A friend wrote in his blog while hiking the Appalachian Trail, “Part of what makes an adventure an ‘adventure’ are the unexpected events that take place along the way.” Well, I totally agree with that observation although my adventures of the unexpected kind haven’t been on a hiking trail. Mine have been on the road to lust and lascivious exploits.

Starting years ago, one of my summer jobs was washing windows at my parent’s house. My dad asked me, well told me, to get the job done “pronto!” I had finished the first three windows then started on my parent’s bedroom. The blinds were open so I could see my mom in bed. It was unusual for Mom to be napping in the afternoon because she liked watching the afternoon soaps. Even more unpredictable was that she wasn’t alone. Mom was with the next-door neighbor, Mr. Appleton, who owned Appleton Home Decorators in town. I was old enough to know that they weren’t discussing window treatments. So, I briefly became a ‘peeping Tom.’ Until that day, I had only fantasized about engaging in the exuberant activity that Mom and Mr. Appleton were enjoying. Thanks to my girlfriend, those daydreams became a reality later in the summer.

Amy was my steady girlfriend since our junior year in high school. She was more mature and confident than me who had self-esteem problems. Needless to say, I fantasized about having sex with her but had no idea how to approach the subject.

After a lazy summer beer and pool party, I drove Amy home when she took my hand and led me upstairs to her bedroom. She was leading me to my first visit to heaven.

While she removed her bikini top, I stood weak-kneed in front of her trying to look cool and self-assured, of which I was neither. “You like my tits, don’t you Kevin,” she taunted.

“What makes you say that?”

“I saw you staring at my boobs today at the pool. You didn’t even try to hide it. At first, I thought you liked my bikini, but my girlfriends said you were leering at my body.”

“How could they tell what I was looking at?”

“My friend Tina noticed the large bump in your swim trunks like the one you have now.”

I couldn’t deny it. She was right. I couldn’t get enough of her prodigious tits. “Yeah, I like your trophy boobs,” I admitted. “They deserve lots of attention.”

Pulling down her bikini panties she said with a lecherous smile, “There‘s more of me that needs attention, Kevin,”

I was naïve but not dumb, so I pretended dumb and asked, “Like what?”

“Take off your trunks, then I’ll show you.”

I yanked down my swim trunks over an excited erection that popped out like a genie in a bottle. Amy looked at me giggling, “Wow!” then she reached into the bedside table pulling out a three-pack of Trojans. “Looks like we’ll be needing these. I hope they fit. You are huge!” she exclaimed. Then she rolled into bed spreading her legs so I could get a bird’s eye view of her nicely shaved pussy.

She showed me two perfectly swollen pussy lips that were as bald and smooth as cue ball. “I shaved it for you, Kevin. Kiss my little button here,” and she pointed to the top of her pussy lips.

I had no trouble finding her pearl size clit and caught on quickly as she begged, “More, more, more.”

Taking my hand, she whispered, “Put your fingers inside me.” To my surprise, my fingers slipped in easily, and was amazed at how wet and warm her pussy felt. “Oh, oh, oh,” she moaned. “That feels so good.”

I can’t say if it was five or ten minutes later when she ripped open a foil condom wrapper and helped me roll it on. My balls ached and I almost came before I was fully covered.

I was inexperienced and tried my best not to show it. With a women’s intuition, she knew I was a rookie and helped me follow her lead. Amy took hold of my titanium hard cock and guided it in the front of her slit.

“Push in slowly, Kevin. I like it slow at first. Later, when you are all the way in, you can fuck me like a wild animal.”

Later came far too soon. I never got to the wild animal part. When I finished and Amy put her arms around me, I fell into a serene trance. She kissed me saying how she had dreamed of us making love, although she wished it had happened much sooner. Finally, she said, her patience had paid off with "A day, I will cherish forever." We stayed wrapped around each other until her lips engulfed my semi-limp cock getting me up for another round.

The second time lasted longer and was more athletic. She wanted to be on top and ride me like a cowgirl. She even said she had an orgasm on our third try.

We were out of condoms, but Amy said, “Before you go home, Kevin, I want to feel you inside me without wearing those nasty rubber thingies. Pull out before you get me pregnant.”

