middle age man


The appointment was set for 9am but the traffic and weather delayed me by ½ hour. When I arrived, the receptionist informed me that my attorney assigned a junior associate to meet with me. Apparently he was due in court at 10 am which left little time to discuss the merits of my case.

I was seated in the conference room when an attractive young woman introduced herself as Ms. Brenda Thomovich and proceeded to discuss my impending lawsuit. During our discussion, she seemed to scrutinize me carefully; perhaps a little too carefully.

As Ms. Thomovich finished writing some notes on a yellow legal pad, she looked at me and asked if I was any relation to a Mrs. Macalino who taught fifth grade at Walton Street Elementary School.

The sudden change in direction surprised me but I was more than familiar with this type of question. My ex wife was a very popular teacher at the aforementioned school and former students often inquired about her.

“Yes, ah, well I was.” I answered in an uncharacteristic stammer.

Ms. Thomovich was regarding me with cold eyes and when I briefly explained that we had recently divorced, her demeanor changed and a chilly air descended on the room.

Many of my ex wife’s former students idolized her and she was indeed an exceptional teacher. However, our marriage was much less than idyllic and especially so towards the end.

My ex wife, Kate, threw herself into her job with total abandon and it left little time for anything else. Our social life was sporadic and sometimes non-existent. Her off hours were spent correcting papers and in general, doing something school related.

Ms. Thomovich was regarding me with a cool stare and I got the impression that she was hesitant about accepting the case. But, her expression softened and she indicated that another appointment was necessary before she could reach a decision.

A couple of days later, I was seated in the same conference room waiting for Ms. Thomovich to appear. The receptionist popped he head in and explained that she was on her way back to the office and if it wasn’t an inconvenience, to wait for her arrival. I expressed my desire to remain and the receptionist handed me a cup of coffee.

At 5:30pm, Ms Thomovich was an hour overdue when she walked into the conference room. She didn’t apologize for her tardiness and her demeanor bordered on unpleasant.

For five minutes Ms. Thomovich bombarded me with questions and in a manner I would associate with opposing council. I probably had a disgusted look on my face because she stopped her questioning blitzkrieg.

“Do you treat all of your potential clients in this manner?” I asked coldly.

Ms. Thomovich had a surprised look on her face.

“Perhaps I should seek council elsewhere.” I stated and stood up.

Ms. Thomovich had a look of regret on her attractive face but it did little to soften my anger.

“Please accept my apology.” She said with sincerity.

“It’s just that…” she stated but I interrupted her before she was finished.

“…you can’t believe anyone would divorce dear, sweet Mrs. Macalino. Am I correct in that assumption Ms Thompson?” I questioned with conviction.

Ms. Thomovich was staring at me in disbelief and appeared to be thinking of an answer.

“Ms. Thomovich…” I started to say.

“Call me Brenda. It’s less formal and considering your age more appropriate.” She stated with wit and humor.

The effect on me was instantaneous and I smiled at her.

“Ok. BRENDA.” I stated with emphasis on her name.

“Given the late hour, we should probably meet for further discussion at another time.” I finished with sincerity.

“Would it be a terrible inconvenience if we discussed the matter at a quiet restaurant about a block from here? My treat” She said factually.

I studied Brenda’s face for a moment but accepted. Looking for another law firm to handle my pending legal matter would be time consuming and possibly more costly.

At the restaurant we finished discussing the details.

“There’s a very high probability that an out of court settlement can be achieved.” She said coolly and continued.

“If their attorney is smart, he’ll push for that and in the amount that the insurance company is willing to pay.” She said flatly.

Brenda accepted my case and with the formal business portion of the dinner completed, visibly relaxed. For the first time, I looked her over. Her creamy complexion, blonde hair and brown eyes were attractively packaged with a slim body.

While we waited for coffee, we talked informally but I sensed something was on her mind.

“Mrs. Macalino was by far my favorite teacher. She was patient, kind, understanding and thoughtful toward each student in her class. I achieved a level of academic success that had escaped me with previous teachers.” She said with admiration and pride.

“And, she would be very proud of you. It’s a testament to her teaching skills.” I stated firmly.

