More Driving Lessons

Hi! My name is Anita and I recently shared with you an exciting experience I had whilst taking driving lessons. I'm twenty, with a small petite frame which make my DD's look massive. I have jet black hair, chocolate brown eyes, and from certain angles I give away my Asian descent. My mother's family come from China, but we've never been, and I wouldn't say I look Chinese, but apparently sometimes I do - So there you are!

I told you before how I had started driving lessons in early January, and that my penchant for flashing had led me to flash my elderly instructor, Henry. He's in his late sixties, chubby with white hair circling his balding dome. In the last lesson I told you about, I had engineered a way to become topless in front of him, and he had taken the opportunity to cop a feel of my boob. After the lesson I had watched him in the car, masturbating after the experience, but was disappointed that he chose not to finish.

This is now my aim. My mission is to make Henry cum.

I must apologise, it's been much long than expected to update you. Things got quite busy, but now the entire world seems to be in lockdown over the Covid-19 pandemic, I find myself with quite a bit of time to fill you in on what you've missed!

After that, somewhat eventful, driving lesson I found it hard to think about anything else. I kept daydreaming about how it felt to have Henry's chubby fingers squeezing my boobs, and the image of him jacking off in his car was now etched in my mind.

The next lesson was Thursday and it soon arrived. I found myself practically skipping from my front door to Henry's car. He'd already swapped over to the passenger side. He greeted me with a smile, and I set up for a couple of hours of driving.

Now, I'm going to disappoint you here. I decided that I wouldn't do anything naughty during this lesson. Whilst my imagination clearly wanted me to tease him, I was definite that I needed to keep control and show restraint. Whilst flashing him was a lot of fun, and I meant to keep my goal of seeing the old man ejaculate, I didn't want him to think I'd be flashing him every lesson. Whilst I enjoyed distracting him, it was also distracting me, and I do actually want to learn to drive! So, this lesson I was fully covered.

I don't know if Henry was disappointed, or relieved, because he acted perfectly normally. We went over parallel parking again, and he got me to do an emergency stop a few times. We'd already gone over these aspects, I guess he was just seeing if I'd retained the knowledge. I won't bore you further with this lesson, as there truly was nothing remarkable about it.

At the end, the next lesson was scheduled for Monday, midday. Perfect, I knew my parents would both out all day. I thanked him and quickly let myself into my home. Once the front door was closed, I raced upstairs to look out of my bedroom window to see if I could catch him masturbating again. I was a little disappointed to find he wasn't, he was already driving away to his next appointment. I hadn't offered him anything to masturbate over, to be fair. Monday, however, that would change.

Monday arrived quickly (don't they always seem to?) and I had already planned what I was to wear. I was going to ignore the fact it was pretty cold outside, if anything that was going to help my endeavour. I chose to wear my sky-blue denim shorts, revealing my legs. Now I wouldn't say my legs are particularly my feature, but they looked good. I'd waxed over the weekend and I must say they were looking kind of silky. I was impressed with myself. I'm not stupid though, I know what my true assets are, and the trick was finding a new way of exposing them... and I had just the thing!

I had a pink cropped shirt. Quite a thick fabric, and not in anyway see-through, but with it being so cold today my nipples were noticeably poking through. I would normally wear a sports bra, or something underneath, but obviously I wasn't going to be today On a girl with smaller boobs, the top was cropped low enough that it wouldn't really show anything but midriff, but my big boobs were problematic. To be honest, my Dad had made it quite clear he didn't like me wearing it as it shows too much... and he was not wrong. With my arms down, everything was covered, but I tend to gesture with hands a lot when I talk, and my under-boob games was strong. I knew that whilst driving, my hands on the steering wheel, Henry would be afforded many views of my boobs, the bottom of them at least. If I lift my arms up - well, there they are. The edge of the top rises well above my nipples, fully exposing them to the world.

