Cherry Boy

Cherry Boy – a term to describe sailors and Marines who are new to the nightlife scene of various Philippine cities, such as Subic Bay, Angeles City and Manila.

That was me back in 1990. A newly-commissioned ensign in the United States Navy, on my way to my first war. I was stationed aboard the flagship of the U.S. Seventh Fleet and we had just been ordered to the Persian Gulf to head up the forces that would soon take on Saddam Hussein.

Making matters worse, there were two huge typhoons bearing down on the Philippines, where we had to go to pick up additional reservists and extra supplies. It was miserable. To save time, the ship went through the first typhoon. The ship tossed and turned and the crew ate up a six-month supply of saltines in about three days.

Subic Bay is a shell of itself now (the military only just decided to put a few ships back in there to fight Abu Sayyaf). Back during Desert Shield/Desert Storm, it was the second largest naval base in the Pacific. The town of Subic catered to the base and there were dance clubs, night clubs and massage parlors galore. For a new ensign like myself, it was like wandering into the Twilight Zone.

Overall, it was a weird experience. Because of threats from Philippine rebels (later they merged with Abu Sayyaf), everyone had to go out into town in pairs. I was stuck with George, this big, goofy junior grade lieutenant. Anyway, all the officers not on duty went into town first. I was in the engineroom and got stuck aboard due to a problem with a condenser. So, I had to go into town by myself but under orders to meet up with the rest of the officers ASAP.

I got about a block into town before I was pulled into the hallway of a massage parlor. A bunch of cute girls felt me up and said I needed a massage. Being somewhat naïve and also getting hard as a rock, I let them take me upstairs. Yeah, I was gullible but soon, I was in a room, naked, with three girls rubbing me and a fourth staring at my huge ten-inch cock like she was in a trance. The other girls laughed and pushed her head down. She took the hint and started blowing me. She barely got the head of my dick in her mouth.

At that point, the massage stopped and the girls took turns blowing me. A girl named Jenny was the best. She got most of me in her mouth. I, meanwhile, had my fingers and tongue in all of their pussies, which showed how naïve I was. STD's were nowhere in my mind.

Jenny finally begged me to fuck her. I had no condom and none of the rubbers the girls had were close to being big enough. Jenny said I could pull out before cumming, so I said hell yes. Man, she was tight but the other girls cheered her on as I fucked the shit out of her. I felt myself about to blow, so I pulled out.

She begged me to come inside her and I was so horny, I started to put myself back in. That's when a girl named Tia leaned forward and wrapped her lips around my cock. I busted nut after nut down her throat and she swallowed it all.

Afterward, Tia and the other two girls tore Jenny a new one. Turned out, she already had three kids and they said she didn't need a fourth one.

Anyway, Tia made me promise to fuck her brains out before my ship left. I agreed, figuring I'd probably never see her again. I went on to the club where the rest of my ship's officers were hanging out and the girls were all over me.

My senior watch officer explained that the girls had been told I was a "cherry boy." There was a ritual about showing cherry boys the ropes. There was even a drawing to see which girl would get to take me to her home. For that purpose, though, I had to call myself "Ricardo," which was what the other officers had told the girl my name was.

A short girl with freckles and massive tits won the lottery. Her name was Michaela and she was gorgeous. Mixed race. The Philippine people are essentially a mix of Castillian Spanish, Oriental and Polynesian. Add in DNA from American sailors, Marines and airmen and you get an exotic mix, sort of like Brazil.

My night with her was dashed, however. Remember how I said officers had to go in pairs. Well, George had found a hot number named Dana, but I could see she was a vamp and was playing him because he could have been Gomer Pyle's other cousin. I had to go to her house with him and spend the night with Dana's roomie, Salita.

Salita was cute but she was strictly traditional. No oral sex. Just straight missionary. Sex was awful because, as I showed before, I need lots of oral sex – giving and receiving – to get a girl ready for my huge dick.

After she fell asleep, I went to the bathroom to sulk. A moment later, Dana walked in and started looking under the sink. George had fallen asleep after shooting his wad in five minutes. Now, Dana was pissed. She'd misplaced her mad money.

I dug out a wad of bills and offered them to her, with no strings attached. I mean, I was about to go to war and no one knew how it would turn out. And Philippine pesos were not really valued anywhere else, having a poor exchange rate outside of the country. She took the money and thanked me, the first sign of real emotion I'd seen from her. I guessed that she'd been running a game so long she couldn't show real emotions.

Then, she crawled up to me and got between my legs as I sat on the toilet. In seconds, she had my shorts off and was playing with my cock. She said maybe she should have palmed Salita off on George and gotten with me. She started sucking my cock and she was fantastic, taking almost all of me. I should have busted a nut then and there but she gripped the base of my cock like a human cock ring to keep me from coming.

She had me get up and first asked me to fuck her from behind against the sink. We thought better of that because the sink wasn't too sturdy (Filipina homes were not well-constructed). So, she got back on all fours and leaned on the toilet lid. I got behind her and started going down on her pussy, which caught her off-guard. Soon, I had her squirming and she got wet, her juices running down her thighs.

I then got behind her and slid in balls deep. She took me all in and I fucked the bejeezus out of her. She slapped a hand over her mouth, lest her cries of ecstasy wake George or Salita. Then, she came hard, her pussy clamping down on my dick like a vice. There was no pulling out now and I shot wad after wad into her.

The next night, I again got off late but I had trouble finding any other officers. I just said fuck it and went out on my own. I went to Dana's house but she wasn't home. She also wasn't at her club. But, Michaela was.

We went back to her house and fucked all night long. I came about five times and stayed with her until the dawn. See, the base's main gate closed at two a.m. and reopened at five-thirty. I would have to wait until then and be back aboard in time for officers call at 0800 (freshly-showered and in a clean uniform).

The sex got better because someone knocked on the door. Michaela thought her roommate had forgotten her key again, but it turned out to be Dana. Yeah, I was surprised as hell but Dana had found out from girls at the club that I'd gone home with Michaela. Now, it was sort of an unwritten rule that you didn't take a man from a fellow club girl. However, Michaela asked Dana to join us; I'd worn her out.

Truth was, I'd come five times and I was not getting it up a sixth time. Dana fixed that. She played with my cock and blew me to another erection. She then rode me to my final climax.

I had one more night in Subic but I also had duty. Around 11 p.m., my department head took pity on the junior officers and let us off the ship for one final night, since our next stop was Kuwait.

It was too late to see Michaela or Dana, as club girls found their dates for the night long before 11. So, I went to the massage parlor and found Tia. She was with two other girls I didn't recognize but she told them I was a cherry boy with a huge dick. We all went upstairs.

The other two girls were intimidated by my dick, so they just played with each other and sucked my balls while Tia went down on me. I then pulled Tia on to my dick and fucked the shit out of her. She came about three times before I pulled out and let the two girls suck me off.

For the next two hours, I fucked all three and then slept until dawn. At first light, I woke all three up by going down on them. Then, I fucked the two girls, as Tia egged them on. They ended up with ropes of cum all over their stomachs.

I cleaned up, went back to my ship and it was off to war. Those were the good old days. I haven't been able to come even half as many times as I did in those three days before I went to war. Maybe it was the fear I'd get killed. Maybe I was naïve and full of energy. Maybe it was just what happened to all cherry boys.