It had become the highlight of my day, sitting out on the bench in front of the apartment complex I called home, waiting for the school bus to drop the students off. This gives you an idea of how exciting retirement was for me, but at 65 you take your thrills anyway you can.
Each day at 3:35 or so, the Catholic school girls go by, dressed in identical outfits that were as stereotypical as they come.
White short sleeved blouses, red and white plaid skirts and white knee-high socks. I rented a porn movie that had girls dressed almost the same way, so maybe that’s why the outfits put a little lead in my pencil.
There’s four of them that go by usually, three of them walk together and go past my bench first. I say something pleasant like, “Good afternoon ladies,” and they giggle among themselves without responding.
That hasn’t stopped me from continuing to speak to them all year, but the year is almost over so I guess time is running out. The fourth girl is different though. She walks alone, behind the others, trudging very slowly with her books clutched to her chest. Her I like.
She’s a loner, much like I was back then. Not as pretty as the others, but she has a nice smile. Nicer now since she had the braces taken off, and I’ve managed to make her smile recently when she started responding to my greeting.
And here they come. Only two of them in the main pack today, and they giggle when I wish them a nice day, probably thinking that I’m an old pervert wanting to get into their britches. Perceptive little snots.
Then comes Madison. I found out her name last week, and I thought that she was giving me her last name when she said it.
“No, that’s my first name. Madison. Madison Moore,” she told me, blushing as she spoke. “Dumb name, huh?”
“Not at all,” I assured her. “It’s nice. Different. Bob. Now that’s a dumb name. There’s a billion Bobs, but not many Madisons. You’re unique.”
“I guess,” Madison said with a shrug before continuing home that day.
“Good afternoon, beautiful,” I proclaimed as Madison approached. You’re even prettier than this beautiful sunny day.”
“Hi Mister – Bob,” Madison said, correcting herself after recalling that I had insisted that she call me by my first name.
“Tough day at school?” I asked, and she nodded.
“They all are.”
“Well, in a few weeks you’ll be done for the summer,” I reminded her.
“Boy, those are pretty,” Madison said, referring to the lilac bush in front of the building.
“Lilacs? Yeah, they are something. Too bad they don’t last long,” I said. “Have you ever been back there? There’s a whole lot of them.”
I gestured across the way at the patch of woods about the size of a football field. There had been a FOR SALE sign in front of it for about a year, and I was always afraid that somebody would buy it and level the only thing resembling nature around there.
“Really?” Madison asked. “I would like to see that someday. Maybe I could take some home. I know they would get mad if I took them off of this bush here.”
“I could take you back there now, if you like,” I offered. “Unless you have to get home that is.”
“No. Mom doesn’t get home until after 5,” Madison offered.
“Then let’s go!” I said, jumping to my feet and leading the way, hoping that nobody was watching me bring this schoolgirl into the woods.
How old was Madison, I wondered as I led her to the path that led to the lilacs. She looked about 16. What was that old saying? Old enough to pee, old enough for me? Well, having managed to avoid anything more than a parking ticket over 65 years, I had no interest in going to jail for a little piece of tail, no matter how tempting the prospect.
“So Madison, what grade are you going into next year?” I asked, trying to figure out her age from that.
“Freshman,” she said. “College, I mean. I graduate next month.”
“Really?” I said. “I had no idea. How old are you?”
“Eighteen,” Madison said. “Last month.”
“Oh. Happy belated birthday,” I said.
“I know I don’t look it,” Madison complained.
“It’s not that,” I said, but she was right.
Madison was about 5’6″ or so, but was skinny, without much of a figure as far as I could see. She always had her books clamped to her chest, but the peeks I had managed to get didn’t show much. That was fine by me. My wife was an A cup and I loved those little titties of hers until the day she died.
“You’re very mature,” I said. “Much more so than your friends seem to be.”
“They aren’t my friends,” Madison said as she stepped over a fallen branch, referring to the other girls that rode the bus with her. “I’m not very popular.”
