Permission To Play . . .

By eight on Saturday morning, Ian and I were already on the road, eager to begin our spring break. I settled back into the passenger seat, pulling my white cardigan tighter around me. Beneath it, I wore only a pale blue sundress. Seeing as how it was mid-March, my outfit wasn’t exactly practical, but it was perfect for what I had planned. Even my ballet flats had been chosen for their easy removal.

It was as if Ian read my thoughts as he followed the flow of traffic on the interstate, for he glanced over at me and asked, “Aren’t you a little cold in that dress?”

I shrugged. “It is spring break, after all,” I replied, trying to sound innocent.

“Yeah, but it still feels like winter this morning. Want me to turn up the heat?”

“Nah, I’m okay,” I said. “It will warm up fast now that the sun is out.”

Ian was sensibly dressed in a long-sleeved shirt and jeans. As I studied him, I noticed that his light brown hair needed a trim; it kept falling into his eyes, and I had to resist the urge to brush it back with my fingers.

“Thanks again for giving me a ride,” I said.

He offered me a sweet smile. “It’s really no problem, Libby.”

We were both sophomores at the same university, and Ian’s girlfriend, Tess, was my best friend. The three of us had met during our freshman year and become quick friends, but Tess and Ian hadn’t started dating till last fall. Even though they were madly in love, they made a point to include me in many of their plans, which meant a lot to me.

Just last week, my car had died on me, and it was now in the shop. My parents said they would loan me the money to buy something more reliable once I was home for the summer, but for now, I needed to have my current vehicle repaired. Ian didn’t hesitate to offer me a ride; he passed right by my hometown on the way to his, which was just an hour farther west, so he insisted that it was no trouble at all. His car was almost as old as mine, but it was in far better shape.

Tess lived halfway across the country, so she was taking a flight home. I glanced at the dashboard clock. “Tess should be in the air right now,” I said, tucking a strand of my chin-length dark hair behind my ear.

“I hope she has a great time back home, but I’m going to miss her.” Ian’s voice sounded wistful, and it was painfully clear how much he cared for Tess.

I kept my tote bag, zipped tight, between my feet, and as I stared down at it, I started having second thoughts about my plan. Well, the plan Tess and I had come up with together. What if Ian wasn’t interested?

It was difficult to imagine that he would lack any sort of interest; he was a twenty-year-old male, after all. Still, his devotion to Tess might very well prevent him from loosening up enough to enjoy what I had in store.

While I was preoccupied with these thoughts, Ian and I rode in comfortable silence. We were making good time covering miles and miles of interstate, and with the sun streaming through the windshield, I grew warmer.

Closing my eyes, I tried to let my imagination run wild, mentally picturing Ian’s reaction when I opened that tote bag.

“Are you trying to go to sleep on me over there?” Ian asked, a smile in his voice.

I opened my eyes and turned to him. “Nope. I’m wide awake.”

“It’s okay if you want to grab a nap,” he said, “but we’re going to be getting off the interstate soon, and as you know, the rest of the drive will mostly be on rural back roads, so if you need to get something to eat or use the bathroom, speak up now.”

I quickly shook my head. Ian had stopped for gas an hour ago, and during that time, I’d gone into the convenience store to pee and buy sodas for us. I was too nervous and excited to even think about food right now. “I’m fine if you are,” I told him.

Looking out the passenger window, I watched as we left the interstate. “This part of the trip can really drag on,” I said. We would be spending the next hour on two-lane roads, surrounded by woods and farmland.

“Don’t I know it,” Ian replied, “but at least I have great company.”

We smiled at each other, and I looked down at my bag once more. It was now or never, I realized.

Just the thought of what I was about to do made my pulse race. My cheeks flushed, and my mouth grew dry from nervousness. Yet despite my anxiety, I was excited, too. Already I could feel an insistent throb between my thighs.

“I can think of a way to make the trip more exciting,” I finally worked up the nerve to say. There was a slight tremor in my words that I hoped Ian didn’t notice.

He glanced over at me, his face a question. “I’m open to suggestions.”

I took a deep breath, then grasped the hem of my dress and began to slowly draw it up my thighs. My heart was pounding so hard, I could hear it as a roar in my ears.

“Libby?” Ian’s voice was filled with confusion.

I didn’t dare look at him—not yet. Instead, I kept lifting my dress until my lacy white panties were visible.

