Am I Messed Up?
I just split up with my girlfriend of almost twenty years and realized how strange a relationship we had. She used to ask me to do some pretty weird stuff (in my opinion, anyway) and now I find myself doing it because I enjoyed it. As Rick James said, "She's a very kinky girl," but that only covers half of it. At first, I thought it was funny, as a change from the "conventional" kind of relationship. I'm open to "other" options and here's what she/we came up with. She liked the idea of me dressing up in her clothes. The reason she gave me was that she still felt more comfortable talking to one of the girls and I wasn't equipped accordingly. I decided to humor her and dressed up in some of her clothes one night before she came home from work. I did a little online research about cross-dressing and followed some of the advice. When she walked in the door, I had on one of her dresses, some pantyhose (with the "boys" tucked away as I had read how to do it), a bra with water filled balloons as filling, and a wig that she had. She almost passed out from excitement on the spot seeing me like that and we had the wildest night yet. As time went on, she asked me to dress up like that more and more. At first it was once or twice a month. Then it was pretty much weekly. This whole time, we were going out and getting clothes that were more my size so I didn't stretch hers. She went online and ordered a pair of silicone breast forms, a pair of panties with foam in the hips and butt, a bra with pockets to hold the forms, and a "gaff" to keep the boys tucked away. I thought she may be a closet lesbian, but the sex that came with the dressing up made me think again. The more I dressed up, the kinkier things got. We got into some bondage; both me tying her up and her tying me up. We also had me dress in skin tight leather or spandex pants and giving it to her with a strap-on (it never went the other way). I can be as open-minded as the next guy and this didn't really bother me. After having done it for the past ten years or so, it wasn't a big deal. Now that we've split up, I look back at it and go, "What the heck were you thinking?!?" If it's not bad enough that I did that stuff with her, now I find myself doing it when she's not in the picture. When the split happened, I ended up with all the "other" clothes and accessories to be, well, let's call "her" Kelly. Now, Kelly has become a major part of my single life. I find myself coming home from a difficult day at work and "Kelly" is my escape from the stress. I often walk around the house wearing a teddy, nightgown, or sweats; all with the breast forms, wig, and gaff in place. Half my life has become female. On the plus side, I make one very ugly women, so having "her" go outside the house is not an option. Still as a plus, I've learned to respect part of the female perspective. As far as emotions go, it won't happen, but I can respect the everyday hassles women face having to wear bras, put on the make-up to look pretty for the boss, etc. As the saying goes, "Walk a mile in someone's shoes."
— Steven, 41