Introduction and first date

Hey guys, I’m Emma, I’m your normal 19-year-old teen girl who loves to party and hang out with friends, I go to uni studying fashion design and play on the field hockey team. Most people who walk past me would assume I’m the cutesy, innocent, curly-haired blonde girl who is friendly and nice to all she meets, which I am, but like a lot of people, I have my deep, dark secrets.

In public, I keep my squeaky clean girl next door, Uni athlete, image, a role model to my peers and family but I’m far from being the angel my parents think I am.

I’m no fashion model but I’ve always had no problems getting a date, my long, toned legs lead up to a small, peached-shaped butt which I’m really proud of, my best feature if I were to be asked. I’ve always had a lean and athletic type of body, flat stomach, thin arms, small waist, tiny chest, which I hate, especially having always been around girls in locker rooms, and seeing what they were blessed with really made me wish my breasts were bigger. I’m taller than average, standing at around 5’8, I have a heart-shaped face with soft features, small lips, bubbly cheeks, striking, round, blue eyes, and shoulder length, strawberry blonde, curly hair.

I use to date a fair bit in high school, it was enjoyable for a while until I got sick and tired of the same old boys who all did the same things, it just felt stale and repetitive which is what led me to search out other options that were out of the norm. Everyone has heard of dating apps and internet sites that offer adults the platform to meet strangers for whatever reason they choose, and for a time I was happy to try out the more common and mainstream options but a strong part of me always wanted to see what it would be like to join a more risky, niche site, catering to specific wants and needs.

Like most at the beginning, the standard cons always seemed to outweigh the pros when making my decision, “what if my parents found out?, what if I came across someone I knew?, was it safe to meet randoms?, are people going to find out about this?”, all these thoughts racked my brain but the more I read the reviews and testimonials, reading articles online and in mags, but mainly because it got me so aroused and wet thinking about it I eventually took the leap.

A lot of sites had their appeal, but what really got me horny and excited was older men. I had always been curious from a young age but never found the courage because of what people might think, I still have those concerns which is why I wouldn’t openly date an older man, at least not until I was a bit more mature myself, my parents would freak if I brought home a guy in his 20’s let alone a man that might be twice my age.

After doing some more detailed research I decided to join a sugar daddy site, not the most popular one of course because I was still afraid of running into someone I knew, instead opting for a less well-known option that still had great reviews. I was happy to learn that girls could join for free if they got verified rather than paying the steep members fee, I sent the photos required for verification that night and went to bed excited about my decision.

The next day I was happy to receive a message informing me I had been verified and details on how to set up an account, I was tempted to skip uni and dive right in such was my exhilaration but bottled it up for later that night.

My friends were quite disappointed I chose not to go out that night, they were starting to wonder why I had lost interest in dating but I couldn’t really give them the real reason why. I rushed home, showered the sweat from hockey practice, and jumped straight on my laptop.

The site was set up a little like Facebook where people would create a profile and others were able to view it and send you messages, like pictures and see your interests. The site was free initially for a month but you had to earn a certain amount of points for it to stay cost-free. Earning points was simple enough, posting pictures, engaging in the forums, positive reviews from other users all earned you points, it was just like any other social media site and I was having fun setting everything up.

I’m a bit of a perfectionist and didn’t even realize I had been playing around on the site for a couple of hours, I was finally happy with the job I did, posting a few pictures from a holiday in Thailand 2 months prior, nothing too naughty or risque just some swimsuit pics and ones I found cute before I activated my account for all to see.

In the meant time while I waited for any interest I profile hopped as you do when discovering something new for the first time. Most profiles keep it pretty simple, men ranging from their 20s to even 70s were members. It was so intriguing reading what these men wanted, most just looking for a random hookup while others were searching for a fuck buddy type arrangement or sugar baby. I wasn’t interested in anything long-term for now but the thought of being a sugar baby kind of got me wet, I had seen and read a lot about these types of arrangements, it was definitely appealing but not for me at the time.

It wasn’t long after my profile went public that alerts started popping up notifying me people were liking my pics, I was blushing and excited, feeling that rush you get from being validated, it was different from people liking my pics on Facebook or Instagram, that just became normal but knowing the nature of were these likes were coming from made it thrilling.

I started reading a few comments guys had posted on my pics, most nice and sweet and very gentlemen like but a few were crude like “ hot ass, love that little body” or “ you just made me hard AF”, I’m not naive, I knew what I was getting into, I actually loved all the comments no matter the nature, they were all positive and got me grinning happily.

