Brittany Moore's First Time free porn video

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I had been crossdressing since I was 13 years old and had been making online purchases of everything from wigs and makeup to boots and lingerie. I always had the desire to be with a man as a sluttly girl. I decided that it was time. It was when I was 29 years old and was weighing a nice 180 lbs and 6'2. I live alone and I decided to dress up in my favorite black thigh his stockings, my lacey garter belt, my thong black panties and a sexy sheer black bra. I put in my silicone implants. I modeled for myself and felt my ample tits as I faced the mirror. It was time for me to take out the makeup. I sat at my makeshift vanity and began to apply my foundation to my face. You could not see any part of facial hair as I put it on thick. I then proceeded to put on my black Maybelline eyeliner. Drawing a perfectly done line around my eyes. I proceeded to take out my extra length black mascara and extended my lashes very well. I completed my eye makeup by using some subtle eye shadow to complete the job. I then moved to my lips as I applied long lasting wet shine purple lipstick on my lips. I puckered my lips to taste the awesome taste of the sexy and slutty color. I then applied another coat to insure it did not come off easily. I put on a long black wig with straight hair, which rested right below my shoulders. I crossed my legs like a lady and proceeded to light up a Virginia Slims 120 cigarette. I sat there taking a sexy drag satisfying my smoking fetish as well as my crossdressing fetish. When I finished smoking it I went to my closet and took out my favorite black leather skirt. It was tight and sexy and really showed the shape of my ass. I then put on a tight v-neck purple blouse. My 36 c breasts were very formidable as I was wearing it. My nipples showed through the tight blouse. I then put on my black knee-high boots and zipped up the sides. I was now feeling like a true woman. A woman with her clitty getting hard. A woman who desired a man. I poured myself a glass of wine and lit up another cigarette as I sat on my couch. Legs crossed again. I turned on my laptop and went online. I had been talking man to an older man from my area for some time now and he was online as well. I began talking to him again and told him that I was dressed and a little horny. We had spoken for about 30 more min before I decided to invite this so called "CD admirer" over to my home. After the arrangements were made I dimmed the light in my home and lit a great many candles. I knew it would take him about 10 minutes to get over to my place. I paced around smoking my cigarette thinking about how I would be during this experience. He had told me this was an unexplored fantasy of his. He insisted he was not gay but he thought he would enjoy the company of a crossdresser. I finally began to relax and sat on my couch. 5 minutes later a knock was at the door and I simply told him to come in, in my feminine voice. He walked and rounded the corner and same me. I smile went over his face. He was in his late 30's and was wearing jeans sand a white button down shirt. He was well built and attractive man. He was glancing over at (in my opinion) a sexy, slutty looking girl sitting on the couch with a glass of red wine in front of her seductively holding a long cigarette in one hand as her crossed legs revealed the tops of her silky thigh his and the garters which supported them... I walked over to him and he introduced himself and Jim as I introduced myself as Brittany. I invited him to sit with me and offered him a glass of wine. He accepted. We began to talk as he expressed his nervousness as did I. After a couple of minutes the talk shifted as he began to be very complimentary of outfit and look. I kept saying "thank you" in my feminine voice and reached with my left hand to touch his thigh. He moved closer to me and began to move in to give me my first kiss as a woman. His lips touched my purple lips and his tongue slowly entered into my willing mouth. The soft and sensual kiss continued as he reached to grab my tits. He pulled away for a second to say, "Brittany you are so fucking hot." I responded to this by moving my tongue back into his mouth. This time the kissing was more intense. I reached my hand down to his jeans and felt his huge cock in his jeans. Jim's breathing became heavier. I got on my knees in front of him and he pulled off my blouse to reveal my pretty tits through my sheer bra. I unbuttoned his shirt and began to suck on his nipples. Light biting of them made him squirm in excitement. As I pulled away he asked me to hold on as he took off his jeans. I reapplied my lipstick. Sharing my fetish, he asked if I could light up one of my Virginia slims 120's. I obliged and began to talk dirty about his cock, saying how I wanted it in my mouth so bad and how I wanted to taste his cum. He obliged. I took a sexy drag and exhaled and then moved into his cock and put it in my mouth. Kissing the head followed by a lick up the shaft. I took it all in my mouth and began to give him a hot blow job. He was calling me a whore and slut as I sucked it and held my long cigarette, taking breaks to take a drag. After about 10 minutes he asked my to get up and turn around. I obliged and he pulled down my skirt. He began to pull aside my thong and lick my man clit. As he licked it he spanked my ass asking me how I liked it. Of course I loved it. This went on for a short time until asked me to lay down on my back. I did and he pulled my legs back and began to fuck me. He again asked me to hold/smoke a cigarette during this as well. He fucked my pussy good even though it did hurt, but in a good way. I began talking dirty back to him asking him to make me his cum slut and to fuck me like the whore I am. He obliged. As he neared orgasm he pulled out to cum on my face and tits. He did so so well. It was awesome. My cum covered tits and face loved every second of it. Since I had not concentrated on handling my own orgasm he did me a favor at my request. He took my vibrator and used it in my pussy ass as I stroked my cock. I came shortly. After this I laid there as he gave me a cigarette and lit it for me. He also opened up the lipstick tube and as I laid there he reapplied my lipstick. Shortly after we talked some more and he left. I had completed the first erotic session as a slut. I never had anything like it. Since this time I have only been with Jim and meet with him a couple times a month. We have done other sexy things including his dressing with me, but that's another story. I will always remember that night and believe it was the most erotic night of my life. Brittany Moore

