Pretty Girl of the Day, October 16, 2016

“I never liked seeing a girl’s underwear,” says today’s pretty girl.

“So even in high school, whenever I wore this dress, I never wore any underwear under it, because it’s so thin that if I wore underwear, then you would be able to see it. Some of my teachers didn’t like me to wear this dress, though. Some of them said it was too short, but I never thought so. What do you think?”

“As you can see, my dress is the perfect length — long enough for me to feel decent, but short enough to be sexy.”

“Other teachers got annoyed with me because the top of my dress sometimes shifts. They thought maybe I should wear a bra, but that’s just ridiculous. You can’t wear a bra, or any underwear under this dress! And what do they want me to do? Never spin around? I’m a girl! I need to be free! Ha ha ha!”

“I think my high school teachers should have just lightened up a little, don’t you agree? I mean, we all know that tits have a way of falling out of dresses, that’s all. Nothing to worry about.”

“Most of my teachers would just say something to me about the dress, then let it go, because they understood that a girl likes to be sexy, and, well, it’s a sexy dress, for sure. The only teacher who ever punished me for wearing this dress was my science teacher. He liked to punish girls by spanking us. I don’t blame him, though. Most of the girls deserved it. Like maybe they didn’t do their homework, or they weren’t paying attention in class, something like that.”

“For a proper spanking, of course, a girl has to have a bare bottom, so whenever our science teacher called on one of us to come up to the front of the room for a spanking, we knew to take off all our underwear and bottoms (bra, panties, pants, short, skirt) and leave them at our desk, but we could keep our top or dress on, so it wasn’t too bad. The teacher sat in his chair, facing to the right side of the room, and the girl would kneel with her back to the class and her knees spread apart as wide as possible. Then, for her spanking, she would lift up her dress or top all the way, and lay her bare chest in his lap.”

“Our teacher liked to tease the girl a bit, you know, before spanking her. It was fun for him, and for the class, too, to see the girl tense up, when she thought the slap was coming, just to discover he just wanted to gently stroke her bottom a little before spanking her. Sometimes a girl would get sexually excited, you know, just from the anticipation, and she would try to close her legs, but the teacher wouldn’t let her. If it looked like she was about to cum, he would stop spanking her, and just tease her instead, keeping her on the brink of cumming for as long as possible before finally letting her cum.”

“So when it was my turn to be spanked, I was really caught off-guard. I didn’t do anything wrong! But I guess he really didn’t like my dress. So I came up to the front of the room for my spanking, and knelt down before him. I was about to lift up my dress when he told me I had to take it off. Why? I asked. That’s when he yelled at me, and told me I had to obey him. Okay, okay, I said, no problem. I stepped out of my dress, and assumed the position. He just spanked me a couple of times before I was completely wet, which he noticed right away, and he began rubbing my pussy, and not like a man, either. He rubbed me like a girl. I mean he knew how to do it, gently at first, dipping his finger into my vagina, then gliding it inside my lips to my clitoris, and then back into my vagina. First one finger, then two, a little more firmly and faster, until… Just when I was about to cum, he completely lost interest in my pussy, and started tickling me! It was the strangest experience! I knew just one more push into my vagina was all it would take to cum, and here he was, raising the little hairs on my back! I moaned, and rubbed my face back and forth in his lap, but he wouldn’t release me. I begged and pleaded for him to finish me, but he wouldn’t do it. He wouldn’t do it, that is, until I offered him a trade.”

Your dress?

“How did you know? Yup, my dress. If I agreed to leave the class completely naked, he would let me cum. So I agreed. And then, he was soooo sweet to me. He gave me a backrub, then a butt massage, gently stroking my cheeks, and between my cheeks, oh, it felt so gooood! I was so close to cumming, and he knew it, so he used firm pressure all over, between my legs, and rubbed me fast at first, then slow, and gentle. I relaxed, and smiled, and stroked his hard penis as I came. Mmmmmm, it felt so good.”

“Then the harsh reality began to set in, which was that I had given up my dress just to cum, what was I thinking?? But I took my punishment like a girl. I finished the day in the nude, and took the school bus home. When I got home, my mom asked about my dress, so I told her the story, and she said I had to get it back. So, the next day, I asked my science teacher if he could give me my dress back, and he said sure, any day I come to school completely naked, he’ll give it back to me. Well, I didn’t want my dress that badly, so I wore clothes to school every day, until my mom asked me again about the dress, so I told her the deal. I thought my mom would be horrified, and say what a terrible deal that was, but instead she said I would have to come to school naked, if that’s what it took to get my dress back.”

“Now, do you remember high school? Coming to school naked isn’t something a girl can just do, right out off the bat. She has to warm up to it, you know, start slow. My mom understood that, so she suggested just going to school topless for a few days first. It was such a relief not to have to go to school naked, I almost didn’t mind going topless. I asked my mom if I could wear a long skirt, and she said yes, on the first day. Then, on the second day, she let me wear a skirt again, but it had to be a miniskirt. Then the next day, she made me wear a micro-miniskirt, and this was a problem for me, because of our high school dress code. It’s pretty standard across most of the high schools in our area, and I actually like it, because it lets girls get away with a lot. But one thing you can’t do is let your underwear show, so that means no panties under a micro-miniskirt. It was hard, but I did it.”

