The Wicked Stepsister |

I stood in front of my bedroom mirror as I held my stepsister’s panties out in front of me. My hands were trembling from nerves and excitement as I stared at her slightly seethrough, pink undies. They had slightly frilly edges along the waist and legs. Unlike most of her gothic, black panties, they were feminine and typical of what most girls her age wore. I had been curious about what I would look like wearing women’s underwear for some time, but I finally worked up the nerve to raid Lizzie’s panty drawer.

As I bent over at the waist and stepped into one side of them, my erect cock was already getting in the way. After maneuvering my foot through the other leg opening, I started to pull them up, only to find that my thighs were slightly thicker than Lizzie’s. As I pulled the sides up to my hips I could tell that they would actually fit pretty well, if only I didn’t have a cock (in this case an erect one) and balls to try and fit inside them.

I didn’t expect my undersized member would be that much of an obstacle, but even my slender, fourandahalfinch pecker was quite problematic. It was impossible to keep it inside the waistband when pointed directly upward. I tried to distract myself in hopes that I could make it go limp and tuck it down, but I couldn’t get it to stay soft enough to pull off that maneuver. Instead, I elected to swing it to the left and tuck it inside them near my left hip.

At 5’6” and one hundred and twenty pounds, I’m about as slender as a twentytwoyearold guy can be. My delicate frame and mostly hairless body made for a pretty feminine presentation.

I spun around, trying to get a good look at myself from every angle. As I touched the surface of the panties, the fabric was incredibly soft and made any contact feel more intense than normal.

Not able to control myself any longer, I hooked my left thumb inside the waistband and pulled the panties down slightly. With my cock exposed, I stood in front of the mirror as I masturbated rapidly. In less than a minute, it felt like I was going to shower the mirror with my massive load. Instead, it was more like a volcano, as my cock released a patheticlooking little dribbler that wet my hand as well as Lizzie’s panties.

In a state of panic, I tried to pull them down and out of the way, but it was too late. I contemplated trying to sneak them into the wash, but I feared that Lizzie would know if she hadn’t worn them in a while. Instead, I did my best to wipe them down and dry them off, before I returned them.

My name is Cody and despite being twentytwo, I am still a virgin. I like both girls and guys, as well as others who may identify differently, but they don’t really seem to like me. If they did like me, it probably wouldn’t matter because I’m incredibly shy and I struggle to make new friends in person. Even in school, I was “ually invisible” to everybody else. Neither the girls nor boys seemed to see me, and I struggled to find a way to get their attention.

My stepsister, Lizzie, is a different . We have only lived together for about two years, that was when my mother married her father. Although she is three years younger than me, I remember seeing her when I was still in school.

She was very independent and confident. Usually clad in goth clothing and makeup, she was mysterious and sultry. Any fools who dared to poke fun or flirt with her were quickly sliced to pieces with her razorsharp tongue.

Lizzie was slightly slender and had long, straight, black hair and pale skin. She mostly wore dark lipstick and fingernails, as well as a few assorted piercings. Although she didn’t show a lot of skin, she did like to show off her midriff and her pierced navel. Most short skirts were accompanied with dark leggings, and she didn’t usually wear stuff with exposed shoulders.

I expected that living in the same house with Lizzie, I would get a free peek at her every now and then, or at least see her in her undergarments. That would not be the case, though. I did see her wearing a bikini a couple of times during family outings, but Lizzie didn’t usually spend much time in the sun.

My growing curiosity made me increasingly interested in Lizzie. Whether it was going through her panty drawer or her dirty laundry, I scrounged for any sort of cheap thrill that I could find. I am not even sure that she had any idea how much I was attracted to her.

The first time that I wore Lizzie’s panties would not be my last. It became an increasingly frequent occurrence, and I fully intended on wearing every single pair at least once.

One night, I was inside my locked bedroom as I tried on a pair of Lizzie’s black, hipster panties. Shortly after I put them on, I heard a “thunk” sound that made my stomach drop. Lizzie charged into the room, having freshly disengaged the lock with a small screwdriver or something similar.

“Yeah, I knew you were taking my panties, you sick pervert. Does that get you off, you less little man?” Lizzie barked.

I begged and pleaded with her not to tell our parents. As I did, Lizzie’s eyes lit up.

“If I agree not to tell them, you have to be my slave…Forever!”

I immediately agreed and thanked her repeatedly. When I asked her if she wanted her panties back, she responded, “Put them in the wash…This time!”

Although I was still nervous that Lizzie would tell people about what I had been doing, I was relieved that she seemed to be cool about it. When she didn’t make me do any of her housework the next couple of days, I thought that maybe she was going to give me a free pass. Even better, maybe she realized how attracted I was to her and felt the same way.

