A Day, Interrupted free porn video

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A free day. Are there any better words than those three to the ears of a closet crossdresser? For Sam Simons, the answer was no. A free day to take his time with his make up. A free day to pick out the perfect outfit, wear it, take it off and pick out three more that are just as good. A free day to relax, chill out and take a break from himself. This is what stretched out far in front of him. Hours of uninterrupted crossdressing. A free day. Sam woke up earlier than he usually ever would on a Saturday. He had planned to meet his oldest friend, Donny, today but they had put there plans on hold till Sunday. They had no real plans anyway. Just the kind of vague ideas friends comes up with for a lazy Saturday. Sam's new plans were much more appealing to him. He first headed to the kitchen. As giddy as he was about the prospect of a whole day dressed up he knew breakfast was still important. Something light, he reasoned. Something a lady concerned about her figure might eat. Yogurt and a banana. Perfect. Sam had never known why he had begun crossdressing. As far as he could tell very few did. He had heard stories of domineering girlfriends forcing it upon their men, of discovering a taste for it after a halloween party, of women stuck in the wrong body. All of these seemed alien to him. He just started because he did. That was the only reasoning he could ever come up with, as unsatisfying as it was to him. While laying out his make up for the day, Sam felt the familiar relaxation that came with dressing. For him crossdressing was stress relief. A chance to throw off all the worries that came with his job, his love life (or lack thereof) and his social life. It was a chance to be a new person for even a short while. It was the chance to be someone confident, sexy and free. Sam was none of these. He figured a lot of crossdressers felt exactly the same way. As he applied a thin layer of foundation to his face and shaped his brows, something he had been doing for years now, his mannerisms shifted ever so slightly. His knee cocked as he leant over the bathroom sink, straining to push every last hair on his brow into place. He daintily lifted the eyeshadow brush and stroked it across his face, expertly blending light and dark tones into a smokey eye look. Sam knew he wasn't transgender. He knew he wasn't a girl trapped in a boys body. Any time he tried to spend more than a day dressed he found himself unable to do it. He was a boy and after a while he always needed to be a boy again. But he had recognised the change in the way he held himself as a girl. He was aware of the slight swing in his hips when he walked, of the way he held his legs together when sitting, of the pout he found himself currrently displaying as he slid the slick, lip gloss across it. He knew he wasn't transgender, but he knew when dressed he felt like a woman. Sam looked over at the outfits he had set out for himself. He stood there, hands on hips, wearing just a bra that he could only pretend to fill. He had become a dab hand in the art of padding. All three of the outfits would do. One black, one blue, one gold and sequined. They all complimented the heavy, dark make up he had created. They were all short, tight dresses. His deliberation didn't take long. He was a sucker for a little black dress. Just the kind he liked, miles away from the bland, functional clothing he wore as a boy. Sam had always dressed somewhat provocatively. He loved the slight constriction of a tight dress, and the way his legs looked in high heels and short skirts. He figured it was all part of becoming that other person. The slight tap of the heels on tiled flooring as Sam entered the kitchen made him smile. He loved that sound. He loved that he was making that sound. He brushed a long strand of blonde hair from his wig off his face as he bent down to check the fridge. It was lunch time. Time for food. Something light. A chicken sandwich. Perfect. Sam grabbed the ingridients and layed them out across the counter. He looked out across the New York street from his window. When he had first moved to the apartment Sam had made an effort to close all the curtains so as not to be seen. He was terrified of being found out. Of having this relaxing and personal past time exposed and stripped away. That was over a year ago now. By this point he had stopped caring. He knew on some level just how good he looked. He had pictures, videos, and comments from people online confirming it. He knew that anyone looking in through the window wouldn't see a boy in a dress. Just a girl. A girl with too much make up and wearing a very short dress for a saturday afternoon, but a girl all the same. After lunch the camera came out. Sam couldn't pin point exactly when he had begun to take pictures of himself but he knew it was one of the more fun aspects of dressing up. The chance to pose and pout and achieve a look that was even more sexy and confident appealed to him greatly. He also knew he loved to be looked at. To be seen as a sexy confident woman. He guessed in some ways it was a chance to push this side of himself out into the world, without having to risk actually exposing himself. It was safe. Despite