We Both Wanted It

After high school and before college I spent a year working in Florida. Just took some time for myself. I worked at a landscaping company. It was hard, hot work, but I enjoyed it. The office manager, Jane, was a cute woman a bit older than I by maybe 10 years. Jane’s boyfriend, Ted, who she lived with was a captain on a yacht, the owner of which was a NY real estate guy.

I became friendly with Jane and her bf. Maybe half way thru my time in Florida Ted needed to take the boat to Nassau in the Bahamas for the owner who was flying in with his family. Ted liked to have help when making a crossing of the Gulf Stream and Grand Bahama Banks, so he asked me. The pay was good and I knew boats, so I was in. The trip from Ft Lauderdale to Nassau by boat was about 12 hours. We were leaving early in the AM so Ted suggested I sleep aboard the night before, as he planned to do.

I had barely settled into my cabin when Ted suggested drinks before dinner. I quickly saw a side of Ted I’d never seen. He was quite obviously a switch hitter when the opportunity presented. As it happens, so was I.

Before long I was on my knees orally servicing Ted’s sizable cock. He knew I had the hots for his gf Jane and as I was sucking his cock he’d say things like “that cock was in Jane’s pussy this morning , or “do you taste Jane’s asshole on that cock”? or “that’s just how Jane sucks my dick, only deeper”.

I have to admit my bisexuality was in high gear when Ted teased ne and then fucked me and I couldn’t help imagining that I was Jane. The more I encouraged Ted with comments like “Is Jane’s pussy this tight”? Or “are you fucking me as hard as you fuck Jane’s c**t”? the harder Ted pounded me. It was like some mindless primal fucking and I loved it. When Ted came deep in my asshole I moaned with pleasure and told him Jane was lucky and so was I. Ted just smiled….then fucked me and filled me again.

Although I did not know it at the time, Jane knew Ted planned to seduce me and it became a topic of discussion when the 3 of us were later together. Well, you guessed it. The three of us had great sex together on many occasions and I got to enjoy Jane’s pussy and asshole…just like Ted.

Comments

Anonymous

by Anonymous on Jun 18, 2025 at 1:01 PM

This is not a gay or bisexual story. It's the fantasy of a frustrated heterosexual. It's how he imagines gay sex, not how it is.

When a man gets fucked he's not pretending to be the top's wife. Being a bottom is not necessarily a feminine role, nor even a submissive one. The masculine versus feminine dichotomy is usually imposed from the outside, as a way for straight people to catalogue gays.

When I fuck men I like them to fight back, not to submit. If I hold a guy down I want him to resist. I don't want it to be clear who will "win" until my cum is dripping from his hole. It's not at all like the sex I have with my wife. If I wanted to fuck a woman, that's what I'd do.

This confessor also has a fixation on oral-anal contact and anal sex between men and women. Anal play is exceedingly rare in heterosexual couples. Only a handful of women consent to such play. Based on this guy's confessions, you'd think it happened every night, behind closed doors in Florida's suburban ranch houses and dilapidated concrete condo towers!

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Anonymous

by Anonymous on Jun 18, 2025 at 4:27 PM

To each his or her own but the whole tale of sailing and sex with Ted and then being lucky enough to have threesomes with the two of them is absolutely terrific and despite the above commenter's take on it, if it actually is mostly true, the OP is one very lucky fellow indeed.
I'd be very happy to have a couple of friends like that myself and I'm a randy old man.
I sure would've loved that even more when I was young and full of cum.

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Anonymous

by Anonymous on Jun 19, 2025 at 6:16 AM

Many years ago in my early 30’s I met this guy at work. We became friends and drinking buddies. One day at the bar he started to mention his hot wife and talked about their sexual activities.
His wife was a total knockout. Very sexy and beautiful. Long dark hair big boobs small waist nice ass and the best looking legs ever. The longer he talked the harder my dick got. All I thought about was fucking her then he told me she was out of town visiting family and he invited me to their house to continue drinking. Once we were there he opened us a beer then asked me to follow him so I did.
We went to the back bedroom where he pulled a shoe box out of a closet and opened it and it was full of pictures of his naked wife in different poses and her using sex toys. Then pictures of her sucking his long fat dick. Cum shots and pictures of his dick in her ass and fucking her pussy in different positions.
Even pictures of her spreading her pussy open with cum running out of her and cum dripping from her asshole. My dick was hard as a rock and he knew it because he started asking me if I would line to fuck his wife and he talked about how she wanted a threesome then he dropped it on me. He told me he was bi curious and his wife knew it and wanted him to have sex with a guy in front of her and she wanted two men at the same time.
Then he invited me to get naked with him and see what we might enjoy together. I told him I was IK with that because looking at all those hot pictures had me horny and I was a bit on the bi curious side myself. I spent the night and he and I sucked each other off twice then once in a 69 where he really got into making me gag on his big dick. We both swallowed each others load that third time while we were in a 69.
We fell asleep but just before dawn he woke me up with his arm over my chest and his body up close to mine as he rubbed that big hard dick on my ass. It felt good and I had always been curious about getting fucked and I had explored it with different things and a couple of times I had even bought a dildo to play with. So when I felt his pre cum on my ass and he started to hold me tighter and tell me he wanted to fuck me I told him we could try it but to go slow as his dick was pretty big. He rushed to get the lube from the other bedroom and he knew just what to do and not long after he put some lube on my asshole and fingered me he lubed up his big dick and was on top of me trying to put it up my ass.
Once the hard was in my ass it stung pretty bad but he waited then slowly pushed until I felt his big nuts touching mine. Both of us excited a lot of moaning and groaning and heavy breathing then he started to fuck me real slow using the entire length of that long fat dick. Before long he was pounding my ass and made me cum all over myself and as maid there in my own cum he fucked my ass and shot two big loads way up inside of me.
It was Saturday so I stayed all day and let him fuck me numerous times then he wanted to calm his wife and tell her what we were doing and once he told her she wanted to listen to us fucking so she fingered herself while he fucked me and she was on speaker phone talking dirty to both of us and heard her husband moaning out loud when he came in my ass.
She cut her visit short and was home late that evening and as she requested he and I were both still there and made sure we were in bed in a 69 when she walked in. In a few minutes the sexiest woman I had ever seen was sucking both of us and I was eating her shaved pussy. Then she and I got in a 69 and she guided her husbands big hard dick in to my asshoke then she sucked my dick while he fucked my brains out and when I came in her throat she squirted her juices all over my face as he shit his load up my ass.
After that he and I fucked her in the pussy ass and mouth and him in her pussy and me up her ass then both of us in her pussy. I watched him fuck her ass while she sucked my dick about two weeks later they asked me to move in with them and for about a year I was their sex toy and we did things that I will never forget. She fucked me with strap on cocks while I sucked his dick he and I fucked her in every way possible she watched him fuck me and she played with sex toys watching us we tried bondage and they bought a sex swing and had me in it pretty often fucking me up the ass they would take turns on me him fucking my ass then her with a big strap on fucking me
I let them use me however they liked and the sec was the best I have ever had and I will never forget fucking such a hot sexy beautiful woman and how she enjoyed being fucked up the ass like I did.
I often wonder where they are these days and think about all the things we did and I still jack off thinking about them.

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Anonymous

by Anonymous on Jun 19, 2025 at 11:07 AM

I love sucking my BIL’s cock after he fucks his wife, vice versa.

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