Stories by cdbottom2

11
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cdbottom2

Telling Mom I'm A Cross Dresser Part 19: Christmas Special

Missy's Christmas story :) Enjoy and please rate and comment.

Christmas Special It was now around Christmas time and I couldn’t have been happier. Any other year we would have had family over which meant I had to dress normal because the other members of our family still had no idea or at least weren’t talking. However this year we had no plans at all, our cousins were off on vacation to Mexico until new years, my grandparents were not in a...Read On

Added: 26 Dec 2012 | Category: Incest | Avg Score: 4.73 | Views: 2,034 | Tags: incest  crossdressing  toys  lingerie  christmas  anal  bisexual   | 2 Comments

9
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cdbottom2

Telling Mom I'm A Cross Dresser part 18: Missy's Halloween Party

Part 18 is about halloween. Hope you all enjoy despite i was a little rushed for this one.

I had enjoyed my week of sex with Thomas and Lemar but in the end it left me sore and used but not like I was complaining. It was now getting close to Halloween and mom and I were making plans to go to a Halloween party a few city blocks away from us. Yeah, sounds kind of boring I know but it was no ordinary party with costumes and drinking alone. It was an orgy for bisexual people. It...Read On

Added: 31 Oct 2012 | Category: Crossdressing | Avg Score: 4.56 | Views: 3,142 | Tags: orgy  gangbang  bisexual  halloween  milf  toys  oral sex   | 3 Comments

7
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cdbottom2

Telling Mom I'm A Crossdresser Part 17: Seven Days Of Sex, Days 1, 2

Part 17 of Missy, Sorry this is long but i hope you will like it.

This is a fairly long story but I broke it into two parts so that you can read the first half in one sitting and find your place easier if you want to come back and read some more. Also, I would like to say that this will be the start of a seven day sexcapade for Missy involving two of her past flings. Please enjoy and rate and comment at the bottom. Happy reading!! ;) It was now Monday...Read On

Added: 04 Sep 2012 | Category: Crossdressing | Avg Score: 4.86 | Views: 3,742 | Tags: crossdressing  gay male  group sex  anal  oral sex  interracial  exhibitionism   | 4 Comments

2
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cdbottom2

Telling Mom I'm A Crossdresser Part 16: Hot talk With Mom

A story in a story. Not much Missy but dips into the mom's life. I hope you enjoy :)

My night with Laci was amazing, It was like I could tell what she wanted and when she wanted it by instinct and she could do the same for me. All that weekend it was all I could think about as I continued on with a normal weekend. Nothing to special really just washing my normal and my Missy clothes as well as taking care of chores around the house. I went off with some friends at times...Read On

Added: 28 Aug 2012 | Category: Lesbian | Avg Score: 4 | Views: 2,376 | Tags: lesbian  milf  masturbation  crossdressing  toys  exhibitionism  anal  

34
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cdbottom2

Mom made me a Fluffer

another story between Missy adventures. Enjoy and please rate and comment all stories. :)

For most of my life I never knew exactly what my mom had done for work, neither did I know who my dad was. As such I just continued with life and thought to myself that I would find out what she did in time. My curiosity first peaked when I was 16, I was looking for my moms purse so I could exchange some of the money I got mowing lawns for people around my neighborhood for different bills....Read On

Added: 27 Aug 2012 | Category: Crossdressing | Avg Score: 4.91 | Views: 10,790 | Tags: crossdressing  oral sex  masturbation  quickie sex  bisexual  porn star  milf   | 7 Comments

5
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cdbottom2

Telling Mom I'm A Crossdresser Part 15: 2 Kinky Girls.

Part 15 is finally here :) plz enjoy as Missy enjoys a night with Laci alone!!

It had been a week since Mom and I spent the 4 days at the spa and hung out with my old babysitter Laci and for a while it was back into our old routine of working and coming home. Day after day I kept thinking about how her warm wet pussy felt wrapped around my cock while the feel of a sexy thong rubbed against my asshole. I came home one day to find my mom was packing a bag. I asked her...Read On

Added: 15 Aug 2012 | Category: Crossdressing | Avg Score: 5 | Views: 3,393 | Tags: crossdressing  straight sex  pegging  vibrator  anal  oral sex   | 1 Comment

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cdbottom2

Telling Mom I'm A Crossdresser Part 14: Back to the spa and a familiar face.

