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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The funeral was a gloomy affair as funerals go. I am somewhat irreverent and remember clearly my twin brother and I giggling all through my Uncle’s funeral because his widow had the price ticket still dangling from the back of her hat. John and I shared a sense of mischief and humour. At our Grandfather’s funeral, we’d been unable to look at each other during the hymn ‘Praise my soul the king of heaven,’ because John had written an alternative verse that was utterly filthy and we both knew what...

Lesbian
2 years ago
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Wartime Passion

A few years ago, my wife was having a midlife crisis while I was away serving in Iraq. She was both lonely and horny. She had been without me for nearly 8 months and I still had four more months to go on my tour of duty. Char is an attractive 40 year old woman, 5'8" tall with blonde hair and green eyes. She keeps herself in great shape and still has a body to prove it, 36-30-36. Our sex life is absolutely wonderful when I am there, and I would not change a thing. She is a Hottie and we are...

2 years ago
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I was a wartime TV for the US Army

  'I was a Wartime Transvestite for Uncle Sam!              TJ Ryder                                          Chapter 1          Reform School Romance!    I couldn't believe that all I got from my uncle Bill when he died after all he said to me about my being hisfavorite grand nephew was an old diary from World War II.   I mean I thought we got along pretty darn good, and its not like he had any money or anything, just another oldgeezer in an assisted care center who if he ever had anythinghad...

Crossdressing
4 years ago
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Summertime Fun0

Summertime Fun After my divorce I got my daughter every other weekend and for the entire summer. Now that she was fourteen and developing quite nicely I was enjoying her even more. I also indulged her desire for sexy revealing clothing, since her mother wouldn’t. Holly was pleased that I had purchased a summer home alone the beach. We used to go to the ocean when we were still a family. Another thing that I did to piss my wife off after the divorce. It was a very nice place and I...

2 years ago
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Summertime Chapter One

Summertime: Chapter 1 By Tommie Summertime, and the living was easy. I had just graduated college and I was home for the summer. My parents were on vacation and I had the house to myself. I had settled into a relaxed routine. Up late, lazy breakfast, a little bit of work on the computer to keep my hand in for the programmer's job I was starting in the fall. Then, as often as not, a lazy afternoon reading in the back yard before soccer training in the evening. Soccer had paid my...

2 years ago
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The Saleswoman

Well I have always had a fantasy of a saleswoman coming to my door, wearing high heels, sexy stockings, a tight skirt and low cut blouse. She knocks at the door and I invite here in. I let her start her pitch but soon interrupt her by asking "Did it hurt? When you fell from heaven?" for which I get a smile. I the ask "If I told you that you had a great body, would you hold it against me?" at which she laughs some more. I then say "nice outfit, it would look even better on my bedroom floor". The...

2 years ago
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Door to Door Saleswoman

Door to Door Saleswoman Susanna says: - This story, along with the tale of the Handyman and the Blind date, were three of my earliest stories and were focussed more on gratification and lesson character, but I like them as it shows my journey as a writer. Here is a story that is always just around the corner for many T-girls and TVs, it also takes some courage to make a spur of the moment decision like the one in the story and not all of us have had that courage when...

4 years ago
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Rape Of The Saleswoman

Here's the info I can think of  ?????????????????????????????????? RAPE OF THE SALESWOMAN Kim is a very hard-nosed saleswoman. She may be small in frame, but she is tough as nails when it comes to getting what she wants. She has been working at the same large company on the east coast for over 10 years. Over that time, she has gained a well-deserved reputation as a bit of a bitch. That said, it has served her well professionally as she heads the sales department now after starting as a...

3 years ago
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Being Treys Wingwoman

"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...

Incest

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