[Something_Awesome]

A small (just a small) part of me is making this post because I feel like it'd "rock the boat" a bit. However, I say that in a respectful way (I'm not trying to suggest that the users here are "squares"). The main reason I am posting this is because I think it's interesting. This story happened about 1.5 months ago, but it covers a period of a few weeks. So here we go...

My GF has a fancy teeth whitening gizmo and I thought I'd take a crack at it. She has amazing pearly white (hyper white) teeth. I'm not quite on her level, but that's not to say my teeth are bad. I mean, I don't drink coke or coffee, or smoke (those three things are known to stain teeth pretty bad). LOL, can you tell I'm being a tad self-conscious? The teeth whitener requires that you brush a gel-like chemical onto the teeth before using the device. I am guessing the process is a little similar to how you whiten things using diluted hydrogen-peroxide and sunlight.

WTF Chemistry!? Sorry, don't fall asleep on me...

So when using the device my GF advised me to not swallow my saliva. She gave me a couple reasons as to why, but honestly, I thought she was wrong and that she probably did not read the manual. Whatever. I decided to take her advice. I was not going to swallow my saliva.

My GF told me that I am supposed to remove the device from my mouth every 7 minutes, spit my saliva build-up, and re-apply the gel (supposed to repeat this cycle a few times). However, once I started the procedure she decided to let me know that she was running low on the gel and that I should be able to go 21 minutes with the first application of the gel. So yeah... 21 minutes without swallowing or spitting...

Anyway, while using her machine I still thought it'd be funny to goof off with my GF (bad idea). I don't remember exactly what I did, but it was something that caused us to laugh hysterically. As you might imagine, my spit began pouring out of my mouth. It was a lot of it too (I was close to the 21 minute mark, so my saliva really built up). The GF freaked out. I freaked out too once I saw the mess I made on one of my favorite shirts. I had no idea what the gel (mixed with my saliva) was going to do to my shirt (discolor it perhaps). I took off my shirt and we threw it in the washing machine ASAP (we were at her place). This is where it gets interesting...

So rather than wait til my shirt washed and dried, my GF thought it'd be best if I wore something. She suggested I wear one of her shirts. I told her no. She kept insisting. She pulled out like this black shirt with femininely cut short sleeves and like a V-neck. I told her I thought she was nuts. I tried to explain to her that she was crazy and that I'd probably rip the shirt in half. She is a petite girl and I'm a pretty big dude. My mind was not comprehending how she could think that I'd fit into one of her shirts. I was trying to be nice about it because I thought she was trying to be real nice but was just maybe having a total mental lapse (I actually started to worry a bit).

Just so you guys can really imagine this. My GF went to a J.Crew store a couple months ago and she bought a great women's blazer that was on sale. You know why it was on sale? Because it was the only one left and it was a size 00. Size double-zero. So now imagine how small her shirts/blouses are. There is no way ANY guy is going to fit in a shirt fitted for a woman that can wear 00.

I honestly felt bad for my GF so I agreed to put on her shirt. As I started to put on her shirt, she got super excited and I had an ah-ha moment. She was not giving me her shirt out of kindness. She wanted me to wear it because she wanted to dress me in women's clothes. She told me "I was always wanted to dress a BF in my clothes!" She sounded pretty giddy about it too.

Luckily, her shirt was pretty stretchy so I was able to get it on; however, I could not lower my arms (I had to leave them suspended in the air sort of like an ape might). I felt like if I lowered them then I'd rip the shirt in half around the shoulders. I did not leave the shirt on long before taking it off as It was just getting weird for me (I didn't tell her that of course). But it gets better...

My GF then asked me to wear her underwear. It was at this point that I realized that she did not want me to wear her clothes. And she did not actually want to dress her BF in her clothes. She was using the clothes thing as a stepping stone for getting me to wear her underwear. I don't remember my exact response to my GF's idea of me wearing her underwear, but I did not exactly express interest and she dropped the subject real quick after that (probably did not want me to judge her). I left the door open for the possibility though... one day...

So a week went by and I thought to re-visit this whole women's underwear thing. Not because I wanted to do it, but because if it's something she really wanted, why would I not do it. Big deal, right? This was obviously something she kept bottled up for a lot of her life (like the pegging thing for those of you that are familiar with that story), so why not? I honestly feel that if the pegging thing never happened, she never would have revealed her desire for me to wear her underwear. But even then, I could tell she was a little timid about asking me to wear her underwear. At least she is beginning to share me with me fantasies she never thought she'd ever share. Feels pretty empowering.

Anyway... We had a wedding to go to the next week in Santa Barbara, so I thought a great way for me to bring up the whole women's underwear thing after I shot her down the prior week was to say something like:

Hey babe, so we got a wedding to go to next week and I think it'd be a good idea for me to try on some of your underwear so we can figure out which pair I should wear to the wedding.

So I did say something like the above, and she was FLOORED. At first she had no reaction. You could tell she was shocked to the point that she could not react. She was paralyzed. When she realized I was serious she bolted to her underwear drawer! I put on a couple different pairs of underwear and modeled them for her (not in feminine poses for those of you that are curious). They were both like a violet/magenta color. One of them she said was "boyfriend underwear" from Victoria's Secret that she usually wears when she is on her period. She though it'd be good to start with that one because it gives my man-parts better support. I did express my concern that I probably was not going to be able to get the underwear on, but I was wrong. I got the boyfriend underwear on with no problem. She liked it, but I didn't. It just was not bold enough, y'know?

She then gave me something more womanly. It was lace type of underwear (lol). It was not a g-string. Just a regular underwear, maybe a thong? I sometimes can't tell the difference. I put the underwear on and, to my surprise, I got them to fit. I was popping out from the sides, but with some adjusting I was at least able to keep the underwear centered so that I popped out only a little bit and evenly on both sides. I modeled them for her and she loved it. I have her a full 360 spin and she though I just leave them on for the rest of the day, so I did.