Her suggestion got me rock-hard again and we fucked until her mom called her to dinner. I headed out the back door hoping her mom hadn’t noticed that I had been with Amy. “Are you staying for dinner, Kevin?” she called out.

“No thanks, Mrs. Petrillo,” as I quickly slipped out the door.

We repeated our carnal desires over the following weeks until I left for a week at tennis camp.

A month after returning from camp, I was mowing the lawn in the yard next to Amy’s house earning gas money. The day was sunny and hot, so I wasn’t wearing a shirt giving me an opportunity to work on my summer tan. Amy’s mom was along the fence weeding her garden. She waved me over. I gave her my best fake smile and stopped to say hello.

Her name was Betty Petrillo with many of Amy’s best features, the same cute nose, and full lips. I remembered that Betty had just turned forty because Amy invited me to their family birthday party. I never thought Mrs. Petrillo was sexy until that day in the yard when she wore a wide-brimmed hat, sandals, and loose-fitting overalls. When she leaned over to deadhead a petunia, her breasts were in full view. Apparently, she was wearing nothing more with her horticultural attire.

“Hi, Kevin! Gosh, it’s gotten hot. You’re sweating bullets. Why don’t you come over for lemonade when you are done mowing? I have a question for you. Do you mind?”

I didn’t mind but was a little nervous. She was sure to ask about me and Amy. There was enough time to dream up a few excuses if pressed too hard on our relationship. It was two-thirty when I knocked on her door. “Come in, Kevin. I’m in the kitchen.”

Mrs. Petrillo had put on make-up but still wore the overalls. Her hat was on the kitchen table. “Let’s sit on the patio, Kevin. Are you hungry? I can fix you a sandwich.”

“No, Mrs. Petrillo, I’m fine but the lemonade sounds good. Where’s Amy?”

“She’s babysitting until five or six depending on when the parents get home.”

Mrs. Petrillo put on a pair of sunglasses and led me outside to the patio. We sat on opposite sides of a round table engaging in small talk. There wasn’t anything to be nervous about except when she unfastened the straps of the overalls and let the top fall exposing her breasts.

“I hope this doesn’t embarrass you, Kevin, but I don’t like tan lines.”

Talk about being surprised, I was stunned but in a good way. Her tits were large but firm. They showed no signs of sagging. She was a picture-perfect forty. A certain urgency began to rise between my legs.

“Do you think they’re attractive?”

“What, your boobs? They are GOATs,” Mrs. Petrillo?”

“I hope that’s a compliment, Kevin.”

“Of course. ‘Greatest of all time,’ Mrs. Petrillo. They’re ’ready for adult viewing on the internet.”

“They might already be there. At nineteen, I was naïve and did some modeling a few times, if you want to call it modeling. It was a long time ago, Kevin, and I have nothing to be ashamed about. I wanted some excitement in my life, liked the attention, and found that I was a bit of an exhibitionist. I guess that’s why I’m not shy about showing off my body. Back then they called us emancipated women. Now we are liberated.”

“What did you model, Mrs. Petrillo?”

“I did a few photos for a startup magazine just getting into light porn. Their idea was to take pictures that accompanied erotic scenes in romance novels. One of my boyfriends in college said it was a good way to get into films.”

“How many college boyfriends, Mrs. Petrillo?”

“How high can you count, Kevin?”

“So, you majored in boyfriends.”

“I guess you can say that. Anyway, the magazine dressed and undressed me as an airline stewardess romancing the pilot. I did others as a nurse with a handsome doctor, a secretary with the boss, a farmer’s daughter with the ranch hand in a barn, and one as a high school cheerleader flirting with a teacher. They were pretty explicit but stopped short of showing penetration. It was more of an illusion of having sex. Some vintage photos are out of copyright and were put on the Internet, so mine probably are there. What I did was sexy even erotic, but they hardly qualify as porn these days.”

I adjusted my crotch that was trying to find a way out of my shorts.

“Let me refill your lemonade,” she said. “I’ll be back in a minute. Don’t go anywhere,” and she gave me a peck on the cheek. It felt like a scene from the movie The Graduate where Mrs. Robinson was seducing Benjamin.

Mrs. Petrillo came back to the patio wearing her gardening hat and sandals but nothing else. I couldn’t believe my eyes but appreciated the unobstructed view.

Sitting armchair to armchair she said, “I know you and Kitty are sexually active,” she said.

