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Jangles Unchained: The Day I Lost My Virginity To a Man

March 12, 2017

He laughed, "I'll make you as comfortable as I can and won't do anything you don't want to."

It was back in April of 1986 when I first joined the United States Navy at age 17. I was in transit from just getting out of boot camp to catch up with my ship somewhere in the Mediterranean.

They flew me everywhere, but once I landed in Diego Garcia, I remained there for about 82 days. It is a small island in the Indian Ocean, mostly inhabited by Filipinos. Back then the Navy only allowed men on base: A woman  was a rare site and every man would stare at her. Freight liners would come and go to the island for refueling and supplies. The merchant marines got a chance to get off the ship for a few nights and go relax on land for awhile before headed back out to sea, the harbor held a nest of these freighters.

My job to pick up litter along the beach, I could of done this for life; walking along an unused beach in shorts and a hat as the weather was always hot and the Navy dress code was very subtle. Surprisingly enough from being away from my family and friends, and cut off without any type of communication, I was very content.  
I had a friend, he was more or less my supervisor, we shared some interest in music, and swapped dubbing recorded cassettes. Other then that I was pretty much alone and I spoke through letters to my girlfriend and to my parents.

I had my own trailer, the living quarters were somewhat primitive, it was a single wide trailer with about 8 beds and dressers in it, I don't think it was more then two rooms, but it was empty and I was alone. Bath houses were close by outside. Being by myself came in handy as at age 17 as I masturbated quite often.
I would think of the girl I just left three weeks ago and the only time I ever had sex, it wasn't much, we both were scared and didn't know what we were doing. We did it twice as I don't think the first time couldn't of lasted more then a minute.
Other times, I masturbated with my ass up against the bed post: I loved the feeling of my asshole being touched and played with, I had played with a few objects at other times before, but on base, nothing was really available to have fun with.


There was a small bar where the enlisted and the merchant marines could go down and have a drink, play some pool and cards or just socialize. I really didn't know to many people, but was told this is the only place to have some down time.
One evening I decided I be social and cleaned up, put on a nice black buttoned collar shirt, donned on a classic pair of tight Lee jeans, and my dingo boots with a bandanna wrapped around the ankle of the boot, what I sight I was I'm sure, but every generation has it's looks.
I played pool with a few fellas, and was drinking screwdrivers as I yet acquired a taste for alcohol at this point. After a few cocktails I was feeling pretty good, just hanging out enjoying what was going on around me.

I didn't even notice a man was checking me out, I really never considered any male to be attractive or wanted to have an encounter with, so why should I notice if someone was checking me out?!
He approached me and asked if he could buy me a drink, I looked at him, he was much older, I say in his late 20's to early 30's. He was a short man, but I was pretty small myself at the time so we looked eye to eye. His physical appearance consisted of a bit chubby, balding forehead, and black hair. I hesitated my answer as I was caught off guard, for the first time in my life I was being hit on and didn't know how to react.
I was brought up to be nice so I accepted his offer to a drink, and saved some money.
We spoke about what brought ourselves, where we came from, small talk while sipping on cocktails, nothing I thought was out of the ordinary.
He ask if I care to sit down at a table with another drink, at this point I was getting more then a calm buzz, but I had nowhere to be in the morning and this was kinda my mission anyways: To go out and tie one on, much to my surprise later...
We sat down and he reached over and touched my hand, I flinched, but let him keep his hand on mine. "I have a question for you, if I may, it may seem a little strange."
Okay,"  I replied.
He said he found me quite attractive and would like to take me back to his room on the ship out in the harbor and have sex with me, on top of that he be willing to compensate you for doing so!
I was flabbergasted to say the least, I couldn't, wouldn't, but yet...  I was eager to hear more as an arousal was shifting in my pants.  To myself I was like This could not be happening, but to my surprise I was more willing then I let on.
He told me he would have me back by morning and that he be willing to pay me $1,000 in cash.
"Wow ", I said,. I'd never had anyone make an offer to me, or even considered the possibility of someone doing so. He talked about what he found in me to be so interesting and how I looked and attracted him to me. Of course, everyone loves compliments, and I really never got any, so this was very exciting to me. He asked if I wanted another drink, I declined and said, "I will accept you offer, but if we go now."

We left the bar and took a small boat taxi out to his ship, it was a massive tanker, I was so scared, so excited, and so overwhelmed of everything that was going on around me. Between the new adventures of being on a ship for the first time in my life, to knowing a guy wanted little ol' me for sex, and to top it off I was feeling the effects from the alcohol and the ride in the boat.
We made way though the maze of hallways and cabins till we reached his cabin. He asked if I was feeling okay and wanted to know if I'm having any doubts about this,
"I'm okay, but also, I'm very nervous."
He laughed, "I'll make you as comfortable as I can and won't do anything you don't want to."

We got inside the small little room crowded with a desk, a bed, and a handy little bathroom off to the side.
We both freshened up, I did first, returned to his desk and sat down while he went into the bathroom. At this time I was alone and all I could think about is how far I should let this go and my new worries about STDs.
The nervousness came over me in waves.