I had found that out the hard way, in the lounge one evening. I'd stretched and my Dad accidentally looked directly at my exposed boobs. He got quite angry and forbid me to wear it again. My mum reasoned with him and explained that normally I'd be wearing a bra so that wouldn't happen in public. He would definitely not approve of today.

Henry's car pulled up and I trotted out, locking the front door behind me. He immediately clocked my outfit, his eyes hovering over my top... I think he already knew what was going to happen. I could be wrong, but I think was trying his best to repress a smile.

I got into the car and adjusted the seat, as I always need to, along with the mirrors. I wouldn't say that Henry was 'watching' me, but he was aware of what I was doing. He knew my order of things and knew what was next. I reached back, lifting my arms up to adjust the headrest. Instantly I felt the material of my top rise, and my erect nipples were now on show.

I couldn't help but glance over to him, to see if he was taking in the view. He was and I smiled to assure him it was okay.

"Very nice," he beamed. This took me by surprise a little and I let out a giggle. I took a bit longer than necessary to make the adjustment, and Henry took in every moment. I did wonder if he would reach out, like he did least time, but sadly he didn't. Notice I said sadly, I found myself wanting him to touch me.

I started the engine and the lesson got underway. Throughout, I felt my top rising and lowering with my manoeuvres, and I was aware of Henry's gaze. He was spending more and more time checking me out than my driving. I love it, and I loved how excited he was becoming. He had to arrange himself a couple of times. Each time I was mentally willing him to just get his cock out but I knew he wouldn't. His bulging was very noticeable though. I found I was having to remind myself to keep my eyes on the road.

The end of the lesson was fast approaching, and he noted that we needed petrol again. I pulled into the station to fill up. Normally I would do the filling up, he'd watch and then go pay, but he suggested that I did it all. He asked me to put in twenty and gave me the appropriate money. I got out and did as I was asked. I got the payment bang on twenty - I'm seriously a pro at that - and I was just about the head into the shop to pay, when Henry called me. I hadn't shut the petrol cap properly. I tutted at myself and went to deal with it, dropping the car keys in the process. Ever the gentleman, Henry got out the car immediately to help. It was then very clear why he had chosen to remain seated.

Henry was rocking quite the erection. His trousers did nothing to hide how big he was. I hadn't realised, as had only seem it in a sitting position, but now he was standing... I was impressed. He noted me looking and for a moment attempted to cover. The keys were retrieved, and the cap closed. He asked, with something of a red face, if I was still happy to go and pay, which I was.

He went to return to his seat, but I did something that surprised us both. My left hand went out and I found myself running across the length of his member. He looked at me with shock, and he leant back on the car. I wasn't rubbing him, nor was I squeezing, but I could feel him throbbing through the cloth of the fabric. In reality my hand couldn't have been there for long, maybe only a few seconds but in the moment, it felt like ages.

I let go and went and paid, as Henry collected himself and got back in the car. Once I'd paid, the only thing left to do was to drive back to my home - which I did - and we the journey was pretty quiet. Had I overstepped? I mean he had touched me, so was it such a massive faux pas to have returned the favour? I pulled up near my house and the lesson was over. We arranged the next lesson for Friday, and I considered getting out the car but... was that really it?

Henry was still hard. I could tell from his bulging crotch. I wondered if I raced in and upstairs if I could catch a glimpse of him wanking himself off again, but instead I decided to offer him once last morsel of inspiration. The seatbelt now unbuckled I decided to give a stretch. I didn't need to but I knew this would reveal my tits to him again and it would be more likely he'd want to 'sort himself out'.

I faked a yawn and felt my breasts become visible to the world once again, and I looked at Henry. His gaze lifted from my boobs to my face and he went to say something but I pre-empted his thought.

"You can if you want," I nodded, and sure enough his soft right hand was holding my left tit. His hand moved across to get a feel of my right, and I decided to share my secret. "I saw you," I whispered. "The other day, I watched you from my bedroom window."

