I had worked with charlotte Mays for roughly two years now in a small office that supported a large-scale contractor. My job was to track the progress of our crews and follow-up with the clients who outsourced our work. Charlotte supported the operations manager of our office, and was a no-nonsense, but sweet lady in her early fifties. Charlotte and I had a good relationship, even though I was only 24 at the time. Charlotte was a medium-toned black woman standing about 5″6, with a plump, but not fat figure. She carried a pair of 38 FF’s that had me sweating from the moment I met her. I was fascinated with her breasts, which just had that beautiful natural hang to them, and couldn’t be hidden by even the firmest of business suits. Sometimes I thought she would purposely wear tight sweaters that revealed a lot of cleavage, and bend over in front of me……or stand overly close to my face as I was seated at my desk. I would frequently race to the bathroom at work and rub out a quick load.
The good news was that charlotte was a divorcee who lived alone in a large house in the suburbs. One Friday after a long week of work, she asked if I wanted to hang-out at her place the next day and check out her newly remodeled living room. I quickly and not so smoothly accepted.
I arrived at her home the next day around 2:00pm. Charlotte wore a thin white v-neck sweater that contrasted with the smooth brown cleavage spilling from her chest. She gave me a detailed tour of her home, and finally arrived at a door in the upstairs portion of her house.
She told me that she had lied, and this was really the room that she had remodeled. I walked in to find a dimly lit room with sheers surrounding what looked to be a massage table.
Charlotte asked what I thought of it, to which I replied; “it looks great…..what’s it for?”
She told me that she had recently gotten her masseuse license, and that she would be working from home on the evenings and weekends.
I told her how exciting it was, and that I was happy for her.
She then asked me if I wouldn’t mind being her first customer.
I practically started shaking with excitement, and managed a nervous acceptance of her offer.
She asked me to remove my clothes down to my underwear, and to lay underneath the white cloth and await her return.
I readied myself for her return, and began to wonder if I would have to lay on my back at any point, thus revealing my hard-on. She re-appeared wearing a silk black robe that was slightly parted in the middle, revealing a canyon of mature black tit-flesh.
She asked me to just relax, and lay on my stomach. She worked her way all over my back, neck, shoulders, and finally down to my feet. She slowly eased her way up my calves and thighs where I thought I was going to die.
I had a raging hard-on and hadn’t even been looking at her breasts. My breathing was becoming more rapid, and she asked if I was ok. I said yes, that I was fine.
She said, “you don’t sound fine, why don’t you roll over so I can give you a facial massage on the temporal lobes—-sometimes that really does the trick.” I rolled over flushed with excitement. She noticed this, and probably my hard-on for that matter, and said “boy, you really are all worked up aren’t you?”
One thing that worried me the most was that not only would she be able to see how excited I really was, but also how small my penis was through the thin cotton sheet. Charlotte began rubbing my temples as her breasts hung tantalizingly over my face. I just gazed into their valley for what seemed like ages, when she said;
” Brian, is that little dick of yours all worked up over my big old breasts?”
I nearly passed out. I said; “wwh wh what?”
She said; “I’ve known for awhile now that you’re infatuated with my huge black tits, but I had no idea your dick was so small.”
I told her that I didn’t know what to say, and she said; ” why don’t you show me that little thing of yours so I can see just how little it really is.”
I told her I didn’t want to, and she said that was nonsense, as she swiftly pulled off the cover, and yanked down my boxers while walking to the foot of the table.
I was completely naked on the table now, my 4.5″ skinny little penis rock hard while she bent down with her huge black breasts swaying directly over my shins.
She ran her hand up the side of my leg and said; ” relax Brian, its ok that your dick is tiny. Did you know how small it was?” of course I knew. She then began to fondle my testicles with her fingernails and told me that I had to admit to her that I had a small dick.
I hesitated, and she told me that it was the only way to be ok with it.
She said: ” now tell me what a pathetic little dick you have Brian.”…as she ran her hand along the underside of my puny shaft. I said that I couldn’t, but she told me again that I had to…..I finally uttered:
” I have a puny little dick.”
