Oh, she is just amazing, truly perfect.

Of course, I’m talking about Megan, the girl from my psych class who is just perfect in every way. She’s cute, sweet, funny, and all-around a wonderful person. She has dark brown hair, brown eyes, and she’s quite petite, but honestly, I don’t mind the smaller proportions because she’s still perfect just the way she is, but also, to be honest, I’m not picky, mainly because I may have never had a girlfriend before.

I’m a typical loser, scrawny, and not much to look at. Most women wouldn’t give a second thought about ignoring someone like me, but Megan seems to enjoy talking to me. I don’t know how I managed this, but this insanely cute girl actively enjoys my company. I think it’s safe to say I’m in love, but first, I need to ask her out, and I do not nearly have the confidence for that yet. However, I am starting to suspect she might know the truth.

One day right as psych ends, Megan approaches me, looking rather excited. “Hey! So I’m throwing a party with my closest friends, and I was wondering if you wanted to come,” she said with enthusiasm.

‘No. Fucking. Way,’ I thought. ‘I’m one of her closest friends?’ A big smile comes across my face as I try to keep my composure. “Yeah, sure, sounds like fun,” I try to say in a calm demeanor, but ultimately still sounding dorky.

“Awesome! See you at eight.”

She smiles and touches my shoulder before leaving. I have never been invited to a party before, let alone one hosted by the girl of my dreams. This will be the most incredible night of my life and the perfect opportunity to tell her my feelings.

*****

I arrived at Megan’s house precisely at eight, I didn’t want to look like a loser who shows up early, but I also didn’t want to look like a jerk who shows up late. She answers the door in an adorable blue sundress.

“You look amazing,” I manage to work up the courage to spit out.

She responds with, “Aww, thanks, bud!”

Not the best thing for her to call me, but I think I could potentially win her over tonight. As I walk in, I see two other girls, I don’t know them personally, but I recognize them from campus. One is Hannah. She is a redheaded girl who has the best ass I’ve seen. I’ve probably stared at her more often than I’ve stared at my phone screen. The other girl is Bethany. She is tall and powerful. The few times I’ve tried going to the gym, I’ve seen this black-haired beauty outclassing everyone there. On top of all that, she has excellent proportions all around, especially her giant tits. Luckily or unluckily, each girl was wearing something that highlighted their best feature, Megan wearing a dress that makes her look adorable, Hannah wearing leggings showing off her perfect ass, and Bethany wearing a top that is so low-cut that I’m surprised I can’t see any nipple.

We all had a blast drinking and playing party games, and to my surprise, the other girls were having as much fun in my company as Megan has. We eventually decide to try playing truth or dare. Everyone agrees that it could be a lot of fun, and I can use this to learn more about Megan and how I can try to seduce her. Everyone mostly chooses truth, and nothing exciting comes of it, so I decide to pick dare on my next turn, to my eventual dismay.

The girls huddle together, and then Hannah says, “We dare you to strip for us.”

Of all thing things, they pick that? I was hoping maybe they’d make me kiss Megan or something, but stripping for them would be downright humiliating!

“Sorry, I’m not comfortable doing that,” I say, looking like a complete coward, and the girls agree.

“Wow, I didn’t know you were so lame,” Hannah says.

Bethany then says, “Come on, we’re all friends here.”

Still not convinced, I am prepared to stand my ground when Megan grabs my hand and says, “Please, for me?”

My face immediately goes red. The other girls figure out the situation real fast. Before I can articulate a response, Hannah blurts out, “If you do it, Megan will show you her tits!”

Now both Megan and I are both blushing a deep shade of crimson. Now, this is the opportunity of a lifetime. Getting to see her cute, perky breasts in their naked glory would be enough to satisfy me for life, so I reluctantly agree to these terms.

“Ok. Sure.”

The girls all observe as I begin to strip. My face has yet to get any less red during this process. I first take off my shirt to see the unimpressed looks on the girl’s faces. Of course, my scrawny physique wouldn’t do anything for them. I hesitantly pull down my pants, revealing my boxers. They now look a little more intrigued. Now’s the hard part, I’m not exactly the biggest guy around, and with how uncomfortable I feel at this moment, it’s probably not even at its full flaccid size.

Regardless, I freeze up and can’t seem to bring myself to drop my underwear. “Sorry girls, I don’t think I can.”

Then all of a sudden, Hannah pulls my boxers down to my ankles. Hannah and Bethany immediately break into laughter, holding their fingers together, while Megan looks away, clearly trying her best not to laugh. I somehow manage to blush even harder, and my hands shoot down to cover my tiny privates.

“There’s no use covering. We all already saw your baby dick,” she says as she slaps my ass.

