Chapter 5: Babysitting the Boys

Arranging to meet Regan again was tricky. As I said, she didn’t want me fucking her in her house when her boys were there, and her coming to my place was problematic, as you might imagine. We were pretty much limited to hookups on the weekends when her ex had the boys. So, I was surprised when she called me up on a Wednesday night and invited me out for a drink. She said she had something to talk about.

She was already there at a table when I arrived, a glass of wine in front of her. I ordered the same at the bar and went to join her. We kissed, just a hint of tongue as it was a public place and while the lights were low, it wasn’t that dark. I sat beside her, and we chatted for a minute or two. And then she got to the point.

She was heading out of town for a business conference and wouldn’t be returning until Saturday. She had arranged for a neighbor to watch the boys, but she had canceled at the last minute. Ed, her ex, was also out of town.

“They’re probably old enough to be left on their own,” she told me, “But it makes me nervous. If anything were to happen ... so, I was wondering if you might watch them.”

“I have to check with Susan, but I’m sure it will be all right.”

“And remember what you said about pimping out your girls? I think spending a few days in the company of two girls would be good for them.”

“You want me to get them laid.”

She laughed. “Well, I wouldn’t object. But I was thinking of just letting nature take its course. Female company and maybe a little necking and heavy petting. You know, teenage stuff.”

“Well from what I saw, they’re a bit beyond that stage, but I get your drift.” I didn’t say anything to Regan, but Susan and I had had a similar conversation about the girls, how it would be healthy for them to date other teens. That was one reason I thought Susan would agree.

Regan continued, “And if it turns out one or both of the boys is really gay, maybe you could help them along. Give them an alternative to ... incest.” She silently mouthed that last word in case anyone in the bar was eavesdropping. “It would be good to have an older man who I trust show them the ropes.”

“I draw the line at having sex with teens, and especially my students.” That was a lie. There were my girls, of course, and I figured that sex with Tony Williams would be in the offing soon. “That’s a guaranteed career-ender, if not a jail cell.”

“Who’s going to complain? I give you a hall pass for sex with my boys. But you don’t have to if you would rather not. I’m just saying I wouldn’t complain. And in any case, I think your girls will occupy them enough.”

That much was truer than she thought. My girls would eat those boys alive.

Susan was a bit annoyed when I told her.

“Sex with that woman is one thing, but now you’re babysitting for her?” She made a whipping motion and noise as she said it. But she admitted that it would be good for the girls.

“And besides, there are three girls here, not just two. If she gave you leave to fuck them, she can’t complain about me.”

Leah and Kenzie were ecstatic. They were so excited that they came up with a way to bring Susan and me into the action. They used their laptops and phones to set up a wireless link from their bedrooms so that we could watch what went on. They even had the forethought to encrypt it, so no stranger could eavesdrop—I love my girls. What they set up wasn’t as sophisticated as the one Isiah Williams had set up, the cameras had only one view and the sound quality was terrible, but it got the job done. And their efforts had the added benefit of getting Susan excited about the houseguests.

The next day I brought the boys home with me after cross-country practice. Susan showed them Leah’s room and told them they would sleep there. The girls would ostensibly sleep in Kenzie’s room. Of course, the kids could sleep wherever they wanted as far as we were concerned, but we didn’t tell the boys that.

After dinner, the teens disappeared into one of the bedrooms, and Susan and I settled down in front of the television, turning up the volume to make the boys think we wouldn’t be able to hear them. We just tuned our phones to the wireless link and settled in to enjoy the show.

At first, it was rather dull. They lay on the bed and talked about movies and video games and the like. When they got to talking about school, it was mildly interesting to hear what the boys had to say about their teachers—my colleagues—when they didn’t think adults were listening. But all the while, Leah and Kenzie were edging closer to one another, until they were touching. Then Leah began rubbing her hand along Kenzie’s thigh, and Kenzie turned to her sister, and they began a deep tongue kiss.

The boys just stared, mouths agape.

The girls broke the kiss, and Leah turned to the boys and said, “Are you gay or just stupid? Are you gonna join us or what?”

In a flash the boys were next to them, Adam necking with Leah and Aidan with Kenzie.

Susan turned to me and said, “It’s finally starting to get good. About time.”

The two pair kissed for a while, then Leah pushed Adam off of her, sat up, and started unbuttoning her blouse. Once the blouse had been shed, she did the same with her bra. Reaching out, she pulled Adam’s head toward her until his mouth was on her nipple, and he began suckling in earnest.

Noticing what her sister had done, Kenzie mumbled something to Aidan, something like “do you want that too?” and then she pulled off her top, unhooked her bra, and let him go to town on her puffy, little nubbins.

After a few moments, Adam started up, “What about your parents?”

“What do you mean?” responded Leah. “Are you worried we’ll get in trouble, or do you want them to join us too?”

“What?!”

“They will join us if you want. All we have to do is ask them.”

Adam just lay there confused. Aidan had also paused and was looking quizzical.

Leah smiled. “Don’t worry. They don’t care if we have sex. Now, do you want to eat my pussy, or do you want me to suck your dick?”

Adam was the poster child of indecision.

“Okay, I’ll suck your dick,” she decided. And with that she leaned over and unzipped his pants. She pulled out his erect cock and said, “Mmm, nice and big. You may be shy, but you’re packing.” Then she dove down and took it into her mouth.

By this point, Susan had reached over and was stroking my cock through my pants.

Aidan was staring at Leah and his brother, so Kenzie put her hand on his chin and redirected his gaze to her. “Do you want to eat my pussy?”

Aidan nodded and mumbled something we couldn’t hear.