One Saturday afternoon, while our parents were off on a weekend getaway, I heard Lizzie pop my bedroom lock. She walked inside and shut the door behind her.

“It’s time to pay up, PantyBoy!” she chirped.

I could see a pair of panties in her hand.

“I want you to put these on for me.”

Confused as to what Lizzie’s intentions were, I cautiously took them from her hand and waited for her to leave or at least look away.

“Go ahead, strip! Take everything off, socks and all.”

I slowly removed my loungewear, starting with the least revealing stuff. I tried to turn away as I pulled down my briefs, but Lizzie insisted that I make no effort to cover myself.

It was already the closest thing to a ual experience that I have ever had. My cock was already rock hard and Lizzie was looking directly at it. I wondered if she liked it and if this could possibly lead to some sort of ual interaction between us.

“Keep going, put them on! I don’t need to look at your Chapstick any longer than I have to.”

Unfortunately, Lizzie was less impressed than I had hoped. I put the panties on, which were larger and more roomy than some that I had tried before. While they still showed a clear outline of my erect penis, I could position it in any direction without it poking out.

Lizzie pulled out her phone and started snapping pictures. I shouted and tried to cover up, but after a reminder about the deal that we made, I was forced to pose for her. She giggled and smiled as she ordered me to model in all kinds of positions. Then she ordered me to rub the front of my panties. Nervously, I slowly rubbed a finger up and down the length of my cock.

It only took a brief while for me to cum. Some of it stayed inside the panties, but a few drops seeped through the material only to be absorbed by the outside layer. Lizzie laughed at my subdued orgasm but seemed like she enjoyed watching the show.

She ordered me to immediately take off the panties, gather the laundry, and start up the washing machine. I followed her instructions and paraded back and forth through the house unclothed while under Lizzie’s close supervision. Once the wash was started, she told me that she didn’t have any further need for my services on that day. After that, she headed back to her room and closed the door.

I felt like after that moment, perhaps the two of us had bonded somehow. It seemed like our shared secret would have at least made us friends, but the following days proved that Lizzie didn’t feel the same. My efforts to make small talk with her were always quickly dismissed.

It would soon become apparent that Lizzie hadn’t had her fill of manipulating me. Roughly a week later, she once again invaded my bedroom. This time, she had a complete outfit that she wanted me to dress up in. There was a bra and a layered top along with panties, leggings, and a skirt. Lizzie even brought some cosmetics and applied them to my face.

With her phone in hand, she directed my every movement. Whether it was posing me or the slow striptease that she had me performing, it was clear who was completely in charge of the situation. The session ended with my panties pulled down to my knees and my skirt hiked up as I squirted my load all over myself.

Afterward, my instructions were much the same as before. I removed any remaining clothing, took it to the laundry room, and started the washing machine.

These sorts of interactions would become quite a regular occurrence. With our parents recently married and two adult children still living at home, they spent most weekends having quick getaway vacations. Though I could never quite put a finger on what Lizzie was getting out of these sessions, it was obvious that she was enjoying it in some way. I, on the other hand, was becoming increasingly infatuated with her and cherished our interactions, even if they were uncomfortable at times.

Lizzie’s behavior became increasingly domineering as time went on. One time, she presented a large hairbrush for use as a paddle and claimed that she wanted to see me get spanked with it until my ass was bright red. Because there was usually little physical contact between the two of us, I was immediately excited. I soon found out that I was expected to paddle myself.

Another time, Lizzie showed up with a dog collar, a lead, and a dog food bowl. All of them belonged to the family dog, Champ. The bowl, in particular, didn’t seem like it had been washed thoroughly, if at all. After stripping naked and putting on the collar, I was forced to eat Honey Nut Cheerios out of the bowl. Then, I was ordered to kiss Lizzie’s bare feet.

There were other humiliations that I would have to suffer, as well. Sometimes I was ordered to perform faux fellatio on random objects. Other times, I had to spread my legs and finger my boypussy while I repeated whatever Lizzie wanted me to say.

Then, I got the biggest surprise to date. Lizzie entered my bedroom one night with her tablet in hand. She pulled up a typical porn blog website and showed me an account called The Wicked Stepsister. I soon found that Lizzie had been posting pictures, GIFs, and videos from our encounters with her commentary included. It had been in existence for a couple of months, at that point, and had garnered a modest twelve hundred followers. Fortunately, she had edited the photos so they didn’t display a clear look at my face.

