Blondie's Humiliation Stories

For Age 18+ Only.
Chapter 21: Blondie
Tue Feb 5, 2019 2:57pm

Periodically I would lay on my bed and daydream about the humiliation sessions that I'd experienced. Often I'd come up with some new scenarios that I would put into play down the road.

During these daydreams inevitably my thoughts would steer toward Blondie. One evening I came up with a new idea. I had been requiring him to wear his tighty-whities every day, but I already had Johnny Boy wearing his tighty-whities. Bobby, as you may recall, is not allowed to wear anything underneath. So I wanted to do something different for Blondie. And I remembered how embarrassed he was and how cute he looked when he had to wear a pair of panties that night on my thirteenth birthday. And now, heck, with him being so smooth all over it just seemed appropriate to panty him. And so delicious, I might add! Also, it would be a fun surprise for the girls.

So I texted him that evening. I included his sister Becky. Here is the exchange:

Me: Blondie, I have news for you. You don't have to wear your tighty-whities anymore.

Blondie: Okay. Thanks.

Me: But I would like you to wear panties from now on.

Blondie (after a long pause): Okay.

Dear boy. He knew me well enough to know it would be fruitless to protest.

Me: Beck, would you mind helping Blondie with this? You have very good taste when it comes to Blondie's attire.

Becky: My pleasure! [grinning emoticon] I've been laying out his shorts and tee shirt on his bed every night. Now I'll put a pair of panties on top for him.

Me: Excellent. He'll look so cute. Maybe he can model them for you before he puts the rest of his clothes on.

Becky: Good idea! In fact, I think tomorrow he can serve me my breakfast in his panties. Our parents will already be at work.

Me: Yes! I'm sure he'll love that.

I was about to finish up but I pictured Blondie cringing as he read our banter so I sat back and continued. Becky played her part to the hilt.

Me: I'm sure he'll be blushing like a little schoolgirl.

Becky: I know. Don't you love how red he gets when we play with him?

Me: He's the best. I've gotten other boys––and girls, for that matter––to blush pretty good but nobody does it like Blondie.

Becky: LOL

Me: Are you blushing right now, Blondie?

Blondie: No.

I didn't believe him.

Me: Come on, Blondie, are you sure you're not at least a little pink in the cheeks?

Becky: I just peeked in his room. He was definitely a little pink and he turned red when he saw me.

Me: I figured as much. Blondie, you lied to me. You should know better. I'm afraid you'll have to be punished.

There was no response.

Me: Answer me, Blondie.

Blondie: Okay. Sorry. I didn't know I was blushing.

Me: I'm not buying that, Blondie. Don't you feel your face get hot when you blush?

Blondie didn't respond, so it was time to implement his punishment.

Me: Becky, are you in your room?

Becky: Yes

Me: On your bed?

Becky: Yep

Me: Good. Are your parents home?

Becky: No, they're at a fundraiser.

Me: Perfect! Blondie, I'd like you to get naked and go into Becky's room. You can sit on her bed, facing her. And bring your phone.

There was no response, and I was relentless.

Me: Blondie, are you there?

Blondie: Yes. I'm doing it.

Me: Okay. Let me know when you're in Becky's room.

About a minute went by.

Blondie: I'm in Becky's room.

Me: Are you naked?

Blondie: Yes.

Me: Yes, what?

Blondie: Yes, I'm naked.

Me: Becky, is he naked?

Becky: As the day he was born. [smiley face emoticon]

Me: Blondie, are you on Becky's bed?

Short pause.

Blondie: I am now.

Me: Are you blushing?

Blondie: I guess.

Becky: He's blushing. He's naked on my bed and he looks very embarrassed.

Becky: He just read my last text and turned even redder. This is so much fun!!

Becky: [Picture of naked Blondie sitting on the bed, covering up and looking very uncomfortable]

Me: Thanks, Beck! He's looking marvelous tonight. He's been doing a fantastic job keeping his hair away and his skin so smooth.

Becky: I know. He's got the girly-girl legs and arms. I can't wait to see him in panties.

Me: Same here. How often does he shave his legs?

Becky: So I went online and searched for the best hair removal cream for men. I bought some for him and showed him how to use it. It's awesome stuff. It's completely non-irritant so I even had him use it on his privates. You apply it with the spatula that it comes with, let it sit for 5 or 10 minutes, then scrape it off. All the hair comes off. It's amazing how smooth it makes him. I think if he shaved there would be a little stubble after a day or two. But this stuff keeps him silky smooth. And it lasts a long time. He could probably go longer but I've been having him do it once a week. That way he'll always be smooth in case you want to check him out.

Me: Thanks for that, Beck. Do you watch him do it?

Becky: No. I tell him he has to do it or I'll tell Felicity. Then he locks himself in the bathroom while he denudes himself. He's such a bashful one, that Blondie. The only time I get to see his little goodies is when you make him get naked. So he's hating this right now.

Me: Is he still covering himself up?

Becky: Oh yeah. It's funny how self-conscious he is about his little penis. I mean, it's not like I haven't seen it before.

