Charlie

May of this year marked a turning point in my life. I turned 18, I graduated from high school, I was accepted to our State college and I happily lost my virginity in the most incredible way.

My folks had promised to help with the cost of college so I wouldn’t have to get a student loan but I did have to get a job and live at my Aunt Charlie’s house which was in the same college town. It all sounded good to me because I didn’t mind working and I had had the hots for Charlie since I discovered women when I was about 12 years old. An aunt by marriage, Charlie was 59 years old now... old enough to be my grandmother but she had always taken pride in her appearance and had taken really good care of herself physically. Her age was beginning to show a little in her face but I still thought she was very attractive... crows feet and all. Her body on the other hand was incredible for a woman her age. She was a gym rat and stayed in great shape. Living with her would surely give me frequent opportunities to see her in a skimpy night gown or some other immodest situation. Little did I know as I drove the 70 miles to her house just how good these peeks and opportunities would be.

Charlie’s husband Tommy, my grandmother’s youngest brother, had died about 5 years ago leaving her a very wealthy widow. Although she had a very nice house and pool, she seemed pretty frugal with her spending except for the money she spent in her back garden and around the pool.

She was definitely a looker and as I got older I was surprised that she never seemed to have a man in her life even with her great looks and money. Beyond her beauty she was a really cool lady and we had always gotten along famously on the frequent family visits to her house.

As I pulled into her circular driveway behind her black Lexus I had no idea what lay in store for me the next four years and especially the next 36 hours.

I parked and took three bags out of my beater and knocked on her front door. About thirty seconds passed and I knocked again when the door abruptly opened. I couldn’t believe my eyes. Charlie looked better than I remembered. Her hair didn’t have a speck of gray (wink) and was stylishly cut. Her makeup was applied perfectly which meant you couldn’t tell she was wearing makeup at all. She was bare footed and wore a very, very short tennis skirt which showed off her great legs. She had on a deeply scooped yellow ribbed cotton top which showed her ample tanned cleavage... hmmmm... no tan lines. The best part, however, was that her top was loose fitting and allowed her ample breasts to move freely. I would have bet 10-1 she wasn’t wearing a bra. Her breasts were large - probably a C cup or a small D - and looked firm but not saggy... they were just heavy and perfectly shaped. From the loose fit of the thin top and the movement of her soft globes there wasn’t much doubt she was naked under the thin material.

“Oh, Billy, it’s so good to see you again! (hugging me while pressing those big soft beauties into my chest) We’re going to have so much fun these next four years! Here let me help you with this bag and I’ll show you to your room.”

As she bent over to pick up my bag, my guess was happily confirmed. She was not wearing a bra and her magnificent melons hung down allowing her loose top to ballon out so I could see both of her braless tits. Her nipples were pink and had to be 2 inches in diameter. I had never seen breasts as beautiful as Charlie’s... not even in a magazine.

She walked in front of me down the hall and I admired her broad, womanly hips and her gorgeous smooth legs. Her bottom moved freely under her skirt. I had masturbated a thousand times since I was 12 thinking about Charlie so these first few minutes of getting a peek at her naked tits and watching the motion of her beautiful mature ass was an incredible treat for this horny “college man.”

What happened next was beyond anything I could dream up.

Charlie asked if I wanted a beer while we talked and got caught up. Naturally, I said yes. I went into her large den which looked out over her incredible backyard and very private pool. I plopped down on her beautiful white leather sofa... the entire room was done in white and looked very elegant. Charlie went for the beers.

Within minutes Charlie re-appeared with my beer and handed it to me. She then sat down Indian style facing me at the other end of the sofa about three feet from me. As she looked up and took the first swig of her beer I glanced down between her legs and what I saw almost took my breath away. Charlie wasn’t wearing any panties... with the short tennis skirt and her legs crossed underneath her, her pussy was completely visible and open. When I say open, I mean open. Because it was completely shaved, I could plainly see every delicate crevice and fold of her treasure... her fat outer lips, her crinkled pink butterfly lips, her little hooded clitoris and the inviting opening to her probably neglected vagina.

I was startled and made myself look back up immediately. I began talking to her rapid fire hoping she hadn’t caught me looking between her creamy smooth thighs at her delectable pussy. Man, she was a beautiful and sexy woman even in her late fifties. How I’d love to fuck her with my eager young cock and fill her to over flowing with my hot, sticky cum!