She said: “now tell me that you have a puny little dick, and you wanna stick it between my huge black breasts.”
I said: “Charlotte, I have a puny little dick, and I wanna stick it between your huge black breasts.”
She smiled and softly caressed my penis, as she stood up and asked me: “would you like to see them?”
I nodded yes. She undid her robe and out fell two of the largest, mot beautiful chocolate colored breasts I have ever seen. They were the size of watermelons, slowly easing their way up my legs and finally resting onto my little dick. She took my dick in her hands, applied some lotion to it, and then worked it in and out of her beautiful valley until I exploded deep within her mammaries.
I let my head fall back, emotionally spent from the most powerful orgasm I ever had.
She ran her hand through my hair and said: “you’re going to be my little white boy-toy aren’t you?”
I nodded in obedience……..When I returned to the office Monday morning, I didn’t know what to expect. Since my visit to Charlotte’s house, I had masturbated six times in less than two days, re-living the incredible experience from her massage room.
The way she so delicately exposed my insecurities about my small penis, and completely manipulated me with the power of her enormous breasts. The fact that she was black, and 30 years older than I, somehow made it all the more thrilling.
I was apprehensive, nervous, and excited as I made the walk from my car to the entrance of our building. Somehow, in the back of my mind, I knew that Charlotte Mays would lead the way, and I would have no choice but to follow…
Charlotte was of course already there when I arrived, wearing a tight black turtle neck that beautifully hugged the enormous curves of her huge natural breasts. I attempted to steal a glance at her breasts as I walked by her desk, but she inevitably caught me looking, and gave me a knowing grin. I was completely infatuated with her tits. There was no getting around it. I had to see them again, and soon.
Later that evening, as I was wrapping things up for the day in my office, Charlotte came into my office to “talk” about things.
Before she began, she assured me that we were the only two left in the building. God, her breasts looked SO enormous as she made her way to the other side of my desk. She had a seat across from me, and began to speak…
“Brian, how’s my little boy doing today? Did you have fun the other night? You must have, ’cause I’ve noticed you looking at my breasts even more than usual today. Has your little dick gotten all excited thinking about my big ‘ole titties today?”
I could barely speak I was getting so excited just listening to her. “Well?” She said.
“Yes, Charlotte, they look amazing today, you turn me on so much.”
“Good, Brian, that’s just what I wanted to hear. We’re gonna have a little fun tonight here at the office. Don’t worry though, I’ve locked all the doors so no one can get in.
Here’s the bottom line Brian; I know that you can’t stop staring at my breasts, and that you’ve got a skinny little pencil dick in your pants there, but you’ve managed to get a higher position than mine with this company. I think its only fair that you help with some of my more menial tasks. What do you think?”
“Anything you want Charlotte, anything.”
“That’s what I thought you’d say. Before you get started though, I’m gonna have you take those clothes off first ok?”
“Ummmm, do you think it’ll be ok?”
“Why Brian, are you afraid someone may see that little thing hiding in your pants?”
“Whatever you want Charlotte. I will do it.”
“That’s my good little boy. Now take ’em off.”
I did as I was told. Self-consciously removing my shirt first, then my shoes, socks, pants, and most reluctantly…my underwear. I was no to surprisingly rock hard when my boxers were finally removed.
“Aaaaaawwwww isn’t that sweet. Brian you’re all hard and excited aren’t you? Are you embarrassed by your small dick?”
“Y-y-y-yes, yes I am.”
“Well, you should be Brian. Its just so darn skinny; and short too. Does the fact that I’m black scare you Brian?”
As she asked this question, Charlotte moved within one foot of me, and stuck her breasts out while doing so, tantalizing me with their amazing sway.
“Well, does it? I think you’re embarrassed by the fact that your dick gets so hard for a black woman. Especially one as old as me. But I think we both know why that is, don’t we?”
As she asked that final question, Charlotte gently pressed her huge breasts against my chest, and looked down at them; as if to say, ‘tell me I’m wrong.’
Charlotte then began having me file some papers for her stark naked; poking fun at my small dick and saying things like: “Hurry up oscar meyer weener, I don’t have all night.”
