How it Started: Toy Anal

After giving my first blowjob I couldn’t get the thought of it out of my mind. I only saw him a few times before he moved away and he would always make an excuse to leave. Still every night in bed when I started to jerk off I would close my eyes and see his throbbing cock. I would see the purple head of his shaft glistening in the light from the TV screen. I would see the veins of his shaft and the occasional throb. I would image the feel of my fingers rolling his balls and gently squeezing. I would image the taste of his cock on my tongue and the feeling of his cum hitting the back of my throat. It would never take me long to cum. I would lick my fingers and hand clean, slowing swallowing my own seed.

Then I didn’t have any chances to get my hands on any other cocks, but I would watch porn movies and fantasize at night. I started to wonder about anal sex and my mind struggled a little with the idea. I knew I wasn’t gay; I wasn’t attracted to male faces or bodies, just their cocks. I lusted after the female form and their features. Still, at night, cock in hand; I would wonder what it felt like to have something move in and out of my ass.

I used to have these permanent markers that were maybe six inches long and maybe a nickels width. I would lick on the end getting it wet and slowly slide it up my ass. Laying on my back and reaching a hand under my hip I would move the marker in and out as I stroked my cock and imagined his cock back in my mouth. Forcing it deeper in my throat, even though I had a strong gag reflex, deeper until I choked. Close to coming I would push the marker as far as it would go and hold it there until my cock gave out its last spurt.

Before long I moved on to using the handle from the plunger. A little Vaseline on the end and it would ease right it. It went a lot deeper than the marker and I loved the pressure. It would hurt occasionally as it slid in deep, causing me to flinch a little, but I loved the feeling just the same. With the plunger I started getting back into the tub so I could jerk off and cum on my face. The warm cum landing all over my face felt so good and warm.

My parents separated not long after my anal escapades began. My father packed up all the stuff my mother left behind and put the boxes in the storage room. One day when he was at work I went through the boxes and stumbled across a vibrator. It was pinkish with little bumps on it, about seven inches long, a little bit thicker than my own shaft, with a screw bottom to turn it on.

I pulled it out of the box and looked it over. I could feel the knot of excitement in my stomach and my mouth went dry. My cock grew hard and my balls began to ache slightly. I hid the vibrator under my mattress and went outside to play football with some guys in the neighborhood. All through the game I kept getting this stupid, excited smile on my face. It seemed the harder I tried to stop the smile, the bigger it became. I couldn’t wait to try and slide that vibrator up my ass.

That night I didn’t even climb into bed. I made a beeline to the mattress to retrieve my prize, headed for the bathroom, grabbed the Vaseline, and stripped. Using two fingers I scooped out some lube and smeared it over my waiting hole. First I slid one finger in and out, and then a second joined. After smearing the vibrator I stepped one foot on the side of the tub and leaned forward on hand on the wall.

I pushed the vibrator against my ass; I didn’t want to go in. I pushed a little and still it wouldn’t budge. I started to push it in and out against my hole. It would move a little more, but not go in. I started to get frustrated and my cock and balls started aching. I pushed harder and I could feel it starting to slide in. The first pain hit, I jumped and my cock grew soft. I wasn’t prepared for pain. The marker and plunger handle hadn’t hurt.

I stood there for a second trying to catch my breath. My hand back on the wall, I leaned forward again and started pushing the vibrator into my ass. It started to slide in again and I was moaning through gritted teeth, “Come on, go in.”

With a sharp pain it slide in and I held it there trying to catch my breath. I pulled back a little and could feel my hole close as it slide out. Slowly I eased it back in and the pain was a little less. Pushing it in deeper my hand slipped between my cheeks as it went in to the thicker base. I didn’t move for a second, when I shifted my legs I felt my softened cock move, almost swimming in precum. I felt a slick string hit my knee and land against my inside thigh.

After a few moments of adjusting I started to ease the vibrator back and forth. Within a few strokes the pain was gone and I was experiencing a wonderful fullness and pressure. Stroking in and out faster I suddenly came to a stop and froze. A feeling came over me as if I really, really had to go to the bathroom.

The feeling passed and I started stroking in and out of my ass again. The bathroom feeling came back and this time I kept going. I couldn’t believe how good it felt. Holding it deep in my ass I turned the control at the bottom and it hummed into life. I gasped and my cock started to grow hard as I moved to my knees and leaned over the tub.

It was a little uncomfortable but I managed to fuck my ass with the vibrator and stroke my cock at the same time. My cock was so covered in dripping precum that I could hardly hold on to it tight enough to jerk off. A few minutes later I came so hard that it hurt. I could hear the f***e of my cumshots hitting the side of the tub. I squeezed my balls hard and my ass clinched. I moaned loud as a new vibration hit me. It felt like it was inside right behind my balls.

Letting go of my throbbing nuts I slid the vibrator out of my ass and it sent a shiver through me. I rolled over onto the floor. I lay there for a while with the vibrator still resting between my ass cheeks, cum leaking from my cock, forming a puddle on my waist and running down my hip, my hair a sweat mess. Easily I slid the vibrator back into my burning, aching hole and turned the vibration off. I started fondling my softening, slimy cock and at some point I fell asl**p.

75% (7/2)
Categories: AnalMasturbationTaboo
Posted by jekylhyde
6 months ago    Views: 1,691
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1 month ago
only thing better is to get caught
5 months ago
Great story!
6 months ago
wow that was wild it's like the first time I fucked my ass pussy with a vibator it was amasing