Young man fulfills old fantasy with family MILF friend

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I’ve known Mrs. Kaufman since I was a child. She attended our church, and she was the wife of one of my father’s business colleagues. When I was young, I did not give much thought to Mrs. Kaufman, but as I entered my teens I admired her large breasts. Hers were not the enormous balloons that look fake, but they were prominent and always well-displayed.

As a new college graduate home for the summer, the sight of Mrs. Kaufman still aroused me. Now in her 60s, Mrs. Kaufman had maintained an appealing figure to go with her lovely face. Her well clipped hair had once been jet black, and now it was silver with just a lone streak of black to remind me of her former color.

When I was young, Mrs. Kaufman had been the subject of some of my fantasies, and she hadn’t lost that allure.

Her personal interactions with me have always been of the most proper kind. She had always been cordial and polite. Once in a while, she and Mr. Kaufman were guests in our home for dinner. She always took an interest in me but in an adult way toward a young man.

As I grew older, I did not see her as often. But this summer, after my college years, I saw her around town a few times. She never failed to smile and greet me and ask about my plans. As we would talk, I wondered if she could tell that I was looking at her breasts and reliving my youthful fantasies.

My eyes searched her blouse for little gaps that let me see just a bit of her bra. Even though she dressed modestly, occasionally I could glimpse the color of her bra or a bit of lace and nylon that held up those amazing breasts.

One day, my mother asked me to deliver an item to the Kaufman’s home. I drove over and knocked on their door, and Mrs. Kaufman opened the door for me. Their home was spacious and traditionally decorated, and she invited me to come to the living room and have a seat on the sofa. She thanked me for the delivery and asked if I would like a glass of iced tea.

“Yes, thank you,” I said.

Mrs. Kaufman was rather dressed up in full skirt with a turquoise cotton blouse that buttoned up the center. The last buttons were left open to reveal the smallest glimpse of a white bra. She sat in an armchair across from me, and we made small talk as I sipped my tea and contended myself with quick glances at her figure, her attractive face, and her legs.

“I’m working on a big project to save old family photographs,” Mrs. Kaufman told me. “And I must say that it takes a lot of time.” Then she asked me, “Do you know any shortcuts for imaging photos?”

“I might,” I replied to her. “Can you show me what you’re doing?” I was delighted to extend my visit in her home.

Mrs. Kaufman walked into another room and brought back a box full of old photos. “For example,” she said, “I have arranged them by subject, and here are ones of me as a child.”

I was intrigued to see photos of Mrs. Kaufman as a child, then as an adolescent, and a teenager. She sat next to me on the sofa, close enough so that our legs touched as we looked at the photos together. I was loving this, and I began to wonder if this visit might present an opening for my old fantasies.

“I love these old photos of you,” I told her. “Look how cute you were.” Then I caught myself and added, “Oh, I mean you still are cute, of course.” I looked directly into her face and said, “Once beautiful, always beautiful.”

Mrs. Kaufman blushed. “Oh, you’re so nice to say things like that, but I’m afraid you’re too generous with your compliment.”

She had looked away, but I kept looking at this stately lady who was somewhere between two and three times older than me and said, “No, I’m serious, you have a rare beauty that hasn’t faded.”

Again, a blush.

She opened a new package of photos of herself as an older teenager, and that’s when I decided to take a step toward the undressing of Mrs. Kaufman. It was a long shot, but with care and patience I might convince her to bare her breasts to me before I left that afternoon.

The photographs showed the young Mrs. Kaufman as she was just beginning to develop. In the first photos she was a cute new teen with small tips barely tenting her shirt to reveal the first phases of womanhood. Later photos showed a teenager with fuller and fuller breasts, even a few in bathing suits that left less to the imagination.

I couldn’t resist.

“Mrs. Kaufman,” I asked, “do you mind my asking you a personal question?”

“Why no,” she replied.

“Well, I don’t know how to put this,” I hesitated, “so I guess I’ll just say it.”

“Go on,” she encouraged me.

Sitting next to this perfect specimen of aging womanhood, still very attractive and still with large breasts that I would give anything to see, even though I was sure they sagged now and were only held erect by well-selected lingerie, I asked, “What did it feel like then?”

Mrs. Kaufman looked puzzled.

I continued, “Well, you were a girl, like all girls, with a body that was a lot like the boys, and then all of a sudden…”

“Oh!” she exclaimed as she probably understood what I was asking.

I decided not to wait for her to speak, and I added, “I’ve always wondered what it would have been like to go through such a change and what it must have felt like to go from having a flat chest to these.”

As I said, “these,” I reached out with both hands and very gently rested the tips of my fingers under her two breasts, touching them ever so slightly.

