Dear Diary
By SubKaren92
Even though I have recently cracked the 30 year old mark, OK it was four years ago, I still go by Katie instead of the more mature Kate or Katherine, my given name. I also still write in my diary, I tell people it is a journal, almost every day. It is something I started in primary school as a class project. I found I liked doing it and never stopped. My teacher warned us not to detail anything we wouldn't want someone else reading. That was fine for the assignment, but as I got older, my entries got far more personal about my feelings, wants and desires. By the time I got to college, honestly, I would have been pretty embarrassed by what I wrote about myself.
If you had found my journal (I carefully hid it from my roommate) you would find that unlike some college girls who use their new found freedom to experiment sexually, I was into full scale research. My first couple of years I fucked a lot. I kissed some frogs looking for my sexual prince. My diary kind of morphed into a record of my exploits and ratings of my partners. I finally found my prince, at least my perception of a prince at the time, early in my junior year.The thing that made him different? Unlike so many college boys, he wasn't interested in seducing me or what I was feeling. Toward the end of our first date, he just told me I was coming back to his apartment and we were going to fuck. You would think I would have been offended and kicked his ass to the curb, but my body reacted with an unexpected wave of arousal and I meekly agreed.
He was definity a 5-star lover in my diary and I was his fuck bunny. It was also during this period that I licked my first pussy. He had told me we were going to have a three-way and he provided the other girl. He was probably fucking her on the side too, but honestly, I didn't care. He knew how to play my body better than anybody I'd been with and I wasn't prepared to give that up. Sure it was awkward the first time I had to share him, but I found I loved the taste of pussy. I'd tasted my own, of course, licking my fingers after a successful masturbation session, but she was different. Not better or worse mind you (I liked the taste of my own juices) but different. Eating her out while getting drilled from behind was an amazing experience. When we switched places and she ate me out, I had zero jealousy that my boyfriend was fucking her. Part of that was she was more skilled at eating pussy than any partner I had ever had to that point. She made me cum twice before my boyfriend pulled out of her and sprayed her back. Like the good girlfriend I thought I was, I licked her back clean. Then we kissed. It was the first time I'd kiss anybody when I had jizz on my lips. I found that very erotic.
At the time, I don't think I understood exactly why it turned me on so much for him to just tell me what to do sexually, but I certainly craved that treatment. Before you ask, no he wasn't my Master, a term I didn't even know about back then, and no I wasn't his submissive. In retrospect, I had submissive tendencies back then, but for me, it was just about being with a strong, self-controlled man. And women. I enjoyed when any other women he brought into our bed would also be firm with me and tell me what to do. It was one of our three-way partners that also taught me the pleasures of solo women-on-women play. She earned a 5-star review in my diary too and I found the satisfaction of getting her off was similar to the satisfaction I got from making him cum.
We parted ways after graduation as our employment brought us to different cities. I knew better than to try and make a long distance relationship work with someone who would be fucking other women all the time. Besides, our relationship, such as it was, was mostly physical. I figured I could replace that and hopefully find an emotional connection as well. It turns out that was easier said than done.
I drifted through a number of relationships as I built my career as a marketing director for a small ad agency. I had both male and female lovers, some better than others, some more demanding of me than others, but I never found "the one" like I had in college. During this time I learned more about sexual submission online, but I still wasn't ready to classify myself as a sub. If you read my journal and my descriptions of which fantasies got me off the best when I masturbated you wouldn't think that, but it was true. I confessed my needs to one woman I dated for a few months, but she lacked the desire to take control of me and we broke up. Then the house next door to me went up for sale.
I live in a solidly middle class neighborhood in a cute two bedroom cape cod style house. The mortgage is cheaper than rent and I am able to keep one bedroom as a home office. Since COVID, I primarily work from home going into the office as little as possible. I found I was much more creative when separated from the distractions of the office and my bosses were pleased with my output so it worked for everyone. At least for a while. Then I got distracted.
A couple about ten years older than me bought the house next door. While they were moving in, I did the neighborly thing and went over to introduce myself. To say I was infatuated with them immediately would be an understatement. Infatuated with her at least. He was a bit overweight and was starting to bald. She looked like she worked out every day, had an amazing smile and the deepest, bluest eyes I had ever seen. When she introduced herself, her voice was dripping with the strength I had been missing in my relationships and I stammered when replying with my name. Fortunately she didn't seem to notice and introduced her husband. Janice and Jim were their names and that night I masturbated to the fantasy of her ordering me to fuck him. I came very hard, twice, and dutifully wrote down every sordid detail in my diary.
Over the next couple of weeks, Janice and I became friends, but I never got the sense from her that she swung both ways so having her as a lover seemed impossible. Jim was always cordial, but he was also aloof and I didn't know him too well. Still, they were good neighbors and we exchanged keys to each other's houses in case of an emergency. My fantasies had moved on from having them in starring roles, although I admit I occasionally jilled one off thinking of Janice and an afternoon tryst. I also had another boyfriend during this time, but I knew he would be a short timer and I basically kept him around for my amusement. That amusement ended on Memorial Day weekend when Janice and Jim invited us over to grill out.