“Don’t worry, I’ll guide you through it.” And with that Kenzie slipped out of her shorts and panties, spreading her legs for the boy, who lowered his head between them.

To Leah’s disappointment, Adam quickly came. Some of his cum must have dribbled onto her lips and chin because we saw her wipe it up with a finger and then stick it in her mouth. She said something to him that we couldn’t make out, then slipped out of her pants and panties and like her sister, guided his head between her legs.

By this point, Susan had pulled the sweatpants she was wearing down around her thighs, and my left hand was in her crotch. With my right, I undid my pants, releasing my cock so Susan could stroke it in earnest.

It wasn’t like watching a porn film; our view was obstructed by various body parts most of the time, and the voices were mostly unintelligible. But seeing our two girls being pleasured was more stimulating than any professional porn film. Despite the poor audio quality, it was clear the girls were giving the boys lessons in the finer points of cunnilingus. And soon enough we were watching our two teens going through the throes of orgasm.

By this point, the boys were hard again, and Kenzie laid back on the couch and let Aidan go at her missionary style, while Leah got on her hands and knees while Adam entered her from behind.

Susan and I looked at each other, and silently decided that it was time to let the girls proceed on their own. We headed upstairs, pausing at the kids’ bedroom door to listen to the moans. Then we went into our room, shed our clothes, and fell onto the bed.

We lay there facing each other, her hand slowly stroking my cock once again and my hand between her legs, rubbing her vulva. We just lay there, slowly pleasuring each other and looking into each other’s eyes.

After some time, I leaned in and kissed her, and I felt her tongue returning my kiss. Our hands left each other’s crotches and roamed about our bodies. Somehow, we had silently agreed that tonight would be one of slow pleasure.

I felt the soft flesh of her breasts, accented by the hardness of her nipples. She ran her nails along my buttocks, a tease that I found delightful. We kissed again, gently but persistently.

I knew that she was already very wet, so after a while I positioned my cock against her vagina and slowly pushed forward, entering her. Susan moaned softly, biting her lip as I pushed past her labia.

I slowly stroked in and out, and soon Susan stopped me, holding my cock hard against her clit and biting her lip again. Then she eased up, and I began stroking in and out once again. Then again, she stopped me, holding me tight against her, before letting me resume. Then again, it happened. Then I realized she was having a series of orgasms, not her usual moaning and thrashing, but quiet welling of pleasure. This went on for some time before I felt my own orgasm slowly build, and soon I was jetting cum into my sister’s pussy. It was my turn to hold her tight against me, keeping the pressure on my cock and prolonging my pleasure for as long as I could.

We kissed again for a while, then Susan rolled me onto stomach and straddled by back, giving me a shoulder and neck massage, occasionally leaning down to rub her breasts against my back. And after several minutes, I again felt stirring between my legs.

I rolled over underneath her, so her pussy was up against my cock, and pulled her down and kissed her again, all the while her pussy grinding against my ever-hardening cock. And when it was ready, she reached down between her legs and slipped my cock into her. Then began to slowly rock back and forth.

I looked up at her, my beautiful sister riding my cock. My hands reached up and cupped her breasts. She closed her eyes and smiled, rocking herself to another orgasm, followed by another by me.

Breakfast the next morning was interesting. The boys had a guilty manner about them and were uncharacteristically silent. Susan caused them to turn beet-red when she asked, “Well, did you kids have fun last night?”

It was all I could do to keep from laughing out loud. Susan had a wicked smile on her face as she said it, a smile that I and the girls could read but the boys were oblivious to. They didn’t answer the question.

“Yeah, it was cool,” said Leah finally, rescuing the boys from their guilt-ridden silence.

I drove the kids to school, and there was cross-country practice afterward, so it was just the boys and me when it came time to drive home. I couldn’t help making them squirm. As we passed a pharmacy, I asked, “Do you guys need anything from the drug store? Snacks? Condoms? Anything?” Silence, then “Last chance before we pass it.”

“No thanks, Mr. Kendricks, we’re good,” squeaked Adam.

“Friday night is family movie night, so think about what movie you’d like to see. Anything on HBO or pay-per-view is okay.” Friday was really sex night for us, not movie night, except occasionally we watched a porno to get the juices flowing. But for the moment it seemed wise to maintain a front of respectability.

After dinner we settled down in the living room for the movie. The girls had chosen Boogie Nights, which I thought was a little too on the nose. The boys were visibly embarrassed to be watching it with Susan and I, not to mention the girls. Yes, they had had sex, but that doesn’t mean teens wouldn’t still be embarrassed to watch a movie about porn and sex, even with other teens they had fucked.

The girls sat on the couch between Susan and me. Adam was in the armchair, and Aidan was sitting on the floor. When the movie began, Kenzie snuggled up to me and Leah to Susan. By the time of the first sex scene, where Roller Girl has sex with Dirk, Kenzie unzipped my pants, pulled out my cock and started slowly stroking it. For her part, Leah had her hand up Susan’s skirt, rubbing her vulva.

Aidan, being the closest, was the first to notice. Even in the darkened room I could see him redden. A few moments later, Adam’s jaw literally dropped when he noticed what was happening on the couch.

Kenzie leaned down and started sucking my cock, and Leah slipped off the couch and buried her face between Susan’s legs.

Susan and I both enjoyed the oral for a minute or two. Then I heard Susan say, “you boys can join us, if you want. Or feel free to watch and jerk off if you’d rather.”

They didn’t answer.

After another minute or so, Kenzie lifted up her head and sighed. She leaned over, took Aidan by the hand and guided him next to her between my legs. She went back to sucking my cock, letting Aidan watch from close up. But he remained frozen.