She Wanted to Win

I was in the cockpit of my boat, doing chores. I sensed someone on the dock and looked up. A small figure was looking down at me with a tentative smile.

"Hi, I'm your new crew. Brian sent me."

She was about five-six, slender, with dark hair and a very direct gaze.

Hardly anyone except Brian, who had been stolen from me by a wealthy Swedish yacht captain, knew I needed a new crew member.

The odds of my taking on a female crew were very low. My behavior when racing was crude and nasty. I was just enough of a gentleman not to inflict that on a woman. But if Brian sent her, I should let her make her case.

"Why don't you come aboard and tell me how you know Brian."

She stepped agilely down and seated herself next to me. "We sailed against each other in school."

"How often did you beat him?"

"Most of the time. He wasn't very nice about it until we went out on a date and I softened him up."

She added, quickly, "I didn't go down for him, either. I kissed him and hugged him and told him he was going to have a brilliant racing career and not to mind if a girl beat him now and then."

"You got him to buy that line?"

I was in the process of seizing the end of my mainsheet, and not doing much of a job of it. She noticed and took it out of my hands. "It's easier with smaller fingers."

"Do you have a name?"

She looked up and smiled. "Before I tell you who I am, I would like to go for a sail, so you can make a judgment without a name attached."

It was a blustery spring day. If we went out, it was going to be cold and wet. "That's why you have your gear on?"

"Yes. I was hoping you would be nice enough to give me a chance. Brian said you didn't think much of women sailors."

"Did he tell you about my foul mouth and evil Irish temper?"

"He said you could be fierce at times, especially in a close race. I'm pretty fierce too. I like to win."

She was charming the pants off me. Mystery girl, who probably didn't weigh much over a hundred ten pounds.

"How come you are so skinny? Even on a trapeze, I don't know how much good your weight will do."

"I'm a runner. We don't carry much extra. If you are sailing well, you don't need a ton of weight out there."

I looked at her and saw the challenge in her eyes. Sailing well, eh. She was at least going to get a trial.

"I have to go to the car to get my gear. The sails are under that counter. We'll use the small jib and the regular main."

When I got back, the boat was almost ready. "What's the best way to get out of here?"

She looked around and said, "The jib will take us downwind out of the basin and we can do the main in clear water."

"Right you are. Hoist it and I'll cast off."

I had barely got the stern line free when a big gust hit us and we scrambled for control. She was down in the cockpit with the jib sheet with no prompting from me. I aimed for a slot between two anchored boats and we zipped right through. In a minute, we were clear and I headed into the wind.

"Take the tiller and I'll do the main."

In a few minutes, we were reaching for the breakwater at a good clip. My 24' class boat was new, courtesy of a supportive dad who used to sail himself. It had all the new winches and hidden halyards and an adjustable back stay. Given half a chance, twenty knots on a reach was easy.

We were next to each other on the high side. "Give me something of a name to call you."

She turned and smiled. "Amy."

"Been out on one of these before?"

"No, but I spent a lot of time in the seventeens."

"Handling the light sails on this is a big deal compared to the smaller ones."

"I saw one cartwheel in Biscayne Bay last winter on break. It wasn't pretty."

I was warming up to this girl. "Want to take the tiller?"

"I thought I was trying out for crew?"

"So far, I like your instincts. Show me your winning style at the helm."

We changed places and she yelled in my ear, "This isn't fair."

"It's whatever I say it is, Amy." My voice was harsh.

"Yes sir," came back in a hurry and she concentrated on the wind and sail trim.

"Are we heading somewhere?"

"Take a line on the lighthouse. There's a buoy in front of it. We can go round and head back."

Small or not, I could tell I had a real sailor on my hands. Her touch on the helm was smooth and sure. Her instructions to me about jib trim, and her own handling of the main were perfect.

"If we were racing, and had competition within a boat length, how would you take the mark?"

"You think I give up my racing secrets that easily? Where's the offer to take me on?" Her smile was wide even as another wave doused us.

"You must be as Irish as I am."

"I don't swear as much."

She cut me off, calling "Ready about."

I ducked under the boom and we went around smartly, with a rattling of sheets.

I suddenly realized who she was. This was Amy McGonigle, whose dad had been World Champion in Stars several times.

We could relax a bit on the downwind leg back to harbor. "Did Brian tell you about my racing plans?"

