The Lady is a Tramp

"The Lady Is a Tramp" is a show tune from the 1937 Rodgers and Hart musical "Babes in Arms." It was introduced by former child star Mitzi Green. That song has nothing to do with this story.

I was a fairly normal teenager -- except that I was really big for my age (not fat), all over, and I had been held back one year in school because I had a year-long illness when I was six years old. When I was 18, and a junior in High School, I was six foot four, 235 pounds, could bench press 350, and squat 500. I was considered a "gentle giant" however since even though I was stronger than any guys on the football team at the High School that I attended I didn't play football. Instead I was in High School theater productions.

Only one person ever tried to mess with me in High School.

As I and four other theater students (three girls, one guy) were leaving the theater when after-school rehearsals were over a group of four or five football players were walking in the same hallway, having just finished football practice. I knew the football players, though not well; I did know that one of them, John Brandt who was a senior defensive tackle, was a bully and an asshole.

As we walked along for some reason John got it in his pee brain that he could mess with me. He called me a sissy because I was in theater (he had never seen my gym workouts) and caught me by surprise when he pushed me over.

My friends tell me that I went ballistic -- I don't personally remember anything that happened once I hit the floor except for five foot three inch Jessica Steele -- the very brave female lead in the play I was in at the time -- holding my face and saying "Calm down Lucas Higgins -- it's all right -- it's me, Jessica -- you can stop now. He's unconscious; you don't need to hit or kick him again."

When my mind regained clarity I looked down at prone John Brandt. His face was a pile of goo, and he was out like a light. Two of his teammates were tending to him; they had bewildered looks on their faces. My friends led me away with encouraging words.

I later found that when John Brandt was released from the hospital he said he didn't remember anything about the attack. In his case I think that it was a lie -- in my case it was the truth.

Up until that time I was a virgin. While I had dated quite a few times most of the girls were under 18 and not in theater. For some reason the fact that I knocked out a bully football player and didn't even remember it was like an aphrodisiac to the senior girls in theater (who I found were much more free-spirited than most girls in our school, and all over 18). Jessica was the one to take my cherry (I didn't take hers), and we hooked up on and off for the rest of the schoolyear. Carolyn, Charlene, Betsy and Winifred all gave me a try (actually several tries each) after I got rave reviews from Jessica. Although none of these were serious romances they were eminently enjoyable because all five of them were extremely active and passionate. I do believe that I was the most sexually satisfied male at Redmond High by the time that the summer after my junior year rolled around.

*************

The centerpiece of this story is not the senior girls in theater, but Desiree Cain. The summer between my junior and senior years when I was still 18 Desiree Cain was a thirty-something woman in our neighborhood. She both terrified and intrigued most of the teenage boys, and all of the teenage girls. She fascinated most adult males, and offended many adult females.

Desiree was married to Samuel Cain who seemed to be kind of a quiet, milquetoast guy who also happened to be the wealthiest person in the suburb of a big Midwestern city that I lived in. While his and Desiree's house was the nicest, it wasn't pretentious. From what I knew by keeping my ears open listening to adults talking, Samuel could have afforded to buy all of the houses in our entire neighborhood.

Desiree was more flamboyant than Samuel, but seemed to keep a relatively low profile for most (but not all) things. He drove an innocuous two or three year old Mercedes sedan; she drove either a new Tesla S Plaid, or a Lamborghini Aventador SVJ (suggested retail price $522,000) depending on her whim at any particular time.

The reason why Desiree fascinated and frightened so many people was because she was beautiful, rich, mean, nasty, and exuded sex. It seemed that the only person she treated well was Samuel. She went through domestic staff like water going over a dam. She didn't seem to have many female friends, although she did seem to have a group of hangers-on who followed her around probably because she bought things for them when shopping, and because they thought that being associated with someone as beautiful and sexy as Desiree made them "cool."

To make money I started mowing lawns and landscaping during the summer. I knew Samuel Cain only well enough to say hi to him; the most I ever talked to him was about fifteen minutes during a neighborhood barbeque with two or three other people. He was always friendly to me, however.

