New Man Pt. 05

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

She let go of her ass for one of my hands. We brushed her mound together, taking our time, enjoying ourselves while we had this moment. Unlike our first time together with Isaac in the house, we had no trouble being quiet. I think we were too drunk on each other. Her hand slid with mine lower, and we brushed her clit, her lips wrapped wide around my achingly hard prick. She leaned down and kissed me, whispering two words I loved to hear.

"I'm close."

"I'll help you," I murmured back.

Jenna nodded and I began to grind my cock up into her as she rocked her hips. She stayed low, and I wrapped the arm that wasn't rubbing her clit around her, keeping her there as my cock and her pussy did their slow dance together. I did not fuck her. I don't think I pulled back out of her once during that whole exchange. We just sort of rocked, and it left both of us feverish with need.

Her lips found my cheek, and in between butterfly kisses, she moaned almost silently, "Lionel, my Lionel..."

I murmured back, "Let me see it. Fuck, you're beautiful when you come."

She sat back upright, hands all over, ending up at a breast and her neck as her pussy rocked on my cock. A soft his of pleasure escaped her and her mouth opened in an O. The orgasm rumbled through her like thunder on the horizon, low, slow. She shivered with it, her ass clenching, her pussy driving down on me harder. When she came down, she dropped again, and I held her tight to me as she caught her breath and clung to me.

Finally, she pushed herself up so she was staring me in the eyes. One of her hands went to mine and guided it to her bottom. I arched an eyebrow and she nodded, smiling. We pulled apart from each other, my cock still hard. From my underwear drawer I pulled out a bottle of lube. Jenna got on her knees on the bed, but that wasn't how or where I wanted our first anal session to take place. I curled a finger at her, and she hopped off, looking confused until I opened the doors to the balcony.

"Naughty, naughty," she whispered to me as she passed, gripping my cock and pulling me along behind her.

"The neighbor on the other side of the fence is gone for the week," I murmured into her ear as I wrapped my hands around her and rested my cock against her back. It was the only house with the right angle to see the balcony.

I turned and shut the balcony doors. Jenna leaned on the balustrade, shivering slightly. From the cold, from the anticipation, I didn't know. But she was beautiful in that moment, staring out over the yard, her bottom up, waiting for me.

I slicked up my fingers with the lube and stepped behind her. She whimpered as the digits touched her cleft, teased around her hole. I kissed her shoulder as I slid them in, easing the lube around and enjoying the preparation of her. Slowly she relaxed, and I went just a little deeper, getting her body used to me. After I added more lube to her cleft, I stroked my cock, keeping myself hard.

"Ready?" I asked her. Jenna nodded, and looked over her shoulder at me as I slipped my fingers free and guided my cock to her bud.

Slowly, carefully, I sheathed my tip into her. Even with the plug she used earlier, she was still tight around me, and I gave her a long moment to get used to the sensation, to give me the tiniest nod over her shoulder before I eased further in. It was slow like that at first, me inching in and resting, inching in and resting. She wasn't going to take much more than an inch or two of me but that was plenty.

I've always considered anal the most intimate a couple can be if they're doing it right. It forces you to be slow and feel your partner's responses. It's not about taking. It's about giving. Your partner is giving you access to one of the most delicate parts of the human body, and it's going to hurt, at least a little. So by giving them what they need, you're making a promise to them -- I will take care of you.

I took care of Jenna.

With crickets chirping in the yard and beyond, Jenna rested her elbows on the balustrade again, swaying back and forth as my cock slid back and forth through the first couple inches of her ass. I reached around her, circling her clit with two fingers on one hand while the other teased her folds. She moaned when I slid my middle finger into her pussy.

"So full," she whispered.

"I love your ass around me," I murmured. "This sexy ass."

"Mmm. T-taking me good..." She twisted her head, and I could see how flushed her cheeks were, what this was doing to her. "Come inside me, okay? I want to feel it."

I leaned down and kissed her shoulder. She turned her head back towards the view. My finger inside her turned to two, and I began to rock my cock in and out of her ass with a little more force. Not much, but enough to drive up my own pleasure. She liked that, rising up on her toes, her body tensing. I paid more attention to her clit too, finally quitting my teasing and stroking it with every thrust. Her need made her so wet her thighs were slick with it, and I longed to taste that pussy again before the night was through.

"Faster," she whispered, "but not deeper."

