Reconnecting – First Time – Literotica.com

“Adam? Is that you?”

I paused mid-stride and looked around, unsure of where the voice had come from and a little wary while out in the dark. I didn’t see anyone at first, but then movement caught my eye, and I had to concentrate to see the silhouette of a woman slowly approaching me.

“Yeah?” I said, squinting to make out who that was. The voice had been feminine, which was the only reason I hadn’t kept moving. Women usually didn’t represent a threat in a dark parking lot.

“Oh god! I thought that was you,” the woman said, stepping closer. The light from the Walmart sign illuminated enough of her features for me to identify her as Kayla McHenry, my regular babysitter from eight years old to twelve. Mom and Dad were both ambitious career people who regularly worked late into the evening, and Kayla had become a regular part of my life during those formidable years. They must have paid her a small fortune between her Freshman and Senior year to look after their only child. Many of her weeknights and weekend evenings were spent watching movies with me, playing games, or driving me to various extracurriculars.

I hit puberty during those years, too, which meant that she’d also featured prominently in my imagination during my hours-long gooning sessions at night. She had thick, straw-colored hair that hung to her shoulders and had developed before she’d hit high school so that she had B-cup tits the day I met her that had developed into healthy D-cups by the time she graduated and left for college. She’d pursued a degree at a college across the country and had seldom returned for visits, which was good because our hometown was tiny, with barely anything to do.

That was a big part of the reason why I left. I wasn’t attending a college across the country, but an hour and a half away in a college town was a better option than staying around here. I was pursuing a degree in computer science, which kept me from sticking around to bag groceries at the local Walmart or work at the hardware store.

“Kayla?” I asked. “Is that you?”

“Yeah! I can’t believe it’s you! It’s so good to see you!”

“You too!” I said. She came over to me, and I hugged her, noting her large breasts crushed against my chest.

“What are you doing here?” I asked. “Didn’t you get out of town?”

“Well,” she said, “You know what they say about this place. You eat the Dairy Queen once after graduation, and you’re doomed to return.”

“Shit,” I said. “You ate the DQ?”

“I’m a sucker for their steak fingers,” she said with a laugh.

She still had a good figure. Her large breasts had grown if I remembered correctly, and it looked like she’d put on a few extra pounds, but they made her look good… especially her ass.

“Listen,” she said, “I need to get home. My dad’s watching Caleb and has to go into work soon. Are you doing anything?”

“Not really?” I said. ” I was supposed to hang out with a couple of people, but they canceled on me, so I was just going to head back to the house and study for a while before turning in.”

“You want to come over?” she asked. “I wouldn’t mind catching up with you. If you’re not busy, that is.”

The invitation felt like it came out of the blue and caught me off guard. Why would Kayla want to hang out with me? Sure, we had spent much time together when I was younger, but that was years ago. What sort of things would we have in common to talk about? Still… I had nowhere else to go. I shrugged, opened the maps app on my phone, and handed it to her. “Sure. Type in the address.”

Forty-five minutes later saw us sitting on her couch, laughing at some of the old bullshit I put her through as we sipped red wine. That is, I sipped my first glass. She was on her third.

“Hahahaha,” Kayla said, brushing her hair out of her eyes for the third time as she cut a glance over at me. “God, you really would not shut up about that book.”

“That was your fault,” I pointed at her accusingly. “You’re the one reading me scary stories.”

“It was in school libraries all across America!” she said in mock defense. “How was I supposed to know they would be that bad?”

I chuckled and sat the half-empty wineglass on the table, and Kayla eyed it.

“Don’t like it?”

“Not really,” I said. I’d had beer at college, but drinking red wine was a first for me, and I wasn’t impressed. “I’m more of a beer guy.”

“Typical man,” Kayla said with a shake of her head. “Just like my husband.”

“Yeah,” I said, looking around. “You never mentioned where he was.”

She sighed. “That’s why I came back here. He left me for a younger model about nine months ago. I tried to make it about three months in Seattle without him, but it’s expensive. Especially with a kid. My mom convinced me to come back here until I got back on my feet.”

She flashed me a sad smile, and it deepened when she saw my look of pity. “It’s only for a little while. Once I get on my feet, Caleb and I are out of here.” I found out that Caleb was her one-year-old, who was asleep in the back room.

“I’m sorry,” I said. “Divorce sucks.”