After several meetings with Brenda to discuss the aspects of the suit, I got to know her. She was witty, charming and intelligent. But, she also exuded a sex appeal. Sex appeal is a trait that exits effortlessly inside an individual and is part of their personality.

I started looking forward to our meetings and made every effort to engage Brenda in conversation after the business portion was concluded. After one late meeting, I invited Brenda to dinner as repayment for her earlier kindness.

At the same restaurant, I couldn’t shake the feeling that she wanted to ask me something that didn’t pertain to the lawsuit. It was the same feeling I got at the previous dinner. I tried to shrug it off but it persisted.

“Is there something you want to ask me?” I questioned searchingly.

Brenda stammered a little but as I scanned her facial expression, I knew I was right.

“Is it about Mrs. Macalino and our divorce?” I asked quietly.

Brenda blushed and I objectively stated what I believed were the causes for our divorce.

“After twenty years of playing second fiddle to her job, I wanted more out of life. She was rarely interested in my thoughts, wants or needs. I remember one Saturday afternoon, she brought lunch home but only for herself. When I asked why, she stated that she didn’t know what I liked. Twenty years of marriage and she didn’t know what I liked to eat! But, in all fairness, for most of the marriage, I overcompensated by doing almost all the household chores and grocery shopping.” I explained with sadness.

Brenda was gazing at me with a sympathetic look. But, I was only giving her the highlights because there was more, much more.

“I loved her Brenda and a part of me still does. But, living with her became intolerable. No one party is at fault. We both were responsible for the events that led up to the divorce.” I stated with tears in my eyes.

Brenda placed her hand over mine and gave it a sympathetic squeeze.

“It’s laughable but she never felt that she was a good teacher. I told her countless times that I thought she was an excellent teacher. Her student testimonials and awards were the proof but she never had faith in her abilities as an educator.” I remarked sadly.

“But, I want you to remember her for what she meant to you; an excellent teacher who inspired you. I wasn’t paying her lip service, I truly believed her to be an example of high quality teaching.” I spoke with regret.

Brenda eyes were rimmed with tears and I felt responsible. After several apologies, I called it a night and walked her to her car. As we approached, she unlocked the car with her keyless entry and I offered my hand for a goodbye shake.

Brenda shocked me when she embraced me and whispered goodnight. As I drove home, I regretted my decision to speak the “truth” about my marriage. I had tarnished Brenda’s image of my ex wife and I felt like a real schmuck.

In bed I kept replaying the earlier events in my head like a chronic self abuser. Efforts to banish those thoughts from my head were useless. I was attracted to Brenda and that explained why my faux pas was causing me so much anxiety.

“Think about something else.” I kept repeating in my head.

Don’t ask me why but I remembered one of the few times I was unfaithful to Kate. It was one of the most memorable sexual experiences of my life and somehow I never tired of reliving the thrilling event.

TWO: During my senior year at college, a buddy got me interested in weightlifting/bodybuilding. In one year with the help of a certain muscle enhancing supplement, I lost twenty pounds and had a defined but not overly muscular look. All the bulges were in the right places and I was getting more attention from the opposite sex than I ever dreamed possible

Back home for summer vacation, I was spending a lot of time at Kate’s house. We had been dating for almost two years and with my new look, she wanted to screw me more frequently.

Kate’s sister, Diane, was the youngest of three girls and had a very sexy way about her. From the start, we had a flirty but playful relationship. That summer she wore the skimpiest outfits that left little to the imagination. Her favorite was a bikini bottom and spaghetti strap T that showed off her nice and lean body. Although her chest was small for an eighteen year old, she had a hot little butt and toned legs that made my mouth water.

One sultry evening Diane and I were sitting on metal lawn chairs opposite of each other in the back yard. I was waiting for Kate to return from her friend’s bridal shower. She asked me to wait for her when she left and I was about to discover how fortuitous my agreeing to wait would be.

Diane and I had been flirting most of the day and a sexually charged energy filled the air. As the glow of the setting sun illuminated the sky, I noticed that her thighs were a little too far apart and I could see the faint impression of her pussy lips on the bikini bottom.

Diane noticed I was looking and spread her thighs farther apart. Her blatant display was causing a reaction in my shorts. With her parents and middle sister in the mountains for the weekend, I felt free to indulge in a “harmless” fantasy.

