The Mammoth Book of Urban Erotic Confessions

by Barbara Cardy

  I stayed up half the night masturbating, and I don’t normally do things like that.

  After that, I was hooked. Any time I got a little privacy, I got the butt plug out and stuck it up my ass. I’d never come so hard or so often. I even started taking little trips with it inside me, like to the grocery store, where I could shift from one foot to the other in line and give myself that secret grin I remembered from the woman at the sex shop. My experience made me wonder if she’d been wearing a butt plug herself while we were talking.

  I wasn’t sure how to bring all this up with my boyfriend. I especially worried about how to explain what caused my change of heart. Hoping to avoid having a conversation about it, I just came to bed one night with my butt plug in and started making out with him.

  The sensation in my ass got me much hotter than usual right away. My boyfriend was grinning and muttering about how sexy I was and how good he was going to make me feel. I felt bold that night. I moved one of his hands to my breast, then took a deep breath and put his other on my ass.

  He kneaded the cheek while we kissed, but before long he brushed the flared end of the butt plug, which was big enough to stick out a little from between my cheeks. He froze and frowned, then very slowly prodded it with his fingertip. “What the hell?” he said.

  I bit my lip, half because I was nervous and half because the way he made it shift around inside my ass made me want to squirm.

  “What is that?” he demanded.

  I told him it was a butt plug. I knew he was shocked, but he also seemed a little turned on.

  Still, he repeated what I’d said several times, like he’d never heard the words “butt plug” before.

  I still hoped I could salvage something, so I smiled like the store girl and told him I wanted to see if we could get his cock in my ass.

  He blinked a lot and said he didn’t know I was that kind of girl. The rest of the night didn’t go well. I was pretty mad the next day, and after work I didn’t feel like going home or calling him. I rode the train a fair bit too far, distracted and staring out the train window and trying to figure out what to do. Maybe this was my subconscious plan all along, but pretty soon I noticed that if I got off at the next stop, I’d be right near that sex shop.

  I told myself the whole way there that I couldn’t expect to see the same woman again. For all I knew, it could have been her day off. I got myself so nervous I nearly talked myself out of going in.

  When I finally did go in, though, she was there, helping another customer. There wasn’t anyone else in the store except a manager type who was lugging a bunch of big boxes into a back room. The shop girl gave me her big smile when the door chimed behind me, and I hoped that meant she remembered me.

  Now that I’d wound up face to face with her again, I had to come up with my next step. I decided I wanted to ask her advice, so I lurked around pretending to look at vibrators until the other customer left.

  She came over to me right away. She winked and raised her eyebrows and asked how things went with the stuff I’d bought the last time.

  I did blush, like I’d been afraid I would. I found my voice pretty quickly, though, and explained that it had been great for me but not so much for my boyfriend. I told her how freaked out he’d been, and how curious I still was about trying some of the things I’d seen in that book she sold me.

  I even asked her how she thought it would feel if I used a really big dildo instead of a plug in my ass – though I thought I was going to die of embarrassment trying to get that question out of my mouth. I couldn’t believe how much had changed about me in the short time since my first trip to that store.

  She winced sympathetically when I told her about my boyfriend’s reaction, and seemed impressed when I described how much I’d gotten into wearing the butt plug around. She warned me to be careful about sticking a dildo up my ass, though – apparently, it’s really important to be sure everything that goes up the asshole has a flared base so it can’t get lost inside.

  We talked practical details like that for a while, then we stopped and I sort of just stared at her. She seemed even prettier than I remembered. Her lips were full, colored bright pink. She had on a flowery dress this time, and I couldn’t stop speculating about what kind of underwear she wore beneath it, or if she was using any sex toys at that very moment.

  Right away, I started to worry that she’d catch some idea of what I was thinking about. I got flustered and stammered a little.

  She just cocked her head to one side and looked amused.