“How have you been, Charlie? Have you got a boy friend yet?”

She answered in the negative and said, “None of the men my age interest me... all they want is a one night stand or my money. ...and I guess the stigma of an older woman with a younger man has kept me from dating someone much younger although I would be open to that. I just got in a non-productive dating rut.”

“Good grief, Charlie, that’s a long time... what’s it been?... 5 years since you lost Tommy?”

“Yes, 5 years next month and I have to admit I miss having a man around... being kissed and held... you know all that romantic girl stuff. I also miss the physical intimacy of living with a man.”

“Well, it’s certainly not because you’re unattractive. I think you’re an incredible fox and I know you’re in your mid 40s (wink).”

“Why, thank you, Billy... that’s very nice of you to say that... I do try very hard to look my best.”

“Believe me, Charlie, keep doing whatever you’re doing because it’s working. I don’t know if I can think of a more beautiful woman than you... especially considering the young air head bimbos my age.”

“Hey, come in the kitchen with me and I’ll make you a burger for supper.”

“Sounds good.”

When we got to the kitchen, she scurried around preparing some incredible hamburgers for us for supper. All of her moving around provided me with some wonderful braless eye candy especially since her top allowed her big beauties to move so nicely. Her tits swayed and bounced with everything she did. On two occasions I got a long look down her front like I did when she picked up my bag at the door. I’ve got to tell you, her tits were big and heavy and beautiful.

We ate at the island in her kitchen on tall stools. I may be dreaming but I think she purposely sat on her stool so I could get another long look at her exquisite pantiless pussy? I just couldn’t get over getting these peeks at her most private area. I’ve never seen anything so sexy and desirable. This was going to be a great 4 years.

After our burgers Charlie suggested that we go back to the den and drink some wine. I positioned myself as before hoping she’s return to her cross-legged position at the end of the leather sofa. She did not disappoint. She had lowered the lights just a little so it was a little easier for me to stealthfully gawk at her pussy. What a treat... the sexiest woman on the planet sitting across from me with her legs open boldly exposing her pussy and the tiny opening to her vagina.

We were working on our third bottle of wine and were feeling pretty fluffy when Charlie suggested that we go for a swim. I told her that I’d swim in my shorts and I put my wallet and keys on the coffee table. She told me she’d meet me out by the pool in a few minutes.

I went out the double french doors into her very private and perfectly manicured back garden and pool. Charlie had spent her money well back here and during the warm months this part of her home was surely nirvana.

The moon was full so it wasn’t particularly dark and I could clearly see Charlie coming out of the house in stylish little sandal pumps and an elegant white coverup. She had brought another two bottles of wine - like we needed it - and big fluffy towels for both of us. Then she turned and bent from the waist to place a folded towel in the seat of her lawn chair. Oh my! Charlie wasn’t wearing any panties again and I could see her beautiful mature ass and the rear view of her sweet pussy tucked between her creamy thighs. Wow! I pinched myself... had I won the lottery?

Charlie turned and in a slightly slurred voice - we had had quite a bit to drink - announced, “Billy, since you’re going to be living here with me for four years, you might as well know from day one that I sun bathe in the nude and am a nudist... in fact, I spend most of my time around the house naked... I just needed to get that out in the open.”

With that said she turned and opened her coverup and laid it over the back of her chair. I’m sure my mouth dropped open when she turned to face me and I got my first full frontal view of her naked body. Amazing!... she was absolutely beautiful without a stitch of clothes on. Beautiful face, heavy large breasts, a sexy mature tummy, gorgeous creamy thighs and legs and the most beautiful smooth pussy I had ever even dreamed of.

“That won’t be a problem for you, will it, Billy?”

“No, no,” I stuttered actually thinking, ‘please don’t throw me in the briar patch.’

“What a nice day it’s been... especially with your arrival. This is so relaxing. Billy, please pour me another cup of wine so I can keep this little buzz going.”

She crossed her yummy legs and leaned back in her chair. She was beautiful in the moon light especially since she was completely naked. Her breasts had parted slightly and hung heavy. Her nipples were pink and large but complimented the beauty of her perfectly shaped tits. Her 59 year old tummy produced a small roll but her body was still perfect in my eyes. Her legs were crossed so I could no longer see her pussy but I was confident that would be short lived.

