01 - The Wooldridge Family

1. The Wooldridge family

I'm Sasha Wooldridge. A 20 year-old University student, living with our family of four in a quiet area of Toronto. Well, it was quiet. A lot has happened in the last year. I grew up a simple country girl, and was raised in the highlands north of Peterborough. It's a beautiful area, with lovely wooded rolling hills, landscape thick with evergreens, lush meadows, and cold flowing streams. The kind of idyllic surroundings that people in the bit cities dream of escaping to for a tree-change.

My childhood was blissful and quiet with my Mom, Dad and little brother Robbie. He's just turned 18 now, and has gone away to College in the US, though I live at home and commute to my classes in the city.

We moved to Toronto when I was 10 years old. Dad was a lawyer, and moved on from his small-town legal practice to a high-flying corporate law firm in Toronto where he was going to be a partner. I still don't know exactly what they do, but they do earn a lot of money. We have a big house. Actually, it's a mansion. It's on a sloping block, in a nice leafy suburb where we have an ideal view of the city, and access to everything.

When we first moved, I didn't like all the noise and hustle, even though we were a lot better off than most people. But the overriding memories of that period are more negative, because as soon as Dad made partner at the firm, he started acquiring the other kind, as well. He had affairs with both his private secretary and one of the firm accountants in his first 18 months in the job. Nobody seemed to bat an eyelid, either at home, or amongst his work friends. It was just what these powerful men at the company were able to do.

I only found out because I used to eavesdrop on Mom's tea party conversations with other wives from the office. When they were all together it was a happy gaggle, but as soon as they got down to twos and threes, the war stories started to come out.

"So, Janice, how are you managing as the wife of a Partner? I hear John's finding the company work fulfilling," Sally McMillan said suggestively, leaving it hanging.

Mom sighed and exhaled, "Yes....in more ways than one, I guess."

She returned Sally's gaze with a grim set of pursed lips. It wasn't easy for a stately Christian lady of sound upbringing, to know how to deal with Dad's misbehavior.

"Have, um....have you...ever had to...?" Mom was struggling to get the words out, even though she and Sally were both on the same wavelength.

Sally spared her the struggle: "Yes, plenty of times. But I just don't think about it because it consumes me. Years ago when I heard about a brief dalliance of Gordon's, I confronted him, but we only ended up fighting, and then he was sullen for the next three weeks. I thought he was ashamed at the time, but looking back it was just boys being boys. Heavens, Mr. Wentworth, the director, actually sent him one of his secretaries as a 'reward' for landing a big client. I only found out because the poor girl apologized to me at a Christmas party! But what could she do? If she'd said a word, her job would be on the line."

Mom was clearly distraught at hearing this. She hadn't confronted Dad about whether he had kissed a secretary, though deep inside, she knew there had been much more than that over the years. But, pretense was a good defense mechanism for now. She felt sinful just thinking about Dad calling those petite girls, hardly a year or two older than his own daughter, into his office. Maybe he was asking them if they needed a shoulder massage, then slowly unzipping the back of their dress, unclipping bras, watching their lingerie and bodice fall to their lap as they looked up at his face with their pure virgin gaze.

I guess Mom was probably also insecure about the fact that she wasn't the typical tall, thin lady of grace who enjoyed elevating herself above others in 4-inch heels. She was a shapely woman, that you might even call 'thick', with a large chest that she kept well hidden, and a voluptuous figure. Probably not the sort that is used to being whizzed around in ballrooms and affairs of state.

The thought of having to survive in the world without a rich and powerful husband, when she didn't particularly know what else to do, would be enough to shame Mom into being silent and standing by her man.

Anyway, I'm sure Mom refused to think about any of these illicit fantasies, but I certainly didn't. I had grown a lot in my teens, and also had a big pair of breasts, and I wanted to know and learn as much as I could about this whole new world of love and romance. Little did I know, it consisted mainly of powerful men taking the flower from untouched pale virgins with sweet innocent expressions.

I wondered if I would be such a one, imagining myself being taken in to the boss's room, seeing his hungry gaze, feeling his hands brush my breasts, and kissing me on the cheek while his strong cologne filled the air. I didn't really mind the idea. I wanted to explore love. I had only had one proper boyfriend, and that was already three or four years ago. I just wanted it to be with the right boy, and most of the ones I had known at school were bad news.

