Do Me a Favor

Note: Everyone in this story is over the age of eighteen.

Families sometimes drift apart, and sometimes get back together. My sister Anna and I had grown up on the east coast, but we both had a kind of wanderlust. When I graduated from high school I went off to college in the midwest, and during my first year only came home for Christmas. By the end of my freshman year I had a summer job lined up in Chicago, so I only went back home for a few days around Labor Day, just before school was supposed to start. My sophomore year I got involved with a girl, and didn't go home for Christmas. The relationship didn't last, and I decided I would surprise Anna and show up at her high school graduation.

She was thrilled, my folks were glad to see me, and everything went well. A couple of days later, Anna and I went out to lunch, and I asked her what her plans were.

"I've had enough of school for now," she said. "I don't want to go to college. I want to see some more of the country, have some fun. I'm going to San Francisco."

"Wow, big step!" I said. "What do the folks think about that?"

"Well, they're not happy, but I'm eighteen, so there's not much they can do."

"Any idea what you'll be doing?"

"You remember our cousin Ralph?"

"Vaguely. He's a lot older than we are, right?

"Yeah. Well, he's a big shot in some tech company out there, and I wrote to him and asked him for some suggestions. He got me a job."

"That's great!"

"Oh, it's just entry level, and I'm sure boring as hell, but it's in San Francisco!"

The next day I headed back to Chicago, and we promised to keep in touch. But of course we didn't.

------

Fast forward eight years. I had gotten serious with a woman my junior year, and when we graduated the next year we had gotten married. I was working for a management consulting firm and traveling a lot, and she had a job as a paralegal in a Chicago law firm. She didn't like being left alone, and one thing led to another, as they say. After five years we agreed to call it quits. Last I heard she was dating an attorney and applying to law schools.

So for three years I was single again, still traveling a lot. Other than exchanging Christmas cards and what I picked up from my folks, I hadn't heard much from Anna, but to be fair, she hadn't heard much from me either. I had my buddies, I had some women I dated, and Chicago had great entertainment. So I wasn't too happy when my boss called me into his office.

"Tom, you're a good worker, but we're top-heavy here. Headquarters says we have to get rid of some overhead. So -"

"So, what? Are you firing me?"

He laughed. "No, nothing like that. I'm offering you a position in the San Francisco office."

I resisted at first, but realized I didn't really have that much in Chicago. Friends I could make anywhere. Women - well, as the boss said, in his own sensitive way, "The ratio of women to straight men is about eight to one out there. You'll get more ass than a toilet seat."

So we negotiated. I got a bump in salary, and they agreed to pay all my moving expenses, and even sent me out for a few days to try to find an apartment. The folks in the San Francisco office were very helpful, with advice on where to get this and that, how to take the bus and subway, and where to go for a good dinner. I felt a little miffed when I found out that my salary increase would just about cover the increase in state taxes, but all in all things went pretty smoothly.

Just before I left Chicago I had called my folks to let them know. My mother said, "Oh, good. Check on your sister. We haven't heard from her in a while."

So after I had unpacked in my new place I gave her a call. "Hey, Anna, it's Tom. Guess what? I got transferred to San Francisco."

"You're here now? I don't believe it. We have to get together."

So we made plans to meet for dinner in a restaurant she said had great seafood. I thought it was a little strange that she didn't invite me to her place, but maybe after eight years she wanted her privacy.

Anyway, we met for dinner at the appointed hour, and I was amazed. The last time I had seen her she was just graduating from high school. Now she was a woman, and a very good-looking one. She obviously exercised regularly. She was slender and toned, her brown hair was styled, and her dress made her look sexy and elegant at the same time.

I gave her a kiss on the cheek, and told her she looked great. She smiled and said, "Thanks," then changed the subject, asking about my move here, where I was living, and so on. Then she said, "So how does Marcie like it here?"

Marcie was my ex-wife. "I said, "You didn't hear? We split up three years ago."

"Oh, no! I'm so sorry!"

"Don't be. It was mutual. But didn't mom and dad tell you?"

"I - well, I haven't talked to them much. They were all like, when are you getting married? I couldn't deal with it."

"Yeah, I get it." I paused. "So, when are you getting married?"

I meant it as a joke, but to my great embarrassment she started to cry. "Anna, I'm so sorry, I shouldn't have said anything..."