She showed me some of the comments and chat messages from other users. Of the ones directed toward me, some were from other mistresstypes claiming that they would enjoy dominating me. Most of them, however, were from assorted men wishing to use me for their personal enjoyment.

The most frustrating part, however, was that the bulk of the interactions were from people throwing themselves at Lizzie. All of this was going on despite the fact that a picture of me kissing her bare feet was the only image that she was even included in. It was the of my life all over again.

With Lizzie’s secret now exposed, our sessions took a slight turn. She would tell me that she had received a particular request that we were going to perform. Perhaps I would be expected to lie on the bed while she dripped hot wax on my body, for example. Most weeks would also include a brief update on her recent interactions with her blog followers.

Despite the fact that Lizzie had a new boyfriend named Mike, she still continued to use me as her submissive. Of course, I was insanely jealous of Mike, who couldn’t possibly have connected with her the way that I had. I’m sure he would never have gone to the lengths I had to please her with no sort of reciprocation.

Since our bedrooms had an adjoining wall, I could sometimes hear them quietly having . It always seemed to be relatively brief, and I wasn’t convinced that Lizzie ever got much satisfaction from Mike. I was positive that I could bring her so much more pleasure if only given the opportunity. None of that confidence was based on any record of past performance, but I was sure that my focus on her pleasure first and foremost would make me a superior lover to Mike.

One night, everything seemed to finally come together. There was the familiar sound of Lizzie popping the lock on my door. She still did so, despite the fact that I certainly would have let her in at any time. What was unexpected, though, was the fact that she was wrapped in her black bathrobe and from what I could see, nothing else.

Lizzie smiled and put her hand on my chest. My heart was pounding and I felt as if I was going to melt into a puddle on the floor.

“How would you like to lose your virginity tonight?” she asked.

Although I felt slightly embarrassed that she knew that I was still a virgin, it was still everything that I had hoped to hear from her.

“Yes! Yes, please!” I responded. I almost called her mistress, but I was sure that this wasn’t one of those scenarios.

Lizzie left the room and returned with a pair of thong panties and her makeup kit. She ordered me to strip off my clothes and then put on the panties. Afterward, she applied the makeup and styled my hair, as she often did. Lizzie sat on the bed and opened her robe, exposing a matching set of black undergarments. Although I had hoped that there was nothing underneath, it was as close to naked as I had ever seen her before.

She told me to get on my hands and knees, to which I quickly complied. I reached for her and she swatted my hand away. Lizzie pulled her phone from the pocket of her robe and aimed it at me.

“Are you sure that you want to lose your virginity, PantyBoy?” she asked.

I nodded affirmatively, to which she responded, “Come in, Baby!”

That sounded like a really strange response. It didn’t seem like that was how she would ask me to penetrate her. Did she mean something else?

My questions were quickly answered when Mike entered the room. He was completely naked, other than the condom that he was wearing. Mike was a lowlevel jock and not in terriblyimpressive condition. He was the sort of guy who played on the offensive and defensive lines on the football team as a void filler. That wasn’t the only thing about Mike that wasn’t very impressive. His cock was only slightly larger than mine, both in length and girth. If I were to be generous, he was perhaps on the low end of average in size.

Lizzie cackled at my response, and I immediately realized what she had planned for me.

“What? You didn’t think that I was going to fuck you, did you?”

Mike was behind me, struggling to keep his normalsized condom from sliding off of his manhood.

As Lizzie held up her phone, she ordered, “Do it, Baby!”

Mike knelt down and slid my thong to the side as he guided his cock toward my ass. As he pushed it inside me, I groaned and my upper body collapsed onto the floor. Despite Mike’s modest size, he was much larger than one of my fingers. It felt like he was going to tear me in two, and that seemed surreal considering how small he was.

Mike laughed at my response and boasted, “Yeah, how do you like this big cock!”

Lizzie piled on, praising Mike’s impressive manhood and cheering him on as he started to thrust away. She ordered me to extol the virtues of Mike’s prominent member as well.

As my body started to adjust to Mike’s cock, I noticed a strange sensation. I could feel every little wrinkle in the condom, which was a result of Mike’s underwhelming size. Just as I felt as if I could possibly try to enjoy the experience a little bit, Mike grabbed my hips tightly and held himself all the way inside me. As he cried, “Fuck!” I felt his cock twitching inside me, followed by a mild warmth as he pumped his load into the receptacle.

Lizzie congratulated Mike on his impressive performance although he finished in less than two minutes. Mike was breathing heavily as he staggered to his feet. The two of them leaned over my body and met with a lipsmacking kiss. As I looked up, Lizzie was rubbing the outside of her panties.

“Mmm, you are so good at that,…