But, I wasn’t prepared for Diane’s bold and daring display. Without losing eye contact, she slowly pulled some fabric aside to reveal a portion of her pussy. With darkness falling rapidly, I doubted that any of the neighbors could see what was going on.

By now my boner was straining against my shorts and I opened my legs for Diane’s stares in the dwindling light. She gawked at it for a minute or two and responded by pulling her bottoms aside until her pussy was completely visible.

Unable to control my desire for Diane’s fur covered snatch, I was on my knees in front of her aching for a taste of her scrumptious pussy.

Diane scooted her butt forward until it rested on the edge of the seat. I was at the “point of no return” and skinned the bottoms down her legs. She opened her thighs and I gaped at her hot pussy framed by downy brown hair. As I lifted her firm butt, I saw some fluid leaking from her slit and down into the crack of her ass.

Diane squealed with delight as I gently licked her moist gash. The sweet/sour flavor of her luscious young snatch was intoxicating and I proceeded at an unhurried pace to maximize the pleasure for both of us.

Diane’s gaze was fixed on the spectacle between her thighs and instinctively put her legs over my shoulders. She gripped the arms of the chair for leverage and rocked her slice in unison with my thirsty tongue.

My lick/suck technique drew Diane’s creamy juices into my mouth and I greedily swallowed the pungent fluid, marveling at the exquisite flavor only a young pussy could provide.

Diane was panting in rapid but shallow breaths as I relentlessly devoured her swollen slit.

“Oh God! Eat me!” She bellowed.

I complied with her request and sucked voraciously at her hole and clit and Diane broadcasted her orgasm to the neighborhood.

“OH! Oh! Oh!” She yelled over and over.

My cock popped with a small orgasm from the exquisite joy of dining on Diane’s pussy. When her breathing returned to normal, I picked her up and cradled her in my arms as I carried her into the house. She had her arms around my neck and a dreamy, after orgasm, look on her face.

“Is Tarzan going to fuck Jane?” She asked with girlish innocence.

“Oh Yeah! I growled.

“Does Tarzan have protection?” She questioned.

Diane could see by the look on my face that I had none. But, I loved her play acting and found it to be a real turn on. I gently placed her on Kate’s bed and gawked with yearning at her semi nude body.

“Jane doesn’t want Tarzan’s jungle juice inside her to make a baby.” She remarked with serious intent.

I realized that Diane had been totally in control from the very beginning of our flirting relationship. At eighteen years of age, she had a maturity and joie de vivre that easily eclipsed her two older sisters.

“But, Jane knows how to make Tarzan happy.” She said in an exaggerated stage voice and pulled my cum stained shorts down my legs. As I rested my back against the headboard, I gaped with admiration and awe as Diane sucked my cock with an expertise that is acquired only from first hand knowledge, no pun intended.

My head rolled along the back of the headboard as Diane’s very talented mouth worked my cock into a bubbling frenzy. She fondled my nuts like they were priceless jewels and took the entire length of my throbbing meat into her mouth.

I was groaning and moaning like never before and a mammoth orgasm was nearing release from my balls. Diane came up for air and stared at the end of my distended cock oozing pre cum. With amazing virtuosity, she engulfed the head and in one long plunge, swallowed the entire length to the balls. She repeated the process until I screamed.

“I’m cominggg.” I shrieked and watched as Diane grasped the shaft and held it in front of her open mouth. Thick jets of cum shot into her gaping maw as my cock jerked with each contraction. When I was spent, I watched in amazement as she closed her cum filled mouth and swallowed.

I slowly slumped until I lay flat on my back. Diane joined me and regarded me with an amused expression. When I asked if she enjoyed my “lip service”, she made a few hesitant sounds. Then,

“Are we going to be honest with each other?” she asked in a serious tone.

“Of course.” I exclaimed.

“You were very good but about the same as Eric.” She stated truthfully.

Eric was her boyfriend.

“Don’t get mad but Kate has told me many times how you love eating her pussy. I admit I was curious and under the right circumstances I wanted you to eat me too.” She stated with honesty.

Diane proceeded to tell me that oral sex was considered a safe and accepted alternative to fucking by her peers.

“But, compared to a woman performing oral sex on me, guys are novices, no matter how much experience they have.” She said with conviction.

