Cruise Doubledate with My Sister

"Does she have any regrets about our summer together?"

"None. She had a great time and knew it was only for the summer. She told me you were hot in bed."

"Well, if I was, it was because I did all the things you told me to do. Three times with Jacob on Sunday? It sounds like you're an animal in the sack."

Caitlin flushed. "How was Rebecca?"

"In bed? Okay. She wasn't in the mood as often as I wanted. I don't think she was ever comfortable having sex. You know how fundamentalist kids are. Always the missionary position. When she was in the mood for sex, she would take her panties off right before getting into bed. If she left her panties on when she got into bed, there wasn't any way of convincing her to have sex. Lisa was more fun, but the only reason I dated Lisa was for the sex. With Rebecca, sex was more of the cherry on top."

"Earlier, you mentioned the Rebecca. What's that?"

"It's a long story."

"I'd like to hear it."

Oh, what the hell.

"The first time Rebecca and I slept together, we were just friends. We had watched a movie at my place on a Friday night and afterward we talked a long time about the movie. It was past midnight when Rebecca decided to go home and I told her not to, that only drunks would be driving so late. I asked her to sleep with me with the promise that we would both stay clothed and I wouldn't make a move on her."

"You slept together fully-clothed?"

"Well, Rebecca wore one of my T-shirts and panties while I wore a T-shirt and shorts."

"Why didn't one of you sleep on the couch?"

"I don't know. I wanted to sleep with her and she went along with it. We got in bed and I wanted to give her a hug. I somehow scooped her up and deposited her on the right side of my chest then hugged her there. I liked it and didn't want her to move off me, so I recounted our evening together; how much I had enjoyed hanging with her. At first, she had been uncomfortable but she gradually relaxed. When I was done, she asked if she could sleep on me and I said yes. The next morning, she told me she had loved the whole bedtime experience. The next Friday, she slept with me and asked me to tell her about our day again. So that became the Rebecca."

"And the Full Rebecca?"

"Well, the clothing steadily disappeared. My shorts got replaced by underwear. Then I left off my shirt. Then I bunched her shirt up high so I could feel her skin against mine. Then her shirt disappeared. Then my underwear disappeared. So we called our sleeping together with her in her panties and me naked the Full Rebecca."

"That's crazy. Or romantic. Or something. I can't imagine two adults dragging things out like you did. When I like a guy, we fuck on the first or second date."

I didn't respond as I was thinking about Rebecca. God, I missed her. I pictured her next to my bed wearing only her panties as she had on so many nights. Her long blond hair peeked out from behind her back. Her breasts jutted out proudly. Her soft skin was ready to slide against mine.

It was easy to push thoughts of her aside when Caitlin and I were doing stuff, but they never went away. Now I was surrounded by memories of good times Rebecca and I had had together. Loneliness engulfed me.

"Come on," said Caitlin as she pulled on my hand to get me out of my chair. "Let's dance some more."

"Sounds good."

* * * *

It was two when we staggered back to the cabin. Caitlin went into the bathroom to do her bedtime stuff and when she came out I grabbed my shorts and did mine. When I came out, Caitlin was under the covers and I could see the top of her nightshirt. I got under the covers and lay down on my back.

I expected Caitlin to go right to sleep, but instead she said, "Thomas, the Full Rebecca sounds really neat. Could we do it tonight?"

"You're too big and heavy to sleep on me."

"I know, but I want to do the rest."

I stuck my arm out.

"Okay. Come put your head on my shoulder and I'll talk about our day."

Rather than move towards me, she did something under the covers. I took me a moment, but I realized she was taking off her night shirt.

"Caitlin, what are you doing?"

"Getting dressed for the Full Rebecca. Take your shorts off."

"Caitlin, what the hell? You're my sister. Put your shirt back on."

"Come on, Thomas. Just this once. I won't see anything and neither will you. I want to see how it feels."

I rolled me eyes. I loved to cuddle and cuddling with a mostly-naked woman would normally appeal to me, but it wasn't right with my sister. At the same time, it was what she wanted and there wasn't any harm. No one would find out about it.

"Oh, alright. Just this once."

"Now take your shorts off."

