The tip of a cock being forced into my ass for the first time was something I'd been anticipating ever since I'd accepted being one of the girls to attend this bachelor party. Perhaps not anticipated so much as being resigned to. In the car bringing us to the party, the other two ladies had even joked about how sore their pussies and asses would be afterwards with this many men to satisfy. Since 'good girls' would never allow a cock up their ass, I'd never tried it while dating. So, I'd waited nervously for my first anal experience.
In the time since volunteering for the party I'd bought an enema kit. Late one night when my parents were sure to be asleep downstairs, I'd practiced giving myself enemas. Maybe as a youngster I'd needed an enema but, if so, I didn't remember it. The slender nozzle was the first thing I remember being in my ass other than what was meant to be there. It wasn't so bad.
The warm water filling my colon gave me the uncomfortable feeling that I needed to take a huge dump. As the pressure built inside me I began thightning my anus, thinking, Just a little more, a little more... Withdrawing the nozzle and finally releasing brought me a great deal of relief and a somewhat pleasurable feeling. It wasn't so bad.
With my colon cleaned out I returned to bed. After sliding my six inch vibrator into my pussy until it was good and wet, I put the tip to my ass. I pushed to experience what a cock might feel like inside me. It wasn't so bad...
It wasn't so bad... That thought was going through my mind as the groom pushed the tip of his cock against my anus until it slid into my ass. His grunts and my cries of pain as he continued to bury his length deeper up my ass with hard thrusts caused the men waiting for their turn to laugh and call out lewd things like, If that bitch's ass was cherry it ain't no longer! I hadn't told anyone my ass was indeed cherry, not that it mattered now. My last cherry was well and truly gone. I learned something as the cock burried itself deeper up my ass. I learned that there is a huge difference between taking a smooth, lubricated plastic cylinder up my ass and taking a much larger girth of barely wet human cock.
If I'd known what he'd intended I would have asked to use the bathroom and used the douche bottle to lube my ass. Instead, after my short rest in the pool, he'd taken my hand and led me to a table beside the pool. Bending me over the table, he'd started fucking my pussy until his cock was wet. Seconds later all I could do was grip the edges of the table and press my forehead hard into the surface as he began fucking my ass.

Pulling out, the groom placed me on my back and, lifting and spreading my legs, again began fucking my ass. All I could do was grit my teeth. In far less time than what it felt to me, I felt him push hard against my ass cheeks as he came deep in my ass. No sooner had he moved away than there was another man to take his place... And another man after that one. By now my ass was stretched by cock and lubricated with cum and I wasn't in any more discomfort than feeling like I needed to shit. Some men came in my pussy but all fucked my ass as well. By the time the sixth or seventh man had come in my ass even the feeling I wanted to shit was gone as cum leaking from my ass and pussy combined to wet the table underneath me until my ass was sliding in a pool of cum.

It was when the men tired of taking me one at a time that they led me inside the house. One man laid on a couch and others positioned me on top of him. Facing upwards as his cock took me in the ass, another man moved on top of me to fuck my pussy while yet another stood to the side of the couch and began fucking my mouth.
It was in the time that followed that I began to feel the extreme pleasure of being mastered. Not with handcuffs or any form of binding. This was not the feeling one has during BDSM which, no matter how realistic, one knows is just playacting. No, this was the feeling of knowing that these men were in control. They could and would do what they wanted with my body. I had no control of where, when or how many at a time would fuck me and, God help me, I was enjoying that feeling as I relaxed to accept whatever was coming. I wanted to be mastered. When I realized that and totally surrendered my body to their use, I knew my pussy was wet from more than just their cum.

The three of us ladies weren't given a rest until evening when the main meal was served. We ladies were allowed to wash off in the pool before the meal, which was very pleasant. Cum from our pussies, ass and bodies were washed away. Naked, we sat, ate and drank at the groom's table. I was feeling light-headed from the champagne when the meal ended. After the meal the flasks we'd filled with cum were presented to us as the our host gave a toast to the groom. I made the mistake of smelling the cum collected inside. It wasn't pleasant even though it had been refrigerated until now... I knew that to drink the contents I'd have to hold my breath. I had one ace up my sleeve. I knew from being taught how by boys I'd dated in high school that I could shotgun a beer in two seconds flat by relaxing my throat and letting it pour past without swallowing. What was in the flask was probably a little less than a beer can's worth. I'd just do the same and shotgun the cum.

