During the summer before my senior year, my Aunt Jo offered me to come stay with her in Pennsylvania because of a great job opportunity. She worked for a finance company and needed someone to work in the office. I decided I could not turn down the opportunity to make so much money, so I went. In late May, I flew across the country from my home in California to live with my divorced relative for a few months. My first day at work is when I met Tyler and we hit it off right away. After some casual flirting, we quickly advanced to becoming an item in less than a week.
During a late June evening, I was at Tyler's house and we were in his room hanging out on social media and playing video games before we started kissing. He was also 18 and like a typical boy that age, he was pressuring me to have sex. A friend of mine had gotten pregnant during our sophomore year and it had terrified me so much that I was really leery about the subject. Even with my reluctance, my own hormones were just as active and I was really curious about other types of sex outside of intercourse.
"Look what I got," smiled Tyler as he held up a packaged condom.
I sighed, "You know my rule."
"C'mon, we have been together a month now and I'm gettin blue balls over here," he whined.
I was wet from our make out session, so I offered, "Lock the door. I will...you know," as I made an open fist and moved it up and down to signal a hand job.
An excited Tyler, jumped up, locked the door and within ten seconds, had his pants laying on the bean bag chair while he laid on his back across his bed. He had a thin, smooth six inch cock leaking all over his belly. Seeing seminal fluid in real life for the first time was stimulating to me. I sat on the bed beside Tyler and jerked his cock while using that leakage as lubrication.
Sliding my hand up and down, I wanted reassured, "Am I doing it right? Does it feel good?"
He groaned, "Oh yea. Do it a little faster. Yes, just like that. I'm going to cum."
Upon request, I jerked faster when Tyler let out a large moan while shooting cum all over his stomach and the back of my hand. Tyler was satisfied as I looked around for something to wipe my hand off with. While watching it squirt out along with feeling it on my skin sent butterflies through my own stomach. It was sexual, different, and once again, exciting. Giving my first handjob inspired me to go back to Aunt Jo's and masturbate for over an hour. It also inspired me to jack Tyler off every single day for the next week. He wanted me to progress to the next step and suck him off but I still wasn't quite ready for that.
That Monday evening, Aunt Jo's company met several other financial firms at a local restaurant for a large dinner. I wanted to look as professional as I could, so I wore a matching pin striped business skirt with high heels loaned to me by my aunt. Following Jo's advice, I also put my long dirty blonde hair up to "convey a serious presence." Ideas, clients, vendors, business deals were all discussed as several dozen of the local business men and women ate, drank and enjoyed each other's company in a private reserved room. Having only been working a short time, I mostly just listened and tried to learn as much as possible.
While waiting in line at the bathroom, one of the business men from our room walked past me, stopped then held out his hand, "Hi, I'm John and you are very stunning."
I smiled, held out my hand and shook John's as I responded, "Thank you. I'm Brittni, Jo's niece. I'm working with her over the summer."
It was obvious John had been drinking when he said, "I mean it. You are very pretty." He pulled out his card and handed it to me while continuing, "Seriously, if you ever need anything and I mean anything, don't be afraid to contact me."
I laughed, "Sure thing John. I don't have a card but my email is in our online directory. It was nice meeting you."
The next day, bright and early at work, I noticed I had received an email from John. He was asking me to lunch in the lobby of a five star hotel located on the other side of town. It was sweet, but I didn't know the guy, he was much older than me, and I had a boyfriend. I respectfully declined as I told him that I needed to get to know him better.
He then continued to email me throughout the day so that I could "get to know him better," and he would ask me questions as well. For some reason, I could not stop responding. Maybe it was because he was an attractive older man that was built well. Maybe I was flattered. Maybe I was just curious.
I did find out he was 38 years old, was single and owned his own financial consulting business which explained why he was at the dinner. He also told me that he was a firefighter along with other personal information. The emails gradually turned from casual to more personal to sexual. I couldn't stop replying as I was quickly getting drawn into this stranger's life. He asked me for my cell number and my intrigue caused me to give it to him.
The first text I received from John was a picture of his cock and it was rock hard sticking straight in the air with the caption, "What do you think of this? It's 8 ½ inches of raw power," with a winking emoji after it.
I was blown away with his brashness but I was not angry. That cock looked huge to me. It was definitely something to show off with the massive thickness to go along with the length. The head was large and I could see all the veins bulging up the shaft even though the lighting was dull. I have to admit, I was aroused by the pic but I was also a little nervous. This was getting so real and I was still a virgin who only started whacking off my boyfriend a week earlier.
John continued to text me and I would respond. He begged for nudes and for some reason, I couldn't say no and later that evening I sent them via snapchat. I made sure to keep my face off the pictures in case they leaked out. I turned down his offer for lunch several times but he was very persistent. I finally agreed to meet him for lunch on Friday because Aunt Jo let me take a half days off on Fridays. He also requested that I wear the same pin striped business skirt and pumps that I had worn at the dinner when we met.
That evening, I was jacking Tyler off in my room when I couldn't help but fantasize that his dick was actually John's huge dong. I was making myself horny from the thought and when Tyler's cum flew up in the air and a glob landed on my arm, I almost orgasmed.
I had trouble sleeping that night and debated with myself if I had made the right decision on meeting John. What if he expects more? What if I can't say no? That dick of his did look amazing so I wrestled with my sanity all night.
When Friday arrived, I finished up at my desk around noon. Per John's request, I was wearing the skirt with the matching blazer. On the drive over to the hotel to meet John, I continued debating with myself with negative thoughts such as, "Brittni, this is how people end up on Dateline," and positive ones such as, "He is a respected businessman and a firefighter in the community." I also had to tell Tyler I was meeting a potential female business client that Aunt Jo requested I see.