“Bet you’re a good student,” I suggested, and she nodded. “Jealous of you because you’ve got beauty and brains.”
Madison shook her head, but while she knew she wasn’t pretty in a classical sense, she liked being told that, even by an old fart like me. And to me she was cute.
“Oh wow!” Madison said as we reached the lilacs, which were just hitting their prime. The aroma was strong and the purples were brilliant under the filtered sun that lit them up.
I helped Madison pick some flowers to take home, and after we got done I suggested that we sit on the stump of a tree before heading back. I didn’t need the rest so much wanting to stretch these moments out as long as I could.
“You live alone with your Mom?” I asked. “No sisters or brothers?”
No. I have an older sister, but she’s married.”
“Your father?” I asked, and Madison shook her head no briskly.
“Do you have a boyfriend?” I asked, and Madison shook her head again, but not briskly and with a little smile.
“Me? Omigod no.”
“Oh. Are you a – you know?”
“A lesbian?” Madison said, and burst out with a laugh, a bright and happy laugh that was so melodic that I joined in. “No, but maybe I should try that. Maybe they aren’t as particular as boys are.”
“I don’t know why you say that, because I think you’re a lovely young woman,” I assured her. “If I were your age I’d love to be with you.”
“Boys like girls than are more, you know, like girls should be,” Madison said, and when I told her I didn’t understand, she explained.
“I’ve got a big nose and a flat chest, for starters,” Madison said. “Hairy as a bear too.”
I had noticed the hair on Madison’s arms, but the long downy fur didn’t repel me like it may her generation. I adored it, alone with the faint down that circled in front of her ears, and it made me wonder if she was also hairy down below.
“You know, a lot of men find this attractive,” I said as I reached my hand over to touch her forearm, finding the hair just as soft and fluffy as I had expected.
“I’m sorry,” I said when I realized what I had been doing. “I don’t know what I was…”
“That’s okay Bob,” Madison said. “That felt nice.”
The hairs were now standing straight up on her arm, and Madison’s pale white skin was covered with goose bumps as the result of my touching her.
“And you aren’t flat,” I said as trickles of sweat rolled down my spine.
“Padding – mostly,” Madison said as she looked down at her blouse and the small swells that pressed against the fabric.
“That’s okay,” I said. “My wife? I’ll bet her breasts were smaller than yours, and she was as sexy as they come.”
“They’re really small,” Madison said. “If we had money I would get implants.”
“That would be a shame,” I said, and then suddenly suggested that she get a second opinion.
“Here?” Madison asked. “What if somebody came back here?”
“We’ll hear them coming a mile away. Remember how noisy we were coming back here stomping through the underbrush?” I reminded her, realizing how pathetic I was acting in practically begging the poor girl to take off her top for me.
A woman, I reminded myself. Madison’s 18, and the only thing I’m probably guilty of is being a lonely and horny senior citizen who still managed to get hard without help much of the time.
“Nobody ever wanted to see them before,” Madison lamented, and then after a moment of awkward silence she was putting the flowers down and unbuttoning her blouse.
Her hands were shaking more than mine were, and mine were gripping my own thighs so hard that it hurt. One button, two buttons and then the third. Now she was pulling the blouse out from under her skirt and pulling it off.
She was beautiful, and just as I startled to tell her so my eyes caught a sight that I hadn’t expected. A vision so magnificent and natural that my heart skipped a beat.
“OMIGOD,” Madison muttured when she saw where my eyes had gone. “I’m sorry.”
“Sorry?” I whispered as I gazed at the hairs that were peeking out at me from the fold of her underarm. “For what?”
“I don’t – I mean, I shave my legs,” Madison explained, nervously babbling while I tried not to faint. “I didn’t know anybody was going to see me like this. I mean, I shave my pits if I’m going to the doctor or something, but otherwise it’s like nobody would ever see them so I don’t bother. You know?”
