Engaged

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A frustrated teen seeks advice from his old babysitter.
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Rob ran past the fountain in the courtyard and pressed himself into the building's entrance to get out of the rain. He found her name immediately, an apartment on the second floor. He pressed the button and waited, hoping. Just before he was about to press again he heard her voice. He recognized it at once, even through the tinny intercom. "Oui?" she said. "Qui est-ce?"

"Uh, it's me, Rob. Rob Burton."

"Rob - Robbie? My little Robbie?"

Rob blushed. "Well, yeah, but I'm not, you know, little any more."

Her laugh bubbled through the intercom. "No, I guess not," she said. "It's been a while since I was your babysitter. You remember that, don't you?"

"Oh yeah," he said quickly, "I do, sure."

There was a pause. "Hey, Robbie, here's a little test - what was our favorite babysitting game?"

"Tie-up," he said without hesitation.

She laughed. "Right!" she said. "Okay, you pass the test, come on up." The door buzzed and Rob pushed it open. A staircase on the left led upwards. He walked up one flight, and knocked on one of the two doors in the hallway, the one with her number on it. It opened immediately.

"Robbie!" The woman who greeted him was tall, with a trim yet voluptuous figure, and blond hair that was tied back in a pony-tail. Her face was startlingly pretty and intelligent, with clear blue eyes and full lips. She was barefoot, and wore faded jeans and a light blue sweatshirt.

"Uh, hi, Anita."

"Get in here, you," she said, "Oh my God, look at you, you're taller than I am now!" She took him by the shoulders and pulled him into the apartment. Stepping back she looked him up and down appraisingly. "Oh, Robbie," she said, "it is so amazing to see you!" She moved to him and gave him a hug, pressing herself against him. She pulled back and looked into his eyes, then kissed him full on the lips. The kiss was brief but he felt a fleeting touch of her tongue between his lips before she stepped back again, beaming at him. "But you're soaking wet!" she said. "Come get this wet stuff off before you catch your death."

Rob took off his jacket, and Anita insisted that he take off his sweater as well, which had gotten wet in the downpour.

"There," she said, "that's better. You feeling cold? I'll turn up the heat."

"No, I'm okay," he said, "this is good."

"Don't be silly," she said, and adjusted the thermostat on the wall. "Now go sit down and I'll make some hot tea." She pointed to a long leather couch against the wall in the living room. "Or I could make cocoa for you, the way I did when you were a little boy. You feeling like a little boy tonight, all cold and lost?" She winked at him with a mischievous grin.

Rob laughed. "No, tea is good," he said. "Can't remember the last time I had cocoa."

"Well, we'll have to stir up some old memories when I get back," she said, disappearing into the kitchen. "It's been years!" Rob started towards the living room, then looked down at his feet and stopped.

"Uh, Anita," he called. "Is it okay if I take off my shoes? They're kinda wet and I don't want to get your rug all messed up.

"Of course!" she said, poking her head around the corner of the room. "You can take off anything you like!" She wrinkled her nose playfully and winked. "Just kidding," she said, and disappeared back into the kitchen.

Rob kicked off his shoes and went into the living room. He sat down on the couch, running his hand along the luxurious, tawny leather of the cushions. A coffee table was in front of the couch, covered with several books. They appeared to be text books and journals on psychology, as well as an open notebook. He glanced at the notebook whose pages were covered with writing in a neat, precise hand, which he took to be Anita's.

"Were you working?" he called out to the kitchen. "I didn't mean to disturb you - I mean I could go if you're busy, maybe come another time?"

Anita came into the living room carrying a tray. "No, don't worry about that," she said, putting the tray down on the coffee table next to the books. "I was ready for a break anyway." She gathered up the books and papers and moved them to another table, then sat down on the couch next to him. "Here you go," she said, handing him a cup. As he took a sip she took a plate of small flakey pastries from the tray. "Here, try one of these - real mille-feuille, I got them at a little pâtisserie on Saint Denis." She took one and nibbled at it delicately as she offered the plate to him.

"Good," he said. "Nice." He took care not to drop any crumbs on his lap or the couch. He looked towards the books on the table across the room. "So, were you studying or something?" he asked.

"Yeah," Anita said, "doing research, actually. I'm a little behind schedule on my master's thesis, so I grab what time I can when I'm not in school or working."

"Master's, wow," Rob said. "I heard you were going to school but I didn't know you were going, you know, so far."

