by Jessa James
I squeaked out a “yes.”
My eyes remained closed as his fingers continued to move and assault my ass. A part of me was nervous, the other half excited, at the idea of his dick entering me from behind. I bet none of the other girls were getting their ass fucked. They’d all said Mr. Parker was the hottest teacher in the school, but I was the only one who’d get him.
Just the feeling of his fingers moving in and out was already more than enough. I couldn’t even begin to imagine what his dick would feel like. It had to be bigger than his fingers. I’d soon find out.
He pulled them out, and I opened my eyes when I heard the sound of his belt and jeans coming undone. I heard the splattering of more lube coming out of the bottle, and I began to shiver as I waited for him.
“Patience, Jane,” he said softly, his voice deep and strong still. “I’m getting my dick all slick. I don’t want to hurt you. We’ll take it slowly. I’ll guide you through everything and give you the best experience you can ever have.” I nodded my head and hunched my back when I felt his tip teasing my entrance.
At that moment, heart skipped a beat. We were having a hot and passionate moment, but my heart felt calm, relaxed…and wanted. He sounded like he cared for me, like he didn’t want to hurt me, like this wasn’t just a student-and-teacher role play. He sounded like he was truly concerned for me and the experience he was giving me, and I couldn’t help but let my feelings for him grow. He wasn’t just the experienced teacher whom I wanted to lose my virginity to; I wanted to spend more time with him now, get to know him better, have him become a larger part of my life.
“Hm-!” I squeaked when he began to push his dick in. He kept a strong hold on my hip, making sure I wouldn’t pull away when he would push in more. I gripped the blankets to distract myself from the feeling of his full dick trying to push its way inside my tight ass. I couldn’t explain the feeling. It didn’t hurt as he began to stretch me open; it felt good, but at the same time, the feeling was both familiar and unfamiliar. I couldn’t explain it.
“Don’t overthink, Jane,” he said, as he gave my shoulder a kiss. “I can tell you’re stressed and nervous. Relax and take a deep breath. Let it out and push back. Good.”
I did as instructed and felt his broad head pop inside me. I heard him suck in a breath at what just happened, and it was music to my ears when he breathed, “Fuck.”
I couldn’t help but wiggle my hips and he took it as a sign to work his way in, and when he finally was, he started to thrust in and out. At first he took it slow, letting me get used to the feeling. As he continued to push and pull in and out of my ass, he reached around and cupped one breast and pulled me closer until my back was flushed against his chest. He pounded me from behind, and I loved the feeling of his body right behind mine. I felt safe and protected, like no harm was coming to me, like he would protect me from everything outside our own little world. Even when he was doing the dirtiest, most wicked of things to me.
“You like that, Jane?” he asked, and I nodded.
“Yes, sir.”
“I’m going to go faster now. Hold on.”
Another nod from me. He kept his promise and began to pick up his pace, moving his hand from my breast to my clit. It was then I finally opened my eyes and saw stars.
“Oh, Mr. Parker…” I couldn’t help but moan, biting my bottom lip to stop myself from screaming. “This feels so fucking good…”
He gave my ass a slap and then another one, working my ass from both from his hand and his dick. “You’re a Catholic school girl. You’re not supposed to curse.”
I replied with a louder moan this time. He continued to assault my ass, and I was letting him do it all too willingly. I wanted this. I wanted more. I wanted him, and to pass the message, I moaned louder and heavier until they crossed the boundary and turned to screams.
“Yes, Mr. Parker! That feels amazing!”
“Hmm…” I heard him, as he gave my ass another slap. “Who knew a prim young lady like you would like it in the ass?”
I couldn’t hold back anymore. His fingers pressed against my clit, and I could only close my eyes and scream at the euphoria.
“Mr. Parker,” I moaned his name. “I’m gonna cum. I’m gonna cum…I’m gonna…”
“Cum for me, Jane,” he said, his tone both caring and demanding. “Let go.”
