Who Loves Ya', Baby(sitter)

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"We?" I peeked around the corner. Alyssa was on the sofa, hands folded in her lap.

"I want her to see that intimacy can be pleasant," said Emily.

"With me?"

"There's no male role model in our household. Emily says nice things about you. She even told me you've caught glimpses of her, uh, endowment. And that you kissed once."

"At the stroke of midnight, but that was -"

"Emily's first, if you must know. She asked you for help, and you refused. At least some of this is your fault. You could have prevented it, with some good advice."

"I'm so sorry. Emily has been a delight with Annie. I never wanted anything like this to happen. But you have no idea what she asked -" To touch my prick, for one. And who knows what would have happened after that?

"I know she asked for your help and didn't get it. So you'll help her now."

"Anything." My mind raced with therapists, counselors, folks trained in this sort of thing. I wasn't rich, but I'd contribute to the cost.

"You need to make her feel like an attractive woman."

"But she is."

"You know that and I know that, but that young lady in the next room doesn't. So you're going to go in there and prove it to her. She trusts you. Maybe the only male on the planet she does right now. Be tender. Be loving. You'd do this for your own daughter. Be there for her. She needs you now, more than ever."

I nodded and opened the door. Alyssa sat on the couch, sniffling. Tears tinted with eyeliner streaked her face. I sat down beside her and put an arm around her shoulder. "There, there." She leaned her head against my shoulder. We were comfy. At least, I was. "Talk to me."

"I'm so humiliated," she whimpered. "How could I ever believe that someone would think I was pretty."

"I turned my body towards her. "But you are! A beautiful young woman."

"Yeah, right!" She slumped forward, elbows on bare knees. Her dress had ridden up. Her legs were shapely, and the dark pantyhose she wore accentuated them.

I looked at her mother. She made a "go on" face and waved at me.

"Do you remember our first kiss?" I asked.

Alyssa startled upright. "Mr. Marcus! My mom!" She tilted her head in her mother's direction.

"It's okay, sweetie. I saw you two, on New Year's Eve. Did you like kissing?"

"Sure." Alyssa's smile drooped. "Before tonight."

"Remind her what a tender kiss feels like," said her mother.

It's only a kiss. I held Alyssa's face gently and moved forward, brushing my lips against hers with a modicum of pressure. Her lips vibrated, and I pressed a bit harder. This was turning out to be quite a kiss, much more intimate than New Year's, which was a peck in comparison. I broke off first.

Alyssa opened her eyes. "Wow! That was great! I felt something real. You DO think I'm pretty, don't you?"

She threw her arms around my neck and immediately we were lip locked. I glanced over at her mother, who was smiling, with a look that said, 'Don't you dare break this girl's spirit.' So I kept kissing. But there's only so long in kissing before touching is mandatory. So I reached up to hold Alyssa's waist. At that instant, she pulled back.

"What's wrong, dear?" asked her mother.

"I remembered Jake holding me down.." Her voice choked up.

I shrugged at her mom, who waved again, as if we had a script and it was my line. "I'll never hurt you," I said. And I meant it. I put one hand on her waist. "There, okay?" She nodded. I put my other hand on the other side. "See? Gentle."

She nodded, and leaned forward to resume kissing. That's when I noticed that I was getting aroused. After all, sitting and kissing someone, getting excited was difficult to avoid. Then Alyssa's lips parted, and her tongue slid against mine. Startled, my mouth opened, becoming Alyssa's playground. She probed for my tongue. I held it back. I didn't sign up for Frenching. She pressed her face harder against mine, determined to make contact. Rather than suffer lip or tooth damage, I pushed my tongue forward until it touched the tip of Alyssa's. She bucked up on her knees and squeezed me tighter. One glancing blow was not enough for her. So I joined her game. We toyed with each other, tongues dancing and sharing each other's mouths. Each rub was electric. And now I had an undeniable hard on.

Alyssa melted back. "Wow, that was so much better than Diedre said."

I didn't ask about Diedre. I was too busy sorting out my thoughts and feelings. "Better?" I asked. I looked at both mother and daughter.

Alyssa nodded. "Uh huh."

"Good. So we're done here?" I straightened myself on the couch, hoping my erection wasn't obvious to Emily. What would she think, a grown man getting erect from foreplay with her daughter?

"How are you, sweetie? Better?" her mother asked.

Alyssa was flushed. "Was it wrong, what I did? I mean, letting Jake touch my breasts?"

I let her mother answer. "It depends, I guess. You shouldn't do it casually with just anyone. Perhaps if you had a strong relationship with someone-"

"Like Mr. Marcus?" Alyssa asked.

