Caught Crossdressing By My Neighbor Down Stairs free porn video

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My story is a true event that happened when i was in my early thirty's. I was renting a up stairs apartment, My down stairs neighbor Tom was a ruggedly handsome guy in his mid forty's. I work the over night shift so my sleep habits are different which leads to my encounter with Tom. Tom and i became good friends we would hang out together when we were not working. Tom would borrow things from me from time to time. I had a key made up for Tom so if he needed to borrow any thing and i was either sleeping or not there Tom could let himself in get what he needed and just leave me a note telling me he had stopped by. One day after work i was feeling very horny so i got dressed in my favorite lingerie. This consisted of a pink satin bra and pantie set,white garter belt and white thigh high stockings. I then poured my self a drink and put in my favorite tv/ts porno dvd. After i worked my self up to the point of a powerful climax i drifted off to sleep. The next thing i knew there was Tom standing over me smiling from ear to ear i was mortified . I started sobbing because i figured our friend ship was over . Tom sat down on the couch next to me he gently started to wipe my tears away. Tom then pulled me up to a seated position and slide right next to me. Tom told me he always thought that i acted more feminine than most guys he knew but never would of guessed that i liked to also dress as a woman. Tom then out of the blue cupped my face and kissed me. I was shocked and pulled back. Jamie did you not expect me to kiss you. I told Tom that him kissing me was fine but i did not figure he would seeing that he liked other woman not some guy dressed as a woman. Tom then said you look so damn sexy dressed like that i could not help but to kiss you he then kissed me again and this time i melted in his arms. Our mouths locked together his tongue was giving me a deep french kiss. Tom then asked me if i would go on a date with him tomorrow night i was stunned do you think i could pass as a female? Tom just smiled and said you will be fine. Tom said he would buy me something sexy to wear all i needed to do is give him my sizes. I was awakened by a knock on my door it was a delivery guy he had flowers for me they were incredible. Tom stopped by later and i greeted him with the biggest hug and deepest kiss he just said wow. Tom had me model what he had picked out for me a bright red dress that was about knee length and matching flats. Tom said i should wear what i was wearing the day he discovered my secret, After doing my make up i decided since i was wearing a red dress i would become a redhead the wig was the final touch. I looked at my self in the mirror and i did look like a female no doubt. Tom picked me up at 7:00 he said you look gorgeous on the way to the restaurant he could not keep his one hand from running up my leg to my thigh and almost touching my pantie clad crotch i just smiled i was so hot. At the restaurant Tom ordered for me and bought a bottle of wine as we waited for the food Tom had managed to work my dress up to the point where he could clearly see my panties . Tom then had me raise up a little with one final tug my dress now was bunched up around my waist my panties clearly visible to Tom. Our food came the server i am sure got an eye full. She just said i hope you enjoy your selves here. We left the restaurant both hot and bothered. Tom said we were going for a drive i knew better as soon as we left the city he found the nearest secluded place to park Tom pulled a blanket from the trunk we sat on it finishing the wine from the restaurant then we started making out like some teenagers. Tom had me stripped down to just my bra and panties i had Tom completely naked i took his throbbing member in my mouth and gave him the best oral sex that he ever had his cock was 7 inches and rather thick. I was going down on him like a lust starved girl. Tom quickly started to shake and filled my mouth with his hot cum some of it leaking out of the corners of my mouth. Tom and i just giggled i just gave my neighbor his best blow job ever. As we dressed he told me he wanted to fuck my sweet tight ass i just smiled because i wanted it to. The drive back was short and all Tom talked about was how it was his turn to please me. When reached my place he told me to put on my favorite night gown and nothing else. I looked great in my see through baby doll night gown Tom was more than happy his cock was hard as steel Tom had me get on the bed on all fours Tom started with some lube first inserting one finger then two into my eager ass i wiggled it back and forth to turn him on further. Tom then put me on my back and said that it was now my turn to be pleasured Tom now guided his hard cock into my waiting ass it hurt for a little bit but my ass quickly got used to his size. We developed a rhythm and our love making seemed to last forever until i heard Tom groan he quickly pulled out of me and shot his wad all over me including giving me a facial. I was in heaven we then fell a sleep in each others arms like lovers do.