“Libby, you need to put your dress down,” Ian said, and I almost winced at his harsh tone. Out of the corner of my eye, I saw him squirm in the driver’s seat, clearly uncomfortable.

I turned to him, but he wouldn’t look at me. Instead, he kept his stare fixed on the empty road ahead. “Tess knows about this,” I said quietly, “and she’s okay with it. In fact, it was her idea.”

Ian gaped at me for a moment before reluctantly looking back at the road. He knew I wouldn’t lie about this—I valued Tess’s friendship, and his, far too much. Still, he seemed to be choosing his words carefully when he spoke again. “What exactly do you mean about this being her idea? She’s okay with you flashing me?”

“More than that,” I said. “She was aware that we’d be cooped up in the car together for hours, and she also knows that I’ve been, um, kind of sexually frustrated lately. It seems like my roommate is always in our dorm room, so I hardly ever get a chance to masturbate—”

I heard Ian draw in a sharp breath, and once again, his eyes grew wide.

“And I haven’t gotten laid in months. So Tess came up with this idea,” I hurried on. “She suggested that I do some playing once you and I reached the back roads. She said the thought of you watching me, and also touching yourself, makes her really horny.” My breathing grew shallow, and my voice was strained with barely contained arousal. Just speaking those words aloud had gotten me wet.

Ian’s mouth dropped open. “I can’t believe this,” he said, then grinned in spite of his astonishment. “Actually, I can believe this. Tess is pretty… open-minded when it comes to sex.”

“But,” I said, holding up a finger, “we can’t touch each other. She trusts both of us to behave, and I can promise you that I will not betray her trust.”

Ian swallowed hard and nodded. “The last thing I ever want to do is hurt her.”

“I feel the same way, so we’re going to obey the rules. But Ian, I think you’re cute and sweet, and it would make me so excited to masturbate in front of you.” My voice was just above a whisper, and when his eyes met mine, I gave him a tender smile.

“I think,” he said, his voice husky as he returned my smile, “that I have the best girlfriend ever.”

I couldn’t help but laugh. “You certainly do. So I’m going to have some fun now, if that’s okay?”

“God, yes, please go right ahead,” he said, his gaze moving over my bare thighs.

“One more thing,” I told him as I pulled the crotch of my panties to the side. “Tess wants you to call her tonight and tell her just how bad we were during this trip.”

Ian released a groan, and I knew it was a struggle for him to keep his eyes on the road instead of watching me slip my fingers between my pussy lips. “I know you have to focus on driving,” I said, my voice breathy, “so I’m going to do a lot of talking and let you know just what I’m doing, and how it feels.”

He nodded eagerly, then sneaked a glance while I pressed a fingertip against my clit and began massaging it.

“Mmm, I’m already really wet, Ian. Just thinking about playing with my pussy got me so turned on,” I murmured. “My clit is swelling… it feels incredible to rub it. Can you hear how wet my pussy is?” I worked my fingers over my clit faster.

“Fuck, yes,” Ian whispered, and it was then that I noticed the bulge in his jeans. The sight of it made me grin.

“I hope I don’t leave a big damp spot on the seat.”

“Oh, don’t worry about that,” he said, grinning back at me.

A truck approached us from the opposite direction, and I took the opportunity to lean forward so I could open the tote bag and withdraw a little bullet vibe with a pointed tip.

Once we were alone on the road again, I took off my seatbelt and then lifted my ass off the seat so I could remove my panties. After tossing them in my bag, I hiked my skirt up around my hips and spread my legs wide. Then I held up the vibrator for Ian to see.

“This one is nice and quiet. Sometimes I can get away with using it when my roommate is sleeping, but it doesn’t have as much power as I’d like.” I pressed the power button, and the bullet began humming softly. “The pointed tip feels good on my clit, though.”

Again Ian glanced over and watched as I used the vibrator to pleasure myself. The stimulation from the bullet made me groan, and I let my head fall back against the seat. I was so excited that my inhibitions disappeared completely, and I was consumed by the desire for Ian to watch me getting off.

I looked over at him, and our eyes briefly met before he turned back to the road once more.

“I’m such a bad girl, playing with my pussy in front of you,” I said softly.

“So bad,” he moaned while stroking his cock through his jeans.

“Take your cock out any time you want,” I told him, staring hungrily at his erection.

“I’d better not,” he replied even as his breath hitched in his chest. “I’m likely to shoot my load way too soon. I’m so fucking worked up right now, Libby.”

