Recommended for TV section in Transgender. Karra's sissy journeyBy: Karra Violet
Having secretly dabbled in dressing up for about 10 years I found my desire to dress more difficult to keep down. In my late teens through my mid 20s would wear panties bras and stockings every so often but hid that side of me. As life went on and I settled into the life I was expected by social norms, I started to get depressed when my wife Amber and I would go shopping. I loved helping her pick out clothes in the women's section of various stores but it made me also feel jealous that those clothes weren't for me, and on top if that she was 1 or 2 sizes smaller than me so even trying it on behind her back proved to be very tricky.
Amber is beautiful. 5' 7" 220lbs with brunette hair, light but tan skin. Shes curvy with D cup breasts and a nice thick booty! We had been married for 4 years and we had a really great marriage all things considered but I knew that my life was passing me by with out living the feminine lifestyle I had often dreamed of. As the urges grew stronger I knew I needed to come out to her. She was adamantly supportive of LGBT people but told me about a person she dated once who was transitioning to female. She said she enjoyed dating her but in the long term thats not what Amber wanted.
To me that meant Amber wanted to be with a man and I felt that since thats what she signed up for that I would massively disappoint her if I told her of my feminine feelings. It was very difficult and I decided to play things step by step to see how far it would go... below is the timeline of events of my journey into becoming the sissy I was born to be:
February 2016:I complained of having a difficult time sleeping for a few nights due to my genitals flopping around and struggling to get comfortable. One night she brought me an old pair of her panties for me to wear to sleep. They were light blue cotton breifs, size 9, they were kind of big and streched out for her liking as she usually wore size 8. I acted like I wasn't sure but of course agreed to "try it out." Deep down i was so happy! I ended up wearing them to bed a few nights in a row but with the need to wash them so frequently I took it upon myself to go buy more panties at walmart on my own! I figured since she was ok with me wearing them she certainly worldnt mind me buying my own. Years prior panty shopping was a terrifying experience due to the check out, but with self scan registers and a little bit of past experience, I felt brave and just did it. I settled on two packages of panties. A set of microfiber and a set if cotton high cut panties. Both packs had mixed colors. Black, gray, white, blue, pink, purple, and some with cute patterns! When I got home with them Amber chuckled at me for buying 12 pairs of panties and it made me nervous, but she said she didnt care and was glad I got my own rather that ruining any of hers.
March 2016:While driving up north to visit her family we got on the topic if my nightly bed time panties when she tells me that she doesn't mind and wouldn't mind if I wore any kind of women's clothing. I said "so if i dressed all the way as a woman you wouldn't care at all?" In kind of a sarcastic tone. She said "nope, go for it... its just clothes.." I told her ok and that I would order stuff online.
A week later I had a few deliveries. A couple of white satin bras, a black lace push up bra, black lace trimmed nylon stockings, a black dress and a wig. One night after work I dressed in all of it. I was a nervous wreck leaving the bathroom because my self confidence was quite low. Even though I shaved from head to toe I felt like I looked bad as a girl. But I went through the door and into the living room. My voice was trembling and I was scared. But, Amber was very nice about it and went for her make up so she could teach me about applying it. I learned some good basic tips of makeup and started doing my own over the next couple of weeks.
April 2016:I would dress at home a couple nights a week and then would undress and clean off the make up and go to bed, but I hated not having anything femme other than panties to sleep in so i got a purple nighty. So silky and soft! I loved it! I started wearing it every night and eventually bought 2 more in the same style. One burgundy color and one in pink.
June 2016:Our sex life started to change. Although I always wanted to try being fucked by a man or a strap on I was worried about bringing it up. I told myself I was still the man she signed up for, I just like to dress up.
One night we started fooling around like we usually do. First some touching and kissing, then my face buried between her legs until she told me it was time to fuck... but this time i was down there for 30 plus minutes and 3 orgasms. She then decided she wants to try using her sex toy in me that night. I am so happy inside and proceed as she wishes but I wasnt sure if I was supposed to still fuck her after. I was afraid to ask so I laid back as she fucked me with her toy and I ended up having an amazing orgasm as I came she said "good gurl.." I loved every second of it.
August 2016:Amber buys a strap on and fucks me with it for my birthday. Best birthday ever! Our traditional sex continues to decrease. She claims a lack of sex drive but sends me to the bedroom with a dildo to fuck myself with more regularly.
October 2016:I order a skirt, another wig a couple of women's shirts to wear with the skirts as well. The skirt is black and goes just to the knees when sitting. One shirt is purple v neck with no sleeves and a white v neck that is also sleeveless.
November 2016:After increasing my panty inventory to around 24 pairs, I realize one day while getting ready for work that I only have 5 pairs of boxer breifs and none were clean. Curious as to why i felt some boxers were missing, Amber told me they were falling apart or had holes in them and that she threw a lot of them away. I nervously decide to wear black microfiber high cut panties to work. That day I quickly learned that I would not be able to use the urinals and would have to sit down to pee in the bathroom the stalls at work. Although this is stressful as I worry about others in the bathroom noticing my panties, I convince my self nobody would be looking, plus I love having panties on all day!