“Who is Kitty, Mrs. Petrillo?”

“That’s Amy’s nickname. The family has called her that ever since she got her first kitten. She went around the house purring thinking that was the way cats talk.”

“How did you find out about us? Did Kitty tell you?”

“No. I found a used condom while cleaning her room. It had your name written all over it.”

“Funny, Mrs. Petrillo, but I don’t autograph my work.”

Mrs. Petrillo smiled and said, “Time to get her on birth control before you knock her up.”

I was silent for a minute before mumbling, “Yes Mrs. Petrillo. It seems like the right thing to do. We don’t want unexpected surprises.”

“I’m a bit jealous,” she said putting her hand on my thigh, “You see, since my divorce, I don’t get to be with a man very often. It might surprise you that women my age need sex. In fact, Kevin, I think women get a bit hornier at my age; certainly, I have. Finding sex at forty isn’t as easy as it was when I was Kitty’s age.” With that said, she slid her hand further up my thigh.

Changing the subject, I asked, “Why did you get divorced, Mrs. Petrillo?”

“Please call me Betty.”

“Okay, Betty, but what happened?”

“It’s a long story, Kevin. My husband suggested we celebrate our wedding anniversary at a nudist resort in Jamaica. I loved the idea, so he made the reservations for a week. That anniversary changed everything.

“He made it clear that we needed to leave our inhibitions at home. He told me if he met an available woman, he would sleep with her. I was free to do whatever I wanted.

“On the second day, my husband was flirting with every approachable woman on the beach. That meant most of them. I watched as he took a lady with voluptuous boobs and a great ass to a beach cabana. It was an open-air tent with no privacy, so it was easy to see them making love. They attracted quite a large following. She was enjoying it as much as my husband. I was annoyed.”

Mrs. Petrillo took a few sips of lemonade before going on. “That was the first of several women he humped at the resort. I was not among them.

“I wasn’t in the mood to hook up with strange men until one evening I was lounging at the pool alone except for a well-endowed black guy with a great body. He was looking at me and started stroking himself. Watching him masturbate turned me on. I couldn’t keep from pleasuring myself as he whacked off. What the heck, I thought. Maybe I should join him. It would be a shame if we didn’t gratify each other.

“I sat on his cock and we didn’t stop until dawn. Imagine, Kevin, I was twenty-two and it was the first time I had an orgasm, actually several. Not only was he big, but he was also potent. I had his sperm swimming around in me for hours. Turns out he was a cabana boy at the resort.

“When we I got back home, my husband didn’t stop philandering. I caught him fooling around with a neighbor, then his secretary and then the college girl we hired to water our plants when we were at the resort. I wanted to get revenge and started sleeping around and eventually got pregnant. To be honest, Kevin, I’m not sure who Kitty’s father is.”

“You are beautiful, Mrs. Petrillo, so I can see why men would be attracted to you.”

“Thanks and I think you are a hunk, Kevin. Look, we’ve been honest with each other so let me suggest that we get to know each other better. I’d like to show you what an experienced woman can do for a man like you. I might be able to help you with that bulge in your shorts if you follow me upstairs.” She moved her fingers to lightly touched the bulge.

Copulating with a woman my mom’s age wasn’t part of my life’s plan, but I followed her with little resistance. She stripped down my shorts and began with a killer deep throat. I loved the way she toyed with my balls and massaged my prostate. Betty Petrillo was right. She was an experienced woman.

I sucked her erect nipples before slurping on her juicy cunt like Amy had shown me. It was obvious she didn’t need much foreplay. Mrs. Petrillo just wanted my cock and the sooner the better.

“Oh Kevin, don’t wait. Hurry! Put that fat dick all the way in.”

So, I mounted her and stuffed my pulsing cock balls deep. She was like the road sign that reads Slippery When Wet.

“Keep it in, Kevin, and fuck me hard. Don’t pull out. I want every last inch of your thick cock deep inside and feel you explode when you cum.” Her dirty talk just made me bang into her with even more enthusiasm.

In a few minutes, I obliged her by filling her with a powerful load without an inch to spare. No condoms required.

