Harry Herrick and the MILFs: Part 1
This story continues from Harry Herrick's Naked Summer. While it isn't necessary, it's best to begin there.
Working for Ellen
The summer couldn't last forever, and by the middle of September, the majority of my friends were at university. Judith and Stuart had settled into what was essentially a conventional marriage. At 20 years old, my parents were understandably tired of me sitting around without any plans. They gave me an ultimatum: if I wasn't going to university, I had to find a job.
Although I had secured a job in a local real estate agency, I lost it when the owner's son, who was attending university, was given priority. Alternatively, I could have taken a position at the local poultry plant, but it didn't interest me at all. So, my only option was to search for new employment. I could have considered the chicken factory, but it didn't appeal to me either. It's possible that my life would have taken a different path if I had chosen the plant.
While job hunting, I rotated through clothing and interacted with people in a professional setting. This significant departure from my sun-soaked summer days didn't feel natural. Luckily, Colin, the man who initially offered me a job, found one at another real estate company. However, this company was located in a different town, and there was no suitable public transportation, and the previous job didn't offer enough compensation to cover the high cost of living.
While traveling around the new town, I came across a job opening in a local cafe. I hesitantly went inside to investigate and encountered Ellen, someone who had made a rather memorable impression in my past. Her previous memory of me was of her passed out and drenched in my cum. I anticipated being immediately rejected, as she held power over my mother. To my surprise, she didn't kick me out. Instead, she instructed me to wait in a corner at a designated table.
Since her divorce, Ellen had become sober and lost a significant amount of weight. She had also made a dramatic shift in her life, accepting a job as a manager at this cafe. While I recognized her, she hadn't acknowledged me, leading me to assume that she had forgotten our past encounters.
After completing her work, Ellen removed her apron and joined me at the table.
"I need to hire more staff because we received an alcohol license, and now we'll be open three nights a week as a cafe-bar. Angie, who's in charge right now, will be managing these events," Ellen began. "We have plenty of staff for the cafe, but we're desperately in need of someone to work the bar. I'm seeking a man for this position, but I'm not looking for a bouncer. Instead, someone like you, young and fit, would be a bonus regardless."
"Would you be interested in the position?"
I expressed my interest but emphasized that I couldn't start immediately because I was still looking for a place to live.
"This shouldn't be a problem. Angie is moving in with her partner, so she's vacating the spare room in my home," Ellen said. "You're welcome to stay in my home until you find a suitable place of your own. Don't be concerned about your mum, either. I've been discreet about the situation and assured her that you were simply helping me get some sleep on your bed after a night of drinking."
I was startled by her admission of our old encounter. During our limited interactions since this event, Ellen had never mentioned anything about it. It crossed my mind that my parents might have been aware of my summer adventures, but I couldn't then know how widespread the knowledge would become.
Ellen then mentioned, "From what I've heard, you'd be a better fit now."
I looked at her in astonishment and questioned how she'd come to know about my recent conquests. "I thought I'd been quite discreet, but if you're aware, did my parents hear about it?" I wondered.
"No, your mum didn't hear anything from me. She knows about the issues I faced with Joe and Alice. She would undoubtedly want to understand how I handled it."
Joe and Alice were Ellen's children, who were around two years older than me. The eldest son, Joe, had caused a scandal by impregnating the headmaster's daughter. Alice had initially fallen victim to drugs, ultimately resulting in a hospital stay. With their father abandoning them both for a much younger woman, it wasn't surprising that Ellen's life had taken a turn for the worst.
The lady's doing fine. She's taking control and is going strong in her second year of training to become a Mental Health nurse. She's got a boyfriend who's also on the same course with her. I do worry sometimes, but I think she's going to be alright. Her ex, Joe, is the one who got another woman pregnant this time. He seems to be a bit more dedicated to this one, but let's see.
I couldn't help but think, "Phew! Fortunately, no one got pregnant there." Then I remembered how careless I was before and how careful I had become.
"It's not about being lucky or sensible, it was mostly lucky before."
I apologized to you, Harry. I know it was a stressful period for you.
Smiling wide, "I wasn't exactly trying to rape you. I was just too drunk to really do it."
"Don't put yourself down, Ellen. You're not that old."
