My last summer job. My 43 year old boss and me. 100% True story.

This is a 100% true story from my younger days.

When I was 22. I had a summer job working at an apartment complex. I used to help out a maintenance guy who was like 60 years old, and was the biggest pervert. He was about 5’5” and weight like 300lbs. He used to tell me all about his “pokers”, his booty calls. I had never before and since heard someone use that term for a hookup. I still smile thinking about that fat bastard. Even though he could be a dick sometimes, overall he treated me pretty well. I had to basically just do everything for him and I would spend most of my days cleaning out old apartments before they got rented again. Looking back on it, it was pretty gross cleaning people’s apartments. Stains on carpets, sometimes smelling cigarettes and sometimes Indian food, which I love but the smell can get to you. I remember once I found naked pictures of a woman who I used to see at the complex pool and thought she had a great body. She wasn't the most attractive but damn she had a body! Totally forgot about her until just now when I was thinking about all the gross shit I used to find.

It wasn’t a bad job for summers in college. I made good money and most days I could nap for a bit after finishing my work. I even life guarded after hours, so I would get there around 8, and finish around 9pm. Life guarding was great bc it was mostly moms wearing bathing suits hanging at the pool with their kids. I loved checking out the moms. I thought I was slick when I would creep on them but once an older woman with a heavy German accent was laying on her back, legs spread when she noticed I would come up for air after swimming my eyes would freeze and stare between her legs. She glared, stood up, and turned her chair around facing the fence. lol. What a horny pervert I was. I remember thinking she would tell my boss but nothing ever happened. After that I did not try to sneak glances at her pussy though.

The best part of my job though was the property manager, Sandy, she was a 43 year-old divorcee who was incredibly attractive. She used to wear short skirts every day and sit behind her desk. I made it a point to go into the office multiple times per day. Number one because she told me to come in and get water whenever I wanted from the water cooler, and number two because she was so sexy. I took full advantage of her offer of getting water, and I took every opportunity to look at her legs from the water cooler. The water cooler was about 15 feet away from the side of her desk, so I always got a great view of her legs with her mini skirt halfway up her thigh. Every time I would come in She would back her chair away from her desk and cross legs to talk to me. Every time she did that I couldn’t help but look down at her legs. She knew I looked, I know she did because she would wait to cross her legs until I was done filling my water. At the time though I didn’t think she knew anything.

I was in love with Sandy. She was kind and always so good to me, in addition to being gorgeous. I had worked there for three summers during college and I got to know her pretty well. She would always ask about school, and if I was dating any girls, and would always say “I bet all the ladies love you.”

I never did anything or try anything with her until my last day ever on the job. There was a company party on my last day, not for me, but she said it was my going away party anyway. Everyone was drinking, and as a 22 year-old I of course partook in the festivities. She did too.

It was a hot August day, and she took off her coat that matched her skirt. It was yellow and she looked so good. I’ll never forget that. By the end of the party I was pretty drunk and I could tell she was too. We were laughing a lot, telling funny stories about the residents of the complex. Towards the end of the party we were chatting, and I was trying to flirt with her. I remember asking her if she was dating anyone, and she replied something like. “no way, guys my age are not attractive anymore.”

I remember laughing and saying “oh, so you like younger guys then?“

She laughed, and said “you have no idea.” And actually winked at me. So I said “really? Are you dating younger guys?”

She smiled drunkenly and said “well, not exactly dating.”

As she said I can clearly remember that my dick twitched. I could tell she was feeling me.

So I took my shot. “Ohhhh wow, so who are the lucky guys?”

She laughed and said “Do not worry about it!”

I played along and said “Well,those guys are so damn lucky.” Then I added “You're so attractive.”

She smirked and said “Oh I’m lucky too, you know I got divorced a couple of years ago right? Well right after, I found out my ex husband was cheating on me for the last few years of our marriage so I decided to start having a good time myself.”

Little did she know that I knew all of it, the old guy used to tell me all of this stuff bc he knew I thought she was smoking hot. He actually used to call her Slutty Sandy. Haha. He said she knew she turned into a whore after she got divorced.

I said to her “I thought I heard someone say that but I wasn’t sure”

She laughed again and just said something along the lines of “I figured people were talking about it. Did anyone mention I’m dating anyone at work?.” And smirked at me.

Jim had said she was fucking the owner of the company(which I later learned was true.). My buddy’s dad was the owner of the management company so I got all the tea from him. I said “oh no, not at all. I haven’t heard really anything.”

I finally said to myself, “It’s now or never. Quit being a pussy and say something.”