I try to reach down and grab my clothes when Bethany pins me to the ground, holding onto both of my wrists, leaving me uncovered completely. I would be mad, but I got to see the best possible view of Bethany’s breasts from this angle, and now I’m starting to get hard. While in this position, Hannah took advantage and decided to take pictures and steal and hide my clothes. Bethany is just so strong I couldn’t even fathom getting free.

Once Hannah is done, she tells Bethany to get off of me, and she says the real fun will now begin. I demand that she give me my clothes back, but then Bethany holds my hands behind my back, exposing my little friend again.

“Listen, loser, we have pictures or your small cock, and if you don’t want those to go up on social media, you have to do what we say.”

I look down in defeat. There was no way out of this.

“Good boy, or should I say good girl, because, for your dare, you are going to go home, only wearing one article of clothing.”

Confused, I ask, “What does that have anything to do with being a girl?”

Hannah replies, “Because I’m so nice, you get to pick one of our panties we are currently wearing to put on for your walk home.”

I don’t know what would even be more embarrassing, streaking or walking only in panties. I guess I don’t have much choice, plus I suppose it would cover my dick.

“Megan,” I say, at least in some form of victory, I’d get to take home Megan’s used panties.

“Excellent choice,” Hannah says.

Megan blushes as she slips her panties down from under her dress and holds them out to me. They were the most adorable panties I’ve ever seen. They were pink and said ‘princess’ on the butt clearly, they suit her very appropriately, but this would be incredibly embarrassing for me. I slip them on. They ride up a bit in the back and feel tight in the front, despite having a small penis, but feeling the warmth from Megan’s private region against mine almost made this worth it.

Hannah slaps my ass again. “Alright, time to go home, Princess.”

They push me out of the house, and I start my run. I have never run so fast in my life. A few cars spotted me, they usually honked, but I was determined to get home. I finally get back and go to my room and drop onto my bed where I can eventually end this humiliation. I was so exhausted I didn’t even bother taking off the panties. I just pulled out my phone and saw one new message. I opened it to a picture that blew my mind. It was a picture of Megan’s breasts.

*****

Days have passed since the stripping incident, and I haven’t even talked to Megan since, but I have jerked off to that picture of her tits at least 20 times.

I’m just not sure how to talk to her again after that humiliating night. I’m sure she thinks less of me after running home in pink princess panties, so what could I possibly do now to try and salvage any form of relationship?

I mind my own business throughout the day until, surprisingly, Megan texts me asking to hang out today. Indeed a perplexing situation. On the one hand, I do still like her, but I’m not going over there again just to get humiliated by her friends, so I text back, ‘I’m not so sure.’

She responds with, ‘My friends won’t come this time. It will just be us.’

This immediately changed my attitude, just us, all alone? It didn’t take much time to tell her, yes, and I got excited about seeing her.

I get in my car and start heading over. She texts again, and I only see the first part as I’m very focused on driving and refuse to use my phone. ‘Oh, and don’t forget to bring—’

I wish I caught the rest of that, but I can’t afford a ticket for texting and driving. Plus, I’m already halfway there. It wouldn’t be convenient to turn back for anything. I get to her house, and she answers the door. She notices that I’m nervously looking behind her.

“It’s okay silly, they aren’t here,” she says reassuringly. She then says, “Did you remember to bring a swimsuit?”

So that’s what she texted. I completely forgot once I got there. “Oh no, I’m sorry, I didn’t see your text.”

She says, “It’s okay. I just really wanted to go swimming with you.”

Now I feel horrible. Not only did I make her sad, but I also lost my opportunity to see her in a swimsuit, so I said, “Do you have a brother I can borrow a suit from?”

She responds, “No, I only live with my mom, but I… Nevermind.”

She cuts herself off. “What’s that? I’m willing to do whatever it takes to make this work.” I am becoming more determined.

“Well, I do own two different suits. Perhaps you could borrow one.”

I cannot believe I’m getting put into a situation where I wear women’s clothing again. “I’m not so sure,” I say when she starts tearing up a bit. I didn’t know this meant so much to her. “Okay, can I see the options first?” I say, immediately regretting, but she perks up, and she grabs my hand and leads me to her room.

She pulls out the two suits. One is a black and white striped bikini, the other is a one-piece light blue swimsuit, both seem like bad options, but at least one would cover me more. I say shyly, “I could wear the blue one.”

She gets very excited and hands it to me. “You’re awesome! You can go get changed in the bathroom.”

I smile hearing her compliment me, but now I am forced into cross-dressing again. I get naked and stare at the suit. It at least looks normal. Maybe I can pretend it’s a wrestling singlet. I put it on, and it’s comfortable, it feels very light and free, but then I look in the mirror and feel embarrassed again. It’s so thin I can see the entire outline of my tiny dick, and it also shows a considerable amount of butt check. It’s almost looked like I was checking out a woman’s ass, was mine always this feminine? I must have been staring for too long because Megan knocks at the door, asking if everything is okay. I respond and open the door, covering my crotch.

