A sailing trip with first gay play turns into a sexual exploration for a few friends.
WARNING - Bisexual content FFM, Some Hetero Sex FM, if its not your thing, please dont read.
We arrived into port at the same time as the big trawler. The captain was a big solid bald guy, probably early 40s. He waved to us in a friendly way as we tied up to a guest mooring. As we packed up, a few crew came over in a dinghy and offered us a lift to shore when we were ready. We readily accepted as the yacht had no dinghy.
Fifteen minutes later we were picked up and dropped off behind the trawler, which had taken up the entire jetty. They were unloading lots of seafood boxes, so I assumed they had a good catch.
George and I walked up the street to the Hotel and George booked a room. Once we got to the room George called the yacht's owner and told him we were in port and all was good. Once off the phone George told me the owner was driving down next day with family, and we would drive back to the city in his car.
I tried the bending and moving trick to get George interested in one last fuck, but he clearly had no interest. I tried to talk about the 'boat' but he pushed me hard up against the wall and said "You ever breathe a word of that and I'll kill you, do you understand?" I nodded, but was very disappointed.
I felt that the guy sex had been fun, and although I still fancied girls, I wanted to play that game any time we were without girls. The room had a big double bed and a small single bed. George pointed at the small bed and said "That's yours, don't come near my bed"
We went to the bar in the Hotel and had quite a few beers. Some time in the late afternoon George picked up a barmaid who stayed drinking with us after she finished work. George eventually invited her to our room. She looked at me and smiled saying "You coming too? Theres enough woman here for both of you boys." George didn't say anything so I tagged along.
Once in the room they started kissing, and George was quick to get her top off. She had lovely firm D cup tits and big red hard nipples. George was in a big rush and had her shorts and knickers off pretty soon and was shoving some fingers into her pussy. As he went down to lick her pussy she beckoned me over with her hand. As soon as I got close to her she started kissing me passionately and squeezing my cock. I realised I was rock hard.
George stood and bent her over slamming his big wonderful 9" cock deep into her pussy doggy style. She was swearing and saying "Fuck me, oh do me, fuck me" Then she pulled my shorts down and took my entire hard cock deep down her throat, until her lips touched my pubic bone. George was doing his best to fuck the life out of her and his thrusts kept forcing her face onto my rock hard cock.
After 10 minutes of rough fucking she stopped him, pulled her pussy off his cock and turned, taking his big 9" cock down her throat. Her wet open pussy was pointing straight at me. I pushed my rock hard cock into her. She started orgasming as soon as I was fully in. She was cumming and trying to talk with George's big cock down her throat. We just heard gurgles. She had an awesome firm butt, so I smacked her ass cheeks a few times each side. She must have liked it rough, as she started cumming again.
She had somehow pushed George up to the other bed and soon he fell back sitting on the bed. She instantly pulled her throat off his cock and moved forward pulling her pussy off my hard cock. As she kissed George, she managed to impale her tight wet pussy onto his rock hard 9" cock.
She said "Fuck, do all you sailors have 9" cocks? I would have been giving you free drinks all day, if I knew you were both so fucking hung."
She turned to me and said "Shove that fat cock in my ass, dont go slow, just fuck my slutty ass, havent had two big cocks in me for months. DO IT NOW"
I took my own cock in my hand and lined it up with her perfectly presented pink ass hole. I started to push and nothing happened. I could feel Georges ball bag rubbing on my ball bag. My cock was pulsing with desire. I could not stop thinking that I was about to do to her, what George had done to me 6 or more times in the last day. She pushed back and my cock head went into her ass.
She screamed "Fuck, that's a big cock. Fucking fuck me"
George was squeezing her nipples hard. She screamed again and came on his cock in her pussy. She squirted from her pussy and squeezed my cock out of her now wet ass hole. I grabbed my cock again and lined it up with her ass. I shoved in hard and got 3" of my cock up her ass. She pulsed and screamed then shouted "Fuck me I love it"
I shoved hard again and my cock went another 3" into her ass. I had fucked girls asses before, but never with a big cock in their pussies at the same time. I could feel George's big cock pulsing in and out of her spasming pussy. I pushed hard and the final 3" of my rock hard cock went into her ass.