So I walked a little closer like I was looking at something on her desk. I stood right next to her. She smelled amazing. Her perfume mixed with a little booze and cigarettes bc we had shared one earlier. My eyes were on her desk but I could tell she was looking at me. I remember getting closer, until our hips were touching. When I did that she immediately got even closer. Right in front of me, her ass was just to the left of where my dick was attempting to rip through my shorts like it had a mind of its own. My heart was racing. I was nervous as shit but also horny. I had been fantasizing about her for three years. Three years standing at the water cooler looking at her in her skirts, knowing that she maybe liked it because maybe she knew I would stare. At the time I thought she maybe didn’t know, but looking back on it I was such a fucking perv that I know it was obvious.

Anyway, back to the office. I remember lifting my arm and calculating where I should put it. On her waist? Ass? Legs? I almost touched her ass but at the last second I went for it and put it right on her waist. As soon as my hand touched her she kind of stood up, looked at the door, which was unlocked, but once she saw no one was coming in she grabbed my hand mom her waist. Fuck! I almost came in my shorts right there. You have to remember I was 22 and I was a horny bastard. Still am, lol, now that I think about it.

I actually asked her “Is my hand okay?” She turned and looked back at me and said, “of course.” At this point her face was about 8 inches from my face. I didn’t really know what to do, my hands were still shaking, I was nervous as shit but I just stared at her. I put my other hand around her waist as I stood behind her. After a few seconds my hormones took over and I pulled her gently against me. I know my cock was right up against her lower back. Because she looked back at me again and smiled. We stood there for a bit and I slowly just moved her by the waist while I moved my hips slightly. Ugh what I would give to have my hands on her again. She’s gotta be in her 60s now but I’m sure she’s still sexy. I was rock hard and her ass was pressed against my dick.

So I stood there gently pressing my dick against her when I heard her let out a sigh. Fuck me I knew she was feeling it but I was so damn horny my shaking hands couldn’t move. Finally I moved my right hand up towards her chest. As I did that she grabbed my hand and stopped me. My heart sank. I thought I was going to get cock blocked. She stopped, walked to the door, and locked it. Fuck. I remember thinking she was leaving and when she locked it I went crazy inside. I wanted to bend her over the desk right then and there but she stopped a few steps short and said, “what apartments are empty?”

I remember thinking “oh shit oh shit oh shit” and said “ughh I’ve been working in building two, first floor but I can’t remember the number.”

She said “okay, you go to building 2, find the empty unit and call my desk. I couldn’t txt back then but I had a cell phone. This was circa 2004, and not everyone had a cellphone and texting wasn’t that common. So I nodded and said “okay, sounds good, but why don’t we just walk there together?” Honestly i was afraid she would have second thoughts but she said “I can’t walk there with you. Everyone would know what was happening.”

I nodded and said okay but I was still thinking she wouldn’t show, so I got close to her, put my arms around her waist and got nose to nose. She had this amazing smell, I wish I knew what it was, If I ever smell it now I’ll know for sure it was her perfume. She took a breath and just got a little closer and kissed me. Just a peck on the lips, but I wanted more. She glanced at the door again, no one around, and gave me the most amazing kiss I have ever gotten. She put her tongue in my mouth, im sure i was slobbering all over, haha, but we kissed for about ten glorious seconds. She stopped and said “go, I’ll meet you there.”

So I walk over, building 2 was like 200 feet away, so not far but I had to not be seen by the other workers. I remember thinking i was fucking Tom Cruise in Mission Impossible and peeking around corners to make sure I wasn’t seen. Haha. I was pretty drunk so I probably was looking like a fool stopping, starting, walking, looking around the corner. SMH.

Anyway, I get to the building and I’m trying to remember which unit it was. I had keys to unlock every apt but I didn’t want to make a mistake and go in the wrong unit. So I walk around and I think I find the right unit and I put the key in. It turns and I knock and say “hello?” No answer. I take a breath and open the door fully and see my tools I had left earlier. I walk in, call the office and it rings once and she answers. “Blank apartments, this is Sandy.” I respond and say “hey, it’s unit 108.” She says “okay, be there in a second.”

I waited for what felt like an hour when I finally hear a knock. I stand up off of the floor and go open the door and she walks in.

I remember just smiling and looking at her and she smiled back. The only thing I remember her saying was “ugh finally.” So I kiss her. Really kiss her. My hands are all over her. On her ass, around her waist, and finally I muster up the courage to grab her tits. She simply moaned “ugggh, I love that.” She starts kissing me more, our tongues in each others throats and I lift her shirt up, I get my right hand under her bra and grab her amazing tits. I’m pretty sure she knew how nervous I was, she chuckled a second but was into it.

