Ms. Barbara and Me - Lesson 01
Most of this story is true. Names slightly altered.
I graduated one quarter early from high school back in the 1980's, so I decided to take some classes at the local Junior College that spring. I was almost 19 and was very much looking forward to meeting new people and mingling with the college girls. I needed some extra money, as most of us did back then, so I answered an ad that had been posted on the bulletin board in the student center. The ad went something like this:
Wanted: Real Estate Assistant. To help with office work, photographing target properties, and other tasks, as assigned. I think it was something like $9 an hour.
I had done a fair bit of photography in high school and I was planning on being a finance major, so this seemed to fit better than something like a restaurant job. I called the contact, Barbara Beason, and we set an appointment to meet at her home one afternoon. Ms Barbara, as I would come to call her, lived in an upscale neighborhood close to Atlanta. I knocked on her door and saw a somewhat attractive 50ish woman making her way to the door. She had medium length brown hair, a pleasant smile, and she looked quite busty underneath her very conservative business suit.
We sat in her kitchen and got to know one another. She was an empty nester and her husband had passed away 8 years prior. She sent her kids to the best private schools for high school and college and only one remained in college... somewhere in the northeast. She came off as very controlled and together. She was very pleasant. She spoke quite precisely and somewhat formally, but it was more comforting that off-putting. We hit it off immediately and she even knew some of my parents friends. It was agreed that I would start the following week. One or two afternoons a week, as scheduled and needed.
I enjoyed the work very much. She would make copies of the local atlas and mark the approximate locations of the houses and townhomes that she needed me to photograph. I would take pictures and take the film to get developed (yes, developed, remember this was in the 1980's). Then I would head back to Ms. Barbara's house and help her with whatever else she needed. Sometimes it was office work and sometimes she would ask me to do a few household things. Blow off the driveway or her tennis court, maybe help her move something heavy. She lived alone in that huge house, after raising 4 boys in it, and she badly needed to downsize.
In May of that year, something happened that would change our friendship tremendously. I came back to her house one afternoon after taking photos. I did a few things and we sat down at the kitchen table. This was pretty much the routine at this point. I would wrap up whatever needed doing and we would sit down and chat. Even though she had moved from the northeast, she had fallen in love with southern sweet tea. She would pour us both a glass and we would just talk about life. How were my parents... What her boys were up to, etc..
This particular afternoon, Mrs. Barbara had removed her business suit jacket and she was just in her skirt, nylons, and silky blouse. She had undone a few buttons on her blouse because it was starting to get warm. I honestly do not think she had anything in mind when she did that... but this is what happened:
Apparently, I kept looking at her magnificent cleavage and she took note of that fact. When she caught me looking one more time, she paused whatever she was talking about and I could tell I was busted.
"So, Michael, I couldn't help notice that you keep looking down my blouse."
I was somewhat mortified, but not totally embarrassed. "Oh, Mrs. Barbara, I am so sorry about that. I will do better, I promise."
"Oh no, dear. It is perfectly natural for a man of your age to do that. I'm actually flattered that you want to look."
After a pause, she looked me dead in the eye, and in her serious business tone, she said, "Tell me, Michael. Would you like to see them?"
My eyes widened and she could see the excitement on my face. "Definitely!"
With that, she slowly unbuttoned her blouse while watching my eyes feast on the unveiling. Finally, she reached behind her back and unhooked her fortress of a bra. When she pulled her bra out of her blouse, I could finally see those gorgeous breasts.
She had some freckles on her upper chest, but her breasts were as creamy as milk. Her areola's were quite large and I noticed already that her nipples were hardening. They had a beautiful deep pink color.
"Wow. They are fantastic! Really gorgeous!"
Ms. Barbara actually blushed at my compliment!
"Why thank you, Michael."
With her serious, but sweet, teachers tone, she said to me, "Now reach out and touch them. Gently at first."
I moved very slowly, wanting to savor every second of this. When my hands finally engulfed her breasts, they were soft and warm. I lightly squeezed them and played with them. "That feels very nice, Michael. Yes." She closed her eyes a bit as I caressed them.
"Michael, would you like for me to teach you some things... You know, about between a man and woman? I only want to do this to help you be confident and know what to do when you go off to school. And, of course, only if you want to."
