It didn’t take long before both of us began moving our hips. I thrust mine upward driving my cock in and out of her mouth while she drove hers downward, banging her pubic bone against my chin. Soon we were sucking and fucking and licking and stroking.
I came first. I fired a thick wad of hot spunk deep into Amanda’s throat and she swallowed every drop. I continued stroking her clit with my tongue. A moment later she shoved her ass back against my face, nearly smothering me with her hairy pussy as she came.
When she finally rolled off of me and turned around there was no denying what I had suspected all along. Before I could say anything, Amanda pressed a finger against my lips to silence me. Then she covered my lips with hers and we could taste each other’s sex when our tongues met. As we kissed, she reached down between my legs and took my saliva-and-cum-covered cock in her hand. It didn’t take her long to massage it back to life.
Then she swung around and mounted me in a reverse cowgirl. She grabbed my ankles to support herself, I grabbed her hips. She rode me fast and hard and I met each of her powerful downward thrusts with powerful upward thrusts of my own.
She came first this time but I slammed up into her another half-dozen times before I came, sending my second wad of hot spunk deep into her throbbing, spasming, clenching pussy.
When her pussy finally quit trying to milk every drop of cum from my cock, my sister-in-law dismounted me and climbed off the bed.
“You’d better shower,” she said, “while I change the sheets.”
I did just that and returned to bed fully satiated. After quickly falling asleep in the coolness of the fresh sheets, I dreamed, and in my dreams had sex with my wife and her sister and both of them together. I tossed and turned and finally woke to find my wife and her sister preparing dinner for the three of us. I was a bit nervous, but Amanda didn’t act as if anything out of the ordinary had happened that day.
Neither of us said anything about what had happened and I certainly didn’t tell my wife. At first I thought our sexual encounter was an anomaly, that Amanda had simply been so horny that she would have fucked any available cock.
I was wrong.
She woke me again three days later. This time, though, she didn’t try to pretend she was my wife. I was lying on my back, my nocturnal erection apparently tenting the sheet. She threw back the sheet, climbed on the bed, and mounted me. She was already slick and I found out later she had applied a touch of lube to get herself that way. By the time my cock was fully encased in her pussy, I was wide awake. I started to say something, but she shushed me by leaning forward and covering my lips with hers. Our tongues met in an oral wrestling match as I wrapped my arms around her and held her tight against me.
I thrust my hips upward, drilling in and out of her. Her breasts were trapped between us and jiggled as I fucked her, her erect nipples playing my ribcage like a xylophone.
I rolled us over so that I was on top of her. Then I reached down and pulled her legs up, hooked my arms behind her knees so that her pussy was pointed almost straight up. I slammed into her again and again and again as she encouraged me to go harder, faster, deeper.
My sister-in-law came first and then I came. When my cock finished unloading within her, I rolled off of her. She curled up in my arms and rested her face against my chest. I didn’t know what to say so I said nothing.
After a bit she suggested a shower. I thought she meant she would change the sheets again while I was in there, but she had other ideas. As soon as I was in the shower, she joined me. With a dollop of liquid soap in the palm of her hand, she bathed my balls and brought my cock back to life. As soon as I was fully erect she turned around, leaned forward, and braced one hand against the shower wall. I took the hint and pressed the head of my cock between her pussy lips. Then I grabbed her hips and thrust my cock into her. I drew back and did it again and again and again.
We fucked as the hot water cascaded over us. Though she was braced with one hand against the wall, Amanda had the other hand free. She reached back between her thighs and cupped my hairy ball sac in her hand, kneading my nuts as I drove into her. I couldn’t hold back and I came.
She wasn’t quite there yet, so she moved her hand from my balls and stroked her clit with the tip of her finger. Her long fingernail teased the spasming shaft of my cock as she did that. And then she came and came hard, her pussy spasming so forcefully that it expelled my softening cock and made us both laugh.
We finished the shower together, dried each other off, and then changed the bed sheets. I returned to bed and she went off to do whatever it was she usually did during the day while my wife was at work.
