“Some.” replied the girl. She was a foster child, and her parents were a little more lax than some of Andrea’s other friend’s were. Cindy was allowed to go on boy dates on Saturday nights.
“What’s the furthest you’ve ever gone?” Andrea asked.
“Well, I’ve made out tons of times.” Cindy told her, smiling.
“That’s it? Just kissing?” Andrea asked her. “Heck, I’ve done that much under the bleachers at the game.”
“I wasn’t done.” she continued. “I let Bobby Franks put his hands on my… my breasts a couple weeks ago, and Darren Harding wanted me to touch his thing inside his pants last weekend.” she said.
“Did you do it?” Andrea asked eagerly.
“NO!!” Cindy said emphatically. “But I did get to look at it. He took it out of his pants after I refused and asked me to do it again. He practically begged me to do it, but I got out of there and walked all the way home. I’m not that sort of girl.”
“Why not?” Andrea asked. “Can I tell you something? A secret?”
“Sure.” Cindy said. “We’re best friends. You can tell me anything.”
“I did a lot more than that this weekend.” she admitted. “I gave a boy a blowjob and let him finish in my mouth.”
“NO WAY!!” Cindy exclaimed loudly, then ducked her head and blushed. “Who was it?” she whispered.
“That’s the secret part. I can’t tell you who it was. I promised.” Andrea confided. “I know what he really wants is to go all the way, but I don’t know if I’m ready for that, yet.”
“Oh my God, Andrea!” You’re serious!!” Cindy giggled, suddenly excited. “If I guess, will you tell me?”
“Can’t.” Andrea replied. “Besides, even if I gave you three tries, you’d never guess who it is.”
“Bet me.” Cindy said. The girl loved to gamble; she was addicted to it like nothing else. “If I don’t guess in three tries, you can blindfold me and he can have me all the way instead.”
“No way. You’ll just lose.” Andrea laughed.
“Well, give me a hint, then.” Cindy demanded. “Can’t you see I’m going crazy here, not knowing?”
“It’s not a long trip for you. You’re already crazy!” Andrea laughed.
“No changing the subject!” Cindy protested. “Just tell me who it is!!”
“No can do. A promise is a promise!” Andrea told her.
“Jeffy Webber.” Cindy guessed. Andrea shook her head with a smile.
“Not even close.” she said. “You’re never going to guess it anyway, so give it up.”
“Give me a hint!” Cindy demanded. “Have you ever been on a date with him?”
“Nope.” Andrea told her. “We just hooked up for the first time this week.”
“I saw you talking to Tommy Martin in the Library on Monday.” Cindy said. “It must be him.”
“TOMMY Martin? No way!!” Andrea laughed. “All he wanted was to know if he could copy my math homework because he didn’t get his done.”
“Did you let him?” Cindy asked, curious.
“No.” Andrea answered. “He even offered me $5 to get it, but I still said no.”
“One more hint.” Cindy demanded. “Does he go to this school?”
Andrea nodded, with a secret smile. “If you guess wrong, you have to come over to my house tonight, let me blindfold and strip you naked, and the guy will get to do anything he wants to you, right?”
“That’s the bet.” Cindy said. “And since I only have one guess left, I’m going to watch you all day to see how you act around the boys. Glad we have the same schedule!”
“Okay, but you have to make your last guess before the end of school today, right?” Andrea challenged. “Or you can guess two right now.”
“Andy Thompson or Gregg Forrester!” Cindy guessed quickly.
“Nope and nope.” Andrea said, smiling. “See you after school!”
“Oh my God! Are you really going to make me go all the way with him?” she asked.
“Yep. Blindfolded, too. You’re going to lose your virginity to a total stranger, and you’ll never know who.”
“That’s not fair. It wasn’t a fair bet!”
“Bullshit! You’re the one who came up with the terms, you boob!”
“Andrea! Please! You know how crazy I get when you keep secrets from me! It really wasn’t a fair bet, and you know it!”
“Sorry, Cindy, a bet’s a bet, and you lost. My house after school, be there, or be… a welsher.”
“Did you really suck it?” Cindy asked, blanching and changing the subject.
“Yup, I did.” Andrea told her proudly. “And I swallowed, too.”
“Cool! What was it like?”
“Well, at first I was grossed out by just the thought of it, you know? But then I really tasted it, and it’s not so bad. Truthfully, I kind of liked it.” Andrea told her. Cindy’s eyes were shining as she listened, nodding.
“Do you think he’ll let me do it to him, too?” Cindy asked.
“Yeah, right!” Andrea rolled her eyes. “What guy on the planet is going to say no to a blowjob?”