Part 14, yes I feel it is long but please read the whole thing you will not be disappointed.

Part 14: Back to the spa I'm sorry this story is a fair bit longer then my usual ones however I didnt want to separate thes and have another story with almost no sex in the first one so soon. Having said that I hope you enjoy my story and please read the whole thing. I promise you will not be dissappointed. I woke up the next morning lying next to mom in her bed. I was wearing a pair...Read On

Added: 21 Jul 2012 | Category: Crossdressing | Avg Score: 4.71 | Views: 3,478 | Tags: exhibitionism  crossdressing  lesbian  milf  old babysitter  oral sex  straight sex   | 4 Comments

6
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cdbottom2

Telling Mom I'm A Crossdresser part 13.5: Missy Brings Home A Stud

the continuation to Missy going out and finding a man.

I told Thomas all the details of why I was out this night and he loved the idea. He took one of his Viagra and he led me out of the bar. I felt a little embarrassed at all the cum leaking down but some of the cross dressers were just smiling at me like they were saying “you go gurl!” which made me a little proud. Thomas followed me in his car until we got to my place and I took him by the...Read On

Added: 14 Jul 2012 | Category: Crossdressing | Avg Score: 4.33 | Views: 2,986 | Tags: crossdressing  bisexual  cream pie  anal  bedroom hopping   | 2 Comments

5
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cdbottom2

Telling Mom I'm A Crossdresser part 13: Missy's Turn

here is part 13 part 13.5 will be up ASAP Plz enjoy and comment and rate at the bottom :)

Sorry not much sex in this one but its a lead up to 13.5 and I hope you enjoy both of them. :) Once mom and I had gotten our car back, we took it out for a spin and I have to say it worked and looked like new. It had everything from a new paint job to new parts in the engine. Now in all honesty, I did have to go back a few times and give Ray a few blowjobs to help pay for them but it...Read On

Added: 13 Jul 2012 | Category: Crossdressing | Avg Score: 4.4 | Views: 2,374 | Tags: crossdressing  oral sex  bar  blow up doll  milf. lesbian practice   | 4 Comments

5
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cdbottom2

Telling Mom I'm A Crossdresser Part 12: Tow Truck Driver's Big Score

Missy gets her car towed and makes a deal with the tow truck driver

Sorry it has been so long since my last story. I have been busy with alot of things and I thank you for your patience. Lately, I’ve been working part time at a restaurant to make a little extra cash on the side along with my nights as Missy. I was saving up for a cruise I wanted to go on that I heard was for like minded people such as Missy. When people ask me about what I want to do...Read On

Added: 10 Jul 2012 | Category: Crossdressing | Avg Score: 5 | Views: 3,282 | Tags: anal  crossdressing  tow truck driver     | 4 Comments

18
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cdbottom2

Telling Mom I'm A Crossdresser Part 11: Girl time

sorry it took so long and that its a bit longer then my last one but I hope you enjoy. com at bottom

Part 11 It had been a while since my last time as Missy. I had been doing some jobs for people, nothing special mostly working on decks and mowing lawns for neighbors to not only keep up appearances so as to not give to much suspicion of where my money was coming from. This continued for what seemed like 2 weeks before and started to wonder if my fun as Missy had ended. I walked in the door...Read On

Added: 12 Jun 2012 | Category: Crossdressing | Avg Score: 4.72 | Views: 4,798 | Tags: anal  group sex  lesbian  toys  bisexual  milf  oral sex   | 8 Comments

9
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cdbottom2

A Master For Julie Jizzbucket

A story i have written in regards to my master and myself

I had spent the last couple months indulging in some mild cross dressing. After a few nights wearing clothes that made me feel so sexy and womanly. Until recently I had only worn panties, bras and a few sets of stockings and teddys that I had bought for an old girlfriend before she broke up with me to date a guy that had more money. I have also been going online to a site called Lush...Read On

Added: 30 May 2012 | Category: Crossdressing | Avg Score: 5 | Views: 3,643 | Tags: anal  exhibitionism  reluctance  toys  spanking  fetish  bdsm   | 2 Comments

14
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cdbottom2

First Time, First Fuck, New Porn Star

A story I wrote while on a short break from my Missy series. Don't worry, I just need inspiration.