Snapping out of my romantic funk, I peered through the folding glass doors to the alfresco, where Mom and Sally were sitting. Mom seemed to have been lost in a similar daze to me, as she was bright red in the face, clearly ashamed of her own thoughts.

"Are you OK, Honey?" Sally asked.

"What? Oh! Yes, fine...fine," Mom blurted out, with no conviction at all. "Um...would you like some more tea?"

"No, I'm fine, Darling. Sorry...I shouldn't have blabbed so much."

"No, it's fine. Really," Mom continued, "I guess there's positives and negatives with any job. I'm really lucky to have the place here, and it's a great area for the kids to grow up." Mom forced a smile.

________________________

Sally smiled back. She could see Janice was still struggling to come to terms with the realities of her life, but, for a woman seeking to move from mediocrity to the higher echelons of society, wealth and, possibly, power, it was a matter of supporting your husband and maintaining the image of the perfect family. She would come around, in time.

What Sally had never mentioned, though I had sensed it was a possibility from her loose talk, was that two could play these games. At Sally and Gordon's country estate, there were more than just a few pool boys who had entertained her, on occasion. Her smile broadened as she went off into her own blissful thoughts, particularly the previous summer, when Gordon had been called to work in British Columbia on a complex litigation case. In those weeks, she had found a sudden need for thorough pool cleaning.

She remembered fondly, batting her eyelids at the thirsty young men who stood before her in her bikini, as she interviewed them about conducting a thorough job. It was not above a high society lady to enter the realms of the MILF. Not by any stretch!

Her favorite had been Todd. He came early in the day and was prepared to stay all hours. When she offered him a glass of cold cordial to beat the heat, he gladly accepted and seated himself at the poolside bar on a high stool, his manly shaved chest beading with sweat from the morning's work.

With the girls away at college, Sally made her move. Heart thudding and throat dry, she approached Todd from behind, curving both her arms around his muscular stomach, thanking him for his efforts, and asking if he minded if she would 'help' him out a little. He was only too happy to oblige as she, continually massaging his firm abdomen with her petite hands, worked her way around to his front, looking straight at him with big eyes.

She nodded, as both her eyes asked his permission and the sultry sounds of a submissive, drawn-out "Yeah? Do you like that?" escaped her lips. She had continued working her hands down into his shorts until she ran into his already-firm member.

"Aaahh...Ohhh...Mrs. McMillan!", Todd had gasped, as she firmly took control of his throbbing dick, cupping her left hand around his baggy testicles as though to make sure they wouldn't detach.

"Yes, Baby...you like that?"

"Oh, yes Ma'am," he replied, already breathless.

"Do you want a rich MILF to give herself to you today?" Sally continued, coaxing him with questions she already knew the answer to.

"Oh, yes...yes, please Ma'am."

She was now stroking his meaty erection with long and slow strokes, his dick large enough to allow a two-handed thrust. She continued to nod and smile at him, which led him to do the same with his lips parted, trying to maintain a stable breathing rate, before she neared him and plunged her tongue deep into his mouth, scooping, licking, exploring.

Though nearly fifty years old, she was in fine shape, and proceeded to show him her slender and stately body, her petite B-cup breasts, before slowly sinking to her knees before Todd, whose mind was about to explode at what he understood was about to happen. She looked up at him for permission briefly, then sank her hungry mouth over his large cock head, working her way as far as she could down the shaft, using her tongue to stimulate his frenulum, knowing that that would be the ultimate source of his ecstasy.

Her head bobbed rhythmically in and out to maximize his pleasure. As she did, she imagined she was a pert secretary at the law firm, obliging a senior partner's thick cock, and then returning to her desk with a trail of semen down her chin and cum stains on her blouse. Shortly after, her hand that had been resting on his hard abdominals sensed a further tightening, coupled with an increase in his breathing.

Todd confirmed his oncoming orgasm by announcing, "Oh! Mrs. McMillan!"

Sally paused just long enough to retract her mouth from his pipe, smile up at him sweetly and ask, "Yes Baby? Yeah? Are you ready to give it to me?"

"Oh yes Ma'am!! Oh yeah, I'm gonna cum!!" Todd exclaimed.