"I'm not sure about the rumors regarding you and Judith. Did you go on your honeymoon with them?"
I chuckled, "No, I didn't, and I'm not going to talk about her or Stuart either. They're my friends, and I don't gossip."
"Would you accept the job offer? We can start training you here before the cafe opens."
"I'll take it. I need to finalize some matters with the agency so we can start on Monday. Can I come back here afterwards to complete the rest?"
"Of course." Only a few minutes' walk from the agency, it didn't take long to wrap up. I headed back to the cafe. The staff had just cleaned up for the evening customers. Once done, Ellen took me upstairs to show me the room while Angie secured the cash from the register.
The room was surprisingly large, with plenty of space for a double bed, a wardrobe, and some drawers. There was a table in the bay window, which I was amazed to find had a small watercolor painting.
"You're an artist, Angie? So am I!"
"Regretfully, I'm taking the table. I got it to use as my workspace, and I'm moving it to our new place."
"No problem, I'll use my easel instead."
We talked about the practicalities of moving in, the rent (so low compared to what I predicted), and a start date.
"If you can start on Monday before the bar opens, we can train you on the till then, and once the bar opens in a couple of weeks, you'll be ready."
"I still don't have a place to stay. Angie will still be here."
"No problem. The couch folds into a bed. I'm certain you won't mind sharing space with two women, right?"
Angie chuckled. Probably knowing about my summer, she was watching my reaction. However, I was determined not to complicate the situation here until I had moved in and settled down. Ellen was still attractive, with big boobs, broad hips, and striking dark blond curls. Ellen also slimmed down and lost weight over the past year. Her large breasts no longer sagged but instead popped out perfectly into a stunning cleavage. Her hair was cut close to her head now. She was still pleasantly plump but didn’t seem to be wearing a girdle like a year ago.
I realized I was staring at them intently. I saw a glance between them, but otherwise, they acted naturally. Thankfully, they hadn't gotten upset or offended by my stare.
"Ellen, where do you live?"
"Molly Thomas is my sister."
"Molly Thomas is your sister?"
"Don't worry, Molly tells me the details we usually keep from our mother. So I know quite a lot about you, Harry Herrick," Angie replied, smirking.
Grr. I couldn't help but let out an internal groan. The whole situation with Ellen was tough enough, but to add Molly to the mix, it was just a whole different level of messiness. You see, Molly was one of the many summer girls I'd been with that year, and apparently, she claimed me as her first. Rumors about me having a knack for winning a woman's virginity had spread through the town.
It was a sweltering summer day when Molly and I found ourselves alone in Judith's summerhouse, and she got quite excited. She was still quite timid, so her sudden burst of energy led to a noisy, passionate moment between us. I'd been given the key to the summerhouse by Judith herself, so I wasn't shy about inviting some girls there. And also, I recall we had a fun afternoon with Molly there - into the sunset. Her personal preference was the missionary position, with me on top, and she definitely enjoyed all those sessions.
"Hey," Judith started, "just make sure you don't show up unannounced with Stuart around."
"And if you thinking of bringing some girl here," she continued, "only do it if she's into it, too".
"So, you mean Molly told you about me?"
"Molly told me, she used to babysit for Judith when she was young and knows the whole story about us," she replied.
My ears went red as I fathomed the implications of her words. Word was spreading quick - I'd slept with like over 40 girls in the span of a few months. That's quite a toll on a town like ours.
"The gossip has been heavy. All those girls talked about you," she said, "and from what Molly told me, you and she were quite busy that day".
"And judging by what she's told me, she was encouraging her too."
"Ellen would sometimes babysit Molly when she was younger. She shared her own experience and how gentle you'd been with her."
"So you think I'm well-known?"
"You're the teen guy who has had it with almost every girl around. It's hard not to be noticed."
"So we're going to widen the range of customers? Is that it?" I had to laugh at the absurdity of the situation.
"I don't know if you've gotten that many, but many," she added, "but it's quite a number, so yeah," she laughed, "your reputation of being a skilled lover has spread far and wide."
"I actually wasn't so well-informed about your previous relationships", I admitted.
"You must know I spent my youth getting close to 40," she replied.
There was an awkward silence when we continued the ride, before she abruptly said,
"I'm envious of Molly."
"Of Molly? How's that?"
