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A Millennial’s Guide on Losing Your Anal Virginity

Sex Ed

A Millennial’s Guide on Losing Your Anal Virginity

There’s a reason why a woman would stick her tongue out at the thought of anal sex. It’s gross, it’s painful, and it ruins your natural bowel movement.

However, you have to take a seat back with your cup of Earl Grey tea and think that something so bad, could actually be quite good. I thought the same thing when I lost my anal virginity to a guy that came home from his Christmas break from his studies in Finland.

We already knew each other before he went abroad, but we kept talking to each other during my first year at university. I will always remember that one message he sent to me on a weeknight, which said:

“Next time you come back here, we are going to do anal.”

I won’t lie, I was a bit scared that something unexpected would happen, something that should only be concealed in the bathroom. I also remember being scared of the potential pain; the pain of a fleshy zucchini with a circumference of 4 cm sliding into my butt with the aperture of only 1.5 cm.

However, curiosity never killed my cat, and thank god that it didn’t kill my butt. In fact, I really enjoyed popping my anal cherry, even though it was quite rough at the beginning.

Nevertheless, in time and practice, I ended up learning how to have anal sex without any hassle or worry that my body would do something stupid.

Preparation is Key

If you are planning to lose your anal virginity soon, then it’s advised that you what day you’re going to do it, and what time you’re going to do it. Well, time doesn’t really have that much of an importance, but if you’re really concise, then it would be a good idea to let your partner know the time that he will come over to your place.

In terms of meals beforehand, I wouldn’t recommend eating anything that has an excessive amount of fibre in it, such as figs, artichoke, and bananas. Avoid bananas on the day of your first time. A shower before the date will give you more confidence in the bedroom when your partner will go down south. It’s worth the effort to stay in the shower for an extra 5 minutes, so you can groom your tush to perfection.

Additionally, you can never have too much lube sitting on your bedside counter. In fact, painting your guy’s penis in Aloe Vera lube would help reduce the initial pain, which would put your anxiety at ease when he would be sliding himself inside you. Therefore, one full bottle of lube on your counter can never go amiss.

I cannot stress the importance of condoms during anal sex. You may have encountered guys that wouldn’t even think about wearing a rubber during intercourse because it either reduces the sensation for them, or thinks that it’s just an extra layer that you don’t want to feel.

If your partner doesn’t want to put a glove on it when he’s inside you, tell him to ‘don’t bother coming.’

How to Start Popping Your Anal Cherry

Depending on how you’d like to start the night, you can do a variety of therapeutic activities with your man before you pull your lacey thong in front of him. My natural therapy is alcohol, but too much alcohol can make you sloppy if you consume over your daily recommended dose.

If you’re teetotal, then a nice cup of ice tea would be a good alternative. Seriously, you should try it! Once you got to the point where he’s on top of you on your queen-size bed, start getting into the foreplay; it’s just as important in anal sex as it is in normal sex. The important thing that you have to think is not to think, just relax and soften your muscles as your partner would begin to play with it. You could also keep the lube next to your thigh if it makes you feel more at ease.

Next, you have to loosen your sphincter a bit. If you let your partner slide a finger or a thumb in and out, it would make you feel prepared for what would come your way (little pun intended).

Personally, it’s best that you’re in control of the movement, so you would be able to adjust to the sensation at your own pace. Best starting position? Doggy Style. Why? Because you’ll be able to move your bum back and forth of your own accord.

Another tip would be to keep your partner’s whole length inside you for at least 10 minutes, especially if he’s bigger than the average male…Afterwards, you can begin to slide slowly up and down his shaft, before you’ll start to enjoy the feeling and move a little bit faster. If you manage to have an orgasm during your first time, kudos!

Hygiene is Just as Important as Pleasure

It’s completely natural to feel weird bowel movements after you’ve finished your anal sex session. Don’t be scared to run straight to the bathroom after you’ve finished having your fun, you know what they say; it’s better out than in!

It’s advised that you stay away from anal sex for the next couple of days, so that the sensation would slowly dissipate, and you wouldn’t have to wince every time you sit on a hard chair. Make sure that you check for any little cuts or tears around the skin, the last thing you want is an irritable infection that would get on your nerves for the rest of the week.

Other than having a packet of baby wipes kept on top of your toilet, there isn’t much else that I can advise you to do when you’re preparing to pop your anal cherry. If you end up liking anal sex, that’s fantastic; you’ve found a kink that you enjoy indulging in every now and again. If you end up disliking it, that’s fine, at least you tried it once!


Zoe Jaspers has been writing about sex, porn, and the world of escorting for nearly two years, and she still continues to enjoy writing about all of those topics, along with her sexual encounters. Even though she is informative in her written work, she likes to include a bit of humour in it too, because she believes that sex can be both fun and funny. Follow her at:

Website: https://www.escort-scotland.com/

Social Media: Twitter – @ZoeJaspers
Tumbler – zoejaspers.tumblr.com

Personal Linkshttps://medium.com/@ZoeJaspers


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Zoe Jaspers

Zoe Jaspers has been writing about sex, porn, and the world of escorting for nearly two years, and she still continues to enjoy writing about all of those topics, along with her sexual encounters. Even though she is informative in her written work, she likes to include a bit of humour in it too, because she believes that sex can be both fun and funny.

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