flying with an Airman

With the event seeming to be winding down after the host handed out a pile of door prizes I decided to head to the patio for a bit of fresh air before getting the final drink for the night. I had dressed in an orange Search and Rescue flight suit with a leather aviator jacket. I knew that it got a lot of looks but no serious offers. I decided to grab a drink before heading home. The bar's serving area was busy but that never bothered me. Behind me, I hear a voice say, “So did you cause much chaos tonight General?” I turned and saw someone dressed in a green flight suit with a sage green jacket over it. His wedge, which looked like it was made of leather, was positioned in the American style. He could have been an extra for the movie “Top Gun” except for the fact that the flight suit was unzipped to his navel.

As the bartender asked for my order I added, “I’ll pay for whatever Top Gun here is having.” our orders were quickly taken care of and I headed back out to the patio to grab a seat. I was quickly followed.

As he sat next to me, he introduced himself, “I’m Drake, Thanks for the drink.” I nodded and wondered if I might be interested in getting fucked. “Search and Rescue orange, have you rescued anyone tonight?”

I grabbed his thigh, then ran my hand up towards his crotch and asked, “Do you want to be rescued?” He paused before nodding. I placed my drink on the table before I leaned over wrapping my left arm around his neck so I could pinch his nose and locked my lips over his mouth. It was not mouth-to-mouth but more of a long and deeply passionate kiss. With my other hand, I gave his left nipple a squeeze before I worked my way down under the flight suit to his crotch. His cock and balls were in a jock which I slowly massaged till he was getting hard. As I finished the kiss, I left my right hand over his cock and asked, “Like my version of mouth to mouth?”

Before he replied, he yanked my flight suit zipper down, reached in and gave my cock a squeeze, and found seven inches of hardening cock hidden inside. ”Yes Sir. I do.” he left his hand in place giving me the occasional squeeze as we finished our drinks. With both of us zipping up to looking presentable to the public I invited him home. As we headed out, I was able to press him against a wall for another long kiss which allowed me to run my hand down his back and grab his ass and bring a knee into his crotch. He was wearing a special flight suit that allowed access to his ass. I could fuck him while he was wearing the flight suit.

The cab ride was uneventful except for his hand in my crotch as if to make sure I did not disappear. Once in my apartment I offer him a drink and found him on my bed without his jacket or his boots but with the wedge still in place and the sunglasses back on. I guess he wanted me for him to strip out of the flight suit but I had other ideas. I hung up my jacket and noticed that his flight suit had Captain's bars sewn onto his shoulders.

As he finished his shot, I gathered his glass and slowly pulled the zip fully down on his flight suit before straddling his chest I was also able to clasp his hands over his head just to show who was in charge and knocking his wedge off in the process. I wanted to get him as hard as I could before I would let him cum.

After a long deep kiss, I worked my way down his chest giving both his nipples a working over sucking and biting them which caused him to groan in pleasure. His moaning intensified as I savaged his pecs by biting harder. I knew that I had found this Airman’s weak point. I wondered how he would feel if I also gave his cock the same treatment. I did not get a chance to do that.

He suddenly bucked his hips tossing me off of him with him and I found him on top of me. He quickly unzipped my flight suit and dove straight onto my hard cock. I was surprised that he did not swallow me whole but spent his attention on the head of my cock. He had also positioned himself so that I could access the zips and buttons hiding his ass. The few buttons holding the back flap were easy to undo revealing a beautiful ass ripe for a fuck. The perfect 69 position.

As he worked on getting me fully hard, I gave his sweet ass a true tongue lashing diving deep along his ass crack and into his hole. The deeper I drove my tongue into his hole the stronger I felt his tongue over the shaft of my cock and then my balls. I think he knew that I was getting close when he stopped with one final lick and said, “I want you to fuck me, Sir”

After he rolled off me, I was able to grab a towel, lube, and a condom from my nightstand before I ordered, “Assume the position for close formation flying Airman.” As he positioned himself so that he could watch me fuck him in the closet mirror on all fours with his legs being far enough apart to show off his tight ass I slipped the condom on. I gave his ass another quick lick before I slid a couple of lubed fingers into his hole to get him ready for my hard missile. The deeper I probed the louder his moans became.