"It's because she got to have the good sex with someone who cared."
"What do you mean by 'cared'?"
"You know, the kind of sex where both parties offer their pleasure to one another. The kind that many women crave for but don't often experience."
"So what about Gerry?
"Gerry is a great companion, but he's never made me come."
This surprised me, "You've never had orgasm in your entire sex life?"
"No, never," she said, looking a bit shy.
"What? Not even with me?"
"No," she admitted, "not even when I was properly aroused."
I couldn't help but feel sympathetic at her story - she was lamenting the loss of experiencing what she considered to be 'good sex', which she'd heard so much of that I was capable of providing.
"You mean you had to rely on pleasing yourself?"
"Uh huh," she giggled a bit, "I was too embarrassed to divulge that at first. But there was one instance, just before I went into the army, I had some drinks with friends of mine."
"We were chatting about men," she shared, "and one of them, older than me, was frustrated about her boyfriend who was only keen on please himself."
I could sense the tone of the story taking a flirtatious turn, "She said that women would be happier if men hid away until they truly needed them for reproduction."
"I quipped that I thought women would benefit more from better sex, and she teased me to ask why I missed out on sex. All I could quote from those casual sexual encounters was the lack of an orgasm by my partners, since things had only gone as far as them rushing to climax, apart from the few pecking inside me."
"I was young and naive and didn't fully comprehend the idea of self-gratification - but she was gracious enough to initiate me into that realm."
"And?" I prompted, slightly curious about the upcoming development, "curious to find out"
"It was amazing. I never thought pleasing a woman could feel that good! It was far better than anyone could have offered me any other way," she said.
"And the other time was in the cafe?" I asked, curious about the other encounter.
"A girl in the cafe was hitting on me and I thought, 'why not?'"
I was amused by the seemingly haphazard but spontaneous casual encounters but there seemed to be a lot of roguish adventures hidden in this story.
Gerry puts in effort but has never succeeded. He's okay with it if I end things afterward, and I've taught him how to do it. I wish I could experience what Molly had with you at least once though. Please, Harry, can you make it happen for me? I'm not as stunning as Molly, but I'm not unattractive either.
Considering the circumstances, I was inclined to refuse. However, I was intent on experiencing her supple breasts. She was grasping for tears and I crumbled.
"When are you leaving Ellen's place?"
"The following weekend."
"I'll start work on Monday. From Monday to Friday, I'll visit your bedroom to try my best to make you climax as much as possible. I can't guarantee anything after that."
Her back and forth movements caused her to sway dangerously.
"I'm already getting wet just imagining it."
Her face brightened.
"If I come to pick you up on Sunday, that gives us another night, and you won't have to lug your belongings on the bus."
I kissed her cheek and she drastically steered.
"Sorry."
"That's fine, thank you."
My Second Meeting with Mollie
Upon informing my parents of my new work ventures and relocation, they were supportive in light of the newfound adult status I'd be adopting. They were especially delighted for Alice, who'd sampled the struggles of life first-hand.
I then went to visit Judith and Stuart. They were both overjoyed to see me. Judith continued unabashedly, yet I could empathize with her through my newfound insight. Even though she'd described Stuart as droll, he was enamored with her. I shared my recent employment details, including Ellen. Judith knew my initial encounter with Ellen but had kept her mother's identity a secret.
"Every opportunity you have with her, show her what she missed, my dearest son."
Incredibly, she didn't try to fuck me.
"I'm being a bit more patient these days."
Given her comment, I feared she might be ill. She must have sensed my concerns, as she embraced me tightly.
"Fear not, love. I'm not ill. I simply found out I'm pregnant. I can't believe it at my age, but it's true. Avoiding any hersitis was our top priority but you'll be relieved to know Stuart is definitely the father."
Her words prompted me to contemplate if I could be the father. Judith smiled and held Stuart's hand in assurance.
"Don't worry, dear one. If there was even the slightest possibility, I wouldn't consider anything without your knowledge and consent."
They both hugged me and I reciprocated their eager expressions. I was equally elated for them.
"Do you know how Ann feels?"
"She's starting to accept the situation."
I recognized the implication, recalling her enjoyment of the spotlight. With a baby on the way, significant changes would affect their relationship. I presumed Ann's distanced residing in Cambridge would be another contributing factor.