“Can I see?” I asked/begged. “Please.”
“I’ll show you mine,” I kidded, and that got Madison to smile.
Slowly, painfully slowly, Madison lifted her arm, and as that slender pale limb was raised, my eyes took in the wondrous sight of her unshaven armpit. The deep hollow was overflowing with rich dark hair, and although I had been lucky enough to have dated several women who chose to remain natural in my time, none of them had armpits as spectacularly hairy as Madison’s were.
“Amazing,” I managed to say.
“This is embarrassing,” Madison said, and although her face was beet red she left her hand behind her head.
“You have no concept of how beautiful I find you,” I said. “May I?”
My trembling hand moved up, and then I was touching her. Her underarm hair was as soft as a cloud, and as my fingers moved into the thick tuft I heard Madison breathe in through her teeth.
“Told you I was as hairy as a bear,” Madison reminded me sheepishly.
“Are you – down there also?” I asked, and Madison nodded as she bit her lower lip.
“Nothing to be ashamed of,” I said, and as I started to tell her that quite a few men found body hair on a woman very sexy, I saw Madison’s eyes widen as she stared at my crotch.
I glanced down, and saw that not only was the fact that I had an erection painfully obvious even though my slacks were baggy, there was a large wet spot at the bulge.
“My turn to be embarrassed,” I said, and then realized that Madison might not understand. “I’m not incontinent, just excited. Very very excited.”
“Really?” Madison said.
What a pair we were, I thought. A 65 year old man whose cock was drooling pre-cum and an 18 year old girl with her arm raised so he could play with her underarm hair. Who cares, I figured. How much longer do I have, and when is this chance going to come again?
“Can I see it?” Madison said shyly.
“Never seen one before? I asked.
“One,” Madison admitted, her teeth sinking into her lower lip.
“Did you touch that one?” I asked and she nodded.
“Lucky guy,” I said, and with great reluctance I stopped playing with my young companion and stood up to fish my erection out of my trousers.
“Omigod,” Madison mumbled as she saw my cock swaying out of my fly and almost in her face. “It’s way big.”
“Not really,” I said, and it hadn’t been anywhere this big since it was in my wife four years ago, because I was sporting an honest-to-goodness erection, not the semis that I often got when I would masturbate out of boredom.
Every vein and ridge was swollen as the thick seven inches strained tautly for inspection, The outline of the head of my cock was threatening to burst through my foreskin, and I heard Madison gasp when I retracted the hood to expose the bulb of my member.
“That’s cool,” Madison said as I sat down before my erection poked her in her eye.
“You caused it,” I told her.
“I bet it wouldn’t stay hard if you see my breasts.”
Ah! Madison’s breasts! That was how we got this far in the first place.
“You’re on,” I said, and then Madison stood up and reached behind herself, making a face as she struggled with the hooks.
I could see the bra was padded, and there was a little pink flower between the diminutive cups. Madison had no cleavage, her collarbone was rather prominent, and her ribs showed a bit, but none of that mattered when she pulled her bra straps off of her slender shoulders.
“You’re not flat, honey,” I said as I stared open-mouthed at the cutest pair of titties I had seen in what seemed like forever. “Your breasts are beautiful.”
Madison’s hands came up briefly to cover them, but then she lowered them and allowed me the pleasure of devouring them with my eyes.
“They’re so small,” Madison whined, and while it was true that they were tiny, they were incredible.
Madison’s breasts were indeed small, and almost all of them were nipple and aureola, the plump blossoms dominating the little cones they rested on, but the way her breasts jutted out such that they defied gravity was what made them spectacular. The presence of a couple of tiny hairs on the edges of the aureolas did nothing to make the sight of here any less amazing.
“You lost the bet,” I wheezed, standing up so that Madison could see that not only did I still have my erection, the usually pale tube was now crimson, and there was a long rope of pre-cum dangling off of the tip of my erection.
