Melanie The Caretaker

I first met Ivan the second semester of my junior year while studying art in Florence. He was a friend, or I should say, a business associate of my father's and he called me up in late April to invite me to dinner. I had never met Ivan, but I remember my father telling me stories about him. He was rich, rather eccentric, and a serious collector of sculpture. He lived on an estate along the Connecticut coast and traveled the world extensively.

It was hard for a starving student living on pasta and pizza to pass up an invitation to dinner. No doubt it would be a dining experience. Ivan said to bring a friend, but preferably one of the female persuasion. I knew my girlfriend at the time, Cathy, would enjoy a good meal as well, so we headed off together to meet Ivan at one of the fanciest hotels in Florence.

Ivan was in his late sixties and looked worldly and wise. He hadn't become wealthy without having a bit of dash and swagger to his personality. We enjoyed drinks in his suite and then headed out to a very posh restaurant. I could see right off the bat that Ivan enjoyed and appreciated women, as he spent more time flirting with Cathy than he did talking to me. Cathy is a great flirt in her own right and the two of them hit if off well.

Cathy is very attractive, tall and slender with a beautiful rear end that she knows how to show off with the clothes she wears. I was used to seeing her in jeans and tiny tops. But tonight she had dressed for a fancy dinner and looked better than I could remember. She had on a fairly thin, clingy dress with spaghetti straps. Her breasts were small, but very pert and the dress did nothing to hide her erect nipples. And her ass looked amazing slinking around under the silky fabric. I sure noticed, and I know Ivan couldn't keep his eyes off of her.

Ivan admired the sway in her walk as she excused herself to go to the ladies room. He leaned over to me and said, "That girl is a keeper. Great superstructure."

The food was wonderful, wine flowed, Ivan pontificated, but in a very interesting and amusing way. We actually had a terrific time, but it was Sunday night and we had to head back to get some sleep. Ivan let us go reluctantly; trying to get Cathy to stay for one more drink – he was definitely looking to extend the party. But we thanked him profusely, bid our goodbyes and headed off into the Tuscan night. Before leaving, however, Ivan extended an invitation to me to come visit him in the summer so he could show me his sculpture garden. I told him I would call. And while Cathy and I both had to get up early the next morning, Cathy was decidedly turned on by the flirting and attention she had received from Ivan. We went back to my apartment and fucked our brains out that night..

In late July I decided to take Ivan up on his offer. My father urged me to maintain the connection with Ivan; he was the kind of fellow you want to know, he said. So we made arrangements for me to visit one Saturday for lunch and a tour of the grounds. He told me to bring a bathing suit in case I wanted to go for a swim.

I wasn't all that familiar with the Greenwich area, but as I looked for his address that beautiful summer Saturday, it became evident that I was looking for an entrance gate as opposed to a house. The entrance to his estate was a gap in a huge hedge with stone piers and ornate wrought iron gates. I buzzed the intercom from my car and was instructed to follow the drive to the main house and park in the circular driveway near the front door.

I weaved up the long winding driveway and arrived at the main house. It was an immense Tudor structure and the grounds leading up to the house were manicured to the hilt. I did as told, rang the bell and was shown in by a lovely young blond who showed me into the parlor. Ivan walked in a few minutes later in an effusive mood, shaking my hand and smiling like we were long lost friends. He gave me a tour of the interior of his beautiful home and we ended up on the terrace where lunch was set for two. The terrace looked out over the sloping yard and here and there were sculptures tucked into the recesses of the gardens and hedges. The grounds were immaculate.

Lunch included a bottle of fine Bordeaux, so as we set off on our tour of the sculpture gardens, we were enjoying a nice early afternoon buzz. The sculptures were exquisite, contemporary and very impressive. It was as we were walking by the pool that I first noticed her. The arbor we were walking along came out on the edge of a hidden pool, surrounded on three sides by a pergola and hedges. At the far end of the pool was a grouping of chaise lounges and in one was a beautiful young woman sunning herself. I noticed three things immediately, even from my vantage point at the far end of the pool: she was incredibly beautiful, she was very tan and she was topless.

