It was about 4:00 pm on Friday afternoon. Shirley decided it was time to

start getting ready. She went to the bedroom, stripped off all her clothes

and took a shower. She finished, dried off, and laid down on the bed for a

few minutes. She was lying on her back and thinking about tonight with

Dan. She wants to masturbate but decided to save all her sexual energy

for Dan. She was thinking of what to wear. She decided on something

entirely different than what she usually wears. If he wants panties, then he

will get panties.

She got up and went to her dresser. She opened the drawer with her

underwear. She took out her white garter belt and put it on. Then she got

her white stockings, sat down on a chair and put them on and hooked

them to the garter belt. She stood up and looked at herself in the full

length mirror. She thought she looks pretty sexy for a middle age woman.

She then went to the drawer and got out her matching white panties and

put them on. She liked it better without panties, but Dan asked for

panties. She also got out her matching white, half bra and put it on. She

had bought it at the state capital after seeing Anna wear one. It supported

her breasts but leaves her nipples exposed. Then she put on a matching

light blue top and skirt. She finished the outfit with light blue loafers.

Again she looked in the mirror and she felt she looked hot. She hopes that

Dan will agree.

She went to the living room and sat down on the couch. She started

thinking about Monday morning’s session with Alice and Richard. She

wanted it to be a normal session but with Alice being her best friend it

would not be normal. But she would try to make it normal. While she was

thinking about this the doorbell rang. She opened the door and it was

Dan. He pushed his way inside, kissed her, and his hands went to her

breasts. When he stopped kissing her, he said this is different tonight.

You look beautiful. Are you ready to go, he asked? Yes said Shirley so

she handed her bag to Dan and they went out and got in his car. He drove

to his house, got her bag, and they went inside. Dan’s housekeeper was

there and she handed each one a glass of wine. Dan said follow me and

led Shirley out on the deck where a table was set for dinner. He seated

Shirley and himself and the housekeeper brought the dinner. As soon as it

was on the table he excused the housekeeper and followed her to the

door. He came back and asked Shirley to stand up. When she did he

started undressing her. His deck was secluded and no one had a view of

it. He had everything off but her garter belt and stockings when he stood

back and took a good look at her. He said you are beautiful and I like you

like this. Let’s eat with you only wearing your garter belt and stockings.

So they sat down and ate dinner. They both had a couple of glasses of

wine along with the dinner. It was baked chicken and was delicious. Dan

got up and helped Shirley get up. Dan’s deck was large with both a

covered and uncovered area. As Shirley looked around she said his hot

tub which they had been in before. She also noticed a large air bed on the

deck with sheets on it. As she was looking around Dan said it’s time for

these to come off and finished undressing Shirley. She said I want you

nude and started undressing Dan. Soon he was nude also and their

clothes were all over the deck. Dan said Shirley do you want to have sex

in the hot tub or on the air mattress. Shirley said well the hot tube is

attractive but I did that one time and the water destroyed my natural

lubrication so it wasn’t that great. Dan said lubrication is no problem. I

have a special tube of lube that is made for having sex in a hot tub. It will

not lose its lubrication properties because of the water. Shirley said then

get the lube and we will get in the hot tub. Dan had the tube of tube on a

small table along with three lube shooters full of the lube. He put some

lube on Shirley’s vulva, took the three lube shooters and emptied them in

her vagina, and put a good amount of the lube on his erect penis. He then

got in the hot tub and sat on a seat at the edge. Shirley followed him, and

got on her knees facing him and lowered her vagina on his penis. When

he was fully in her she kissed him.

Dan’s hand immediately went to her clitoris and started rubbing it. His

other hand was holding her right breast and caressing her nipple. It didn’t

take long for Shirley to orgasm and Dan stopped and just held her. After a

couple of minutes Dan started again and soon Shirley had another

orgasm. Dan could feel her vagina spasming on his penis. Once again he

stopped and just held Shirley. Soon Shirley started riding Dan’s penis.

She was raising and lowering her body on his penis and soon she had a

third orgasm. Dan could feel her vagina spasming on his penis. Shirley

just kept going and soon Dan was shooting his semen up in her vagina.

They were kissing passionately as Dan held her breasts. Soon Shirley

stopped moving they just held each other until Dan’s penis slipped out of

Shirley. Shirley and Dan stood up and reached for towels on the table next

to the hot tub. Soon they had dried each other and Dan led Shirley to the

air mattress. They laid down on the air mattress, covered themselves with

the sheet, and held each other tight. Soon they were asleep.

When they woke up it was morning. They got up, went to the kitchen, and

Dan made breakfast. When they finished breakfast Dan said let’s get

dressed and head out. He said I would like you to wear one of your sun

dresses without panties. Shirley said but you told me to bring panties.