With him primed for take-off, I positioned myself, ready to impale his hole. As the head entered I grabbed his shoulders and pulled back, forcing him partially upright and fully onto my cock. He let out a gasp in the suddenness of my first thrust. As I let him fall back down on all fours I gave his hole time to adjust to the girth of my seven inches.

His hole was tight, perfect for close formation flying. Grabbing his thighs, I started with a slow easy fuck leaving just the head inside his rosebud and ending balls deep. I was massaging his insides rubbing his prostate with each stroke. He raised his ass a little as he dropped his head onto a pillow allowing me to increase my pace and give his ass a real pounding.

I could feel him flexing his ass muscles bringing me close and with a final thrust, I grabbed his shoulders, pulling even closer, and blew my load deep in his hole. As I recovered my breath, he had gathered the lube and the towel under himself and was still slowly riding my cock. “Keep fucking me Sir, make me cum.”

I slowly raised him up so that he was resting on my thighs and I could still thrust into his hole. As he jerked his rock-hard cock, I was able to reach inside his flight suit and slowly play with his nipples. That set him off and he let his load fly over the towel with a very loud moan. As he cleaned his weapon, I made sure that his bomb bay was clean and secured.

I offered him another drink as a parting gift with my phone number. I certainly would want to fly with this wingman again. As he left he remarked, “That sure is a weapon of ass destruction General. I’ll keep in touch, I do have to ensure that I log a certain number of flying hours to keep my wings.”

He does indeed.

play

The Boy had told me that I needed to expand my comfort zone as his Sir and suggested a play party would be the perfect thing to do that. He even bought us tickets for the next one coming up. I knew that the Boy would be in his standard leather gear of chaps, jock, complex harness, and combat boots so I chose similarly with my chaps, jock with the removable pouch, and my biker jacket. Since the Boy was always turned on by tall boots I choose my engineer boots to complete the look. I also would pack a few toys in a backpack that I could check at the door.

That day of the event I took extra care to look the best. The leathers were all cleaned and polished including giving the boots an extra layer of grease to make them shine. I thought about adding a harness but with the jacket, I decided that going bare-chested would be best. As I geared up, I thought about the best way to get to the event and finally decided that a cab would be the best. In the backpack went a small flogger and paddle, a pair of police gloves, and my Muir cap. Into the jacket's inner pocket went the condoms, lube, and a pair of handcuffs just in case.

For the cab ride, I decided that my black tear-away rain pants would be best, I didn’t think the driver would like a bare ass on the back seat. With a few blocks to go, I suddenly got a text. It was from the Boy.

<Sir, I must apologize but something has come up and I will not be able to join you>. Attached to the message was my ticket. The Boy would not have canceled without a very good reason. He wanted to go to this more than I did.

<Understood Boy, Take care of yourself. I will miss the opportunity to fill with that sweet ass of yours> I replied

<Have fun Sir but not too much fun, I still want your load> the response came a minute later.

The play party location was not exactly a bar, more of an event space that you could rent out. They had divided it into three levels. The first had a stage and the dance floor, the second was where the bar was, the third was contained private playrooms, washrooms, and a gallery overlooking the dance floor.

I found Al a mutual friend working the door. “Where’s the Boy. I thought he was coming to this as well?” All I could do was shake my head briefly before he pointed to a spot I could gear up so he could help the next ticket holder.

Once out of the rain pants, I secured the flogger and paddle to my left side, slipped on the gloves and Muir cap before shoving the rain pants into the backpack. As I check the bag I told Al that the Boy had canceled at the last minute. He shook his head and replied, “Well try to have some fun, I think you need it.

I went to the bar and grabbed a cider before heading up to the gallery. From there I could see that the place was still filling up with most that most of the crowd being either on the dance floor or chatting with friends on this level. They had set up two portable slings up here though neither were occupied at the moment.

In a way, with the Boy not here I could scout around and maybe score some action but no one at the moment caught my interest. With a sigh, I decided that I might as well hit the dance floor for a while and wait to see who might show up.

The play party had hired a very good DJ for the event with most of the songs having some form of sexual hint in it He even played my Boys favorite S & M. With that I exited the dance floor and headed back to the gallery to finish off my cider and cool off a bit.