Anita shrugged. "I like it," she said. "I wasn't really the student type when I was a kid, but then I got interested. Especially in psychology, what makes people tick and all, you know?" She drew her legs up on the couch and turned towards him, moving very close. "But tell me about you, Robbie, what have you been up to?" She reached up to move a strand of wet hair off his brow.

"Actually, I'm in school too," he said. "Concordia, I started last year."

"Really! Good for you. What are you studying?"

"Not sure yet; maybe engineering."

"Fantastic! I always knew you were a smart kid. Gosh, when did we last see each other? Was it a wedding or something like that?"

"Yeah, when my sister Dory got married."

"Right! I remember now. How long ago was that?"

"Uh, about five years ago. Yeah, five."

"Wow. Yes, I remember. You were so shy at the reception. I made you do a slow dance with me, remember?"

Rob blushed. He often remembered that dance, especially during solitary self-pleasuring sessions in bed at night. He hadn't yet shot up in height, and had been a full head shorter than nineteen-year-old Anita. As he danced with her he found himself staring straight ahead at her ample bust, at the tops of her breasts swelling above the neckline of her low-cut dress. He felt a twitch between his legs at the memory. "Yeah," he said, his voice cracking. He cleared his throat. "Uh, yeah, I hope I didn't step on your feet too much."

"Oh, you were so cute!" she said, tousling his damp hair. "No, you didn't step on my feet. You were so serious, concentrating on your steps, I guess. I couldn't even get you to look up at me!"

"Sorry," he said. She laughed and gave him a light punch in the shoulder.

She took a sip of her tea then put the cup back on the table. "So tell me," she said. "You have a girlfriend, Robbie? Meet anyone nice at school?" She watched his face over her teacup.

"Uh, yeah," he said, "well, sort of."

Anita raised her eyebrows. "Sort of?" she said. "How can you 'sort of' have a girlfriend?" She chuckled. "Does she know she's your girlfriend?"

Rob glanced at her quickly then looked away. "Well, yeah, of course she knows," he said. "I mean, I'm not stalking her or anything." He shifted uncomfortably on the couch. "She's just ... well, it's sort of complicated."

Anita put her hand briefly on his leg. "I'm sorry," she said. "I was just joking. So - it's complicated. How do you mean?"

Rob took a deep breath. "She, well, she ... I mean she says she loves me, and I love her, but when we're together she doesn't seem to, you know, seem to be interested in doing things that are ... well, fun."

"You mean sex?" Anita said.

"Uh, yeah, I mean we get real hot together, you know, and she seems ready to really get into it, but then she'll just say something like, oh, it's late, I have to get home, or she's not in the mood, or she's not ready, even though just before she said things that really sounded like she was ready! I just can't figure her out."

"Hm," Anita said, taking a sip of tea. "When was the last time you saw her?"

Rob was silent for a long moment. "Tonight," he said finally.

"Tonight?" Anita said. "You saw her tonight?"

"Yeah, uh, I was with her before I came here."

Anita grinned. "And why did you come here?"

Rob stared at the floor, embarrassed. "Uh, I thought, I don't know, I thought maybe you could give me advice or something, I mean I've known you a long time, and..."

"Advice from the one who taught you how to play tie-up?" Anita interrupted.

"No! I mean yes, or maybe, I thought ... Oh I don't know!" He was blushing furiously now. "I was just walking around in the rain and I thought of you ... oh shit I'll just go now, I was so dumb! This is weird." He started to get up.

"Don't be silly," Anita said, pulling him back down on the couch. "You're not going anywhere!" She pulled him around to face her. "It's not weird at all. You've been having frustrating experiences with a girl, and it's totally natural for you to be drawn to someone you had nice times with in the past. Many men sometimes have fantasies about their mothers for that reason."

"My mother!" Rob cried, shocked. "I've never..."

"No, no, I didn't say that you have! All I'm saying is that early crushes can have staying power. When I was your babysitter - how old were you? - ten, I think, when I was fifteen? - we had nice times together, and those warm memories will be with you forever. So when you have difficulties with your girlfriend...what is her name?"

"Danielle."

"When you have problems with Danielle then it's not only natural for you to seek out someone like me again, it's inevitable."

"I guess," Rob said, shrugging. "But I don't think of you as my mother!"

"I hope not," Anita said, laughing. "I'm only five years older than you, and I don't think your mother ever lay on the floor with her hands behind her back, pretending to be tied up, and then tied you up and tickled you!"

"No," Rob laughed, "I think I would have remembered that!"

