I Don't Know How This Happened

Edward sat outside waiting for me. I felt a little excitement, and a little annoyance at how I knew our night would go. He'd badger me for details (annoying), and then fill me up.

I wasn't exactly right. Yes, Edward badgered me for details: "Did he pull your hair?" "Did he call you names?" The closest Edward got to achieving a full erection was when I told him about offering my throat to Bro, and he showed a little more interest in when I told him about showing Bro's roommates a little extra skin.

"So this is it," I said. "He makes love to me like a real man, and you can't get it up. He chokes me with his dick and calls me a whore in a dingy restaurant office, and you fly full mast. What is wrong with you?"

He looked down. "I jerked off in the car," he said.

"Outside the restaurant?"

"Outside his apartment."

"That was hours ago."

"I did it four times," he said.

I pushed his head down to between my legs.

"Tell me what you thought about," I said. He told me his fantasy lick by lick, taking things slow and building his arousal.

"In my fantasy, Bro told us that you weren't allowed to wear any clothes to his house. So you wore a long raincoat for the ride down. When you knocked on his door, you took it off, only, Bro didn't answer the door. His roommate did. He said, 'Bro, your new slut is here,' and closed the door again.

Bro made you wait. When he finally came to the door, he made a show of introducing you to his roommates. You tried to cover up, but he pulled your hands away. There was another girl there, and she said 'Bro is really hot, but you gotta be really slutty to just show up naked to a guy's apartment and let his roommates see everything.'

Bro laughed. He took you back to his room and grabbed you by the hair. He said he was going to fuck every hole, and that he was going to video tape it, and if you ever told him no he would show it to people. Then he had one of those sand in the hourglass things, and he said 'If you can't make me cum by the time this hourglass runs out, I'm going to spank you with this wooden spoon.'"

In my mind, I thought of myself furiously, desperately sucking cock to avoid a spanking. Edward increased the pace of his licking, and he brought me to a short, sweet orgasm. I hadn't realized how much I attention I was paying to this story until Edward stopped talking, at which point I realized that this tale of humiliation and exposure deeply aroused both of us. Edward climbed on top of me, and slid himself all the way to the hilt, a rarity given his size. He fucked me hard, and harder. He was spent from having jerked off in the car, and fucking me wildly trying to bring himself to orgasm. He came with a low guttural moan as he filled me with spunk.

He softened in my pussy, and as we lay panting, I said "In your fantasy, did I make him cum before the timer?"

"No," Edward grinned.

Bro wasn't on the schedule for the next couple of days because he had decided to take a rare weekend off over a break. But on Saturday night he called the restaurant. He got right down to business: he wanted me delivered to his apartment the next morning.

I told him I'd get back to him with a decision, as my husband and I couldn't be expected to change plans on a whim, but I already knew Edward's reaction.

Edward drove me to Bro's apartment a bit before noon on Sunday. I was wearing a raincoat and heels, a nod to my husband's fantasies, and Bro's demands. For my own sanity, I wore a floppy hat and sunglasses, because one never knows who you'd run into.

When I knocked on Bro's door, I didn't disrobe. But when Bro answered, I unbuttoned my raincoat slowly as Bro realized that I'd worn nothing to his apartment. He pulled me in with a long, passionate kiss as his hands roamed my body. I melted, lost a bit, and breathless, when I realized I wasn't alone.

"Milf," I heard.

I turned my head to see Bro's two roommates, the ones I'd shown some skin to last week, sitting on the couch. Bro began slowly lifting the back of my raincoat, exposing my bare thighs, and then more.

"Bro, please. Don't," I whispered.

He didn't listen.

"Just giving them a little show," he said.

He exposed my ass, showing these two idiots that I hadn't worn anything to their apartment.

"That lady is naked," one of them said.

"Bend her over," said the other.

"Don't be an asshole," Bro told them.

He let my raincoat fall and led me by the hand to his room.

"You wore heels," he said. "Good girl."

I took my hat and sunglasses off, then removed the raincoat by letting it fall past my shoulders, using my arms to frame my boobs.

When he took off his t-shirt, I swooned a little. I realized that my raincoat exhibitionism was an attempt to feel like I was the hot commodity here. Seeing his abs, his taut athletic body, served as a reminder that Bro was the object of desire, and that his interest in me had much to do with my inability to say no to him.

