Diane a Gentleman’s Valentine


Journal entry Wednesday, February 14, 1968:

“Today is Valentine’s day. (Happy birthday mom, you made it to 40!) It’s hard to study for Friday’s calculus test because I saw a beautiful girl today and I can’t think about anything except her. Someone said she’s a freshman transfer student from Tennessee but she looks like she should be in college. She does look more mature than most the other girls in school but she is by far the prettiest. Her hair is a soft blonde, and so long and wavy it nearly covers her upper body. Her eyes are a dreamy light brown and her smile is friendly and teasing. Today was her first day at our school.

Her name is Diane.

This has to be love.”

On Valentine’s Day, 1968, she dared to wear a red silk mini skirt and a white long sleeve cashmere rib tickler with a small pink heart over her left breast embroidered with the initials; DKS. The twin tailed pink ribbon in her hair teased her teardrop rump and the sparkle of a gold ankle bracelet complimented her white-laced socks inside white sandal high heels. It was also delightfully obvious; the girl was not wearing under garments. When she sashayed down the halls with her heels clicking the linoleum and her beautiful bottom and pouting firm breasts with erect nipples wiggling under the cloth, she affected everyone she passed. All the pretty girls instantly hated her with passion and testosterone dripped from every boy’s body, especially this young soul of eighteen. Diane literally … stole my heart.

People could only guess who Diane was and rumors about her whirled around the school halls like tornados. My friends and I guessed her real age to be 18 or 19, and her body measurements to be 34c-24-32, all packed into a 5 foot 2 inch frame and we jokingly guessed her profession to be illegal. Diane was an anomaly. She was single handedly responsible for the girls’ sudden interest in wearing sexy clothing on campus and the boys’ disappointment with the following administrator’s change in the school’s dress code.

Almost four months later things settled down and I got the courage to ask Diane out on a date. It was Friday and the student’s energy level was at its peak. I scrambled from hall to hall desperately trying to find Diane and when I saw her talking with two girls I approached cautiously. Almost magically she looked in my direction and we made eye contact. I waited patiently as Diane nodded her head at one of the girls then she backed away and walked toward me. When she was closer she smiled and shifted her books to her other arm, slid her purse strap higher on her shoulder and stopped right in front of me. Her perfume was so hypnotizing and her spirit so powerful I almost forgot what to ask her. When she said softly, “Hi,” I blurted out the question and was so overtaken by her beauty I almost didn’t hear her say, “Sounds like fun, sure, I’ll go out with you.”

After recovering from the shock of a positive reaction from a beautiful southern girl with an alluring accent wiggling her breasts in front of me, I was easily manipulated into picking her up at a place other than her home, but those were her terms and I agreed. Cruiser’s was a drive-in restaurant in a district where girls gathered on Saturday nights for a special type of date but if I wanted to take Diane out for an evening of fine dining, I’d have to drive the distance. I wasn’t concerned about renting my father’s 63 Lincoln convertible with a penalty clause beyond three hours of use to do so, would be a costly decision. I was so excited about my date with Diane I had an erection the entire time I was getting ready to be alone with the most beautiful girl I had ever seen in my life.

I arrived at Cruiser’s a few minutes early and saw some teens had gathered under the drive-up canopy. The weather was perfect. It was cool and dry with a slight breeze and I decided to drop the convertible top. After releasing the latches, I pressed the button and the massive top on the car began lifting as the motors whined lifting the trunk lid to accept the canvas sail. Some of the girls under the canopy howled and whistled, poking fun at the seemingly rich kid with a fancy car but they had no clue where I came from or who I was, and frankly, I didn’t give a damn where they came from or who they were. I was on a mission, and praying the fancy car’s machinery did what it was supposed to so I wouldn’t be embarrassed driving away with a half opened convertible top like a sail in the wind, or worse, without beautiful Diane by my side.

At precisely 7:00pm, Diane appeared at the southeast corner of the building and stood glancing around the parking lot. One of the boys barked an obscenity at her but it didn’t affect her search. When she saw me leaning against the passenger side of the Lincoln, I waved and smiled then she pranced like a runway model straight toward me as the whistles and howls echoed under the canopy.

