Transgendered

Never Shame the Family -3

As the weeks quickly went by my breasts grew. I don’t really know if it was due to the hormones or all the cum I was swallowing or Kim playing and nursing on them. He loved watching them grow and I loved his nursing on them whenever we had the chance. I started spending more time at Kim’s place, momma didn’t mind as long as I gave her the money from my “dates” and got a small allowance back. By the time my 18th birthday came I was filling out an “A” cup bra. For my birthday Kim gave me a diamond pendant. It was beautiful and he kissed me deeply as he put it around my neck. I took off my shirt and bra to show it off hanging between the folds of my growing cleavage. Kim cupped my breasts and kissed me again deeply and as our tongues played in my mouth I knew what I wanted then and Kim did too. He led me back to his bedroom and spun me around and slid my skirt down as he kissed me passionately. I opened his shirt and kissed his chest as I made my way to my knees. Finally in front of my loving target I opened his pants and took his flaccid penis in my mouth. Kim moaned as I made love to his penis with my mouth and soon I was rewarded with a rock hard penis to make love to me. He gently pushed me back on the bed and kissed his way down my neck to my developing breasts. After a few minutes of licking and sucking on my nipples he looked up at me with puzzled look. I asked what was wrong and he said that it started to taste funny when he was suckling my breasts. I looked down and saw a drop of clear fluid on the end of my nipple. Kim licked it and was not discouraged by the taste so he continued to nurse on my young breasts. Our love making continued and while I could not decide where I wanted Kim to give me his seed he did and I was not disappointed.
I woke early and stayed in my panties without a top as I fixed Kim’s breakfast. I found that I liked the feel of my chest moving and jiggling freely as I moved about. Kim came in and also commented that he liked the look of my naked chest so it was an unspoken rule that I would go at least braless around the place when I was here. When I arrived home I told my momma of my concern of the fluid from my nipples. She looked at my chest and after much discussion she told me that with the added and constant stimulation that my breasts were trying to produce milk. I started to cry because I was so happy then it dawned on me that I was no longer just a man dressed as a woman, but that I was becoming a woman. We talked for a little while not as mother and son but more like mother and daughter then I had to get ready for my “date” with the photographer.
I went to the studio he had set up in an apartment and things went as usual. We had some drinks and talked about what was going to happen while he got the cameras ready. The two hour session went as before with me posing in various positions and slowly undressing. Once fully nude he would have me pose and masturbate while he took many pictures. After we finished and he said he had enough photographs of me we settled down and he made love to me. After we finished I went to the bathroom to let his seed drain from me. When I came out I saw him looking at the pictures on his laptop. I looked over his shoulder and admired the way my skin had softened. How my hips had rounded out and my budding but firm breasts were developing. Then the horror hit me. I saw that my backpussy no longer was the puckered little bud, it was a small gaping hole left slightly open from the many times it had been used. Jason paid me well and gave me a kiss as I left but the thought of my little hole disturbed me as I thought about it on the way home.
I saw my sister sitting in a little shop and went in and joined her. We talked for a few minutes and then headed for home. On the way she asked me what was wrong; she could tell I was troubled about something. I burst into tears as I told her of my abused hole. She put her arm around me and quickly calmed me down and said that she knew some exercises that would help me and that she would show me when we got home.
When we arrived at home she took me to her room. She told me to lift my skirt and get on her bed on my hands and knees. After I got into position she took her hands and gently spread my cheeks. I felt her fingers gently probe and massage my tired hole as she said that I definitely needed to exercise back there. “Let’s get naked and I’ll show you what to do.” She said as she got up. We both stripped our clothing and got back on the bed. She got on all fours and presented me wither backside. Even though it was my sister, it was the first vagina I had seen since I started this oddity as a woman and the sight was arousing me. She showed me how to contract and relax the muscles to exercise them “Now it’s your turn.” She said as I took the position. I started to contract and relax the muscles as she taught me. As I worked out I heard her breathing become heavy. I felt her hand cup and massage my penis and scrotum as she said it had been a long time since she had felt one of these things. You see, since she had started as a working girl she has gone exclusively to women who are more gentile and pay more. This attention to my member was getting me aroused and I stopped my exercises and rolled over on my back. She leaned forward and brought her lips to mine. Our breathing got heavier as we passionately kissed and our tongues danced together. “I need this now.” She exclaimed as she lifted up and reached between her legs and took hold of my now hard penis. She guided the head to her warm and wet womanhood and sank down on it. We both let out a soft moan as we became one. It had been about a year since I had another woman and while I had grown to love the feel and taste of a hard penis this was something I also missed. She started moving up and down on me as we made love. Her hands cupped my breasts and she was massaging them as she slid up and down on me. We made love for many minutes when she began to moan and breathe heavily. I knew she was about to have an orgasm. When it hit her she sank down and buried my penis all the way in her and started shaking. This triggered my own orgasm and I unloaded a massive load of my seed into her. Sexually exhausted she fell on top of me and we both went to sleep satisfied.
