One thing I knew for sure from my unfortunate experiences was how to please an older woman sexually. I heard she lived on the Upper East Side but never had I thought that I would actually run into her. She pulled out a book and began to read. I was looking for my angle and I found it. Without hesitation, I walked over to her.
“Excuse me, Ms. Whitfield, I just wanted to tell you that I’m a big fan.” She blushed then broke into a big grin. Got her!
“I’m not Lynn Whitfield. Is that the best you got?”
I retreated momentarily but this was chess not checkers and I was able to regroup with the swiftness.
"I see you’re reading Monique Gilmore-Scott. She’s dope. You a student at Hunter College?
She blushed once again then erupted into a big smile. Got her twice! That’s the rush I was seeking, the thrill of the chase and the eventual and inevitable kill. But I like to play with my food first. "You’re cute. I'm old enough to be your mother,” her fine ass said. “ But thank you anyway. I teach African American literature at Columbia."
"Get outta here! I would have thought for sure that you’d be taking classes not teaching them. I bet you were a Noxzema model growing up, weren’t you?"
Blushing doesn’t show through on ebony skin, but I could tell she was flush. And that snapper was surely getting moist. My desire for older women, or should I say “mature” women, always lurked nearby. What gravity and time had taken away, they were able to make up for in style and sophistication. I continued with the same kind of fact finding I did with the Smith’s; only I was trying to bag some tail instead of a sale this time.
"So I have all the qualities you're interested in, right? Good looking, articulate, family-oriented, spiritually connected? So what day is better for us to go out? Friday or Saturday?"
I clammed up and smiled, showing off the $5,000 investment my mother made in braces to straighten my teeth when I was a teenager.
"Friday," she replied.
And seven times out of ten I got the sale. I was becoming a master.
“And for the record, Lynn Whitfield is my cousin!” No shit.
Mrs. Robinson
If the first one who talks loses is the Golden Rule of sales, then not far behind would be when the customer agrees to the sale, shut your ass up, don’t say another word and walk them straight to the register.
We continued our conversation at a small local bar over on 66th St. near 3rd Avenue, not too far from the park. We picked over appetizers while watching the NCAA basketball tournament. Actually I was paying more attention to her tantalizing bosom across the table from me. She kept fidgeting around with a smile on her face like her chipmunk was tickling her. I bet it was. We sampled different Merlots and Pinots as this sizzling forty-something enhanced my knowledge of fine red wine...over Buffalo wings, usually a faux paux.
“So, I see you like basketball?”
“Yeah, a little bit I guess.”
“I would have thought that you played. Looking at your yummy body,” she flirted.
“What? This old thing?” I was far from gorgeous, but I was sniffing around in the ‘being attractive’ neighborhood again. “I was All State coming out of high school and got a full scholarship to play at Rutgers.”
“Wow. So how come I don’t see you up there on the TV playing? I could have been one of your groupies, laugh out loud.”
“That shit wasn’t fun anymore and became more like a job. Three to four hours of practice per day was making my grades drop. I knew I wasn’t going pro so I needed to get up outta there with my degree. Not to mention I was riding the bench mostly.”
“How come you didn’t get any time if you were that good?”
“Because at the Division I level every player was “the man” on their high school team. Everybody was All State, for the most part. I went from being the man to being the twelfth man.
“That sucks,” she said. “And so do I!” She had her tongue in cheek and it wasn’t for the figure of speech. She was letting me know what she intended to do with my third leg. When the customer agrees to the sale shut your ass up, don’t say another word and walk them straight to the register.
Without delay we took it back to her apartment (the register) up on 86th St. She lived in the actual Jefferson's deluxe apartment in the sky-y-y building. The Upper Eastside had over two hundred thousand people residing their alone, of which only two percent were African American. She must be doing something right to be able to live up here.
