Mildred's Sexual Evolution

How Mildred Became Millie Chapter 1 - The Lessons

The sun was rapidly warming my bedroom when I finally awoke after my first good night's sleep in a week or more. I rolled over and looked at my watch, it was already 10 AM. I was still somewhat tired and might have been able to go back to sleep for another hour or so, but the increasing heat indicated that it was time to get up.

The reason for my poor sleep in the days before was pulling several all-nighters in my panicked efforts to finish out my freshman year at college without flunking out. This last-minute panic was entirely my fault for enjoying too many spring parties. Of course, I resolved to do better next year - assuming, of course, that there was a next year. Another reason for the hot morning was that the college I attended had experienced a major fire in a key building over the previous summer. Our start of classes was thus moved back, so that classes had ended late in June

So, I'm Matt. I have an older sister, Karen, and a younger sister, Becky. We live in a nice neighborhood on the edge of a medium-sized town. The town center isn't very far away, but we back up to some nice open woods that lead down to a river.

When I finally stumbled groggily down the stairs to the kitchen, my sister, Karen, was there to greet me.

"Welcome home, looks like you pulled a few all-nighters at the end of your semester".

"You're right, how did you know", I replied

" Well, you look just like I must have looked after my first year at college. Too many spring parties perhaps?"

"You got that right, but I think I managed to not flunk out, so I will get a chance to do better next year".

"When I heard you stirring, I put some coffee on. Would you like some eggs and bacon, or will it just be cereal?"

"Eggs and bacon sound great, but why such royal treatment?"

"Because you're my brother, and I can totally relate to how you're feeling right now. College has been great for me, and I too worried that I might not make it past my first year".

So, I gratefully drank my coffee, ate the breakfast my sister cooked, and finally began to finally feel 'normal' again.

Before I had finished my second cup of coffee, my mother returned, having dropped Becky off to do a community service project with her high school class - picking up garbage along one of the state highways that run through our town. She would be back for lunch, though.

Karen then suggested that she and I should take a walk down to the river to breathe some fresh, if warm, air. I agreed that I needed to 'get off my butt' after all my studying. I was wearing gym shorts and a t-shirt. Karen had on some loose long pants and a t-shirt. She then said she was going to change into something more appropriate for the now-warm morning. She soon returned from her room wearing some very short shorts and a tank top that didn't reach all that far below her breasts.

Mom said, "Karen, are you really going out in that outfit?"

"But Mom it's hot, I'm just going with my brother, and no one else is likely to see us".

Mom said, "O.K., good, I guess I'm glad that you are comfortable with that sort of dress within the family".

So, we started off to the river, and I caught myself suddenly realizing just how hot my sister was. When we got there, Karen reached down to check the temperature of the water. "The water's warm for this early in the season, so let's go swimming."

"But we didn't bring our suits" I protested.

"Who needs suits? We're brother and sister, there's no one else around, we'll just skinny-dip".

With that, Karen started peeling off the few clothes she had on. Soon, she was totally naked and I gasped at her full, firm breasts, tight stomach, and long, toned legs. Somehow, I had only just a few minutes ago thought of my sister as 'hot', but hot she was as she stood there naked.

Now, I had an immediate problem. My 'dick-has-it's-own mind' had risen in my shorts and I really didn't want to reveal myself in this compromising position to my sister.

"I don't think it's warm enough for me to swim in the river just yet,"

"What's wrong, little brother, embarrassed about the erection I can see in your shorts? I'll take that as a compliment any day."

"Oh, I'm so sorry. I never thought I should have any sexual thoughts about my sisters, and until now, I never have".

"Don't worry, as long as you don't try to rape me. I actually like your reaction to my nakedness; and I'm sure Becky would feel the same way. Now, do you need some help shedding those shorts?"

And without waiting for a reply, Karen came over and forcibly pulled my shorts down. As she bent over after the pull, my fully erect member sprang up and hit her in the chin. She just smiled and finished the job of removing my shorts.

