The Self Love Chronicles Ch. 01

The law of averages is the commonly held belief that a particular outcome or event will, over certain periods of time, occur at a frequency that is similar to its probability. In my case, that means that the more often I masturbate, the probability of my being discovered or caught increases. This the first in a series chronicling my masturbatory activities, and the incidents that have become known to others.

The first time getting caught pleasuring myself was without a doubt the most embarrassing thing to ever happen to me in my life at that time. It wouldn't be the last, but as time has passed, the memories and the impact on me have changed as I've gotten older.

The first time happened to me many years ago shortly after I got out of college and moved into my first apartment. In previous Literotica entries that I wrote to Playboy Playmate Carrie Jean Yazel and Penthouse Pet Anja Josefsen, I've talked about the autonomy I finally had being out on my own and living alone and not having to worry about interruptions during masturbation sessions. On several occasions, that turned out not to be the case.

I moved into my first apartment when I was in my mid 20s and was living alone at the time in a building with about 100 other tenants. One of those tenants was an early to mid-thirties (I'm guessing 33/34 years old) woman named Cheryl who lived across the hall from me. Cheryl was about 5'6" tall, 120 lbs. (at most), short sandy blonde hair she wore as a bob, and brown eyes. She was a really beautiful woman. She was a professional, working woman (based on how she dressed) and had a boyfriend. I don't know if he lived with her or just came and went. The building has an underground parking garage and my assigned spot was on the lower level, Cheryl's was on the upper level.

One evening I got home from work a little later than usual after stopping by the groceries to pick up something for dinner. I parked in my spot, slung my bag over my shoulder, and grabbed four plastic bags of groceries out of the trunk and slowly carried them over to the elevator. It was a lot to carry in one trip, but I was determined to do so all at once so I didn't have to go back down to my car. I hopped in the elevator and pressed 2 to take me up to the 2nd floor where my apartment was. The elevator stopped on the upper garage level and Cheryl stepped in the elevator.

My god, she looked stunning. She was coming home from either work or a business trip because she had a rolling back with her but she was dressed professionally with a dark grey skirt that hugged her hips and really showed off her curves, a matching jacket, a white blouse, and knee-high black leather boots. She was also wearing the most wonderful perfume; I couldn't figure out what it was. Based on how she was dressed and how she smelled, I got an erection in my pants in the elevator standing next to her, and it was a firm, stiff, raging hard on in my pants. Thankfully the elevator ride up was short and quick so she wouldn't have time to see and notice.

The elevator stopped on 2 and Cheryl walked out first. I was going slower since I was carrying my bag and my groceries so I ended up about 2 to 3 paces behind her. She had the most beautiful body and the sexiest ass and I got a good view of it watching her walk and seeing that ass move right in front of me. Having that view of her was absolutely heavenly and I'm glad she didn't turn around and look at me because she would have caught me gawking at her with a huge bulge in my pants.

Cheryl gets to her apartment, which is right across the hall from mine, unlocks her door and goes inside. I get to my door and have to put down my groceries so I can go through my bag to get out my keys. I unlock the door and bring my groceries into my apartment one bag at a time. My apartment door has an automatic door closer at the top so every time I go in the door closes behind me. I bring in all 4 bags of groceries and set them down on the kitchen counter just inside my apartment and set down my bag. I could still smell Cheryl's perfume and I was still aroused by it and by the image of her in her outfit and that walk down the hall. I wasn't going to make it to the bedroom for this. I went over to the patio door and drew the blinds because I was going to need privacy for what I was about to do. I then made my way to the couch to unwind, and unbuckled my belt, unbuttoned my pants then unzipped. I can see the bulge in my underwear so I lifted my ass up off the couch and pushed my underwear and pants down my thighs just above my knees. I couldn't wait and grabbed my penis with my right hand and started to slide my hand up and down the shaft. Oh god, I so needed to do that and it felt good. I let out a soft moan and sigh at the sensation of my stiff penis gently sliding in the palm of my right hand.

