How I [M] Ended Up Fucking My Married Cougar Occupational Therapist [F]

[TLDR Version: I (M39) ended up fucking my married older Occupational Therapist (F55) after she reached out to me by e-mail when I was no longer a client. Long.]

The garage door was open – just like she said it would be. To my right I saw that the door leading up the stairs to the living area was open slightly – just like she said it would be.

I parked my car next to hers and entered the house. As I began ascending the dark wooden stairs I called out softly, “Hello?”

A sultry reply came back from her den where soft music played in the background. “Hello,” I heard her answer. “Come on in. I made you a drink.”

She sat on the couch with her legs curled under her wearing a short black dress like I told her to since I wanted to have easy access to her pussy. Underneath, she had a classy black and white brassiere that cupped her small breasts. Under her dress she wore a pair of black lace panties that I’d told her to wear since it turned me on.

Her toenails were painted a light pink color on and she’d put on a bit of makeup.

Haleigh looked all of her 55 years and I was slightly unsure if I was even attracted to her, but I definitely knew I wanted to kiss her and I knew I wanted to eat her pussy and I knew I wanted to see my cock in the mouth of the woman who had been my Occupational Therapist for four months – a woman with whom up to this point I’d only had a professional relationship. A woman whose husband was currently at work. The same place where I worked….

I then thought to myself, “Is this actually going to happen? How did I get here..?”

*CAMERA FADES OUT*

It all started when I tore my ACL as part of my job as a firefighter for a small but affluent county on the West Coast. While the pay wasn’t all that great, the local government was run by well-meaning Progressives who made sure their local employees were well taken care of and had access to good medical resources when injured on the job. As part of my recovery, I was permitted to go to an Occupational Therapist three times per week to work on regaining mobility.

The first day I went in I had a meeting with Haleigh. She was an older but cute woman, 55 years old, about 5’5” or 5’6” with short blonde hair going gray with mischievous brown eyes. She didn’t have a knockout body, but she looked fun and petite. I never really saw what the rest of her face looked like as everyone was required to wear masks in the office because of COVID. Haleigh brought me into the back room for some privacy as I explained what had happened and what brought me to see her and she asked a lot of questions about my injury and what I was hoping to accomplish. After about 30 minutes of that she told me to lie on one of their padded tables while she did some mobility exercises with me. As she was manipulating my knee and leg, she asked where I worked. “I’m a firefighter with Harrison County.” “Oh,” she answered. “Which engine?” “Engine Number 35 out by the airport.” “My husband works there,” she responded. Curious, I asked, “Really? What’s your husband’s name?” “Terry Jeffires,” she replied. “Terry?!” I exclaimed. “I know Terry. I work with him.” “That’s OK,” she retorted. “We’re getting a divorce.”

I was caught up a bit short by that one so I just muttered something to the effect of, “Well, I’m sorry to hear that.”

We continued through the session and later agreed on a schedule to see her for OT. Three times a week I’d go in to work on my knee and we established a teasing and fun relationship. She had a playful sense of humor and enjoyed listening to classic rock music, which I also enjoyed. Through the course of our appointments I learned that Terry was soon to move out out of the house and she would be living with her 21 year old son, David, who was finishing up college.

At one point after I felt we’d gotten to know each other pretty well, I said to her, “Hey, Haleigh, if you don’t mind my asking, why are you and Terry getting divorced?” Haleigh paused for a moment and said, “I married Terry when I was pretty young. He was much older than I am – over twenty years. We’ve been married almost 30 years and I had settled into a routine. You wouldn’t believe it but I wasn’t always this small. Actually, I had gotten quite big. But a few years ago I decided I didn’t want to be fat anymore and started to watch what I ate and to begin working out. And one day after I’d lost some weight, I had a patient who I liked and after an appointment he said to me, ‘You are the most beautiful woman I’ve ever seen. Your husband is lucky to have you.’

No one had ever said that to me. At least not for many, many years. I had thought of myself as unattractive and old. But now I began to realize that might not be true. And that’s when I realized Terry was kind of taking me for granted. He never showed me any affection and never would hold my hand. He just wanted to do his own thing and be left alone. And when I let him know this and told him I wanted him to treat me better, you know what he said to me? He said, ‘I don’t know if I like this new YOU.’

