Boating Ch. 2

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He's introduced to the pleasures of a threesome.
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Part 2 of the 3 part series

Updated 11/02/2022
Created 09/14/2001
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Chapter 2: The Awakening

I first fucked our corporate attorney, Janice, on my West Wight Potter sailboat. It was great. Our maturity and experience created an open comfortable atmosphere without inhibitions and without worry about showing a little gray hair, or a little extra padding. Since then, we managed to either boat, or find business trips with common destinations about twice a month. I grew accustomed to licking her clit, and to her sucking my cock with no provocation. She loved cock.

One weekend I told my wife that I was off to sail and explore the coast of Lake Michigan. She hates boats because she thinks they are uncomfortable, and was happy to have the weekend alone (that's another story). I headed to the marina, thinking about getting a great fuck and suck from Janice. I could just feel my tongue sink deep into her juicy pussy before I reversed and put my cock where my mouth had been, and vice versa. I loved the taste of her juices, and the taste of my cock on her mouth when we kissed. It was a good world.

When I arrived at the marina, however, she was not alone on her cuddy cruiser. A gentleman in shorts and no shirt, broad shouldered with a modest midriff and gray hair said "hello, you must be Janice's friend." Janice then stuck her head out of the cuddy cabin and said "HI!" in a very cheery voice. Her eyes seemed to twinkle more than usual. She had on a low cut white T-shirt with no bra that showed her cleavage and her D breasts. I could see her nipples through the cotton. She was just pulling up black shorts. I caught a glimpse of her mound through her white panties and a bit of smooth thighs as she arranged the shorts. I had licked those soft ample thighs many times. I wondered who the guy was.

The look on my face must have given my thoughts away as I glanced at her gentleman friend. He said "I hear that you have been fucking my 'ex' and that she likes it." My mouth gaped open in surprise, and both he and Janice laughed. He offered a hand to help me aboard and continued to smile as I stepped over the gunwale. He appeared to be sizing me up as he kept my hand in a firm grip until I was solidly aboard. As our hands parted, I felt a mild electricity and was a bit confused.

Janice said, "This is Bob, my ex-husband. We were married about five years until I caught him with a lover."

"She caught me with my business partner, Rick," Bob added. Janice explained that she was so surprised and revolted at the time, that she filed for a divorce and got it.

I still must have looked confused, so they handed me a beer and told me their story. She and Bob's sex life in the marriage had been excellent. She just could not understand him taking a lover, let alone a man. After the divorce, they did not see each other for over 20 years. About three years ago, Janice was 47 and Bob had just turned 50, the two saw each other when they were vacationing independently in Wisconsin. By then, old wounds had scarred and they decided to talk and catch up on each other.

One thing led to the other, and Bob said to Janice, "You know, I am not gay, just bisexual. I still love sex with women." Janice said, "That's a relief. I thought that you were faking it in our marriage and that there was something wrong with ME. I was really hurt and depressed." Bob explained that he had loved Janice, and truly enjoyed their sex. He just needed more from time to time, something a woman could not provide. He had wanted to explain at the time, but he did not have the words, and Janice was not listening. Janice told him that she was listening now, did he have a boy friend along on this vacation? Bob felt like she had hit him when she said that. He explained that he and Rick had parted company, both in body and business, several years ago. Since then, he has seen several women, and a few men. He never remarried, nor had she. She said that the night of their reunion encounter she felt soft hearted and horny. They ended up having a great fuck. Since then, they have seen each other about twice a year.

Janice has opened her mind a bit over the last few years. She explained that during a rendezvous with Bob, after a particularly good one-on-one man-to-woman sex match, she asked Bob what he saw in men. So, he told her.

His main sex interest is women and he loved pussy, but he knew that he was not repulsed by men. He loved to masturbate, and when watching porn flicks, he was not satisfied unless he saw good cock. Cock entering cunts. Cock being licked and sucked. Cock being stroked. Cock cumming all over a fuck partner. He could feel himself cum when "the cock" came. He ended up tasting cock when a good oral-cock scene came on. He realized, he wanted some cock too.

He knew that his business partner was a little different. Rick was married, but Bob knew that Rick had looked at his crotch from time to time, and occasionally held eye contact longer than men usually do. A few times after a firm handshake, their hands lingered momentarily and their was electricity between the soft parting of skin that Bob could feel go right to his dick. A pleasurable sort of feeling. Bob was not sure if it was just him, his imagination, or something mutual. Bob finally brought the subject up. "Rick," he said, "this may sound funny, and I know you are married, but have you ever fantasized about.. uh.. about.. being with a man." Rick looked like he had been caught with his hand in the cookie jar. He said, "Is this really a private conversation? Totally confidential?" Bob said, "Yeah, just between you and me. I asked the question remember?" Rick confided that he did fantasize about men. He had had an experience in college that he enjoyed quite a bit, but was afraid of being discovered and ostracized. Besides, he liked fucking women too, especially his wife. He was afraid to do anything now because of AIDS and because of the social stigma. Bob told Rick that he was in the same boat.

