First Time In Panties

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Story about the first time he wore panties.
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So, I was 27 and had just moved in to my girlfriend's place. She worked during the day and I worked from home. One day, I was feeling extremely horny and grabbed one of her Vic Secret catalogs. I was not only drawn to the beauty of the women, but the panties and lingerie caught my attention even more. I found myself mesmerized by the sexiness of it all, and wanting to feel it on me. So, I walked over to her panty drawer and started going through them, feeling the softness, the sheerness, and then I noticed....the stretchiness. I started rubbing them on my cock, the softness making me harder than I ever was before, but I wanted more...so I looked in her closet, and there they were, tiny little black vic secret vstring thongs....rolled up in a ball, the same ones she wore the day before. This would be perfect I thought, as I picked them up, shaking in anticipation of how naughty I was about to be. I slid my own pants off completely, along with my underwear, and slid one leg through the panties, then the other, and then slowly slid them up my legs, noticing how I had to wiggle my butt to get them on. Also, noticing how my hard cock could not be contained in them. And that "annoying" thong? I loved how it felt in between my butt cheeks. I felt so sexy, so feminine, and had pre-cum oozing from my cock. I laid back, pulled the panties to the side, and stroked my cock, rubbing faster and harder until I was ready to cum. Uh-oh I thought, where do I shoot my load? But it was too late, as I exploded all over my belly, chest, and yes, her panties. I felt ashamed but turned on at the same time. So turned on, that I wiped up some cum with my finger and licked it off. Little did I know that I had just peeked inside the door that I have since opened wide!!

I started coming home early just to put on her panties and masturbate. It was consuming me. At the same time, I realized I had tapped into a whole other side of mine, one that fantasized about sucking a guy's cock. NOt that I looked at guys and thought they were hot or not, but the idea of sucking a cock, started to sound more and more like something I could really see myself doing. Of course my wearing her panties only led me to wanting more, so I started trying on her outfits, damn petites!! But it didn't stop me, as I now started venturing out of the house while wearing her panties under my regular clothes.

So a few years go by and I have only gone so far as to wear panties and talk to a few guys on the phone while wearing them, telling them how I would suck their cock and maybe even let them fuck me. One suggests we meet. Uh-oh!! Was I ready for that? Not only does he want me to meet him, he wants me in panties and stockings, and even suggests I shave around my cock to look a little more feminine. Well, I try shaving, and love the look and feel, especially the feel. Then I get the idea of guying to the store to buy my own panties and stockings, since my girlfriend's stocking wouldn't fit me, plus I was afraid I would ruin them!! I can't even describe the level of excitement I experienced when I went to the store for the first time, knowing I was buying something sexy for me!! Once I bought a few pairs of panties and a pair of black thigh highs, I raced home and slid on the thigh highs.......what an incredibly sexy feeling!! And now the idea of being dressed for a guy, kneeling down in front of him and taking him in my mouth seemed like the logical next step, and I sooo wanted it. I started tasting my own cum more and more, and even played around with my butt, sliding a finger inside as I stroked my cock from time to time. Finally, the guy I have been talking to (met him on a phone chat line) invites me to his house...his wife would be at work, we'd have the house to ourselves. Nervously I accept his invite, and he tells me to make sure I am shaved smooth, wearing the stockings and panties, I eagerly agree. More on what happens at his place in my next posting. Stay tuned!!

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NCPantyguyNCPantyguyalmost 5 years ago

Tell more please ....

AnonymousAnonymousalmost 8 years ago
lovey

my first time in panties was a few years ago a older lady I know I was helping her one day with some house work moving some thing around the place when my pants ripe open I said dam my pants just ripe she look at me and you are not wearing under wear I said no I am not well I can fix them but I can not have you bare ass running around here I told here she told me if you do not mind wearing a pair of women panties till I get your pants fits I told I told well I guess it would fine it be the first time I ever had women panties on it just be fun well then let go find you a pair she toke me to her bed room and open a drawer now lets see what kind should you wear I told her any kind she just laugh I am going to like this you be my first man I put in panties as she look she throw out a few bras one fell on the floor as I pick it up she look well I see you have good taste if you want I have the panties that go with that bra as I look at the bra and saw the panties she ask well I said I do not know about this she said look let me put it on you if you do you knot like I will take the bra off I said all right well she put it on me and hook it up and but two fake breasts well I look in a mirror and I look like a man in a bra she ask well what do you think I look silly but it fine now put the panties on I did as told when I pull them up they felt really soft and nice and tight I saw a full mirror and I saw I look nice in panties I thought I should been in panties years ago she walk over well look at you in my panties and look sexy cute I told well I do look cute well then do you want to just wear them or some thing else I told her if I do you will not tell any one no it be just us two I said you can put any thing you want on me if I do will you wear it I said yes she told me I make you look like a girl and you be my knew girl friend well it toke her five hours and when she was done I look like a girl you could not tell I was a man I had my face made up and my nails done after that she told me lets go out for supper I ask her you I can not go out like this she said yes you can and will she hand me a small lady bag put some lips stick in and make up then we walk out to the car we went to dinner once we were sited the lady ask you lady like a drink we said yes please miss and lady you look lovey in that out fit well after that we had dinner and when we were done the lady ask if we want anything else my lady friend said what have you got she ask her are you two a couple she said no knot really why you ask well she just look good and I like her bra my miss said what time are you done I be finish in a hour well then will you turn around and put your hand down her blouse and feel her tits she just did that well are they really no knot yet if you are still want to she a he she said yes then we will wait she came out and we all went home as I walk in the house I saw my miss kiss her I was hoping you like are knew bitch yes and just think he make a good girly bitch and that what happen

AnonymousAnonymousabout 9 years ago
womanly

I had no idea what he would do but i knew i would not back out even though excitement and fear confused me into thinking i had control. You see he didnt force me but at that moment i was at his mercy and he had little. flat on my back legs pulled back tangled in his arms i was pinned down saying please go slow but before i could reach down to keep him from me he was already introducing 8 very thick inches way to fast for comfort. Panties made made me fem but after a two hour dominate fucking it wasnt about my ass anymore it was about my pussy.

BadMarieBadMarieover 10 years ago
Interesting

Its always interesting how the silkiness just grabs and brings out a whole new side in a guy willing to slide on a pair of women's panties. Now just a thought to all those out there that also wear nylons... the feeling is much more exciting if you shave your legs. Great story and so looking to reading about your adventure.

JohndawgJohndawgover 11 years ago
Thankyou, got hard. Woof

Hot story, I am wearing my ex girlfriends panties and lingerie right now.

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