My Anal Training Ch. 01

The four of us had stayed at the bar, drinking and flirting long after the others had gone. Our engineering firm had taken one of our managers who was transferring to another location out to get him appropriately hammered as a nice farewell. Also as a lovely and thoughtful going-way present, Gina, the big-breasted, black-haired receptionist, had given him a nice hand job under the table and had also taken him home with her. She had led him out by his tie to much applause, and the party had pretty much broken up except for us stalwarts—me and my three best friends at the firm: Tim, Todd and Bob.

It's not odd for a woman in such a male-dominated field to have almost all male coworkers, nor to have friends among them, but it has always been my tendency to have close friendships among men usually either leading up to, during or following a sexual relationship. Take these three: Bob and I had struck up a friendship soon after he was transferred to my department. Canadian by birth, he was blond, baby-faced and had a sweet, childlike openness. He loved to joke around, and I enjoyed talking to him. His roommate, Tim, a tall fellow with dark hair and a more brooding personality, didn't work directly with us, but we often took lunches together with Bob, so we got to know each other bit by bit. There was a lot of sexual chemistry between us, and Bob, who was seeing someone else, happily encouraged it. Tim and I developed a hot relationship, screwing each other pretty regularly, but we kept it casual—we both wanted to keep our options open.

Which is where Todd came in. A dark blond, stocky ex-Marine, Todd was a fun dude, sometimes aggressive with other men but putty in this chick's hands. He became drinking buddies with Tim and Bob and we had fucked a few times, one of which was a threesome with Tim. They didn't get into it with each other, but didn't mind sharing me. God knows I didn't mind it!

So there we were, all together, and naturally the talk turned to sex. "Damn, Marshall's going to have a hot time with Gina tonight," Bob observed with a leer, "Girl's gonna give him a nice sendoff."

"I wonder if she's going to let him fuck her in the ass?" Todd wondered with a speculative grin. "I heard she takes it that way."

"That's a rare woman, then," I offered mildly, "It's pretty difficult for most of us." Tim gazed at me with a rueful smile—he'd been trying for months to get in my back door. I loved his tongue in my ass and enjoyed being finger-fucked as well, but I wasn't ready to accept his cock. I had already had a couple of painful experiences when I was younger, and I decided that even though the thought of anal sex sounded hot, I just didn't have the physical ability to handle it. My cunt is so tight nobody really complains, though.

"Mmm, that's the fun of it," laughed Todd, "It feels nice, don't get me wrong, but the reason it's so hot is because it's so fucking wrong and dirty, you know?" he gave a delighted shiver as he proclaimed this. The others laughed at him.

"Don't you want to try it, Red? Maybe you'd like it," Bob asked me, jokingly, but in an almost wistful tone. He had broken up with the woman he'd been seeing for several months, and while he hadn't made any moves on me, he had seemed to appreciate my companionship more.

"Oh, of course I've tried it," I confided. They all looked at Tim with big smiles. "Long time ago," I clarified, as Tim shrugged. "Not fun. Really painful, in fact," I explained, with a grimace.

"It might not be so bad with the right guy," Tim smiled encouragingly. I smiled back—his persistence was cute.

"Or guys," added Todd lustily. We all had a hearty chuckle at that.

While everyone laughed, I thought about a book I'd read that had advice on how to have anal sex without pain. Apparently, the secret is to penetrate just slightly at first to get past the outer sphincter muscles, and then wait a minute or two for the inner sphincter to relax. Just pushing on ahead before that inner ring relaxes causes tearing, and that's what hurts. I read this with great interest—I had no idea there were two sets of sphincter muscles! That helped explain why some women seemed to love getting assfucked—they know the secret! I didn't say anything about it to Tim, but I decided to see if I could train myself to take a cock in my ass. It would be a nice surprise for him...

The day after the party, a Saturday, I headed off to the friendly neighborhood porno shop (okay, it's across town, actually, but they are friendly) and bought a nice cock-shaped soft latex dildo about 8" long. The head of the dildo was very bulbous, so when I got it home, I trimmed it down with scissors so that it was a bit more tapered at the head. I left the shaft at the regular thickness. I did have a small, 4" dildo that I could take in my ass, but I thought I might be ready for more and I wanted to be able to accept a man-sized dong.

I got myself laid out on the bed and worked myself into a very horny state, which was pretty easy, as I'd been wet with anticipation even before I'd left the store. Unfortunately, my butt doesn't provide its own lube so obligingly, so I had a tube of KY handy. I lay on my side because one of my gay friends says that gives you more control over how it goes in (although he was talking about being with another person, it seemed easier, anyway). I squeezed out a generous blob of lube onto the head of the dildo, reached down and started rubbing it against my tight little asshole.

I liked the feel of the cool, slimy lubricant squishing over the sensitive skin of my puckered rosebud, and the dildo rubbing against it felt wonderful, building up a delicious anticipation. I started pressing the dildo into my hole, very gently. The head went in just a tad; I couldn't see it, of course, but it felt like it was maybe about half an inch in before I felt some resistance. That's my inner sphincter, I thought, and I wondered how I was supposed to get it to "relax"? I have heard that you should bear down like you're having a bowel movement, and that's supposed to help, so I did of that while pushing the dildo in gently.

It still seemed pretty difficult. I'm by myself here, and I can take all the time I want, I thought. I stopped pushing and relaxed, and I really did feel it relaxing! I pushed slowly but firmly, and I felt my ass open and take the dildo. It was in! But it wasn't in very far, yet—the thickest part had passed through the barrier of my sphincter, but when it was in only a few inches, I felt some more resistance and discomfort in my rectum. I gave myself a minute and I seemed to relax again, so I pushed it in a little further—it was probably about 5" in or so—but it hurt again. I decided to switch positions to open up my ass a bit more. I got on my hands and knees, spreading my legs wide. Not only was this position more comfortable, it was much hotter! I could imagine Tim standing behind me, sodomizing my sweet ass like a jackhammer. The rest of the dildo slid home up my butt.

I was super excited, but I didn't want to mess anything up and hurt myself just as I was having success, so I let it sit for a moment, enjoying the sensation of my tight asshole stretched around the fat cock and the feeling of all eight pinches packed tight into my rectum. My pussy twitched and throbbed with pleasure. I could have come so quickly if I had touched my clit, but I wanted to have the pleasure of being reamed first. I wanted to see if I could take being fucked good and hard in my butt.

I couldn't wait any longer, so I reached around and started working the dildo slowly in and out of my ass in short strokes. It was a little difficult at first, but either my ass opened up some, or the lube got spread around better, because soon I was poling myself with that latex cock like a damn steam piston, and I was loving it! It felt so fucking good, and I could shove it into my ass as hard as I wanted once I got going.

I fucked my ass with that dildo until I lost the strength in my arms—oh, how I wanted a real cock inside me then, backed up by the driving, thrusting power of strong legs and buttocks—but I enjoyed the feeling of it jammed inside me while I tickled my sloppy clit to a massive, shuddering orgasm. My asshole pulsed around the dildo to the waves of pleasure pumping through my pussy. I knew that after I'd gotten enough practice to be sure I could do it right, I would happily surrender my ass to Tim.