My first time with anna
Introduction:
This story is somewhat true. I like to believe it made it this far but she went no further than down my pants.
It all started earlier that night when I went to a movie with my parents. After the movie we drove to pick up my little sister from her friend, Abby’s house. Abby had an older sister as well as one younger and their parents were good friends with mine. Abby’s older sister, Anna, had been a friend of mine for a few years and in the last year or so we had stopped talking as we went to different schools and never really saw each other.
Upon arriving to the house Chandler, my sister, coordinated a “show” for the parents along with Abby and the other little girls around.( Who’s presence surprised me, considering that it was already 9 pm). After chilling in the living room for a while I got bored and began to text Anna. Knowing she was home and probably in comfortable, springtime cloths. I jumped at the offer to come upstairs and listen to music with her. Very shortly after that I found myself at her closed door. Without thinking to knock I bestowed it upon myself to let myself in.
She jumped slightly and scrambled to hide a Corona she had no doubt stolen from the ice bin full of them downstairs. Upon realizing it was me she relaxed and set it back on her windowsill. As I entered her room I was delighted to notice she was wearing a pair of cheerleading shorts with loose legs and a low fitting tank top. Under the tank top I immediately noticed her hot pink bra supporting what I assume to be ample b cups.
She was sitting on her bed cross legged with her shoulder length, natural, bleach blond, wavy hair in a loose bun. Her room was fairly messy, (mainly cloths and soccer stuff) so the one chair in her room was piled with a purse and some socks, which left the only open seat on the bed next to her. (I wasn’t complaining.)
I sat down next to her and was embraced with an awkward silence for a few seconds. “Want one?“ she asked, breaking the silence as she picked up her drink. “Um…Sure.“ She reached behind her bed and returned with a bottle slightly wet from condensation. We started talking about sports and high school drama and eventually relationships while we enjoyed our drinks.
After a while I got up to stretch and moved a few feet away to the chair where I sat after removing its previous occupants. From my new seat I noticed that by her sitting cross legged I could see her red panties. Almost immediately I felt my cock stirring up so I tried not to look. However being a teenager who had been sex deprived for almost 3 months I found this to be very hard.
After a few minutes she shifted her legs which hid her covered pussy from view. We continued talking for a few more minutes when Anna decided to organize some photographs for school. Without getting off her bed she leaned over and began to rummage through them on the floor, leaving me with a perfect view down her shirt. After a few minutes of rifling through them she straightened and walked to her dresser to put the box of pictures away. Still talking the whole time she shut the door and walked straight back to me staring at me right in the eyes she stopped just short of me. “Ryan why have you been looking at my boobs? Do you want to see them? Do I impress you as the kind of girl who would just give that to you?” She asked very deliberately never breaking eye contact. I was lost for words, even if I could have found words I don’t think I could have spoken.
“Well do I?” She asked again.
“I.. umm… well… you..” I stammered. “Looks like your having trouble keeping your dick to yourself.” She noted, now stepping towards me and pushing me back into my chair as I tried to get up and moving my hands as I tried to hide my now raging hard on.
“How does it feel Ryan? To have someone starring at you? Do you like it? Does this make you hard?” She asked as she pulled her shirt up, stopping just below her bra.
I sat in my chair like a dumb kid when the teacher asks a question. Here I was trying to get away with a few glimpses to turn into a video in my head that night and now I had a girl, nearly half naked, teasing me. I stammered again. “Uh….Anna we…well..-” “Aah, no talking for you there, I’ll ask the questions. Do you like this? Would you like me to stop?” She asked rhetorically leaving her shirt which clung to her tanned athletic body like a glove not budging an inch as she slowly moved her hands down to her shorts where she hooked a thumb in either side. Again I stammered but this time I managed to get it out.
“Anna our parents are downstairs, you sisters..” she cut me off. “Well if you want me to stop then I can.” She said this with no intent of stopping as her hands left her hips and began their way up my legs slowly from my knees.
