I worked a lot of part-time jobs to supplement my income between college and when I started university.
One such job was for a small haulage company run by a family that needed holiday cover for the summer.
My versatility allowed me to transition seamlessly into mundane administrative and accounting positions within the company, even though I was qualified to study medicine.
A man in his late forties, whom I will refer to as Chris, and his significantly younger spouse Holly, who handled secretarial work, ran the business.
Chris was a large man who was equally tall and round in shape. He was also significantly overweight, a heavy smoker, a heavy drinker, and a potential heart attack victim.
In contrast, Holly looked stunning, was obviously married for financial gain, and was at least ten years younger than Chris. Holly had long, dark hair, big, dark brown eyes, a slim build, and legs that seemed to go on forever. She was of average height.
Holly was only in the office three days a week because of her childcare duties, but when she was there, everyone in the office was happier. Holly was not only gorgeous, but she also had a wonderful personality. She was friendly and talkative.
Holly had a perfect sense of style. She wore clothing that highlighted her best assets, which included her cute ass, full breasts, and long legs.
Even though her tops were cut so low that her breasts nearly protruded, her skirts were short, her heels were high, and Chis barely noticed her—unlike the other male staff members.
After more than a month on the job, Holly and her two small sons, who occasionally had to accompany her into the office, and I had grown quite close.
She would often bring them in, and I was trusted to take care of them while she finished writing an urgent letter or taking care of other things. I was even trusted to get them ice cream and other treats.
Holly would always respond to this with a peck on the cheek and a twenty-pound note shoved into my pocket as a token of appreciation.
On one occasion, I turned my head because I did not anticipate a kiss on my cheek, which led to a kiss on my lips that probably lasted a few seconds longer than it should have. She smiled when she realised that she had forgotten to put her hand in my pocket and ended up on my swollen cock. No apologies were offered or anticipated.
As I was about to leave one evening, I heard raised voices. Chris was talking to someone on the phone and was becoming agitated. He ended the call and summoned me to his office.
He clarified that his sitter had let him down, and he and Holly were supposed to be attending a black-tie dinner for charity.
Holly tried every one she knew, but naturally, everyone in their friend group was there as well.
He asked if I could watch the kids for him and then stay over in the spare room because the kids were small and would be sleeping, and he would pay me well if I watched TV, played games on his console, had a drink, and invited a friend.
I agreed, but I had to go take a shower and change at home. I also had to get to his house before he left. He repeatedly thanked me, shook my hand, and gave me a bear hug.
Chris met me at their enormous detached house in his dinner suit, which appeared a few sizes too small. As soon as I walked inside, I saw the stunning Holly coming down the stairs, which stood right in front of me.
Holly looked like a model for a fashion show wearing a long, black dress that was cut to the waist to showcase her amazing, long, thin legs. The cut was long enough to show me her creamy white thigh and the lace at the top of her black, silky glitter stockings.
My cock went from limp to erect in record time at the sight of this gorgeous woman because of her high, seductive heels, which made her legs look amazing. Her dress was strapless, and her breasts gave off the impression that they would pop at any moment.
"I was going to ask if you approve of the dress," she whispered in my ear as she hugged and kissed me on the cheek as she descended the stairs, thanking me for saving their night. "I can feel you do," she said, placing a hand on my erection.
After a brief explanation of my role and a list of contacts in case of emergency, the couple left the house a few minutes later.
Before they returned at about four in the morning, I frequently checked on the sleeping kids, watched TV, ordered pizza, and played games on the console.
I had not anticipated that they would have separate rooms, but Chris was so inebriated that he needed assistance getting upstairs to his bedroom. After stripping him down and putting him to bed, we went downstairs to the lounge and split a bottle of wine.
Her feet hurt from all the dancing, so Holly took off her attractive shoes and laid her attractive stockinged feet in my lap, asking for a foot massage.
I gladly obliged, taking one at a time as she ran her free foot along my crotch, causing my cock to wake up and swell. Soon after, I had an erection in my tracksuit bottoms, forming the shape of a tent.