“Then came the weekend, which was a relief for me, because I could finally wear clothes again. Or so I thought. My mom thought it would be good to practice wearing as little clothing as possible, so around the house, she actually made me stay naked, and when the doorbell rang, I had to answer it! My mom made it really hard for me — she ordered pizza, then invited the neighbors over, including their kid, who was in middle school. I have no idea what my mom told them, but none of them made any comment about me being naked, not even the kid. By the time they left, I felt almost natural being naked in front of them.”

“But then, on Saturday night, I had a date with my boyfriend, for which I absolutely had to wear clothes. I begged and pleaded with my mom, and eventually we came to an agreement. I could either wear a crotch-length top without anything under it, or else a shorter top and panties. That seemed like a no-brainer. I would wear a top and panties, like I’ve done so many times before. But there was a catch. If at any time during our date, my boyfriend asked me to take off either my panties or my top, I would do it, no questions asked. I laughed when my mom said that, because there was no chance in hell my boyfriend would ask me to do that, except maybe in the car on the way home, so I said sure, no problem. I put on a cute belly shirt, and a pair of shiny bikini panties, and came to the door when my boyfriend arrived. I hollered, by mom, and off we went.”

“I was really excited when I sat down in his car, I almost came! Something about wearing clothes after being naked for so long really got me going. Where are we going, I asked. To the Bottomless Buffet, he replied. I gulped. When they say ‘Bottomless’, they mean girls who go there can get a discount if they don’t wear a bottom. I had been there before, and they’re very relaxed about what counts as ‘bottomless’. You can wear a t-shirt that almost completely covers you, and as long as you lift it up to show them you’re not wearing panties, you get the discount. But today, I was just wearing a belly shirt and panties, which if I took off, I would be almost completely naked! Maybe he won’t ask me to take them off, I thought. After all, lots of girls go there wearing bottoms, and just pay full price. My boyfriend wouldn’t be so mean as to make me strip half naked just to get the discount, would he?”

“We parked. He didn’t say anything. We got to the restaurant. 30 minute wait. We sat down. Whew! He was being a gentleman. He put his arm around me, and it felt good. I felt my hard nipples press against my thin belly shirt, and my pussy felt warm and wet again. It’s time, he said. What? I said. It’s time, he repeated. Time for what, I asked. I’m so sorry, honey, but your mom told me I had to ask you to take off your panties before we sat down to eat. I feel so bad for you, darling, I’m so sorry. But if you just go into the ladies room and… He almost started crying, poor boy, I could see he felt bad. I stroked his hair, and said sure, honey, I’ll do it. I know you didn’t want to ask, but you had to. It’s okay.”

“I went into the ladies room, my heart beating a mile a minute. No one else was there, so I just took off my panties and threw ’em in the wastebasket. I looked at myself in the mirror, took a deep breath, and opened the door. I felt like covering my pussy, but then I thought that would just attract more attention, so I tried to act natural. My boyfriend was already standing when I got to him. Our table is ready, he said. We followed the hostess, who, by the way, was wearing a black shirt and no bottom, very cute! Seeing her bottomless really put me at ease. My boyfriend and I sat on the same side of our booth, and he didn’t object when I undid his pants. He had been waiting for me to do that, I think, because he wasn’t wearing any underwear, and his dick was already hard when I liberated it. When we got up to get our food at the buffet, I suggested to my boyfriend that he lose his pants, and join the bottomless crowd, but he declined, alas. Still, we had a great time, and I didn’t feel out of place at all, with so many of the girls almost as completely bottomless as me. When we were done eating, I turned around and straddled my boyfriend, and let him slip his dick inside me. It went in easy, because I was wet, and he was hard. He asked me to take off my top, and so I did. It felt so good, kissing him, and feeling him push inside me, up and down, up and down. I came, but I tried not to say anything that would disturb his concentration, but then I came again, and I couldn’t help it, I gasped, maybe even yelled, and then he yelled, too, and we collapsed into each other, it was glorious!”

“That was the first time I ever made love in a public place, and it was one of my best orgasms ever. I didn’t even mind that I was naked, it was such a silky, dreamy experience. As I began once more noticing my surroundings, it seemed that people were clapping and cheering, and I thought maybe there was some kind of stage performance, like a band or something. Gradually it dawned on me that they were cheering for us, for our love-making! We both laughed, and I got up and took a bow.

“We were already out of the restaurant when I remembered I was naked. Oh! We have to go in and get my… I started to say, when he held out my top in his hands. Such a gentleman! I put it on, and nuzzled his neck with my face and lips. Such a happy date!”

“On Sunday, I kept my belly shirt on as a reminder of my funnest date ever, and when a couple of my girlfriends came over, I stayed bottomless, which for some reason, they took as an invitation to fondle me and try to make me cum. Stop! Stop! I told them, secretly wanting them to keep going. Boy, we had fun that afternoon!”

