A potential "gradual" approach
Undercover,
I suggest first focusing on your wife taking you with her strap-on. It's simpler in a psychological sense, because it involves only one other person you know well (your wife) instead of three people (you, your wife, and one of her lovers). A way to approach it would be to treat it like an imaginary stage performance, in which you — in a shy, bashful fashion, sort of like a virginal young girl — confess that this is "very embarrassing," but you wonder if she would be willing to discuss one of her fantasies that she's mentioned in the past.
Your wife, with a combined look of interest and curiosity (no doubt), will say: "And which fantasy would that be, darling....?" You, again looking bashful and hesitant, could say: "Oh, it's just too embarrassing to even bring up. I'm afraid you wouldn't 'respect me' in the morning." Your wife would then, perhaps, sense the need to play the "suave man" seducing a reluctant young girl (you), and might say something like: "Oh, there's no need for you to worry your little head, sweetheart.... of course I'll still respect you in the morning. You can tell me.... please, sweetheart, don't be afraid....". You, looking *very* shy and hesitant, could then say: "Well, it involves your strap-on...."
Your wife — now sensing the need to "play" seriously, because you're on the verge of granting her something she's wanted for a long time — could then carry on with coaxing and mollifying you, until finally you confess you've secretly been wanting to take her strap-on in your mouth. But, you are *very* concerned for your reputation, and you *do* hope she will still respect you in the morning.... (etc. etc.). Your wife, presumably, will go on gently seducing you and reassuring you she will still "respect" you in the morning.
Finally, you will allow yourself to be seduced, your wife will go off to get her strap-on, and you can suck her "cock" in whatever way(s) she prefers, bringing her to orgasm (one hopes) in that way. You might then begin a program with her of learning to deep-throat her strap-on by being down on all fours with her on her knees in front of you, pushing her "cock" a little farther down your throat each day until you can finally take it all the way down.
Alternatively, you could lie on your back on your bed with your head tilted back over the foot of your bed, and with your wife on her knees at the foot of your bed, and she could push her "cock" a little farther down your throat while you suck her "cock" each day, until you can deep-throat it all the way down. (This may take on the order of two weeks to a month, depending on how effectively you can suppress your gag reflex.)
At some point during this process, you could hesitantly and bashfully confess to your wife that you have secretly been wanting her to fuck you up the ass with her strap-on, but (again) you are *very* concerned with whether she will still "respect" you in the morning. Your wife will continue to play her role, no doubt, and gently reassure you.... then fuck you up the ass (with her strap-on *very* well lubricated).
Once your wife is fucking you up the ass regularly with her strap-on, and "requiring" you to suck her "cock," (all while gently reassuring you that she "still respects you," of course), her role with respect to you will begin to change. Soon enough, she will order you to suck her lover's cock — and you can then do it, without feeling demeaned, because you will not have confessed you "want" to do it. Rather, you will be able to do it because your wife has ordered you to do so.
—Custer
Undercover,
undercover said:.... And that is where it gets sticky (excuse the bad pun), when I think of fulfilling her fantasy (and mine - secretly) of sucking off and/or being fucked by another man in her presence, or letting her put on her strap-on and make me her bitch. I guess it's that age-old question: "Will my wife still respect me in the morning?"
I suggest first focusing on your wife taking you with her strap-on. It's simpler in a psychological sense, because it involves only one other person you know well (your wife) instead of three people (you, your wife, and one of her lovers). A way to approach it would be to treat it like an imaginary stage performance, in which you — in a shy, bashful fashion, sort of like a virginal young girl — confess that this is "very embarrassing," but you wonder if she would be willing to discuss one of her fantasies that she's mentioned in the past.
Your wife, with a combined look of interest and curiosity (no doubt), will say: "And which fantasy would that be, darling....?" You, again looking bashful and hesitant, could say: "Oh, it's just too embarrassing to even bring up. I'm afraid you wouldn't 'respect me' in the morning." Your wife would then, perhaps, sense the need to play the "suave man" seducing a reluctant young girl (you), and might say something like: "Oh, there's no need for you to worry your little head, sweetheart.... of course I'll still respect you in the morning. You can tell me.... please, sweetheart, don't be afraid....". You, looking *very* shy and hesitant, could then say: "Well, it involves your strap-on...."
Your wife — now sensing the need to "play" seriously, because you're on the verge of granting her something she's wanted for a long time — could then carry on with coaxing and mollifying you, until finally you confess you've secretly been wanting to take her strap-on in your mouth. But, you are *very* concerned for your reputation, and you *do* hope she will still respect you in the morning.... (etc. etc.). Your wife, presumably, will go on gently seducing you and reassuring you she will still "respect" you in the morning.
Finally, you will allow yourself to be seduced, your wife will go off to get her strap-on, and you can suck her "cock" in whatever way(s) she prefers, bringing her to orgasm (one hopes) in that way. You might then begin a program with her of learning to deep-throat her strap-on by being down on all fours with her on her knees in front of you, pushing her "cock" a little farther down your throat each day until you can finally take it all the way down.
Alternatively, you could lie on your back on your bed with your head tilted back over the foot of your bed, and with your wife on her knees at the foot of your bed, and she could push her "cock" a little farther down your throat while you suck her "cock" each day, until you can deep-throat it all the way down. (This may take on the order of two weeks to a month, depending on how effectively you can suppress your gag reflex.)
At some point during this process, you could hesitantly and bashfully confess to your wife that you have secretly been wanting her to fuck you up the ass with her strap-on, but (again) you are *very* concerned with whether she will still "respect" you in the morning. Your wife will continue to play her role, no doubt, and gently reassure you.... then fuck you up the ass (with her strap-on *very* well lubricated).
Once your wife is fucking you up the ass regularly with her strap-on, and "requiring" you to suck her "cock," (all while gently reassuring you that she "still respects you," of course), her role with respect to you will begin to change. Soon enough, she will order you to suck her lover's cock — and you can then do it, without feeling demeaned, because you will not have confessed you "want" to do it. Rather, you will be able to do it because your wife has ordered you to do so.
—Custer