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A Freaky Weekend Part 1

"A boat trip to help a friend, turns into a long distance freaky event."

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We have a long-time friend Tony. Now I’ve known him way before I met Terry. When I bought my first boat, Tony was with me. He’s been sort of my first mate for as long as I’ve been boating.

When I met and started going out with her, I started to bring her along on weekend trips. They took to each other and became close friends.

Now Tony looks like a football player. He’s about six-three and weighs around two-fifty. Believe me, it’s all muscle, but he’s a gentle giant. He wouldn’t hurt a flea, and he’s so polite, he scares me.

As time progressed and Terry got used to Tony, she started to be more open around him. She started to go topless to sun on the deck. She wouldn’t worry about him seeing her nude after her shower, and one time she gave me a blowjob while I was at the helm with him right there watching. He never once in the years that we’ve been boating together been anything other than a gentleman when around Terry. Then one trip, everything changed.

Tony started to bring a girl along once in a while. Her name was Barbara. At first, Terry had to make sure she didn’t go walking around the boat topless, but after the third trip, the two of them were doing it. I was like Tony in the respect that I didn’t go after Barb, just like Tony didn’t bother Terry.

Terry and I were waiting on the boat one Friday evening. The four of us were heading up to Newport for a night of dinner, dancing, and maybe a little fucking, but in separate cabins.

I was at the helm and saw Tony coming down the dock. He didn’t have either Barbara or his gear for the weekend.

“Hey, buddy. Why the long face and where’s your girl?”

“She broke up with me. I can’t believe it. I’m not going. I wouldn’t be good company.”

He just started to walk back up the dock, when Terry came out, “Big boy, wait!”

She jumped off the boat and ran up to him. I couldn’t hear what they were saying but were talking for a good fifteen minutes. Then I saw them kiss. This kiss had a little more in it than I’ve ever seen.

They both came back to the boat arm in arm. She didn’t say anything and went back inside to continue getting ready to leave. He came over to me and said, “Thanks, Chuck. You two have been so nice to me.” Then he went inside.

We got underway and Terry came up the ladder to the upper helm. “What did you two talk about on the dock? He couldn’t stop thanking me.”

“Well, I just told him that we need him aboard the boat and he wouldn’t need her for anything that I couldn’t take care of.”

“Ah, you know what you said can be taken two ways… right?”

“I only said it with one meaning in mind.”

Now she had tried to get Tony to open up more than a few times. All with no success. When I said gentleman, I meant gentleman. He’s your giant teddy bear, but don’t cross this bear.

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~

One day there was just Tony and me on the boat. We pulled into the Harborside to get a drink and talk to some friends. We were standing a few feet from the bar when a man that was arguing with his girl or wife, pushed her. she landed on the floor hard.

Tony saw that and handing me his drink went up to the guy and asked him why he did that. When the jerk pushed Tony, he uncaged the bear. I won’t go into detail, but I ended up bailing him out of jail, and the guy spent the night in the emergency room. The schmuck sued Tony, but when we went to court, the girl was there and after telling the judge what happened, Tony walked out and they arrested the guy for assault and battery.

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~

“Well, at least you talked him into coming. I wouldn’t feel right if he wasn’t along.”

“Me either. Who else would I expose myself to.”

I decided to let her do her thing, and if she could get Tony to loosen up sexually, more power to her, but I had my doubts.

We got underway and right away, Terry put her micro-bikini on. Now I don’t know about Tony, but she never fails to give me a tremendous hard-on when she wears it.

I was at the helm trying to avoid other boats in the narrow channel getting to the east passage when she showed up next to me. She reached down and felt my cock through my shorts.

“Well well, what have we here? Would you like me to take the edge off?”

“Of course I would, but let me get clear of other boats first. I don’t need to explain to the Coast Guard about hitting another boat while getting my cock sucked.”

“Good point. I’ll be back in ten minutes. I’m going down to tease Tony a little.”

“Be careful. He may not appreciate the view right now.”

“Oh, I think he appreciates it, I just don’t know what to do to get him to take advantage of it.”

“I’ll talk to him alone sometime today. In the meantime, just do what you always do but don’t scare him.”

I was out in the bay cruising along when I heard Terry come back. “You can take the edge off now.”