My inbox was filling fast, it was almost daunting to see the amount,” how on earth do I sort this out”, I thought to myself, I didn’t want to offend people by not answering them but I knew I couldn’t give my time to everyone. I came to the conclusion I just had to check profiles and when I saw one I liked I would reply.

The first few profiles didn’t peak my interest, not that the men weren’t attractive, a couple were but I just didn’t get a good feeling reading their interests and what they wanted, some were just way too old or way too young in age, I was looking for someone in their 30’s to late ‘40s, who just wanted to keep things casual. I had narrowed down my list to 3 from the 30 or so men who messaged me and typed a short reply to each.

The website had an incognito mode where you could be invisible to all except for the members you allowed to contact you, it was great knowing I could still use the site without getting swarmed with messages and feeling bad about not answering.

Most of the messages were simply getting to know each other ones to build some chemistry, after half an hour or so one guy really started getting most of my attention, His username was Tony42, and as you might have guessed he was 42 years of age and worked in the construction industry. Tony had a great rating on the site and had been an active member for more than 4 years. His profile was full of positive reviews from girls and he had many threads on the forums, the most popular being his online journal where he described his exploits with various women.

Tony looked well built and muscular in his photos, definitely a gym goer, he wasn’t ripped like a bodybuilder but had a sexy definition and tone to his physique. He described himself as a confident, sexual person that didn’t like to be tied down by marriage or kids, he wanted to meet and fuck new people without the drama, especially younger women, honest and straight to the point which I found sexy as hell along with his dark, short hair and light beard.

We chatted for some time and I explained what led me to join the site, he understood my reasons and had met other girls who felt the same way. It wasn’t long into our conversation when Tony suggested we chat through cam, maybe an hour or so had passed, and I readily agreed surprised at how fast things were going, it was the most fun I’ve had interacting with a man in some time and it wasn’t even in person.

I quickly looked around my room and touched myself up a bit to look presentable, I was so nervous as his cam feed came through, like me, Tony was sitting at a desk it looked like, he smiled and gave me a little wave as we tested our mics.

“hello ... hello can you hear me ok”, I spoke into the mic.

“yes perfect Emma ... how do I sound?”, he replied, his strong, raspy male voice very much to my liking.

“great ... Really good ... all clear”. I relayed shuffling in my seat to get comfy, my left hand fidgeting with the strap of my pink singlet top which I tend to do a lot when I’m nervous.

“perfect ... Your’e even more beautiful than I thought when looking at the pics you posted, I’m one lucky guy being able to do this right now”.

Tony’s compliment made me blush and the way his dark, hazel eyes were staring straight at me through the computer screen got me tingling, he looked just like he did in the photos on his profile, they must have been recent, I was very pleased and relieved.

“so I’m convinced ... How about we meet up tomorrow ... I can pick you up at 7”. He confidently offered before grinning and smiling almost smugly.

I returned his smile and giggled playfully at his bold suggestion, he was definitely a cocky type of guy and full of charm, “You’re really funny ... what makes you think I like you that much already?”, I retorted. His smile grew larger as I watched him through the screen, almost as if he knew I would agree (which I would, eventually) but I didn’t want him to know just yet.

“I just have a hunch ... but I’m happy to sit here and think about what you would look like naked until you agree to meet me”, He countered with.

I couldn’t help but laugh, it was pretty clear we had some chemistry, I’ve never had a guy talk to me in this manner let alone in the first hour of the conversation, It was really having an effect on me sexually. “ well I guess you are the more experienced one, I’m just a naive teen girl”, I cheekily said pouting at my cam.

“I’m definitely full of experience ... which I’m happy to share if you meet me ... I think you would like it a lot ... it’s fun to share”, he boldly said trying to entice me further.

“I can tell you are full of a lot of things but you’re in luck ... I like to give people a chance so I guess we can meet tomorrow and I’ll decide if I want you to share your experience with me or not”, I put forward confidently.

“great ... that’s all a man can ask for, are you ok with meeting at my place or would you like a hotel meeting, I’m happy with either”.

“I think a hotel might be best”, I quickly agreed, showing signs of nerves for the first time since we started chatting.

“of course, I understand ... I’ll set it all up ... wear something pink ... I like that color on you”, Tony devilishly added causing me to blush once more.

