Candy's Adventures

Story Info
Tammy visits her trans sister Candy and friend in dirty tale.
15.8k words
4.53
21.4k
48
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Strong transgender and incest themes.

***

"Candy, come with me. This guy will pay us fifty bucks each to have sex with him in the bathroom," said my friend Jasmine who was shouting in my ear over the thumping beat of the dance music. It was a Friday night and we were out at Club Bumpers. Jasmine and I often went there just to dance and party but we got picked up more times than not and when the guys paid us it was a bonus. We would fuck guys for free if we were really into them but if it was the usual older, married men who were trying to figure themselves out and were still in the closet, we would ask for money.

Jasmine and I were both twenty years old but she had more experience than me. Jas is Vietnamese and her family disowned her and threw her out when she was seventeen when they found out that their son liked to wear girl's clothing and makeup. I met her at the YMCA just after I got a similar treatment from my dad. I was eighteen at the time though. I had a black eye and a suitcase to my name which had mostly my older sister's hand me downs. When I got to the Y, Jas could tell that I was a femme boy. She walked around in a skirt and wore makeup already which made me more at ease with myself.

Since then Jasmine and I have been best friends and part time lovers. She was the first one to call me Candy instead of Taylor when I coloured my blonde hair pink. It stuck. She taught me about turning tricks and we eventually made enough money from that and our regular day jobs to rent an apartment together. We have been room mates for over a year now.

On this night, Jasmine was wearing a little dark green dress. She is slim with long, bronze legs, slim arms and silky black hair that hung down almost to her ass. Hormone pills had given her a curve to her ass which stuck out because she wore five inch stiletto heels on her cute, open toe, black ankle boots. She had a green scarf on too which added to her feminine allure. Her breasts were still A cup but she had a padded bra to give her a little curve up there. Jasmine's makeup was flawless. She was so pretty and very passable as a girl. Her Asian eyes gave her an exotic appeal.

As for me, born pale and white, I went for a different look. I wore a lot of pink. Tonight I had on a black leather miniskirt with pink fishnet stockings, black, lace up granny boots with a four inch heel, my pink zip up hoodie with just a black bra on underneath. I also wore a black silk choker. Hormones had given me some nice, natural boobs with puffy pink nipples but I jacked up my bra with silicon cutlets to make them look bigger. I was zipped low enough to show off a bit of bra and my sexy cleavage. As you could imagine, my makeup choice was very pink and I wore false eyelashes to show off my baby blues. My lips were naturally plump with a pronounced bow for an upper lip. I wore glitter as well. My shoulder length pink hair was blown out and kind of wild. I chewed bubble gum too for the sake of character. I had more curves than Jasmine, with strong thighs from bike riding and my bum was already round before hormones. It was really juicy now and my sexiest feature in my opinion.

"Come on Candy, this guy is a frat boy and really cute," she emphasised as she pulled me by the wrist to the men's room. We giggled as we forced our way through the crowd of the gay night club. When we got there, we met Andy, the college boy with young Tom Cruise looks. As Jas introduced me, I pressed my body against his and gave him a soft kiss on the lips. He aggressively grabbed the back of my head and shoved his tongue in my mouth. I moaned in the kiss and sucked his tongue. I like aggressive, rough guys. Jas had already dropped to her knees and was unzipping Andy's jeans. Andy grabbed my ass under my short skirt and mauled it as we made out. Jas soon had his thick, circumcised cock in her mouth and was slobbering all over it. She really loves sucking cocks.

"Oh my God, you sluts are hot," Andy stated as he broke our kiss. He pushed my shoulder down indicating that he wanted me to join Jas on my knees. Jas was bobbing her head on his shaft so I started licking his plump, shaved balls. I gave them nice long sucks and also licked the base of Andy's cock. As Jas went deep our tongues met and I tried to force mine into her mouth while she sucked. It was difficult and Jas pulled off Andy's cock for a second leaving a long, stringy saliva trail. I locked my mouth on hers and kissed her sloppy mouth. This pleased Andy. Our kissing shows were always turn ons for guys. I broke away so I could get a taste of his cock. I went deep on the first suck and could taste a bit of salty pre cum. Jas grabbed his cock back and we took turns taking long slow sucks on it.

Andy started to get impatient and said, "Come on Jas, I want to fuck you."