George and I started pulling out 5" together and pushing all the way back in. Her ass was tighter than anything I had ever fucked. She was constantly pulsing and constantly squirting cum on our ball bags. George had put both his hands on her hips and was pulling her hard onto his big cock. I got both my hands on her fabulous firm D cup tits and squeezed them as hard as I could, making her cum even harder.
I was thinking about the ass fucking George had given me that day and my ass was pulsing. I took my right hand from her tits and shoved 1 finger into my ass. It felt fantastic, so I shoved another finger into my ass up to the knuckle. She was screaming and cuming then I started cumming as well. I screamed out a massive cum with her tight ass squeezing my cock like a vice, and my now 3 fingers pumping into my ass.
When I withdrew my fingers from my ass, and my cock from her ass, she lifted off Georges cum covered cock and span around. She took my right hand and licked the 3 fingers that had been in my ass and sucked them deep into her mouth. She said "Fuck! You had your fingers in your ass. Thought you two guys were a bit close. You fuck don't you? I can taste cum, you have his cum in your ass"
I denied anything and so did George, but he was angry so he threw me out of the room so he could continue fucking the barmaid. I dressed quickly and walked down to the beach. After walking along for a while I headed back to the jetty. I walked out along the jetty and the trawler was still tied alongside.
The skipper was in the wheelhouse working on a laptop. When he saw me he came out on the aft deck and said hello.
We chatted for a while about the nice warm night. He asked me why I wasn't at the hotel with all the crew. He said they were celebrating a big catch and their bonus. I told him my skipper George was celebrating with one of the barmaids in our room.
He looked confused and said "Oh, thought you two were more into each other than barmaids"
I asked "Why is that"
He said "Well I saw the two of you on your boat through my binoculars. You seemed to be enjoying helping each other ease the boredom of the trip."
I actually blushed and said "Well that was a bit of a first for us. Think George is trying to prove his masculinity is still ok by fucking the barmaid half to death."
The skipper said "And what about you, how would you like to spend the night?"
I blushed again and said nothing.
He said "Why don't you come on board for a nightcap"
I nodded and walked over the ship's rail and followed him into the ship's cabin. He poured us both a small glass of port and handed me mine. He gulped his down, so I followed him. He immediately refilled both our glasses.
He said "I must admit I like the odd bit of manplay on a boat. Can't fuck the crew though, it's bad for business. I saw him hit you. If you wanted to suck my cock I would never hit you. Won't see the wife for another 2 weeks and sure could use a hand to calm my cock down"
I looked down at his shorts and a very large looking bulge had formed at the front of his shorts.
I tried to say I had never done that or wasn't gay, but no words came out. He just took my hands and guided me down in front of his rapidly hardening cock. He pulled down the elastic front of his shorts, then the top of his boxers. His cock sprang free. His cock was not as long as George's or mine, perhaps 7". It was very fat. Perhaps twice as fat as George's.
I put both my hands around his cock. I was mesmerised by how wide it was. It was easily as wide as the cans of beer I could see in the ship's bin off to the side. He was cut and the head was the size of a small apple. His cock slit was leaking a huge amount of pre-cum. I wanted to taste it.
I bent my head down and sucked the head of his cock, tasting my first pre-cum. The skipper put a hand on the back of my head and encouraged me to take more of his cock into my mouth. I opened my mouth as wide as it could go, and he pushed his cock into my mouth. It was so wide it hurt my mouth and his cock scraped on my teeth, top bottom and sides.
He held my head with both hands and started pumping his cock into my mouth. On a few in strokes he pushed too hard and got a gag reflex out of me. On one particularly deep push he had me coughing. As I coughed he pulled me to my feet, turned me around and pushed me knees down onto a couch.