Henry jolted back and looked out from the windscreen up to my window and then back to me, with a look of horror on his face.

"I'm so sorry, I don't know what to... "he trailed off, with a heavy swallow. His face had gone white.

"I don't mind," I laughed, "I liked seeing it. Hope I get to see it again." I smiled and left the poor man dumbfounded in the passenger seat. Normally I'd leave the drivers door open, but I actually wanted him to stay where he was. I coolly walked to let myself into the house, and once in raced upstairs to my window. I knew he had to still be there this time.

I looked down from my window to find Henry, still in place, looking back up at me. I realised he needed one last bit of encouragement so, without a hesitation, I whipped off my top, throwing it back onto bed and then looked back down to my audience. I was now completely topless. It was quite possible other people could see me, but I had my target.

Henry smiled, and it looked like he took a breath. He seemed to mutter something to himself as he looked around before looking back up at me. I was surprised when he adjusted the seat, pushing the back down a bit, I realised that he was actually readying to give me the show I was hoping for. He positioned himself and once again returned his gaze up to me. From this point his eyes never left me. Almost involuntarily I began to feel my own boobs. Caressing them, squeezing them.

Henry started touching himself at the sight of me playing. Over his trouser at first but, still with his eyes fixed on my body, he unbuckled his trousers, unzipped his flies and unleashed his yearning cock. This was another level. Before I had been a spectator, but now I was here topless watching this old man jerking himself off to my nudity. I was wet and I was anticipating his climax.

Something stopped him though. He sat up and hid himself, looking off up the drive. I quickly grabbed the curtain to cover myself too, his reaction causing me to panic. He clearly had thought someone was turning in and would catch him. False alarm though. He relaxed and looked back up at me. He revealed his dick to me, still hard thankfully. I let the curtain drop away and he started to stroke again, but this time I was the one to stop it. I gestured for him to wait. He seemed confused but nodded.

I had not planned this, this was by no means my intention, but as I grabbed my top, quickly putting it on as I navigated the stairs, I knew what I was about to do. It wasn't going to be enough seeing Henry cum from the window, I wanted to be there.

I raced to the car, and got in the driver's seat, pulling the bottom handle to push it back to allow more leg room. Henry was still in the passenger seat but covering his modesty. I quickly checked around and removed my top.

"Please continue," I said, with a happy chuckle. I knew he need encouragement to continue.

His instinct to feel my bare breasts meant, for the first time, I could see his cock in all it's glory. It was much bigger than it appeared from my window, and I couldn't help noting the girth. It was thicker than my ex boyfriend's. As his hand explored my body (not just my boobs now, he was mapping my back, shoulder, waist), I couldn't help but touch him. With my left arm propping me up, my right hand reached over and he moaned appreciatively as my palm wrapped around his throbbing cock.

Henry got braver and allowed himself to reach for my arse. I had to move myself close to allow it. I was still wearing my denim shorts, but his grip tightened over my cheek as I started to stroke his shaft. His eyes kept darting between my boobs and what I was doing. For a moment he closed his eyes, and his hand moved around as if he was trying to reach my pussy from behind. The angles were wrong for that, and soon his fingers found themselves up on my tits, playing with my nipples.

Aware of what his hands were doing, I was aware of what effect mine were having. There was a trickle of pre-cum spilling from his penis, and I found myself using my thumb to use it to lubricate the rest of dick. I could feel it hardening in my hand as I stroked. As I ran some of the liquid over where the helmet meets the shaft, I could feel Henry's entire body start to tense. He was close.

"Stop," he said hesitantly, catching his breath. "Please, I don't want to..."

"You don't want to cum?" I questioned.

"It's not that, it's just..." He looked down at himself. "I don't want to make a mess. I've got another lesson in a bit and- "

"There won't be a mess," I intervened. Okay, I really, truly had not anticipated this. I guess I should have, really. I had created this situation; I should have realised this might be on the cards.

