Diamond in the Rough Pt. 02

Author's note: These characters were introduced last year in the first part of this series, under the "First Time" category, because it was Anna's first time. I recommend starting there. I wrote this second part because people didn't seem to like the way I left the characters up in the air. What you see here is where I always saw this leading. Even though it starts out looking like something of a First Time story for Brandon, it doesn't stay there, hence its placement in the "Romance" category, where perhaps this series always belonged.

"Brandon...do you want to fuck me?" Anna, the 33-year-old Librarian, who had been a virgin until just days before, let the words just hang there, deliberate and unmistakable. Those words had been directed at a sweet, shy young college freshman who she knew from his high school stint, two years prior, on the Library's Teen Council.

Brandon swallowed hard. His nervousness rose up and almost choked the voice in his throat, almost, but not quite. He looked straight back into her eyes and said..."Yes."

"Good," said Anna. "That's good. Can you get away tonight?" No sense in waiting, she thought. She was horny. He was willing. Let's do this as soon as possible. She thought about pushing for later that same afternoon, but it was already nearly 3:00 p.m. and she didn't want to have to deal with the possible complication of meal time.

"Yeah, I think so."

"Here's my address." She wrote it out on the corner of the paper he was taking notes on. "Be there at 7:30 tonight. Don't be late."

"OK. I'll be there. I'll tell my mom I'm meeting someone to study."

"Good. See you tonight." and with that, Anna got up and walked back to resume her position behind the desk. She remembered the days of living under mother's wing. She didn't envy him that.

Brandon watched her as she walked. He couldn't believe what had just happened. This was the stuff of fantasies, but this was no fantasy, it was real! Brandon was a virgin, but tonight that would be over. Tonight he was going to have sex with a real woman! And a pretty decent looking woman too, a real MILF he remembered fantasizing about back in his high school days.His hard-on raged in his pants.

Anna was thrilled with herself at how adventuresome she'd become! Where did that come from? She wondered. Was it the sex? She had really liked having sex with Paul. She definitely wanted more of it, and soon. She recognized that she was horny. But why now? Why so suddenly, and with Brandon of all people? He was a boy! Fully legal, but still, comparatively, a boy! Did she just have some hunger to flip the power dynamic? What the hell was going on with her? Anna didn't know.

What Anna did know is that now she was committed. She'd just invited this boy over to her house to have sex with her that very same night, less than five hours from now! Her anxiety started to creep in. Could she get out of it? How? Did she want to get out of it? She wanted to have sex, but she didn't want it to be all complicated, like it was getting with Paul. She wanted to feel safe. She wanted to feel secure. She wanted to feel in control. As she thought, that's what she supposed it was. Brandon was almost certainly still a virgin, he was sweet and very nice-looking, and she thought that with him she could be in control.

Brandon was excited. This will be perfect, he thought, a sexy older woman who could give him some experience. Experience was what he needed to give him the confidence he was lacking with girls his own age. Quickly, he gathered up the research materials he'd been collecting for his paper, put his laptop back in his backpack, and left the Library for home. He wasn't going to get any more studying done today anyway, that's for sure!

On the way home, Brandon stopped to buy condoms. A gentleman can't assume a girl's on birth control, he thought. A gentleman needs to come prepared. He wasn't really worried about diseases with Anna, but you couldn't be too safe there, either. One thing high school sex ed was good for was giving you a thorough fear of sexually transmitted diseases.

As soon as he got home he made himself a sandwich. Don't want to be hungry or too full at 7:30, he thought. Best to eat now. He told his mom he'd be going over to a friend's house to work on a project, and might not be back until late so don't wait up. He'd been a good kid. She trusted him, so nothing to worry about there. After the sandwich he took a shower. Gotta make sure I don't smell, he thought.

In the shower, his cock was rock hard. He figured he better rub one out to relieve the tension. There was no way he wanted to embarrass himself with Anna by coming too early. With all the excitement he was already on a hair trigger. As he thought about sliding his dick in between her beautiful tits, it didn't take long before jets of his cum were hitting the walls of the shower stall. He made sure to rinse that all down and thoroughly remove the evidence.

Out of the shower, Brandon first shaved, then agonized in indecision over what to wear. He didn't want to dress too nicely, or too sloppily. What was the right thing? He tried about a dozen combinations before finally settling on khakis and a sweater. He looked at the clock. It was 6:55. Shit! Time to head over there. She said not to be late! He got there by 7:15 and sat and waited in his car.