"Well, I guess so," said Emily. "I mean, he's not someone you'd date."

Damn right. Going out on dates with young women, taking them to submarine races? My prick jerked at the thought. What's wrong with me?

"I didn't mean that. Maybe Mr. Marcus could play the role of my date. Just so I can see what I'm supposed to do."

Alyssa's date had undressed her, touched her, fondled her. I couldn't do that, supervised or not. "This is not a good idea."

"On the contrary. Alyssa needs to understand proper behavior versus improper activities. I think this is a marvelous suggestion. Good idea, sweetie. So, where do we start?"

This smelled like a slippery slope. I prayed that Mrs. Bollard would provide the moral compass to keep me out of trouble.

"What can I let the boys do?" Alyssa asked. "While making out, kissing I mean, should we touch each other?"

I waited for her mother to provide expert advice. "How do you mean?"

"Well, Jake touched my breasts." Alyssa took my hands in hers and raised them.

I resisted, but her mother nodded approval. I'd done worse in my kitchen, so what the heck? The shape and resilience were different, but that was due to her blouse and bra. Thank goodness they were covered. I pictured them bare, warm- Shit! I needed to stay in control.

"It sure feels good, even through my clothes."

"And does it feel good to you, Mr. Marcus?" asked Emily.

I nodded enthusiastically.

"Then that's fine, probably as far as you should go."

Emily was keeping this exercise safe. I appreciated her support.

"And can I touch him back?" Alyssa asked. "Like this?" She placed one hand on my chest and the other on my crotch. "Gee, you're really stiff."

The question and Alyssa's action seemed to take Emily by surprise. "As long as you keep your clothes on, I suppose that's okay. How stimulating can it be?"

Plenty! Alyssa had wanted to touch my prick last time but I refused. Now, in our role-play, she'd achieved her goal.

"So, touching your date is all right. Glad that's settled." I pulled my hand back, moist with sweat. There were fingerprints on her blouse.

"But Jake saw them naked," Alyssa said. "He pulled my dress down and insisted I take my bra off."

"He did?" asked Emily.

"Didn't you listen? I was bare from the waist up. Exposed. Humiliated." Alyssa's voice cracked.

"Calm down, honey."

It was clear that Emily was slowly losing control. She needed my help to prevent this from getting out of hand. "You are feeling better, right?" I gave Alyssa a hug.

She held me close but continued the dialogue with her mother. "Just like all the guys at school, Jake was fixated on my breasts. Even Mr. Marcus couldn't take his eyes off them. Tell her."

I held my breath, hoping she wouldn't expose the details of our bare breast incident. "Alyssa's breasts are unavoidable. I'll admit it. I've stared at them. Occasionally."

"You have?" Emily seemed surprised. Hadn't she noticed Alyssa's tits?

"Maybe we should do what I did with Jake," said Alyssa. "So I'll understand."

Unbutton her blouse and hold her breasts? "I don't think that's necessary." I looked at Emily, praying she'd agree with me.

I checked her mother's expression. No adverse reaction. "Alyssa has a point. It happened, after all. Perhaps Alyssa can learn something, if we play it out."

I knew how this would play out. Badly. Sexually. "Can't we just talk about it?"

"Don't worry. I'll be here to supervise, after all."

Great help that had been up to now. Alyssa's mom didn't know this would be the second time. I fumbled with her buttons and froze. Alyssa shrugged off her blouse and popped the rear clasp of her bra. There they were, large and round and - oh God, this has gone too far.

"They're hideous," Alyssa exclaimed. "Jake wouldn't touch them except for his penis. Except he never got that far."

I was not going to tit fuck this young woman, and in front of her mother yet. I kept my hands down.

"Now, Mr. Marcus, what kind of signal does that give? Alyssa obviously feels uncomfortable about her breasts. Perhaps if you held them. Go ahead, touch her."

"Yeah." Alyssa thrust out her chest. Her tits wobbled in a "come and get 'em" sort of way.

Mrs. Bollard waved me closer. Tentatively, I reached up and hefted her breasts. My palms were sweaty as I placed them under her tits. God, I wanted to press my lips against them, kiss them, suck her nipples until they were hard and puffy - No! This wasn't right. Despite her mother's presence, this was way over the line.

"That's all, right?" Emily asked. "I mean, after you were half naked, he pushed you down."

Alyssa looked at my crotch. "Almost. He put my hand on him. Between his legs." Without asking, Alyssa put her hand on my erection for the second time. "Mr. Marcus has an erection, just like Jake did."

"Of course. You're an attractive young woman. His physiological response proves it."