We kissed for a bit more when I got even more handsy. I had been wanting to get my hands on her legs since the day I met her. They were so tan and toned. I remember lifting her skirt and putting my hands on her legs. She was basically climbing on me at this point. Her shirt untucked, skirt above her ass and my hands everywhere. I wasn’t sure how far this was going to go, but I was content with that. Kissing an older woman who I had been smitten by, while touching her everywhere. She was turned on.

She kept moaning and groaning quietly but I could tell she was loving it. Then, she started unbuttoning my shorts. I swear my mouth had to be gaping open as she undid the zipper. She pulled my pants down slightly, reached into my waistband and took my cock out. She jerked me first, smiling but also saying “ohhh my… it’s big.” I was 6’1 about 225. I was in great shape as I was about to start my last college football season. I knew I had a nice cock but I loved how she said that. I was about 8” when hard. I remember her looking at it, stroking with both hands, pondering what she wanted to do with it.

She stroked me for a bit while we kept kissing, and after a minute She bends over and takes my cock in her mouth. I gasped. lol. I remember she looked at me and said “did that hurt?” I quickly said no and got on my toes to put my cock right at her face again. She sucked me for a minute then grabbed my hand and walked to the counter. I was in heaven. I had my hands on her ass, She was wearing full back panties that were jet black and silky. So soft. I kept caressing her tight ass as we walked towards the counter.

She stopped, looked at me and said “I want you inside of me.” I pretty much melted and almost fell over when she said that. I wasn’t too experienced but I knew what I was doing. She bent over the counter and lifted her skirt up. She looked back at me and that’s when I knew I was going to fuck her. I remember I was so fucking horny I fumbled with my dick, went up behind her and tried getting my dick in. Like an idiot I couldn’t get it in right away so she reached between her legs and grabbed it gently, rubbed it around her pussy until I felt warmth. It was the most glorious warm feeling I had ever felt in my life. Sure I’d had sex but this was my number one fantasy. This 40’something year old gorgeous woman just pulled my cock into her. I started fucking her. Fast and hard. Too fast and she said “easy easy” after about 30 seconds and put her hand out behind her so I didn’t get too deep. I slowed down and just let her take over. She kept her hand back making sure I didn’t get too deep while she slowly backed her ass up onto my cock. The other hand I realized was on her clit. I even asked “omg, are you rubbing your clit?” She smiled and said “yeah, it feels amazing when I rub my clit while I get fucked.”

I kept pumping in and out at a slow pace, her pussy was incredible. She was shaved but not bare. She kept a thin black strip right up to her clit. I can still clearly remember how fucking hot her pussy looked. So shiny and soaked. She was enjoying it. After a bit I could get balls deep. Her pussy had adjusted to my dick and she started going faster. I’ve always been fortunate to not cum fast. To this day I can hold off on orgasms for a long time. So I start plowing her. I mean I’m fucking her hard. She’s starting to let loose and her fucking pussy was just leaking. At one point I pulled out, and got on my hands and knees and said “I want to eat you out.” She nodded and smiled and I sunk my tongue into her pussy. My college girlfriend once called me a god with my tongue so I was pretty good at it, I just had to adjust my technique to what I could tell she enjoyed. The entire experience was unforgettable but my favorite part was getting on my knees and seeing her bent over, pussy dripping, asshole right at my nose, as I plunged my tongue in her. I spent a bit fucking her with my tongue but I knew that the key to a woman was the clit. Her pussy was perfect and her clit stuck out slightly, engorged from the urge, looking absolutely delicious. As I started on her clit i could tell she was loving it. Not just the moaning but just how she would move her hips and ass so I hit just the right spot. I know she was close to cumming but she also was jonesing to get fucked more. She ended up standing up and kissing me more and saying “wow. You’ve had some experience buddy.” I smiled as she grabbed me by the arm and we went to the living room.

The apartment was empty so i remember it was echoey in there. We got to the living room and she said “sit.” I quickly sat down and as I sat she spread her legs, walked about half way up my body and squatted. My cock was right at her opening when she grabbed it, adjusted, and fucking stuck my cock all the way in. She groaned. I was a horny mess. I just wanted to fuck the shit out of her. She closed her eyes and got to her feet with my cock balls deep in her and just started squatting onto my dick. The sounds that came from this woman were ungodly. She was moaning loudly, her pussy was echoing in the empty living room, making wet noises as her ass and pussy slapped onto my body. I remember reaching up and grabbing her tits. Her shirt completely unbuttoned and my hands grabbing onto her perfect tits. I’ll never forget when she said she to me “pinch my nipples.” I obliged but I was too soft with my fingers. “Harder. Squeeze harder. I like my nipples pinches hard.” I squeezed hard and she groaned “oh my god fuck. Keep doing that.” I kept pinching her nipples and clumsily tried to do a situp to get my tongue on her. She pushed me back down and grabbed my hands and just smiled and said “pinch.”

