Wild Oats - The Cruise

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Sally introduces a virgin 18 year old to sex.
3.2k words
4.04
47.6k
11

Part 20 of the 27 part series

Updated 09/10/2020
Created 10/11/2014
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"Jason, a 'Fun Ship' is trying to fill the last few cabins and we can get a four day cruise for $50 bucks each. Are you in?"

"I'm in!"

A week later when we boarded, we found that we had booked a tiny cabin deep down in the ship. It had four single bunks that folded into the wall and a tiny bathroom. It was clean and we did not plan on spending much time in the cabin so that was not a problem.

We told the steward we would just use the top and bottom bunk on one side of the cabin so we would have more space.

We had a mandatory lifeboat drill and explored the ship until it was time for dinner. We were in the first seating which would give us plenty of time to enjoy the evening activities.

Our assigned dinner table was a table for eight. Our group consisted of Jason and me, a couple in their 40's with an eighteen year old son, and a young couple with a ten year old daughter.

Jim, the eighteen year old, gravitated to us and, with his parents' permission, hooked up with us for the evening.

It seems that 'Jimmy's' parents are very protective and have been very controlling. Jim is an eighteen year old virgin who will be a freshman in the fall at the same university where I will be a senior.

I was the only one of us who was old enough to purchase alcohol, so the boys ordered cokes and shared my drink when they thought no one was looking. We bonded during the evening, danced a bit and agreed to meet the next day to go ashore on the private island beach where the ship was stopping.

Jim's parents decided to stay on board.

We met at 10 in the lounge to be called to go ashore. I wore my bikini under a loose top that came to mid-thigh and sandals. Jason and Jim both wore swim trunks and t-shirts with flip-flops.

On shore we ate, drank and played. Jim seemed to enjoy watching my DD's bounce as we played volleyball.

We each got a plate of food and looked around for a quiet place to eat and enjoy the sun. We walked down the beach and around a bend. We noticed widely scattered couples and singles sunbathing and swimming in the crystal clear water. Many of the women were topless. The boys suggested that this would be a good place for us to enjoy our picnic.

We spread our three towels together to give us a nice space and we settled in. After eating, the boys went down to the water's edge and I decided to work on my tan. I took off my top and was enjoying the sun on my front with my eyes closed. Suddenly the boys were back and Jim was getting his first good look at a woman's breasts.

He seemed to appreciate the view because I noticed the tent that rose in his trunks,

I appreciated his admiration and tried to act as natural as possible. I did nothing to cover up. In fact, I sat up to talk with the boys and they told me about their trip to the water's edge. They had waded, but not gone swimming.

I suggested that we all go for a swim. I left my top with the towels and began walking to the water. As the guys ran past me, I joined them in racing into the water.

I arrived in the water third and when we reached waist deep water, I started a splash fight with them. Jim went under water behind my legs and Jason pushed me over him. The side strings on my bikini came untied and my bottom floated away. I could see it in the clear water and grabbed it before it was totally lost.

Seeing me naked stimulated Jim's cock and he was now standing in front of naked old me with a stiffy in his swim trunks. Actually it was not all in his trunks, it actually extended several inches out the leg opening. He was embarrassed and quickly turned his back on me.

"Jim, don't worry, it's a natural reaction. From what I saw, you will have no problem pleasing any woman. In fact, if you want to lose the 'virgin' title attached to your name, I think I can help you."

"You mean you would let me do you?"

"I mean we could make love. No one is going to do anyone."

"What about Jason?"

"Jason is my friend, not my steady boyfriend. He can be there if you want him to be or he can take a walk."

"I would rather make love to you just you and me."

"Why don't you come down to our cabin after dinner tonight? You will have to act normal at dinner. And remember, this is something private between the two of us."

"We should probably head back to the ship so we can clean up before dinner."

I walked out of the water and up to our towels naked, carrying my bikini bottom. When we reached the towels, I casually dried myself and put on my bikini.

The three of us walked back to the ship boarding area hand in hand with me in the middle.

In our cabin I showered, shaved, and groomed my pubes. I dressed for dinner. Jason and I made our way up to the dining room.

After dinner, Jason and I returned to our cabin. Jim told his parents he was going exploring and also made his way down to our cabin.

When Jim arrived, Jason gave him a smile and a gentle punch on his shoulder and left us.

I kissed Jim gently on the lips and we sat on Jason's bottom single bunk and talked. Jim was sitting there talking with his hands on his knees and a bulge in his pants.

I put my hand on his bulge and ask him if he would like to touch me.

Jim didn't say anything, but tentatively put a gentle hand on one of my breasts.

"You've already seen me naked, why don't you help me out of these clothes?"

Jim fumbled around some, and I think my bra was the first he had ever unfastened, but eventually I was naked.

"Now may I undress you?"

I gave his cock some attention as I undressed him and then, "Jim, I am going to lie down on the bed. I want you to do anything you want with me. You can kiss me, touch me, and make love with me. Anything goes and don't hesitate to ask questions."