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“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
4 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
2 years ago
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An Introduction to Crossdressing Pt 3

As I was following Jackie to the hotel I couldn’t stop looking in the rear view mirror at what was a complete transformation in my mind. I kept doing that thing where you look away and then back hoping to catch your reflection not keeping up with you because you are sure it is not you. It is probably a good thing that there were not very many cars on the road since I wasn’t paying any attention to it while I was admiring myself. I did see Jackie’s turn signal and brake lights just in time to...

Crossdressing
2 years ago
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An Introduction to Crossdressing Pt 2

So as Jacky was going through his story about how we ended up in this shop, I started to look around. I found that my initial belief that the shop was just a hair dresser was completely wrong. The shop was split in two, long ways, with the left side having about four stations for regular hair work, two stations for nails and a couple of closed rooms for massages, waxing and tanning. The right side had several racks of all sorts of women’s clothes including lingerie, dresses, shoes, wigs and...

Crossdressing
3 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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A Crossdressing Story

***A crossdressing story***(All characters are fictitious...maybe…!)I had been dressing for a number of months when this adventure occurred. While I felt that I was learning the basics of makeup and dressing, I needed some expert advice and so I placed an AD in a local TV/TS newspaper for an understanding woman to help me with my feminine side. Little did I know what an erotic journey this would take me on! I got a number of good responses, but the best came from a woman named Debbi. Her...

2 years ago
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Steve the Crossdressing Cat Lover

My boyfriend, Steve, has a lot of cats. I can't tell you exactly how many because the little critters come and go out the pet door and scatter as their furry little paws please.Steve lives on a farm. Well, it's kind of a farm. I mean, he has a lot of land, but he doesn't exactly grow anything on it except cats from what I've seen. And he has a barn, too. You'd think with all that land Steve has that he'd keep a couple of horses to ride but no. The barn is filled with cats that curl up and sleep...

Crossdressing
2 years ago
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Mother and Crossdressing Son Fantasy

Mother and Crossdressing Son FantasyThe story is about how my passion for wearing women's lingerie helped me to establish a more intimate relationship with my mother.I'm a 42-year-old man and I still live at home with my mother. My Father passed away 20 years ago. We live in a suburban bungalow and I have a nice little apartment in the basement. It's not as private as I would like. That's important because four years ago after discovering a number of chat sites where men present themselves in...

4 years ago
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Crossdressing at the cinema

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...

3 years ago
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Wifes crossdressing fantasy Part 3

This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental. My Wife's Cross dressing Fantasy 3 Then my wife looked at me and said “Happy anniversary darling.” How did she know the effect this experience would have on me. I was changed forever. It was such a wonderful experience. She deserved that I come up with something just as exciting for her, but what? I thought and thought, but I couldn't think of anything to equal what she did for me on our anniversary....

Crossdressing
4 years ago
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Wifes Crossdressing Fantasy Part 2

This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental. Since my wife shared her fantasy with me and made me her bitch, our love life has changed. Now I always have something cute and satiny on, whether it is panties under my boy's clothes, or a silk nighty at night in bed. I love being my wife's bitch and I can never go back to who I was before. When our anniversary came around, a month or so after my initiation to dressing up, my wife announced to me...

Crossdressing
3 years ago
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Wifes Crossdressing Fantasy

This is a work of fiction. Any resemblance to persons or incidents is coincidental. My adventure began while I was a senior in high school. My mother took me to the dentist. It was late afternoon and shortly after I was called into the examination room the receptionist and assistant went home. The dentist then closed the door of the room we were in. He walked over to me and started making small talk... I guess to make me feel at ease. We talked about many things. He told me I was cute and that...

Crossdressing

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