With that, Sally immediately returned her tongue to its business and took in his full length, just in time for the first spurts of semen to squirt into her throat. It had been a long time since that thick, tasteless and yet bitter, salty glue had been in her mouth, and yet, it was as though it was yesterday.

She held still as he gripped her head tightly with both hands, exclaiming "Aaah! Aaah!" breathlessly.

It was at least ten seconds before the squirting stopped, at which point she had swallowed once and still had a mouthful of his man cream. He released her head, and she slid off his member, looking up at him like a proud kindergarten girl, her lips still glistening with his cum.

The illegality and naughtiness of what they were doing gave the bitter cum such a sweetness. Sally could not contain her malicious joy in thinking about a lady of status such as herself being a slut behind her husband's back. And probably giving Todd a much better time than his young and inexperienced secretary would be delivering to her middle-aged husband. She swallowed once again, smiling deeply and genuinely at Todd, as if to thank him for his gift of semen, then proceeded to get her breath back.

"Oh, Mrs. McMillan. That was incredible!" panted the breathless Todd.

"Good boy!" she replied, licking the top of his knob once to remove the final vestiges of his load, and then smacked him lovingly on his buttock.

"Now, go and finish off the pool, and I'll call you back on the weekend!" A few days later, she kept her word, but upped the ante by meeting him in only her bra, and immediately proceeding to have him fuck her on the outside deck. The thought of the climax his hefty meat had risen her to brought a smile and far-away gaze to her eyes.

It was the warm sun on her chest that brought Sally back to reality, and the fact that she was not on her knees offering her ass to Todd, but sitting with Janice on our alfresco. Oh my! How long had she been reminiscing about her earlier dalliances? It felt like an hour. Sally looked guiltily at Janice, who was looking at her with a funny smile on her face. Sally smiled back.

"What?" smiled Janice.

"Hmm?" Sally was confused.

"Now it's my turn!" smiled Janice, "what are you thinking about?"

"Why?" Sally asked, now turning a bright red herself, realizing she may have been indiscreet.

"You just seemed to be thinking happy thoughts," Janice smiled suggestively, which she promptly realized was inappropriate, and paused.

"Oh! My apologies," Sally cheeks were still flushed, then a wicked smile briefly crossed her mouth.

"You know, Janice Honey, the men aren't the only ones who can play games!"

"Oh!" Janice drew breath sharply, "Why, Sally! You couldn't possibly!"

The lowered sultry gaze and smile she received in return was enough to tell her that Sally could very much 'possibly' play games. There an awkward extended pause in which they maintained their respective expressions of shock and cheeky defiance, neither prepared to give. Janice was eventually the first to snap out of it: "Well - I guess I'd better get the dinner on."

"Of course!" Sally sprang up from the outdoor lounge, quickly gulping down a glass of water. "I need to be off, too. It was lovely to see you, Darling!"

She and Janice exchanged kisses on the cheek, and Sally departed.

________________________

Though Mom had brushed it off in a few words, I had been watching and focused on Sally the whole time. Her 'brief' exit from reality had lasted the better part of half an hour, in which she went from smiling sweetly off into the distance, to nodding her head gently and moaning quietly.

Mom had become embarrassed quite quickly at these sensual noises, and moved inside to tidy up, still not noticing my presence. I was transfixed on Mrs. McMillan, as I realized she was pleasuring herself purely within her own thoughts, without actions. I suddenly had a fierce urge in me to explore, to conquer and be conquered, to lust and to hold and have a man feeling and controlling my body. For one of the first times, I notice my vagina tense involuntarily and my legs clenched themselves together in a sudden pang of desire. I realized there was something strong at work. I wanted it. I wanted to feel those feelings Sally McMillan had been feeling.

That evening, after Mom and Dad had said goodnight and moved from the living area to the Master wing of the house (yes, it really is that extensive). I went to my room, and for the first time in my life, searched up porn while I wrapped my other hand around my muff and started working it. I had no idea just how much there was out there. It blew my mind. Guys with enormous dicks, girls with ridiculously big boobs, mom and stepsons, family incest, and, of course, pool boys galore!

