I had just gotten my first real job in the city and was excited with all that came with it, after having done mostly labor jobs until that point. I had my little cubicle and was finding my way fairly well. I had to go through various trainings as part of the onboarding process, and part of that was an IT training to go over our systems.
The company I worked for has offices in various locations, and the IT training was scheduled to be done remotely, as the woman who was to train me, Karen, worked in an office a few states over. Karen called me and remotely took control of my computer as the training started. We didn’t see each other, so it wasn’t a flirting type back and forth we had, but she was friendly and funny and made a decent time out of what was a boring training session.
At the end of the training she mentioned that she periodically travels to the various office locations to help roll out new programs and that she would introduce herself when she came to town. A couple months go by and as I was making my way back to my desk from the bathroom, I passed by a woman I didn’t recognize. She flashed a smile that I returned as we walked past each other. She seemed to be 45 or so and she had blonde hair, a little shorter than shoulder length in what seemed to me like a typical “mom” haircut. I wouldn’t say she was gorgeous but she was cute and of course I noticed she had a nice rack.
Not much longer after I’d sat back down at my desk, I received a message on our work’s internal messaging system from Karen, “Hi! I am in your office today and I think I may have just walked by you.” I responded, “Yes I think that was me! I didn’t realize you were in our office today.” We went back and forth messaging for a while. It was all friendly and innocent, but I assumed there must be a mutual attraction as we ended up chatting back and forth throughout the day.
The following day came and a couple hours in I receive another message from Karen: “Hey, I’m in your office again today. If you have a minute you should stop by my office so I can show you something I meant to go over in your training.” After a few minutes I walked over to her office and was greeted by her friendly smile. She told me I could come around behind her desk so I could watch her screen as she pulled up a program. I walked around her desk and stood over her behind her chair as she sat.
Whatever she was showing me didn’t seem very important which made me think she was just looking for an excuse to see me, which was fine by me. She was wearing a shirt with just a bit of cleavage and I took full advantage of the view as I stood over her from behind. I desperately wanted to slide my hands down her shirt and grab a handful of her wonderful breasts. I stayed and chatted for 10 minutes or so before making my way back to my desk. I was all hott and bothered to say the least.
A little later that day I see another message pop upon my computer from Karen and I decided to send her my phone number. I sat nervously at my desk, I had the strong sense she was into me but once I sent her my number I began to wonder if I made a mistake, until minutes later I receive a text from an unknown number: “Hi! you read my mind. I wanted to transition this over to text messages but wasn’t sure how to go about it.” I told her I was so relieved she felt that way as I wasn’t sure if I crossed a line. “are you kidding me, you are so cute! I actually can’t believe you want to text with me.” I responded and told her that it took everything in me not to make a move on her while in her office.
That’s how it all started. We continued texting for weeks. Turns out she was going through a rough divorce with her husband who she had a couple kids with. They’d been together since they were young and grew apart over time. Her sex life was basically non-existent for a couple years at this point. We slowly started getting naughtier with out texts. She was new to “sexting” and sharing pics, but I think she was excited to get some passion back in her life. Things got really steamy and we were both very eager for her next visit to my office.
The company put her up in a very nice hotel when she traveled, and the plan was for me to meet her at the hotel next time she was in town. Finally, she was back in town for a couple nights and it was time to put the plan into action. I could hardly contain myself seeing her in the office that day. I had to work a bit later than she did, so she got to the hotel and got situated and starting drinking wine while she waited for me to get out and meet her.
She quickly opened the door as I knocked and let me in. She was wearing the bathrobe from the hotel and fuzzy slippers. I put my bag down and she flung herself into my arms and we shared a soft sensual kiss. I tasted the red wine on her lips and tongue as made out just inside the entryway. I unbuttoned by dress shirt and she helped pull my undershirt over my head as she slid her hands down my bare chest and abs. She knew I planned on showering once I got to her room, so she advised me to hurry and shower as she slipped off her bathrobe and quickly got into bed and pulled a soft black mink throw blanket over her naked body.
I took a quick shower and dried off quickly. I walked out of the bathroom with a towel tied around my waste which revealed the bulge of my semi hard dick. She opened up the black mink blanket to invite me in as I slid off my towel and joined her on the bed. I went in to kiss her as I laid next to her, our naked bodies nestled against one another. I felt her big natural tits smother against my chest as we kissed and pulled closer. I began sucking her big right tit as I slid my right hand down to rub on her inner thigh. I wanted to really work her up before touching her, but I pretty quickly felt a trickle of wetness running down her thigh and I could not resist.
I slid a finger insider her already very wet pussy as she moaned deeply. I worked a second finger in as she pulled my head up to give me a very sloppy kiss before biting down on my lower lip as she stroked my hard cock. After a couple minutes I pulled away and climbed on top of her. I slowly made my way down her body, moving from her lips, to her tits, and slowly down to her wet pussy. I knew she loved oral and hadn’t received it in a long time, so I was determined to please her. Following her body language and cues, I really got her going and she started grinding her hips as her stomach was pulsing. I reached up and firmly grabbed her tits as she essentially fucked my face.
She said it was her turn to taste me and guided me up over her as she lay flat, head supported by pillows. She took my throbbing shaft right into her mouth and grabbed my ass cheeks, pulling me closer. I moved her hair out of her face as I gently thrusted into her mouth. After a few minutes she asked if she could climb on top. We had already discussed some of the particulars as we had texted a lot leading up to this, and knew that we didn’t plan on using a condom. I watched her as she climbed over me and slowly slid down my shift, her big natural tits dangling in front of my face. Her juices felt so sexy pouring down my hard cock.
She kept riding me and I think she came a couple times. She could tell I was trying not to cum at times as I wanted her to get off first, so she finally told me it was my turn. Again, we had previously discussed some of the particulars, and I knew if it all went well, she wanted to feel my warm cum shoot inside of her. I told her I wanted to finish on top so she spun around and laid flat at the end of the bed on top of the mink throw.
I grabbed her big tits and start thrusting getting closer and closer to climax. She gave me another sloppy kiss and as she firmly grabbed my ass cheeks I could no longer hold back. I kept pumping as I came hard, feeling my cock pulsing with each shot. Her hands remained firmly on my ass cheeks as I slowly stopped thrusting and rested inside of her cum-filled pussy. I pulled out and watched my cum trickle out of her.
Source: reddit.com/r/gonewildstories/comments/10ay1j4/the_visiting_it_trainer_f_invited_me_m_back_to
Your description of her is awesome!