As I got drowsy, she turned me on my back and sat on my face letting my cum dribble out of her cunt on my lips and chin. I had never tasted semen before. I didn’t mind. It added to my excitement but was more unexpected than pleasure. Her comment was, “A lady needs to remember to give back when a gentleman gives her a gift.”

After a while, she wanted more. I didn’t object and she mounted me for a much longer session. There was no pretense as my performance improved while she turned to show me how she liked it. Being with Mrs. Petrillo was a teachable moment.

Mrs. Petrillo’s orgasms came early and often. She wasn’t as tight as her daughter but tight enough for me to cum twice. My God that felt so good without being covered. The release I felt was incredible.

We lay on the bed together until she said, “We’re both sweaty and stinky. Let’s cool off in the shower.”

We cooled off alright but that’s not all. Mrs. Petrillo blew me until I was hard again, then I plunged into her until the hot water ran out. She sucked me dry squeezing out the last drops when I came for a third time. She purred, “That’s what I love about young studs like you. You always have more to offer a lady.”

While we toweled off, she said, “This has been wonderful, Kevin. I needed a real man inside me and you were perfect. I can see why my daughter loves being with you. You’ve got what it takes, Kevin. You make a woman very happy.

“Kitty will be home soon so it’s time for you to go home. I hope what we did this afternoon will stay between you and me. I can’t tell you how much I need that. I’m sure my daughter will enjoy many orgasmic pleasures with you just like you did for me.”

On the way home, I began to wonder if Mrs. Petrillo’s resort story was true or encouragement to follow her to the bedroom. Either way, it had excited me, providing no doubts about what she was after. At home, I felt like a different man. Doubts about my low self-esteem had vanished. It was no longer an issue. Would she seduce me again was my only question?

That didn’t happen. Instead, Amy and I dated and fucked until graduation. Sex was our main and only form of entertainment. Eventually, I got up the nerve to ask her who was her first. She said I was her first. I chuckled and said, “Look, I know that isn’t true. The first time we did it, you were as experienced as a porn star. In fact, with your body and the way you love sex, you’d be a terrific porn star.” I almost said, like your mother.

“That’s nice of you to say, Kevin, but you are right. My first time was with Uncle Herb a month after my seventeenth birthday. He wasn’t really my uncle but a very close family friend that I had known growing up. He kept telling me how beautiful and sexy I was and wanted to give me a belated birthday present. So, Uncle Herb picked me up from school just before summer break and said he had something to show me.

“We drove miles out of town, so I was really excited thinking we were going to the pet farm to get another kitten, maybe even a dog. Instead, he drove to a motel that I knew about because it was where my best friend, Martha, and her boyfriend shack up.

“There was no secret to what he had in mind when we went up to a second-story room. I didn’t care. I was wildly excited, even more than getting a dog. Uncle Herb was Robert Redford handsome with a great body. He knew right away I was a virgin. Uncle Herb was so kind and gentle, loving and tender while showing me things that our sex-ed teacher didn’t bother to mention. It was a birthday present that kept on giving all summer long.

“Kevin, I always wondered why you didn’t want me sooner. I had to seduce you to get me in bed. I mean, Uncle Herb was kind and thoughtful, but he was older. I wanted someone young and sexy like you. Believe me, Kevin, you didn’t disappoint.”

*****

College life is filled with unexpected and unanticipated moments. I joined a fraternity and found the sorority girls to be ready and willing. There was no need to be in an exclusive relationship since it could lead to institutional sex called matrimony that I was not ready for. Most of the girls I dated were eager to get laid, even on our first dates and I was only too happy to oblige. Obviously, I no longer was shy, and my confidence was at an all-time high.

Each girl had a little surprise for me. Gloria wanted to try it bareback. Gloria said she had gotten free birth control pills from the Student Health Center and wanted to try sex without a condom. We both were thrilled with the results. She wasn’t prepared for how much cum was inside her and joked that we needed a larger Kleenex box next time. I liked that about Gloria. She had a great sense of humor.

Melody was an appropriate name since she hummed while giving me a blow job. Angel loved fucking in quirky places like draped over a washing machine in the laundry room. She said sex was more exciting thinking we might get caught. Marlene wanted her roommate to watch us and for her to watch me fuck her roomie.

But wait, there’s more. Beautiful Natalie was a steaming hot girl who I dated for a while. She said she had never gone on a date without screwing the guy, even back in high school when she was voted the Homecoming Queen. We continued following her dating custom for a semester.