One Saturday morning when I was getting ready to go out and mow a couple of lawns for clients, and trim their bushes, Samuel Cain approached me. "Hi Lucas, good to see you," he said with a smile, shaking my hand. After a few minutes of chit-chat he got to the point.

"Lucas, our third landscaper this summer just quit. Apparently my wife Desiree is difficult to work with. I was hoping that you could take over mowing our lawn and doing some other minor landscaping work -- and maybe something else," Samuel said.

"Uh, I am looking for work Mr. Cain, but what makes you think that I would be able to get along with Mrs. Cain any better than the other landscapers?"

"For one reason, I've made it clear to Desiree that if she alienates you she'll have to do the lawn herself. Another reason is that the other landscapers used their own equipment which included many gasoline powered implements which she claimed were polluting and too noisy, whereas I want you to use the ride-on mower and other tools in our gardening shed, all of which are battery powered electric. If you're interested can you give me a price?"

"Gosh, Mr. Cain, that sounds really good. Do you know how much lawn area you have? I know that you have a big back yard with a fenced-in pool."

"According to the other landscapers, who I believe are correct, the lawn area is right around an acre and 1/4" Samuel replied.

I gave him a price that was 25% more than I normally would have charged, anticipating problems with Desiree. He smiled in reply.

"That's very reasonable, Lucas, I'm happy to agree. However, I have another proposal that is in addition to landscaping. How would you like to make twice that for helping me out with something else that should not require much of your time?"

"Wow -- I probably would," I grinned.

"I am concerned that some of Desiree's activities are not the most appropriate or desirable. I want you to do mowing every Monday and other landscaping work every Thursday, and keep your eyes and ears open and report to me anything that seems off-kilter."

'Uh...you mean...like...spy on her?" I stammered.

"No, not really; don't go out of your way to monitor her activities. Just keep your eyes and ears open and report anything suspicious. On this card," he continued, handing me a business card, "is my personal cellphone number."

After I thought for a few seconds I said "You don't want me to go through the trash, or install listening devices, or anything, do you?"

"No Lucas; just keep your eyes and ears open when you're around our house, or her," he smiled.

"Great...yeah Mr. Cain, but you don't have to pay me twice what the landscaping costs to do that," I humbly replied.

"Great! I insist on that payment Lucas, and prefer to deal in cash. Here's a thousand dollars up front; you just call my cellphone when the cost of your services exceeds that, and I'll give you more cash. I do not want an invoice at any time. Please start this coming Monday; when you arrive knock on the door to let Desiree know that you're there, then just go to the shed; here's a key for the shed; it also works on the lock for the pool fence gate."

I was blown away -- but not too startled to refuse the cash, which I brought inside my house after Mr. Cain left.

So Monday at 10 a. m. found me knocking on the front door of the Cain mini-mansion. When Desiree answered the door herself -- not a maid -- I knew that this job was going to be both really challenging and rewarding. She had on a string bikini that left little to the imagination. In two seconds I had the answer to the question often speculated on by teenage boys: "Are her DD tatas real or fake?" The answer was definitely "real."

Hoping that I wasn't gap jawed or tenting my pants when Desiree asked "Yes?" in a tone more bored than nasty, I replied "Mrs. Cain, Mr. Cain said to knock on the door when I was ready to start to mow your lawn. With your permission I'll go to the shed now and get out the riding mower and other equipment."

"OK, knock yourself out," she replied as she closed the door. Again her tone was more bored than nasty but the smug look on her face seemed to say "Caught you looking at my tatas, pervert."

My Johnson was at half-mast just from a five second look, and I had already started to sweat even though it wasn't yet even 80°F.

Monday and Thursday proceeded without incident. The second Monday when I knocked on the front door there was a two or three year old Ford in the driveway next to the four car garage. A maid answered the door. She was cute, obviously of Eastern European extraction. I asked her to tell Mrs. Cain that I was there. Her English wasn't good but I thought I understood her to reply "Mrs. Cain know you here and is to look around pool before go." I told her that I would; I found out later that what she really meant was DON'T look around the pool.

After I mowed the lawn with my key I opened the pool fence gate. The pool fence was seven feet high and solid to provide maximum privacy, undoubtedly because Desiree tanned topless given the golden brown hue on her tits when I saw her the first Monday.

