A Superhero Sidekick’s First Time

Note to the reader: All characters in the story are at least 18 years of age, even if not stated in the story.

My name is Jennifer and I am a superhero crime fighter. Or at least a sidekick to one. Or at least training to be a sidekick. Two years ago I was a top ranked amateur gymnast. Making the Olympic team wasn't an impossibility for me. I was approached by a woman named Macey. She wanted to offer me a chance to be something more. Sure, gymnastics was a great sport, but was I truly going to make the world a better place by performing on the uneven bars better than my Polish counterpart? She showed me a path where I could save lives, fight actual evil and maybe even save the world. She could make me a superhero.

Macey was secretly 'The Busty Wonder,' likely the most famous super heroine in the world. Her name means she 'bust' crime so good it's a 'wonder.' I've heard men talk about her name meaning other things of the more sexual manner, but I know the real meaning behind the name. Yes, she did have very large, ahem, breast. And yes, her iconic costume top was a green leather corset that showed off a large amount of cleavage, but that was for maneuverability. As was the lacy green bikini bottoms that she wore. I did wish they would cover more of her butt though.

She also donned a dark green mask that hid her identity. No one knew that Macey was the Busty Wonder, except me. In revealing this secret to me, I knew this was my calling and I agreed. As far as my parents know, Macey is a private gymnast instructor who agreed to take me on as her only student. While she did have me continue to practice gymnastics, she taught me so much more. Fighting, small weapons, survival methods, the psychology of criminals, everything I could possibly need to join the fight against crime. I was eager to get out into the world and practice my skill in real scenarios, but Macey wouldn't let me until she was certain I was fully trained and ready.

For over 2 years we trained 3 to 4 hours a day. My parents had no clue what was going on. I would attend the occasional gymnastics competition to keep my parents from questioning what I was doing with my training time. I'd aim for a 3rd place finish typically. Good enough to show my training was worth it, but not so good where I could get picked up by the national team. I also kept up with my school work. Macey insisted that my grades stay high.

She also encouraged me to have a boyfriend, which I did finally get in the form of my classmate Daniel. He's sweet and cute. I am unwilling to go any further than kissing with him and I won't risk a pregnancy derailing my hero career before it even starts. He respects this, again very sweet. I don't get a lot of time to spend with him, but he doesn't complain.

I am now 18 years old and a senior in high school. I'm in peak physical condition with lightning reflexes and the strength of almost any male student in the school. My costume, after a lot of iterations, is ready for its debut. I went with an almost identical mask to Busty Wonder's, but I've attached black hair to it to hide my shoulder length blond hair. I went with a green leather top with straps. It shows more cleavage than I'd like, but less than what Macey pressed me to show. I'm not as large in the chest as her, but I'm still a D-cup despite all of the psychical training I do. Otherwise my bottoms are skin tight black bicycle shorts. They hug my butt tight but I wasn't willing to have any of my butt showing. Macey claims one day I will want to have less material down there constricting me.

While Macey gave me more freedom to design my costume, my superhero name she was insistent on me taking the title, "The Curvy Wonder."

"Oh, because of my right hook is so strong and my arm curves when I do it? Almost like a wonder," was what I said when she first presented it to me.

She stared at me a replied, "Right, that's why."

I felt embarrassed as her tone of voice obviously means I misunderstood that the name was actually in reference to my great ability to dodge. One of these days I'll confirm that with her.

One afternoon I was finishing up my mandatory 30 double back flips for the day. I was wearing the thong and sports bra Macey insists I train in. It's embarrassing showing off so much skin but it's just us two here. It's also more than Macey herself trains in as she likes to 'let her body be free.' On that day Macey finally gave me the news I had been hoping for. She was going to take me on my first mission as her sidekick. A local criminal organization has been smuggling advanced weapons in the area and the rumor was they were doing so with the help of high school students at one of the local schools.

"Which school is it," I asked.

"Mountain Hill High School, your school. Have you heard anyone talk about weapons or dealing with criminals at your school," Macey asked me.

