Wednesday, July 15, 2009



Last night on my way back to the hotel from shopping I stopped at a quick-mart for a water and a bottle of beer. Much to my luck this girl was at the counter in front of me. The clerk was quizzing her on her ID. I'm not sure what she was buying, but he said that the photo on the ID didn't look like her. She was able to recite her address and other details, and explained that she just turned 21 a few days ago. That bought me enough time to snap this picture.

Monday, July 13, 2009

4ht of July Parade


DSCN6427A
Originally uploaded by SheenV
This woman was with her son in our town's 4th of July parade. I see her every year and she always wears a similar outfit - heels that are too high, an outfit that is more for the clubs than a morning parade. I do look forward to seeing her though. I'd love to ger her legs around me and have some fun with her feet.

Friday, July 10, 2009

Tuesday, July 07, 2009

The lack of posts is not for a lack of activity. I was in Miami Lakes last week for another trip and did manage to have some fun. It was a very rainy week. No new shoes.

I did make e-mail contact with another CD that lives in the town. She tipped me off to a clothing warehouse nearby that sells cheap lingerie and some other women's clothing. Cheap prices and kind of cheaply made too. The clothing styles cater to the Latino crowd and I think I was the only English speaker there. No problems though. Lots of nice bras, panties, sets, jeans, shorts, and some tops. I just bought a pair of over-the-knee socks (which were short) and a stretchy tank top. Next visit I may go for a pair of jeans and a bra/panty set.
I also was listening to the Sex Spa with Kitty Stuart show on BlogTalkRadio. I can't remember what the topic was, but she was interested in talking to CDs. I only caught the end, but she asked me to send in my thoughts on being a CD. I sent her an e-mail and hopefully will be able to talk more the next week.

Here's some fun from the airport on the way back. This girl was sitting across from me at the gate, busy with her cell phone.


Wednesday, July 01, 2009

To say that this video is a close-up is an understatement, but I do like watching it.

And here's one of Nina Hartley, and extremely talented actress. I love her personality and how she's in control of the scene. Everything she does she does because she knows the affect its having on him and her. The look in her eyes and that grin on her face completes the effect. And those are the things that make a good actress (or actor). She's just not going through the motions or along for the ride.

Tuesday, June 30, 2009

Okay, I'm in the hotel room, its pouring down rain, and I'm in my panties at the computer. And I'm watching these:

I'd so love to be the guy in this, this, and this

These girls are sooo lucky in this, this, and this

Monday, June 29, 2009

As mentioned earlier, I'm on a business trip this week. If you're available to chat in the evenings (or maybe during the day), I'm "JanCD66" at Yahoo, or comment here, or send me an e-mail.

After landing and before heading to the plant I stopped at Kohl's to find a girly running outfit. No luck. It seems that the sales they're having are doing the trick as there wasn't much of anything in my size that fit the bill. I tried T.J. Maxx and Ross, both strike outs. Maybe I'll head back to Target after work if its not too late - I don't want to sacrifice a chance to run on not having an outfit.

Wednesday, June 24, 2009

Wednesday Weirdness #60

Its the time for Wednesday Weirdness #60

1.) To you, what makes the perfect body the perfect body? Proportion - nothing too big or too small for the body size. From there for women, its all about legs and feet! There's no particular size or shape that I'd say is better than others.

2.) What part of your body do you obsess about the most? Probably my stomach. My legs are in good shape from running, but its my 2-pack stomach that needs transformed into a 6-pack. I mean, its not a beer belly, I just need to do a lot more sit-ups.

3.) What makes a house a warm, welcoming, comfortable home? I like smaller rooms as opposed to large open spaces with high ceilings. Plush chairs and couches are nice. Thick carpets that feel good in bare feet. And quiet. I don't want to hear the heater or air conditioning, or the outside if the windows are closed. Not too bright lights.

4.) What fabric feels sexiest against bare skin? Silk. Its smooth, sheer, and warm.