I gave it a few strokes while gently running my left hand up and down the inside of my left thigh. "Don't cum yet" was the first thing that came to my mind. "Take your time and enjoy yourself" that inner voice said. Slowly my pant went from my thighs, over my knees and down to my ankles. My left hand started to unbutton my shirt and I can feel the air on my chest as my nipples got hard.

I continued to fondle myself, while fantasizing about Cheryl. The first scenario that came to mind was taking her from behind in the elevator that we just shared and either dry humping her with my pants on and rubbing up against her skirt and her ass, then dropping my pants to my knees (where they currently were) while rubbing my erection along the crack of her ass. She would look over her right shoulder and give me a kiss, then push her hips back into my crotch, rocking them into my dry humping.

"Ooooh god, Cheryl" I softly whispered and moaned while I continued sliding my penis up and down the palm of my right hand. I moved my left hand back down between my legs and switched off, bringing my left hand around the shaft while my right hand caressed my inner thigh. My hand would eventually move from there to my balls as I gently fondled them and ran my fingers through my pubic hair.

I then kicked my shoes off one at a time and let my pants and underwear fall all the way to the floor and stepped out of them, leaving me with just my socks on. I took a quick moment to take off my socks and drop them on the floor then I completely removed my shirt and left it on the couch beside me. Now I was completely naked and unencumbered by any clothing and could really start to get into my masturbation even more.

My mind started to drift to my second sexual scenario with Cheryl. I started to visualize what it would be like to have her mounted on top of me riding me cowgirl style. I went from the couch to the floor to continue and what was once a light gentle stroking technique with my right had been much more aggressive and passionate. "Ohhhh fuck, Cheryl" I moaned. This time it wasn't a whisper; it was a little louder. I started to pump a little faster in rhythm to what I was fantasizing about Cheryl, then I took it to the next level.

I stopped pumping with my hand and held my right hand completely still. I was on the floor, flat on my back with my feet on the floor and my knees up. From this position, I lifted my hips up, bridging, and thrust them into my hand like I was fucking Cheryl from underneath. I started to work a good rhythm where I was literally fucking my right hand for Cheryl. OH GOD CHERYL. It wasn't a whisper; it wasn't a moan this time. I was getting louder and getting closer to orgasm, then it happened.

I'm fucking my right hand full throated calling out her name OH CHERYL CHERYL CHERYL I'M GOING TO CUM OH MY GOD I'M CUMMING CHERYL. At that very moment the door opened and Cheryl took half a step into my apartment and saw me on the floor, naked, thrusting my hips and my raging hard penis into my hand. I looked up and made eye contact with her seeing that I had been caught. I was past the point of no return and there was nothing I could do. She saw my shoot three streams of cum all over my belly as I released. The orgasm was so intense there was nothing I could do and could not stop. Cheryl had a look of complete surprise and shock at what she was seeing and, given the situation, took a step back and closed the door in front of her.

After I came down from my orgasm the situation had finally started to register. Cheryl just caught me masturbating and moaning her name during orgasm. Then I thought to and asked myself how she got in then I realized that I forgot to lock the door when I brought the last bag of groceries and the door closed behind me. I was so embarrassed and ashamed about what happened that I could never look Cheryl in the eye ever again. I avoided her everywhere if possible: in the elevator, in the mail room, the laundry room, the pool, or any other common area. I always wondered if she ever told anyone like the apartment manager (who I've previously mentioned in my letter to Anja Josefsen and revisit in part 2 of this series), her boyfriend or any of the other tenants. I also ask myself why she came in to my apartment. Did she hear me and was responding to what she might have thought of as a call for help? I ended up living there for another 6 months before I moved (after a second incident with my apartment manager Janice stay tuned for part 2) and never saw Cheryl again.

I look back at that incident with an older and more mature perspective and have a much different attitude. I didn't do anything wrong. I was in the privacy of my home and not out in public in a location where that activity would be inappropriate and didn't intrude on her with my sexual energy. Now, I find the incident to be a huge turn on, and would welcome her into my place to watch me from start to finish this time.