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Double Penetration

My younger sister and her college friends planned to spend their last Spring Break sailing in the Virgins. Jobs and grad schools were resolved, so final exams held no threat. This was to be the big party before things got real.

They had booked a bareboat charter – a sailboat hired with no professional captain or crew. My sister was the lynchpin of this project, since only she had extensive big boat experience. My family members were all wharf rats. We sailed constantly and vacationed in our small family ketch for most of my life.

So it was unfortunate when my sister called to say she had broken her leg skiing in trees with her boyfriend, Hans. She should never have put these two vacations together, but she was never a planner. The doctor had told her she couldn’t even fly home. But the charter was paid for, all six air tickets were non-refundable, and Spring Break waits for no one. She dragged me into her role. Resistance was futile.

Actually, resistance was negligible, because my sister was a popular girl and her friends, whom I had met casually over the years, were pretty and charming. So I found the best air ticket I could on 2 days’ notice — a 4 AM start with only two transfers — and told her I’d handle it.


My cab pulled into the charter base at cocktail hour. The rest of the group had arrived hours earlier and was already drinking, but they all jumped up to greet me.

The quickest was Amber, a friend of my sister’s since grade school. She was a pretty redhead with ultra-fair skin, but I quickly nicknamed her Trouble. Maybe it was that my sister had said “Amber is trouble.” But in addition, she had an over-the-top effusive manner. Every move screamed ‘look at me.’ She grabbed and hugged me like a long lost dog, exclaimed about everything, and generally swanned around holding as much attention as possible.

Next up was Becky, whom I eventually nicknamed Plush. She was a medium tall brunette with flawless alabaster skin and, while not fat, she was soft and rounded at every corner. She had a couple of enormous, plush round spots in front. She had a tongue stud and possibly nipple bars. In contrast to Amber, she seemed calm, self-possessed, and comfortable in her own skin. But at the risk of seeming shallow, her immediate appeal to me was that her boobs were simply sensational and very lightly constrained.

The third was Becky’s physical opposite. An obvious athlete, Delia stood nearly 5’10” and was one of those people who seem perfectly proportioned and endlessly graceful. When she moved everything rippled — muscles, tendons, whatever. I later learned she was all-state in two sports and almost an All-American. What a machine. I called her All Star.

Fourth was Deirdre, the evident leader of the group. She didn’t chatter, but when she did talk everyone stopped and listened. I had met her only once before, years ago, and hadn’t remarked on her personality. Maybe I was getting more observant. Without wasted words but with a fabulous, natural smile, she said it was nice to see me again and thanks for saving their trip; she hoped my rates were reasonable. She hugged me appropriately but I still felt the bumps. Competent, beautiful, and funny – I named her Triplethreat.

Last but hardly least was Liz. I had met her fairly recently, but how quickly things change. She was still on the small side and still quiet and shy. She stood at arms’ length and looked at her feet as we demurely shook hands. But now she had a serious case of porn bod — fantastic face, boobs just barely short of too big, shapely legs – you name it. Her waist was so small that her cut-offs couldn’t hug it, so there was an entertaining gap all the way around. She had long, straight blond hair, which just made her girlish face look younger and sexier. I wondered how she handled the effect she had on men. I called her Lingerie, because that’s all my brain could think of.

We would stay at the charter company’s hotel for one night, then get briefed, provisioned, and sent off for a week of sailing wherever. But first, more drinks and reggae were needed to shake off civilization. We ordered more rum, got out a chart and discussed possible routes and harbors based on where there were restaurants and hotels and where there were none. Everyone got into it.

The girls were a lively bunch, especially after drinking for several hours. The kidding was getting a little racy. When the steel drums started playing calypso, they danced with each other and Trouble even pulled me up onto the dance floor. She danced around me laughing and yakking and rubbing up against me, which was interesting. Being two years older and in grad school, I started to wonder what my responsibilities were. The whole scene made me feel old.