"Busty (I'm never allowed to say her real name out loud while we train), you know I'm not very popular at my school. All of the guys at school only want to comment on my chest, except for my boyfriend Daniel who doesn't think about that. And all of the girls also only want to comment on my chest, but meaner. It's sad that girls with large breast like us have such a hard time getting popular in our society," I said impressed with my own ability to so poetically sum up unfairness in our society today.

Macey gave me an odd look, "That's entirely not true... you know what I'll address that later.

She continued on with the briefing, "I'm going to need you to help me gather intel and track down these criminals. This mission will require you to be both Jennifer and Curvy Wonder."

The thought of me fighting crime as myself and not my hero persona was exciting as it was dangerous. I'm not sure if even Macey has ever done that.

"You can count on me. Justice will meet the face of Jennifer, and it will be sorry." My hero quips were greatly improving I thought to myself.

"Just shut up and listen," Macey interjected. "This is your first mission. But it's more than that. This is when you will show me if all my time training you has been a waste or if you actually have what it takes to be Curvy Wonder. Perform poorly in this mission, and I'll never work with you again."

I went pale upon realizing how much was riding on this mission. This time tomorrow, I could be out of the hero business forever.

Macey continued, "You need to show me you will do whatever it takes to track down these villains. Failure will mean innocent people will die." My throat had gone dry, and I felt cold hearing this.

"Also, what is the most important thing to a superhero?"

My voice cracked but I managed to answer, "Their secret identity."

Macey nodded, placing her hand on my shoulder. "If your identity is revealed in this mission, I will have to abandon you. Criminals will hunt you down your whole life. You won't be able to be a superhero or even a stripper."

Macey had told me stories of other super heroines who had taken on young women to train and become sidekicks. However as soon as they got in the papers for their hero work, they turned around and became world famous strippers. It was a serious problem for super heroine recruitment. A lot of early work with Macey was focused purely on determining how much I desired to become a stripper. Very odd tests.

"I won't fail. I will be the best super heroine I can be," I said, finding the courage to respond.

"We shall see. The mission starts tomorrow morning. I want you to attend school as normal but meet behind the science hall at 7:30. Dress sexy," Macey said staring at me intently.

Despite what she thinks, I can dress sexy. "Yes Busty. The criminals will see the vengeance of law in the fist of my law bringers," I said clinching my fist very bad ass like.

Macey turned around to respond, stopped herself, took a breath, then simply told me to be ready at 7:30. She often doesn't know how to reply to my quips, something for her to work on I guess.

The next day I grabbed my sexiest outfit. I wore blue jeans but on the butt were several kitty patches. For a top, I wore a pink sweater. What really sold the outfit as sexy was a brooch I attached that had a multi color daises attached to it. They weren't real flowers, but everyone else didn't need to know that.

I got to the area behind the science hall early at 7:20 and within a few minutes I heard Macey's voice above me call out. "What the fuck are you wearing? I said dress sexy," she said standing over me on the roof.

"This is sexy! Daniel asked me out wearing almost this exact outfit," I said in rebuttal.

"I've shown more skin at funerals. Jesus Christ you are off to a bad start." Macey's comments startled me. I think she doesn't know what guys my age like. I'm the one with a boyfriend I thought.

Macey moved on to the task at hand, "I need you to start asking around and find a lead on the weapon smuggling. We can't take all day on this though. I will meet you back here at 9. Don't come back empty handed. I want a real solid lead."

I nodded back and replied with a hero quip I had thought of last night, "The path of the justice..."

Macey interrupted me saying, "Lose the fucking flower brooch at bare minimum."

I sulked and took it off. "It's not actually a real flower believe it or not," but when I looked up she was gone.

I got to work, walking around the halls asking anyone I could find if they knew anything about smuggled weapons. After the 9th person in a row replied with a comment regarding what I was hiding under my sweater, I tried taking a new approach.

I walked up to a group of guys, slickly saying to them, "Hey guys, nice apparels you are all wearing. So anyway, I'm tired of the law and want to work on crimes. The weapon smuggling variety. Do you know where I can go to do that?"

I was willing to do anything for the mission, even going as far as to pretend to want to do a crime or two. They looked at each other, and they waved me to come in close. This is it, I finally found my lead. I leaned in to hear all of the secret crime info.