“Yeah, I guess you’re right.” Cindy admitted, grinning. “Maybe he’ll get off so hard that he won’t be able to get it up again and do me all the way.”
It was Andrea’s turn to laugh at that. “Haha, yeah, right. He can go three or four times in a row, trust me on that.”
“Oh, man, I can’t wait until tonight!!”
Classes seemed to drag on forever that morning, and at lunch, Billy sat at his sister‘s table, waiting for her to arrive. She was late for lunch, having been talking to one of her teachers, as usual. Today, however, Cindy joined him, foregoing her usual table with the rest of her friends to gossip and giggle.
“Hey, Cindy, what’s up?” he asked, surprised that she was sitting with him.
“Hi Billy. Could you do me a favor and tell me who your sister has been seeing lately? She won’t tell me and it’s driving me crazy.”
“That’s a pretty short drive for you, Cindy. You’re already crazy.” he joked, and she pouted.
“Does your family know any other jokes? Andrea told me the same thing this morning.” She batted her eyes at him and smiled coyly. “I’m coming over to your house tonight, you know. I could give you a special treat if you tell me.” She licked her lips provocatively.
“Really? What sort of a treat?” he asked, playing dumb.
“Oh, Billy, don’t be dense.” she said. “What sort of a treat would you want?” She batted her eyes and licked her lips again, even more suggestively this time. She teased her lips with one finger and stared right down at his crotch.
“Gee, I don’t know, Cindy. Why don’t you give me a hint?”
“Okay, Billy, but I can’t just say it; let me whisper it in your ear.” she said, leaning closer to him. He leaned over towards her, too, and got a nice look down inside her blouse as she put one hand on his thigh, the other on his shoulder, and began whispering into his ear.
“Imagine me, topless, on my knees in front of you and opening your pants. Now do you know what sort of treat I mean?”
He leaned back in surprise. “Cindy! Do you mean what I think you mean?”
She winked and nodded, smiling as she licked her lips once again. “And all you have to do to get me to do it is tell me your sister’s boyfriend’s name.”
“But… but, I don’t know his name!” Billy told her. “She’s been keeping it a secret from both me and Gram!” he said. “If you’re coming over for dinner, though, I guess you’ll meet him same time we do.
“You… don’t know his name.” she said, tonelessly. “Shame. I was looking forward to doing… that… with you tonight.”
“Cindy? Can I ask you a question?” he asked hesitantly. She nodded. “Why would you offer something as… personal as that for the answer to a simple question?”
She bit her lip and looked down. “The truth?” she asked softly. “Well, I lost a bet with your sister, and she’s going to make me go all the way with him. Tonight. Blindfolded. If I could’ve got her to go double or nothing for one more guess, I was going to be able to win.”
“So… why that? With me?” he asked.
“She told me she did… that… with him last night, so I figured if she could do it, I could too. And with you… well, I kinda like you, Billy. I wouldn’t mind so much doing it to you, I guess.”
“Really? You like me?” he asked, surprised. “Cindy, I’m really flattered by that. Because I’ve always liked you, too, and if any girl was ever going to do that to me for my first time, I’d want it to be you.”
“Aww, that’s so sweet, Billy!” said Andrea, coming up behind the two of them with her tray. “I’m afraid someone else has dibs on her cherry, though. Too bad, I can tell that you two are kinda sweet on each other.”
Both Billy and Cindy blushed, knowing that their innermost feelings for each other were now out in the open, at least as far as Andrea was concerned.
“Andrea, would it be okay if I… if I did the bet with your brother tonight, instead of your mystery man?”
“Sure… if you want to be known as a welsher.” Andrea replied dryly. “No, you’ll give it up to my mystery man, blindfolded, just like you agreed earlier.” she said. “Of course, if you want to give Billy sloppy seconds, that’s up to you.”
Cindy looked at Billy, a sad expression on her face. “Billy, I’m sorry, I made a bet with your sister, and she’s not going to let me out of it. I really do wish you could be my first, but…” she said, a tear starting to form.
“That’s okay, Cindy. It’s all right, really. You gave your word, and knowing you have the integrity to keep it is worth just as much as taking your cherry, really.” he said. “So… I can look forward to having you tonight, then?”
“Well, sure, if you don’t mind getting… sl-sloppy sec-sec-seconds!” she stammered, sobbing hard now. Billy put his hands on her shoulders and pulled her close, hugging her.
“Hush, it’ll be okay, I promise!” he whispered to her. “Just don’t give him everything; I want at least one of your virgin holes to myself, okay?”