About this time during their story telling, both Janice and Bob noticed my hard on. I admitted that I was also in the same boat, pun intended. I asked Bob to tell me more, if Janice didn't mind. Janice said that if it gave me a hard on like that, Bob should continue. In the meantime, she would cast off and drive us out into the lake.

Bob told of his first encounter with Rick… After they both knew that the other had fantasized about being with a man they agreed that they should do something about it. They locked the office doors one evening, told the cleaning people they would be working late and not to bother to come by that night. Then they looked at each other.

They did not know what to do, or where to start. Bob, being forward by nature, unzipped his pants and pulled out his half hard cock and stroked it, all the time looking at Rick to see his reaction. Not knowing what to expect, Bob had a "fight or flight" adrenaline rush. Rick's eyes riveted on Bob's dick, and he seemed to melt. He knelt down on his knees, looked up at Bob and said, "May I touch it?" Bob nodded and pulled his own hand away. Rick gently stroked Bob's cock and then took the head in his mouth. He sighed and said hmmm, and lowered his head and mouth completely onto Bob's cock and began sucking and stroking. Bob leaned back against a desk and ran his hands through Rick's hair as Rick worked up and down on his swollen shaft. Bob gently stroked the side of Rick's head and he could feel himself through Rick's cheek as his cock moved in his mouth.

After a minute, Bob said stop. Take off you pants. Both of them had their pants off in seconds and stood naked from the waist down with their dicks standing a full attention. Bob pulled Rick to him and kissed him, tasting his own cock as he flicked his tongue between Rick's lips. As they drew close, they both shuddered as their cocks rubbed their smooth sensitive shafts together. Bob then knelt and took Rick's 5 inch cock and licked up one side and down the other, lingering on the head for a moment. He cupped Rick's balls in one hand while stroking the base of the cock with the other. While stroking and cupping, Bob sucked in Rick's cock down to where his fingers gripped the base and sucked and stroked in rhythm.

Rick said, "God that's good! My wife can't do it like you do!"

"Let me taste your prick again!" The two lay on the carpet in a 69 position and sucked and stroked each other like starving men. Rick came first, a little to Bob's surprise. He had felt Rick's balls tighten and his dick seemed grow in his mouth, but the sudden twitch and hot explosion caught Bob slightly off guard. Bob felt the cum fill his mouth so he swallowed and sucked and stroked and milked until Rick was dry. It tasted good! A tinge of sweetness with a touch of yeast loaded with SEX. Bob could feel Rick work on his six inch shaft with vigor until he came. Bob's felt as if his cock were enveloped in the smoothest silk that was warmed perfectly just for him. His cock felt like it had expanded to twice it's normal hard-on and he was hard as steel as he began to shoot in Rick's mouth. Rick took it all in, and worked Bob's cock as Bob had done his. The head of Bob's dick became hypersensitive as Rick licked it clean. When they both finished, there was nothing left to clean up.

They both put on their pants and looked at each other sheepishly. Bob leaned over and gave Rick a kiss on the lips, smelling and tasting his own cum. Then he said, I liked it. Rick said that he loved it! Thereafter, they met on a regular basis and sucked each other. Frequently, they would begin their sessions by telling each other about the latest sex they had had with their wives and turn each other on by visualizing their partner's dicks sliding into soft cunt. They became ready to suck dick by thinking about pussy.

As the boat planed swiftly along the lake shore, I told Bob that I found his story facinating. I had never had a dick in my mouth, despite my age, but had thought about it for a long time – as long as I can remember. I think I like cock and am not repulsed by a man. Bob looked at me for a moment, then took his prick out of his shorts and started stroking it, much as he had done on his first encounter with Rick. I looked at Janice, who was behind the wheel of the boat, and she smiled and nodded toward Bob's dick. She said, "I'm more open minded now, and I have plans for both of you later. Go ahead and try something new. Besides, I want to watch." She slowed the boat to crawl and slid one hand into her pants. I could see her rubbing her clit as she watched us.