So, I realized I didn’t want to die like that. I didn’t want to grow old like that. I wanted more out of life. And with David being old enough, there wasn’t really the reason to stay together as before.”

Having been in a relationship in which the other party took advantage of my generosity and goodwill, I certainly empathized with Haleigh and told her as much. After that, our relationship got a bit more friendly as we began to talk openly about our lives and our hopes and dreams. We exchanged e-mail addresses and I sent her links to some good restaurants and bars she should visit in order to begin re-exploring life. One bar in particular, The Alcambra, had good bands on Friday and Saturday nights and she later wrote back and said she had gone and had a great time. We talked more about music and I told her about a great record shop in a nearby town here she could buy actual vintage vinyl records. On one trip to that town, I bought an extra copy of the Rolling Stones’ “Sticky Fingers” and dropped it off at her office before she got to work.

The next day I got an e-mail from her thanking me effusively saying how much she appreciated the gesture and how much she was enjoying the music. She then sent me a screenshot of a picture from her Instagram account in which she posted a picture of the record I had given her propped up against her record player with candles in the background and wrote, “Thank you to my amazing client for giving me this wonderful gift! I am having a drink and enjoying it right now!”

I was happy to have been able to help her out but in no way was I doing it to try to butter her up for any type of sexual conquest. I was just trying to be nice to someone whom I liked and who had been having a rough go of things. Besides, I was 39 years old (though I’ve been told I look younger) and wasn’t on the market for an older woman – let alone my Occupational Therapist. But, after we got to know each other a bit more, I began to have fleeting fantasies of doing something with her.

My schedule changed so I couldn’t come in during the early afternoons and I ended up coming shortly before closing time. Haleigh worked with a staff of about five other women and they were always working with other clients while I was there. But when I changed my schedule, there were fewer of them there since most clients didn’t want to have their appointments later in the day. Also, I’d still be working my exercises while many of them would be packing up to go home and turning off lights. On several occasions, Haleigh and I were on the back table and most of the office lights had been turned off and it was just the two of us.

In the early part of our professional relationship, Haleigh had me on the recumbent bicycle working my knee very intensely and doing all kinds of exercises. But after we got to know each other, she had me doing less of that and more time receiving “TLC” (as she called it) from her on the padded table. During this part of our appointments, I’d be face down on the table and she would be working my knee and leg with her hand. Sometimes I’d be on my back and she would grab my calf with one hand and move her other hand up to my thigh and work the knee backwards and forwards. I’d always wear loose running shorts and on several occasions, her hand went under the shorts on the upper part of my thigh near my buttocks. She was always abnormally quiet when she did this and I began to think perhaps there was more going on here than what appeared on the surface. After that I began to have a serious desire to have her grab my cock and to pull off her mask and kiss her.

I wasn’t all that attracted to her, but there was definite chemistry between us and I began to wonder what it would be like to fuck a sexy older woman.I still had absolutely no intentions of doing anything with her as I didn’t want to get involved in her personal situation with the wife of a guy whom I worked with, but I did on occasion tease her a little by pulling down my mask and smiling for her so she could see what my face looked like. She liked that so she pulled down her mask, too, and we teased each other about giving each other the Coronavirus.

But after a couple of months I felt my knee getting much better and having to go out of my way for an OT appointment was beginning to interfere with the rest of my life so I went in one day to tell her I was ready to graduate. We had previously talked and she had told me how well I was doing, how much I had improved, and that I could be the one to decide when I was finished with the therapy. So, while my announcement didn’t come out of the blue, I think she was still a bit shocked when I actually told her.

There were about three other therapists in the office working with clients and Haleigh was in the back room with another one. When I got to the front desk the receptionist said, “I don’t have you on the schedule today, Mr. Mitchell.” “Oh, that’s OK. I was just going to tell Haleigh this was my last appointment anyways.” From the back room I heard Haleigh shout, “Hey, Mark! How are you?” “I’m fine,” I replied. “I’m going to graduate myself today.”Haleigh looked very disappointed and came out to where I was standing. “Are you sure?” she asked. “Do you want to just skip the exercises today and I’ll give you some TLC?”

“No, that’s OK,” I answered. “I’m much better. I really appreciate everything you’ve done for me. And we’ll stay in touch. We’re friends now.”

