I started experimenting with anal masterbation when I was about 16 and I have enjoyed every moment of it. Not only does it feel sexy to be penetrated but it feels amazing during masterbation and orgasm. I am not homosexual just bi, and I have had many female partners who happily oblige to give me a hand back there. My current girlfriend enjoys anal play just as much as I do. This story is just a history of my experimentation and I hope that my stories inspire both men and women to try out a new form of fun.
I always try to incorporate my entire body during masterbation, rubbing my balls, pinching my nipples, tasting myself, and once when I was about 16 I would spank myself and start touching around my anus. Just running a finger around my hole felt great, so naturally I pushed one finger up there a little way with the help of some lotion. I would occasionally work my finger in and out of my hole but just the feeling of having it up there was amazing. Soon one finger turned into two, wich turned into three and all I had for lube was lotion and spit. As I got more comfortable with my anus I graduated to candle sticks. I would put ice cubes up my ass to start off the fun. The ice would make my ass numb and then melt, I would expel the melted water from my anus which worked well in cleaning it out. I once melted two 1.5' diameter candle sticks together and shaped them (a tedious effort) to form the perfect dildo. I used that candle stick until I turned 18.
It never got to be any thing more than this until I turned 18. A trip to the local porn shop taught me a lot. I purchased an enema bag, a large bottle of anal lube, a string of 1' diamater anal beads, a penis shaped suction cup dildo with balls and a medium vibrating butt plug. I felt so awkward at the counter lol.
After returning home I prepared a warm water soapy enema, in the shower I was clean in 5min. I ran to my bedroom, locked the door and positioned myself on a towel in front of my mirror. I ripped open all the boxes and pored lube onto my hands. I worked my middle finger into my ass followed by my index, once I was sure I had my self lubed up well I reached for the anal beads. I lubed those as well and easily pushed them one by one deep into my hole. I fitted all five of them inside me rather quickly, I stood up and felt them rolling around inside ever so slightly. I began a series of yoga poses concentrating directly on the pleasure issuing from my ass. My cock was throbbing. Removing the anal beads was the best part, as each one shot out my cock issued a line of pre-cum.
I grabbed the butt plug next. Again I applied more lube to both the toy and my anus. The butt plug was quite large and it took about 5min to work into my ass, screwing it back and forth. Once I got past the larger end of it my ass sucked up the plug, my anus closed around the end as it slid comfortably into place. I had never felt so full, the plug felt so large inside me that it almost hurt. I had very limited motion with it inside me, every move I made sent a shock through my body, somewhere deep inside my ass was the epicenter. It took some time to remove also, when it finally popped out, my ass remained agape, wide open dilated to the size of the plug, I could see clear inside. With a squeeze of my muscles my anus shrunk back to size.
I looked at the dildo on the ground. It was a flesh toned cock, 7' long 3' thick, it cost me $60 and was the most realistic penis they had. It had foreskin and a scrotum with two free floating weighted balls. At the end of the dildo there was a large suction cup and a small bag which you could fill with liquid and the cock would ejaculate through the tip when you pressed on a hose attached to the bag. It also had a vibrating egg inside it with five speed functions. I suctioned the penis to the second door of my dresser and filled the bag at the end with some lube, I lubed up the shaft well and positioned myself on all fours in front of the dresser. I backed my ass up as close to the dresser as I could and placed the tip of the penis to my ass, my other hand grabbed onto the door and slowly opened it causing the dildo to press into my anus. I could feel the head slip into my ass as I continued to open the door forcing the shaft into my butt. I began to close the door after the dildo was half way in, then opened it again slowly. I was suprised how realistic the dildo felt, I could make out every inch of the penis like anatomy as it moved inside me. I gave the bag a little squeeze and felt the warm lube ooze into my ass making the dildo slide around easer. My hand began to move the door faster and faster. Soon I was fucking my ass with such vigor that without even touching it my penis began to erupt. I sped up, my eyes rolled to the back of my head and I had the greatest orgasm to date.
I eased forward and the cock slipped out of my ass which once again gaped wide open, straightening up it closed and I could feel warm lube drip from my anus and down my legs. I was shivering from the intensity of the orgasm, my cock was still hard as a rock, I looked back at the dildo and down at the pool of cum. Taking my cum in my hand I turned back to the cock hanging there, ripped it off, stuck it to the tile floor and lubed it using my cum. I crouched down and lowered my ass down on the dildo once more. I turned on the first vibration level and just sat there rubbing my cock. My ass was on fire, every vibration was so precise. Soon I started rocking back and forth on the dildo, then up and down. I started to ride the dildo up and down sliding it in and out of my ass once again. I was pouring sweat and getting a great work out from all the up and down motion. After about 5min of humping this cock I erupted once again all over my floor. I stood up and the dildo fell out and laid on the floor lifeless. I had the largest smile on my face as I went about cleaning up. I took about a 20min shower and went right to bed.
Now that I am 23 I still enjoy anal masterbation. I highly encourage people to divulge and learn more about their bodies. Candles work great and so does your spit...I have since bought new toys and have had experience teaching both men and women the joys of anal play. My current girl friend is amazing and is the best addition to my 'toy' collection!
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