Diary of John: Dana

This is a work of fiction, everything in this story is fabricate to create my own personal ideal world. All characters in sexual situations are 18 years of age or older.

*****

Captains log: entry #1

Star date in earth years...

Nope, nothing I do makes a diary sound cool. I'm writing this so I can relive the memories of my sexual adventures. From when I was a teen to now. Cause god I had some good times. I know I'll be judged for the most part, but I hope you understand.

Memory 1: Dana

It was the eve of my 12th grade year and just before summer started I had just gotten myself a new girlfriend. You know, a part of me wish's I stayed single back then, I was popular with the ladies, I may have been called the "not gay gay best friend" more times than I could count but it had its perks, girls trusted me with every little secret, they would always came to me for advice and I was always the only guy invited to their slumber parties. I had recently found out that a majority of them would have gladly fucked me if I had made a move and if I did not have a girlfriend at the time. But having a girlfriend did not stop me from getting some ass on the side.

Hold up, let's back up a little so you understand how all this came to fruition.

It was my first year in this new school for my 11th grade year. My parents were in an accident when I was in 10th grade resulting in me moving from England to Canada to live with my Godparents. Let me tell you, North American girls are easy to woo, all you need to do is look good, sound smart, know how to talk and have a big dick and an accent.

Anyway, summer had just started leading into my 12th grade year and on the last day of school I had learned that all my mates that I usually hung out with would be gone for the summer. My girlfriend of three weeks was gonna leave for her yearly trip to visit family abroad. With a huge chunk of my new mates gone for summer vacation with their families the majority of my summer was spent with Dana.

Oh my god Dana, at 5'6 she was a dancer. She was part of the school program that had her leave school after lunch so she could go to dance class, she had flowing brown hair that she draped over her chest mermaids style, her hair along with her green eyes complimented her naturally tanned skin.

She never had time, or she never made time to spend with her mates, (I could never tell which it was) she always sat off to the side of the group at lunch, she would never make an effort to talk to others and she never spoke to any of the boys. When she did talk though, I couldn't help but notice that she had a cute round face and a gorgeous smile. she always wore sweaters that were 2 sizes to big so I could never tell what kind of body she had. Although I knew she was fit because every time she stood in front of me during chemistry I couldn't help but notice she had toned slender legs and a small round firm ass that seemed ready to pop out of every pair of pants/leggings she ever wore. No doubt a bonus that came with being a dancer. I always made an effort to grab a seat behind her. A: to get to know her better and B: to watch that ass. I always fell behind in class cause I spent most of the time fantasizing how her ass would feel cupped in my hands.

I asked Dana if she wanted to hang that weekend, even though school would be over tomorrow she was still participating in dance classes over the summer so I took that into account. I honestly thought she would have said no but her response surprised me.

"Sure" Dana said with a smile, "what do you wanna do?"

"You're gonna hang out with John?(btw my name is John), Dana?" Our friend Nat interjected, "good job James! I've been trying to get her out of her house for weeks now."

"Really?" looking at Dana questioningly.

"Yeah" Dana's cheeks flushed as her eyes made their way to the ground "I don't like leaving my room but, my parents told me to hang out with friends this summer or they won't teach me how to drive."

Nat and I just laughed, breaking the laughter was Nat whispering into my ear "I'm gone this summer so you take care of her, get her out of the house as much as you can. She will probably only hang out with you cause she trusts you. She has issues with boys in general. So try and have fun at her pace, Kay?"

Dana, face now beet red threw an irritated fist "Nat, what are you saying?" Clearly upset she was left out of the secret, a secret probably of her.

Smiling at her cheek to cheek "well, I promise try and make it more fun than your room."

I spent the next four days hanging out with my girlfriend, trying to get as much time in before she leaves, trying as hard as possible to coax my hands into her pants but to no avail. I was her first boyfriend but she was not my mine and I was horny as fuck. My cock hadn't seen pussy or mouth since I came to this fucking school. I hated meeting new people, making friends, building bridges. As horny as I was I wanted to fuck the gentleman way... or so I thought until Dana and I eventually hung out at the beach.