5.) What is the lamest lie you have heard in the last month? I can't remember any one standing out.

6.) What always makes you feel better when you're upset? Running, chocolate, and a good beer.

Speaking of running, I ran another 5K last night. It was a new course as compared to the last time I ran that race two years ago. Very much hillier than before, and probably the most challenging street race I've done. Not sure about my time as the clock said 24:52 as I crossed the finish line and the print-out said 23:29. I'll check the website once the results are posted for the official results.

And next week I'm back in Miami Lakes for a few days. I need to find a running outfit that will push the boundaries a bit more.

Monday, June 22, 2009

Some new and interesting Star Trek links:

Artist Devorah Sperber's unique ways of depicting Star Trek.

Treknobabble from Filmjunk.com. I wish I found this months ago when it started. Lots of great info!

And from Daphne's Desires blog, the latex uniform.

And UGO. Don't forget to check out the Hotties of Star Trek.

Thursday, June 18, 2009

Not much new going on lately. Tuesday I was out with the running club and ran 6 miles with them. Afterwards we had pizza and beer. My only choices were Bud Light, Miller Lite, and Coors Light - and water (just about the same as the first three). I chose Bud which I haven't had in years. I should have picked the water. I mean, Bud Light has so little taste and body that water really is a better choice.

And does anyone know the differences between rugby and Australian rules football? They've been showing one or the other on cable lately and I'm not sure which one it is. It is from Australia, and they do call it "rugby". Not being too familiar with either confuses me. They're not wearing traditional rugby shirts (heavy cotton, stripes, etc.).

Another trip coming up on June 29. Not sure what plans I have for that week other than running. And masturbating. Any suggestions?

Edited on 19JUN09 to add from Miss AJ:

"Well for starters there are a lot more men on the field in aussie rules. Also there isn't the same degree of physical tackling so a lot less opportunity to watch men coming to grips with each other. I don't watch AFL although living in the home state as I prefer rugby league. Rugby league is a dumbed down rugby designed for the viewer rather then the player. So it still has physical tackling but the players have to get up quicker and get the ball moving faster. AFL has a lot more kicking and the players have to get rid of the ball faster. I have never understood footy rules so can't help you there.

So how many men are on the field with the shows you are watching. If it is 18 on each side and they pass the ball to each other very quickly it is likely to be AFL. If there are 13 men aside and they hold on to the ball longer and get down and dirty with each other it will be some form of rugby."

Great information, Miss AJ!

Wednesday, June 03, 2009



Tonight was a very fun night. I left work on time and changed at the hotel. I put on a pair of pom-pom socks, the polka-dot panties I bought last night, white short-shorts, a bra, and a polo. First I went to the grocery store and three teen-aged girls in the checkout line behind me did notice. Their laughter when they left confirmed it. Then I went to Starbucks. Lots of women there and few men. Like last night they read me quickly. When I left I took the long walk around the outside and went past these two very hot Latinas at a table. The one facing me immediately read me - her eyes widened and didn't leave me. I think they noticed me when I was in the store. She motioned to her friend and they both looked right at me. The rush of humiliation got me walking taller past them. I heard a few whistles as I walked back to my car.
I then went back to the hotel to change into the white pants from yesterday. Again, the panties were very visible - and the heels even more so. My first stop was the adult store. I browsed through the large selection of videos, lingerie, magazines, and toys. There was a pair of girls who did notice me, but gave no real reaction. A couple then came in and she noticed quickly. There was a single girl that was buying some lingerie. She didn't notice me until I went up to the counter to get change for the video viewing rooms. The clerk had to do something for her so that gave her more time to look. Once I got my change and headed to the booths, I could see both of them looking at me and talking. I then went to another Starbucks. This one was packed with people, mostly women again. The girl sitting by herself outside saw me first. The girl at the table with two guys saw me second, and I think they took my picture with a cell phone. Their friends came in a bit later - two couples, and they tipped them off. When I left there was a table of two ladies and another of about 4 girls and 2 guys. The girls noticed the sound of my heels right away and tipped off the guys. I walked around a bit and noticed that most everyone was looking at me. The humiliation was exquisite! When I left I did one final walk-by and got a few whistles.