I obliged, and her breaths turned jagged and sharp. She rose up, reaching back behind her head for mine as I fucked into her ass, my big cock spreading her so wide around me. She gripped my neck and hiccupped once, twice, three times before she moaned, "Lionel..."

Her legs rocked. It was the only real sign she came, but a moment later her hand dropped from my neck to my fingers against her clit.

"Too, too sensitive..." she moaned.

"Need me to pull out?" I asked her.

"No, God no."

I chuckled and kissed her neck. I wrapped my arms around her waist, my cock going faster now, nearing my own edge. I wish I could take a picture of this moment, us on the ledge, rocking together. Then again, I doubted I'd ever forget it. I sucked at her neck as I neared, my breath hot against her skin. I think she might have come again, I'm not sure, but she shook in my arms, whimpering my name over and over again.

"Lionel, my Lionel, nnn, come in me, come in my ass, baby..."

I delved in one last time, my cock straining to go deeper, to fight my self-control, but then I was erupting, spilling into her so hard and so much that when I finally pulled away, gasping, she leaked me all over her thighs and down onto the ground. I stumbled backwards against the wall, panting, trying to stop the world from shaking, and she came to me, laughing breathlessly, kissing me, squeezing my ass.

"Holy fuck," I finally managed. "That was... mind-blowing."

"It was," she agreed. "Shower?"

"Just... just give me a minute," I said weakly.

I don't know why I was so drained, but sometimes, holding back like that takes it from me. Jenna headed in and started the shower, and in a minute, joined me with a glass of water from my bathroom. I drank it gratefully before kissing her again, and then it was my turn to take care of her, guiding her into the shower and cleaning her with gentle strokes from a washrag. We fooled around a little bit more in there, mostly just playful kisses and quick gropes, but she was sore and I was drained. Soon enough we were drying off, and I kissed her again before saying, "You could stay."

It wasn't the wrong thing to say. But it wasn't who Jenna was or who she wanted to be. Her smile was sad, almost pained, and I knew her answer before she said it. "I think... that would be pushing the casual part of this too far, Lionel."

I nodded. "Then let me walk you to your door at least."

The pain in her smile slipped away, replaced by something more genuine. "I'd like that."

We dressed, and barefoot, I walked her across the street to her door. We kissed again, a sparkle in her eyes now. "Sarah is going to be furious," she said, and squeezed me in my slacks again. "Mm. Okay. Good night."

"Good night, Jenna."

* * *

Jenna wasn't wrong. Sarah called me sometime just after dawn, the world still highlighted in pinks. I was belly-down in bed, my head twisted against an enormous down pillow. The thick comforter around me felt like heaven and I was toasty warm. I was so comfortable and pleasantly drained I almost let it go to voicemail.

But eventually my fingers spider-walked across the bed to my nightstand, and I pulled the phone to my ear. "Yullo," I muttered.

"Why did that slut get to take it in the ass before I did?" Sarah squawked. "You promised you were going to-"

"Ungh," I said, and hung up on her.

She called again in seconds. "You ass-"

"Try again."

I hung up a second time. It was a full ten seconds before Sarah tried again.

Through what had to be gritted teeth, Sarah said, "If you hang up-"

"Sarah."

"What?"

"I own you. Pussy, mouth, and soon your ass. You don't own me. If you're going to call, you be quiet and respectful. Otherwise next time I see you I'm going to buy a ping pong paddle and leave that ass as red as the Abernathy's Porsche. Got it?"

A pause, then, "How is that a punishment for me?"

That took me by surprise, and I laughed. "All right, fair point. And now I'm definitely buying a paddle. Look, you're not my only girl. You know that. What happened with Jenna isn't some statement on who I like the most. You, Yvonne, Jenna, I'm crazy about each of you. So why don't you come over tonight, meet Isaac, and I'll make you dinner too?"

"Well... I... yes. Actually, that sounds nice." A pause, then, "But... why don't you two come here? I trained to be a professional chef before my life took a different route. I like cooking for people and I don't get to do it often enough."

"Wow. Yeah. That sounds great as long as you let me return the favor sometime."

"Perfect."

We talked menu for a bit, and I promised I'd bring a bottle of wine.

"Hey, Sarah?" I asked before we hung up. "The whole dominance thing, if it's too much..."

"No," she murmured. "No. Okay?"

"Got it. See you tonight then."

"God yes."

I yawned my way through a shower and dressed for work. When I was finishing up, I heard the shower run from Isaac's bathroom upstairs. That was new. Not that he didn't know how to run the shower, but my boy was definitely a bath guy. Sometimes it took every bit of my patience not to drag him out of there if he got to reading in the tub.

