I will refer to the guy as Buddy. Every time I needed a hard fucking, he was there with his full erection. Always made me cum first. Never denied me a fuck when I wanted one. A true woman-pleaser.
After about a month of fantastic sex, Buddy starts hinting at putting it in my ass to which I respond “No, I have never done it before and do not want to.” He goes on talking about how he’s done it lots and many women enjoy it. Tells me I am just the type of woman that would enjoy it and should at least try. With him. His big dick in my ass. Still I say no. But he keeps bringing it up. Not forcefully. Just hinting that I would enjoy it.
One day I am curious. I cover my mascara tube in lube and slide it in my butthole. That was not bad at all. I am amazed at how easy that was. Next I take my hairbrush handle and cover it in lube. I do the same. It is a bit more difficult but still, easier than I thought. I call Buddy, tell him what I did, and that he should come over immediately.
Buddy shows up not too long after. He is really fucking happy and his cock is already hard as a rock in his pants. I present to him how I am able to slide in a hair brush handle. I slide it back out and see no poop on there. I hold it next to his full hard-on. Mmmmmm….the hair brush handle is much smaller. But I am so excited about getting this far with the household objects, that I still want to try. We use lots of lube. He starts pushing it in but my ass is really tight. After a bit of that, he forcefully jams it halfway in. Now I am screaming in pain. This does not feel good at all, nor is it enjoyable. “Get it out! Get it out! Get it out! Get it out!” I push back at him, but he stays in position reasoning “Don’t give up now. You just have to bear through this. Trust me, it will feel good.” I am not having it though. The pain is too much and he reluctantly removes his cock. We try again a few times, but it is just not happening.
Fast forward a few weeks. Buddy and I are meeting in a hotel. I am moving across the country and may never see him again. He struts down the hall and enters the room. As soon as he gets in, I say “I know what you like”, get down on my knees, unbutton his pants, and start sucking his dick before he can even take his jacket off. We fuck in every corner of the hotel room – I ride him on the bed – he bends me over the couch – in the chair – he stands and holds me as he fucks me in front of the mirror – on the bathroom counter- everywhere. I cum many times and he comes twice. Cum all over the place. There is cum in my pussy and on my face and hair. He is in full porn star mode.
After we got that out of our systems, we relax on the bed and start to actually have a conversation. I am super relaxed and happy after cumming so many times. I decide I want to try anal again. A smile spreads right across his face and he starts fingering my butthole. What about lube? There is no lube. He gets one of those little bottle conditioners from the hotel bathroom and explains that this works sometimes. I am skeptical but go with it because I may never get to try anal with him again. He rubs conditioner on his dick and managers to get the remainder of the bottle’s contents in my asshole.
For the next twenty minutes, we struggle like we did last time. It is just too fucking painful. But I am determined and keep trying. He sits on the edge of the bed and tells me to sit down on his cock myself, with my behind facing him. The first time I do this, it goes down farther than it normally did but still super painful. I pull out but I am determined, especially now that I am finally making progress. The second time, I slowly lower myself on his hard cock, the conditioner helping it ease in. It does not hurt. “I does not hurt!” I exclaim “Is it all the way in?!” Yes, I had sat myself on the full length of his cock and it did not hurt. Just felt incredibly full and dirty, in a good sexy way. I start moving up and down and it feels alright. I do it a bit more and it actually feels pretty good. I feel so naughty and sexual. But I want him to fuck my ass from behind also. I tell him and he turns me around, keeping his cock in my asshole. I am on all fours on the bed, with my ass high up in the air. “Slowly!” I yell. He starts fucking me slowly and it feels really good. I am getting super turned on and am really proud of myself. I can’t believe it. The end of his cock is stimulating me somewhere and I start playing with my wet pussy. It feels so odd playing with my pussy during anal – there is no cock in there, but I am still getting fucked. I am getting turned on enough from the anal and touching myself that I tell him to go faster. He goes up to medium speed. Holy shit, it feels good. Oh my god, am I actually going to cum?! Wtf, I am going to cum. “Ahhh I am going to cum! I am actually going to cum!” I have the most intense orgasm I have ever experienced in my life, to this day. It was so powerful.
