My wife insisted that I fuck my 40 year old virgin sister. Part 1

My parents had been married for 40 years and they wanted to do something special for their anniversary and so they invited the whole family to a Hawaiian vacation with a luau dinner on the date of their actual wedding anniversary.

I’m 30 years old and my wife is 35. We have a couple of kids but they didn’t come on the trip and stayed with my wive’s parents. We were going to treat this trip as a much needed vacation.

Everything went smoothly. The flight was uneventful, we got the rental car, we checked in. The room was magnificent. It had huge windows that faced the ocean and so we did what came naturally- we fucked each other senseless. I leaned my wife against the windows facing the ocean, lifted up her dress, inserted my dick into her, and rammed her until I exploded my seed deep in her womb. Well, not really - you see, I had a vasectomy after our last kid and so I was shooting blanks.

That first night we met up with the rest of my family and had a great dinner. The luau was three days away and according to my father the most important thing was that we get matching outfits. The hotel had a shop that custom made shirts and dresses and we were ordered to go to the shop 1st thing in the morning to get fitted. My wife was all kissy kissy and she even managed to grab my dick through my pants under the table. Everyone seemed to be having a good time except my sister, Wendy. She looked miserable. After a while my wife, Truly, took an interest in my sister.

What’s wrong? She asked Wendy. I can’t stand it said Wendy, everyone is so happy and in love and I don’t have anyone! No worries said Truly, I’m sure you’ll find someone soon. Are you looking and making yourself available? Heck, I’m sure we can go to the hotel bar and find you someone tonight. No, replied Wendy, I don’t want a one night stand. I am of the church and I don’t want to partake in today’s hook up culture. I need a man of god. I promised my parents that I would honor the teachings of the church and I must keep my vows. Wait, said Truly, are you telling me that you are a virgin?
Wendy began to cry, and said Yes, I’m a forty year old virgin and I fear that I may not be able to have kids if I don’t find a man soon.

Oh honey, said Truly. Come here and she hugged Wendy. They began to take shots and both got drunk as skunks, lol. Dinner ended and the girls decided to take the party up to our room. We said good night to my parents and headed to our room. I don’t drink so I was the level headed one in the group. We got to our room and after a bit Wendy and my wife had passed out on the bed. I placed Wendy on one side of the bed but in doing so her dress had risen up her body and exposed her panties. She wore granny panties lol. I don’t know why but I leaned down and sniffed her panties. Wendy smelled like piss and musk. She smelled delicious. I rubbed her crotch and worked my way up to her tits. They were massive. I was rock hard now that I had molested my older sister.

I laid my wife next to Wendy and pulled off her red thong panties. I dove mouth first onto her pussy and licked her lips and clit. I felt my wife convulse a few times and so I pulled down my pants and entered her wet hole. Her pussy immediately took a hold of my dick. I thrusted and pushed and pulled inside of her. It seemed like the more I pulled out the more her pussy pulled me back in. I was a man on fire. A man on a mission. I wanted to fuck her raw but the more I fucked the more wet my wife got. I grabbed at her tits and then I remembered - Wendy was laying next to us. So I grabbed at her huge tits. The sensation was so great that I exploded into my sleeping wife. I stood up and place blankets on my wife. As I did it I caught sight of her pussy and dipped a finger into her hot and wet hole. Her juices were super sticky. I don’t know why but I walked over to my sister, opened her mouth, and rubbed my wives pussy juices on her tongue. I took off my clothes except for my boxers and jumped into bed next to my wife.

The next morning I woke up to commotion. Both my wife and my sister were bouncing around like rubber balls around the room. Groggy I asked, what the actual fuck?! My wife yelled, we are late! I asked, late for what?? She said, the fittting! We need to go down to the tailor shop get up and let’s go! I got up and walked toward the bathroom at the end of the room. That’s when Wendy bumped into me, looked down, and said, will you please put that thing way! I looked down and saw that my dick was sticking out of boxers. I didn’t move and Wendy didn’t move until my wife said, Wendy and I are going to the shop. Take a shower and meet us there ASAP!

I side stepped my sister and headed to the shower. Ok, I said, see you in a bit. I took a quick shower concentrating on the important parts and headed to the shop. Everyone was in there laughing and having a good time. The shop keep came up to me with a pineapple juice. She said, everyone is having mimosas but we understand you don’t drink alcohol. That’s right, I said, thank you. I walked in and my dad said, son go behind the curtain and they will take your measurements. I went behind the curtain and found my sister in her bra and panties. Really?! She yelled. I laughed and told her dad had instructed me to go behind the curtain. I looked at her and said, well, you saw my dick this morning why don’t you show me your girls?! You have always been a pervert she said and then yelled, Get Out!