Before Henry could reply I repositioned myself and, attempting to avoid the gear stick, lowered my face towards his cock. My palm still stroking his shaft, I allowed my tongue to flick over the tip and circle the head, before locking my lips around him. I quickened the pace of my hand as my tongue worked his cock inside my closed mouth.

"Fuck!" Henry announced should as the experience become to much for him.

His hand latched tightly onto my boob and I felt his body tensed, his cock hardened and... wow. An ocean of hot cum released into my mouth. There was so much. I swallowed, doing my best to keep my mouth on his spasming member. More cum flowed out and I found myself swallowing another load.

Henry moaned with pleasure and I felt his hand loosen its grip from my boob. I continued to work his cock for a bit, making sure I got every drop. Once I was sure he was done, I used my tongue to clean him up and I sat back to put my top back on.

"Thank you, Anita, "he gasped, trying to get his breath back. "Is there anything I can do for you?"

"I wanted you to cum," I announced, matter of fact. "I just got what I wanted."

Henry nodded, possibly a little bit confused by what had just happened. I looked down and saw his cock, still out but now flaccid. He became shy and started to put it away. I stopped him for a moment and decided to hold it my hand.

"This is the oldest penis I've seen, let alone touched," I admitted.

"Yes, I should imagine it is. How old are you?"

"Twenty."

"Do you have a thing for older men?" he quizzed.

"I don't think so," I pondered. "I enjoy flashing, and teasing. I didn't intend for this to happen, but after I saw you from my window, I guess I wanted to follow this through."

"Okay," he nodded, seeming to understand. "So now this has happened, does that mean you won't be showing off anymore?"

"Do you want me to stop?"

"I didn't say that."

"You want me to keep on flashing you?"

"I'm old enough to be your grandfather."

"That wasn't an answer," I laughed.

"Can I be completely honest with you?"

"Of course," I nodded, interested to see where this honesty would go.

"After your first lesson with me, I went home, and I masturbated for the first time in a long time." Henry took a moment before continuing. "You've been something of a fantasy for me, and then you started showing off your body to me. You have a beautiful body."

"Thank you."

"Professionally, I need this not to happen again," he frowned. "Personally I want it to happen every week!"

"Okay then," I smiled, hoping to reassure him. "What if, I do flash you every now and then? Not all the time, not every lesson. Just sometimes? How would you feel about that?"

He took a moment to consider before laughing.

"Anita, I couldn't get a twenty-year-old to suck my cock when I was twenty, I certainly didn't expect it now. I would love it if you were to show me your body every now and then. That would make me very happy."

"Okay then, that's a deal."

There was a moment's silence as we both contemplated. I could still taste his cum in my mouth.

"May I touch you?" he asked, bravely.

"Okay."

He reached across and lifted my top, placing his palm on my boob.

"They are magnificent," he enthused. "I've always loved big breasts, but my wife has quite small ones. They were very nice and pert, but yours are perfect."

He finished playing and it was time for him to go and pick up his next student. He was already late. We both got out our respective sides, he shut his door and I left my open for him as normal. I started to head to my front door as he got into the car, but I sensed he was hovering.

"Everything okay?" I asked.

"May I," he began, cautiously, "possibly be allowed to see your pussy on one of these little teases?"

I thought back to him trying to get to it via the back of my jeans earlier. I thought for a moment on whether I would let him go there.

"Henry, I will make you a promise," I stated, "if you're a very good driving instructor, and if I manage to pass my test first time... you won't just be allowed to see my pussy, I'll let you cum inside it."

With that mic-drop, I turned and let myself into the house.

Since then, I've had a couple of flash-free lessons, but the world is in an interesting place now. I'm in self-isolation and I've not got any planned driving lessons until everything has blown over. I do have other stories to share though. Henry isn't the first person I've flashed, or teased, and I promise I won't take as long to share those experiences with you.