She blushes and says shyly, “You look adorable.”

I couldn’t help but notice how cute she looked in the bikini. I respond, “You too.”

We both then head out back to her pool.

I stare into the water. If I get in, I commit myself to swimming in a women’s swimsuit. I’m contemplating when Megan just pushes me in! She then jumps in as well. I emerge at the surface when she comes up behind me and hugs me.

“Thanks for coming over,” she says sweetly.

We then have a lot of fun playing in the pool, so much that I completely forget that I’m wearing her swimsuit. We bounced a beach ball, played with water guns, pool noodles, etc.

I decided to grab her gun and take it away to tease her. I had it up out of the water where she couldn’t reach.

“Hey! That’s not fair. I’m defenseless!”

She swims up to me. Her breasts are pressed against my chest as she reaches up for the water gun. I blush and stare into her eyes. Then she stares back. Then at the moment, we kiss. Never expected my first kiss to happen like this, but I’m certainly not complaining. We kiss for a good few seconds until she feels my boner poking her leg, and she pulls away.

“Sorry for that,” she says, blushing immensely.

“No, no, I’m glad,” I awkwardly say, smiling.

She then decides it’s about time to dry off. When I get out, I’m once again covering my crotch, but this time it’s because I want to hide my erection. We dry off, and I head to the bathroom to change. I noticed that the swimsuit had ridden up more than before, and most of my ass was on display. ‘That’s it,’ I think. ‘No more cross-dressing.’

I change and meet with Megan before I leave. “Thanks again for coming over. It was a lot of fun,” she says.

I respond with, “It was a lot of fun coming over.”

We then hug before I walk out the front door. I drive home, thinking about everything, and despite the weirdness that came with wearing the swimsuit, this was the best day ever.

*****

I’m daydreaming about Megan, the perfect girl, and now my first kiss in class. I’m sitting there in bliss, thinking about how wonderful life is when I suddenly get woken up by a sharp tug at my underwear. I see that it’s Hannah.

“What’s up, nerd?” she says, giving me a wet willy.

I pull away, trying to adjust by boxers from the wedgie and clean the spit out of my ear. “What do you want, Hannah?”

She responds with, “What, I can’t say hi to my new friend?”

Friend? The only encounter I’ve had with her was being stripped and forced into panties against my will. How are we friends? I try to ignore her, and I keep walking out of the lecture hall, when she pantses me, luckily no one was left as I was daydreaming for too long earlier. As I reach down to pull up my pants, she slaps my ass.

“Hey, baby dick, why don’t you come over to my house tonight.”

I am staring in complete confusion, but before I can respond, she cuts me off.

“And remember, I do still have pictures of your little friend. It’s only one press away from letting the world see it.”

I have no idea why she wants me to come over, but I can’t let those pictures get on the internet. “Fine,” I say, defeated.

“Good boy. Now, be there in two hours, don’t leave me waiting.”

She then kicks me in the balls and leaves while I fall to the ground in pain.

*****

I showed up at her house on time. It turns out Megan gave my number to the other two, so Hannah could just text me her address. I knock on the door, and Hannah wears a long T-shirt and black panties. My eyes widen at realizing she isn’t wearing any pants!

“Good, you made it. I hope you know you won’t just be here to hang out,” she said.

I figured as much but precisely what she’s planning is beyond me.

“I need to get my place cleaned for a party, and you’re going to be my personal maid.”

This is ridiculous! After everything she has put me through, I can’t believe she dares to make me clean her house.

“Now, I’ll give you an option of your outfit. You can be my hardworking maid or my loyal puppy.”

That’s a new one. Getting a choice? Of course, the maid outfit would involve cross-dressing again, and I’m no furry, but the sound of wearing a dog costume doesn’t sound bad at all in comparison. “I guess I can be the dog.”

She responds, “Puppy, you don’t have enough dick to be considered an adult dog.”

She then leaves to grab the outfit, but when she comes out, I realize it wasn’t what I expected at all. Coming out, she is holding a headband with dog ears on it, a dog collar, and what looks like a cosplay tail.

I start to put them on when she interrupts me, “No, dumbass. You have to take off your clothes first.”

There it is. That’s where the real humiliation takes place. I take off my clothes, not too embarrassed this time as she’s already seen my dick a couple of times (let alone she has pictures she probably looks at frequently). I quickly put on the ears and collar, but I’m confused about the tail. The end is this weird-looking round piece of metal. What is this supposed to connect to? I ask, and a devilish smile creeps upon her face.

She says, “Allow me to demonstrate,” and she grabs the tail out of my hands. She then swiftly shoves the metal part right up my ass.