“Wh-what do you mean?” she asked, her breath hitching as she tried to get herself under control. “I only have the one. And I have to give it to…” she started crying again. “I don’t even get to know his name or see his face!!” she wailed.
“You totally have more than one virgin hole, Cindy.” he told her. “There’s your mouth, and your, umm, asshole.”
“Okay.” she whispered back. “I’ll save both of those for you, okay?” She looked at him, her makeup a mess from the tears. “You really want to do me… back there?”
“Hell yes, Cindy!” he said. “You got the nicest ass in the school! Fuck yeah, I want to fuck it! Doggy style, okay?”
“Okay.” she agreed. “But… you will stop if it hurts too much, right?”
“Of course I will, Cindy! I’d never hurt you on purpose!”
Just then, the bell rang, and it was time for them to go to their classes. Cindy looked at Billy and game him a seductive smile over her shoulder as she left the cafeteria.
Andrea stayed behind a few minutes to talk to her brother before going off to class.
“Okay, here’s the deal.” she said, in response to Billy’s questioning look he gave her. “I bet Cindy she couldn’t guess who I gave a blowjob to yesterday, and the penalty for losing was that she has to go all the way with the mystery man tonight, blindfolded.”
Billy smiled at his sister.
“So… I get to have her all the way, and then guilt trip her afterwards?” he asked. Andrea nodded.
“What if I… don’t want my first time to be with her?” he asked his sister softly.
“Wh-what?” Andrea asked, shocked. “You’ve always lusted after her; why wouldn’t you want to do it?”
“I didn’t say I didn’t want to do it.” he said with a secret smile. “I said I didn’t want my first time to be with her. I want to do it for the first time with the girl I’m in love with.”
“Billy, don’t say that!!” Andrea insisted. “I’m your sister; you can’t be in love with me; it’s not allowed!”
“Tell that to my heart.” he said, quietly. “We have to go to classes. Talk to you later, sis.”
“Count on it, little brother. See you after school.” she replied. They parted company, each going off to their separate wings for class.
At the end of the day, Billy and Andrea got on the bus together that brought them home. They sat next to each other, but didn’t say anything until they were inside the house.
“Gram, I’m having my friend Cindy over tonight, okay?” she asked.
Their grandmother shrugged, but then spoke up. “Just make sure you get your schoolwork done before she gets here.” she said. “And I don’t want to hear a peep out of you three upstairs tonight. My pain is acting up again, and I need my sleep tonight.”
“You won’t, Gram, we promise.” Billy said. “Is there anything I can get you before she comes over?”
“No, Billy, but thank you. You’re such a good boy.” said the elder lady. “I’m just going to go lay down and rest. Don’t bother bringing me a plate tonight; I can tell I won’t be up for it. Besides, I ate a little earlier. You kids be good tonight, and have a good time with your little friend.”
“We will, Gram, and feel better, okay?” Andrea gave their grandmother a kiss on the cheek, then let the lady go into her bedroom and close the door.
Andrea went to the phone and dialed up Cindy, who answered it right away. “Hi, Cindy, are you ready to come over? Our Gram said it was okay.”
“Is he there yet?” Cindy asked. “I can’t wait to meet him.”
“Yes, he’s here, and he wants to meet you, too.” Andrea told her. “Billy’s here, too, and he want’s to ask you something.” Andrea gave the phone to her brother.
“Uhh, hi Cindy.” Billy said into the receiver.
“Hi, Billy, what did you want to ask me?” she replied. Billy looked at his sister, who grinned.
“No panties” she mouthed at him. He grinned back and nodded.
“Well, I was wondering if you would wear that blue mini skirt for me tonight, when you come over. I really like the way it looks on you.”
“Sure, Billy, is that all?” Cindy asked.
“Well, there was one more thing…” he trailed off, blushing.
“What is it?” Cindy asked. I like you, Billy, there’s not much I wouldn’t do for you if you asked.”
“Well, I was wondering if maybe… maybe you could come over without wearing any panties.” he said.
“Billy, you naughty boy!” she giggled. “Well, maybe I will, and maybe I won’t. I’m going to let it be a surprise, but I promise you’ll find out tonight, after I get there.”
“Okay.” he agreed. “I’m kinda getting hard thinking about it already.”
“Well, don’t get it too hard.” she said. “After I do… what I have to do, with Andrea’s mystery man, then I am sooo looking forward to getting with you and doing everything else.”
“You are?” he asked. “Even the second thing I mentioned today?”
“Well, I’m a little nervous about that, but I trust you, Billy, and you promised not to hurt me, and that you…