"Wow. I would love that, Ms. Barbara."
"Ok, then. We will call them your Lessons."
"First, I want you to lightly run your fingers across my nipples... mmm, yes... Like that. You want to tease them a bit. You see, they are already standing at attention and that is good."
"Now, put them between your fingers and lightly squeeze and tease them..." As I did so, she took in a slightly sharp breath... "Oh, yes... Yes... That's it, Michael. Keep going... Ok... a little harder, Michael... Squeeze my nipples, now."
I was fucking mesmerized! Completely. Watching her face and her enjoyment and her breasts and nipples in my hands.
"Yes, Michael. That feels so good. Some women can have an orgasm from simply playing with their breasts and nipples. Have you ever given a woman an orgasm, Michael?"
"Not that I know of, Ms Barbara," I answered honestly.
"Ok. We will get to that at some point. It's important to learn."
At that point, I had to take one hand away from her breasts and adjust my cock as it was straining against my jeans. It had almost gotten painful in the position that it was in.
"Oh yes. I did notice your hardness. I think I can help with that."
With that sweetly removed my hands from her breasts and asked me to stand up. We were in two chairs facing each other, so when I stood up, my crotch was right in front of her.
"Alright," She said, "Let's see what we have here"
She expertly worked my belt buckle, button and zipper. Once she did, she went ahead and slid my pants to the ground. My cock was peeking out of the top of my boxer shorts. She pulled those down gently and sat looking at my cock.
"Oh my. Yes. You have a wonderful cock, Michael. Can I proceed?"
"Oh my God! Yes, please, Ms Barbara."
She started by using only her fingertips and fingernails, which were fairly long and painted a conservative red... She moved them up and down my shaft for what seemed like forever... Then she gripped my cock more firmly and began giving me the best hand job I had ever experienced. Keep in mind, I had only experienced a few before then. But it was clear to me in that moment that experience mattered... and mattered greatly.
I loved watching her work. The fingers of her other hand were caressing my balls and she would even run one finger in between my legs and back towards my asshole. How did she know all of this... After a few minutes of this she looked up and said, "Are you getting closer, Michael? It is important to communicate with each other during sexual engagement."
All I could do is mutter an affirmative, "Mmmm hmm."
"Ok, Michael, I want you to tell me when you are getting really close."
She quickened her pace. Jerking firmly and softly somehow at the same time.
"Oh, Mrs Barbara. I'm getting close."
"Ok. I am going to take you in my mouth now... I want you to cum in Mommy's mouth, ok?"
"Ok... Yes..."
Then her soft, wet mouth engulfed my cock... She was pumping the base of my cock, but her soft warm mouth and tongue were working the top half of my cock...
She removed her mouth from my cock to give me encouragement.
"Cum for me Michael." Then louder, "Cum for me, Michael. I want you to cum deeply in Mommy's mouth! I need you to cum for me, Michael!".
That was so hot to hear... It pushed me over the edge.
"Oh my God... I'm gonna cum, Ms Barbara... I'm cumming!"
This time, she removed her hands and she took my cock so deeply into her mouth, I couldn't believe it.
Ecstasy had arrived. She bobbed her head up and down and I had my hands in her hair. I thrusted into her mouth and she took it wonderfully. Then I came furiously. I tend to orgasm for a very long time, but this seemed to be a world record. I could feel and hear her moan as my cum was shooting into her mouth and throat. I could hear her gulping it down with greed.
She finally removed her mouth from my cock for a moment.
"My, my... You certainly came quite a bit... Let me make sure you are all drained, now."
With that, she went back to work. Working to suck every bit of cum out of my balls.
She finally deemed that the job was complete and she told me to sit down. She went to the kitchen and returned with a slightly damp cloth. She lovingly wiped down my cock and then her mouth. As I recovered in the kitchen chair, she went to the sink. I buttoned up my pants and just said, "Wow."
I could see her from the side. That made her smile.
"So, that was lesson one. Breast and nipple stimulation. You did quite well. I will work on a "lesson plan" of sorts and we'll work through them in the coming weeks, okay?"
"I certainly wouldn't call that work, Ms Barbara. But I am all in on that. Thank you so much."
"Oh, it was my pleasure, too, as you witnessed."
We wrapped up as normal and I drove home slow and easy, not quite believing what just happened.
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