I quickly stepped out of my shoes, lost my t-shirt, and jumped into the river. Mercifully, the cool water quickly deflated my erection, so I didn't feel like a pervert as I swam upstream next to my sister. As we swam up, the flow below some mild rapids became stronger. This wasn't a big river, and no spot was really above my head. There was enough water to swim, however, and my sister, a competitive swimmer in high school, recognized that this was a natural 'endless pool' where one could swim forever at a certain pace and neither gain ground nor be pushed back.

So, with me a few feet back, where the current wasn't quite as strong, we swam for 10-15 minutes before my sister decided she was a bit cold. We then waded out onto dry ground and took up seats on opposite logs to dry off in the sun.

After having just talked about school on the way down to the river, my sister wasted no time starting to interrogate me about my 'love life' in college.

"So, Matt, any hot dates your freshman year?"

"No, a few coffee and movie dates, but nothing steady".

"Did the movie dates lead to anything more, if I may ask?"

"No, not much more I replied. Some kissing and a bit of feeling-up, but that seemed to end it".

So far, I was proud that I was sitting and looking at my hot, naked sister and remaining totally flaccid. I would soon learn, however, that 'pride goeth before a rise'.

"So", says my sister, "how did you feel them up. Was it like this?" as she grabbed the sides of her naked breasts and pulled them forward toward her nipples.

"Yes, I guess that was about how I felt them up".

"Oh, so some of us girls call boys like you, 'milkers' as though you worked in a dairy barn or something. Here's how girls like for boys to 'caress', not "feel-up' their breasts".

With that, Karen started to gently stroke her breasts, starting from the bottom and continuing up over her nipples. She then noted that, done properly, the nipples should become erect with this stimulation, pointing out that, with just one brush, her nipples were now totally erect. And that wasn't the only thing that was now totally erect!

"Oh, I see you liked that little demonstration. Can I ask if you ever take care of that 'little problem' with your own hand?"

"Well, er", I replied, "most guys do, I guess"

"I'll take that as a 'yes', and humbly request that you demonstrate your 'relief technique' for me. You see, I've given guys hand jobs in the dark, and, as you might have suspected, I've had guys come in me; but I've never seen what it actually looks like when a guy comes. You are the perfect subject to fill me in".

I couldn't believe the proposition my sister had just made, and I tried to think of a way to get out of my predicament. Just then, however, she sensed my reluctance and upped the stakes with an offer to show me more of herself.

"O.K. little brother, I'll show you the rest of me, for your ongoing education of course and to make sure that the feeling in your rock- hard member becomes irresistible".

My sister then spread her legs and provided me with a very intimate anatomy lesson of her nether regions. My erection was now pulsing like it never had, and the only relief seemed to be to assume the familiar position.

"I thought that might do it", my sister said, "now let's see what you can produce".

So, while still feeling quite embarrassed at this turn of events, I started my usual pumping. Faster that I could remember, however, I felt the rising sensation of an imminent orgasm. I aimed myself away from my sister and let go with some spurts that went several feet past her. She thanked me for both the demonstration and for missing her as it was time to head back to the house and there wasn't time to go back into the water to wash off.

Back at the house, we, now including my sister Becky, sat down to a nice lunch of chilled tuna salad, cold lemonade, and even, unusual for us, ice cream for dessert.

Karen then related our walk to the river and noted, "You know, I think I'd like to go back and swim there this afternoon because it looks as though the current at the head of the pool is just right to be an endless pool".

Somehow, I managed to keep a straight face while I said that I agreed and would like to go back as well. At first, Becky and Mom didn't indicate that they would join us because Becky had to be at the tryouts for a local summer soccer team that would travel to other towns during the summer. There seemed to be some question as to exactly when Becky had to be there.

Meanwhile, Karen and I changed into our suits, grabbed some towels, and headed down to the river. When we got there, Karen said, "We didn't need these suits this morning, why do we need them now?"

"Well, I think we better at least return with some wet suits, or there might be questions", I replied.

Karen agreed, and we plunged into the water. We had just begun to make our way up to the head of the pool when we heard voices. I quickly considered my 'call' to wear suits a very good one as soon Mom and Becky came down to the bank of the river.