Anna was nervous too, but not anywhere near so nervous as Brandon. She got home at her regular time after work, about 5:15. She did shower, but other than that, and a little fragrance, she didn't make any special preparations. She didn't eat. She had no appetite. She wore the same outfit as she had with Paul a few days earlier, except this time she did wear a bra, although it wasn't an especially sexy one. She was still having second thoughts, but reassured herself that if she wanted, she could call things off at any time. Even if she just gave Brandon a handjob, that would still probably be more than he'd ever had, and he'd go away happy. If everything worked out, she'd give him a real night to remember, and have one herself too.

Brandon rang Anna's doorbell at precisely 7:30. "Hi," he said as Anna opened the door. Suddenly the thought occurred to him that perhaps he should have brought flowers.

She could see that he was nervous. Sweat stains were already beginning to form in his armpits, even though she was sure he was wearing a shirt that must have been freshly clean an hour before. "Hi Brandon. Come in."

"You look beautiful," he told her.

"Thank you. You're looking very handsome yourself." She giggled very slightly. "Please, have a seat." She gestured toward the couch. "Can I get you something to drink? Water? A glass of wine, maybe?"

"Water would be great, thank you." Brandon had only tried wine twice before. He didn't like it. Should he have said yes? Would that seem more romantic? Oh no, I'm blowing it already, he thought to himself.

"Coming right up." Anna was glad he had declined the wine. She knew he was over 18, but hadn't really thought the offer through. She would have felt funny about furnishing alcohol. Anna got him a glass of water and handed it to him.

"Thank you." Brandon took a sip, and then a good sized gulp.

"So Brandon, tell me: What did you think when I asked you my question today? Be honest." Anna wanted to take control of this situation right away. She sat on a chair next to the sofa, but turned her shoulders to face Brandon.

"Surprised of course, but excited, really excited. I always thought you were pretty. I just never dreamed that you...but I'm really glad you did!"

"Tell me, when you were on Teen Council, did you ever fantasize about me?"

Brandon was embarrassed. "Yes. Sometimes."

"What was your fantasy? What did you fantasize that we would do?"

"I had this fantasy that I'd come for the council meeting, but I'd be the only one, and then you'd let me stay until after the Library was closed, after everybody else had gone home, and then we'd do it on the floor in the meeting room."

"Oh my!" Anna feigned playful shock. "Well I think my bed will be much more comfortable. Don't you?"

"For sure." Brandon laughed.

"Would you like to go back there now?" Anna thought there was no sense in delaying things. They both knew why Brandon had come to her house that night. His shyness was cute. Sex with Paul had been great, but she had felt at such a disadvantage, and it had been stressful to pretend she knew what she was doing when she really didn't. This time she had the advantage.

Brandon was trying to play it cool, but they could both see that he wasn't very convincing.

Anna held out her hand, "C'mon." Brandon took it and she led him back to her bedroom.

"Would you like to undress me, Brandon?" Anna asked as she faced him, standing next to the bed.

"Sure!" Brandon stood there, looking at Anna, but seemed uncertain what to do next.

"Brandon? Are you a virgin?" She didn't want to embarrass him, but his inexperience was really showing, and she thought it best to confirm, so she could be sure what she was dealing with.

"Sorry. I guess it shows, huh?"

"It's OK. Everybody has to have a first time. Let me help you." Anna moved in, wrapped her arms around him, and kissed Brandon on the lips. The kiss was tentative, sweet. Brandon seemed unsure. He didn't kiss her back at first. When he did, Anna brought in her tongue, but Brandon didn't meet it, then he did, but it was all wrong. Anna wasn't feeling anything like she had with Paul. It was all just sloppy saliva exchange. "Brandon, was that your first kiss?"

"Sorry. I'll get better. I promise!"

"Oh I'm sure you will. Don't worry. We'll work on it." Anna was thinking this would be work. Why had she not expected this? She should have expected this. Hopefully he's a quick learner. She kissed him again. The second time was a little better. The third time maybe better still, not great. She still wasn't really feeling it, but it was better. She hadn't brought him here to kiss, anyway, she thought. She'd brought him here because she wanted to feel his hot, young cock buried inside her. Best get to that. Maybe the rest of him would catch up. She backed away.