I didn't hear him return: All I felt was a hand lightly brush over my chest as he approached me from behind. Chills ran though my body as he caressed my chest and moved his hands upon my shoulders massaging them deeply. He moved to my neck, then kicked my chin back, ran his thumb across my lips, I shuddered, and opened my mouth a little. He stretched over and leaned down and kissed me. He was gentle, he lightly pressed his lips into mine, then more firmly, as he  started to make out with me. I felt his stubble on my chin, he slid his tongue into my mouth, I gasped and I broke off: "I can't do this! The kissing I mean, it doesn't feel right."
"No problem," he said and went back to rubbing my shoulders and neck.
His hands started going down, rubbing my chest, feeling my nipples, caressing me, the chills he produced were amazing to me. I never felt this before.
He slid the chair outwards and unbuttoned my shirt. Kneeling, he began to kiss my chest and stomach, his hand caressing my bulging crotch. I could feel my underwear soaking in pre-cum...  I never knew I could be so turned on.
He stood me up, unbuttoned my jeans, he knelt and dropped them and my underwear to my ankles, he looked at me and my penis, as he gently took a finger up my shaft to the head, and wiped a drop of precum off and into his mouth. He stood, gathered my shirt's hem, pulled upwards, and dropped my shirt to the floor. I was naked in front of him. He stood there, looking at his prize, for a minute before he took my hand and guided me to the bed.
"Are you okay?" he asked as he sat me at the edge
"I think so, I'm okay, yes," I replied nervously.

He propped my legs up and had me lay back on to the bed.  He caressed my legs, and I remember shivering in excitement and nervousness. He put his fingers inside my legs, motioning me to spread them, I opened them up as his hands started sliding from my knees to my groin, the sensation was amazing.  I gushed more precum as he worked his way down my inner thighs, kissing them gently, as he made it to my penis. He licked up the shaft, licking the precum that was flowing like a faucet. Then, for the first time, I felt the warmth of a mouth over the head of my dick, and down the shaft...
Utterly amazing!
I let out a huge moan, and tried to choke it down like I wasn't supposed to do that. He gave me a few strokes with his mouth before he ran along the shaft with his lips. I got up on my elbows to watch, licking my lips and moaning in pleasure. He started sucking my balls, licking them from one side to the next, I arched my hips each time I felt his tongue hit the back side of my balls. He went back up and began sucking me, from my raging pulsating head all the way down to the base, he had no problem taking all of me in to his mouth.
I didn't last long as his mouth rode up and down me, he knew I was about to blow, and just as I did he stopped all the way down with his mouth at the base of my shaft. I came hard, arching my back, paralyzed, as I was convulsing hot loads of cum down his throat. I could feel his throat muscles tighten and with small movements up and down to drain me for what I had.


He kept right on going, sucking me, making me buck from the over sensitive glans just after cumming. I never lost my hard-on and he was going to make me cum again. He did so, from one orgasm to the next, within minutes of him sucking me and caressing my balls I came again.  He never stopped going up and down on me, bucking wildly, my legs crushing his head. He stopped, looked up at me and asked how I was doing.  I was speechless; I could only muster huge breaths and a little laughter; and motioned  the hand gesture for "Okay".
He ran his hand up and down my dick caressing my balls, "I think you got more to go."
He lifted my legs behind my knees, exposing my ass. His tongue once more licked down my head of my dick, down the shaft, he stopped sucked on my balls feverishly, then lifted me higher and made his way down my taint, sucking it and finally reached my asshole.
He began licking, I began moaning, squeezing the life out of the sheets with my hands, I pushed hard into his face as his tongue slipped into my hole, I never felt so much pleasure from any other part of my body, I was arching up as high as I could go so he would have total access to do what ever he wanted. He licked and gave me his tongue for awhile, which to me felt like forever, my dick was fully hard again.
I wanted him so badly to fuck me!
I wanted his cock buried in my ass!
I wanted to be taken!
I wanted to see his face as he came inside me!
But the thought of getting some sort of STD kept me from doing so. He went back to my cock, returning to the head, biting down just below it sending me into more ecstasy. He rode his mouth all the way down and started licking my balls while my cock was still in his mouth, his fingers caressing my asshole.
I blew again, he took it all while in that position. He slid his mouth off and looked at me with a big smile, "You taste amazing I think your done for the night."
I laughed, "I don't think I could go again, I'm exhausted."
He rubbed the inside of my legs for a minute, his chin resting on my knee. He reached down touched the head of my dick with his thumb, and said, "I like you to do this again, can we?"
"It's a possibility." But I knew deep down inside I would not, next time I would not be able resist the temptation of getting what I yearned for in the last round.
I got up cleaned up and dressed. He waited for me at the door, opened his hand and pushed money down my front pocket, patted my crotch, "Thank you,  you were well worth it and I hope to see you again."

He opened the door and explained how to get back to the base. For a moment I felt horrible about myself, but thought more deeply as it was at the time the best anyone has ever made me feel about myself...

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