Diane was carrying a white clutch at her side and wearing a black leather Escort Kız trench coat with the sleeves rolled up creating blood red cuffs at her forearms. The coat was just long enough to cover her upper thighs and she had it buttoned to cinch her body perfectly. Her white hose accented her shapely legs and her black sandal heels teased her gold ankle bracelet hiding under her hosiery. The closer Diane got to me the more I could see she wasn’t wearing anything else. I was so overwhelmed by her beauty and her risqué outfit my body flushed with heat and my heart began to flutter. Then as the scantily dressed beautiful woman strutted straight toward me like a confident predator assured her prey was exclusive, I began to feel timid.

When Diane was an arm’s length in front of me she stopped, smiled, took a step closer, lifted on her toes and kissed my left cheek. “Hi,” was all we said simultaneously as we stood so close I could feel the heat emanating from her body. Her fragrance engulfed me as her shoulder and hair gently brushed me when I opened the door, then she slid into the white leather seat as if she had sat there before.

As the juveniles under the drive-up canopy applauded and gaggled facetiously in the background I glanced quickly down Diane’s body. I couldn’t help but notice the girth of her puffy vaginal lips and the wet spot on her white panty hose nestled between two powerful thighs. When I was satisfied she was comfortable, I devoured Diane’s magnificent cleavage making sure it was tattooed on my mind then with a growing penis in my pants, I quickly snapped the door shut and rounded the car to enter the driver’s side before the scantily clothed gorgeous woman sitting in the fancy carriage got away.

With the insane traffic on Whitney Street, backing out of the parking lot was hard enough, but the crude comments emanating from the pranksters at Cruiser’s were enough to push me to escape as fast as possible. When the traffic cleared and the car was finally pointed in the right direction, I hit the throttle and the rear tires squealed. It was something I didn’t think the massive hunk of iron could do. As we shot down the street like a rocket ship quickly catching up to the taillights ahead, I began to sense I needed to do everything in my power to protect the precious live cargo to my right.

As I slowed to the speed limit, the smell in the car changed from burning rubber to roses and lavender. It was a pleasant combination of fragrances not used by girls those days. Diane simply giggled, wiggled closer to me, leaned against me and gave me a gentle kiss on my right cheek. Her touch sent my mind into a whirlwind of ideas about what was going to happen in the next three hours and it sent my penis into overdrive. Then Diane sat back in the seat and said, “Hum … no tunes,” then with a soft singing voice she toyed with a popular song at the time, “Knights in white Oxfords … blue jackets and boxers … and … brown boat loafers,” then she sat quietly scanning the dashboard apparently looking for the radio.

“Want some music?” I asked as I glanced down at Diane’s gorgeous legs. Diane tapped my thigh and said, “That’s, ok, I like the sound of the engine, it is on, isn’t it … or is all the stuff I see outside the car going the other way?”

I reached for the radio knob but Diane swatted my hand as if to scold me for interrupting her. It quickly became obvious to me, Diane was very observant and deviously cleaver, but mostly she made being inside her body an art form. I became curious as to why she became suddenly silent and I became more aroused when I looked down while driving and noticed her left palm holding her clutch on her lap and her right hand hiding under the clutch. Her legs were separated much more than girls spread their legs when sitting, and she seemed to be gazing out of the car as if she was on a fanciful journey, then it dawned on me. Diane was masturbating right next to me. She made a comment about how refreshing it was to be treated like a lady, but I was so overwhelmed by her sincere sexuality, her comment went right over my head and my penis continued to react to the vision of her gorgeous cleavage.

The scene at the porte-cochère of the prestigious PGA golf club was another chapter of a night to remember. One of my coworkers was working the valet station at the club that evening and when he saw the cream colored Lincoln pull up with Diane sitting in the front seat nearly on top of me, his jaw dropped. When he opened the passenger door for Diane, he got a close up view of real feminism and his eyes nearly popped out. I knew Diane’s crotch was soaked and by the look on his face he probably thought I had been fondling her the moment she sat her pretty little butt into the sinful carriage. The look I got from Jerry teetered between warlike and murderous.