“Your parents are going through it too?” Kayla said. “I heard about that.”

I shrugged. “It’s not like I didn’t see it coming. I’m sure you saw the signs, too.”

“I did. Still doesn’t make it any easier,” she said. She leaned back against the couch and threw back her wine glass, killing the remainder of the crimson liquid gathered at the bottom. She sat it on the side table, and we silently stared at the opposite wall for the next few minutes.

I finally looked at her and caught her looking over at me, her eyes slightly unfocused, and while she wasn’t fully drunk, she was clearly buzzed.

“So, are you seeing anyone in town?”

“No,” she said, laying her head against the cushions and giving me a wistful smile. “What about you? Do you have a girlfriend at school?”

“I’m talking to a girl, but we haven’t made anything official yet.”

“Have you kissed?” Kayla asked.

“Yeah,” I said with a wistful smile as I recalled our first kiss a couple of weeks ago. It had devolved into a two-and-a-half-hour makeout session while watching one of the Fast and Furious movies. Vin Deisel gave his speech about family while I had my tongue down her throat.

“Just kissing?” Kayla said. Her eyes blinked slowly as she gave me a strange smile.

“So far,” I said.

“Mmm,” Kayla said.

We fell silent again as we stared at each other a bit longer. Finally, Kayla spoke up again, “Did you ever do it with what’s-her-name? Felicia?”

“No,” I said.

“Wait,” Kayla said, her head rising off the couch cushion as her focus became very clear. “Have you ever done it before?”

I was hesitant to answer, afraid I was about to get mocked for the truth, but too nervous to lie. Kayla had known me for nearly a decade, and I was pretty sure she could tell when I was lying despite having not seen me for almost six years.

My hesitance was enough of an answer for her.

“Oh my god, you’re a virgin,” she said.

“I’m… well…” I trailed off and looked away, searching for a good excuse to leave. The next few minutes trailed off in silence, and I eventually looked back over at her in morbid curiosity. Her head was back on the cushion again, and she stared at me with a half-lidded expression.

“It’s nothing to be ashamed of,” she said, giving me a soft smile.

Unsure of what to say, I shrugged and looked down at the floor.

“Would you like to change that?”

My head whipped back around to look at her. “What?”

She slid one foot out from under her leg where it was tucked and placed it on my thigh, and I glanced down at it. She’d recently painted her toenails a deep burgundy, but I could see that time had worn away some of the paint on them as her toes slid across my leg.

I looked back at her face and into her light brown eyes, hardly believing what was happening. I remembered countless nights imagining what her tits looked like and wondering what her lips would feel like on mine. Thanks to the internet, I knew what a naked woman looked like. I’d seen all shapes and types of the female body, and I wondered which she most resembled. She’d been a gymnast in high school, so her body had been more svelt in those days.

Now, she had the full figure of a young mother, with wide hips, large tits that stretched the fabric of her shirt, and a Pixar mom ass. If I had just seen her from behind, I probably wouldn’t have recognized her, but while her face was a little more round, it was otherwise unchanged. She still had those large, expressive eyes, a cute upturned nose, and that wide, expressive mouth with those slightly bee-stung lips. The woman who I’d fucked countless times in my dreams was coming onto me.

She brushed some hair behind her ear and ran her toes down my thigh. “It’s been ten months since I’ve had any, Adam. I’m buzzed, and I’m horny. Would you like to lose your V-card tonight?”

She swirled the remaining bit of wine in her glass around as she studied me with a half smile. The hand that had brushed her hair back slid down her neck and chest, and her fingertips played across the stretched fabric of her shirt in small circles very close to where I could see the vague impression of a stiff nipple.

I slid my knees under me and got on all fours, slowly making my way across the couch toward where she sat on the other end, gauging her reaction as I reached her for any sign that she was messing with me. She looked me up and down and bit her lip.

“Fuck yes,” I said.

Kayla threw back the remainder of her wine, set the glass on the floor, and leaned forward so our faces were inches apart.

“Be honest, Adam,” she said, her voice barely more than a whisper. “Did you ever think about me?” I could smell the fruity wine on her breath.

The truth was too embarrassing, but it also had to be flattering for her, so what was the harm? “All the time?”

“Mmm,” she said and lay back on the couch, spreading her legs as she ran her hands up and down her thighs. “How old were you the first time?”