As I am cumming, Buddy starts fucking my ass hard and fast. Occasionally going all the way in and out. As soon as my orgasm is over, reality hits that I am getting fucked in the ass super hard. My asshole tightens up again, I look back at him and yell “Fucking cum already!!! Please, cum NOW! CUMMMMMMMM!! AGHHHHAHAHAHH!!! CUUUUMMMMMM!!” I look back and see that he is furiously pumping away, his face red and I can tell by the expression on his mouth that he is going to cum soon. I see by his face, that he is cumming and deposits his semen in several thrusts, deep inside my asshole. Finally he pulls out. My whole body is shaking from the orgasm and the pain. Later, one day, he tells me that seeing me screaming in pain for him to fucking cum already was one of the hottest things he has ever experienced.
Source: reddit.com/r/gonewildstories/comments/3r46y1/how_i_got_talked_into_trying_anal_and_having_the
> After a bit of that, he forcefully jams it halfway in. he’s the type of guy that ruins a girl over anal for anyone that really knows how to do it
So, umm… where "across the country" did you move? :-)
i… i cant even begin to describe how wrong you went about this…him forcing it in…using CONDITIONER!!…full-on wtf. Please anyone reading this…this is a guide on how NOT to have anal sex.
… You have no idea how to anal do you? Please don’t give yourself an anal fissure.
Good girl, now you are broken in. The rectum is a muscle and can be trained to except larger objects such as plugs and the head of a larger cock. Tons of lube and more lube always help
So where would one start to do it the right way?
But I love anal now…
Yes sir, this is great advice
/r/sex’s FAQ is a great source, here’s their link for [anal 101](https://web.archive.org/web/20140329044425/http://www.sexpertslounge.com/2011/08/08/sex-for-noobs-anal-101/). In general, go super slow, use way more lube than you think you need. The best painless way to do it is have your partner start training their ass with plugs/dildos for a couple days before you fuck them.
I would definitely recommend lube over conditioner, but we did not have any that night. We did spend a lot of time playing with my butthole beforehand though so there was some preparation.
a bunch of anal white knights. If she had a good experience with conditioner, who cares.
I did indeed have a good experience with this particular conditioner. It was a better option as opposed to using nothing. At a later date, I did use conditioner for anal sex again because I had such success with it before, but that second time it was one of those strongly scented ones. It was horrible the moment it touched my butt and sex was no longer happening that day. Basically, lube>unscented conditioner>no lube>scented conditioner :)
haha awesome, you are doing gods work. Ive used all sorts of different things for lube so i know where you are coming from..
Coconut oil. Pure magic
Yeah I had an AP that came really hard from anal the first time we did it. First time anal orgasm for her she said. That was the benchmark until oneday I bit her clit hard… That grunting continued through PIV sex. Don’t try this at home unless she’s really submissive.
I tried jerking off with conditioner once, it got in my urethra and I felt like I was pissing fire for the next two days. Would not recommend.
Because you had a good attitude about it and wanted to try again. My girl had an experience like this prior to being with me, and convincing her to try again is like trying to convince a lion to become a vegetarian
Same here. Wife had a unsuspecting experience once. Now we can’t even talk about doing it. I’m not one to pressure her to do anything she don’t want to do. Expecially when I know how upset even talking about it gets her. But damn it, I would like to try it once.
Conditioners usually have some form of alcohol (e.g. cetyl) which can be VERY painful, even damaging, to mucus membranes. Not to pick nits, but are you sure it was conditioner? Could it have been a hand lotion? Those also contain alcohols and other potential irritants, but if it was a high-end hotel you might have gotten lucky and found one that was mostly waxy/fatty ingredients. Otherwise, I have no idea how you ever got past "oh my god, this hurts!"
After doing it initially, I definitely did not want to try anal again. Owie! But then later I felt so wonderful cumming multiple times and wanted to please him so bad that I did it anyways. Even then, it would initially only go in if I lower myself down in his cock as opposed to him moving. Glad I discovered that. Once relaxed, it feels awesome.
Not so much white knights as folks who probably tried it themselves (c’mon, let’s be honest now) and realized /r/instantregret