“So, by Monday I thought I was ready to go in to school naked. I came downstairs for breakfast in the buff, and told my mom. I thought she would be happy and say yes, but instead she said, Honey, you’ve had a big weekend, you had sex in public with your boyfriend, and then you did that finger-fucking with your girlfriends yesterday, maybe you should just take a breather. What about just wearing a pair of panties to school?”

“I know my mom was looking out for me, but I really felt ready to go to school naked. But now my mom, who had been pushing me to wear less clothes, was now telling me I should take it easy, and wear clothes to school. What about wearing just a t-shirt, then, honey, she said. I just think you’ll feel better if you have something on when you go to school today. I sighed, and went upstairs, and looked through my tops to see if there was something I could wear when I spotted it. A thin white crop-top that looked super-sexy on me. I ran downstairs to show my mom, and she shook her head. It really doesn’t cover your bottom, she said. I know, mom, I said, but look, it covers way past my belly button, almost to the top of my pussy, see? Yeah, honey, but only while you’re stretching it. Let it go, and look at yourself in the mirror, she suggested. I still think it’s okay, mom, can I wear it? Please? She thought about it, and finally said okay. I was so happy she let me go to school in that top. It was the very first time I ever went to school completely bottomless!”

“When I came home from school that day, I was so happy! I made it through a whole day, completely bottomless, and nothing bad happened. Sure, lots of people noticed, especially the boys, but they all said it looked good on me. The next day, I begged my mom to go to school naked, but again, she insisted that I wear just a top. But this time, she didn’t fight me when I suggested wearing just a sports bra. I gradually wore my mom down to the point she said if I can go out on one more date with my boyfriend, and I let him strip me naked and let him fuck me in public, then she would consider letting me go to school naked. I hugged and kissed my mom, and said oh, thank you, thank you, thank you! I was so happy, I called my boyfriend, and he came over while I was still bottomless.”

“I’m so sorry, I said as I opened the door, let me finish dressing. He followed me up to my room and helped me pick out a pair of panties to wear with my sports bra. After I was dressed, I confided in him the deal I made with my mom. So, let me get this straight, he said. You’ll spend the whole weekend with me, and whenever I feel like taking off some of your clothing, I can just go ahead and do it? Um hmm, I said, nodding. Or you can tell me to take something off, and I have to do it, no matter where we are, in public or in private, I added. He couldn’t believe his good fortune. So if I ask you right now to pull your panties down onto your thighs, you would just do it? Instead of answering his question, I did it to show him it’s true. Your dad and your little brother are in the living room. Would you just go out there with your panties down if I asked you to do that? I gulped, and nodded. He laughed. Don’t worry, I won’t make you do that!”

“Okay, I said, but there’s one more thing. At some point, we have to be in public, and you need to strip me naked, and fuck me. Do you think you can do that? He thought about it, and then nodded, and smiled. On Saturday morning, he called me and asked what I was wearing. I told him the truth: he woke me up out of a sound sleep, and I was naked. Good, he said. Put on just a t-shirt, then go downstairs, and lie on your couch on your back, with your legs spread apart, pretending to be asleep. I did as he instructed, wondering what would happen next. Sure enough, within a few minutes, the doorbell rang, and my little brother answered it, while I continued to feign sleep. My boyfriend along with another boy and his girlfriend came in, and took pictures of me, then my boyfriend shook me and told me to wake up, which I pretended to do, while also pretending to be completely unaware my pussy was on full view to his two friends.”

“Good morning, sleepyhead, he said. Come on, let’s go. Wait, I said, can I put on some clothes first? Not necessary, he said. But she’s half naked, said the girl. At least let her put on a pair of panties, don’t you think? Like I said, said my boyfriend, it’s not necessary. Let’s go. So I followed them out the door, wearing just a t-shirt, and we piled into the boy’s car.”


“The rest was a blur, which I might tell you someday, but for now, yes, no surprise, I lost my top at a McDonald’s, but there were a lot of little kids around, so my boyfriend had the decency not to fuck me there, thank God! We went to the beach, where he bought me a cover-up that didn’t quite cover me up, but I guess it helped make me feel a little more decent. We went to a bar where the girl and I were forced to strip for money, most of which the boys spent on drinks, While we were naked, the boys treated us as their sex slaves, which was kind of fun, and a little kinky, especially the part where the boys ordered us to pleasure each other, much to the enjoyment of everyone at the bar. The next day, the boys bought each of us a little t-shirt for the trip home. The best part of all, my mom let me go to school naked that Monday, where I reclaimed my dress.”

2 thoughts on “Pretty Girl of the Day, October 16, 2016

  1. Picklepuss

    I’ve always loved Richard’s high school stories but this has to be his greatest yet. ♥ I wish there was a book-length version of it!

  2. Anonymous

    This girl came out of her shell and began happily being naked and having sex in public. She’s ready for the College!


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