Before leaving, Judith said:
"The summerhouse remains unused this weekend. Just in case.."
I giggled and waved before pedaling back home. I didn't have any concrete plans for the weekend. The girls in my life had either pursued higher education or were too young or not attractive enough for me. I did, however, have Molly's contact information - you know, the real Molly, not Angie. And the summerhouse was unoccupied...
Without further ado, I called. Molly answered, which confused me instantly as I had assumed Angie was home. She passed the call to Angie without comment. I conveyed my weekend blueprint, which left Angie slightly shaken. She hesitated but soon recovered.
Molly interfered and whispered to me.
"Gerry is at my mother's birthday celebration too."
"Thanks for offering to help out Angie, Harry."
"She already informed you?"
"Of course."
After a brief silence.
"Harry, how about we meet up sometime this weekend? Before you begin work. I'm returning to college on Sunday night."
Throughout her speech, I could hear the pleasant tone in her voice.
"Is it possible?"
"Absolutely. Whatever occurs will be enjoyable."
"This afternoon suitable?"
"As long as I make it back in time for mother's party that night. Angie and she will be shopping in the afternoon, so..."
"I'll meet you around two o'clock."
Smiling to myself, I sat back. I never had two sisters before, but it appeared I would have the pleasure of sleeping with Molly today and Angie tomorrow. They didn't resemble each other, but I wondered if there would be similarities in other ways. It was one wild and unique way to transition from school to work.
As I returned to my parents' house through the back gate, I noticed Judith lounging by the house. She waved and sent a kiss in my direction. My feelings for her were still strong, but the intense sexual attraction I used to have towards her had vanished, replaced instead by a strong familiar affection. It was likely due to Stuart's presence, as well as her status as a mother. I took a moment to reflect on the weekend before their wedding when I had easily satisfied her insatiable desire. I recalled how she lay in the king-sized bed, limbs outspread, and a satisfied expression on her face.
"No more," she had said. "I'm finished."
I doubted our weekend escapades would be as frequent in the future, but I was certain they had a good understanding of that reality.
My reverie interrupted by Molly's arrival, I experienced a sudden sense of déjà vu. She too had been an athlete at school--playing tennis and hockey, and running long distances. However, unlike her sister, she still retained her lean, muscular frame, sporting long, dark hair. Clad in a short tight denim skirt and a cotton shirt, her long slender legs were bare. Standing near me, she looked absolutely stunning.
"You look utterly gorgeous today."
She smirked.
"I know."
"What happened with the athletes at college?"
"There were a few moments of glory. But nothing compared to our time together here before."
"I appreciate being remembered."
"Do you plan on exceeding the previous weekend's exploits with me?"
"I live in hope, but to be frank, I came by wanting a decent fuck. It's somewhat addictive."
Step by step, she stepped nearer, pulling me in for a lingering kiss. I tasted the sweetness of her lips, while her figure, clad in a hot skirt, straddled me. After ending the kiss, she slowly removed her shirt and unfastened her bra, exposing her firm breasts. Afterwards, she discard her panties, revealing her uninhibited body. I caressed the back of her calves, running my hand up and down.
Bending down, I took off her shoes and socks, then helped her with her belt and zipped fly on her trousers, taking them off. A similar process unfolded with my boxers. Unzipping my trousers, she delicately removed my shirt, leaving myself naked, vulnerable to her touch. Seated on my lap, my erect dick standing proudly between us, she started removing my shirt. Now both bare, Molly straddled my lap, teasing my dick. Unable to contain my own arousal, she touched every part of my body, from the smoothness of my skin to my errant pubic hair. Continuing on, she brandished her backside, tight firm cheeks, contrasting starkly with her sister's heavier build. As she stood, her breasts, contrary to Angie's more hefty bosom, didn't jiggle, instead gracefully maintaining their shape. The rest of her physique was toned to perfection, but topped off with that silky skin, demonstrating her attractiveness to the male eye.
Sitting, she slowly removed my belt buckle and unzipped my trousers, sliding them off, before discarding my boxers and leaving everything in a heap on the floor. Finally, she locked my gaze with her smile as she settled himsson between my thighs with my erection pointing skywards.
