Friday Night Crossdressing free porn video

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Silky long sleeved blouse and skirt?

A dress?

Or just lounge around in my lingerie.

Parking my truck my anticipation only grew to full out excitement, a huge smile was plastered on my scruffy face.

I was almost skipping up the sidewalk. I'm sure some of my nosy neighbors saw me but I didn't care. It was a long week to hide Lisa within me.

Once inside my apartment, I quickly got undressed from my work clothes and stood in front of the floor length mirror to admire my lingerie I always wear under my male clothes.

It's at that time that Lisa takes over and god only knows what she's gonna dress me in.

First the three SSS. Shit, shave and a shower.

Then I sat in the armchair staring out my living room window. Living on the top floor that looks out the river valley is nice, believe me.

Once I was dry I started picking out what I wanted to wear.

I decided I wanted to wear satin white everything.

Push-up bra, super shiny silky stockings with garter belt and of course matching crotchless panties. My cute little steel chastity cage peaks out the front. Lol.

I went to my vanity to apply some lipstick but couldn't decide what color so I used bright red outlined in sparkle dark pink. A new look for me but I loved it. A little lavender scent and I was ready. I didn't want to do a full make-up job as I wasn't planning on going out.

I sat in the living room just staring out the window relaxing while I sipped a little bourbon.

A knock at my door woke me up a while later. I got up without thinking and answered. My gay neighbor from the main floor stood there completely shocked as I asked what's up.

Suddenly I realized what I had done but he saw the way I was dressed so I decided to see where this went.

A long awkward silence followed as he took in the sights. I could feel his eyes examining every inch of my body. It excited me.

So what can I help you with, I ask?

He obviously was in some kind of shock. He didn't answer so I turned away from him and walked back to my armchair then sat on the love seat instead. He followed a moment later. I assumed he closed the door.

He stood at the entrance to my living room and stared some more.

I asked him if he wanted a drink. He shook his head yes so I got up, went to the mini bar and poured him a bourbon. I walked right up to him and handed him the drink then turned and walked back to the love seat and sat down.

So you've never seen me like this, I get it I said. This is how I like to relax.

Yeah is all he said.

What did you need?

Oh ummm, his eyes are still studying me. I was wondering if I could get a ride across town but you look busy so.

Give me twenty minutes and I'll see you downstairs ok.

Oh no I couldn't…

No worries, I explained.

Okay. Sounds good. Thank you so much he said then left.

My heart was racing as I went to the bedroom to change but Lisa surprised me. Instead of changing out of my lingerie I found myself getting into a bright white minidress and high heels. Some eyeshadow and blush finished my make-up. I grabbed a small purse that I keep filled with lipsticks, condoms and lube and I headed downstairs.

The weather in August is always hot so I didn't need a jacket.

Steve was waiting for me at the doors.

He was more shocked to see how I was dressed now than before I think.

I walked up to him, my heels clicking on the tiled front entrance. So where do you need to go?

Umm just to…

I'll show you…

To the umm…

Relax bud. It's just a ride, right.

Oh yeah. I no, but damn you look good.

Smiling and saying thank you I pass him heading out the doors. It's 10:30 so everyone is already in their suite's but I still wasn't sure I wanted to be seen by anyone else.

Not thinking I pushed my remote starter and my truck came to life with the headlights shining right at me.

The drive to the other side of the city takes about half an hour. We made a little small talk but it seemed like he wanted to avoid the elephant in the China shop so I left it alone.

He told me he was going to a friend of his for the weekend.

Up ahead I saw the lights for the gloryhole. I thought to myself on the way back home I'll stop in there and see if maybe I could have a little fun but the next thing you know I'm parking in the parking lot. Without saying a word I got out of my truck and went inside.

The place was very busy. I got some tokens and went into the booths area. I was obviously the only gurl there because I was getting hit on left and right.

