My name is Dan and I am 32 years old, single and passionate about flying. I have my pilot's license & am certified to fly twin jet planes. I don't own one but my army buddy has an aviation business and lets me use one of his planes as long as I pay for the fuel.
My girlfriend's name is Katheryn (Kate) and she is 28. We have been going together for a couple of years now and our relationship is getting serious. So, I decided that I was going to do something romantic and fly her to San Francisco for dinner, then stay overnight at a nice hotel and fly back the next day. I figured we can join the Mile High Club too, something she mentioned once or twice. I was even going to propose to her.
I called Kate and said, "How would you like to go to San Francisco this weekend? I've made all the arrangements and we leave tomorrow around noon."
"That sounds great but I am stuck with Emily for the weekend."
"No problem, bring her along."
"Are you sure? She can be a pain in the ass."
"Don't worry, bring her...see you at noon. Love you."
After I hung up I had to figure out how I was going to do this. Her sister is 19 and the wild child. She is gorgeous, like Kate. I thought, maybe I'll get her to join the club too.
The next morning I went to check out the plane, a Gulfstream, got it fueled and put some food and champagne aboard and then headed to pick up my passengers.
When I got there they were ready and each had a small overnight bag with them. Kate was dressed in black tights and a red tank top, clearly without a bra and Emily had white tights and white tank top also without a bra.
It took us about 45 minutes to get to the airport and it took us a few minutes to board the plane.
They were both amazed at how nice the inside was. Kate laughed when she saw the bed in the back of the plane. We stowed everything away and I closed the door and told Emily to buckle up and I took Kate into the cockpit with me.
We settled in and I started the engines...then got clearance to take off. In a relatively short time, I was taking off and climbed to 10,000 feet where we would cruise to the west coast. I put the plane on automatic pilot and Kate and I ventured back to the cabin with Emily.
As soon as Emily saw me she said, "Why is there a bed on the plane?"
"It's to sleep in," and I laughed and continued, "It's the mile high bed."
"What is that?"
"it's for people who want to fuck and join the Mile High Club."
Kate gave me stare and shook her head.
Emily asked if we were members of the club and I told her we weren't but will be after this trip. Again I got a stare from Kate.
Then Emily asked who was flying the plane and I told her it was on autopilot.
I took out some snacks which we all enjoyed and I told them that the flight is about 6 hours long so we could all relax.
We chatted a bit and enjoyed the flight.
Then Emily said, "So, when are you guys going to do it?"
Kate & I laughed and I said, "When you fall asleep."
"That's not fair. I want to see you guys do it. I wouldn't mind if Kate saw me do it."
I laughed and told her that she wasn't going to join the club on this trip, just her sister.
"Come on, let me see. I've seen my sister do it before...please."
Kate looked at her and said, "What do you mean you have seen me fuck?"
"I saw you a long time ago...so let me see now. Besides, I want to see Dan's cock."
"That's enough little sister. Behave or we will turn back now."
"Kate, I am going to turn back. We'll do this another time. I'm sorry."
We turned back and landed at the airport. Then I took them home. When I got home, I called the restaurant & hotel and cancelled everything and apologized.
The next day I called Kate who apologized for her sister's behavior. I told her it wasn't a problem and for her to let me know when she would be free to try again.
Over the next couple of weeks Kate & I spoke on the phone but we didn't see each other as our schedule conflicted.
One night Kate called me and told me that she had the next two weekends free if my offer still held and I told her it did, so we made arrangements for the upcoming weekend.
I called her and told her everything was set and that I would pick her up Saturday at noon and she said she would be waiting.
That morning I checked out the plane, loaded some goodies and went to pick up Kate. There she was, a vision of beauty. She got in the car and off we went. In 45 minutes we were at the airport and boarding the plane.
As soon as we were ready, I got clearance to take off and away we went. I climbed to 10,000 feet to cruise to the coast. I was in the cockpit about two hours and then I set the autopilot and went back to the cabin.
As soon as I exited the cockpit, their was Kate, laying on the bed naked waiting for me. She looked radiant. Her red hair, green eyes, red trimmed pussy and, oh those toys...what more could a man ask for?
I went to her and smiled and said, "This is starting off better this time, don't you think?"
"I couldn't wait any longer. I wanted you so badly. Come join me."
I wasted no time in joining her. My cock was already hard as I laid beside her. "Are you ready to join the Club?"
"I have been more than ready. Let's get started."