"Here. Let me help," she said, as she grabbed her sweater and pulled it off over her head. She noticed Brandon's eyes were glued to her still bra-covered tits. She reached around behind and undid the clasp, removed the bra, and tossed it at the foot of the bed.

"You're so beautiful," Brandon said, as he bent down, reached his arms around, and planted a kiss, straight on her left nipple, then he pulled her to him and crushed his face up against it.

"Whoa! Slow down! Take it easy!" Anna had to admonish the over-eager boy. Of course he'd probably never seen tits before, either, she thought. Maybe this would get better if she could just see his hard cock. She gently pushed him off her.

"Sorry," Brandon said. "I guess I got carried away."

"Maybe just a little," said Anna. "Now hang on..." and she slipped off her jeans and pulled off her socks, leaving her only in a pair of red lace panties. "Now you."

Brandon quickly removed his shirt, unbuckled and dropped his jeans, removed his socks, and stood facing her in just his boxer-briefs, which were straining to contain his obvious erection. Anna could see a small wet spot at the tip of the "tent pole."

"All of it."

Brandon removed them and stood in front of her. His cock curved upward slightly and it looked very stiff. It stood at about a 45 degree angle from his abdomen. It looked about the same size as Paul's, maybe a little smaller around, she couldn't be sure. She noticed he was not circumcised. Paul had been.

"Somebody's happy to see me." Anna cooed as she grabbed his cock with her right hand while she threw her left around his shoulders and brought him in for another kiss. His member felt warm and firm in her hands as she gave it a squeeze. "Mmmm" she hummed as she kissed him.

Brandon gasped at the shock of her hand wrapped around his cock. He closed his eyes and focused on the feeling as he tried to return Anna's kiss. He could also feel her breasts teasing his rib cage. He felt like maybe he was starting to get the hang of kissing her.

Anna also felt like his kissing was getting better. Not great yet, but better. She liked the way his cock felt in her hand. She could feel it pulsing slightly as the blood pumped in to keep it stiff. She had been slightly aroused for an hour before Brandon arrived. Now she could feel herself getting a little bit wetter as she imagined that cock sinking into her. She pushed him away again and peeled off her panties. We might as well get down to it, she thought.

Anna threw back the covers on the bed and climbed on, sliding to the middle, on her back. "Come here," she commanded as she spread her legs, knees up, and beckoned Brandon with her finger.

Brandon climbed on and started to assume the position. On his way he began to lower his head toward her pussy. Briefly, she considered it. She had loved having Paul's lips and tongue feasting on her, but to be honest, she didn't trust Brandon not to clumsily kill the mood. He couldn't even kiss. How was he going to eat pussy? To get that cock inside her, that's what she really wanted. That was simple biology. He couldn't mess that up, could he? "Maybe later," she told him. "Right now I want you inside me."

Brandon was nothing if not obedient. He did pause to kiss her breasts, and that was OK. It was pleasant. She didn't feel the tingles rocket straight to her vagina, but it was nice. Then she felt his cock make contact, but he was too low, and it occurred to her that maybe he wouldn't be able to find the right hole. She reached down to rub his head against her opening. He had some pre-cum and she felt just wet enough that she thought she could probably get him in. She rubbed his head around a bit more. "Are you ready?" she asked.

"Oh yeah!" Brandon said. "So ready!"

"Now go slow," Anna said. "Push in, but go slow, and stop if I say stop."

"OK." answered Brandon, and he began to push.

"That's it. Just a little more." the head of his cock sunk in. "OK wait..." she paused to feel herself adjust to the size of him. "Now more..."

Brandon pushed. "That feels so good," he said. "That feels incredible."

"Now just a little more..." then Brandon was in. She could feel his balls. "Now slowly out, and back in again." Brandon drew back and pushed in, drew back and pushed in. "That's it. Just like that."

"Anna, I think I'm gonna...Uhhhh!"

Then Anna heard him, and she felt him surge and collapse against her.

"Oh no, I'm sorry. I'm so sorry! That was too soon! It just felt so good! Anna, I'm sorry."

"That's OK, Brandon," she said. "It happens. Next time it'll be better." Brandon was embarrassed, and sincerely apologetic. He was a nice kid. She didn't want to scar him, she didn't want to make him feel bad. But clearly for her, this was...this was not exactly what she had hoped for. She felt his cum start to leak out of her as his dick got softer and he pulled out, then rolled to her side.