I entered a booth with holes on both sides. I didn't have to wait long and both holes were filled with cock in no time. I sucked the bigger one while stroking the other until I swallowed the first load of the night. The other guy pulled back. I guess a handjob wasn't what he wanted. Soon both holes were filled again. Again I sucked the bigger one while I stroked the other. This went on for a while then I opened the door to leave and Steve was in line next so I went back in and sucked the guy in there.

Then I looked through the hole to make sure it was him. It was. He pushed his sizable cock through the hole. I decided I was gonna treat him to a no hands blowjob.

I started at the base as close to his balls as I could and slowly licked all the way to the tip, taking extra time to lick his already leaking slit. Then sliding my tongue down the side as far as I could. Allowing his cock to slide over my face as I moved to the other side then licking up that side again stopping to lick his slit. Then I opened my mouth and took his head in using my tongue to swirl around the head. I pulled off sucking really hard making a popping sound. His cock jumped and got harder.

I slipped my lips over the head and slid down part way savoring every inch. My tongue was ahead of my lips as I went down on him.

I wanted to take my time and enjoy the experience as much as possible.

Over and over again I slid his delicious cock into my mouth then I pushed down a bit further until he was sliding down my throat. I was totally relaxed as I slid him back and forth in my throat. Breathing through my nose as I did.

Then I picked up the pace and kept my lips tight around his love shaft. He pulled back so I planted my lips on the hole and he slid into my throat. I held as still as I could while he fucked my throat through the hole. He slammed into my throat hard and fast now. Then he groaned and pushed all he had into me and filled my stomach with warm cum. I wanted to taste some so I pulled back and sucked his twitching cock head as hard as I could. He let out a loud groan as he filled my mouth. There was so much cum I couldn't swallow fast enough and some spilled out the corner of my mouth onto my dress. I caught up to him swallowing his cum. He pulled back and I watched him tuck his cock back into his pants and left. I waited a moment then I left as well. I made my way to the bathroom and freshened up my lipstick then went to the truck. He was waiting for me.

I got in and started it and left the parking lot.

He didn't say anything until we got to where he was going.

Then he asked if I wanted to come in for a while.

I thought about it and said no. He should go and have fun with his friend.

The outside light to the house came on. He asked again if I'd come in with him.

Again I thought that it would be fun to have a couple young studs to play with.

That's when the drivers door opened and a good longtime friend of mine stood there saying, holy fuck dude. I thought that was you.

Mark and I have been friends since grade four. I didn't know he was gay and obviously he thought the same about me.

Steve shut the truck off and got out quickly with my keys so I thought what the hell. I might as well enjoy myself too.

I got out and Mark had me spin around for him. I fuckin knew your ass would look good in a dress he says.

I told Mark, I go by Lisa when I'm dressed like this

We all went inside. Mark had a few other friends there.

Candice and Tim were a married couple.

Gail and Don were engaged.

Robert, John, Seth and Mel I didn't know but as far as I could tell they were single.

Mark introduced me to everyone as Lisa and we all sat in the living room and drank while laughing at jokes and such.

Candice saw the cum on my dress and said it looks like I had a headstart tonight. She wiped it off with her finger and licked it. Smiling she laughs and says yep, it's cum alright.

After a while I asked to use the bathroom. Steve said he'd show me so we got up. Everyone made more jokes about a guy and a gurl going to the bathroom only meant one thing.

Laughing, I followed Steve.

In all honesty it would have been difficult to find without help. The house is rather large. I stepped in the bathroom and closed the door, not tight mind you in case Steve wanted round two.

I hiked up my minidress and sat down. I tucked the short tip of my cage under the seat and let the pee go.

As it tinkled into the water below the door opened. Steve comes in with his hard cock pulled out the zipper. I licked my lips and said I was hoping for round two.

He grabbed my head and pushed his cock in until I felt his Smooth skin above his cock touch my nose. He slammed my throat hard and fast then pulled out cuming all over my face. He then dared me to come back to the living room just like this.