I inputted data on her spreadsheets naked as well, while she stood behind me at the computer with her breasts massaging the back of my head. She then reached down to my leg and gently squeezed my penis saying: ” I can see your little one is turned on isn’t he?”
Charlotte finally allowed me to take a break, and asked me to join her in the employee lounge. I walked into the lounge and Charlotte asked me to lie down on the floor.
I did as I was told and awaited her next move. In an excruciatingly slow movement, she removed her turtle neck. Her breasts remained encased in a non-push-up white bra. This bra contrasted amazingly with her huge black tits, and she knew it.
“You like the way my black breasts look in this white bra, don’t you Brian?”
“Yes, Charlotte, I love your huge black tits, and I am turned on by the fact that your are black.” (there was no holding back now) “I have always been turned on by black women Charlotte, especially the ones with the huge breasts, and definitely the older ones too. I guess, a part of me has always been ashamed by that, but I can honestly say now, that I have nothing to be ashamed of.”
“You don’t?” She said, as she looked down at my tiny little dick, and began to stroke it. “Well, I guess this little thing could be bigger.”
“You’ve got that right!” I said. Charlotte then stood up, removed her pants & panties, and straddled me in one fluid motion; easily engulfing my penis with her mature vagina.
As she faced me, she unhooked her bra, and thrust her breasts in my face. Charlotte rode my little cock for about 30 seconds before I exploded not so deep within her.
Those were 30 of the greatest seconds of my life, as her huge boobs swung in front of my face, brushing my lips back and forth, while I eagerly grasped at them, and attempted to suck on her nipples.
“You’ve passed the first test Brian. I am proud of the way you admitted some of your darkest fantasies. I think you’ve earned the right to attend a course in boobology 101…”
Loretta walked into her room, where she had a makeup station by her bed, and closed the door behind her, only so that the door hit the arch, and she went to lay down over the queen-sized mattress. When she laid down, her legs were separated and she untied her robe, white as snow, to expose her pantyless hairy vagina to the air, as well as her diamond-shaped navel that was surrounded by thunderbolt-like yellow stretch marks.
She still wore on her head, the water-resistant shower cap. From a pocket of her robe, she reached for her nail filer and began filing her nails, blowing away any of the leftover white powdery dirt.
Maxwell peeked in between the door, but unfortunately all he could see was her head, and the end of the bed. Much to his luck, there was a hidden peephole drilled into the next wall from the storage room next door, but even that was useless as it was only good for seeing straight ahead, where Loretta and the bed was not.
Maxwell moved to that location anyway, going into the storage room, moving all the office drawers and boxes from the way to look through the hole and wait.
Loretta finished scraping away at her nails and got up, removing herself from the bed. She walked toward her dresser, walking right past the direction of the unsuspected spy hole where her son spotted her. She always knew the hole was there due to the door knob but failed to be aware of the fact that he was using it as a peephole for perverted reasons.
Maxwell saw that her robe was untied and started to get excited, as he could only see just a bit of her black hair in between her legs. His penis started to swell. He could also see the bottoms of her bare breasts shaking back and forth in between her white robe.
Maxwell spied as he saw, through the hole, Loretta grab for a pair of blue silk panties from her drawer and she put them on with her legs spread. Her blue panties were tight around her big beefy pubic region and a bit shiny. The erection of his pants grew harder and harder.
Loretta grabbed for her strawberry-scented lotion and poured a portion of the cream into her hand palm. Then she began apply the lotion to her plump abdomen, rubbing in round circles. She had a diamond-shaped deep navel with a lot of stretch marks around it.
Maxwell’s eyes could not leave the sight as he started to masturbate to this. What did him in even more is when she slid her hands down her tight panties to apply some of the lotion to her crotch. Loretta went to lay back down. Maxwell could not see her though his peephole but he was mad horny as he masturbated and eventually shot his load of white liquid onto the wall.
Loretta was doing the same thing, masturbating, stroking her clitoris softly over the silk of her blue panties. She even started to moan loud for the longer she kept this up. Her legs seemed to have move themselves as she massaged her forefingers on her clit, over her blue panties. Eventually, she felt the warm thick liquid come out of her and settle in her blue silk panties, making a dark navy circle in the fabric.
