The 50 Something Volunteer

I have a lot of ideas and fantasies, one that I have been enjoying a lot lately has been meeting an early 50s woman through volunteering at the local community centre. There is a real-life version of this lady but it's more of a generalized archetype really. Divorced for a few years, kids grown and moved out, living on her own with her cat and having the time of her life.

We are on a committee together to update the website, something I do on the side for contract work, but I'm donating my time to help out. She is in charge of the committee and putting together the content for the site and approving the design. I have admired her appearance, and professional demeanour, and her strong but kind personality with her intelligence shining through. We share a quick word after the meeting and she tells me how excited she is to work with a "real developer" like me on this project. I let her know that I'll take a week or so to work on the site on my own for the most part, with some emails back and forth.

Eventually I get to the phase where we need to talk about some design choices and get some content up, so we are emailing back and forth a lot. She tells me that often it works better for her when we can chat in real time, and suggests we use a Google meet for chat, file sharing and video calls. My heart beats a little quicker at the prospect of getting to chat with her 1:1 and I'm glad I have upgraded my video call setup to look really good in the background.

We are project focused but as we chat over text, I tell her a little about myself, and being the overeager over-sharer that I am, I talk a bit about my relationship difficulties, which she says really sounds a lot like her situation had been. It's hard to tell for sure through text chat, but I can feel like there is a connection growing and that we have a lot in common. The language shifts into more familiar and friendly banter, as we talk about different topics and things we are watching on tv, reading, cooking, etc. Eventually she gently brings the topic back to relationships, and volunteers that that her dead bedroom wasn't something she could put up with and that I shouldn't have to either, that it is human to have urges and needs, and that I deserve to have those needs met one way or another. It's a slightly awkward conversation moment between us, but we move on and focus back on the work for a little longer and call it a day around 11pm.

A few days later we are working together again and she suggests a screen share to show me some feedback she has on the design, so we jump on a call and she shares her screen. This time totally professional, she has her glasses on, very little makeup, and we keep focused on the website. I notice in the little video window of her that I keep glancing at, that she has been enjoying a glass of wine as she works, and I can tell she has loosened up a little by this time.

We go over it and then she says that she will upload a new version of the logo. She clicks the upload button and it opens the file selector to a folder with images. All normal from what I can see but then she scrolls down I spy one picture that... Stands out. She keeps scrolling, but it's obvious to us both that I've seen it, I can see her blushing in the little webcam window alongside the full size screen share. She definitely noticed my raised eyebrows and look on my face, which I did not do a good job of hiding, to be honest.

We move on, continue working until late that night and we are both at a point where we are tired, need to stop. We talk a little about the weather and our plans for the weekend, and some small talk, and then she confesses to me that she's still thinking about what I saw on her screen and how sorry she is, and how unprofessional it was. I laugh it off and assure her that it's not a big deal, I'm definitely not a prude.

I remind her that we are just volunteering for a community centre website and that professionalism doesn't really factor in. I admit that I did see it but that I'm sure I have similar stuff on my computer or phone and not to worry about it. She laughs and says that she can guarantee that I don't have this photo on my computer, which confirms to myself that this really is a picture of her! It was relatively tame but super hot, burned into my memory.

I picture it in my minds eye... She's leaning forward taking the picture into a mirror. Her face isn't visible but her breasts are exposed hanging naturally, nipples long and erect, and her other hand is between her legs, where I can see the base of a vibrator pressing into herself. Her face is not visible, other than her mouth open in a frozen moan as she is clearly enjoying herself.

She can see the far away look in my eye and asks what I'm thinking about with a smirk on her face and a blush on her cheeks. With a somewhat shaky and hesitant voice, asks if I enjoyed the view and I admit that it's all I can think about.

She says that a few weeks ago, she had been chatting with this guy and had taken her first racy pics and shared them with him, but deleted them when the chat fizzled out, except for this one which is her favorite. It's smutty without being too much, although she admits she shared some "really nasty ones" with him. I say "lucky fella" and she gets a gleam in her eye and her smirk deepens along with her blush.

She asks if I'd like to see it again, and I say "only if you are comfortable sharing". She says that she has enjoyed the liberation of showing off her body and knowing it is being appreciated, something she missed for years in her marriage. She brings it up on the screen at full size, and she can see my eyes widen and hungrily take it all in, watching my pupils dilate and my eyes fly around. She can tell where my gaze is focused, and says "I have a whole collection of toys, but that one is my favorite". I gulp down a swallow of water and almost choke on it, which breaks the spell. She closes the image and says that she doesn't want to make me uncomfortable. I joke that there is definitely some discomfort happening, but that I was not complaining.