The thought of the coming events with ironically transforming my life as I transitioned from adolescent to working adult.
I reached up to hold her breasts, feeling them harden under my touch. She gazed down at me while I caressed them gently, rotating my palms slowly on her rigid nipples. In response, she leaned in to kiss me again, kissed me for what felt like forever. Her hands were on my chest, keeping me just barely apart from her. After a long time, she began to kiss me everywhere - each inch from head to toe. For the most part, she kissed softly, sometimes even nipping or sucking at my skin, her attention focused so completely that I was afraid to breathe, lest I disturb her.
Finally, she returned to my most sensitive areas, careful to examine every angle of my cock, as if she was trying to store this image in her mind. Then she gently wrapped her mouth around my cock's tip, caressing every inch with her lips and tongue until I was nearly ready to explode. I was tempted to say something, but I knew better than to interrupt her elaborate and stunning performance. The feeling was indescribable.
Driven wild by her slow but meticulous caresses, I teetered on the edge of release for what felt like an eternity until, with a surge of relief, she increased her pace, deep throating me. Relishing this seemingly endless pleasure, she swallowed my ejaculate as I lost myself completely.
I fell back, breathing heavily, but that didn't stop her. Her touch continued, kissing me here and there before I felt myself rising again. This time, I attempted to flip her over, but she would have none of it. Instead, she allowed me to enter her, her body pressed against mine, our nipples and pubic bones practically fused together.
As I stayed there, she pressed against me, applying pressure against my cock that seemed to ripple through my entire body, as if I was being bathed in her body despite not having reached an orgasm myself. Her body writhed some more, sending impulses through my excited flesh, making me feel like I was hers to command. Eventually, she permitted me to sink deeper. Our connection was complete, and she sat on me, gripping my hips, welcoming every thrust. A few moments later, I felt her muscles tensing, and she let out an exuberant but controlled scream of pleasure. My body tensed as well, brought closer and closer to a release I'd been waiting for throughout this distant dance.
Coming to an end, I began thrusting with even more vigor and pressure, occupying every nook and cranny of her and hers of me. Feeling her shudder from head to toe made me even more spasmodic, and in response, she climaxed once more.
We collapsed into a heap, entangled in each other's limbs, shaking and spent. Through gasps and shudders, I somehow managed to ask for her to change positions, and she immediately did. With a sudden burst of energy, neither one of us could have anticipated, I thrust upwards, preventing it from being seamless, but when we settled down, she held me close as we danced together, finding new levels of closeness. In the end, she kissed me one last time before slipping away and disappearing into the sunset.
Feeling completely drained but intent on not going home, I couldn't move for a while. Stuart approached through the doorway, asking if I was ok.
"We saw her leave and came over to make sure you were okay."
I followed Stuart into the house where Judith greeted me with a big hug and, after seating me with a warm drink, offered me some support.
"Remember the weekend we all went away before you two got married?" she asked.
"I don't suppose I'll ever forget that," I replied.
"I feel like I've had a similar yet different experience, but unlike you, I felt depressed afterwards. I think I'm unlikely to experience such intoxicating moments again."
"Nothing is permanent, Harry." Stuart reminded me. "Each moment is a one-off event - something to treasure."
I couldn't help but laugh at his insight.
"What's so funny?" Judith questioned.
I couldn't tell if she meant my response to Stuart, the entire evening, or the entire magical night. I tried to think it over, attempting to find the words for what I'd just experienced.
Hey, tomorrow and the days following are going to be eventful. And it's just that the person who'll make these events happen is Molly's sister. I only got to see Molly today because I attempted to contact Angie.
Discussing love life
"Harry, hasn't anything changed about you?" She continued, "Girls are always falling for you. It's like second nature to you. How many girls have you slept with since you started with Ann? I don't think you've even kept count."
"Actually, I do. I've been keeping a record since I was 15. I've not tallied them up yet. Let's say they're around 30 to 40, give or take."
"Do you understand that some people only have a handful of partners in their lifetime, not to mention 30 or 40 in three months? How many of them got bitter with you?"
"I don't think any of them are bitter. I never made any promises beyond trying to make it enjoyable for both of us, and sometimes even the three of us." There was a moment of silence as I remembered a particularly memorable encounter. "Or, in one case, there were four of us."