While I made waffles and cut up some fruit, he meandered downstairs. His hair was slicked back with gel. Also new, and I thought I finally figured it out.

"Morning," I said.

"Morning."

I finished up making breakfast, and when I settled at the table, I could see the beads of gel still in his hair. I sipped my coffee and said mildly, "I like the new look."

"Thanks."

"Can I make a suggestion?"

As Isaac took a waffle, he blinked up at me. "What?"

"When you use the gel, you only need a dab. Just a little bit, like maybe twice as much as you'd use to brush your teeth. Then dab your comb in it, and run the comb through your hair."

"Did I do it wrong?" he asked.

"There's a lot of gel in there," I admitted. "Come here. Leave breakfast for a minute."

I guided him up to my bathroom and waited for him to wash out the extra gel. When he emerged from the shower and dressed again, I showed him how I did it. I also gave him a part that added about three years to his boyish face and broke my goddamn heart to look at, even as I fought down a surge of pride he wanted to become more of a man.

"Can you teach me to shave too?" he asked.

"You don't need it yet, but sure, I can show you the basics. Tomorrow, though, okay? We gotta go eat breakfast quick." I pretended to think something over. "Unless you want to take your time. I could drop you off at school."

Hastily, Isaac said, "No, no, really, I, um, I like taking the bus."

I deserved an Oscar for fighting down my grin and nodding solemnly. "Okay. Then we'd better go eat."

* * *

A light rain fell that night, but I decided we should walk anyways so I held an umbrella for us both. Isaac was dressed pretty darned stylishly in a black button down we bought after school and a good pair of gray jeans. He spent ten minutes trying to restyle his hair just right that evening until finally I growled at him that we were going to be late.

He had no clue whose house it was we were going to. He knew who Sarah was, and had been enamored with her since the first day we saw her jogging down the street, so it was going to be fun watching his eyes bulge when she opened the door.

Along the way, at the Ayer house, Isaac's young friend George looked out the window and soon rocketed across the street. "Hey, Isaac, you want to come over and stay the night?"

Oh, I was tempted to say yes. But Sarah wanted to meet Isaac, and truth was, I wanted to de-mystify her for Isaac too, to get an honest gauge of how the two interacted. I tried not to think about it much, but in the back of my mind, I always wondered if one of the women I was dating might not make for a more suitable motherly figure in his life. Jenna was out, but both Yvonne and Sarah were definite possibilities. Then again, I wasn't in a hurry to rush into anything long-term. It was a strange dichotomy, but not an unpleasant one.

"Can I?" Isaac asked me.

"I'm sorry, bud, but we said yes to dinner elsewhere. But afterwards, if it's okay with Garth and Christy, yes."

"Cool!" George said. To Isaac, "I'll call you in a minute."

"Okay!"

We continued on, Isaac's steps lighter. Well, that worked out, but I'd really need to look into a good babysitter for date nights. Garth and Christy would definitely be the ones to ask about that. Wait. How would date nights even work with three -- and potentially five, if the twins were really as interested as they seemed -- girlfriends?

What a problem to have, right?

I mulled on it with the biggest, dumbest grin of my life as we approached Sarah's house. As I turned up the sidewalk, Isaac kept going. I grinned and said, "This way."

He turned and stopped. "Wait. George told me..." He made big round motions with his hands in front of his chest. "...she lives here."

"You're all class, Isaac. And yes. Her name is Sarah, and she's a very good friend."

"A very good friend like Jenna and Yvonne?"

"Yup."

"You're my hero," he breathed.

I laughed, and we headed up the sidewalk. Isaac rang the doorbell, and we waited until Sarah opened the door. I had mildly worried she might dress inappropriately around Isaac, given a certain tendency to flaunt herself around me, but tonight she was dressed in a cashmere turtleneck and white slacks. Sexy? Yes, but also terrifically beautiful and classy.

Sarah came equipped with two smiles -- a cocky, arrogant one that made me want to drive her into a mattress until she screamed unintelligible obscenities, and a sweeter, more open one that could melt my heart just as easily. Right now, she gave us both barrels of her sweet smile, her hand on one hip as she stood back away from the door.

"Hello," Isaac said very quietly, his eyes as wide as I'd expected, and then some.