  I wanted to talk to her more, but I didn’t want any other customers to come into the store while I was in the middle of any really personal revelations, and I didn’t want the manager to overhear either. I wanted to meet her after she got off work, but worried she’d think it was creepy if I asked. I figured people probably wanted to see her outside of the store all the time. All this thinking meant my mouth just opened and shut for a while as she watched me.

  She saved the day, though. She gave me a really quick hug, then said she’d be at the coffee shop across the street from the sex store for a couple hours after seven, when her shift ended. Then she excused herself quickly, and went behind the register.

  It sounded like store policy didn’t really allow her to hang out with customers, because she’d hinted we should meet up later without coming out and saying it. I didn’t ask her any more questions, because I didn’t want to get her in trouble with her manager. Instead, I bought another bottle of lube (I was running low from all my masturbating with the butt plug), shoved it into the bottom of my purse, and went to kill a few hours.

  I showed up at the coffee shop about a minute after seven, really keyed up and nervous. I beat the store girl there, so I ordered a drink and took a seat toward the back, where I could watch the door. She showed up not too much later, waved at me, and came over with a double espresso.

  I’d expected the conversation to be awkward, but we talked like we’d known each other forever. Her name was Nina, and for a while we just traded favorite music and stuff like that. It was fun, and I liked her more than ever.

  Then she leaned over the table, bringing her face really close to mine, and asked me to tell her more about what happened with my boyfriend. I went into the whole long story, and she was really sweet about it. I’d left my best friend behind when I moved, and hadn’t found a replacement in Boston. I hadn’t had a chance to talk to anyone about this, and I also gave Nina way more details than I would have given my best friend back home!

  I finished up by trying to explain what had happened to me since the first day I came into the store. I lowered my voice almost to a whisper, but no one else seemed to be paying any attention to us. I went ahead and told her how I’d gotten really obsessed with wondering how anal sex would feel now that I’d learned to like the butt plug. I said I’d spent the day trying to figure out what to do. As crazy as it sounded, I was thinking I might have to break up with my boyfriend if he wouldn’t try this with me. I wanted to so badly, I didn’t think I could go without it.

  She held up a hand at that point and told me not to break up with him yet. She reminded me that I’d told him at the beginning that I never wanted to do anal, and he probably needed time to adjust. Then she got a sly expression and pointed out that it might be hard to find someone to fuck me up the ass if I broke up with my boyfriend, anyway. (Now that we were in the coffee shop, she’d abandoned the clinical words she’d used at the store.)

  I sighed and admitted the dirty thought I’d been having all day – I felt so desperate to try anal sex that I’d been thinking about posting a personal ad for it on an adult website.

  Then she really started grinning. She told me she had an idea that might save me having to screen a bunch of people. I could be getting it up the ass that very night, she said.

  I’m not stupid, so I knew right away she was suggesting something to do with her. The thought aroused me so much I could barely see straight. All I could manage was, “W
hy me?”

  She said she’d been looking for someone to join up with her and her boyfriend, and I was the first person she’d met who’d gotten as excited about ass play as she was. She called me her “budding little ass-slut”. That didn’t offend me the way you might think – really, it turned me on.

  She told me she’d have her boyfriend fuck my ass (and promised he’d be very good at it), if I agreed to make out with her a little since he liked seeing her with other girls. I paused for a long while before I answered her. I felt sort of bad about doing this behind my boyfriend’s back, but I really, really didn’t want to pass it up. Given how much Nina loved getting it in the ass, her boyfriend had to be an assfucking pro. And I’m not a lesbian, but I was so fascinated by Nina that I liked the idea of kissing her a little. I still couldn’t understand how that butt plug had unleashed this slutty side of me that I’d never known existed, but I was too excited to question it anymore.

  I agreed, and she took me home right away. She seemed really excited. She chattered at me the entire short walk to her place, and practically bounced. When we got to her apartment, she flung the door open and sang out, “I brought you a surprise!”

