Only Good thing to cum out in 2020

My first shot at a one shot piece. I am always trying to push myself in new directions. This piece is fictional, all characters are just that, fictional. It is written for your entertainment and hopefully it makes you smile and little wet in a indiscreet places.

Thank you all for reading, and hope all you have a great 2022.

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I lost my job in July of 2020, and rediscovered my love of crossdressing. I was a programmer and in really high demand. I applied for a out of my range job at a very lucrative paying company that would have me over 6 digits. Jamie Lynn Boyde is my legal name and I made sure not to identify as male or female. My lock down had been spent learning about makeup, growing my hair out and losing weight. I had found a dress my sister had worn in high-school that was my goal dress. It hung in my small, country house as constant motivation.

Of course Amazon was a godsend. I was able to buy hair removal, spanks and I spent my days at home locked up feminizing myself. While collecting a very nice buy and out unemployment checks. August, I asked my doctor on a video chat about hormones and such since. My old company was paying my insurance till January 2021. Needless to say, telemedicine and I started hormones at age 24. By October things were opening up and I was down some 50 plus pounds and my butt was popping. I decided to go to a street costume party as a sexy witch.

Back to Amazon, hose, heels, and a really tacky sexy witch costume. I had been gaming as a female character, practicing my female voice and not one person called me out for being a guy. So I was pretty sure my voice could pass. Masks were required so I was sure I could pass if I didn't, just say it's Halloween.

The day before the party I did a test run. Shaved, lotion, Naired, and teased my now shoulder length hair. I even scheduled a hair appointment at gay friendly salon, yay chat support sites. I stepped out in black tights, a white blouse and black jacket top. My three inch heels, now second nature to me, clicked as I walked to my car. I caught a guy checking me out as he drove past with his wife. I blushed behind my sunglasses.

As I drove, I realized I like the attention I was getting. By the time I was at Horizons hair studio I was buzzed and on cloud nine. The internet had said Wear a pad for leaks, definitely glad I listened. Becky, my stylist, a very cute pink haired thin rail stylist was giddy as she worked on my hair. She complimented me on my looks, and my feminine voice. She was so happy, bragging I was more feminine than 90% of the clients, she gushed on compliments. I told her my idea, she was like.. raven black, tight curls with a green streak around your eyes. She asked if I wanted my ears pierced as well I was like of course I am yours to create with. She either heard cha-ching, or was actually excited because she blindfolded me and went to town on me. My butt did not leave her chair for two solid hours. When the blindfold came off I had three studs, in each ear, raven black hair and a green streak. I looked amazing even without makeup. She did my makeup for free. I walked out 300 hundred dollars poorer but looking and feeling like a million dollars.

I was on cloud nine as I left feeling super confident, and of course that meant shopping. I felt lots of stares, and the more I relaxed the more natural I felt. Men held doors open for me, women asked how things looked. I even went and got my nails done. I even snapped a few selfies for my tg support site, profile.

I was sitting at the food court, when a man sat across from me. He looked me up, and something seemed familiar about him. He took his hand and made a circle. "Jamie?".

My eyes got big, and felt my stomach drop. Turning slowly I smiled. "Yes?"

"It's me, Jason. Jason Wells. We worked at Grayson's together before the Covid layoff. We used to raid and hang." He looked me over. "I guess this is why you went missing." He held his hand up, "Not judging but look amazing, wish I had known."

I smiled as confidently as I could. "Yeah I kinda cut all my old life out. Since coming out." I pressed my lips together.

"Well if you ever want to hook up and raid... or need to vent." Nerd speak for trying to ask me out and say he is cool with the new me. He handed me a note with his phone number on it. He started to get up and my hand found his.

"Jason, do you have plans tomorrow night?" Jason was a bigger nerd loner than me. He was barely 130 pounds soaking wet. Short blonde hair baby face with blue eyes.

"No..o." His weakness made something in me snap.

"Am I pretty Jason?" He nodded. "How pretty? Am I a goddess or just average?" My voice firm and hard as I squeezed his sweaty palm.

"Ggggooodddessss" He stuttered.

I licked my lips looking up at my trapped little bird. "What would you do to go out as my date, little bird?"

"Annnyythhhhinggg" He stuttered.

"Anything?" I smiled evilly. "Prove it."

"How?" He spit it out.

I opened my contacts called Becky. Asked Jason for his cc and told Becky I had a client coming. Gave her his cc, and told him to go to this address to ask for Becky, once done come to my place, do not go home, nor call anyone. He nodded. I smiled as I had him. I smiled as he left in a flash.