Ivan waved as we walked by. "Hi Melanie," he yelled. She looked up from behind her sunglasses, smiled and waved back. I couldn't help but notice her breasts jiggle and sway as she waved. I tripped on a stone paver at that point and almost took a header. Ivan smiled at me and continued walking.

"So is she the lifeguard?" I joked.

"Not exactly," he replied. "She's the caretaker."

"The caretaker? What does she take care of?"

"Me," Ivan said. I could tell he wasn't joking. "So if you care for a swim when we're done, I'm sure Melanie would love the company." I love sculpture, but I was ready for the tour to end now. But I humored Ivan for another half hour as we ended up back on the terrace.

"So grab your suit and take a swim. You know where the pool is and there is a changing room in the pool house next to the pool. Just stop in and say good-bye before you go." He smiled in a knowing way and let me take my leave. I tried to act cool, but I wanted to run as fast as I could.

I thanked Ivan profusely, grabbed my suit out of the car – it was really more a pair of nylon running shorts – and headed down through the dense garden paths to the pool. I had no idea in the world what awaited me.

I approached the pool and ducked into the pool house changing area. I realized that running shorts I had brought weren't going to look like a bathing suit, but at that point I didn't really care. I changed, donned my sunglasses and left the pool house, walking nonchalantly toward the far end of the pool where I had last seen Melanie. As I approached I saw that she was sitting up on the chaise and her top was back on. Even more disappointing was the fact that she appeared to be packing her bag to leave.

"You're leaving already? I was hoping for some company." She looked up from her bag and smiled.

"I didn't really have any reason to stay."

"How big of a reason do you need?" I queried.

"How big of a reason do you have?" she asked as she cocked her brow.

I stepped out of the batter's box on this line of questioning and took a new approach. I extended my hand.

"My name is Ben." Her petite hand felt warm and her grip was surprisingly strong.

"Melanie. You were walking around with Ivan before." She gave me the once over. "You're a lot younger than most of the old geezers Ivan trots around the estate."

I explained why I was here and we began a friendly discourse. I found out she would be a junior at UConn, was from Westchester, as was I, and was spending the summer on the estate. I gave her some background on myself and we settled into nice back and forth patter. I remained standing while she sat on the edge of the chaise. We both had sunglasses on and we both knew we were checking the other out in that casual sunglasses kind of way.

She had looked attractive from afar; she was absolutely stunning up close. She looked to be of Hispanic descent, maybe some Asian? It was hard to tell, and I never asked, but she was definitely exotic. Her hair was dark black and very long, smooth and straight, tied up on top of her head with a clip. Her face was exotically beautiful with large dark brown eyes, high cheekbones and very well defined features. She was wearing a very small bikini, white with blue polka dots that starkly contrasted with her dark skin. The top of her bikini seemed to barely have enough material to hold in her large round breasts. Even sitting I could see that her stomach was smooth and taut. Her long tan legs were crossed at the ankles and the bottom of her bikini was tucked into a tight triangle at the top of her thighs.

While I was checking her out, she was doing the same. At the time I was very slender, but muscular in a very sinewy way. My abs were tight, my hair somewhat long and I had never been embarrassed to show off my body to a woman. Melanie sure seemed to be checking it out.

"So I'm told you're the caretaker."

"So to speak," she answered.

"How does one get such a job?" I asked.

"Well, you may not believe it, but I answered an ad in City Magazine. It said something about a summer job on an estate and asked for photos. I sent in a rather innocent, but telling photo of me in a bikini and received a call a week later for an interview. I was told later that Ivan received over a hundred responses and they interviewed 10 young ladies. Missy and I were hired...?

"Wait a minute. Who is Missy?"

"Missy is the other caretaker. We work 4 days a week and overlap on Saturdays. Usually she'd be here today, but she had a wedding to attend. Too bad you missed her."

"Does she look anything like you?"

"Much more all-American – blond, blue eyes, fair skin, but big boobs. Ivan likes busty women, as if you couldn't tell."

"So how did you beat out the competition?"

"Well, my charm and intelligence, and these don't hurt." She cupped her breasts and squeezed them twice, then let them drop back into place. Damn, I couldn't take my eyes off her. She was the kind of woman you see walking across campus that you just know is out of your league. But here we were getting comfortable with one another.

"So is the pay good?"