I slid my shorts off and was naked. Caitlin moved up next to me so her head was on my right shoulder. I pulled her close with my right arm and held her against me. I wondered briefly what panties she was wearing. I hadn't seen her naked tits, but I already had an excellent idea of what they looked like from seeing her in her bikini. I knew they were pressed into me, but I couldn't feel them distinctly. What I did feel was her soft skin covering the right side of my body.

"Okay, what did we do today?" I asked rhetorically. I recounted the boat ride, the hike through the jungle, and the exploration of the ruins. I talked briefly about our stay at the pool. I recalled the pleasures of shopping with her, seeing the show with her, dancing with her and having a late-night snack with her on deck. I finished with our final dance session and our doing the Rebecca.

"That was wonderful. Rebecca was stupid to give this up. We'll have to do this again tomorrow night."

"Caitlin," I growled. "You said just this once."

"I know, but I didn't know how great it would make me feel."

"You're taking advantage of my being a conflict avoider."

"I'm taking advantage of you being an awesome big brother who will do anything I ask to make me happy."

"You don't fight fair, Caitlin."

She gave me an evil laugh.

"Was Jacob good at cuddling?"

She snorted. "He was awful. After sex, he would say something nice and give me a kiss, then roll over, face away from me and go to sleep."

"I love to cuddle. Rebecca loved to be cuddled at home. When we were with friends or in public, all she would let me do is hold her hand. It really bugged me."

"Well, you don't have to worry about that anymore. There are lots of available girls who love being cuddled. Including me. I love you, Thomas." Caitlin gave me a long, sweet kiss on my check.

"I love you too."

"Good night."

"Good night."

Wednesday, Cayman Islands
My eyes felt glued together when the alarm went off. I fumbled over and turned it off. I then realized a problem with Caitlin's plan for us getting undressed for the Full Rebecca. How was one of us going to get out of bed without exposing ourselves to the other? One of us had to go to the bathroom so the other could get dressed for the day alone.

Caitlin of course solved the problem easily. She sat up so her body faced away from me, got out of bed, bent down to pick up her night shirt and put it on. I could only see her backside while she didn't have her night shirt on. What a nice backside it was. She was wearing pink, low-cut panties. I had some serious morning wood. I hadn't cum on the cruise and I was getting close to blue balls zone. I had occasionally thought about getting away from Caitlin for a while to beat off, but I had decided against it because I wanted every minute of the day to be good for her.

Today's excursion was a cruise out to the Stingray City Sandbar. Caitlin dug out her orange bikini and went off to the bathroom. I pulled on my swimsuit.

Unlike yesterday, we were relaxed and having fun with each other right away. The excursion was incredible. First, we went to a shallow reef and snorkeled in crystal clear water. The weather was perfect. We saw gobs of tropical fish. If we had stopped there, it would have been a really good excursion. Instead, we went to the Stingray City Sandbar. The stingrays were everywhere and had no fear of us. Both of us held one. It was amazing.

Once the excursion was over, we had lunch, worked out and showered. I showered first and tried to beat off while Caitlin was in the shower, but she came out before I was done. Once she came out, we took a nap. It seemed natural to sleep in one bed together. I was afraid Caitlin would want to do the Full Rebecca at nap time, but all she wanted to do was to hold hands.

Like yesterday, we did dinner, show, dancing and a midnight snack. As we sat and ate, I said, "When we were walking around the deck on the first day, you said you were looking to do four things on this cruise - excursions, drinking, dancing and fucking. I obviously can't do number four. How am I doing on the other three?"

"Great. I'm having a great time. I'm probably a poor substitute for Rebecca but you are more fun than Jacob. I was getting so tired of the drama."

"Anything you want to add to that list?"

Caitlin thought for a bit. "I enjoyed hanging out at the pool, but I don't want to be asked about Jacob so I'm fine with avoiding it. I'll stick with my initial list. How 'bout you? Are you having a good time with me?"

"You aren't Rebecca, but the things you want to do on a cruise are the things I want to do. I'm having a good time."

"Good." Caitlin paused for a bit. "Let me ask you something. When was the first time you slept with Rebecca?"

"Around Labor Day? I think the weekend before."

"And when was the first time you fucked?"