“I can stop now if you want?” She said as she began to lower herself onto my knees. ” What’s a matter, afraid of something? Our parents are drinking and having a good time they wont bother us, none of them will want to walk up the stairs anyway, they’ll just yell for us.” She took my hands and slid them to her ass as she stood back up now leaning over me. Making eye contact again, and never breaking it, she slid her hands to my almost painful hard on. She flipped her wrist and began rubbing my balls as she undid my belt and the button on my pants with her other hand.
“Lets see what little Ryan is packing.” She said as she attacked my zipper allowing my very average 7 inches slid out and stand as tall as it could. “Maybe this will help someone stay where he belongs.” She said as she broke eye contact to look down and spit on my throbbing dick.
“Still want me to stop?” She asked as she gave me a sloppy hand job making eye contact again with her beautiful light blue eyes. “Hell no.” I regained my voice as my heart slipped out of my throat.
Her ass was perfect, not too big but defiantly not small, it was soft and felt like a cloud through her shorts, I couldn’t wait any longer to get to it ”Aah, aah, ah!” she warned as I tried to slip my hands under the legs of her skimpy shorts. ” Ill be in charge of what you get tonight mister.” She stood up looking at me with a slight pout about her face, my cock still standing, now wet from her spit. She walked to her nightstand and picked up her phone. Before I knew what she was doing she snapped a picture of my dick. “Now if you don’t do exactly what I want you to do. This picture will get sent around your school faster than aids travels around a frat house.” I just sat there speechless again. She set her phone down. “And don’t worry about a condom incase you were hoping for that excuse. My mom put me on the pill months ago when I switched schools. She doesn’t trust any of the guys in public school. Now come here.” She said sitting down on her bed and removing her shirt now exposing her bra. It was hot pink in color with green splashes all over it. “Ever seen one of these on a girl in person before?” She asked.
“What’s it to you?” I answered.
“Looks like someone needs a reminder of who’s in charge here.” She said with authority. She stood and walked over to me, again never breaking eye contact. She walked up to me and slapped me right across the face. “ Listen to me closely Ryan. You are going to fuck me. Tonight. In this room. If you have a problem with that I’ll tie you down to that chair and do it. I’ve gone too long wanting your dick inside of me and your cum in my belly to let it pass now. Now stand up and take those cloths off. NOW!”
She didn’t have to tell me twice. I leapt out of my shirt and shorts but left my boxers on. Still being somewhat new to sex I wasn’t as comfortable with myself as I could have been. “So you think you can hide from me?” Anna asked in a joking tone. “Well then it looks like I’m going to have to do some work after all tonight.” She turned around from her desk where she set her now empty drink down. “I said off!” She demanded as she tore my boxers from my waist letting them fall to my ankles leaving me standing in front of her completely naked now. She looked admiringly at my dick for a few moments before looking back at me. “Ryan you have no clue how bad I want you rite now. I’ve been waiting for this moment as long as I can think. Ever since two years ago at the beach house when I noticed you spying on my while I was changing, yes I saw,” she added as a look of surprise crept across my face. “Ever since then I have spent every moment I could teasing you. Trying to get you to make the first move. But you never grew the balls to do it so now its my turn and we are going to do this my way now.” She now was squared to me and lunged into me forcing our bodies and lips together as I fell back onto her bed. While making out she began to grind her hips against my dick, somewhat painfully considering her shorts. No longer able to wait I moved my hands up to her ass again, glad to notice the slight moan that escaped her lips as I did. I grabbed both sides of her ass and squeezed. If at all possible her ass felt even more inviting than it did just a few minutes ago. After a few more moments she slipped her right hand from my back to my hand and brought it up to her concealed breast. After depositing it there she inched down to my dick which she began stroking slowly again as she rolled off me. Even over her bra her breasts felt like little slices of heaven. I had only had sex with one other girl but I had had more than a few trips up shirts with different females, I was no expert but these were more than perfect by my standards. Now releasing her whole breast from my hand and moving upwards I gently rubbed her soft skin from just under her collar bone, working down as slow and painfully as I could. It seemed to be working too as she began kissing harder and stroking furiously. “Want me to stop?” I asked with no intent of stopping regardless of what she said. “No, please don’t.” She begged. “Well I’m not just that kind of guy, your gona’ have to deserve this now there cutie.” I joked her not thinking of what she may do to ‘disserve’ it. She backed away from my face looking at me with an evil smile written across her face. “I have to disserve it?” She asked questioningly. Fine then, I’ll earn it.