She looked me squarely in the eye. "Ivan will pay all my tuition for the coming year, room and board here is free – we live in the caretaker's cottage on the grounds – plus we get spending money, he buys us tons of sexy clothes and takes us on an occasional exotic trip to some far-off place. I can't complain."

"So what do you have to do, exactly? Where's your rake?" I joked.

"Well, Ivan was pretty upfront when we were hired. We have to be at his beck and call while we're here. We have to look good, entertain guests, run errands, if necessary, and – this is the kind of weird part – let Ivan watch us." She looked at me to gauge my reaction.

"Watch you how?" I was getting curious now.

"Well, he likes us to be topless or nude at the pool. And we dress up sexy for dinner each night we're here. And sometimes, he asks us to – this is kind of embarrassing – to masturbate for him, up at the house, like after dinner sometimes. I'll do a little strip show and lie down on the couch and – get off for him. He has never actually touched either one of us, but he loves watching us, if that makes sense."

"Damn, what a summer job. So he has you jerk off for him? What, does he just sit there in a chair and watch?"

"Yes. He rarely says anything. He loves to watch us use a dildo, or our fingers, or whatever, and he sits in a chair and watches. And he watches us here at the pool. In fact he's probably over there – don't look around right now – he has a little hidden room over there by the pool house where he can watch me, or Missy. Sometimes he likes to watch how his guests react when we're topless by the pool. He gets off on that kind of thing."

"You mean he's probably watching now?"

"Just forget about it," she said. She reached behind her neck and undid her top. Her beautiful breasts came into full view. She had to be a full D cup and her breasts sloped down exquisitely from her slender shoulders. She had large dark brown nipples that were very erect at the moment and sat proudly on her full breast, tilting skyward. She had the kind of breasts that move and sway with the slightest movement – an incredibly provocative sight. I felt my cock begin to twitch.

"Maybe you should take a swim. I'll make us a couple of gin and tonics." She smiled and got up from the chaise and walked toward a little outdoor bar. Her ass was tight and round and twitched pertly as she walked away in her tight little bikini bottom. I dove into the pool and began to swim laps. As I was breast stroking my way back after a few laps, she came swaying back to the lounge area with two drinks in her hand. Her walk, her face, her body, her whole demeanor screamed sex.

I finished a few laps, showing off my strokes, and then walked up the steps from the pool. The nylon shorts I was wearing were clinging to my partially stiff cock. Melanie looked at my crotch, then she looked up into my eyes.

"Nice centerboard. Must help you swim in a straight line." She smiled.

I smiled at her humor and sat down on the chaise next to her. I perched on the side and she handed me a drink. She kept looking at my crotch and I didn't care because I couldn't keep my eyes off of her either. She took a few swigs of her drink and then turned over on her stomach.

"One of the reasons I was leaving was there was no one to put lotion on my back. You're elected."

I dried myself off, took a giant gulp of my drink, grabbed the lotion and knelt down towards the end of the chaise. Her skin looked radiant and her cute round butt poked seductively into the air. I thought of Ivan watching this spectacle and, while the thought had unsettled me at first, it now got me kind of excited.

I put one knee between Melanie's thighs and leaned over with a full load of suntan lotion in the palm of my hand. I began at her shoulders and kneaded and squished it into her upper back. I massaged her while applying the lotion and she let out a soft moan. I could see the sides of her breasts squeezing out from underneath her torso. I kept applying lotion and worked her back, upper arms and sides. I applied pressure down the center of her spine – very slowly. Her skin was smooth and bronze and I detected no tan lines.

As I worked my way south, I also started to gently press my thigh up into her crotch – just applying a little pressure as I worked her lower back. She kept letting out soft moans and sighs as I worked my magic fingers. I finally reached her supple ass and I slid my fingers underneath her bottom so I could massage her ass cheeks. She felt so good and so soft. I could tell this was having an effect on her as she began to raise and lower her pelvis in a slow rhythmic motion, rubbing her pussy against my thigh. It was such a beautiful sight.

I was rock hard now and enjoying this little massage game. I began to slip my thumbs down lower and lower toward her pussy as I massaged her ass and upper thighs. As I massaged her ass cheeks deeply, I could her little squishy sounds coming from her pussy. She was definitely getting wet.