To top off the night I walked into the hotel's lobby to ask if they could give me a new key as mine
"didn't work". She's seen me before dressed so its no big deal.

Tuesday, June 02, 2009

Had some fun tonight. After work I went running in the new women's singlet. Excellent! The larger arm holes and the T-back are great for keeping cool and keeping the shirt from riding up. The fit was just clingy enough to wick away the sweat but not tight.

After running & showering, I went to to Victoria's Secret for the sale. Only two pairs of panties this trip. Then to the shoe store to buy a pair of heels - t-strap pumps with 2-1/2" heels. Then I went to Starbucks for coffee. I put the heels on and got noticed right away by a table of two teen girls that giggled very nicely. There was another table of two 30-ish women. I know one noticed, and I'm sure the other did too. I walked around as I drank my coffee, lifting a pant leg every now and then or extending a toe to show off the heels. On my way out a table of guys & girls sitting outside gave a few whistles.


Can you tell what I was wearing underneath the pants?

Monday, June 01, 2009

Ok, I'm in Miami Lakes again today through Thursday. After landing and before going to work, I stopped by Target to buy some women's running clothes. I picked up a singlet and socks, but no shorts. They didn't have the bun huggers that I saw on their on-line store. And the other women's runnig shorts weren't really feminine enough to diferentiate them from men's. So, here are my purchases:



After work I changed and went to the local mega-grocery store for water (and a lipstick). Not sure how many people picked up on my outfit. I think one lady did. As I was looking for lipstick, she and her husband walked by and stopped about 15 feet away. She stopped and made a comment to him using her hand to indicate something small. I think she was saying that I had the little cotton balls on my socks. Can't tell if anyone else noticed. Anyway, I then went to get a salad for take-out. No running tonight as its pouring rain.

And this looks like fun (NSFW).

Friday, May 29, 2009

Hi everyone! As if I didn't have enough of Florida yet, I go back for work next Monday through Thursday. I'll have time to chat in the evenings at Yahoo (JanCD66 there) as well as at Chatropolis, or wherever you might tell me you're at.

The crossdressing jogging thing has got me thinking over the last few days. I've found some nice running clothes at Target that I'll pick up while I'm there. Stay tuned for pictures and stories! And I think Victoria's Secret is having their semi-annual sale in June, so I'll stop by there. Maybe I'll wear my white short-shorts with a pair of brightly-colored panties underneath to the store.

Wednesday, May 27, 2009

Wednesday Weirdness #57




I was away on vacation from 5/20-25 at Disneyworld in Florida. Great place to go if you've never been. It was my first time there and I'm ready to go back! For those that haven't been there, its more than just another amusement park. There's so much more to see and do beyond the rides. I could go on about it, so ask me if you have any questions.

On to this week's Wednesday Weirdness:
1.) How easily are you insulted? Not very. I don't take people's insults very seriously, you know, "sticks and stone..." Go ahead, try to insult me!

2.) How often do you perform oral sex on your SO? As often and as long as she'll let me, which is not much in either case. She says she's too ticklish down there. I think she thinks that its "just not the proper thing to do".

3.) What brand of shoes do you find to be most comfortable? Doc Martens. I have pairs in black and brown. If you're on your feet all day or walk a lot, they are the best choice IMO.

4.) What are 3 to 5 items you NEVER leave the house without? Cell phone, wallet, some change, keys, handkerchief.

5.) Who did you look up to as you were growing up? (In no specific order) Neil Armstrong, Captain Kirk, Dad. Who do you look up to now? Warren Buffet, Steve Jobs, Dad, Neil Armstrong.