Anita laughed and clapped her hands. "You're getting your sense of humor back, now that's the little Robbie I remember!" She reached for her tea cup, then put it back down. "You know what," she said, "I'm in the mood for some wine. Would you care to join me? Are you allowed to have wine, little Robbie?" She winked at him, her blue eyes sparkling.

"Well, I guess it's okay as long as you don't tell my mother on me," he said with a grin.

"Good!" she said, jumping up from the couch and heading for the kitchen. "Now don't you run away," she said, wagging a finger at him as she left the room. "I'll just be a minute or two." In the kitchen she took an opened bottle of sauvignon blanc out of the refrigerator and put it on the counter. Then she went across the hall into her bedroom. When she came out a short time later the jeans had been replaced by a short, tie-dyed cotton skirt, and her hair had been released from the ponytail and now hung loosely in gentle waves to her shoulders. She'd removed the sweatshirt, leaving the loose, midriff-baring t-shirt she'd worn underneath it. Her breasts swayed under the cutoff tee as she walked, unencumbered by a brassiere. She retrieved the bottle and two glasses from the kitchen and returned to the living room.

"Here we are," she said, holding up the wine and glasses.

"Wow," Rob said, taking in her change of wardrobe. "You look nice."

"Well, it's a special occasion, you know," she said. "It wouldn't be right to stay in my knock-around clothes for a reunion with my little Robbie." She walked to the couch and set the bottle and glasses on the coffee table. Sitting down next to him she poured them each a glass of the pale yellow wine. She raised her glass and clinked it against his. "Here's to tie-up buddies!" she said, winking as she took a sip.

Rob grinned shyly. "Yes," he said, "and to my favorite babysitter!" He raised his glass and took a large sip. He choked a little and lowered the glass.

"Easy there!" Anita laughed. "You sure you're old enough for wine?"

"Sorry," he said. "Guess I'm not used to fancy stuff." He put the glass down and looked at her. "I'm...I'm glad to see you again," he said.

She smiled at him. "And I you," she said, touching his cheek tenderly. "Imagine, my little Robbie, all grown up." They began to talk about their earlier lives, recalling memories that made them both laugh. Anita asked about his sister Dory, and was surprised to learn that she was expecting. "We'll be calling you Uncle Robbie soon," she said, holding up her glass in a toast. He asked about her family, too, none of whom he had seen since his sister's wedding.

"And, uh, how's your sister Michelle?" Anita had sometimes taken Rob to her Uncle Jack's big cabin in the country when she went there on family outings. Michelle was two years older than Anita, and Rob remembered how she used to swim nude when she and Anita would take him down to the little river that ran through the property.

"Oh, she's fine," Anita said, eyeing him with a twinkle in her eye. "I guess I know why you remember her," she said. "She enjoyed teasing little boys like you. You were so cute, trying so hard not to look at her, but you managed to get plenty of peeks, didn't you?"

Rob was blushing again. "I, uh, no, I just remembered her, I mean being your sister and all, you know?" He reached for his wine glass and took a large gulp, not meeting Anita's eyes.

"Uh huh," Anita said, giving him a poke in the ribs, "right." She took a sip from her glass then put on the table. "By the way," she said, "did you know that she's gay?"

"Huh? Your sister? She is?"

"Yes, she came out last year. I mean, we all knew she was - except for Uncle Jack, he's so clueless - but she finally made it official. She seems a lot happier now."

"Wow, I never would have thought, I mean, she's so, so..."

"Why, because she's pretty? You think you have to look like a big, rough dike to be gay?"

"No! No, I just meant that she, she just didn't seem to me..."

"You can't tell just by looking at people, Robbie," Anita interrupted. "Anybody could be gay - me, for instance." She looked at him with wide eyes.

"You?" he said, stunned. "You mean, you..." His voice trailed off. Suddenly she laughed and clapped her hands.

"Oh, you are so easy to tease! I really had you going there, didn't I?"

He smiled sheepishly and shrugged. "But Michelle, is she..."

"Yes, she really is," Anita said. She leaned closer to him and looked into his eyes. "But I am not - definitely not." She held his gaze for a few seconds then picked up his wine glass and handed it to him. "Drink up," she said. "There's plenty more where this came from." She picked up her own and took another sip.

"Now," she said, putting her glass back on the table and turning towards him, "this girlfriend of yours, this Danielle. What's she been doing with you?" She leaned closer. "Or not doing." She winked. "You know," she said quietly, putting her hand on his leg, "I couldn't help noticing that you were in a state when you arrived tonight. You still are." She ran her fingers over the discernable bulge in his pants at the top of his thigh. "She do that to you?" She withdrew her hand and looked at him.