Yes said Dan, but you won’t need them today. So Shirley put on a sun

dress, fixed her hair, put on some makeup and said she was ready. She

told Dan she was going to pick up her clothes from last night. Dan said no

need, my housekeeper will pick them up, wash, dry, iron and fold them. I

can’t let her find my clothes scattered all over the house. She knows we

have sex said Dan. Well I guess but I still have to pick them up. So Shirley

gathered her clothes and repacked her bag. They went out and got in

Dan’s car and he started driving. Where are we going, ask Shirley. It’s a

surprise said Dan. How long will it take. About 4 hours said Dan.

Shirley knew Dan was driving north and after about two hours they

stopped at a rest stop. Dan was kissing and caressing her before she got

out of the car and when she got back in. He finally started driving again

and after about 1 1/2 hours he stopped at a place for lunch. They went in

the restaurant and he suggested a light lunch. They both had a bowl of

soup and a few crackers. When they finished they got back in the car and

Dan drove another 30 minutes and then parked at a small airport. He was

in front of a building that said Mile High Air. Shirley wondered about the

name but didn’t really think much about it. They went inside and there

was a man there about 30 years old. Dan announced his mane and said

he had a 1:00 p.m. appointment. They man said yes, I am at the pilot and

everything is ready. The restrooms are down the hall. Both Shirley and

Dan used the restrooms and then the man led them out to a small, twin

engine airplane. It said Mile High Air on the outside. He opened the back

door for them to get in and Shirley noticed the back only had a large

mattress on the floor. There were no seats but only the mattress. The

man told them that he would be in the front flying the airplane and that

there is a solid wall between the front and back so he could not see

anything in the back. He said the only thing he would do regarding them

was when they were 1 mile high he would announce it on the pa system.

Shirley finally figured out the name and she said Dan, are we going to join

the mile high club. Dan said yes. The pilot also reminded Dan that he had

reserved two hours for the flight. Shirley and Dan climbed in the back and

the pilot closed the door. Soon they heard him in the frond of the airplane

and they heard the engines start. Soon they felt the airplane moving. At

this point Dan didn’t waste any more time. He kissed Shirley and took the

straps off her shoulders. Since they were laying down, she had to raise up

for him to get the dress off her. She then started undressing him and soon

they were laying next to each other nude and they could feel the airplane

was in the air. Dan was kissing her and caressing her breasts. Dan loved

her breasts and was always holding and caressing them. She loved it

when he rubs her nipples and sucks on them. Dan was going slow in the

foreplay she presumed because he wanted to wait an put his penis in her

when they were a mile high. But soon he was rubbing her clitoris and she

was orgasming. She lost track but she thought she had four orgasms

before the pilot came over the speaker and said we are one mile high. At

that point Dan rolled her on her back, spread her legs, got on top, and

inserted his penis in her vagina. He pushed it all the way in and stopped.

He stopped to kiss her and said that he loved being inside her. She said

she loved him being inside her as he start moving. So he started thrusting

his penis in and out of her vagina and soon she had another orgasm. He

rested a minute or so and pulled out of her. He asked her to get on her

hands and knees and soon he pushed him penis in from behind. She liked

this position because his penis would go further inside her than in

missionary. After only a few strokes she had another orgasm. Dan once

again rested and then asked her to lay on her side. He got behind her and

soon his penis was back in her vagina and he was thrusting it in and out of

her. Again in just a few strokes she orgasmed and Dan did too. She felt

his warm semen shooting up inside her. Dan stopped and just rested with

his penis all the way inside her. She liked feeling his body so tightly

against hers. She liked feeling the warmth of their bodies together. After a

few minutes he lost his erection and her vagina pushed his penis out but

they just laid next to each other talking softly. In a few minutes they fell

asleep. They were wakened by the feeling of the wheels of the airplane

hitting the ground. She quickly got dressed and were ready when the pilot

opened the door. Did you enjoy the flight he asked? They both said yes at

the same time. They got out, thanked the pilot, and headed for the car.

When they got in the car Shirley asked Dan how he got the idea for this

flight. He said he saw an add for it somewhere and decided to surprise

her with it. Did you like it he asked? Yes said Shirley you know I love

being nude and having sex with you. But I don’t think I will be bragging to

my friends about joining the mile high club. Well I won’t either said Dan.

Let’s head for the motel and get ready for dinner. It’s only a few minutes

drive.

Soon they pulled into a motel parking lot and Dan got out and checked in

and got the key. He carried their bags and led Shirley to the room. Once

inside he closed and locked the door and quickiy had Shirley’s dress off. It

took her longer but she got all his clothes off. They laid down on the bed

and snuggled. It was so nice to lay next him and hold him so tight. They

just held each other and talked for an hour or so when Dan said I am going

to shower before dinner do you want to join me. Of course said Shirley.