“Ahhh,” I yelled. I don’t know what’s worse, the stinging of having my backdoor invaded or the cold metal inside my body. “What is this?” I say, upset.

She responds, “It’s a butt plug. How else are you going to wear a tail while you’re naked?”

I stand in front of her awkwardly. Maybe it’s because I’m still uncomfortable being naked in front of her, or perhaps it’s this thing that’s shoved up my asshole, but I just feel weird.

“From this point forward, I will be your mistress, and you will only address me as such when you are in uniform.”

I respond, “Yes.”

She slaps me. “Yes, what?”

I respond, “Yes. Mistress.”

She says, “Good boy. Now to show your unflinching motivation to be my bitch, you need to do something to prove you are beneath me, but what should that be?”

I get annoyed. “Hell no, this is already humiliating enough. I’m not kissing your ass any more than cleaning your house in this humiliating outfit.”

Her eyes light up. “That’s it! Kiss my ass!”

I look at her, dumbfounded. She turns around and pulls her panties down, mooning me with her perfect ass. “You will prove you are my bitch by literally kissing my ass.”

My cock starts to twitch at seeing such a magnificent sight, but kissing her ass didn’t seem to be my favorite course of action, mainly because I have no idea how I’ll live this down. I hesitate, weighing my options, when she yells, “Now bitch! Or every girl on campus will see your pathetic cock.”

I lean forward and stare at her ass in all of its glory. I’m not opposed to touching it or kissing it. For that matter, it’s the principle of how humiliating this act is. I then pucker my lips and place a kiss on her left cheek.

Hannah says, “See, was that so hard? Now that you are officially my bitch I want you to check in after every chore and kiss my ass so I can make sure you stay on task.” She then pinches my cock between her index finger and thumb and leads me to the bathroom. “First, I want you to clean this toilet, make it so clean you could drink out of it.”

I get started on my task, knowing it’s not worth fighting anymore.

I finished cleaning the toilet, and I gotta say, I think I did a fantastic job. Perhaps it was the fear of having my secret revealed, but this toilet almost looks like new. I call her in to inspect, and she does seem impressed.

“Well, now it’s up to the test,” she says.

I respond, “What test?”

She says, “Well, let’s see if it’s clean enough to drink out of. Go ahead, puppy.”

There’s no way she expects me to drink out of a toilet, even if I did clean it. While I’m hesitating, she grabs me by the balls hard and says, “You are in no position to refuse.”

I get down on my knees and slowly stick my face in the bowl, I pucker my lips, and she slaps my ass. “Like a puppy,” she demands.

I stick out my tongue and start lapping up the toilet water. It doesn’t taste particularly gross, but knowing it makes me want to vomit.

“Good boy, now for your reward,” and she pulls down her panties, and I place a kiss on her right cheek, leaving a bit of toilet water there as a result. “Next, you will clean my room,” she says as we head there.

Upon inspection, there are clothes all over the floor. I begin this pick them up when she says, “Actually, I want you to pick them up like a puppy.”

Although a little more humiliating, this isn’t that big of a deal, I do blush when I have to pick up her bras and panties with my mouth, but this is not nearly as bad. She comes in when I finish, and I know the routine, I kiss her left cheek again, and she explains the last chore.

“Now, I want you to clean the pool.”

She wanted me to go outside? It’s one thing to humiliate me in front of her, but it is another to take it outside, but knowing I’m not in a position to argue, I agree and follow her outside. I come out covering my dick when she tosses me the cleaning net and goes inside. I try to clear out the pool as fast as possible, constantly looking around to ensure her neighbors aren’t out.

She then comes back wearing the skimpiest pink bikini I’ve ever seen. She then lies down on a towel to sunbathe. “Keep going, puppy. You don’t want my neighbors to call the cops for exposing your fun-sized package.”

I kept moving quickly, splashing water around the pool as I cleaned it, which wasn’t a problem until I accidentally splashed Hannah.

She gets up and grabs me by the balls and pulls hard, her nails digging into me. “Listen, you little shit, make me mad again, and I’ll make you walk home like this.”

My knees start to tremble from fear and Hannah’s pressure on my testicles. She stares into my fearful eyes. I look like I’m about to cry when she kisses me? I look at her in complete confusion when she pulls away and then knees me in the crotch harder than she ever has, I fall to the ground, and I swear it felt like my balls were temporarily inside my body.

After the pool, she says I’m free to go and gives me my clothes back. I head home thinking about the kiss and wondering what it means. She then texts me later that night saying, ‘Tell anyone about that kiss, and this is going online,’ and she sends a picture of me in the dog outfit with a thong in my mouth, my unimpressive cock exposed. Well, if I can take any solace from this experience, at least I got Hannah to kiss me after I drank from the toilet.

 

To be continued…?

 

*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Remember, even with limited editing. It doesn’t mean any possible major flaws in this story were fixed.