I can still remember the day like it was yesterday. My sister, Sandy, Ann, her best friend, and I went out on the Delta in kayaks. We started at the marina at the end of Bethel Road near Franks Tract, bird watching. We each had single kayaks and were finishing our day. We were just crossing one of the channels marked by some levee remnants, when some guy came barreling down the channel way too fast making a huge wake and it caught Ann just wrong. Over she went into the water. 

I was so surprised by her tipping over I didn’t get the name of the boat, Sandy was closer and went to help first. By the time they were able to get it empty of water and the recoverable stuff back in with Ann in too, I just got there.

Ann called out, “Ray, did you get the name of that f-ing boat? I can't believe anyone would be that stupid going that fast here, where there could be anything hiding in the water, including invisible kayaks!”

I answered, “Are you all right? Did you lose anything important? Uh, no. I was too far away, I didn’t. Uh, Sandy?” 

Ann looked like a drowned rat, with her soaking tee shirt molded on her body like she was a participant in a wet tee shirt contest. Someone that got her hair soaked too. That was the drowned rat part. The rest was a woman, all woman. Whoa, I’d never noticed the all-grown-up Ann. Both Sandy and Ann, her best friend were twenty-two coming up on twenty-three. I knew because Sandy and Ann had birthdays one week apart.

I must have noticed because I wasn’t surprised. I’d seen the changes but just never noticed. Today I did, and it was a shock. Why was I ignoring Ann? Maybe because she was almost a sister and my real sister’s best friend. Hell. 

As I said, the shock and surprise had a noticeable effect on me. I’d have to be careful when I got out of the kayak. We got back to the dock and loaded the kayaks on the trailer and Ann was partly dry. There was a small restaurant at the marina and Ann was able to change out of her wet clothes. We sat down for a bite to eat and Sandy commiserated with Ann about getting caught by the wake. 

I was able to carry on my part of the conversation well enough that neither Sandy nor Ann commented on my preoccupation. I was spending most of my time thinking about Ann, nothing I could share with either of them. No, I wasn’t thinking about getting in her panties. I’m not a cross-dresser, I wanted my cock in her pussy and a lot of more interesting ideas. 

At the folk's home, I unloaded the kayaks while Sandy and Ann put the other stuff away, then left for their apartment. All I could think about was Ann is Sandy’s best friend. I want to screw Sandy’s best friend. Hell. When I got to my apartment I took a shower and relieved my sexual tension, thinking about Ann, naked Ann. Ok, I’ll admit it, naked Ann being fucked by me. 

I had to stop thinking about her that way, probably not going to happen, so stay away from her and Sandy. The next day I invited them both to our favorite hang-out place, Smitties’. It’s a combo restaurant/bar/pool hall/dance place. Shit, I guess I’d decided on a second option, screw Ann and I hadn’t even realized it. 

Well, at least I didn’t have to come up with smooth pick-up lines, since I haven’t had any since I’d pulled Marcy's pigtails in fifth grade. By the way, that didn’t work any better than my later ones. Smooth with the girls or women, I’m not. I was wondering, what made me think I’d have any success with Ann. I used to think of her as just my sister's best friend, she probably thought of me as just her best friend’s annoying older brother. 

When we got there, I realized what I’d walked into. Smitties, where guys were going to be hitting on her. Hell, it was worse than I’d remembered, or maybe worse because I was noticing it more. There were a lot of their friends there, and they came by in ones, two, and more. 

This was not just a failure, it revealed my lack of any idea of what to do. I proved I’m an idiot when it comes to women. Sandy, I had no problem with, Ann, my sister’s best friend, I had no problem with.  It was Ann. The Ann I no longer thought of as Sandy’s best friend, I had a problem with. 

I was sitting at Smitties’ pouting, trying to think about how to get out of the ‘best friend’s annoying older brother zone.’ I could take them for a hike, I knew some magnificent hikes. I could invite them to the river for a picnic and swim. We could go to San Francisco to visit Golden Gate Park for a day. 

