My First Time Going Out Dressed Like A Woman free porn video

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A few months back I met a dominant woman. We got along really well. After dating a couple of weeks, Melissa and I were out having drinks. She began asking me super personal questions. I was reluctant to answer her questions. She began buy whiskey shots. I believe in the intent to make me confide in her my most inner fantasy secrets. After a couple of shots, I confessed to her that when I feel submissive I'll put on some female items I had bought. Then I'd watch Shemale and crossdressing porn and masturbate. She continued to ask questions along these lines and asked me if I thought I could ever go out in public dressed like a woman or pursue the things I saw in those videos I watched. I told her I wasn't sure, that I didn't think so.

A couple of days went by and Melissa called me up and asked me to come over. She told me she wanted to take me shopping. We got in her car and drove about an hour to a larger town. The first place she pulled into was a plus size woman's dress shop. I asked what we were doing here since she is not plus size. She informed me she was going to help my fantasy become a reality and part of that was going through the humiliation and giving into my true desire. She took me into the dress shop and we looked around. After a few minutes she asked a saleslady if she could help her friend (me) find the perfect dress. I was shocked, but went along with it. The woman found several dresses for me to try on. I went into the changing room and changed into each dress. Coming out of the changing room and getting the opinion of Melissa and the lady. I felt so humiliated. With there advice I picked out a blue floral dress. I made the purchase and we left the store.

Our next stop was at a woman's shoe store. We browsed shoes for a little bit. Then again Melissa asked the salesman if he could find me a pair of heels that would fit me. He brought out several pair and I tried them on. He kept glancing at Melissa. After trying on several pairs of heels and walked around in them I settled on a black, short heeled pair. We made the purchase and he kept looking at Melissa as he rang up my purchase.

She drove for a little bit and asked me if I was satisfied with my purchases? I told her I like what I had bought, but felt awkward and humiliated trying those things on in front of others. She told me that's part of the excitement of it all. She then pulled into the mall. She walked directly to the lingerie store. She found a few pair of panties and stockings and suddenly stopped one of the workers and asked, "Do you think these would look good on my friend?" She clerk blushed and replied, sure. She had picked out a pair of black satin panties and black stockings.

On the drive home, Melissa said our next purchases will have to be made online. I was fairly silent on the drive home, but felt strangely excited about my new items of clothing. Once we got back to her house she went online and started looking at wigs. She asked me what color of hair do I want to have. We picked out a nice blonde wig. She then maneuvered to an online transformation site. She said we want you to look as real as possible when you make your debut. She found a sleeve to hide my cock in so I would have a bulge. Then she found a padded girdle so I had a more feminine looking butt. It was padded as to look real. Then she found some fake breast with the right touch I would look like I had real boobs.

Over the next couple of days she showed me how to apply makeup and lipstick. She told me before I go out, I have to shave my entire body. She had found some makeup to hide my 5 O'clock shadow when I finally went out. Melissa took me out to get a manicure and pedicure. Finally she had me put everything together and get dressed so she could see how I looked. Melissa said she was amazed, although I was tall and had an athletic build, I could pass for a woman. She told me it was almost time for us to go out in public.

With short notice I was told at work I would have to go out of town for several days for a conference. Melissa said it would be good for me to make my first appearance as Kathy out of town. That way I wouldn't be so nervous and there would be a lot less chance somebody might recognize me. She suggested that I pack my Kathy clothes in a separate suitcase and when I got the chance I should go out in public. She told me to call her and she would help me get ready.

I flew out to a large East Coast city. The first two days I was too busy with the conference and was too tired afterwards to go out. On the last night I was there I called Melissa and she took me step by step to get ready to go out as Kathy. She talked me through applying my makeup and lipstick, getting my wig on right and secure so it wouldn't come off. After almost two hours of prepping I was finally ready to go out and make my debut as Kathy. I thought it would be best my first time to go to a dark club or bar. I got a taxi and in my best female voice, I asked him where I could go have a couple of drinks.

