Meeting an Online Friend

He was naughty from the very start. Most guys were. But there was something about him that kept me interested. Maybe because I'm into older men, or maybe because his approach had class. He was a businessman and traveled quite a lot. He wouldn't tell me his age but would always say that he was still young enough to please any woman and then leave with a naughty smile. Which usually means he's in his forties or fifties. He was very sweet; always greeting me good morning, checking up on how I was doing in my schoolwork. And every so often he would send me some naughty emails.

For example:

Good morning Sunshine!

Have you recovered from your flu, and catching up with everything since that?

I was in the middle of something, and I thought of a little vignette that I thought you would enjoy...(and, maybe this is the right medicine for your sore throat...:)

From where our story last left off, we get together again and you've secreted yourself into my offices for a very personal meeting. My secretary doesn't know you are here.

Being your naughty, playful self, you 'clumsily' (with great skill and accuracy -lol) drop your pen under my desk and venture to get it. Crawling underneath wearing your tight work dress and high heels you push your ass up to generate more excitement from me, as if you weren't enough as you are. All the while I am on zoom call discussing business.

While under my desk, your hands dig into my pants and opened my zipper...

any ideas on how to finish this?

hurry up with you answer... I desperately need it now!!!! (before I burst) );

Kisses,

Alex

I would often play along, this was a safe playful place. It was also about the time when I learned how to type with one hand ;)

I zip open you fly, stick my hand in your pants, and grab you by you stiffening cock through your boxers. I pull on it a few times to release it from its bound prison. Finally free, it's throbbing in my hand hold.

You mute your call, and you forcefully shove my head back. I look at you, shove you cock in my mouth, and you begin to pump while tongue dances on your cock.

I wonder what happens next...

Kisses,

Kate

And on cue he replies immediately.

Fuck Kate, I'm really at my work desk right now... Here's what happens:

My mind periodically blanks during my call, but you don' t miss a beat, and you succeed in making me lose more and more self-control while you take more and more control of my mind.

I prematurely end the call so I can pay more attention to your heavenly work. My secretary knocks on the door one more time, and I tell her not now.... she enters anyhow just as I was cumming in your mouth. She sees your head bobbing on my lap and the stupid smile on my face.

Kisses,

Alex

We exchanged emails like that all the time; he even helped me write my other stories here. Each time, he would put in a short comment like. "I really wish you were here sitting on my lap right now. So I could feel your tight ass rub against my cock." Or "Can you imagine what it would feel like if I slipped my cock deep in your pussy?"

I knew what he was doing. Boys will always be boys. I was enjoying it as well so I kept playing along. The thing about me is that I'm really drawn into whatever story I write. It takes me days just playing with ideas in my head. And as I write the story, I would really believe that I was there, even more so than what my readers would say that they felt. So drawn in, that I would sometimes need to stop writing and just lay on my bed on the edge of orgasm. I would become partially out of breath and my mouth would just dry up from the arousal.

Our emails became more and more risqué as we went along. Soon we were asking each other to perform some dares.

I want you to go to school without any underwear today Kate. Tell me how it felt when you get home.

Or...

Why don't you wear a low-cut shirt to school and flash your cleavage to your professor. I'm sure he would lose it in class.

Out of sheer excitement, I would often do his tiny dares. And in return, I would also give him a few dares of my own.

I felt that our online relationship was very healthy. For one, I was perkier in class despite the weight of all my schoolwork. I always felt a tinge of excitement when I see his emails. They offered me release from all the tension I was under.

The dares became kinkier and kinkier. We started taking photos of our dares to show each other as proof. Like one time, he asked me for a selfie wearing only my bra. I complied but cut out y face from it. In return I asked him to jack off to my pic and show me the cum on the printed pic. I think that one he would have done without the dare. But it makes me feel hot knowing he did that for me.

It was only time that we would move to online video calls. For most other boys, that's the time I would ghost them. But not for him.

"Hello Sunshine."

"We've known each other for a long time now; maybe you'll let me see you on cam?"