The sun was just coming up when my eyes opened and I felt the soft lips of her mouth on my penis. I softly moaned as her mouth made love to me. She sensed I had awoke and moved so her womanhood was above my lips. As I licked her lips I could taste some of my own seed I had deposited the night before. Eagerly I cleaned her out and then rolled her onto her back. We made love again and after another powerful orgasm we cleaned each other with our tongues. Oh how I fell in love with the taste of my own seed dripping from her. We showered together and got ready for our appointments, hers with an older woman and mine with a slightly older man.
When I arrived at the meeting place he was waiting for me. He was eager for me and wanted to waste none of his time he was paying for on small talk. Once inside his room we quickly got naked and I knew what I had to do. For the next two hours he used me as nothing more than a receptacle for his penis and seed. Oh how I hated these sessions. I was sore all over and sticky with his seed all over me, both inside and out. As I left he paid me well for my abuse and I headed to Kim’s place where I would feel safe and loved.
As I entered the door I fell into Kim’s arms held him tightly. Kim could tell something was wrong but did not pursue the matter, he just held and cuddled me all night long. I woke first the next morning and went in the kitchen to fix breakfast. I didn’t hear Kim until his arms came around me from behind. I leaned back into him as he kissed my neck and whispered how beautiful I was. As I leaned forward to tend to the cooking I felt Kim probe my bottom and slip inside me. I just stood there and moaned as he rocked in and out of me making love to me in the morning the way he liked it. I lost all track of the task of cooking breakfast as he made love to me. When I finally felt him stiffen and release his seed into me I smelt that breakfast was starting to burn. He pulled out of me and I turned the oven off as I felt his seed run down the inside of my legs. I started to cry about the burnt food and Kim quickly hushed me saying we could make our own breakfast. I wiped the mess between my legs with my fingers and sucked them clean as we headed to the bedroom. He lay down and I climbed on top of him and took him into my mouth to suck his nourishment out of him. He must have been really turned on because in about 5 minutes he filled my mouth with his delicious seed. I swallowed every drop and lay down spent from my work. Kim rolled over and started to suckle on my now milk producing breasts. It had been a couple of weeks since that first time Kim noticed the fluid leaking from me and now I could produce proper milk. He drank from me till I was empty and this turned him on so much that we made love again.
Some of my customers liked the fact that I was producing milk and some didn’t care. I was making good money for the family and despite the profession, my family was proud of my sister and I. For two years now we had not shamed the family.

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Cooking with Gas

I was a young 20 years old with big dreams and I just had moved out of my mother’s house and into my very first apartment. It wasn’t the greatest place but it was my place. It was an old converted hotel. They had knocked out a wall and made one room into a bedroom and turned the other room into a kitchen, living room and a dinning room. Needless to say there wasn’t much room left.
After moving my stuff in, I realized that I had no food in the joint. “Off to the store.” I thought to myself. And with that thought I went on my quest for food.
Once I got to the store I grabbed my cart and began to hunt. Well at least the modern day type of hunting a naĂŻve kid does. I never realized how much crap goes into cooking until that time.
“You seem lost.” A sweet voice said to me. When I turned to respond, I was greeted by the most beautiful green eyes smiling at me. “Ah” was about the only thing I could say. “You have never shopped before have you?” She was pointing to my cart which only had a box of Captain Crunch and canned beans. “How could you tell?” I squeaked. I quickly coughed to try and look some what manly.
“My name is Elizabeth” extending her hand to shake my hand. “Will” I responded. I think she knew I felt a little awkward. I couldn’t help not being awkward! She was kind of tall for a lady, about 5’9” and maybe 145 pounds but I was never any good at guessing weight and she was in her early 30’s. I found out 34 later. Elizabeth also had emerald green eyes and fiery red hair which draped over her shoulders. She was wearing a very professional looking pinstripe dress and she had radiant white skin. Almost like a porcelain doll.
