When I was 21 I started working at a company doing medical billing. My mom has worked at this company for a long, long time and this is how I got the job. I had worked some odd jobs there over the years, but this was my first time being employed full-time. In previous stints at this place, when I was in High School and college, I would be working with other individuals my age. There were two girls during this time that were very attractive. We generally worked in an unoccupied doctors office, or in the basement, and I always fantasized about fooling around in one of the offices with one of these beautiful girls. Unfortunately, that dream never came true.
When I was hired on full-time, I found myself – a 21 year old, fit young man – working in a department of all women. This time, however, there wasn’t an attractive one in the bunch. Given that it was a large employer, there were quite a few attractive doctors, nurses, receptionists, etc. working in the building, and I still fantasized about messing around with someone at work.
One of the women who caught my eye was a latina woman who happened to be about twice my age. At the time, I didn’t have any particular inclination toward cougars, or MILFs, but for some reason I was drawn to her. She wasn’t even my body type – she was a little thicker than women I was generally attracted to in the past. However, she was short, which I like, and with that thickness came some lovely curves in all the right places.
She probably had DD breasts, and her bottom was very plump, which I definitely appreciated. I think what attracted me to her the most was her general pleasantness, and joyous personality. Every time she passed me in the hallway she had a huge smile and always greeted me warmly.
That being said, we had never really had a conversation until one day I when sent her an email. The email was a thank you note for setting up a class on nutrition. I attended hoping to get some tips on staying fit, but I ended up getting much more than that from the class.
My thank you note was very brief, but it sparked a year long conversation. From that day on we exchanged messages on a near daily basis. We had no reason to interact with each other during the normal course of our jobs, so our communication was almost exclusively via email. She was married, and I had a girlfriend, so texting after work was out of the question for both of us.
Back to the note.
I can’t remember how, or why things took off from this note, but they did. I’ve always had a habit of being very flirtatious, but I’m not overbearing about it. I like to take my time and really test the waters. The first time I knew she was willing to flirt back was when I played a small joke on her.
One day I decided to make a fake discipline form and send it to her. I copied our companies letter head and made it look official. I wrote her a warning for spending too much time flirting with a co-worker and at the end for the consequence I wrote it would be at my discretion and signed my name. After finishing off the form, I printed it, and sent it through the interoffice mail. This made it appear even more official.
The next morning I received an email from her. She said she was so nervous reading the form, and thought she was going to be in HUGE trouble, until she saw the form was signed by me. Then, she asked me what her consequence was, and asked that I not be too “rough” on her. This caught my eye and honestly made my cock bulge. (It’s bulging now just thinking back to this time.) This is when I assumed I could turn up the flirting a little. I replied that I wouldn’t be too rough on her, but she was actually in “huge” trouble and ended with a ;)
After receiving this message from me, I think it occurred to her what was going on. When she had asked me not to be too “rough” on her, I now believe it was just a joke. You see, she was definitely the naive, and ditsy type. She hadn’t meant to be flirty, and it probably hadn’t occurred to her that someone half her age had taken an interest in her. That’s exactly what had happened, though. If she wasn’t aware before, she was now. Now we were both playing the same game.
She didn’t message me back for awhile, however, and I got nervous. I thought I read her wrong and had scared her away. I sent her a followup message and apologize for my previous comment, and said it was just a joke. I told her I had a bad habit of being a little flirty. She messaged me back almost immediately, and said she had been occupied with a coworker, otherwise she would have messaged me back sooner. She assured me I had nothing to apologize for, and told me to meet her in exam room 16 at 4:00pm – she’d be willing to accept her punishment at that time – and ended her message with a ;)
What. The. Fuck.
How the hell did this happen? I did not see that coming.
At. All.
I had never become instantly hard, and had a panic attack simultaneously. This was everything I had fantasized about happening at work. But also, it’s at work! What if I get caught. My mom works here, and everyone knows her. Could there be anything more embarrassing than getting caught fooling around with a receptionist twice your age at the place your mom works? But how could I NOT go?
Do I go to exam room 16, or do I play it safe, and message her to say I was just joking around?
After thinking about the potential consequences of this momentous decision for around ZERO seconds, I instantly messaged her back, “See you then. Don’t be late ;) ”
This was around 2pm. I couldn’t think about anything else for the next two hours. I had no idea what to expect, or how to handle this situation. I’d been with plenty of women before, but this was different.