He took off the loose fitting track pants he had been wearing, his boner springing free.

"You know what to do," he said.

I sunk to my knees and grabbed the high heels with my hands, pushing my tits forward. Instead of putting his cock in my mouth, he stepped a bit closer, rubbing the length of his shaft on my face, forcing me to look up as I licked the sensitive nub of nerves just below his cock head.

"I have something for you," he said.

I put my lips over his dick and started bobbing up and down. I didn't need to ask what it was. Eventually, he'd tell me.

Though I'd given him free range to fuck my face - my hands were holding my heels - Bro was gentle. Yes, he was plunging deep into my mouth, but it wasn't enough to gag me, and he wasn't going so fast that I felt like my tonsils were getting punched. This wasn't an attempt to cum, this was foreplay.

He lifted me off my knees, reaching down to feel my pussy. Two fingers probed my channel and an electric shock went through me as one finger glided over my clit.

"Dirty little slut gets so wet with a dick in her mouth," Bro whispered.

"What did you get me," I said, coquetishly

"I've noticed that you really like it when I play with your ass," he said.

"I do?" I asked.

"Drives you wild, from what I've seen," Bro said. "I want to take it further."

"You want anal," I said. I wasn't surprised. It was... a very common feature of porn these days.

"Eventually. But I'm not sure you're ready. I bought this."

He reached into a drawer and produced a butt plug.

"It looks big," I said.

"Do you trust me?" Bro said.

"Not really," I replied. This was true. I did not trust this man. Though I reveled in the fact that Bro always seemed to have a boner when confronted with my curvy, old-enough-to-know-better body, I knew that Bro was capable of treating me like a total object, that he had, and likely would continue to push my sexual limits.

He laid me gently on the bed and pressed his lips to my already wet slit. He'd never done this before, even in our encounters in the restaurant office when he only needed to use his fingers to bring me off.

I was in ecstasy. Again, this felt loving. A way of giving me pleasure without taking any. Soon I felt one, then two fingers inside me, curled up and teasing my g-spot in time with the flick of his tongue over me.

Quickly, I was on the path to a massive orgasm. Bro stopped. I begged. He grabbed lube and coated the butt plug. I watched with a not-insignificant degree of anxiety. He spread more on his finger, and used it to coat the rim around my rosebud.

"May I?" he asked.

I paused, then relented.

Gently, he glided the plug into my little hold, and I felt it stretching. He went slow, I can't say it was entirely painful, but my whole bottom was consumed by a dull throbbing as he worked the fat end of the plug. Back and forth.

As I winced, Bro bent down and licked my clit again. I was surprised to learn that despite my focus on this large object entering a hole that had only been used as an exit before, I was still turned on. The echoes of my near-orgasm returned, and Bro's tongue had me on the brink again. He licked for just a few seconds, and, sensing my orgasm approaching, backed off.

"Ughghggh. Why," I whined.

"Because I want you to feel this all the way inside you. Now, relax. Just a bit," he said.

I untensed as much as I could, and felt my the fattest part of the butt plug pass my ring. Oh my fucking God, this felt big. Full.

Bro began licking me, and from the first flick of his tongue I was overwhelmed. Wave upon wave began to wash over me as I moaned and yelled for what seemed like ages.

I realized after what I think was a third consecutive orgasm that Bro was going to keep licking, but my whole pussy was so sensitive that I couldn't take it anymore. I pulled at his head. A fourth washed over me. I pulled again and yelled please. Then a fifth. He delayed one orgasm, and then continued giving me orgasms until my body wanted no more. This was a man that knew things.

This level of total body spasm had happened in the early years of my relationship with Edward, and was quite common in the early weeks of dating as I adjusted to the size of my future husband's cock. But I assumed I had outgrown this.

Bro said "I'll stop when you tell me you'll do anything." He continued stroking my g-spot while he spoke.

I didn't even think.

"I'll do anything," I replied.

With that, he got on top of me and began fucking me missionary style. He whispered in my ear.

"Tell me you want to get fucked in the ass," he said.

"Nnnn,"

"I want to be clear. You said you'd do anything," Bro replied. What he meant was 'If you don't say you want to get fucked in the ass, I'll tease and torment you until you do.'

"Ok, Ok. I want to get fucked in the ass," I said.