I spent the next hour picking a sexy fairy outfit, then a black cat outfit. I got some panties and a bra and a cute nightie for him as well. Even stopped by an adult store for some lube and a plug. I was almost skipping as I got a text from Becky saying she was almost done asking if I wanted a picture. Make sure you do make up and tell him I am waiting.

I drove home with my presents almost giddy, having never done anything like this before in real life. I bit my bottom lip. It was Jason's fault for being so shy and diminutive. Something in me wanted to see him on his knees looking up, calling me mistress. I wanted..I needed to see his face when I took his cherry. I felt so deliciously evil. I was never so hard in all my life.

I was in my little black dress, and heels Ruby red lipstick on, wishing I had bought a skin tight dom dress. My tuck popped out regularly and I was so hard I didn't care. I heard a car pull up in the drive. I waited patiently as I waited for a knock. Finally a soft knock came. I forced myself to take my time and wait for a second knock. I saw him squirming as he timidly reached to knock again.

I opened the door, his hair was a short pixie pink do. His face was cute as button Becky had done a super job on his make up. I licked my lips as I smiled. "Mmmm Jason.. you look adorable." He looked at his feet. He was blushing. "Well what do you say?"

"Um, thank you." He looked down.

I stomped my heel for effect as I spoke. "Thank you Mistress Jamie". I lifted his chin. "Say it, correctly."

He was trembling. "Thank...thank you.. Mistress Jamie." I smiled and I caressed his face then leaned in and blew softly in his ear. "Remember you said anything." I whispered as his body shivered.

I wanted him right now. Honestly, I wanted to tear his jeans off and claim him right there in my doorway. "Now, Jason, before you enter you need to understand, you will be my date to the Halloween party tomorrow. But if you come in what I say goes."

"Yyyesss Mistress," He stuttered.

"If you don't want this then turn around now." I paused. "But when you come in you are mine. If you do not follow my orders I will kick you out." He nodded. "If you feel you can't do this at any time. Say butterscotch and leave."

"Yes mistress." This time it came more naturally and I knew I had him.

I smiled as he started to enter. "Only ladies and sissies allowed in this house, at this hour. Since you dressed like a guy I take it you are a sissy. A sissy needs a sissy name." I put my finger to my lip. "Mmm I know you are my sissy Jasmine. Jazz for short." His eyes lit up.

"Jasmine. Yes, mistress." He stepped in and I smiled as he looked at the many gifts I had waiting for him.

"Ok, Jasmine, strip." I gave my first real order. Without hesitation clothes fell off. His body was pretty smooth and so pasty white. "Undies too Jasmine." He was reluctant and I slapped his ass and the tighty whities fell. I looked down at his tube socks. He removed them. I looked him over, biting my lip. Letting his mind torture him while he stood naked before me. I looked at his cock three inches hard as a rock. Pre dripping like a facet. I smiled and grabbed his hard cock. Firmly handling it. "You ever had another guy handle your cock?" He shook his head. "I bet your girlfriend laughed at it." I leaned in, "I promise I will never laugh at it." His whole body shivered as I bit his ear lobe and sucked it. He started cumming right then. Years of cum, erupted in my hand as I dodged as it squirted on my hardwood floors. His whole body shivered and I lifted my hand to his mouth. "Suck it clean." He started to protest but I pushed my fingers and the wad of cum into his open mouth. He relaxed as he sucked my fingers. "Sissy never had cum before?" He shook his head. "You like it don't you." Not a question but a statement as he licked my fingers clean. "Lick it off my floor Jazz before it dries." She fell to her knees licking it with a hunger only true sub would have.

I smiled, she looked so adorable and obedient. I picked out some lacey pink panties. "Jazz stand up", I handed her a tissue to clean herself. She did as told. I handed her panties, "Slide these on." Without hesitation, she put them on and I reached and tucked her properly. "That feel better?" She nodded, I smiled.

"Jazz, I am going to make you into a sissy girl." Her eyes got wide. "For the next 48 hours you will be my sissy. Understand?" She gave me a worried look, then nodded. "Any questions?"

"Are you going to make me into a girl like you?" I nodded, and smiled. "Only if you are the only one to use me, is all I ask." I paused and thought about his request.

I smiled, "Until this date is over in 48 hours. Only I will use your body for my pleasure. Fair enough?"

She nodded.

