Not Taking It Up the Ass Ruined My Marriage, and Five Other Stories About Anal Sex

Note the first: CN for true stories of dubious consent, sexual pressure, cheating, unpleasant early sexual experiences.

Note the second: For outside-of-UK readers: 16 is the legal age of consent in my country.

Note the third: If you want the hot ones, skip to #5 and #6.

Forgive the clickbaity title – inspiration for this piece came from a conversation with Exhibit A in which I said that sentence and I decided it was the perfect intro to the post about anal that I’ve been wanting to write for quite a while.

Three butt plugs, one black silicone, one glass and one gold-coloured metal, sitting on a hardwood floor. For post about anal sex.

One.

I am fifteen and a virgin. My first boyfriend doesn’t want to take my Technical Virginity and comes up with the Amazing Idea that we should do anal – that way, he gets his end away while my “purity” (that’s a rant for another post) remains intact. Exactly what I am supposed to get out of this arrangement remains unclear. I refuse, but his obsession with my butt doesn’t cease until…

Two.

…I am sixteen and the same boyfriend has taken my Technical Virginity but is still heavily into the idea of doing anal, which does not appeal to me At All. One night, I realise I forgot my birth control pill – my boyfriend hates condoms, so this means we can’t have P-in-V sex. To make it up to him, I agree to try anal. We make it to two fingers. It hurts. We try the head of a cock. It REALLY hurts. I cry and we stop and I let him have unprotected vaginal sex with me. The next morning I realise I’m a fucking idiot, and I panic inside until my period arrives. We don’t do anal again until…

Three.

…I am nineteen. I’m now engaged to Mr Virgin Fetish, and we’ve opened up our relationship. I am occasionally playing with a much older Dom guy. MODG wants me to try an anal plug. So, somewhat nervously, I agree. He goes slowly and uses a lot of lube and does all the right things but the damn thing is Just Too Big. Determined to please, I push myself to take it all. I don’t like it and say I’m not going to do it again. BS&VO Boy is delighted – if I can take one little plug I can take his dick now, right!? My fear of having to do anal sex I don’t want is a major contributing factor, among others, to the time we don’t have sex for six months. Until…

Four.

…I am twenty and I catch him cheating, which makes No Fucking Sense in a polyamorous relationship. It has been going on for six months. A day after he lets it slip, he’s telling me that his new girlfriend is better than me. When I ask why, he rattles off a list. Amongs the reasons: she’s thinner, she needs him more than I do, and she’ll do sex acts I won’t do, anal chief amongst them. I’ve been replaced. I hang up the phone, sell my engagement ring, remove every trace of myself from his house, and try to pick up the pieces of my life. For a long time, I tell myself that my not taking it up the ass might have ruined my marriage before it started. I write anal off as a hard limit, until…

Five

…I am twenty four. We’ve been in love for quite a while but, for the first time, the man who will become Mr CK is in my bed. Our cyber-and-phone-sex explorations over the preceding weeks have awakened thoughts I never thought I’d have again. I want his fingers, his toys, his cock in my ass. I tell him I want to try it. This first time, all he does is lube up one finger and slowly, slowly, slowly slide it in. He holds my hand, reminds me to breathe through the initial pain, tells me I’m amazing. With his finger in my ass, I rub my clit and am quickly brought to an incredible orgasm. We experiment with fingers and small toys a few times, but I am nervous to try anything bigger (like his definitely above-average cock.) Until…

Six.

…Last year. We are at one of our favourite kink clubs, locked away upstairs in one of the private play rooms. He throws me down on the massage-table-cum-bed. He tells me he’s going to fuck my ass. There’s no softness this time. He wants me and he is going to take me, but only because he knows – because I have told him – that this is what I really want. I want to be ravished, to be used, to be his anal slut. His cock slides into my ass, an inch at a time, until he’s buried deep in me. And then he’s fucking me hard. I’m not getting any stimulation to my cunt or clit, but I can feel something building within me. I realise a moment before it happens that I am going to come. My ass clenches around him as my muscles spasm in my first anal-only orgasm. Watching me get off this way tips him over the edge too and he tenses, moans, and I feel him come in my ass.

Afterwards, we cuddle. I say, ‘hey, remember when I thought I didn’t like anal sex?’ Turns out all it takes is love, trust, patience, lots of lube and no pressure.

The picture featured in this post was taken by me. I own the copyright and it must not be copied or reproduced without express permission.

3 thoughts on “Not Taking It Up the Ass Ruined My Marriage, and Five Other Stories About Anal Sex

  1. Brilliant recount of an evolution into anal.
    I agree with your conclusion, although it would be a unusually mature 16yr old to know how to broach the topic of anal with the finesse required.
    Great that you have now discovered how good it feels. Well done to your boyfriend for taking it slowly and building the trust with you..

  2. Oh I loved this. I have never read anything quite like this before. For me, who has never had anal, this is a complete eye opener. For this reason I found this piece very moving.

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