That day we went to many small towns, ate shaved ice, and went visit a black sand beach. We were all happy except my sister. That evening we congregated in my parents suite. Dad, mom, and I sat around the common area and my wife and sister in her room.

Are you telling me that you’ve never kissed a man? Asked my wife to Wendy. I have, said Wendy, I done everything except had sex. Were you comfortable sucking dick, asked my wife. I haven’t sucked sick, said Wendy, I’ve touched a dick. Ok so you have a hand job, did you swallow the sperm? No! Said Wendy. Truth be told, I’m scared, said Wendy. Holy shit, exclaimed Truly. Don’t be blasphemous said Wendy. Ok, said Truly, what you need is shock therapy. You need to handle a dick and you need it now?

Truly, told Wendy to meet us in our room and dismissed her. And then went to sit with me and my parents. She pulled me aside and asked, do you want to get your dick sucked? If so then we need to leave now! I yelled bye to my parents and followed my wife out the door. I swear I heard my dad say, good they’re finally gone come suck my dick. lol

We go to our room and I was hard and ready to fuck my wife. She stopped and started to kiss me and said no matter what happens done freak out! We kissed and she opened the door and the sight of my sister deflated by dick. Um ok Wendy time to go back to your room, I said, the adults have stuff to do. Thank you very much. No, said my wife, Wendy stay right there. Tom, your sister has a problem, she is scared of dicks. She’s never given a hand job, she’s never sucked a dick and she is a 40 year old virgin. We need to help her.

I haven’t sucked sick tried to help her I said, I’ve set her up with guys, my friends, my coworkers. Hell, I even tried to set her up with my doctor. He’s too tall, he talks too much, he has kids, he doesn’t go to church. She finds a reason to not connect to them and so they leave. Actually, it all her church shit that gets in the way. “Wait till marriage, have a chaperone, dress modestly “ I mean really, I think she could go down stairs and find a fuck buddy at the bar but no, God keeps her from allowing a guy to get close to her. She is a 40 year old virgin for a reason. Unless she changes then she is going to be a 50 year old virgin! Don’t be mean said Truly. She needs our help and we are going to help her. Now pull down your pants and lay down on the bed.

Are you joking I asked, with a boner forming in my pants. No, said truly as she undid my pants and then pushed me on the bed. Your sister is terrified of dick. It is your obligation to help her. We are going to help her. With that, my wife started to suck my dick in front of my sister. She stopped and started to stroke me and said, Wendy look at what I’m doing. You need to keep the shaft well lubricated and with your mouth pay special attention to the mushroom head. Swirl your tongue in the head and every once in a while relocate the shaft with your saliva. You can spit on it. Spit on your hands, or take the whole thing down your throat. Truly was sucking and jerking me off while she gave instruction.

When you rub down then rub back up and lightly squeeze the mushroom head when you rub up. If you swirl your tongue on the head then suck on it and swirl your tongue on the underside and then on the top. A man’s dick is the easiest thing to use. It literally a stick of nerves. Have you ever masterbated, truly asked Wendy. Yes, said Wendy, then think of it as a huge clit. You stimulate it by rubbing and applying pressure. This is your brother but his dick is no different from any other dick. Well, he is a bit on the big side but over all they are all the same, shaft and head. I’m gonna make him cum and you are going to eat his cum. Fuck! I thought as I exploded into my wife’s hand.

Come here Wendy said Truly. Come kneel next to me. Wendy did as she was told. Now, lightly lick the cum I have in my mouth. Do it lightly and softly. I don’t want to over power you with this taste. It’s gonna be like nothing you’ve ever had and you will learn to love it. Wendy came over and licked my cum like a cat licking a bowl of milk. Then the licks got bigger and longer. Then my wife told Wendy to suck the cum off my dick. Wendy placed my dick in her mouth as I saw Truly lick the remainder of my cum off her hand.

Is he clean asked Truly. I think so said Wendy. Good said Truly, now make him cum for you. Wendy grabbed my dick and started to beat me off. I was already hard but the touch of my sister in my dick got me rock hard. She did exactly as my wife had previously instructed and after a few minute I yelled out, I’m gonna cum!
Put your mouth near his head, instructed my wife to my sister. Keep rubbing, and wait for his cum. My sister did as she was told and then she licked the head. That’s when I exploded, most of my cum went into her mouth, some on her cheeks. I was exhausted but my dick was still hard as a rock. My wife had taken off her clothes and mounted me. She asked Wendy, are you wet? Yes, said Wendy, I feel like I’ve peed through my pants. My wife said, that’s how you know your body is ready to get fucked.

I think you are gonna have to fuck your 40 year old virgin sister, said my wife to me.

Part 2 coming soon.