The full size is everything I remembered and more and I admit to her that it is a major turn on... She quickly wraps up the conversation and leaves me hanging... Meanwhile my hand has been idly rubbing my rock hard erection the whole time through my pants, and I finally am able to free the beast and take care of it properly. I close my eyes and picture her leaning forward over me, her breasts tantalizingly close to my face, the scent of her hair and deodorant and light perfume like an intoxicating cloud, her smooth skin so warm and inviting, freckled and creased and tanned in the most delectable way. I realize I am in big trouble here and that I should not let this progress... But I want her more than anything in this moment. It's all I can think about, and as I stroke myself to one of those mind-leaving-the-body orgasms, I picture the huge load I produce landing on her chest, with her purring "good boy, that's a good boy" and I know that this is the path I'm on, and it feels good.

The next day I get an email from her asking if I want to get together in person for our next meeting in a couple of days, and invites me to her house which happens to be just a couple of blocks away. I immediately click on Yes and then just as quickly feel that hot flash of doubt and guilt from my head to my toes. Am I doing the right thing? But the erection straining against my pants is screaming at me to just let go, let it happen, allow myself the joy and satisfaction I have missed for so long.

Finally the day arrives, turns to evening, and I arrive with my laptop in hand, at her door, with the intent of working, but silently praying that my fantasy will become real.

She opens the door with a smile that could stop traffic, invites me inside and her house is spotless, like it's ready for a magazine photoshoot. Her hair is gently curled, like she has put in some serious time getting it just right. Her makeup is light but highlights her beautiful eyes, long natural eyelashes and her lips are wearing a muted, unobtrusive but lovely shade of gloss. I know she has been anticipating this moment just like I have been.

She has a fairly typical 50s "woman who takes care of herself without being a gym slave" kind of body. Curves in all the right places and a wonderful full bosom in a black tank under a white overshirt, and a slim stylish pair of jeans with bare feet. I notice a sparkly anklet and bright red toenails.

She catches me taking the full inventory and gives me a little twirl laughing "enjoying the view?" And all I can do is nod and swallow hard. We sit and I pull out my laptop and we get to work for about 15 minutes, but the screen is small and she's leaning in close, pressing her chest against my arm.

Finally I ask her a question and the eye contact remains as the answer trails off... She moves in and we are locking lips with urgency. She grabs my hand off the laptop and places it on her breast where I can feel her hard nipple stiffen under my palm. She is not wearing a bra, and I wonder what else she is, or isn't, wearing. She moans lightly as I roll it between my fingers and finally breaks the kiss and says that she needs to be taken care of immediately.

I guess she has decided (correctly) that I am somewhat of a sub and would love to be owned by a strong willed woman who knows exactly what she wants. At least, that's what I'm hoping for. She tells me that her nipples are very sensitive and that she needs me to pay attention to them. My mouth moves down to the stiff nipple poking through her tank, and as she feels my warm moist breath through the material, a shiver runs through her body, and I can tell it is having a big effect.

She gently caresses my cheek and lifts my chin to look into her eyes, asks me if I'm OK with this happening and all I can croak out is "I will do whatever you want, ma'am". Her eyes widen and smile deepens and I know I have just unlocked something within her.

She opens the closed door to her bedroom, and leads me in, and I can tell she has obviously been planning ahead, and has her collection of toys on prominent display, including a little bullet, a "satisfier" clit stimulator that I recognize, a couple of vibrators in different sizes, a pair of clips that I can only assume are for her nipples, and a couple of butt plugs, one of which is jewelled, and the other has a pretty serious handle. I can tell she means business.

She sees me eyeing the inventory and asks if there's anything catching my eye. She says that there is more to the collection but that I need to play my cards right to see more... I wonder what else she has put away, my mind eagerly imagining what else she might be interested in.

She tells me about how she has been imagining me coming over just like this, since she sent the meeting invite, and that she needs me to pick one to start with. As I'm looking over the collection I can hear rustling and I turn to see she has removed her jeans and her tank is really a leotard. Not much to the imagination as I can see she is not wearing anything underneath and the playing field is smooth as silk.

She stands there and slips her fingers in from the side and exhales with a low moan as she touches herself. Watching a woman pleasure herself is one of my all time biggest turn-ons and this is a literal dream come true. My erection is painfully hard at this point and her eyes are locked on the bulge in my jeans as her fingers explore her most secret place.

I select the smaller of the vibrators, not wanting to jump right to the big pink rabbit with the clit attachment and the little ball bearings... Just a simple one. She purrs... "That one is my favorite. Hits just the right spot every time..I've cum using this one hundreds of times". I realize this is the one she was using in the picture.