"The only smuggling I know of are those giant titties you got smuggled under you sweater." "GOD DAMNIT," I yelled stomping away. Make that 10 in a row.

Before 1st period I got responses ranging from being told to flash my tits, engage in oral pleasures, stick objects in my vagina, and of course undergo sexual intercourse. And those were the responses I got from just the girls in my class. I had stopped asking the guys a while ago for my own mental sake. During 1st period I felt like crying. I had nothing and was going to fail being a superhero before I even got a chance to don my costume in public.

No! Justice doesn't give up and neither will I. I slammed my fist down on my desk as a show of my resolve. The whole class stared at me. The teacher whose lecture I interrupted responded to my out burst.

"Macey, I understand girls at your age can have strong... sexual feelings... but you can't let them interrupt class."

"No! That's not what..." but before I could explain myself he started lecturing again while the rest of the class giggled at me.

Once class was over and I disposed of all the crude notes I got asking about my strong sexual feelings, I came up with a new plan. Jacob was known throughout the senior class as the guy to go to for the latest rumors and gossip. After 1st period I saw him hanging out in an empty class room in the east wing. Inside, he was alone, texting on his phone.

"Hey tits," he said as I entered, not even looking up from his phone.

"It's Jennifer actually. Tits isn't a name anyone actually has. Hey, I really need information. You are the coolest guy in the school so I figured you would help me out." Awesome compliments like that are used to convince a source to reveal info to you.

In response all Jacob did was laugh to himself and turn to face away from me.

"Please Jacob, this is important to the school, even our whole community!" I pleaded and pleaded but I was getting nowhere. Looking at the clock, I had 15 minutes until I needed to meet back with Macey.

I knew what I had to do. It was embarrassing to offer, but I know it's something almost every guy desires. Guaranteed to get Jacob to talk.

"Jacob, if you promise not to tell anyone about it.... I'll show you my bra. I'll give you a minute to recover from the shock of such an awesome offer. But after I show it, you have to give me the scoop."

I took a deep breath. I hadn't even showed Daniel my bra, despite him actually asking for that one time. I was mortified and he never brought it up again. I felt really bad showing it to Jacob first, but this was for justice.

Jacob finally gave me notice. "Show me your bra? Are you fucking serious? Are you a time traveler from the 40s?"

"I'm not," I said confused by the assertion. Was that a thing?

Jacob continued, "Get you giant tits fully out, I don't give a shit about your bra, and give me a blow job. Then I'll talk. No negotiations. You are welcome to leave me along if you don't like the deal."

He wanted me to show him my naked breast? That was taking things way too far. No guy has even seen me in a bikini and now this guy that I have never talked to before today wants to see me topless. Oh crap, he also wanted to a blow job! I have never even seen a penis in real life before, let along touched or tasted one.

"Jacob I..." but before I could get anything else out he spoke up, "Just leave."

This was it. This is where I had to commit fully to being a hero. I approached him and got on my knees in front of him. I bumbled my words while I slowly lifted my sweater over my head.

"I.. I'm going to need access to your penis for this... I think."

My sweater was fully removed, my white bra was fully on display for him to see.

"Oh fuck, we doing this?" Jacob said standing up and undoing his pants.

My shaking hands reached behind my back, trying to find my bra hooks. I nervously responded, "Is there a style of blow job you prefer?"

I figured there must be different styles of blow jobs.

"I like the kind that where you rub those lips up and down my shaft until I release a gallon of cum in your mouth," he helpfully explained.

I was relieved to hear that because that's the only type of blow job I was aware of. I finally got my bra unhooked which caused my heart to skip a beat. I had no other steps to complete before this guy gets to see my fully naked D-cup boobs.

His pants were at his ankles and he was ready to pull down his boxers. I took the opportunity to simultaneously remove my bra as we would at least be equally embarrassed showing off our nudity at the same time. Maybe he was even more embarrassed as he was exposing his penis while my vagina stayed hidden in my jeans. I was now faced with a fully erect penis several inches away from my face. Again, I was relieved. He was already erect and I didn't know what to do get a guy hard. Maybe simply exposing himself was exciting enough to cause the erection. Having my naked breast on display was certainty causing a reaction to my vagina.

