Hopelessly Anal?

I knew I was hopelessly anal when my new friend Frank asked if I had ever had anything like a dick up my ass. He was sleeping over in my room. Almost without hesitating, I rolled over for his dick. 

I was fifteen and had been sticking things up my ass since I could remember. Starting with the little black enema nozzle, attached to the red bulb, that my parents kept in the medicine cabinet and used on me when I had a fever. I hated the enemas! But something about being laid over my mom's lap, with a bare penis and bare bottom, and having that nozzle slid into my little hole, imprinted on me. From then on, I would crave it; sneak into the bathroom just to look at it. I would lay in bed at night thinking about it. Before I could even get a hard on, before I knew what masturbation was, I was sticking that nozzle, or my mom's longer douche nozzle, up my ass whenever I could. 

And when I started beating off, it was obvious! I would penetrate my little hole with anything I could find. My mom's roll-on deodorant bottle. A hairbrush handle. So when Frank popped the question, I didn't have to think much about it. Oh, of course I hemmed and hawed to protect my self-image. But the thought of a warm, hard penis in my tight little hole was...Mmmm...irresistable!

In my 20s and 30s, it was asking my wife for a finger up my ass while getting a blow job or masturbating together. I felt a little ashamed and abashed to ask for it. Like a naughty, pervy boy. But I couldn't help it, I had to have it! And oh god, it felt so good! Sometimes, before the sex started, I would go into the bathroom and put some Vaseline on my warm little hole, knowing I was going to want her to finger me. Then, I would be laying there, craving it, and working up the nerve to ask. I can feel that desire, that craving, as I write this years later.

In my forties, my anal cravings discovered a discarded toy. If you can picture it, a spindle on a stand with plastic rings on it, with the smallest ring at the top and the largest ring at the bottom. The spindle started an inch or so in diameter at the base and tapered up to a little ball-shape at the top. Perfect for entering and stretching my still-tight little hole. I would kneel in front of a Penthouse magazine, opened to the centerfold, and lower myself until I felt the little ball at the tip touching my hole; teasing myself with it until I just HAD to have it in me! I fantasized that the girl in the picture, with a finger on her clit, was seeing me beating off, KNEW I had something in my ass, and thought it was sexy.

In my fifties, on business trips, I would have the luxury of time alone in a hotel room, where I could do anything I wanted. One evening I went to a produce market and bought three different-sized zucchini squashes, carefully chosen for their shapes. Took them back to my room and spent hours fucking myself with them, starting with the smallest and working my up to the one I almost couldn't imagine getting into me--but craving it and loving it like crazy! I would bunch the pillows under me and kneel, like I knelt on Frank the third time I had his dick in me. I was in heaven, feeling those almost-penis-like, fleshy objects deep inside me while I teased and stroked my bare, erect penis.

Later, I graduated to dildos. I don't know why it took me so long, because what I really craved was to relive the feeling of Frank's bare hard dick in my ass. The warm, fleshy tip. The flare of the head. The straining and stretching. The "popping in." The deep penetration.

Then the problem of how to hide them. The silly fear of getting caught. The shame. The explaining. What if I got hit by a bus and my kids found them? Eventually, I would cave and throw the dildo (or dildos) out. And just as inevitably, the cravings would build up until I found myself in another adult toy store ogling the shapes and sizes of penises hanging on the wall, looking for just the right one. Sneaking it into the house. Dying to get naked and feel it touching my hole, challenging my hole, stretching me, popping in; penetrating me all the way up my ass. That feeling!!

If you're hopelessly anal, you know it, just like I do...