Condo Maintenance Man
Copyright© 2026 by Seafarer
Chapter 2 Madeleine and Holly
Fiction Sex Story: Chapter 2 Madeleine and Holly - Jackson was a blue-collar guy working in A/C & R at a Health Maintenance Organization (HMO). That job fizzled out, so he applied to work at a large condominium. He got the job as the maintenance man. He was hired to replace the previous maintenance man, who is retiring. Oddly, a lot of needy ladies live in the all-female condo. The maintenance logbook, which was passed down, has some cryptic euphemisms in it.
Caution: This Fiction Sex Story contains strong sexual content, including Ma/Fa Workplace Mother Son First Oral Sex Petting
Holly’s tits are so wonderful. They bobble and sway just a tiny bit as she fucks me. Mesmerized by the view, I thought of my Mom’s cousin, Madeleine. I had seen her bountiful tits.
When I was 15, Mom had a cancer scare, and she had a long surgical procedure to remove her tumor. After that, the chemo and radiation were going to be done.
Mom’s cousin Madeleine came to visit and help her through it all. They were like sisters growing up, so Mom told me to use the honorific “Aunt Madeleine” when talking to her.
I had always loved Madeleine. She always gave me a comfortable womanly hug growing up. She loved hugging in a way that always rubbed her titties on me. If she was Mom’s cousin, whatever. I didn’t care -I worshiped the ground that affectionate woman walked on.
Aunt Madeleine is a short, stocky woman with wide hips and big soft breasts. She likes to display a lot of cleavage. I once heard her say, “If you got it, flaunt it, baby.” I liked that concept as she would shove my face in the middle of her tits whenever possible and hug me silly.
Aunt Madeleine likes skin-tight shorts. Although she has had three kids, for a middle-aged 40-ish woman, she is pretty damn hot. She looks great, but her attitude was what propelled her through life. I especially love Aunt Madeleine’s long, curly black hair. It moves around when she moves her head the slightest bit. It’s like it’s alive or something.
At 15, I was indeed in love. First, Aunt Madeleine is not snotty like the high school girls I am around every day. Aunt Madeleine seems genuinely interested in me and talks with me often. She tells me she hears me with a thousand little touches, hugs, and kisses on my cheek.
The girls at school are snotty or catty. Most think they are prime stuff. They are interested in weird things and can’t talk about anything I feel is significant.
Women and girls all seem to want to maintain a feminine superiority of some sort over us males. Aunt Madeleine doesn’t act that way. Ladies at church and female teachers I come across are all about their position.
After Mom’s surgery was done late in the afternoon. We were told she would be out of it and sleep through the night. We should go home and return in the morning.
Aunt Madeleine and I discussed it. As we left, I felt worried about Mom. A never-ending list of “What-ifs” ran through my mind.
We stopped for a burger and fries on the way home. I only ate a little of my fries and put my burger in the fridge at home. Aunt Madeleine seemed to nibble at hers, too.
She excused herself to get comfortable, so I went in, changed into shorts, and came back out. She sat on the couch in short shorts and a loose top. She patted the sofa next to her, so I sat down.
Aunt Madeleine pulled my face to her lap. As I shifted down, my face rubbed on her big boobs, and I knew enough to feel she was bra-less. Well, she said she was going to get comfortable.
As I lay there, I began to smell her. I loved her perfume, but this was a different scent and was heady. I felt my dick get hard. I glanced down, and my shorts had poked out lewdly.
Aunt Madeleine chuckled and patted it. I was mortified.
She said, “I used to change your diapers. That thing was big even when you were a baby.”
She continued to gently touch it. I wanted to jump up and run away, but nothing like this had ever happened to me. My brain froze up. I didn’t know what to do or how to behave as my sort-of Aunt kept playing with me.
She put her hand on my waist and ran it inside my shorts until she had me in her hand. She gently massaged my balls as I started moaning. I realized in my moving about I had started rubbing my cheek on her big titties. I took it into my mouth and gummed her through her top.
After a while, I realized she knew exactly how to caress me. Whenever I got close to cuming, she would do something different, like rub my lower belly or gently tug my balls. Aunt Madeleine was playing me like an instrument. She did this for some time, and my balls began to really ache in need, a wet spot spread across my shorts.