I am just a normal guy however I have what some would call an abnormal fetish. I am a 23 year old guy and I like to wear and dress up as womanly as possible. I am 5’9, a little chubby but can still pass as a woman, with brown hair, brown eyes and a 5 inch cock. One night I had gone out with one of my friends and had gone drinking to a few bars. As we went from place to place we started...Read On

Added: 10 May 2012 | Category: Crossdressing | Avg Score: 4.64 | Views: 9,350 | Tags: anal  reluctance  toys  first time  gay male  crossdressing   | 4 Comments

13
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cdbottom2

Telling Mom I'm A Crossdresser part 10: Another Day With Mom

YAY!! part 10 :) hope every1 enjoys it and please comment at the bottom of the story or on myprofile

It was about 11am by the time I woke up and found myself still in bed with mom. I looked over to see she was still sleeping and still in her lingerie as was I. I got out of bed carefully and as soon as I did I felt how sore my ass really was. I decided to tighten up my stance a little by putting my legs together and squeezing the muscles in my ass tight as I walked. It was a lot like my sexy...Read On

Added: 07 May 2012 | Category: Incest | Avg Score: 4.77 | Views: 4,534 | Tags: anal  incest  mature  taboo  spanking  toys  bisexual   | 5 Comments

17
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cdbottom2

Telling Mom I'm a Crossdresser Part 9: A New First for Missy

Miss has a few new exeriences when she realizes she has the house to herself, or does she?

It was a few days later after my night with Greg and being his police bitch for the night when I found myself sitting on the couch in a pair of nylon stockings, thong, bra and of course my new brown hair wig and breast forms. That night mom had to work late so I had the house to myself. For the first half of the night, I walked around the house and watched some of my favorite zombie...Read On

Added: 19 Apr 2012 | Category: Crossdressing | Avg Score: 4.94 | Views: 5,441 | Tags: masterbation  interracial  threesome  bisexual  toys  group sex  incest   | 4 Comments

11
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cdbottom2

Telling Mom I'm A Crossdresser Part 8.5: Cops and Prostitutes

What Missy needs to do instead of going to jail for prostitution. (continue of part 8)

When morning came, I told mom what had happened the previous night. She had a surprised look on her face and I could tell she was feeling uneasy at the thought of me getting arrested while dressed as Missy as well. We talked for a while and she was glad as well that the police officer was a Missy fan. “We can definitely let him have a free night in exchange for not getting a criminal...Read On

Added: 31 Mar 2012 | Category: Crossdressing | Avg Score: 4.91 | Views: 4,560 | Tags: crossdressing  gay male  roleplay  quickie sex  prostitution  toys     | 5 Comments

15
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cdbottom2

Telling Mom I'm A Crossdresser Part 8: Bus Driver's and Cops

Part 8 enjoy and please comment at the bottom ;)

My mom and I spent the next few days practicing and exercising with the stripper pole until we felt confident and extremely sexy while doing it, which I have to admit did not take long. One night I came home late from my part time job I had at a local restaurant and took the bus home. I didn't have a car because I hadn’t decided on what car I wanted to get yet and what I could afford. I...Read On

Added: 20 Mar 2012 | Category: Crossdressing | Avg Score: 4.87 | Views: 4,055 | Tags: crossdressing  oral sex  anal  bus driver  police officer   | 4 Comments

11
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cdbottom2

Telling Mom I’m A Crossdresser Part 7.5: Amateur Pole Dancers

I thought I would try something a little different and involve more teasing to my story. enjoy :)

After our time at the spa, I spent a lot of time in my room trying out all the new sex toys we got from Richard and Monica. They were all exciting in their own ways and I came so much with each one. Some vibrated, some went deep and some felt good stretching my ass wide. The feeling of all the sensations I could get from my new plastic and electric friends were amazing and found myself...Read On

Added: 18 Mar 2012 | Category: Crossdressing | Avg Score: 4.64 | Views: 3,887 | Tags: crossdressing  pole dancing  teasing  masturbation  toys  milf  voyeur   | 3 Comments

20
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cdbottom2

A Story About Summer

I hope you like this story, I have wrote it by request from a friend.

