Sailing Adventure

A friend provides a memorable erotic boating experience.

For months I had been looking for a sailboat, I scoured all the local newspapers and could not find what I was looking for. This was before the Internet, as we know it today. Just so, you get some idea of how long ago it was, there wasn't any internet and computer were still using punch cards.

I was at one of my customers' seashore sites and telling the beautiful keypunch girl, Barbara, of my dilemma. It was just an excuse to talk to her every Thursday when I came for computer maintenance. She asked if I would like her to bring in the local Sunday classified every week, I replied that that would be so nice of her.

Therefore, every Thursday she would give me the classifieds and we would chat about sailboats. She seemed interested and often said she would like to go sailing since she had never done so before. I told her I taught a sailing class at the local high school in my home area every other week, but she said it was too far for her to travel. I offered her sailing lessons on my sailboat once I got it; she said she was in for that.

After months of searching, I found the sailboat of my dreams, a 28' sloop that slept 6. It was loaded with all the amenities and made for cruising. I was able to purchase and move it to my yacht club marina just in time for the summer.

I could not wait to tell Barbara of my purchase, I let her believe that it was one of her leads. I said I would thank her by taking her on a sail next weekend. She was ecstatic and so was I; the thought of having a beautiful blonde thirty something alone for a sail was too exciting. I made sure to tell her to bring a bathing suit in case she wanted to swim.

Saturday came and Barbara showed up wearing short shorts and a halter-top, wow. It's the first time I ever saw her legs, they were long enough to reach her very shapely ass. She turned heads when walking down the dock to my boat; I could see people gawking trying to get a better look. It's not as if she was a supermodel, but she was very stunning. At about 5' 8" she was almost my height and had long blonde hair flowing back as the wind blew down the dock. With each step, her medium size breasts bounced in slow motion, almost like a beer commercial.

Once on board, I told her that I had a picnic lunch packed and we had cold beer and wine in the cooler, so we didn't have to rush back. We set sail for a small cove down the river to anchor and have lunch. I let Barbara take the wheel and steer us leisurely down the river. I snapped a few pictures with her at the helm, the wind blowing her long hair; she looked the part of a sailing goddess.

After anchoring, we broke for lunch, eating sandwiches and drinking a few cold beers. Barbara looked so gorgeous setting across from me; I just couldn't take my eyes off her. We exchanged casual chitchat after lunch and relaxed.

I was about to ask if she would like to go for a swim to cool off, when she asked, "Can we swim here?"

"Sure, did you bring a suit?"

"Yes of course, I got a new one just for this weekend," as she reached in her bag and pulled out a very small bright yellow string bikini that looked more like dental floss and Band-Aids.

"You can go forward to change; the door closes off the bunk area so you will have privacy."

I quickly changed into swim trunks in the main cabin area. Barbara came out, my eyes just about popped out of my head. This was the smallest bikini I had ever seen in person. Her breasts were just barely covered, a good portion of them hung out on either side of the small triangles covering her nipples. Her ass cheeks are fully exposed and just a thin strip covering over her pussy.

I set up the swim ladder so we could get into the water. Barbara let me go in first to test the waters, she didn't have to ask if it was cold, I yelped as I eased into the water. She cautiously followed, as she entered the water, her nipples begin to react to the cold. Two very hard nipples began to push on the bikini top; they looked like they might rip through the cloth at any moment.

She just let go of the ladder and fell in, instantly letting out a, "Fuck, this is cold."

She swam over to me and tried to hold on to me as if I was a life raft. My head went under briefly and as I came back up, she began to laugh, "Got you." I grabbed onto her and tried to push her under, my hand went past her head and hit her bikini top, and one tit fell out. She just looked at it and continued to play, grabbing me back. The more she struggled in the water the other tit fell out also, now two very nice breasts and hard nipples are on display. She did not attempt to put them back the bikini top. I thought I would orgasm right there; my hard cock was trying to push its way out of my suit. Fortunately, the water covered it up for the time being.

"I am getting cold can we get back in the boat Bob?"

"Yes, I'll help you up the ladder, just be careful."