Let me make this clear now: I've only seen his face once from a photo he sent me. And he's only seen my profile picture here. Aside from the body pics I sent.

"You don't have to show your face of course, but maybe I could see those pert little tits of yours."

I was, of course, wary but very excited. After a bit more prodding, I finally gave in and set up a video call. To be on the safe side, I only showed him my body from the neck below. For those of you who have already read my stories, you should have an ample description of what it looks like.

The dare started simple.

"Open your blouse Sunshine and let me see your bra."

"Very nice! I just love those sexy shorts you're wearing. It would be much nicer if they were on the floor, don't you think?"

Each command he made was so smoothly said, that I felt very little hesitation to obey. That was what really attracted me to him. Anonymity always made me feel safe and secure despite our naughty dares. And the air of mystery around him made him even more attractive.

"Can you imagine how it would feel if I were there right now Sunshine?"

"You'd be sitting on my lap, as I played with your nipples."

I would gently do what he said and imagined he was there. My arousal was building up by the second.

"Why don't you let out your bra down Sunshine, and imagine that I'm licking your nipples. Love those tits sunshine"

"Can you feel my cock under your ass? Move your hips so you can feel it more."

"I just love massaging your tits; your nipples are very hard now aren't they? Almost as hard as my cock? Do you want to feel my cock inside your pussy?"

"I'll show you my cock now Sunshine; imagine how it would feel inside your pussy."

"Why don't you put your finger in your pussy Sunshine? Wow, did you shave that just for me? Imagine my cock teasing your clit."

"You like that, don't you? Fuck yourself faster. Can you feel my tongue circling your nipples while my cock fucks your pussy?"

"You're damn hot Sunshine; I can't stop stroking my cock. I'm almost cumming. Ride me Katie. Fuck, you're so hot."

"Faster Sunshine, can you feel my cock about to burst? I can feel your pussy tightening around my cock. I'm almost there."

"Ahhhhh, fuck yeah..."

I was moaning the whole time, imagining every single line he wrote. I did all I could not to scream when I brought myself to orgasm. For a couple of months, we talked online always with dares. Always about fucking when we meet. My school papers finally caught up with me and I was no longer able to spend as much time on the net as I would have wanted.

It was a few weeks since I last logged in when a familiar email jumped right out of the screen.

Hello Sunshine,

Glad you're finally writing again. I loved how you finished your story. I do hope we can continue writing ours'.

Oh, by the way, I'll be in Singapore for a few days this week. If it's ok with you, maybe we can meet there in Manila for a layover. Tell me soon so I can arrange a short stop-over on my flight home.

Kisses,

Alex

PS. I'll to give you a good pounding when we meet. 😊 Kidding. Just dinner and drinks I promise

"Oh god, he's actually coming here," I let out a whisper. I felt excited and unsure of what I should feel. Here's a stranger who I've been really intimate with but completely shrouded in mystery. Now that shroud is about to be removed. I didn't really know what I wanted so I just let the email sit for 2 weeks and sent him my usual ghosting reply.

Subject: Manila

Hi,

I'm sorry I'm a bit late with my reply; I only opened my email today. I've been a bit busy with school and all.

I would have loved to meet with you here. I'll give anything for a good pounding right now 😊 Kidding. Anyway, I'm sorry I wasn't able to reply in time. I guess you're already back in the US. Maybe we can set it up when you fly again. I'll be sure to meet with you then.

I'll always be here to email you if you're still up for it.

Kisses,

Kate

Can you imagine my surprise when, after just a few minutes my messenger popped an icon "New Message: Subject: Re: Manila"

Hello Sunshine,

You caught me in the nick of time. I thought we wouldn't be seeing each other... ever. Fortunately, my trip was moved this week. And I've already booked a flight to Manila even before I came here, just in case. I figured if you didn't reply then I'd have wasted a few hours. It turns out that gamble paid off. 😊

My flight leaves at around 2pm tomorrow, so I'll be in there at around 8pm. It'll be just a short stop over, as my flight home will leave at 7 the following morning

I think that should be enough time for us to have a dinner and few drinks, if that's ok?