I was still coughing as he pulled my shorts and boxers down. I was kneeling on his boat couch, ass in the air without my shorts or boxers. He then knelt down behind me and started tonguing my ass. Electric flashes were going off in my head. I had never had a tongue in my ass. I loved it.
After minutes of being tongued, I knew my ass was ready for fucking. He said "Would you like my big fat cock in your ass?"
I answered "Yes please but go slowly you are huge"
He slapped my ass really hard with his big gnarly fishermans hand, then said "I'm the captain answer properly"
I answered deliberately "Yes please Captain, fuck my tight sweet ass with your huge cock"
He stopped licking my ass and stood up behind me. I knew it was going to hurt to have his big cock in my ass. I still wanted it badly. At least he was not a reluctant top fuck buddy. He wanted to do lots of man sex things, not just fuck me.
He pushed his big fat cock upto the entrance of my anus. I started hyperventilating in fear of his thick cock. He held my hips each side. He then started to press forward with his cock. I could feel my anus stretching. I could feel his cock pulsing, or was that my ass pulsing? I could not really tell. My ass was on fire with pleasure and pain.
He held his massive fat cock pressed into my anus. My anus held him out firmly staying closed. The pain was searing hot. The pleasure was electric white hot. Soon they both melded and my tight sweet ass could hold out no longer. My ass slowly yielded to his massive hard cock. The head slipped into my ass. I started stroking my cock but the pleasure of his cock stretching my ass was so intense, my cock started going soft. I squeezed my balls for more pleasure and he kept pushing that massive baseball bat sized cock up into my guts.
He said "Tell me you like my cock"
I said "fuck, your cock is awesome. I've never felt such white hot pleasure, fuck me Captain, please fuck my ass"
He continued to force his fat cock into my poor tight ass, until his tummy came to rest firmly against my butt cheeks. I knew what was going to happen next. He started pulling out slowly at the same slow pace he had pushed in.
By the time I could feel his fat bulbous cock head at my anal ring, I was begging him to fuck back into me again. He would not speed up. He just kept slowly fucking me, fully deep in, then fully pulled outside of my anal ring. His cock was burning a hole in my insides and I loved it. I wanted him to fuck me hard and was begging him to speed up.
My soft cock was dripping cum or pre-cum, I didn't know which. I used my hand to get some on my fingers and sucked it off. It taste wonderful , though I still didn't know if it was cum.
The Captain started to increase the pace, pushing in fast then holding in. Pulling out fast and holding out, then repeating the fucking. I started pushing back hard onto every in stroke. I was babbling incoherently for more cock on the out stroke.
Soon the Captain was forcing his rock hard massively thick cock into me at a high speed. It felt fantastic! I was loving it. His cock was pistoning in and out of me like a big piece of hot metal. My insides were on fire and my soft cock was pulsing in a way I'd never felt. As he started gasping for breath and fucking me even harder, I was slamming back onto his massive tool, getting every last bit of exhilarating feeling from his cock.
His big cock started pulsing and I knew he was going to cum. I pushed back onto his cock and milked his magnificent cock of every last drop of cum. When he finally pulled his cock out of me I span around and said "Please Captain, may I suck you"
He just nodded and I sunk my mouth over his rapidly deflating but still huge cock and sucked it for all I was worth. I loved the flavour of cock, ass and cum all mixed together. I must have been doing it well as he started to get hard again until he was too big for my mouth. I stopped sucking and turned on the couch offering my ass to him.
He wasted no time and impaled me with his massive cock in one go. I literally saw stars as he shoved his 3" diameter cock into my ass. He was very strong and just grabbed my hips and started fucking me crazily. He was forcing his cock as roughly as he could into my almost virgin ass.
He rapidly built to his second cum and pumped a second big load into my ass. This time he pushed my hungry lips away from his cock as he pulled out.
The captain told me to go before the crew came back, as it was hotel closing time. I made my way back to the hotel room. I was leaking cum all the way down my legs by the time I got back to the hotel.