She started up the ladder, stopped and tried to push her tits back under cover of her bikini. I wanted to say don't bother, no one is here, but that wasn't actually true, there was another boat coming into the cove.

Once back on board, we went down to the cabin to dry off. I had some large beach towels on-board and started patting her dry, as I came close; she grabbed me and planted a big kiss on me. I must have looked puzzled; I didn't expect that to happen. She responded back, "Didn't you want to kiss me?"

"Well, yes, but I didn't think ... that you ... would be OK with that."

Next she started putting her tongue in my mouth, we started going at it like a couple of teenagers. She removed her top and asked me to finish drying her. I did a very good job of drying off her tits especially her nipples. She responded by pulling down my swim trunks and started to dry me off. My cock had recovered enough from the cold water to come to life, as she held it in her warm hand.

She pushed me down on the main cabin cushion, got down on her knees, and put my swelling member in her mouth. She obviously had done this before; she sucked cock like a pro. I was going to come and was going to pull out, but she held me tight and let me come in her mouth.

Rapture, the feeling of her warm mouth on my cold cock and now the release of my cum in her mouth, what a feeling. Normally, when my wife gave me a blowjob she made such fuss at my cum touching her let alone coming her mouth, that it always ruined the climax feeling. Nothing like someone jumping up and gagging on my cum, to take away that wonderful feeling. Barbara, licked the cum off her lips like it was gourmet treat and smiled at me.

I wanted to reciprocate by eating her pussy. I removed her bikini bottoms and just stared at her blonde bush. Just as I was really getting into it, I heard another boat outside. I didn't think anything of it since we were down in the cabin, until I hear a voice call out, "Bob, you down there?"

"What the fuck," it was my friend from the yacht club, Jim Smith. Damn, what a way to end a moment, crap, did he see what was going on?

Barbara grabbed her bikini and headed for the forward bunk. I was trying to pull my wet swim trunks back on when Jim peered down inside the cabin.

"Hey, what are you up to?"

"Just having a swim," trying to sound nonchalant.

"Who's with you?"

"A friend from work," hoping that reply would put him off and would leave.

Barbara after putting her bikini back on came back into the main cabin. She looked embarrassed and had nowhere to retreat. Trying to ease the situation, I asked Jim, "Hey, do you want a beer?"

By now, Barbara relaxed a little and said she would take one too. I told Jim we would move up to the cockpit and sit. We all sat in the cockpit and had idle chitchat and drinking beer. Jim kept queering Barbara about her life; she just innocently answered his questions. The whole time my mind was racing wondering what did Jim see and when did he see it.

Jim was really looking over Barbara, as if he was trying to place her from a past meeting. Suddenly one of Barbara's answers triggered Jim's memory, "I know now, you and your husband are in the Monmouth civil war reenactors group."

Oh shit, Jim knows who Barbara is and knows her husband. Jim says, "Your husband is Carl and he won the black powder shooting contest last year."

Barbara hesitantly answers, "Yes."

Oh great Barbara's husband is a gun toting reenactor, my life is over. I suddenly got a flash of the newspaper headline, "Jealous husband kills boater with musket."

By now Barbara is feeling the same way, she is looking at me and has this "I have been caught" look on her face. I try to end the small talk and see if I can get Jim to leave, but he just continues talking away. Now he shifts the conversation to my wife, how's Dotty doing? ... How's the kids?

I think we have just been trapped; Barbara's husband and my wife are unaware of our sailing afternoon. Jim could "spill the beans" to either one of them and we're so fucked.

Jim, while in his 50's, is still in good shape and maybe even sexy for an older guy. We have been sailing friends for years, but not what you would call best friends.

I want to bring this to and end by stating, well, I think we should be getting back before the tide goes out. I tried to steer the conversation to some other non-threatening topic. Barbara agrees, not knowing what the tide comment is about, but she wants to leave. Jim takes us by surprise, "You know Barbara you might want to change out of that bikini before you go back. Matter of fact, you might want to get out of it right here."

Barbara stutters, "What are you saying Jim?"

"I would hate to see you get into trouble, by wearing that bikini."

"What trouble?"

"People could get the wrong idea about you two, if you know what I mean."

"What people?" she asks

Jim replies, "You know, your husband and Bob's wife."

