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My Hawaiian Cadet Iolana  

JimmyB7474 59M
0 posts
3/28/2017 12:59 pm
My Hawaiian Cadet Iolana

The first thing I recall was the blinding light and the crashing of the galvanized trash can as Drill Sergeant Martin Gill kicked the thing across the barrack floor. The second thing was a voice that sounded like thunder in a small cave bouncing between the lockers.

“Get UP! Kay DETS! Get the FUCK UP! We’re burning DAAAAY-- LIGHT!!!!”

Oh my god… how the hell can that voice come from a human throat? If you could imagine a cross between the base singer of the Stamps Quartet and a male lion then you would be close. Listening to Drill Sergeant Gill actually makes your fillings vibrate when he cuts loose. And he does that ALL the time.

The crash of the Gill Can (we called it that cause that’s the only person allowed to touch it) continued as Gill held up the lid and banged it against the side again and again. Why did I have to get the top bunk? The lights overhead were right in my face…..UUGH! I hit the deck in full attention as Drill Sergeant Gil began inspection of all the cadets standing in our skivvies. The female cadets were housed down the hall in smaller rooms with doors and were already up.

“Calisthenics DOWN STAIRS in FIVE minutes Kay DETS! Move it!” Gill Roared.
“Pants.. socks…belts….boots…. RUN damn it Run!” Thunder in a small cave.

Moving as fast as I could I covered the four flights of steps two at a time without breaking my neck. Considering I had been fast asleep only moments before…. I think I finally woke up during push-ups. Exercise drills ended with a one mile jog to the mess hall for our 30 minute breakfast. We spend 25 minutes in line and 5 minutes to eat. I got lucky, they still had bacon.

March back to the barracks and get ready for the day. Schedule says rifle range which meant a 4 mile hike with full web gear and weapon. As we lined up outside for company formation, I remembered it was my turn to play company commander so I lined up facing the men and read out the program for the day. I was to turn over the company to the lieutenant cadet to make one announcement and order the platoon sergeants to take command of their platoons. The cadet scheduled as my lieutenant was Cadet Iolana Pelei. The cadets in my platoon pick nick names based on where you are from. Makes it easier to remember individuals I guess. I was called Tennessee and Iolana was Diamond Head. Yeah I realized the double meaning behind the name but apparently Iolana didn’t get it. I called her Lana for short.

Time came and I turned over the company to Iolana and she marched up and immediately froze. Stage fright had set in. I watched and waited for the announcement but she was completely mortified. We had done a few rehearsals the night before when Sergeant Brown informed everyone of their positions for the following day. We both knew what had to be done.

Iolana just couldn’t bring herself to bark the orders. After about a minute of awkward silence, I broke protocol and marched up to Iolana and took back command. I made her announcement and barked out the order for sergeants to take command of their platoons. The rest of the morning ritual went off without a hitch. Iolana kept thanking me over and over again for saving her “bacon”. Drill Sergeant Gill wanted to know what was I thinking - breaking protocol like that. I told him that my fellow cadet was in trouble and someone had to do something, so I did. He gave me an odd look and walked away.

Later at the rifle range I wound up in line behind Iolana (on purpose of course). Yes, I was milking the “hero of the day” for all I could get. Iolana stood about 5 foot 5, extremely athletic body and very long black hair surrounding a deeply tanned Polynesian princess face. Her voice was deeper than some of the guys in my platoon. Very sexy and almost hypnotic black eyes that held innocence that contradicted everything else about her. The most beautiful thing about her was her personality, always happy and smiling. Well, almost always. When she froze in place the look of panic in her eyes forced me into action. I had to help her out. Protocol be damned, I was in love.

The firing range went well. I found out why Iolana was in the ROTC program. She is a natural with a rifle. I was shocked when my friend pulled a perfect score with the M16. My marksman score paled in comparison. When we talked about it, I found out she was on the rifle team at her school. Me, I hadn’t shot a rifle in about 5 years before going to Fort Knox. The rest of the day went off without much to write home about.

During the next week we were scheduled for orienteering. This is a fancy way of saying “reading maps.” Our platoon was given a class on maps and compass reading then we were dropped off in the middle of the woods somewhere on the base. Our platoon was broken up into teams of two and given one map and one compass. Wherever the teams were dropped off was designated as Alpha Base. No two teams were to be dropped off in the same place. As luck would have it, Gill assigned Iolana to me. I had no idea Drill Sergeant Gill even liked me that much. Thank you Gill… thank you thank you!