this he had often thought about leaving the building dressed. The idea of being outside in heels and a dress and make up was exciting and terrifying in equal measures. The furthest Sam had manged was opening his front door and stepping out into the apartment block hallway. The slamming of a neighbours front door just a floor above him had sent him scampering back inside. He had not attempted it since. Still, there was a part of him that wondered. Sam checked the camera, scrolling through picture after picture of himself. He looked good. He knew he did. No one could have guessed the girl throwing her hair back, biting her lip and standing prone on all fours in these pictures was a boy. Sam smiled. The loud knock at the door wiped the smile straight from his face. He froze. The knock rang out again louder than before. Sam edged slowly towards the hallway, taking care to not make a sound. He held the camera close to his chest. The door banged again. From the other side a deep voice rang out. "Sir!?! Mr Sam Simons!?! Can you please let us in!" "Who is..." Sam caught himself before he could finish. He cringed and held his head in his free hand. What had he done? Not only had he let whoever was out there know he was inside the apartment but he had answered in a voice that was definitely a mans voice. "Mr Simons!?! Is that you? This is the NYPD!" "Fuck," Sam whispered to himself. The police? Why were the police here? He frantically wracked his brains to think of anything it could be. He kept a little weed in the drawer in his wardrobe. He had a small unpaid parking fine. A stupid, irrational part of his brain even questioned whether crossdressing was illegal. Another loud knock at the door brought him round, "Sorry. What is it? What do you want?" "Can you just open the door, Sir!?!" "What do you want?" "We have reason to suspect you are in possesion of a large amount of illegal substances! We have been authorised to search this flat!" A large amount? He had one small bag, enough for two spliffs at most. "I think you've made a mis..." The voice on the other side of the door interrupted, louder and harsher than before. "If you do not open this door we will be forced to break it down!" "What!?!" "We have been authorised to search this apartment! We have been authorised to break down this door if necessary, Mr Simons!" "What? No, please d..." "I wil give you to the count of ten to comply! If you do not open the door within this count I will break this door down! Ten!" Sam dropped the camera in shock. What could he do? He was stood there in his shortest dress, with full make up and a wig on. The officer knew he was a man. "Nine!" If he opened that door he would be exposed. "Eight!" If he didn't he would be exposed anyway. "Seven!" He didn't even have that much weed. Why was this happening? "Six!" Why didn't he just leave the apartment today? Why did he stay in? Why did he crossdress today of all days? "Five!" Sam tried to catch himself. He forced his breathing to slow but his heart and his mind were racing. Maybe the officer wouldn't care. He was NYPD. He has probably seen a lot weirder things than a shy crossdresser. "Four!" He's probably had training in what to do in this situation. He probably has to be mindful of other people. It's part of his job. "Three, Mr Simons!" There wasn't a large amount of drugs anyway. The officer would come in, see that there was no issue and Sam would get a slap on the wrist. He'd show the officer where the weed was specifically. He would be in and out in ten minutes. "TWO!" What other choices did he have? "ONE!! "WAIT! I'll open the door!" Sam braced himself. Perhaps he had been too late. He fully expected the door to fly off it's hinges as NYPD stormed in. It never happened. "Quickly, Mr Simons!" The voice was impatient and angry. Sam took a deep breath in. His heart was pumping so hard he could hear it in his ears as he approached the latch. He cursed himself for not renting an apartment with a looking hole. The sound of the chain was as loud as it had ever been as he pulled it across and let it swing down from the door. Part of Sam wanted to run. To go and hide in the bathroom. To rip off the wig and wipe away all the make up and hide. It took a lot for him to ignore this part of himself. Instead he reached up for the handle. With his free hand he smoothed out his wig and his dress. He didn't know why. The door slowly creaked open. The hallway was empty. Sam stood there bewildered. Staring back at him was nothing but the blank wallpapered drywall across the hallway. The only sound was the heart beating inside Sam's chest. He shifted nervously in his heels. "GOTCHA!" Sam slipped back from shock, his tall heels catching on the wooden floorboards. He fell hard on his backside, his short skirt riding up to reveal his lacy, black underwear undernath sheer pantyhose. He hit his head on the wall behind him, sending his blonde wig off at a strange angle. He sat there in stunned silence. It felt like he was going to have a heart attack. Through the blonde haze across his eyes he could just about make out Donny, his oldest friend stood in the doorway, his smug grin slowly shifting to that of utter horror at what was in front of him. "What the..." he began to say. "Fuck," whispered Sam.

