My First Anal

I am straight. I love *****. So I'm wondering how many other guys out there enjoy stimulation in the butt, that haven't said anything :)

Okay so it started with me feeling really horny as usual. Everyone in the house is asleep, and I am in my room watching **** and playing with myself. I had been curious about anal play but it was 100% new to me so I was nervous. I found a Highlighter on my desk and got a naughty idea. I went quietly down to the kitchen and got a little bit of my moms cooking oil. I mixed it with some water in a little bowl and dipped the end of the highlighter in. I got on my back and held my legs up so my *** was in the air. For a while I just made circles around my tight virgin ***, rubbing the oil around. It tickled a little and I liked that. Then I thought I should get some oil inside, so I slowly pushed the little highlighter in. It was smooth and felt interesting.. a little cold, probably the water oil mixture. But it was a pretty small marker and I thought I could go for a little more. I think the next thing I tried was a jumbo Sharpie, also from my desk. This marker was a little bigger but still didn't give me any crazy, this feels amazing, anal. It just felt like there was a little something in there. I don't remember all the things I experimented with but I remember going up in size until I saw a tiny bit of blood. I got freaked out and stopped right then. I was still crazy horny, so I used a little of my oil mixture to jerk off. I sprayed hot *** all over myself, cleaned up, and went to sleep.

I didn't experiment much more after that, but I noticed slipping a finger in my *** while I was ************ felt really nice. I think I was going slow at this for a while before I got the confidence to try again.

It was just after Christmas, and I got one of those gift card credit card things as a gift from a relative. I was struck with an amazing idea: I could use this credit card, which had 30 loaded on it, to buy the sex toy I had always dreamed of ;D and I was dreaming of the Super Head Honcho ***********. I ordered it, along with a big bottle of lube, and said merry christmas to me!!***********-13277.aspx

I had ordered a DVD from this site once before, and when I did, it came with a free gift of three other DVDs which were okay. As I was checking out, they told me that this order had also qualified for a free gift. I thought: cool more DVDs. and pressed ORDER. The free gift is supposed to be a surprise and boy was I surprised! my box of pleasure finally arrived in the mail, and my mom asked what it was. a late christmas gift is what i told her ;) from me to me lol. So as you can imagine I just couldn't wait to put my **** in this thing so i ran downstairs to rip open the package. The head honcho came in a box with Sue Johanson on it so I knew right away I had made the right choice, and was in for a knee shaking ******. This put me in a very excited, horny mood. I pulled the bottle of lube from the box, which i had almost forgot about and my excitement doubled :D no more homemade veggy oil lube! this was actually very nice because the stuff i was using, which did work well, was very runny. ran away from my *** and down my back when i tried to use it. This new lube was more viscous, and more effective at lubrication so I was a very happy boy.

Then down at the bottom of the package I noticed another box. that's weird those aren't DVDs was my first thought. That's a really big box of grape flavored condoms was my second. This last box was a big purple vibrating *****. I thought they were condoms at first because it was not a smooth plastic vibrator, it was a rubber like one, had a big hard vibrating head, and veins that ran down from there. It looked very realistic. This was no small vibrator either, probably 9 ". I called the company and told them they had made a mistake, sending me a vibrator with my purchase of a ***********, it didn't make any sense. but the man on the other end told me the gifts were random and there was nothing he could do. it was free so i didn't really care i just threw it back in the box. I didn't think I would ever be using that thing. I didn't see it as a possibility at that time, it didn't even occur to me. I remember thinking, if i try to give this to a girl i know as a gift, we will no longer be friends she will think i'm a weirdo that had a *****. hahaha. ANYWAYS I probably used that head honcho 5 times that night. It felt more amazing than anything I had felt before. It completely drained me. There is a hole at the end so you can take your finger on and off of it to get a sucking sensation (and sound haha). I was in love.

I'm pretty sure the way this worked was every day I would think about that big purple ***** and get a little more and more curious and horny every time. One day I was home alone and just said **** it why not. I laid a towel down on the bathroom floor and got everything I needed ready. I got my *** lubed up and started to press against my little hole with the huge head of this thing. i thought there was no way it was going to fit. I got into a few different positions, I tried doggy, reaching around but it was a little difficult. I decided the easiest was just to put some lube on the ***** and put it on the floor standing up. I lowered myself down to it, just like i had seen all the women do in **** when they were about to ride the dude cowgirl. I screamed as the head entered me. it was stinging and i think i almost fell over. I took it out and was about to pull the plug on the whole thing. im not really sure why but i decided it was worth one more try. I laid on my back like before, with my leg over my head. I pushed it in and it didn't hurt. I was relieved but i wanted to lube it up more so i did, and for a while i just pushed it in and out about 2 inches getting used to it. I started to feel more comfortable and started to rub my ****. I got hard. this was a good sign to me. Having a big **** in my *** didn't feel good, but it didn't feel terrible either so i was only a little disappointed. I remember the tip i had heard for women which was that breathing is very important. I practiced for a while and got it about half way inside me. By then my *** was filled up. this ***** was by far thicker and longer than anything i had put in my *** so for the first time it felt good. stuffed. before it was just like i could kind of feel something in there, now it was like filling me up and i liked it. I started to stroke my ****. I had my back against a wall, and the ***** on the ground. I held onto my **** and started to bounce up and down trying to keep my hand static. I was trying to get the feeling of going up and down on the ***** to match up with the feeling of pushing my **** in and out of something. The head honcho was always able to make me blow my load in about a minute so i didnt want to use it. I wanted to enjoy my time with this *** stuffing *****. up until now i had totally spaced the fact that it was a vibrator. I turned the dial on the bottom slowly and it turned on. I didnt feel much. I turned it all the way up, and holy ****. I think I sprayed more *** at that moment than i ever had. all my life ive loved shooting loads, and prided myself on the amount of **** i could produce, but even this surprised me. I was barely rubbing my **** but having a huge vibrator suddenly go crazy in my tight *** was enough to send me over the edge.

From that day I started ************ with it in my *** a lot more. I eventually got it all the way inside me. I did try the head honcho one time, but i think i lasted like one pump haha so i just use my hand ;) hope you all enjoyed this story, and i cant wait to hear from ya'll

blujay666 blujay666
18-21, M
2 Responses May 24, 2012

Wouldn't you like it better with a partner?

awesome recount of your first time with a *****, I remember mine and it turned me on so much too. I sprayed so much *** while the vibrating ***** was in me and I was pumping on it.