Anal Exxxplorations

My boyfriend and I have been trying to have anal sex for a large part of our 2 ½ year relationship. Every few months we’d get a little tipsy and start to have sex and he’d sexily whisper in my ear “You know what I think we should do?” and I’d breathlessly reply “What?” His response always made my breath catch in my throat. “I want to play with your ass.”

The last time this occurred was quite a long time ago. We started out with a small vibrator that is pointed at one end, perfect for slipping into a tight virgin ass. Once that was comfortable, he removed it and used a bigger dildo that was actually shaped like a penis, although much smaller than his. Then he tried to actually fuck my ass, but was only able to get his dick in a few inches before I couldn’t handle it anymore.

Now I had never played with my own ass before…..everything we did that night was completely new to me. I liked it a lot, in fact I did orgasm when he had the larger dildo in there. I’ve always wanted to try it again, but I think my boyfriend may have given up on the idea. He probably thinks it just won’t ever work and doesn’t want to go through the frustration of trying again.

The purpose of this story is to help out anyone who has found themselves in this same situation. I have done a lot of research and “practice” in the last few months, and I am now confident that we CAN have anal sex, and that I WILL enjoy it immensely. This is what I did this afternoon…..

After looking at some anal porn online and reading some erotic stories I was good and horny. My pussy was dripping wet, and I started fingering myself while sitting at my computer. After a while I turned the computer off and went in the bedroom. I spread a towel out on the bed and took off my clothes. I pulled our box of toys out from under the bed and opened it up. “Hmmm, I thought, what should I do today?” I took some nipple cream out and rubbed it into my nipples, making them rosy red, shiny, and erect. “Very sexy, I thought. I wish Michael was here right now.” Then I put a little China Nympho on my clit and within minutes it was throbbing.

I laid down on the bed on my back with my knees pulled up to my chest. Every so often my knees would brush my erect nipples, sending chills through my body. I rubbed my throbbing clit, but stopped right before I orgasmed. I pulled out the little green vibrator and covered it liberally in KY, and fingered my tight little asshole, lubing it up as well. I gently slipped the vibrator in my hot ass and turned it on. “God that feels so good!” I wiggled it around and pushed it in and out until it felt comfortable. Holding my larger pink dildo in my teeth, I kept up the motion with the vibrator with one hand, while lubing up the dildo with the other.

I slowly removed the vibrator from my butt, and quickly pressed the head of the dildo against my rosebud. Slowly the head slipped past my sphincter and WOW, instant pain. I wanted to pull it out so bad. Instead I started rubbing my clit and focusing on that sensation instead of the pain in my butt. Gradually I got used to it and starting moving it in further. Every inch I gained caused more pain, but I just kept rubbing my clit, and the mix of pleasure and pain kept me going. Once I had the dildo all the way in I just left it alone for a few minutes letting my butt get used to the feeling.

After a while I could feel the tight ring of my anal muscle loosening around it and it actually started to feel very good. I experimentally started moving it back and forth and pretty soon I was pounding my butt with my dildo. All of the sudden, instead of feeling pain, I wanted more! I wanted something bigger! So pumping away with one hand, I started rummaging around in the box with the other hand. I came up with a very large vibrator with an enormous mushroom head. The shaft of it twirls around and wiggles. It was much bigger than the dildo I had in my butt already, but just looking at it made me so hot!

The dildo was about as fat as my boyfriends cock, but not quite as long. I figured if I could get that in my asshole, I could definitely have anal sex with Michael. So I put a little dab of anal ease on the head of the vibrator and coated the rest of the shaft with more KY. I slowly pulled the dildo out of my ass and positioned the larger vibrator over my puckering asshole. To my astonishment it slid right in with no pain at all!

I switched it on, and the feeling of the shaft twirling around in my asshole, loosening that passage up for my boyfriend later on sent me over the edge. Rubbing my tits with one hand and fingering my clit with the other, feeling the sensations of the vibrator in my ass I came…..hard. With a sense of triumph I pulled it out and cleaned up.

Tonight when my boyfriend gets home from work I’m going to tell him I have a special surprise for him. Before he gets here I’m going to give myself an enema to avoid some of the mess I experienced this afternoon. I’m going to shave my legs and paint my toenails and dress up in this nice black vinyl outfit he loves. I’m going to have a bottle of wine ready and lead him into the bedroom. Then I’m going to tell him to take off his clothes, and sit back and watch. I’m going to prepare myself for him instead of trying to guide him through it, at the risk of him getting overexcited and making me too sore for the real thing. I’m going to do exactly what I did this afternoon, and when it’s time for the biggest vibrator I’m going to tell him to fuck my ass instead of using the vibrator. By that time he’ll be so hot from watching me play with myself that I know I have a good hard ass fucking to look forward to! And I know I’ll enjoy it!

I’ll let you know what happens if I get a good response to this story.