The Step Sister

This story happened during my senior year. I changed names for privacy. Everyone except the parents (obviously) just turned 18 at the time.

Backstory: My father remarried in my early teens, and I ended up living with them for most of the rest of my teenage years. My stepmother had a daughter, Jessica, who also came to live with us for a few years. Both were tall blonds.

Being the boy in the family, I was asked to sleep on the couch and finally into the spare bedroom extension we were building. All was fine, but since it was a slow project, I would constantly have to move my bed and dressers in and out of the room for painting and electricity or whatnot on the weekends. And in the early days, there was no door yet, but luckily the room was out at the other end of the house, so I still had my privacy.

*****

The first incident I had with my step-sister was on a typical after-school day. One of those days when I thought I was alone at home. I took the opportunity to just hang around in a towel after my shower for as long as possible anyway.

I eventually did go to my temporary bedroom. First, I tossed my towel on the bed and just enjoyed being nude briefly. Next, I grabbed my homework and laid it out on my dresser for later. And finally, being the healthy boy I was, I got a little too excited in my nudity that I started jerking off on my bed.

The thing is, my bed was facing the opposite side of the room, so someone would see me jerking off if they just walked in. They just wouldn’t see anything until you reach the end of the hallway. And I would normally hear when people would be coming. No worries since I was alone, or so I thought.

Well, this time, I barely heard footsteps. It was so faint, and me thinking I was home alone, I just pushed the thought aside and kept jerking off. Well, after a few minutes, I finally came and jumped from my bed and went to reach for some tissue. That’s when I heard her gasp quietly. In that instant, I was so mortified someone had caught me. It was definitely the first time it happened. I pretended I didn’t hear her and walked to clean myself off. And went back to just laying on my bed, this time clothes, just thinking about what to do if she was really there.

Finally, I confirmed my suspicions when I heard her try to walk away as silently she could. I wasn’t really sure what to think about it. I never really thought about anything with my step sister in a sexual way, but what had just happened felt strange. I fought the inner struggle of if what happened was wrong but became so excited about it. I discovered my exhibitionist side that night.

The rest of the evening was pretty uneventful, but I did confirm later it wasn’t just my imagination and that she had been, in fact, home. And there she was. Just doing what I assumed was homework. Instead, she gave me an innocent smile as if she is asking if I needed something.

*****

The second incident happened a few weeks later when I got home early again. I saw her get home ahead of me. I decided I’d try my luck again and see if I’d get a spectator. I walked in and pretended as if I was alone again. I went for a shower and headed for my bedroom. I tossed my towel on my dresser this time so it’d be out of reach and grabbed a book out of my backpack, and started reading naked in my bed.

Once again, I heard her coming and just kept pretending to read before tossing my book on the floor. I was getting so turned on, but I didn’t start masturbating yet. I just laid there for about 2 minutes, thinking someone was checking out my penis. Then, finally, out of the blue, I said she would only hear me from the hallway in a low voice.

“Jess, are you there?” I waited for a second: nothing but silence. Then, finally, I jumped out of my bed and called again. “Jess?”

I went to the doorway and looked in the hallway, where I saw her smiling at me in embarrassment.

“Yes?” she said shyly before unsubtly looking down at my bare penis.

“Enjoying the show?”

“A little, but there’s not much to see. You know?” I thought she meant the confused idiot I was, as in I wasn’t jerking off like last time.

“Well, maybe you can help me out.” Jess laughed it off and shook her head, which I was a little disappointed with, but I guess I’d settle for a spectator. “Or just watch, you know, whatever.”

“Sure.” She came in chuckling a bit and just kinda sat on the end of my bed, waiting for me to lay down again. I was so turned on. She just seemed to be anticipating what was coming next. I definitely got my exhibitionist fetish solidified that day. “It’s just so small.” She said after I laid back down.

“Small?”

“Yea, like definitely smaller than what I’ve seen.”