"It's okay," she said, wiping her eyes. "It's a long story. Do you have plans for the rest of the evening?"

"No."

"I don't want to talk about it here, but I want to talk about it. It helps. Can you come to my place?"

"Sure."

We finished eating, skipped dessert, paid the bill, and headed out. I followed her to her apartment in an area that she called "the avenues," and we went inside. After the usual formalities, we sat in her kitchen with a glass of wine.

"So," she said, "when I came out here I didn't know anyone but Ralph, and he was like twice my age and then some. I went to work, and made some friends, but it was pretty lonely. Then I met Ed. I was coming out of the grocery store just as he was going in, and I dropped one of my bags. He helped me pick everything up and got me to my car. He was handsome and seemed kind, and like I said, I was lonely. I gave him my phone number. After a few days, he called me and we made arrangements to go out. I had a really nice time, no pressure. We saw each other pretty regularly, sometimes dinner, sometimes a movie, but only on weeknights. I have to admit, I fell for the guy. Well, things progressed, I invited him here for dinner, and we ended up in bed. That's when he told me he was married."

She took a long drink of her wine. "I was pretty pissed, but he was very persuasive. It was a marriage in name only. She was a strict Catholic and didn't believe in divorce. So on and so forth. He said meeting me was the boost he needed to get out of the marriage."

She took another sip of wine. "So we kept seeing each other, and kind of settled into a routine. He'd come over here, we'd have dinner, we'd make love, and he'd go home. And never on weekends. After a while I started pressuring him. He always had some excuse. 'Oh, the time isn't right, my wife is sick, my parents wouldn't understand.' Finally about six months ago I gave him the ultimatum. Her or me. He hemmed and hawed. The next time he came over I wouldn't let him in the house, and I told him I would show up at his place over the weekend and have a discussion with his wife. I haven't seen or heard from him since."

"That's - that's horrible," I said. "Much worse than what I went through. Have you told anybody else?"

"Just a couple of girlfriends from work. But I'm beginning to wish I hadn't."

"How come?"

"Their theory is that to get over Ed I have to get out and date. I said I wasn't ready, but they're being pushy. Which means they're planning to fix me up with some dork who's a friend of their boyfriends. You should see these guys. All they do is sit around and play computer games on their phones. Complete nerds. If I'm gonna date someone I want to be able to play tennis with him, go on hikes, go swimming."

"Yeah, you always were kind of a tomboy, but I have to say it looks good on you."

"Why, thank you, sir." And she laughed, for the first time that night.

It was getting late, so we said our goodbyes and promised to do this again soon. I went back to my apartment and went to bed.

A couple of days later she called me to ask if I wanted to take a hike with her on Saturday. I had nothing planned, so I agreed. We met up early Saturday morning, drove over to Marin County, and hiked up Mount Tam. It's only 2,500 feet or so, a pretty easy walk, and we took our time and just enjoyed the day. We got back to her place around four o'clock.

"Come on in," she said. "I can make some pasta for dinner."

"You don't have to feed me," I said. "You probably want to take a shower and rest."

"Actually," she said, "I've got a favor to ask."

"Okay, ask."

"Not yet. I want you in a good mood."

I laughed. "Okay. Pasta it is. You want me to go get some wine?"

"Do you mind? There's a grocery store not too far from here."

I drove to the grocery store and picked up a couple of bottles of chianti. By the time I got back she had taken a shower and was making a salad. She had on a tee shirt and running shorts, her hair in a ponytail, and she smelled like floral shampoo. "If you want to take a shower, feel free," she said. I had my running gear in the car, so I went and got it. Luckily it was clean. I just basically rinsed the sweat off and got into clean clothes.

"I'll put the pasta on now," she said. "It won't belong. How about opening some wine?"

I opened a bottle and poured us each a glass. Soon the pasta was ready and we had a nice dinner. We cleaned up, put the dishes in the dishwasher, and refilled our glasses.

"Let's go sit in the living room," she said, and, it being her house, I followed her and sat on the couch.

"So here's the thing," she said. "I told you about my friends and how they want to fix me up with some nerd."

"Yeah."

"Well, I told them I had met someone, and it wasn't necessary, and they said great, let's all get together at the beach on Sunday."

