Another Office Encounter with a [M] Much Younger Woman [F]

It’s been a few months since I told a story here, and this is the third and last in a series of stories I had promised to post about my get-togethers with much younger women in my office. The first two were delightful encounters with small BBWs in their mid-20s — this was some 3 years ago, and I was in my early 60s — and this last one was a similar adventure with a young Latina that took place no more than 6 months or so after the first two. You can easily find the two earlier posts and others by clicking on my profile link.

As I related earlier, I work in an office near a major university in a major Texas city. Before the pandemic broke out, there would be 8+ people working out of this office on a typical weekday, especially in the afternoon, and most of them would clear out by 4 PM or so. My own job involves lots of writing and telephone work, mixed in with meetings sometimes at the office but mostly somewhere else, at all hours of the day and evening. My supervisors are all out of state, so I have broad latitude in shaping my work schedule — opening up all kinds of opportunity for play.

A Not-Quite Office Encounter Turns Into a Tryst [M] With a Much Younger Woman [F]

As I wrote in my last post, a few years before craigslist shut down its personals sections, I had within a short period of time three NSA hook-ups with younger women  … much younger. I was in my early 60s and all three of them were in their 20s. This first young lady, the one I wrote about most recently, answered an ad I placed on cragislist looking for an office blowjob, but the second one — the one I want to talk about now now — placed her own ad. And of course I answered.

I work in an office not far away from a major university in a major Texas city. My work affords me a very flexible schedule, as it involves in-person meetings at various times of the day and sometimes into the evening and weekends, or at least it did pre-COVID. So if I have someone(s) over for a meeting in my private office, or if I head out at any time for a meeting, no one questions it. I do work closely with my office colleagues, but my supervisors are all in other states, and I have enormous flexibility in structuring my work week — as long as I get done what needs to get done.

A Craigslist Confession: A Young Women [F] Sucks and Fucks Me [M] In My Office

Two years or so before craigslist suspended its personals ads, I got with two different women for sexual play in my office and with a third woman in her apartment not far away from my office. I was already in my 60s, all three women were in their 20s, and I met all three thanks to those personals. Here is the story about the first one.

My office is a short walk away from a major university in a large Texas city. As I mentioned in some of earlier posts here, the Great Recession forced my employer to lay everyone off except me and close our office back in late 2009; I worked from my home and from cafes for the next two years. Somehow I managed to bring in enough work to re-open our office and add new staff in late 2011. By the time these encounters happened, I’d say sometime in 2016, we had 10 or so people working with us at any given time.

A Hotel-Room Affair: MILF [F] Joanie Showers Me[M] With Affection

Several months after my most recent affair (with Helen) ended, I struck up a hotel-room only relationship with a woman I am going to call ‘Joanie.’ Joanie lived in a Texas city I visited once or twice a month for work, so our affair was long-distance and intermittent due to the challenges of synchronizing our schedules. But it was plenty of fun when we could get together. Joanie is the only regular lover I exclusively met in hotel rooms, never once over drinks or coffee. She had an enormous sexual appetite and was by far the most prodigious squirter I have ever encountered.

I met Joanie thru the same vehicle I met most of my other longer-term lovers: an ad in the craigslist ‘Men Seeking Women’ section. As always, my ad made clear that I was looking for a married woman who like me needed more TLC (read: sex) than marriage provided, someone politically left-liberal like me, someone who would be fun to hang out with, and not least someone who did not want to disrupt their current domestic situation in any way. I added that I lived in another city but came to town regularly, which I think made me more attractive since, as I wrote in some of my first posts on this forum, some women prefer to hook up with an out-of-towner to avoid complications. I used this line a few times when I was looking for a one-time thing in my own town while my wife was away, and I had some success with it; but this time it was true.

I [M] Share Sushi, Anal Pleasures and More With MILF Helen [F]

Here is my story of a delightful affair I had with a married woman some 8-9 years ago. It lasted a little over year. She would always bring sushi and a small bottle of red wine we’d share after lovemaking, and after a few sessions she asked me to take her anally as well. And of course I did.

This began like most of my other affairs, with her responding to an ad I had placed on craigslist, looking for an ongoing sensual friendship with a married woman. My ad was very similar to the one that had attracted Katie, and the one that drew in Louisa whom I had to cut loose after she proved to be crazy (details in my earlier posts). In fact, this woman — let us call her ‘Helen’ — saw the same ad Lousia had answered, and finally screwed up the courage to respond, but not till right after I had pulled it down. So we just missed each other at first. This unfortunate turn cost our affair a number of months.

