Confession Mentor Fucks Mentee

My name is Taryn. I'm 21, a size 00 blonde with long hair at 5 foot 4. As you're imagining, I'm tiny. My upbringing was upper middle class in the suburbs of an affluent city. I've always been a book-worm and never really fascinated with anything sexual. I do have a sister, Raena, who is definitely more on the risqué side (more on her in a future chapter as she'll end up servicing my mentor too) but I'm certainly more reserved.

Many years ago, I got my first break right out of school at a large tech company serving as an intern. Truth be told, I think it was a combination of being at the right place and at the right time because I am certainly not someone who knows a lot about technology. Granted, it was in marketing. The guy who hired me was also the guy who was doing the job so I figured that since he chose me then he probably knows that I'd be a good fit for the job. My upbringing to this point did not really prepare me for this role but I figure I'd do my 8 months, learn from it and see what comes of it. I was 21 when I joined that company and, candidly, was still a virgin. It's not for any ulterior motive other than the fact that life was busy in University and it's not like I was one of 'those' girls in high school. The most crazy thing I did in life up to that point was being a cheerleader...

Anyhow, shortly after my internship began, the person who I was hired by and as such replaced, got hired full time by the same company and a very long story short, he became my mentor. He was super friendly, approachable, and definitely smart. He was always there when I needed him and he sort of became like a big brother over the upcoming months. He was 28, Asian, and was unhappily married. I think it was more of a combination of him trying to adult sooner rather than later and he made a number of poor decisions while his career was taking off beyond his wildest imaginations. I think, if anything, I slowly fell for him as opposed to his looks and really respected his style of work. He gave back to many of my colleagues and was always there to try to help others. If anything, I very much admired his success and his demeanour.

Like any good story, you've probably figured out the plot twist. I mean, this guy was married and I was the intern. I'll never forget one day he had sent me this article from HBR that he read which he thought was a good source of truth. The article talked about how a woman should handle herself at work and how she should dress (no panty lines, no bra lines). I'm still not sure, to this day, why he sent that to me. I mean, from that day on I wear thongs underneath my skirts/dresses because I was guilty of visible panty lines. Was that him sexually interested in me? Maybe.

One day, after a very very long day for both of us at work (we were in the middle of launching a new product), we headed to the cafeteria downstairs just to grab a free soda and to grab a few chips to snack on before heading home. We must have lost track of time because it was probably around 8pm and though the cafeteria was open concept, there was no one left in the building (outside of security). We talked about a number of typical mentor-mentee topics but things started to get personal as he opened up about his frustration with his marriage. He was obviously escaping life by working hard and so on this very interesting evening, I did what he did to me many times which was to be an active listener, and nothing more.

We were situated in a booth type arrangement in the caf and one thing led to another and I could tell he got really sad so I ended up sitting next to him and I put my arms around him. Everything to this point was 'professional' but then I did something I didn't expect. I kissed him on the cheeks. To this day, I honestly do not know what made me do that.

I also don't know what made me say that I did at that point, which was "Vincent -- you're a good man, a wonderful mentor, and you too deserve happiness. I've fallen for you very heavily. I talk about you all the time at home and I'm so proud of everything I've done here. Here, come with me". Now, at this time, he was beyond startled, speechless, and I led him to one of the private bathrooms and locked the door behind us. It was at that point that I revealed to Vincent that I was a virgin. It wasn't shortly thereafter that I realized Vincent must have had a thing for me.

I was wearing a business appropriate blouse and skirt, and he had a suit on. I went for him, and I went for him hard. I took off his jacket, threw it on the vanity, put one finger to his mouth, and went on my knees. To be honest, I had no idea what to do what I was about to do, but I undid his belt, unzipped his pants, and pulled them down. I was so taken aback by his really large bulge hiding behind his Calvin Klein black hip briefs. I smelled (what I later learned to be dry cum) something that smelled like chlorine and I was a bitch in heat. I could feel my thong soaked through and through and immediately pulled down his brief and licked his cock up and down.

The sight of my first cock, and the smell of dried cum on his cock was so intoxicating. He had a nicely trimmed, thick, 6.5" cock and though I had watched porn every now and then, well, I was still unprepared to handle him. I did as best as I could and choked and gagged along the way. I did my very best to please him. I licked his shaft, gagged on his cock, licked his ball sack, and went feverishly while begging him for his cum. His initial reaction was very stiff (well, I mean his demeanour and not just his cock) which was clearly because he was in shock but as the minutes passed, he started getting aggressive with me. He'd hold the back of head while thrusting his cock into my throat. At this point, I was actually pretty proud of what seemed to be a lack of a real gag reflex. He called me his "good little girl" a few times and I instantly called him my master. It wasn't long until I could tell he was ready to cum and like a good little girl I begged him to cum in my mouth so I could swallow all of his "alpha seed". That was enough to send him over the edge and there he was ramming my head all the way down his cock as he shot load after load into my mouth. The taste was, frankly, overwhelming but I needed him so badly that I swallowed all of it.