“That’s okay,” I assured him. “We still have plenty of time.” I wanted to come multiple times during this trip, so I turned off the power to the bullet and tossed it back in my bag, then retrieved a larger pink vibrator that also applied suction to my clit. I turned it on, and its powerful buzz filled the car.

“This is my favorite vibrator,” I said. “The way it sucks my clit is amazing, but unfortunately, it’s kind of loud, so I don’t get to use it often.”

“Just how many toys do you have in that bag?” Ian asked. His face was flushed, and his tongue glided along his lower lip.

“A few,” I said with a sly smile. “Just because I don’t fuck all that often doesn’t mean I don’t get horny as hell.”

Ian stared as I slid the vibrator between my folds, coating it with my juices. Then I pressed it directly against my clit and let out a loud moan. “Oh, it feels so fucking good, Ian. I’m gonna make myself come!”

“Ah, Christ, do it, Libby! I want to see and hear it!” he urged.

I grinned and began rocking my hips, writhing in the seat. My clit was already pulsing and engorged from my fingers and the bullet, so I knew it wouldn’t be long before I had an orgasm. The vibrator sucked and stimulated my tender nub even more, and I began panting. My body tensed as I trembled, and I then felt the familiar slackening of the muscles in my ass and thighs which let me know that the first orgasmic spasm was imminent.

That sense of relaxation was deceptive, and it made the fierce contraction that gripped me even more powerful. “Fuck!” I wailed, my thighs clenching around the vibrator. I resisted the urge to remove it from my clit and instead prolonged the climax. As I squeezed my eyes shut and shuddered, the groan that emerged from my throat was guttural. My body kept seizing as the orgasm coursed through me.

Finally I couldn’t bear any more stimulation, and I took the vibe from my clit. Slowly opening my eyes, I gasped for breath, my skin hot as I turned to Ian.

He stared at me as if I was a stranger. “I saw your face when you were coming, Libby,” he said. “It was so damn sexy, watching the orgasm overpower you.”

I grinned and brushed my hair back from my face. My clit was still throbbing, and I knew it would be tender for a good while.

Growing even braver, I shrugged out of my cardigan, then yanked down the straps of my sleeveless sundress. I wasn’t wearing a bra, so my tits with their hard pink nipples were on display. Ian actually whimpered when he saw them. I put the cardigan back on in case I needed to cover myself in a hurry, but I left it open so he could easily view my breasts.

“Fuck, I’m burning up.” Ian rolled down his window halfway, and I squealed when the chilly air caressed my bare skin.

“That’s making my nipples even harder!” I cried. “See?” Ian once again glanced in my direction and watched as I drew lazy circles around the erect peaks. Then I began fondling and tugging at my nipples. While my breasts weren’t all that large, I had big areolas. Each time I took my nipples between my fingertips, I felt a surge of arousal travel directly to my cunt.

“I come so much faster when my nipples are touched,” I told Ian, my voice weak with desire. “And my clit is still so swollen, I know I can make myself come just by rubbing it. “Do you want me to come again, Ian?”

He was breathing hard and fast, maintaining a white-knuckled grip on the steering wheel. “Please, Libby, I’m so fucking hard right now.”

I used my left hand to play with my nipples as I slid my right between my thighs. “I’m definitely leaving pussy juice on your seat,” I said, laughing low and soft. I thrust two fingers into my cunt and mewled with pleasure. “Hear that, Ian?” My fingers made a squelching sound as they moved in and out of me. “I’m finger fucking myself right now. My cunt is desperate for something to fill it.”

Ian made a sound in his throat like a growl, then took one hand from the steering wheel and worked at the button on his jeans. As much as I wanted to help him, I knew I couldn’t.

“That’s it, take out your cock,” I coaxed him. “I want to see it so bad!”

“You want to see how hard I am, you dirty girl?” he gasped.

“Oh fuck, yes!” I began furiously rubbing my clit, my stare riveted to his crotch.

Ian finally unbuttoned and unzipped his jeans, and when he freed his cock from his underwear, I felt a pre-orgasmic shudder grip me. His circumcised dick was fully erect, and the head, slick with pre-cum, was flushed a deep crimson.

“Just the sight of it’s getting me so close!” I cried. “Fuck, I love all that pre-cum!”

It was more difficult to resist touching him than I’d imagined it would be, but I was glad for the rule Tess had set. In a way, it was more freeing to focus solely on my own pleasure without worrying about a partner’s, even as I got to enjoy seeing Ian’s cock.