"Exactly a month ago." It seemed so long ago now. At the time, I thought it would be a date I'd always remember. Now, it was a date I wanted to forget. No, I'll remember the first time with Rebecca and forget Monday.

"It's hard for me to wrap my head around how long it took you two to go from more-than-friends to lovers."

I shrugged. "Once or twice a week we took a step forward in our relationship, but the steps were so small that it took us a long time to reach the point of making love. It was all about getting Rebecca comfortable with the physical side of our relationship."

"I've made you talk about Rebecca long enough. Let's go dance some more."

* * * *

Once again at two we staggered into our cabin. I felt a little silly putting my shorts on for bed, knowing I would take them right off. When I came out of the bathroom, Caitlin had her night shirt on.

"What is your shirt made of?" I asked.

"Silk. Feel it."

I did. "Feels nice."

"The girls like it," she said as she shook her tits. My cock stiffened.

I got into bed and stripped off my shorts. "Do you always wear a night shirt when you sleep with a guy?"

"Depends on the guy." Caitlin got under the covers and took off her night shirt. Again, I saw nothing. "If I am going to cuddle all night with a guy, I sleep naked or in panties. With someone like Jacob who wants to sleep by himself, I wear a night shirt."

I raised my arm and she put her head on my shoulder and snuggled up to me.

"Instead of doing the Rebecca, I want you tell me step by step how you got Rebecca to make love to you."

"Caitlin? Really?"

"Really. I'm just so curious. What were all the little steps?"

"I don't want to talk about Rebecca right now."

"Thomas, you promised."

I had promised. "Oh, okay," I said, feeling slight exasperated. "On one condition - if it starts making me sad, I stop."

"Agreed."

"So I'm starting with the first night we slept together...The next morning when we woke up, Rebecca gave me a kiss on my cheek and said thanks for the great night's sleep. That was our first kiss. She left right after we woke up to get dressed at her place. The next Friday, she slept with me at my place again."

"Did she bring clothes?"

"No. I don't think she would admit to herself that she wanted to sleep with me."

"Go on."

"So we slept together and she gave me another kiss on the cheek in the morning. Next week, same thing except when she left, I told her something like, 'get out of here as I have some pressure to relieve.' A joke about how I was going to beat off once she was gone. That night when I went over to her place, I gave her a kiss on the cheek. She gave me one back. We did something, went back to her place to talk and we exchanged kisses on our cheeks when I left."

"Did you think about asking her out on a date at this point?"

"No. We were both very upfront that we didn't want to date each other. We were just being extra friendly." It seemed odd now, but it had seemed normal then. "Next weekend was the same including the parting comment. You have to understand that when Rebecca and I slept together, we always woke up together. The next Saturday after we woke up, Rebecca said, 'Stay here and take care of the pressure while I fix us breakfast'."

"She told you to beat off?"

"She knew I was doing it when she left. She had brought some clothes in her car and we were going to do something together that morning."

"I'm starting to see what you mean about small steps."

"Next Saturday, she again made me breakfast while I beat off. Usually, Rebecca likes to sleep a half hour to an hour more than I do. The next Saturday when we woke up, she said that she wanted to sleep some more so why not take care of my business then go make us breakfast."

"So you beat off while she was in bed with you?"

"While thinking of her the whole time. All she could see was the covers going up and down. I used some underwear and when I was done, I went out to make us some pancakes while she slept some more."

"At this point, you aren't just friends."

"But what were we? You can't say I was getting any benefits from her." I organized my thoughts some more. "This was the beginning of October. Our schedule at this point was that she slept over at my place on Friday nights, we spent Saturday together and we did something together once or twice during the week."

Back to the story.

"So the next Saturday morning, she again told me to relieve myself then go make breakfast. So I was lying on my back, beating off when she started giving me lots of little kisses on my check and running her fingers through my hair. I loved it. I came really hard that time."

"This is so hot."

"Saturday night at her place, we were watching a movie on cable and I put my arm around her. I figured that after all those kisses this morning, why not? She was uncomfortable at first, but she didn't move my arm. Eventually, she seemed to accept it. From then on, I would always put my arm around her when we watched something on TV."

"So you are definitely more than friends at this point. What did people at work think of you two?"

