Evolution of Shitty Anal love, it started early

I have always had a fascination with the female ass, since a very young age. And by chance, my very first sexual experience was anal. That is the truth, but it’s because I was d***k and inexperienced. I fooled around with my girlfriend’s tits, and fingered their pussies, but real sex was just around the corner.

I was a freshman in high school (always the youngest in my class) and a girl named Sandra transferred to our school early winter. She was from Texas, and I lived in the north east. I was hooked on her curvy frame right away. She walked into class wearing tight jeans and a fluffy sweater. She had big tits, about a D and quite saggy for her age, just two years older than me. Her thighs were thick and her ass was round, but also lacked the firmness I was used to seeing in most girls that age. Like I said, she was two years older than me, so also not the sharpest tool in the shed as a freshman. She must have been left back at least once, maybe twice. She was a ditzy southern blond (dirty blond), begging for attention. I eventually amused her with some jokes and misbehaving in class, and invited her to a party at my house. My parents were separated, and my dad worked some nights, now I had to plan a party.

I never really got around to planning anything or inviting anyone, so it was just me with 2 six packs of beer, blasting Van Halen on the stereo when she showed up. She made some kind of joke about the big &#034party&#034 but didn’t seem to mind that I tricked her into the house alone. But it did take a while before she took off her coat and relaxed. We talked, smoked some weed, and drank all the beer. She looked at me and said &#034now what&#034. I was pretty naive and unsure how to make my move, lucky for me, she was not.

She said, &#034can I see your bedroom?&#034 As soon as we got there, she laid back on my bed. Her big ole titties sagged to both sides under her sweater and her legs spread slightly. She reached up her hand, I grabbed it and lowered myself on top of her, my crotch spreading her legs further apart as I fell right into place between them. I could smell some cheap body spray perfume, I wish I could remember the name. Possibly something from Avon, or maybe something she shoplifted from the d**g store. I did not mention, but she was quite poor, living with only her Mom in a run down rental cottage.

Man she was so soft, I was so buzzed, and we just started kissing naturally. I remember that I had a bit of dry mouth from the weed, but her tongue was super fat, wett and slippery. She had very soft full lips as well and my hands just went crazy exploring her tits and then down to her wide hips. Her jeans were already unbuttoned and unzipped! So my hands went right down both sides of her asscheeks as I pushed her jeans and underwear down to her waist. I sat up, and there was plenty of light from the livingroom for me to see some cellulite dimples on the sides of her thighs, an amazingly hairy dark blonde bush and big satiny panties around her knees. My dick was pushing hard against my jeans, so I stood up and dropped my pants and underwear straight to the floor. My cock sprung straight out like a jack in the box on steroids! She was Keeping pace, her sweater was pulled up and her tits hanging out. Her Aureoles and nipples were huge and a very light brownish pink color. Her pants were completely off and I could see a big meaty gash with long cunt flaps between all that hair.

She grabbed my rock hard boner, and her hands felt hot on my skin. I fell on top of her and used one hand and my opposite knee, to push her legs apart. I wanted to just ram it in, but also wanted to explore her body some more too. So I sucked on her nipples and rubbed her hairy mound. I could not believe the amount of hair for such a young girl, I truly could not find an opening from my position on top of her. So I just kept rubbing the bushy mound. She was moaning in my ear and rubbing my cock back an forth quickly. Then she lifted her legs up and parted them enough for me to find a hole down there. I grabbed my dick in one hand while my finger loosened up her tight hole. It was very tight, much tighter than I expected for such a large, soft, curvy chick. But there was plenty of slippery precum oozing out of my dickhead, so I slide it straight in. She started whispering something in my ear, but I could not hear with the music still blasting. I just started pumping slowly, and then picked up speed. Still, so suprisingly tight that on one of my out strokes, I was all the way out.

When I reached back down to guide my rod back into place, I realized something… I was in her asshole that whole time! So now I could feel her pussyhole, super wet and loose like I expected it to be, and right below, was her asshole (which was very very tight for what I thought was her vagina, but very loose for an asshole). I could not believe that my dick was up her poopchute that whole time. With no lube other than precum, and whatever must have dripped down from her cootchie.

Well, now I decided to try her big wet cunt on for size. By dick plopped right in and it felt like a hot drippy wet sauna. I started pounding hard and she was moaning like crazy, I was too young to know it at the time, but I’m pretty sure she had her orgasm right then. I on the other hand was having trouble getting close to cumming. I think it was too much weed and beer. So I said what the fuck, I already fucked her asshole. And the thought of sticking my wiener back up there got me really excited. So I slide it out of her gash, and in one stroke, I was back up her ass. Man it felt nicer this time with the extra lube from her slutty love tunnel. But after 5 minutes, I could tell I was just not going to cum.

She could tell I was having trouble and said, &#034what do you want me do &#034 &#034Just ask, anything you want&#034, she said. Since I have never had a girl perform oral sex on me, I said &#034how about a blowjob&#034. &#034No&#034 she said. My heart sunk, then she said &#034that was up my ass, I can’t do that&#034. So I decided I would do things backwards, and had her give me a handjob while I fingered her holes.

It was great, now I could really see what was going on down there and it felt great to have her jerk me off while I hade a finger in each of her holes. All I could think is &#034what a great first sexual experience&#034 I had done everything in one shot, except oral. Man, her holes were really loose now. My fingers were so wet from her overly lubricated puss. She really got wet. And the view of her wet gash and loose asshole made me cum hard. I was still kneeling between her legs, but I overshot her waist and covered her saggy boobs and face with about 5 squirts of thick goo. She did not mind a bit.

So, that was my introduction to Anal sex. It did not get messy or dirty or shitty. But I was well on my way. The evolution of a shitty anal lover will continue in my next story about my first &#034serious&#034 girlfriend Isabella. She was a beauty, half Italian, half Jewish. She could not walk, without her hot young thighs rubbing together. But she was curvy and firm from all the dance classes she took. She was a real spoiled rich princess too. With lush jet black hair, big brown eyes, fair skin and had a few unique freckles on her face and nose. She was a pleaser, that used to do anything I wanted. And what I wanted was to fuck her in the ass!

Well, you’ll have to wait for the rest of my life story.