I’ll start with an introduction first. I’m a 22 years old male, 1m80 tall. I’m pretty skinny and not muscular but apparently I’m still pretty good looking. I always make sure my hair is on point and I’m clothed pretty basic, but still a bit classy. I’m not the most extrovert person on earth but talking with other people has never been a problem for me. COnversations always go fluidly except with that small percentage of people and then it’s awkward silences all time.
Anyways, I’m a good listener. I can’t remember how often, even without asking, people start telling me about their problems over and over again. I don’t know why or how, but people feel comfortable telling me everything and in the end, this creates an emotional bond. I often got the feeling I mean more to them as they mean to me, because I’m only the listening ear most of the time, but this has come to an advantage a couple of times and as you could’ve guessed already: this story is one of those.
I have a weekend job and I always have to work with 2 other people. One person is always the same, the other used to vary from weekend to weekend. At a certain time, the ‘variable’ person was the same woman every other saturday. Let’s call her Wendy. Wendy is halfway her 40ies. She’s about the same length as me, has dark brown eyes, shoulder length straight brown hair and she’s got a good figure for her age. She also has many freckles on her face, not the ginger kind of freckles but more brownish. If I would have to rate her, i’d say she’s a 6/10. No eyecatcher, but not ugly either. She’s divorced, has 2 sons (20 and 17 years old) and she’s got a lot of problems with them. As she’s pretty talkative, she always asked how I was, how school was etc. and to be polite I asked how she was too etc. She’s also the kind of person that gets too stressed at work, she always tries to do too much and when it becomes too much she complains about it to me. I always said that she’s right, comforting her and telling things will get better soon. As we got ‘closer’ (aka she dares to tell me more) she told me more about her problems at home, and one day we kept talking for about an hour after our job was done. After this talk, she thanked me for listening and I noticed she wanted to give me a hug but I saw her hesitating. This was probably because she thought it would have been inappropriate and I wasn’t too sure about it either. I quickly said she’s welcome and that I had to go home, so i said her goodbye, making a waving gesture with my hand and walked away.
Not much later, due to some troubles at work, the boss decides to appoint 2 fixed persons instead of varying all the time. This means I only saw Wendy passing by once in a while, giving us no more chances to have a conversation going further than a short hello.
As the months went by, I suddenly realised I haven’t seen her for a while. After asking around, I get to hear she’s staying home for at least 6 months because she’s depressed. I’m not sure how much time went by, but at least another couple of months.
Sometimes, it occurs that there’s no work for a minute or five and then my thoughts drift off. I don’t really know how, but suddenly I notice she’s still not back, and I wonder how she would be doing now. I don’t have a phone number, no last name, no adress, nothing so I quickly give up on the thought. Later that day, I was bored and decided to look on facebook for her. (I dont add anyone from coworkers on fb). I search for some coworkers on facebook and check their friend list if possible. Eventually, I find her profile and ofcourse her last name too Then suddenly, an awesome idea pops into my head.
I take the phonebook, search for her name and after a while I find her number! I put it in my phone and decide to call her in the evening. I was super excited, and I didn’t know why.. I honestly never did this before, I was just going to call some coworker and ask how she is doing. What the actual fuck was I thinking? I rarely make phonecalls and if I do, it’s because I need to ask something. At about 8pm, I decide to make the call. I bring my phone to my ear, and feel my heart racing. Why am I so nervous?! Suddenly, she picks up the phone. Or no, she doesn’t, its her voicemail.. Normally, I never leave a voicemail but I quickly say it’s me, the coworker, that I was wondering how she was and I decided to give her a call. That’s it, I wasn’t even sure she would want to call me back or maybe she’ll be weirded out when she hears it.. I’m already regretting what I just did. But then I feel my phone buzzing in my pocket. Once, then a second time.. but no third time. If it buzzes 2 times I know its a text, if it buzzes more than twice its a call. I fish my phone out of my pocket, and I see it’s a text indeed. It’s from her! She says she can’t call back right now, but she’s doing okay and is happy I called her. I text back she can call me back whenever she wants. What the hell am I doing? I keep asking myself this. Does this mean anything or is this just being friendly? Ofcourse I start to think about what would happen if it would become more than friendly, but I can’t get my mind straight on it, so I decide to see what’s going to happen. It’s not like there’s something to lose, whatever the outcome may be. The thing that weirds me out the most, is the fact she could have been my mother, she’s twice my age. It feels inappropriate and nothing even happened..
