My gf, Amy and our friend, Hyun, pay off a lost bet to me. (MFF 21) (role playing) part 1

This is continued from a long series about my gf Amy.

After eating some breakfast and sitting around awhile, Amy, Hyun, and I were going to go to the science building to check our final exam grades for molecular biology. Hyun and Amy both told me that if I scored higher than them on the exam, they would both put on their old Catholic high school uniforms and we could do whatever I wanted.

We left my apartment walking across campus on a cold, dreary, December day. It was the Friday right before winter break and all of us were done with exams. We were all staying until Sunday, only because my band had a gig Saturday night. Sarah walked with Amy, Hyun, and me, but when we got to the science building, she headed off to her own apartment. Sarah said, “See you later, I don’t want to set foot in that building ever again.” Sarah started as a chem major freshman year and rapidly decided to change to a non science program.

Amy, Hyun, and I went up to the biology level. We found our exam grades posted on a bulletin board in the hall. As we looked at the scores, I said, “Fuck yes, I beat you, get out those plaid skirts girls.”

Hyun grinned and said, “You scored higher on the exam, but look, Amy and I both did better than you for the final grade.”

I said, “Wait, that’s not fair, we were talking about the exam score…you were going to put on your Catholic school uniforms…we were going to have a threesome, if I scored higher on the exam,
not the class.”

Amy said, “Calm down Jack, I think she’s fucking with you. It was the exam, not the class, we’re going to honor the bet.”

Hyun laughed and said, “You’re no fun Amy, I was going to mess with him. Look how desperate he is, he wants us so bad.”

We heard a throat clear and realized our professor’s office door was open just a few feet away. I thought he was probably gone for the semester. Pretty sure he heard all of that.

The professor called out from his office, “Jack, you did well on the final, you really redeemed yourself. It sounds like you had some…inspiration from Amy and Hyun?”, and he chuckled quietly.

Amy and Hyun were both embarrassed and we all looked at each other wide eyed. Amy mouthed, “Holy shit,” and shoved me towards the professor’s open door.

I said, “Yes, we studied together and we kind of had a bet about who would get the highest grade, sort of…it’s no big deal…just a funny bet,” and I pulled the girls into the doorway.

Amy and Hyun said, “Hi,” to the professor sheepishly.

The professor said, “Jack, you did well having these two as study partners…very well indeed. The two smartest and most beau…well, I’ll just leave it at that,” as he looked over the top of his glasses up at the girls and chuckled a little. “Enjoy yourselves.” He trailed off into laughing and shaking his head, as we moved away from his office door and said, “oh,
to be young again.”

Amy said, “Have a nice break professor,” as we all scurried down the hall to the stairs and started laughing.

Hyun said, “He definitely heard us.”

I said, “Yes and I think he is more than a little envious of me.”

I was practically bouncing along as we left the science building, walking to Sarah and Mary’s apartment, looking forward to a threesome with Amy and Hyun. Amy said, “We should do it tomorrow. We already fucked today Jack and you should rest up for this.”

I said, “Fine, I guess I can wait until tomorrow.”

Hyun grinned and said, “You want me to wear underwear under that skirt, right?”

I said, “Yes, specifically, like some ordinary white cotton…doesn’t have to be white…but like some ordinary cotton panties…maybe?”

The girls laughed. Amy said, “You’ve got like a real specific idea here, you’ve really thought about this.”

I said, “Yes,” kind of sheepishly.

Amy said, “So what are we doing? What’s your plan for us?”

I said, “Can we sort of role play a bit? Maybe I’m like the principal and you guys are in trouble for your skirts being too short?”

Hyun and Amy laughed hysterically. Amy said, “This should be easy to role play, I got in trouble for that all the time.”

Hyun said, “Same.”

I said, “Hyun, how do you feel about spanking?”

Hyun said, “Never really did that sexually, but seems like it could be fun.”

Amy had a big grin on her face and said, “Jack already knows this, but I love getting spanked, Hyun. I like where Jack is going with this.”