But of all those wonderful college girls, the greatest surprise was with the young college librarian. She was maybe twenty-five or twenty-six with beautifully exotic legs and ass. Her name was Mary Ann, but everyone called her Marian the Librarian from the musical The Music Man. I took first notice of her when she was on a ladder retrieving a book on an upper shelf. She was just high enough to reveal that Marian the Librarian wore no panties. I began visiting the library more often after that. On my fourth visit, I asked her to lunch where I learned about her eclectic taste in literature.

We began discussing our favorite classic novels and authors. I tried to be as literate as possible although I was distracted by her dazzling smile and sexy eyes. During dessert she asked, “Have you read ‘Bad Behavior’ by Mary Gaitskill?” I like eroticism in the novels I read. ‘Bad Behavior’ is just that, bold and kinky in places. The book got me thinking about a more liberated lifestyle ”

“No, I haven’t read it. Tell me more.”

“It’s a little bit dirty and rough but exciting. It’s like Fifty Shades of Grey but better written.”

I could have fallen off my chair. “Sounds like fun,” was all I could think of to say.

“We can’t hold it in the library, Kevin, but I have a personal copy if you’d like to read it.”

“Sure. Wrap it in a brown paper wrapper. I’ll pick it up the next time I see you at the library.”

“Sure. Come by tomorrow and thanks for lunch. Just so you know, Kevin, I’m sex-positive and I like to have a little pain with it, physically not emotionally. That’s why the book interested me.”

“Sex-positive? What’s that?”

“Look it up. It’s about liberated women.”

I took her last comments as an invitation.

‘Bad Behavior’ was interesting but not my style. Sex-positive was definitely more like it. Maybe Marian could help me work my way into the bad behavior idea.

On a scalding hot summer day, Marian said, “I’ve got tomorrow afternoon off, Kevin. Why don’t you meet me at my place at three? Bring  swim trunks and we’ll cool off in the condo’s pool.” She gave me the address. I was there five minutes early and rang the bell.

A minute later she greeted me at the door wrapped in a towel that almost covered her incredible body. saying, “Hi, I’m just getting out of the shower. Come on in.

While waving to the lifeguard at the pool, her towel dropped just as she closed the door.

“Oops!” she giggled. “Gosh, it feels so good without clothes. I’ve been so hot and sweaty all day. I’m going to chill out for a while and get dressed later. Do you mind?”

“Of course not. You look lovely just the way you are.”

 “How about a beer?”

“Sure. I could use a beer.”

Marian didn’t bother picking up the towel as she marched off to the kitchen.

When she returned with two beers, I gawked at her body. She had nice firm tits with nipple piercings, a shaved pussy with a clit ring and a tattoo on her ass. She turned so that I could admire every detail.

“Do you like my decorations?” she asked.

“Wonderful,” I said enthusiastically.

“Look, I’ll be honest with you, Kevin. We’re probably not going to have time for a dip in the pool. I haven’t gotten laid for a while and need some attention in that area. You seemed available. So here we are.”

The beer had to wait. We went straight to the sofa. We screwed with me sitting on the sofa and her on top. It was a wet and sloppy fuck that I quickly augmented with my own sloppy creampie.

We drank our beers while I was in recovery mode. The beer was still cold.

“You ever worn a cock ring, Kevin?” she asked.

“Never.”

She reached in her purse and said, “Try this on for size. Get it on before you get hard. It will help you last longer.”

She was right. I hadn’t lasted long on the sofa but didn’t expect a do over. The device she handed me looked like a small sized O-ring they talked about that caused the Challenger disaster. It was black and thick and flexible. She helped me get it on to tightly grip my cock and squeezed my balls. My balls looked swollen and like a taut balloon about to burst.

We got the device on just in time as I quickly became steel rod stiff.

“Let’s head to the bedroom so I can show you my toys.”

She had a huge king size bed that was so disheveled it looked like a hurricane had ripped through the room. By the look of the bed and our squishy fuck on the sofa, it was easy to guess what she meant by ‘a while,’ like a couple of hours ago. I couldn’t help thinking I got sloppy seconds.