I've never once turned down a dare so I wiped myself off of pee and pulled my dress back down to where it should be which wasn't very far down at all. It barely covered my cage and we went back to the living room.

Steve led the way. I could hear everyone talking and laughing then Steve stepped aside and everyone saw me.

Cheers erupted in the room. Steve was getting high fives as Mark walked up to me and asked if I'm okay with this.

I smiled and said sure, it was a dare.

He licked my face and tasted that it was cum then said I'd be the main attraction.

I wasn't sure what he meant by that, he just smiled and turned back to the people and said yep. That's definitely cum ladies and gentlemen. And it's still warm.

Candice got up and licked a little cum off my face next as she slid her hand down to my cage. She was really surprised and asked what it was she was holding. I smiled and told her to have a look. She kneels in front of me lifting my dress up. I don't think she knew what a chastity cage was. She looked up at me confused. The rest of the group were cheering her on. She leaned in and licked the opening of my cage then got up and sat back down with her husband Tim.

She whispered something in his ear and then just watched after that.

Gail went to get up but Candice told her what I was wearing. She said loudly. I gotta see this.

She walks up to me and straight out asks me if I'm a guy.

Embarrassed a bit I told her to look, herself. She lifts my dress and looks then laughs. It's so fuckin cute. You're definitely not a man.

She held my dress up and moved to the side showing everyone as she says what we have her is another fag only this one thinks it's a girl.

She licks a little cum off my face and pulls her t-shirt off revealing her nice plump tits.

Let me know if this story interests you by commenting below.

Please let me know if my writing skills are improving as well.

Thanks.

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Your mom is away a lot with her friends and she has recently divorced her husband. Right now she's away with her friends to celebrate breaking loose from that bastard and getting back on the market. Your older sister is 26 years old and just bought an apartment a couple of towns over. When moving out she found a bunch of old clothes she didn't want anymore so she left them at home for your mother to send to some charity. Now, you're home alone, your mom isn't coming home tonight since she's...

Incest
2 years ago
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Caught crossdressing

The below is a true story so naturally names and places changed but the rest of it remains to be one of my memorable moments!!What seems like many years ago now when I finished university my then girlfriend Lexy and I went down to Cornwall to stay in her parents holiday home for the summer while we worked out what to do. To be honest at this point we both know that we aren’t “the one” for each other but I think we both had the same thought, see what happens over the summer and then make...

2 years ago
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I was his bitch first time crossdressing

My growing curiosity was really starting to take control. I've spent so many years married, hiding my true thoughts and fantasies about sex.My wife and k**s were going out of town a couple of weeks ago and I was going to explore more of what I wanted. As the day they were going to leave got closer, my pulse would race and my palms would sweat.I just hoped I wouldn't chicken out.Finally, I dropped them off at the airport and as soon as I did, I was freaking out. Just thinking about visiting my...

4 years ago
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My journey into crossdressing

The following story is 100% true. Only the names have been changed.About 11 years ago, when I was 28, I met a 40 year old single mum of 2 called Michelle.We met through a mutual friend. The relationship was purely a sexual relationship. I had just broken up with my girlfriend of 3 years, and she had been single for 7 years after splitting with her violent ex.The first day we met, we ended up sleeping together. As we lay in bed afterwards, we started talking about what we liked and didn't like...

4 years ago
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Christmas Crossdressing

Over the Christmas holiday I was in the gay adult book store and some big old white guy asked me to go to a gloryhole booth. I went in and he went to the other side. I popped in my quarters and as I was unzipping my pants an old floppy dick came through the hole. I just heard “suck it boy.” I licked the head and watched it raise and raise and raise. The more I sucked the fatter it got and I was honestly surprised, he was a good 8 inches. He started pumping his dick through the hole into my...