Ian looked down at my hand working between my thighs, then lifted his gaze to my face. “Come hard for me, Libby.”

I spread my thighs even wider and slumped lower in the seat. My clit was almost too sensitive by this point, so I massaged the right side of it, rolling the flesh beneath my fingertip until I knew I’d found just the right spot.

With my gaze fixed on Ian’s throbbing dick, I stroked myself, using a slower rhythm, and my clit readily offered up another orgasm. I shouted as the ecstasy inundated me, then began shaking. I groaned each time my pussy contracted, and I knew I was ready for the last toy I had in my bag.

Before I had fully recovered from my climax, Ian abruptly made a right turn onto a private gravel road. “I have to pull over,” he said, his words urgent. “This is way too fucking distracting.”

We hadn’t seen another car for miles, and I hoped no one came down the drive while we were parked. Woods surrounding us on either side provided a little privacy.

I figured Ian and I had come too far to lose our nerve now, so I slipped out of my shoes, then turned sideways, resting my back against the passenger door. “Now that I have your full attention…” I said to him as I hiked my dress up to my hips and spread my legs wide, placing my right foot on the dashboard and the left against his seat. The night before, I’d closely trimmed my pubic hair, so he now had a clear view of my pussy when I pulled my outer lips even farther apart.

“Oh, my God,” Ian said, gazing at my cunt. His voice sounded choked, like he couldn’t get enough air. “Your clit is so swollen.”

Ian hadn’t yet begun stroking his cock, and I knew he was desperate to, so I reached for my bag and took out another favorite toy.

Ian stared at it with wide eyes. “Holy shit!”

The dildo was fairly realistic, flesh-colored and veiny. It was also quite large, and the bulbous head was downright intimidating.

“I know,” I said. “Turns out my eyes are bigger than my pussy when I go shopping for sex toys.” We both cracked up laughing, but Ian quickly grew quiet when I began sliding the tip of the dildo from my opening to my clit. “It can be a little uncomfortable getting the head in,” I went on, “especially without lube, but it feels really good once it’s all the way inside my pussy.”

Ian took his lower lip between his teeth, and I noticed that he was trembling. “Fuck,” he said, “I want to see you work that dildo into your tight little cunt.”

His words made me moan. “Only if you stroke your cock for me,” I whispered, a grin playing at my lips.

“I’m not going to last long once I start jerking off,” Ian said, and his expression was sheepish.

“That’s okay,” I assured him. “I’ve already come twice, and I think the third time will be my limit. Everything is so sensitive now!”

“I can imagine,” he said, unable to tear his gaze away from my pussy.

I should have been at least a little shy, spread out before him with my tits and pussy visible. I was about to fuck myself with a dildo, and all I could think about was Ian and me climaxing together. “I want to come at the same time as you,” I told him, “so let me know when you’re getting close.”

He hurriedly nodded, then wrapped his hand around his cock.

I brought the head of the dildo to my entrance, then began easing it inside. I winced as it stretched my opening.

Ian slowly stroked his cock, and I loved watching his thumb slide over the head, teasing the slit.

I had to draw in a deep breath as I pushed the dildo farther inside. My God, the head felt huge! Though I was sopping wet, my cunt still resisted the intrusion.

“I know you can take more than that, Libby,” Ian said, and when our eyes met, his stare was hot, his jaw tight with need. “That greedy pussy wants to be filled, doesn’t it?”

I nodded, whimpering as I applied more pressure. I had never encountered this side of Ian before, and it drove me absolutely fucking wild. I ignored the pain and gave the base of the dildo a firm push, forcing it into my cunt.

When the head finally slipped all the way inside me, I let out a plaintive cry.

“Fuck yes,” Ian groaned. “Your pussy is gripping it so tight!”

“It’s almost too much,” I whined, my voice pleading. Though I’d used the dildo dozens of times and knew I could take it, I realized I became incredibly excited when Ian coaxed and persuaded me.

“I want to see it deep in your cunt,” he demanded. “Be a naughty little slut and fuck that gorgeous pussy.”

I did as he said, sliding the dildo in and out. I had to be careful to keep the thrusts shallow so the tip didn’t strike my cervix. “You want to see me punish my pussy with this big cock?” I said through my teeth.

Ian began jerking faster. “Yes, Libby!” he urged. “That’s the only thing that will satisfy you, isn’t it?”

I hurriedly nodded and fucked my pussy harder with the dildo. With my free hand, I rubbed my clit, and helpless cries escaped my lips.