Charlie’s eyes were closing and I didn’t want this pool time to end so I continued our conversation and said, “Charlie, may I ask you a very personal question? I’m not sure about ‘nude protocol.’”

Her eyes opened and she said, “Sure, Billy, you can ask me anything but not until you join me by taking off your shorts.”

“Charlie, I can’t right now.”

“What do you mean, ‘you can’t right now?’”

I answered her by pointing at my crotch.

She paused for a moment and realized, “You’ve got an erection? You’ve got to be kidding, Billy... a 59 year old woman gave you an erection?”

“Believe me, Charlie, you are not the typical 59 year old woman... besides, I’ve had a crush on you since I was 12.”

“Wow, Billy, I’m flattered on both counts... but don’t worry I’ve obviously seen an erection before. Go ahead and take off your shorts and ask me your question.”

“I can’t, Charlie, it’s just too embarrassing.”

“Oh, pooh... let me help you.”

With that she stood and came over to where I was sitting and bent over and grabbed the sides of my loose fitting shorts. Her heavy tits hung down and swayed like soft pendulums as she tugged and pulled my shorts down. By this time I wasn’t resisting just enjoying being that close to her two hanging beauties. I would have loved to reach out and fondle them but I didn’t dare. She struggled with my shorts and finally as they slipped down my thighs my thick, rock hard 8 1/2” cock popped out like it was spring loaded.

Charlie was taken aback by the strong whipping motion it made but when she realized how big my cock was she gasped.

“Bill-leee, that’s HUGE... that’s the biggest penis I’ve ever even heard of. Wow... it’s so thick!”

“Yeah, I guess it’s kinda big.”

“It’s NOT kinda big, Billy... it’s a monster... I’ve NEVER even heard of one that big!” It’s so thick... you’re going to make a lot of these college girls very happy.”

“I’m embarrassed, Charlie, can we get in the water?’

“Yeah, come on.” She took me by the hand and lead me over to the pool steps and down into the warm water. She was obviously having trouble resisting gawking at my cock which remained hard and at attention.

We both slipped down to our necks in the water. I was no longer embarrassed but I couldn’t drink in her naked beauty either.

“Did I really do that to you, Billy?”

“Yes, Charlie, you are very beautiful and very sexy!”

“Even at 59?”

“You look fabulous, Charlie... believe me, age never entered my mind... seeing you naked is what caused me to get hard.”

“I guess I’m flattered but I never intended to have that effect on you. What was your question, Billy?”

“Now even my question is really embarrassing.”

“Oh, pooh, Billy go ahead and ask.”

“Actually, I’ve got two very personal questions to ask.”

“Okay, go ahead and ask.”

“Charlie, I’ve seen pictures of thousands of breasts online but I’ve NEVER seen any woman - young or old - with breasts and nipples as perfect as yours.”

“Billy, that’s not a question but thank you very much. I’ve always thought I was blessed to have these. What’s your question?

“Charlie, are your breasts natural? They just seem so perfect.”

“Yes, Billy, they are natural... would you like to feel them to make sure? You know what President Reagan said, ‘Trust but verify.’”

“You’re kidding aren’t you, Charlie?”

“No, come over here and feel them.”

I couldn’t believe what I was hearing but she was a little tipsy so I seized the opportunity and moved close to Charlie. I reached up with my right hand and cupped and lifted her left breast and squeezed. Man, did it feel good. Not wanting to miss this opportunity I cupped her right breast in my left hand and began to knead both of her magnificent soft melons.

“Okay, Billy, that’s enough. What do you think? Are they real?”

“They’re so soft... they feel like heaven, Charlie, they’ve got to be real. Wow, what a beautiful pair of breasts!”

“Thank you. What’s your second question, Billy?”

“I’m too embarrassed to ask, Charlie.”

“Go ahead, Billy, I can handle it.”

“Will you answer me honestly, Charlie?”

“Well, of course I will.”

“Charlie, how many different men have been inside of you?”

“Wow, that’s a bold question, Billy. Do you mean ‘how many different men have fucked me?’”

“Yes, how many men have fucked you?”

“The answer may surprise you, Billy. I lost my virginity in college to a guy I found out later was interested only in deflowering virgins. He was inside of me only once and never again. Then, believe it or not, the only other lover I’ve had is Tommy. Any more questions?”

