Jack’s Answers
1. When is the last time you or your loved one had their prostate checked?
The last time I had my prostate checked was during my last physical, which was…well, suffice it to say that it’s probably been too long.
2. Besides a medical professional, how many other people have had their finger up your ass?
Just that overzealous TSA who felt I didn’t look “American enough”. Racist bastard.
3. Have you ever given or received a prostate massage? Did you like it? Did you cum or orgasm?
No, I have honestly never had my prostate touched as part of sex play. I know it’s supposed to be great and lead to intense orgasms. But my ass is pretty much off-limits. Now, I know what you’re thinking: For all my sexual open-mindedness, I’m apparently afraid to put my money where my mouth is when it comes to ass play. But the truth is that I’m not in any way, shape, or form squeamish about the implications of being on the receiving end, nor am I necessarily worried about pain. No, my reluctance to switch the sign on my butt from “exit only” to “entrance” is due primarily to my squeamishness about the primary function of that orifice. If someone ever tried fingering my ass and got more than they bargained for, I don’t know that I’d be able to live it down.
4. Do you enjoy anal play–rimming, fingering, penetration, etc.?
Yes, I enjoy all of these things as the pitcher. For the reason mentioned above, I am not fond of catching.
5. Ever had anal sex?
A. No, and I don’t want to.
B. No, but I am dying to try it.
C. Yes, but it is just okay.
D. Yes, love it…can’t get enough of it.
E. That’s the way I like it. Anal sex is the best sex.
I’d go with D. I really do enjoy anal, though I don’t think I’ll ever enjoy it as much as vaginal intercourse. Given the opportunity, we’d have much more anal than we have been having lately. I’m thinking once a week would be good.
6. You are about to have anal sex, which method would you choose:
A. Finger up the ass
B. Prostate stimulator
C. Penis–real or strap-on
I’d go with C. We are talking about my penis here, right? Not my ass.
Bonus: Show us your Movember moustache. Post a photo.
Ask and ye shall receive.
Bet you didn’t know I’m a natural redhead.
Jill’s Answers
1. When is the last time you or your loved one had their prostate checked?
Whenever I am asked about my prostate I always forget that women have one. The female equivalent of the prostate is the Skene’s gland, which is basically the G-spot. It’s been stimulated many times, but as far as having it checked, unless they do that during a pap smear, I don’t think it’s ever happened.
2. Besides a medical professional, how many other people have had their finger up your ass?
Two people have fingered my ass. The first was an old fuck buddy of mine who enjoyed that sort of thing. The other is, of course, Jack.
3. Have you ever given or received a prostate massage? Did you like it? Did you cum or orgasm?
I’ve never massaged anyone’s prostate, but I have had my G-spot massaged many times, by Jack. To say that I like the experience is an understatement. I love it! It gives me the most amazing and intense orgasms, and I squirt everywhere.
4. Do you enjoy anal play–rimming, fingering, penetration, etc.?
Yes, yes, and yes! I enjoy it all. I love it when Jack fingers my pussy as he rims my ass. Both of those sensations together get me so hot and usually make me cum hard. It’s so intense. I also enjoy having my ass fingered, usually while Jack is fucking me doggy style or in the missionary position. I think of it as double penetration lite. And I do enjoy penetrative anal sex as well. We don’t do it as often as either of us would like to, but when we do it’s worth the prep.
5. Ever had anal sex?
A. No, and I don’t want to.
B. No, but I am dying to try it.
C. Yes, but it is just okay.
D. Yes, love it…can’t get enough of it.
E. That’s the way I like it. Anal sex is the best sex.
D. As I stated in my answer to #4, I really do enjoy it. It helps that I have a patient partner who knows the importance of moving slowly. To elaborate on my previous answer, we don’t have anal sex as often as we would like because we rarely find ourselves with the necessary time to devote to doing it properly.
6. You are about to have anal sex, which method would you choose:
A. Finger up the ass
B. Prostate stimulator
C. Penis–real or strap-on
I would choose all three! When we have anal sex, it tends to begin with Jack rimming me slowly and sensually, usually while he fingers my clit or my G-spot. When I am sufficiently warmed up he fingers my ass while continuing to play with my pussy. And when I can’t stand it anymore, when I literally can’t bear the thought of not having his cock in my ass for another second, that’s when he fucks me.
Bonus: Show us your Movember moustache. Post a photo.
Does a milk moustache count?
It really is milk.
How to play TMI Tuesday: Copy the above TMI Tuesday questions to your webspace (i.e., a blog). Answer the questions there, then leave a comment below, on this blog post, so we’ll all know where to read your responses. Please don’t forget to link to tmituesdayblog from your website!
Like you Jack Gene is leery of it but he has allowed it a time or two, and enjoyed it when I got him to relax about it. Like you Jill it takes prep but soooo worth it when done right..
Love the pics guys!!
I can’t wait to try Anal, but scared cause everyone keeps telling me how much it hurts!
Great answers as always!
Jill, are ya sure is milk??? hehehe
Hugs
Aluv
Time for the gay mans perspective on Anal sex.
I was a top for a long time but I enjoy anal sex, so much more as I have matured. There have been many occassion, when my prostate has been massaged by another man, they usually have to be well endowed. But even the thoughts of having another man in me, is such an incredible turn on.
@Jack
1. Jack! Get your full physical exam and that prostate checked, please. BTW, I am giving all sexy bloggers free prostate exams. Bend over and cough 😀
3. There is a ritual to prepare for deep penetration so no icky occurs.
6. No honey you cannot put your own penis in your ass. But we will still accept answer “C” just understand that I will be pegging you 😉
Bonus: So cute & creative
I’ve disappointed at the lack of bloggers showing their ‘staches and many normally post photos all the time.
————-
@Jill
1. Have your loved one get his checked, he doesn’t need to wait ’til he’s 50 yrs old.
4. I think we ALL knew Jill’s answer to this.
6. Greedy, greedy girl.
Bonus: AWESOME
(sure it’s milk)
Jack and Jill thanks for showing your ‘staches
-H
@Mind of Mine: Your comment is an incredible turn on.
-H
I am so glad to hear that Jill loves anal after her inital experiences with it.
Jack. you stole my photo idea!!! 😛
1. You two sound perfect together.
2. This makes me miss my honey-bunny, who is traveling this week. I won’t see her until we stay with her family over the holidays, so I guess we’ll see how quiet we can be about all of this, with her mom sleeping in the next room.
Um. That milk mustache is super hot.