It wasn't long before I had pretty much nailed what I think Mrs. McMillan might have been up to herself, though it would be some time before I found out the truth. I carried on working until my hand was sore, then flopped back onto my bed and promptly fell asleep.

The next morning, Mom and I were having coffee around 9 a.m. when her phone rang. It was Dad, who had already been at the office for a couple of hours.

"We're opening a new office in Montreal. Mr. Wentworth needs a partner to establish it for 3-6 months. He's asked me."

A pause. "OK... What are you going to say?"

"I think it's a great opportunity. It's the sort that would prepare someone for running the entire business eventually."

Mom was nodding her head slowly, silently, processing the thought that her life might be about to be uprooted again. She didn't like Montreal, not that that needed to be a decisive factor.

"How long did you say?"

"At least 3 months"

Mom pressed in a little. "Sasha's settled at the moment, I wouldn't want to interrupt her studies."

"Could we put her in college accommodation?" Dad replied, "We're already doing it with Robbie."

Mom looked over at me, at once realizing I had the entire conversation in hand, and had already made up my mind. The slow shaking of my head confirmed what she had thought, and, it dawned on her, wanted to hear.

"I don't think she'll like that idea. You know she's not particularly independent, even though she's older."

"Well, she'll have to learn at some stage. This might be just the thing for her."

"I don't know, John...I really wouldn't want to rush the decision, anyway. There's also the ladies' club, and the Church," Mom replied.

"Yes, I know there's all that. The thing is, the boss is keen. If I don't give him a 'yes' today, he'll probably move onto someone else, and that might be it, in terms of job progression. You know what I mean? I know it's a lot to take in at once, but we need to move quickly on this one." Dad was definitely keen to get an answer.

"Of course, Dear. Well, if you're really keen on making it work, how about just give him a 'yes' now, and in the worst case Sasha and I can survive here for a week or two at a time, if you got a small apartment and traveled back and forth on the weekends."

The reality of Mom's words sunk in quickly for Dad. Even though neither of us were in the room with him, we could somehow hear the gears turning in his mind. I could tell he was kind of happy with this outcome, and even happier that it had come from Mom, rather than himself. This would give him full freedom to take a fresh young female back to an apartment in inner-city Montreal, and have her fulfill all his desires.

At the same time, I realized that it might actually be what Mom wanted as well. Not so much the reluctance of moving house, or leaving her happy circle of girlfriends and wives from the firm, but not having to think about Dad and what he was up to - just taking Mrs. McMillan's advice and letting him roam free. This was a form of acceptance on Mom's part, that she was accepting Dad's behavior.

He broke the silence with a feeble attempt at pushing back, "Who's going to cook for me?" as if to say he couldn't bear to be without us.

"Oh, I guess we could find a local housekeeper of some kind that you could hire a few days a week," Mom replied swiftly.

I could tell she was actually restraining herself from showing her enjoyment at this, almost coaxing Dad into sowing his oats abroad and satiating himself at his convenience with no pretense of late office hours, offsite meetings, weekend corporate visits, etc.

Then she sealed the deal for him. "I think it's a marvelous opportunity, Darling, and I want to see you succeed. You go for it!"

Mom was closing the sale like a professional, "I'll be so proud to be the wife of a senior executive."

Once that was said, the few remaining minutes of the conversation were meaningless chatter. Dad rushed off the phone to Mr. Wentworth's office like a rat up a drain pipe, and Mom simply hung up and sat staring into space.

"Are we moving?" I asked, to break the tension.

"No, Dear, but your Father is going to be away for a little while. I want you to have stability while you're studying."

"Is that what you wanted, Mommy? To stay here alone while he goes away to Montreal?"

I simply had to get an answer from her, and had just enough courage to ask while the situation allowed.

Mom stared directly at me, "Of course not, Sasha. I want to be wherever your Father is, to support him. We'll just need to make some alternative arrangements for a while."

I went over and have her a long hug, which she returned. "Thank you, Mom", I said, to which she was silent. Her words had come out automatically, like a kind of official answer, but I knew that inside her there were other feelings going on. Whether or not she was able to accept them would be another matter.

I don't think she or Dad realized how distant they had become from one another with him only working, and her at home and effectively being a full time socialite, not to mention that he was probably obtaining most of his sexual satisfaction from sources other than his lawful wife.