He thrust even faster now, his fingers moving in circles against my clit. I squeezed my eyes tight and breathed out heavily. I felt my nerves relax a bit, and it was then that I was able to let go. I felt the whirlpool peak and break, and before I knew it, my pussy was flooded with my own juices and I knew his fingers had to be coated.
He thrust deep one last time and held himself still. He shouted his own release and I felt his cum spurt hot and thick deep inside me.
Slowly but surely, he pulled his dick out of my ass, and I felt that there was an empty hole inside me, both literally and figuratively.
But then, I smiled automatically when he pulled me closer to him and laid me on my back on the bed. I felt his hot cum slip from my used hole. I no longer had a virgin ass. The slight burn, the cum, were proof.
He planted a kiss on my lips. Our first kiss.
“I’ll be right back,” he said, and I nodded in response. He went to the bathroom and came back with a warm washcloth, which he used to carefully clean between my legs. “You were amazing. Would my little student like to spend the night here with me?”
“Yes,” came my quick reply. “No one’s home anyway.”
No one was home, yes. But I didn’t want to leave his side. I wanted to spend the night with him.
Chapter Seven
Gregory
“My parents don’t give a shit.”
Not a lot of things scared and shocked me. I could sleep and snore through horror movies. I’d jump out of a plane for just the thrill and fun of it. I’d eat disgusting insects, be it a dare or not. My friends would prank me and try to get me to break my cool and calm façade, but they always failed.
Except for Jane.
Hearing those words leave her mouth made me suck in a breath. I met her eyes and kept the contact, looking right at her. Her lips were pursed together, as her eyes remained searching mine for a reaction.
What could I say?
That this Sunday had been one of the best days of my life? That I wouldn’t be able to sleep later because I’d be thinking about… everything? We didn’t do anything extraordinary even, not today and not even during the days before. Jane had stayed the night in my place one more time after that first night she slept over, that night I’d claimed her ass.
We did everything, from cuddling to oral sex, and now, I always teased Jane about how giving me blowjobs was her new hobby. She’d initiate and do it out of her own accord.
She woke me up twice by sucking me, and after, we’d just spend the rest of the day cuddling. She’d undo my jeans and pull them down while I was trying to get some chores done around the house. I’d stopped wearing boxers to make it easier for her.
She’d even tried to do it to me in a public park, but I told her we’d try that in the evening when there were less people. I wouldn’t have anyone else see Jane on her knees.
I’d made a mental reminder to follow through with that.
I’d yet to fuck her pussy, to finally take her virginity. Waiting the seven days was hard, but I’d shown her all the other ways to pleasure each other.
But now, I couldn’t keep Jane out of my mind. She’d done something to me, and I wasn’t complaining. I’d never complain when it came to her. These past few days, we’d spent tons of time together, and I was starting to realize that she was everything I wanted in a partner and more. I was getting to know her, the woman underneath that shapely body, and I was dying to find out more.
For her age, Jane was mature, both physically and emotionally, yet the youthful energy was obvious, especially in bed. Or on the kitchen table. Or up against the front door.
She was
always wanting to please me and make me happy, be it in or out of the bedroom, but at the same time, she still spoke her mind. The women I used to date always ended up saying “no” more than “yes”. They weren’t adventurous and would rather stay in and have sex unless I took them out to upscale and fancy restaurants. With Jane, she was up for anything. She knew how to be both boring and fun, and even that already made her a cut above the rest.
“I care about you,” I said when minutes of silence passed. “You’re one of a kind, Jane, and it’s a shame your parents don’t see that.”
“I—”
I froze in my seat when her voice cracked for a split second. We were in my living room after a whole day of exploring the city. We’d gone to the local museum and library, and for lunch, I’d taken her to this new café a friend of mine owned, and she was able to meet him. Since she was mine, I wanted to show her off. Not many eighteen-year-olds could start and carry a conversation with people over a decade older, yet Jane did it effortlessly. She was young, yes, but she was exquisite. I didn’t give a shit what people thought. She’d be on my arm for events and reunions with friends. She’d easily fit right in.