My heart was racing a million beats a minute, and I was nervous about making such a daring move, a move I had no intention of making when I arrived at her home that afternoon. To the touch, the underside of her breasts were firm, and I didn’t know if she could feel the gentle pressure of my fingers as I let them trace the curve up to where her nipples must be.

I withdrew my hands.

Mrs. Kaufman sat still and erect with her chest thrust out toward me, and she did not react in any way but instead she became calm and pretended not to have noticed my touches as she stared at the old photos and considered my question. Had I gotten away with a little feel?

Actually, when I touched her, I tried to do it in a way that seemed natural and matter-of-fact. We were sitting so close and looking at photos of her as a teen in a bathing suit, and it just seemed like it was part of my question when I touched her breasts so casually. It was as if she might not understand what I was asking if I didn’t use some “hand language” to make myself clear.

Then, she answered, “Gosh, no one has ever asked me that question. But it was a memorable time for me.”

“Please don’t say more if it is unpleasant,” I said.

“No, it’s ok, but you’re the first person to ask me about it.”

I decided to keep taking a risk and asked her, “Not even your husband has asked you how it felt to grow such large breasts?” As I spoke those words, and as if to illustrate my question, I again touched Mrs. Kaufman’s breasts. This time I very gently lifted them.

I thought my words and actions might cause Mrs. Kaufman to react with alarm or to scold me and order me to leave. But instead of showing concern, she apparently took my question and even my touching as rather natural.

Mrs. Kaufman took a deep breath, increasing the size of her chest and giving me more to look at, then she let it out with a sigh, “Yes, those were fitful times.”

“Why,” I asked.

“It’s probably true for every girl, except those who never ‘develop’ very much.”

“I’m curious,” I said, “and I’d like to know more.”

She looked at some of those old photos as memories coming back to her mind.

While she was thinking, I added, “I saw girls go through this when I was a teenage boy, and of course the boys were intrigued and mystified. But the boys saw all this in sort of playground terms. I mean, boys can be cruel and see all this as objects for their entertainment.”

Mrs. Kaufman quietly nodded in agreement.

So I went on, “But from the female side, how did it feel?”

Mrs. Kaufman was still reflecting on what she might say, so I took it to a higher level, “What did it feel like to have not just breasts but these?” As I spoke, I reached over and more firmly and deliberately held her breasts. I could feel the seams of her bra and let my finger trace the seam of each cup to the tip of both her breasts. But I restrained myself from adding a tiny pinch of her nipple area.

At any moment, I expected her to throw me out, but she did not. After touching her breasts like this, I now felt that she enjoyed the flattery, even though I sensed that she was a proper wife who would not let herself lose control. My work was cut out, but so far, so good.

Finally, Mrs. Kaufman said, “It was surprising to see myself change, first just a little, and that was fine. But within a year or two I had to learn so much that I had never known before. How to dress, how to handle the boys who made crude remarks, and how to deal with people who stared ‘there’ more than at my face. I wasn’t able to run as fast. I’d been a tennis player, but those – she pointed at her breasts in a photo – got in the way.”

“Well,” I added, “they’re still there. How did you get used to the changes?” “What about the weight?” I asked, “Did it hurt your back to carry this new weight?”

Again Mrs. Kaufman sighed, “You got that right. Girls with larger endowments have to be careful about their posture and sometimes use extra support. Yes, that was part of it, too.”

She turned over a few more photos and held one of herself with a date at a high school dance.

“Who is that?” I asked. “Was he a boyfriend?”

Mrs. Kaufman said, “Not really, he was just a boy in my class who I’d known since third grade.”

Her gown showed a lot of cleavage, so I asked, “That dress looks daring. Did you enjoy showing off your endowment?”

Mrs. Kaufman replied, “Ha, I suppose I did back then, but I learned that there is a price to pay.”

“A price?”

“Oh yeah, the guys get ideas, and this one sure did. After the dance, later that night, I had quite a wrestling match with him to keep him from touching me ‘there.'”

I asked, “Did that happen a lot?”

Mrs. Kaufman replied, “No, some boys were polite, but others weren’t.”

“Do you think I am polite?” I asked her.

“Oh, yes, you’ve always been a perfect gentleman,” she answered.

“I’m glad you feel that way because I wouldn’t want to bother you with these questions,” I said. “I have another question.”

“That’s ok, it’s actually kind of nice to be asked about all this. I’m actually flattered that you are curious about this sort of thing,” said Mrs. Kaufman.

I took my next leap. “What about nipples? At first, were they small, and do they change over the years?” I was quiet for a moment then added, “I hope that isn’t too personal to ask.”

Mrs. Kaufman looked at me and said, “Of course that is a very personal question.” She paused, and I thought that was the end of my prying and playing with her. But she went on, “I can’t speak for every woman, but my nipples have changed over time.”