“Take the edge off of what?”

It was Tony, not Terry, “Oh. Ah, not important. Things ship-shape down below?”

“Yeah, but we’re going to have to replace the exhaust gasket on the port engine.”

“I think we have one on board. We can get to it if we get back early enough on Sunday. Oh, I need to talk to you.”

“Sure. If it’s about Barbara, don’t bother.”

“No, it’s about us, I mean the three of us.”

“Ok, what’s up?”

“We’ve been friends for years. What do you think about Terry’s openness with nudity and sex in general?”

“Well, I was hoping that some of Terry would rub off on Barbara. I thought she would on this trip and then the bomb hit.”

“I’m sorry it didn’t work out, but maybe you’ll talk it over when you see her.”

“No… Barb is history.”

“Well, you do know that you have Terry.”

“What do you mean?”

“I’ll be blunt. She wants you to fuck her so bad, but every time she approaches you, you run away.”

“I can’t do that. We’ve been friends for too many years to do that to you.”

“Think about it. You’ve been with us when we’ve had parties. I know that you’ve seen her either fucking or sucking another man. That’s what you wanted to happen with Barbera, right. You’d be willing to let me have Barbara, so you could have Terry, right?”

“Well.”

“You don’t need to bring a token girl to trade for Terry. All you have to do is accept her.”

Just then, Terry came up the ladder, “You ready for me to suck the cum out of your balls?”

She looked and saw Tony for the first time. “Oh, Tony. Sorry, I didn’t see you there.”

I was just going below. “Let me know about that gasket, Chuck?”

“I will Tony, and thanks for letting me know about it.”

He went below and Terry came up to me. she held my cock through my shorts again, “Did you talk with him?”

“Yes. I wouldn’t rush it and I wouldn’t be surprised if he rejected you, but I told him that I gave my blessing to whatever you did together. That’s when you came up.”

She started to unfasten my shorts, “Well, I’m not going to force him into anything. I would never push him away from you just to fuck him with that huge dick of his.”

“Well, that’s… wait!... what huge dick! Have you seen it?”

“Down boy. Just teasing you.”

My shorts hit the deck about the same time as her knees, and a few seconds later she had my rapidly hardening cock in her mouth. she started sucking and using her hand to jack me.

“Oh, fuck!! I can never get enough of your wonderful mouth. That feels fantastic.”

She took me out of her mouth and stroked me as she said, “I love feeling you get hard in my mouth. It gives me a sense of power. I don’t get that very often with you.”

“I hate to be a party-pooper, but I’ve got a large boat to try to fit into a small slip.”

Then she got to work. She used every trick in her book on me to get me off quickly. And she succeeded. I came… and came… and came, and she swallowed it all, well, almost all.

After a few minutes of recouping and groping each other, we got un-naked and went to the main salon. 

Terry was just holding her top in front of her until she got in the cabin. Tony was sitting at the bar when she walked by him and dropped her top on his lap. Then she sat on the seat next to him.

He didn’t look at her or make a move. Then he took her top, folded it nicely, and placed it on the bar. then she pushed it further by taking off her bottoms and dropping them across his shoulder. He took it slowly off his shoulder and folding it carefully, he placed it on top of her top. He never looked at her.

“Tony! What the fuck does it take to turn you on?”

He turned his head slowly and looked at her, “I am turned on.”

“Well, God damn it. Are you going to do something about it?”

“Yep. I’m going to my cabin.” and with that, he got up and left.

“What is wrong with that man. I’ve never been turned down before.”

She was pissed and I was laughing.

“Don’t you know when he’s teasing you? I told you not to be in a hurry. You know that he’s in there beating his meat with a vision of his cock buried in your pussy. I’ve got a feeling that tonight will turn out just fine.”

Terry got dressed, if you can call shorts, a tube top, and sneakers, dressed, and went shopping at the brick marketplace. She was gone about three hours and when she climbed on the boat, Tony and I were sitting on the deck drinking beer.

“We’re going for dinner around seven. I want both of you to wear pants and not shorts. Look presentable. I’m going to take a shower.”

We sat there and continued talking about girls and boats. It was about five-thirty and I asked Tony if he would get another round. He got up and went in. when he came back about ten minutes later, I asked him,

“What the fuck took you so long. I thought you fell off the boat.” I was laughing but stopped when I looked at him. His t-shirt was wet and so was the front of his shorts.