I wrote this story by request from a friend and I hope you will enjoy reading this as much as I enjoyed writing it. J My name is Summer and I am a transsexual. I have a B cup chest and my hips are a size 30 and I have an 8 inch cock and I love to be a naughty little whore. It was the summer after high school for me and I was waiting for my admission letter from college to arrive....Read On

Added: 14 Mar 2012 | Category: Trans | Avg Score: 4.83 | Views: 6,066 | Tags: prostitution  group sex  spanking  transexual  bisexual   | 2 Comments

18
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cdbottom2

Telling Mom I'm A Crossdresser Part 7: The Spa

Missy and his mom go to a spa and meet some new friends.

I could barely sit for days after Mistress Keri thoroughly tanned my hide and I had to take almost a week off so that I could heal. My mom knew this to and said we should go on a “girls” weekend to a spa for cross dressers and women, she also said that since it was for others like me then I could spend the entire trip as Missy. I loved that idea and hurried upstairs to pack Missy’s bag....Read On

Added: 05 Mar 2012 | Category: Crossdressing | Avg Score: 4.83 | Views: 5,894 | Tags: crossdressing  anal  oral  exhibitionism  group sex  mature  toys   | 7 Comments

20
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cdbottom2

Telling Mom I'm A Crossdresser Part 6: Missy and Mistress Keri

Missy has her first BDSM experience. Plz rate and comment

Up until now, I have enjoyed my time as Missy. My mom had kept me busy with clients and we pulled in a lot of extra income and I was able to experience a lot of different fantasies, However I had not had the chance to try anything involving BDSM, or not yet at least. One day I came home from mowing the lawn for an elderly woman when I walked in the door to find my mother smiling deviously at...Read On

Added: 03 Mar 2012 | Category: Crossdressing | Avg Score: 4.72 | Views: 5,818 | Tags: crossdressing  anal  straight sex  bisexual  spanking  bdsm     | 5 Comments

27
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Audio version available
cdbottom2

A Hotel With Candy

originally an audio story however became a short story. plz rate and comment.

I got out of bed and looked at my sexy green camisole with bright pink fishnets, bra and panties that I liked to sleep in after I had just spent the night masturbating with my favorite dildo. I looked back at my nightstand to find it was still beside my pillow where I had left it the previous night and stilled wrapped in a condom all sticky with my favorite lube, strawberry flavored. I...Read On

Added: 28 Feb 2012 | Category: Crossdressing | Avg Score: 4.8 | Views: 11,478 | Tags: oral  anal  first time  spanking  crossdressing   | 7 Comments

25
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cdbottom2

Telling Mom I’m A Crossdresser Part 5: Movie Night and Gangbangs

5th installment of Missy, Plz rate and comment. :)

I had decided to take a few days off from being Missy after Stan and Roger had left and my mom and I were finished with our little girl time. I spent the next few days just continuing with life as normal except for the throbbing pain in my asshole and my cock from the 3 days of constant sex. I couldn’t stop thinking about all the things I had done as Missy and all the kinky fetishes I...Read On

Added: 26 Feb 2012 | Category: Crossdressing | Avg Score: 4.91 | Views: 8,812 | Tags: crossdressing  anal  oral  gangbang  milf  exhibitionism  group sex   | 3 Comments

22
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cdbottom2

Telling Mom I’m A Crossdresser Part 4: Repeat Business and Roleplays

4th installment of Missy :) please rate and comment :)

When my mom and I had gotten home, I immediately ran into the house to take a shower and change as quick as I could. I re-shaved my entire body and removed my makeup so that I could start from scratch and apply it again. Once I was finished with my makeup, I see a new outfit laid out on my bed. This was a cute nurse outfit with a short tight skirt that barely covered my ass. It was also...Read On

Added: 25 Feb 2012 | Category: Crossdressing | Avg Score: 4.85 | Views: 8,150 | Tags: crossdressing  roleplay  anal  oral  toys  group sex   | 7 Comments

23
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cdbottom2

Telling Mom I'm A Crossdresser Part 3: Missy's Weekend

Part 3 of my Missy series :) enjoy and please rate and comment.