That made me a little self-conscious, but I didn’t really care. I started jerking it.

She just kept her eyes on my crotch. “You’re not embarrassed, though?” She genuinely asked after a few seconds.

“Nah, it’s kind of a turn-on.”

“But it’s so small.” Jess scooted herself closer and started comparing her fingers to me. Then, she started putting her fingers right next to it and pull her fingers away, keeping her fingers apart with barely any room in between.

I shook my head at her, and she would just giggle.

“Hey, keep going. I’ll be right back. Don’t finish before I get back,” Jess said as she pushed herself off the bed, running out of the room.

I was just so excited at that moment that I came right when she left. She might even have been in the room still when I did. I was a bit ashamed that it ended so fast, but after a second, I got up to clean myself before she came back.

“You’re done already?” She said with a grin, shaking her head and sitting on the bed again. “God, it doesn’t even last long either. Tiny and speedy.”

“Come on. It’s not THAT small.” I was a little hurt; she thought I was small. So I figured I was probably average.

“Come, sit down.” She patted on my bed.

I was a little reluctant. I had already cum. And I wasn’t ‘at the moment’ still, so I wasn’t really sure if I wanted Jess here still. But after a second and her patting the bed again, I just kind of gave up and complied.

“Thank you.” She smiled and looked back down to my penis before reaching for a ruler she had brought with her. She grabbed my soft dick and propped it up next to the ruler.

I was a little nervous having a girl touch my penis for the first time, but it quickly turned to pride. So which was shattered pretty quickly?

“See? Not even one inch.”

I looked down and kind of just shrugged.

“It’s pretty small, John. I’ve seen a couple, and you’re like half their size.”

“Whatever, Jess”

“Hard,” she added.

“How old were they? And who’s showing you their dicks anyway? You don’t even have a boyfriend.” So I was convinced they were older boys, and I’d still have some growing left, right?

“Well, Lenard.”

Fuck, a boy from her grade (one grade lower than me)

“He showed me it last year because I was curious.”

Fuck so, two years younger than me.

“And Kevin when we were going out.”

What the fuck? That was 2 years ago. “Well, whatever. It gets bigger when hard. I’m a grower, not a shower.” I tried to argue and then realized she was still holding onto my penis. The thought had me getting a little excited again.

“Yea, barely. I remember 5 minutes ago, John. That ‘grower’ was about two inches. But whatever, maybe I need a better angle, right?” She smirked and finally let go of me. She reached behind her again and grabbed the camera, and began snapping pictures of me.

“What the fuck, Jess?!” I tried to hide a bit, but it was probably too late. I was so pissed at that moment.

“What? It’s just for me, and I’m not gonna show anyone. Plus, I’m not getting your face, so nobody will know it’s you. See?” She showed me the last picture she took, and it was just a really zoomed-in picture.

I kinda just shrugged. Maybe Jess will think of me later, kind of a win. Right?

She snapped a couple more and moved the ruler closer again. And got a few different angles. “Can you hold it next to the ruler?” She asked as she took some more pictures.

I rolled my eyes and propped it up as she did. Then, finally, she came off the bed and took a few more head-on, and then put the camera down.

“Well, what now, tiny dick?” Making sure to emphasize ‘tiny.’

“I don’t know, and you want to show me some of you?” I tried.

“No way. You barely showed me anything yourself.” She was relentless with her jokes.

I just smiled and shook my head again at the insult. “Homework then. I guess.”

“You’re no fun.” She rolled her eyes and tossed the towel back to me before leaving. “Fine. See ya, Little dick.” She then wiggled her pinkie at me and walked out.

*****

Nothing really happened for a few weeks after the incident. We played some sims together, and she’d make small penis jokes about my character. Overall it was pretty uneventful until a day when I got home earlier than her. I had been watching tv.

She then got home and immediately went into the bathroom.