As we started feeling each other up and hugging and kissing, she told me to fuck her. I mounted her and just as my cock was at her slit I heard the radio..."This is an emergency weather alert. Severe weather is moving into your flight path...ceiling is 2,500...please deviate your flight path immediately."
"Damn, get dressed. I have to go up front...buckle in."
As soon as I got to the cockpit I saw dark, thick clouds in front of us. I started to climb to get above the clouds but I couldn't. I then turned around to try to out run the weather but soon the plane was engulfed in clouds. I started going down to get under the clouds but I just couldn't get clear.
About a hslf hour later, the weather broke and I started looking for a place to land. I didn't even know where we were but I had to set the plane down.
Somehow I saw a flat piece of land and I brought the plane in for a landing and we landed safely. I looked out to see where we were and it looked like we were in the middle of nowhere in the Midwest. At least we were safe.
I went to the cabin and asked Kate if she was ok and she said she was. I hugged and kissed her as the heavy rain and wind pounded the plane.
"Now, where were we before we were so rudely interrupted?"
"If I remember correctly, we were going to join the club but I guess we can't now."
"Well, we are in a plane, aren't we. And nobody has to know how high we were, do they?"
"Mmmm, I like your thinking."
We got undressed and got on the bed. In seconds we were all over each other. We wasted no time in getting into 69, Kate's favorite position. The feel of her warm mouth on my cock got it even harder. As I was eating her, she was squirming underneath me.
Soon, she was bucking her hips and I knew she was ready to explode. Just then I felt my balls swell up and my cum shot out into Kate's mouth. Then she came, her body shaking. After a few minutes, we both came down from cumming and rested.
"Kate, that was amazing."
"You filled my mouth...tasted good."
"It was like the plane wasn't even moving...it was so smooth."
We laughed and just laid there, cuddling.
About an hour later I decided that we better take off before we had company. I got the plane up and we continued on our journey to San Francisco. In flight I called the hotel & restaurant and advised them of our delay and that we would be arriving a couple of hours late.
As I was in the cockpit. Kate joined me naked, which was a pleasant surprise. I looked at her and she said, "Well, this is the cockpit, isn't it?"
"Yes, it is."
"So let me see your cock."
I put the autopilot on and managed to get my cock out. As soon as I did, Kate had her mouth wrapped around it, giving it a good sucking. A few minutes later, I shot another load in her mouth. She opened her mouth to show me my cum, smiled and swallowed every drop. "Did we join the Mile High Club?"
"No. We have to fuck to join the club."
"Don't worry, we'll join on the way back."
The rest of the flight was without distractions and we made up some time but still arrived late. As soon as we landed, we took a cab to the restaurant for a late night dinner. I had everything arranged and the waitress took good care of us. The food and service were delicious.
Over the course of dinner, we were able to chat with the waitress, Diane,who was really delightful and cute. She told us that she was supposed to go to NY, where we just came from, but because of the pandemic she was afraid to fly commercial.
Then, out of nowhere Kate said, "Why don't you come back with us? We are leaving tomorrow."
I looked at her and she said, "It will be ok. Trust me."
"It will be fine."
Then she said to Diane, "So, you want a lift? It won't cost you anything either."
"Yeah, sure. Thanks a lot."
"Diane, there is one thing though. Have you ever heard of the Mile High Club?"
"Sure, I wanted to join it a couple of years ago but I never did."
We laughed and Kate said, "Well, Dan and I want to join it too and because of circumstances, we weren't able to coming here but we are going to join it going back. Would that bother you?"
"Hell no. I wouldn't mind it at all."
"Good. Then be at the airport tomorrow at noon. We will meet you at the front entrance then go to our plane."
"That sounds great. Thanks so much."
We finally left the restaurant and headed to the hotel. We checked in and went to our room which overlooked the bay. Everything was perfect.
We undressed and showered together and had an incredible night of sex. After a few times of fucking, we laid in bed and held each other. I then reached out to the nightstand and took a small box that I had put there earlier and said to Kate, "You are the most incredible woman I know and I want you to be my wife." I handed her the box and she opened it and put the ring on and said, "Of course I'll marry you . "I smiled as we fucked again until we fell asleep.
In the morning, I had breakfast brought up and we ate in bed, naked. We really had a nice time. Before we knew it, it was time to checkout and head to the airport.
We arrived a little before noon and Diane was already there. She looked even cuter than she did last night. She had on tight jeans, t-shirt and it looked like no bra. She had an overnight bag with her.
We walked over to the plane. I checked it over as the women boarded her. The jet was fueld and ad soon as I put food and wine on board, we were ready to go.