This was a timed event. We were to navigate from Alpha Base to check points Bravo, Charley and Delta before finishing up at Echo Base. Two advantages, I had spent a lot of time hunting in the woods as a and my sense of direction was pretty good. One disadvantage: Iolana had never been in woods before so…. By process of elimination, I was in charge.

Bravo and Charley were easy to find. The terrain was a little rough but I felt we made great time. As we were moving through the woods, Iolana decided it was time to stop and rest for what I thought was going to be a minute or two. It turned out to be a little bit longer than that.

“Tennessee,” she said, “I never did get to thank you properly for what you did last week. I think what you did was way beyond the call of duty wasn’t it?” She stopped and sat on a fallen log in the middle of nowhere. She pulled her canteen out and offered me a drink. “Need to keep hydrated Jimmy.”

I was a little impressed that she knew my first name. Everyone called me Cadet Bond or Tennessee. I don’t think anyone outside Drill Sergeant Gill and Sergeant Brown knew my first name. Well there was Cadet Bell but she wasn’t here. “Thanks Lana.” I said.

“No Jimmy. It’s Iolana ( EYE oh LA na) not Lana.” She smiles as she wrinkles her nose in that cute way I like. “Iolana is Hawaiian for “Flying Bird” and I prefer that over “Diamond Head”. She giggled a little as she took a swallow from the canteen and passed it back to me. Then she said the last thing I ever expected to hear.

"I want to make love here on this log, so the whole forest can see and hear us cum."

I spit out the water I was about to swallow as soon as I heard…. “Wha..WHAT?” I stammered.

Iolana turned, spoke seductively. "Now do you see anything you like?" She slid her fingers slowly down her belly and over her perfectly formed ass under the green uniform. Her fingers worked together to unhitch the web belt and quickly pulled off the top half of her uniform. The white tee-shirt and bra soon followed. I began to fumble with my own uniform, my hands were shaking with excitement and I watched as she slid a finger inside her pussy and then brought it back out to lubricate her clit. She closed her eyes and started to pinch her nipple with her other hand leaning against the log.



I felt my penis start to rise as I watched her masturbate. I wrapped my fingers around it and very slowly started to stroke it. I was pacing myself because I wanted, no, I NEEDED to watch Iolana bring herself to an orgasm!!!

She opened her eyes and smiled when she saw me stroking myself. "Don't cum yet baby," she said softly, "I want to finish you myself, but first I'm going to cum for you, let you watch what I do when I'm all alone. Do you like watching me Jim?"

"Oh god YES! I think it's the most beautiful thing in the world.” I was mesmerized by the sight of my Polynesian princess here in the woods doing this… just for me.

I was so turned on that I forgot to pace myself for a moment and had started to stroke myself a bit harder. Then I moved closer to her body to get a better look at her fingers rubbing and stroking her pussy.

She had thrown her head back and closed her eyes, her fingers worked deftly between her legs and her other hand squeezed, pinched and pulled her dark nipples. Her breathing had become labored and small whimpers escaped her lips from time to time.

I studied her body. She was pretty fucking perfect! Good looking, long dark hair, deep tropical tan, nice tits, great butt and a really tight pussy. Her legs were<b> muscular </font></b>and very shapely. But what I liked about her most of all was she obviously had no qualms about sex. She wanted me and by god, I wanted her.

Her whimpers had increased and her fingers had sped up and I could see her inner thighs glistening with pussy juice. The hand that had been teasing her breast had moved to her ass and she began finger fucking herself in the butt.

She then let out a gasp, her thighs started to twitch and I could see her pussy juices run down her inner thighs as she rubbed her clit furiously. She stared at me as she rode her orgasm and I stroked my cock harder. She suddenly dropped to her knees and took my cock into her mouth. She sucked deep and hard as her fingers caressed my balls and ass. The tension rising and my balls tighten up. "Oh god Iolana, I'm gonna cum!"