Jas stood up and bent over the toilet. I slowly pushed up her dress to reveal her sexy ass. She wore a black thong which I gracefully pulled down. Andy was stroking his hard on with his hand. He had opened up his shirt to show off his firm, gym body. His pants were still around his ankles. Jas pulled her ass cheek open with one hand while bracing herself to the toilet with the other. I was behind her in a squatting position and spread her wider as I began licking her ass crack. Andy moaned as I rimmed her asshole with my pink tongue. I made it sloppy and wet as I tongue fucked her poop chute. I pried her open with two fingers as I continued licking her. Andy's cock was pretty fat with a large mushroom head so I worked Jasmine's anus really good to loosen her up. She was good. We took cocks up our butts often enough that we really didn't hurt any more but being wet and loose always made it easier.

Andy was pushing forward and I could feel his cock against my face. I turned and gave him one more sloppy suck before sliding to side so he could force his way into Jasmine's asshole. I watched as he shoved it in one thrust. Jasmine moaned loudly. It might have been for show or she really could have felt the stretch. "Fuck Jas, you got a tight shitter," Andy groaned, forcing himself inside.

Andy was hard and rough. He pulled her hair and pumped his cock in and out of her ass. Jas cried out as he did it. Andy looked at me watching and said, "Make yourself useful Candy."

I couldn't get a decent angle to suck on Jasmine's bouncing erection with the toilet in the way so I moved behind Andy and started kissing his bare ass. He made no objections so I licked his rosy pink pucker hole. Some guys get touchy about that so I was careful for a reaction. Andy grabbed the back of my head and pulled me in tighter so I stiffened my tongue and plunged inside his sphincter muscle. I kept time with his pumps into my friend's ass. I tongue fucked him as he fucked Jas. Andy was grunting and groaning. He fucked Jas harder and harder until he couldn't hold back anymore. He slammed into Jas deep and emptied his balls into her bowels. I slipped my tongue out of his asshole and moved back beside them. Andy breathed deep and grunted as the last of his joy juice drained from his cock.

Andy pulled out finally with his funky cock slimy with cum. I immediately wrapped my lips around it and started sucking him clean. It tasted of salty cum and Jasmine's musky ass. I swallowed down as I licked his cock pink again. As he steadied himself, I turned my face to Jas and got between her cheeks to lick her ass clean. Big dollops of dirty semen ran out of her gapping asshole. I licked them all up and swallowed. Andy caught his breath and said, "Damn, you are one nasty bitch." I giggled because yes, I was.

With Jasmine's ass clean, she turned to me and I stood up to meet her kiss. The two of us made out and she savoured all the nasty flavours in my mouth to show that she was as much a freak as I was. Well, almost. We were still making out as Andy zipped up. He pulled out two hundred and said, "Keep the change. That was one of the best fucks I ever had." Then he left.

Jas and I were still hot and bothered though. We both had stiffies. I pulled up my skirt and pulled my raging erection out of my fishnets. Jasmine's cock was already bobbing in the breeze. I pressed mine against hers. She knew what to do. She squeezed both of cocks together and started fist pumping them. Jas has a slim, smooth, seven inch uncircumcised penis that got hard a lot. Mine is six inches, circumcised, and quite thick. I kept my pubic area shaved clean too. I got hard all the time despite the hormone pills. I gyrated my hips to the rhythm of the music as our dick skins rubbed together.

We continued kissing, savouring the musky fuck tastes in our mouths. We were both so horny that it didn't take long. I went off first, spraying my spunk all over her hand and her cock. As she felt my hot sperm on her shaft, she went off soon after. She kept pumping until we were both drained. Then we both went to work licking her hand clean. I sucked her fingers as she tongued her palm. After we were clean and satisfied we fixed up our makeup and went back to the bar for some expensive drinks.

It was a typical night out for us; dancing, drinking, fun, fucking and cash. When Jas and I got back to our apartment later, we kicked off our shoes and got ready for bed. We had separate rooms but after I changed into my pink pyjama top, and nothing else, I snuck into Jasmine's room. She was still awake, wearing a black silk robe, masturbating with her hand. She stopped when she noticed me. Her hard cock bobbed up and down involuntary. I crawled into bed next to her and kissed her softly on the mouth. Then I rolled onto my side with my back to her. I wiggled my bare round ass against her erection. "I never got fucked tonight," I whined. "Can you help a sister out?"

