Anal while dildoing vaginally? (DP)

My g/f recently admitted she was curious about getting DPed with a sex toy+myself. So I figure I'd go buy a toy and try it (we've already had anal a few times). Im guessing the best way to go about it would be to enter her anally doggie style, and then... wrap my arm around and try and dildo her vaginally? Is this possible or would it be too awkward a position or simply not enough space?

And yes I have to be the one dildoing her, she doesn't like doing things herself.

 

I've found the best way to go about this, is to do it sideways or "spooning." That'll make it much easier for you to reach around with the toy.... although I'm kinda curious why she doesn't like to handle the toy herself...in my experience, it's distracting and kinda difficult for the man to try to coordinate thrusting and toying at the same time.

 

Now that I think about it, I believe you're right. The side position does allow for a comfortable reach around and good access to the vagina. Thanx for the tip. More experiences are welcome!

As for your curiousity, idk she's just a very submissive/not sexually...dominant? person. She rarely ever masturbates (yes its true), and in the years I've been with her I can count on my hand the times SHE has really initiated sex (aka actually pull down my pants or spontaneously perform foreplay). BUT, she loves sex, never really says no to me, is almost always in the mood, and is open enough to talk about what she likes etc. Idk.. just a submissive but still horny person lmao. Stuff has to be done TO her.

 

Interesting....I know many submissives who actively initiate and participate. Anyhow, it sounds like you two are happy and enjoying a healthy sex life, so good for you.

 

I think most couple who indulge in anal sex also experiment with something in the front.
It's nice!

I would actually go the other way - put the dildo in first, have her lay on her tummy and you take her gently from behind.

BTW - It in NO WAY resembles a "live" DP.

 

Have her lay on her stomach? I'm not sure how I'd be able to handle the dildo. Remember I'd like to actually coordinate my thrusting with my manual thrusting of the dildo. Obviously it'd have to be slow and maybe a bit of a challenge, but it does seem like I could do that from the side position. Care to explain a bit more of your idea?

 

I've done both (toy in ass and toy in pussy) and I'd recommend using the toy on the pussy.

Most toys are less flexible than your penis even when rock hard and you should be concentrating more on being smooth anally. Also a nice trick is using the toy to massage the wall between her ass and vagina which if done correctly should feel for you going up and down your shaft. This should make it easier for you to give her anal and also maneuver the toy in her pussy.

 

Do you mind sharing what position you were successful at pumping the dildo and your cock at the same time? In my mind the spooning position is winning.

 

The side position or spooning as you said is nice but me personally I prefer taking my partner from behind. Her ass aimed high which should result in a good curve and her using her forearms to rest. That position is easiest to manipulate the vagina while I'm inside her ass.

 

My wife (we're lesbians) fucks me in the ass with a strap-on and adds a dildo in my pussy too! When we do it I lay on my left side and she kneels at my ass and fucks it. Imagine my shoulders and upper back flat like missionary position and hips and ass like spooning. She is in a doggie style position but with her knees spread wider to lower her angle of penatration. After we are comfortable with the fit and pace, etc., I start begging for her to fuck my pussy. She will grab my right foot and put it over her shoulder so she has wide open access to both holes. She will fuck me with the dildo and the strap-on and most of the time I will add a vibrator for a little extra. It is the absolute BOMB to come like this!

 

Use one of these. This way you can fuck her in her pussy and ass at the same time and leave your hands free. My girlfriend absolutely loves this toy!!