Maxwell could hear her moaning in the other room. She must be having an orgasm. He couldn’t help but to walk into the room.
He saw his mother. She had her big legs opened, forming a diamond with the soles of her bare feet almost meeting. Her chubby hands rested on her inner thighs that featured wide dark spots on each thigh. Not only that, Loretta was still in her white robe, bra free, and in her blue panties, tight on her thick pussy, and on the crotch of her panties was a darker navy circle. As he just walked in on her Loretta was dead embarrassed. She gave her son an innocent look with her fat bottom lip slightly puckered. With that chubby, plump, face of hers, Loretta looked so innocent, so shy, and so young for a woman of 36.
“So mom, I see your pussy is wet,” he couldn’t help but to say to his mother.
Maxwell slowly approached his mom, and she locked her eyes onto his, more shy and nervous. His penis remained stiff and hard as a rock as he saw her plump nipples protruding through the thickness off her robe.
He climbed up onto the bed and straddled her thick legs, and he and his horny mom locked eyes for a good minute.
“Maxwell,” she said her son’s name in her deep voice. “I know you wanna see my titties so allow as I show them to you.”
Then, Maxwell eyed her chest very closely as she pulled apart her robe, flashing her son her large breasts that now separated themselves, falling down to the sides of her arms. Maxwell grabbed both tits, squeezing them and caressing each tit. Maxwell’s faces descended to meet Loretta’s and the mother and son shared a deep long tongue-to-tongue kiss. His cucumber-long and thick erection brushed against the fabric of his mom’s panties. As they kissed, Loretta felt both her extended nipples press against the skin of her son’s palm.
Maxwell was enjoying this, a bit more than Loretta was as she seemed to have gotten more than she bargained for. Loretta pressed her chubby hand against his flat and bony chest, pushing him back in the sitting position.
“Did you not enjoy that mom?” asked Maxwell, a bit concerned.
“No…” said mom as she got herself into a seating position over the edge of the bed. “I gotta go get dressed.”
“You going somewhere?”
“I have to work tonight.” she replied.
“Let me feel your titties.” Maxwell demanded, his hand reaching for his mother’s bare breasts.
Much to her shyness, she sheepishly tightened her arms against the outer sides of her large swollen breasts. Then his hands brushed horizontally over the soft warmness of her breast meat, lightly massaging her swollen nipples. Loretta released a moan. Her nipples were so hard that they start to hurt and her son’s penis mirrored the same action.
Maxwell softly groped the left breast, gently grabbing it as he stared at the width of her lovely black areolas. Her black areolas were so lovely. Loretta sighed again as she started to feel uncomfortable.
“That’s enough.” Loretta softly moaned. But the softness of her voice didn’t do much.
Maxwell wasn’t listening. He rubbed his hand over her large breasts, stroking each baby-feeder. “But mom…” he softly protested. “I wanna drink the milk outta your breasts.”
“No.” she said firmly and seriously as she yanked her son’s hand off her, getting off the bed afterward to get dressed and ready for work.
Loretta walked over to her dresser. She opened one of the drawers and grabbed for another pair of panties and her white pantyhose. Maxwell stared. She closed the drawer and went into her closet, now modest and not horny anymore. Shy and modest, Loretta pressed her big body into the corner of the closet, hiding her front. She turned back once more.
“Can you turn around or get out?” asked Loretta.
“Oh sure mom!” he lied, turning his back. But he and she both knew that Maxwell was going to turn back again.
Loretta turned back to getting undressed, slapping her clothes on the upper shelf of the closet. Maxwell turned back to look at his mother, watching as she pulled down her blue panties, bending over. It excited him as she bent back, sticker her massive fat bottom toward the direction of her son, wagging her butt back and forth as she rolled down her dirty panties. “WOW! Her butt is soooo big!” he thought. “SOOO hot!”
After she stepped out of them, Loretta discarded her panties onto the floor inside the closet and dropped her white robe to the floor.