6.) If you've ever been a strip club of any type, what was one of your most memorable moments? We took one of our co-workers to one for his bachelor party. In the first 20 minutes we were there he drank so much that he was out in the parking lot throwing up. A while later another guy was taken up on stage by one of the strippers, she took his shirt off and put her camisole on him. Nothing happened to me that night. Another time I went to one on my way home from work driving from one city to another. I was one of the few folks there at that time of the day so one of the strippers paid all of her attention to me. She kept sitting down on the stage in front of me and would then grab my head, push it into her crotch, and then clamp her legs around the back of my head. Oh my! I was in heaven. I could smell her perfume all the way home!

7.) Should prostitution be legal? Why or why not? Yes! And not just for the selfish reason that I could hire a prostitute and hope not to get arrested. If it were legal, I think it would clean things up a lot. It would get it out of the back alley and into some nice places. Regulation could ensure that the prostitutes are drug and disease free.

Tuesday, May 19, 2009

WW #56

1. If your boss says, "I would like to talk to you about your Internet usage" what would your first reaction be? Feign ignorance and ask what she'd like to talk about.

2. If your SO asks you "Does this make me look fat?" how do you answer? "No. You look fine, but are you comfortable? In fact, let me help you out of that..." and then down to business ;)

3. What is one thing that you pay for, but resent having to do so? Checked luggage on an airplane. Why don't they just raise prices a few bucks? I find it easier to pay a higher price and receive a lot of services than pay a low price and then pay extra for everything. I understand the reason for charging extra (people wouldn't normally use a "free" service if they had to pay for it), but it just irks me.

4. A day is being created in honor of you. How should we celebrate it? If by "we" you mean me and a handful of very willing women then: First, we start off with a nice long run, maybe 7 miles or so. Then a hot shower, and a big breakfast with pancakes. Then we'd get ready to go shopping - I'd get to pick who's panties I'm going to wear that morning - and we'd all get dressed together (and I'd watch them fool around while doing so). We'd go shopping for clothes and they'd get to dress me in anything they like - lingerie, shoes, pants, blouses, etc. - and they'd pull and pick at me to make sure everything fits well. Manicures and pedicures next. Back to home I'd have to put on a fashion show for the gals so they could pick out an outfit or two for the evening. The show would soon enough degenerate into sex, maybe something like the videos I linked to in yesterday's post. Once we've all had enough, showers for all and we dress for the evening out on the town in some kinky places.

Actually, a great day would begin with a long run and then brewing beer.

5. What CD or Album in your music collection do you secretly enjoy, but would be embarrassed if others heard you grooving to it? Genesis and Phil Collins. I didn't like them in the '80's when they were so overplayed. But now I can sing along to almost every time I hear them on the radio.

6. How long do you think you would last if you were a contestant on Survivor? Not long. I'm not a very competitive person, and most of those folks are so overly dramatic. I'd lose just to get away from them!

Monday, May 18, 2009

This looks like fun. Anyone care to wear the catsuit? Definately NSFW. And I think I'd love this too.

So does this, this, this, this, and this.

I'm horny today.

Friday, May 15, 2009




This very attractive lady was sitting across from me at the airport gate yesterday afternoon. Just wish my cellphone's camera was a bit better.


Have you seen the new Star Trek movie? If you haven't, then you MUST!! I saw it Wednesday night at a theater that had a DLP (digital light projector) and I was just amazed!! It was stunning!! I want to go see it again. I know there's been a lot of chatter among the fans about controversy of the movie not strictly adhering to past Trek canon, but I think everyone will agree it's a great flic. Lots of action, lots of references to the television series, and a good story. And no you do not have to be familiar with Trek to enjoy it. Now go, stop reading, and go see it!

Wednesday, May 13, 2009

Didn't post as much as I wanted to so far this week. Monday after work and checking into the hotel I went for a run and then to the grocery store. I was wearing singlet & splits as they call them in the running world. To everyone else I was wearing a tight tank top and very short running shorts. Comfortable to run in, but I don't think folks around here are used to see a guy in such skimpy clothes. Oh well. Then I went to Chicken Kitchen for a chicken Caesar salad that I ate at the hotel. By the time I showered it was ~9PM. I wanted to go shopping, but it was a bit late so I just logged on and spent the night chatting at Chatropolis and checking out the programs on Blogtalk Radio.