  Then she pulled me inside. Before I had time to hesitate, her mouth closed on mine. She was more aggressive than I expected from a girl. She slipped her hands under my shirt and pushed me back against the wall. I was sort of dazed and stunned by everything that was happening, but I didn’t want to stop her.

  In fact, I tried to give as good as I was getting. I grabbed Nina’s ass and pulled up her skirt, feeling for a butt plug between her ass cheeks. It was there.

  A low whistle interrupted us, though, before I could find out anything else.

  Nina pulled away from me and grinned at one of the hottest men I’d ever seen, who’d just walked into the hall where we’d been making out. He was fit but enormous, easily a foot taller than her, with a really sexy, arrogant cut to his jaw. I thought about the cock he was probably packing and shivered at the thought of it filling my ass.

  Nina introduced us and explained what I’d come to do. Without further ado, he scooped me up in his arms and carried me to their bedroom, his fingers already reaching into my panties, which I’d drenched.

  I didn’t even think about asking him to slow down – I was so turned on by then that I almost came the moment he dropped me on the bed.

  Nina asked if I wanted her to be the one to warm me up. I moaned and nodded. She lubed my ass and started putting fingers inside me. I’d never had someone else’s finger in there before. It drove me crazy when she wriggled them or curled them. She lay on top of my back, fingerfucking my asshole and kissing my neck. She talked dirty, too, whispering about how nice my ass was, how easy it was to stretch, and how much it would stretch around her boyfriend’s big cock.

  She looked up quickly to tell her boyfriend to let me borrow her vibrator. He fumbled with some cords beside the bed – I wasn’t paying attention to anything but Nina – then this really loud sound started up and Nina pressed something to my clit that just about made me fly off the bed.

  Whatever she used for a vibrator was about three times more powerful than anything I’d tried. I came just about as soon as it touched me, but she didn’t let up at all. She kept that vibrator trained on my clit while she went at my ass with her fingers, and I came until I lost count. I came until I drooled – from my mouth and my cunt. I swear she could have put her whole hand up my ass and I wouldn’t have complained.

  Sometime around then, I started asking for her boyfriend’s cock, but I was so incoherent with pleasure I have no idea what actually came out of my mouth. Nina seemed to get the idea, though, because she had him lie on the bed next to me. I waited for him to roll over and take me, but that obviously wasn’t her plan. She pushed me up to all fours.

  Eventually I understood she wanted me in her favorite position – girl squatting on top. I wasn’t sure if I could hold myself up. In fact, I just sat there limply while she kissed him a little and put a condom on him. Luckily, they didn’t seem to mind that I was already so spent.

  Nina came back to me after a minute and gave me a friendly kiss on the cheek. She explained her boyfriend was great for assfucking because he could stay rock hard through anything. I could feel free to go as slow as I wanted while I got used to it. He’d love every minute of it, she promised, with no pressure at all for me to do more than I wanted.

  By then I would have fucked anything she’d let me, but I didn’t tell her that. I just crawled into position on top of her boyfriend. He looked up at me and petted my cheek a little, which I liked because it made me feel pretty. We were both way too horny to mess with any more foreplay, though.

  Nina helped guide me into that squat. She even spread my ass cheeks for me. Her boyfriend helped to brace my thighs, which were trembling already.

  It turned out I just didn’t have the energy to draw anything out. My ass was so slick and so ready and so relaxed that when I worked the tip of his cock into me, the easiest thing to do was to sink all the way down.

  That moment changed my life. I’d never felt anything so delicious. I just sat there a minute with his cock buried all the way in my ass and savored it. I met Nina’s eyes and knew she understood exactly how I felt.

  I didn’t bother with going slow. I asked him to fuck me hard while Nina helped me hold the vibrator. It was the first time I’d ever come so much, though certainly not the last.

  After that night, I broke up with the guy I’d been seeing. Eventually, I found another man who loves Nina and her boyfriend as much as I do. Now I have not one but two men who love to fuck my ass and a best girlfriend to share it with. I couldn’t be happier.