When we got to the apartment, Josie was in town to see Mary and come to my band’s show the next night. Josie came up and hugged Amy and me. Josie said, “Who is this hot chick with you guys?”

Amy said, “This is our lab partner, Hyun. Hyun, this is Josie.”

Hyun said, “Hi Josie, I’ve heard a lot about you, and you’re like even more beautiful in person than I imagined.”

Josie blushed a bit and said, “So, Hyun here has been…she’s into…”

Sarah said, “I was with her last night and she is into it, believe me. She’s fucking hot.”

Hyun was looking at Sarah and blushing now.

Mary said, “Sarah got to be with Hyun, that’s not fair. What are you doing this weekend, Hyun?”

Amy chimed in, “Hyun and I are paying off a bet with Jack. We have to put on our old Catholic schoolgirl uniforms and do whatever he wants because he got a higher grade than us on the final.”

Josie said, “That’s so nerdy, but hot. I want to see you guys in your uniforms. Well, someday I hope you would join Mary and me for some fun, Hyun?”

Hyun just giggled and nodded yes enthusiastically.

I made it to the next day, Saturday, without fucking Amy or masturbating. I arranged for Ben to be away from the apartment all day, although he was pretty intrigued by my bet with Hyun and Amy.

In the early afternoon, Hyun and Amy showed up at my place and they were both wearing their old high school uniforms and grinning when I opened the door. They both had their skirts well above their knees and their white, button down shirts unbuttoned pretty low. I hate getting dressed up, but I actually put on dress pants and a shirt and tie, because I was into this role play.

Amy had a very innocent expression and said, “Principal O’Neill, why did you call us to your office?”, as they stood in the doorway. I liked how she gave me a name and launched right into it. Amy liked this as much as me.

I said, “Come in here. Look young ladies, I’ve been getting a lot of complaints from teachers about how you are wearing your uniforms. Do you want boys looking at you like that? Putting impure thoughts in their heads?”

Hyun gave a very innocent look and said, “Principal, what’s wrong with our uniforms?”

I said, “Look Hyun, you’re a good student, I hope you’re not sassing me…the handbook is pretty clear that your skirts have to be below the knee.”

Hyun said, “it’s like that when I leave the house, but it just rides up during the day.” Amy nodded in agreement.

I said, “I wasn’t born yesterday girls, that doesn’t happen on its own. And, Hyun, I heard something really disturbing about you. I’m embarrassed to even say this, but I heard you sometimes don’t wear any undergarments.”

Hyun feigned shock and said, “I’m wearing underwear.”

I said, “Mr. Slater, the science teacher, said he had the misfortune to notice you weren’t wearing any underwear the other day. He’s a family man, do you think he wants to see that?”

Hyun broke character and giggled involuntarily. Amy elbowed her.

I said, “Oh, that’s funny to you?”

Hyun said, “No sir, I really just forgot them one day. I was really embarrassed.”

I said, “Well, even if that’s true, he said you were opening your legs to show a boy across the room?”

Hyun said, “I just get fidgety. I’m so embarrassed if someone accidentally saw up my skirt.”

I said, “Fine, girls, show me your underwear.”

They nervously looked at each other and at me.

I said, “Come on, I have to make sure you are wearing underwear. Do you think I like this part of my job?”

The girls lifted the front of their skirts to show me their panties. Hyun was wearing white cotton panties and Amy was wearing pink. I had a measuring stick in my hand and I slowly moved it up Hyun’s inner thigh and rubbed it on her crotch. She bit her lower lip as I rubbed her pussy through her panties.

I said, “imagine if you weren’t wearing any underwear and I did that, Hyun…it would be bad right?”

Hyun moaned, “That would be so bad, sir.”

I said, “Okay girls, turn around, now the back.”

Amy said, “you’ve already seen that we are wearing them, why the back?”

I said, “The handbook is pretty clear, that your underwear needs to cover at least 90% of your bottoms. I need to make sure these are appropriate.”

