Need Advice re: Best Friend's Daughter

Dilbo said:
I am a sort of an old guy and still a Virgin here at Lit, but I am still very potent. Recently, she (see title), who is 41 years old, is pleasingly plump and has a grown son and daughter, has asked me, privately, to send pix of my wife, who is her age, the sexier the better, and of my privates, aroused. I've sent a few to her, and she wants more. So far, I've sent some coy, semi-revealing nudes of my wife alone and one that my wife took of me alone in the shower in a semi-erect state. She loves 'em. Now, is there a subtle way I can ask her for any progressively sexy pix of herself in exhange as a "fair is fair" proposition? I don't want to scare her off, or destroy my lifelong friendship with her dad (who has no clue so far re: what we're up to), but what I eventually want to build up to is some pix of my wife and I naked together having eating and fucking pleasure, hoping for something like the same back from her. She lives 800 miles away from us, so the chances of us ever actually getting together are remote. This is no fantasy. What or how do I proceed to getting her to send me pictorial feedback? Any suggestions from any of you "really experienced" folks?

Well, just casually ask for exactly what you want - go along with the "picture for a picture" idea. Just say, "I've send you some pictures and you really enjoyed them... I know I'd enjoy pictures of you just as much as you have mine - so do you think you could share a few as well? ;) " Always put a wink afterwards because if it doesn't go as well as you thought then you can say you were just joking, hence the safety of the wink. :p

It should work though, just act casual about it. The more you worry about it the harder it'll be, so just bring it up in conversation when she's talking about the pictures you've sent her or something. :)
 
Thanks, Sexychik and Retrieval............It worked! She claims she doesn't have anything "interesting" on the Computer, but will send me something appropriate by snail mail. I can't wait to see what I get...she claims she was an Artist's Model to earn extra money while in college and that what she is sending me relates to that. If it is as good as I think it will be, I'll get back to her with far more explicit things of my own. I'll keep you guys posted!
 
Now she tells me that she doesn't really have any "hot" pix of herself, and what she is sending are pix from when she says she was much younger and sexier, and modeling. And further, she says the pix I've sent her of some of them from my bare ladies with bare pussies collection don't really turn her on, but one that I did send her of me sporting a semi-erect cock was very "hot" for her. I guess what I'll do is send her some more naked me cock shots, and then spice them up with one or two of a girl's hand jerking me off, and see what that leads to. Stay tuned. I'm also going to urge her to get her own, private Digital Camera. That could put us on an even par pretty quickly, no?
Am I still missing something here?
 
Dilbo said:
Now she tells me that she doesn't really have any "hot" pix of herself, and what she is sending are pix from when she says she was much younger and sexier, and modeling. And further, she says the pix I've sent her of some of them from my bare ladies with bare pussies collection don't really turn her on, but one that I did send her of me sporting a semi-erect cock was very "hot" for her. I guess what I'll do is send her some more naked me cock shots, and then spice them up with one or two of a girl's hand jerking me off, and see what that leads to. Stay tuned. I'm also going to urge her to get her own, private Digital Camera. That could put us on an even par pretty quickly, no?
Am I still missing something here?

Yes, definitely keep sending pics of what she wants, if she wants your cock then be happy that she does and keep em coming to her! ;)

A digital cam will definitely spice things up a bit, good idea suggesting it. :D
 
Have you ever thought about why she wants these pics? What is she doing with them? You probably think she's using them to get off, but are you sure that’s the case?
 
She can do with them whatever she wants. I have no inhibitions. Today, no pix were exchanged, but we were just on the verge of some cybersex when Hubby came home from Labor Day work, so we had to shut it down. She told me, among other things that she and her main squeeze now have a lack of interest issue on his part. She also has a very hot daughter who is just a year underage for Lit, so no more will be said about that possible cyberconnection, at least here on this site. Again, stay tuned. She's willing to go out and buy a digicam, but the first results she gets will undoubtedly need some coaching as to improvement in their sexiness. I'll take on the job. Tomorrow I'll send her a picture of my flaccid cock, up close and pernal, and see what commen that brings.
HEY, I'M NO LONGER A VIRGIN HERE! Since the last time I was a virgin in reality was in 1961, I'm glad to have graduated.
 
Update....

Well, guys and girls, it's taken me awhile and the exchange of some relatively innocuous pictures between us, mine being the most graphic, but as of today, we have come down to this. She is now telling me that about 15 years ago, she and her husband, as 30-year-olds with a very young daughter, began swapping with their next-door neighbors, also young parents of one child at the time, when her neighbor's hubby was a stay-at-home Dad, and she (my friend's daughter) was a stay-at-home mom. He was a big flirt with her, and the two couples started entertaining each other in their homes. She had been disappointed lately with her husband's performance in bed. He was very well hung, and came very big, but couldn't manage or didn't want to bother to get her off. Her neighbor suggested that he could, so they plotted to bring the other two together in the bedroom to give themselves some privacy to do the deed. It worked, the other two went upstairs and my friend's daughter and her male neighbor retreated to the basement, stripped each other naked, and had an hours-long fuck session. He gave her orgasm after orgasm. Her neighbor's wife was a blow-job specialist, she learned later from her hubby, and sucked him off several times while his wife was being fucked in the basement. My friend's daughter's in laws had a resort home and the parents went away for a couple of weekends, so the two couples went there and did nothing but fuck the entire weekend. At one point, she was taking on both of the men at the same time. That's where we are in the story today, with another installment coming this evening. How'm I doin', with this, so far?
 
Last edited:
Indynudedude said:
Geez, this is like a "Dear Penthouse" letter. I'd be surprised if any of it were true.

Well, she jacked me off by cybersex for the first time today, and I almost got her off the same way, but she had to thrown on a robe and stop when her hubby and teen-age kid came home. And I swear to got this is true! Who needs Penthouse when there is Literotica.
 
Back
Top