Again we didn’t speak of what had happened, and the rest of the summer continued much the same. I fucked my wife at least once each weekend, but I fucked my sister-in-law two or three times during each week. She always gave as good as she got and we didn’t limit ourselves to just the bed and the shower. Knowing we were unlikely to be interrupted, we also did it on the couch and in the recliner, on the kitchen table and once in the backyard.
When it came time for Amanda to leave us because her new apartment was ready for her to move in and the school year was about to begin, I knew I was going to miss her presence in our house.
Carol and I helped Amanda pack her car and then we stood in the driveway saying our goodbyes. She hugged me and kissed me and thanked me for my hospitality. I couldn’t help it but my cock began to stiffen as she flattened her breasts against my chest and pressed her pelvis against mine. I almost parted my lips to shove my tongue in Amanda’s mouth, but she pulled away before I could.
Then she hugged Carol and said, “Thank you for your hospitality and for everything you shared with me this summer.”
After she drove away I took my wife’s hand and practically dragged her into the house. We didn’t get past the living room before I peeled off her sweatshirt and unfastened her bra. I cupped her breasts in my hands and teased her nipples with my thumbs as I covered her mouth with my lips and we kissed deep and hard.
Apparently Carol was just as horny as me and we quickly stripped off each other’s clothes. She dropped to her knees and took my cock in her mouth. She had never been able to take in the full length but she certainly tried. I held the back of her head and pumped my cock in and out of her oral cavity. I came quickly, sending a thick wad of hot spunk splashing against the back of my wife’s throat. She swallowed every drop.
Then she stood, took my hand and led me back to the bedroom where I mounted her and fucked her hard and fast. Her fingernails scratched at my back, leaving red welt designs and, when she was about to come, she grabbed my ass, dug her fingernails in, and pulled me tight against her.
She came hard. She screamed. And I rode her writhing pussy until I came, too.
As we lay together afterward, my wife asked, “Did you like my sister?”
“Sure,” I said, not knowing where the conversation was headed. “Why wouldn’t I?”
“She really liked you.”
“That’s nice,” I said.
“She liked you so much, she wants to come back for Christmas.” My wife rose up on one elbow and looked into my eyes. “Do you think you’ll be up for that?”
And that’s when I realized my wife had known all along what was happening while she was at work. She and her sister were still sharing everything.
“Yes,” I said with a smile. “I think I will be.”
I’m looking forward to this Christmas. Maybe my present will be to fuck both of them together.
The Mentor Behind Me
Michelle, Boston
The first few times I tried anal sex, I really didn’t like it. I only did it to please the guys I was with, and it didn’t feel very good to me. Pretty soon, every time I started dating a guy, I told him I didn’t do anal, and I only stayed with the ones who seemed OK with that. I figured I’d never have to suffer through it again.
Except that once I didn’t have to worry about it anymore, something
happened that got me totally obsessed with it.
It started the time I went into a sex toy shop. Where I grew up, that kind of store seemed really seedy. After I moved to Boston, which is a really liberal city, I started noticing nice, clean stores that catered to women. I went in and looked at their vibrators, of course, but I couldn’t help also noticing this row of really colorful toys designed for the ass.
They had a whole display with lube and books and these alien but friendly looking toys. I snuck over and picked up one of the books. Inside, there were pictures of people having anal sex in positions I’d never imagined before. The times I’d done it, I lay on my stomach and hoped for the best. These ladies were squatting on top of the guy or sitting cuddled in his lap or bent over the bed. I knew these were photo shoots, but they looked genuinely excited. At first, I kept looking because I was curious. Then I got turned on. I’ve never been that aroused in a public place before. I stood there holding that book with my heart pounding. I held it tilted at a funny angle, too, trying to keep anyone else from seeing the title on the cover.
