What's "Up Chuck"?

As many of you know I have had my fair share of sexual experiences. I’ve done a lot and had a decent amount of partners in my life. I’ve busted my nut in many orifices and on countless boobs, but there is one place I’ve never had the pleasure of ejaculating. That one place my friends would be in the anus, also known as the booty hole (in case you’re not familiar with fancy words). Notice I said “in” and not “on”. I’ve shot a load or two onto a nice booty, just never in......until this past Saturday night.... Before I get into the meat of the story, so to speak, I must provide you with a little background info. I’ve never been with a woman who was interested in allowing me to park my “beef bus” in her “brown garage”. For some reason I could never strike up enough interest in any of my previous partners. Susan has been the same way. We’ve talked and joked about it, but it’s never come to fruition. There was one time, back around Thanksgiving of ‘04, that we tried. We had been partying with Susan’s sister, and her now ex husband, and they mentioned that they occasionally enjoyed a little anal lovin. We had been drinking that night so when we retired to the bedroom we thought we’d give it a try. We relaxed and got nice and lubed and I gently began to insert lil’Chuckie. I got only the head in and Susan freaked the fuck out! She said it was too painful and she just couldn’t go through with it. Over the next year and a half I kinda got used to the idea I’d never be getting any anal. I’d even kinda convinced myself I wasn’t really all that into it. About two weeks Susan again brought up the subject, but when I’d press she’d say something about me being too big, or it hurting too much and the subject would be dropped. Fast forward to last Saturday. I’m standing in the kitchen talking to Julie on the phone. As usual we were just conversing about all you other bloggers out there, and how wonderful you all are....Suddenly I hear Susan say, “Is that Julie? Let me talk to her.” Shocked, I take the phone to my spouse so she could talk to my other wife. Having no idea what Susan wanted to talk to her about I hesitantly handed the phone over. I was shocked and dumbfounded when I heard Susan ask, “So do you like butt sex?” I obviously could only hear one side of the conversation, but it went a little something like this.... “Really? You’re kidding? Hmmm...I see....Does it hurt? You don’t say....okay, thanks...” I took the phone back and continued the conversation feeling just a wee bit on the weird side. After I was done I went back into the living room and Susan informed me that since Julie likes it okay, she’d be willing to give it a try later that night. I must say I was terribly encouraged, but still doubted it would happen. I told her she’d probably want to get her drink on so she’d be really relaxed and she informed me she’ll need more than booze....she was planning on taking a Valium as well. And then, ladies and gentlemen, it happened. Last Saturday night, sometime around eleven, Yours truly lost his anal virginity. At first, when we discovered we were out of lube, I thought the festivities would be called off. Luckily she suggested we try Vaseline. The vaseline worked, but let me just say it cuts down on the sensitivity factor big time. I’m surprised I was even able to come with such a thick layer of that shit spread all over my cock. We started out with her laying on her side and me loosening her up a bit with my fingers. I had one finger in there and she seemed pretty comfy till she said, “Well that ain’t too bad, but of course your dick is bigger than your finger.” I added another finger and continued to loosen her up. Meanwhile I was growing rock hard. It really surprised me that I was getting such a reaction from just fingering her ass. After a while she got up on all fours and I re-lubed us up and slowing began to slip it in. One inch, two, four, six...I continued on slipping it in till I was balls deep. Like I said before, I couldn’t really feel too much thanks to the petroleum jelly wrap enveloping me, but I was able to relish in the tightness. It felt great! She, on the other hand, wasn’t all that sold on it. She was bracing herself with her arms so firmly she really couldn’t get into it much. She did try to rub her clit at one point. Julie had said the orgasms had during anal were the best ever. But she couldn’t focus on rubbin’ her nub when she was so tense. After a good fifteen minutes or so I was able to get up enough rhythm going to get off. It was pretty damn good. I really enjoyed it and I think she might have too. We’ve talked about it again since, and she said it could definitely be something we’d do on special occasions. Well lets see, today is Valentine’s Day....so I’m thinking tonight just might be special enough to get it again!! Maybe she’ll be more relaxed this time... I do hope this wasn’t too TMI for y’all, but if it was I’m sure you’ll get over it! That's just the way I am. ;-) Oh, by the way, I guess I’m back to blogging. I reckon I just needed a little break after all. I hope I haven’t lost too many of you in my absence. Talk to y’all again soon! I hope your Valentine’s Day was ever so romantic!