Goddamnit, I internally cursed.
This wasn’t about just being physically attracted to her and teaching her everything she needed to know about sex. I wanted her before, during, and after sex. I wanted to hang out with her more and take her out. I wanted her in my life. I’d known it from the start. I wasn’t giving her up.
“What’s wrong?” I asked, wrapping an arm around her shoulders and pulling her close to me. “You look worried.”
“I’m scared you’ll leave me once we’ve had real sex.”
I almost broke out laughing but held it in. I knew Jane would take that kind of reaction the wrong way. It was just funny to me how, while I knew she was never going anywhere, she was worrying that I’d leave her.
If only she knew…
It was then I hooked a finger under her chin and tilted it up, so I could stare at her.
“You’re mine, Jane,” I began. “How many times do I have to tell you?”
She gave a slight shrug. “Maybe a few more.”
I grinned. “Perhaps you’re more of a hands-on learner.”
With a gentle push, I forced her onto her back. With one knee on the couch and a foot on the floor, I levered myself over her, tugging her so she was spread before me. I liked her wearing flirty skirts and this moment was why. I just had to toss up the short hem and her pussy was bare for me.
“Yes, Mr. Parker. Perhaps you need to show me.”
She shifted so she could pull her t-shirt over her head, her bare breasts swaying as she settled on her back once again.
As I lowered my head to one plump nipple, I murmured, “You a very eager pupil.”
* * * *
Jane
“They’re back.” It was the first thing I said when he opened the door. He was in sweatpants and t-shirt, and the sight instantly made me horny even if I was feeling down. “I don’t want to stay there tonight.”
Mr. Parker immediately knew what I was talking about. My parents – they’d just gotten back from Europe. They’d returned with a mountain of souvenirs, from designer clothing to Swiss chocolates and the finest wines from France and Spain. They were all for me, even the alcohol, but after they’d said their “hi’s” and apologized for missing my graduation, they excused themselves and went to their home office. Mom needed to catch up with emails, and dad had a business dinner with some corporate partners. In a second, the mansion was back to being empty, and I felt lonely. After spending every day of the past week with Mr. Parker, the difference between the feeling of being alone and having someone to spend the day with was as clear as night and day.
Mr. Parker and I talked about meeting at eight tonight, but I went to his place a couple hours earlier. Why wait when there was nothing to do in the empty mansion? Besides, it’d been exactly a week. We both knew what tonight entailed, and I’d assumed he’d want me at his house sooner rather than later. It was time for him to take my virginity. He’d kept his word, nothing had gone into my needy pussy. Yes, he’d eaten me out and fucked my ass, but he’d kept my pussy as virgin as could be, ready to be stretched open first by his bare cock. During the drive, my imagination went wild.
I was already thinking about the dirty things I was going to say to him, how I was going to remove the tight-as-a-glove dress I wore. I was playing out the possibilities of later in my head. Would I keep my heels on or off? Maybe, I could ask that in a naughty way. My thoughts were racing, and it was a miracle I even got to his place in one piece.
“I haven’t cooked dinner,” he said to me, but that was honestly the last thing on my mind. I wanted to eat something else. Ever since that first time I’d given him a blowjob, I found the beauty in sucking dick. His dick. When he was in my mouth, I owned him. I was powerful and beautiful and more important, irresistible.
It was so much fun to do, and the shape of his tip and the length of his shaft was definitely a sight I could stare at all day and night. He’d tease me regularly that sucking him was now my new hobby. I’d laugh him off every time, but deep down, I knew he couldn’t be more right. “Come in, Jane. Sorry,” he apologized quickly. “I’ve been studying for the bar exam the whole day. My mind’s burnt.”
