Try a compromise for awhile; Try you taking her anally and your friend doing her vaginally and maybe in time she'll get to where she might like to have you two switch; once she's use to his size in her vagina.

You could always switch who is going to put what is where. You could also get a good size dildo, and have her play with it analy while you penatrate her vaginaly. If it is to much with the dildo, it will likely be to much in the flesh, but you could practice until she is comfortable. This is one of my fantasies, and worries about it as well. Let me know how it works out for you guys!

Roofies

Turn the lights off. The sight of his penis will terrify her. Also, use your fingers and tongue on her anus for a long, long, long time. She will relax, and it will fit just fine.

You never do it with your wife. You do it to someone elses girl.

You do the anal and let him fuck her pussy, start it with this and later you can change holes.

The easy answer to make her comfortable is to explain how you will both respect her and if it doesnt work then you will stop. Knowing she can stop at any time is the easist was to reassure her.

get her drunk

Tell your wife to try double penetration with a well hung bisexual male and tell your wife that she would have nothing to be nervous about,because a bisexual male who is well hung has the experience not to make anal sex with a heterosexual female painful because he has a lot more experience with having anal sex with a heterosexual female, then a heterosexual male has experience with having anal sex with a heterosexual female and a bisexual male is also a expert having anal sex with a bisexual female,and if you or your wife have any more questions that needs answers to a subject like this I will be able to answer them for you only if you want me to in the future.

I think that if your wife found out how good that it feels when a well hung bisexual male has his penis inside of your anus,while he is having anal sex with you while you are having sexual intercouse with your wife,your wife will find out for herself that having anal sex with you would also feel good to her then your wife would not be nervous about having anal sex with a bisexual male while your wife is having vaginal sex with you and I also thibk that if your wife found out how good it feels when a bisexual male is licking the inside of your anus that your wife would also would want to lick the inside of your anus and I also think that if your wife found out how good that it feels to you when she and a bisexual male is taking turns performing oral sex on you that your wife and you will no longer have a fear of male bisexuality and if you and your wife is no longer have a fear of male bisexuality your wife and you will have a lot more orgaisms after your wife and you become bisexuals and there are more bisexual males then gay males and there are just as many bisexual females as they are bisexual males and there are more bisexual females then lesbians and there are also just as many bisexual males as there are heterosexual males and there are just as many bisexual females as there are heterosexual females according to a poll that was taken may of 2007.

We decided to enlist the help of another male and make a movie of us to keep to remind us of how things were when we get older, we found a friend on a contact sitem, met him and worked out a plan, he was to film us and had to get naked as we did so as not to be to formal, we took a lot of time with foreplay as he took video of us. Slowly we all got naked and he was very close and had a very long fat cock that was hard. As my wife and I made love we spoke about the friend who came in range, my wife reached out and took hold of his cock. He moved closer and slipped it into her mouth, she responded now both of us, thus I watched as he reached down and touched her pussy. By this time the filming had stopped. I slowly moved away to give them freedom. My wife turned towards me and reached with her eyes for my consent before putting herself in a perfect entry position for our friend’s big cock. I held her hand and said enjoy. At that moment he slowly pushed his far bigger dick into her pussy. She gasped and said GOD HE IS BIG. I looked at him and requested him to fuck her hard and fuck her good and long. I moved away and watched for almost an hour as he did just that. My wife was riding on his very big cock and I was simply overwhelmed seeing how her little pussy took his cock all in. I could not have imagined in my dreams that her pussy could hold such a big cock. This was a few years ago. In the meantime, my wife went through her changes and has not found her taste for above again. On top of that I seek advise how I can get her interested in her receiving a cock in each of her holes at the same time. She was many times happy with a big dildo and my cock in her pussy at the same time. I know that she would love a live encounter. Her body is petite, but her appetite is great and her pussy is "open minded" (see attached pic and you may imagine more). You want to use some oil and massage her anus. Take your time. If you go too fast it is over in 5 minutes. If you take time, she will love to welcome both of your cocks in her two holes. Of course, some alcohol, a porn movie and squeezing her nipples and sucking her pussy helps beforehand to get her horny enough to keep going. Hope this helps.

I discovered that giving her time and let herself get her holes used to a dildo will allow to penetrate her much easier in both holes and not matter how big each cock is. Once she is wet and her lust is more than horny, you will see an enormous and almost uncontrollable self-dynamic. Here a pic of her just before she used her brown dildo to get both her holes used to be penetrated. And then a quite bad pic when she got first her pussy used to a big cock. Greetings from 3someencounter

I'd say the best way to reassure her would be to have her watch YOU get assfucked by this guy, and then I think she'll be reassured. Get it?

...let your wife use a similar one by herself. Give her 30 minutes and you see wonders....

Ow???.... Put something small in the butt.

The only way forward here is for you to fuck her pussy and to DP her with a dildo first. That will get her ready for the feeling and you can buy the dildo to the right size (i.e. large). If she doesn't like that, then you fuck her ass and put the dildo into her cunt. Then she can see if that works. If that is ok then your friend will get her pussy and you can do her up the ass. Is there any specific reason you want him to fuck her in the ass rather than you?

i agree with answer 10. fair is fair...she's gonna be filling 3 holes in this threesome, and it would be only fair if you donate your 2 orifices to the pleasure of the occasion. it could be quite sexy if she's into that