I had the girls bend over the couch and lift the back of their skirts, to show me their asses. They were both wearing ordinary panties that mostly covered their asses, but they did ride up into their cracks a bit…there was a little bare ass cheek showing.

I said, “I’m glad to see you aren’t wearing that thong underwear, but these are borderline, I’m going to have to measure.”

I went up to Amy and pulled her underwear down to expose her bare ass.

Amy said in shock, “Principal O’Neil, why do you need to do that!?”

I said, “I have to measure the width of each side of your bottom from your anus to your hip with no underwear first and then remeasure with the underwear back up. It’s the only scientific way to do it. It’s all spelled out in the handbook. Spread your cheeks.”

Amy muttered, “what kind of handbook is this?”, and giggled, as I knelt down and used the measuring stick to measure from her puckered butthole to the side of one cheek and then the other.

I said, “You think this is funny young lady? I have had enough.”

I stood up and smacked her bare ass hard. I let my hand linger a bit, caressing her ass. I gave it another hard smack.

Amy said, “I’m not sure you should be touching my bare bottom with your hand like that.”

I put the polished wooden measuring stick through her legs, above her pulled down panties as rubbed it on her bare pussy gently.

I said, “Would you prefer the stick?”

Amy quickly said, “No, principal O’Neil, you can use your hand.”

I put my hand back on her bare ass, lingering again and put it between her legs, gently touching her pussy, (she whimpered a bit as I removed my hand) before pulling it back out and smacking her ass again.

I said, “Alright, Amy, let’s see if these underwear meet code,” and I pulled up her underwear again. I measured again with her underwear up. I put a hand down the back of her underwear and in between her cheeks to find her butthole with my finger. She said, “What are you doing?!,” and clenched her butt cheeks as my finger lightly pressed on her butthole.

I said, “that’s where I start the measurement,”. “Alright, those seem to be within the rules,” and I lightly smacked her ass.

I moved over to Hyun. She was bent over, with her skirt lifted, displaying her panty covered ass and her thin, long legs.

I said, “Hyun, I don’t even need to measure, those are not covering your ass.”

Hyun said, “These are not a thong Principal.”

I said, “Don’t tell me how to do my job.” I put my hand on the exposed part of her butt cheek, caressing her bare skin.

I said, “Hyun, do you feel that? I’m touching your bare bottom, aren’t I?”

Hyun said, “Sir, it’s just that my panties have ridden up.”

I said, “Stop arguing with me,” and I yanked down her underwear. Hyun gasped in surprise. I smacked her ass hard, leaving a red mark. Hyun grunted. I smacked it again. I moved my hand down between her legs and rubbed her pussy, I inserted my middle finger, wetting it and then rubbing her clit.

Hyun turned her head to look back at me and said, “Principal O’Neil…” with a shocked tone and expression.

I smacked her ass again and then put my finger back in her pussy, then continued rubbing her clit. She made a disappointed groan as I pulled my hand away. I pulled her underwear all the way down, lifting her feet to completely remove them.

Hyun said, “What are you doing with those?”

I said, “These are inappropriate for school, I’m going to have keep these.”

I was still in a squatting position from removing Hyun’s underwear, so I leaned my face in. I had a nice view of her pussy. I spread her labia with my two hands taking a careful look inside. “Have you had intercourse Hyun?”, I said.

Hyun said, “of course not,” pretending to be offended.

I leaned in and licked her pussy from behind briefly. She just turned her head to face me with a stunned expression.

I stood up and said, “Alright girls, get on your knees. I need to measure your skirts.”

The girls got on their knees on a throw rug in the living room. I said, “Your skirts should be touching the floor. They aren’t even close.” As I stood over them, I could see down Amy’s blouse. I said, “Amy, unbutton your shirt. I think that bra might be another violation.”

