Olderman And Mature Crossdresser Part 1 free porn video

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It was just a normal friday day so I went to the store to buy some food for the week.I wore a jean mini skirt and pink t-shirt and tan pantyhose with my 3"heels and make up and all.
As I made my way down thru the ailse I notice a older tall gray haired slim man following me.Well I gave him a couple bending over shots and eye contact.I made my way to the check out an seen him in other line.I finshed checking out when I got outside to load my bags in my car he was parked next to me.He spoke to me and said that he was sorry for following me around that he was not some kind of crazy killer but he wanted to tell me how nice and sexy. I said thank you and we talked for few minutes and I explained I was fulltime crossdresser.To my surprise he asked if I would be offened if he asked me out to dinner and a movie. I said well if you asking yes I would go on date with you. He gave me his number and I gave him mine.
I was at home and just got done putting away all the stuff I bought when the phone rang. I picked it an said hello and it was him he asked if I would like to go out tonite.I said sure and he said he pick me up about 7 pm.That gave me time to take bath and shave smooth and do evreything I needed too.
I did my make up and went into my room.I picked out a pink corset with pink gartor straps on it matching thong and bra glued my fake silcone breast on an tucked and tape my cock down flat. I put on a pair of tan seamed back thigh hi stocking an hooked the gartors straps to them.I hadn't picked out a dress yet but my mom and aunt stopped by and picked one out for me. They picked a black tight mini dress out that zipped in back that was sexy but nice looking.Well I put on my new open toe 5" stilettos with ankle staps so he could see my toe an finger nail were painted same glitter red and due to just had my nails done and filled.I put on my choker with silver cross and hoop earrings in my top holes and long chain type ones in my bottom holes.I finshed putting my rings and braclets on amd purfume.
Well at it was 6:45 pm when he pulled up he came to the door an knocked and I open the door his first words was you look beautiful I said thank you and got my purse and locked the door.He was a gentleman open the car door and shut it for me. We ended up going to a high end restraunt. We talked during dinner and he was vey sweet and a complete gentleman.He always held his arm so I could hold on to it.
Well he always open my door an closed it for me.We got to movies an he got our drinks an a seat in the theater.I let him hold my hand during the movie.He whispered during the movie to me how he liked my sexy smooth legs so I took his hand put it on my thigh so he could feel them.He gentle rubbed them during the movie.When the movie was done we held hands back to the car. It wwas about 10:30 and he asked if I would like to go down to a little park that had a water fountain and lights an sit and talk.I said yes.
We walked around for few minutes talking and sat down on a bench there.While we sat there talking I was thinking to myself how much of gentleman he was, but wishing he would make a move on me.Well he must have read my mind, because he if I would get upset with him if he tried to kiss me.I said to him nope.I turned so I was faceing him shut my eyes our lips meet chills went down my spine as we kissed. We sat there good bit talking and kissing.When we notice some drunks acting stupid and loud. So we decided to leave he asked me if I like to go for a drink at bar I said that bars were packed around there.He asked if had anything at my house I said yes but my dogs were there and they be crazy when I got there so I suggested we stop by his house and have a drink.

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It was a 200 mile journey from the city to the outskirts of a small town by the countryside where I live, I have hitchhiked this road many a time but this day proves to be an exhilarating adventure into my first cross-dressing sexual encounter, I had my large backpack I carried with me with my belongings including in secret my lingerie, heels makeup etc. about 60 or so miles out a 4 wheel drive hauling a horse trailer pulled up alongside me, rolled down the passenger window a man who seemed to...

1 year ago
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My first time with another crossdresser

In this story, I'll go in depth on how I became the "girl" that i am today. It all started when i was about 5 years old. I obviously wasnt sexualy active way back then, but thats the age i remember i fell in love with pantyhose. One night after my parents came back from a wedding, i was home with my brother and sister. They came home, changed and what not and went to bed. well my mother who changed in the bathroom left everything that she wore in there. i happened to pick up her pair of sheer...

3 years ago
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Crossdresser wanting some dick on the road

I`ve been crossdressing since I was 20 years old.One of my favorite things to do is get all dressed up in womens clothes and drive around on the open road.Several years ago I was mad at my ex wife for doing some stupid shit with our checking account and we were split up for some well needed cooling off time.The more I got to thinking about her stupidity the more I got to smoking some pot and drinking a few mixed drinks to get the crap off my mind.I got pretty stoned and decided to get dolled...