I go to Chatropolis because there's always a lot of pervy-minded people there. The one thing that disturbs me about it is that a few folks seem to like posting pictures of the underaged. I don't like that kind of stuff, even if they're clothed. But chatting there, like anywhere else, is hit or miss. Sometimes I find someone that I hit it off with and we have a good chat, and other times its like bumper cars - meet for a few minutes and realize that its not going anywhere. There was a m/f couple that was going to call me, but for some reason they didn't. Another CD did though, and we both go off together. I was up way too late - I think I went to bed at about 2AM.

Last night I went running again after a late day at work, so no time for shopping. I've been thinking all day about getting out to a mall to buy some panties, stockings, a bra, shoes, or a skirt. First I'd shower and shave, then put on some of my girl-clothes - stockings & garter, panty, bra, the pair of white women's pants that I brought with me on this trip, and a shirt. The off to the mall or a women's clothing store. It'd be fun to try some new things on, and maybe take a few pictures in the dressing room for posting here. Not tonight, though. A co-worker and I are planning to go out for dinner and then see "Star Trek". Not sure if I'll do anything interesting after that.

I was chatting with a friend earlier today and Twitter came up. She does, I don't. I joked that I didn't think anyone would be interested in my posts as they would be something like this:

"At work, thinking about sex."

"At work, thinking about sex again. Maybe not sex, but at least masturbation."

"At work, just ate lunch. That cute brunette with the bob hair style wore a nice pair of heels today."

"At home, thinking about sex again. No time as the grass needs to be cut."

See what I mean?

And I like this video.

Monday, May 11, 2009

I'm in Miami Lakes again this week, so look for me in the evenings on Yahoo chat. Maybe some interesting posts & photos, too!

Edit: Now that I'm in my room after work and a 3.5 mile run, its time for a short update. No pictures of this week's hotel room just yet. I'm at a Marriott Courtyard. Nothing spectacular. Raves: A mini-fridge in the room, more chanels on the TV, big lobby. Rants: Further away from work, smaller room.

I've been inspired by a tanalizing woman. I hope to do some shopping this week for a skirt. Mini maybe. I'll see what they have in my size.

Monday, May 04, 2009

I found a new way to waste time over at Armorous Rocker's site. Its a game where these little cartoon characters fight eachother. There's no way to control them, so one just picks an opponent and then sits back to watch the fight. If you go to the link below and fight my character, then it gains experience. There's no obligation or need to sign up if you don't want to.

Sunday, May 03, 2009

Thursday, April 30, 2009

Thursday's Rant

There are a few things that I like about traveling, and a few things I dislike. One thing I like is the variety of rental cars I've been getting. Driving new and different cars is fun. Most these days come with satellite radio and sometimes Bluetooth connectivity. The Bluetooth is cool - nothing like being able to talk on the cell phone hands-free with the sound coming out of the stereo speakers.

Sirius satellite radio is also nice to have in a city that has some pretty awful local radio stations. My favorite channel so far is 22 The 1st Wave. Its all '80's new wave music. The biggest disappointment is Playboy channel 122 (or somewhere around that number). I'd never heard it before, and I'm wasn't sure what to expect. Sure, listening to sweet-voiced playmates talk about sex is great. Its nice to hear women talk very openly, plainly, and graphically about all the aspects of sex as most people don't do so in daily conversation. A few of the women don't have too much upstairs and that makes for a poor DJ. They really have to work on the male talent there, however. I'm not sure who they male DJ's are, but they have a lot to be desired. Their voices are hardly sensual or pleasing. They're more like George Costanza than Will Smith. They play the wise-ass side-kick or "mind in the gutter" roles. How about someone with some intelligence and with a nice voice?

And that's my rant.