4 years ago
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caught my son crossdressing

I had come home early from work and found my son, Jamie, sitting at my vanity, putting on make-up. He was wearing one of my cocktail dresses -- and my stockings, my high heeled sandals and, it appeared, my lingerie. He hadn't heard me come in, so I just stood silently in the doorway watching him put on mascara, blush and lipstick. He was completely mesmerized by his own ladylike reflection, completely entranced by the girl in the mirror. He did a very good job with his make-up; clearly he...

3 years ago
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My Early Crossdressing

I started cross dressing around 12. At first it was knickers or tights. As I got older I started to get more serious with it. Just after I turned 16, I'd often go out round the streets round town dressed in full girls clothes. I'd always prefer going out late in the evening in winter, as I'd not pass many people and id normally only pass a few cars, some would slow down as I walked along the side of the road.One day I was home alone, my parents were away for the week and my sister was staying...

2 years ago
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my first cock experience true story crossdressing

I will never forget my first experience with another cock , it was the only time I have ever been with another man, now saying that I do date ts women, I love them as much if not more then I do genetic women. I was 12 years old and like any young boy , very horny . At that time my best friend liam and I would have sleep overs and do normal k** stuff , sports , video games , camping , never did I think that one day I would have his warm milky cum in my mouth or his warm hard throbbing Dick...

1 year ago
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Crossdressing

Hi back again… This is my friend new story. I met him in London last week .his name was mike. So let start… It all started a few weekends ago when I (mike) had been incredibly horny and my girlfriend was out of town. She wasn’t expected to be back for another two days and I needed some relief. She always wore really sexy panties and I loved the way they felt when she would grind up against my bare cock during foreplay. Being as horny as I was I went to the dirty clothes hamper and found the...

Gay Male
1 year ago
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First time Crossdressing

I am a bisexual man, meeting straight, bisexual or gay men for our sexual pleasures. I post messages on various message boards like Squirt and Adam4adam that allow members profiles and posting messages. I also post to local Yahoo groups in my area that allows one to post messages to a small geographical area or to a distant user group. However, the best place to find no-strings attached meeting is on Craigslist where you can post an advertisement for a geographic area in a personal group erotic...

She Males
2 years ago
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Friday Night Surely its my turn now

A few moments ago we had been sitting on the floor drinking sweet, black, coffee. The scene could be of three best friends chilling out, chatting about everything and nothing, except for us being naked, that is. Are we friends? Well Lennie and I have known each other since before first grade but we had only met Tia a couple of hours ago. Since then Lennie and Tia had thoroughly enjoyed each other’s bodies while I had watched on. I guess we should be called ‘friends’ after our night's...

Group Sex
2 years ago
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Friday Nights Date A Cuckoldress Gets Her Just Desserts

Bobbi Jo had checked her emails on her favourite dating site for hot wives and swingers when she saw one from a local man named Paul. He professed to be a strict Dominant, knowledgeable in the finer arts of BDSM and fetish play, and he loved to date married ladies.A brief flurry of correspondence ensued, and a date for Friday night was set. She eagerly told her husband, Lance about the coming tryst, and in true cuckold fashion she made him feel humiliated by the prospect of yet another stranger...

Cuckold
2 years ago
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Friday is the wifes date night

On Friday after work I normally go to one of the restaurants and have a few drinks and to eat before going home. You see Friday night my wife usually has a date so I must fend for myself. But last Friday I got a call from my wife to come straight home, she said she would explain why when I get home.As I entered my house I was met by my and she gave me a quick kiss on the lips. She was wearing her long bath robe but I could see her legs where encased in black nylon and she had on her fuzzy...

2 years ago
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Friday Night Spanking

Friday Night Spanking Friday Night Spanking   Joe relaxed and leaned against the wall of the kitchen, watching as Pita finished the last of the dishes. He looked down her long copper-red hair to the edge of her pink, cotton skirt that ended about three inches beneath her ass. He watched intently when the material swished with her movements. He knew there was nothing under the soft fabric except even softer skin. He could feel his hand itch with his want for her. Tonight was to be...