December 2016:Amber usually buys me underwear for Christmas but decided not to this year because I have more panties than she does.
February 2017:I can't bring my self to buy mens underwear and choose to wear black, gray, white, and blue panties to work almost everyday now. Sex between Amber and I is minimal, but she did ride my face to orgasm and strap on fucked me for Valentine's day. I loved it!
March 2017:Amber tells me she would like us to move to an open marriage so we can see other people for sex. I am a little concerned but excited about having the opportunity to meet a man. She and I agree to ground rules around open and honest communication and safe sex. She takes some pics of me dressed up to start a dating profile. The next day she puts on her strap on and tells me to suck her dick. I said I wasn't sure if it would fit in my mouth as it was thick looking. She said "I didn't ask... I told you to suck my dick bitch!" I got to work. She made me suck it for about 40 minutes as she gave me instructions through out on what to do with my tounge and mouth and my pace. She told me if I was gonna see men I needed to know what I was doing. It was exhausting... she commented on how wet my panties were when it was over saying "looks like you enjoyed yourself" with a smirk on her face.
May 2017:Online dating brings me a really nice man who I agree to meet. He is interested in taking pics of me so I have more for my profile. We meet up for 3 hours in a hotel and after a bunch of photos are taken I ended up with his dick in my mouth. After sucking him for 15 minutes he came in my mouth. This was my first experience with cum in my mouth. I quickly swallowed it down and was surprised that it was kind of enjoyable.
June 2017:Amber and I move to our new house. I am excited because being out of an apartment means I can dress all the time, even go outside dressed with very limited visibility to the public due to its location.
July 2017My last pair if boxer breifs are tossed and I continue to wear panties only, but now its no longer a choice. Now instead of having to wear black panties when I can't find boxers, its having to wear pink and purple panties when I can't find black. Amber buys me a new set of bras. Black, purple, and deep red. All lace with padded C cups. She encourages me to wear my silky white bras to work everyday. I agree and begin doing so.
August 2017:Having some fun in bed leads to her asking me to fuck her doggy style like we always used to. I try but struggle. My cock feels smaller than it used to. I used to get like 5 inches hard.. i was struggling to get 4 inches. She gives up on that and the night ends with me using toys and my mouth to get her off.. she tells me if I want to cum I better get a toy dick in my ass. She calls me a cock whore and tells me to ride that big cock as I finished.
September 2017:She decides shes ready to find a man and had some luck with a guy she met on tinder named Paul. He is 6'2" shaved head and dark skinned. Even I like the looks of Pauls puctures.
Around that time, Amber buys me a surprise. A small pink chastity cage. She puts it on me that night and strap on fucks me until I cum in it. She tells me it looks so cute on me and to wear it a few hours everyday. I agree since she didnt ask, and I liked it.
October 2017:After a few weeks of busy schedules, Amber meets Paul for dinner and seems very interested in him. She asks if its ok to have him over and if I am comfortable with that. I said of course. She tells me to plan on sleeping in the guest bedroom that night.
That night arrives. The night before halloween. She and Paul sit and talk while I bring drinks. Paul tells me I must be quite a sissy if I can't take care of Ambers needs. Amber giggles and defends me my saying that I still do somethings very well. I smile and carry on cleaning up the kitchen. Paul and Amber start making out on the couch before they retreat to the bedroom.
I hear Ambers moaning and Pauls grunting for 2 hours. Paul leaves and Amber is glowing but looks wrecked too. She tells me he fucked her better than she has ever been fucked and his thick 9 inch cock is a master piece.
December 2017: Paul is over once or twice a week to fuck Amber. As I am used to his visits and I am usually fully dressed when he visits. Paul gets comfortable with our situation and grabs at my big ass and compliments my femme look. This leads to he and Amber asking me to suck his cock to get it ready for Amber. I am also instructed to lick ambers pussy too. It becomes common for me to go back and forth between them as they lay next to eachother making out in bed, or to have Amber sitting on my face as I stroke Pauls cock. Once they're ready to fuck Im told to go away and let him fuck her.
February 2018:Amber tells me that since I am not really a man that she would like me to make the guest room my perminant room. She says my growing wardrobe needs its own space and shes tired of our stuff mixing together. What she says makes sense and I agree to my own room. She also tells me I should pick out a girl name for myself. After a night of research I settle on Karra. I love it!
Having my own space leads to me having time to pleasure my self when I want as I wont disturb her reading in the bed next to me. Typically I would get out my toys and fuck myself but once decided I was too tired for that and would just stroke myself to orgasm. It didnt feel right. I kept going limp and even when I was hard it was only like 3 inches tops. I was wondering if something was wrong and asked Amber the next day what she thought. She laughed at me and said "use it or lose it! Oh and that cute cage of yours has that effect." I am relieved that its nothing serious and think shes right, i dont need it much anymore so no big deal.
