[MF] The Mature Assistant

Recent lurker but it’s time for me to contribute with my first reddit ever post. I apologized in advance for the vagueness and length.

This is very true and was about 2 years ago. I was 26 and just getting settled in my new job. In the office we had a vacant desk yet to be filled, my assistant and the boss. It was positioned in a way that if you wanted to see the boss, you have to come through either me or my assistant. It usually takes a while for me to be completely comfortable with a new staff, I normally hold back some of my personality just to gauge the environment such as what jokes I can get away with. Which leads to my assistant.

She was 39, two kids and have been in the business for 19 years. She had an extremely fit body which gave her a much younger appearance. Whenever she got carded, she would always get a double take because she looked barely 30 if that. She was soft toned, reserved and seem to be only interested in supporting her kids and working out. Although she had an incredible figure, she was not my type. Also in my line of work, that is one of the few things you do NOT do. You never date or appear to date anyone you are directly over. It’s never allowed and it will get you fired. Do to this fact, I have a strong sexual barrier for coworkers. It took a while to be comfortable having small talks with her because it seemed to be a wall between us.

As time went along, maybe 2 months, the mood got much lighter. We worked in the same room, did a lot of the outside work functions and lunches so it came naturally. We started casual office chats. It was mostly about interests, personalities and preferences. She soon got hints of me being a complete nerd because I liked sciency stuff, programming and such. Even though she despised everything I liked, she seemed to like men who were nerds. She told me the guy she divorced was one which was surprising because she was a gym buff (I guess opposites attract?). At this point, I knew we could be good friends and just enjoy ourselves within the restrictions of work policy.

Not too long after that, she started the probing phase. I’ve dated much in the past, not in the recent days but I know when a girl is interested. Once she started asking about my last serious relationship, what kind of girl I like and such, I knew that there was a possibility she might think I am attractive. More concerned about not losing my job, I would never give a straight answer, or try to change the subject. Again she was not might type, and my barrier held strong to prevent creating that high school crush environment.

I would say close to month 4, it became more apparent that she started to become interested in me. She became much more comfortable calling me cute and complimenting me. The innocent questions soon became more sexual, like “Do you think I am cute?” “What hand do you use to masturbate?” “Do you like tits or ass?” (She asked that a lot because she had the most amazing ass but was super self conscience over her breast after they ‘deflated’ from losing weight). Again, I would always try to avoid answering these questions but she was very persistent. No matter how much I would try, she would always get her way. At this point, I didn’t mind her having the fantasy in her head as much. My barrier held strong and I was really concerned about losing my job. The sexual tension was there but somewhat masked because people just did not think it could happen.

Now the turning point, she just got news she will be temporarily transferred out of state to another office in a few weeks. This devastated her. At the time, I didn’t know why it did because that’s what we do in our job. She was mad at the world for something so minor as being gone for a single month. As I thought it through, I realized what it may have been. There was also talk to move me up early. If I accepted, we would never see each other again. I didn’t think she was that invested but deep down I figured that was it.

The mood was bad for a couple of days then out of the blue, she says, “I want to see ‘the city.'” If she would have made this offer 2 months ago, I would have declined but because I knew we did not have much time and she has been feeling down, I obliged. She did all the planning and paid for most of it. I was just the driver, bag carrier and emotional support guy. She also insisted in staying the night and leaving the next day. Assuming I would get my own bed, I again just went along.

The night was average. We did the touristy things, sightseeing, went to a really good restaurant nothing out of the ordinary. The day was winding down so we made our way to the hotel. We got to our room, put the things we bought down and proceeded down stairs to the hotel bar. It was very localized with all sorts of local beer and wine. We probably spent 2 hours there trying out drinks and chatting. It got late and we were getting tired so we went up to call it a night.

I was a bit buzzed but a really good buzz. I am usually fearful of this because this weakened my barrier. When I entered the room again, I was shocked at how I missed the fact that our room was a single bed. I remember asking her, “Can I trust you to resist?” in a flirtatious way and her replying something like “I think you can or maybe not?”. My good buzz allowed me to process that without much concern or after thought of leading events.