She rode me for a few minutes. After a bit her legs got tired so she got to her knees and just started to grind her pussy onto my dick. Each time she would get it deep she would pause and open her mouth and let out a moan. She kept rubbing her clit too. I loved that since my college girlfriend used to do that for me all the time. To this day it’s my biggest kink. I absolutely felt like a porn star.

After that I got a little more confident and I took her and without letting my cock slip out put her on her back. I remember her legs spread, my cock inside her pussy and looking at her. She looked amazing. I remember being on my knees, my cock balls deep in her, and seeing that gorgeous pussy. Fuck I still masturbate to that view all the time. I leaned down, and kissed her. Like really kissed her. No awkwardness, no smirk, just a passionate kiss with this amazing woman that I’d been turned on by for years. I started fucking her fast. First with my weight on top of her, then I put my weight on my hands and tips my toes and just pounded her. She was going crazy at this point. Still rubbing her clit, but now I could tell she was trying to cum. I fucked her for a few minutes when her breaths got longer, her eyes were closed but when I would kiss her she opened them to look me right in the eye. I slowed down to let her get into a rhythm, and she said “that’s it. Like that. I’m gonna cum soon.” I just drove my dick in and out slowly. Watching for her own rhythm with her hands on her clit. As I watched her my own pace started to match her rhythm. She would slow down and I slowed down my fucking. Then she would go fast and I’d match her. She just kept saying “keep going, oh god babe, keep going, I’m close.” As she said that I could tell I was getting closer. I said “I’m gonna cum with you, where do you want me to cum?” Her response basically started my orgasm. “Cum in me. I want to feel it.”

Ballgame. Not 15 seconds later I feel the rush coming on and I say “oh fuck, I’m cumming, oh fuck I’m going to cum inside of yo…”

Eruption. I busted a huge load and started almost yelling. I groaned “ohhhh fffffucccckk. Ffffucck. Im cumming inside of you.”

As soon as she knew I was cumming,her orgasm came in like a fucking freight train. She said “I’m cumming, I’m cumming omg, fffffuck.” She came sooo hard. Her hips moving up and down as she screamed and groaned. I actually got nervous that someone would hear us but no one did. As her orgasm died down I saw her face. Smiling, breathing, eyes closed just in pure bliss.

I had never cum inside anyone before. I actually said that. “Omg that’s the first time I’ve ever cum inside someone.” She smiled and said “not a worry, I’m on the pill.”

We laid there for a bit. But eventually I knew she had to get back. I was done. My time at the apartment complex ended 15 minutes after I creampied her. I don’t remember much of what we talked about afterwards. I think maybe she was having some post nut clarity but she didn’t say it. I was just smiling. I think I kept trying to awkwardly kiss her but I could tell she was done kissing. We said goodbye a few minutes later. She left through the front door and she told me to use the patio door. I gave her one last kiss goodbye and said “thanks. Ive wanted you since the first day I saw you.” She smiled, kissed me and said “I know. Me too.”

I never saw Sandy again. I finished my last year of college the following spring and graduated in May. That was my last summer of freedom before I started my first adult job. When I was home the following summer I wasn’t working until August so I would occasionally drive by the complex to see if I saw her walking out. I never did though. I started my first adult job and thoughts of Sandy became less and less. I found out a few years later that she ended up marrying my buddy’s dad. Haha. It was true! I remember my buddy told me his dad was getting married and he said “You know her, Sandy, from blank Apartments.” I froze for a second, tempted to say something, but I never did. I figured Sandy was happy, and I really liked her so I never said anything. I’m glad I didn’t and I hope she’s doing well. I lost touch with my friend so I have no idea how they’re doing but just last week I was with my family and on the way home from a volleyball tournament with my kids and wife I passed the complex for the first time in years. I said “Hey guys, I used to work here.” They almost didn’t say anything but my youngest asked “what did you do at an apartment complex?” My wife and kids looked at me and I just said “I helped a guy named Jim. I loved that job. There was a really nice lady that worked here that used to always wave me in to get a drink of water from the cooler on hot days.” I stared straight ahead, smiling, thinking about my last day with Sandy. Everyone lost interest but I spent the last twenty minutes of the ride thinking about that day.

This is the first time I’ve ever told this story. Not sure why. I still think about her at the most random times. Sometimes when someone says “oh man she is hot for an older woman.” I think and smile about those legs and skirts.

Sandy, wherever you are I hope married life is going great. I hope you think about my last day as fondly as I remember it.

100% true story. Feel free to message with questions.