We rushed into the elevator past the doorman. He shot me a knowing wink wink as if he had seen this movie before. I didn’t care. I had been a boy toy many times while I was living in L.A. I would go to dinner with my pet cougar and the other mountain lions in the room would nod approvingly as to say, “You go, girl!” I decided that this gorgeous specimen fearlessly ravaging my neck while we were in the elevator riding up to the penthouse would be my black panther (cougar).
The elevator doors opened and we exited right into her apartment. That was cool as shit. I had never seen that before, so I was thoroughly impressed until I saw the rest of her apartment. It was right out of Architectural Digest with a sunken living room, crystal chandeliers, imported Italian marble floors, three fireplaces, and a Steinway grand piano.
She had enough of the tour, so she began to woo me by biting the top button off of my shirt. Then she poured me another glass of Pinot. But before I could take my first sip, Gorgeous planted a savory wet kiss on my parched lips. I really don’t know why I was surprised because we had taken it back to her high-rise, so what did I think was going to happen? Play chess? Watch television? Talk? I was a little rusty regarding the game, but I got my sea legs back quickly. She easily slithered her tongue in my mouth, inviting me to take things further.
Kissing was an indication of what was to come. I liked to make out more than I liked to have sex. Intercourse was just the physical act of copulation to me, but kissing was more intimate. Through this easily overlooked gesture I was able to gauge how far and what type of relationship the woman and I were going to have.
It brought to mind Meghan Boston from college. She was a freshman with an endearing innocence. She was already an established runway model by time I met her. She towered at six-foot-one, weighing in at about 107 pounds, four pounds too heavy, according to her agent. Meghan had several tear sheets from various magazines such as Seventeen and Vogue, having already worked in Milan and Paris.
Her problem was that I hated how she kissed. Looking back on it, I should have understood her inexperience, seeing as though she was only a sixteen-year-old college freshman who scored an astounding perfect score on her SATs. She frenched sloppy and wet. Saliva would trickle down my chin and onto my shirt. It would have been more hygienic for her to just spit on me. Nevertheless, it turned me off and I had to let her go because of it.
Gorgeous tenderly placed my hands on her perfectly augmented breasts. A lot of guys don’t like implants, but I could care less. If you could afford them, then do whatever makes you happy. I decided to drop my hands a little lower guiding them past her hips and run them up the inside of her buttery thighs.
As my hands made their way back up to her assets, they made a brief pit stop at the small chasm that split her two legs. She made sure to cock her legs wide open for me, welcoming me to take things to the next level. I tickled her labia with my index finger and pressed firmly on the top of her clit with my thumb. It didn’t take long before a river of expectancy stream down my forearm and a delirious moan called out from deep inside her cave. “Oh,Dapper.”
Then her voice took another tone and turned naughty. “Enough of the foreplay.” She turned the tables on me and insistently ripped my clothes off, popping every button off my Ralph Lauren oxford shirt. “Don’t worry about that, honey. I will buy you two more.”
I pulled her skirt up over her head, revealing the most perfect body I had ever seen. “To tell you that you looked good for your age wouldn’t do you any justice. You looked good f
or any age.” I gawked.
“Thank you, baby,” she smiled. “All the yoga and Pilates must have paid off . I also toured with the Dance Theatre of Harlem back in the day.”
She felt the need to give me her resume so I let her. It makes them feel better when they can proudly recall a time when gravity wasn’t necessarily the enemy.
I laid her down on the white leopard skin in front of the fireplace and worked up a lather between her legs with one hand as I gently coaxed my hard-on with my other.
“You’re so fucking hot,” she moaned.
When both of us were ready I effortlessly pushed my thickness into her famished pussy. She gasped. And so did I. She had the tightest pussy I had ever felt and I could feel its walls stretching and pulsating against my throbbing penis. She had no kids and an ex-husband who didn’t bring it like he should have to thank for it. She was also careful not to have sex more than once a week because she didn’t want her shit all beat up. After about twenty minutes of fornicating in every position from cowgirl’s helper to the wheel barrow, she finally had enough.