I [M] Tease, Tie Up and Fuck MILF Katie [F] for the Last Time

Just before Halloween of 2009, my three-year affair with MILF Katie came to an end end. It was the time of the Great Recession, and my employer had laid off all of its Texas staff except me. The unpleasant task of clearing out the giant office fell on my shoulders. I had to get rid of file folders and filing cabinets, desks, staplers. chairs, tables, rolls of tape, paper clips, trash cans, scissors, everything you might imagine that an office would have. For this I used craigslist, the same vehicle I used to find sexual encounters, mostly one-time things but others blossoming into full-blown affairs. My affair with Katie was one of these.

There was so much to her that kept me wanting more: her poetry, her generosity, her kisses, her joyful breasts, her powerful thighs and hips, her oh so wonderful pussy that shook with delight when I ate it and emptied myself into it, even the pitch of her voice and its East Coast accent. I knew she fucked other men but she kept bringing her bounty back to me, me, over and over. If she weren’t fucking so many others, I’d even say she was loyal to me, and I guess in her own way she was. I still can’t explain this and neither could she; once she wrote me, I don’t quite know where to put you in my head or my heart.

I had also come to understand that there was much darkness in Katie. Some of it came from the harsh reality that her oldest son was autistic. She wrote poems about the shocked and cutting glances they’d receive when she’d take him shopping, poems of how other mothers would want to get together with their children for play dates but backed out once they saw or heard him. One poem began, It starts when they tell you your son is broken … and goes on, It starts when they tell you you are broken … it being I suppose both her battle with depression and her desire to lose herself in pure raw sex. It stemmed too from her first sexual experience of having been raped, and from the unwarranted feeling of guilt that came from that. It stemmed from her rebellion against the way girls are raised in our society, dressed up as toys for men to desire and pursue but shamed as sluts if they enjoy being caught, and especially if they do the catching. No wonder Katie took money from men in suits, men in positions of prestige and power, for hand jobs and blow jobs where she’d decide how and when and where they would cum.

But this still does not come close to capturing Katie. She loved sex, wanted to experience its full glory and sordidness. She was omnivorous and wanted to taste it all. Everyone needs a hobby, she wrote on a poetry forum; why won’t they let my hobby be fucking strangers?

Towards the end of October, I invited her to meet me at a bookstore up her way. We met in the store, cafe, then we each perused different sections of the store, rendezvousing by the registers with our choices. She was picking up Christmas presents for family and I selected two volumes of Rilke’s poetry and gave one of them — Love Letters to God — to her. I would have taken her back to my office and fucked her but her schedule did not allow, so she sucked me off in her van as a little thank-you and well, because she enjoyed it.

No matter, she came down to my office the following Friday. She knew we were shutting down and I asked her, Hey do you want any of these office supplies? Well of course she did. She has a weakness for office supplies, she wrote back, like the good PTA mom that she was. By the time she arrived I had everything neatly sorted in piles on a long table, in a room in the back with no windows: scissors here, rolls of tape there, paper cutters next to these, staplers and staples and paper clips, brown pink and blue clipboards, rulers and a couple of yard sticks, folders and round and rectangular stickers for color-coding them, even a ball of string and packets of star stickers. It was a dream come true for a mother of three boys who lavished cookies, time and gifts on their teachers. She grew excited as she began filling up the bags she had brought along.

Hey wait a minute, I told her. Not so fast! You are going to have to earn those items, oh yes you are! You are going to have to do me a favor or two. This excited her too. I told her to strip off all of her clothes and lie down on the floor on her back. She complied. I then directed her to stretch her arms above her head, towards a chair I had positioned there. She did. I cut off a length of string and tied one end around her wrist and the other around one of the chair legs; then did the same with her other arm. I picked up one of the rulers. Have you been a good girl? I asked. Oh yes, she said, and for that I kissed her lips and put a star sticker on her cheek. Good girl, good! But why are you here? She said she’d come down to get office supplies — and to fuck me. Naughty naughty, I said, and swatted her nipples, first one then the other, with the ruler. She winced in painful joy.

I reached for a cup of ice I had picked up from a nearby restaurant before she arrived and held a piece to her nipples, chilling them before sucking them with my warm mouth; then did the same with her clits. Oh she liked this, she did! When she admitted she loved the naughty things we were doing, I swatted her pussy five times with this face of my open hand. Oh, she said! Oh! No one has ever spanked my pussy before, thank you! For that she earned another star. And so it went, as I covered her cheeks with star stickers and her body with licks and kisses when she was good, but swatted her again and again with that ruler when she was naughty, here there and yes even there. Of course she could have easily freed herself, but of course she didn’t. Of course I ate her, long and hungrily and roughly, and of course I then fucked her, teasingly at first just barely slipping my dick inside her, moving it in and out at the opening of her sex, then deep and hard, pushing my cock to her very bottom and holding it there as she came. Again and again and again we did this, and finally I licked her clit with the very tip of my tongue, barely touching her at all, as lightly as I could. This brought her to a delicate and intense orgasm.