"Ben, you have great hands. I think I need to turn over. Ivan has got to be loving this."

I had honestly forgotten he might be watching. I stood up and let her turn, her breasts flopping with the movement. She looked at my stiff cock poking out from my shorts and laughed.

"I guess I'm not the only one enjoying this."

She lay down on her back and looked up at me with her big brown eyes. Her breasts were magnificent – full, round, beautiful and upright as she lay on her back. Her nipples were distended and her aureoles were quite large and dark brown.

I squirted a ton of lotion into the palm of my hand and began to work her breasts, massaging and kneading them. I tickled her nipples and she sighed. I worked her boobs in and out, up and down, and then slowly started to head down toward her belly. It was smooth and tight. I gently rubbed the lotion into her skin.

I finally arrived at the top of her bathing suit and, without hesitating, I slid my middle finger under the top of her bottom and down into her wetness. Her pubic hair was incredibly soft and full. She moaned, arched her back to receive my finger, and grabbed my hand and pushed it deep into her cunt.

I leaned down to kiss her while I slid her bikini bottom off. Her whole mouth attacked me and her tongue slid into to meet mine. She held my cock softly in her hand as I began to jack my fingers in and out of her sloppy wet pussy. She was slippery and my fingers made slurping sounds as they built up a rhythm. She pulled from our kiss and began to let out little cries. Her labia lips were wet, flush and extended, moving loosely between my fingers. The inside of her pussy was smooth and very snug.

I could tell she was getting close to coming, so I used my other hand to gently rub her clit while I impaled her on my two fingers. She lifted her butt off the chaise to meet my thrusts and suddenly gave out a scream and went rigid. I kept rubbing and thrusting with my fingers as she came intensely – her eyes clamped shut and her mouth wide open.

She slowly came back to earth and looked at me.

"Holy shit," was all she said.

After a minute of recovering, she stood up and told be to lie down. I reclined on my back, my cock pressing against the thin nylon fabric of my shorts. She leaned down, grabbed the waist band and yanked my shorts off. My cock sprang into view, bouncing around looking for attention. It was solid, thick and rock hard. Melanie eyed my cock, grinned slyly and sat down on the end of the chaise. She straddled the chaise, lifted my legs up and over her thighs and nestled between my legs. I lifted my pelvis up, she grabbed my cock and she began to look at it while she gently stroked it.

"I'm so glad you stopped by," was all she said. "Now it's my turn."

She bent over and took the head of my cock in her mouth. She began to swirl her tongue around the head, teasing me while she smiled seductively at me. She took the head into her mouth, sucked her cheeks in and then let me cock pop out of her mouth with a little sucking sound. With one hand she cupped and massaged my balls, with the other she formed a ring with her first finger and thumb and began to slowly slide up and down at the base of my cock, all the while focusing on taking me deeper into her mouth.

I pressed my feet on the ground, my elbows into the chaise and lifted my pelvis up to meet her hungry mouth. She'd let me cock fall out of her mouth, lean underneath to lick the underside from stem to stern, then she'd re-engage and take me deeper then before. She had done this before, there was no doubt about it, and I could feel my balls beginning to swell.

"You know, I'm going to come if you keep doing that," I exclaimed.

"Good," she said, and then took me even deeper. She began to build up a rhythm with both hands backing up her skillful sucking. She began to moan as she bobbed up and down and I knew I couldn't take much more of this rhythmic tongue lashing.

"Here I come," I whispered. She increased the pace just slightly, then opened her jaws wide as I unleashed 5 or 6 spasms of cum into her open mouth. She continued to suck and moan and I could see a little of my cum drip down my cock as it escaped her lips. It was an incredible sight, watching her dark brown face absorb my fair skinned cock. She didn't miss a drop.

"Melanie, that was fucking unbelievable," I stammered.

"I know," she giggled, cum dripping from her mouth.

She grabbed a towel and began to wipe and clean my cock. I touched her hair and stroked her face.

"You are incredibly beautiful," I stated, master of the obvious.

As she smiled and looked up at me, the phone over by the pool house rang. Melanie hopped up and jiggled over to the bar to answer. I couldn't hear her conversation, but she had a huge smile on her face as she returned.