"I'm about 15 years older than you," Stuart mentioned. "By the time I was 20, I'd slept with one girl. I didn't sleep with another until I was 25. By the time I met Judith, I was barely in double digits. Harry, you're incredibly rare. Not only because of the number of girls, which is extraordinary on its own, but also because you're still on good terms with all of them."
I reflected on the girls I'd been with since Ann asked me to be her first, right after July. Out of all of them, I was the most removed from Ann, not because of her actions, but because of her own feelings. After she propositioned me following the wedding, she had admitted she felt somewhat guilty for becoming so infatuated with Paula. I had told her then, and still believed it, that sex does not equate to possession. Maybe I was shallow, but when I was with a girl, all I offered was a promise to make the moment enjoyable for both of us. I wasn't prepared to make long-lasting commitments.
"I've never had to hunt for a girl. Since Ann and I started, there's always been girls coming after me."
Stuart chuckled.
"If you think back to your first time getting laid, it took me years of pleading and grumbling to make it happen."
The conversation lifted my spirits. I hugged them both and left to go home. Despite the warmth of their embraces, I was already daydreaming about the upcoming week and what might transpire with Angie.
Encountering Annabel
On Saturday evening, I was still restless, so I went to our usual gathering spot. There were quite a few acquaintances in the area, but none from my close circle. I was sitting at the bar, busy with my drink when I noticed a woman on the next stool scrutinizing me from the corner of her eye.
As I tried to flag the barkeep for a refill, I stole another glance at her, wondering if she'd say anything. She immediately shot a look at me.
"I know you," she stated. "It took me a while to figure it out. You often surround yourself with a crowd of pretty girls. I've seen you around this place, at the Unicorn, at the Feathers. You always have a group of girls around you."
"These girls are all off at university. Probably hanging out in studenty bars all across the country now."
"Not you?"
"I wanted to take a breather. I'll likely go back to lectures next year."
"You aren't going to be alone tonight," Annabel said. "Drink with me."
She extended her hand towards me.
"I'm Annabel by the way."
Without thinking, I pressed her hand to my lips instead of shaking it.
"I'm Harry."
She giggled at my odd courtesy.
"So old fashioned."
As she spoke, I noticed a southern US accent.
"How long have you been residing in England?"
"I'm from these parts. However, I lived in New Orleans for years with my ex-husband, may his soul rot in hell. I left him for a young, selfish harlot almost half his age. And here I am, back to my own country."
She downed her drink and signaled the barmaid to fetch her another.
"Why do people like George get away with sleeping around with gorgeous girls, yet when it's the other way around, they're seen as depraved?" She said, her voice lower. "Why are men forgiven, while women get judged?"
She leaned towards me and spoke softly, "So I'm telling you this, Harry, because we women are critiqued instead of celebrated."
"Allow me to enlighten you about this, a middle-aged lady in your bed is like a fierce tiger, while a middle-aged man is typically a damp firecracker."
I smirked.
"I've no experience with that."
"Ah well," she replied, "fancy giving it a shot?"
I was taken aback by this sudden turn in conversation. I didn't expect such a discussion when I took a seat at the bar. She appeared intoxicated, and this brought uneasiness to my mind. She was enjoyable to converse with, but drunkness remained drunkness. To exercise caution, I opted for the safe choice.
"I don't engage in acts of intimacy with someone who's had a few drinks. I've witnessed firsthand how unsatisfactory it is for both parties, and frankly, I don't want to face allegations of rape when she wakes up sober."
"Harry, despite my present intoxicated state, I'm well aware of it. So, would you consider coming up to my place tomorrow afternoon when I'm sober? Would you be willing to crawl into bed with me and engage in a passionate, loud romp?"
"I'm packing my belongings and shifting homes soon, and I begin my new job at dawn on Monday."
"I'll apparently never experience a stroke of luck.
"I'm sorry Annabel. Maybe we'll bump into each other again."
I delivered a cheek kiss and swiftly left. To be frank, I was pulled towards her, but drunk individuals pose a risk. I prefer if the partner of my momentary pleasure recalls every detail after the act of intimacy. My thoughts were also filled with Angie. Although I was drawn to her, I needed to be cautious to avoid life turning complex.