The next day, she calls me at noon. I greet her but I have to tell her I’m at school and my lunch break is nearly finished so we can’t really talk at the moment. She apologises for the interruption but she also asks me if she remembers it correctly that I’m going to school in the center of our town. I confirm this, and she tells me she needs to get some stuff from the mall today and asks me if I maybe have time to meet her afterwards, as my school is close to the mall.
I tell her I can do that and she says she’ll send me a text with what pub/restaurant in the mall she’ll be at. My friends asked me who called but I told them it was my cousin. No way I was going to tell them who it really was, and what I’m planning to do! To be honest, I had no time to meet up. I had class untill 5.30pm and had to be home for dinner at 7, but I was going to skip class as it wasn’t really an important class anyways. The next 2 hours felt like 2 days. I couldn’t stop wondering what to expect. But at last the teacher says class is over. While putting my stuff in my locker, I get another text from her. She says the mall is very busy and doesn’t want to stay there any longer than necesary and wants to get a drink somewhere else. I reply that’s fine, I hate having decent conversations in busy places anyways and asking to meet in front of the mall.
As agreed, I find her sitting on a bench at the entrance of the mall. She’s wearing a blue skirt which ends right above her knees and a shirt with a flower pattern on it, not revealing a lot of chest. Her hair and her looks were still the same, not much has changed in the past half-year or so. Not sure how to greet her, I just say ‘Hi, good to see you again!’ and I put my hand on her shoulder while saying this.
Ok, this might become awkward.. We walk to her car, having some small talk about the weather and when we arrive at her car, I get into the passengers’ seat while she puts her bags in the trunk. When she’s finished and got in too, she asks me if I had a preference where to go. I politely say no, but nothing too expensive as I dont have much money left for this week. She says we could go to her appartment. Its not far away, her sons are at their dad’s place so it won’t be awkward and the drinks will be free, so I agree, not thinking anything more about it. We continue having some small talk about our lives and other unimportant stuff like we always did. When we arrived 10 minutes later, I offer to carry her bags so she could lock her car and unlock the appartment doors more easily. She thanks me, we take the elevator to the third floor and enter her appartment. It’s not big, but it suffices I guess. I put her bags down, she tells me to get comfortable in the sofa and asks me what I want to drink. I ask for some water as I was getting really thirsty from all the talking, and she took a coke for herself. She sits down in the other sofa next to me, which was rotated 90 degrees compared to the one I was sitting in and we continued the talk where we left off. After about what seemed to be 10 minutes but was over an hour apparently, I notice how much time has passed already and I tell her I should get going. I had some more time to be honest, but the conversation was coming to an end anyways and I wanted to avoid any awkward silences. I thank her for the drink, she thanks me for the talk and then I see her hesitating again. I decide to take the lead and give her a hug. But I give her more than just a friendly hug. I noticed she has been acting nervously. She has been twisting her hair around her fingers and often covered her chest with her hand.
Instead of just grabbing her shoulders and her upper back as you would do for a normal hug, I put my right hand onto her lower back. I pull her body firmly against mine. I suddenly realised how badly I wanted to feel her body against mine all this time. It felt so wrong, but I couldn’t help it.
I loosen up my grip, which probably gave her the impression the hug has ‘ended’. Instead of letting her go completely, I put my left hand on her cheek while simultaneously pulling her hips against mine with my right hand and I kiss her passionately. My heart starts racing even faster when our tongues meet, and I feel her inhaling deeply. Her hands start moving over my back, I start squeezing her ass with my one hand while I move my other into her hair, grabbing it gently and pushing her head even close to mine. It doesn’t take long before she puts her hand under the back of my shirt and touches my back, without the shirt in between it this time. I decided to do the same, but I went under her skirt to grab her butt. Damn, it’s so soft and squishy. I push her hips tighter to mine and I feel my cock pressing against her mound trough our clothes. She lets out a little sigh, fuck this is hot. While kissing her, I start pushing her backwards towards the wall. Every memory since then is covered in a cloud of lust and extacy but i’ll try to describe what happened as good as possible.
While kissing her and pushing her firmly against the wall, I start unbuttoning her shirt. Before I know it I’m squeezing and rubbing her boobs. She has these perfect B cups, not too small, not too large and concidering she’s not in her twenties anymore, they still look very good. I start kissing her on her cheek, making my way to her ear, then her neck, her collarbone and reaching the top of her breasts eventually.