Diane and Kate buckled in and I was waiting for clearance from the tower to take off. After a few minutes,we were next in line to go. Finally, I was on the runway and taking off. I climbed to 10,000, my cruising altitude. After about a half hour I put the plane on autopilot and headed to the cabin.
I sat down with Kate and Diane who couldn't thank us enough for taking her with us. She told us that she was going to visit her parents for a couple of weeks. She told us that she was 21 with no boyfriend and was lonely and just wanted to go home for a visit.
As we talked, I figured she had to be about 5'6" and about 110. She had short blonde hair and blue eyes and a perky pair of tits.
About two hours into the flight, Diane said, "Look, you guys said you wanted to join the club. Why don't you get started and I'll go move up to the front of the cabin so you can have your privacy."
I replied, "Thank you, that's very considerate of you."
Then Kate said, "Don't be silly. I'm sure you have seen couples fucking. Just sit back and relax."
I looked at Kate and gave her a state.
"Oh, relax Dan. So she watches us. It's no big deal. In fact, I don't mind an audience."
Then we all laughed and I said, "Well ladies, if it doesn't bother you, it sure won't bother me."
Then I got cute and said, "Diane, I'm sure my new fiance wouldn't even mind if you joined us, then you could be in the club too." Then I laughed.
Kate looked at me and just smiled. "It's ok with me if it's ok with Diane."
I looked over at Kate..."Surprise!" She said.
It didn't register with me right away then I realized my fiance was bi, something I never imagined.
At the restaurant, when I went to use the powder room, I bumped into Diane and I simply asked her if she was bi, because I thought she was, and she said she was. I asked her if she would be interested in joining us and she said yes..."
Diane said, "Thank you both. A trip to NY and joining the club. This is amazing."
Kate smiled and said, "Whose ready to join the club?"
I looked at her then Diane and replied. "I have to go to the cockpit to check on our course. I'll be right back. You two can start without me, if you like."
I went into the cockpit and took control of the plane and checked my heading. I called the nearest tower to find out about the weather and got a good report. We had two more hours to go before we touched down. I put the autopilot back on and joined Kate & Diane in the cabin.
When I went to the back of the cabin, both women were naked and playing with each other. Diane was hotter naked and I envied Kate. I watched them as I undressed. My hard cock popped out and I got on the bed with them.
"You ladies ready to join the club? Which one would like to be first?"
Diane said, "Kate, you should go first, after all you're his fiance."
Kate kissed her, then turned to me and kissed me then whispered, "You have a lot to learn about your future wife. I hope you like what you learn."
As Diane moved away, Kate and I started hugging and kissing as I forgot we had an audience. We got into 69 and really went at it, maybe it was because Diane was watching. But, in any case, we were really going at it. After only a few minutes I told Kate I was going to cum...she said, "Me too."
We continued our assault and as I came in her mouth, she had one orgasm after another.
As we rested, Diane said, "You guys have to fuck to get in the club," As she laughed.
Diane then got in the middle of us and I enjoyed playing with Diane's tits. My hand roamed down to her smooth pussy and my cock got hard again. Kate saw it and said, "Go ahead and let her join the club. I'll join after Diane."
As soon as she said that, I mounted Diane and slipped my cock in her wet pussy. My cock felt so good in her. I wasted no time in fucking her as Kate played with Diane's tits & sucking her nipples. It didn't take me long to cum in her cunt.
Kate yelled out, "You guys are in the club...yeah..."
My limp cock slipped out and I was completely spent. Diane kissed us both and thanked us for everything.
Then she got up and went up front and cuddled in a blanket and went to sleep.
Kate and I cuddled and I said, "So, what else about my fiance that I do not know?"
"You'll find out soon enough...I hope you will be open minded and enjoy what you find out."
"Mmmm, my mystery woman has me curious. I can't wait to find out your secrets."
About an hour later, my cock was ready, again. This time we wasted no time. This time I mounted my love and slipped my cock in..."Welcome to the club." She smiled and I fucked her until I came in her.
By this time I had to get back in control of the plane. I got dressed and headed to the cockpit. We were about a half hour from landing. I told Kate to get Diane up and dressed.
Finally, I touched the plane down and we were back home. After we got off the plane, Late exchanged telephone numbers with Diane and we took her to her parents house & dropped her off.
"Let us know when you are going back. Maybe we'll fly you home." Kate told her.
"Thanks, I would definitely make it interesting for you too."
We both said " Goodbye" at the same time and we drove off.