"Mmmm, delicious then." I ran my nails over her bare shoulders and pulled her close. I slipped a training bra on her. Then slide in my old silicon false boobs. I could see her look at herself in the mirror. I smiled. She rolled her foot checking out her ass.

"It's a cute ass." She blushed. I smiled and pointed to her fairy outfit on the couch. "Put it on Jazz."

She smiled and lifting and sliding it on. She picked up the hose. I told her not yet. Once she dressed I had her spin, and show it off for me. She was too cute. I took both of her hands and we fairy kissed. She was in sissy bliss.

"Jazz, you look adorable." She blushed hard. "You should thank your mistress."

Fear shot across her eyes. As she saw my shecock showing in my dress. It was a thick 7 inch uncut monster and it was hard. She started to get on her knees. I smiled. Looked at the couch arm.

"Please be gentle." She whispered.

I smiled, "I only promise that once I am done fairy, you will never be the same again." She bent over the couch arm facing a full length mirror. I set a phone at the other end of the couch to record.

"What are you doing?" Looking at the camera.

"I promise you will thank me for this Jazz." She looked down, and bent over the chair arm. "Good girl." I pulled her panties down to the bottom of her ass. I rubbed it as she shivered. I had palmed the lube as I squeezed some on my finger. I rubbed lube into her rim. Tight rose bud. She tensed up. "Relax." She slowly relaxed.

I put a condom on and lubed it. I spread her cheeks wide and smiled as I pushed my tip against her entrance. Jazz was so tight, I smacked her ass and she yelped and inhaled and I pushed my head in. She squeezed trying to force me out. Her face pained as I smacked her ass again. "Relax sissy". She gasped and I pushed deeper. She whimpered how it hurt. "Relax Jazz, else I will rip your sissy ass." I rested my hands on her shoulders. Rocking in deeper.

"Please, Mistress its to big." She cried.

I smacked her ass and she yelped and I shoved past her wall. She screamed as I held deep. She tried to escape, but I held her in place.

"Relax, Jazz it's as deep as I can go. Look at the camera." I spoke. I rubbed her shoulder. "I am so proud of you baby. You feel amazing." She tried to smile.

Slowly, I rocked inside here letting the lube work inside her. She clinched as I pulled back. I shoved back and she squealed as I pumped in. "You have to accept I am going to to fuck you Jazz." I grabbed her short hair. Each pump she fought then she relaxed, her ass let me slide in and out faster as my cock rubbed her pspot. Her face was going from hurt to acceptance.

"That is it baby, you are doing so well." I pumped faster as a moan escaped Jazz's lips. Her ass gave a wet fart as I pumped in and out. Her moans came faster as she soon was rocking to meet my thrusts.

"That's it baby." I was in heaven fucking her virgin ass. "Does this feel good baby?"

"Yes mistress." I looked at the mirror, watching me fuck my sexy pixie. Her eyes and body rocking as she moans. Biting her bottom lip.

"Do you want me to cum inside you?" Our bodies were slapping against each other. She tried to answer but her body betrayed her as body shivered and her eyes rolled back as I felt her climax on my cock. I couldn't hold it any longer as I busted my nut in my condom.

I pulled out, my condom, hanging out her tight ass like a tail. I panted as I sat in my chair looking at her cute ass up in the air. Recovering from losing her anal cherry and her virginity.

After a few minutes, Jazz pushed herself from the couch arm and I pulled her into my arms. I pulled the condom out and pulled her panties up. Wrapping my arms around her she laid her head on my breast and cried softly. Realizing she had changed. I petted her head. Kissing her. "Shh, accept it or run from it baby." She curled up in her fairy costume in my lap. "Are you going to be my sissy?"

"Yes mistress." She whispered.

"Then go clean up. Clean your ass pussy with the enema wand. Use the red shampoo. I will have you a nightie hung. There is some lube for you to use." I paused to see if she understood. She nodded.

"Do you want to feel more fem?"

She nodded.

Following her into the bathroom, I gave her some hair removal cream for her privates and chest and arm pits. Rub it in and then wait 15 minutes then wash it off. She nodded. I hung her pixie costume up. I put my dress and underwear into the hamper. I slipped into the shower as she looked over my body. I washed her off and helped her wash and clean up.

She looked at my small b cup breasts, and my body, she leaned and kissed me. I pushed her against the shower wall as we kissed. Her hands cupped my breasts, and kissed my neck. She moaned as I pushed the enema I inside her. She moaned as she was cleaned out. It took four times before the water ran clean. She said her skin burned and I told her it was Nair. Once we were out of the shower I drew her a hot oil bath with a bath bomb. I hung a cute baby doll and headed to bed.

