was no way I was going to suggest that. So, I said, "Let's go down to my bedroom. I want to lose my virginity on my bed." Without a word, he stood up, took off his boxers, scooped me up in his arms, and carried me down the hallway.

He gently laid me down on my fluffy bed, covered with frilly pillows and stuffed animals, stood there smiling at me, and said, "Amber, are you on birth control?"

I really wanted to lie, but I just couldn't, "No. I didn't think..."

"If we're careful, I can pull out just before I cum," John replied.

"Yes. Please. I want you to fuck me, now!"

John climbed on the bed and laid down next to me. As we kissed, he put his hand between my legs, spread them apart, and started rubbing my pussy. Slowly he eased in one finger, causing me to moan, and then, as I loosened up, he eased in more fingers and massaged me. He was so sweet the way he got me ready for what was next.

He positioned himself between his legs, took his big dick in his hand and started using it like a dildo on me. Aunt Sandy had shown me her dildo, but I had never used one. The head of his penis spread me apart a little at a time, until he said, "I'm going to push into you very slowly. It may hurt a little, but it will go away."

The pain from his dick stretching the walls of my vagina was easily overcome as I looked up at him and realized my dream had come true. About half way in, he backed out and then pushed back in. Slowly and gently he continued this motion, going a little bit deeper each time, until he finally pushed into me.

I screamed something like, "Oh fuck! Oh god," a few times and he increased his pace. I imagined it a bit like the porn I'd seen, his ass up in the air while he thrusts his dick back and forth, in and out of my pussy. I knew there would be time for it to hurt later, for now, I just wanted more and more.

It seemed like an eternity, compared to how fast it took Mario to cum when I stroked him a little, and then John said, "Amber, I'm about to cum."

"A little more. Please!," I pleaded.

He increased his rhythm for a wild 30 seconds and then yelled, "Oh shit, I'm going to cum."

As he started to pull back, I became like a sex-crazed woman and clamped my legs around him and felt a surge of hot sperm blast into the back of my vagina. The next few pulses of cum came very quickly until he was finally able to pull himself out and squirt a little more onto my comforter. I collapsed into my bed and was half crying and half laughing in a state of euphoria.

"Amber! What the hell? I just came inside you and you're not protected."

"Oh my god. That was fucking amazing. And, I can always get a morning after pill."

We laid together and cuddled for a little bit and then John got up and started to get dressed. I laid there naked, hoping he'd decide to come back to bed with me, and finally asked, "Do you have to go home?"

"I really should," he told me.

"Can I come with you?"

"Really?"

"Sure. My parents are gone all weekend and I'd like you to be the first for a few more things. Unless of course you don't want to," I say with a very deliberate wink.

As we head to his house, I rub his cock through his pants along the way and John is hard as a rock by the time we get there.

We enter the house and...You know what? I'm going to write more later. There is so much more to tell about our weekend together. Including the hot tub, Aunt Sandy, and whether or not I'm going to take a morning after pill.

Goodnight.

Amber.