Welcome to the Club [FM] | 2016

First post to /gonewildstories so a quick intro: I'm 29, blonde, natural 34c/d, curves in the right places but fit (lots of hotel gym and yoga time since I travel a lot), and I've had a pretty huge sexual appetite since college. A fan wanted to hear a story from my time as an accidental traveling sugarbaby, so here you go!

Welcome to the Club

Once upon a time I was a girlfriend turned sugarbaby to a very wealthy British man who over the course of a year educated me on the finer things in life yet also managed to get me to enjoy utter sexual depravity. The relationship lasted about a year and started normally enough. But over the next year I went down a rabbit-hole: whorish weekend shopping and sex getaways, rough sex, group stuff, and more. It was nuts and I can't believe I actually did all of it without lasting consequences.

"Tyler" was in his early 40s, tanned, had perfectly coifed brown hair, was fit as a hot actor, and spoke with a to-die-for posh but manly, gravely English accent. He worked a lot but for the family company, so he lived on his own terms. I was 24-25 at the time and blinded by the lights, too intoxicated by it all to overthink the negative aspects; those would be dealt with later. I had dumb-lucked my way into the life of "my very own James Bond" and I was having a hell of a good time. This was quite the upgrade from the 20-something year old men I had recently dated, and another world compared to the boys in college.

Tyler palled around with men like him: generally in their late 30s/early 40s, wealthy (some worked, some had no discernible responsibilities), mostly European expats of various nationalities, all in good-to-great shape, worldly, and usually to be found with a 20something girlfriend, mistress, or wife (sometimes it was hard to tell one from the other). Some of the girls were classy while others were bimbos. The group of men stayed intact for the time I dated Tyler, but the roster of girls was fluid: there were some regulars but the bimbos came and went. And the men clearly had a thing for American girls, which almost all of us were except for the occasional European and one of the wives, a Brit. The men had a rich expat boys club of sorts, and about 6 weeks after I started to see Tyler I was invited to join them on one of their regular, much-hyped boating days hosted by Peter, who owned a "small yacht." I guess "small" meant having a cabin the size of a nice one bedroom apartment and a deck begin enough for a bar and 12 people to relax.

I had met some of the men and ladies before, but others were new. There were about 6 men and 6 ladies on the boat if I remember correctly, plus the 2 person crew. A couple of the girls removed their tops as we got out of traffic and away from the coast. Tyler kept teasing me to take mine off, too, but I was too shy. As sexual as I am, I've always been hesitant to show skin in public. Besides, I thought I had a decent tan, but I was clearly one of the two fairest skin girls there. I needed to work on that, I noted to myself. And anyway, I thought my skimpy bikini was enough of a show for all the men.

Some time and many glasses of champagne and negronis followed. The men smoked cigars. It was kind of like a dream and I was trying hard to not seem out of my depth. I had already learned a lot from Tyler, but I was still not used to this lifestyle. More tops had come off and the boys were getting rowdy. Only me and one other woman, the oldest one there in her early 30s, still had their tops on. I came to learn she was Peter's ridiculously tolerant wife, and we later became good friends.

Someone had kicked off a discussion about how everyone was so sexy and drunk enough to be openly ogling each other, how it was a beautiful summer day, and how it was a shame there weren't enough rooms for everyone to shag. Someone called out a couple that had disappeared for twenty minutes but had returned a few minutes ago with big smiles: "looks like they found a suitable room!," someone suggestively yelled as everyone laughed. It was clear they had escaped somewhere to get it on. The girl, a pretty and tanned tall brunette, didn't seem embarrassed at all; the man, a very tanned, very sexy German man, just shrugged with a smile.