I was also worried because, though I had taken a quick dislike to her, Trouble was ultra-cute and I was getting hard. That made her even more annoying. Sure enough, we had been dancing only a few minutes when a slow number started bostancı escort bayan and she tipsily stretched up to wrap her arms around my neck. She was practically hanging on me and her boobs were crushed against me. This, maybe 90 minutes after we had met. There was no practical way of disguising my condition. She recognized the situation immediately and jammed her crotch against me. In the back of my mind I was worried that she would now claim me as her boyfriend, but my caveman brain was driving. She gave me the Meaningful Stare while she started sliding against me, up and down, only roughly keeping time to the music. Then she inserted a leg between mine so that she was massaging my cock and vigorously humping my thigh at the same time. I was beginning to leak. She closed her eyes. She was getting closer. Her mouth was slightly open, she was tilting her head and her lips were extending.

I quickly tickled her sides, ducked out of her arms, backed away and sat down. It took a big effort.

I was tingling for minutes and my imagination was running wild. I finally heard someone say “….isn’t that right?” to me and I had to come back to the conversation. But now I had Trouble to think about, for real.

Eventually I said I had to crash and went back to one of our three double rooms. The girls had agreed that three of them would share another. I wondered briefly how this would work on the boat, but I flopped down exhausted and went comatose until sometime after midnight, when I had to visit the head.

Upon re-flopping, I became aware of a lively discussion outside my window, on the balcony of the room next door. I couldn’t make out every word, and the girls still seemed pretty smashed, but it sounded like it involved who would sleep where on the boat. Deirdre was moderating but the discussion seemed quite animated, given the topic.

Good grief, I thought, time to get these kids under control. I had visions of trying to share a narrow bunk with a girl in only a tee-shirt and undies. I hoped I wouldn’t have a Trouble problem all night, every night. Sort of. But I myself wasn’t sure how to work things out unless I was expected to sleep on deck or on the dining settee, and under the circumstances I doubted they would make me do either.

I found it hard to get back to sleep, even after the talk died down. Visions of boobies in tee shirts danced in my head.


In the morning everything seemed normal. We had a quick breakfast, all wearing our bathing suits plus tee shirts or cover-ups. I noted that Trouble’s shirt stopped well above her crotch, and only a very small triangle of yellow cloth showed below it.

We agreed that most of the girls would handle the provisioning, but Deirdre would go to the Skippers’ Meeting with me ‘in case I fell overboard’. This is, incidentally, a real consideration when only one good sailor is on the boat. If I went over, it is very likely I would be out of sight before anyone could turn a large sailboat around. I was glad Triplethreat was the one attending. She just oozed competence.

After the chart talk she walked me over to the now empty bar and sat me in a corner. She said she had some thoughts to lay on me and wanted me seated.

The girls had not expected me on this trip; it had been a girls’ deal all the way, she said. But now that I was here, everyone liked me, and some were worried that there would be competition for my attention. One of the five might end up getting possessive with me, which would be totally obvious on a small boat, and four people would have a bummer of a trip.

I thought I knew exactly how this issue had come up.

Deirdre continued: a rule that no one date me was the obvious answer, but it would be hard to enforce. And, a majority of the girls had already said they were reluctant to agree to that anyway.

I nearly hurt my jaw on the table. But there was more.

So the proposal was that, with my consent, those girls who wished would share me. Wow. Each night there would be an evening date window and a morning date window, and they would be allocated to the girls evenhandedly. During this window I would be the girl’s fucktoy (my translation), but any girl could choose not to participate, or she could choose to spend her date with me chatting or sleeping so that none of the others would know whether she was a prude or a slut. I would be sworn to secrecy, of course, and I should treat the girls evenhandedly. The whole point was that no one should get treated more specially than anyone else so no one would feel left out and have a bad trip. This was for recreation, not relationships, anyway. An incidental benefit was that I would always get the best cabin, the one in the bow with the big v-berth. The plan had been approved 4 to 1 last night, and a re-vote in the cold clear light of day was the same. What did I think?

I said, how could I pass up that front cabin?

I actually had misgivings about whether I could ümraniye escort hold up my end of the bargain physically, especially with girls I liked less than others. So I insisted on the right to end the arrangement without recriminations, and with that the deal was done. Deirdre was fairly confident we would work it out. But then she was always fairly confident.