He drove for only a few minutes and stopped in front of a nightclub and told me it was a popular place. I got out and walked into the club. I was sitting at a table by myself having drinks and watching the crowd when two men sat down and asked to join me. I said sure and they sat down. They bought several rounds of drinks and made small talk. They complimented me on how I looked. That made me feel good. I wanted to text Melissa and tell her what was going on, but suddenly I felt dizzy and light headed. I tried to excuse myself, but the next thing I knew I was in someone's basement blindfolded and restrained to a padded device.

I heard one of the men say, "We don't care that you are some sissy crossdresser, we are still going to fuck you like a dirty whore and there's nothing you can do about it. I felt one of them move behind me and force his cock into my boipussy. It hurt bad and I screamed. He laughed and said, Nobody is going to hear you down here. He just kept fucking me. Then another one came up and shoved his musky, small cock into my mouth. I sucked it reluctantly. I didn't want to be hurt. I felt so humiliated because after a few minutes the pain subsided and began to feel good with him fucking me. My clit got hard and I began moaning. I sucked the other's cock eagerly and loved being fucked and used like that. They laughed at me seeing that I was turned on by their actions. They took turns fucking me and having me suck their cocks. I felt like I didn't want it to end.

After about 30 minutes both of them had cum in me. I swallowed a load and taken a load deep inside my boipussy. They kept the blindfold on and drove me back to the club. I was barely dressed, my panties were soaked from the cum leaking from me. They shoved me out of the car with the blindfold still on. I didn't bother getting a cab. I walked back to my hotel feeling so humiliated yet turned on.

I got make to the room and took a shower. I stroked my clit while I showered. I didn't text Melissa, but I told her what had happened while I was out of town. She asked me how I felt about it. I told her I couldn't believe how turned on I was by it and how good it felt.

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Right at the beginning of the final two week session of the summer camp, Rebecca was tasked with leading the Eagle Scout prospects out on a long two night hike that would take them completely around the long narrow lake that was far better to canoe or rowboat rather than hike in the dense underbrush surrounding the lush shorelines. She found that there were four male Boy Scouts and three female Boy Scouts in the pool of applicants and it worked out just fine for four two person tents to...

2 years ago
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Wanna Makeout

Dave and Kim had dated early in their life, before they actually new what dating was and after their breakup became close friends. It was after Kim’s boyfriend, John, who was also Dave’s best friend, left for Germany to study there for a year that the jokes began. It started small, jokes with John before he left that Dave and Kim would hookup while he was gone. These jokes always would upset John and make Dave and Kim chuckle. The jokes continued after John left, and even after Kim and John...

2 years ago
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Lunchtime Munchtime

As was his habit at lunchtime, Hal left the building and walked through the office park for exercise. It was a partly cloudy day, and for the moment it seemed overcast. On his way to a small path through the woods, he saw her. Sandy was an attractive redhead with a sensual voice who almost always wore a tailored blouse, a roomy ankle-length skirt, and one-inch pumps. Her wardrobe varied in color, patterns, and material, depending upon the season, but always the same ensemble. Hal watched as...

2 years ago
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Cat and Mouse The Tryout

Cat and Mouse: The Tryout by Bluto "Good afternoon, this is Della Delargio reporting live for WNBC from the financial district. The Protectors, NYC's newest superhero team, has just foiled a bold daylight robbery attempt by The Destroyers, a gang of supervillains who have been increasingly active in recent months. "The Destroyers staged a lightning raid on the Federal Reserve Bank and were about to make a rooftop getaway when The Protectors came charging to the rescue. Here...

3 years ago
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The Dugout

Cherie is a lovely Asian woman. She seems like a typical wife and mother. But there is a dark side to her. Cherie is one of those fiery tiger moms who thinks her son can do no wrong and that she deserves to be in control. Not always. Cherie was watching her son play little league baseball with the other moms. The game was intense, and Cherie was really animated and vocal about what was going on in the field. Her son was at bat and had two strikes against him. Both were questionable calls, in...

2 years ago
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Cheerleader Tryouts

From: [email protected] To: [email protected] Subject: Cheerleading (what else?) Hey Em, it's your very-best-friend-in-the-world, but I guess you knew that when you saw the "from" line, right? Duh, my blond is showing again. Anyway, how are you holding up in godawful Cleveland... I still CANNOT believe that your parents could just up and move from beautiful SoCal to the midwest for gods sake... and break up the dynamic duo of Smithfield High cheereleading... but anyway, I still...