Mom and Becky had also put on their suits at the house and were walking down with t-shirts covering their tops. At the edge of the river, both removed the shirts. Mom quickly noted that Becky's suit looked way too small given how she had grown the past year. Becky, of course, protested that the suit still covered everything that needed to be covered, and so what if it was a little tight. Mom responded that the way it fit it was all too easy for it to come off and give the boys a show they didn't deserve.

Point made, Mom and Becky quickly got in the water. Mom who also had been a competitive swimmer in her day, followed Karen up to the 'endless pool'. Becky, who didn't want to stress her legs in any way before the soccer tryouts, just paddled about before landing and climbing up on a low rock above the pool. As she made to dive off, I cautioned her that the pool wasn't all that deep, so it needed to be a shallow dive. Becky nodded her understanding before launching off on a very flat, shallow dive.

When she came to a stop in waist-deep water, she didn't immediately stand up. She just lay there with her arms fumbling under the water. I quickly realized that, just as Mom had predicted, the top to her bikini had slipped off of her breasts. After a minute or so, Becky stood up, now fully clothed. However, I couldn't resist commenting that just maybe Mom had been right. That comment was met with an icy stare likely reserved for an older brother who reminds her that a parent was actually right for a change.

After about 15 minutes, Mom and Karen decided that they were a bit cold, drifted back down to where Becky and I were. We all then climbed out, Mom and Becky dried off, put on their t-shirts, and prepared to head back. Karen said that we would stay and perhaps take another swim after we warmed up a bit.

Karen and I were again alone next to the river, and I wondered what she had in mind this time. I didn't have to wonder very long, because not long after the others were out of earshot, Karen said that she thought I could use some practical, hands-on training in how to treat a girl. She of course tried to make this sound purely 'educational' and only for the benefit of any future girlfriend I might become intimate with. I certainly wasn't about to protest when she quickly removed her suit, asking me to do the same so that we were both equal. Then she moved closer, took my left hand, placed it on her right breast. She then slowly moved my hand up from the bottom until my hand touched her nipple.

"Just give it a little tweak", she said, "and then go down and start over, this time without my guidance".

Of course, I did exactly as she instructed. When I again had gently stroked up to her nipple, I found that it was good and hard, just as something else had become equally hard. Now, I was instructed to give her left breast the same treatment, and I soon achieved the same result.

Karen then said, "Good, first lesson mastered. Now, let's move on to the next phase of female pleasure - again just for your education and benefit of future girlfriends."

My hand was then guided to between her legs where I was instructed to first gently rub the inside of each thigh. That I did, accompanied by some gentle sighs from my sister.

"O.K., little brother, you are learning fast. Now let me take your hand and give you a tour of what I guess you guys call the 'promised land."

With that, my hand was placed on her now quite wet labial lips and I was told to find her hole, insert a finger inside, and gently wiggle it around. "In some girls", she explained, "you may find their G-spot, which is extremely sensitive, but somehow I don't believe every girl has one. At least I don't seem to have one, but there is still one guaranteed spot that will ultimately please every female - the clitoris."

With that, she gently pulled my hand out of her hole and guided it upwards to a hard little button in the folds above her hole. "Can you feel that hard little bump?", she asked. I said, "yes" and started to gently massage it. This elicited more and louder moans from my sister and finally an admission. "This was supposed to be just educational, but now I can't stop and you need to keep doing that until I cum."

I needed no further encouragement, and continued my ministrations to her most sensitive area, while employing my other hand to resume stroking her breasts. As her moans grew louder, and her body began to twitch a bit, I suddenly felt a hand on my erect member. "Yes, let's cum together, little brother. Keep it up and when I'm ready to cum, I'll speed up and finish you off as well." Sounded like a good deal to me, so I continued for a few minutes more before my sister indicated with a loud groan and a major twitch that I had achieved her side of the bargain. Her hand then sped up and soon I was grunting and groaning alongside my sister as we both came to orgasm. I rated this as my most intense orgasm to date, but had to wait until she finally came down for her analysis.