With his hand still around his cock, Ian’s stroking slowed, and instead he thrust his hips upward, driving his dick through his grasp. “Ah fuck, I’m close!” he said.

I pounded my pussy with the dildo, no longer caring if the toy collided with my cervix. My entire body was shaking with the need to come.

“Libby, please,” Ian moaned, “please come!”

The raw vulnerability in his eyes pushed me over the edge. With the dildo buried inside my cunt, I began spasming once more, my pussy clenching and my thighs shaking. “Ian!” I shrieked. “Ooh fuccckk!”

He quickly yanked up his shirt and aimed his dick at his belly. For several more seconds, he fiercely jerked his cock, and then his hand grew still as his body shook. Ropes of semen spattered his bare stomach, and he shouted with the force of his climax.

“Yes!” I wailed. “Oh fuck, all that cum, Ian…”

Even after he finished ejaculating, he still trembled. We were both breathing heavily, our faces hot.

Before I could lose my nerve, I took my phone from the bag, then angled it between my legs so I could take a picture of my pussy with the dildo inside me.

“Libby, what are you doing?” Ian asked, though he was too spent to be overly concerned.

I looked at him and grinned. “Tess wanted pictures of the end results, after we’ve both come. Do you mind if I take one of you? She’ll delete them right after she rubs one out while looking at them, and I’ll get rid of them as soon as I send them.”

Ian’s eyes widened, and he opened his mouth as if to protest, then released a heavy sigh and leaned back against the seat. “I suppose it’s the least I can do after she let us play like this.”

My grin widened, and I took a picture of his cock, still semi-erect. I managed to get some of the cum in the photo as well.

As I studied the picture, I licked my lips. “Wish I could keep this,” I told Ian.

I had never taken naked pictures of myself before, and I now stared at the one of my pussy in fascination. My hole appeared to be stretched to the limit with the dildo filling it, and my inner folds were glistening from my juices. My clit was still swollen, emerged from its hood.

I sent the pictures to Tess. “I’m deleting them now,” I said to Ian, then giggled. “Just wait till Tess sees these.”

“You can keep the picture of me,” he said softly, and I beamed at him.

“Really?” I asked, and he nodded with a smile. “I promise you can trust me, Ian.”

“I know I can.”

I stared at the picture of his cock with admiration I didn’t try to hide. “This will give me plenty of future orgasms.”

Ian laughed. “I’m glad I can be of service in that area.”

I put my phone away, then retrieved travel-size packs of tissues and baby wipes from my bag. “I came prepared,” I said.

“Thank God,” Ian replied. “I’m a mess.”

As he cleaned himself up, I eased the dildo from my pussy, feeling a twinge of pain as the head slipped out of me. Then I went about wiping off the toys and myself. We placed the dirty wipes and tissues in an empty plastic bag we were using for trash. After Ian put away his cock and zipped up, he pulled back onto the road.

I put on my panties and yanked up the bodice of my dress before fastening my seatbelt once more. “We didn’t lose too much time,” I said, glancing at the clock.

“It was worth every minute.” Ian looked over at me. “You’ve been incredible company, Libby.”

I smiled and rested against the seat, feeling relaxed from my multiple orgasms. I’d imagined this little game playing out in many different ways, but I never dreamed it would be so exciting for us both.

It wasn’t long before we reached my house. My parents came outside and hugged me, then warmly greeted Ian. I desperately hoped they couldn’t smell the sex on us. Since their smiles never wavered as they asked about the drive, I figured Ian and I were safe.

My mom had already fixed lunch, and she invited Ian to eat with us before he headed for his own house. He gladly sat down at our table, and I was relieved at how quickly he and I reverted back to friendship mode. No one would have ever guessed that we had just orgasmed in front of each other.

After we finished lunch, I walked Ian to his car. On the way down the drive, I heard my phone chime and took it from the pocket of my cardigan. The text was from Tess: OMG I am fucking wet after seeing these pics! They’re going to make me come so hard! Looks like you two had LOTS of fun. 🙂

I showed Ian the text, and he laughed, clearly pleased. “I can’t wait to talk to her tonight,” he said. “I have a feeling she and I will both be coming hard.”

I gave him a chaste kiss on the cheek. “I hope you have a great spring break,” I told him. “I’ll see you next weekend.”

He grinned down at me. “Have a lovely break, Libby, and don’t forget to bring those toys back with you.”

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