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2 years ago
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1 year ago
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1 year ago
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We lay on the bed together for two hours, even napped a little. We woke up and talked. Britt said, "Chad, I feel guilty. I'm sad that Amelia is dead but not like I think I should be. I'm just numb ... My life is so different now from a month ago. You're the only constant. I've done nothing to deserve your parents' kindness and love. So many people have been so kind to us and said and done nice things to us and for us. I feel like I'm in a dream. That's why I want to hold you." I...

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Brittany Stevens Office Slut Part 2

Mr Jones, the President of Sharpfield and Jones, smirked as he leaned back in his black, leather chair armchair and took a sip of the coffee his assistant had brought him. There was nothing better than a coffee to perk him up first thing in the morning. Well, almost nothing. He took another sip and glanced down at his assistant as she bobbed and slurped on his cock with those big, pink, glossy lips of hers. He was amazed at the skill and finesse she showed as she brought her lips up and down...

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Brittany and ChadChapter 12

That afternoon was back to pretty much normal. Mom drove up as we were getting out of my car. She was usually home just before, just as, or just after I arrived. Britt finished handing me our books. She put her arm around my waist and we followed Mom inside. Thursday, we were told to meet them at the courthouse. Surprisingly, both of Britt's parents had acknowledged the petition and consented to Mom and Dad as guardians of Britt. We went into the court. Dad went over the original petition,...

2 years ago
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Brittany and ChadChapter 3

That's what happened. I had thought to go but Dad said that I was to stay with Mom. After everyone left, Mom said, "This is going to be different for you. Can you handle your girl friend living in the same house? You know the rules won't change. If anything, they will be more strictly applied." "Mom, that's not fair. We haven't done anything wrong here. Why should we be punished?" "You won't be punished. You will be exposed to the young lady a lot more than you ever thought...

2 years ago
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Brittany and ChadChapter 4

Finally, Britt kissed me hard and said, "Chad, thank you for what you have done. I've never been sure what would happen to me. Lately without you, I don't think it would have been good. I want all of this to work out especially you and me." I gave her a long, gentle squeeze that made her purr in my arms as I cupped a breast and thumbed the nipple through the dress and her bra. I said, "I want things to work out, too. You are a beautiful, nice person. You should be happy." She turned...

3 years ago
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Brittany and ChadChapter 21

As we went upstairs and into my room, Britt asked, "How old is Mitch anyway?" I answered, "He's the same age as Mom and Dad. That would make him about forty or forty-one." "Okay, that gives me a window of ages." "Oh, okay. You're serious about this aren't you?" "As a heartbeat. He's a good man and deserves to be happy. He hasn't been looking. Mom and Dad have separately admitted that he hasn't tried to date." I said, "I guess he's still carrying a torch for Mom and now...

3 years ago
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Brittany and ChadChapter 7

Dad looked over with a slight air of disapproval. Britt saw his face and said, “I don’t care if it’s a little over the rules. This is special. I’m thinking of jumping you and Mom, too.” He grinned happily. “Well, come on!” He held his arms out. Britt jumped up and jumped in his lap and kissed his face all over. Then, she jumped over to Mom messing up her papers doing the same thing. They both looked bemused when she rose. She and I helped pick up and straighten Mom’s papers. Supper was a...