Marian rummaged through a drawer filled with odd-looking gadgets. “Here, Kevin, I love these. Just squeeze and release the ball when you put them on my nipples. They’ll stick and they give me a rush. Then she handed me a set of handcuffs, a gag ball and a leather flogging whip. They weren’t the kind of toys I had in mind.

“Strap this  gag ball on me in case I get a little too loud and cuff me. I’ve been a bad girl today. I need to be punished. Make my bottom rosy red then take me from behind.”

She had her butt up in the air and squealed after a few light strokes. She muffled something that meant to whip harder. I whipped harder but she still wasn’t satisfied. Marian wasn’t satisfied until I whacked her at full strength.

She was on all fours when I shoved into her well-lubed pussy. This time I lasted and lasted and lasted. She groaned and groaned but it was a good groan, a groan of pleasure. I knew she was enjoying it as much as I with multiple orgasms working up to a powerful climax. Banging into her pussy with gusto, I also had a potent climax yelling, “Ahhh, ahhh, oh yeah, yeah, oh oh, ahhh,” as I pumped four or five powerful shots of cum deep inside her twat. We were totally wasted.

I removed the gag and cuffs but left on the nipple suckers “Thank you, thank you, Kevin. You were wonderful. I was afraid you might pull out too soon, but it was great the way you punished my pussy. I had some really great orgasms. You must think of me as a whore. The thing is, I needed a last fling before I get married.”

“I didn’t know you were engaged. Who’s the lucky guy?”

“Look out the window at the pool. He’s the lifeguard.”

“Does he know I’m here?”

“Of course. He saw you walk in.”

“He’s going to kill me!”

“Don’t worry. This was his idea as an engagement present after I told him that I wanted to fuck you. He knows I’m a sex positive girl ever since the night I spent with his brother in their apartment. He believes it’s better that we don’t keep secrets from each other. He told me to go ahead as long has he got first dibs today.”

“Okay, I’m out of here!”

“Well, thanks for everything, Kevin. If you don’t mind, leave the cock ring on the table. We’ll need it for later.”

Amazing isn’t an adequate way of describing my astonishment that afternoon. You never know what is waiting for you around the corner. I’ve learned to accept the unexpected gifts as the best the ones.

By the way, I wasn’t invited to her wedding.

******

On a gloomy rainy day in March, I came upon another ‘gift.’ With my high school reunion scheduled for the fall, my mind began drifting into the past. Where are my high school friends today? Have they experienced unexpected events in their lives like mine?

By Googling Tim Johansson, I found that he was a car mechanic in Idaho. I wondered how he got to Idaho and found he had married a girl from there. Next was Bert Zunovi. He was in jail for grand larceny. How about Todd Sireno? He was in grad school like me. Then there was my girlfriend Amy Petrillo and another surprise.

Amy was now known as Kitty Perv, a porn star and sometimes sex worker. She was still cute with great legs and a tight ass, but her body had filled out with magnificent boobs looking very much like her mother’s. She was now a blonde. The first video I watched was called Sister Love on a Nubile Porn site where she was fucking her brother to help him get over a recent breakup with his girlfriend.

I thought the porn actors were fake but in Amy’s case (now Kitty Perv), the guy she was screwing, including anal, was actually her older brother. He was three years older than Amy/Kitty Perv and I remembered him because he was kicked out of school for threatening a teacher with a gun.

After watching two more of Kitty’s films, one of which she was in the center of a threesome being stuffed in two adjacent holes, I found she had her own website inviting men or women to make an appointment for an “unforgettable experience.” Her motto was ‘The girl that satisfies every lust.’

I thought about getting in touch for old times’ sake but knew it could only result in another unforeseen experience. That didn’t stop me. I contacted her at her escort service website out of curiosity. We met at the local Quality Inn. I got a “family” discount that evening. A week later, we had lunch together. After that, we meet regularly for lunch. Most nights she was busy, so lunch was our best option. Sometimes we got a room before she had to leave for her evening appointments. I was still expected to pay.

Six months after our first reunion, we were officially dating. The fucking was free on the weekends. I asked her to stop hooking. Amy said OKAY but she loved acting and wanted to stay in porn. I agreed and was even an extra in an orgy scene.

In a year, we were engaged. I married her on her twenty-fifth birthday. She was pregnant. I was pretty sure the kid was mine but then, you can’t anticipate the unexpected.