Joining The Mile High Club

Just another weekday morning and with nothing special on the calendar, I had arrived at work early to catch up on some long overdue paperwork. Finding no motivation to start right away I adjourned to the cafeteria for a cup of coffee and some conversation with a few of my fellow early risers. Moving toward our regular table, I noticed that Tom, Rick and Mary were already sitting there and talking to a lady I had not seen or met before. Approaching the table I noticed the stranger looked up and smiled the most intriguing smile at me as I took a seat. Mary introduced me to Jeri and said she was a new employee and would be working in her section. Small talk that morning and for the next several weeks over coffee gave me an insight into the makeup of Jeri.

Let me describe Jeri first, lest you think she was a raving beauty or a goddess. Jeri was, as I soon found out, almost 35, had double masters degrees, had never been married, carried just a little too much weight, was just a little shy of 5’ 5," mousy blond hair and in need of some serious beauty salon work. Mostly though I was taken by her absolute intelligence and what had to be the greatest personality and smile you could ever imagine, friendly and smart she loved to talk about any subject. It wasn’t long before I discovered a side of her I really liked. She was the absolute master of the double entendre, especially the way she could turn any subject it into a sexually related issue.

For the first couple of months our association consisted of coffee early in the morning and an occasional coffee break in the afternoon. Last month on a Monday morning coffee break I commented that I would be out of the office next week attending a conference in New Mexico. I was totally surprised when Jeri announced that she would be attending the same conference. Not wanting to miss an opportunity I offered to buy her dinner the first night of the conference, her response was immediately in the affirmative. I was further amazed to find we would be traveling on the same flight and be staying at the same hotel.

I told Jeri how much I loved to fly and that I had my own airplane and flew locally almost every weekend. Jeri developed this look in her eyes that I had never seen in a woman before and said “I have never been in a small airplane before, would you give me a ride sometime”?

As I had planned a short trip for the upcoming weekend I invited her to come along. Little did I know at the time that we would both be cumming before the trip was over.

For the remainder of the week, every time we talked Jeri would ask questions about flying in a small airplane. But the question that most caught me off guard was when she asked, “if I was a member of the Mile High Club." Now every respectable pilot knows what that club is and most would give one of their testicles to join.

However, I did not understand right then how Jeri could know about this club if she had never been flying in a small plane before. It took me a couple of days to find out her best friend was married to a pilot and she had told Jeri about the pleasures of the mile high club. Not wanting to let an opportunity this good pass me by I asked her if she was interested in joining the Mile High Club.

Her response was an immediate and resounding “yes." Too which my cock began to twitch and suddenly felt very confined in my shorts and pants. I told Jeri that this was a serious decision we were about to make, especially since we had never been out on a date, had never kissed, much less had sex together. Jeri smiled that killer smile and said “I know and that is just the way I want it, just tell me what I need to do and where I am to meet you."

Knowing she lived very close to a local airport I agreed to fly in and pick her up there. Also I told her that she should dress very comfortably, loose shorts and top and preferably with nothing on underneath. Her smile was enough for me to know she fully understood the instructions. Jeri also offered to pack a picnic lunch and with that we agreed we would meet on Saturday at 10:00A.

Saturday arrived and was one of those days pilots pray for, beautiful sunshine, no winds and only a few white puffy clouds floating through the sky.

From the minute I pulled the airplane out of the hanger my cock started to flex itself in anticipation of today’s activities. Following the instructions I had given to Jeri I had dressed in a pair of very loose fitting shorts, no shorts and a button shirt that could easily be removed inside the cockpit.

Arriving at her local airport at 10:00A I was surprised to see Jeri was waiting with a picnic basket and a small overnight bag. After parking the plane I walked over to her and was greeted with most incredible kiss I had ever experienced. Locking her lips to mine she forced her tongue into my mouth and gave me the deepest French kiss I could recall. Breaking the kiss Jeri said, “Well that’s one of the three things you told me we had not done out of the way, and I consider this a date so that is two out of three are out of the way and that only leaves one more." Once again the smile that followed her words give me no doubt as to her intentions.

Escorting her to the plane, I opened the passenger door and gave her a hand climbing up into the cockpit. As she swung her legs into the cockpit I was presented with an exquisite view of her brown pussy hair when the leg of her shorts opened up. Now my cock is really stirring and it is very obvious that she is having a serious effect on me. Leaning over Jeri to fasten her seatbelt I am treated to another wonderful site when the top of her blouse moves and I can see a proud firm tit and a very erect nipple. Fastening the belt I drag my arm across her chest and get my first feel. Knowing my cock is rising and that we need to get moving before I “take off," I move to place the picnic basket and overnight bag in the baggage compartment.

Jeri says, “Please make sure I can reach the overnight bag when we get airborne." I place it on the back seat within arms reach and checking all the doors and locks I move into my seat, belt up and begin the start procedures.

Explaining as I go, I glance at Jeri and observe that the look that was in her eyes when we first talked about flying is back again. I also noticed a very heady aroma that reminded me of an aroused, wet pussy. Looking down at Jeri’s crotch I observe a small wet spot forming on the front of her shorts.

Reaching across the cockpit Jeri begins to stroke my leg, glances at me and says, “I can see your getting aroused like I am, can I touch you”? Not wanting to spoil the moment but recognizing that we are still on the ground I respond, “ this will have to wait for a few more minutes until we can take off and reach our cruising altitude." Jeri’s response is short and to the point, “I hope that doesn’t take too long as you can see I’m already wet and I can hardly wait until I can have that lovely cock of yours in my mouth."

Do you have any idea how hard it is to concentrate when you have a hot babe waiting to suck your cock? It isn’t easy my friends.