I gotta be honest... I wanted to appear as confident as possible when I was in her underwear (I wanted to model the underwear for her sort of stoically; not shyly), but you can't help but feel a little... vulnerable (if that's the best word) while she eyeballs you in her tiny lace underwear.

There was a little more to what happened that evening after I wore her underwear, but I'm not going to go there. Instead I will write about my experience the following week where I wore her underwear the whole day, under my suit, at her friend's wedding! But I'll write about that tomorrow...

Have any of you partaken in anything like this?

[atskitty2]

I've never been involved in that sort of play. Given your sort of submissive role, and willingness to please, I'm not surprised it happened.

[effy2014]

Congratulations for allowing SAGF to explore this part of her sexuality. This has nothing to do with trying to make you a cross dresser -- as Kitty suggested, it is an exploration in her dominance. I am sure that you were well rewarded for your obedience.

I look forward to part 2.

[Something_Awesome]

Part 2... I'll try to condense this one a bit.

So it was the day of the wedding and we were in such a rush (running late and we had almost a two hour drive) that we almost forgot that I was supposed to wear her underwear! I put on her lacey underwear and we hit the road. I decided to drive in regular clothes (since it was a long drive and I wanted my suit to stay crisp) with the intention that I'd change in the car when we got there.

When we finally arrived I pulled into the parking lot of a Panera Bread so I can change in the car. I took my time (we ended up being pretty darn early because my GF lied to me about what time we needed to be there by because she knew I'd cause us to be late). As I was changing she was eyeballing me (because I had her underwear on) real hard. I swear I could feel her eyes burning a hole through my crotch. Sure, she was staring because she liked it, but I know she was also trying to challenge/disrupt my comfort.

I have to admit, at the wedding we had such an amazing time that it distracted us from expanding on the women's underwear play while there (I love weddings; I genuinely do). I did make a few more extra trips to the restroom than the average person so that I could "re-adjust" myself down there. It's not only uncomfortable to have your junk sticking out the side but you don't want it to look like you're going commando either (specifically while dancing). My GF caught on pretty quick that that's what those trips were for

It's funny because after a while you start running out of good excuses for why you need to go to the restroom (when you can't bow out without people paying attention). What's also funny is your GF asking you "what's wrong, baby" after you get back. "Oh, I'm still trying to break your underwear in"

When the party ended I pulled into a dark parking lot so we can change and be comfortable. We knew we'd leave late and have a long drive back, so we were prepared. When we changed I left her underwear on; however, as we were driving back she told me she wanted me to drive back without my pants (so that the underwear was exposed). Without hesitation I took my pants off while driving down the Pacific Coast highway (didn't even have to pull over). After I got the pants off she said "I love you" and dozed off.

We got back to LA in record time. I was speeding almost the whole way. Yes, there was a risk of being pulled over by highway patrol, and it did cross my mind. If you've ever driven on a highway (at night) that is literally right on the coastline, you'd know it is dark as heck, making cops really hard to spot. I would have had no problem putting my pants on before the cop got up to my window, but I toyed with the thought of staying in my GF's underwear. I romanticized the idea that the cop would have found it so funny to see a guy driving in women's underwear that he wouldn't have given me a ticket. I've heard of cops not giving tickets if you got them to laugh hysterically. I think I used that thought though as a reason to convince myself to continue speeding. By the time we got back we were too exhausted to fool around, so the night ended in pretty pedestrian fashion.

BTW, GF looked freakin' stunning at the wedding. She had an AMAZING dress/gown. It was burgundy color. Of course I wore a tie that color matched it almost to the exact shade.

Well, that's it. That's my last sex-related story worth sharing. Have not explored any other sexual frontiers since then. Actually, we have not had sex in more than two weeks (thanks to my surgery on October 30).

Thanks for reading!

[effy2014]

I was rooting for a better homecoming from the wedding, but I can understand her falling asleep on the ride home. Great story!

Did I miss a post on your surgery? How is your recovery going?

[atskitty2]

SA, I'd have probably jumped you while changing in the car after the wedding, while still full of energy...I was surprised that didn't happen. You'd have at least earned yourself a BJ or something for the ride home! I understand the exhaustion tho.

[Something_Awesome]

I know guys, it didn't endmthe way it should have ended. But we were both tired. As for my GF, she'll knock out at like 8:30 but be up between 4 and 5am. She get's sleepy when people just start getting in the mood to party. She used to be a party animal and was always out late at night, but that started to change shortly after she got with me.

I know what you're thinking... I must be boring! Actually, she says late night partying isn't for her anymore. I dunno, I've been told girls can get like that once they are in a relationship

[Something_Awesome]

Oh yeah, my surgery.... It went very well. Pain was pretty bad for the first couple days (surgeon warned me about that) and I did not pop any pain killers.

What sucks is I have to hop around everywhere on one leg, assuming I have to cary stuff, otherwise I can use my crutches. Taking out the garbage sucks, too. My left glute has been getting a serious workout though (whether hopping or using crutches).

Doing anything just sucks. Showering really sucks; can't get my foot wet. I put my right knee on a tall bucket to balance myself (surgery was on my right foot/ankle) when showering.

Could be worse. Like, I could be wearing a cast.

Also, I've been noticing how nice it'd be to have handicap accessible ramps instead of stairs everywhere. Which is fine I guess, except that going down stairs can be very dangerous on crutches and I had a scary moment a week ago with regard to going doen stairs. GF saved me though

[effy2014]

Hope you heal quickly.

[Something_Awesome]

Thanks effy!