You never forget your first time, and in my case the first time was the best time. I was 19 years old and just out of Navy boot camp and radio school, and my first assignment was in San Miguel, Philippines. I had been there about a month when a bunch of guys in my unit decided to spend a few days in Baguio, a resort community in the mountains of Luzon.
Her name was Olivia. She was a working girl, and a bartender in town hooked me up with her. She walked into the bar with an air of confidence, probably about 30 to 35 years-old, taller than average for a filipina, maybe 5'6", shoulder length platinum blond hair, a nice bust line, blood red manicured nails, and a beautiful heart shaped ass that made her jeans look like they were painted on. She was not a super beauty but attractive, with the look of a survivor and the attitude of a street fighter.
She wasted no time in sizing me up, checking my military ID card, commenting on my young age, then following with a hard interrogation; where are you from? Are you married? Do you have a girlfriend in the States? Do you have a girlfriend in the PI? My answers to all her questions were "No," and she was skeptical with regard to my denying the girlfriend stuff.
Olivia stared at me for a moment, and I had seen that look before, put on me on more than one occasion by my mother, grandmother, and various teachers when I tried to BS my way out of trouble.
Satisfied for the time being, Olivia said, "Let me see your wallet."
Without hesitating, I handed it over. She pulled out the money, counted it, then asked, "So what are you looking for?"
Being shy by nature, and pretty much intimidated, she caught me off guard.
"Well, if it's okay, I'd like to spend the night with you."
Olivia smiled, no, it was more of an impish grin while she drummed my wad of bills up and down on the table, "Oh wonderful...we could watch some television, and I could maybe read you a bedtime story?"
In a way, that took the edge off, and I put it to her plain, "No, I hadn't planned on TV and a bedtime story. I want to make love to you...you're gorgeous, I...."
Olivia stopped me, counted out $40, and handed it to me, "Yeah, yeah, okay, this is your pocket money, I'm keeping the rest...let's go."
I watched Olivia pass a few bills to the bartender and put on sunglasses as I followed her out. She held out her hand as we walked down the street, "Here, take my hand."
I grasped her soft hand, and as we walked she told me a bit about herself.
"You know John, I'm married. I work as a school teacher, and I have a son and daughter in grade school. My husband is disabled, and I do this to get extra money, so my kids can go to college after they graduate. They don't know I do this. The bartender back there is my cousin, and he is careful with who he sets me up with. I'm just telling you this....you know, just so you know your first time is not with a street walker or stripper. I'm a good person"
"What makes you think this is my first time?"
She giggled, "Oh, so it's not your first time? You're an experienced lover...been with lots of girls?"
I just gave up on that one, smiled and admitted, "Yes, it's my first time."
Olivia flashed that impish smile again and squeezed my hand, "We're gonna have fun tonight; you have the best teacher."
We left the main street that ran through town and entered the lobby of a small hotel. Olivia greeted the guys at the front desk who seemed to know her, paid for the room, and one handed her a couple of towels, washcloths, and bars of hotel soap. The room we got was small, and the furnishings, a double bed, overstuffed sofa, and writing table with two chairs, appeared to be pretty old. There was a ceiling fan that rattled briefly when she turned it on, and when I looked out the window, I got a nice view of an alley, some trash bins, and several stray cats.
Olivia excused herself and went into the bathroom. I heard the toilet flush twice, then the sound of water running. After about 15 minutes, she came out, barefoot and wrapped in a white towel. She was holding a blond wig and sunglasses in her hand, and ran her fingers through her long, black hair, "Like it?
She was smiling, and I laughed, "I like it better, beautiful eyes, and I love the hair...was wondering about the Filipina Marilyn Monroe."
"Like I told you, I'm a school teacher, and Baguio is not a very big city...I can't be seen...you know, doing this...gotta have a disguise."