Moving into position on the runway and applying full power we takeoff into the wild blue yonder. No sooner than we leave the ground and I hear a slight moan from Jeri and look over to see that she has a finger buried deep inside her juicy wet pussy. Looking at me she asks, “Can I start my surprise for you now”? Responding I say, “I can hardly wait but we must wait for a few more minutes to make sure we have reached the proper altitude of 5,500 feet," well above the mile high limit of 5,280 feet.

As we continue to climb Jeri occasionally lets me know she is eager and ready by sayings things like “my pussy is really getting juicy, my nipples are so hard and I really want your cock in my mouth." All the while she is pinching her nipples and playing with her pussy, filling the cockpit with that delicious smell of an aroused dripping wet cunt. My cock has responded and is trying to escape from my shorts managing to peak its head out from the leg opening. Spying my cock head and its leaking precum, Jeri reaches out and runs her finger over the tip, scoops up the glistening drop and slowly moves it to her mouth.

Watching her suck my juice I almost missed the assigned altitude. Leveling off, I engaged the autopilot and announce, “I am now ready for the surprise." My words have barely escaped from my mouth when Jeri reaches down undoes her seatbelt, removes her blouse, allowing me to get my first full view of her firm round breasts and those delicate hard nipples. Jeri asks me “Please pinch my nipples, I need for you to touch me, pinch them hard." I can’t tell you how long I have been waiting for this moment and slowly begin to roll her hard little bud between my fingers. Rolling it back and forth I can hear her moans of pleasure. Suddenly she yells, “pinch it harder, pull on it, I want to feel it all the way down to my pussy." Immediately I respond and hear her groan louder as I twist and pull her erect nipples.

As she continues to moan, Jeri reaches over and unzips my shorts, sliding them down my legs until she has released all 7” of my throbbing hard cock. Stroking it slowly she uses one finger to collect the precum and each time she deposits it in her mouth. After just a few moments of this she suddenly removes her hand and says, “now it is time for your surprise."

Slowly Jeri reaches down and unzips her shorts and verily sexily removes them. Completely naked I see her proud breasts and juicy wet pussy fully exposed. Turning in her seat Jeri spreads her legs and slowly traces the outline of her pussy lips with her fingers, slipping first one the another finger deep into her sopping wet pussy, she whispers, “could you please reach into the back seat and get the overnight bag, open it up but do not look inside."

Only to willing to comply I retrieve the bag and after opening it I hand it to her. Reaching into the bag Jeri removes the most realistic Dildo I have ever seen and says, “ I could only guess at the size of your cock but this one is pretty close to what I felt a minute ago. The big difference is that this one is battery powered and vibrates like crazy and when the right time comes, no pun intended, I want this one deep inside my aching pussy while I suck on your hard cock, that way I’ll have two cocks in me at the same time."

All this talk only causes my cock to stand at full attention and profusely drip precum. Hearing the vibrator move into high gear I watch as Jeri runs it slowly over her hard nipples and begin a trip south to her hot, wet pussy. Groaning loudly now Jeri begins to slide the vibrator into her eager and waiting pussy. All the while she is talking, “I am so close to cumming, “I can’t wait anymore I need your hard cock in my mouth." As she inserts the vibrator deeper into her pussy she leans over and licks the precum from my cock, licking slowly around the head she says, “it tastes so good, but I want your hot cum in my mouth."

Slowly she takes my cock into her mouth, rolling her tongue over and around the sensitive head, sucking it ever deeper into the most wonderful mouth I have ever felt. Moving with the confidence of someone who has done this many times before, Jeri slowly takes my dick deeper and deeper until her chin is resting on my balls. Looking up with those drop dead gorgeous eyes gets me even more excited as she slowly begins to suck up and down my erect cock. With each movement of her mouth I can see and feel her hand movements as she moves the vibrator in and out of her sopping wet cunt. Even with her mouth full of my hard cock I could tell Jeri was close to cumming by the noises she was making around my dick. Her hot wet mouth was driving me wild and I was awfully damn close to cumming myself.

As her body begins to shudder, her mouth begins to move faster and faster on my ready cock I feel the cum start to move from my balls to the tip of my cock. Yelling out loud I announce to Jeri, “I am on the edge, just a little more, suck me harder, or shit I feel it cumming. Suck my cock, eat my cum, swallow it oh shit I’M CCCCUUUUMMMIIINNNNGGGG."

Jeri eagerly sucks my exploding cock, making sure she gets every drop, she hungrily swallows it all and explodes into her own tremendous orgasm. Shuddering like an earthquake has struck her she continues to suck my cock draining every last drop. As my cock begins to deflate, she licks the very sensitive head and begins to talk to my dick, “Thanks, that tasted so good, I love to have you cum in my mouth, hurry up and rest as I have more surprises in store for you later."

So engrossed had I been in the sexual activity in the cockpit I had not noticed that the autopilot had directed us to our destination and we were just a few miles away from landing at the airport there. Quickly dressing Jeri and I began to talk about how rewarding this experience had been. Both of us agreed that we would like to try it again in the near future.

Upon landing and parking the plane I reach into my Pilot Flight bag and present Jeri with another reward. A pair of tiny gold wings with the words “Mile High Club” emblazoned there on. Pinning it onto her blouse I pull her tightly into my arms and kiss her deeply. As she twists her body into mine my cock is stirring once again and I rub it against her crotch, feeling her respond I reach up and caress her breast. Breaking the kiss, Jeri smiles and says, “Grab the picnic basket and let’s see if we can find a private place to continue our lovemaking." That is another story along with what happened in New Mexico the following week.