“Is this you first time shopping for food?” She said. “Is it the obvious?” She laughed softly “Yes” I must of turned red of embarrassment which she took as anger. “I’m sorry I didn’t mean to make you mad.” “I’m not mad. Well at least not at you.” I lowered my head when I responded. “Where do you live?” She asked. “Down at the old hotel.” “Well would you like to learn how to cook a little bit more? Or do you and the Captain have it under control?” I couldn’t help but laugh. “Sure” I said “What are you? Some type of cook” she coolly smiled and said “Something like that”
After some small chat she gave me her phone number and directions to her house. She said her kitchen as a bit better than my place. First of all I found out she was the head chief of the best bistro in town and she taught at the local college. Her ‘house’ was more like a mansion and her kitchen was bigger than the slum hole that I lived in.
After a few months of lessons I was leaving the Capitan behind and creating my own dishes. “Can I ask you a question?” I said as I was washing some carrots. “Sure, be my guess” as she lifted her glass of wine to her red lips. “Why?” “Why what” She looked at me with a bit of a puzzle in her eyes. “Why are you teaching me how to cook? And allowing me into you house? Not to sound ungrateful but you didn’t even know me when this all started! I could have been one of those crazy people that would have killed you and turned you into a pie or something like that!”
She giggled a bit and said “Because I thought you were cute and besides crazy people don’t eat Captain Crunch” “They might!” I said with a smile “Ok then crazy man, how would you turn me into a pie?” “Ma’am you would be too good to be a simple pie” I answered with a bit of flirtation. “Oh really?” She seemed a little flattered “Really” I felt my face turn flush. “So how are the carrots coming along?” Elizabeth asked. I think she realized I had become a little embarrassed with the flirting.
Time had passed and summer was coming in. That only meant one thing, fresh fruit and good wine. “What are we learning today?” I asked “A simple fruit salad with a red wine dressing!” Elizabeth said with a smile. “Then let’s waste no time. To the kitchen!” I tried to use a super hero’s voice. Elizabeth shook her head “You need help.”
It was a beautiful Sunday and I was with such a lovely teacher, it was almost heaven! “Save the wine we don’t need anymore for the dressing. Besides what well we drink with the salad if we use it all?” “Good point” I said. I watched her stir the bowl of dressing and I thought to myself “Man she is beautiful!”
Elizabeth was wearing a green shoulder less linen sundress that really showed her body off. Her red hair was neatly done and graced her silky shoulders. I had often wondered what it would be like to kiss them and the way to her full lips.
“What are you thinking?” She asked. I must have been staring because she had a strange look about her, like she was looking into me. “Oh nothing” I said. “Right.” She said as she served the salad. “Then why were you staring?” “Staring?!” I was startled by her coyness.
“Look I need to tell you something” Elizabeth said “Let me guess. Over the past few months you have been poisoning my food and now it is time to kill me?” I had jokily said “Not quite” she said “Oh I got it you find me irresistible and you want me to be your man servant!” “Well not a man servant” She smiled “But that isn’t it either” “I see you just want” Before I could finish my next statement Elizabeth blurted “I’m a man!”
It was quite for what seem like hour or so. “And?” I finally said. “Don’t you get it? I’m a man!” Now Elizabeth seemed to be almost crying. “Well almost a man. I’m becoming a woman” She looked away with those words.
“Once again, and?” I said to her like as if she said she wasn’t a natural red head. “Aren’t you a little freaked out?” She asked. “Nope” I responded “Well maybe by the fact I think you use too much salt to your food.” Elizabeth laughed as she wiped tears from her face “Salt adds flavor!” she joked.
We spoke for a long time over dinner and late into the night. “So do you know a lot of ladies like me?” “Not a lot but some” Elizabeth then asked “Are you gay?” “I wouldn’t say gay. More like a lazy bi sexual.” Elizabeth looked confused by my statement. “What do you mean?”
I looked upwards trying to think of the best way I could describe what I meant and it pretty much came down to I like ‘special’ ladies. I told her how I had two encounters with boy during my high school years and almost didn’t have any more. Then I told her of an encounter I had at a Halloween party where a friend and I went and a doctor and nurse.
“He lost a bet” I said. “A bet?” Elizabeth asked. “Yea. To tell the truth I don’t even remember what the bet was but it ended up with him dressing up like a nurse.”
Elizabeth took a sip of wine and asked “So what happened?” I thought for a moment and replied “We went to a party and smoked a lot of weed. My mom wasn’t home for the weekend and my friend couldn’t go home stoned.” I took a long draw from my wine glass “So we called his house and convinced his parents to let him stay at my house. Needless to say we smoked more weed and talked about who we would like to ‘do’ at school next thing I know I was watching my friend, dressed like a sexy nurse, jerking off” Elizabeth seemed to be hanging on my every word “Then what” she said over her glass. “Well” I started “I don’t know if it was the weed or both of us just being horney or even the combination of both, but next thing I know we were in the 69’ position having one hell of a time!”