I just minded my own business, but then I heard the shower going. My imagination started racing. I just sat there thinking about her being naked. I hadn’t thought about her before the incidents, but now I was really hoping I’d get to see her. Then, finally, I heard the water stop. My hopes grew at that moment. I turned off the tv and just sat attentively looking at the bathroom door.

After a second of nothing, lo and behold, there she was in her glory. First, a towel meant to cover everything, and once, she was trying and failing to tie in her hair. Then, with her arms above her, she walked out and into my parent’s bedroom to look out the front of the house, I assume to look if someone was coming home yet.

I caught a couple of glimpses of nipples as she struggled with the second towel.

Finally, she tried again by bringing all her hair in front of her and began wrapping her hair again before flicking it back again. I just sat in silence when finally I got the miracle I wanted. When she flicked her hair the second time, the other towel came loose, and she wriggled her body, trying to stop it without dropping her hands and failed miserably. She stood there weirdly with her legs crossed for a second before giving up and letting the towel drop entirely.

I couldn’t believe it. She was so beautiful. Her breasts were small, but I enjoyed seeing her everything. Finally, I looked down at her bush. Blond too. I must have had the biggest grin on my face and just stared in awe.

Finally, after she finished her hair, she dropped and grabbed her other towel and covered herself again. I knew that even if I didn’t say anything. She’d catch me.

“Wow, Jess” She froze and looked up to me on the couch and shrieked so loud I instinctively went to cover my ears. She ran into her bedroom, and that was that. She didn’t speak to me again that evening.

I tried to knock on her door to apologize, but she ignored me. At first, I was worried I’d get punished or something, but she never seemed to mention it to anyone else. I did apologize to her finally when I saw her the next day, but she just shrugged.

Things were a bit weird after that. I never really tried any more of my shows because I was afraid she was upset with me. At this point, I finally had a door for my bedroom and just closed it for when I wanted to be naked.

*****

The next incident I had with her was during one of my sessions with my door closed. I heard her in the hallway, and being that the bed creaked slightly when I would jerk off, I assume she knew I was also busy. But this time, she knocked on my door anyway. I stopped suddenly and pulled up the covers covering my erection.

“What?”

“Hey, John. Can you help me with my Math homework?” She asked as she came in and sat on my bed.

“I guess, but can it wait?”

The grin gave me such a hard-on. “Yea, sure, I’ll wait.” She put her math book beside her and just looked at me, smiling. Pretending to be waiting innocently.

And as if on cue, I dropped the covers and gave her a full view.

She laughed at my reaction and just stared at me for what felt was one of the best minutes of my life. “Stop for a second.” She said abruptly, and I did. She went to her book and took the infamous ruler last time and shook it playfully at me. She bit her lower lip and measured my erection. “Three and a quarter inches… And you say you’re a grower?”

“Whatever, shut up,” I said jokingly. But to my surprise, she didn’t let go this time.

She slowly started trying to jerk my little dick. “Can I?”

I couldn’t believe it. I nodded furiously.

She giggled at the reaction. Grabbing it tight and tried to stroke, but she was having a hard time on the downstroke. “It’s too small. How do you even jerk it?” She let go, and when I didn’t move, she grabbed it again. “Maybe with just three fingers? Oh, there, that’s better.” She sped up and became more consistent. “Do you like having a girl jerking your tiny dick?”

I just nodded.

“Do you?” After I didn’t answer that time, she let go abruptly. “I’m not gonna continue if you don’t answer me.”

“Yes, I do.”

“You do, what?”

“I like when a girl jerks me off.”

She shook her head and put her arms around her chest in protest. “Not good enough.”

“I like when you jerk off my tiny dick, happy?”

“Finally, you admit it.” She smiled again and continued where she left off. Again, a finger rubbing around the shaft, and finally, I could see myself cumming soon.

I didn’t know what to do. I just rolled my head back in ecstasy and left her to finish. I abruptly exploded on her and heard her gasp. Finally, when I came back to my senses, I could see her frowning at me.

