I think all of us have times that didn't go exactly as planned - sometimes it turns out good & sometimes it doesn't. Even though this one wasn't exactly what I was hoping for, it certainly turned out ok.
I was in college and it all started earlier that evening when my girlfriend Sarah and I (Dave) were taking advantage of her two roommates being gone for the weekend to watch some porn and have sex all weekend. We'd been dating for about 6 months and had been fucking the same length of time - we'd ended up having sex after our first date. We were both very sexual and found we enjoyed almost everything we tried from straight sex to toys, a bit of spanking (especially when we were playing out a 'bad schoolgirl gets detention' scenario) and even a bit of bondage. About the only thing we hadn't done was full anal even though she loved her pucker being teased by my fingers and sometimes my tongue and had squirted a few times while I was eating her and slid a finger up her ass at the same time.
Sarah always said she wasn't into porn but for someone who wasn't into it, she sure got wet and horny when we watched it. I was flipping through different porn vids on one of my favourite sites and depending on Sarah's reaction I either moved to another one or we watched that one. I'd found that she liked the amateur ones better but once she got good and horny she'd also enjoy the more hardcore ones.
We'd watched a few already and if the vids hadn't gotten me hard, I know her hand stroking me through my jeans would have and I was happily fondling her nipples and teasing her pussy through the loose leg of her shorts and her smooth pussy was already nice and wet.
We'd talked about anal a few times and she'd told me that she'd tried it with a previous boyfriend and it hurt too much so she was scared to try again. I'd enjoyed a bit of anal sex with previous girlfriends - it wasn't high on my list but it was good when we did it. Of course the fact that she didn't want to try it made me want to try it even more. Whenever we watched porn, I'd make sure I clicked on more than one that I thought would have anal scenes in it and each time, Sarah would say that she didn't think she'd enjoy something like that and I'd point out that they women seemed to be enjoying it. Her typical answer to that was, "Of course they seem to...they've either been fucked there so often that they can't even feel it, they're pretending to like it either because they're being paid or because they hope the vid will get them into better roles."
Of course I'd point out that if the guy was gentle, used lots of lube and went slowly enough that it wouldn't hurt and would feel good but that never got me any closer to trying it with her. Tonight we'd already had a few drinks plus a couple of pot gummies that my buddy had given me which always made her extra horny so when an anal scene came on not only did she want to watch it, she seemed to be enjoying it but when I casually suggested we try it, I got the same "it's kinda hot to watch but no, it'll hurt and I won't like it."
Normally I'd have dropped it there knowing that before the night was over I'd have shot at least one load into her mouth and likely one or two in her pussy but I'd had a few drinks too so instead I said, "come on...I promise I'll be gentle, take my time and make sure you're well lubed. If it hurts, I'll stop."
I was totally expecting her usual, 'ya right, not interested' so I was quite surprised when she looked at me for a few seconds and then said, "are you sure that if you use lots of lube, go slow and gentle it won't hurt?"
Thinking maybe I'd finally convinced her I quickly said, "I'm sure...I've done it with a few girlfriends and they enjoyed it."
"well, if you're 100% sure...let's turn this off and go to bed."
I damn near tripped getting off the couch and was naked by the time I got to the bedroom. Sarah wasn't far behind and when fell together on the bed she whispered, "Before we do anything else, I want you to know that you're a bad boy wanting to fuck my ass...I think you need a spanking."
As I said, we'd played with a bit of spanking and while usually it was me spanking her, sometimes she wanted to be the spanker and it was a bit of a turn on for me so I pretended to be unsure saying, "you really think I deserve a spanking?"
She got up and as she piled a few pillows near the bottom of the bed she said, "Oh yes, I'm sure...bend over the bed right now."
All I could think about was finally getting a chance to slide my cock into the pucker of her ass so I bent over the pillows leaving my ass totally exposed to her. "I'm not sure you're going to be a good boy and take your spanking without moving so I think I'd better make sure you hold still" and with that she took out a couple of the ropes we'd played with before, tied one end of each to my wrists and the other end to the headboard so other than being able to shift a bit I really couldn't move much.
Next I felt her hand running gently over my ass, followed by a quick slap that had a bit of a sting to it. After a couple of minutes of light to medium spanks she stopped, reached under me and felt how hard I was. Then she leaned over and whispered in my ear... "This was supposed to be a spanking for making such a naughty suggestion but it seems you're enjoying my hand on your ass so maybe I should try something else."
At first I wasn't sure what that 'something else' was but I was thinking maybe the little paddle I'd given her as a joke a few months ago (and yes I'd used it on her a couple of times but just for a few light swats to tease her) and was kind of bracing for it so I was quite surprised when instead of the paddle, I felt a couple of drops of something cool hit my ass followed by her finger spreading it around.
She'd teased my ass with a finger a few times on other occasions but nothing more so I was surprised when she started sliding it in and out, going deeper each time. When she'd gotten one finger in, she asked, "so does that feel ok, lots of lube, gentle and nice and slow or is it hurting?"
"Mmmm, no it feels kinda good!" and then it clicked - that was exactly how I told her I'd be with her ass!
My thought was confirmed when she said "Good!" and then slowly added a second and then after a few more minutes a third finger. It took a bit to get all three in and there was a little pain but once they were in, it actually felt good and when she pulled them out I was kind of hoping she was going to try a fourth finger but instead of another finger, what I felt next was one of her toys pushing against my lubed ass. I wasn't sure which one it was but it didn't feel as big as her three fingers had so I wasn't too worried.