2 years ago
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Brittany Stevens Office Slut Part 1

Brittany Stevens sat down for breakfast and opened the local paper, flicking the pages to the Staff Wanted section. Brittany had not had a job for almost half a year now, and money was starting to run dry. Sure, her parents had helped her with her rent, her car, and pretty much everything else, but they were threatening to cut her off so she decided it was time to find herself some work. Brittany bit into her toast as her eyes grazed down the various want ads. She licked her lips, still tasting...

3 years ago
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Brittany in the Dressing Room

She didn't understand what she was doing here, in JC Penny on a Wednesday afternoon. Her long distance fucktoy, Jordan lived on the east coast. She had, of course, sent him dirty pictures from dressing rooms while she shopped before; usually Victoria Secret dressing rooms. And she had even played with herself in a dressing room while he watched via Facetime. But every one of those times was in a store of her choosing; he had never before specified where she should go. What the fuck was going...

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1 year ago
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Brittany part 4

When it became apparent to Brittany that I loved her long, swollen clit, things got a little spicier than I had anticipated. She was no longer shy about getting her needs filled. She flirted more openly, instead of getting dressed before leaving the shower, she'd go from the shower to her room wrapped only in a towel, whether Lisa was home or not. I'd drive her to school ocassionally and get a hand job along the way, or she'd let me finger fuck her. On one of these trips to school, she was...

2 years ago
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Brittany and Chad Book 2Chapter 3

A few minutes later, Doctor Martin came in and made me sit on the bed. He poked and prodded. He looked into my eyes with a bright light and watched my pupils react. Finally, he said, "You're good. Take care of the head. No active things for a few more days. Keep the dressing clean. Brittany, are you going to change it or is Lois?" Britt said, "I will. I know what to do. I helped Nurse Dan clean it and re-bandage it this morning." "Okay, if you get a headache, if you feel dizzy or have...

2 years ago
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Brittany and ChadChapter 26

On that Sunday afternoon, we were at the house. Mitch had a car come pick up Miller and take him to a holding cell. I think he felt he was safer in jail than anywhere else. Mom and Dad insisted that Mitch and Dora stay for supper. Mom said, "We won't keep you late though it appears that all the excitement is over." Dora looked at her and said, "I think Mitch might stir some up with me later." She smiled impishly and Mitch blushed. "Mom, may Chad and I still invite Missus Thornton to...

2 years ago
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Brittany and ChadChapter 22

The phone rang and it was a happy and excited Amanda. She was tearfully happy thanking us all. She said, "My dad wants to talk to Missus Arnold." Mom took the phone that Britt handed to her, and said, "Hello?" We could hear the other end. "Missus Arnold, this is Tim Grogan. I wanted to add my thanks to hers. Mister Baker called and said Brittany and Chad accompanied by Tony called on him this morning and he is lifting the expulsion. That is great news! He also told me that you...

3 years ago
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Brittany and ChadChapter 23

We were prepared to wait supper for Dad and Mitch to arrive. They arrived a few minutes before our normal time to hugs and kisses. Mom said, "You can tell us all about it over supper. I would think you're both hungry." Mitch said, "Lois, I'm always hungry for your cooking." Mom said, "Good. Remember that you are having dinner with us Friday." "I remember and I get to sit between you two." "That's my Uncle Mitch, always wanting to sit next to two pretty ladies." I had learned...

3 years ago
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Brittany and ChadChapter 27

School had just ended and it was time for a wedding! It was going to be a small wedding until Mom and Dad's class started on it. The situation quickly ballooned out of sight with people all over town hearing the public announcement. Pastor Bob had Mitch assign police officers to the church to handle traffic. It was a good idea. Almost the entire police force was going to be there. Everyone Mom knew at school and all of Dad's working friends including the D.A. and all the judges....

2 years ago
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Brittany and ChadChapter 28

We were both working our summer jobs when the suit with Britt's great uncle was resolved. We had dinner with Mitch and Dora included. After dinner, it became a conference. Dad started it. "Brittany, the suit is over and Mitch and I are the new trustees. The bank in Florida has transferred all the money and I verified it today. Lois and I are your guardians and with Mitch and I now as trustees of the trust, I thought we could sit down and determine some goals and directions." Mitch said,...