"He said you had a new boat you wanted to campaign this summer and take to Nationals in the winter."

"You are prepared to sign on for that?"

"I'm graduating in June, and my folks are letting me take a year off before grad school."

"You are crazy to spend it with a bum like me."

"Brian said you had a Wharton MBA but wanted to sail instead. So, who's crazy?"

"I've figured out who you are."

Her face fell. "Oh shit."

She surrendered the tiller and crawled past me, sitting bent over in a funk.

I put my arm around her and pulled us together. "Hey, I'm not trying to be mean."

Now she had her arms around my neck and was kissing the side of my face. "I know. You are being very nice. It's just that every time I try to do something on my own, people give me all the extra attention because of my name."

"What if you took a professional sailing name? You could be Dolores del Santos, rising young competition sailor from Buenos Aires. With that dark hair and a little Spanish, you would pass anywhere."

She giggled and licked me again. "You're cute. Are we going to sail together?"

"Are you free for dinner? We have to talk."

"Yes or no?"

"Give me a kiss."

She swatted me. "I'm not getting near you until I get an answer."

"I give up. Yes, you are my new crew."

I did get a kiss then. Several in fact.

"You are going to be happy with me. I love this boat and I will work my ass off for you."

"You have to promise me to drink milkshakes until there is more ass to you."

She pulled my hair and said, "I should have known the harassment would start right away. If this was a regular job, you would be fired for that remark."

"I know. You were warned I was a nasty man."

"Well, you've got a feisty broad for a crew, so watch out." She kissed me again and said, "Watch where we are going or your new boat will be on the rocks."

At the dock, she was everywhere at once, stowing gear and making the boat shipshape.

As we walked to the cars, she took my hand and said, "No shit, captain, you've made me very happy. Where are we going to dinner?"

My arm naturally fell around her shoulder and I said. "If you don't trust me, I'll take you to Tony's for salmon. If you do trust me, there is some fresh halibut in the refrigerator, and a nice bottle of chardonnay to go with."

"You are one of these guys who understands that no means no?"

I stared at her, and said, softly, "Yeah, I understand about no."

"Then, Mr. Collins, I would be delighted to have dinner with you at your apartment. I will bring the salad and dessert. You may call me Dee."

The smile was totally impish and I quickly kissed her forehead.

At six-thirty, she appeared at my door with arms full of food. The rest of her looked very nice in a striped blouse and black capris. The boat shoes came off at the door.

I poured two glasses of wine and we sat on the sheltered deck, watching the sun go down. I kissed the back of her hand and said, "With your talent, you could have found a lot better deal than me to advance your sailing."

She had dark eyes to go with the black hair, and they sparkled in the last sunlight. "I'm not so sure of that. Brian said you could teach me a lot."

"I'm just building the summer sailing calendar. Do you want to stick around after dinner and help with it?"

"Yes. Of course. Are we going to have a van or RV to crash in?"

"I hadn't got to that, but yes, it would help a lot, especially for the races in out of the way places. You don't mind what people will say about your traveling around with me?"

"My mother will have a fit, and my dad will say getting romantic with the skipper is sure to ruin a summer of racing." She smiled and almost giggled.

I sauteed the halibut carefully, and dressed it with lemon-butter sauce. The salad had all sorts of goodies in it, the way I liked it. We sat next to each other and ate greedily, with appetites from the cold sailing.

"The dessert is fruit compote. Do we do that in the other room?"

We did. I hadn't been this relaxed in a long time. Having a smart attractive sailing woman leaning on me helped a lot. She rearranged herself in my lap and said sleepily, "This isn't getting the calendar done."

I played with her hair and said, softly,"No."

I was thinking about the calendar and didn't realize the package lying on me was sound asleep. I leaned my head back and let sleep take me too.

A little voice said, "Does the crew get to sleep over?"

"Hmmm. Sounds like a good idea. Too late to be driving around by yourself."

By the time I was finished loaning her a toothbrush and doing my own, she was in the bed, in her underwear, already asleep. What kind of woman curls up in the bed of a guy she met today? I carefully got in behind her, with what I thought were no sexual moves.

The crew was up early and made coffee. She sat on me, on top of the covers, having found my terrycloth robe, and held out the cup.