We were both panting like hounds, and when I reached over and cupped Madison’s breast I felt light-headed. Not even a hand-full for someone with smaller hands than mine, but so firm and perky that their size only made them better to play with.
“I have to go,” Madison said, looking at me with a pained expression.
“I understand,” I said, knowing how I must look, a pathetic old man groping her in her woods.
“I don’t want to,” Madison said. “I have to. It’s five o’clock. We can come back here tomorrow, if you want.”
“You would?” I said, and when she nodded I felt like I was 18 too. “I’d love that. This was the best day I’ve had since – my wife.”
“I had fun too. You make me feel – I don’t know. Special.”
“You are special,” I assured her. “Can I kiss you?”
We kissed, and when my lips touched hers it was like being with Marie again. My erection poked Madison as we kissed, but instead of backing away she reached down and grabbed it.
“Do you want me to…”
I nodded, not knowing or caring what she was offering, and then she stood at my side and moved her fist up and down the length of my cock. Her school ring with the red stone twinkled as she jacked me off.
She had done this before. That one other cock she had seen and touched? That guy was the luckiest man in the world up until now. I reached around Madison’s shoulder and drew her next to me, the tips of my fingers stroking gently under her arm.
“Is this right?” Madison asked, and I nodded.
Maybe it wasn’t right, but it was great. I felt my orgasm build up, seemingly from the tips of my toes, and as it surged through me I grunted out a warning.
“Gonna cum!” I announced, and then I ejaculated like I hadn’t in years, my knees buckling as I did.
Madison’s fist kept pumping as jets of milky seed landed on the forest floor, and even after I stopped cumming and went limp she kept milking it until she had squeezed out every drop.
“Thank you,” I sobbed and unable to stop a tear from trickling down my cheek, took my handkerchief out of my pants pocket and wiped Madison’s hand off.
“Got some on your pants too,” Madison noted.
“If I knew this was going to happen I would have taken them off,” I joked after cleaning up the mess.
“We can do stuff tomorrow if you want,” Madison suggested.
“I wish it was tomorrow already,” I said while helping Madison get her flowers and books together. “I’ll be back here waiting for you.”
We walked to the edge of the woods where I suggested she go out into the real world alone, so people wouldn’t get the wrong idea.
“See you tomorrow, Madison,” I said as she left.
“Okay Bob,” Madison said as she started to walk away before stopping and turning to face me. “I guess you’re like my boyfriend now, huh Bob?”
“I guess,” I replied.
“Never had a boyfriend before.”
“I thought you said that you had been with…”
“No. Never had a boyfriend. That didn’t count.” Madison said sharply.
“In that case, I’m honored,” I said.
“Tomorrow then. Oh. Should I – you know – shave?”
“No!” I said way too loudly than I meant to. “I love you just the way you are.”
I loved at my reflection in the full-length bathroom mirror as I dried myself off after showering, shaking my head at how much I was starting to look my age.
The harsh light of the bathroom was unforgiving, seeming to highlight every vein and wrinkle on my 65 year old body. With about 160 pounds on my 5’10” frame, I was still the right weight but the muscle tone was gone.
Like the hair on my head, the fur that remained on my chest had turned to silver, as had much of the bush around my cock. Even though I had pleaded with Madison not to shave, I decided to do something with the out-of-control forest surrounding my junk, and after weeding it out and cutting it back it looked better.
“You still work, my friend,” I said to my dick, who had not only gotten hard yesterday, but had risen again during the evening just thinking about Madison, and I had to fight the urge to rub one out, hoping to save my energy.
The grinning fool looking back at me in the mirror looked foreign to me. For the last few years that face had been sullen and bitter, showing little interest in living. This guy here? Now this guy was more like the old Bob.
The fact that it took something so juvenile as playing “show me yours and I’ll show you mine” in the woods with a girl barely legal, mattered little. It had been fun, and seeing Madison’s innocent and natural beauty had been a blast from the past as well.