"Oh. Well, look, I don't want to interfere with your plans, and I'm thrilled that you met someone else..."

"Tom, stop. I haven't met anyone. I just said that to put them off, and they called my bluff. So I wanted to ask you if - well, if you'd pretend to be my boyfriend for the day tomorrow."

"Well, yeah, I guess. I mean, we'd need a cover story."

"Best to keep it simple. We knew each other back east. When you came out here you looked me up, and we hit it off."

"Yeah, that works. So, what's the big deal?"

"Well," she said, "there's one more thing I didn't tell you. The beach we're going to? It's a nude beach."

My mouth must have fallen open, and I didn't say anything, because after a minute she said, "I knew this was a bad idea."

"Lemme get this straight," I said. "You want me to get naked in front of four strangers and my little sister, all the while pretending to be your boyfriend?"

"I'm sorry, it was a dumb idea," she said. "I'll just tell them you couldn't make it, and they'll see through me and fix me up with the dork."

"I'll do it," I said.

"What?"

"I'll do it. But we have some work to do."

"What do you mean?"

"It's gonna have to be convincing, right?"

"I hope so."

"Okay," I said, standing up. "Come over here." She got up and came over to me.

"Now," I said, "kiss me like you would kiss your boyfriend."

She put her arms on my shoulders and gave me a quick peck on the lips.

"That's how you kiss Uncle Louie at a family wedding." I said. "Arms around my neck. Good. Body pressed up against mine. Good. Now, let your lips relax and open your mouth just a little."

I turned my head and kissed her, gently but very sensuously, rubbing her back and pressing my body into hers. After a minute she broke away from my lips, but I continued holding her. "Um, wow," she said.

"I agree," I said. "You're pretty good at this. Again."

And we kissed again, this time for much longer and with even more feeling. "I think I need to sit down," she said.

"Nope. One more." This time it was as if she took the lead, pressing her body into mine. To be honest, I lost track of time. When we finally came up for air it was clear that neither of us wanted to stop.

"We'll work on that some more later," I said. "Now. Nude beach. Tell me, have you ever seen me naked?"

"Not really. I used to try to peek at you in the shower, but I never got to see anything."

"And so your natural tendency will be to be embarrassed, right? Your brother, naked?

"What are you saying?"

"I'm saying, you're going to get used to it tonight, so it'll seem natural tomorrow."

I took off my tee shirt and stood in front of her.

"Okay," she said. "Very nice, but nothing I haven't seen before."

"Rub your hands on my shoulders, my chest," I said. "You need to be absolutely comfortable doing that, like it's second nature."

She reached out tentatively. "Come on," I said. "You might like it. I know I will."

And she did. She slid her hands over my shoulders and down my chest, then up my arms and around my neck, and then we were kissing again.

"Mmm," she said, "I could get used to this." She started in again.

"Okay," I said after a while. "Now for the main event." I slipped my thumbs into the waistband of my running shorts and slid them off, followed by my briefs. My cock was standing straight up and throbbing. She kept looking into my eyes,

"Anna," I said, "look down."

She took a breath and did so. "Oh, my," she said, "is that for me?"

"No, it's for the other four women in here. Of course it's for you. Give me your hand." She did, and I put it on my cock, so she could feel it pulsing. "Go on, get to know it."

Unsure at first, she held it loosely without moving, but gradually began to interact. She put both hands on it and began stroking, then reached down and cupped my balls. She bent over and kissed the head, then stood up and kissed me again. My rigid cock was pressed into her stomach. "Oh, god, that feels good," she said.

"Okay," I said, "your turn."

She went to take off her tee shirt. As she did, she said, "Have you ever seen me naked?"

"Not since you were a baby."

"I've changed a little," she said, and took off the tee. Her breasts were a good size, maybe a B cup, but very firm, with dark nipples that stood out like erasers on a pencil.

"May I?" I said.

"Yes."

I walked around behind her, slid my hands up her arms, then down her sides to her waist. Then slowly I brought my hands up her stomach and cupped her breasts, one in each hand, tweaking her nipples and gently squeezing the soft firm flesh. She leaned back into me, her eyes closed, breathing through her mouth. I kissed her shoulders, her neck, and worked my way around to her front, where I took one of her nipples in my mouth, sucking and nipping. I stood up and kissed her, a long, loving kiss.