Upon the gallery, I found myself a quieter spot and considered the idea of a second cider while scanning the crowd. For all the leather and rubber and naked flesh, I saw nothing to really cause my cock to stir in its pouch. I was about to call it an event when Al wandered over to chat. “Any luck?“ He asked. I shook my head. “Well, you once told me that you would love to fuck a skinhead in gear and one just walked in. You can’t miss him.” with that he headed back to the coat check and disappeared in the crowd.

Sure enough I could not miss the sage green flack jacket, faded jeans, combat boots, and a full leather hood in the sudden break in the sea of black and flesh below me. The full leather hood was an interesting addition to the standard skinhead gear and the jeans seemed a bit looser than I expected around his ass but certainly a very hot look. It seemed like he was scanning the crowd as if he was looking for someone. I lost sight of him as he wandered toward the bar. I guess that he already had plans with someone else. As I slowly finished my cider I listened to the next couple of songs and thought about whether I should stick around have another drink or just head home.

I quickly checked my phone for the time and decided that I had time for another. Slotting the phone, I turn to head for the bar and saw the skinhead heading up the stairs. It appeared that he had a dink in each hand. I guess he found his friend. Before I had a chance to move, he stopped right next to me and offered me the tall can that he was carrying and remarked, “Sir.”

I decided to accept his offer and realized that it was the same type of cider that I had been drinking. I had to ask, ‘Did Ian send you up here to cheer me up?” he immediately shook his head before taking another large sip of the other drink he had been carrying. I could now tell that he was a little shorter than I was and though not ripped from too much gym time he had a normal build which meant he spent a lot of his work time on a computer. With the jacket open, I could see a bare chest and a black lock resting on his sternum. The collar of the jacket obscured what it was locked to. Probably a chain-link bought at some hardware store. In some ways, he reminded me of my Boy which caused my cock to stir for the first time but with the full hood in place, I could just see his eyes and well-proportioned lips. As much as I was checking him out he must have been doing the same to me. After taking a drink of the cider I ask, “Like what you see?”

He paused to finish his drink before nodding and reached out to squeeze the pouch of my jock. That gave my cock another reason to harden in the confines of the leather pouch. I saw that he was grinning before he licked his lips. He placed the empty glass on a nearby table before dropping to his knees in front of me and looked up as if to ask permission for a closer inspection. I gave him a slightly evil smile and nodded.

He immediately pressed his face into my crotch and inhaled deeply taking in the scent of the leather and my sweat from the pouch before starting to lick the entire outer surface of the pouch. The sensation of his tongue on the pouch was fantastic and I pressed my crotch harder into his face causing him to moan softly since he could feel my rapidly hardening cock. He paused his tonguing and look up again seeking permission to go to the next level. I quickly nodded and he reached up to undo the snaps holding the pouch in place. His final tug at the snaps was stronger than he had wanted and the pouch landed on the floor just past my boots' heels. As he bent over to retrieve the pouch I watched the jacket rise up his back to show his ass. I saw that the inseam of the jeans had been completely undone giving complete access to his sweet-looking ass and explaining why they had looked loose on him. I also noticed a hanky in his right pocket but in the dim light I could not tell its color and that he was holding the jean up with a pair of suspenders.

With the pouch in hand, he drew it to his face to inhale the scents from the inner surface, found a spot of precum which he lapped up before handing the pouch to me. As I stowed the pouch in the inner pocket of my jacket I could feel his tongue on my balls. From its base to the head my cock was being coated in a layer of his spit in slow, loving laps of his tongue making me nearly rock hard. With the shaft coated he took the head into his mouth and started sucking my dick and using his tongue on the shaft within his mouth.

I was surprised that he did not impale himself on my dick by swallowing it whole till he gagged but, he was concentrating on the most sensitive area of my dick. I was getting a full cock worshipping secession by this Boy. He may have sensed that he was getting me close to cumming that he let my cock slip from his lips and looked up at me and licked his lips. I reached down to caressed his jawline with my gloved hand and brushed my thumb across his lips. With a gentle gesture, I brought him to his feet.