Loretta’s bottom was long, gigantic, with a lot of cottage-cheese cellulite on her bottom and on the back of her thighs. Maxwell almost drooled as his jaw slowly fell. She was naked again. Loretta slipped on her new pair of panties, also blue but with white stripes going across with a blue band.
She would then grab and put on another copy of the bra she had on earlier, a white cotton bra with fabric-decorated butterflies adorned on both cups. She turned to her son who after catching the movement of her head, looked away.
“I know you was watchin’” said Loretta.
“Sorry, mom.” he apologized, a bit sarcastically. “But you just too hot to not look away.”
“Whatever.” Loretta rolled her eyes, then put on her tight nylon pantyhose.
Then she went for a dress, a pink one. It lacked sleeves and was decorated with flowers. Unlike the upper bust area, the bottom of the dress was very baggy, folded to resemble a wedding dress, only the bottom of the thing failed to cover her knees once she put the thing on. The dress’ neck portion was long and wide, tightly straining her large breasts and nicely displayed her 9″ juicy cleavage.
Maxwell quietly moved away to hide under table, at his mother’s makeup station right beside her bed. Loretta heard him moving but she did not say a thing as she took went to her makeup station to take her seat. Maxwell looked right up her dress, in between her legs. Loretta knew he was under the table, but she did not say anything.
Maxwell could not contain his irresistible desire to his mother’s round and beefy crotch. Moreover, her legs were opened wide. He could only imagine pushing the hardness of his penis into his mother’s big twat. He simply loved the curves of the blue stripes of her panties. They were visible, even through the thin white fabric of her pantyhose.
Maxwell’s penis grew firm and stiff to the sight. Her big pussy was so round, so fat, and so mesmerizing. He failed to contain the compulsion to glide his hand into her dress, and lightly felt the fabric of her pantyhose, touching her inner thigh as she was in the middle of putting on her makeup. She was startled by Maxwell’s touch to her thigh, near her private part.
“Stop. No.” she lightly moaned as she sheepishly tightened her legs.
“Mom, can I lick your pussy?” Maxwell deviously asked from under the table.
“Maxwell, that is so nasty!” she said to her disgust.
“You know you want me to.”
“No, I don’t!” she said defensively as she slid back. “Get from under the table, NOW!”
Maxwell did. He followed his mom’s order and went up to sit on the edge of her table. All he wanted was to slide his hard and long penis into her delicious pussy, but the boy was not disappointed at all. He also had her cleavage to gaze at. She slid back to the table and continued with her makeup.
“Why you keep doing this to me?” she asked sheepishly as she stared into the mirror at herself.
“I told you before mom,” said Maxwell. “You’re irresistible.”
“Oh… So then I see you have the tendency to stare at me… and my big gigantic breasts…” Loretta said dryly before placing her hands to her massive breasts. “I’m not a little girl, Maxwell. I have big titties and they move around uncontrollably. They try to fall out of everything that I wear and I get unwanted stares when I go out.”
“So I’m one of those unwanted stares?”
“Yes.” she said firmly as she now pounced her fingers into her cream, making her cleavage wobble again, right before applying it to your face.
“It’s the clothes you wear… It all you’re fault actually for being so sexy.”
“Oh really?” she said. He watched as her long and juicy cleavage wobbled as she pounced her hands into her makeup to apply to her chubby face. Both of her breasts would take turns jumping back and forth.
“Yeah… you know you want your titties fondled by me so don’t deny me anymore.”
Maxwell reached for her breasts. Loretta watched his hand approach her chest as she raised her arms, slightly sticking out her big chest. Maxwell’s hand groped the left breast of his mother. She was uncomfortable but she failed to protest as a smile did not show up on her face. After a soft grope, she rolled back again, telling her son, “I let you do that to me a few minutes ago because I was horny. Now I have to get ready to go to work.”
She then removed herself from the seat, her breasts making a slight wobble as she got up. Loretta got a thin brown coat with a hood, bordered with white and tan phony fur and put it on, zipping it up. Loretta went to give her son a kiss to the forehead and went off to drive to work, leaving Maxwell in the house.