As she spoke, I could feel a change come over her, as if she was dropping her guard. How would she respond if I asked her to let me see her nipples?

“That is fascinating,” I said. “Can you describe how they looked at first and how they have changed?”

Mrs. Kaufman was breathing more heavily, which caused her breasts to rise and fall and put on more of a display that delighted me. She said, “At first, they were just…”

I jumped in, “rosebuds?”

“Yes, like little rosebuds,” she said. “Just little pink flowers on the tippy-top of my breasts.”

“Were they a problem under your clothes? Did you have to hide them from the boys?” I asked her.

“Of course,” said Mrs. Kaufman. “The little training bras that my mother gave me were pretty soon too thin and flimsy, and I got lots of stares in school because of my nipple points.”

“Nipple points?” I said, “That’s a good way to describe the problem. I can see how that would be bad.”

“It would be awful, especially in cold weather,” she said.

“Oh, right,” I answered. “So what did you do?”

Mrs. Kaufman said, “A lot of the girls had this problem, and we used pads or bandaids to hide our nipples.”

I kept probing, “Did things other than cold weather cause pointy problems?”

She thought for a while then told me, “Yes, there were times when they would get rubbed accidently while passing in the school hallways, and even a little bit of touch like that could bring on the problem.”

“Did that cause arousal?” I asked. “Did that sort of casual touch make your nipple points show because it felt good?”

Now I knew I was in the danger zone. So far, it had felt natural to ask Mrs. Kaufman all these questions, and she kept answer them. But now, we were talking with each other about sexual arousal.

As Mrs. Kaufman considered what to say, I took the plunge. I touched one of her nipples with my finger and pressed firmly, moving my finger up and down and from side to side, “Does this cause your nipple to become aroused?”

While I manipulated the tip of her breast, still completely covered by her blouse and bra, Mrs. Kaufman looked squarely at me, put her hands on my shoulders and looked into my face, “This is amazing! I haven’t felt that kind of tingle in my breasts for years. I thought it was gone.”

She went on, “To answer your question, yes! I can feel that.”

“Does it feel good?” I asked.

“It certainly does,” she answered.

“Do you think it would feel better on your bare nipple?”

I did not wait for her to say anything. She let me unbutton her blouse. To her waist and open it to reveal her lacy white bra. Her breasts were pressed tightly against the nylon and lace, and just a bit of pink areola was visible behind the lace.

I leaned back to enjoy the view of this old family friend whose tits I had dreamed about for so long. As I gazed at these prizes that I hoped to soon see completely bare, I marveled at how easy it had been to talk her into feeling comfortable about exposing herself.

All along, my cock had been wiggling and dripping. I feared that she had noticed and might become alarmed. If she did see that there as an eight-inch snake in my pants, she gave no hint, but there was a clearly visible wet spot on my pant leg.

Mrs. Kaufman sat by me and did not resist as I gently massaged her nipples through the bra. I was in no hurry. This was heaven to see her aging but pretty face as she enjoyed the sensations.

In the back of my mind, I wondered about her marriage and Mr. Kaufman. Didn’t he do this for her all the time? Maybe their love making was over? I was certain that any number of men in town would love to be doing what I was doing to Mrs. Kaufman at that moment.

These thoughts only made me more eager to remove her bra and to see how firm her breasts still were and how her nipples looked in the open air. I was just about to reach that final goal when her phone rang.

Her phone was on the coffee table in front of us, and Mrs. Kaufman leaned forward to pick up the phone. A she did, her open blouse allowed me to see how her breasts moved as she bent and twisted and swung herself back to an upright position.

She listened, said ok a few times, then ended the call. “That was Mr. Kaufman. He’s on the way home and will be here in ten minutes.”

I smiled and said, “Oh, then perhaps we should discuss your photo project at another time.”

Mrs. Kaufman’s nipple points were majestic and obviously at maximum size. With regret I pulled her blouse together, covering her bra, and I carefully buttoned her blouse.

As she began to straighten the old photographs, she made no reference to having been felt up in her own livingroom by a young man who she had known for years. I was willing to bide my time and wait for another day, that is, unless Mrs. Kaufman would have second thoughts and try to forget that this had happened.

In a few moments the front door opened, and in came Mr. Kaufman. His wife told him that I had helped her work on the old family photos. He smiled and greeted me and thanked me for helping his wife.

I shook his hand and smiled, “I am happy to help Mrs. Kaufman in any what that I can.” Then I turned to Mrs. Kaufman. She was completely restored to her proper appearance and looked more lovely than ever. I nodded to Mr. Kaufman, then as I gave Mrs. Kaufman a gentle and proper hug, I whispered in her ear, “Your pussy must be very wet.”

With that, I said goodbye.

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