Wednesday, April 29, 2009

I missed a few Weirdness Wednesday's so here's a mash-up of the last three:

WW #53
1. Is there a particular smell that turns you on? If so what is it? Vanilla! Vanilla extract, lotion, frosting, candles, anything that has a strong vanilla smell really gets to me.

3. When you browsing a book store for reading material, do you find yourself checking out a book solely based on the cover design? Sometimes. A really bad cover (i.e., cheesy) is a mark for a bad book.

5. How long do you think could you disappear for until someone would notice your absence and start looking for you? At work, most of the day I think. At home, about 2 minutes.


Wednesday Weirdness #52
1.) What items (if any) do you get embarrassed to purchase? Nothing much anymore. Going shopping for girl clothes used to be, but not anymore.

2.) What sexual position do you and your partner/significant other use most? Missionary. I really like to be on top. Its more fun to have her on top, but I need to be on top to really get off.

6.) How do you feel about anal sex? If using a dildo or vibe on myself counts, then I do like it. I haven't asked her to use a strap-on on me. And I'd have to find a very beautiful TS to take a cock in me.

Wednesday Weirdness #51: Story Time Edition
1.) Tell us how you picked the blog nickname that you write under. Were you considering using a different pseudonym or was the one you wound up with your first pick? I thought about a few different ones. "Jan" is part of my Yahoo ID, but I didn't think it was very memorable. "Sheen" is kind of androgynous, and I do like the character on "Jimmy Neutron". I had to add the "V" as someone else had the name already. "V" is also my middle initial, and is 5 in Roman numerals (my fav number).

2.) Tell us about your worst oral sex experience. She doesn't really like giving head, so I can't say I've had a great oral experience to compare it to. And she doesn't like receiving either, so just when I'm starting to have some fun down there, she pulls me back up. I'm taking volunteers to give me a great experience!

6.) Tell us about the weirdest sexual proposition you've ever been faced with. None yet. Anyone want to propose something?

Tuesday, April 28, 2009

Ok, just sitting here in my hotel room on a Tuesday night. One thing lead to another and now I'm watching this (NSFW). I'd totally change places with the guy!

And I'm totally digging her. And here. And here. And here. Kimber is nice too.
This week's new shoes:
I like the buckle detail.
Round toe.
Nice block heel. Much easier to walk in than a pointed heel.



Need a better picture of the pants. They're from The Limited and have a pin-tucked front, low waist, and very flared legs. And they are very comfortable! I could wear them all day.

This week's hotel room. Its divided into two rooms.





And here's this week's rental car. A convertible!

Monday, April 27, 2009

I'm in Miami again this week. The flight down was uneventful. I did score a convertible for the rental car this week. I just hope I have some time to drive it around. More later.

Tuesday, April 21, 2009

TMI Tuesday #183

I haven't done one of these in a while, so here goes:
1. Marriage and children aside, what has been your greatest accomplishment in life? That's a tough on to answer. Running a half-marathon? Eagle Scout? My job (or not getting laid-off)? College degree? They all don't seem too significant in the grand scheme of things.

2. Aside from healthy and happy children, what is your greatest ambition for the future? I want to go back to college to get an MBA. I want to finally fix the garage floor and repave the driveway. I want to run another half-marathon. I want to go to Disney World (Scheduled for next month. I've never been.) I want to keep employed. Again, none of these seem to be too significant.

3. If we were to enter your real name in a search engine, what would we find? My Plaxo.com profile (empty); a reference to a financial advisor (not me); a reference to a lawyer in Texas (not me); a genealogy reference (not me); a donation to my college (me); and then a lot of not-me references. It really depends on how I spell my name - proper name or nickname, with/without middle initial. Same for pictures.

4. Who is the most famous person you ever met (not just in the same room as, but actually spoke with)? John Cooper (former OSU football coach), Eddie George (former OSU football player & Heisman Trophy winner), and Woody Hayes (former OSU football coach). Man, I need to get out more!