Would it be ok if we met at the Marriott Hotel lobby, by the airport, around 8? I don't really know my way around, and I'll be in a fix if I miss my connecting flight home. I'll book a room right now.

Dinner's on me.

Kisses,

Alex

My mouth hung open when I read and re-read the email. I could hear my heart as it thumped. I didn't really know if it was fear, or excitement, or maybe a bit of both.

The entire day went by like a dream.

My thoughts kept going back and forth:

"Should I meet him? Is it safe? I want to meet him. I don't want to go."

Over and over the entire day, my thoughts mixing with his words:

"Can you imagine how my cock would feel inside you? I'll give you a good pounding when we meet. You'd like that, wouldn't you Kate?"

I was in a semi-hypnotized, semi-aroused state the entire day. Even a cold shower wasn't enough to bring my temperature down.

"What the hell should I wear?"

I thought to myself as I walked into my closet.

I took out a long black dress and looked at it through the mirror.

"Nice, I like this"

I thought, suddenly countered by,

"What are you thinking? You're having dinner with a friend, not going to a prom."

My pantsuit, slacks, skirts, all received similar responses. I felt like I tried on all my clothes, until I finally settled on a white, one-piece, halter top and nice skirt. I let my hair fall on my back and shoulders and looked at myself in the mirror. I did a pirouette which partly lifted my skirt.

"That should do. It's sexy enough but not too sexy."

To be honest, dear Readers, I thought about going out without wearing any underwear, (his words really messed me up... bad...), but decided to wear a white thong and a matching low-cupped bra that hooked at the front. At the back of my mind I knew, that if he wanted to, we were going to fuck that night and I wasn't going to be able stop him.

It was almost 7:30 when I left home. As usual, I had to put on a light hoodie so that my mom won't catch me wearing something so sexy. (Alright, the dress was way too hot but I couldn't help it).

The grab (uber) ride seemed to take forever, I was quite lucky the cab driver was an elderly gentleman. Otherwise, I might have verbally pounded on the driver. I was so high-strung already, and my heart rate was going about 120, so you can just imagine.

I removed my hoodie as the cab arrived at the hotel driveway. The weather was unusually chilly for a late February evening in Manila. The night air embraced my legs and bare shoulders and hardened my nipples as I walked to the front door.

He was already waiting in the hotel lobby, watching the door from where he was sitting on a sofa. He practically jumped up as he saw me enter. It was almost comical, only shows how excited he was.

I've always guessed that he was in his mid forties from his stories. His hair showed some hints of grey but he looked very youthful and may pass as a guy in his early thirties.

Again, we had seen each other's faces only once before, from relatively old photos. We wanted to keep the mystery going, so no other photos were sent between either of us. But that single photo was enough for me to recognize him, and vice versa. He was already quite good looking in the photo, but the photo didn't do him any justice.

His looks were somewhere between a young David Hasselhoff and George Clooney. He approached me and gave a light hug, or rather a touch on the hips as he kissed my cheeks. It felt almost fatherly, which was good because all my fears and hesitations seem to have faded after that. I guessed that he was about 6'1" and dwarfed my 5'2" frame.

"You look really beautiful, Sunshine," he greeted.

"Please, don't call me that," I said with a blush. "Call me Kate."

"Well then, you look really beautiful, Kate," he said with a wide smile on his face, which made me blush all the more.

"Would you like to sit here and talk for a while or would you rather go to the restaurant and chat there?" he asked as he guided me across the hall.

"Let's go to the restaurant, I'm quite hungry," I clumsily replied.

"Ok, I'm pretty famished myself."

He was quite the gentleman. You would never think that he was the same man who kept sending me those naughty emails and giving those sexy dares.

"Maybe he's just like me, naughty on the net but not in real life,"

I appeased myself. But who was I kidding. I saw it in his eyes, he was a predator looking at his next meal. And I was handing myself on a platter.

Dinner went well. We talked for over an hour about ourselves. Pretty soon, we were both laughing as if we had been friends our entire lives. We talked about his work, and he mentioned that he also did some stage play writing as a hobby.