What changed? Janice and Jim had a daughter who was home from college. Kimberly (introduced as Kim) had just finished her first year. She was a spitting image of Janice, just twenty-some years younger, that is to say, gorgeous. I knew from the moment I shook her hand that she would star in my fantasies that night and I dismissed my boyfriend as soon as the party was over. I knew he wouldn't give me as good of an orgasm as my fantasies could give myself. Jilling off to your neighbor's daughter was one thing, but I didn't expect it to go anywhere. How could I have explained myself to Janice and Jim? But thinking back to my own experimentation in college, it was easy to imagine Kim doing the same. My fingers and vibrator did the rest. She was 5-stars (OK 6) in my journal. Then I found out she liked to lay out and suntan in the afternoon.
My second floor home office's window allowed me to see into the neighbor's yard. Kim's insistence on wearing tiny bikinis was distracting to say the least. The first time I saw her, I knew I would be taking afternoon breaks to pleasure myself. That wasn't entirely unusual, but I'd never done it sitting in my office chair with my legs spread and looking out the window before. Over time, I made up an entire fantasy backstory for Kim and I never failed to orgasm imagining myself between her powerful thighs or, as was new to my fantasy life, across her lap being spanked for being a bad girl. Apparently my online research into dominance and submission had rubbed off on me a bit because imagining her spanking me and then teasing my pussy with her fingers gave me spectacular orgasms.
My fantasy life was great and Kim would have probably stayed as a naughty hidden desire had I not had to go on a work trip. I had finally worked up enough courage to order a paddle so I could spank myself and some naughty lingerie. It was scheduled to be delivered the day before I was to leave town. But that day, I got a message that the delivery had been delayed. I didn't want a package sitting for days on my front porch. I wasn't worried so much about it getting stolen, it wasn't worth that much, but I didn't want anybody to know the house was empty. I told Janice of my concerns and she said not to worry, she would watch for the package and put it inside. I felt relieved and wasn't stressed as I headed to the airport.
Alone in the hotel, I imagined what would happen if Janice decided to open the package and found the paddle. That took care of my sexual needs the first night. The second night I imagined Kim wearing the lingerie I bought. I hadn't brought my journal on the trip, but I was able to jot down some notes on the hotel notepad. When I got home, I was relieved to find my package unopened on the kitchen table. My secrets were preserved. Later that day I saw Kim outside doing her afternoon tanning and Janice outside doing some gardening. I went over to thank her and she assured me it was no trouble. In fact, Kim had been the one to take the package in. "Why don't you go thank her," Janice told me. My mind raced thinking that I would get to see her tiny bikini up close instead of from my room and I felt myself getting aroused. "Yes, I would like to do that," I replied.
Kim seemed indifferent to my walking up to her, but was gracious in accepting my thank you and I added a compliment about how much I liked her bathing suit. Her nipples were prominently on display and my trickle of arousal I had when Janice suggested I talk to Kim was quickly becoming a flash flood. "Well, I'd better get back to work," I told her. "Enjoy your tanning." I couldn't see her eyes behind her dark sunglasses, but she did have a wry, knowing smile. I made a hasty retreat, saying goodbye to Janice on the way, and made my way back to my voyeur nest to relieve my desire.
That may well have been the end of the story. Sure I was infatuated with Kim to the point you might call it an obsession, but Summer was drawing to a close and she would be heading back to college soon. Two weeks before that, however, Janice told me she had Jim were going away for the weekend. "Could you keep an eye on Kim for us?" she asked me. "I mean, she is obviously old enough to be on her own, but just make sure she's not throwing a wild party and check in on her a couple times." I assured the nervous mom that I would. Just before they left, I went over to their house. Kim was in her bikini as usual and my body reacted as you would expect. Janice told Kim I would be checking in on her. I assume she had already told her no parties. Kim was dismissive as she had been when I thanked her for bringing in my package.
Jim and Janice headed to the car, Kim to her chaise lounge in the backyard and I to my home office, grabbing the paddle and a vibrator as I went. I also stripped naked, which wasn't my usual routine. Although I wasn't worried about getting caught, masturbating while technically on the clock for work seemed like something I should do with work clothes on and my pants just unzipped. But that doesn't matter right then. I'd used the paddle a few times, but I was never too firm. I just couldn't do it to myself. I'd also never used it when watching Kim. But for some reason, today was different. Kim had positioned her chair so she was facing my window. That wasn't too unusual. What was unusual was she was sitting with her legs spread so I had a perfect view of the tiny wisp of cloth covering her pussy.
My fantasy world went into overdrive. Instead of sitting in my chair, I remained standing and bent forward against the window. I imagined Kim was wielding the paddle. With every swat I gave myself, I felt my pussy get wetter. Then I saw Kim take off her bikini top and start rubbing her nipples. I dropped the paddle and thrust two fingers into my needy pussy. I came immediately and repeatedly. Kim was teasing her nipples as if she was teasing me. My body was reacting as if my submission fantasies were being fulfilled. Her body was twisting as she toyed with her hard points, but she never rubbed her pussy. She had to be close to an orgasm and I was close to passing out from pleasure. Before that happened though, she stopped. She lifted her sunglasses so I could see her eyes and I knew she was looking at my window. Then she smiled and got up to go into the house. I masturbated again, this time fucking myself with my vibrator, thinking about her playing with herself, turned on by having me watch her.