All those would do is reinforce my role in the ‘best friend’s annoying older brother zone.’ Not what I wanted, at all. Then I had an epiphany if I had the nerve. Dump Sandy, invite Ann to any of those ideas. Hell, it was obvious I needed to get Don and Ann alone time to get unzoned. It was also obvious it would be yes or no time. Yes, she’d be willing to consider me not as Sandy’s brother or no, I’m only Sandy’s brother. I’m not a gambler so putting everything one roll off the dice isn’t normal for me, but I saw myself standing up and asking Ann to dance a slow dance. 

She actually said yes. She’d enjoy a dance. 

Ok, step one is done, now step two. I started by saying, “Uh, I don’t know why I’ve never asked you to dance before, but I’m enjoying it. Ah, Ann, uh, how long has it been since you’ve been to Golden Gate Park? Ah, I’d … like to take you there, umm, the two of us, to look around, uh, maybe?”

Yes, as I was saying it I was thinking ‘Smooth Don, smooth. No one would accept an invitation that clumsy. Well, I did get the essentials in there, Ann, me Golden Gate Park, and just the two of us. I hoped she understood the important part, the two of us. 

I continued leading us while I waited for her answer, yes, no, maybe. It was agonizing waiting.

Ann started then hesitated. More agony for me, I could barely stand it, when she asked, “Uh, when were you thinking? Uh, thinking of going? Um, Don.”

I answered, “The next few weeks would be good. I’d like it soon if you can. Maybe we could stop someplace to eat on our way home?”

As the dance ended she looked at me, kind of strangely, and asked, “As a date, you and me?”

I replied, “Exactly as a date. Yes, I’m asking if you’ll go on a date. I’m suggesting all day in San Francisco, Golden Gate Park. Um, if that’s too much?”

She hurried her answer, “No, it’s not too much. You and me on a date? All day? Um, I’d love to.”

When I led her off the dance floor I kissed her, our first kiss. It was wonderful.

The next morning I got a text from Sandy reading ‘What the hell took you so long?’ What did that mean? Unless it meant … I was late to the party?

While I was driving us there, I was holding her hand, at least a lot. Damn bucket seats.  At the park, we spent time at the Tea Gardens, Rain forest exhibit that I’d never been to, aquarium. I found lots of places for kisses that kept getting steamier and steamier. 

We also had time for a casual picnic in a secluded grassy area. Lots of kisses and kisses, until I couldn’t stop myself. I started touching her tits. At first, it was through her blouse until I discovered that she’d pulled it out from her pants. That’s when I reached under her blouse and slipped her bra off them so I could touch her tits skin to skin. It wasn’t long until I forced her onto her back with me kissing her and my hands caressing her tits and pinching her nipples. Neither of us was very coherent when I heard myself saying, “Ann … uh, a question, Sandy … Sandy, when ah, is she expecting you back? There’s a lot more we could do here, uh if you wanted more time here.” I was blushing. 

I stopped kissing her but was still holding her tits. She was breathing hard when she whispered, “Don, what … .” she stopped then hesitatingly continued, “What would you … What do you intend?”

I interrupted, “Ann, I intend … anything you’ll let me, everything you’ll let me do. Uh, what I want to do. If you would let me, I continue what we’re doing right now. All the way you’ll let me …” my voice petered out. 

Ann interrupted me, “Don, you want us to uh, go all the way, sex, fucking me?” She held my hands on her tits and kissed me harder than ever. “Uh, I’ll have to let Sandy know. She’ll know what we’re doing, she won’t be surprised, but she’ll know. She won’t tell anyone but … she’ll know.” 

I answered, “Shall I text her? Make it more obvious that we’re not hiding it?”

When Ann nodded I pulled my phone out and texted Sandy, ‘Hi Sandy. I want you to know Ann won’t be home tonight. She’ll be with me in SF. She’s with me so I’m not going to say she’s completely safe, but at least nothing will happen she doesn’t want to happen. Don’

I showed it to Ann and let her actually send it. and then I kissed her. I didn’t want to stop there, I hadn’t seen her bare tits yet, but then tonight I’d be seeing everything. I guess I can wait. 

We picked up everything and dumped the trash and went to the greenhouses and walked through. By then it was after three and we decided to get a room reservation near the Wharf. We found a place for Ann to get a change of clothes and then went to check-in.