I gazed in astonishment at her and in spite of the age difference was speechless. Diane was experienced with men and women.

“How was the BJ? Better than Kate I bet.” She stated knowingly.

Diane was one sharp young lady. Although Kate adored having her pussy serviced via my mouth, she seldom and grudgingly returned the favor.

“Best I’ve had. No Bullshit!” I exclaimed honestly.

Diane beamed with pride at my comment.

“Want me to do it again?” she inquired in a sexy voice and for the second time in less than an hour she wantonly sucked my cock with fanatic zeal.

I was totally enthralled by Diane’s dazzling performance on my throbbing rod as she enticed the sperm from my nuts with her remarkable mouth.

Another colossal orgasm was developing and I felt powerless as Diane’s assault on my schlong continued at a frenzied pace. Out of respect for my ego, I desperately thought of baseball, anything to forestall the inevitable.

Diane with a mature perception well beyond her tender years, sensed my obstinate behavior and was determined to bend me sexually to her will. She resorted to slowly sinking the length of my trouser snake to the balls then applying a graduated sucking/tugging pressure on the upstroke. On both applications, her gifted tongue rasped the underside nerve ending feverishly.

I was no match for Diane the sexual dynamo; raise the white flag, cry uncle, lay down your arms, I surrender and I surrendered a substantial load to her conquering mouth.

“I’m cominggggggg.” I shrieked in absolute ecstasy.

Diane was a cock sucking phenomenon with a prodigious talent. I had experienced few women who guzzled sperm with the satisfaction and enjoyment that she exhibited.

As she milked the last drop of sperm from my tired nuts, I symbolically placed the olive branch crown of victory on her pretty head. I conceded sweet defeat to her sexual prowess.

However, what little intuition I possessed, informed me that this was a one and done shared sexual encounter. I had a new found respect and admiration for Diane.

During the ensuing years, we enjoyed a close family friendship and her understanding during the divorce proceedings was comforting to me.

THREE: My next two meetings with Brenda were held in the late afternoon. With a settlement offer looming on the horizon, we needed to establish several sets of figures that would satisfy me.

I was still kicking myself over my lack of sound judgment when I disclosed my reasons for the divorce. Brenda was business as usual in our meetings but her demeanor towards me had softened considerably.

On the day we received a settlement offer, I was sitting opposite Brenda and instead of focusing my attention on the details of the proposal, was admiring her trim figure. She had that lean look that appealed to me and I tried to imagine her cup size as I looked at the curves etched in her suit jacket.

“Mr. Macalino? Jack?” She asked several times trying to get my attention.

I must have stared at her with a dumb look on my face because she started to chuckle quietly.

“Do you remember anything I said about the settlement terms? She inquired with grace.

“Ah, yes, I mean no.” I declared and corrected myself.

Brenda put the proposal on the table next to her chair and looked me in the eyes. I dreaded what I thought she would say about my pre occupation with her figure.

“Jack, you need to focus your attention on the settlement proposal and not my legs.” She stated with a humorous air.

Needless to say, I was completely flustered and stammered something incoherent.

“When was the last time you dated someone besides Mrs. Macalino?” She inquired.

Surprisingly, her question had a calming effect on me and I tried to recall my last date with Lynn.

“Oh, probably twenty seven or twenty eight years ago.” I said in a level tone.

Brenda was regarding me with a curious, almost searching look.

“Are you interested in me?” she questioned going right to the heart of matter.

For the first time in a very long time, my face grew hot and I felt like some silly love struck schoolboy.

“Well, yes, but I’m too…” I stammered.

“Case closed!” she boasted and pumped her fist skyward in victory.

“Please Brenda, hear me out, let me explain…” I was saying in desperation.

“Explain what!?” You admitted that you’re interested in me.” She said in rebuttal.

I stood up and started walking to the door.

“Where are you going” She asked in an incredulous tone.

“I have to visit the men’s room.” I stated honestly.

As I exited Brenda’s office, she was doubled over in laughter.

In the john, I splashed cold water on my face and tried to regain my composure. I compared myself to the British Upper Class Twits lampooned in a sketch by Monty Python. Completely pathetic at every simple task they tried to perform.

September 2018
« Feb