“Gross.” She stood up and walked out of my room.

I felt somewhat bad. I had to quickly clean up and go to see if she was ok, but she was already in the shower by then. My stepmom came home soon after, so I just assumed there wouldn’t be much more excitement to the night.

She later came back for her book. “You better warn me next time.” She warned. “You’re lucky to have me even touching that thing, so you better respect it.” She said seriously before smiling again. She grabbed the ruler that was on my bed still and wiggled it around. “Three incher.” She went to walk out, but that’s when I heard her mom in the hallway.

“What’s three inches?”

“Nothing,” Jess said as she walked past her.

“What is it?” She insisted.

“John- Err, ask John.” My step-mom popped out her head in my room, and she just looked at me and asked again. “What’s she talking about? – Do I want to know?”

I shook my head in embarrassment.

She burst out laughing. “Well, I’m ordering pizza. What do you want?”

I couldn’t believe what just happened. I basically admitted to her I had a three-inch penis.

*****

Months went by, and she would occasionally come to my room when she wanted to give me a little help. It was never more. She refused when I offered to reciprocate in any way and never used more than just a hand herself. Finally, she convinced me to leave my door open regardless since sometimes she wanted a show but didn’t want to partake.

It was really exciting knowing she might be looking even when I just convinced myself she was there but wasn’t really. Finally, winter came, and the snow settled outside. She had a friend, Meagan, that she would hang out with sometimes, and she had told me she mentioned my shortcomings a few times. She never mentioned how she reacted to it, but it was fun thinking if it was actually true or not. Meagan never really talked to me or looked at me. I always assumed she didn’t like me.

Well, one after school, I knew Meagan was over, but it didn’t stop me from doing my thing. I had heard them coming down the hall this time. So I covered up in a hurry.

“Come in,” Jess said as she walked in with her brunette friend Meagan. They both stood beside my bed and looked at me awkwardly.

“Hey, John.” Meagan finally said

“Hey.”

“Meagan doesn’t believe me. You’re the guy in those pictures, John,” Jess said. “She thinks it must be some younger kid. She says I should probably delete it if it’s child porn. So… here I am to prove her wrong.”

Meagan chuckled embarrassed and shook her head at jess before looking back at me.

“So I figured you’d show her.”

“Err…” I started, but she just interrupted me and pulled the sheets off me before I could protest.

Both girls burst out laughing.

“Oh my god!” Meagan yelled.

“Tiny, right? Come, look, compare it to your fingers.” Jess said as she put her pinkie next to my little chub.

I just rolled my eyes at them and adjusted for them.

Meagan joined in and put her finger close but was reluctant to touch. My penis was definitely thicker than their pinkies, but they had me beat on length.

“God, you’re so small, John. She wouldn’t even believe me.” Jess said, moving away from me. She stood there in the middle of the room and watched Meagan. Finally, Jess winked at me and grinned devilishly. “I dare you to touch it. Meagan.”

Meagan pushed herself away instinctively. “What? No way! I dare YOU,” Meagan said, flustered.

“Fine.” Jess just grabbed me and made a little jerk motion.

“Oh my god!”

“What? He doesn’t care.”

“Are you really ok with that, John?”

I looked at her, trying my best not to shy away. “Yea, whatever you girls do what you want to do.” And did a not-so-convincing shrug.

Jess let go and moved away, letting Meagan move in and grab me herself.

I still remember how cold her hands were.

“I dare you to give him a blowjob,” Jess said, teasing to see if she actually would.

And without a second thought, she shrugged and wrapped her lips around my dick. In hindsight, she was pretty terrible, but at the time, it was incredible. She would suck and pull until my dick flopped out of her, and then she’d dive back in. “Like this? I can’t really keep it in.” Finally, she tried pushing it all in her mouth at once and easily did. “Don’t know if it’s considered deep-throating if it doesn’t touch the back of the mouth.”