We were going to meet back at that spot again today, and when the morning sun disappeared for a while as ominous clouds passed through, I thought our plans were going to be ruined, but the day cleared as afternoon came.
Dressing as cool and casually as I could, I gathered a few things and headed back about a half hour before Madison’s bus would drop her off. I spread a blanket on the ground near the lilacs, and set up the little plate of cheese and fruit, along with a bottle of wine, and counted the moments.
When it got to be 3:30, I walked back out to the edge of the woods and watched the street. The bus was a couple of minutes late, but it arrived at last, with the 3 snotty girls waltzing ahead while Madison walked behind them.
She dawdled, and then when they got out of sight Madison skipped across the street and towards the woods. I hustled back to the spot and tried to act casual as I waited for my sweetheart.
Madison appeared a minute later, books clutched to her chest, and when she saw the little spread I had set out next to me on the blanket I thought she was going to cry the way her eyes welled up.
“It can’t be that bad,” I kidded as I rose to greet my girlfriend.
“Thank you,” Madison said as we kissed, and my cock was already surging as me held each other.
Those tiny breasts pressed against me, and the aroma of bubble gum and perfume filled my nostrils as we stood there for a minute before going down onto the blanket.
“This was so sweet of you,” Madison said as she grabbed some grapes.
“I forgot that you aren’t old enough to drink,” I said, apologizing for the wine.
“I have a glass of wine at Christmas and special occasions,” Madison said. “This is special, isn’t it?”
“It is indeed,” I said, and poured us some wine.
“Yesterday,” Madison said as she sat across from me, either not knowing or not caring that with her knees raised and her plaid skirt hiked up by sitting like she was, I could see very well. “Yesterday was so much fun.”
“Even more fun for me, I’m afraid. After all, I was lucky enough to – well, you remember.”
“Last night in bed, I was still so excited that I couldn’t sleep. All tingly, you know?”
“And what did you do?” I asked, looking up the skirt of the young lady, and as she bowed her legs open further still it was clear that this was done for my benefit.
“I played with myself.”
“Do you do that a lot?” I asked, and when Madison blushed and nodded and told her that I did too.”
“You do?” she asked increduously.
“Yes. I wanted to last night when I was thinking about you, but I decided to save my strength for today,” I confessed as I looked up at the pale white skin above her knee-hi socks and at her slender thighs.
“Warned you,” Madison whispered as I took a deep breath while looking at the dark brown hairs that spilled out from the elastic of her white panties, the curls peeking out from the crotch and upper thighs.
“You’re beautiful. I want to see all of you,” I said, rolling onto my knees and putting my hands on Madison’s thighs, pushing her skirt down as I reached under to grab the top of her panties.
Madison lifted herself up a bit, which allowed me to slid the cotton undies down those skinny legs. The panties had a slight discoloration in the crotch, and a few curly hairs was also left inside there, along with the ripe smell of her sex.
I peeled the panties off from her ankles and eased Madison onto her back, pulling up her shirt and exposing a bush that fanned over a wide and untrimmed triangle. The hair was dense – so dense that I could barely see the lips of her pussy, which were large and puffy mostly obscured in the pubic jungle.
The smell. I never thought I would ever smell pussy again, and while they were all different in their way, whatever it was that set shivers down men’s spines and got blood surging though their cocks, Madison had. In spades.
I stared at that profusely hairy pussy in wonder, following it down from the little streak of hairs that began under her pert belly button and then fanned out widely. The hair grew way down past her pussy, and the hair continued way down between her legs and up toward her butt.
I lowered myself down, and as my cheeks were carressed by the springy bush my tongue ran over her labia. Madison was quivering and making whimpering sounds, but as my ears were blocked by her thighs, those noises faded.
Trying and failing at my initial attempt to tease Madison’s clit with my tongue, I soon lost all control and found myself burying my face in her sex, using a tongue that had gotten a lot of rest lately to devour her sweet pussy.