Since neither one of us was a top or even dominant in any way, we rarely found ourselves on the top end of a fuck. Jas was horny enough though and she could not resist my plump, round bum. She slid her stiffy between my cheeks and searched out my asshole. I had taken the liberty to finger some lube into my rear passage before paying the visit to Jasmine's room. She had no trouble finding my opening and slowly pushed her cock inside me.

"Awww!" I moaned with satisfaction as she impaled me with her full length. I grabbed Jasmine's spare pillow and placed it between my legs and rubbed my swollen cock against it. It was my preferred method of masturbation. I grinded against her pillow as she fucked my ass in long slow strokes. I could hear Jasmine's breath get heavier and ragged as she pumped my butt. "Yes, yes girlfriend, fuck me with that sweet girl dick of yours," I encouraged. I was getting close to climax too.

I gyrated hard against the pillow as Jas stroked my ass in a faster pace. She bit down on my shoulder and tensed up as she buried herself balls deep in my colon. Cum sprayed inside me, filling me with her warm goo. "Yes!" I shouted as I came too, unleashing a heavy load on Jasmine's silk pillow. I then brought the pillow up to my head and started licking it clean. I placed my tired head down on it and fell asleep with Jas still deep inside me.

The following day, Saturday, I got a call at work from my sister. Let me clarify. I was at my normal job, a clerk at a well-known tech store chain. I had steady business, as I did most Saturdays. I was working alone for the last few hours, until 8 PM. The boss doesn't work Saturdays and trusted me to close up. It was actually pretty cool how I arrived in the situation.

I had been working in another store in the same chain at the mall, out in the suburbs where I used to live when I was still living at home as a boy. I had a good work rep with my bosses there. I was just another geek boy at a tech store. When shit started getting ugly at home and I had to move out, I knew that I couldn't travel all the way back to the 'burbs to my minimum pay job without a car. I was staying at the Y downtown. I told my boss about my predicament and he was very understanding. He said that he would gladly give a recommendation. It was the best I could hope for. Two weeks later I got a call from him, saying that the store downtown was hiring. They had a high turnover of staff and were desperate for qualified help. I had two years with the company and a good rep. He told me that the owner of the downtown store wanted to meet me and had an opening for an interview in an hour.

The problem was that I was out tricking at the time of the call. I didn't have time to run back to the Y and get changed. I was in a denim mini skirt, pink converse high tops, white knee socks and my pink hoodie. I had also recently dyed my hair pink. I was only a couple blocks from the store so I said, "Fuck it! This is me." I went to the store as is. The owner's name is Mister Marshall. He is an older man in his sixties, bald, chubby and with thick glasses. When I walked in, he was alone. He smiled politely and asked if could help me.

"Hello sir, I'm Taylor. Mister Addison at the mall told me that you were hiring and that I could interview. I'm sorry that I don't have a resume with me. I was caught off guard when he called and I was in the neighbourhood." I was using my girly voice. I always had a high voice and I practiced talking feminine all the time. Since I was living downtown, I used it exclusively. I caught myself using it mid sentence and rather than aborting and changing my tone half way, I just went with it.

Mister Marshall was staring at me and squinting through his thick glasses. "You're Taylor?" he asked. I nodded and smiled. I figured that was that and I would have to look somewhere else for a real job.

"Oh! I am so sorry," he said. I sighed but he continued, "Jim emailed me a letter of recommendation for you. Said that you were one of his best employees but had to quit because you were forced to move downtown." I was blushing. He giggled, or more like chuckled. "My mistake. I was thinking that you were a boy. I guess Taylor can also be a girl's name too."

I laughed along with him. "I suppose so. That happens more often than you think," I played along. I was still blushing.

He looked back at his print out of the letter and then back at me. He looked me up and down a few times before saying, "Well, if Jim says you are as good as this, then that's good enough for me. So long as you know your tech, are friendly with the customers, and show up for work on time, I'll be happy. It's hard to find good help in this part of town. Had to fire a lad just last week for stealing. Some quit without any notice when they find something better."

"You don't have to worry about that with me sir. I am very reliable and honest and hard working. I promise," I told him.