Jim knelt on the floor beside the bed, began looking at me and running his fingers all over my body from my shoulders to my toes and back up again.

As he ran his hands over my body, he saw my nipples become erect and stand out like small corks on my breasts and he saw my areolas become all tight and crinkly. He concentrated on my breasts and began licking and suckling.

I could not help myself. I reached down and caressed his cock as he loved my breasts. His hands and fingers moved down and when he got to my pussy he said, as he stroked my clit, "What is this little penis-like knob down here?"

"That is my clitoris and touching, stroking, kissing, or sucking it is a good way to turn a woman on."

Jim tentatively licked my clit and then sucked it into his mouth. As he tongued and sucked my clit his fingers kept exploring my womanhood.

"You have two openings down here. One is your ass hole, what is the other one?"

"That is my vagina – that is where your cock goes when we make love. Some girls will want you to put it in their ass so they won't get pregnant, but tonight I want you to make love with me in my vagina."

"Can we do it now?"

"We can, but when you make love to any woman, take your time and be sure she is ready before putting your cock in her vagina. If you take your time and build up to the main event, she will usually let you know when she is ready."

"Do I just put it in you?"

"Rub your cock through my slit several times to get it nice and slick with my love juice. Then place the head of your penis at the opening of my vagina. You will be able to slide into me easier than with a woman who has had less sex than I have."

I was wet and Jim slid in all the way on his first push.

He moved in and out once or twice and then began pumping in and out as fast as he could.

"Jim, slow down. Slide your penis in and out of me slowly at first and I will begin moving with you. You want to make it as enjoyable as you can for your partner. In the end it is most enjoyable for both of you if you can both have a climax."

"How will I know if I have a climax?"

"Your cock will begin spurting semen."

"Do I spurt into you?"

"You do with me, but when you are with another partner, be sure you know where she wants you to spurt. In fact it would be a good idea for you to use a condom. Especially if it is someone you do not know well or if she is not on birth control."

Jim started fucking me with a smooth, steady rhythm and I met him thrust for thrust.

"Jim, this feels good."

"It feels good to me too, but I am starting to feel something happening down there."

"That means you are getting closer to your climax. Fuck me harder and faster and let's see what happens."

"Oh Sally, I think it is coming."

"Let it come. Fill me up."

He did

"Sally, can we do it again?"

"Jim, I will do it with you as many times as you want tonight. Just remember that I want you to make love with me at least once each day for the rest of the cruise."

"Sally, thank you for being my love teacher."

The morning of our last full day and night of the cruise.

Sally was up first and knelt by Jason's bunk and began playing with his penis as he slept. When he was hard, she began sucking and tonguing his cock until he came in her mouth. By now he was fully awake and said, "Wow Sally, what a way to start the day."

"Jason, if I help you get hard again, will you fuck me and fill me with your cum?"

"Sally, it will be my pleasure, but why today?"

"I want Jim to experience sloppy seconds this morning and I need to be filled before that can happen."

"May I kiss you and touch you before we make love?"

"Of course. Then I want you to go find Jim and send him down. He has our extra key so tell him to just let himself in when he gets here."

Jason had no trouble getting hard again or in filling me with his cum and then he went looking for Jim. A few minutes later, Jim opened the door and came in.

"Sally, you wanted me?"

"Yes, I want you to make love to me right now. I know we talked about foreplay, but just do as much as you need to get hard because I am already ready for you now."

Jim stripped off his clothes and by the time his pants came off his penis was standing at attention.

"It looks like you don't need any foreplay either, so take me now.

Jim positioned himself between my legs and immediately slid in to the hilt.

"Sally, you are so warm and slippery. He started pumping slowly. "OH SALLY, you feel so good. I can't hold back. I'm going to cum. OHHH....

Jim emptied his balls in me.

"Sally, I'm sorry. I came and didn't bring you along."

"Jim, this was an experience I wanted you to have. Jason made love to me just before he went to find you and his cum was already inside me. That's why my vagina felt so warm and slippery."

"Can we do it again? I will go slower this time."

"No, I want to get cleaned up and take a nap. Why don't you come back after lunch and we will make love all afternoon,"

"Do you just want me to let myself in?"

"Yes, I will be all ready for you."

. . . after lunch

Jim came in and sat beside me on the bunk. "Sally, my dad is in the hall and would like to talk to you."

I sat up, exposing my naked breasts. "Jim, this is our time. I am naked in bed for you,"

"This is not bad. My dad is a really cool guy. You can cover yourself. He knows our plans for the afternoon and just wants to talk for a minute."

I wrapped myself in the top sheet and said, "Okay, we can talk."

Jim opened the door and invited his dad in.

"Sally, excuse me for intruding. Jimmy has told me how you have helped him become a man."

"Mr. . ."

"No, call me Jim. In family circles I am known as Big Jim and Jimmy is known as Little Jim."

"Okay. Big Jim."