"They had no idea. By this time, I had stopped visiting her during work hours. I had used visiting her as an excuse for chatting up the other single girls in Marketing but at this point, I was only interested in Rebecca. I would go to parties hosted by her friends at work and she would go to parties hosted by my friends at work, but we showed up and left separately."

Relating my history wasn't making me sad like I expected. It was cathartic to lay it all out to someone else to get their opinion.

"From then on, Saturday mornings kept getting hotter. One Saturday morning, I was beating off in bed and she was giving me lots of little kisses on the side of my face, nibbling on my neck and blowing in my ear. I turned my head and kissed her on the lips. That was our first kiss on the lips. She kissed me right back and soon we were frenching like crazy. She was on my right side as always. I stopped beating off, grabbed her, set her on the left side of the bed then threw the covers off me so I could comfortably beat off while kissing her. That was the first time she saw me naked."

"This is so fucking hot. What was she wearing?"

"Night shirt and panties. At breakfast, I asked her if she wanted to date. She said she was happy being friends. Pretty crazy, huh? If I had told you at the time what was happening, what would you have told me?"

"You're definitely friends with benefits at this point. Was she looking for another guy to date?"

"Not that I knew of. She went to church on Sundays and Wednesdays. She could have been looking for a guy there and I would have never known."

"What was she like after she went to church?"

"Guilt-ridden. It was frustrating seeing her on Sunday nights as she was always so down. She did a video call to her parents every Sunday afternoon and Tuesday night and talking to them always left her feeling guilty. Sunday was a double dose of guilt."

"Had she mentioned you to her parents?"

"She never said. She always wanted to be alone when she talked with her parents. The few times where we wanted to leave right after her call with her parents, she had me wait in the parking lot."

"I've known a few people who had friends-with-benefits relationships and they were all about being able to have sex when they wanted to with no strings attached. At this point, she's not even having any sex. What time is this going on?"

"Mid-November. At this point, she was sleeping over at my place every Friday and most Mondays."

"So what happened next?"

"The next Saturday, it was another steamy make out session while I beat off. I came and was exhausted. I didn't want to get out of bed. So I said, 'Don't you have some pressure built up?'"

"You didn't!"

"I did. Rebecca was all shy and embarrassed, but obviously worked up. I eventually convinced her to get herself off while I stroked and kissed on her."

"Had you seen her naked yet?"

"No, but the night shirt was bunched up pretty high at this point during the Rebecca. She soon ditched it all together. We spent all of Thanksgiving weekend together. Every night, we made out like crazy on the couch. I was naked and she had on only her panties. Then in the morning, a frantic make out session while we took turns getting ourselves off. The first Saturday in December, we were making out while I was beating off and she grabbed my cock. 'Let me give you an early Christmas present.' She then beat me off while kissing me and rubbing her tits all over me. It was wonderful. The next Saturday, I asked her to let me get her off. My early Christmas present to her. It didn't take much persuading. She threw back the covers and stripped off her panties - it was the first time I saw her naked - then I got her off."

"Did she like it?"

"Very much so. For the rest of the Christmas season, we masturbated each other the next morning after we slept together. By now, she slept at my place on Fridays and Mondays and sometimes on Thursday. On Saturdays, I slept at her place and left when she went to church. I didn't like sleeping at her place as her bed was so small."

"You were so happy last Christmas and now I see why. I had asked if you were seeing anyone and I think you said you weren't dating anyone."

"We both thought it hilarious how no one had any inkling how involved we were. So if I had told you all this at Christmas time, what would you have advised?"

"Before I answer, had she mentioned Jacob?"

"A few times. She would mention him now and then when she told stories about college. She talked about her boyfriend from high school a lot more."

"What'd she say about him?"

"She dated Paul her junior and senior years. She had thought at the time it was the ideal Christian dating relationship. They made virginity pledges together and they gave each other purity rings. They kept their desires under control at all times. The only contact they made on dates was holding hands and a kiss on the lips at the end. People at her church held them up to other teens as an example of how young people should date. They broke up when she went to OU and he went to a little bible college. Their sophomore year, he dropped out, moved to Houston and got a job. Her junior year, he told his parents he was gay."