F*ck Around and Find Out with Anna Lee: From woman to woman

Hello, my sweet pumpkin patooties! What’s everyone dressing up as for Halloween? I couldn’t decide between being really scary or being really scarily slutty, and while going back and forth, I ended up with decision paralysis and didn’t buy any costumes. So instead, this Halloween I will be wearing my trusty four-year-old banana costume while I eat a bag of candy corn. Anyway, while that is not very sexy, I will still do my duty to ensure you all stay sexy with sex advice. I’m dedicating this month to women who have written in so you can have a spicy Halloween. Let’s go!

I’m a straight woman and I’m just curious if men can tell the difference between putting their penis in a vagina compared to a butt? Like, what does anal versus vaginal sex feel like for men?  -Tina M.

Tina, if you want to know one thing about me, it’s that although I do not have a penis, I am not a quitter. You wanted to know what the penis feels when it goes into a vagina versus an anus, so I researched, interviewed, and investigated. I can confidently say my speculation seems correct from what many penis owners have told me. The vagina feels like the type of hug you get when you pick up your significant other from the airport after they’ve been gone on a week-long trip. Firm but tender, all-encompassing, and warm all over. Because the vaginal walls have muscles running throughout the whole canal without much change in diameter throughout, it pretty much evenly wraps around the penis like a nice hug. The butthole however, is like the type of hug you get if your significant other is a foot shorter than you and you finally get to see each other after six months apart. It’s the shorter person’s arms reaching and wrapping very tightly around your neck. This is because the anal sphincter is a very tight ring of muscles at the entrance of your anus, while the rest of rectum widens out and has the ability to stretch out quite a bit. So the penis would generally have a very strong ring of grip but beyond the ring will be much more relaxed and spacious.

And hey, there’s nothing wrong with sticking your own (clean) finger in each of your holes. Take advantage of the fact that the penis head has about 4,000 nerve endings and the fingertip has about 3,000! You can really feel it. ;)

I just prefer masturbating with my toys at home rather than going out/hooking up/casual sex. At lunch today, my friends told me that I’m totally unhinged for choosing toys over casual sex, and that I need to get out there and orgasm with humans. I don’t see the problem! Do you think it’s weird? - Alisha

Girl, you are PREACHING TO THE (vibrating) CHOIR. First and foremost, you don’t see a problem and if you’re perfectly happy with it, that’s the most important thing in this case. There’s absolutely nothing weird with toys over casual sex because those are two very different things! There’s a lot of things that can entail casual sex: emotional connection, feeling of safety, unknowns of each other’s bodies, reliability, the social aspect, etc. Sometimes you just don’t need to be concerned with all of that and you just want to get the job done by B.O.B. (your Battery Operated Boyfriend). If anything, my lame joke probably makes me the weird one, not you. You can tell on me to your friends. 

What’s your secret to having the best sex of your life? I’m a woman and I need to know. -Anonymous

I wish I could tell you it’s some wild-*ss sex position I learned while in a 500-person orgy called something like Drilled Fountain Double Blaster 8,000 XXX, but unless someone wants to invent that and let me know about it, my answer is more wholesome and earnest. The best sex of your life happens through the holy trinity: communication, knowing your own body, and letting go. I know most people have heard the advice of communicating with your partners a sickening amount, so I won’t dwell on it, but it's crucial because otherwise they will never know what the best sex ever for you entails, and therefore they can’t help. However, the main hill I’d die on is how important it is to actually learn for yourself your own body and what brings you pleasure and orgasms. Masturbate, self-experiment, and self-explore forever because it will help you do the third thing: learn to let go during partnered sex. I think we can all relate to moments during sex in which we’ve gotten distracted, self-conscious, and/or in our own heads. “Does my body look weird in this position?” “I didn’t shave.” “Should I ask them to go down on me?” I think the best sex happens when you can just FULL HEARTEDLY give yourself the permission to enjoy, be vocal, and just let it all go to be in the moment…aaannnnnd maybe a little bit of THC lube if you can get your hands on it.

I promise you that there is truly NO question too unhinged for F*ck Around and Find Out with Anna Lee. Have a question you’d like me to answer for the next article? Submit them anonymously here!