when i was younger, anal sex never interested me. 

“it’s an exit, not an entrance!” i’d proclaim. 

i specifically laid this out for my first boyfriend. he had no problem with it. about a year into our relationship, he began toying with the backdoor while going down on me. i was suspicious at first—“aha! you crafty motherfucker! you’re just gearing up to rail my teenage asshole!” i’d think to myself. 

he never attempted to go any further. 

after time, i realized that i could enjoy ass play without committing to ass fucking. this was a breakthrough discovery for me. eventually, i would be disappointed if he ate me out and didn’t pay attention to my ass. 

a few years into our relationship, my curiosity got the better of me. i told him i wanted to try anal sex. he was dispassionate. i was shocked! all this time, i had assumed that anal sex was some pinnacle for dudes—that they would beg, borrow and steal for a chance at the forbidden orifice. after a few half-hearted attempts (1/4-hearted, truth be told), we tabled it. 

it wasn’t until the next man i dated that it again came up into conversation—after he “accidentally” broke the seal. i use quotes, because i am not entirely convinced it was a mistake. i mean sure, we were having vigorous intercourse in an angle not ideal for viewing, he came out, and hurriedly put it back it. innocent mistake. never mind that my body language immediately changed from “oh yeah” to “WHOA!”

could he really not tell?!

thank god for my own lubrication and the fact that he climaxed immediately afterwards. otherwise, i think i would have cried. when i brought it up afterwards, he swore up and down that it wasn’t on purpose. “it was an accident!” he insisted. but then, “and if it ever happens again, it will be an accident then, too.” suspect. very suspect. that, paired with the way his ears perked up when i said that i wasn’t adverse to trying it, given proper warning and lubrication, leads me to question the innocence of the encounter. i dissolved our union a few weeks later for unrelated reasons anyway, so i never got a chance to find out. 

there were two dudes after that who were granted access. not because of any particular trust they had earned—i had sex with each of them exactly twice—but more because 1. i was going through an experimental (and mildly promiscuous) phase, 2. they had the two smallest penises of all my sexual partners (unfulfillingly small), and 3. i was drunk. i mean, really drunk. i had been drinking moonshine with the first, everclear with the second. they asked, and i figured, ‘what the hell.’ neither lasted more than a minute or so (note: even if a man’s cock is the size of a circus peanut, if that peanut is going in your unlubed anus, it’s still hella uncomfortable). on the whole, not very memorable. literally. i don’t remember the majority of either encounter. 

started casually/not casually dating/not dating a man for the next 6 months. i asked him if he had experience with it. he had, but had no desire to repeat it. 

“why would i want to do that, when there’s a perfectly good vagina right here?”

i began to think i might skate through life with the ol’ rosebud more or less unsullied.

fast-forward to present day. 

began seeing the current beau. one night, we were discussing pornography and the subject once again arose. he had engaged in it with an ex, but unlike the above-mentioned partner, was not against it. he wasn’t a rabid fan. he never solicited (and, in fact, deems it “ungentlemanly” for a man to request it), but found it enjoyable. for the first time in almost 10 years, though, i took it back off the table. it wasn’t anything against him personally—just against his cock.

this man has the biggest cock of any partner i have ever been with—by far. after we slept together for the first time, i sent a mass text to my girlfriends, saying i felt as though someone had hit me in the twat with a hammer. the thought of that monster invading my very tender backside….well, there was apprehension, to say the least. 

months went by, though, and again, my curiosity flared (that, and my competitive nature. i pride myself on being a being a quality lover, and it irked me that he had shared something with someone else—something that i could also share, save for my own withholding). we discussed it at length, both in a concrete and abstract way, and decided to break the process down into 5 steps; advancement to escalating steps at my discretion:

1. rim jobs and outside play

2. digital stimulation

3. small anal toy play

4. large anal toy play

5. anal sex

step 1 and 2 were simultaneous and pretty immediate, followed by months at step 3. 

a few weeks ago, i decided to skip step 4. after so much time with step 3, it didn’t seem entirely necessary. that, and he was working my body like he had a playbook, and i was feeling especially tawdry. after extended preparation/anticipation, he introduced himself—about an inch and a half of himself. i couldn’t continue but, unlike every experience before, i wanted to repeat it. not to please him (well, not just to please him), not out of a blase experimentation, not because it was some imagined ultimate in kink. it was too much, and there was some uncomfortable teeth-gritting, but on the whole…i enjoyed it.

it’s still not full-throttle—unsurprising, as i am unable to take him to the hilt even when orthodox (i’m telling you—behemoth). probably about 2/3 + thrusting after 3 separate attempts.

some things i’ve learned:

1. silicone lube is king. saliva was immediately disregarded, self-produced lubrication, inefficient. water based lube did the trick for a while, but after silicone, there is no turning back. it’s longer lasting, resulting in less need for re-application, plus it just feels better. it is a superior glide.

2. vibrator play is a plus. a BIG plus. practically a necessity. 

3. the larger actual member was more comfortable than fingers + small toy. i was surprised, but i suppose it makes sense—there’s more give, and he was slower in its insertion. if i were to do it again, i’d shorten both steps 2 and 3 considerably (but not disregard entirely. i think it was an important part of mental prep-work). 

4. r did some research and found that, contrary to what i had believed to be the ideal position (face down, ass in air), most sites recommended the missionary position for first-timers. having tried both, i can testify to that. easier to relax, plus easier access to the other erogenous zones (see 2).

all in all, i foresee updates in the coming weeks.

after all, it’s important to have goals.