"needed help measuring something"
OH MY GORSH THAT IS A ONE-PERSON JOB IF EVER I SAW ONE. WHAT DOES HE NEED TO MEASURE, AN ELEPHANT?

New to Topping might try sitting in a kitchen chair while blowing his partner who could then sit on New to's cock and take care of the penetration and active role at first.

" because I thought it was hilarious and wanted to show it to my girlfriend"

Was it really necessary to blame the wife & her gf, whom the parents already don't like?

Yeah I already said this on the other thread but I never thought it need be fake. My husband accidentally sexted his mom instead of me awhile back.
Since we don't live in the Bible Belt, thank god, a good laugh was had by all and no Very Serious Discussion was needed.

jesus christ nancy, just stick it in.

BE A MAN!

"when push comes to shove" is the line of the week. Good luck bro.

@3: My wife and I both agree that being able to blame each other for things when in the presence of other parties is rather useful. It's most useful when you're only dealing with customer service or something, but you can slide yourself past unnecessary obstacles with the trick on occasion.

Advice to BOY, agree that you will and then at some random time your BF can prepare and just climb on top (or whatever) without a big discussion before. No mental anguish.

I like to think that TEXXXT's in-laws had their eyes opened, à la little Frankie McCourt in Angela's Ashes:

...Bless me, Father, for I have sinned, it's a fortnight since my last confession. And what have you done since then, my child? I hit my brother, I went on the mooch from school, I lied to my mother. Yes, my child, and what else? I- I- I did dirty things, Father. Ah, my child, was that with yourself or with another or with some class of beast? Some class of beast. I never heard of a sin like that before. This priest must be from the country and if he is he's opening up new worlds to me...

I admit that what immediately sprang to mind was that commercial in which a husband says, "Not wash; power wash. Big difference." As I cannot get out of my head that commercial's inclusion among a large group of commercials in which men are presented as incompetent and nothing more than a trial to women, that increases the difficulty in thinking of the term "power bottom" with a great deal of approbation, not that there's anything wrong with great enthusiasm for one's preferred role.

The letter read to me as if the activity in question would occur once or perhaps at most maybe once a calendar quarter in the minds of the two participants, and Mr Savage's reply, which includes a recommendation for "the first few times", seems to assume it will become a regular item on the menu. Editing? Otherwise, tomorrow LW might reply to Mr Savage that neither of the pair intends it to happen more than a few times at most.

Here's what I just cannot wrap my head around: getting called home - as an adult! - to "face the music"...WTF?

I think there have been exactly two conversations about sex with my parents since I was given 'the facts' at like age 8 (by being handed a book). There was one rather uncomfortable convo where my father's prurient curiosity (I think out of a desire to live vicariously) about certain BDSM activities got the better of him...I shut it down pretty quick.

My own advice for BOY? "It's not as if you'll only get to do it once." Even if attempt #1 doesn't go well, practice makes perfect, and it sounds like the partner wouldn't mind a little practice.

If a Top orders a bottom to ream his ass, then it's the bottom's duty to ream it.

@10 you make a good point, but it's a little hard to tell the other guy's preferences. Think of the PANTIES LW in this week's SL column. Five years in, he casually brings up his desire to wear panties, and then suggests it would make a nice birthday treat, for her to indulge him. Yes, maybe PANTIES only wants to crossdress occasionally, but maybe he is interested in doing quite a bit of it.

Similarly, it's hard to tell whether the LW's partner is playing down his interest in being topped to avoid causing anxiety for the LW (as PANTIES backed off with his wife).

I think Dan's point is that anal can be challenging, and thinking you're going to do it once a year is likely to raise the stakes for that time (and thus decrease the chance of it going well). Whereas saying, "oh, you're interested in anal play? Sure, let's add that to our repertoire" reduces the stakes by encouraging toys & fingers as part of the action.

"J...J...JAM IT IN!!!"
"You lost me."

Advice to BOY: My previous boyfriend had similar issues. I'm a 90% top but love getting fucked every once in awhile. His lack of confidence resulted in failure approximately the first 10 times we tried. In every case, I reassured him that I was not disappointed and that one day, it would happen and be amazing. So we would stop having him try and penetrate me and move on to something else. I never wavered on my commitment to making it work. It took a lot of patience and understanding, but eventually, he succeeded, and then became a master top. It was so good that I became more like 60/40 top, and he was VERY ok with that. Initially, he had to finish himself off by jacking off, but eventually he mastered the art of hands-free orgasm. WORTH THE WAIT!

BOY: I've been fucking people for years, and even after all this time, it's still been my experience that nothing kills a boner quite as effectively as "I must maintain this boner at all costs!"

Establish some kind of contingency plan with your partner that takes that pressure off, whether it be toys, fingers, trading places for a bit (maybe something like a playful "You call that fucking? I'll show you how it's done!" if that makes sense within the dynamic of your relationship), whatever. Acknowledge that it might not happen (and that it's okay if it doesn't) and it will be much more likely to happen.

Also, maybe cockrings.

BOY,
Assuming that your BF douches well, I'd recommend rimming him to get up close and personal with the hole you're going to fuck. As Dan suggested, playing with his ass and seeing how he responds to that can also be fun.

Actually saying the words "I'm going to make you feel so good" can work, too. You know how good it feels, BOY

Please note, however, that the definition of a power bottom is «dominant bottom», not a submissive one, regardless of the bottom's abilities or enthusiasm.

Ms Erica - You're comparing OS to SS. I'ts possible, but the odds are rather different. If BF were similar to Mr Salty, LW would almost certainly know. (Pity Mr Salty can't advise BF.)

Interesting problem for a woman to think about. I can empathize with retraining my partner's dick to work with me, as I'm sure BOY is adept at as a power bottom. But the bf doesn't seem to understand BOY's dick. I guess he is used to dicks that love penetration?

Anyway, I think that if BOY wants to top, he needs to hear what his bf is getting out of bottoming. Otherwise his dick is not going to get a rush out of delivering the goods. For example... spending a few hours getting to know his hole... talking about bf's favorite bottoming moments while jacking... hold a dildo still while his bf shows him where his spots are... assuming that bf wants a good fuck. If he just wanted to see what BOY liked as a top, then the answer is nothing until he gets comfortable topping.

I thought the advice was good but a little light acknowledging that it started as something bf wanted and BOY should ask more about before he can be expected to deliver. Now there is a new problem for BOY, who would like to learn to top well to feel more like a "real man" which I guess means he wants to be a more versatile lover.