Amy unbuttoned her blouse all the way down, revealing a lacy bra. I said, “As I suspected, Amy, that bra leaves your nipples quite visible.” I moved forward, with my crotch in her face, as I leaned down over her to unclasp her bra in the back. I had quite an erection from all of this and the thin dress pants didn’t hold it back much, so my boner was pushing on her face. She giggled. She covered her boobs, pretending to be embarrassed.

I stepped back and said, “You think it’s funny, giving men erections? You know that’s what you’re doing to the boys in class. It’s not funny.” I was having a hard time staying in character and not laughing, because I was pitching a ridiculous tent in my pants.

I reached into my pocket and pulled out a folded up piece of paper and held it up. “Mr. Slater gave me this note he saw you two passing back and forth. Should i read it? Should I read it to your parents?”, I said.

Hyun said, “Please don’t read it.” She did not know what was in the note, but she understood the role play.

I opened the note and said, “I’m not going to read it. You will read it aloud to me. I want each one of you to read the part you wrote.” I handed it to Amy first.

She started reading, “Brian’s parents aren’t going to be home this afternoon. I think I might try sucking his dick for the first time. What do you think?”

She passed it to Hyun and Hyun read, “OMG Amy! Do it. I want to know what it is like. I’ve been thinking of blowing Ted.”

Amy read again, “If I suck his dick today, you better do Ted. I don’t want to be the only one.”

Hyun read, “I will do it this weekend. We have a date and we always make out in his car. I’m going to surprise him with a blowjob.”

I interrupted, snatched the note and said, “It gets worse from there. Some of the language…Amy writes something about wanting her pussy (I feigned disgust at the word pussy) licked. Hyun says she has been fingered, but is nervous about getting licked. It’s truly disgusting, what if I showed this note to your parents?”

The girls both said, “No, please don’t,” at the same time.

I started unzipping my pants. I said, “Look girls, I don’t want you corrupting those two young men. If you want to suck a dick so bad, you can try this one,” and I whipped out my boner, moving close to Amy’s face.
The girls both pretended to be shocked and embarrassed.

I smacked Amy in the face with my dick and said, “Go on, do your dirty business.”

Amy pretended to be nervous, she was good at this role play. She closed her eyes and slowly moved her open mouth toward my dick, putting it in briefly, then taking her mouth off of it and making a face. Then she put it back in and pretended to be bad at sucking dick. She used too much teeth and did not really suck, just moved her head slightly.

I said, “Amy, watch the teeth and you need to suck it, like a popsicle, okay. Give it a couple of licks and try again.”

Amy licked the head of my penis a few times and then sucked it some more. I said, “Much better Amy, now open your eyes and look up at me while you do it.” She looked up at me with innocent eyes as she sucked it. I said, “Hyun, your turn now.”

Amy took her mouth off it, with a slurp and Hyun moved closer on her knees. She hesitated and made a nervous whimper, then put it in her mouth. I said, “Very good Hyun, now look up at me while you do it.” She looked up with an innocent expression as she sucked it. I said, “Okay, now Amy again, you girls need to get this out of your system. Ted and Brian are lucky I saved them from this.”

Amy started sucking it like the pro she really is. She let Hyun in for a turn and Hyun really sucked it. They took turns for awhile. I felt like I was going to cum. I pulled my dick out of Hyun’s mouth. I said, “open your mouths girls, tongues out, say ah.” The girls looked frightened, but did as they were told. I said, “Alright, move closer together.”

I jerked off until I started to cum, shooting some on Hyun’s waiting tongue, then aiming for Amy and blasting some on her tongue and face. I jerked the last bit out and shook my dick at Hyun’s outstretched tongue to get the last drips onto it. I put it back in Amy’s mouth and told her to suck some more. Then Hyun.

Amy said, “Can we go back to class now?”

I said, “Oh, we’re just getting started.”

Amy could not help but smile at that.

Source: reddit.com/r/Erotica/comments/wiihz9/my_gf_amy_and_our_friend_hyun_pay_off_a_lost_bet

6 comments

Comments are closed.