"Well, hello, Isaac!" Sarah caught sight of the umbrella. "Oh my gosh, you two walked? Get in here, get dry, get warm." Isaac slid past her, gaping at the living room. I didn't have much time to take it in the last time I was in this house, considering I was a little busy fucking the brains out of Sarah. It was a nice place, cozy. Her furniture was all overstuffed and plush, and she had a trio of game systems in front of her TV that wouldn't hurt my boy's opinion of her in the slightest. "It's great to finally meet you. Officially. I saw you at your party. You're a heck of a swimmer."

I nudged him. "What do you say?"

He blushed. "Um. Thank you. Dad brought you wine."

"That I did," I said, hefting the bottle. She took that from me along with the umbrella, leaving the latter in a corner before we padded together as a herd towards the kitchen.

"Your dad tells me your favorite food is fish, is that right?" Sarah asked. When we talked the menu through for the night, I mentioned it was the one food Isaac hated the most. I didn't need to bother hiding my grin. Isaac was keeping pace with Sarah, looking up at her with eyes approaching worshipful.

"Um... ummm..." he said, flailing. "I'd... I..." He glanced back at me helplessly, and Sarah giggled.

"It's okay, I know it's not your favorite. How does, hm, broccoli cheese soup and meatloaf sound?"

"So good," Isaac said. "Fish. Blaaaagh."

"Now, you say that, but if I do a fish fry someday, you have to try a bite. I promise, I won't make you eat more if you don't like it, but you can't live in this city without trying the fish."

"Okay," he said dutifully.

That was a good night. I don't know what I expected -- Sarah to be full of piss and vinegar, Sarah to overcompensate to play up her subservient role with me, Isaac to be too loopy to keep up a relationship with Sarah. But they actually got on pretty well, and Sarah lacked any of Jenna's reserves about Isaac. I caught myself thinking more than once that yes, this could work, this could be a real long-term thing. I didn't know if Sarah felt the same way, and obviously there were the first-date good behavior walls, but as a starting point, it was probably the best first date I'd ever had. The food was excellent, the talk light and fun. Sarah and Isaac talked games, though she admitted pretty early on she was more into roleplaying and story-driven games than his action-focused ones. That killed some Isaac's buzz over her, and after a dish of cobbler and vanilla ice cream, he asked if he could go to George's and stay the night. I made the necessary call, pleading with the universe for Garth and Christy to say yes, and thankfully they did. It wasn't always going to be that convenient, Lord knew, but that night, I'd take it.

I watched him run down the street just long enough to make sure he was safe -- don't laugh, I know he's old enough to handle being on his own that far but I'm nutty -- and then Sarah and I were on each other, our lips smacking together with a hunger that we couldn't deny a minute longer.

"Your kid..." she gasped before I kissed her again. "...is adorable."

"Has a little bit of a crush on you," I said. "Well... your boobs, anyways." She burst out laughing and I drove her back towards her couch, my hands all over her back as I kissed her neck, her cheek, her ear. Against it, I murmured, "I never did get to finish inside you. Your pussy or your ass."

Sarah shivered and pushed me back. "We'll have to make up for both," she said.

I studied her from head to toe and unzipped my pants. "Strip for me," I told her.

"Your slut is yours to command," she said with a bow. My laugh got a giggle out of her, and I couldn't help but kiss her again.

I settled down onto the couch, my pants and boxers lowered to my knees. I kicked them off while she started up a beat-heavy playlist, something animalistic and hot. Sarah... well, she wasn't a great dancer, but oh, how she tried. She turned her back to me and gave me a look over her shoulder that lit my world on fire. I spat into my hand and lazily stroked my hardening cock as she swayed side to side, raising her hands and bringing them down along her sides. Her fingers slipped under the hem of her sweater, and she started to raise it, showing off just an inch of her tiny tummy before dropping it back down and turning, staring me in the eyes.

Sarah's fingers rose up to her lips, tracing them, giving me a pleading look. One of her fingers slipped in, just to the first knuckle, and she sucked on it for a moment. When she pulled it free, a moan escaped her, and I wasn't entirely sure if it was faked or real. She twirled so her back was to me again, and bent over to put that big ass on full display as she ran her hands up her legs, across her thighs, her hem again. This time when she lifted the sweater, she didn't stop, revealing to me some kind of black bodysuit that looked like a one-piece swimsuit of sorts. The sweater came up and up, past her bared shoulders, up over her head -- and tangled in her twin ponytail pigtails. She grunted something irritable and I snickered, rising up to help her out. She bucked her butt back against my nude cock as I slipped her pigtails under the collar, and I retreated, enjoying the silly, sexy show.