TMI - Tuesday the underwear edition

1. Is there an entertaining story attached to (women) your first bra / (men) your first jockstrap?
Hmmm I don't know how entertaining it is. I remember my first jockstrap. It was in 7th grade and I had to buy it for wrestling. I think the first jockstrap is a little awkward for any guy. "I'm sorry where does my junk go exactly (the cup made it weird), and these straps go where? " I think trying to get my first bra off a woman is far more entertaining. Damn I struggled and struggled with thing. I would like to personally thank my stripper GF Brooke for teaching me pinch and twist.

2. Is there a story to (women) your first try at bralessness /(men) your first encounter with bralessness?

Yes, yes, yes it was in Elementary school. Yep, I had figured out young that I liked boobies. We had this young super blonde librarian like right of the Swedish ski team . I even remember her name Miss Schreiber. How's that for an impression. She never wore bras during the summer when the school library would be open and it was gloriously noticeable. I am sure she never suspected that a 5th grade boy was honed in on those bad boys!

3. How about your first time going commando?

I don't remember my first time, but I have done it often. Actually I did it a lot more after I had kids..Why? because there was never time to get caught up on the laundry! :-) Which really is the only reason I go commando.

4. Or your first discovery of lack-of-underpants in another?

Actually, the first time didn't really involve me per se. I was in line in the mall for the midnight showing of the Rocky Horror Picture show. Two lipstick lesbians in Terry Cloth stretchy dresses started making out right in front of me. The one girl ran her hand up the other girls dress and ..whoa! Hello. I was with my GF and admit I had the hardest time pretending I was not watching. The other time I was involved was some of the best sex I ever had. I mean nothing says welcome when you go for third base and there is no third baseman!

5. Any other good underwear-related tales to tell?

No, not really well I had a GF buy me a G-string once that was an Elephant with a trunk complete with ears and googly eyes. So you can imagine how the trunk all worked out.


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