One question he asked repeatedly was "How could such a pretty girl like you, have such a naughty creativity when writing?"

He kept asking me to share how I was able to draw out my thoughts and ideas for writing. How I was able to relate with the character. What I felt as I wrote the stories.

They were orchestrated questions and his intentions were showing on his sleeves. Anf the more I answered his questions, the more aroused I felt. I should have excused myself at that point but he did it so smoothly, always relating to his hobby as a writer that I didn't feel anything wrong with his questions.

At around 10 pm, the waiter told us that the restaurant was about to close, but we could transfer to the bar. Very politely, he asked me. "It's getting a bit late, is it still ok if you stayed a bit longer?"

I replied by taking his hand and leading him to the bar.

We sat by the bar facing each other. I felt more exposed sitting at the bar. My skirt hiked up as I sat on the bar stool and now my thighs were clearly showing. Fortunately, there were very few other people there.

"Scotch neat," he told the bartender. "How about you Kate?"

I looked to the shelves at the back trying to look for the menu or something. Sensing my inexperience, he said to the bartender, "And a mojito for her."

I never imagined that a bar could feel so romantic -- adding the fact that there were only 5 other people around, it made it very intimate. I leaned my back on the bar and playfully swiveled my bar stool.

We continued to chat about our past relationships. We kept on chatting about something else, everything from the past to the present. Every so often, his hands would touch my arms. Give me a tap on my shoulders. A couple of times, my skirt hiked up a little too high so he would gently pull it down, while at the same time brushing his palms on my leg. He was quite touchy which I thoroughly enjoyed.

He then started sharing his ribald youth and how he drew on those experiences when he emailed me. He said that he felt his youth being re-lived when he chatted with me online. And that our dares made him feel alive again. He felt desired. Soon our conversation became a little more like our emails; naughty, playful, but still with a shroud of mystery.

His questions become more intimate like: "How did you feel when I sent you this email?" or "Did you flash your professor your cleavage (yes I did), it was very arousing wasn't it?"

Our conversation was getting me aroused but I didn't want to show. After all, he's still a stranger, albeit a very handsome one.

I finally had the courage to ask. "Why do you send those naughty emails to me? You don't seem that naughty nor sex crazed as you portrayed."

He laughed hard at my question which made me feel a little embarrassed. "No, Kate don't worry, I'm not as sex crazed as I am in our emails," he said with a wink. Damn that man. He knew exactly what he was doing.

"That's a relief. I guess there's really no reason to be worried,"

I thought as I downed my drink.

"And besides, I can probably say the same thing about you," he said with another laugh.

He leaned over to me and whispered, "I mean, who in their right minds would ask someone they barely know questions like: Can you imagine my tongue circling your pussy all night while you sat there?"

I was a bit taken aback by his statement, or was it a question... I didn't really know. My pussy was already purring at this point. But his question sent chills ran up my spine, all I could think about was his tongue circling my pussy. I tried to stammer a reply but he laughed so hard after his statement that all I could do was laugh with him.

"Actually, I have to apologize for that. I just felt so safe in all that online that I kinda ran away with it," he said. "And you didn't seem to mind so I kept pushing on."

"Like right now, you'll probably slap me if I asked you, aren't you wondering how it would feel to have my cock deep in your pussy, right?" he whispered again, creating emphasis on the last part.

"Uh... yeah... I ah... I guess," I stuttered, uncertain of what I should say.

The more he talked about how crazy our emails were, the more relaxed I felt about him. He kept on whispering in my ear to make sure that no one would hear what he said. But the way he described and stated the emails made me terribly horny. His descriptions were so detailed that I often find myself drifting and drawn into it. I was half-glad that they weren't real and half-wishing that they were.

By most standards, I can carry my alcohol quite well. But that night, I was already feeling tipsy halfway thru my second drink. Maybe it was the stress of the entire day, maybe because it was late, or maybe it was the mood of the place, or possibly I'm just damn horny; but at that point I knew I was no longer thinking clearly. And I could clearly see that he was enjoying every minute of it.