"Alright Taylor, I'll give you a shot. I don't mind the colourful hair. I like to think that I'm a modern man. Hell, you see all kinds of crazy hairdos down in this neighbourhood. So long as you keep it neat. Makeup should be minimal, nothing too shocking. I don't like a lot of jewellery though. It's not very professional," he said. I was wearing double ear piercings with silver hoops. I nodded agreement. He continued, "Do you still have a company shirt?"

He was referring to the black polo shirts with the company logo on them. I actually did and told him so. "Good, good, wear that for now. I can always order you more. Black dress pants are mandatory or in your case, a black skirt, so long as it's not too short with black tights underneath, if you prefer. I will leave that up to you. Can you start tomorrow?"

That was a year and a half ago. I became a model employee, with good sales. He trusted me to open or close the store when he couldn't. I even got a raise after three months and another after one year. He never questioned my gender or sexuality. He was very professional. Some of the other employees who came and went during that time had figured me out, as did some of the costumers. It may have scared some of them away, but I brought in a lot of regulars so it more than balanced out.

I was very happy that I could wear a skirt to work as I always did, with black tights. The hem of my skirt started at my knees when I first started but had inched up little by little as time went by. I was now in a mid thigh tennis skirt with pleats. I got tighter polo shirts in a girls' cut and always wore a padded bra to show my girly figure. Mister Marshall seemed content. He was nothing but nice to me since I started.

So on this Saturday night, I was finishing up, alone in the store when my sister called. I hadn't looked at my phone since my lunch break earlier. I usually had some regular guys texting me for dates. I didn't have many on this day, so I was excited to hear my sister's voice when it rang. "Hey baby brother, how the fuck are you?" Tammy asked.

"Oh my God, Tammy!" I squealed in my high pitched voice. She had heard my girl voice before, many times but was still getting used to it. She giggled from her end. I went on, "Bitch! It is so good to hear your voice. Where are you calling from?" My sister was in the Army. She enlisted right after the fall out with my parents. I think she did it to piss them off.

"I'm sorry babe. I should be calling you my baby sister now. You like to be called Candy, right?" she blurted. She didn't wait for my reply. "I'm at the airport. I got two weeks leave and I was wondering if I could crash with you at your new place. I can't go back to mom and dad and honestly have fuck all money for a hotel. What do you say?"

"I should really clear it with my room mate Jasmine first. But you are my sister, and I am sure I can smooth it out. I would love for you to stay with me. I missed you so much.," I cried.

Tammy had been my rock, my mentor, my best friend, and so much more in my teen years. She defended me against my dad when things got rough which got her thrown out too. She had to drop out of community college which she hated anyway. I had been hoping that she would stay with me and look after me as she always had but she joined the Army instead. I was a bit hurt but I learned to grow up fast on my own. She called me whenever she could. She had been in training for a long time and couldn't call very often but I loved when she did.

We made arrangements and her cab was dropping her at the store as I had an hour left to close. In the meantime, I called Jas and ran it passed her. Jasmine was a bit miffed at first as she thought my sister was too straight and would cramp our style. I assured her that Tammy was cool, that she was the one who helped me become the girl I was. I also assured her that I was responsible for my own sister. I also promised Jasmine a blowjob, my D and G belt and an I.O.U. for any kinky thing she wanted from me. That sealed the deal.

The cab pulled up five minutes before I closed. Tammy climbed out of the taxi and hoisted her olive green duffle bag over her shoulder. She was wearing tight, faded jeans with some holes on the knees and a grey "Army" tee shirt and a black leather jacket. Her ash blonde hair was tucked under an olive cap with loose fly-aways blowing in the early autumn breeze. Her figure looked stockier than before to me. She was always strong and athletic but the Army must have got her even more jacked. Her sapphire blue eyes were the same though. She entered the store and I ran to her and hugged her hard.

"Tammy!" I screamed. She picked me up off my feet effortlessly. She gave me a big kiss on the cheek and let me down. She held me at arm's length to get a good look at me.

"Tay...oops, sorry, Candy! You look amazing. You are so pretty. Oh my god, this hair. It's so long now and so pink," she gushed.

"And you are fucking jacked sister. You could probably beat up my boyfriend and he's a professional football player. How many push-ups do you do every day?" I asked.

Tammy giggled and said, "About a hundred, ...more or less." We hugged again tightly. "I missed you little sister, so much. I never stop thinking about you," she professed. She wiped a tear from my cheek as only an big sister could.