Bro fucked me really hard until he came inside me. I could feel the fullness of the butt plug. We lay next to each other for a few minutes, I could feel his cum leaking from me.

Ok, I realized. This time wasn't a complete repeat of the last encounter. He wasn't completely tender, but he'd shown some tenderness. At the same time, he'd pushed a pretty hard boundary. I wondered if there was a way to take control of this situation, to lay some firm boundaries for future encounters. As I did so, Bro nuzzled into me, turning on his side, and felt his stiffening cock against my hip.

He turned me over and removed the butt plug. I tensed a bit, waiting for his dick to enter me from behind, but that never came. Instead, he laid down, on his back.

"Get on top," he said.

What followed was a long, slow, passionate fuck, my clit grinding hard into his pelvis as he sucked my tits. I had a small orgasm as I rode him, and he came nearly simultaneously.

So... Bro was tender again. I basked in it.

I walked out of the apartment where my husband was waiting for me, acutely aware of the slick feeling of cum in my pussy, wondering whether it would ooze out onto the rain coat I was wearing, marveling at the perverse situation I found myself in.

Edward asked for the details immediately. His cock pitched a massive tent in his khakis.

"He let his roommates see my ass," I told him. I gave him the full story, as I watched him scratch at this boner through his pants, teasing himself.

"Can you touch me," he begged.

"When we get home," I said. I wasn't as angry at being caught between these two men as I had in the past. Maybe it was because Bro had been relatively gentle, and maybe it was because I was coming to accept the fact that there was a part of me deep down that enjoyed the humiliation Bro was capable of subjecting me to, or at least I loved how unpredictable this situation had become. I was assured that Bro would push things a little farther every time, and maybe I enjoyed that.

At any rate, I was looking forward to sex with my husband when we got home.

That, of course, is what we did. I gave his dick a few licks to get him extra hard, telling him, in between licks, how I'd begged Bro not to expose me to his roommates, and how Bro had done it anyway. How he had gone slowly when he lifted up the raincoat to tease the boys, and to prolong my anxiety and humiliation.

I raised myself up to straddle Edward, feeling his cock, his giant, rock hard dick, slide into my sloppy pussy, filled with Bro's cum.

Then I told my husband about the butt plug, how Bro had held me at the edge of orgasm until I'd acquiesced. How he'd made me promise to do anything.

"Use my juices to feel my hole," I told Edward. He reached behind me, and began teasing my little rose bud.

"Do you feel how tight that is? Do you want it," I said. "Stick a finger in."

I began quickening the pace as his fingers probed the crevice of my ass. "Feel how tight that is? God, don't you want to fuck it? It's so tight. But you can't. You're too big. But Bro is going to take that hole. It's practically his. Oh god, do you think it will hurt?

Everything between my legs and on Edward's lower abdomen was slick as I rocked back and forth, bringing myself to orgasm. Edward came in short order, pretty much at the moment I asked if anal was going to hurt.

I realized that if I couldn't control Bro, I could control Edward... or rather, he could not control himself.

*****

I began going to Bro's two or three days per week, Edward dropped me off in the morning on his way to the office. Bro would spend the morning fucking me. He and I would work evenings at the restaurant, and then I'd go home to my husband, recounting the day's events, and emphasizing the parts that excited him most.

"He hid my clothes today," I told Edward during one occasion. "I had to pee so bad. When I went to the bathroom, his roommates saw everything. And I could see their dicks in their pants. What if he wants me to fuck them? Would you say no? I'm not sure they'd care."

splooge.

"Today he made me bring my vibrator. He edged me with it for so long. I was delirious. I begged him. He made me kiss his feet. He made me walk around with the vibrator between my legs. I wanted to be a good girl for him. And when he let me come I said thank you thank you. And when he fucked me I said thank you. And then he made me clean him off and I said thank you. It was the biggest orgasm I ever had."

splooge.

"Another girl had left just before I got there. His dick was... he made me taste it and I could tell he had fucked her. He made me lick him clean everywhere, and then when he fucked me he took a really long time. He kept saying 'stupid fucking whore' and 'you fucking slut,' he was so mean but it made me cum, he fucked me so hard."

splooge.