We boarded our boat at noon. She was a 45′ cruiser and pretty porky, but she was roomy, with a large double v-berth in the bow and another low-ceilinged double under each side of the cockpit. All this, of course, was in addition to the option of sleeping on deck.

I marched right through the boat and put my backpack in the front cabin, and the girls all cheered.

One of them was faking. Already.

Before casting off we made lunch in the galley and sat around the table with plenty of rum. Amber said, “So, we have a plan!”

I wanted to stay quiet until I could figure out the dynamic, but everyone was looking at me, so I offered that I would do my best to make the trip enjoyable for everybody. I’m a square. Becky said she couldn’t wait and engaged in some exaggerated lip-licking, which got the ball rolling again. I continued to be fascinated by the size of her boobs, which were resting on the dinette table and pointing right at me through a worn out tee shirt. Maybe I was imagining it, but I thought she was kind of thrusting them toward me. Amber said she would take the slot of anyone who didn’t want theirs, but Deidre said that was not the agreed system. I got a little flack about pacing myself and some anxious reminders about secrecy, which I said I took very seriously. But the mood was good and they all seemed to be tingling with anticipation.

Deidre held the floor briefly to say she would assign the 8 to 12 shift and the 2 to 6 shift with input from the girls, who should tell her their preferences. Then we cleaned up, cast off and sailed away on our great adventure.

As soon as we cleared the harbor the girls started to go below and re-surface with their bathing suits on. Amber was first out of the gate, of course, with a tiny, narrow, high-waisted yellow string bikini that was so pale she looked nude. Her boobs were nicely boosted and her legs looked great. But she ruined the effect by parading around the deck and posturing until I was gritting my teeth. To stop her, I asked during one close pass whether she was trying out for the Swimsuit of the Day Award, but the sarcasm was lost. It just provoked more strutting and a declaration she had won the Swimsuit of the Day contest. Then she sat down next to me at the helm, leaned against my arm and asked how to steer. I said, “You turn the wheel.” Aaaarrrrrrgh.

Deirdre simply pulled off her cover-up, revealing a simple dark blue bikini that went terrifically with her thick, wavy blond mane. Delia came up with a high-cut, narrow-back bikini that looked small on her tall frame, to great effect, and her legs were simply astounding. Her athletic physique was slightly scary.

Then Becky arrived with the real Swimsuit of the Day, a low-cut black number with many more straps and little chains than were strictly needed to hold up the small modesty elements. My imagination was fired, but I was still waiting for Lingerie, who didn’t seem to be in any hurry to change.

Finally, when we had reached open water, she appeared in a nice blue one-piece. It would have been modest, except that she was so formidable up front that large amounts of side-boob were showing and there could be no disguising the gentle rebounding with every wave we crested. I was entranced and had to I put on my sunglasses to avoid seeming lecherous.

That first night, having had only half a day to sail, we anchored in a cove at a nearby island. We declared cocktail hour, fired up the grill, and cooked our own fish dinner. We played a rowdy game of cards and I could see why the girls got along so well. Amber forgot for a moment that life is a popularity contest. Even Lingerie got slightly crazy. This was going to be a great week even if no one came knocking on my cabin door. But…the vote had been 4 to 1.

We were all tired, it was dark out, and cards were over. I think the tension must have spiked because no one made any racy remarks while we retired to our cabins. I left my swimsuit and tee on, since I didn’t know who was coming or for what. But I left the door cracked open to indicate I had no second thoughts.

About 20 minutes later there was a soft knock and Deirdre let herself in. I had expected Amber and was relieved. She was wearing a neck-to-ankle beach cover-up with tiny buttons all down the front. She smiled her fabulous smile and said, “I’m just here to talk. I want to clear up some points and be sure you are on board. This is a crazy, one-off arrangement. It has some flaws, and you didn’t have much time to think it through.”

I admitted it was a first for me and maybe for anyone. I said the superficial incentives escort kartal were obvious, and if the girls thought I would enhance their vacation, fine. I hoped they were right. “But I see lots of pitfalls — jealousy, dissatisfaction, my own death from exhaustion. I may need some patience. I like all you girls but maybe I’ll fall for one of you or be unable to stand one, and I will still have to treat everyone equally. I’d like a rule that our private moments will not be described, rated, or compared, if you can arrange that.”