And for a good few minutes, I had my first blowjob ever, and it was with my step-sister’s friend. I didn’t manage to cum, but after a while, she just gave up. I remember looking back down and seeing those beautiful eyes staring at her and me finally pulling away.

“Well, that was fun.” She said, and Jess just stood there completely astounded by what she just saw.

“I can’t believe you just did that.”

“What?” She chuckled softly. “He liked it. Right, John?”

“Very much so.”

“See?”

“Yea, but… Never mind, Jesus. I knew you had a thing for him, but I figured after you saw how small he is, you’d change your mind.”

“Who cares that he’s small? Not like he’s putting it in me.” Meagan looked me up and down one more time. “You’re a sweetheart.” She finally let go and walked out without looking back.

“What the hell?” Jess said before leaving after her friend.

The night ended with the family and her eating some mac and cheese at the table. I would just stare at her eating. I wasn’t sure if I just imagined things or if I was lovestruck. I couldn’t really look away.

When she saw me staring, she just smiled back innocently. It was one of the strangest days of my life, but there it was. When I went to bed that night, I saw a note from her. It was just her name and number with a heart crudely drawn.

Jess came to see me the next morning before school and asked if we had been a thing already. And When I said no, that we’d never have talked really before, she just shook her head in confusion.

We both were confused really. That same day after school, she didn’t come over with Jess, so I decided to call her and asked her out. And that’s all it took. My step-sister never came for another show again, but that didn’t matter.

I had myself, my first girlfriend.

*****

My First, Meagan…

My “relationship” with Meagan didn’t last very long, if you even want to call it one.

I would try to do stupid romantic things. The stuff young lovers get told they have to do. But, she wasn’t really into it and not at all in the public romances. I figure she probably had just developed a small crush for me while hanging out with my step-sister. And was a little ashamed of it when it actually became more than just that. Or maybe she just wanted to have a boyfriend for the sake of having a boyfriend, or else she’s ‘not cool.’ I couldn’t tell you why she agreed to be my girlfriend. But naive that I was back then, I was convinced it would last forever. I would buy her stuffed animals and super cheap earrings that she had used maybe once. But all that matters was that she seemed to be horny all the time. What more could a young man have asked for?

Our secret relationship had started with her pretending to come over to hang out with Jessica (my step-sister), and then she’d convince her to go hang out with me. Of course, Jess would soon catch on that we were a thing and just stopped inviting her over. But in those few days beforehand, it was fun to see how subtle we needed to be. She didn’t seem to be bothered by my step-sister, though. Whenever she came into my room, she would just come right up and cuddle right in front of Jessica. Sometimes we’d even have some fun under the covers too. Jess never stuck around when she found out we were doing anything naughty, though. At least, she didn’t stay in our line of sight.

I had overheard her in the hallway the one time. So, I’m not sure how often she would have had stayed for some shows. I had my suspicion that she was jealous of Meagan, but I was a young and horny teen. I didn’t care enough to do something about it.

*****

The first time we had sex really caught me off guard. On one of those days, Jessica and Meagan came into my room, and I was just watching some TV.

Meagan came to cuddle with me, and Jessica went to sit at the end of the bed. Glancing at us now and then. After a few minutes in the show, she subtly grabbed me under the blanket and slowly started to stroke me. I tried not to react too obviously, but I felt like I was in heaven. I stopped paying attention to the show and just closed my eyes. I assume Jess noticed because Meagan started giggling and let go of me.

“Come on, take it off for us,” Meagan said.

Without hesitation, I went to strip my pants. When I did, Meagan just kept staring at me with a small devilish grin as if to say ‘Everything.’ The shirt and underwear went off quickly too. I had to resettle back down again and adjust. I couldn’t help notice Jess just staring at my chub when I did.

