Sissy excursion....(sort of)

[sissyallison]

I just got home after spending the night in another state and I had a 3 hour or so drive home. I was able to indulge a little and wore a pink Megamax diaper the whole way, satin panties over it, and a black skirt and pretty bra. I had on a boy shirt so people driving by couldn't tell anything but it was still exhilarating. I ended up stopping at an adult store on the way but changed back into shorts before going in (I still wore the bra, panties, and diaper of course!) but didn't really find anything I wanted. I know it is old school but I liked the old Penthouse Forum type magazines with crossdresser stories in them but I couldn't find any that I knew had crossdresser stories. Mostly because they put bit stickers on the front blocking the cover summaries of stories

I did end up getting a dildo and strap on for when I have play time with my girlfriend though. Granted, it is to use on her when in sissy mode but I think we can have a lot of fun with it.

The only "bad" thing is that my diaper leaked on the way home but honestly that just re-enforced that I need to be in diapers! It was a very fun drive and I wish I could do it more often. The nice things is I plan to be in a diaper all night and all day tomorrow and try to dress up for most of it as well (we have to go out for a while so no sissy clothes then ).

 

[Peesalot]

I had occasion 2 weeks ago to drive about 2 1/2 hours north for an overnight motel stay. I drove the entire way in my lace panties, women's jeans, women's sneakers, thigh highs, lace bra, DD cup forms, top, makeup, lipstick, pink press-on nails, wig, and jewelry. The young woman at the reservation desk was quite nice when I checked in. I actually had to make a trip back to the front desk when my key didn't work. She made a new key, got on the elevator with mw, and made sure it worked. I went down to the front desk a little latter to buy some snacks. I really wish I could go out dressed on a daily basis; but, that would cross the boundary line of not going out dressed locally as it would cause my wife great embarrassment.

Right now, I'm sitting in our family room with lace panties, a lace bra, EE/F cup forms, jewelry, wig, and lipstick on. I'm skipping the makeup and nails tonight as I'll be going to bed shortly and will have to remove the makeup. And, I'm not going to put on $7.00 nails just to sleep with them on. I will remove the lipstick before going to bed so I don't smear it on the pillow or sheets. What a mess that would be.

The whole point of this little bit is to agree with you, Allison, that dressing is a total joy and what I'd like to do 24/7.

Allison, you said, " (we have to go out for a while so no sissy clothes then )." I'm curious, if your gf didn't have a problem with you dressing as a sissy in public, would you do it? I think if my wife told me I could dress 24/7, I still wouldn't do so where my friends and neighbors could see me as I doubt many of them would be accepting. However, I would do so a lot more and do more shopping out of town. Yes, more driving and more gas would be used; but, it would be worth it. But, that's a fantasy as my wife will never tell me to go for it.

 

[sissyallison]

You know, that is a good question. I think she would be fine with me dressing in public (maybe toning it down so it isn't overtly sissy-ish I guess). The hangup is more on my side right now. Though, I think me dressing in a diaper might be too much for the time being. Even if it was hidden under layers of clothes.

We actually have (or had) a plan to give me a girl's day out (my first) in Chicago but our plans had to slightly change so we are looking at doing it a little after that. She is onboard with it and I really want to go out dressed as least as a woman even if not a sissy. I guess it really depends on how obvious it is I was a sissy rather than any other "woman".

Also, I really liked your story. I am glad that front desk clerk was so helpful and non-judgmental.