Condo Maintenance Man
Copyright© 2026 by Seafarer
Chapter 8: My Cherry
Fiction Sex Story: Chapter 8: My Cherry - 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
Cherry White in #1049 more than made up for Francis.
Cherry surprised me when she opened the door. She is short, very short, yet quite dainty and slender. She looks too young. She’s wearing a short floral robe with a lot of leg showing. Cherry is a cute, young redheaded thing.
She said, “I’m sorry, I was just getting ready for a shower; she pretended to hide the right tittie that was poking out. She shrugged her shoulders and smiled at me as if to say, “What can you do?”
I had seen her a few times and thought she was someone’s granddaughter. Maybe a young adult daughter who was visiting.
She let me in and led me to the bathroom sink drain. It was supposedly stopped up. It could have been the rubber drain stopper covering the already shut drain. I got under the sink on my back and looked up, pretending to look at it.
Glancing at a movement. I saw Cherry’s robe was now hanging open. Oh my!
My eyes went directly to the red, bare, rectangular patch. It sat above her vaginal slit. The carpet and drapes matched perfectly, except the carpet was curlier. The patch was an inch wide and two inches tall. It seems someone else visits that Brazilian lady. Cherry’s tiny pussy looks immature with that hair job.
Julia told me Cherry is going to college and stays here for the quiet and the extra security. Cherry had evidently seen me in the halls as well and asked Julia about me.
My eyes made the slow transition up to her darling breasts. I swear she looks just out of puberty. They are maybe 2 1/2 inches wide. They come out an inch or an inch and a quarter, ending in a sharp, puffy tip. I think the entire end was a nipple. They are dime-sized and dome-shaped at the ends.
The most remarkable thing is that they’re red!
She saw my noticeable interest in my pants and slowly lowered herself onto my lap. She leaned over and kissed me softly. The first kiss was a peck, but the second soon became serious as she sprawled on me and made love to me for a minute. It was uncomfortable. I was scrunched with my head against that sink’s opening,
She got off me and held out her hand. I took it, and she led me to the living room, and she lowered her Murphy bed. She sat on the edge and slowly removed my clothes. She kissed and nibbled the areas of me that she had made bare. She wasn’t in a hurry and took her time.
She had seduced me in the partially open robe. Still, I enjoyed every bit of this girl’s fantasy, because that’s exactly what it was: her fantasy.
I later heard she had fantasized for weeks about meeting me. Julia had told her about the play-acting part. This was all Cherry’s idea of make-believe, to take me and make me her lover.
On the bed she started to caress me, lick me, and nibble some on JJ and the boys. When she took me inside her mouth, I knew she was inexperienced. She probably got her ideas from a romance novel. Women’s porn stories are all shirt-ripper BS. It’s short on usable descriptive text or how-to.
I shifted her body around so I could get at her vulva. Oops! Virgin territory. That was not much of a surprise. I pulled her smallish pussy towards my face, which disconnected her from JJ. The oral wasn’t all that good, anyway.
I probably shouldn’t have taken Cherry’s cherry with my tongue. So I bathed her tender little bits, giving her the tongue-lashing of her young life. After she was squirming and crying for more, I started the alphabet bit on her little clit. I didn’t even finish the first round when she froze in place, shaking and quaking on my face.
“Heavens! OH, Oh, oh, oh OHHhhhhhhhhhhhhhhhh...”
I gave Cherry a half-a-minute pause before I restarted my alphabet thing. I had waited the exact right amount of time because I had her spinning right up again soon after. I went slow to ease her into it the second cum. I dragged it out, but it paid off. She went nuts during her second climax. I was worried security might pound on the door.
“Oh, God! That’s soooo good! Ohyeeeesss ... MMMmmmmmmmmmm ahhhhhhhhh...”
She crumpled onto me and drenched me in her sweat as she lay there trying to get her wind back.
I took advantage of her relative recovery and got her on her back. I maneuvered her legs over my shoulder and put my cock in her pussy crease. I did not enter her, but I masturbated myself in her crease.
Fucking hell, rubbing JJ in her crease made her cum a third time. She was so hot and wiggly that she effectively removed her own cherry by moving wildly enough. I didn’t intend for that to happen, at least not then.
She muttered, “Owwie,” and after a short pause, Cherry went back at it.
I was only in her halfway. I followed her lead regarding speed and depth.
This position was hell, so I moved down until I was on hands and knees and inside her. She started to fuck back at me with more energy.
She whimpered. “So good, so good, ahhh ... So good...”