I was still very close to her from fondling her breasts and still had a massive hardon. I turned towards her so my hard penis would drag along her leg. We were both pretty drunk and I asked her one more question, “Charlie, may I put my penis inside of you?”

“Bill-leee, I’m your aunt and I’m old enough to be your grandmother!”

“You’re my aunt by marriage, Charlie, and I don’t know of a sexier woman on the planet no matter what her age. Charlie, I really want you to fuck me and take my virginity.”

“You’re a virgin, Billy?”

“Yes.”

“Well, that is interesting... a challenge to teach you how to be a good lover and the thrill of being filled and fucked with an eager young penis... let me think about it, Billy.”

“Please, Charlie, I have to confess I’ve masturbated at least 1000 times since I was 12 thinking about you. Please let me put my penis inside of you.”

“It’s time for bed, Billy. We’ll talk in the morning after I’ve thought about it.”

As soon as I got to my room I jacked off thinking of my beautiful aunt who let me see her completely naked and was even going to consider letting me fuck her. Wow! I tossed and turned all night thinking about her beautiful body... especially her perfect tits and her very neglected pussy.

The next morning I woke with Charlie calling me to breakfast. This was going to be decision time although I was expecting Charlie to say no. We had been pretty drunk and I had been bolder than I had ever been in my life... good grief, I had asked my great aunt if I could fuck her. I did decide to accept her offer of being a nudist in her house and I walked into the kitchen naked. Believe it or not my cock was soft as I left my bedroom.

There she was completely naked again bending over a bottom drawer looking for some utensil or something. Since she was bending at the waist I could clearly see her little brown rosebud and her fat pussy lips. She sensed my presence and turned around.

“Good morning, Billy. I hope you slept well. I took two aspirin so no hangover for me this morning.”

Expecting the worst, I said matter of factly, “What did you decide, Charlie?”

“Well, you might be surprised. After mulling the proposal over for some time I decided that with several very strict conditions I’d do it. I don’t mean to sound like it would be a chore for me... for heavens sake, it’s been 5 years since I’ve had a cock inside of me and I’ve never had one as big as your’s in my pussy.”

As I began to speak the blood began to rush to my flaccid cock... up it came like a soldier coming to attention.

“What are the conditions, Charlie, I’m willing to do anything you say.”

“First, you must tell no one of our arrangement... and I mean no one. I can be hell to deal with if someone betrays me... to say nothing of putting you out on the street.”

“Okay, I promise I’ll never speak a word... to any body!”

“Secondly, you must follow my instructions to the T. I am the teacher and you are the student. Whatever I say goes.”

“No problem.”

“Third, assuming this turns into an ongoing tryst, I don’t want you dating anybody. There are just too many nasty things going around and I don’t want to catch anything at this stage of my life.”

“Deal.”

“Lastly, if this becomes something we both enjoy, I want our bodies to be available to the other at any time. In the beginning if things go well, I suspect you’ll want to fuck me 3 or 4 times a day and that’s fine as long as my little pussy can take the pounding. But when the “new” of our affair wears off, if this little old lady needs her young bull to service her, I’ll expect you to fuck me with all of your original enthusiasm.

“Sounds good to me, Charlie. I hope you don’t think this is all physical for me because I really do have a deep fondness for you and always have.”

“I know that, Billy... and me for you... our little secret will be good.”

“Not to be overly anxious, Charlie, but when do you anticipate taking my virginity?”

“This evening, Billy, after supper... can you make it until then?”

“Yeah, I guess I’ll have to but I can hardly wait to have my cock buried in your tight sugar hole.”

“Me too, Billy, just hang on. Sugar hole... hmmmm? I think I like that name for my little pussy... seems to be an apt description for that secret place.”

I was sure this was going to be the longest day of my life.

Charlie got dressed in a very short white tennis outfit and a big hat... she loved big hats. The skirt was pleated and looked great on her mature hips. As she was getting ready to walk out the door, she hugged my neck, smiled and whispered in my ear, “I’m not wearing any panties.” She turned and flipped up the back of her skirt and sure enough there was her beautiful big bare bottom. She wiggled it, blew me a kiss and bounced out the door.

During the day I watched a lot of TV as summer school didn’t start for another two weeks. All I could think about was being inside of my favorite aunt. She returned about 5 PM, showered and prepared supper.