Stilettoscot

Yeah, that's the same (still have it on now)...just took the pic when I got home as the pics from the poker room were too dark on my camera phone. Thanks...the walk out was uneventful as noone was really around at 4am except a couple arguing near the parking lot...

Back in 1994, I worked in Boston as a mailroom clerk for a large finacial company. As a 20 year old who had a closet "thing" for heels, I was just starting to get out (working in Boston helped) and buy some "stuff". Well, I was working 2nd shift then (3-11:30PM), and my shcedule would be such that I would do my last mail pick-up run to another bulding (about 3 blocks from the mailroom) at 10:45, get back to the mailroom about 11:20...sort through the mail really fast, leave, catch the subway and get to my train about 11:50 in time for the 11:59PM train to my hometown (last of the night)... About a month after starting that shift, while doing the last run on the 41rst floor (I'd have to pick-up mail from the 41rst, 42nd, and 44th floors), I noticed a pair of GORGEOUS 3 3/4" stiletto sling-backs in a cubicle on my route. It was obvious the lady who worked there wore her sneakers in and shoes while there. Well, luck would have it she wore size 10....my size! Obviously, late at night (very rare to have anyone there), I HAD to try them on...beautiful fit! Little test walk...awsome! Next day, my plan was hatched to wear stockings under my uniform (black slacks with navy blue collared shirt...went well with black stockings and these sling-backs!). So arrived, slipped off my ugly shoes...slipped on her sling-backs, and went about my route. What a feeling!! Over the next couple weeks, I did this 2-3 days per week, and always enjoyed it immensely! One time, I almost got back too late as time went by a little too fast... So, this random day comes, and I, as usual, slip off my shoes and leave them near the guard station at the elevator bay, walk just around the corner to her cubicle, and slipped on her shoes. No sweat. Did the 41rst floor, no probs, until I got back to the elevator to go do the other floors from the back way and the cleaning crew were in the lobby!! Panic! Run back the way I came! I was a very shy 20 yr old then, wearing nice high heels...but there I was, cringing and anxiously waiting for the cleaning crew to leave before I had a heart attack! They did leave, but I had no time to change back, as I was now running late. Did the other floors as fast as possible in stilettos, got back to the 41rst floor to change back to leave...and the cleaning crew took my old shoes!!!!! Oh MY GOD!! Now what?? So, I ran around, panicking, looking (hoping) for some guy to have left some pair of loafers or something in their cube. NO luck! 11:35PM comes...I HAVE to leave wearing these shoes!! I am ready to cry... Of course, in the lobby were polished granite floors...and I had to walk by the guards on the way out...then 3 blocks along the busy shopping area...then up the elevator to drop off (left it next to the elevator in panic) my mail (unsorted)...and with my head down, click-clicked through the street to JUST make my subway....packed with Celtic fans! Horror. The worst part was walking through North Station (Boston Garden) with hundreds of Celt fans just getting out of the game. The occasional whistle, "hey babe" comments from drunks...etc.... I just made the 11:59PM train. Cowarded in the corner of the furthest car, I still had all kinds of people (it seemd at the time) staring at my feet.... Cab ride home was fun. Talk about shocking yourself into going out in public (that was my first time..and last for a while!). Of course those sling-backs became a nice part of my collection. Occasional midnight walks around town with them... I would, however, have loved to see the lady's face when she came into work the next day! True story.

Not the best looking shoe, but I voted "yes"...with practice. At least for shorter distances. Didn't take me long to learn to walk in 6" (no platform) stilettos pumps back 2 years ago, and could do so after only 10 minutes of trying for decent distances (like car across parking lot to ATM and back...at night of course..).

Echoing most of the answers, I posted "just a man in heels"...except when I go to the clubs. I am (in my eyes) too masculine to completely dress up like a women, but from the waist down, I do wear garter-n-stockings, party heels (clear and slutty), and tight lycra skirt. Feel great in it.... When I go out (hoping to do so more frequently) around town, it's mostly in black denim or blue jeans, and 4, 4 1/2" stiletto pump-like shoes...

Wow! Excellent stories...I wish I could be part of the same (especially hanging where w6ish does!! ) One day....

...take a newbie out in public? I am sure it'd help my condfidence level, to know there are like minded folks in the area willing to go out in theirs with me. I'm from near Boston, but would travel, even to NYC or beyond... Thanks in advance!

Went well. Got to the elevator block in the main entrance, about 6 or 8 people waiting, noone even cared besides a girl (about 19) asking where I got them. I got a few looks from a couple teenage kids with their pants around their knees and hats sideways, but...

Got off the 8th floor, and walked really fast. Then realised it went well!

Thanks for the comments. The outfit...maybe one day soon I'll get a little more comfortable out in public!

http://s175.photobucket.com/albums/w143/Big_Carphuna/?action=view&current=heel.jpg

Not my "best" 'Freestyle', but the only pic of myself in any now. Casual going out last night...

http://s175.photobucket.com/albums/w143/Big_Carphuna/?action=view&current=heel.jpg

Thanks Johnie and Richie!