I entered his house and followed him into the living room. He sat down first and patted the empty space beside him, but fuck. The sweatpants and the even thinner t-shirt only made me feel hornier. If we started a movie, there’d be no doubt I wouldn’t last through it. My eyes flew toward his cock where the length was outlined in his sweats, and I sucked in a breath. I wanted to have sex right then and there. I’d been waiting a full week, and I felt like I couldn’t wait any longer. I wasn’t going to tell him that outright though. I wasn’t going to throw myself at him.
Because I loved it when Mr. Parker took charge, and tonight, I wanted him to take charge as he took my virginity.
I just needed to prod him, so I didn’t sit next to him. Instead, I stood directly before him.
With a smile on my face, I began to wriggle out of my skintight dress. I’d move my ass left and right to get the spandex to ride up my hips. I held the hem with my fingers and pulled it over my body, and when my dress covered my face, my smile turned into a smirk when I heard him elicit a groan. I wasn’t wearing any underwear—just the way he liked me—and in a second, I was full-on naked in front of him. To add to that, I’d gone to the salon yesterday to get a full wax. My pussy was bare and free from any hair, and I clenched when I felt a surge of heat burning inside me.
“Fucking…” Mr. Parker breathed as he stared at me. I threw the dress onto the floor and walked closer to him until my legs touched his knees. “Jane…” he groaned again, running a hand through his hair. I could see the hunger burning in his eyes.
“It’s been a week,” was all I said. I didn’t even need to say that to let him know what was on my mind.
“Not here,” he said, and in a second, he was on his feet and he’d swooped me up in his arms. He raced up the stairs and then kicked open the door to his bedroom. Then, he dropped me onto his bed. “It’s your first time. We’re going to do it the right way.”
“It’s right as long as I’m with you,” I courageously said, letting him know what I felt.
“Such a good little virgin.”
I saw his eyes soften a bit before he moved them down to explore my body. I felt a shiver run up my spine when he began to trace a finger over my skin, from the curve of my neck and down the valley between my breasts, then lower still, over the newly bare pussy lips.
I inhaled sharply when his finger stopped right at my entrance. My eyes widened when he planted just one kiss over my pussy. Then, he rose up to kiss me on the lips. I tasted myself on him. The moment was so emotional and intense. He wasn’t rushing to take me.
He didn’t undress and stick his dick in right away, just as I wanted. By the look on his face,
I could tell he didn’t want to rush tonight. He wanted to take me, yes, but he wanted tonight to be special, too. It was going to be my first time. It was going to be our first time. There were no repeats or refunds for firsts. I could tell what was on his mind with the way he acted and moved above me – caring and loving he was.
And I couldn’t help but blurt out, “I love you.”
My heart instantly froze when those three words left my mouth. Silence enveloped the room, and I was thinking of taking back what I said. He stayed deathly quiet, and I felt like my heart was going to crack the moment one of us moved. I turned my head to the side to look away, but right when I was about to do so, he moved his head down towards my pussy and began planting soft kisses at my entrance.
He licked and laved my pussy, his lips swiping my folds and his tongue trying to push deeper. He sucked once and then twice, all the while his hand continued to rub up and down my thigh while the other cradled my waist. There was nothing rough and eager about the way he moved, and it was relaxing and calming, and it was just what I needed. He continued to kiss and suck my pussy, and I savored the moment with eyes closed and my mind blank and empty. I was in the moment, and it was the only place I wanted to be.
I arched my back off the bed when his tongue started to play with my clit, and I let out a series of moans when I could feel the ember growing inside me. The whirlpool was building up again, and he knew what was about to happen because my moans then turned into screams, and those screams turned louder with every minute passing.
“Gregory…” I breathed, when I felt myself about to tip over the edge. “Please…”
In an instant, he was off me. My eyes widened, questioning, but he only smiled at me as he began to take off his sweatpants.
“Another lesson, naughty girl. What do you call me?”
I wiggled my hips. “Mr. Parker, please.”
He pulled the t-shirt over his head and threw it across the room. Settling back between my parted thighs, his full erection teased my entrance, and I could see some pre-cum drip from the tip.