The summer went by quickly, school was starting in three weeks, Dana would be gone for the last two weeks but nevertheless Dana and I had fun watching movies together, playing video games, going out and going with the flow, I treated her to lunch when she turned 18 midway through summer. We found out we were both late in starting school making us a year older than everyone. Her and I grew really close, my girlfriend kept asking if she should be worried, I kept assuring her that there was nothing there. Dana and I were just close friends, I ended up becoming one of her close friends that she could talk to about anything, I admit I was her only male friend. But there was nothing. Eventually I suggested that we hang out at the beach before she leaves. She hated the beach, every time I brought it up she always shot me down. During the summer I ended up going to the beach with my godparents for my 18th birthday, I invited Dana but with her thoughts on the beach she opted to stay home. I found out that the city had complimentary BBQ Grills at the beach, all you needed to do was bring coal and food to cook. She didn't shoot me down this time when I offered to cook her food.

The beach was hot which is what I liked, Vancouver had amazing summers. I was fairly tall, but still on the shorter end of my male mates. Being half Asian half European at 5"10 with a slim build I took to the gym after my parents passed to relieve my stress and it worked out great for me. I was as tall as I knew I was gonna get and as buff as I wanted to be. Visual 6 pack, perfect guns, nice pecs and according to my girlfriend, a strong jaw line. The beach was the perfect place to show all that off. There I was standing at the grill, preparing the food, waiting for Dana to arrive and indulging myself in women of all ages turning their heads to admire my form. Grinning like a jackass I was startled when hands tickled my sides accompanied by "boo!"

I would like to say I didn't scream like a little girl or that I didn't jump in the air dropping one of the steaks on the ground. But nope. I did all of that, I was honestly surprised I didn't piss myself.

"Oh my god..." I heard behind me as I turned around, palm to the heart I saw Dana standing there in her usual attire except she was wearing white short shorts this time "I didn't think I would scare you that badly... I'm sorry"

"Psh, you didn't scare me..." I said like an idiot

"Wow... now I'm not sorry for interrupting you while you stroke your ego."

"Hehe you saw that eh?"

Yup, sure did. Gotta admit though, you did look hot. Even my mother took notice while she was dropping me off."

Smiling like an idiot I just said "Tell your mum I say thanks."

After cleaning up the mess I just made I helped Dana set up her beach towel and parasol. I couldn't help but notice that her brown hair pulled back in a high set pony tail, she dawned the signature over sized Dana sweater, but this time she wore tight white short shorts that fell an inch shy just before revealing the start of the curve of her tight round ass. This was the first time I saw her bare legs, they were indeed slender, toned no less from years in dance. Just when I thought I saw all I would see Dana stood up and began to take off her sweater.

My jaw dropped, literally dropped open and I'm pretty sure I drooled a bit.

I can still remember it perfectly. It was like time had started to slow down. She reached down to pull her sweater over her head slowly revealing a flat toned stomach. At first I thought she didn't wear a top because I only ever saw her wear those big oversized baggy sweaters. Then I realized why she wore those sweaters, because after the stomach came her breasts. She was wearing a sky blue bikini top with yellow trims that covered her bouncy, perky and firm DD-cup breasts. And that's when the jaw dropped. When she was finished removing her sweater she moved onto her shorts, bending over to allow her perfectly round ass to spring free, covered by bikini bottoms that matched her top. I could feel my cock stir at the sight, this is when I realized how dumbfounded I looked and proceeded to turn around to prepare the meal. Giving myself time to cool down.

"Damn it" Dana sounding irritated. I turned myself around finding myself admiring the body before me "this is why I hate the beach, the sand gets everywhere!"

"Yah, it's annoying but it's nice sometimes" how I wished I could be all over that body... I mean my girlfriend was pretty, but this Dana was HOT.

"Really? How so." Dana asked irritatingly brushing the sand off her sweater and towel.

"I like when it gets between my toes, it feels nice. I don't know what it's like to get sand in your bikini but it can be annoying when you get it in your trunks and it clumps up around your balls."

Dana looked at me and laughed "it can suck when it clumps in the bikini bottoms too."