I knelt down in the boat between Bob's legs. He leaned back on the soft boat cushions and continued to stroke his hardening dick. I put my hand on his and worked it up and down. Then I removed his hand and wrapped my hand around his cock. I licked a drop of pre-cum off the head of his prick. It was smooth and slippery and tasted a little like fresh bread and baby oil. I then licked around the head of his dick and down the shaft. Bob visibly relaxed and said, "You are doing fine. I will want your cock soon." Then I took him deep into my mouth with the head of his cock touching the back of my throat. I did not have a gag reaction. It felt and tasted vibrant, smooth and wonderful. I sucked and stroked Bob's cock and liked it. I had not noticed that the boat had gone silent until I felt Janice kissing my ear and the side of my neck. When I looked up, I saw that we were drifting alone in the lake, far from shore and far from any other boat. As I looked around, Janice took my place sucking Bob's hard cock. I slipped out of my clothes. She was on her hands and knees, so I pulled down her shorts and pushed up her T-shirt. She continued to suck Bob's cock while I kissed the back of her neck and reached around with both hands and cupped her tits and rubbed her nipples between my fingers. All the while, my hard cock had slipped between her ass cheeks and was massaging her anus and the lower lips of her moist labia. Between my pre-cum lubrication and her moist pussy lips, my cock slid up and down along her ass and pussy lips in a smooth, sensual way.

I removed her shorts the rest of the way and spread her legs. She was still on her knees facing Bob as she gave him head. I reached between her legs and ran my hand up and down her moist vulva, touching her clit and then rubbing back with my fingers sweeping deeper into her hole with each rub. I kissed her ass cheeks and then ran my tongue from her pussy lips to her anus. I put my hand back on her pussy, inserted two fingers, and rubbed her anus with my thumb.

She stopped sucking Bob and had him lay down in the boat. She then straddled him and impaled her cunt on his dick and worked up and down a few times. I rubbed her ass and gently inserted a finger while she was fucking Bob.

She looked at me and said, "Put on a condom and stick your dick in my ass!" She must have been really hot thinking about fucking both Bob and me at the same time. Janice and I had experimented with some anal play in the past, but never to this extent. I had hoped to fuck her deep in the ass someday, so I usually came prepared. I pulled a lubricated condom from of my discarded shorts and rolled it down my cock. Bob watched me with blazing eyes.

I knelt behind Janice and moistened her anus with spit, and inserted the head of my sheathed cock. She moaned and said deeper, please, but go slowly at first! She stopped humping Bob momentarily as I shoved my dick up her ass. It was another first for me, and it felt tight and good. She asked both of us to pump slowly and we did. Bob must have been in shape to pump with Janice on top. I kept my weight off her and focused on pushing my cock in her tight ass. I could feel Bob's cock moving in and out of her pussy as I pushed deeper into Janice's ass. It was like locking our dicks together sheathed in pussy and ass making a three-way pleasure machine. All three of us were grunting and moaning and fucking as best we could. Janice was being ridden deep by me, and fucked by Bob. She could not last and moaned that she was cumming. Her orgasm seemed to last a very long moment, or perhaps she had multiple orgasms. She kept shuddering and moaning and saying, "don't stop yet!" Then she collapsed on Bob. My balls tightened and I came, shoving deeper. I felt Bob twitching too. What a sequence!

I pulled out of Janice's ass with a plop, and rolled the condom off my dick. Janice rolled over and Bob's cock slipped out of her cum soaked pussy.

I said that perhaps we should clean up. Janice had some wash clothes in soapy water in the cabin, so I retrieved them. She said for Bob and I to go ahead because she was still catching her breath. Bob took the wash cloth from my hands, and gently washed my soft but still slightly engorged cock. He cleaned and rubbed around the base, my pubic hair, and he reached through my legs and washed from the crack of my ass across my anus to my balls. I mentioned that I had not been fucked there and that he was reaching a bit. He said that it pays to be clean – who knows what the future holds. His careful sensuous motions on my loins, combined with the smell of soap and clean lake air gave me a sense of well being, and the beginnings of a new hard-on. I washed Bob as thoroughly as he had washed me.

We both turned to Janice, who said, to wait just a minute because she wanted to douche. I said, "What, no more fucking today?" She smiled at me and said "Sure there will be, but I like to start fresh each time. It is kind of like setting the table." I understood immediately. Now I understood her secret of why her pussy always smelled and tasted good enough to eat. We watched her douche, then Bob and I washed her entire body and massaged her from neck to toe. She loved the foot massages. Before we dressed again (temporarily) and had lunch, she patted some flowery smelling water on her pussy and ass. I was tempted to move to her and kiss and lick her cunt, clit, ass and body all at one once, but she made me wait. She simply said, "Anticipation…"

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Boating Series Info

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