Caught By The Neighbor Crossdressing While Home Al free porn video

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Do you know a crossdresser who got caught in the act?

This is a real life story of a crossdresser caught in the act!

This happened around when I was 15 yrs. old.

As my sisters were off at college and it was just my mom and I at our apt. I was home from school as we didn’t have any school that day. But my mom was still at work. So I got myself all dressed up looking pretty. As I thought I will make it a girl’s day in. I decided to wear a pair of my mom’s dark navy pantyhose with one of my sister’s jean skirts and a blue and white sweater with some black 3 1/2 heels.

I put my makeup and wig on. I felt so sexy en femme. I just couldn’t believe I was getting a chance to crossdress and not have to worry for a while as my mom was at work. I just ended up crossdressing, doing the things I normally would, which felt so good hearing my heels and hose rub together and my heels on the floor when I would walk.

After a bit I decided to go out into the hall way for a bit and see how far I could get without anyone paying any attention to me or even noticing me. It was nice as I liked hearing my heels crossdresser dressed upin the hall way. After a few walking the hall attempts, I decided to go down and check the mail in our mail box. Our apt complex had its own mail box. So I went down the flight of steps as we were 4 stories up. I was a bet cautious as I didn’t want to get caught. I made it down to the mail box and took the mail. There was a guy there that was checking his but he didn’t see my face. I could tell he was looking at me though, which I did like.

After I collected the mail I went into the elevator and headed back up to my floor. When I got there I went to my apt. You guessed it I was locked out. I forgot to grab the apt key when I walked out. I just had my mail box key. I was thinking how stupid. And then to make things worse here is our neighbor who is an older gentlemen walking down the hall way. I tried to turn away but I couldn’t fast enough. He stopped and was looking at me. I just stood with my back to him. I could feel him walking up behind me.

He said are locked out of your apt miss. I said yeah I am. I was so freaking scared. He giggled and said here come with me to mine. I followed him. Now I was trying not to have my heels make such a loud noise on the floor. I followed him in and stood by the door. He called the apt manager who had all the keys for the apt. Everyone pretty much knew each other so it was a real safe building. He came up and opened up the door for me. But my neighbor said that he thought he heard something and wanted to check it out as he didn’t think we were there and wanted to drop off our mail for us.

The apt manager bought it. As he left I went from my neighbors apt to mine. I told him thanx he said no problem. Smiled and gave me my mail. I was so relieved but nervous as I didn’t know what to make of it. I finished out the crossdresser session with a j/o session and then called it.

Later on my mom came home and we had dinner and just lounged around for a while. Then I went to bed as I was exhausted from the scare that day. The next day was a normal Saturday nothing much happened. But on Sunday my mom was going to church with her new boyfriend. So I was going to be home alone for at least 3 hrs.

red-dress-crossdresserI thought why not dress up again. So I put on some beige hose white bra. Jean skirt knee length and a white top make up and wig. And put on some black heels that were 4 inch. They were my mom’s. As I was just getting done, the phone rang. I answered it and it was my neighbor who wanted to know if I wanted to come over. I thought sure why not. I don’t know why but I decided to come over dressed as I was. I grabbed my apt key this time and walked next door. I knocked and he opened the door. He smiled and told me to come in. I did and sat on the couch, which is where it all took off from here.

He was talking to me about my dressing. When I started and why I did. He also said that he seen others who are crossdressers or dress n drag as well. He said that is a huge turn on to him. Hearing that got me turned on. I crossed my hosed legs in front of him. And begin to caress my legs with my fingertips. I noticed he liked that. I decided to make the first move and leaned in and kissed him. He took me in his arms and we must have been kissing for a while.

Feeling his hands on my legs, rubbing them, I decided to return the favor for getting me back into my apt, so I went down on him which was my first. I was so horny and nervous as I never had done this before. I undid his pants, and pulled his under wear down along with his pants. His cock was right in my face. I started to kiss it and then licked it. And then came of putting it in my mouth. I started to suck on it slowly, with a little trial and error as my teeth getting in the way. I gaged a few times, but I started to get the knack of it. I started to hear him tell me to not stop and keep going, which was getting me excited. I started to rub my hosed cock while I was sucking on his. The he came and it was a lot I could only handle so much and ended up spitting out the rest of it.

