First one got deleted so I reposted. Bored during this hump day so here is another past, work related sexual encounter.
This story takes place a year before Covid. If you’ve read my other stories, this was after Rachel and I were no longer seeing each other and I had hit a bit of a dry spell. I finally graduated college and was working at a hospital-like facility where we had mentally ill clients that lived there full time. We had recently brought on a new therapist (we’ll call her Samantha) and I had never really paid her much attention while I was still involved with Rachel but during my dry spell, at some point she just started looking good. She was (in my opinion) the very image of a cougar. 49 year old Hispanic woman, librarian style glasses, hair pulled back professionally in a bun, light make up, a stern face, and a pantsuit type of woman. She didn’t smile often and was a little socially awkward. She spoke in very matter of fact tones with little emotion and had a very business attitude that said “get to the point” every time you spoke with her.
One day I happened to take a call from someone who asked for her. I took the name and message and decided to just walk down the hall from my office to hers, to deliver it. Once I informed her of the message, she asked me to step inside and close the door. She confessed that the man who called was her soon to be ex-husband and that she didn’t want to accept any calls from him and asked if there was a policy that prevented other staff from sharing info about her with him if he called. I told her there was and I would remind the staff of that policy at the next staff meeting. She thanked me and I said I was just down the hall if she ever needed to talk.
Over time she took me up on that and our interactions got more and more flirty until one day I flirted with her in front of an oblivious client. I could tell right away that my brazenness piqued her interest and after her last meeting, I went into her office. I decided to be straight forward since she had a very pragmatic personality and basically said I noticed we were both at a point where work was interfering in our personal lives and it might be beneficial for us both to spend some time together outside of the office, or even in the office if she felt so compelled to. She turned red, and for a minute I thought I had gone too far and she was about to go off on me. Instead she stared at me for a few seconds, before saying, “let’s have a drink first and see what happens.”
As impressed as I was by my own boldness and this outcome, nothing happened for another couple of months. She insisted that we wait for her divorce to finalize because she didn’t want her ex’s lawyers to have a reason to deny her anything in a settlement. I understood but the next couple months were agonizing, since we continued flirting but nothing more.
Finally after 2 months of waiting, she texted me that her divorce was finalized. I couldn’t wait so I sent her email request for a meeting and labeled it to look legit. This blocked her schedule for the next hour after she accepted. I went down the hall to her office, and walked right in, closing the door behind me. I walked up behind her and grabbed her chest with both hands and told her I couldn’t wait til later, I wanted her then and there. She jumped and said, “are you crazy? Absolutely not I’m not going to have sex in my office.” I was already trying to unbutton her blouse and I told her “fine then pull your tits out and get on your knees.” I took some pillows from the couch in her office and put them on the floor by her desk (because I’m a gentleman) and removed my shirt.
———————-Action here———————————
She stared at me shirtless before saying, “I’m not going to suck your dick. I have TMJ and not only is it painful but I don’t think I could even keep my mouth open that long.” At this point I needed anything so I said “fine whatever just come here.” She looked at me suspiciously but unbuttoned her blouse and got on her knees. I snapped her bra off and FINALLY got to see her huge tits. They were definitely D’s which looked good on her skinny frame. They were perkier than I thought they would be for her age but honestly she had gorgeous tits. She had an attractive body that you could tell she had been beyond hot when she was young but was starting to show some age.The sight of her on her knees with her glasses, hair bun and stern facial expression coupled with her large tits being out already had me hard. I told her “Damn you look good. You’re even sexier than I thought you’d be.” She turned red but smiled and pulled the top of her skirt up to cover her stomach as much as she could. I think she was shy about her stretch marks but honestly she looked good.
I dropped my pants and pulled my dick out. I told her I was going to tit fuck her and she frowned and said, “you’re going to what?” I told her to push her tits together, and when she did I slid between them and moved back and forth. She finally smiled and said, “oh this is new for me but I like it.” Feeling bold I pushed myself close to her mouth and she gave it a kiss and took the tip in real quick before pulling back and saying “no sorry, I can’t. Jaw already feels tender.” I was frustrated but before I could say anything her office phone rang. She froze and looked a little panicked so I nodded and told her to answer it. She let go of her tits and reached over to hit a button, answering the phone on speaker mode.
Her boss’ voice came over and asked her about work stuff but I still had my mind on her. When her boss began asking her work questions she stood up and sat back in her desk chair, still naked from the waist up and was business again. I didn’t want to lose my opportunity so I walked up behind her and slid my hand up her skirt, fingering her while she talked. Her eyes closed briefly but she was able to control her voice as she spoke over the phone. I felt her body tense and she said she was in a meeting regarding one of her clients and asked if she could call him back after. They hung up the phone and almost immediately she grabbed my wrist with one hand and covered her mouth with her other hand as she moaned softly into it. Her breath was heavy as she orgasmed but I continued rubbing.
I rubbed her clit for a few more seconds before I leaned in close and told her “get back on your knees.” She looked at me very sternly but returned to a kneeling position by her desk and put her tits together again. I slid between them and was so horny that I’m sorry to say it didn’t take much from there. I thrusted back and forth between her tits and when I felt myself ready to cum I told her to open her mouth. She opened it slightly but not enough for me to try pushing myself in there, which was fine because I exploded across her chest and into her mouth. She recoiled with surprised but her mouth stayed open for a few more seconds and when she closed it, she looked up at me.
She retained a very stern look but had my cum splashed across her chest as well as dripping from her lips where my shot landed. She licked her lips and said “it’s a bit salty but still tastes a lot better than my ex husband.” I laughed and told her she looked incredibly sexy in that moment and she gave me a brief smile before saying, “I’m going to stand up now, not all of us are still in our twenties you know.” I rolled my eyes and helped her up. I told her I wanted her to leave my cum on her chest for the rest of the day and she kind of glared at me before saying, “fine. I supposed it is good for the skin after all.” We both got dressed and she fixed her make up and double checked her bun before I walked out of her office.
*Unfortunately that was my one and only sexual encounter with Samantha. Out of all my stories this is one is the most frustrating to write because it’s one of my most “what could’ve been” moments. She continued to play coy and when I got tired of waiting around for her to put out, I moved onto another coworker. When Samantha found out about me and this other coworker, she was livid and things got very tense and awkward for awhile. I never got another shot with her and we lost touch soon after.
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from Gonewild Stories https://www.reddit.com/r/gonewildstories/comments/mhhxgc/the_time_i_24m_tit_fucked_a_therapist_49f_mf/
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