I pull down her bra a bit while making my way towards her nipples. She’s having a hard time trying to surpress her moans, especially when I start flicking her nipple with my tongue, while squeezing the other with my hand. I go back to kissing her, get rid of her shirt and bra and then I break the kiss. I tell her to turn around and while she obeys quietly I get rid of my shirt. I grab her breasts with my hands while kissing her neck. I move my right hand down from her breast untill I reachh the edge of her skirt. I unbutton it and it falls down to the floor. While playing with her breast and kissing her neck, I rub my hand over her panties. Her panties were soaked. I never felt a woman being this wet before, she was so turned on! She keeps pushing her butt against my crotch while I keep rubbing her panties, but I can’t control myself, I need to feel her pussy. I put my hand in her panties and feel a small bush. I push my hand further into her panties, finding my way to her valley and the river in between it. I let my middle finger slide between her lips, rubbing her clit with her own wetness and her moans get faster and louder. While rubbing her pussy, I follow the way down between her lips and my finger slides in like it was nothing. I add another finger and she exhales deeply, clearly enjoying what I’m doing to her. After letting my fingers slide in and out a couple of times, I turn her around again, kiss my way down her body towards her panties and I pull them down. I grab one of her legs, put it over my shoulder, and I kiss my way towards her pussy. Like I noticed before, she had a bush but it was maintained pretty well. I could smell her pussy more and more the closer I was getting to it. The scent was so attracting, if not irresistible. I had to taste her right now. I spread her lips a bit with my thumb, exposing her pussy some more and then I licked her, from the bottom all the way to her clit, tasting her godly sweetness. She puts her hand in my hair and pushed my head firmly against her pussy. She was clearly going to cum from this if I proceeded doing this. But I’m not planning to give her have an orgasm, not yet at least. While licking her, I used my free hand to unbuckle my belt and get rid of my pants and boxers. I stand up again, I grab her leg and put it on my hip with my one hand while positioning my cock against her entrance with my other hand. We look each other in the eyes for a moment and then I slide my 7 inches into her while giving her the most passionate kiss ever. Slowly but surely, I keep sliding in untill I’m filling her completely. I start thrusting, building up my pace while she follows my rythm by rocking her hips. This is way too hot. The way she moans, her wetness making its way to my balls and the fact she’s twice as old as me and wants to be fucked byvme. I feel the pressure building and I know I’m going to burst my load soon so I pull out. I direct her towards the sofa to change position. Butsuddenly, she grabs my hand and she pulls me towards her so we’re chest to chest again. We make out some more and then she pushes me down onto the sofa and gets on top of me. She grabs my cock and positions it under her pussy. Yes, this is exactly what I wanted. I love it when women take control, there is no clearer indication they literally want to be fucked.
I feel her opening touching the tip of cock, and then she lowers her weight on it taking me completely inside of her. Fuck, she was hot, and so I told her. I grab her ass while she starts going up and down, and start rubbing her clit with my other hand. We build up the pace and she sighs ‘I’m going to cum, I’m going to cum!’ I grab her butt as close to her pussy as possible, and I feel her pussy stretching as she slides up and down my cock. Her breathing halts for a fraction of a second and she reaches her climax. I push her down onto my cock, going in as deep as possible. I’ve been trying to hold my orgasm since she started riding me, but her pulsating pussy and being that deep in her pulls me over the edge. I shoot the biggest load of my life inside of her. We make out for a couple of more minutes, recovering from what just happened and then she moves her hip upwards, letting my now soft penis slide out. We cleaned up, took a shower, made out some more but then I really had to go.
Because of the divorce, the troubles with her sons and the stress, she hasn’t had sex for over two years. I was the first person in this shitty period of her life to actually care.
I wasn’t the only one not knowing what to expect of this ‘meeting’. As I wasn’t flirting and giving no signals at all, she didn’t think anything would happen. But on the other hand, she told she thought about the posibility that something more could happen but thought was too crazy to be true. We agreed this meant nothing more than 2 adults who needed to have some intimacy and that’s it. When I left, she didn’t hesitate to hug me and she thanked me for the talk. I gave her a final slap on her ass when I walked into the elevator and when doors closed, I told her she could call me again if she needed a good talk and gave her a wink.
Source: reddit.com/r/gonewildstories/comments/4kdsxq/how_i_m22_ended_up_fucking_my_coworker_f40_long