I went out to a friend's house to play poker with the "boys" and gals". Noone seemed to mind, even the people waiting at the elevators. One of the ladies there did inquire about my shoes, how I walk in them, and if we could go shopping one time together!!

This was my outfit. Nothing special, except my shoes. I love 'em!

http://s175.photobucket.com/albums/w143/Big_Carphuna/?action=view&current=heel.jpg

Also try to exude confidence and you win people over. The more I wear heels openly the more I just don't care what people say or think.

I agree with Richie that we should stop scaring each other and put on nice outfits and shoes and go outside.

This is the part I, and I am sure many, other guys are having difficulty with. Good advice. I'll keep saying that to myself when I am ready to go into a public place with my stilettos on, knowing people will see....

I have to get a job where I can wear mine.. I doubt I could get away with it while landscaping..LOL I did wear them a few times, years ago, while driving a taxi.

I have yet to build the courage to go out in public enough to really take notice of reactions. I have been out on numerous occasions, though, but fairly discreetly. I know I've been seen, but besides at a store trying them on, or clubs (where I am not alone), I rarely go where lots of people are....yet. No bad reactions yet. I am hoping that tonight, when going over a friends house, that I won't be nervouse about walking clear into a large apt complex through the main enterance... I'll revisit this thread tomorrow if I do have the guts to..LOL

Nice! In my trials, I have found it best to ask a salelady (especially gorgeous ones) if this would be OK. I have yet to have one say no! 2 or 3 have actually offered advice and it seemed to break the ice! I have worn them out only once, but it was really fun! Of course it was only from a department store (Burlington Coat Factory), but I tried them on first, so knew they fit, and got compliments on the way out!!

From my experiences, the shoe HAS to fit well. Once it does, you'll be able to keep from peeking down, which is a big no-no. Although a muscular man, I have always had good dexterity, and big hips/ass and very strong thighs, which helps. I have been told that I "sway" my hips when I walk naturally, which contrasts my wide shoulders. But, my posture is good, back strong, and I have good balance, which all help, I think. Keep your head up, arch in your back, toes pointed straight, and relax your hips, swaying as you walk. Also, my knees hyper-extend, which I believe also helps in that it takes heels of over 6" (no platform) to have my knees bend while standing. So, I can easily and comfortably walk in 5+" stilettos. I guess I was lucky in that I could do it well from when I was young. Just be careful!

Well, my first post... I am a 33 yr old hetero man, born and raised near Boston, MA. Ever since I can remember I've had a "thing" for women's shoes (and things like stockings, garters, etc...), but even dabbling with it at "safe" times and places (home or out late night strolls), it's been something I've "had" to surpress for years. Was married 5 years, and shared my love for the above with her. Big mistake. Happily divorced 4 years now... Of course that was only part of it, but it hurt me to know the women I loved didn't accept my passions. Only a couple close friends (women) and my older sister knew...except, I am sure, my parents who I bet found some of my items back when I was a teen.. Always could walk very well in high heels, and simply, as I am sure many of you know well enough, feel great in them. I can still remember the excitement when I was first working in Boston of buying a pair of size 10, 5" stiletto pumps. Luckily for me, my feet are very small for my size, and slender. Those were gorgeous shoes (wish I still had them), and how I felt in them was more than I can describe. Heck, I even remember sneaking into my sister's friend's mother's closet and trying on her high heels when I has like 5 or 6. Or finding (and subsequently keeping) a pair of nice stiletto sandals while playing baseball when I was like 12 or 13. Fun time trying to sneak them home rolled into my shirt with a bunch of neighborhood kids around! Now, though, I have been more "brazen" with my heel wearing. Nights, driving during the day, doing errands (even things that I don't really need to do at the time)...just trying to dare myself to wear them in public more. I only own 5 pairs now, all stiletto from 4" L'heroux and pumps, 4 1/2" slingbacks and pumps, and 5 1/2" clear heeled "clubbing" sandals. I rarely buy any other color than black, but my slingbacks are brown to match an outfit I like. I dress in regular (boring usually) men's clothing (unless I am clubbing at a local gay bar wearing my clear heels, garter-n-stockings, and tight skirt), and even with bland men's clothes, the heels look and feels great! As far as my build, well, I'm 6' tall and very muscular (235lbs). Not your typical heel wearer. Wide shoulders, big chest...yet walk well in them. They "slim" my appearance a bit, which I like. Because of my build, I have no interest in dressing like a women from my waist up at all, and besides stockings, rarely do so below. Over the last few months, I have come to grips with my passion for heels enough to "come out" to many people in my life. Family, many friends (especially my friends who are gay/lesbian who are usually way more accepting), etc. In doing so, I have been more encouraged to wear my shoes out in public more. Hoping to feel as confident in doing so as many of you (thanks for the inspiration!! )!! It was an eye opener, but, besides my ex, the people in my life have been good about it. Is there anyone here from the MA north shore area? It'd be nice to actually meet someone who shares in my passion for shoes besides just at a club. Just wanted to say thank you for this site. I will definately stick around! Scott PS, I'd like to learn how to post pics. Wish this forum had the typical "browse" upload system for dummies like me..