She was twice my age. It was at work. There were so many coworkers and patients in the building at this time of day.
As the clock ticked closer to 4:00pm I started to get hard thinking about all the things that I wanted to happen, and wondering what might actually transpire in just a few minutes. Then my boss called me over. My cock couldn’t have been harder in that moment, and now my boss is standing right behind me, calling me into her office. I tucked it behind my belt and walked into her office.
As awkward as it was talking to my boss with a throbbing cock, I was even more concerned that I was going to miss my 4:00pm rendezvous. Fortunately my boss just wanted to ask if I could stay a little later this evening to finish up some work before the weekend. I looked over her shoulder and noticed her clock on her desk read 4:02pm. Fuck. I assured her it wouldn’t be a problem to stay late, and asked if I could excuse myself to the bathroom.
I hustled down the hallway to Exam Room 16. By now my boner was long gone, and I was a bit panicked that I missed my chance at fulfilling this fantasy I’d had for years. I slipped into Exam Room 16 and closed the door behind me. No one was in the room. I spent the next few minutes thinking I’d missed my opportunity. I certainly wasn’t turned on anymore.
Then, the handle moved. I was elated, and terrified at the same time. This could literally be anyone, There I was with my back against the wall. I chose to stand along the wall the door opened toward, so as the door opened I couldn’t see who was coming in, and they couldn’t see me.
Then, as the door closed, she was revealed to me. I think she was more surprised I was actually in the room than I was that she came. I began to speak quietly, and intended to say, “I was beginning to wonder if…” when she put her finger to my lip and shushed me. Her other hand reached for my cock as she removed her finger from my lips and pressed her lips against mine.
Clearly, she had been anticipating this moment, at least as much as I had been.
She kissed me passionately a few times before pulling back and looking me in the eyes. I can still recall her large dark eyes and mischievous smile. I must have had a look on my face, because she asked if I was ok. I assured her I was fine. I just couldn’t believe this was happening. She didn’t say anything in response.
She flashed me one of her smiles, just like she did when passing me in the hallway. I couldn’t help but wonder if she had this in mind for the last two years we’d be working together.
After flashing me a smile she began kissing me again while unbuckling my pants. She was having a hard time, so I offered some help. As soon as the belt was freed she popped my button and I slid my pants down to my knees. My cock, partially erect, hung waiting for her. She slid her hand up my thigh, sending a tingling sensation up my leg. Her finger tips slide along my groin and up the shaft of my cock. She gently kissed the tip of my cock. Her hand glided back down my shaft and cupped my balls as she slipped the head of my cock between her plump latina lips.
I let out a quiet moan. She looked up at at me and locked her eyes on me as she slid my throbbing cock to the back of her throat. As she pulled back, I gently placed my hands on the back of her head and started to rock my hips. She let me slowly slip my cock deeper, and deeper into her throat. I had never had my cock so deep into someone’s mouth before, and it seemed like she could’ve taken more.
Then, all of a sudden, she took my cock out of her mouth. I was so lost in what was happening. She stood up and asked if I was ok. I assured her that I was, and that this felt amazing. She apologized and said she had to get back to her desk.
She gave me a kiss on the cheek and slipped out the door.
I leaned back against the wall, in shock about what had just happened. I can’t believe I just got an amazing blowjob like this at work. Then it hit me. I’m standing here in Exam Room 16, with my pants still around my knees.
I slid them back up, tried to gather myself and went back to my desk. Fortunately, no one seemed to notice I had been gone for an extended period of time. For the rest of my time there I couldn’t help but wonder if this was ever going to happen again, or if she had left me like that because she felt guilty.
Do I message her now? Do I wait until tomorrow? Will there ever be another chance to finish where we left off?
Fortunately, I didn’t have to ponder those questions for long. When I arrived back at my desk I went to my email and saw a message from her. She apologized for leaving so abruptly, and assured me that she was nervous about being away from her desk for too long because she was working alone at the time. I responded by informing her that the written apology was appreciated, however, she would need to do better.
She took the hint, and replied asking “will there be consequences again?”
