Maybe to most people this will seem very kinky and wierd, but to me it feels quite natural and soft and loving.
The brief story 'First Bras' reminded me of my first real 'dress-up.' Just before puberty, I had a jackin-buddy, named Bobby. He taught me to masturbate, and we'd have sleep-overs at his house. We didn't know anything, and so we tried everything we could think of that would pleasure us. One day we were alone in his house and we started going through his mom's drawers and Bobby gave me her lingerie to wear. It just happened, and there I was in some panty hose and a bra, completely turned on. I asked Bobby to put lipstick on me too, which he did. We went down to our 'fort' in the basement and I jacked off with him while wearing his mom's bra.
We never did anything like that again, and I forgot about it, mostly. When I found a bra hanging on a line at our apartment's Laundromat, about a year later, I stole it, and kept it hidden for a long time. I'd slip it on every now and then and have a nice feeling. Since then whenever I had the chance, like if I was staying at someone's house, I'd find a bra and slip it on, if only for a moment, and imagine how it's owner felt, and rub my breasts, imagining they were the size and feel of the ones that were held by the bra.
A couple of years ago, when my girlfriend was away for a month, I slipped into her bra and panties and enjoyed the feeling. I walked around and then lay on the bed to masturbate. I played with my nipples, and rubbed my thighs and belly like I do my girlfriend. I had fantasies of having a woman's body, and my nipples hardened and stung and felt wonderful. Instead of rubbing my cock, I 'fingered' myself between my legs, imagining that I had labia that grew wet and excited. I did this several nights in a row, and when I told her on the phone what I was doing, she got turned on too.
I was excited to go outside with a bra on. First I wore her sports bra, very flat, under a sweater. But I wanted something that could be seen, so I filled out a little bra with silky cloth, which rubbed my nipples under the tight bra. The tight fleshy sports bra, with gentle mounds, made me look like I really had tiny titties, and the idea thrilled me. I went out to dinner, then to a sports lounge. Nobody could actually see anything, but I FELT so erotic!
Finally, one night, I took one of her regular bras, which are 34B and filled it out and wore it under my jacket. I went to a movie, and once in my seat I took off the jacket. It was dark, and very, very thrilling. I got home feeling totally erotic and masturbated three or four times that night.
When my girlfriend returned, I wanted to go out with her with lingerie on. She found it a turn-on. We took a shower together, and dressed each other. She had fun dressing me, and even applied a little lip gloss, and then I remembered that time when my jackin buddy put his mother's lipstick on me.
After a few times I lost interest in wearing her bras; it was enough to keep the feeling of being soft and feminine. Of course I have a couple of special shirts that feel especially good over my nipples, and one very nice heavy white cotton shirt that could almost be mistaken for a blouse. It's a shirt that, well, you could wear a bra under and it wouldn't be noticed. My girlfriend knows that when I wear these I'm feeling a bit girly, and I get special, gentle attention. Sometimes she suggests we go out to dinner, somewhere bright where everyone is on show, and she chooses a bra for me to wear. We always have fantastic sex after one of these dinners!
Now, when I'm reading Solo Touch, I like to get naked and play gently with a firm, puffy erection keeping it wet with pre-cum. As I browse the stories, my nipples are tingly, and I like to take a little pre-cum and rub them gently, as I'm doing now. Then, depending on my mood, when I want to cum, I'll either grab my cock and stroke or gently lay back, spread my legs and rub firmly, softly and slowly below my scrotum. I always cum this way without needing to even touch my cock, and I feel the orgasm in my whole body.
I'd love to hear other stories about men with erotic breasts, or who masturbate like a woman. So hey, guys, don't be shy!