"If you give me a couple minutes, I'm sure we can try again." he said.

"That's OK." she said. "I think maybe we should call it a night." She was over it. The Brandon experiment had clearly been a failure. What the hell had she been thinking! Sure, he was a nice kid. He was good-looking. But she didn't want a relationship with him. Maybe, she thought, she couldn't just jump into bed with a guy like girls do in the movies. Why should that be so surprising? Nope. It wasn't surprising at all. A week ago I was a virgin, she thought. This whole fantasy of hers had been stupid and foolish.

"Whatever you want, of course," said Brandon. For a second she had forgotten he was still there.

"Look, Brandon, you're a sweet guy" she was proud of herself for not calling him a kid," and I'm sure someday you're going to make some girl an excellent lover, but I have to be honest with you. For me...I guess I had some kind of cougar fantasy and that's just not me. I hope that's not unfair to you. I really want to thank you. I don't regret this. You helped me learn something important about myself. I hope you can understand."

Brandon was sheepish, but thoughtful. "Maybe a little, I guess. You're a really nice person, Anna. You're beautiful. And I've got no complaints, really I don't. I was a virgin, and now I'm not. I'd never even really kissed a woman, and now I have. I've got nothing to say but, 'Thank you!' I really mean that. Of course I want to do it again, but really, you've given me so much. You've given me something I've wanted for a long time. I'm sorry I couldn't be better for you."

"Oh Brandon you're sweet." Anna gave him a kiss on the forehead. "Just next time make it with a girl you really think you might be in love with. Can you do that for me?"

"Thank you, Anna. I will."

"Good. Now I think we better get dressed, if you don't mind."

"OK." Brandon and Anna got out of bed and put on their clothes. As he went to kiss her goodbye she turned and offered her cheek. After he'd left she drew herself a bath and settled in for a good, long soak with a bottle of wine. She realized she'd been wrong, and foolish, to try and force things like she had with Brandon. Her experience with Paul had been confusing, but it had been real, not some crazy thing she was trying to make up in her head. The way she'd left it with him, Paul had said he would call her. She really hoped that he would, and that she hadn't scared him off by acting so crazy with him.

Paul had said he'd call her in a few days. He gave her exactly a week. He wanted to call earlier, but he also wanted to make sure he gave her enough time, and he didn't want to seem too eager, too pushy. He really liked Anna. He was willing to forgive her wigging out on him, maybe, but he was also on guard. She had said she was just scared. OK. OK. Maybe that was just it and with a little time they could get past that. But Paul was not completely naive, either. Anna's little panic attack, or whatever that was, was a red flag. He wasn't exactly sure how much "crazy" he was prepared to take, or how much crazy she might be hiding.

On the other hand, Anna, and her little bit of crazy, had done wonders for his writing. In the days since their last date he'd written sixty-five manuscript pages towards his novel, which made just over a hundred pages now in total. It was really taking shape quite nicely, if he did say so himself. Because of this progress, Paul could honestly say this was about the happiest he'd been in the last couple of years. So when he did call Anna, he didn't find it hard to be upbeat.

"Hi Anna, this is Paul" He'd decided he could afford to be a little bit nonchalant. He wanted this to work with her, but if it didn't, that would be OK too-at least that's what he was telling himself.

"Oh hi Paul. It's good to hear from you. How are you?"

"I'm well. I've been thinking about you a lot." Paul paused. "Is it good to call now? If you'd still like a little time, I can call back later."

"No. Now's good Paul. Now is good...I'm glad you called." There was an awkward silence.

"Anna, I'd really like to apologize if I came on too aggressively, or made you feel uncomfortable or unsafe. That's the last thing I wanted, really it is. I really like you Anna, and I thought maybe we might have something between us worth working on. I'd sure like to see you again and see if we could explore that. I can go as slow and easy as you want. No need to rush into anything, but I do want to see you again, and see where that might lead...Is that something you think might be possible?" Paul had worked on this part of the conversation, gone over it in his head, but that was as far as he'd prepared.

"Yes, Paul. Thank you for saying that, but it wasn't you at all. You were lovely. You were perfect. It was me. I just kind of panicked because it was going so well and I got scared. I've had some time to think about it and the only thing I know for sure is that yes, I do want to see you again, Paul, if you can forgive me, if you don't think I'm too crazy. I promise I'm not crazy, at least I don't think I am. I really like you too, Paul. I would love to see you again."