"Last step," I said, and slid my hands into her waistband and slowly slid her shorts down her legs. She was wearing bikini panties, and they had a big wet spot in the crotch. I took those off as well.

"Anna, you are gorgeous," I said, as I looked at her slim, shapely legs leading up to her pussy. She was partially shaved, with just a thin band of hair above her slit. I put my hands on her hips, then knelt down and looked at her pussy. It glistened with her juices. I rubbed my hands down her legs and then up the insides,and very gently touched her labia. She moaned. "You smell wonderful," I said, and put my face close to her. She opened her legs for me, and I licked her, just the outside. Then I stood up.

"Now," I said, "kiss me like I'm your boyfriend." She pressed her body into mine and kissed me with a lot of passion. I slid my hands down her back, cupped her butt cheeks, and lifted her until my cock found the entrance to her pussy. She wrapped her legs around me and held me tight inside her. "Bedroom," she said, tilting her head to tell me where to go. I sat on the bed and rolled onto my back, and she straddled me and worked my cock in deeper. She began moving her hips over me while I thrust up into her, all the while playing with her breasts, her nipples.

She came first, shuddering and clamping on my cock, which got me off. I shot a huge load into her, pumping and pumping while she milked me until we both were completely spent.

"My god," she said, when we had both come down, "I never felt anything like that in my life. The kissing, the rubbing, the whole package. What an incredible turn-on."

"I know," I said. "I've never felt anything like that either. Part of it was probably that we're both horny as hell, but..."

"I've been horny before, and nothing like that ever happened."

She cuddled up to me, and we fell asleep pretty quickly. I woke up later - it was still dark, so I'm guessing it was about three or four o'clock - and when I moved she woke up too. Neither of us said a word, we just began kissing, and we made love in a very leisurely way. She came twice, I could tell by the way her pussy clamped down on me, and I ended up on top and shot another load into her. We fell asleep again with my cock still inside her.

That morning we got up and showered together, which led to a quickie under the spray, but by then we were both pretty spent. We got dressed, had some coffee, got our stuff together, and headed for the beach.

We got to the beach a little after ten, parked the car, and went to find Anna's friends. There weren't that many people, and the groups were pretty spread out, so it didn't take long. Two women, wearing hats and sunglasses and nothing else, standing by a blanket laid out on the sand. Two guys, nude, sitting on the blanket looking at their phones. Anna looked at me and raised an eyebrow.

We put our stuff down, and Anna started to undress, so I followed suit. She introduced me to her two friends, Monica and Shelley. They introduced the two guys, who barely looked up from their phones to say hello, and whose names I didn't catch. Shelley was tiny, barely five feet tall and very thin, with curly black hair and an infectious giggle. Monica was about Anna's height, but - not fat, but fuller. Her breasts were larger, probably a C cup, but still very firm, with very large dark nipples. Both the women were checking me out as well.

We talked for a while, about the things you'd expect - how long have you lived here, how did you meet Anna, how do you like San Francisco, what do you do, and so on. When the conversation ran down, Anna suggested we go in the water. The two guys declined, saying they were in the middle of a game, so we left them on the blanket with our stuff and headed toward the waves. It wasn't too cold, but a little chilly for splashing about, so we all just walked out until the water was about waist deep. All the women's nipples were hard and erect, and I had to force myself to look out at the ocean.

Then Anna said, "Shelley, look at those waves. Let's body surf." The two of them left Monica and me standing there and swam out to meet the rollers.

"So," said Monica, "is this your first time at a nude beach?"

"Yeah," I said. "How could you tell?"

"It's the way you're not staring at my breasts."

I shook my head. "I really don't know the rules," I said, "so please forgive me if this is out of line, but you have magnificent breasts. And those nipples."

"Well, technically, you're not supposed to notice, but I'll tell you a secret. Every woman loves a compliment, especially about her body." She came closer to me. "I think it's only fair that I should get to see your cock," she said. "'Nude beach' being the operative words."

"Let's just move slowly back to shore," I said, and we did, until the water level was low enough for her to see what she wanted. She smiled. "Anna is a lucky girl," she said.

Since we were in shallower water, I could see that she shaved her bush, and that she had a small butterfly tattoo just above her slit. We walked slowly back out to where we were before, in time to meet Anna and Shelley, who had ridden a wave in.