Escorting Diane up the flight of stairs to the club’s massive entrance was another treat. As usual, a couple of young female escorts were assisting rich old drunken golfers and deviants down the stairs. The look on the faces of the girls was priceless as they concluded they were overdressed, under serviced and underpaid. I was so proud of Diane I could hardly control my ego and my hands, but being a gentleman, I placed my right palm gently on the small of Diane’s back as I ushered a living doll up the long flight of stairs to the massive double oak and beveled glass doors cunningly masking the inner sanctum of the temple of corrupt deceivers.

Every individual in the dining room glanced at Diane for at least fifteen seconds. She was adorably sexual and everyone was either jealous or resentful. Ben, the maitre d’, even kissed Diane’s hand, something the club rules disallowed. He even walked us to our table holding Diane’s arm like a father escorting his daughter as they followed the bridal procession down the aisle. Even though Ben was our senior by at least 30 years he acted like a giddy teenage boy in front of people who had employed him for over twenty years, and Diane flawlessly executed her part as the hussy bride to be.

The ravenous looks on the faces of the men, and some women, sitting at the tables when Diane sashayed through the dining room only encouraged her to perform. The scene she created at our table when we ordered could have easily been a perfect opening scene in a pornographic movie. She intimidated the waitress so much, the girl asked to be replaced by an older waiter so she didn’t have to deal with Diane’s overbearing sex appeal and venomous approach toward other females near her man.

Mixed between her seductive antics was her keen knowledge of art, fashion, mathematics and French. She was inquisitive and crafty and she executed a raunchy but clever blonde joke perfectly then giggled like a little girl who got away with something naughty. When I chuckled she appeared satisfied, cocked her head, winked then she stuck her tongue out.

I couldn’t help glancing at her fabulous cleavage when she glanced around the room and into her big sexy eyes when she looked at me. I sensed she was teasing her clitoris under the table and wasn’t really enjoying the conversation, so I felt comfortable steering away from inert topics and toward a subject more suited to our circumstance. I felt the need to steer cautiously though, so I asked her jokingly if her sex life had improved since she moved to Florida.

She responded with a quick, “No,” and suddenly appeared excited. She explained she didn’t understand why some people thought sex was dirty then added she was relieved I brought the subject up. She told me she was proud of her body and what she could do with it and how she liked to make others feel. I was so gleeful she was sexually open I didn’t realize a relationship with a woman like Diane would take a world of patience a universe of understanding and nerves of steel.

I decided to ask her about herself and asked a question I thought would encourage her to talk about her family and where she came from, but it came out wrong. She calmly explained she got her funny accent from her French mother and her looks from an American macho man. She said she was born in Oklahoma in a farmhouse in the middle of nowhere then moved to a big city in Ohio when she was nine, then she wove her body parts into her answer as if she wanted me to ask her more questions about her sex life.

She told me her breasts started growing as soon as she moved to Ohio and they didn’t stop growing until she was 13 when she moved to Tennessee. She said when boys discovered how to undo her bras she jokingly thanked her boobs for helping her discover stiffies. She asked if I knew what it was like to be perpetually horny and I lied to her. I told her I didn’t think about sex much then to my surprise, she opened her coat slightly and proudly displayed a gorgeous and erect pink nipple mounted on a baby pink areola atop a succulent snow-white breast and asked with a girlish giggle, “How about now?” I not only approved of her exposed tit, I approved of her daring demeanor, as did my penis and the patrons in the room watching the frivolity going on at our table.

Her little stunt caught me completely off guard and prompted me to continue our carnal discussion. I hated to sway the conversation but I wanted to know the answer. I wasn’t sure how to ask the question and it came out awkward and immature. “Why date me?” I asked in a low cautious voice.

Diane looked over the top of my head then down as if she was looking through the table then she wiggled a little, glanced across the room, then back at me. Her eyes became cat’s eyes as she grinned like a little girl with naughty thoughts then she said with a serious stare, “I like the way you look at my eyes when you talk to me,” then she looked down at the bread dish and said softly, “you have pretty blue eyes … and a really cute little butt.”