“What the fuck! You're supposed to take a shower without clothes.”

I looked behind Tony to see through the glass slider. Terry was standing inside with a towel wrapped around her head, and nothing else. She was dripping wet. I looked back to him to see him blushing.

I had to laugh, “I’m not going to ask what happened, my friend, but I think my wife just came on to you.”

“Listen, Chuck. I can’t do what Terry wants me to do. We’ve known each other too long. I’d feel like crap if anything happened.”

“Well, I would guarantee that right after it happened, you would feel good, damn good. It’s the next day, that’s a killer. Take my advice for what it’s worth. Let your cock be your guide. When Terry set’s her mind to something, she won’t rest until she completes her task, and right now, you’re her task. Now let’s go up to the club. We can take our showers there. More hot water and space.”

We took showers and got ready to go to dinner. We were just stepping on the boat when the slider opened and Terry came out.

She was dressed for the kill. I’d know that look anywhere. Short black skirt with a slit up one side almost to her waist. One of my dress white shirts unbuttoned and tied below her tits. Black lace top thigh-high stockings. There was no hiding what she had on her legs as the lace, and the bare skin above the lace showed in the slit of the skirt.

She was carrying her black heels as she knows better than wear them on the boat. Barefoot or topsiders only on the boat.

We were wearing khaki pants and I saw Terry looking at Tony’s crotch for signs of endearment. She smiled, so I guess it was working.

I said, “Well, all we need now is a place to eat… food.”

“Yes, and sooner than later. My sugar is dropping.”

“Do you have any candy with you? Make sure you do.”

She handed me some candy, “Put these in your pocket just in case.”

We left the boat and after walking over to where the food was, we managed to get an outside table right on the dock.

Now usually, when the three of us went out for dinner like this, Terry and I sat on one side of the table, and Tony either alone or with a girl, sat on the other side.

Terry was right next to Tony and she sat on his side, leaving me alone. She was bound and determined.

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After baked lobster all around, a bottle of wine, and the ocean air, we were all ready to head back to the boat. Terry was getting gitty, and I knew that when she’s like this, she gets very horny.

We decided on having a drink at the outside bar as it was so warm and there was no wind. Terry sat and we had to stand. The people walking by were drawn to Terry. At one point, I had to head to the men's room and when I came back, her other bodyguard was talking to someone and Terry had four young college kids talking to her. well, mostly trying to look down her shirt or hoping she would turn just the right way.

“Gentlemen. I see you're out looking for a MILF.”

“Hey! I’m not a MILF. Do these look that old?”

As she said those words she pulled open her shirt, showing her bare tits to the young men. The wine was starting to show. I had to pull her shirt together because she forgot to do it and the boys were not going to.

“You mean I can’t ask them back to the boat. They’re all so cute.” I didn’t answer her.

We left the restaurant and while walking back, she untied her shirt and let it open with the wind. People walking by caught a good look at her beautiful tits with her large dark areolae and hard nipples dancing with every step she took.

Thank God there were not many people going to our slip. We helped Terry get on board and we all sat at the bar. I got her a glass of wine and we had a beer. We retired to the other side of the main salon where the TV was. Terry decorated the area with two couches facing each other with a coffee table in the middle. The way they were, you laid on the couch and watched the TV which was at the end, and hangs down. everything in that part of the salon is movable.

I pulled my shirt off and laid on a couch. Tony went down on the other one. Terry started to lie down with me and before she did, she took off her shirt and skirt. This left her in panties and stockings.

Tony said, “Before you lie down, why don’t you put on an action mo1vie. There's nothing on TV at this hour.”

She put something in the recorder and lied down so we were spooning. Then an x-rated movie started.

“Hey! There’s no action in that!”

“Not yet. But I can guarantee you, there will be shortly,” she laughed.

Tony didn’t put up much of a fight, and soon we were watching a guy with a rather large cock having it go in and out of the mouth of a slim woman.

After a few minutes of watching, Terry tapped me on my hard cock and pointed to Tony. I looked over to see him rubbing his cock through his pants. Then she whispered to me,

“Take your pants off.” So I did.