One guy asked what was the harm in doing it in front of each other. None, was the reply from another, noting that it had never been a problem in the past. Tyler assured me there wasn't about to be an orgy on the boat, and that the guy was referring to a wild night at a ski lodge a few months back. I must have been a visible mixture of blushing and aroused. Peter, built like a rugger and the most vulgar of the men, called me out. "I'm surprised your new bird is such a shy one! C'mon, we don't bite!" More laughter from everyone. I laughed along too, trying to fit in with the other girls, who all seemed insanely comfortable. "Has Tyler given you a tour yet?"

"That's a good idea," Tyler said devilishly. He grabbed a half full bottle of champagne with his left hand and with his right, helped me up. As we walked down a short flight of stairs and entered the cabin I heard some cheers and a whistle.

"Your friends are crazy. And pigs," I said.

"Oh you don't mind," he responded before taking a swig from the bottle. "I know you rather like it."

I took a swig too and then he slipped his tongue inside my mouth, powerfully. With one hand feeling me up and the other firmly on my jaw and neck, we kissed as he walked me backward into the bedroom. The bed was made; the other couple must have done it on the couch we just walked by. He was devouring me and I kissed him all over too, and I could see and feel that his dick was hard. He stayed standing as I sat on the edge of the bed. He took my top off and I slide his trunks down, and out sprang his erect cock. Tyler wasn't the biggest I've had but substantial enough at least 7, with nice girth and a fat pulsing head. And he knew how to use it.

I took a swig and handed him the bottle as I wrapped my lips around his cock. I made out with it and enjoyed the awesome sensation of feeling it grow in my mouth. Fully hard, and with one hand on a thigh and the other stroking his shaft, I made out with his cleanly hair-less balls. Then I started sucking. Up and down, again and again. His hand found it's way to the top of my head, sitting there loosely but soon holding my head in place when he wanted to keep his cock completely swallowed for an extra second or two. I genuinely love giving head. My last boyfriend had trained me on eye contact and dirty talk and general porniness, and Tyler loved it too.

I had switched on bimbo mode. "You love that everyone knows I'm sucking your cock right now, don't you?" I said looking up at him, eyes wide and blinking like a bimbo.

He ran an index finger on my tongue and inside my lips, and said "And everyone is jealous." I smiled and continued sucking him. I hummed on his cock [note to guys: humming on our clits feels just as amazing]. He placed one foot on the bed so that he had leverage over me, and began thrusting into my mouth while more firmly moving my head with his hand. I started making that sloppy head noise that comes from not being able to time your breathing or swallowing right, moaning the whole while. He used my mouth like this for a minute or two; I was drooling and my hair was a complete mess.

"Get up," he said, pulling off my bottoms as I did. He cupped my soaked pussy with two fingers and slid them in as I took a swig of bubbly. The moment I sat the bottle down he spun me around, pushed my back down, and slid his cock into me. I let out a loud gasp. I had two hands braced on the bed while bent over, as Tyler gathered his pace.

"Tyler, close the door."

"No one is coming down here." He started sliding in and out of me. Easily. I was so wet.

"Everyone will hear me. And what about the crew?"

He slapped my ass and started slamming me rapidly and hard. 0 to 100. Whatever next protest I had been formulating in my brain was replaced by the visceral sensation of a hot man owning me with his cock. I had ceased to have any thoughts beyond being fucked. I tried so hard not to scream, cutting each one off as they involuntarily began and choosing instead to moan and grunt through clenched teeth. His balls were slapping me so hard, and he was thrusting so hard as I flirted with orgasm. After a couple of minutes my knees buckled and I collapsed on to the bed with a scream. Tyler collapsed with me, on top of me, his cock still in me. "Oh my god, close the door," I said.

I didn't get a verbal response. Instead, Tyler turned me over, stuck one leg straight up over his shoulders, and began pumping me. "Oh fuck, oh fuck, oh fuck, oh fuck, oh fuck" I started whispering but ended up yelling. Tyler was a machine and pounded me. I'm loud in bed and it was getting hard to stop the screams as I got closer and closer to climax. I covered my mouth to muffle the noise. 10 seconds later, without missing a beat of his powerful rapid thrusts, Tyler removed my hand. I covered my mouth again, and with his left arm braced against the headboard, he used his right to uncover my mouth. this time more forcefully. I let out a huge scream followed by an "Oh god, you feel so fucking good."

