Panties For Men

This is the last post in this series, and tells about what started the 'outerwear' part of my cross dressing.

   Carol and I were both 20 when we met.  I felt sorry for her because she had a very troubled past.  She was raped by another guy before we met.  She got pregnant from that and had to drop out of  school and give up her baby boy for adoption.   I thought that was the reason why she was somewhat ‘different’ mentally or emotionally.  Although I wasn’t responsible for her ‘condition’, I gladly became part of her therapy, by both of us doing “girlie time” role playing together.  The role playing was suggested by her rather flaky therapist and had the blessing of her parents.  We did the role playing perhaps 12 or 15 times in the year that we were together.

    Folks where we both worked didn’t know the role-playing was her therapist’s idea, since they said Carol made me do the role playing to humiliate or degrade me. They said she was a man-hater because of being raped, and was taking out her anger on me.  I didn’t see it that way, since she never made me do any of that role playing, I did all of it voluntarily. If I balked, she’d ‘help things along’ by kissing, sweet-talking or fondling me.  I loved our role playing, once I saw how happy it made her.  I was eager to do anything, no matter how ‘different’ it seemed, just to make her happy, simply because I loved her so much.  When we were together, we were always so very happy.  When we finished role playing she’d usually say something like:  “I’m so happy we did that together.  I love you so much.  You’re my best boyfriend ever.”  Then I would tell her that I loved her too.

    Sometimes when we were making out “hot and heavy”, she’d stop and say “C’mon Marilyn, its girlie time!” Then she’d dress me in a spare pair of her panties and lacy bra with ‘big girl’ inserts, followed by garter belt and nylons after she shaved my legs. A ‘special treat’ was when she’d remove her own panties and dangle them in my face, then dress me in them. She’d do that fast enough so her panties were still warm when she put them on me. On the other hand, maybe the warmth in the panties was actually from my hot breath. At any rate, I became sexually aroused by the warm panties. After that, she’d put a skirt and blouse on me. She left my blouse partially unbuttoned to show off the lace on  my bra. All of her clothes fit me well. She finished ‘making me into a girl’ by doing my makeup, perfume, lipstick, eyelashes, nails, Rhine stone ear rings and other jewelry and the “Marilyn Monroe” wig and those damned 4-inch stilettos which were so hard to walk in. The shoes were black patent leather with swirls of Rhine stones on them. Her warm panties and the rest of her clothes that I wore made for an enjoyable and sexually fulfilling time for both of us, even though I never ‘got into her’ in the usual meaning of that expression.

    After she ‘made me into a girl’, she’d admire her handiwork by slapping me on my buttocks on the outside of my skirt with her bare hand and whistling at me and telling me what a sexy little slut I had become. She’d also parade me in front of a full length mirror so I could admire her handiwork and also flirt with myself.  After that, she’d lift her own skirt and wrap her legs around my head and pound my face with her womanhood.

    After I became “Marilyn” and she finished pounding on me, we’d go into her living room and she’d put on some music. She had me ‘perform’ for her by having me walk in my stilettos and dance to the music. After a couple of times, I got the hang of it. She especially enjoyed the scratching sound that the tops of my nylons made when they rubbed together under my skirt as I walked or danced. I’d become sexually aroused by that sound and also by the feeling of my skirt hem brushing against my nylons and teasing my thighs. She’d have me walk ‘heel to toe’ or stomp in my stilettos, which made my white pleated mini-skirt flutter on my hips and made my buttocks jiggle. When I walked that way, she’d whistle at me and then lift my skirt and fondle or kiss my butt cheeks and call me “Jiggles”. If I was wearing loose fitting panties, she’d lift the back of my skirt and have me slap her face with my bouncing butt cheeks.  When I wore a different pink mini-skirt, the hem would sexually arouse me by scooting in and out of my crotch and teasing my genitals through my sheer silk panties as I walked or danced.  When I wore a longer full skirt, she’d have me “twirl like a girl”, until my skirt lifted high enough to show my garters and panties. I stumbled a bit, but managed to ‘stay on my feet’ when doing my “twirly-girly”.  That was followed by wolf whistles and lewd comments from her.  If I was wearing a ‘pencil’ skirt, then I’d do the “Marilyn Monroe wiggle” when I walked. With her finger she’d draw an outline of two hearts on my buttocks, on the back of my skirt. Once in a while she’d lift my skirt and draw the same outline on the back of my panties. That was so very hot!   

    After she was done with all the skirts, she’d masturbate herself, orgasming several times. “Girlie time” would end when she’d put her hand inside my panties and stick her lubricated finger up my butt and fondle my prostate until I orgasmed again. After I came, she’d dress herself in my “used” panties, then climb on top of me and pound my face with her womanhood until she had as many additional orgasms as she wanted.  Because of my multiple orgasms, I became “a buck well spent”, and afterwards would lapse briefly into a deep sleep.

    “Girlie time” gave us both the sexual releases we so desperately desired, but without the possibility of a pregnancy. I believed she was a bit delusional, and maybe she thought that ‘turning me into a girl’ would make me unable to have sex with her in the normal way because I was now a ‘girl’, if only just pretend.  I think her making me have orgasms in her clothes and being sexually satisfied by that was, in her mind, an added layer or level of protection standing between her and the dreaded possibility of another rape.  As I said earlier, she was raped by another guy before she and I met.  I thought that she still had a fear of being raped, although none of my speech or conduct ever gave her reason to fear.

    Here’s another possibility: Maybe she was delusional enough to think that my ‘juice’, which was in our shared pair of panties, would be in contact with her body and then somehow ‘erase’ or cover up her rape nightmare.

Thanks for reading, and stay healthy, safe and beautiful.