Me: I know. That's what I love about him. You'd think he'd get used to it but no matter how many times I strip him he still gets as embarrassed as all get-out. It's such a turn-on for me.

Me: Blondie, move your hands away from your privates and let your sissy see you better. And spread your legs out.

Becky: [Picture of shamefaced Blondie sitting back on his knees, fully exposed. Emoticon of laughing face with tears coming from eyes]

Me: Thanks! So adorable.

I was definitely becoming aroused. It was a wonderful engagement. Blondie was in another location but I was having a fabulous time humiliating him. I had been kneading my crotch unconsciously and just then became aware of it. I then escalated my efforts, massaging in earnest while texting with my other hand.

Me: I just can't get over how smooth he is.

Becky: I know, right? I'm staring at his little pee-pee and balls. It really looks like he still hasn't been able to grow any hair yet. It looks like a prepubescent boy's little package. And he's 16. LOL!

Me: Blondie, how old do you think you look down there? Be honest.

There was a pause, and I'm sure it pained him immeasurably to type the next text.

Blondie: 11?

I loved the question mark.

Me: Yes! 11! You are spot on! Tell me, Blondie, how old were you when you first started puberty?

Thanks to the accounts from Becky, Brenda and my sister Julie I knew he started very late.

Blondie: I think I was 14.

Me: Are you sure? I heard it may have been as late as 15.

Blondie: Maybe. I don't know. It was somewhere around 14 or 15.

Becky: Closer to 15. I remember it was late in his sophomore year when Becky got him naked out at the soccer field. Actually he wasn't quite naked because he was wearing a black bra.[grinning emoticon] Anyway I got a pretty good look and he was still bald as a cucumber.

Me: Kind of like he is right now.

Becky: Yes! Exactly!

Me: It was only a few months ago that Blondie and I were sitting where you two are right now. He had hair then. But when we left the room he didn't.

Becky: I know. You surprised us when you exposed him to us. It was awesome. That's when Brenda said "He’s got a cleany teeny peenie weenie," and we were dying laughing.

Me: That was hilarious. I have to say I like him better without the hair. I think I'll keep him smooth forever. He's so cute when he's all naked and hairless and blushing.

Becky: It must be killing him to be naked like this in front of me.

Me: Oh, trust me, he's just hating this. I mean, he's 16 and all bare against his will in front of his sister.

Becky: God, we've had so much fun with him these last few months.

Me: I'll say. Hey, this little Blondie session has gotten me a little excited, if you know what I mean and I think you do. Would you mind taking over for awhile? Maybe you could tell me a little bit about when you and Brenda took Blondie to Victoria's Secret. I already heard about it from my sister but that's okay.

Becky: My pleasure. And hopefully yours! [grinning face with tongue sticking out emoticon]

Becky: You know the story so I'll tell you the good parts. Julie coaxed him into trying on a teddy. She waited on the other side of the waiting room door and made him hand over all of his clothes over the door. Your sister played her part perfectly.

Becky: Brenda and I peeked over the door. He was blushing like he is now and had both hands covering his little goodies.

Becky: Julie draped a fuchsia colored teddy over the door for him to put on. Then she made him come out and show her. There were a few other people in the store. You can imagine how embarrassed he was.

Becky: Then when he was back in the dressing room she told him about a bra and panty sale and insisted that he try a set on.

My state of arousal was ever increasing over Becky's wonderful recap. I pictured Blondie, both in the store and currently on Becky's bed, probably squirming ever so uncomfortably.

Becky: She even asked him what his cup size was. [laughing face with tears emoticon]

Becky: Then came my favorite part. Julie used her key and went bursting in the room. The shocked expression on Blondie's face was priceless.

Becky: She told him she needed to get his measurements. Can you believe it? LOL! He's stark naked and she needed to get his measurements.

Becky: Brenda and I, plus these two very interested teenage girls all came in the room. I think Blondie wanted to die on the spot.

Becky: So Julie takes her time getting all these measurements, acting very professional like it was something she did all the time.

Becky: She had him raise his arms high in the air so she could get his waist measurement. Julie said it was in case he wanted to buy a corset.

Becky: Then she got down on her knees to measure his hips for proper panty size. She spent a lot of time down there, lol. Finally she stood up and said, "Definitely an extra small." I had tears running down my face I was laughing so hard.

Becky: Oh, Felicity, you should have seen Blondie. You would have loved it.

I wasn't there, but needless to say I was loving it. I had already climaxed but had let Becky go on for a minute while I luxuriated in the moment.

Me: That's okay, Becky. You made me feel like I was there. That was fantastic. Thanks!

Becky: Glad I could help! [smiley face emoticon]

Me: And thank YOU, Blondie. Once again you've given me a lot of pleasure.

Me: See you, Beck. Have fun setting Blondie up with his panties.

Becky: Will do! [grinning emoticon]


It somewhat surprised me how much I enjoyed that session, considering I wasn't physically there to witness Blondie's humiliation. It proved to be a portent of things to come, as I subsequently had numerous pleasurable experiences in the same manner when I took control of Miss Joplin. Once again, Blondie unwittingly opened new doors for me in my wondrous exploits in humiliation.

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