So there he was, and there I was: two sexually charged animals in an office complex bathroom completely spent. I had lost my oral virginity, he had cheated on his wife (orally, not that anyone cares). I was dishevelled, and his hard cock was starting to get flaccid again. The next few minutes felt like a lifetime as we were both trying to collect ourselves. It's still quite a bit of a blur but over the next half hour things were a bit awkward. I asked to keep his hip briefs (no idea why I did this) so I could be close to him in an exchange to drive me home (which he did). If you haven't figured out that this is a confession versus a fantasy, this should be a give away. Like, this is just a strange plot twist, and again, no clue why I did that. Over the next few days, we mostly kept to ourselves but boy did I finger myself a ton while smelling (and licking) his cum filled briefs. It honestly took a few days for me to even think about how to even go back to work but time eventually passed and we were both back at the office.

I was expecting a period of insane awkwardness but sure enough I ran into him and he pulled me aside. He said to me "Taryn, I want you, and I need you. Will you be my good girl?"

Unsurprising to anyone, the answer to his question was "yes, master". Within a matter of minutes, I held his hand *at work* (which people knew he was married) and we walked across the street and checked into a hotel. This time, though, it was he who a finger to his mouth and summoned me not to say a single word. We were dressed similarly to the night I sucked him off because, well, business professional attire is always more of the same.

I don't know if he remembered that I told him I was a virgin (honestly though, what guy would forget that), but the reason I'm sharing that now is because he was pretty rough with me. Within a matter of what felt like seconds, I was in my bra and thong, and he was in his black Calvin Klein briefs again. He threw me to the floor where I pulled off his briefs again and started sucking him off. He was as big as I remembered him from that first night. I struggled as I did last time and after a few minutes of doing the best job I could, he got me to get up, threw me onto the bed and made *me* take off my thong and bra. Here's the thing I want you, as the reader to remember.

Remember my size, height, and now my weight (100lbs). I'm tiny, and he was probably around 6 feet, 130lbs. Think this through, I mean, I look young and since he was in his 30s, I wonder if there was an age gap delta that really turned him on. Most girls my age would really want their first time to involve love making and my sister and friends all lost their v-cards this way. Guys would be super gentle with them while fumbling around but this case was different. This was an unsatisfied married male in a long term relationship that sucked. He had no interest in pleasing me (not that I wanted anything more than to please him anyway) and so he was rough with me. He climbed into bed, made me take off his black CK hip briefs, wet his cock with my mouth, and then told me to climb on top. I later learned that his favorite position was this and his only care during sex is his pleasure. I loved that about him then, as I do now.

Vincent was rock hard and dripping pre cum and there in the middle of a hotel across the street from work, I lined up his cock to my super duper tight pussy, and I felt his arms bring me close to his chest as his hands grabbed both my hips on one side and my butt on the other. Just like that, he thrust himself in me and incredibly hard ripping through my hymen and converting me from a virgin to a 21 year old fucking my mentor who just so happened to be cheating on his wife. I don't think neither he nor I cared though.

I've only experienced one deflowering, but I had never imagined it would be with 1) him 2) at work 3) with a married man 4) done so incredibly rough. I will give him credit due where it's due though. It only hurt for a very brief moment (though sharp). I loved the fact that my mentor who I had deeply fallen emotionally for had his thick and long married cock inside of me and that I was bringing him the pleasure he so desperately wanted in his marriage. I squirmed and squealed like a bitch in heat while I recently thanked my master again and again for using me.

Vincent just went hard and fast throughout all of it and we remained in that one position for all of it. I was so turned onto the fact that this guy was just using me like a piece of meat with no regard to my pleasure. That level of alpha-ness actually caused me to submit to him even further. Vincent kept on pumping and pumping in me and I think at some point I was wondering what I should say to let him know where he should cum because while I was on birth control, we literally jumped into bed moments ago and didn't even talk about that. As my mind was processing how to bring things up (and in between the three or four orgasms I had), Vincent pulled me very close to him, grabbed my ass as hard as he could, and filled my womb with cum. He.didn't.even.ask.

After things sort of came back down to Earth, he gave me a hug while his cock was still in my pussy. He was starting to get soft when he whispered to me: "Taryn, you do your best to keep my cum in you all day. Now get off of me, suck me clean, put my CK hip briefs back on and it's time to get back to work". So, I did just that. We didn't cuddle, we barely talked, and in a blur of a moment later, we were both back at work in the same conference room in a meeting. His cum was dripping into my thong, his wedding band was still on his left hand, and I was left wondering what the fuck just happened. Logic aside though, I was in fucking heaven.

Vincent - if you're reading this, I miss you. Thank you for taking my virginity and I wanted you to know I still sniff and lick your CK hip briefs. It gets me off often.