Meagan grabbed me again and started giving me little pumps. Which I guess was more like she would grab the base stroke up until she reached the head and then fail to get a good downstroke. After a while, she just grabbed my little guy with her index finger, middle finger and wrapped it around with her thumb. Had a much easier time with that method.

Jessica just kept glancing back and forth from the TV and the action. She seemed so uncomfortable, which I didn’t really get why considering she had done things pretty similar to me herself a few times.

After a while, Meagan went in for a kiss. And that was when Jess got up.

“Well, I’m gonna leave you two, then.” She walked out of the room.

“Ok,” Meagan said a bit too late, not wanting to break the kiss early. That’s when she looked at me with such lust in her eyes.

I could not have been more turned on at that moment.

“I got a present for you.” She said, grinning. She pulled a condom from her pant pocket.

It took me a second to realize what it was. And then another to figure out where this was heading. I almost got a panic attack when I realized what was actually happening.

She took off her shirt to show off her purple bra and just hugged me putting her chest right in my face. “Take it off for me.” She said with my face completely covered by her boobs.

Desperately I went to pull it off. I tried yanking it every which way; I tried grabbing one end from the shoulder strap and nothing. I felt like I was failing at the most basic of challenges.

She just started laughing. “The latch is in the back.”

The idiot that I was, I had to really concentrate on it to the point of completely forgetting a girl’s boobs were in my face. Those didn’t matter at that time. My sole purpose in life was to get that fucking cock-blocking bra off. I eventually found the strap, but after pulling on it from every which way, she finally reached to it and unhooked it herself. I was defeated.

Without waiting for my help this time, she pushed herself away from my face and pulled the bra off.

I must have had the biggest grin on my face at that moment. I couldn’t believe it.

But she didn’t stop there. She stood up on my bed and knocked her head on my low hanging ceiling.

We both stopped and laughed.

She slowly started pulling her pants down and finally tossed them on the floor. Looking at me one last time, she seemed a bit nervous. But with a quick breath, she finally pulled down her panties. And there she was, completely naked… And all just for me. She then dropped down on top of me, her head going to my chest. She reached down and started playing with my dick again. Looking down to it and back to me. “You know. I just grabbed a condom from a public bathroom. I don’t know if it’s a ‘one size for all type of thing.”

“I’m sure it’s gonna be fine,” I said naively.

“Yea.” She kept stroking and then reached for the condom that she had dropped in the commotion. She let me go and started opening it. And being as we were both completely unfamiliar with it, she just started unrolling it in her open palm. When it was completely unrolled, she has compared it to my dick and just burst out laughing. “Yeah, I don’t think it’s supposed to be THIS loose… Maybe I needed to ask for the extra small condoms.” She teased, looking back with a tongue sticking out.

I just shook my head at her. What could I say? She had her proof right there.

She still tried to put the condom on. It did slip on pretty easily, which two dumb kids should’ve clued in that it could also mean it’d come off just as easily. But we didn’t think that far ahead. She then got up again. I saw her looking at the door briefly but didn’t really think too much about it since she didn’t really react. She then lowered herself a bit but had to reposition herself when she didn’t quite get the angle she wanted. She grabbed my dick to align herself, and finally, she looked back at me. “Are you ready?” She asked nervously.

“Always”

She smiled and looked back down. Then she lowered herself on what would be one of the most painful interactions in my life. My dick hardly pushed inside her before bending and getting squished to the side. We both recoiled in pain, and she flipped back on my bed.

“Ow,” I said, breaking the silence.

“I guess you weren’t hard or something?” She said, thinking that might have been the issue.

We later figured out it was because she was still too anxious. But being inexperienced, I just agreed.

“Well…” She started as she was rubbing herself. “Want to taste it?” She spread her lips for me, giving me a good view.

I didn’t need to be asked twice. So I moved in and pushed her to lie on her back.

She seemed to gasp at first, at the touch of my tongue, but after a few different angles and remembering to do the ‘alphabet,’ she began relaxing and let me reach further in.