Haleigh looked like tears were welling up behind her eyes and she softly asked, “Well, can I at least get a hug?”“Sure you can,” I said and I bent my 6’1” frame down and wrapped my arms around her. She melted into me a little bit and smiled and I said, “OK, I’ll be seeing you. Thanks for everything.” And I walked out the door expecting nothing more than to have a virtual e-mail friend whom I would occasionally send a good music or restaurant recommendation. No expectations or desire for anything more.

That Halloween I got an e-mail from her standing with three of the other OTs in their costumes. The others had on actual costumes, but Haleigh just wore a pair of bunny ears. And she looked really good. She’d lost some more weight and even with her COVID mask, I could tell her eyes still had that mischievous grin that I’d seen many times before in her office.I replied with a mildly flirtatious, “Looking good!” and thought that would be the end of it. Instead, a couple of nights later, I was sitting at my computer when I got an e-mail from her. “How is your night going?” she asked. I smiled and curtly replied, “Fine. How’s yours?” A short time later she wrote back, “If you ever go out to The Alcambra you should let me know.”

I thought that was a bit forward for a married older woman, and I still wasn’t trying to get in the middle of anything so I replied, “That’s more a dance place that I thought you’d like. The only dance I know how to do is the Batusi from the old Batman TV show.”

A few minutes later is when she hit me with the shovel.

“Well, if you ever want to come over to my house for a drink, let me know…”

I laughed to myself and quickly texted my good friend Marcus. “Holy shit, Marcus! My married cougar OT is fucking flirting with me! She wants me to come to her house for a ‘drink’!”

Marcus quickly texted back, “You’d better fucking do it, you piece of shit!”

I decided to be bold rather than beat around the proverbial bush and wrote to her, “Haleigh, I get the feeling you’re flirting with me. I’m not averse to it, but I just want to make sure I’m not reading things wrong.”

A short time later came her reply: “I am.” Along side it was a smiley face emoji and the fire symbol.

I took a short breath and said to myself, “OK, well, here we go. Let’s see what happens.”

Deciding to play it cool, I wrote, “Aren’t you worried about Terry?”

Haleigh quickly replied, “You could come over when he’s not here. On the down low…”

Now it was my turn to be forward. I responded, “Have you ever had a man lick you. On your ‘down low’?” There was a momentary pause before she wrote back, “Oh my god.”

I decided to play with her some more and asked, “What do you think would happen if I came over when Terry wasn’t there?”

“Pleasure. And sweet release,” was her reply.

Now she had me seriously considering her offer. Again, I wasn’t looking to shit where I eat workwise or with a married woman, and I wasn’t all that attracted to her. But the idea of fucking an older, sexually charged woman who had been neglected for years (if not decades) had me extremely intrigued. But, still trying to stop what was beginning to feel like the inevitable, I decided to see if we should pump the breaks on this reckless behavior.“Haleigh,” I wrote. “Are you sure you want to go down this road? I don’t want to mess up anything with you and Terry.”

And after that, there was radio silence for a while.

I decided to go to bed but couldn’t really sleep so I got up in the middle of the night and checked my e-mails.There was one from Haleigh in which she wrote:

“I’m sorry. I was just being silly. Please pretend I never wrote what I did.”

I figured she’d probably been drinking that night, gotten lonely and horny, reached out to me, but had sobered up and regretted what she had written.

But now that she had me thinking of what it might be like, I wasn’t quite ready to let it go. So I wrote back:

“Haleigh, I don’t think you were being ‘silly’ at all. I think you meant every word.

It’s a shame because I’d be very interested in showing an attractive mature woman some things that she had possibly been missing out on for many years….”

I went back to bed and the next morning I received Haleigh’s reply.

“You have my attention. It might be fun to see what would happen if we had at least one collision.” along with the fire emoji.

Rubbing my hands with evil glee, I got her telephone number and we began to communicate using the more efficient text messaging system. I asked her what her schedule was looking like that week and when she might be available to “collide”?

She said she had time on Thursday at 5:30 PM when Terry went in to work a night shift and I agreed I would come over. She said she had a two car garage and would leave the door up. She noted I should pull into the slot next to her car and shut the garage door so her neighbors would not see my car. The door leading from the garage to the upstairs would be left open as well.

