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."
That said, Olivia took me by the hand, "I thought we could get to know each other better by taking a bath together, come, come..."
I followed her like a puppy and saw the tub, an old and partially rusted white clawfoot number, and the bathroom was steaming up.
Olivia smiled and started to untuck her towel, "Get undressed John."
I had already kicked off my shoes and had my shirt and pants off in seconds, pausing briefly to watch as Olivia shed her towel. She was magnificent, no hint of shyness what-so-ever, like nudity came very naturally to her, and she was used to men seeing her naked.
She had an olive complexion with tan lines around her hips and breasts showing that when she went to the beach, she wore a bikini. Her breasts were perfectly symmetrical and lovely, maybe a little more than a handful, with very dark brown nipples and large areolas.
I moved closer and fondled her left breast...must've been clumsy on my part because
Olivia turned away and leaned over to turn off the water. Then she stood there with one hand on her hip and the other cupping her vulva, "Are you getting in with those undies, or will you be taking them off?"
I stood there for a moment, aware I was becoming erect, then pulled down my Fruit of the Looms. I started to cover myself, but Olivia stopped me, "Nice, can I?"
Without waiting for a response she took my penis in her hand and squeezed gently which startled me. No one had ever touched me like that, not even the doctor who administered our sports physicals.
Olivia told me to relax and kept stroking my cock. She took my hand and placed it back on her left breast, "Here, you can touch me too, but let me show you how."
She positioned my hand so that her nipple was between my middle and ring finger, and showed me how she liked her tits played with...soft squeezes with slight finger pressure on her nipple, maybe four or five times, then roll the nipple between my thumb and forefinger and repeat.
"You see, that's how you do it...my titties aren't silly putty...be gentle."