I ask, "What are you trying to tell us Jim, you going to rat us out?"

"I could be convinced to keep it confidential with a little inducement."

Here it comes; Jim is going to blackmail us. Shit, what does he want? Money? No, its sex.

Jim says quite bluntly to Barbara, "Take off your bikini and give me a blow job right here and I'll forget all about you two. That way you can tell my wife what I did if I say anything."

Barbara, looks like she has just been smacked upside the head. "I can't do that, Jim, I don't know you."

"Oh, you have to know someone to give a blow job?"

Barbara asks, "How do I know you will keep your word?"

"You will just have to do a really good job."

You can almost see the wheels in Barbara pretty head spinning. Hesitantly, Barbara stands up and removes her bikini top.

Jim says, "The bottoms too."

"Barbara, you don't have to do this," I say as she steps out of her bottoms.

Barbara is now standing naked in the cockpit; anyone motoring by could see her in all her naked glory. Jim makes a comment on her fine tits and reaches out to grab one.

"No don't back away, let me feel them puppies."

As she leans closer, Jim grabs her nipple and pulls her closer. He took the opportunity to suck those nipples and continued to feel her tits. He slowly moved his hand up to her pussy, felt her wetness, and slipped his finger into her pussy. I don't know if she really wanted him get her off, but nature took it course and she was moaning in pleasure. He looks over at me and asks if I have been tapping this great pussy. I just shake my head no. Just then, Barbara lets out a sigh, a few OH's and shakes to a climax.

Jim stands up, drops his shorts, pulls out his cock and presents it to her to suck. For a brief moment, I thought she was going to back out and not go through with it. I don't really want to look at Jim's cock, but I can't resist. It's not threateningly huge, it looks quite normal.

Barbara goes down and starts sucking away, doing the deep throat thing she did to me. Jim's face is making all sorts of expressions; I can tell he is about ready to cum. He grabs Barbara's head and pulls it in more, so she can't pull his cock at the last moment. He groans as he shoots his load down her throat. He relaxes the hold on Barbara's head and she pulls his cock out and licks off all his cum. She looked like she really enjoys sucking cock.

She looks at me and asks, "You ready for another blowjob?"

I can't pass up a blowjob, so I respond, "Yes, go for it."

As she is sucking me, Jim starts playing with her tits. This is more "friendship" than I am used to, I can't say I ever had my cock out in front of another guy except in the gym shower. I thought I would not relax, but I was wrong, I came again.

Barbra went down in the cabin to put her clothes back on. She came back in the cockpit wearing her shorts and halter-top. Jim say he thought it would be fun if Barbara steered the boat back topless, I thought for sure she would object.

"You are some piece of work Jim, she can't do that."

"I think she can and she will enjoy it almost as much as we do, if she knows what's good for her."

I decided to motor back, as the wind wasn't favoring sailing back. As I pulled up the anchor, she took the helm topless and Jim stayed along the side of us in his boat to monitor her. I took the opportunity to snap a few photos with my Instamatic, what a sight, Barbara's nice tits out in full view and her long hair flowing in the wind.

She continued topless all the way back to the yacht club, many boaters waved at her on the way back, as if it was completely normal for a topless woman to be steering a sailboat. As we pulled up to the dock there wasn't anyone around to see her, before she covered up. I don't know if I was disappointed with no one at the club seeing, it was titillating, but probably not worth the commotion, it would have caused.

After tying up the boat to the dock, Barbara kissed me passionately. I started to apologize for the Jim incident, because I thought the incident would have put her off for future meetings.

Barbara interrupted my apology, "The thought of my husband finding out about me spending a day out sailing really would have triggered his wrath. He has terrible temper. He has hit me for much less. Jim's advances was the lesser evil, and I didn't want to chance ruining your life."

Smiling she said, "This was more fun than I could have imagined, when can do it again? ... Can you keep my bikini on the boat, so I'll have it for next time, I don't dare bring it home?"

Adding a final thought, "Just don't have Jim for the next time. I want you all to myself."

I'll have to wait until Thursday to see her again and see if she still feels that way, I hope so. I wonder where I can get the Instamatic pictures developed and printed discretely.