3 years ago
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Brittany and Chad Book 3Chapter 6

Our house is finished and we have the occupancy permit! Chad and I wander through the rooms in awe. Mom and Dad have been out here with us. Today is Saturday and we have friends coming to paint. Chad and I have picked the paint and put out drop cloths and gathered brushes, trays, and rollers. Our bedroom will be painted the same color as our bedroom at Mom and Dad's. We both love that color and that room has special meaning to us. The most difficult decision was furniture for our bedroom. We...

3 years ago
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Brittanys Morning Walks

Introduction: I had already uploaded a version of this story under a different name. This version, however, is quite a bit longer. Brittany strolled downstairs with the wind on her naked body. She began every day like this. Her shower was on the other side of the kitchen from her bedroom so she would use this as an excuse to expose herself to her family on the trip there and back. She had just turned 14 and this was her last summer before grade 9. Over the last term of her grade 7 year she...

4 years ago
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Brittany was assigned to do a story on the annual fetish fest

My name is Brittany. I am a reporter from Little Rock Arkansas. I am a thin, but curvy brunette. We have a fetish Festival every year and this year I was chosen to interview one of the participants. I have always been interested and intrigued by some of the of the people that go there. It was a hot morning but I wanted to look really nice, so I dressed in a pair of tan stockings and high heels, with a tight fitting blue curve hugging dress. I looked at myself in the mirror and realized...

2 years ago
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Brittany Jones BBC Correspondent

I was so looking forward with great anticipation to my upcoming weekend in Paris.It was the perfect time of year to be outside of the UK in the city of romance and eternal youth. One of my side issues that filled my waking hours with the seeds of guilt was the need to converse in French with native speakers so I might improve my terrible Midland’s accent, to at least the off chance I might be from somewhere more appropriate in the average French person’s thoughts of an ideal environment.I...

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2 years ago
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Brittany and Chad Book 2Chapter 4

We were right to dress. Starting about five minutes after we came downstairs, there was a steady stream of well-wishers coming through the house. While I was talking to Pastor Bob, Britt went into kitchen to fix us a late lunch. She came out with a plate and a glass of tea. Mel had two TV trays. She set them up side by side. Britt placed a plate and a glass of tea for me on one. She went back into the kitchen and got her plate and glass. We talked to Pastor Bob while the crowd went...

2 years ago
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Brittany and Chad Book 2Chapter 7

We returned home and unpacked. We then washed and dressed. We pulled up at Louis just before seven in our new finery. Dad parked and our men handed us out. We were stopping traffic. One man even walked into a car! As we reached the door, Mitch and Dora walked up from the other end of the lot where there had also been a disturbance. I now understood why. Dora was wearing a rose colored mini dress with soft black prints of flowers on it. The top was a halter and had to have built-in bra...

4 years ago
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Brittany and Chad Book 2Chapter 10

We waited and a few minutes later a car pulled into our drive. Mister Anderson came to the door. Dad said, "Come in, Ben. Where's Judy?" "She's waiting in the car." Dad said, "Will you go and bring her in or should I?" Mister Anderson said, "I want my daughter or I will call the police." Dad said, "Why don't I call my friend from before high school, Mitch? He's the chief? You might also remember that I'm the Senior Assistant District Attorney for the circuit. Now, your bluff...

3 years ago
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Brittany and Chad Book 2Chapter 11

[Chad] Thanksgiving was coming fast. We had talked to Mel and Dan and they were driving in over Wednesday night to arrive late. The only question Mom asked was, "One bedroom or two, dear?" Mel's answer was "two." She admitted to Brittany that they were somewhat active but she wasn't even slightly ready to carry it further yet. Dan was talking about marrying over the Christmas holidays. Dan would be able to take the time off albeit without pay. It would be a simple wedding and...

4 years ago
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Brittany and Chad Book 2Chapter 17

In the morning, I eased my way out from between the two females. Mel was topless though I knew that because she had rubbed against me in the night. By the same manner, I knew that she was wearing the requisite panties. I got downstairs and Dad said, "Good morning. Having Mel sneak into your bed must be inhibiting?" He grinned. "It would have been worse about ten minutes earlier." I chuckled. I continued, "It will work out. She is trying to change from what she was expecting to what is...

