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…