They went into the bathroom and took a long shower together, caressing

each other all over as they did. When they were finally finished they dried

each other off and Shirley ask Dan what he wanted her to wear. He said a

sun dress with no panties. Shirley put the sun dress back on and Dan got

dressed in a golf shirt and slacks.

Dan had picked out a steakhouse for dinner. She had a nice dinner with

wine and then back to the motel and went to bed. They always slept

nude. Shirley woke up in the morning when she felt her nipple being

sucked. As she opened her eyes she saw Dans head above her right

breast. When he realized she was awake he moved and started sucking

her left nipple. After a few seconds he moved up and started kissing her

and soon his tongue was inside her mouth. The kissing progressed and

soon his finger was on her clitoris and she was orgasming. After two

orgasms Dan laid on his back and motioned for Shirley to get on top of

him. She did and started riding his penis and soon they both orgasmed

together. Shirley waited a few minutes and then got off Dan and laid next

to him, holding him tight. Soon she said lets shower and go get some

breakfast. After the shower Dan said this morning you will want to wear

either slacks or shorts and panties. Why, asked Shirley. You will have to

wait to learn why said Dan. Shirley got dressed in slacks and a sweater

and they checked out of the motel and headed to breakfast. After

breakfast Dan drove back to the airport, but on the other side from

yesterday. It was a bigger building and the sign said Skydiving on it.

When Dan stopped the car Shirley said we are not going skydiving are we.

Yes said Dan. I have never done it before said Shirley. I know said Dan, it

is a tandem jump. You will have an instructor strapped to you. The

airplane will take us up to 12,500 feet, we will jump out, and at 3,000 feet

the rip chord will be pulled and we will glide down under the parachute.

And I have two other skydivers who will video tape the entire dive. OK

said Shirley, I’m in. They got out of the car and went inside. They were

greeted by two men who said they were sky diving instructors. They were

led to a hangar and given about an hours instruction in what to do, etc.

Then they were put in jumpsuits, the equipment was strapped on them,

and they went out and climbed in the airplane. It didn’t have a door on it

and there were only the six people, Shirley, Dan the two instructors, and

two guys to video the dive. Soon the airplane was climbing and the pilot

announced they were at 12,500 feet. Each instructor completed the

strapping to the other one and the other instructor checked everything to

make sure they were ready. The pilot slowed the airplane and the

instructor pushed Shirley and him out of the airplane. When she got her

composure she looked and sad Dan and his instructor falling next to them.

There were two other men on each side with cameras. It seemed only a

short time and the instructor told Shirley to pull the rip chord. She did and

the parachute went flying up above them and then she felt it tug on her

body as it slowed them down. Now they were going slow and she could

watch everything around her. It was wonderful, seeing Dan and his

instructor gliding down next to her and her instructor. Soon there was

more room between them and the instructor told her to pull her feet up. In

only a few more seconds the instructors feet were on the ground and he

told her to stand up. He unfastened the straps and Dan was next to her.

She and Dan were hugging and kissing and she told Dan how great the

sky diving was. A large golf card came and they got in and it took them

back to the hangar. They took off their jumpsuits and got the videos which

were on a thumb drive. They thanked the instructors and left. When they

got in the car they kissed some more when Dan finally started the car and

they headed home. It was another 4 hour drive home. Shirley enjoyed the

conversation as they drove home.

When they got to her house she invited Dan in and as he closed the door

she took off her clothes. When he turned round to see her she was

already nude. He grabbed Dan and undressed him and led him to her

bedroom. He kissed her and said Shirley I am an old man and I don’t think

I can get another erection but I want to give you oral sex. She laid down

on her bed on her back and spread her legs wide. He got between them

and soon his tongue was on her clitoris making circular movements. It

didn’t take her long to orgasm. He let her rest and continued until her

second orgasm. He let her rest again and put his finger in her vagina and

found her G spot. He was rubbing her G spot when she had her third

orgasm. After she recovered she told him she couldn’t do any more and

they just cuddled. She told Dan she had a wonderful weekend and offered

to fix him some dinner. He said OK but only if you will stay nude. Shirley

said exactly my thoughts and got up and headed to the kitchen. She fixed

them sandwiches and they ate while still nude. After they were done Dan

said he had to go. He said he had an early appointment at the hospital

and needed his rest. He got dressed and Shirley followed him to the door.

She kissed and hugged him and he opened the door and left. She closed

the door, picked up her clothes, and went into her bedroom. She put the

clothes up and laid on the bed. She was thinking about the wonderful sex,

all the orgasms she had (she had so many that she lost count), and how

fun the sky diving and mile high club were. She then started thinking

about her session with Alice and Richard in the morning when she fell asleep.