Madison was writhing on the blanket like a woman possessed, clutching at the cloth and sending snacks flying, and when she came I knew it because my face was hit with a blast of fluids. I held onto Madison’s hips and kept her close to my face, showing her no mercy as I lapped away furiously.
Madison came again a couple of minutes later, and she was almost off the blanket when her orgasm finally ebbed. I raised my face from her crotch and rose to my knees, looking at Madison, whose face was red and drenched with sweat, her short hair and tangled mess.
“Oh wow,” Madison mumbled as she used her hands to get her up to a sitting position, looking dazed and confused. “That was a lot different than it was last night.”
“Better, I hope,” I suggested, and Madison grinned and nodded, reaching over to my damp cheek and plucking a stray hair off for me.
“My turn,” Madison said, and with that I found myself on my back, looking up at the sky and my girlfriend, who was undoing my belt and tugging my slacks and boxers down.
“Looks even bigger today,” Madison opined as she lifted my erection off of my stomach and gave it a couple of strokes before lowering her mouth down on the tip of my dick.
“Probably not good at this,” Madison said after her lips went up and down the shrouded glans a couple of times, and while technically it might not have been great, my cock was loving it almost too much.
I pulled Madison’s head off of it and rolled her onto her back on the blanket, and with my cock in my fist I brought it to the furry opening of her sex. I was just about to plunge in when I realized what I was doing and stopped.
“Please Bob!” Madison practically cried. “I want you to!”
They say a stiff cock has no conscience, and although I thought up until then that I was the exception to that, my actions proved me wrong because I did. I shoved the fat head of my cock into that sweet young thing, and when I met a barrier I forced it myself through it.
Madison screamed as my cock slid deep into what felt like a keyhole, but she pulled me down on top of her and sunk her teeth into my neck while wrapping her legs around my butt. Her tears were offset by her crazed smile as I humped her madly, and while I tried to make it last, when I felt that wet and narrow opening clamp down around my cock as she came, I did too.
“It’s okay Bob,” Madison was telling me after I had satisfied my animal-like urges and had started to sob and apologize. “I wanted to do it, and it hurt but it was good. Really good.”
“I thought – thought you said you had been with a guy before,” I said as I looked down at what I had done, the evidence of her previous purity very obvious.
“That was just doing junk – you know,” Madison explained. “Not that.”
“Your first should have been with someone you love.”
“Well maybe I do love you,” Madison suggested, and I shook my head and embraced Madison, holding each other tightly until it was time for her to go.
That wasn’t the last time we would made love, but it was the best. All good things must come to an end, and although I had hoped it might last until Madison went away to college in the fall, our affair came to an abrupt end as her summer recess started.
It was an afternoon to remember, that last time, and it was a case of us getting greedy. One day it rained, and instead of sneaking Madison into my apartment complex I let her talk me into going to her place. After all, her mother didn’t come home until 5.
Except for that day. Madison mother didn’t catch us doing it, although if she came home a few minutes later she might have. Not that what she saw when she opened the door was much different.
That was the first time I lost an erection with Madison. There’s something about sitting on a couch getting your cock sucked and suddenly looking up to see a 50 year old woman standing in the doorway with her mouth open even wider than her daughter’s was at the time.
“You fucking pervert!” was the nicest thing she said, and it was a crazy scene, with Madison trying to keep between me and her umbrella wielding mom while I tried to pull my pants up and get out the door.
The last thing she screamed was something about calling the cops on me, but there’s no law against having sex with an 18 year old. She did have a bit financial control of Madison though, so while we had a few conversations before she went west, that was the end. After all, even I realized that there was no real future in our relationship, and she would be soon moving on with her life and I would be alone again.
“You’re the best!” Madison said as she kissed me on the cheek the last time I saw her while sitting on the bench on front of my apartment
I took satisfaction in that, even if I might have been the best simply because I had been the only one, at least then. Chances are she has others to compare me with by now, judging by the way she seemed to take to sex, but I only hope she’s happy.