The first time I tried anal was actually the first time I tried having sex. My first real boyfriend was a sweet guy, but very slow to initiate. We had gotten into fingering and HJs and BJs, but that was about it. My girlfriend suggested that if we weren’t ready to have sex, we could try anal (her words). So I suggested it to my boyfriend and he got really excited, which got me really excited, so we tried it right then. Bad idea. I had done next to no research, and he just tried to stick it in with no prep or lube or anything. It was really intense, then hurt, so I asked him to stop. I started to cry because I felt really stupid and embarrassed for suggesting it and then immediately bailing on him, like I’d let him down. We don’t try anal again.
But here’s the thing, I think the experience turned anal into this thing for me. It was going to be my first time, and then it got denied, so anal became this like special goal. Even though he didn’t want to try again (he was really sweet and didn’t want to hurt me), I started slowly fingering myself back there when I masturbated and started to really enjoy it. Long story short, here I am talking to you all. But I have to think it was that first time, and the way it became a sort of “forbidden fruit” that got me obsessed with anal. Anyone else interested in anal because their first time was a failure?
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Your first anal experience is more common than you think, particularly if, like me, had very little experience of any form of penetration. Its good to see you remained curious and are not afraid to try again. My first anal experience was horrible. 3 years later I love it!
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I’m glad to hear I’m not unique! Sometimes, I wish I had approached it more carefully the first time, but then I’m not sure it would have become this turn-on for me.
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Looking back, my horrible first experience of anal sex made me appreciate the pleasure and amazing experiences I now enjoy. It didn’t happen overnight but I was focused and I have the most amazing boyfriend who has supported me and joined me on our anal journey.
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“I wish I knew then what I know now”. Truer words have never been spoken when it comes to anal sex.
Years ago, another member said “anal is a journey, not a sprint”. Patience, care, and communication are needed and make the experience so much better than vaginal intercourse.
Foreplay focusing on the ass is key to successful anal penetration at first. I advise men new to anal to play with the woman’s ass until she craves penetration. Analingus, gently massaging the hole, and shallow penetration with a finger help.
Plugging before anal can also help a woman warm up for penetration. I recommend a quality stainless plug.
As the anal receiver, it’s up to you to communicate with your partner to make sure your experience is pleasurable. I guarantee this approach can work. My wife went from someone who swore I’d never penetrate her ass to the woman who wants only anal.
There is nothing more intense than anal sex because of the connection and communication between partners. Enjoy the journey and know there are many here willing to provide support and advice.
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One of my first relationships broke apart because of two reasons:
a) vaginal penetration wasn’t possible and she refused to see a doctor about it
and
b) she insisted we keep trying despite me no longer being interested and the pain it caused her.
And the other option was right there, but she also refused to even try. She claimed it was like me saying “huh, it doesn’t work there, gonna jam it up the backside instead.” Which, as you all can guess, was not my motivation. I broke up with her not long after, in no small part because she couldn’t accept that there would be no penetrative sex.
Did it make me want anal more? I’m not sure, but I was anal only with the next girl I dated, except for one experiment we both didn’t enjoy.
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