We took turns taking showers, I went first. After she was done she asks, “Can you give me a back massage?” The words “liquid courage” never been so true because I didn’t put up much of a fight and accepted with my crippled barrier. She turned around and laid flat on the bed. She was wearing her bra and panties still but my god, I was able to gaze her body without fear of being caught. I never given a massage in my life but I tried. This was also the first time I really touched her intimately. I basically semi straddling her, supporting myself with my knees making slight contact with my butt with her legs. In hindsight, I think she wanted me to make a move then, like unhooking her bra or massage more than her back. I did think about but declined because I still had an ounce of my barrier left. When I finished, she said it was good massage but i’m sure she only said that to not ruin the mood.

The last straw was her returning the favor. She asked me, “Your turn, where do you want your massage?” I responded, “My shoulder please.” I said this because I legitimately needed one. We change positions to a semi cuddle position. I was lying flat wearing only my boxers and she was on her side facing me. She started very slow and sporadic. I think she just wanted to feel me up and forgot it was suppose to be a massage because she always complimented my muscular build. Then it became more melodic. Next thing I know it, she was roaming. She started to do my chest, then abs. She stayed on my abs for a bit while ever so slightly inching her way to my pelvic area. I was cleanly shaved so she had no problem getting every inch of that area.

Then the moment that pushed me over the edge. She kept inching lower and eventually brushed against my cock. I was already hard as a rock but it was pointed down to not show as much. She felt it, I felt it. It shattered what was left of my barrier and I began to respond to all her advances. Heavier breathing, touching her breast and butt. We stayed like that for maybe 10 minutes or so, her brushing against me and myself full on groping her. I can’t remember what cause her to briefly sit up but I made the final move. While she was looking away, I pulled my cock out the fly to let be free. Since I was lying down and fully erect, the weight of it made it rest across my pelvic area stopping on at my belly button. When she laid back down, she returned to abdominal massage and got a quick surprise. She looked at me, smiled and asked, “How did that get out?” and grabbed it. She gave it maybe 10 long and deep strokes before she made her own move. She slid down the bed to position herself just right and swallowed the tip. At this moment, I can feel all the sexual tension just explode in pleasure as the woman, the assistant who sat across my desk was performing oral sex on me. That moment was one of the best moments of my sexual life and one for the spank bank.

The blowjob lasted around 7 minutes or so before I started to come to my senses. I didn’t want the night to end with just a blowjob because I wouldn’t be able to last much longer. I also need to return the favor. I slowly pushed her had away and moved towards the end up the bed to eat her out. Let me tell you, I always returned the favor but I never found much pleasure in performing. This was an one off. She was cleanly shaved (obvious had this planned out) and had such a clean vagina (I had bad experiences so this was a plus for me). I enjoyed every minute of it, hearing her moan for the first time, seeing the reserved woman squirm in pleasure and the anticipation of world ending sex that was about to happen.

After about 10 minutes of that, I was ready, I grabbed a condom and went in missionary. During the first stroke, my mind was racing. I was thinking about how wrong this was. The decisions that led me to this point, the age difference, the possibility of losing my job, being publicly embarrassed, even picturing myself with a kid in 9 months. All that did was further intensified the sensation of penetration. I don’t know, maybe I have a fetish for guilty pleasure but I was in an euphoria of sexual gratification. I’m not usually a porn star but that night, we had to have gone at for about 45 minutes. My first orgasm happened at around 12-15 minute mark. I have an extremely small refractory period and was hard again before I finished cleaning myself off after removing the condom. She briefly blew me again and I went to town. The second time is always takes much longer for me to climax to the point where I have to take small breaks because I physically get tired. This night, I powered through because it felt too good.

The next morning, we woke up and it was a weird mood. We didn’t talk about it but she was obviously treating me like a makeshift boyfriend. Cuddling in bed before washing up. Walking around half naked and being touchy. We got dressed and went out for breakfast. We both worked out often in the morning so we were up well before checkout time and back in our rooms with a couple hours to spare. Then I said to myself “I’ll break ice” and asked, “Did you like last night?”. “Yes” she answered. “What do you want to do now?” I asked. She responded, “I don’t know”. Still being horny from yesterday I just went for it and asked, “Do you want to continue from last night?” I guess she was too flustered about the whole situation, she only responded by nodding her head. We were at it again with mind blowing sex. That’s when I noticed how much she squirts. The sensation of a woman’s juice slowly dripping off your balls as she rides you is like no other. When we were done, it looked like we had a water balloon fight in the bed.

We washed up and went home. We had a couple more encounters before we split. I will consider writing about it if this was good. I apologize the probable grammar issues. I got tired of correcting mistakes.

Source: reddit.com/r/gonewildstories/comments/5o85am/mf_the_mature_assistant