Now my hard-on was polking her right between her legs. Then she lifted one and trapped my cock between her thighs. She started to move her hips like she was fucking. The friction was getting to me quickly and I had to pull myself out to take a break.

Then she got up and went over to Tony. She stood there for a moment before getting on her knees next to him and reached for his belt buckle. He put his hands up and grabbed her wrists.

“I don’t want you to fight it, big boy. You're going to become one of the family.”

I noticed that he wasn’t fighting much. She swatted his hands away and he didn’t put them back. she unbuckled him and slowly unzipped him. He put his hand up again.

“Oh, no you don’t. you just lie there and enjoy what I give you.”

When she had him completely unzipped, she reached in and extracted his cock.

“Oh, my fuckin word!! You’ve been hiding this from me all these years?”

Even I didn't know he was hung. I didn’t have a lot of light and Terry was blocking a little, but he looked to be about eight inches, but what I think had Terry in a state of shock was the thickness. I figure about the size of my wrist. I was looking forward to watching her try to fit it in her tight pussy. She better have a bottle of wine first.

I think Tony has given up. He just laid there and covered his eyes with his arm. She reached with both hands and held it straight up.

“Fuck, it weighs a ton. How the hell do you walk around with this?”

I was surprised when he answered softly, “I don’t walk around with it hard like it is now.”

“Well, I’m not quite prepared for this, so I’m just going to jerk you off. Do you mind?”

“Terry, I’ve fought you long enough. Chuck's told me that he’s fine with this so all I can say is have at it.”

Terry pulled his pants off along with his topsiders and straddled one of his legs. I noticed that she made sure that I could see everything. She reached over next to her and grabbed a tube of lube that she so strategically placed there. She squirted an ample amount down the length of his cock and began using both hands to stroke him.

“Now you let me know if I’m doing it right. Faster, slower, grip tighter or looser and you better fuckin tell me when you’re going to cum.”

She continued to stroke him with both hands, then she took her oily hand and wiped the leg she was straddling. I knew what she was doing and smiled as she looked over at me.

She started to rub back and forth on his leg. She was rubbing herself off on his leg. I saw her close her eyes and then look down at his stiff cock. When she started moaning, she was close. She quickened her pace on his leg and then.

“Oh, fuck Terry! I’m cumming! Gonna… cum… right… NOW!”

She must have felt his load cum up the tube because she waited even after he raised his hips. Waited till the first thick wad of cum was right at the opening, and then clamped her lips over the crown. It surprised him and he jerked his hips up hard, just as she was coming down. the result was her mouth was stretched to the limit with his cock.

She took her hand off him and held her head still. I watched as his cock contracted with each shot of cum. I think it was a show for me as she looked at me and winked.

She told me later that she has never had that much cum in her mouth before. No, I didn’t ask. should have, but didn’t.

She struggled to swallow it all without spilling any but managed pretty well. She waited until she was sure she had it all and then took a couple of deep mouth strokes to clean him.

She leaned down so her face was right above his, “Well, what do you think now?”

“I think that I should have given in years ago. I can’t think about all the times we could… .”

Terry interrupted him, “Yep, just think of it, and now that the cat’s out of the bag, I suppose you’re going to want to make up for lost time?

“Well… I.”

“You’re going to have to work it out with Chuck. I’ll do whatever he tells me to do. Now I’m going to the head and take a shower. Would one of you hunks get me a wine?

When she left I asked Tony, “Well, was it worth waiting for about ten years?”

“Chuck, I have never in my life had a hand job like that, and the finish? I think I’ve cum in a girl's mouth only one other time, and she spit it out on the seat of my car.”

“I’ll take that as a like.”

I got terry’s wine and brought it to her. she was just getting out of the shower and I handed her the glass.

“So you happy now? You finally have Tony. You sure your up to taking care of the two of us?”

“I’ll give it my very best. Oh, what have we here? is that for me?”

She started to get down on her knees when I stopped her.

“No, I think we should get some sleep. We’ve got another two days to have fun.”

The three of us were tired. I think I was asleep before my head hit the pillow.

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~

I woke up at around five, and the first thing I noticed was a strong smell of coffee. I managed to detach myself from Terry, make a pit stop, and head to the galley. Tony was sitting at the table nursing a Cup of coffee.