"Except Mr. Marcus's is bigger." Alyssa held on tight. "Is having an erection painful?" She grabbed my groin hard, as if she wanted the last drops from a plastic ketchup bottle.

"Owwwww." I jumped from the sudden constriction.

"Oh my goodness. Poor man. He must be suffering from constriction. Let it out, dear, before he passes out."

"Hold on, I'm fine." I was in no condition to faint, yet I was super excited at the prospect of showing my erection to both women. Alyssa had my pants open and my jockeys showed a large bulge.

Emily came closer. "Oh my, you certainly are well endowed." Her eyes were glued to the site.

"I guess so. Maybe you should take your role as chaperone a bit more seriously now. We really are getting to a dangerous point here." Perhaps now they'd leave and I could jerk off in privacy.

"Momma! My panties are soaked!" Alyssa stood up and raised her skirt. Sure enough, the fronts were wet and transparent. Her labia were clearly visible, along with sparse pubic hair. Her skirt fell back to cover the treasure between her legs. I breathed a sigh of relief. Except she sat back down in my lap, arms around me.

"Can I touch it? Mr. Marcus's penis?"

"Of course not," said Emily. "That would be dangerous."

Thank God for small favors.

"Why is it dangerous, Mommy? Alyssa asked.

"Because you might get too excited, physically I mean."

"You mean all juiced up? I think I already am. Isn't that why I leaked in my panties?"

"Yes, precisely. Which is why we should stop now."

Silently, I cheered. Emily was calling off this pretend encounter, just in time. I hadn't removed my hands from her tits. Two nipples pushed against my palms.

"So what else should I do on my next date?" asked Alyssa.

"Haven't you done enough?" asked her mother.

Good. Emily was keeping the brakes on.

"I guess. But what if my date wants to go all the way?"

"Absolutely not."

I nodded in agreement. Alyssa was vulnerable. And in this role-play, I wasn't going to be the seducer. Ditz was an isolated incident, I told myself. I was only fondling Alyssa's breasts as emotional therapy.

"Couldn't my date and I pretend to have sex?" asked Alyssa.

"What's pretend sex?" asked Emily. "Either you do it or you don't."

"You mean dry humping?" I asked.

"I've never heard that term before. What is that?" asked Emily.

Shit. Now I have to explain it. "When a woman and a man position themselves with groins in contact, with clothes on."

"Like this?" Alyssa swung a leg over, displacing my hands. They itches to return. She straddled my crotch. My erection hid beneath her skirt.

"Contact through your clothing? Oh well, I guess that's okay."

She pressed her groin against my prick. "Oh, Mamma, this feels good. Mr. Marcus's erection is very stiff. "

With two layers of cloth between us, the head of my dick was nestled at her wet pantied pussy.

"Jake wanted me to take his penis out and slide it between these." She pressed her breasts together, a voluptuous target if I'd ever seen one. "I would have seen his penis naked. Can I-"

"We should stop here," I said. Would I have any self-control with Alyssa's tits around my naked prick? Even with her mother standing there?

"Mr. Marcus is right. You've gone far enough."

Alyssa put my hands back on her tits. I didn't resist. We already had permission, and compared to what we could be doing, it was quite harmless. Except every fondle of her boob flesh kept me excited and erect. Alyssa took every advantage, wiggling her hips to provoke contact under her skirt. This dry humping was the most extended not-sex exercise I'd ever participated in. Usually, after a while, my date would claim chafing or just get bored.

"This is uncomfortable. Can we touch bare?" Alyssa pleaded.

"You mean exposed genitals? Absolutely not!"

Thank God. How could I deal with Alyssa if she was any more undressed than she already was?

"Why?"

Emily swallowed hard. "Uh, you might like it too much, and then where would we be?"

"You could supervise my touching, Momma. And I promise I'll never touch a boy's penis on a date. Ever!"

Alyssa had held my cock in my jockeys, and pushed against it outside of her mother's sight. Wasn't that sufficient? "We shouldn't do anything else-"

"Pleeeeeeeeze. Never ever."

Emily evaluated our position. "If you promise, all right. Just this once."

My head nearly exploded. "Mrs. Bollard! What are you saying?"

Alyssa moved quickly. She slid back and reached into my jockeys. They slid down as my erection came out into the open. "See, Momma, see how big and stiff Mr. Marcus is." Alyssa stoked her fingers gently along its length. "But it's so smooth."

Mrs. Bollard approached and slid her hand up my dick. What was this? Two at once?

"Yes, dear, he has a very nice penis. Be careful with it."

Alyssa resumed her previous position above me and sat down. Now it was just her panties, and they were retreating into the folds of her cunt. My bare cock was skimming the surface of her exposed lips.