My cock began to bulge in my pants at the thought of her taking me in her mouth again. I told her there would definitely be additional consequences for her actions, and then tucked my hard cock behind my belt, got up, and went to the bathroom. I couldn’t resist jerking off in the bathroom to the thought of her finishing me in her mouth. I wanted to see the look on her face as the head of my cock pressed against the back of her throat and my cock throbbed while my thick cum shot into her throat. She seemed to have no problem taking 7 inches of cock down her throat, but could she take a load like that without choking? Or would she let it drip from her mouth onto the cleavage of her supple DD breasts? Only time would tell.
Finishing myself off in the bathroom was a disappointing end to an otherwise exhilarating day. I cleaned things up and returned to my desk again. I shared some exchanges with her again about her weekend, and wished her well. The next chapter of this story would have to wait until the following week, I hoped.
The next week was spent messaging each other constantly about our weekend, the nutrition class which had led to our paths crossing in the first place, and other mundane things. Mostly, we talked about our desire for each other.
Our encounter had lit a sexual spark in her that I believe had been dormant for a long time. Her marriage was stale, and she hadn’t been the subject of such intense sexual desires in quite some time. The idea of being craved by a man half her age was titillating. To me, the idea that this curvaceous, mature, Latina woman had spent the last two years desiring my cock, and was willing to devour it in secret at work was such a turn on.
It was harder than I imagined to make arrangements for a second meeting. It turns out a receptionist job is pretty important in a large doctors office, and they don’t have many opportunities to step away from their desk to suck cock. They do have plenty of time to exchange salacious messages, though. And we did plenty of it.
I enjoyed expressing my desires and fantasies to her, and she got off to listening to them. She would tell me how wet my fantasies made her while she read them at work, surrounded by her coworkers. I bought her some sexy lingerie and left it at her desk for her in a discrete package. She told me she would think of my cock when masturbating at home, and she craved it almost daily.
Finally, almost two weeks later, we were able to meet again in the Exam Room 16. This time she beat me to the room, and was ready for me. She had worn a button down white shirt, and there were very few buttons left to be undone when I quietly slipped into the room. This time she let me take the lead.
I gave her an approving smile, and dropped to my knees. I began unbuttoning her top and as her soft skin was revealed, I began to kiss her tummy and slide my tongue along her body, toward her large breasts. I cupped her breasts and massaged them as I stood up. She began stroking my cock through my khakis as I passionately kissed her plump red lips.
She slid my zipper down, pulled my cock out and began stroking it. I kissed my way down her neck and my tongue inched toward her breasts along the edge of her bra. I kissed between the large gap of her DD breasts, and pulled her bra down to reveal her tiny perky nipples. I cupper her breasts again and took her nipple into my mouth. I circled them with the tip of my tongue, nibbling gently and sucking gradually harder.
Then she dropped to her knees and began licking my balls while stroking my thick cock. It looked even bigger than usual in her small hands. Her tongue glided up and down the shaft of my cock as it began to throb in anticipation. Her tongue teased the head of my cock, caressed my shaft and massaged my balls. She placed her hands behind me and pulled my cock into her mouth as deep as she could. I placed my hand behind her head and began to fuck her throat. I fucked her as hard and fast as I could without making her gage and giving away our secret.
Eventually she pulled back a bit to get some air and then began stroking my cock with her hand while sucking me off. I began fucking her mouth again until I couldn’t hold back my cum anymore. I began to moan a little and I think she knew I couldn’t hold it back any longer. This caused her to start pushing my cock as deep down her throat as she could until she felt my cock begin to throb. She pulled it out and stroked vigorously, threw her head back and provided her huge tits as a pleasing target for my load. She continued stroking my cock until every drop of thick cum had dripped onto her tits and then sucked the little drop that was left on the tip of my cock.
Then she buttoned her shirt, and put on her blazer. She kissed me on the cheek again, and thanked me for a good time. I insisted I owed her the thanks and promised that next time I would return the favor.
We exchanged many sexually explicit messages after this encounter, I got one more blow job, but nothing further ever transpired. I left the company shortly after this. To this day I wish I could have returned the favor, but it was not to be. I’m just glad I got one hell of a story and 3 amazing blow jobs out of it!
I hope you enjoyed my story about Exam Room 16.
Source: reddit.com/r/gonewildstories/comments/izzgcp/mf_work_fantasy_cum_true_with_mature_latina_cougar
This was a fantastic read. Thanks for the story, and I’m glad you got to live your fantasy.