"Oh my God", she said, "that was one of my most intense orgasms ever. I guess it was because I could instruct you every step of the way. Now, most girls, and I'm one of them, like a long, intense hug as soon as possible after they've orgasmed." I willingly complied with about a two-minute and very tight hug before my sister said, "Lesson over. let's get back in the water to clean off, and as far as I'm concerned, this never happened. Right?" "Right", I replied, "I won't forget the lessons, I'll just manage to forget who taught me."

We then went back in for a short dip before drying off, putting our clothes back on, and heading back to the house.

How Mildred Became Millie Chapter 2 - The Meeting

When we got to the house, we both took a long drink of water, given our earlier exertions, and Karen indicated she might take a nap. The way she announced her intention made it clear that I was not invited to nap with her. So, having slept late that morning, I thought I might as well get on my bike and pedal the 15-minutes or so over to the field where my sister's tryouts were being held.

By now, the tryout was on to scrimmaging, and I watched as Becky expertly dribbled down the field, encountered a defender, rolled the ball back, and kicked it with a foot behind her lead foot. This totally confused the defender, and she took another two or three dribbles before expertly passing the ball to the center of the field. I figured that she would make the team, and indeed she did.

After watching that performance, I noticed a girl standing near me who was also holding a ten-speed bike similar to mine. I recognized her as Mildred Miller, who had been a class behind me at my high school. She was of about average height with shoulder-length, light brown hair and a pleasant, if not spectacularly beautiful, face. Her breasts seemed a bit larger than "average", but otherwise one didn't see anything other than a "nice" girl. I hadn't really known her that well in our years together in the same school, but I had heard that she wasn't much fun on a date. In fact, some who had taken her out described her as "downright frigid".

Nevertheless, since we both were there with our bikes, I went over to say 'hello'. I knew that she had played soccer, and asked why she wasn't out there trying out. She indicated that she was never that good, didn't really like playing in the heat, and didn't really like team sports all that much anyway.

She went on to say that she had been relieved to be given a special way to fulfill her final phys-ed requirement for graduation. In her sophomore year, she had been sick and therefore couldn't do any sports. Our school had a strict policy of the number of semesters that one had to either be in a PE class or had to be on a sports team. So, Mildred said she was one credit short, but the school athletic director knew that the last thing she wanted to do was be on the girls' softball team. So, knowing that she liked to bike, he offered her the option of a daily ten-mile ride around a particular loop with some good hills to climb along the way.

Mildred said that she loved that option, and quickly agreed to it. She said the athletic director told her he would trust her to do that daily loop and to never check on her. However, she gleefully noted that, one day early-on when she was riding, she detected the hood of the distinctive car owned by the athletic director parked back in a driveway where he thought he was hidden. She said she just rode on by and never looked that way, but never saw that car again. I said I was pleased it worked out for her.

Then, she said, "Would like to ride that loop with me?" Well, how, exactly could I say 'no". So, we started out, and I soon realized that all those trips around that loop had put her in better shape than I was from just pedaling around the campus. Nevertheless, I made the needed effort, drafted her when that helped me, and managed to finish the loop still with her.

We then seemed to have a bit of a bond, so I boldly asked her if she wanted to go to a movie with me that night. She said, "sure", what's playing. I said that I had seen that "The Sting" was at the theater not far from where she lived, and that it was supposed to be a good movie, given all the Academy Awards it had won.

"It's 'R-rated', I think. Is there a lot of sex in it?" she asked.

"No, I don't think so. just a bit of violence and a complicated plot that gives it the 'R' rating."

"O.K.", she said, "What time?"

"I'll double check the marquee when I head home, but I am pretty sure the early show is at 7, so I'll come to your house about 15 minutes before that. But give me your phone number in case I realize that it is a different time. And I think I have enough money for the tickets, but can you pay for the popcorn?"

"Deal", she said.

When we sat down for dinner as a family, Becky proudly announced that she had indeed made the team and repeated some of the compliments given her by the coaches. I then said that I had run into Mildred Miller while watching the tryouts, had taken a bike ride with her, and was now going to a movie with her.