When we went to our room, we walked in and I just stood there looking at Ann.

This is what I’ve wanted since Ann’s kayak adventure, and I didn’t know how to start. Should I take it slow and savor each piece of clothing I removed and savor each piece of skin I exposed? 

Or should I just strip her and fuck her? 

What I wanted is a strip and fuck. I also wanted a memory I could hold forever.  We’d kind of edged around condoms but both of us wanted skin on skin. It’d be Ann’s first-time bare sex and I decided I wanted it to be a memory she could savor for years to come. 

I said, “Ann, I want to take our time. I want to enjoy each second of our time here. I want to kiss you first.”

With that, I stepped forward and took her head, and kissed her mouth touching her lips with my tongue, ever so softly. When Ann kissed me back, the temperature went up ten degrees. She pressed her breasts against me with her hands holding me closely. I was realizing Ann had breasts, not tits like all the other girls I’d fucked. I also realized what I wanted to do with Ann was make love, not fuck. 

As I was realizing this, Ann pulled me onto the bed unbuckling my belt and unzipping my pants, when I tried to stop her she kissed me harder and unbuttoned my shirt. Before I realized it she had my shirt off and my pants half off. Then I realized she’d put my hands on the buttons of her blouse and I was unbuttoning it. When I undid the last button on her blouse she’d pulled it off and my hands were on her breasts, no not tits they, were Ann’s breasts. I was sure of it. 

We continued kissing but I was moving my kisses down to her neck and shoulders. That was when I felt my shirt come off then my tee shirt over my head. God, were those Ann’s hands reaching inside my pants, touching my, uh penis, or was it my cock. I couldn't tell. 

My kisses were moving down off her shoulders and I noticed somehow her pants were off, panties too. Uh, my pants were on the floor and I was naked and my hands were behind Ann’s back unfastening her bra. And there they were, her breasts. Really, her breasts? Shit, they were her tits, her wonderful tits. God yes, her tits. My kisses had moved down to her tits sucking and licking. One hand reached down between her thighs to her pussy. 

When I was thinking about her pussy I realized we weren’t making love, we were fucking. I was going to fuck her, Ann. I was fucking Ann. I’d lost control of what was happening, Ann was in control and she wanted to be fucked. 

Okay, I can do that. If she wants to be fucked, she’ll be fucked.

I pushed her back onto the bed and I started pulling on her nipples holding and squeezing her tits. I was saying, “Is this what you want, is this enough on your tits? What about your pussy, Ann. Do you want to fuck?”

We were both naked and I was over her with her tits in my mouth, sucking. My cock was just inches from the entrance to her pussy. I could tell my precum was oozing from the tip of my cock. It was too late to slowly make love, I was going to fuck her, immediately, and my cock pushed inside her. 

It was what I wanted, but not what I’d decided on. I was able to hold on long enough to feel her start to spasm in her climax which made mine start. God, it felt … wonderful.

I’ve just fucked my sister’s best friend. A girl that just a few weeks ago I’d thought of as an almost sister too. What will Sandy say when I get her back to their apartment? I’m just going to have to deal with it. Unless that comment ‘what took you so long meant something. I don’t think this is the last time we’re going to want this. 

When we woke, we went out to eat at Scoma's on the Wharf. We had a nice time while ignoring the elephant in the room. On the way back to our room I told her I wanted to make slow intimate love to her tonight. There was an alcove where I kissed her with my fingertips just barely touching her tits and I heard her sigh, “Yes, I thought … “ then her voice trailed off. 

Making love to Ann was even more fun than fucking her. For one thing, I could take enough time to admire her. I could take enough time to kiss her everywhere I wanted. Oh yeah, and Ann could do the same for me. I loved being able to enjoy what I could do to her, and what Ann did to me.

I was able to get Ann to climax twice and when I came, we held each other and slept until morning. After our shower, and a not-too-brief interlude during the shower, we got dressed and found a breakfast place across the street. While we were eating, we decided to visit some places I knew, that had galleries to look at, and then the Ferry Building and then back home. I did take some opportunities to do more kissing and at the Ferry Building, a little breast touching too. God, it was confusing, Ann’s breasts turning into Ann’s tits.