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Walking toward the house; reflecting. ..., I think back to the phone call I received two hours ago from Jimmy. Jimmy is my nephew. It seems Jimmy is at a party which has gone wild. Jimmy told me that there were a couple of girls there, one of whom had been at Jessica’ wedding; who were hiding. He mentioned three black dudes who were terrorizing the party and he was; ‘afraid for his ass’; as he worded it. I gave Willie a call as Sally is still in China. I told Willie I’d pick him up with the...

2 years ago
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Thursday1

... After yesterdays debacle I wasn’t looking forward to meeting a Congressman’s wife, Dania I think her name is. After calling J & J‘s security to get ‘Jackie’ a 24 hour security detail I received a couple of phone calls. Willie called to find out what the score was; and, to my surprise, Gino called to check up on me. The call from Gino has me meeting this woman tonight. I guess I will have to pay for Jackie’s security personally. There is a rally tonight at Janet’s Hotel. I’m to meet this...

3 years ago
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Wednesday1

... Memo: Bob, we have a situation in accounting. Leonard, a long time employee has been observed looking at Kiddie porn at work. Signed: ... Wallace, Chief of security. Sitting back in my chair I look out the window. Leonard yet, what the fuck was he thinking. Jeez, he has two children of his own for fuck sake. Give them a bath; put them to bed; anything but porn at work. Know I have to do something. I phone security Chief Wallace. “Wallace ..., Bob here.”... “Fine Wallace, and...

2 years ago
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Tuesday0

Three months after Jessica's wedding Jess came to see me. We chatted in the office for an hour or so, at the end of which Jess invited me over for supper the following Tuesday night. The rest of the day was the usual. I went to a ball game in the evening sitting in a box seat. Some of Gino's people were on hand. Gino showed late and we had a few. I enjoyed a good night. Tuesday evening I show at Jessica's new house for dinner. I parked in the garage as per Jess's instructions. I...

4 years ago
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Monday2

... 12:01am ... “Ring ...,Ring ..., RING..., RING...,” “Hello.”..., “Bob Smithe here." “Mr Smithe, this is Richard's from the fire department. There has been an accident at the Halpern Construction site ...,..., a fire was accidentally set on the roof and two men were injured sir." " Who.? " ... " A security man named Monty sir, we have no last name. ...,and the site Super. A Mitch, or Mr. Mitch sir, again our information is preliminary. "...

3 years ago
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Sunnydayzwithu

He was looking forward to going to Verna. It could only be for a limited time but there would be other visits. Even traveling a considerable distance, he thought it well worth the time, there was no sacrifice. Eventually, Verna started to come into view, he slowed his approach and savoured the anticipation, smiling at the butterfly sensation in his stomach. With all the thoughts, feelings and emotions during his advance he neglected to observe one very crucial thing. A mistake was made, a major...

3 years ago
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Mondays Child

***Monday’s Child is fair of face, Tuesday’s Child is full of grace, Wednesday’s Child is full of woe, Thursday’s Child has far to go, Friday’s Child is loving and giving, Saturday’s Child works hard for a living but the Child born on the Sabbath Day is fair and wise and good and gay.*** Analisa Soto didn’t own a mirror. Not after the accident. She couldn’t bear to look at herself. Not just because she had single-handedly killed her entire family, but also because the beauty that she’d had had...

3 years ago
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FundayFriday

It’s a Friday morning — I start the day by getting up at 7am for my 8am class. Before getting out of bed, I wrap myself around you, run my hand through your hair and shower you with gentle kisses. Innocent at first, but I quickly make my way down your warm body that is entangled in heavy blankets, first your neck and collarbone, then slowly trailing down your abs, all the while my hands are grabbing your ass. You’re still in sleep mode and with your eyes still closed, you moan and shift your...

4 years ago
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Daystar Swimming

The sun slowly sinks below the horizon as we sit in silence on the isolated beach. Late October, a beautiful time for the shore. True companions of the sea come to the sandy dunes at this time of year to listen to the Divine power whisper truth across the foam that settles at your toes. Day stars glitter and captivate you to open your soul to all that is to be in this universe. Only those who are of the sea come here and listen. There is no need for us to talk. We hear each other clearly,...

4 years ago
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Holidaying with a school friend Part 1

It was the last day of the summer term and I was full of the holiday spirit. In less than a weeks time my parents and I were off to the Caribbean for a two-week break. For the last few days I have been talking about nothing else. Friends in my form must have been getting fed up with me, I am sure Cora was and told me as much. “Anna you might think the holiday sounds great, but you could have as much fun on an English beach.” Jealous or what? The bombshell was dropped during one of our rare...

2 years ago
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Holidaying with Miss Greenslade

I woke up the next morning and wondered how soon it should be before I called Kate. After last night I was certainly keen to meet her again, but didnt want to seem desperate or needy. Contemplating on my stupid dilemma I rolled over to look at the clock. Shit, it was 11 already. I got up and pulled a T-shirt on as I left my room. My sister Jill came out of the bathroom, brushing her blond hair and wearing nothing but a towel around her athletic body.      ‘I wouldnt go down dressed like that...