Then I came in my hose. Oh did that ever feel so good. After my first sucking encounter he said I should probably get back to my apt I agreed. As I got back to my apt, I got undressed and cleaned up. The phone rang shortly after and my neighbor told me he wanted to see me again sometime all dressed up again soon. I thought we could do that.

After which my mom got home with her new boyfriend.

November 29th, 2009

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I placed an advert on Craigslist as I fancied something new. I'd been crossdressing for a while and had met a few people for fun but wanted to try something a bit more exciting. My advert was looking for someone to meet in public for sex with me dressed in lingerie. A few replies came but the one that caught my eye wanted to meet in an adult cinema in London near city road. I heard of this place and fancied trying it out. We agreed to meet at 11am in a coffee shop nearby and go to the cinema...

2 years ago
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Crossdressing at the truck stop

Hello this is my first story I really hope you enjoy it I am a crossdressing truck driver and with my job I have a lot of time to enjoy dressing up in my truck. One night I was all dressed up in one of my sexy outfits watching some porn and thinking about trying to find a nice hard cock to suck. So I put an ad on Craigslist and got a few but none of them wanted to come to me then I got a message from a guy, he said that he was a driver and was at the truck stop. I ask him what he wanted to do...

3 years ago
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The Many Tales of Crossdressing

This story is open to anyone who wants to write a crossdressing story, it doesn't matter if it's an original story or a fanfiction. Please respect Chyoa's rules, so Bestiality, underage sex (younger than 18 years old) and extreme violence are not allowed. I would like to keep this story as organized as possible. For example, if you're writing a fanfiction, before you really start the story, make a chapter with the series the fanfiction is about in the title. Have fun!

2 years ago
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The Neighbors Daughter V A Mature Neighbor Comes to Call

It had been several months since Henry had been asked to introduce some of his neighbors’ teenaged daughters to the world of sex. The girls and their mothers had wanted, no they had almost insisted, Henry at over fifty years of age take the girl’s virginity and show them how wonderful sex could be. The mothers were afraid their sixteen-year-old daughters would end up getting screwed and knocked-up in the back seat of some boy’s car unless they knew what they were doing sexually. It had been a...

Mature
2 years ago
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Ashleys Crossdressing Adventures

It's Sunday and Mommy wants to hear what sissy things I have been up to, and don't leave anything out Sissy Ash, Don't be shy, out with it sissy, I already know you love being a complete sissy!Did you buy anything sissy? Yes Mommy, I did, I want to hear, everything you bought you little sissy, let mommy remove your bra, to access your sissy nipples,Mommy I bought 4 pairs of sheer nylon panties to add to my collection, pink, blue, white and yellow.What else sissy? I ordered 3 packages of...

Crossdressing
2 years ago
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First time crossdressing with a friend

My lovely new Malaysian friend emerged from the bathroom, moving shyly in the low light. He was wearing thigh-high stockings, cute little panties and a matching top that was tied at the front.My heart leaped at this gorgeous sight. He had advertised that he wanted to hook up with someone who appreciated fembois, and I was very eager to indulge his fantasies and mine!We had agreed that we were going to enjoy a girl's night together, and so he started playing some lesbian porn on his computer....

Crossdressing
3 years ago
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Sex with a crossdressing in a public toilet

Friday came and I'd bought a new outfit just for the occasion. I slipped into my low rise boy shorts (black with white spots and white lacing), tucking my penis in where it wouldn't get in the way of course. I put on my matching bra, filling it with my C cup breast forms and then put on my black stockings with pink ribbon at the top, pulling them all the way up my thighs. I put on my very short black skirt next, sliding it up so far as to just barely cover my rear end. Fortunately, I'd...