The rest of the day I keep catching myself staring at Dana, admiring her body, wishing I could touch that body. We talked about nothing and everything. I found out that she would be back 3 days before school started, I also found out that the yearly 'before school starts sleepover' that the girls had would have all the boys there. Apparently Lauren wanted to have big campfire at her house and invite the boys, eventually that led to "let's just let the boys sleep over too." Being now one of the boys I was also invited. The idea of sleeping next to Dana was turning me on so much that I had to lay flat on my stomach to hide my erection.

That night, I masterbaited to the thought of ravaging Dana. The thought of my hands all over her tight body. Slamming my cock deep into her virgin pussy... that night, I knew I had to have her.

Which takes me back to the eve of my 12th grade year. There I was sitting around the fire pit with all my mates. My girlfriend who had returned the night before was sitting next to me enjoying a conversation she was having with Nat about their summer ventures, I was trying to hold a conversation with my mate but all that was on my mind was the girl who was on the other side of the fire. Dana. She was wearing the usual Dana attire paired with overly thick pajama pants. It was a cold night, but not that cold. I don't know why she always wore those sweaters but if it wasn't for those sweaters you would never had guessed she was a walking erection popper, my eyes kept undressing her and I wondered how those tits would feel wrapped around my cock. Our eyes kept meeting and we would alway exchange smiles and return to our respective conversations. When she got up to go to the bathroom I got up and took a seat on the bench next to where she had sat. Starting a conversation with Lauren I thanked her for inviting me, trying to be all nice when I felt someone squish up against me on the bench. Turning my head I was happy to see it was Dana who picked up where the conversation left off with Emily.

After exchanging pleasantries with Lauren I looked over to make sure my girlfriend was occupied before making a very uncomfortable pivot, making sure to rub my body against Dana's before turning my attention to the fire.

"You want a s'more?" I asked Dana

"Sure! I've never had one."

"Really? They're amazing!" Puffing out my chest clearly about to spout some bullshit I say "Back home they call me the s'more master."

"Sure sure 's'more master' just make me my s'more"

I burnt her s'more. I ended up eating it and making her another one, less burnt but still burnt. We talked and laughed, then I noticed her wince when she turned her neck.

"You okay?"

"Yeah" she replied plainly "while I was at dance camp and injured my back on the last day."

"Fuck" my mind was already racing with thoughts of massaging her body "I took massage classes with my mum back home before she passed, if you want I can take a crack at it sometime."

"that would be nice." She says massaging herself " it's been hard to just move."

The rest of the night went along without a hitch and then it was bedtime. We all had to wake up early so that we could catch the bus for the first day of school so it was an "early night" they all finally passed out at 2am. We all slept in the game room, all 14 of us sprawled out on the floor. The boys on one side the girls on the other but head to head. I made an "effort" to sleep next to my mate which just so happened to put me head to head with Dana, all I needed to do is look up and I would see the top of her head. My girlfriend was sleeping soundly on the other side of the room next to Nat. Lauren had earlier offered Dana the guest room down the hall, she said it was sound proof cause it was the only room in the basement surrounded by concrete, so she wouldn't hear us if we stayed up late gaming and talking. She didn't want Dana to sleep on the hard floor or the couch with us cause of her back but she politely refused because she wanted to be with everyone.

2am passed and the room was silent with some sounds of light snoring rolling across the room and the only other thing making noise was Dana, she was restlessly moving around trying to find the right positing to sleep on the carpet floor.

"Pst! How's your back?"

"You're not asleep?"

"How can I sleep when all I can hear is your anguished moans? How is your back?"

"It hurts..."

"Get up, I'm taking you to the bedroom."

"No, it's fine"

"Everyone is sleeping they won't notice you missing, come on let's go. A soft bed will help your back, not hard carpet floor."

I didn't give her enough time to think it through, I got up and slowly eased her to her feet then bridal carried her to the spare room. Closing and secretly locking the door behind me, placing her on the bed I told her to lay on her stomach and she did. I then straddled her just below her butt and told her to relax. Which she did, she knew I was going to give her a massage.