Which I did to the cheers of the men watching. I tried not to think about what I was pouring down my throat, Just get it down, I thought. Hopefully it would stay down. I had no interest in knowing what upchucked cum tasted like. To more cheers my empty flask hit the table first and I was declared the winner of the second contest. That money is all mine, I thought as I grimaced at the sour, cummy after taste.
The girl next to me made the mistake of taking the time to swallow and had choked on the taste or the smell or both. Coughing, cum ran out the corners of her mouth as she set her almost full bottle on the table as I was declared the winner. Men began shouting for me to drink her flask and our host held up his hands for silence. "Now, you can't expect her to accept this dare for nothing, can you? She's won all my money already, so why not take up a collection? Perhaps that will persuade her."
Money was passed forwards and quickly piled up on the table in front of me. When the host declared the pile tall enough he handed me the second flask. Mixed in with the cum from either my first flask or this second, I knew I'd be drinking another woman's pussy juice for the first time as I raised another almost full flask and drank. Slamming the empty flask onto the table,I grabbed the money and held it over my head in victory as I tasted a not very pleasant, cum flavored burp.
I was given time to run into the house to put the money in my purse and, leafing through it quickly, I counted over three thousand dollars! Along with the money I was being paid and the two prizes I'd won, I had my apartment and much, much more! It would be months of being a whore before I equaled the amount of cum I drank that single five minutes but it was worth it.
I was more than willing to drink more cum and there would be lots more cum during the night as men came in my mouth or collected cum from my pussy and from tributes on my tits and stomach in cups and glasses. There was more pussy juice, also, as men pushed us ladies together wanting to watch lesbian action as we drank from each other's pussies.
***********************
Sitting on the floor of Danny's apartment in front of a coffee table cluttered with the remnants of pizza, I wasn't thinking about all the cock and cum I'd had in the two years I'd been a whore or while dating in high school. I was thinking about the thrill, the excitement I'd felt that night during my first gangbang as I surrendered to the uncertainty of knowing someone else was in control. Just as I was uncertain now as I gave control to my date.
On dates I like a guy to be in control. He might ask what movie I wanted to see or what I might feel like eating... But I liked him to make the first moves. I'd gotten Danny this far. Anything after this point was up to him.
Finished with pizza, Danny microwaved the popcorn as I selected one of the movies to watch. I'm not sure we even remembered any of the movie the next day. We spent most of the time sitting on the couch talking and exchanging stories of our growing up. I carefully kept from asking about any of his high school years.
I knew Danny was thinking about our kiss as much as I was but he made no move to kiss me again. He didn't even try to put his arm around my shoulder or sit close enough to do more than brush our shoulders together now and then. I was secretly enjoying his obvious indecision on what to do. I sure as hell wasn't going to initiate anything. Like I said, I'd gotten the two of us this far. Anything further was up to him to initiate.
Danny had to start his weekend job as a waiter at a diner early in the morning and I'd told him I was spending the weekend at my parents so we headed for the train stop about ten-thirty so I could catch the last train. The idiot did at least muster the courage to hold my hand during the walk, but it was only as the train pulled in and stopped that he hesitantly leaned forward to kiss me. This time I waited to see if his tongue... It did. But we had no time for more as I boarded the train for home and our date was over.
We waved as the train pulled out and I leaned back into my seat. I was very satisfied. Not by the sex I'd had during the day. Truth is, I wasn't getting any thrill from any of the sex I had as a whore except for the rare gangbang parties I could attend. Regular sex with my regular clients... It was like acting in a long running play. You might be able to fake it for your audience, but your thrill of the first night's performance was missing. I'd seen so many couches and desks and beds... Being on a real date as I hadn't in many months? That excited me! As I moved my legs, I knew the wetness in my crotch wasn't from the three men I'd fucked earlier today...