When I walked into the pool area it sure looked like Desiree was naked on a chaise lounge and a nude big dude was above her. They both saw me, and I quickly closed the gate, and exited, red-faced. I immediately went to the shed and put all of the equipment away. As I was walking past the pool fence on my way to my pickup truck the pool gate opened and the guy who had been with Desiree -- now clothed -- came out, followed by Desiree.

"Hey asshole," he snarled as he approached me. "I don't like my privacy invaded and I want to be sure that you'll keep your mouth shut."

I didn't like his aggressive approach and I was just trying to leave when he grabbed my arm, spun me around, and pushed me as he snarled "Did you fucking hear me asshole?"

Just like the situation with John Brandt in High School I again zoned out. I have no real idea what happened until I saw Desiree (fortunately with shorts and a decent top on) standing in front of me with her hands lightly pushing my chest and pleading "Stop, please Lucas; you knocked him out; don't hit him again; please calm down; there's no threat!"

I stared at her blankly not really registering everything although apparently I was no longer enraged; I did see the obnoxious dude on his back with blood all over him. After Desiree was sure that she had calmed me down she tended to the unconscious asshole. She apparently determined that he was still breathing, given her sigh of relief. Then she looked up at me and said "We've got to get George back to his house. Can you put him in his Ford -- which is in the driveway -- and I'll drive him to his apartment. You can follow me in my Lamborghini and then I'll drive you back."

I didn't see a reason to drive her car instead of my pickup truck, but I wasn't about to refuse a chance to drive an Italian sports car -- if I had known then that it cost over $500,000 I might have not agreed.

I picked the unconscious dude up -- he had to weigh 240 pounds -- and with great effort was able to sling him over my shoulder. Desiree opened the back door of his car and I tossed him in -- his head hit a glancing blow on the roof, but I didn't really give a shit. Desiree handed me the keys to the Lamborghini, gave me a quick tutorial, and said "Follow me."

I did as instructed, marveling at the sexiness of Desiree's vehicle; it was almost as sexy as she is.

Fortunately George's apartment complex was only about three miles away. It was also important that it had an elevator since his apartment was on the fourth floor. I fireman-carried him up to his apartment and deposited him on his bed. As Desiree was cleaning off his face he came to. When he made eye contact with me his entire body flinched backwardly.

He had a groggy conversation with Desiree. He eventually assured her that he was OK as he held two different ice packs on two different parts of his face, and she told him where his car keys were, and to call an ambulance if he had a relapse. Then we left.

Desiree let me drive back, even encouraging me to gun the Lamborghini to peel away from stoplights -- which I declined to do. When we got back to her house, in the garage with the door closed, she approached me and put her hand on my chest. "I need to give you a reward, big boy, for getting George back to his place; and afterwards I'm sure that I can rely on your discretion."

She then smiled at me and ran her hand lightly over my crotch; my traitorous cock immediately boinged to half-mast. "I have a luncheon that I have to get to right now, but be ready for the time of your life Thursday," she continued, roughly pulling my head down by yanking on my shirt, and placing a quick kiss on my lips. Then with an evil grin on her face she turned and sashayed away, purposefully swinging her perfect ass.

I went into my pickup truck and beat my meat, the image or her naked body in the pool area popping into my head and providing plenty of motivation for my ejaculation. After a quick cleanup I went home to change clothes before my next job.

I was flabbergasted that my violent outburst that I had no control over and didn't remember in the slightest was -- just as it had been to the High School seniors -- some sort of weird aphrodisiac to Desiree. However, I didn't like having these outbursts regardless of the reason and ultimately went to see a therapist. She diagnosed it as dissociative localized amnesia. I eventually got treatment and by the end of this story no longer had such episodes.

**********

Monday night I had a little devil-angel dialogue with myself about whether or not to tell Samuel that Desiree was cheating on him. I finally reasoned that I had to -- he was paying me to report anything significant, and I'd be the cheater if I didn't report this because there is no doubt that it was significant. I didn't want to call when he was at home Monday night but about 10 a. m. on Tuesday I rang him. He answered immediately.