I was expecting her to stop, but she sucked even harder and ran her finger delicately from my ass to the back of my balls. This sent me over the edge and I shot my load straight down her throat. She continued to suck, making sure she swallowed each and every drop I had to give. She looked up as she released my cock from her mouth, still caressing me with her tongue. She grinned and giggled softly, "Did you enjoy that baby?"

"That was the wildest blowjob I have ever had. Given by the sexiest woman I have ever met." I gasped for breath.

“Now you know why I have that nick name.” she said with a sly wink. “And you can call me “Diamond Head” anytime you want.”

She looked up and saw I was watching her and she gave me that sexy wicked grin again. Shifting her gaze to my semi hardened cock, she laughed and said "Come over here lover, and let me deal with that beautiful erection you have there." My cock was already getting hard again.

I moved slowly over to her, watching her run her tongue across her lips and she focused on my cock. She reached out and took it in both hands as if she was receiving a precious gift. Her lips wrapped around the tip and her tongue danced across the small opening, before she pushed her head forward and engulfed my whole shaft in one smooth movement. Sucking the life back into it.

God, here I am, naked in the middle of the woods, with a naked woman who just fucking loved sex, being sucked hard and deep while her fingers caressed my balls and asshole. I reached down and gathered up her long black hair in one hand, while the other traced fingertips around her nipple. She started to moan as her nipple was teased, pinched and pulled. I then realized she had one hand between her thighs, rubbing her wet clit again.

She pulled away from my cock and said. "Fuck me like an animal Jimmy - Fuck me HARD!" With that she turned around and got on all fours on top of the log, her pussy wide open and glistening with her juices.

I moved in behind her, lined up the tip of my cock with her gaping pussy lips and then thrust it deep into her.

"Oh fuck yesss!" She screamed.

"Fuck me hard baby, make me squirt."

I began to thrust into her, bringing the tip almost out and then ramming it back inside her as I gripped her butt for better purchase.

She began to moan loudly and push back to meet each thrust. I slid my fingers between her butt cheeks and began to play with her little rosebud. Her moans got even louder and for a minute I was worried that someone might hear us. There were other cadets in the woods at this time of day. I slowly pushed my thumb into her ass, and her moans started to get to increase as I started to match each thrust of my cock with my thumb in her ass.

Suddenly she let out a loud cry and I felt her pussy juices spray down my legs as she began to spasm all over.

"Oh God, it feels so fucking good, thank you baby." She whimpered as the orgasm took over her bodily controls. She dropped her head onto the log and just stayed there for a minute with her ass stuck up in the air.

Eventually she turned and whispered. "Baby, fuck my ass, my pussy is too tender to play at the moment.”

I leaned over and dropped a mouth full of spit onto her tight little hole, then once again pushed my finger into her. And I began to lubricate it with a combination of spit and her pussy juice. I pushed the head of my cock against the hole and began to push against it, feeling it slowly open. I slowly pushed it past her sphincter muscle and up inside her, feeling the tightness engulf me. I started to fuck her and her inner muscles flexed and caressed my cock until I could hold it no longer! I let my thick cum shoot up inside her. She flinched and then reached back and cupped my balls in her hand, kneading them, trying to empty every drop of me deep inside her. My vision suddenly turned purple around the edges and I collapsed on top of her, every muscle in my body was a quivering mass. I shook until the feeling passed.

After I lifted myself up, I pulled out of her and lifted her gently to her feet, kissing her passionately and holding her tightly. My god… that was amazing……..

"Thank you sweetheart and my cock thanks you too."

"My pussy and ass both feel very honored" she replied. “and a little sore.”

It took a while but we both rested on the log until we got our strength back. Both canteens were emptied. I looked at my watch and realized we had lost almost a whole hour.

“OH SHIT!” I said, “Gill’s going to kill us if we don’t finish this course!” With that being said, we threw on our uniforms, took our bearings and headed out to find Checkpoint Delta.

“Yeah, he might, but it was worth it ….. my hero” Iolana said while we were “humping it” over the terrain.

Later that night in the barracks...



My blog JimmyB7474 is called Into The Woods (erotica) entertaining stories about a guy named Jimmy. Enjoy.


JimmyB7474 59M

3/28/2017 1:04 pm

To all the military personnel on this site, Thank you for your service. Jimmy B.

My blog JimmyB7474 is called Into The Woods (erotica) entertaining stories about a guy named Jimmy. Enjoy.


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