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?"