With that she stood up and out of her shorts, and fell to her knees where she grabbed my cock again. “Time to convince me you need this Hun. What will you do for this?” “Anything, name it. I’ll do anything.” “Fine then. Anything? I want a video of you jerking of. By next Friday when your mom comes over to watch my little sisters. If you don’t leave it my little snapshot will start to multiply. Deal?” Quickly considering my options I agreed. The end of “yes” wasn’t even out of my mouth before my dick was in hers. She later confessed to having a sexual relationship for a few months with a senior which would explain why she was so good at this! Again I’m no expert but I’ve had some experience and this was heaven! She forced all 7 inches into her throat only to bring the whole thing back out, dripping with her spit, and lick the head a few times, only to return it to the back of her throat. After a few trips she licked up and down my shaft a few times and returned to her previous activities. I suddenly realized that if I came I wouldn’t be able to enjoy fucking her as much as I would have wanted to so I began to focus on anything other than her bobbing head. After a couple minutes she rose and looked me in the eye. “Friday” she mouthed as my hands rose to her chest to tear her bra off. Her breasts were flawless. She had a slight tan line but it was obvious that she had tanned in the nude, or at least topless, a few times. As I wrapped them in my hands I was almost impaled by two nipples that could have put an eye out. “Ryan I’m so wet, please make that itch go away” she moaned to me as she crawled back up onto my chest. Without giving her a chance to object I tore her panties off, depositing them on top of the growing heap of our cloths on the floor. She wasn’t lying. She was wet. Very wet. I reached under her leg to investigate and was greeted by a very well groomed patch of pubic hair and under that a her warm beautiful pussy. The aroma of her arousal had already swept up to my face and it smelled delicious. “How bad do you want this?” I asked trying to turn the tables. Truth be told I didn’t quite know how long I could wait either.
“Ryan, please.” She moaned as she mounted me.
Without allowing her to beg any more I pulled her marvelous ass down and forced my naked dick into her pussy.
The only girl ever willing to fuck me previous to Anna was defiantly not on the pill. Nor would her mom want her to be so I had never had sex without a condom before which might I add is an intensity above all others.
Anna moaned deeply as my dick slid into her tight pussy. “OOH Ryan please…ooh” She moaned as I slid in and out of her slowly enjoying this new sensation very much myself. “OOH yes, yes Ryan RYAN, YES!” Worried someone would hear I grabbed her mouth with the palm of my hand. In the process I also decided to take command and flipped her off of the top of me and onto her back.
Taking a hold of her hips I now began to fuck her like the world ended in five minutes. My balls began to slap against her firm little ass cheeks with every thrust. Our breathing deepened. Suddenly she began bucking and spazing (something that wasn’t new to me, I had just never been inside of a girl when it happened) As she began to climax her pussy contracted. This added with my already saved up load put me over the edge “ooh I’m gona come baby. I’m gona come inside of you rite fucking now Anna.” And I meant it. I came harder then I’ve ever before. My thrusts slowed and my breathing began to return. I collapsed onto her already limp body and slowly kissed my way passionately up her chest until I found her lips. “Thank you” she whispered as I got up to get dressed. After I had my cloths back on I found a pair of clean panties for her and dressed her returning her red panties to my pocket for a good memory down the road.
To Be Continued.