"My God! Are you ever going to cum?"
I hadn’t had sex in two years and I was going to savor the moment.
I finally came like a freight train and by the bucket load. Three years, two months, and twenty-seven days of forced celibacy finally over, just like that. I rolled off of her and onto my back, satisfied. In no time, she rolled on top of me ready for round two. However, I was slow to answer the bell.
“That was incredible. Let’s do it again.”
"Whoa, Momma! Unlike my boy, I don't take Viagra."
"Well, maybe we need to call him over here, too. I've been with two men before. Have you?"
"No. I haven't been with one man before, thank you very much."
"I'm surprised. You said that you lived in LA, right?”
What's with these chicks? It's almost like they want us to be gay. I jumped up and started to get dressed. She thought she offended me. She actually did, but I didn't let her know. Searching for an excuse, I came up with the most popular.
"No. Of course not. But, I’ve got to get up early tomorrow."
She stood her perfect body up, kissed me, and then lit a cigarette. I gaped at her statuesque outline. She was perfect in every sense of the word. Powerful, rounded shoulders and flawless traps supported her delicate, slender neck. Her trim obliques, flat tummy and streamlined thighs highlighted the rest of her physique. She had the lines of an Italian Maserati.
"I like you. Actually, I like fucking you and I'd like to continue, if that's okay with you?" she said.
"I've got no problem with that." Shit, what man would? That was the cool thing about fucking an older woman because they had already been through all the bullshit and knew the game. It was about them getting their shit off and not being alone. They just wanted someone to respect them, be nice to them, and go out to dinner every once in a while. Usually she will pick the check up anyway so how much will it hurt?
“I’ve got a lot of money, Dapper, and no one to share it with. All this could be yours if you want it.”
How many times in my life had I heard that? Once upon a time that was appealing to me, but not anymore. I wanted my own shit. I could take care of myself and the only requirement was that you be able to take care of yourself. Nothing in life is free and all these cats running around living off of women were going to have to pay the piper one day, whether it be giving her a baby or having to listen to her bullshit— both of which I am not with.
I didn’t even catch her name. I didn’t ask either, come to think of it. I didn’t want to know anything about her or her past. I just wanted to have fun. That’s what I was about. If you want to have fun, then I’m the guy you’re looking for. If you are searching for more, then I’m probably not the guy for you. I decided that I would call her Mrs. Robinson.
We Don't Need No Water
It was after seven o’clock and I was behind the register counting out the drawer to close up for the night. Mike had gotten used to leaving me alone at night to hold down the fort, confident that I could keep the sales numbers up and I could total over $11,000 today. It was the end of the month and I was approaching $70,000 in personal sales, which would mean a fat commission check on the fifteenth of next month. My cell rang and I ignored it at first, not wanting to lose track while I was counting out George Washingtons.
But then I noticed a familiar number. It was fuckin’ Green Eyes. I had a good mind not to answer it at all after she stood me up the other night, but I was heating up with the ladies and I wanted to keep it going.
“Hello?” I asked faintly.
"It's me."
"Who's me?"
"The best sex you're ever going to have."
"Like I said, who's me?"
"How many girls do you know that are five foot three, forty double D, black hair, green eyes, and a pierced clit?"
"Carmen Electra?" I actually did know Carmen Electra from when I lived in Hollywood. She lived in the same apartment building as me. Then she landed Baywatch and the rest is history. That was the cool thing about L.A. One day you could be a nobody and the next day you could be on top of the world. Just like that.
"Whatever! Dap, I know I've been unreliable. I'm sorry. But I want to make it up to you. Is that okay?"
"I don't know. You've got a little too much game for me." And she did. I was starting feel like a sucker and I hate feeling like that. She had me wrapped around her French-manicured finger.
"Well, how about me, you, and my girlfriend hook up at my place?" Naaaaa. Stop bullshittin'!