“It was the winter before you left,” I admitted, crawling between her legs until I hovered over her. “And constantly for about two years after that.”

Kayla gave me a shy smile. “Really? That long?”

“I think you were my first serious crush,” I said. “You wore baggy shirts a lot, but all those yoga pants. I always remembered your ass in those. I never could stop staring.”

“I haven’t been on a balance bar in years, Adam,” Kayla said. “I’ve put on a little weight since I left.”

“Kayla,” I said, looking her up and down. “You’re still hot!”

She smiled again. “Kiss me.”

Not needing any other encouragement, I crushed my lips to hers and immediately invaded her mouth with my tongue. The sudden attack must have caught her by surprise because she squealed and didn’t immediately react, her body stiff underneath me. Then she relaxed, and I felt her tongue press against mine as it began lashing at it. The taste of wine was strong on her lips and tongue.

We spent the next twenty minutes making out. Her generous lips feasted on mine, teeth nipping at them. She sucked on my tongue as if it were a small prick and used mine to scrub every single inch of her mouth I could find. I was a tornado of desire and need, years of hormones making me wild with need, and I threw myself into her with wild abandon. She was also a wildfire but more controlled and contained, reciprocating the passion I craved but also directing me in more useful ways.

If it were up to me, I would have just flogged the inside of her mouth with my tongue for hours, but she showed me a better way. I shivered as she cupped my face in her hands and gently ran her lips over my skin. She kissed my forehead, nose, and lips, then turned my head to the side and ran her lips along my jawline. She nipped at them with her teeth and worked her way up to my ear, nibbling on it. I could already feel my cock on the verge of exploding, and its only action had been a few minutes of friction on a couch cushion as we made out.

With her lips pressed to my ear, Kayla whispered, “Take my shirt off, Adam.”

I obliged, grabbing the hem of her shirt and tugging up on it. She sat up just enough to help me get the shirt off her and raised her arms, and I slid it off of her and dropped it to the floor. This was the most I’d ever seen of my former babysitter, and as she lay back on the couch, I just took her in. Her belly was soft and smooth and looked like it had fully recovered from her pregnancy. I had heard that women who maintained their fitness before pregnancy had a better chance of full recovery, which made sense. Even though she claimed to have not participated in gymnastics in years, she must have at least had some sort of fitness routine. Her hips flared beautifully, and her waist was still an hourglass shape, leading up to a chest that supported large DD breasts encased in a thin floral-print bra. There was little padding, and her nipples caused the fabric to protrude.

I licked my lips as I stared. She licked her lips as she watched me.

“You want to undo my bra?” she asked. I nodded and slid my hands behind her, my face once again mere inches from hers as I fumbled with the clasp. She gave me a flirtatious smile and said, “It takes some time to get used to these.”

Then, the back of the bra snapped loose, and we grinned at each other.

“I’m a quick learner,” I said.

I slipped her bra off her shoulders and pulled it away from her chest, getting a look at her breasts for the first time. They hung from her chest as she settled back down on the couch, pooled against her chest by gravity. Large dark pink areaola stretched across their peaks and were capped by thick nipples.

I leaned forward and closed my lips around one of her nipples, suckling on it gently. She wrapped her hands around the back of my head and pulled me into her tit as she hissed. “Harder.”

My tongue lashed against the little nub as I increased the suction. I tried to pull away from her tit, but the hold she had on the back of my head prevented me from moving.

“Harder,” she groaned. “Bite me.”

My incisors sank into the soft flesh of her tit; it wasn’t enough to do any real damage, but enough to get her attention. She hissed again, and it turned into a long groan as her back arched off the couch, and she crushed my face into her breast. My left hand wandered across her other breast, kneading and squeezing the large mound of flesh before focusing on her nipple, pinching it as I chewed on the other.

I spent the next several minutes swapping back and forth between her breasts, licking, sucking, and chewing on one while twisting and pinching the other. Kayla thrashed underneath me, her hips rocking back and forth as she humped at the air.

“Stop. Stop. Stop,” she said. Abruptly, she shoved me off her, and I went up on my knees, unsure if I’d hurt her or not.

She got off the couch and skinned her yoga pants and panties off her ass and down her legs, leaving them on the floor in a pool as she stepped out of them. Standing in front of me completely naked, she hauled me to my feet and grabbed my shirt. “Get this shit off,” she muttered as she yanked it over my head and threw it behind her. She unsnapped my jeans and yanked those down my thighs with the frenzy of someone desperate.