"Don't get used to this, I am not the coffee girl forever. But you took me in when you didn't have to, and didn't attack me in the night, so you get brownie points."

"What are we going to do about the fact we already have the hots for each other?"

"You are such an arrogant guy!" Her eyes blazed, and then softened. She climbed off me, stood at the side of the bed, and slowly let clothing drop to the floor. She gestured to the sheet and I lifted it for her.

"We have to get this over. I'm not going around wondering whether you want me and if you do, whether we are good together. Now is your chance."

The kiss was totally incendiary. The small breasts were rubbing on my chest. Her hand was stroking me to full erection. My hands had a grip on the small tough behind, rubbing her sex on my hard cock.

"Hurry. I am very needy. Get busy."

This was a woman who knew what she wanted. Her hand guided me home to a wet, tight place that bucked up at me with a grunt and a moan. "Yes. Like that. More."

It was over too fast. Way too fast. She was full of my stuff and I wondered about protection. I turned us over and she lay on me catching her breath. When the head finally raised up, the eyes were bright and her tongue was out, searching for mine.

"Did that work?"

Silence. Her pelvis wiggling on me. Finally, "Yes. That worked. That worked the best ever. If good fucking wins races, we are way ahead."

"Your father doesn't think we can screw and win."

"After we win three races, and are still having sex every day, we will go to him and discuss the matter."

"Shit, I'm liking this more and more."

"Don't get overconfident. We haven't even been in one race yet, much less won it."

We were good for each other. The days and weeks went by quickly. The del Santos disguise was working. After a dozen races in a dozen places, we had four wins, three seconds, and a bunch of other finishes or DNF's when something broke, or the tide got us, or we just screwed up. It was the best record in the fleet and we were feeling good. On a Saturday in late July, we were sitting in the RV with drinks, feeling good about another win. Amy's younger sister Sheila was with us, having sweet talked her sister into letting her stay for a weekend, allegedly to get over a big breakup with a long time boyfriend.

At the moment, she was standing next to the dining table, dripping from the shower and trying to dry her hair without the skimpy towel covering the rest of her going on the floor. She failed. Amy and I looked at the hot, lush body, headed for Brown in the fall. "Are you being slutty again? He is my guy. You will please find yourself another boyfriend. You are a walking sex object." She reached out and pinched one of Sheila's prominent nipples. I pinched the nearest cheek. She turned to us with a great big smile. "I knew you would take me into your bed tonight. You won that race going away, and need a good fuck. So do I."

I took Amy's hand and kissed it. We rolled our eyes at each other. She gave me an imperceptible nod. I smiled in response and went to work on the barbeque while Amy tried to lower the temperature. It didn't work. I came back and they were in each other's arms, sipping on refreshed drinks.

"Ever since we were little, we need time touching and loving. I used to think we were lesbians, but that was before I found out about guys and fucking." Sheila giggled and kissed her sister.

Amy said, gently, "I tried to turn down all the sex drive, but it didn't work. She is just made that way."

The charcoal wasn't ready so I sat on the bed and pulled Sheila in between my legs. She leaned back against me and I rubbed the fine tits and kissed her neck.

"Sis, will you share him? It's only for tonight"

"Absolutely not. You might imprint on his cock, and then what would I do?"

I was doubled over with laughter, nibbling on Sheila's thigh and making her twitch.

I said, "Yes, that is a terrible hazard, imprinting on a guy's cock."

Sheila whispered in my ear, "Don't laugh. You are the first guy Amy has ever fallen for, and she has fallen hard for you. You may have to marry her."

Amy's head jerked up and she gave me a strangled look. "Sheila, I am going to beat you black and blue if there is any more of that talk. I'm not trapping anyone, especially Mark, into marriage."

Dinner was waiting, but Sheila and I got Amy between us and went to work.

I said, "A little loving and a little marrying, eh?"

She wailed at us, but Sheila overcame resistance and got the sailing clothes off. I fastened my lips on the big nipples, and Sheila dove into the wet pussy. It wasn't long and my lover was coming and shaking in my arms. Sheila lay on top, kissing wherever she could.

"Sis, tell him the truth. If he asks you to marry him, you will say yes."

Amy turned to me, crying, and said, "Yes, yes, yes."

I wrapped her in my arms as tight as I could and just hung on.

"Oh, god," she sobbed, "this isn't how anything is supposed to happen."