  Barcelona

  Maggie, California

  I have a cousin whom I have always wanted to fuck. But don’t worry – we’re second cousins once removed and he’s adopted so there’s only a hint of taboo associated with the attraction, but that hint has always been enough to give my imagination a bump when he’s around. That, and the fact that Eric is terribly sexy in a quiet sort of way with his pianist’s hands and mossy green eyes – so much so that I’m usually halfway through mentally undressing him before I even realize I’m doing it.

  There was a point in our early twenties when it almost seemed as if something might really happen. He was studying abroad at the time. Our families have always been close, so that summer my mother and his parents decided to visit him in Barcelona. I, never missing the opportunity to travel (or to see him, I must confess), came along. I still remember how hot the city was that summer – sultry and intense, with a sky so blue it looked like turquoise. Sunny Spain. We ate, we drank, we walked and smoked and laughed, drawn crazily to each other, even as we trailed our adorably oblivious parents. One night, when the music from a discotheque pulsed into the heated space between us, we nearly kissed. Nearly. So nearly. It was the most sensual nearly that I’ve ever experienced in my life. But we didn’t. My tipsy aunt found us and joyfully poured us more wine, effectively breaking the moment. And that was it. We left. He stayed. I married. He married.

  It’s been nearly ten years since that night in Barcelona and I still think about it sometimes, deep in my secret self. In fact, I was thinking about it last week when Eric and his wife, Hannah, came to visit us (us meaning my husband, James, and me) for a few days. Hannah and James have always gotten on, so it made sense for them to run errands while Eric and I made food for the big family dinner we were having that night. I had chosen my menu’s theme carefully: southern Spain, ostensibly in honor of our parents’ upcoming venture back there, but mostly as a quiet wink to Eric, one I had no idea he would even see to receive . . . which would have served me right. I had no business stirring that pot after so long, but I just couldn’t drop the spoon.

  Anyway, that’s where my mind was while I was chopping tomatoes for gazpacho that afternoon – in Barcelona, steeped in self-recrimination and the ever-insistent presence of my attraction to him. Meanwhile,
Eric was on the other side of the small kitchen cutting lemons and herbs. I was just veering into a quiet appreciation for the way his fingers tucked under as he minced (yes, I am truly pathetic) when he looked at me, something obviously on his mind. Then he turned abruptly back to his work. I cocked my head.

  “So . . .” he said a moment later without looking up.

  “So . . .” I repeated, after a lengthy pause.

  “So,” he said, again, still chopping. By now, the lemons were pulp. “Hannah wants to sleep with James before we leave.”

  “Really,” I said.

  “Yeah, she does.”

  I put down my knife and leaned against the counter, surprised but not at all shocked. Both of our marriages are intensely committed but non-monogamous, and Hannah and James had always had a bit of a thing between them. I had rather been expecting something like this to come up. What I couldn’t tell was how Eric felt. I’d always been able to read him, but I couldn’t read him now. It was that fact, rather than the thought of James and Hannah, that completely deflated me.

  “That’s fine,” I said, aiming for matter-of-fact. “James and I have already talked about it. She’s lovely. He wants her too. I’m sure they’ll work something out.”

  Finally, Eric turned around. He looked at me for a moment, gauging me for something, though I couldn’t have said what.

  “So, you’re all right with it then?”

  “Of course it’s all right,” I said, mildly exasperated. “Besides, Hannah could have talked to me if she wanted to be sure. Why are you the acting liaison?”

  “Because.” He stopped and looked away. Then looked back at me. My nearly unflappable cousin was nervous. Maybe he wanted to sleep with James too . . .

  “Because,” he repeated, “I want to sleep with you.”

  I opened my mouth. Nothing came out. I closed it and tried again.

  “Oh.”

  I blushed, mortified that, at thirty-one, with a sexual history the size of a small planet, my cousin could make me blush. He put his knife down on the carving board and walked towards me, clearly taking the blush as a good sign.