I was raised in your standard white bread family, my parents are still married after 42 years, still happy together, my brothers and sisters, ( I have 2 of each ) are happily married, raising families of their own. I am the only one still single at the young age of 23, and not looking for a permanent relationship as of yet.
I was laying in bed a few nights ago reminiscing on how I learned about sex, and it sure brought back some fond memories of my first real woman. I had been cutting yards for years for the same people around my house, some since I was 14 until I left home after High School. One that sticks out was Mrs. Janson, at the time I started cutting her yard I was 14 she was 47, nice as could be too.
She always asked me in after I was done with the yard for something cold to drink, I didn't ever notice for the longest time how her eyes always lingered on my sweaty body, as I was enjoying the cool air and cold drink. Not that I didn't stare at her every chance I got, She had the largest tits I had ever seen, and once when I used her bathroom, I glanced in her laundry basket and found a used bra in it, the tag said 44 DD, I didn't know what it meant, but I knew from seeing my moms and sisters that it was fucking huge!
I even smelled it, and I smelled her perfume and the slight twinge of her sweat. I had an instant hard on and had to wait a few minutes before I could get out of there so it would go away. Mrs. Janson was no raving beauty, in fact she was semi homely, and rather large, always wore plain dresses and I don't ever remember seeing her with any kind of make up on. But she was always nice to me and paid me well for the yard.
The summer I turned 18 I was just finishing up her yard when she called me in for something to drink when I was done, which I was more than happy to do since that day was hotter than Hell with no wind at all. I finished the yard and pushed the mower to the back door, knocking on it, she answered the door, this time, unlike any other time since I had done her yard, she answered it in her dressing robe. I took a double take, and saw her smile as I stared at her larger cleavage. She welcomed me inside and told me to sit at the table while she got me something to drink. I watched as she opened the refrigerator, she bent over to get the container off the bottom shelf, as she did, the robe tightened up on her large ass and I could see the outlines of her panties showing through the robe.
My dick popped up immediately, and I barely had adjusted it when she turned back towards the cabinet for a glass, she was turned slightly towards me and I saw the side of her tit showing where the robe had slid open some from her movements. I was shifting on the chair, trying to find a comfortable position to accommodate my hard on, and hopefully keep it from showing through my shorts. Mrs. Janson went back to the refrigerator and got some ice cubes and filled the glass with her homemade lemon aid.
She came to the table and leaned over when she gave me my glass, my eyes could only see down her robe, where those two large tits hung down in open sight, I even caught a glimpse of one of her nipples. I was young, but not so young as to not know what she was doing, or doing to me. I saw her eyes look down my body as she slowly backed away, they slowly looked down my chest which was still covered in sweat, and my nipples that were now hard from the cool air, and they continued on down to my crotch. My hard on, which I had shifted, was sideways in my shorts, showing every part of the 7"s I have.
I saw her hesitate before moving to her chair when she saw it, and I would swear she licked her lips as she did. We had a small conversation about the yard and it moved on to things going on in my life, what I had planned after school, work, girls all the normal things, but today's conversation was anything but normal. She had sat closer to me today, and more of an angle, her eyes kept moving down to see my dick as it was almost pulsing with my heart beats, I could not will it to go away, not with her tits almost in my face.
I looked at the area where her robe was open and saw the side of her tit hanging about 6"s, I was stuttering responses to her questions and she was enjoying it. I was ready to leave, but was embarrassed about my hard on so I stayed and endured more. I finished my lemon aid, and she got up and refilled my glass, again bending over, giving me a good view of her ass then showing even more tit as she leaned over to give me the glass.
She sat back down, a little closer this time and asked me, "Tim, have you ever had sex with one of your girlfriends?"
I was shocked at the question and mumbled a response, too low for her to understand, so she asked what I said. "Well, uh, I, uh don't know if you would call it sex." I was about to die from embarrassment as I answered her question.
"What would you call it Tim? What did you do?" she smiled.
" I don't know if I should be talking about this Mrs. Janson, It's uh kind of personal and all!" I stammered.
"Oh come on Tim, we have known each other a long time and we have never had secrets from each other have we?"
"No ma'am, but we have never talked about that before." I blushed as I said that.
"Well, if you don't want to tell me I respect that, I was just interested is all. And I am interested in you and your well being." She smiled again, this time with a little more smirk than smile. "I just wondered what you kids do these days compared to what we did in my younger days."
I decided to turn the tables on her by asking, "Oh Yeah? What did you do in your younger days?"
She laughed and said, " Oh we did many things, some more than others." A look of remembrance crossed her eyes then she said, "I used to give my boy friends hand jobs a lot, that kept them from getting to much, but enough to keep them coming back for more, and some I would even give a blow job if they would take care of me also."
I was in shock at what I was hearing from her, never would I have ever expected we would be talking about our sex lives, and since she had opened up to me I felt it was only fair for me to tell her some of what I had done.
"Well, I know some girls who do those things, and I did actually have sex with one once, but she moved, most the other girls will only do as much as they have too around here."
"You poor boy." She said and I felt her hand on my thigh, "No one should have to do without something as important as sex at your age." her hand slid up to my dick, and I felt her fingernails as they raked up and down on it. " I know what I would do if I could." she grinned at me again.
I swallowed hard, it was nice, the feeling of her feeling off my dick, but scarey since she was an older woman by many years, even though she had not been married as long as I had known her, it is not something you would ever dream of happening.
"I saw you looking at my breasts, I enjoyed that a lot, it made me feel younger and after seeing you get an erection from looking, it was exciting to know I could do that to a young man still." Her eyes on her hand on my dick, her voice barley audible as her hand moved lightly on it.
I leaned back in the chair and opened my legs wider for her, she took the initiative and grabbed it firmly, then asked, "May I see it Tim? Would you take it out for me?" Her eyes looked with desire.
I cleared my throat, "Sure Mrs, Janson, if you want." And I stood up then unzipped my jeans, she took the waist of them and slowly pulled them down past my knees, then looked at my hard on pressing against my underwear, a small wet spot on them from the pre-cum that had escaped. She ran her fingernail over the wet spot and my dick jumped at her touch. I stuck my hands inside the band of the my underwear and pulled them down, my dick popped up, bouncing with each one of my nervous heart beats as I stood in her kitchen with my pants around my knees.
She sat back in her chair and stared at it, a look of pure lust showing on her face, her hand absent mindedly went to her big nipple and squeezed it gently. I stood there not knowing what she wanted me to do next, I didn't have to wait for long, "Jack it off for me Tim, I want to see you jack off."
I reached around it and began to jerk off slowly, after a couple of minutes she opened her robe, showing me those monster tits, and dark areolas, each tipped with a thick nipple that stood out at least a half an inch. Her fingers went to each nipple and she pulled on them, even pinched them as she stared at me jacking off.
"Oh my Tim, That is the most exciting thing I have ever seen, Do you like my breasts?
"Yes ma'am, they are beautiful, I've never seen any as large as that before. Doesn't that hurt? When you pinch them like that? I asked as my hand started moving faster on my hard on.
"Oh no, I like to have them treated roughly, it excites me even more to do it. Would you like to touch them Tim? I would like for you to touch them for me."