Average Guy finally hooks-up with secretary [MF]

Before I begin with this story, I just wanted to provide a brief update and say thank you to everyone who read my previous story. I never thought it would be so well received, so thank you for the support!

UPDATE: So, sadly, I do not have an update on my search to reconnect with Sara from the story. I was able to track her down through our mutual friend group and I even got her new number. Prior to messaging her, I found her on social media and I saw that she recently got married. She is as gorgeous as I remember and honestly not much changed about her.

However, after learning she was married, I gave up and decided to not even tempt myself. After going through a cheating divorce, I could never do that to another guy. So, Sara will always be the one that got away for me, lol!

Sorry everyone, I wish there was a happier ending to that story but the story below, in my mind, is just as wild, so enjoy!

So this story is recent and I am still wrapping my head around it so hopefully, yall will enjoy this.

So, a little back story before the good part, I own/run a part-time consulting business where I work with mid-level managers and executives on leadership. Nothing too crazy and not like super powerful people but I love it.

The business recently took off and it quickly became more than a part-time job for me. Not able to quit my full-time job, I figured the next best option was to hire a part-time assistant.

Not wanting to field applications, I hired an outside recruiter to find three applicants and I would interview the three and then hire the best candidate from there. I ended up with one male and two females. I won’t bore you with the details of the other two but the star of today’s story.

I had interviewed the other two candidates first and both were great and qualified but they did not have exactly what I was looking for. For the sake of this story, let us call her Kaitlyn. Not her real name of course.

Not having a real office space and still with covid going on, our first interview was over Zoom and as soon as she entered the call, I was immediately blown away by how gorgeous she was. After searching for a look-a-like, she looked very similar to Gemma Arterton. Shoulder-length dark hair to the one side, gorgeous green eyes with glasses, and just a natural beauty about her.

I did my best to remain professional and we finished the interview without any issues. She was not only pretty, but she was smart and funny, and you could tell she was goal-oriented. To be honest, over-qualified to work for me but she was between undergrad and grad school and she wanted a part-time job in the consulting world that paid well.

No one come after me for what about I am about to stay, but oh well. After the interviews, I decided to hire one of the other candidates for the job despite Kaitlyn being the best person. I know I know, I know, I am a crappy person. I just was afraid I could not remain professional working alone with her (spoiler alert, I was right). So, I hired the male applicant instead.

After a week or so working for me, the young kid decided he wanted to travel and this part-time job was in the way of that…great… wasted the time. So, I called the other female applicant and she already had found another job.

So, lastly, I called Kaitlyn, thinking that she too already had found another job but I was desperate for someone at this point. She picked up almost right away and she happily accepted the job but she needed a week before could start. Too easy.

Fast-Forward about two months or so, everything is going smoothly, Kaitlyn handles my consulting schedule, booking new clients, follow-ups with old clients, you know…typical work stuff. The business again is running smoothly thanks to her and is continually growing.

Over the course of her first three months, we spent countless hours together at coffee shops and over the phone but we always only talked about work. She did not ask about my personal life and I did not ask about hers. She was great at her job and I truly valued her.

So, after the first three months, I decided to give her a raise and a small bonus in the form of a gift card to one of the fancier restaurants in the city to show my appreciation and thanks for all her hard work. Again, I worried about crossing those lines, so I figured a gift card was the perfect way to do just that. If she had a partner, they could go and have a good time.

So, I invite Kaitlyn to our usual meeting spot and quickly get the business things out of the way and share with her the raise and bonus. She was so genuinely happy and excited, it made me happy! After our meeting was over, we got up to leave, and she hugged me and said thank you. It was the first time we had ever physically embraced each other than a handshake.

I awkwardly hug her back and for the first time, I felt how firm and amazing her body was. I awkwardly tell her I have to go and we go on our separate ways.

Fast forward about two weeks, we meet again to discuss a bigger presentation that I will be doing and once we are done with it, she excitedly tells me that she is finally getting around to using that gift card I had gotten her this Saturday.

She apologizes almost as soon as she said it, “I’m sorry, I know we don’t talk about personal stuff, I just wanted you to know!” I assured her it was ok and that I am happy, and told her to have fun! We finished the semi-awkward small talk and left.

Two days later, we meet again in the evening and this time, as soon as she walked in, you could tell that she had been crying and was upset. I tried to ignore it but you could tell she was not ok. So, I stopped talking about work and broke my no personal talk rule and asked her what was wrong.

She said that she had found out that her boyfriend was cheating on her and for the first time, she poured out her whole life to me without me even really saying a word. After she collected herself, she apologized repeatedly and kept saying how embarrassed she was. So, I decided to share with her about my ex-wife cheating on me while I was deployed and I ensured her that if I could move past it, a beautiful young girl like her would be able to as well.

People talk about moments you know that you into the person or that you crossed that platonic line, well I will never forget this one. She lifted her head and in the most sincere and sweet voice said “you think so?” There are ugly criers in this world, but I do not know how this woman looked so amazing despite crying so much. Her gorgeous green eyes penetrated my soul and I knew at that moment, it was over for me.