We sat there blissfully for a time, listening to the French songs I had cued up on my laptop. I had never seen her so pleased and satisfied, and I was floating too. This was to be our final time together, the last time we shared intimacy.

A day or two later she emailed me to say that she had concluded that she was a sex addict and needed to put herself in therapy, for her own sake and for the sake of her family. Sex was consuming her and she had to stop all of it, stop meeting any and all men, me included. Of course I respected her decision.

We continued to write each other into the new year, and as a poetry reading approached that I felt certain she would attend, I went as well and there she was. I sat some distance away as she chatted with a friend across the cafe, but soon she came to me and I bought her a beer. When it was time for me to go, she followed me outside and reached out to hold my hand. I know I could have taken her to my car and had my way with her, and I know that is what she wanted in that moment. But I was not going to enable what I now understood would be self-destructive behavior. No, not any more. I quoted her the lyrics of Townes van Zandt’s song Rake — this was a poetry reading, after all — said goodbye and walked away.

Not long after this I received an email from her explaining that her therapist had counseled her to cut off all contact with me. That is just how it would have to be. The last three words in that email were these: I love you. I never heard from her again.

I [M] Ate Two Different Craigslist Women [F] in a Single Week

During a time when I was between two long’ish affairs with married woman, I hooked up with two different woman with no other purpose than to eat their pussies. This would have been back in late 2010 or early 2011. Both happened as a result of ads I placed on craigslist, and they happened no more than a week or so apart. And both women were much, much younger than I was.

I was a frequent user of the personals page on craigsist in those days, scouring Women Seeking Men, Mscl Romance, and Casual Encounters. I’d answer the relatively few ads from women that seemed worthwhile, and I’d post a few of my own but was not having much luck. But then I posted an ad seeking nothing more than to go down on a deserving woman, either at her place or in a hotel. My ads made clear I was not concerned about body type age or race; I just asked that they be clean, playful, and ready to be pleased!

The Bald Bull: MILF Katie [F] andI [M] Have Another Threesome

This is the story of my second and final threesome with MILF Katie, and one of the last times we saw each other. Our first threesome, the one with the trombone player, was delightful, but this one had a very different outcome. It did lead me to discover a key truth about Katie, and helped me decipher the mystery that surrounded her, insofar as I have managed to do that.

I had begun seeing Katie more than two years earlier and we had had some wonderful extra-marital adventures. She was the classic mother-whore, sweet, naughty, with a boundless appetite for all things sexual, and a poet. You can easily find out more about her and our times together by clicking on my reddit handle. As the year 2009 wore on, Katie and I continued to connect, but less and less.

This was not a good year for me. Before it was over, our Texas office was shut down, due to the recession and bad decisions by our new leadership. We once had 25 or so people in our employ, and by October I was the last man standing. I had the unpleasant task of selling off or giving away everything — computers, chairs, desks, tables, all manner of office supplies and odds and ends.

Confession: I [M] Fuck Jolene [F] Repeatedly With Her Husband’s Consent

During the second half of 2009, I struck up a FWB relationship with Jolene (not her real name), a married woman in her 50s I met through OK Cupid. I already had a long-term thing going on with a married woman named Katie. You can click on my reddit handle to find the many posts about my times with her. Katie still wanted to see me but made it clear that she wanted full latitude to see others, and I felt I had slipped to her backburner. So I went looking for someone else too, with her encouragement.

You probably know how OK Cupid works. You create a profile and can run searches with the criteria you select — how far away do they live, what are they looking for and so on. In those days they had a category for married people looking for outside lovers. I am not sure they have it now. Remarkably, it was free of charge, even for men. I am not sure how they covered costs.

I [M] Fuck MILF [F] Katie to Tears, Break It Off, And She Lures Me Back

My affair with Katie that had been interrupted by her third pregnancy recommenced when she surprised me by going down on me in her van parked outside a crowded cafe in the middle of the afternoon — as her youngest child sat in his car seat right behind us. This was harlotry at its best, but not the sort of thing I wanted to repeat with the son around. You can read the details in my last post.

So Katie and I were off to the races again, and began meeting in our usual hotel and my office when we were both able. Or so I thought. I soon found out — actually she told me — that she was hooking up with other men, even on days when I wanted to get with her again.

I need to say something about my mental state at this time. This was 2009, and the Great Recession was well underway. We had also had a change in leadership at work and the new guy made all kinds of bad decisions that put the Texas office at risk. Other offices had already been shut down, and we were tottering on the brink. I was deeply concerned about my financial future.