2 years ago
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Telling Mom Im A Crossdresser Part 2 The Adult Store

I awoke the next morning a little groggy as I slowly recalled the events that had taken place last night. I rubbed my body up and down feeling how the latex had now become a little sticky and how my ass and cock were still sore from the pounding I had taken. I read the note again left by my mother and decided to make breakfast as I was for when she arrived. It was just past 9am when I heard a fumbling at the door, my mother had walked in with her heels in her hands and her clothes hanging loose...

Crossdressing
1 year ago
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Strange RelationshipsChapter 10 Armand Mixes in the Hernandezs Affairs

Armand Wilson sat in his home office/study sighing. From the office, things had looked pretty good; business was on track, and Sharon appeared to be handling her new situation well. But in the car on the way home, Armand began getting bad vibes, and when he arrived at his mansion, things were even worse. Everyone on staff was walking around as if on eggshells. It took Armand about twenty minutes' worth of snooping, but the situation resolved itself -- the Hernandez' quarters were an armed...

4 years ago
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CANDY FINDS HER SON HANDY AND DANDY

by Oediplex 8==3~ The sweetest mom discovers her boy is both convenient and delightful. [She also recounts when her dad fucked her at nineteen!] Like the name of Madame DeVille's moniker, Cruella, some names fit the personality they are bestowed upon. Disney came up with that evil woman's apropos handle. My mother's folks named their only child, a daughter, Candy. This was shortly before the infamous 1968 movie was out. Though there were aspects of mom that paralleled the...

1 year ago
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Crossdresser and I at Costco

I went to Costco over the weekend with my friends girlfriend. She went off shopping, and I went off to get a few things. I walked down some random isle, and saw a girl leaning down. I snuck a peek at her butt and saw a little bit of a thong showing over the top of her shorts. She was wearing a blue hoody. I looked up and saw that she had really short brown hair. I tried to see her face, when she stood up. A box fell from her hands and onto the floor. Being the nice guy that I am, I picked it up...

3 years ago
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First Crossdressing Sex After Marriage With A Mature Guy

Before I bare the details of the night that took me back in time, I should tell you a bit about my past, and my present. Before marriage, I used to cross-dress quite often for tops who enjoyed my slutty alter-ego. I enjoyed being the dressed up slut, begging and hogging on cock. I had shoulder-long hair, pretty slim body, and I used to keep it hairless. Despite all that, in normal life, I looked pretty much like any straight guy. But with the right dresses on, a bit of makeup and lipstick, I...

Gay Male
4 years ago
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Crossdresser to Trans Escort Part 3

This is a continuation of my Crossdresser to Trans Escort series.After my first fuck for money with the restaurant owner, things escalated. I arrived at work the next morning wearing a pair of black trousers, black blouse and flat ballet shoes. The owner called me into the back office before we opened up for the customers. He was sitting behind his desk wearing a tight black t-shirt which showed off his tanned skin and bulging muscles. 'I really enjoyed our transaction last night' he grinned,...

3 years ago
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My Date with a Crossdresser

A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity.We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready yet and asked me to wait half an hour. I agreed.Half an hour later, I returned to her room, but she still wasn't ready. She was apologetic, and asked me if I would rather come back in another half hour, or...

2 years ago
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Crossdresser ke saath maza

Hello frnds.How is everybody.I recently got another hot encounter in July 2008.It happend at my sis home.Both my sis and her husband work for an MNC.They had recently employed a new maid.They were supposed to go to Pune for some seminar from their company.Since this new maid is new in town and has nowhere to go so my sis said me to stay at her at home so that maid will not face any difficulty.i said ok.I understood the problem and said ok for the proposal.So i reached her home on the day on the...

Incest
2 years ago
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CL Memories 1 Crossdresser True Story

I used to get a lot of fun out of CL. I'll post some short stories about some of my experiences there. I sure do miss it. This happened about 10 years ago. I was divorced and living alone, and playing whenever I got the hots and had a good opportunity.I checked CL one weekend night to see if there was any fun to be had, and found a post from a crossdresser visiting a nearby city and looking for company. She (I'll use that pronoun here) had a room in a local motel for the night. I responded to...

3 years ago
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AutoRide Made Me A Crossdresser Whore 8211 Part 5

Except for some dirty and humiliating ones, most of Raghav’s dialogue will be in English in this part about the crossdresser whore. I thought that it is easier for me than translating each of the dialogues. The ride home was uneventful. I just sat dumbfounded in the back seat while Ragahv just fled the auto fast. In a short time, we reached my place. I picked my bags and climbed the stairs. Raghav followed me, carrying another small bag. Where did he get it from? I am sure he was spotting a...

Gay Male

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