I made conscious effort to act all flimsy because of her baggy sweater, but I continued to massage as "best" I could. We talked about how she got her dance injury, I then asked where it hurt then proceeded to tell her that the muscles are all connected and that her problem might be solved if I massage her legs or feet as well, but I still continued sloppily massaging her back through her sweater. About 10 minutes in I suggested in removing her sweater so that I can get a better grip on her back. Without giving her time to think I moved my hand under her sweater sliding my palms up her back to her shoulders. It was then I realized she wasn't wearing a bra, I mean, she had the comfort of her big sweater hiding her breasts so why not go braless? Besides she doesn't even talk to the guys, except me so she was 'safe' right? Reluctantly she let me take her sweater off, with promises that I won't look or touch her.

Massaging her back I noticed how slim and fit she really was her back, like her legs were toned, not overly muscular but just enough to keep a perfect feminine physique. Her light body squishing her breast against the bed, looking at her from behind I noticed that the sides of her breasts peaking out in a teasing manner. My hands were so close, yet so far. In other words she had a perfect hourglass body. Her skin was tanned, smooth and flawless, and she had a small mole just below her right shoulder blade. Asking again where it hurt I moved my hands slowly to her lower back.

Now the guy who taught my mums massage class was a real creep. Short old Indian man. He would hit on all the ladies, but not my mum. He knew my father would have him deported if he lay a hand on my mother. But he did give me 'secret lessons' when all the people were packing up their massage gear. He taught me of places I could touch a girl while massaging her back, legs, arms and feet if I wanted to get her "ready for a pussy poundin." After every class from then on he taught me more and more moves I could do, I could tell he wasn't lying because every lady he used as a demonstration would get all hot and bothered, then after class was done he would take them to the back room for their 'weekly appointment.' I admit I had tried them out on a few girls from my old school back home and it worked. That was my first fuck. But this, oh this I was going to savor every moment of touching Dana's body.

"This feels kind of awkward..." Dana sounded uncomfortable.

"Really, how?" I asked still massaging her back.

"I'm topless in front of you..."

"It's not like I'm touching you or looking at you." I realized what I said after I said it.

"Uuhhh..."

"Okay, I'm touching you and looking at you. But you know what I mean." Trying really hard to not sound nervous and stupid I said "here, I'll take off my shirt too." With speed I didn't know I had, no doubt fueled by sexual desire, I took my shirt off and plopped it in front of Dana's face so she could see it. Realizing what I just did, I was about to apologize when Dana started laughing.

"You know, it's not as awkward anymore when you act like an idiot."

Laughing with her I said "Sorry, but I'm glad I made you laugh. I just want you to feel comfortable with me. Besides it's me, you're in safe hands." Saying those words I felt guilty that unbeknownst to her I was guilting her into letting me seduce her.

"You're right, I do feel less tense. So thank you."

"It's what I'm here for!" With my hands back on her perfect body all that guilt slipped away and was quickly replaced by lust.

First was the sweater. Now I had to find some way to get her out of her pants.

"Here right?" I asked as I applied pressure to the mid section of the left side of her back. "And here, right?" Applying pressure to the right lumbar area of the right of her back.

"Ow, fuck. Yea. It hurts the most there" Dana squirmed her body to the pressure I applied. While she squirmed I held her down pushing my hands into her shoulders and my hips into her soft plump ass.

"Stop moving so much, you'll only make your back worse" while she struggled she pushed her ass up into my crotch causing me to slowly get a semi. I didn't want that yet so I eased off the pressure and she relaxed.

"Sorry... I just didn't realize how bad my back really was until you started massaging me."

"It's fine, if it hurts to much I can stop." please don't say stop, please don't say stop...

"It's fine, you're actually helping. It's starting not to hurt as much and I'm starting to feel good" she relaxed all her muscles. I could feel her body go slack under me "thank you for taking care of me."

"What are friends for?"

As I continued to massage her back and the arms at her side gently gliding my hands to her ass. She tensed then slowly relaxed, I'm assuming that since I eased some of the tension in her back she figured I knew what I was doing.