The three of us lay there, rocking back and forth, as twilight turned to darkness.

The sobs died out and she was mostly asleep when I said, "Will you marry me?"

The head stayed down and the crying started all over. Sheila's arm came up and she high fived me.

I left them in the bed and went back to work on dinner.

When we sat down to the meal, Amy had washed her face and was completely silent. Sheila and I tried to make conversation, but were talking only to each other.

Finally, Amy stood and grabbed a big handful of hair from each of us. "I should torture and murder you both. You take me and turn me into a sobbing blob. The two people I most love in the world are conspiring to make me even happier. The only guy I've ever loved actually wants to marry me! God, I'll probably cry all night."

She kissed and licked and cried. We got her back to the meal, and she took a few bites before another fit of crying.

Sheila and I were astonished. The tough sailor woman, all broken up? I decided to move things back to the bed, and we got the dessert and some liqueur lined up. Amy took the position between my legs and pulled Sheila in close. "The two of you have to promise to take care of me."

Sheila and I kissed and we made soothing noises for the patient and tipped up the booze glass. Sheila skinned out of her underwear and said, "Now that you are going to marry him, is it ok if I play around a little?"

Amy stuck out her tongue. "No, you tramp. You are trying to take advantage of me when I'm down."

This gave Sheila an idea, she crawled under the blanket and Amy wailed as a tongue invaded her sex. I helped by pulling Amy legs back to her chest. The view of all her parts was terrific and Sheila went to work with a vengeance. I leaned down and kissed my fiance, who jerked violently and came.

The orgy went on most of the night. Sheila got my briefs off and her cunt settled down on top of my very hard cock. The two of us kept Amy's body on my chest between us, torturing her. Sheila found a tube of lube and soon Amy was a slippery body able to be maneuvered into almost any position. I took her from the top, from the bottom, and from the side. She moaned and tried to get back at Sheila, who was also getting a lot of attention from my cock.

In the morning, Sheila stood by my side of the bed with coffee and her naked body. "That was sure some engagement party. Can't remember when I've had more fun."

Amy moaned weakly, "I'm going to get you."

I lifted her up and squeezed the two of us into the tiny shower. There was lots to wash off.

We took turns drying each other. "Did I really get engaged last night?"

"I'm afraid so, unless you want to call it off."

The punch was instant and hard. "Brute. Torture me all night and try to renege? Not on your life."

She stepped into my arms and whispered, "I love you."

Sheila said, "Oh dear, they mean it. I will fix breakfast. You stay here."

We quietly stood in each other's arms, just enjoying the closeness. "All I said to her was that I was falling for you. She thought up the marrying part all on her own. Is it really ok?"

I nuzzled into her shoulder. "It couldn't be more ok. I love you dearly."

"Please don't let me cry again."

"Want to wrestle?"

She thought about that and gave me a giant push to the bed. We really went at it, landing blows everywhere, calling vile names, and saying what lousy lovers we were. Exhausted, we lay back laughing and looked up at Sheila, with plates in her hands.

"That's a hell of a way to celebrate getting engaged, but I guess it takes all types. Here is your breakfast."

Amy was fixed up. She couldn't stop smiling. She pulled Sheila's hair and asked about the sex I provided.

Sheila blushed. "I'll marry him if you won't. Never had that many orgasms in my life."

Amy said, "You are going to meet some rich, smart, well hung guy at Brown who is going to sweep you off your feet and give you the hot sex you need."

Sheila was silent for a while and then said, "What if he doesn't? Can I come back to you for therapy?"

That completely broke us up and started another round of wrestling. Amy beat on Sheila's big behind and made comments about taking up running to trim it down. I fastened on to a plump boob and worked it over good. She screamed and threatened retaliation.

Sheila had to leave in an hour. She lay back, legs spread wide, and said, "Brother in law, please take care of your needy sister one last time."

Amy's hand stroked me and did the insertion honors. Sheila moaned and cried out, "Yes, yes, yes."

The orgasm was powerful and loud. We hustled her into the shower. Amy dropped to her knees and cleaned me up. I got a hot kiss from a messy mouth and a message, "Don't expect that every time."

Sheila was off and we were busy getting the boat on its trailer and leaving the yard. The next race was in Bar Harbor in ten days, and we talked about calendar over a sandwich lunch in the RV.