Having established what we were planning to do, we began to furiously sext each other throughout the day. I began to ask her what she liked to do sexually and what her turn ons were. I asked her if she liked a forceful man, or someone more gentle? She responded that she was out of practice and wanted someone to be gentle with her at first, but that he could become more assertive later. I asked her what her favorite sexual positions were, and she said she didn’t even know but was getting wet just thinking about it. I told her I wanted to eat her pussy and when I did I wanted her to grab the back of my head and pull my tongue into her. She replied back that I was making her so wet and she was going to have to play with herself to relieve the tension. Haleigh then said she had never felt so sexually alive and informed me she was multi-orgasmic.

I began to feel even more bold and wanted to push to see what her limits were. I wanted to give her the most amazing sexual experience she’d ever had, and knew many sexually repressed older women had fantasies they wanted to engage in but were too timid or shy to do so because of the generation in which they’d been brought up. But that didn’t mean those desires weren’t there. They were just well hidden. And it would take someone with a bit of knowledge to bring them to the surface.

So, I asked her if she liked to be held by a strong man, if she liked kissing, if she liked spanking, if she liked to be held down? Haleigh replied that she adored kissing and wanted to feel safe and secure with a man before going further.She then surprised me and wrote, “I need to ask you a question.” “Go ahead,” I replied.“I have this thing I like to do.” She wrote. “I really like to suck cock. And I like to drink your cum. It’s my thing. Would that be OK?”

I laughed out loud. “Of course.” I wrote. “You can do anything you want. And I mean ANYTHING.”

Now, I really began to push the sexting to see how far she’d be willing to go and we began to get hotter and hotter. She told me she was so fucking wet texting me that she had to get one of her “toys” and play with herself. I asked her what she was thinking about when she was playing with herself and she wrote, “You standing in my door stroking your cock watching me as I orgasm.” I wrote, “Would you like to see a picture of my cock or would you like for it to be a surprise?”

Haleigh responded, “I would love to see it.”

Now, on Reddit it seems like every guy has a monster cock. 8” thick gigantic meat monsters. Sadly, I’m completely average. 5.5” on a good day, and as I’ve gotten older I have less and less sexual energy and have a harder time getting an erection, though all this sexting with Haleigh was giving me a permanent chub with plenty of pre-cum leaking out.

So, for the first time in my life I unzipped my pants, angled my now decent looking engorged cock to the right and snapped a picture, which I then texted her.

She quickly wrote back, “Oh my god. It’s gorgeous.”

Rather pleased with myself but not wishing to disappoint, I replied, “It’s actually smaller than it looks. The camera adds 10 pounds…”

Haleigh laughed at that quip and responded, “Good. I am rather small and very tight down there.”

I wrote back, “I knew you would be tight…”

“Oh my god,” Haleigh replied. “You’re making me so wet…”

However, all my fine dreams and well-thought out schemes of fucking my married middle-aged former Occupational Therapist almost came to naught when I woke up the following morning to a text from her:

“I am so sorry. I can’t go through with this. I am absolutely terrified. I am sorry I instigated this. We can’t do this. I just want to be friends. I am so sorry.”

Somewhat taken aback, I replied, “Haleigh, I am certainly not going to try and talk you into doing something you don’t want to do, but I find you very attractive and would love to have the experience of being with a mature woman who is finding her new freedom and wants to explore things with a younger man. We could take it as slow as you want. We don’t have to do all that crazy stuff we talked about. I could come over and we could sit on the couch, have a drink, talk, do some light kissing, then see what happens from there. But you need to make a decision one way or the other. I’m not going to force or pressure you into anything.”

And then I hit send.

And then there was radio silence.

For a whole day.

I texted my friend Marcus, “Dude, I think she’s bailing on me. I have a massive case of blue balls. I’m going to have to rub one out to relieve the tension.”

Marcus sagely responded, “Just play it cool. She’ll come back around.”

I was headed into work that Thursday morning (where I knew I’d cross paths with Haleigh’s husband Terry) when I received a text from her.

“OK. Just this once. And only for a short time. And just so I can suck and swallow you…”

TO BE CONTINUED….?

Source: reddit.com/r/gonewildstories/comments/jqd80l/how_i_m_ended_up_fucking_my_married_cougar