I was exhausted, usually I slept in panties and a cami. Tonight I was in my cami, pulling my hair up and working in my overnight conditioner. I laid back in my satin sheets and felt all tingly. I had sex as dominant woman for the first time in my life. I had gone out in public en-fem. It was a great day.

Jasmine walked tenderly, and unsure. I had no idea what to do. I patted the bed beside me. "Mistress will protect you." She smiled and slid in next to me. She felt amazing. I wanted her again. As she sucked her thumb, beside me. I turned to cuddle her but she was passed out.

I awoke to an empty bed the morning of Halloween. The party was tonight. I walked into my living room. Jasmine was looking at her pile of Jason clothes. She looked every bit the sissy without makeup, the pink hair was too cute.

"Do you want to back out?" I asked, grabbing a cup of coffee.

"One part of me screams, yes run away." At least he was being honest. "The other part of me knows you are right about me."

"I did warn you." I smiled. "You know as well as I do, your body is made to be fucked not actually fuck someone."

I opened my arms, my satin cami nipples erect and hard cock invited Jazz to me. He paused, unsure.

"Jasmine, come to your mistress." Without thinking she leaned and pressed into my arms.

"Mistress, I am scared." She sobbed. My hands held her. "I am afraid I won't be able to go back."

"But you make such a lovely girl." I lifted her chin. Kissed her lips. Her hesitation was only brief as her lips parted sucking my tongue. One hand pressed against my chest the other of her soft hands caressed my cock.

"Have you ever been wanted, Jasmine? Truly wanted?" She shook her head. "Hun I want you. I want you to be beside me knowing you are wanted. Knowing you are desired, needed, and at any moment about to get fucked."

"Really?" She looked scared. "But it hurt."

"Because you fought it, yet at the end you came so hard." I kissed her forehead. "At least your first lover, held you. All my lovers nutted, then made me leave."

She held me close. "I didn't know."

"Do you want to try it again?" My hand squeezed her panty clad ass.

"Will it hurt?" She winced.

"Only if you fight it." I rubbed her sore ass. "You want it, second, give into it." Her body pressed to mine.

"I want you to fuck me, mistress". She presses against my hand. "I have to know Jamie."

"Go the bedroom, panties off ass up, on your knees. Put a pillow under your belly for support." She skipped to the bedroom. I got the medium butt plug and rinsed it off.

Following her into the bed, her red star fish was on full display. Her skinny white girl ass was in the air, her nails spreading her cheeks wide. I smiled, I set the cell phone camera to video her face.

"Why the camera again?" She asked unsure.

"Last night I fucked a man into a becoming a sissy. Today I am going to fuck my girlfriend Jasmine for the first time." I spread large amounts of lube into and around her pussy ass. Deep as I could, almost half a tube. Jazz was already pushing back on my fingers.

"Does that feel better already, your pussy clean, lubed, and stretched?" I gave her porcelain ass a swat.

"Yes Jamie" She almost moaned.

I slid my cock in. She gasped and clinched. I let her adjust then as she relaxed and pushed deeper. Each wall we slowly pushed through. Till I was all the way in her. Her body tensed, I held deep till she rocked forward and pushed back.

"That's it baby, accept your getting fucked." I could see her eyes closed short breaths as I grabbed her hips and took my sissy. I pulled almost out and shoved back in. She let out a lust filled moan. Then buried her face in the pillow as she whimpered, "oh fuck...please don't stop".

I broke her, long thrusts as she sang so beautifully with her whimpers and soft moans. Her body trembled and I am sure the pillow was cummy mess. She couldn't get enough of the pain and the sensation of having her pspot rubbed. Even after the second climax, her body was on autopilot and she bounced back on my cock.

I wanted to be rough and cum in her fast and hard. But she needed this, I needed this. I wanted to give her something I never got, not yet any way. She moaned and cried. Throwing her head back she pinched her tits that had yet formed and begged for more. She was in full blown ecstasy. As she clinched on me, I couldn't hold back anymore. I started cumming in her ass, hard and more than I ever had in my life. My cock twitched. It felt like I pushed out huge globs of cum that were all trying to escape into her fertile pussy at one time. Till I fell on her back gasping together both realizing we had changed each other's world forever.

It was silent for a while, she squirmed. Then I knew. As a pendulum swings one way I felt hers swinging back hard. "Shhh, it will be ok.. I have you." I tried to calm her. She pulled away.