I didn’t think Diane was aware I existed, but maybe she was aware. We were only in one class together and talked occasionally, however, I always felt her indifferent toward me and never dreamed she saw me in any other way. I had to conclude she made up the response to keep the conversation going the way she wanted. Regardless, whenever I was near her I didn’t feel rejected, and believe me, I knew Diane was capable of shunning when she told a boy one day in front of the entire class to take it to a hayloft, and jerk it off alone, and that guy was my coworker, Jerry.

I decided to pursue our discussion a little deeper and asked her, “What kind of guy are you looking for?”

She appeared puzzled and seemed to be searching for an answer then suddenly she said softly, “Gosh … I don’t know … I look at all sorts of people … boys, girls, men, women, you know? … My senses tell me I can have fun, then I have fun, sometimes even ménage à trios, and sometimes … well, you get it.”

It wasn’t the answer I expected to hear but at least she was honest and in a flash I forgot why I asked the question, and to ask her what the foreign words meant so I started to gaze at Diane’s beauty again. I felt flush all over and so overwhelmed by her I felt like a little boy in a brothel in the midst of naked whores without a clue as to what to do with any of them.

Watching her fingers weave through her gorgeous wavy hair was sensuality in motion. Diane was a natural beauty and a sexy woman with a hint of demure tossed in as an appetizer. I couldn’t believe how naturally beautiful she was. She didn’t appear to be wearing makeup, not even lipstick, and her fingernails were natural and perfectly manicured with eased curves. The more I studied her the more I felt I was in the presence of a very complex and powerful woman who loved being who she was.

I was enjoying her attire as well and gave her a compliment on her choice of clothes for the evening. She giggled under her breath then she said her mother always insisted she wear clothes to hide her body, and then she asked, “What’s the point of wearing baggy clothes, or any clothes, if you got a great body?” I excitedly agreed.

Feeling comfortable with her I pondered asking her a very personal question, and when I got the courage the question was as simple as asking her if she remembered the first time she had sex.

Without hesitation she said she clearly remembered and what she did. Diane explained calmly, “Girls like doing it as much as boys … and more than you’d think.”

I couldn’t agree with Diane’s hypothesis based on my experiences when I was growing up. Girls always told me the opposite was true when it came to sex. In fact, I had been conditioned to believe girls hated sex. All I could do was sit and listen to Diane enlighten me as to why every time I tried to explore the inside of a cute girl’s clothing, all of them, except one, lied to me in order to keep their panties welded to their hallowed hips. but Diane’s story was an incredible eye opener.

I had to admit, Diane was not only sexy, she was obsessed with sex, and I felt I was getting closer to loosing my virginity by force as each minute ticked by. I wanted to ask her a question but she kept talking softly about how they rubbed their candies together until they got so hot they had to taste each other. As I watched her finger a baguette like it was a hard penis, her eyes appeared to be in a dream world as she slowly stroked the piece of bread. I finally realized I was watching a girl daydreaming right before my eyes. Just before I started to ask her another question, Diane looked into my eyes as if she snapped out of her alternative world and the question popped out of my mouth, “What did you like the most about your first time?”

Diane grinned and winked at me, picked up the baguette and slowly took a bite off the end. Then she toyed with the bread in her mouth until she swallowed. Her eyes looked at mine like she was looking right through me then she took a deep breath. I wasn’t expecting her to answer my question but after she exhaled, she looked straight at me with a sensual glare and spoke with a nearly evil tone, “The spanking after getting caught.”

I didn’t know what to say so I grinned at her and looked deep into her gorgeous eyes in an attempt to show her I knew what she was inferring. My penis was so hard it began to hurt and I wanted so badly to stand up and pull my pants down to show Diane she had succeeded in affecting me. Instead I simply sat still and watched Diane fiddle with the baguette as pre-cum moistened my briefs.

There was silence for a few seconds as Diane wiggled in her chair obviously making her happy button more comfortable, then she abruptly asked, “So … you remember your first time?”

I shrugged my shoulders and didn’t have to lie that time. “Yes I do … It was quite a revelation … I told Diane all about it and she listened intently, then I said, “We were so exhausted from doing it, we fell asleep in the middle of it.” I said lovingly as visions of my first experience flashed though my mind.