I sensed another scream coming and covered my mouth. He tried to remove my hands again but I resisted. Slap! He slapped my face hard enough to remove my hands and then pinned my left hand down under his right one. Still pumping, he leaned in to give me a reassuring and long deep kiss. I had mentioned my growing interest in rough sex and in recent weeks Tyler had started to turn up the heat.

He arched back up and raised my second leg. Both legs were straight up now, and he was fucking me like a madman, with a maniacal grin. We locked eyes. Slap! My face was on fire and my mouth was wide open and my eyes darting between the sight of his cock pummeling me and the sight of his face looking down at me. I was going to cum...I was moaning and panting ever harder, and the staccato screams were close to erupting into a wail. I hadn't even tried to move my other hand, now limp as I was being fucked like a doll, at his complete mercy. He put his finger in my mouth and I sucked on it like a pacifier as he pushed my tongue down. "Scream for my cum," he said. I just kept moaning. "Scream for my cum." He removed his finger from my mouth and squeezed my tits.

"Give me your cum," I said breathlessly.

"Louder."

"Give me your cum, Tyler, wherever you want."

Another hard slap to the face. "Louder!"

"Give me your fucking cum!" I screamed. Tyler started to lose it, pounding me harder and faster than ever. He was close. I started to orgasm. I started wailing in pleasure, letting out a string of high-pitched yeses, oh fucks, god yeses, and more fucks.

What a man...he had been visibly holding his own cum so I could orgasm. Now it was his turn. "Give me your fucking cum, baby, give it to me!" I begged. His first shot of cum exploded inside my pussy as he pulled out, with his head just inside. My legs dropped and he straddled me. I think he was trying to get to my face but the second shot came right away, landing in a trail on my stomach. The third blast thankfully went straight into my still open mouth. Mmmm I squeezed my lips around his cock as he spasmed again, feeding me a few more small shots of cum.

Breathless, sweaty, and covered in cum, I just sat there in a daze as Tyler rolled to the side and collapsed as well. We took swigs of the bubbly and finally got up. He slipped his trunks back on. I was about to walk to the bathroom when Tyler grabbed me, kissed me passionately, and said to keep his cum in me until we got back to his place in a few hours. I agreed and slipped my bottoms on. It was in that moment I realized that I didn't have a brush to fix my hair, and besides, everybody had probably just heard me scream like a whore for the last 15-20 minutes. Oh. my. god. In the bathroom I cleaned the cum off my stomach with a towel, looked in the mirror, and realized that I was right: I looked like I had just been fucked senseless. Because I had been. I straightened my hair the best I could, looked in the mirror, and thought, "Well, fuck it; what's the point of keeping my top on now?"

We emerged from the bedroom to find a man named Felix on the couch happily receiving a slow blowjob from one of the bimbos, who was on her stomach next to him. I didn't know what to say. How long had they been right outside the bedroom? Did it matter? Everyone on the deck probably heard anyway. We momentarily paused at the sight. Felix smiled and the girl looked up for a second to say "You guys sounded so hot" before putting her head back down. Who were these people?? It wouldn't be the last time I saw Felix's cock.

We exited the cabin to a round of applause, woots, and whistles. I had lost all shame, or at least tried to pretend I didn't have any, and just smiled and laughed with everybody else. With a huge smile, Peter said "Welcome to the club." Some of the girls came over to me with big smiles. One handed me a freshly made cocktail; they complimented me on my boobs, asked if they are real (they are) and said it sounded like I had fun. What the hell...what crazy people had I fallen in with?? Just who was Tyler?? One of the girls echoed Peter, saying, "Hey girl, welcome to the club." I took a big gulp of my negroni. I had no idea what they meant, and what was in store for me as Tyler and his friends' new toy.