4 years ago
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Holidaying with a school friend Part 2

I took my shower earlier the next morning. I usually do not mind showering with Cora, but today was different. I did not want her, to see the welts on my bottom. Unfortunately, Cora had also decided to take an early shower. “Morning, Anna” “What! Oh good morning Cora” “Anna, your bottom, was it Alex?” “Yes” “Did he fuck you?” “Yes,” “Were you?” “Yes, he was the first boy I had sex with” “Poor Anna” “Cora, has he done it to you?” “The spankings and canings yes, sex no” “Sure?” ...

4 years ago
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MILFday At The Spa

Background: After winning a bet with a demon in a dream, you are able to mind control whoever you please. You are at a spa relaxing in the waiting room because your car is getting fixed down the street. While staring into the hallway, you see a familiar figure walk into a room. You follow in and see....

MILF
3 years ago
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Gameday Slut for BBC

This past weekend i got a call from one of my fuck buddys ,Jamal. He was having some friends over to watch the NBA Playoffs and asked if i would dress up and serve them during the game and be their fuck slut for the night. So of course i agreed to help. I had no idea who the friends were or how many friends would be there. I quickly started to the closet to decide what i would wear. Black see through lace night gown, heels, and black thigh high stockings was the choice. I would go as a blonde,...

3 years ago
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Manday Mania Part Four

When Ned woke me up, I did not know how long I had actually been asleep but I immediately got scared that the video of Tom and me fucking was still on the video. When I looked at the video I was relieved to see that I had been asleep for almost three hours and the video machine had automatically shut itself down due to no more input. Ned had already started to go upstairs so I got up, retrieved the flash drive and put it in my pocket. I then turned off the lights and followed Ned up to our...

4 years ago
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Yestrerday at the porn theater

As a fan of gloryholes and porntheaters, I'm a more or less regular guest at the local porntheater. It's a relatively small theater but it's safe, it's good enough and there are always some horny bitches and cock hungry guys present to fulfill anyones' needs.... So yesterday was one of those days. After a really shitty day at work, I wanted to relax and enjoy a good porn movie, preferably in good company, because as a single guy, sex doesn't cum easy these days.... When I entered the...

4 years ago
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Manday Mania Part 3

. I turned around but was shocked to find it was my husband’s friend, Tom, and not Ned. (I thought Ned had awakened and saw me and wanted to fuck. I was surprised to see Tom and I backed away a little.) He said “relax, I heard what went on here today and decided to come over check to see if you are ok. I also came over because I have wanted to fuck you since the first day I saw you but I didn’t want to hurt Ken. We have been friends since we were k**s but when I heard what happened today with...

4 years ago
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Manday Mania Part 2

That was when I looked up at the TV and saw that there was a different video on and not the one with the two guys and the one girl and her “husband”. I also noticed that the video had a different look to it. However, it showed one woman, sandwiched between two guys but it was from the side and only showed them from the shoulders down. She looked a little familiar but I figured that at my current state of mind after the pot and wine and intense sexual activity I was just imagining things....

2 years ago
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Gameday Mania Part 1

I remember this as if it happened yesterday. In fact, whenever I think about it I get still get so hot that if I’m fucking my husband I start to orgasm almost as soon as his cock slides into me. If I’m alone and at work I have to go to the ladies room, go into a stall, and masturbate until I cum. At home I will masturbate, use my vibrator or fuck myself with my dildo until I cum. That’s how good that day was. I am not a big football fan but my husband, Ned, is. He and some of his friends will...

3 years ago
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Dayani is a horny bitch

Dayani was her name, she had worked with Luxmi for a quite a while now and the two got on so well.Luxmi had liked Dayni since they started work together; she was about 4½ feet tall, with shoulder length black hair and a slim curvaceous body that were topped with a good-sized pair of 36C breasts.Both were 23 however Luxmi had long black tint hair and about the same sized breasts as her friend and workmate.“Hi Luxmi nice day isn’t it” a chirpy Dayani said as Luxmi came into the shop where they...

4 years ago
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Hoiday in France Wifes Story

She and her brother had after Madges' intervention and instruction been fucking since the weekend her parents when to a wedding leaving Madge in charge. Madge moved out soon after and left the k**s to it, my wife's new favourite thing and a new way of draining her brother balls of cum. The only disappointment was that she rarely got to taste his cum pure as it got mixed up with her pussy juice. Anyway, the annual holiday to France was planned and the weeks before gave the k**s plenty of chances...

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