I didn’t have a clue what I was doing. I just kept losing track of what the next letter was after ‘H’ since that seemed to get a good reaction from her. It was a lot of fun to experience all these new experiences with her. I don’t really know how long the whole thing lasted, but at some point, she just pulled herself back up and pushed my face away. I didn’t really want to stop. But I guess she had enough.

She reached down and slipped a finger inside herself, pulling it out quickly before putting it to my lips. “I think I want to try again.” She finally said.

“Okay”

She shifted around on the bed and repositioned herself again. I laid back down, not really noticing I wasn’t hard for a second try, but she definitely had. She was already stroking me.

“Your little guy needs to be awake again, I think.” The room was pretty quiet for a moment. I was just waiting for it to get up again. “You’re really tiny, you know. It’s pretty hard to stroke.” And that was all it took from her for me to get hard. That was probably when she realized (much earlier than I did) that I enjoyed it when she made fun of my penis size. “I wonder if I’ll even feel it when I finally get it in me. The condom fell off, so lemme put it on again.” She reached for it and started putting it on me. “Probably cause it’s so small, it just falls off.” She continued with her insults.

The barrage of the kind of flustered me. But that aside… Finally, it was time.

She propped herself up again and rubbed herself a couple of times. I just waited there for her. Trying my best to keep my hard-on as stiff as I could.

And in an instant, she dropped down, and it was done for real this time. She smirked at me as if proud of herself. She tried wiggling around. And then she started grinding on my little chub for a bit.

The bed started making a lot of noise at this point. It had me a bit worried someone would hear us even at the other end of the house. But that came second to what was happening. My first time someone fucking me. It was awesome. Even though nobody had an orgasm, I didn’t want it to end. It was like a life goal was reached for me.

After a few minutes, she went to move again. But when she did, my dick again slipped out of the condom. She just hovered there for a second, with the condom dropping out of her vagina and flopping down on my chest. Finally, she kind of just sat back beside me in disappointment. “Yea… Maybe we should stop.” She said. But before I could react, she grabbed the condom and playfully threw it at me.

I got grossed out for a second and smacked it off quick in disgust.

She was just laughing. She was already getting dressed again at this point, but not before going in for a quick kiss. “It was fun, though. We just need to get a condom more…” She looked down at my little chub again and back. She grinned and showed me her fingers barely an inch apart. “Let’s go with smaller.” She started laughing.

Meagan left the room pretty fast when she finished getting dressed, and we didn’t really hang out again that night. I guess she had gone to hang out with Jessica again, but neither of them said anything when she left for the night. I was overall pretty happy with the night, though, obviously.

I quickly came to realize, in the days after remembering the night, that she had figured out I would get turned on when she made fun of me the right way. So, unfortunately, and luckily, the teasing had continued.

She even went as far as doing it in public places. She eventually admitted she liked seeing me embarrassed. But she didn’t want to be mean about it either.

*****

Meagan never let down the humiliation after figuring out it turned me on. The night we first had sex was definitely all the information she needed to torture me.

I remember a few memorable phone calls from the phone in the kitchen. (This was before cell phones were as widespread as they are today) My parents were making dinner while I was talked to her on the phone, and she would start talking as loudly as she could about my penis and how small it was. I’m completely convinced they heard some of the comments since the phone was pretty crappy. Luckily though, they never brought it up.

We did have sex a couple of other times, but we had many problems with condoms slipping off. And worse was that after telling my parents we were dating, they started checking us when she came to my room. So sadly, sex became a no-go at my place. And she had always said her sister would kill any boy she’d bring over to her house. So it all put a damper on any chances at actual sex until we could find a new spot.

That didn’t stop us from fooling around, though. Whether it was handjobs during lunch breaks in the bushes or a blowjob at some boring movie, we couldn’t be fully deprived of our primal instincts. So I tried my luck at eating her out a few times too. We had some fun, but what I was beginning to enjoy the most was her teasing.