My cock bobbed in the air as Kayla dropped to her knees in front of me. The head glistened with precum, and I feared the slightest breeze would set it off. I knew if that happened, it would be over, and I wouldn’t get a chance to put my dick in her again.

“Oh god, yes!” Kayla said and lunged at my cock; she took half of it between her lips and began working them up and down the shaft. Her hands grabbed my thighs to keep me in place as she gave me a hands-free blowjob in the middle of the living room. She moaned around the cock in her mouth and looked up at me with her pretty eyes.

I immediately lost it.

“Oh fuck fuck fuck fuck!” I yelled and reflexively placed a hand on the top of her head. I felt overwhelmed as my cock exploded in her mouth. Spurt after spurt of my semen unloaded into my old babysitter’s mouth as she gazed up at me, and my head swam with all kinds of incredible sensations as I achieved one of the best orgasms of my life.

At the same time, I felt disappointed that it was over. I’d only gotten to third base with her before completely losing it. Looking down at her, it was hard to feel too disappointed, though. Kayla continued to suckle gently on my cock as it still released smaller loads into her waiting mouth. I could see her throat working up and down as she swallowed what I gave her, and I felt a surge of lust coarse through me at the thought of her eating my semen like that.

She released my cock from her mouth with a sound that was somewhere between a contented hum and a giggle and ran her tongue up the underside of my shaft. Grabbing the base with her hand for the first time, she nuzzled the sensitive head with her lips and then kissed it before letting go.

“Now that that’s out of the way,” she said as she stood up and laid back on the couch, her legs splayed. “Get that thing in me.”

I grinned, glad that it wasn’t over, and dove between her legs. My cock was still hard as steel and bobbed under me as I stayed on all fours and lowered my head between her legs. Her pussy was drooling; a bead of thick, clear liquid was slipping down her thigh toward the couch. I started to inch closer to her cunt, but she grabbed me by the hair and directed me to look up at her.

“Nuh-uh,” she said. “Not this time. I’m wet enough. I just need it in me. You can do it another time.” She reached for my shoulder with her other hand and tugged at me, encouraging me to crawl up her body. I did so, taking the time to press my lips to her soft skin as I quickly worked my way up her body.

I found myself hovering on top of her, looking down into her beautiful eyes, when I felt the head of my cock connect with something hot, wet, and extremely soft – the folds of her pussy.

“Yes. Fuck yes,” she said, wrapping her arms around my neck and legs around my waist, encouraging me to move forward as her legs tightened around me. The mushroom tip sank into her depths like a warm knife through butter, and my eyes grew large as I felt myself inserted into a woman for the first time. It felt incredible! She was so wet and slippery, but her canal gripped my member tightly, giving me the friction I so desperately craved as I continued to bury myself inside her. In one single stroke, I was able to slide the entire thing inside her.

Kayla let out a long, loud groan, “Yes… Adam, please don’t stop!”

Her legs loosened around my waist, and I set to work, thrusting in and out of her hot, wet snatch. As I fucked my beautiful blonde ex-babysitter, I stared down at her face, studying her lovely features while her eyes were screwed shut. This moment would be set in stone in my mind for eternity; it was a filthy dream come true, and it had been better than anything I could have ever imagined. The most basic reality of her was better than the filthiest fantasy.

Kayla’s eyes were still screwed shut as she tossed her head back and forth and crooned. She was clearly enjoying herself, so I decided to turn it up a notch. I reached down and grabbed one of her tits, marveling at its size as I squeezed and kneaded it. Then I wrapped my fingers around one of them as much as I could and lifted it as I lowered my face so I could suck on her nipple once more. She squealed and once again grabbed the back of my head and crushed my face into her tit. Her groin thrust back at me as I continued to fuck her.

A few moments later, I felt her shudder underneath me as she started to squeal. She yanked my head off her tit, crushed her lips on mine, and let out a blood-curdling scream into my mouth. Her legs tightened back around my waist, locking me in place with my hard cock buried deep in her, and one of her arms wrapped around my naked back. I felt her nails dig into my skin, and I groaned back into her mouth in a mix of both pain and pleasure as we stared into each other’s eyes.

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