Seeing a penis this close was crazy. It was weird looking for sure, but also beautiful. I moved my head around it to see it at all angles. Did all of them look like this? I hoped to see more in the future to better understand that. But looking wasn't enough for me, I really wanted to touch it. I ran my finger along the side of it. I hoped this was okay to do as Jacob had only asked for a blow job, which only involved my mouth touching it. But I didn't hear any complaints from him.

It was so smooth and rigid. It reminded me of a flexed muscle. I put both of my hands around it and rubbed up and down his shaft. It was firm yet pleasurable to feel. As I was stroking it, I realized I hadn't actually started the blow job and Jacob was probably getting impatient. I looked up to apologize, but he seemed very content staring at my naked tits while I explored his penis. In just a couple of minutes I had gone light years farther with this stranger than I had in the 5 months dating my boyfriend and I was intending on going further. For justice.

I got to work and took his penis in my mouth, wrapping my lips fully around his perimeter. I don't know if it was the taste, the texture, or the fact that I was excited about willfully putting a strange dick in my mouth, but I immediately let out a moan, albeit muffled by the penis The dick rubbing up and down on my lips felt awesome. I completely forgot that I was blowing him for his pleasure, instead I just focused on leaning into the fantastic feeling of his dick on my lips. The taste was also awesome. I started rubbing the tip of my tongue on his shaft to experience more of taste. I kept expecting him to yell at me to stop using my tongue but he never did.

My moaning didn't stop and my pussy got more and more moist. My hands, now unable to hold onto the dick as I was able to fit the entire member in my mouth found themselves caressing my naked tits which felt better than ever. I lost track of time as all I had on my mind was dick. Suddenly I had a hot, salty sensation in my mouth and I realized he had ejaculated. I was startled and backed up suddenly. His dick continued to spray out semen onto my face and tits.

"I hope that was what you wanted. I've never done that before," I blurted out as I stood up.

After catching his breath he opened his eyes and looked at me with awe saying, "That was your first blow job? You decided to walk into this random classroom and give the first guy you see your oral virginity?"

I stood there with cum covering my lips and splattered on my face and bare tits, which were heaving up and down rapidly from my breathing.

"No! I came here to get information, remember? I'm letting you be the first to see my boobs and giving you oral pleasure in exchange for knowledge you possess!" I tried to explain to make it sound like I wasn't as slutty as he made me sound.

"I'm the first to see those massive tits as well? Jesus." He wasn't wrong but that wasn't what I wanted him to focus on.

I realized I never even told him what information I was looking for. Did he even know anything about students working with criminals or smuggled weapons? Did I just give my oral virginity away for nothing? I became very scared that I might be the first woman ever to blow a guy without anything to show for it, other than those fucking awesome feelings I got. Focus Jennifer!

"Tell me everything you know about any students helping criminals smuggle weapons in the school," I said forcibly while trying to subtly lick some of the cum off my lips. I needed to taste more of it.

I held my breath as my hero career depended on what I heard next. "I don't know. I think Daimon and his two loser friends, Greg and Dan, have gotten into some kind of shady dealings. They hang out in that unused shack behind the school."

Yes! I got the lead! I even know who Daimon is. I was so happy I jumped up and down, flinging some of the cum that was on my tits around the classroom. I composed myself and thanked Jacob.

"Thank you so much. You've done the community a great service!"

"Right...," Jacob replied, still staring at my cum covered breast.

I ran towards the door as I had only 5 minutes till the meeting with Macey. I stopped myself realizing I wasn't in a state to walk the halls on the account of all the semen on my face and my exposed breast (also covered in semen).

"Do you have a towel," I asked Jacob who was back in a state of ignoring me.

Using my hero improvisation, I started wiping up the cum with my hands and licking it off. I hoped I had future missions where I needed more information from Jacob. But I doubt there will be more crimes based out of my school. Maybe I trade him again for information on future tests, sports schedules or what people want for their birthdays, I thought while lifting my left breast up and licking the ejaculate directly off of it. I finished cleaning my self, got dressed and ran to the agreed upon area with Macey.