"She, uh, I mean we..." Rob stopped in mid-sentence tongue-tied. The way Anita had turned to face him had caused her short skirt to ride up, revealing a small triangle of white panties between her legs. To his horror Rob realized that his erection was growing visibly larger. Anita noticed this and smiled.

"Well, let's talk about this, shall we?" she said softly, running a fingertip slowly along the length of his hidden penis. Rob looked at her, and then down to her hand. He swallowed hard, unable to speak. "So tell me, Rob, what did she do to get you like this?" She moved away from him a bit and rested her arm on the back of the couch, her skirt rising higher as she did so. She gazed at him expectantly.

"Uh, she...she sort of touched me," he said, looking away.

"She touched your penis?" Anita said. "Your cock?"

"Yeah. I mean we were touching each other, you know?"

"Where were you?"

"In her dorm room. We went there after going to a movie."

"You do that a lot?"

"Yeah, I guess so. I mean, we're dating, you know?"

"So she touches you often? On purpose, to get you hard?"

"Well, yeah, after we got to know each other. I mean, it's not like..."

"And is she good at it? Do you enjoy it?"

Rob rubbed the back of his neck, embarrassed. "I like it, sure, I mean who wouldn't?" He attempted a small smile, which failed. "It's just that, uh..."

"Yes?"

"She, uh, well we never finish, you know? We don't really have sex."

"What happens instead?"

"Well, we mess around for a while like I said, and she tries to get me harder, so we can, uh, you know, but... Anyway, pretty soon she'll say something like it's getting late or she has something to do, or maybe we should try again another time. Stuff like that."

"She's never brought you to climax with her hands?"

"Uh...no."

"Poor Robbie!" she said with a little pout. "Could it be she doesn't know how?"

He shrugged. "Maybe. I don't know."

"Have you ever talked about it? Told each other what you each like?"

"Uh, no, things just sort of go along without saying anything."

"Do you masturbate, Robbie?" She laughed at the blushing this provoked. "That was a silly question, I guess," she said. "Of course you do! And you know exactly what it takes to get you off. So maybe it's time to educate Danielle." She got up on her knees and moved closer to him. "But first we need to learn more about Robbie." She reached down and began to lower his zipper.

Rob stared at her and instinctively drew in his breath and covered his crotch with his hands. "Now don't be silly!" Anita protested. "I've seen you before, you know. I was the one who would get you ready for bed when you were a lot younger than ten." Rob exhaled in resignation and put his hands down at his sides. "That's better," Anita said, and gazed at him as she slowly unzipped his fly. "Let's see just how Danielle has left poor little Robbie." He was wearing boxer shorts, so it was easy to work his penis out into the open, which she did with practiced deftness. "There!" she said, looking down at his erection, which was standing straight up from between his legs in a rigid, curving arc. "Oh, my! I really shouldn't be calling you my little Robbie any more," she said, winking at him. "You have certainly grown - lucky Danielle!" She delicately grasped the shaft of his penis near the base with thumb and index finger and swayed it gently from side to side as she examined it carefully. "Well, she did get you nice and hard, I can say that for her," Anita said, although she knew full well that Rob's erection had more to do with what was happening now than what had gone on in the dorm room. "Still," she continued, "I think we're going to have to teach Danielle the proper way to worship Robbie's beautiful cock!" As she said this she ran her fingertips lightly up the underside of his shaft and off.

"Oh!" Rob gasped at the sudden, fleeting pleasure and looked at Anita in surprise, his eyes full of confusion.

She opened her eyes wide and said brightly, "So, let's find out what it is that Robbie likes! Let's do some experiments." She pressed a finger against her lips and frowned in thought. "Hmm. Okay, so do you like this?" She grasped the middle of his penis in a firm grip and moved her hand up and down slowly, alternately tightening and loosening the skin of his erect phallus. Rob closed his eyes and moaned softly. "Or how about this?" She encircled the top of his penis with her fingertips and fluttered them rapidly and lightly around the head. Rob's moaning grew louder. "Or how about this - do you like this, Robbie?" She formed thumb and forefinger into a ring and moved it gently up and down at the top of his shaft, delicately teasing the engorged head and its underside with slow, sensuous strokes. "Does Danielle do this for you, Robbie? Would you like her to?"

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