I kept going back and forth between her feet, caressing them and running my hands up her legs to feel the smooth stockings against my skin.
Holly told me to take off my tracksuit so she could see my cock, and I did not object when it came out. She gasped and wrapped her feet around it, pumping it. It was my first time experiencing something so sensual and new.
After only a few minutes of this treatment—I was young and inexperienced—I erupted all over her gorgeous feet, covering her stockings with what seemed like a gallon of stick-hot semen, and she continued to pump her feet until I was empty.
When she was unable to take any more from me, she stopped and gave me the order to take her stockings dirty from my semen off for her. I reached under her dress and ran my hands up her legs, unclipping her suspenders and rolling her stockings down her legs one by one before tossing them onto the floor.
I remained seated, my pants still around my knees, and my nine-inch cock firmly in place and aimed upwards.
Holly was impressed that I was still able to maintain an erection; she took her feet off my lap, grabbed my cock, and began pumping it. After giving me a thorough licking and removing any leftover semen, she took me in her mouth.
I slid the zip down on her dress' back as she bobbed her head up and down on my cock. I needed her assistance, but I was desperate to get to her breasts.
Holly complied as expected, letting her dress fall to the ground, revealing her nude appearance save for her suspenders. The sight before me nearly took my breath away.
Holly had a huge, firm, round breast area with large, pink, fat nipples that cried out to be sucked. Her pussy was completely bald and shaved.
The nude Holly pulled off my tracksuit trousers, leaving us both essentially nude. Instead of giving me a blowjob again, she straddled me and lowered her dripping pussy onto my cock, resting on my balls and putting her tits in my mouth.
Holly lasted only a few minutes before her first orgasm ravaged her body, and she threw her head back as I alternated on her breasts. She then rode me, squealing and moaning as she pumped up and down on my length.
Holly had to switch places; she sat on my lap in a reverse cowgirl position, lowered her pussy onto my cock, and rode me hard while I cupped her breasts. When I was finally ready to fill her, she experienced another orgasm.
I could not resist and shot my load into her, hoping that she was using birth control since I was not ready to become a father just yet.
We had no place to hide when we heard footsteps on the stairs after an incredible session. We did not need to worry because Chris went through the lounge in a daze, went to the kitchen, got a glass of water, and went back to bed without realising we were hiding behind the sofa in our underwear.
We kissed, picked up our clothes, and hurried to our bedrooms because we did not want to risk it.
After getting ready, packing my things, and heading to the kitchen, I saw Chris and Holly sipping coffee. Chris gave me a nice payment, and they thanked me for helping them. Holly then offered to drive me home, but I said no, preferring to go for a walk and get some fresh air.
Holly called me that afternoon, requesting to get together, since Chris had gone back to bed due to a hangover. Despite my doubts, I agreed. After Holly picked me up, we went to a remote picnic area. Holly looked amazing with her white t-shirt, stilettos, and micromini skirt.
Holly rested her hand on my thigh or on my cock for the majority of the drive. Holly was all over me kissing and attempting to take off my shorts as soon as we stopped. Since it was getting late and the parking lot was empty, there was little chance of being caught.
As I undid Holly's t-shirt and unclipped her bra to reveal her gorgeously large breasts, I assisted Holly in taking off my shorts so she could access my cock.
I was caressing Holly's large breasts, pulling and pinching her nipples as she lowered her mouth over the head of my cock and began to use all of her oral prowess on me, pumping me simultaneously with her free hand. Holly said, "I did not finish that blowjob last night." I suddenly poured shot after shot of hot, sticky, salty semen into her mouth as she continued to lick and kiss my erect cock for an extended period.
She choked at the explosion, but Holy sucked me dry until she had every drop. When she had finished cleaning me up, she stopped, and we shared another kiss; this time I could taste the salty semen from her mouth. To my surprise, she went over the edge and experienced an incredible orgasm as I continued to suck and caress her breasts.