2 years ago
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Brittany and ChadChapter 8

Dad said, "I've heard about that suit from your mother, Son. She will tell me how it looks when I get home." He smirked. I was curious and looked at the two of them smiling innocently. I was in trouble. It might be good trouble but it was trouble. "Okay, I'm going up to take a shower and shave. Enjoy your golf, Dad. I just wanted to say thanks and see you off." I gave Britt's hand a squeeze and headed upstairs to shower and get ready for the lake. Britt told me later what she and Dad...

2 years ago
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Brittany and ChadChapter 9

We got there in time to share lunch. We ate and then frolicked in the water. The guys kidded me about my suit until they noticed how the girls were looking at me. Everyone loved Britt's suit and the fact that our colors matched perfectly. There were a few ouh's and ah's when Britt told them that my mother helped her pick both suits. Toby had one of his rare moments of saying something right. He held up his cola can and said, "Here's to two beautiful, wonderful people, who make a perfect...

3 years ago
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Brittany and ChadChapter 11

In the morning, it was Monday. I woke early and beat Dad. The coffee had made and I was half way through my cup before he came down still looking tousled. I said, "Are you feeling okay, Dad?" "It was a combination of sun and wine. I'm a little tired yet but, fortunately, it's a light day in the office. I'm going to keep it that way." "You look fine." "Yes, Sir, I'm more used to the sun and didn't have much wine." We heard some noise upstairs. Britt and Mom came down together....

2 years ago
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Brittany and ChadChapter 14

I reached over the bed and gently but firmly pulled her over onto it. I lay on my side and pulled her to face me and gently kissed her lips. She moaned. "How do you always know what to do?" "It's simple. All I think about is pleasing my ladylove. It also brings pleasure to me to bring pleasure to you." "I want you to wear me out." "Ah! We don't have to do that. We have tomorrow night and the night after that and the night after that for as long as we live. Tonight, I want to love...

2 years ago
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Brittany and ChadChapter 17

We went into our room and dressed in shorts and better tops than tee shirts. We pulled on our sneakers. We could meet the world but were dressed to perform light work. We stripped our bed. We brought the sheets and the damp mattress pad down putting all in the washer and starting it. On the way up, Mom said, "Mattress pad, too?" We blushed and she laughed lightly. Once in our room, I said, "What do we work on first?" Britt sat on the bed. "Let's talk about furniture. We could use...

2 years ago
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Brittany and ChadChapter 24

Mom and Dad went shopping while we started another load of clothes. Britt was bent over putting clothes from the washer into the dryer. She was wearing her gym shorts that had wide legs. I could see her slit and pushed my hand into a leg and slid a finger along her slit. She moaned and, to my surprise, was wet! I pulled my cock from my shorts and pushed into her through that open leg. She moaned and said, "I've been wanting that all morning but Mom never gave us enough time. Oh! Do it! I'm...

2 years ago
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Brittany and Chad Book 3Chapter 3

[Chad] It's March and our house is coming out of the ground. The weather has been good and Mister Charles is elated. He wanted to be ahead to give extra time later if it were needed. It's also close to birthday time. Britt was visiting with Grandmother Thornton when Mom and Dad approached me. Dad said, "It's getting close to a birthday. How much are you short?" I blushed. "Does it show that I'm nervous?" They nodded. "I still need four hundred fifty-one dollars and forty-two...

2 years ago
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Brittanys first time

Brittany's view:I had just graduated high school and wanted to take a job at a recording studio. I had always wanted to be in the music business and I thought this would be my way in. The closest studio was in the city, and I'm a small town girl, but they had an internship open and they offered it to me. My first day on the job they showed me around, telling me the ins and outs of the business. I quickly came to the realization of what I was getting myself into. I was the only girl at the...

3 years ago
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Brittany in the Dressing Room

She didn’t understand what she was doing here, in JC Penny on a Wednesday afternoon. Her long distance fucktoy, Jordan lived on the east coast. She had, of course, sent him dirty pictures from dressing rooms while she shopped before, usually Victoria Secret dressing rooms. And she had even played with herself in a dressing room while he watched via Facetime. But every one of those times was in a store of her choosing, he had never before specified where she should go. What the fuck was going...

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