About a month or so goes by and at this point, the business has grown enough and I started renting a small office space for the business which meant no more coffee shops or libraries. We are preparing for another big presentation which means staying late after my full-time job to work on it.

After about 10 pm, I told Kaitlyn to go home, I would be staying to finish but she did not need to stay. She asked if I was sure and then left for the evening. About an hour or so later, I received a message from Kaitlyn asking me if I was still working in the office and if so she was going to stopover.

I told her, she did not have to but I never got a response, but sure enough, about twenty minutes later she walked into the office. But she was not wearing normal clothes, she looked like she just come from a date. She was wearing a tight black dress that showed off her amazing figure, black heels, her glasses, and her hair pulled up in a black clip…she looked incredible. I mean breath-taking.

She caught me completely off guard and I could not help but check her out. She is about 5’5 5’6, petite/athletic frame from working out, amazing ass, and average to small tits, but they are firm and she walks with the confidence of knowing she is gorgeous. I always knew that she was gorgeous but seeing her in these clothes left me speechless.

As calmly as I could, I asked her why she was all dressed up and if she forgot something. She replied no and that she had been on a date but it did not end well and she ended up ditching him. I could not help but laugh and she laughed as well.

She then said to me, “is there is something wrong with me? Like how hard is it to find a guy? Am I not attractive? Am I boring?” She went on complaining about guys and dating and I just sat there listening to her, completely lost in her beauty and admiring her dress, her curves, my god she was gorgeous…and then out of nowhere, she stopped mid-sentence, and said, “are you single? “I bet you aren’t single.”

I laughed at her abrupt question trying to defuse the tension but I just said, “yeah, im single, im just too busy to date right now.”

Her green eyes cutting right into me, “that’s a lame excuse, you need to get out there.” I had tried for so many months to not cross that line with Kaitlyn, to remain professional, but here I was with this insanely gorgeous young woman sitting in my office, I just said fuck it, I am going for it.

I responded in the most flirtatious and direct way I could muster, “oh yeah, what do you recommend I do then?” She very confidently responds with “me…”

I have to pause here before the good part after reading everyone’s comments last time, I have no idea how I get so lucky or what I do that allows me these moments. But damn do they make me feel good.

She then stands up and walks over to me behind the desk, “what is it going to be boss?”

I stood up and embraced her and we started making out right there in the office and my god… she was incredible and I could myself already getting hard in my trousers, after what felt like minutes but was probably only 30 seconds or so, She pushed me back into my office chair and she dropped to her knees, rubbing my cock with her hand.

She then looked up at me and maintained eye contact the whole time as she undid my belt and I lifted my ass as she pulled my pants down. As she did my cock sprang out and she began stroking my cock until I was completely rock hard.

She then took her tongue and licked from my balls to my head slowly and softly before taking my head into her mouth. There is a sub on Reddit called dicksuckinglips and my god did she have the most perfect dsl I have ever seen.

As soon as she took my head into her mouth, I rolled my head back and closed my eyes in pure pleasure as she masterfully sucked my cock my office. After a few minutes, I could feel myself getting close to cumming and I grabbed a fistful of hair and pulled her head off my cock and she looked at me with sincere disappointment and she begin slowly stroking my cock.

I told her I was getting close and asked if she was ready and she shook her head no… I begin to panic like I did something wrong but she said “I want to taste your cum, please, I need it.” I wanted to fuck her, I needed to feel her… but how could I say no to that??

So, I grabbed her hair again and said “are you going to be a good girl and make me cum?” She gave me a smile and said “yes sir” and immediately went to take my cock back in her mouth but I held her head back, making her beg for it… “please, please let me suck it.” I released her hair and she went back to work.

I soon felt myself getting close to exploding and I grabbed her hair again and slowly pulled her mouth off cock, for anyone who read my previous story, I have a thing for giving girls facials and I needed to paint Kaitlyn’s gorgeous face, so while holding her head, I said, I am going to cum on your face, ok?” she eagerly nodded.

She began stroking my cock and she opened her mouth and stuck out her tongue in anticipation of my cum right as I was about to cum, she said my magical words, please cum on my fac…” and before she could finish my cock explode a rope across her cheek and then another on the tongue and another on her lips.

She did her best to swallow the cum but I could quickly tell she was not the biggest fan of the cum on her face, so I stood up and found a napkin to help wipe my cum off her face and she giggled and I apologized.

She promised it was ok and asked me how it was… I still was speechless and the look of pleasure on my face was good enough for her. We sat there in silence for a couple of minutes just looking at one another like what did we just do? And then she broke the silence by saying “your place?” I laughed and said let’s go…

Part 2 to follow if anyone is actually interested!

Source: reddit.com/r/gonewildstories/comments/tut6ec/average_guy_finally_hooksup_with_secretary_mf