One day while watching T.V, my mother had come in and told me Missy’s services had been requested for the entire weekend and we needed to go shopping. I smiled as we got into the car and went to the store to buy lots more sexy clothing for me to play in. After we had bought all the clothes and makeup needed for the weekend, my mother and I went home so that she could give me the details of...Read On

Added: 22 Feb 2012 | Category: Crossdressing | Avg Score: 4.71 | Views: 7,695 | Tags: anal  oral  bisexual  group sex  straight sex     | 5 Comments

19
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cdbottom2

Telling Mom I’m A Crossdresser: Part 2.5 My New Toy

This is a simple intermediate story i wrote between part 2 and part 3. Plz rate and comment :)

It was a few days later after my night with mom at the adult shop, and my ass was still sore and I could still remember the taste of the cum in my mouth from that man. I could also still feel the pain in my ass from having to walk all the way home with my mom’s dildo in my ass. My mind wandered as I thought about how my mom reacted to getting her dildo and how horny she got just by looking at...Read On

Added: 21 Feb 2012 | Category: Incest | Avg Score: 4.74 | Views: 9,401 | Tags: crossdressing  incest  anal  straight sex  toys  spanking  taboo   | 2 Comments

39
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cdbottom2

Telling Mom I'm A Crossdresser Part 2: The Adult Store

Missy goes out and meets her first gloryhole. Please comment and rate all of my stories. :)

I awoke the next morning a little groggy as I slowly recalled the events that had taken place last night. I rubbed my body up and down feeling how the latex had now become a little sticky and how my ass and cock were still sore from the pounding I had taken. I read the note again left by my mother and decided to make breakfast as I was for when she arrived.   It was just past 9am when I heard...Read On

Added: 20 Feb 2012 | Category: Crossdressing | Avg Score: 4.84 | Views: 13,089 | Tags: crossdressing  glory hole  anal  oral  milf  toys  masturbation   | 10 Comments

46
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cdbottom2

Telling Mom I'm A Crossdresser

A story of me being open with my mom as a crossdressing slut andher becoming my pimp. Plz comment :)

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5'10" in height. She is also a fairly busty woman with a 30DD chest with about 35" hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first...Read On

Added: 19 Feb 2012 | Category: Crossdressing | Avg Score: 4.83 | Views: 20,358 | Tags: crossdressing  anal  oral  condom  toys  spanking  first time   | 13 Comments

15
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cdbottom2

The Slut Within part 2

part 2 of the slut within and if you like it PLZ comment :) enjoy!!!

As I continued on my knees, I felt my little thong riding up my tight little butt. My skirt got in the way of spreading my legs and my tube top and my skin was all sticky with cum. Thankfully, I wouldn’t be wearing any of this much longer. Their watching eyes so aroused my slutty nature. I took off my tube top and skirt leaving my fishnets and six inch heels. I also wore a black thong and...Read On

Added: 18 Jul 2011 | Category: Crossdressing | Avg Score: 5 | Views: 13,084 | Tags: anal  exhibitionism  group sex  voyeur  bdsm  fetish  interracial   | 8 Comments

28
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cdbottom2

The Slut Within

This is my first story. If you like it please comment and I will write chapter two :)

I was 22 years old at the time, and I had been crossdressing for a few years. For some reason I could never control my desire to put on women's clothes and prance around my apartment looking all sexy and slutty. Normally I can never decide what specifically to wear as I like to change it up all the time, from wearing latex lingerie to sexy roleplay outfits and beyond. I am 5'9 with a...Read On

Added: 29 Jun 2011 | Category: Crossdressing | Avg Score: 4.81 | Views: 18,768 | Tags: group sex  fetish  bdsm  spanking  toys  first time  interracial   | 11 Comments