2 years ago
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First time out dressed as a woman

I have crossdressed for a long time but was always to scared too. Now i sometimes, have panties or a thong on underneath my jeans when i go out and have put on one of my bras but no padding as it would be noticeable and i like to give myself a big boob look. So i had gone out with a black satin thong on and my tiger print bra on underneath my regular guy clothes and went to a local store, walked around for a bit, nobody noticed anything about me.I had brought my padding with me and went to a...

2 years ago
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The United Kingdom of Zoo A fake BBC documentary seriesS12 E16 Tamara Cooper 32 from Southampton

We start this week’s show with an establishing shot of St Mary’s Stadium, home of Southampton Football Club ... Then spinning around to look over the River Solent, zooming in on a large, gray-green structure with little round windows ... Then we cut to that building – on a dusty industrial estate - with the river and St Mary’s Stadium in the background. A sign on the front of the building reads “MAIN AGGREGATES”. Our host steps into frame from the side, immediately making the scene better to...

1 year ago
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Wartime

Elizabeth Fleming told me some of this story in the years before she died, aged eighty, in 2010. The more graphic scenes are mine but the emotions and surrounding history are hers. She was my Great Aunt, great in so many ways for she was the third family member I ever revealed my sexuality to, the first two being my parents. I had known since girlhood that she shared a cottage in Hampshire with her friend, Portia, but had never known their relationship was more than sisterly. When I told her...

Lesbian
1 year ago
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The Outlaw and the Innkeepers Daughter

Author’s Note: This story was written at the suggestion of a medieval re-enactor friend who served as the template for the main character. She has recently passed away and this story is now dedicated to her memory. Goodbye Artemas Innkeeper of the Inn of the Drunken Hare, March 5, 2008. * The two forest outlaws watched nervously from the edge of Barnesdale Woods. Well concealed, they took their time to assure themselves that no one along the Nottingham road would see them approach the old...

2 years ago
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The Grim ReaperChapter 37 Outpost Zulu and Other Iraqi Delights

July 2006 - September 2006 Things got back to normal. The next day our families flew back home, and Bravo Three was kicked out of the Al Faw Palace and sent back to Anaconda Three. Riley looked even worse that morning; he was storing up debauchery for the future like a squirrel storing up nuts for the winter. We pretty much had to carry him out of there, and Bixley asked us what he had done to get in his condition. “Sarge, if I told you, you wouldn’t believe us. Riley committed every sin in...

2 years ago
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TangentChapter 10 Outpost

Judy was woken for the second day in a row by a kick on the foot. She cracked an eye and saw Tanda Havra once again standing over her. "Breakfast," Tanda informed Judy. "Then horse or wagon." Judy looked around the tent, empty except for the two of them. She must have been tired to sleep past the others getting up! "Horse," Judy said almost without thinking. She'd seen the wagons yesterday. They bumped and jolted you; there were no springs. "Be ready, be quick!" Tanda told her,...

1 year ago
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Outdoor playtime

True story.We were out on a date in Columbus Ohio, had a few drinks and dinner, I was thinking about fucking Lee all night long, I must have slid my hand up her dress at dinner at least 10 times. It was warm and clear that night (unusual for Columbus) so I suggested we drive over to a local park/lake for a walk over the dam and she agreed. We were both feeling good, the wine and drinks were having the desired affect on her libido . . . we were both feeling very horny. It was really very dark...

1 year ago
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The Lust of a Sunday School Teacher and a Churchgoing Boy

Introduction: Mrs Maggie Henderson is the pastors wife who out of growing sexual frustration seduces a fellow church member Clay Nicholas who use to attend her Sunday School group, but will an unexpected house visit later in the day threaten to turn the small Christian community upside down. (told from the boys perspective) Mrs Maggie Henderson The Pastors Wife and Sunday School Teacher The Pastors Wife I was brought up to go to church and believe that there is a God who will send me to hell...

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