Grabbing his jacket I quickly pulled him closer and forced my tongue between his lips. As the kiss deepened I wrapped my arms around him into a strong bear hug pressing our bodies together and felt my hard dick rubbing against the denim covering his crotch which was already bulging with his hard dick. I knew what I wanted next. I had tasted his lips and I wanted to give his ass the same treatment.

We had slowly maneuvered closer to the club's wall as we kissed till we were bumping into a table where I quickly spun him around forced his chest onto the tabletop exposing his ass. I forced his leg apart a bit further opening the denim wider and began to explore his ass crack first with my gloved hand, then with my tongue. The coolness of the leather caused him to shiver slightly and my tongue for him to moan loudly. His crack was hairless by either shaving or by having it waxed regularly but the slight layer of sweat was sweet to the taste as I bathed its length. Every time my tongue passed over his hole he let out a moan of pleasure. He reached back to pull the denim giving me a fuller view of his ass before driving my tongue deep into his hole. I gathered my spit from his wet crack onto a couple of my fingers before I slowly inserted them into his tight hole. The spit and the leather made his hole open up a little. He was ready and willing to be impaled on my dick.

I could have fucked him right there, prone over the table as I rubbed my hard dick along his wet crack but he had other ideas. He pointed to the now-empty sling and understood exactly how he wanted me to fuck him. We quickly walked over to the sling and he slid onto the leather with his leg in the air waiting for me to secure them to fill his ass with my hard cock.

With his legs secure I looked down and in the light with the jacket wide open I saw the chain secured around his neck. I remembered weaving each link of this collar and instantly recognized it. This hot secured and hooded skinhead before me was my Boy and I knew exactly what he wanted from his Sir. This boy was going to get exactly that. I would give his hole a proper raping.

First, he deserved to be teased a bit before I impaled him. With my hard cock rubbing his crack and hole I gave his sensitive nipples some attention, getting them hard by dragging my teeth across them. I started to work my way down his torso with my tongue leaving a shiny trail of spit. When I reached his crotch I used my teeth to open his fly releasing his rock-hard cock.

I started to edge him with slow strokes before swallowing his cock whole. This was driving close to the edge and I knew then that he was ready for a hard pounding. I gave the head of his dick a quick nip before I told him that I was about to give him the fuck of his life.

From the breast pocket, I pulled out several packs of lube and a condom. After slipping the condom on I lubed his hole with a gloved hand and slowly let his hole accept two fingers. He was squirming in the sling in excitement on the thought of what was to come. I aimed my cock right at his hole and slowly pressed the head into his hole. The boy must have been working out since his hole felt tighter in this position. Grabbing the chains holding the sling I drew the boy further onto my cock till my balls were pressing into his ass crack.

He was starting to moan in pleasure as I hit his prostate for the first time and I saw his flex in reaction. I started to withdraw before ramming back into him. I wanted him to feel each hard inch as I rode his ass. With me filling his ass I paused to pinch both nipples before I started the real fuck. The sling made it easy to ensure that he was getting a full-length fuck.

Our scene was causing a bit of an audience. Soon he had two people sucking on his nipples from the sides of the sling as I started to build a rhythm toward blowing my load. It was rough and fast as I tried to have each stroke hit his prostate. I could tell that he was enjoying this as his moaning got louder the harder I pounded his hole.

With a final thrust, I blow my load in his ass. I had to lock my knees so that I could still have him impaled as the waves of a powerful orgasm wash through me. I wanted the boy to still feel that his ass was still filled as I began to jerk his cock which had been leaking the entire time. His climax was load and his load soon coated the leather palm of my glove. I rubbed the gloves together working his cum into the leather. Nothing better than a boy's protein to condition them.

As my softening cock slipped out of his hole I grabbed a wet nap to clean his ass and my cock before releasing his legs from the restraints. I reached down and grabbed the chain collar to force him to his feet for a long deep kiss. As I released him I told him to hit the washroom to clean up as I cleaned the sling completely.

As I waited, I reattached the pouch to my jock and stood next to the sling. When he returned he asked for help removing the mask. Once that was off I kissed him again before we headed to the bar for another drink. I was sure that there was a tale behind all of this subterfuge but that could wait.