She said she would stipulate that but that in a one case, it might be hard to enforce. I nodded. She asked about my impressions so far. At this point we were both sitting on the edge of the berth, but now I shoved myself back and leaned against the hull for a longer discussion while she pulled her legs up on the mattress and supported herself with one arm. I said that Amber worried me because she thrived entirely on other people’s admiration and seemed insatiable. If I fed her ego she would be insufferable and if I didn’t there would be hell to pay. I mentioned her bestowing the Swimsuit title on herself. I told her about my nicknaming and that Amber was “Trouble.”

Deirdre said I was pretty perceptive. Amber was on the cruise because she had known my sister for so long, not because she was a best friend. Delia, who was also very competitive, didn’t like her. But her competitiveness made her very vivacious so she could be a lot of fun, too. We would just have to be careful, since we were all locked up together for a week, like on reality TV.

She proceeded to profile the other girls without saying a bad word about anyone, which I always find attractive. Becky was a quiet tiger who would dare anything. She didn’t give a rat’s ass about other people’s opinions. Sometimes she did things that were cringeworthy, but then you still admired her strength of mind. Delia was bright enough but interested mostly in sports. She was highly competitive in all things. She could probably swim faster than we could sail. I told her Delia’s nickname and she nodded. “Don’t get crushed!” she said with a smile.

About Lingerie, all she would say was that Lingerie preferred to be a woman of mystery. “Underestimate her at your peril!” she said with a grin. I resolved to do a mind-meld with Lingerie as soon as possible. And to be sure to use her real name. If possible.

“What about you?” I asked. I was enjoying this and settled down with my head propped up on an elbow. I stayed a respectful distance away, and she copied me. I noticed there was no bra under the cover-up. Any guy would have.

“What’s my nickname?” she countered with a grin. No self-exposition, another attractive feature. I explained, and she said that was too complimentary but didn’t argue much. “You’re petty perceptive for a guy.”

I asked whether it would be useful to know who had not voted for the guy-sharing plan, and she said it was her. I said I thought that was sensible but was disappointed. She teasingly asked why, and I had a ready answer: I liked her … brain. I said usually women were a mystery to me but that I admired her logical approach to these arrangements. It takes someone smart to make things complicated, but someone really smart to make them simple again.

She grinned more than I expected. “You don’t know the half of it,” she said. “Also, women are a mystery to everyone, but if you keep your antenna up, there are sometimes hints.”

“Like what?” I said, and she grabbed the front of my shirt, pulled, and gave me a nice, tongue-free but unmistakably long kiss right on the lips. “Like that,” she said. She didn’t actually let go of my shirt. I asked if she was changing her vote. “I didn’t need to vote for this. The vote passed just fine without me.”


I said I would see her hint and raise her one. I grabbed her dress right over her boobs and I kissed her twice as long.

“Let’s take off these inconvenient clothes,” she said.

Her tiny buttons all undid themselves with one long, slow pull. That was all she had on. Without even taking her arms out of the sleeves, she snuggled up and said, “No noise!” She pushed down my trunks. I was totally, and obviously, happy to see her, and we went into a lengthy full body contact kissing session. Despite the time limit this was not going to set a speed record. There was much back-rubbing, face-kissing, leg-twining, and crotch pressing. Eventually, she lay on her back with a sigh, hands over her head and her lovely hair pooled around her in mock surrender. I ran a hand slowly and lightly down her stomach to her pussy. She shivered as I started to run my finger up and down her pussy lips. They parted in short order. I played only a little longer before she rolled toward me and guided my cock inside her. We started a slow, languorous motion with her on top. “I’m happy with my choices,” she whispered. “I’m happy with you,” I said. She said “Shhhhh!,” pressed her finger over my mouth and scowled humorously at me. I started to pump faster and she gave a little squeak, so I put a finger across my lips and she stifled a laugh. We worked slowly to a crescendo. We arched our backs and came nearly together. Then we fell into each other’s arms. Textbook.

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