5. Parents aside, who is your biggest hero? There are a lot of people that I admire. Growing up near the Pro Football Hall of Fame, we'd go to the parade and the enshrinement ceremonies every year. I'd hear the players and coaches talk about how the game changed their lives for the better and such. Very inspiring when you're six, and still a very positive message from today's inductees. I never played organized football. Listening to these guys talk about the game makes me want to strap the cleats on and toss the pigskin around.


6. Someone once worked out the sexual version of Six Degrees of Separation - Celebrity A slept with B, who slept with C, who slept with D, making as sort of connection between A and D. Are you connected to anyone famous through six or fewer bonks? Depends on how famous. There's a sportscaster in probably less than six. For more than six, I am related to Madonna through marriage. My father's cousin married a woman who's grand father was a brother of Madonna's great-grand father. I just found this out recently.

Thursday, April 16, 2009

A while ago JamieLin and I had a short discussion on crossdressing and running, and that made me think of women's running clothes and perhaps why I haven't started wearing them. Crossdressing or not, there are several advantages and disadvantages of men wearing women's running clothes.



Advantages:
  1. The tops and bottoms are much more form fitting then men's. Not baggy and loose. I like feel of the trimmer fit.
  2. Trimmer fit may be less be less chaffing than looser clothes.
  3. Form-fitting clothes usually have some Lycra that provides more support for the jiggly parts, e.g., belly, thighs, and the twig & berries.
  4. Trimmer fit does a better job at wicking away sweat.
  5. More stylish - colors, patterns, and cuts - and more thought is put into the details.
  6. And reviewing men's options for underwear, I couldn't find anything smaller that a boxer brief. Women have available to them bikini styles that are great to wear under running tights or compression briefs.
  7. Bun huggers! They fit like a second skin and feel fab!
  8. Running tights feel wonderful! Even men's tights feel like heavy pantyhose. And you can wear pantyhose under them for another layer of insulation in the winter (I have many times). And support hose provide some massaging of the legs during and after running.
A few examples of bun huggers. Very short and form-fitting. I like the piping detail on this one.

Another, plain. Front:

Back:

One more. I like the swoosh of color:

Disadvantages:

  1. Form fit shows off the bad jiggly parts, e.g., the 10-pack abs.
  2. The shoes - since men are usually heavier than women, a woman's shoe may not provide the same support as a men's shoe in the same overall dimension.
  3. I can't imagine wearing a wig while running would be comfortable. The body looses a lot of heat through the head, and a wig would just trap it and all of the sweat. Better let your hair grow out if you want to be passable.
  4. And better find some sweat-proof make-up if you're so inclined to wear it.

There's the issue of discretion. Looser shorts & tops and generic colors may not draw much attention to the fact that the clothes are women's, but:

  1. If you're running a local race in full female mode, its best to be very passable, otherwise you will get a lot of strange looks. And you might hear "Mommy, why's that man wearing a dress?" a lot. By in large the running community is very friendly and supportive, but there's no reason to purposely stick way way out. Keep to places where CDing is much more acceptable (group meetings and other CD-friendly events) (I wonder if there are enough CD runners that there could be an all CD race?). However, there is a guy that does wear a pink leotard, tu-tu and wand to major races every year (there was a short article about him in Runner's World some time ago); and I've seen a guy in a red dress with shoes spray-painted red, too (neither trying to pass). There are some races where many people show up in costumes.
  2. Better be in top shape if you're brave enough to wear only a sports bra for a top.
  3. Although I very much adore running skirts/skorts, use good judgement to pull it off in public.

Here's some women's shorts that I like. I like them because they are shorter than most men's shorts. And they are better looking than similar length men's shorts. They could be worn without too much notice.


These last ones are generic enough for either men or women:



Here are a few tops. I like them better than men's as they are more form-fitting. Front:
Andit has a really cool design on the back:
This is nice too. Large arm openings without being baggy. The interior bra may be tough to hide though.
And these long and short sleeved shirts are too cool!

Shoes. Other than the pink ones there's really nothing that makes them stand out as women's.