When we got to Sandy and Ann’s apartment, Sandy was waiting and seemed to want me to leave, now. Well, I didn’t want to so I was able to get an offer of coffee from Ann. I finally was practically escorted to the door. As I was slowly closing the door I could hear Sandy asking Ann, “Was it as goo...“ and that was all I heard because the door closed. 

I wonder what Sandy wanted to talk to Ann about. I guess the main thing is what Ann thinks. Did I go too far? I want to spend more time with Ann. I can text later I guess. I hope Sandy doesn’t object, please.

Later that evening I texted Ann, ‘Hi Ann, just a note to tell you how much I enjoyed our trip to SF. I had fun touristing at Golden Gate Park and the rest of SF. I have to add our time at the motel was wonderful too, maybe even better.

‘I’d like to spend more time with you, doing whatever you’d like. When is a good time to call you?”‘

About ten minutes later, Ann called. “I got your text. Uh, what did you have in mind? Ah, Old Sac, or … uh, or something more … um more private?”

“I hadn’t thought that far along Ann. Umm, either, both? I was just checking if you’d be willing to spend time with Sandy’s brother. Ah, what did Sandy say when she got you alone?”

Ann hesitated for a moment, “What does Sandy have to do with it? Do you think Sandy objected to our trip to San Francisco? 

I slowly answered her, “Well, I was wondering, when I dropped you off she seemed to want me to leave, immediately. I was afraid it meant to … “

She interrupted me by saying, “No, she didn’t say anything that was bad, in fact, uh, … “ her voice trailed off. Then changed the subject, “Do you have a roommate? I seem to remember you don’t?”

“No I don’t, not since Steve moved back to Washington. Why?” We were talking about Sandy then my ex-roommate. Oh, god, I’m slow. She has a roommate and I don't. 

I caught her rolling her eyes as she said, “Maybe we could hang at Smitties tomorrow and then … uh, maybe … you could show me your apartment? “

Hell yes, show her my apartment. Oh, yeah! I’d love to do that.

What I said was, “Smitties, last time we went there, I almost got in a fight with all the guys hitting on you.”

“Oh you poor dear, I’ll protect you from my friends. Maybe if you hold my hand it’ll protect you? What do you think?”

“Well, I guess if we acted like a couple, maybe.” The opportunity to show her my apartment is more than enough incentive to brave the horde of Ann’s friends.

We decided I’d pick her up at her apartment at seven. If Sandy’s there, I might pick up an idea of what she’s thinking. 

When I picked her up, Sandy was there. She gave me a hug and a smile and then hugged Ann with a murmur in her ear. As I sat in the driver's seat I asked Ann, “Okay Ann, what did Sandy say as we left? Inquiring minds want to know.”

Ann just waved her hands and muttered, “Nothing much, just have a good time.”

I sat in the car looking at Ann, shook my head, and replied, “And she couldn’t let me hear that?”

Ann hesitated then, “That’s what she meant. She didn’t exactly use those words. She wants me to have a good time tonight.”

“Okay Ann, exactly what words did she use?”

She looked back at me, blushing then replied, “um, ‘You go girl.’. Okay, Ray. She said, ‘You go girl.’ You satisfied?”

“Ah, that’s what she said?” And I started the car and started off. “So, she’s not against you seeing me then. Okay, I’m sorry for making a big deal of it, but I was afraid she’d be against it. Now, I’ll just drop through the car and drag along under it.

“I have an idea, how about we skip Smithies, get a burger or something, and let me introduce umm, to my apartment? “

I waited for Ann to reply. “I’d like that. Just so you know, um, Sandy wouldn’t be surprised if I didn’t get back until six in the morning. In time to get ready for work. I wanted lots of time to get acquainted with your apartment, and maybe some other things there.  

And that’s what we did. She got acquainted with my apartment and reacquainted with some other things there. It was almost as much fun as our night in San Francisco. The main problem we both needed to get to work the next day.

One year later Sandy was Ann's bridesmaid and I found out that Ann had been trying to my attention for months. Oblivious, thy name is Ray. The other thing is that both Sandy and Ann saw the change in me after our bird-watching trip in the Delta. The very best capsize in our lives.