“Morning, How are you feeling this morning?”

“Good, I guess. I'm still trying to digest what happened last night.”

“Well, don't think too hard. You've got two more days with her, and I think she's going to want her fill of your cock.”

I poured myself a cup and sat down. We talked about what we were going to do today.

“Well, I think we should take a ride over to the block. A very slow ride.”

We both looked to see Terry standing in the doorway. She had shorts on but nothing else. She poured herself a cup and sat with us.

“The day looks like it's going to be warm. It will be a good ride to the block. I'll be able to lay out and get some sun again.”

We finished our coffee, and Tony and I went to get the boat ready to leave. We were checking lines when Terry came out and told us that she needed a few things, and would be back shortly.

Now I know Terry, and her short time turns into over an hour. she was carrying three bags. I learned a long time ago not to ask.

I started the engines, and in a short time, we were on our way to the block. It was about nine in the morning. I looked down from the helm and watched as Terry came out with only her micro bikini bottoms on. I knew we were in trouble when I saw a large glass of wine.

Tony came up to the helm, which he doesn't do very often.

“If I didn't know any better, I'd say you were trying to stay clear of her.”

“You might say that. It's a little early for sex.”

“Don't tell Terry that. Her time frame for sex is anytime. The only thing I can say is to say no.”

“Easy for you to say. I used to be able to handle it, but after last night, I'm not sure I even want to.”

I figured what the hell and pulled out a can of beer from the small fridge. Tony was right behind me. When I looked down at Terry again, she was still lying down but without her bottoms. I called Tony over, “Look. Now she’s naked.”

But when we looked, she had her legs spread wide with her feet on the deck. She had her right hand strumming on her clit and the other pulling and twisting a nipple.

“Oh, crap. Now she’s gonna want to be taken care of. I’ll flip ya for it?”

Tony said, “No, I think you better take care of this one. I’ll take the helm while you do her. Oh, and do it right there so I can watch.”

I didn’t say anything. I got another beer and went down on the deck. With the engines running at two thousand RPM, it was easy to sneak up on her.

“Boo, you look very content. Did you get off yet?”

“I was just about to before I was so rudely interrupted.”

“Well, in that case, let me help you, while you think about Tony's big cock.”

I got down on my knees between her legs. I put my hands on her knees, pushed them apart as far as they would go, stuck my face in her sweaty Pussy, and started licking.

As soon as my tongue touched her clit, I knew she was hot as hell. I had to grab hold of her ass cheeks in order to keep myself attached to her.

In her condition, she wasn't going to last long. When she started to come, she reached down with both hands, grabbed my hair, and suddenly I couldn't breathe. I didn't know what was worse, the pain in my head from having my hair pulled, or almost losing consciousness for lack of oxygen.

“My God. I needed that. Thank you so much, my love, you're always there when I need you. Where’s Tony?”

I pointed to the bridge, “Up there steering the boat and watching you.”

“You mean he's been watching us all this time?”

“Yes, and right now, he's probably jerking off. I hope he cleans up after himself.”

“Well, he should have come down here. After I finished with him, he wouldn't have to worry about cleaning anything up, except maybe my chin.”

We got into the block at about noon. After checking with the dockmaster, we tied up at our slip. Tony and I spent the next hour cleaning the boat. You can't leave the saltwater on. It will eventually eat through anything.

We decided to eat in. I had a couple of menus aboard that we went through and ended up with pizza. While we waited for it, we sat at the bar having a beer. Terry was working on what must have been her 4th wine, and she was starting to slur her words a little.

She was wearing a tube top that was bunched up so just a small strip was covering her boobs. Her shorts left the bottom half of her great firm cheeks showing. She was a walking erection.

We took our drinks out on the afterdeck and settled in the lounge chairs. After a few minutes, Terry got up and went over to Tony. Without saying anything, she sat on tony’s lap and reached under the leg of his shorts, and took hold of his cock.

“like me to relieve some of the pressure I can feel? I could go for an appetizer.”

Tony thought about it for a minute, “Sure.  I don’t have to say no anymore so, Yes, relieve the pressure." She was just about to get up and lead him into the boat when a loud "TERRY!!" came booming in.

 

Stay tuned for Part 2 soon.

 

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