“So.” Elizabeth said shortly “You like ‘ladies’ like me?”
“Yes” “Do you like older ladies?” Elizabeth asked with a hint of evilness.
I smiled back at her “Only if they know how to cook”
At that time Elizabeth excused herself and told me to stay put. I felt my heart skip a beat knowing what was about to happen. “I’ll stay right here” I said as coolly as possible.
As soon as she disappeared from sight I started to freak out! I was about to have a night of passion with one of the sexiest creatures on the planet. Her lovely red hair, her green eyes staring at me!
At that time I don’t know if it was the wine of the raw emotion of fear, but I stood up and then promptly passed out.
“Are you ok?” I looked up into Elizabeth’s eyes. “If dying and going to heaven is alright then I’m more than Ok” She smiled.
Elizabeth took my hand and helped me up “Come with me” and she guided me to her bed room. She was wearing a black corset with matching stockings. She was also wearing a pair of black panties that didn’t hide her bulging cock.
“Do you like what you see?” She asked. My voice failed me and I squeaked “Yes!” I turned beet red. “Relax and let me make you happy.”
She moved in slowly and pressed her soft lips onto my lips. Slowly our lips parted as our tongues danced with each other. Elizabeth pulled way from me so she could unbutton my shirt. After she pulled my shirt off of my body she leaned in and kissed my nipple. “Oh!” I shuttered. She let a slight moan out as she continued to kiss and lick both nipples.
“You have me so turned on!” I said. She gave me an evil smile. “We haven’t even gotten started.” At that time she had turned me around and pushed me onto the bed.
Elizabeth then began to straddle me and kissed me deeply. “MMM you do like me!” she said noticing my growing erection. “Can I see?” She asked “Please do!” was the only response I could offer. She slowly kissed down my chest and belly and slowly unzipped my pants. “Oh!” Elizabeth gasped “I guess someone did eat their veggies” and with that corny line she had pulled my hard cock from its cotton prison and wrapped her hot mouth around it!
“Sweet mother of God!” I screamed. Her mouth was so hot that it almost caused me to cum. I was so turned on I thought my cock was going to rip in half. I looked down to see Elizabeth’s emerald green eyes looking at me. Then in one deep swoop she took my entire cock into her mouth.
The combination of red lips, green eyes staring at me and all of my cock in her caused me to lose it. “Oh Damn!” is what I said as I exploded in her mouth. Elizabeth bobbed up and down my cock taking every drop of lust I could give! “God that was a lot!” She said.
“I’m sorry I couldn’t hold it!” I was a little embarrassed. Elizabeth laid beside me and said “Don’t worry we have all night” With that I kissed her.
I could feel her cock against my leg poking me through the silky fabric of her panties. I reached down and felt her. She was hot and hard with a small wet spot. I then laid her on her back kissed those silky shoulders, it was nirvana! After a short time I found myself pulling Elizabeth’s panties to the side so I could taste her. Her precum was sweet and thick it was divine!
The moaning of the goddess had caused me to get excited again and I found myself filled with lust. “Put in me” She said. “Put that hot cock in me now!” I rose up and lifted Elizabeth’s legs to my shoulders. Her eyes, those beautiful green eyes, begged me to turn her into a woman.
I began to ease my cock into her, slowly at first. Then with each thrust I went deeper and faster. “Fuck Me!” Elizabeth demanded “Fuck Me Hard!” I watch as my cock disappeared into her and I watch her cock dance against her black corset.
“Harder you bastard!” she screamed “You like this don’t you? Bitch!” She moaned loudly with those words. I stroked her cock as I reamed her hard!
“You want it Bitch?” “God yes” She screamed. All of the sudden her eyes grew wide and her mouth opened. I felt her cock twitch in my hand and I got to see her white cum drench her corset! I also felt my cock to become more sensitive and I felt that intense feeling before release.
“Oh my God!” was the only words I said as I began to fill Elizabeth. We both trashed and screamed. So much so if you didn’t know any better you would had thought that we were killing each other.
We laid silently and then drifted off to sleep. We saw each other for a long time learning how to cook. After awhile I joined the military and last I heard she had gotten married. I just hope her treats her well because if not. I will.

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Cloudberry Chronicles Part II: Meltdown

Cloudberry Chronicles is an erotic web series that follows the eponymous adventures of Cloudberry, an elf on a mission to save her homeland and bring peace. It predominantly features lesbian, pansexual and polyamorous characters who are both cis and trans for your reading pleasure. Each story is a fully contained adventure, and the beginning of the smut (if you want to skip the lore and get right down to business) is marked in bold. Follow my writing on: http://dresspockets.tumblr.com/