She says that I should really make myself more comfortable and remove my jeans so she can see my bulge more clearly. Her direct tone and words arouse me to a new level. My stretchy boxer briefs leave little to the imagination and i moan as she steps close to me, reaches down with her free hand, and caresses me through the stretchy smooth fabric.

She grasps me and gently leads me towards the bed where she lets go, and sits on the bed with her head directly facing the bulge in my shorts and her other hand still between her legs.

"I want to watch you stroke yourself right in front of me. I know you have been thinking about my picture when you are all alone at night in your basement office bedroom, right? Show me what you do when nobody is looking". I reach into my shorts and readjust, grasping myself and sliding my hand back and forth a few times.

"That is hot, but I want to watch the real thing." and her manicured nails hook the waistband and pull down, releasing me. I don't think I've ever been so hard, and it springs to attention proud and angry and thrumming with excitement. I'm not huge, but an adequate size and she purrs as she compares it to the vibrator I selected, I suppose subconsciously choosing one to match myself.

"That is a perfect size, just how I like it", while gazing up into my eyes. She holds the eye contact and wraps her hand around me, gently stroking back and forth as she brings her glistening pink lips to the tip. I close my eyes and despite being completely agnostic, say a silent prayer to the Force or whatever else, for allowing this dream to become real, as she takes me into her mouth and her hands move to caress my balls.

Her tongue swirls around the head, and a low moan escapes my chest. Her hand moves to cup my strong butt muscles (hockey player lower body 😉) and she squeezes and I feel her nails dig in a little. I involuntarily shiver and it feels like my soul leaves my body for a second.

Now she doesn't know this, but I've never finished from a blow job and I know I'm not about to right now, before the main event. But she says "ah ah not yet" as she pulls away and lays back on the bed.

While my eyes were closed, her other hand had been unsnapping the crotch of her leotard and she presents her bare pussy to me with not a single ounce of shame in her demeanour. Legs spread wide, surprisingly prominent clit at attention, slight gleam of wetness visible, it's like a vision composed from a thousand pictures and videos I have seen over the years, somehow the most perfect flower I have ever seen, and I kneel before the altar I know I am about to worship. I lower my head to taste her but she stops me, and says, "good boy, but not yet. You will use that toy you forgot about, remember? I want you to pleasure me with it, but you cannot touch my skin until I give you permission. Not my legs, not my breasts and definitely not my cunt. She only belongs to someone that has earned the right."

The vulgarity of the word is like a shock to my system and yet turns me on to a new level and I want nothing more in the world than to be worthy of putting my mouth on her... cunt. I don't use that word but in this moment it reverberates through my skull and feels so naughty. It's been a somewhat vanilla existence, I realize.

I leave the vibrator turned off for now and start by rubbing it along her inner thigh, down to the crook between her leg and glory, lightly brushing across her glistening wetness, and up to circle around her clit. Although it's not abnormal, it is engorged and very prominent, something that has always turned me on when I see it in porn, certainly looking urgent and ready to be pleased. My mouth waters as I consider the prospect of feeling it under my tongue but I know what my orders are and I control myself. Barely.

She is close enough that I can feel the heat coming off her on my face. I dip the vibe back down and enter her slowly, a bit of a tease. Watching this from so close up is fascinating. My wife has never liked using toys other than a little bullet vibrator and isn't into letting me watch... Unfortunately for me it's one of my biggest turn ons, maybe that is why. Being right here, inches from the action in real life, is making me feel light headed.

The sound as it slides into her is almost more arousing than the sight or the clean musky smell of her sex, like I am intoxicated. She moans and tells me to turn it on, so I do so. The buzzing sound attenuates as i slide it in and out and her hips buck gently with the sensation.

She has pulled the leotard down and one breast is free, her fingers pinching hard on her nipple as her other hand grasps mine and pushes the vibrator all the way into her, hard. My knuckle brushes against her stiff button clit and she tsks at me, scolding for "cheating", which feels wrong and naughty and sexy and like something I have been wanting for so long.

She tells me after a minute or two of moaning with pleasure that she is ready for my mouth to taste her, that I have been a good boy and earned my prize. I pull out the vibrator and it is creamy with her juices, I've never seen a woman so wet in person before and I wonder if this is an every day thing or just because of my attention. Her flower opens to me, glistening and deep red with arousal, with her soft puckered anus pulsing just below, a slow trickle sliding down out of her and along the wrinkled surface. I want to immerse myself in every part of her more than anything in the universe at this moment.

I hungrily dive in and feel the electric zap as my tongue tastes her tangy sweet salty soft skin, and all is good in my soul.