2 years ago
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Friday Night1

As soon as I turn I feel my doubled over belt smack across my ass. Even through my jeans it hurts and it causes me to yelp in surprise. You quickly smack me two more times and then tell me to turn back around. “Now, you will do everything that I tell you to do or you will not be able to sit down for a week. Do you understand?” you ask. I feebly tell you yes ma’am. You smile and order me to take off my clothes. I take off my shirt, jeans and socks. You order me to turn around again and...

4 years ago
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Friday Night Fun

Friday Night Fun by Girl PUP ? It was late Friday afternoon and I had just returned home after a long day at work. The minute I walked in the door, I knew the evening would be a mixture of indescribable pleasure/torture. My wife, Connie greeted me at the door with a glass of wine in her hand, and a gentle kiss on my cheek. As she greeted me, she ran her hand down my back and softly squeezed my ass, casually feeling to make sure I was still wearing the camisole and panties she makes me wear...

2 years ago
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A Nightmare on Elm Street invades Hollywood Freddy Kruegers Sexual Nightmares of female celebrities

Freddy was real there was never no movie, He was restless he hated that he had thought that revenge would feel better once he did so, but it did little to ease his wicked mind, however the dream demons had told him that the Elm Street sign was going to be planted in Hollywood, and that he could invaded the dreams of any eighteen year old and older celebrity in Hollywood, however Freddy was not allowed to kill any female celebrity, and also that his premiere purpose was to sexual own Any female...

2 years ago
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Friday Night Alchemy

(Author’s note – This is a 90% non-erotic story. The only erotic scene has been submitted separately as the short story ‘alone at last’.) It was April. It was raining. It was hardly a surprise. The weekend had started well: boy had met girl and the Friday night alchemy that turns alcohol into meaningless sex had just begun when the spell, or rather a Budweiser bottle, was broken by a not-quite-ex-boyfriend who mistook me for the villain in the tragedy that passed for his love life. I was in...

3 years ago
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Friday Night Magic

Friday Night Magic. Unfortunately, it's not as romantic as it might sound. I actually run a small comic book and gaming shop, and Magic is the biggest selling card game ever. Every Friday night, I would have anywhere from ten to twenty guys in the shop, playing cards until 11:00pm or later. As fun as it was, it didn't leave much as far as time for a social life, and my lack of sex was getting to me. I'm not the bar hopping, club bouncing type, so going out after the shop closed wasn't really an...

3 years ago
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Friday Night Maid Part 3

Friday Night Maid – Part 3 – by Diane Leonard[I walked towards his side of the bed, stood just out of reach. Took my models pose, leaned back, and said, ‘Good evening sir. May I stay here for a while? I have no place to sleep anymore.’ part 2 ending]With that, Roger got this huge smile, jumped out of bed and almost broke the door off as he closed it. He walked over towards me, stood about 5 feet away and began to take in the image. Walking over to me, his hands began to touch me softly. I stood...

3 years ago
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Friday Night Maid Part 3

Friday Night Maid - Part 3 - by Diane Leonard [I walked towards his side of the bed, stood just out of reach. Took my models pose, leaned back, and said, "Good evening sir. May I stay here for a while? I have no place to sleep anymore." part 2 ending] With that, Roger got this huge smile, jumped out of bed and almost broke the door off as he closed it. He walked over towards me, stood about 5 feet away and began to take in the image. Walking over to me, his hands began to touch...

2 years ago
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Friday Night Maid Part 3

Friday Night Maid - Part 3 - by Diane Leonard[I walked towards his side of the bed, stood just out of reach. Took my models pose, leaned back, and said, "Good evening sir. May I stay here for a while? I have no place to sleep anymore." part 2 ending]With that, Roger got this huge smile, jumped out of bed and almost broke the door off as he closed it. He walked over towards me, stood about 5 feet away and began to take in the image. Walking over to me, his hands began to touch me softly. I...

Crossdressing

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