On one of those fun lunch breaks, she had convinced me to come with her to rebuy some condoms. We had figured that we would eventually get to use them. So we decided to go to the drug store furthest from our school so that none of the kids we knew would be around.

After going inside, I was a bit surprised she knew exactly which aisle the condoms were located. I was looking around, pretending to grab some random box of condoms and putting it back. Just shrugging at her. I didn’t really know what to look for.

She grabbed my hand and pulled me to the left end of them. “We need to get one of the smaller ones, obviously.” So she grabbed a couple that had these subtle descriptives like ‘snug fit’ or ‘slim trim’ and some less subtle ones that just says ‘small.’ She put them all away and started looking around. That’s when we saw a female store clerk nearby who was checking on stuff near us. Conveniently showing up to ‘rearrange’ some items on the shelves. Most likely making sure we weren’t just going for a five-finger discount (stealing).

But instead of getting weirded out by the clerk, Meagan gave me the biggest, most devilish grin and pulled me along. “Excuse me, mam.” Maegan, with the most innocent voice I’ve heard, said. “We’re looking for some help.”

“What can I do for you.” I saw her just grab a bottle from the top rack and just put it one bottle behind. Obviously not being productive.

“Well, we’re wondering if that’s all the size condoms you guys have?” Meagan asked.

“Oh, I mean, I think that’s all the sizes, but it’s pretty much in order of sizes.” She grabbed one of the standard boxes and showed it to Meagan. “See here it shows the measurements so you can kinda go further one end or the other based on that. Most of them are roughly this size, though.”

“Oh yeah, but that’s way too big.” Meagan quickly quipped. She grabbed the ‘snug fit’ box on the small end and continued. “Yea. See? This is too big too.” She turned the box to her and then showed it to me.

I just blankly looked at her knowing full well she was doing it on purpose.

“Right?” she asked, fishing for a response from me.

I’m amazed she kept a straight face the whole time. “Yeah,” I said as quietly as I could.

“Oh, I mean…” The clerk started getting flustered and picking up and looking at other boxes. She never looked at me again, funnily enough. “Yea, they’re pretty much the smallest the condoms get to, I think.”

“Oh… okay,” Maegan said, pretending to sound disappointed. She just relished on that silence a little longer, glancing at me every second or so.

“Well, I can go look in the back to see if there’s more. But I wouldn’t think so.”

“Oh, awesome! Would you please? If you could check. Honestly, the smallest ones you can find would be perfect.” The clerk grabbed the ‘snug fit’ box again and started down the aisle. “Something like extra-small or something like that!” She started talking so loud I’m pretty sure anyone in the store would have heard her at this point. Unfortunately, the clerk was far out of view, and she just looked at me, cracking up.

“He’s just … you know. Too small,” she said just to me before going in for a kiss.

God, I fell in love right there and then.

She handed me a box and started walking out in a hurry, pulling me along.

I quickly put the box in the wrong spot and followed her out. I noticed the cashier looking at me funny, but at this point, I didn’t care anymore.

When we got out, Maegan started laughing out loud. “Did you see her face? Oh my god!”

“Yea, I’ll never be able to go back to there again. Thanks for that.”

She just rolled her eyes at the thought. “So what? Who cares if some random lady knows you have a small penis.”

I got alarmed when she said it outside in public. But, we did get one guy from the bus stop looking our way.

“See? this random dude probably doesn’t care either.”

The guy just looked away. I’m not sure what I was expecting.

She was still chuckling to herself before she reached for something from under her shirt and tossed it to me. And, of course, it was the ‘snug fit’ condoms.

I was now an accomplice to petty theft, I thought to myself.

We never did get to use the condoms, though. There were a few times we could’ve maybe done something, but being the idiots, we were, we didn’t just carry a condom ‘just in case things happen. And sadly, nothing happened.

 

Read Tiny John 2 – Click Here!