Warming my boyfriend up to anal play has been a challenge thus far — to say the least. The last time I wrote about our forays, which was in January, I noted that I was disheartened by my boyfriend’s strong physical reaction to his asshole being touched. The truth is, it was so disheartening that I just didn’t even want to try for a while.
When we did try again several weeks ago, I tossed some rimming into the mix. He wasn’t adverse to it, but it tickled him too much. I ended up with the tip of my finger in his ass, but so much time had passed by then that he asked if we could stop. So I took the condom off my finger and sighed. For not the first time, I was frustrated and upset. It seemed like we weren’t making any progress, and it really sucked to keep seeing him squirm and grimace while I tried to get him to relax.
He was bothered too. If this process involved only his mind, I’d be fucking him with a strap-on up the wazoo right now. But his body is stopping us. His very strange physical reaction to anything coming near his butt is stopping us. He has never, until recently, regarded his asshole as a sexual spot. He is trying to change that because he knows how much it means to me. But even knowing how much he is trying, I am usually left with tears in my eyes, feeling like we will never succeed.
But things took a turn for the better the other night. I don’t know what it was, although it may have helped that he was slightly buzzed. We fucked first, with the Throe under us and the Bootie in my ass — that is, until it kept popping out. I was so relaxed that it just would not stay in. This was actually my first experience of double penetration with a sex toy and a real cock, and it was awesome while it lasted (I’m going to try it with the Romp next time, definitely). But that was just the build-up to the ass play…
My goal was to keep him hard for as long as possible while I played with his ass. I was somewhat successful. I propped his ass up on the Wedge and put on sky blue non-latex gloves — the first pair out of a newly-purchased box, our first box of gloves — and began slowly touching his ass with a lubed finger while also slowly playing with his cock. There was minimal twitching this time, and it wasn’t long before my finger was halfway in his ass.
“Does that feel good?”
“No, but it doesn’t feel bad.”
This is an improvement. It may not sound like it, but it is. My finger was halfway in his ass, he was not grimacing, and I was ecstatic. His erection faded, but he was not uncomfortable and didn’t immediately want me to stop. When I eventually took my finger out of his ass, I felt far more optimistic than I ever have.
As a finale, he fucked me with Mr. Man while I held the Hitachi on my clit. And yeah, I was happy.
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July 21st, 2009 at 1:30 pm
*dances a happy ass play dance* woot for progress!
July 21st, 2009 at 3:43 pm
I was the same way when I first tried to stick things in my ass. Like your boyfriend, I never thought of it as a sexual place until I saw anal sex in pornography, and I really wanted to try it. And I knew from my gynecologist appointments what having something up my butt felt like–foreign, weird, almost painful. That was always in the back of my mind, even if I didn’t want to admit it, which I think was my major barrier to butt play.
But after months and months of trying, I managed to get anal beads in to my butt and kept them in for a decent amount of time during masturbation, and I liked it. I still don’t LOVE anal, but I got over that unconscious clenching, and I know a lot of guys who get over the same thing end up loving it cause…damn, they have a prostate.
Seriously, though, this is great news. Now that his body isn’t rejecting things going up his butt, it’s sure to open up even more to the idea as time goes on.
July 21st, 2009 at 6:38 pm
It’s great that he is open minded enough to try and that he keeps making attempts to enjoy it. My wife doesn’t consider the sexual possibilities of her ass, but indulges my desire for having my ass played with. This last weekend she fucked my ass with the njoy pure wand and jerked me off to the point that I reached an orgasmic plateau where it felt so good and lasted so long I really couldn’t tell when I shot my load.
Keep on working it and good luck.
July 22nd, 2009 at 9:16 am
He’s a lucky guy to have somebody so patient to introduce him to all the wonderful erotic possibilities. Keep up the good work!
July 22nd, 2009 at 4:45 pm
As a male butt afficianado I would highly reccommend Anal Pleasure & Health by Jack Morin. It addresses issues such as societal taboos and subconcious fear about the anal area that most of us have had instilled in us from childhood. The book also goes over several exercises and techniques for warming up to anal experimentation. It can be much more complicated than just lubing up a finger and adding a bit of pressure. Knowing how to find a p-spot and proper ways to relax and relieve tensions are a must. If nothing else encourage him to experiment on his own, especially to learn his own body and anal region so that he may guide you to his pleasure and comfort zones. Sorry for the long response but I find myself ever more interested in anal play and health and would love to address or comment on any other forays or experiments you may have in the future. Don’t give up!
July 22nd, 2009 at 5:08 pm
@David: Thank you for the suggestion; I will look into it. We have already discussed him trying it on his own. Currently he is not interested in that and would much rather me do it. Hopefully that will change in the future, as I think it would be very useful for both of us.
July 26th, 2009 at 7:23 pm
Belated congratulations on your progress you two; just wanted suggest you might be interested in the Pro-Touch from Tantus soon. It’s nicely graduated, designed to mimic the popular come-hither fingering style, and ,best of all, you can stick a bullet inside.
Looking forward to hearing more as you two keep exploring, keep it hot and sweet!
July 26th, 2009 at 7:42 pm
@LLars42: Yes, I have seen that toy. Currently we are more interested in using my fingers because then I can feel whether or not he is relaxed, but toys will definitely come into the picture eventually.
July 27th, 2009 at 10:37 am
wow… sounds like quite a challenge, but congrats on making some headway
the only men i’ve penetrated anally were really into it, and with one of them it was new territory for him, but he took to it so quickly and enjoyed it so much i didn’t need to do anything to coax him into it… i’ve never tried to broach it to a guy who i thought wouldn’t be into it or wouldn’t have considered it before mostly because of embarrassment on my end :/
so yeah… good for you guys, and hope you’ll make more progress next time
July 29th, 2009 at 6:47 pm
@Epiphora: Doh! I forgot the most important part: it was my first butt toy, and more to the point, a blast to play with both then and now. Still, glad to hear it’s under consideration ^^