This post comes courtesy of a wonderful writer and perversely fucked up friend of GetOffended, @2ndcitysaint and her blog, The Blog of Shame
Run away now, boys. This is a story about pegging. Oh? You don’t know what pegging is?
My favourite definition comes from urbandictionary.com:
“When the tables are voluntarily turned on heterosexual anal intercourse and the female servicee becomes the servicer for the man. Because most women don’t have penises, a strap-on dildo is necessary.”
So, you’re probably wondering: DEAR GOD WHAT TYPE OF MAN WOULD WANT THAT!? Well, some guys are curious. And it’s completely normal and not gay at all. Yep, not gay at all… even if my ex had sucked one of his friends’ dicks before. Plus, it’s not like a girl’s gonna go all out on you and use her 12” double-wide on you. No, she saves that for herself and no amount of begging could possibly make her want to put it in your asshole. Fun part of this story: the strap-on was HIS, not mine.
Moving on. Andrew, the ex in question, was the first guy I ever slept with on a first date. He bought me a $120 dinner at a fine dining restaurant here in town… how could I not? (To be honest, I fucked him because I wanted to, not because he bought me an expensive dinner, although I realise it seems that way). After that, our entire relationship was doomed destined to be extremely sexual in nature. It was to the point that he’d pick me up for dates, and we’d go back to his house and fuck before we even went on our date. And, then we’d come back from our date and fuck again until he bitched about it being 4AM and he had to work at 9. And then I’d wake him up again around 5AM for another round. Get the picture?
The chronology of when exactly the pegging happened is fuzzy in my mind. But we had discussed things like it right from the beginning of our relationship. I believe it first came up on our second date. I had gone to his house to cook him dinner, and we ended up making out on the couch while our dinner was in the oven. He was sitting and I was straddling him, rocking my hips against him. I guess the thrusting was pretty satisfying because it prompted him to say something like, “the way you move your hips, I bet you’d be great with a strap on.” So, I continued to tease him like that until the smoke alarm started going off and his dog started going crazy. After that, our attention shifted more toward dinner and less toward sex, for that night.
After a couple more dates, we were fucking and he decided he wanted a blowjob. My head was propped up by a few pillows, and he straddled my chest. THIS! This is a great position if you want to do the finger-in-the-ass trick because his legs are already spread, so you don’t have to try and spread them under other pretenses just so you can sneak a finger in there! So, I started with the usual shaft-stroking during the BJ… then moved my hand to his balls… then to his taint… and then I circled my finger around his asshole and gently pressed (after all of this happened, we actually randomly got stuck watching a pegging instructional video with the MOST ADORABLE woman who described this pressing the asshole as “ringing the doorbell.”) So, I rung his doorbell and he seemed to enjoy it… enough that he passed me the lube from his night stand. I lubed up, and in went the finger. He really enjoyed this, so after awhile he hopped off the bed and went rummaging through his drawers for his strap-on. Once again, I don’t know why he even owned one in the first place, but he did. Fun story: IF a guy owns a toy, it’s more than likely GUARANTEED to be smaller than his own cock. And, this was, in fact, smaller… which made me giggle a little. But, like a good, obedient girlfriend, I strapped on. Apparently, it was quite the site. He enjoyed it and just kinda stared at me for a bit, and I knelt there on the bed feeling slightly awkward, and also slightly powerful (kinda like a really nerdy guy with a really big [ok, less than average] sword).
So, we started out with him on all fours, which we quickly learned is not a great position. Thrusting something that you can’t feel because it isn’t attached to you… not as easy as you might think! But, we quickly found a great position: me on my back. He was able to be in control of the thrusts (because I was apparently a little too rough when we were trying it with him on all fours), he could play with my tits, and I was able to give him a handjob. After while, he started to get really into it, which quickly degenerated back to him being on all fours, so that I could spread his ass cheeks and pour more lube in there. If there’s one thing I learned, it’s that guys’ assholes are fucking DRY (and hairy).
By this time, I had finally figured out how to properly thrust something that wasn’t physically attached to me. We continued until after he came. Of course, neither of us realised that he came at first. I didn’t realise it, and he didn’t notice that he had until he started going soft and he saw the wet spot on his sheets (that, for once, wasn’t my fault). I didn’t get anything out of it, to be entirely honest. He came, so he obviously enjoyed it in some sense, and he told me he enjoyed it. I didn’t get anything out of it. But, for about 20 minutes after the fact, he got really awkward about it. Then after the 20-minutes-of-awkward phase was over, I felt really awkward; we were on the couch, and he got really cuddly… and then he decided it was an OK time to gingerly let out multiple farts… while we were still cuddling.