You have to have trust between you and love each other. Secondly, you have to have friends you trust also. I can HONESTLY tell you that my FIRST entree into dp sex first happened about 5 years ago--it was great--no pain--just pleasure, because the guys I'm with KNOW how to pleasure a woman--I'd had anal sex with my husband and other friends of ours but never dp sex. HERE is a typical night/morning/evening of dp sex for me and my husband and our friends: We begin lots of TIME--you can't rush good sex--we begin with foreplay to loosen me up and get me comfortable, and we use LOTS of lube as well--edible lube works best for ME. We don't rush. I have to be thoroughly relaxed to give my husband and me what WE want. Our friends also have to be pleasured too, and of course they have to pleasure me. See, YOU want YOUR wife ready to feel physically what she wants to feel, and to pleasure you too. I love & trust my hubby and we also have great friends who KNOW how to pleasure me. Our first venture was a blast--so enjoyable and pain-free. It was the BEST decision we ever made. Personally, I LOVE length and width. I ONLY insist in having dp sex with guys who are well-hung. My hubby is about 12"L 3"W (ex-jock--all our buddies are well-hung). NO offense, but SMALL penises do NOT work for me, I have to feel EVERY inch inside me. After dinner, lunch, or breakfast we talk about what we want to do--then DO it. Hubby's in the background filming away, and enjoying himself manually--I KNOW I'm pleasuring him and myself and our friends. We begin by tongue kissing, fondling my breasts then putting nipple clamps on my nips then both guys manipulate my breasts and pull on the chains--very pleasurable. I love nipple clamps on during sex, but the guys usually end up pulling them off by accident--things get very active as you might imagine. Then we tongue kissing continues--then they explore my body, both finger me to make sure I'm wet--which I usually am LONG before the sex begins. Then, they both begin oral sex on me simultaneously--VERY pleasurable getting oral sexed by 2 men or more, more breast play from them also. After about 15 minutes, I'm extremely lubricated--loose and ready. But we're still not starting dp sex. I give them oral sex simultaneously. VERY much a turn on--Hubby is still filming away--watching and getting his hard on. Then after 20 minutes of foreplay and after both guys are hard and erect the fun begins. I get my edible lube, then lube the erect penis of the friend I'm mounting. I mount and I ride him about 15 minutes while giving oral sex to our other partner. After about 10 minutes, I'm ready for more. We change positions and partners, and I ride some more for about 10 minutes on the other guy I was blowing. I mean, I'm ready to pass out this feels SO good. But the guys to their credit mostly always hold onto their erections for long periods of time--which is great for me, because they're so damn big. Now, normally hubby films and we have another friend I give oral to while I'm being dp'd but sometimes, hubby wants to join in and get blown while I'm being dp'd. I'm still mounted and very comfortable then our friend enters my bum very slowly and the strokes begin slowly also. See, slow strokes in my bum make the difference to ME, and after about 2-3 minutes of slow strokes, I tap his stomach for harder and sharper strokes in my bum. Then the guy on the bottom starts up slowly thrusting--after a few thrusts, they don't need me to say anything--they're experienced and the motion gets harder and faster--I'm usually on my belly for about 15-20 minutes screaming like a fool. Then, I dismount, and the other guy's penis who I was riding goes into my bum and vice versa. These positions take place for about 45 minutes to 1 hour and sometimes even longer (It helps that we're all in great physical condition). But you're talking about pure pleasure--I'd rather have sex than eat food, and although this is about dp sex, YES I swallow and hate using condoms. I know its very risky now-a-days--NOT using condoms, but we're all very close with our friendships, and normally we keep the same set of partners--all of us are married--and we don't practice risky sexual behavior because of our professions IF that makes any sense, and we have to have AIDS tests also because of the professions some of us are in (law enforcement, firemen, teachers, one is an MD). I've never used condoms because for me, They get in the way, and I NEED to taste, feel, and see the cum and the penis also. For you, using condoms may work and I wouldn't want to stop you from using them. Now swallowing turns me on--cum on my body, and feeling the hot ejaculate go inside me--I'm very sensitive to this--making love without ejaculate is a waste for me. I'm never gonna stop enjoying dp sex. It's part of me and my hubby's way of life. It enhances OUR marriage-gives US stability--generates trust for US--we have very few boundaries, and we're so happy with our sex lives--and you and your wife will be too--provided you follow the guidelines I laid out--I'm a woman--we're not all alike, but I KNOW your wife wants patience and understanding--and pleasure--any woman does--But you have to make sure SHE wants to do this--never force her to do something she doesn't want to do, because if she's tense and you HURT her, or you don't listen to her concerns, you'll have a hard time convincing her to do or try again. YOU have to have patience with her. SEX is part of life and is to be enjoyed--not just something to do because you have time and you 'have' to do it. I've given you a night of what normally happens when me, my hubby and with our friends when we engage in dp sex. Now sometimes, we're off a bit, but MOST of the time, things go very smoothly like clockwork--we operate on ALL cylinders. Both me and my husband are educators who love living life, and who love being teachers. We're both in our early 30's and enjoying LIFE. Good luck to you and your wife in whatever you end up doing, but do it from LOVE and for pleasure.

I prefer the little dick up my ass and the big guy in my pussy. She is doing this for you, do you have anything mind to please her. How about eating your buddies load out of her when you are done.

Maybe you could be the one to put it in her ass, assuming you are smaller than your friend.

YOu need lots of lubricant....Case load...Let him put it in Vaginally and you anal for now..Once you cross this path, there is no looking back..remember that...so be prepared for it...Go for it...Condoms..

For most woman DP is very painful. She has every right to say NO and mean it. Anal is painful it self, those woman that say it's not has never been buttplugged! A well endowed man has no business in the exit only region. Don't force the issue as will become an issue you don't to deal with, trust me on this!

I'm was in a similar situation where me and my boyfriend had just started to explore DP Sex about 1 year ago. I was nervous at first because I'd never been with two guys at once, but since I was not pressured to it, and since my boyfriend was very patient, used LOTS of lube and since my boyfriend and his friend were good lovers, things went very well for me, and now I really enjoy dp sex. I'm usually with 4 guys at once--that's my limit for now (lol).