3 years ago
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Crossdressing Domina gets a new slave

I have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This is a story about my favorite slave I have ever trained. I had been anticipating the arrival of my new toy all week, and he was moments away. My new slave, eager to be trained under my heels. The first time I saw him I had brief fantasies of my hands and mouth exploring every inch of his petite and...

2 years ago
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Forced Crossdressing Stories

All of these stories share a central theme of Crossdressing. Rather than add yet another story for one of my ideas, new ones will now go here. I'm making the call, out loud, for additional authors to add their own threads and work with me. I would love anyone interested in any of these stories or my previous ones to add their own threads. If writing isn't your thing but you have ideas, send me a message. I'd love to hear of anything you come up with.

Transsexual
3 years ago
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Crossdressing for sex

The act of crossdressing for sex is incredibly arousing. It gets me in the mood for the debauchery to come and allows me to come Brooke the cock loving whore. Even having been dressing for over twenty years, I still look forward to it. Adding to the experience I like to dress while my lover waits in another room. I want them to sit there thinking about what I am doing, what I’m putting on, what I will look like when I enter the room. I want their imagination to flow, and I want their cock...

2 years ago
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An Introduction to Crossdressing Pt 6

After Steven leaves me at the table with Jackie and his new friend Chandra, I start to fill them in on the details. I tell them, “It’s really Jackie’s fault that I got fucked so good; since he was being so aggressive with his dance partner, I got jealous and grabbed Steven’s ass.” Then I continued with, “This led to Steven grabbing mine beneath my skirt, and then stroking my cock and balls under my panties.” Jackie interrupted with, “Forget about the dance floor, tell us what happened in the...

Crossdressing
4 years ago
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An Introduction to Crossdressing Pt 4

In Part 3, Jackie and I had our way with each other for the first time and then headed to the shower to ‘clean up’. As I was removing my feminine attributes - the wig, makeup and lingerie - it occurred to me that even without those items I still felt rather girly. Previously whenever I would change out of my lingerie back into my man clothes, my attitude would change as well. Maybe my attitude hadn’t changed this time since I had dressed all the way and given myself completely as a woman....

Crossdressing
2 years ago
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Bookstore Crossdressing

It was at an adult book store in the north part of Denver. I had just gotten a nice pair of stockings with the latex band to keep them up and I had a hot pair of heels that brought out the tramp in me. I always entered the store with the heels tucked in my jacket, so they weren’t that noticeable. Once I was inside a booth, the heels came out the clothes came off and the slut came out. The hallway was empty where the booths were so I ducked into the booth that had a video of a luscious...

Crossdressing
2 years ago
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Married Crossdressing Fun Ch 3

“Mikki?” Caz asked. “Yeah, babe?” “I’ve been thinking...” “Always a dangerous thing,” I said, cheekily. “Yeah, whatever. Seriously, I’ve been thinking about what happens next.” “What do you mean, what happens next?” “Well, you are really beautiful but I was thinking of stepping it up a notch.” My wife Caz is the most beautiful woman I know. I love her with all my heart. She is sexually voracious. We played a little game a while ago. She saw how turned on I got when she treated me like a bitch...

Crossdressing
2 years ago
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Married Crossdressing Fun Ch 2

Caz and I had been living in our new home for about two months. Our life was wonderful. We loved each other more deeply every day. Caz enjoyed her new job and she was really good at it. She was a beautiful, sexy woman and in the field of international finance surrounded by mainly middle-aged men, she had the advantage and wasn’t ashamed to use it to further her cause. Her company was making record profits and she had already had a pay rise. She was also in line to get a huge bonus at the end of...

Crossdressing
3 years ago
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Married Crossdressing Fun Ch 1

I was lying on our marital bed blindfolded, with my hands cuffed to the bedhead, wearing a pair of sheer black knickers. I was waiting for my beautiful wife to come home from her date with Antwan, her big black lover. I thought back to how this all began. Caz and I met when we were both studying at the State University. I was doing an MBA having completed my degree in Business. She was finishing her degree in International Finance. She was the most beautiful woman I had seen and I thought I had...

Crossdressing

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