But then she put her girl, Claire, on to say hello. She sounded sexy too, which led me to infer that she was probably huge since that is always the case. But I determined that I would decide for myself when I got there.
Green eyes answered the door. She looked sensational in her low rise True Religions and baby doll tee, drawing attention to those mammaries I adore so much. “Wow! You got here fast. What, did you do take a cab?”
“Hell no. I ran over this motherfucker!” And I did. At least I did from the subway that was located six blocks from her Prospect Heights flat.
I entered the apartment out of breath and she introduced me to Claire. She was the exact opposite of what I thought initially. She was a natural-looking sista with beautiful Hershey-colored skin and the biggest, brownest eyes to accent her short, tangled locks. Green Eyes really does have Jungle Fever, huh? It was always interesting to me how old school names would find their way to the cutest girls. Names like Ingrid, Helen, and Eleanor were some heavy names to carry around for a little girl. Luckily for them, most would blossom into beautiful women who just happened to be named Harriet, Martha, or Marjorie.
After a brief, bullshit game of Spades to break the ice and a little puff of Purple, I entered a new frontier—sex with two women at the same time who weren't prostitutes. It was always awkward for me trying to make that move from the living room into the bedroom, but Green Eyes and Claire were old pros.
Coolly, they both French kissed me simultaneously. Our three tongues fiercely intertwined, each trying to “one up” the other. After three passionate minutes of dry humping we made the move to the bedroom without saying a word, careful not to break the hyperactive silence. There, each of us helped the other disrobe. First was Green Eyes. She was as I had imagined her to be, her kitty clean shaven like a little girl. Her ass and legs were thick like she played lacrosse or field hockey once upon a time. Nonetheless, the partying and smoking and lack of exercise had already begun to take its toll on the twenty-five year old and she started to thicken up. She was a sofa according to Caesar. She displayed a tramp stamp of a shamrock on her lower back and modeled perfect, natural double D’s. She must have been whom Bode celli had in mind. Next was me.
The two femmes tore off my shirt, revealing my carefully chiseled upper body. My shoulders were broad; my back was solid, and my pecs were powerful. I was narcissistically pleased when they looked at
one another with an obvious glance of approval. Their shea-buttered hands glided over my hardened biceps and abs, careful to explore each and every indentation.
I could see they fancied my inguinal crease, the suggestive sexy line separating the upper body from the baby maker. Green Eyes licked the left crease as Claire licked the right.
“Delicious” they said in concert. The approval the two vixens displayed was intoxicating and making both of my heads big.
Then it was Claire’s turn. She was wiry but athletic, graceful and sleek like a Bahamian swimmer. Exceptionally leggy and lean, she reminded me of a frog on steroids. Her muscle bellies were full and her coffee skin was flawless. Her tangled locks showed her identification with her Caribbean roots while her pierced lip, navel, and clit displayed her openness and nonconformity. She was all natural, sporting a small, triangular bush to conceal her thick labia.
Instantly, we were all entangled with one another into a mound of interracial flesh.
There was something about Blacks and Whites having sex that was taboo, yet exciting. It was the contrast in skin tones. Everyone like Oreos!
The session started out just like I had dreamed it would be like. Both girls were all over me—licking my neck, biting my chest, sucking my toes. That felt really weird but nonetheless, they seemed to be enjoying it so go ahead and knock yourself out.
I would lie between the two sirens and insistently push their heads together, encouraging them to kiss. They longed to comply. Green Eyes was passive and gentle. Claire was precise and dominant. She gave direction that was clear and succinct as to what she wanted us to do. First she instructed Green Eyes to gently slide her hand up and down my shaft until fully erect. That was going to be no problem.
Claire gave instruction like a collegiate rowing coach. “Faster…” Stroke… “Harder…” Stroke.” She conscientiously never let her raspy voice rise above a whisper. We were more than happy to accommodate her hedonistic commands.
Dapper Carter's 8 Rules of Dating Page 11