First Time Dressed As A Woman free porn video

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Ok, this is an absolutely true story.

I'm a married white guy, stocky, 6'1" with a 5-1/2" cut dick. I've been dressing up on and off since I was a p*****n, starting with my mother's lingerie and dresses. I love makeup, but especially lipstick. I used to masturbate by stroking my cock with a blood red lipstick while reading those old trashy porn novels you could pick up in the seedier luncheonettes.

I always denied my cock loving side, imagining myself as a lesbian for the most part, but I fantasized a lot about sucking cock and getting fucked. Once I'd cum I'd feel ashamed and try to put it out of my mind.

I never had a same sex experience until about 2004 when I had been frequenting a local gay forum where the person who had started the forum was only about 20 miles from me and offered first-timer's a crack at his dick. I traveled to his house and after some hesitation dropped down to take his dick into my mouth. It was not as I had imagined it would be. It was surprisingly spongy, where I had imagined it would be much harder.

I didn't end up doing much. I went up and down for a little while and eventually just left. But I had finally done it. I had sucked a cock! And it was OK.

Now let's move ahead a few years. I was getting more and more turned on by CD's, TS's and TV's and frequenting the cross-dressing forums and chat rooms. I began building up a collection of lingerie and lipstick, plus a few dildos and some DVD's. Gotta love the internet and anonymous shipping! Got some really sexy red fuck me pumps too which I loved to wear with my seamed black stockings.

It was about this time that I got up the nerve to respond to a Craig's list ad. It was an older gentleman who said he liked to cross dress too and so I made a date to meet him at his apartment. This time only about 10 miles from me.

I put on my thigh high stockings, some sexy panties, my red Frederick's of Hollywood corset, a red satin chemise over the top of that, stuffed by high heels into a backpack and put on my street clothes over the top of everything.

I was shaking I was so nervous! I got to his apartment and he excused himself to put on something comfortable. I took the opportunity to strip down to my girl stuff and put on the shoes. He came out wearing just a negligee and sat down next to me on the couch. He leaned over and took my cock into his mouth. God it felt good! After a few sucks he suggested we get on the floor and we got into a 69 position. I gobbled up his cock feeling like such a slut in my outfit and he came quickly in my mouth. He moaned with my cock in his mouth and I was just so turned on that I came too. He swallowed my cum but I didn't swallow his, instead letting his cum dribble onto the carpet. I really wasn't ready for that yet, not with someone I'd just met at least.

After we talked for a few minutes (it was obvious our date was over) and he said next time maybe we would fuck. Well, I never did see him again, but eventually I did get fucked by another guy and I loved it!

I'm still hoping to meet someone who's discreet and cool to hang out with for regular meet-ups that doesn't freak out after they cum. It's really hard to meet someone like that for some reason, so if you live near Smithtown on Long Island, can handle a "bear" type with a beard who likes to dress up (or not) and who's into oral, anal, kissing and more (no pain or playing with poop please) you can email me at [email protected] and we can chat and see what happens from there.

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09.10.2021
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"Fuck it; you've had your ten minutes," I whined, pushing the shower door open."Mom, come on, I'm in here, can't you wait your turn?" he griped, peeking at me."What, you've seen me naked, both while being on top of me and on the bottom too. You're gonna take all the hot water too," I mentioned, getting in front of him. "So, you're going to share.""Fine, Mom," he moaned.I giggled and let my hair get wet. "Will you wash my hair for me, son?""Sure, Mom."A few seconds later, I...

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