"Hi Lucas -- do you have something to report?" was how he cheerfully answered the phone.

"Uh, yes I do Mr. Cain. It might be better to talk to you in person, though. Is it possible to meet?"

"Yes -- let me treat you to lunch at the Baker Deli on the corner of Baker and Chestnut Streets -- you know where that is, don't you?"

I thought that what I had to say was going to destroy his lunch, but I didn't think that I really had a choice so I replied "Sure; what time?"

"11:45 if you can," he responded.

"See you then," I concluded.

At lunch I told him the entire story from the time that I opened the fence gate to the time I went to my pickup truck, of course leaving out the masturbation session. I was surprised that he took it in stride. When I was finished talking, and we both were almost finished with our Rueben sandwiches and tall iced teas, he got pensive.

"This may really seem weird to you, Lucas, but this is what I want you to do. I will have cameras installed both in the pool area and the blue guest bedroom in my house by Thursday. I want you to let nature take its course and do whatever comes naturally if Desiree seduces you. It will be filmed by the cameras and I assure you that you will never be identified in the videos. In fact, I'll have my attorney draft a contract and deliver it to you tonight," he pensively said.

I was gobsmacked. "Uh...you...uh...well...mean...uh...that you...want me...uh...to have sex...with your wife?" I stammered, sure that my face was beet red, and that my mind was about to short out."

Samuel sighed, and then continued. "I know that sounds really odd and I'm not that aberrant type of guy who wants to see his wife with another man. However, this will really help me out in my planned divorce."

"Divorce?" was my intelligent reply.

"Yes, divorce. I have suspected for quite a while that she's been unfaithful and I won't put up with it. In view of my prenup with her I will save several million dollars if I can catch her cheating. I'd rather have her cheat with you than the guy George you described, or any of the other guys I have suspected in recent times. Will you do it?"

I'm not sure how I remained sitting when he said that -- I would have thought that I'd fall off my chair. I gulped hard, remembered her naked body including DD real-life tatas, and said "OK -- if you're sure; I certainly don't want you hating me afterward."

"I assure you that that won't happen, and the contract delivered to you tonight will make that clear," he smiled.

We shook hands, he paid the bill, and I went to my next landscaping job. Fortunately it was a fairly simple mow so I could go on autopilot because my mind was on Desiree's tatas and pussy, not grass.

True to his word, Samuel had a contract delivered to me that night. It absolved me of all responsibility if I had sex with Desiree, assured that videos of us having sex would not be disclosed to anyone except him and his attorneys and that if a court required something different that my face would be disguised. In the envelope with the signed contract were five $100 bills -- no explanation.

***********

I actually took the day off the Wednesday before my meeting with Desiree on Thursday. I worked out, slept, kept my hands off of my cock, and ate foods that theoretically increase sexual prowess. Also, I stole one of my father's little blue pills "just in case" it turned into a long session.

I also brought along half a dozen condoms; all the High School girls required their use, and I assumed that Desiree would too.

Thursday finally came; I arrived at Desiree's house recently showered with much nicer and cleaner clothes than I normally wore. She answered the door herself in a white string bikini, with a big grin on her normally stern face.

When the door closed she planted a kiss on my lips hot enough to melt metal, and then took my hand and led me to the pool. "How about a little swim," she chortled.

"I didn't bring a swim suit," I replied.

"Who said anything about swimming with a suit on," she chuckled as she quickly disposed of her top and bottom. Looking at her when she was naked within arm's distance from each other seemed to cause my eyeballs to pop out, and my dick to emulate a steel rod. She was without the slightest doubt the most beautiful sexiest thing I had ever seen in my life, not just live but in any media.

I quickly disrobed with my cock sticking straight out. "I knew that you were a big boy," she cackled after taking notice of my crotch, and then she turned and dove into the pool.

I dove in after her. We splashed each other a few times, swam a few laps, and then got into a clinch. She didn't waste any time. As we smashed out lips together she maneuvered my uncut cock head to her vaginal vestibule and temporarily moved her lips from mine and growled "Fuck my brains out you bastard!"