March 2018:Im struggling to find a good man. I had this idea of having a boyfriend but it wasnt working out at the time. Amber sends me some exercise apps for my phone to help get my ass looking better. So i started doing the squats, leg lifts, wall sits and more. We also went shopping together at the thrift store. I wore womens jeans in public for the first time. I was self consious the whole time and asked if I looked ok. Amber told me not to worry and that I had cute panty lines. This made me both happy and terrified at the same time, but we found more cute tops and jeans as well as some cute shorts. I ended up enjoying myself other than sweating at the register as she left to start the car while I checked out.
May 2018:Paul still visits 1 to 4 nights a week depending on their schedule, and how often he wants to fuck my wife. I am very used to this relationship at this point and am glad theyre happy. I enjoy my participation when requested but keep to myself and clean up around the house or keep busy while the fuck. Paul stays the night from time to time and I enjoy his presence overall. I feel safer when he is around.
June 2018:June 13th to be exact on this one. Paul came by as usual to fuck my wife. They were making out as usual but Amber was uncomfortable. I thought she may have been sick as she complained about her stomach. She went off to the bathroom and returned to tell Paul she was not going to be able to fuck because she just started her period.
Paul was not very pleased and said he really needed it. Amber askes him if he would fuck me instead. I was surprised and said "Im not sure if Paul would want that but I can suck him if you guys want?" Paul agreed and took me back to Ambers room and told me to get to work. I pulles out his BBC like usual and started sucking his huge cock. I wasnt sure how long it would take to get him off cause I always left after he was ready to fuck Amber.
I sucked his cock from my knees for about 15 minutes. Then he told me to get up a d turn around and put my ass in the air. I was still wearing a skirt, purple lace bra and panties and a white and purple top. Since he didn't tell me to take my clothes off I just got on the bed and put my ass in the air like he asked. He started rubbing my ass through my panties telling me he has never fucked a sissy before but that my ass looked real good. Amber came in and asked if I was being good for him. He told her i was just fine and he was gonna fuck my big white ass. Amber smiled and went to my room and got my lubricant in my toy collection. She retuned as Paul was pulling my panties down over my ass. My legs were tight together squeezing my little clit. He started squeezing the lube onto me and rubbing the lube around his cock.
I layed there nervous and excited as he was preparing his huge cock. Amber told me it might hurt a little but I should be fine since I use pretty big dildos. She was right.. Paul started pushing his cock into me but it wasnt getting in. Amber told me to relax and take some deep breaths. Paul was getting a little impatient and said "dont make me shove it all in at once, bitch" i said I was sorry and took a breath and relaxed and told him I was ready again. He started pushing against my boi pussy and Amber kept saying relax and let it happen. Finally I felt him break through and it felt like a shot of burning pain followed by an intense pleasure. Paul pushed him self deeper and deeper until he was all the way in. Amber said "good guuurrl" as the last inch went in. My god all that dick felt intense and I just let out this loud moan in my most feminine voice with out even trying. It felt natural to have this mans big hard cock buried in me!
He began slowly going in and out when reminded me of similar sensations of using my toy but this was warm hard raw cock and it just felt so right. Paul continued to pick up his pace and started fucking me pretty hard and fast. Every change in pace has this different effect on me but i was so happy. At one point I said "mmm fuck me daddy" with out thinking about it. It just slipped out. I was then a little nervous if he would even like that, but he quickly thrusted hard into me and said "take that daddy dick sissy!" I felt like i was going to cum right then but that feeling never ended. He fucked me, fucked me, and fucked me more, while I moaned and wimpered. Man has some stamina! Amber watched and cheered us on. Telling me to take his cock like a good bitch and telling him to fuck me good. I was almost numb with pleasure and after fucking me into the bed for what must have been almost 40 minutes I felt him tense up and let out a few grunts before I felt his dick explode inside of me. I felt 3 huge spirts of cum soak my insides before he slowed down and came to a stop like a train pulling into the station.
He pulled out of me and went to the bathroom to clean his giant dick off. Amber threw a towel in my direction and told me to get ready for his cum to start dripping out. I rolled onto my back and my panties were soaked and sticky. Although I didn't have a big orgasm like i was used to I was leaking cum the whole time.
Paul ended up leaving for the night and before going he told me I did a good job filling in for the night! I was very proud to have taken my first real cock and was happy that Amber was there to share that moment with me. I took a shower and got into my pink satin panties and purple nighty. Amber told me that his cum is going to be leaking out of me all night and handed me one of her pads to tuck into my panties. She showed me how to put it in and sent me off to my room for the night.
I was so happy to have my femme life fantasies come to reality!
August 2018:This month has been good. I am dressing everyday when I am not at work.. other than the bra and panties anyways. Ive been going out in public in womens jeans alot lately. Im sure I will continue to grow more and more into my femme life.
Paul has fucked me once more but usually prefers Ambers body over mine which I respect. I have lost interest in women and find myself craving big cock a lot. I still haven't found a boyfriend yet but i know that if I keep working on mt body that will come in time!
I gotta admit.. I am such a sissy and ut feels good to be what I truly am!