We didn’t chat for much longer after that, it was past midnight and my eyes were getting strained at being on my laptop for almost 5 hours, Tony also felt the same but not before cheekily asking me to show my tits, I playfully started to left my top up before closing my screen. Tony sent a disappointed emoji message to my phone which I giggled at before apologizing and telling him I was looking forward to tomorrow.

Around midday I got a text from Tony outlining where and when our meeting would take place, I was impressed he had booked a pretty fancy hotel for the night, part of me felt like I was being hired as an escort for this older man’s pleasure and laughed at the thought if anyone found out.

The excitement was building as time got closer, I told my parents I might stay over at a friend’s place tonight and not to worry, I hated lying to people but I had to admit it was adding to the buzz I was already feeling. I think I swapped and changed into about 10 different outfit combinations before deciding on a long sleeve pink, bodycon, knitted dress that was both elegant and cute, it covered up most of my upper body but showed off my legs nicely and hugged my small curves, along with white heels, matching handbag and large hoop earrings I was finally ready to head out. I usually take the bus when I went out but there’s no way I would take one today dressed this nicely so Ubering it was.

Knocking on the door to a strange man’s hotel room was a first and oddly empowering experience, I guess there was no turning back now as he opened it and we laid eyes on each other, he seemed very pleased to see I had not chickened out and took his time giving me an approving once over, his eyes darting up and down my body like a hungry hyena.

I was at a loss for words letting him have his staring contest with my dress until he finally invited me inside licking his lips and closing the door behind me. The room was nice with one large queen bed in the center and a leather couch to the side, the windows had an amazing view of the city and opened out onto a small balcony.

“I’m very happy to see you made it, you look amazing by the way, love the dress”, Tony pointed out as he walked around me, his eyes probably getting a good look at my ass before doing so.

“Thank you ... And thank you for getting this room ... it’s really nice”, I acknowledged while standing like a stiff corpse frozen with nerves.

“It’s no bother, I’m more than happy to spend a bit of money if it means I get to spend time with a girl like you Emma, you are a real stunner, I’m very lucky”, he declared standing a few feet away from me, his confident grin on full display.

I closed my eyes a took a deep breath, I’m usually not shy on dates and I told myself this was just like any other, I shook my arms out and put on my best smile trying to re-focus. “ well I really appreciate it, looks like we could have a lot of fun here don’t you think tony?”, I proudly said finally able to shake off my insecurity.

“a lot of fun indeed young lady, would you like a drink to get warmed up?”, he offered which I took up gratefully.

Tony poured me a glass of sparkling wine and we made small talk as he gave me a little tour of the suite, he was funny and charming, and mature, all the things I found attractive in men. Our tour ended with us out on the balcony enjoying the views, Tony pointing out the buildings he and his company were responsible for constructing which was quite impressive. I couldn’t help but get a few selfies of myself behind this amazing backdrop, Tony offered to help be my photographer as I posed for him like a would-be model. It was all in good fun and I was having a great time.

“You should post some of these on your profile, they look great”, he expressed scrolling through the pics he just took.

“Yeah? let me see”, I replied hastily making my way over to him, I hunched myself close to Tony as we both admired the photos, “Wow, you know how to take a great photo, I should hire you to take more”, I teased, looking up at him with a flirtatious grin.

“Well taking photos of hot girls is a hobby of mine but I don’t do it for free, what would I get out of it?”, he fired back grinning smugly.

I held a finger to my upper lip and put on a show of myself thinking long and hard before coming up with an idea,” what if I let you take a few that wouldn’t be suitable for my social media?”, I proposed, letting my wild side shine through.

“interesting ... you might have to give me an example ... I just can’t commit that sort of time and effort without getting a better picture of what I’m getting”, he countered with, his dark eyes daring me to push past my limits.

Being competitive in nature I just had to show him I wasn’t kidding around, I backed myself towards the railing, stopping as the cold metal hit my tushy, I wriggled my arms free from the long sleeves of my dress, moving them up and out the top before peeling down the top half to expose my little pink, lace bra.

“I think I’m getting a good picture of what you’re offering Emma but I’m still not convinced”, Tony arrogantly said, his eyes feasting upon the sight of my tender flesh.

I simply nodded my understanding loving the impromptu roleplay, my hands reaching back to unclasp the bra letting it fall to the ground, my small B-cup breasts unveiled standing high and perky on my chest with just a hint of jiggle.

“that’s great but I think I’m going to need to see more, my time isn’t cheap young lady”, he let me know.