She knew she had done enough when my hips started to move instinctively. She took me by the hand to Mom’s room, pulled my shorts off, and pushed me towards the bed. She pulled her top off, and there they were.
Those big tits that had always been in the forefront of most of my adolescent male dreams.
They were significant. As she moved, they moved in an opposite direction. Her areolas are at least three inches across, oval-shaped, and pointing sideways. Her nipples are pretty long. I did not know boobs could look like this.
I dearly loved my Aunt. She has somehow conditioned me to want her like this. She pushed her shorts down. They were so tight that she had to wiggle a little. There it was, my first look at a real live pussy.
Now I knew the source of that sexy smell; once bared, it flooded my senses. As far as a close look at her pussy, all I saw was this big thatch of shiny black hair. I knew there was supposed to be more to see.
She prodded me onto the bed and joined me. She began kissing me. She started easy and gently. As she continued to kiss me, she ran her hands over all of my body. I began trembling and then shaking all over as she made love to me.
She tickled me with her fingertips. Her nails were short, but wherever they passed, she left goosebumps in their wake. My Aunt is a mean bitch. She tortured my poor body for I don’t know how long.
I did not realize she was teaching me. She became my lovemaking teacher, and I was her student. I would do anything in the world for her. He paused in the kissing for a moment, and I moved my head and captured a teat between my lips. God, her nipples were fat and long. I felt the rubbery texture as she wiggled and groaned.
Aunt Madeleine said, “When you were a hungry baby, your Mom let me hold you like this. You would suck at my nipples to beat hell. I loved babies and nursing them keenly. At the time I nursed you, I had no milk, but I sure loved you trying. Suck my nipples, Jackson. See if anything comes out.
Thus began my tutorial on breasts and nipples. Aunt Madeleine liked it rough. Her theory was that big tits are less sensitive compared to small ones. She told me you have to figure out what works for each girl or woman. It’s a baseline of sorts that big tits like it rougher, and small ones do not.
Later, she would tell me that she experimented with other girls at college. That’s what informed her bout girls and women. It helped her when she began dating men.
She found that well-equipped men and lesser-endowed men reacted differently. Size matters, but mostly because it affects how people’s sense of touch excites them.
Aunt Madeleine swooped down at some point and took just the tip of my dick in her mouth. She used her tongue and then suckled just the tip alone as she used a hand to tug and handle my balls artfully. I doubt my dick was in her mouth for more than 15 seconds before I heaved up and squirted into her mouth.
My whole body became jittery, and I tingled everywhere.
My Aunt then taught me how to eat pussy. She started by holding it open and describing the parts I was seeing. She explained how doing different things made her have different sensations.
She explained that what one woman loves might turn another one off. The idea is to experiment carefully for several minutes to map out a woman’s erogenous zones. To also understand her responses.
My Aunt taught me to lick a clit gently and wetly and to lick the alphabet on the tip of her clit. Some women want it lightly and work up to a frenzy; others wish it firm. Or you can wiggle your tongue side to side or up and down instead of the alphabet thing. Some women prefer those methods.
She taught me how to finger a clit. Above all else, keep it wet. Every three swipes across the clit take another dip for pussy oil to keep her clitoris lubed. One dry rub can ruin a girl’s evening.
She taught me that some women do not like to be penetrated with a finger or a penis. It makes them feel uncomfortable or anxious. Some women need to be titillated until they can’t help themselves. They may demand penetration then.
Only then do you give it to them. Others never like it, and I had to be sensitive to that. Oral sex or mutual masturbation beats no sex at all. Be grateful for what you get.
You go slow and easy with inexperienced girls and with experienced women at their pace. It’s challenging for men to go slow. However, the rewards later are much better than three pumps and a dump, as Aunt Madeleine called it. It really beats an angry date, too.
Being attentive to girls’ or women’s needs is the most fun you can have.
I licked my Aunt to several cums. I got a second blow job; this time, I was not as quick. Eventually, she took me inside her Muffy. She called her pussy ‘Muffy.’ Why not? Men have names for their cocks or dicks.
Muffy really suited her cunt. She’s the one that named my dick JJ for Jackson Junior.
To read the complete story you need to be logged in:
Log In or
Register for a Free account
(Why register?)
* Allows you 3 stories to read in 24 hours.