Letters Continued 1

Debbie was not a mommy thing. Not openly, and only from my point of view, I never let her even smell the idea of it. I was genuinely attracted to her from the moment I saw her during the first week back to work. At one of the staff meetings, I saw her chatting during a break, eating a muffin, and drinking a coffee. She looked just like Michelene but with tan skin and ultra-white teeth.

Michelene, the woman I dated for over two years, loved, loved her children, all six of them, and never once got under her panties. Debbie looked just like her. Her mannerisms during the staff meeting break reminded me of Michelene and I decided in that moment that I would court and bed her, eventually.

It was a flashing thought really, just a way of amusing myself and I put the thought out as quickly as it had ignited. I went on with that first week back stuff. You were a part of that too. You and TW were basically my only friends there. That year we were back in the remodeled building, totally dialed in, technically forward-thinking environment, and we were all on separate floors and hallways, so I spent a lot of time stopping in at teachers' rooms and chatting, making small talk. I made a special stop at Debbie's room.

She was very friendly and I made her laugh almost immediately so I knew I would like her. I know I was projecting all of Michelene's characteristics onto Debbie, but she seemed to fit. I was aware even then that I needed to look at her objectively and not in comparison. I was constantly calibrating my perception of her to account for my inclination to see Michelene in everything she did.

I could make her laugh just as easily as I could make Michelene laugh. It was so natural. And we became work buddies. No one ever suspected it because of the age difference. Hell, I didn't even suspect it at first, I was playing the long long game. It wasn't until I really began to get to know her that I began to calculate my moves. Debbie had no clue. I know this because when I kissed her for the first time, she literally asked me if it was some mommy/son thing. She said she couldn't go along with that. And that's where the fantasy was born.

She put it in my head. Up until that time, it was all about her uncanny resemblance to Michelene. Now my aim was to treat her the way I imagined a submissive man might treat his mother if he were in love with her. I made sure always to give her oral. I was always licking her pussy and asshole, I was always at her feet. She had wonderful feet. And shoes. God damn sexy heels. And she wore a girdle, stockings, and silky dresses and blouses when we went out. She was smooth. And I know what you're thinking, honestly, I never looked at her pussy. I just used my senses, and closed my eyes, like a Jedi. I am very good when I want to be.

I'm getting ahead of myself though. It was during that last year that I was also dating a Japanese woman, she had two teenage kids. I went to some Asian buffet with her and her kids one time. I think we also went to some Zoo or amusement park thing with them too, because I remember driving a long distance with them in the car. She was cool. She licked my asshole. I was shaved of course, as I always was, pubis, balls, asshole, and thighs. She loved it. When she found out that I liked it too, she did it every time we were together and wet. She salivated. She fingered me too. She fucked me Amazon-style. She was like Japanese porn when the woman is the dominant one. I was hooked on her, but in a way that I could put her off, but if I called her, she would be johnny-on-the-spot and ready to rumble.

I was also getting my first taste of cock, but you know the boring details of that. I will say, that during this time, I was very busy socially and lived a very full life. My sissy play was nothing back then. And yet, it did take time. If I had a long weekend I would spend the whole Saturday dressing up, drinking, taking percosets, and smoking weed all day, then at night solicit cocks to my door.

And right around that time, during Christmas holiday, I asked her out to a place on the beach, a tiki bar, live Jimmy Buffet, margaritas, that sort of place, just to celebrate. She accepted. I got there early and got us a pitcher of original margaritas and took my little one-hitter so smoke in the bathroom.

We got along great. Like I said, we were kind of work buddies. We'd stop in and see each other in our respective rooms, sit with each other at staff meetings, and have lunch with each other, that sort of thing. But it was strictly platonic, but friendly, more like girlfriends. Our age difference probably threw most people off of any suspicions. She was so easy to talk to and I opened up to her at dinner that night. We had a great time. We went back to her place and she showed me around and we ended up looking at her family albums in her study. It was such a turn-on to see her as a young woman, the photos looked like photos of my childhood, still a boy. That's when I grabbed her close to me and kissed her.

That's also when she asked me if this was some mommy/son fantasy. To which I assured her by telling her the story of Michelene. I let it all out. I didn't tell her the part about the two of them being twins, that would be crazy. I parlayed my tragic love story with Michelene into a sympathy vote. I told Debbie how happy and lucky I was to have met a woman like her, so sexy and sure of herself. I told her how arousing her ferocity was. I gave her all the power.

She was convinced because that night she fucked me in a way I'd not been before. I still use it as part of my arsenal during sessions. I'm lying back in the center of this huge couch that's in front of the TV. My feet are planted on the ground and Debbie is sitting between my legs, back facing me, and squatting down on my cock. She uses her thighs to spread my legs wider and I lift them up so that my shaved asshole is wide open she grabs onto my feet and uses them like braces to steady herself and then uses them as leverage as she pounded me over and over. With my legs spread wide, my asshole exposed, I begged her to slap my balls, I said it and I didn't care, and neither did she. She began slapping and playing with my balls and I fucked her hard thrusting up from beneath her pounding as hard as I could so that my balls slapped up and down against her pussy and her fists.

She tuned into that little kink and she broke it out quite often to please me. That's the thing about an older woman, very attentive.

But I treated her like a queen. We would go to plays or musicals, the symphony. We dressed up nice cleaned up good, and went out on the town.

With Debbie and Toyoko (that was the Japanese woman's name) and my side gigs getting cock, one more thing happened in that time. M contacted me and came down to spend a weekend with me in the Keys. She had work and my sister's husband had a boat so I fucked the shit out of M that whole weekend. It was amazing. I was only 40 years old then. Damn. I have had some good runs. No casanova, but a couple of good runs. I never really thought of it like this before but I'm starting to realize I had it pretty good there.

Eventually, I just stopped calling Toyoko. One day, long after I'd thought the matter settled, she called and she was upset. I apologized. I didn't relent and I mourned our loss, mostly the sex part, but still, I mourned the other things too. M flew me to New York for a weekend and we fucked Amazon-style in the hotel all weekend. She told me stories of her wild times in Vegas at some annual convention. She was very sordid and her stories enraged me, yet when she whispered in my ear the same stories as she fucked me with her cock Amazon-style I forgave her instantly.

Debbie was angry when I told her I was moving to Europe, she even wanted to come along. She offered to wait for me. I was shocked, but also I felt bad because in my mind it was never a long-term affair. It was easy for me to leave it all behind.

I think of her and have a smile always. Just like with M and Michelene, and you.