"Why did Daddy leave us?" asked Alyssa.

Emily choked. She didn't expect that question, in the midst of our role-play. But it was oddly relevant, if Alyssa's interpretation of the facts were accurate.

"I guess I've never told you the whole story. It started after Rodney attended his ten year high school reunion."

"Don't tell me - his first love was there?" asked Alyssa.

Patches of pubic hair were tickling my dick. The head pulsed, and precum flowed.

"That's just it," continued Emily. "She didn't show up. That made him nuts. He tried everything to find her. I was completely humiliated. Then one day he came home whistling. He'd been assigned a new secretary. Leslie! God, how I hate that name. Leslie this and Leslie hat. Young, perky -"

Alyssa interrupted. "And big tits! I saw her once, at his office."

"She was well endowed all right, but that's not what he talked about. It was her smile, her enthusiasm for life, her limitless future possibilities."

"So it wasn't her tits?"

"If it were only that simple, I would have gotten implants. No, it wasn't physical. In our last conversation before he left, Rod told me it was my lack of confidence, my personality that killed our relationship. I was dragging him down. Leslie was lifting him up."

And probably getting him up. Just like Alyssa had done with me. I put my hands on Alyssa's hips, to slow her undulation.

"He was a jerk to leave you and run off with her." Alyssa kept humping me as her mother told the story. I sensed that her panties had retreated into the folds of her pussy, and that the tip of my penis was prodding her bare pussy lips. If not for her panties, given the force of her bouncing, I'd have penetrated minutes ago.

This had to stop, or we'd all regret it. "So that's how dry humping works." I tried to make my voice dispassionate, authoritative. "And that's enough, I think. More than enough."

"I agree," said Emily.

Finally, some support.

Alyssa ignored my comments. She was having too much fun. "Mr. Marcus's penis doesn't feel dangerous."

"Well, it is. If your hand enjoyed the feel, your vagina would like it even better."

"Really?"

"Yes. I'll show you." Mrs. Bollard came around to the back of the couch. "Pull your panties to the side."

What was Emily doing? Testing my resolve? She might end up disappointed.

Alyssa fumbled, extracting the wet panties from her gash and smoothing them over her labia before lifting her skirt.

"Now, promise me you'll never do this on a date, right? Pull them aside."

Alyssa nodded vigorously as her cunt came into view.

God! There it was, exposed, moist, available-. "Emily, this has gone far enough. I've massaged Alyssa's breasts and we've dry humped. Don't you think we should stop-"

"Shoosh. I've got things under control. See how his penis feels against your bare skin?"

Alyssa held my prick and rubbed it against her moist opening. "Hmmmm. It feels real good. The harder I press, the better it feels."

It was electric on my side. The tip of my cock meandered against her cunt lips.

"Not too hard, or it might slip in."

Alyssa giggled. "That's silly. Mr. Marcus's erection would never fit inside me. I'm too small."

Ms. Bollard stood behind me, a silent witness. I knew that Alyssa's pussy would stretch nicely to accommodate my prick. Didn't Emily? She seemed fixated on the sight of my dick at the entrance to her daughter's cunt. Why wasn't she willing to admit it out loud? So I spoke up. "Maybe we should stop here before-"

"See?" Alyssa aimed my dick at her pussy and pulled. Her juices and my precum lubricated the path.

I tried to pull back, away from Alyssa, but I was pinned against the couch. Nowhere to run, nowhere to hide. Alyssa scooted closer, taking aim. The head of my dick edged past her outer lips.

"Noooo." This was wrong, so wrong. So why did it feel marvelous?

"What are you doing?" asked Emily. It was like seeing me penetrate her daughter's cunt brought Emily out of a coma.

"You said it wouldn't fit. But it does!"

"Get up from there, young lady."

"But Momma, Mr. Marcus's penis fits. And it fits gooood!" She lowered herself a bit more, and my prick advanced, deeper into her channel.

All I could think about was the heavenly feeling of young, firm pussy around my prick. I was way too distracted to object. Besides, I didn't want to impose limits. That was our chaperone's job.

Emily shouldn't have been flabbergasted at our coupling, but she was. "You're too young to be doing this."

"I'm eighteen. Besides, would you rather I do it in a car with some stranger? At least you're here to supervise." Her weight moved her down my pole. "Is this fucking, Momma?"

We were joined, and I'd penetrated, but we weren't fucking.

"I don't know. Mr. Marcus?"

I had no answer but felt obligated to speak. "Not in the technical sense of the term." What, I was supposed to admit doing something I was trying desperately to avoid?