"When I got there, Bro had just gotten back from rowing practice and was so sweaty. He told me I had to wash him in the shower. Oh god baby, it was so hot touching every part of his hard body. He told me every part of him had to be clean enough for me to kiss. I thought he just wanted a blowjob, but then he turned around and reached behind my head, he used my hair to guide my face right to his ass. I tried to pull away, and he said, 'I'll give you one more chance with the soap.' So I washed in between his cheeks. I was behind him on my knees, and I was jerking him. At first I tried to do it with a little bit of my tongue, but he grabbed my hair and pulled me in. He said something like 'Act like you actually cleaned it." I just licked and licked. I was kind of thankful that the water was running down his back. But then he turned around and the water was right in my face. He stuck his dick in my mouth and just... I couldn't breathe. Between the water trickling over my nose and his dick so deep. Every time I could take a deep breath, I got water up my nose and i started coughing, and he just didn't care.

Splooge.

"He made me wash him after practice this time. I was nervous because I wasn't sure I wanted to stick my tongue on his butt. I also knew that if he did, I wanted to do a really good job. That's so slutty isn't it? Like, I'd never want to lick a man's asshole. For him, I want to do it. I'd never do it for you. Bro wanted a blowjob, and he was so hard. Oh my god, then his roommate knocked and said he had to pee. Bro said come on in. I tried to get up, but Bro held my hair down and kept fucking my mouth. I could hear the roommate peeing, and my mouth was stretched so wide. There was just a thin curtain hiding us. Bro came in my mouth, and then he said "don't swallow." He opened the curtain and told me to open my mouth. God. This is so out of control. I was on my knees, totally exposed, and Bro just showed me off. Like, he came in my mouth and showed his friend, and I let him. Is there anything I'd say no too?

Splooge.

"He knows everything now. He made me tell him about you. He tied me up and teased me with a vibrator, and it went on for so long. God, I needed to cum so bad. And he just kept teasing me. Bringing me so close. And so I told him. How the only way you get hard is when he treats me like a whore. How you probably wouldn't care if I fucked his roommates. God. He knows that I whisper in your ear like this every night, and that's what makes you come."

Big splooge.

Throughout all of it, Bro kept training me for anal. The butt plug slid in easier and easier. The fear I had to the butt plug had gone away, and I found myself looking forward to the completely full feeling I had with the plug in one hole and Bro's penis in my vagina.

The night before Bro took my anal virginity, he sent a link to my work email that opened a .pdf with instructions on how to prep for anal. Bro told me to print it out and follow the instructions. There was a catch. He knew that that in printing this at work, I was risking quite a bit of humiliation. First was the fact that our boss likely had the ability to read our emails. The second risk was the act of printing it itself. The printer was in a shared space, used by the hostesses, for example, to print the day's menu.

It turns out that one of them, a 19-year-old college sophmore named Hayley with perky tits and a tight, size four ass intercepted the print. She turned it over to Bro, of course, because she was always looking for a reason to talk to him. I looked in the printer, to see it empty, and Bro made a show of handing it to me.

He smirked as my face turned crimson. I had half a mind to fire him. Certainly, I could frame the email he sent to me as sexual harassment. But then I realized that the act of printing this document would likely raise questions if Bro were to challenge that decision and tell our boss about our relationship. Rage flagged through my brain, but I merely grabbed the paper, pretended to be shocked at its contents, and told Bro and Hayley that I'd get to the bottom of whoever printed this disgusting material.

Later that night, Bro and I found ourselves alone in a storage area.

"I ought to fire you for that," I said.

"Relax," Bro said, which enraged me more.

"You humiliated me," I told him.

"But you like it," Bro said. "And besides, you can fire me, but would your husband really like that?"

This fucker, I thought. He was threatening me.

"Don't push your luck," I said.

"Don't push yours," he smirked back. And then he got close, grabbed a wooden spoon from a nearby rack, and swatted my ass twice with it. "There's more to come. I want to see you in the office later tonite."

"Fuck you," I said.

"And I think Hayley should be the last hostess working."

A nervousness enveloped my stomach. I was willing to accept - and expect - rough treatment. I'm ashamed to admit that I was a little turned on by the idea of Bro manhandling me, and then going home to my husband to tell the story of how I'd been punished. But why he wanted Hayley to work late was beyond me. Was he going to fuck my mouth in the basement and then take this hot young thing for an after work date?