"I think it is important that you know why Jimmy was so sexually ignorant as an 18 year old. – After Jimmy was born, his mother, my wife, decided she had done her duty and said no more sex. She considers hugging, touching, kissing, etc. all sex. So there has been none of that as well as no sex talk of any kind."

"You mean you have been celibate for the past 18 years?"

"Yes, anything sexual has been forbidden in our home."

"Jimmy, will you step outside for a few minutes and let me talk with your dad?"

"Sure."

I stood up and dropped my sheet as I said, "Jim, as a woman I would like to give you a hug."

I gave him a full-body, naked hug. He hugged me back and as he began to feel more comfortable, his hands began to move over my back, caressing me. I pulled back, kissed him on the cheek and settled back into his arms.

His hands dropped down to my ass and he cupped my cheeks with his hands and pulled me close. Is he cupped my ass and pulled me close, I could feel something hard pushing between us.

I leaned back again, kissed him gently on the lips and said, "Jim, your manhood is definitely still working."

I moved one of his hands to a breast and kissed him again.

His hand explored my breasts, his fingers began tweaking and circling my nipples which by now were sticking out like small corks.

I ran my hand up and down his cock from outside his pants. I kissed him again and said, "Jim, will you make love to me?"

His head dropped to my breast and he began to suckle. He loved my breast with his mouth and tongue. While he was doing that, I unfastened his pants and pulled them down along with his underwear. He toed off his shoes, stepped out of his pants, and pulled his shirt over his head.

He laid me back on the bunk and knelt between my legs. He began making love to me orally. He was so gentle and so thorough. I know my juices were flowing because I heard him slurp the excess fluids as he explored my vagina and clit.

"Jim, I'm ready for you."

He lined his cock up with my vagina and came as soon as his penis head entered me.

"Jim, it's okay. When you are ready we will do it again."

He kissed me, really kissed me. I moved over on the bunk and ask him to join me. Naked, we cuddled and caressed each other on the bunk.

Little Jim chose this time to let himself back into the room. "May I join you?"

"Only if you and your dad are willing to share me."

"Dad?"

"I can't think of anyone I would rather share with."

Little Jim dropped his clothes.

We rearranged ourselves. I took Big Jim's cock in my mouth to help him get back up. Little Jim lined his cock up with my love hole and just before he slid in, I said, "Jim, you can love me, but please don't cum in me until after your dad has cum in me. Your sexual satisfaction is important, but right now your dad's sexual satisfaction is even more important."

Little Jim entered me and gently fucked me, but not to climax. As Little Jim fucked me, I was able to bring Big Jim back to a full erection.

"Okay guys, time to switch."

Big Jim was big! He was long and thick.

"I can see why everyone calls you Big Jim."

He entered me. It felt so good. He knew how to use that beautiful tool.

"Jim, you feel so good. I'll probably have multiple orgasms, but don't stop. Please keep loving me until you cum. Please fill me with your love juice."

As he stroked into me, I pushed back to meet him. It took a few minutes, but we got into a love rhythm. I was producing lots of love honey and could hear the squish – squish as his cock stroked in and out of my vagina and slap – slap as the flesh of our bodies came together in love.

Little Jim just sat back and watched. I hope he was learning, but my whole concentration was in making love with Big Jim. I had multiple orgasms with him. After about 30 minutes his cock began to swell and spurt his love juice deep into my love center.

We were both fully spent. I wrapped my legs around him to hold him close while we both enjoyed the post-coital bliss.

"Sally, thank you for reminding me what it is to be a man. I need to go. This was supposed to be Little Jim's afternoon.

"It will be, but can we all get together again tonight? It's our last night,"

"I don't know, I would like to but . . ."

"Dad, mom said she was going to take a sleeping pill so she didn't get sea sick. Once she goes to sleep we can do whatever we want."

"Let's all meet down here after dinner. This is Jason's bunk so we will need to include him also, but I know for sure that I want you to make love with me again tonight – as many times as you can get it up. Now give me a kiss and go do what you have to do."

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4 Comments
AnonymousAnonymousabout 9 years ago
Contrived and hard to believe

The story started out hard and fast (pardon the pun), but quickly became silly and unarousing. There's absolutely no way an 18-year-old dude wouldn't know female parts, and the dialog with the cougar teaching him sounded like the bird and the bees talk. Boo, hiss!

AnonymousAnonymousover 9 years ago
Juvenile and silly

There is no way an 18-year-old wouldn't know what a vagina is and that a cock comes when stroked.

The dialogue was childlike. The story read like it was being written by a 14-year-old guessing what sex might be like.

Not much here to turn on anyone.

NateBiDudeNateBiDudeover 9 years ago
Sweet

I enjoyed this story. Sweetly Erotic. I didn't lost my virginity this way, but I shared several women with my dad like this story.

thebuffalothebuffaloover 9 years ago

This piece had a ton of potential, but none of it survived. To me it read very trite and juvenile.

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