Dating: How's your luck? - Page 90

Make your sex right now as kinky as possible. If all you do is missionary and you suddenly drop the anal bomb on her it's probably not gonna work. Taking baby steps towards anal. Not really sure what you're doing right now but you can do any combination of: blindfold, tie up her hands, tickle with feather, ice cubes, fruit, clothespins and then try different positions, maybe get drunk. Also give her massages, foot rubs, really take your time and let her feel safe and that she is much more to you than just for sex. This can take weeks.

After you have done all that and your sex is nice and lively you can start to slowly touch her anus.

Initiating anal touch would be best while you take showers together. Lather each other up, let her clean you and you clean her. Massage her whole body, taking your time, and then down to her butt cheeks and then just lightly slip a finger between her ass and brush against her asshole in a "I am cleaning you but you are sexy" kind of way. Make it short and light. Do not try to stick your finger in. If she doesn't seem to mind then do it a couple more times, and move onwards down her thigh, legs etc. The point is to not make it a big deal. If you can then makeout or bang in the shower. If she seems upset about anal touch then back off. The key is to slowly introduce anal sensations to her without her even realizing you are doing it to her.

Other times would be when you are banging or eating her out, and she starts to get near orgasm, just lightly making circles around her anus and then back off and let her cum. Usually she won't bring it up. Do this a few times when you have sex, this can take weeks. If she starts asking you after sex "hey what were you doing just now to my ass during sex?" just say something like "oh sorry girl, just caught up in the moment u know. why? you didn't like it?" Hopefully she will think about it a little and think it wasn't that bad. If she seems ok with it then go on to the next step.

When banging, best is doggy style but I'm sure other positions can be good too, when she is close to cumming, press a lubed finger (spit or pussy juice) on her anus and just slowly press it like a button, gently and firmly, maybe making small circles or other movements. Make her comfortable with this feeling and always be stimulating her vagina or clit in some way so that she will link the two sensations together. Again, try to do this while she is near cumming since most girls won't stop you at that time no matter what you are doing. If later on she is calm and asks you about it, admit to what you were doing but just shrug it off as something you didn't do deliberately. This can also take weeks.

If she finally seems comfortable with you touching her, you can try to put something in. This would also be the time to talk to her about anal play, saying how much it turns you on and how you will listen to her and stop when she asks to etc. Buy some lube, I like water based since if it goes thick and dry you can just spit on it. Oil based will get everywhere and takes ages to clean out. Start with something thin and smooth, a toy would be best since your finger is more textured and poop can get caught on your finger and that will most definitely freak her out and can set you back a lot of time. If you use your finger, put a condom over it. Going SLOWLY, don't even try to push too much, just gently massaging the area, the whole time fucking her slowly or licking her, using your hands on her belly, thigh or legs etc. Try to spread her attention as much as possible and not let her focus on her ass.

There are two sphincter muscles. The outer one you can see and she can consciously control, and the inner one she cannot control. Usually when it hurts it is the inner one that has not loosened up and it is being forced open. Ask her to push against the toy as if she is passing a bowel movement, this usually loosens the inner sphincter. If she cannot, then do not make a big fuss, just put everything aside and go back to vaginal sex and try another time. Once the toy slips past this part, the rest of it goes in rather easily, so do not rush. One small mistake and you hurting her could mean the end of your anal quest, she loses all the trust and sexual connections you have built up. Slip your toy in a little at a time, letting her get used to the feeling of something being inside her ass. There is no need to go very deep, the aim should be to gently loosen her sphincter muscle by using thicker objects. Again, butt plugs and sex toys are more suitable and safe for this reason.

Once you can get in a toy as thick as your dick, you can try getting your dick in. Too much lube is just the right amount of lube. Go slowly, a centimeter at a time, the whole time talking to her, asking if there is any pain, kissing her, caressing her, saying how good it feels, massage her clit, etc etc. If at any point she says to stop, do not pull out like an idiot, pull out very slowly as well. After you are completely inside, take a while for her to get used to it, and then start moving in short thrusts, very slowly. The anal membrane is very thin and tears easily, so go slowly. After a while she should be quite loose and you can go as fast as vaginal sex. Sometimes she can get even more loose, at which point it stops being any fun.

It is rather common for there to be a little blood, so don't freak out or anything if you two see any. If you two are squeamish about seeing poop then I would suggest a dark room with an old towel laid down, or even in the bathtub. Don't eat too much the day before. Light some scented candles to cover the smell of ass. And don't put anything that's been in her ass back into her vagina, bacteria and risk of infection.

Anyway good luck. Hope that helped.

I am a male unkissed virgin, 23 years old. Ever since I hit puberty I’ve been a very quiet and a bit of a anti-social person. Basically I was (and to some extend still am) the term “beta” personified. My looks are average at best, I’m fairly muscular, and I have 0 fashion sense. I spent a lot of my childhood playing games, and I basically spent all of my teenage years playing World of Warcraft with friends from my gymnasium (10 to 12th grade) class.
This has led to me not having many friends at all, altho the few friends that I have I am very close to. And I especially have never had any female friends or any experience in talking to women (besides my sister whom I’m also very close to).
My first encounter with love was brief during summer 2012, where I sort of fell in love with a woman at my summer job, but I quickly learned she was in fact a lesbian (that’s what I get for having a thing for women with short hair, eh?) so that love didn’t really have time to manifest, and I got over it quickly. Looking back, I think I basically fell in love with her because she was the first woman I’ve met who didn’t seem to mind talking to me, and looked at me for more than 0.1 seconds. (Full beta, or what?)