After a while, one of the women who worked at the store came over to check on me. She asked if I had any questions, and I must have turned purple with embarrassment. I couldn’t get it together to form any words, so she gave me a cute little smile, like she had a secret, and just started talking. At first, she sounded clinical. She explained how you have to warm the ass up and sort of stretch it before a man tries to penetrate it. This made me laugh a little, because I got a mental picture of my ass trying to do aerobics or yoga.
My amusement must have encouraged her, because she kept going. She told me the toys were for those warm-ups – though she threw in that you could also masturbate with them. She explained about lube, and how to buy the right kind. She picked up the book and pointed out specific pictures and positions and talked about them. Those pictures turned me on even more when she described how they would feel while I looked at them.
At this point, she started getting personal, saying things like, “What I love to do is . . . ” and, “It feels so good when my boyfriend does . . .” She said anal sex made her feel really full inside, way more than when her boyfriend puts it in her pussy – though I don’t think she said “pussy”. She kept using scientific names for everything, I guess because she was a store employee, but I’d feel too weird writing it down that way.
She said lots of great things about anal. She said she likes to use a vibrator while her boyfriend sticks it in her ass, that it makes everything way more intense. Sometimes, she even puts a dildo in her pussy at the same time so she can get even more of that “full” feeling.
I don’t think of myself as sheltered, but I’d never heard a woman talk like that before – about anal sex or anything else. I couldn’t picture her getting it in the ass – she had this really soft look about her, like her skin was made of cream. She wore black-rimmed hipster glasses and looked sort of intellectual. I could see her reading a book while having sex, even though it sounded like she got way too wild to manage anything like that.
In fact, the more she talked, the more I caught myself imagining what she would look like doing the things she described. My brain got really fascinated with this. Even though it felt rude to mentally undress her like that, I couldn’t stop wondering about personal details, like what her boyfriend looked like so I could get an accurate mental image of him, too. She’d already told me her favorite position for anal – woman squatting on top – and how she liked to prepare for it – with this one squishy butt plug which she would put in a few hours before she and her boyfriend wanted to do it.
I wanted to know how often she fucked her boyfriend this way, and what kind of face she made when he first got his dick inside her, and what it felt like for her to have his cum in her ass.
“You really like to do this?” I blurted the question out before I considered how stupid it sounded after everything she’d been telling me.
She blinked at me, then grinned really wide. That was the moment that sealed the deal for me. When she smiled like she’d just helped me discover Christmas, I had to believe anal sex was great.
She told me her boyfriend hadn’t even wanted to try anal at first – he thought it would be gross – but she’d convinced him. That was definitely the first time I’d heard about a girl talking a guy into doing anal.
She gave me a few more tips about how to prepare for it, and then led me toward the cash register. She really had me by then. She asked what I wanted to buy, and I just stammered and nodded at everything she put on the counter. By the time she finished, I’d bought the book I started out looking at, a bunch of different toys, and the special lube she recommended. Normally, I’d have paid more attention to what she was telling me, but I was in this aroused daze.
I’ve never been attracted to women. I don’t think I wanted to have sex with her. I think I wanted to be her, and I’d gotten the idea that buying all this stuff would help me do it.
She gave me a big smile and packed all my stuff in a paper bag. She told me to come back and let her know how it went for me, and promised she’d be happy to help if I needed any more tips or recommendations. I blushed just thinking about trying to do the stuff she’d described to me or, God forbid, telling her about it afterwards.
In the back of my head, I knew I shouldn’t buy all those things if I had no intention of using them, but I didn’t have the heart to hand anything back or try to return it later. I didn’t want her to think I wasn’t cool, or that she’d wasted her time with me. And I guess, honestly, I wanted to look at the pictures in that book some more.
So I tried not to worry too much about how much money I’d just spent. I took everything home and stashed it in the bottom of the closet. I didn’t think I’d do much with it, but found out I was wrong later that night when my boyfriend couldn’t come over like he’d planned.
I was lonely and bored. I didn’t want to go out, but I didn’t know what to do if I stayed in. I wandered around my apartment for a while, and finally got into the bottom of the closet. I spread the things I’d bought at the sex shop out on the bedspread and just looked at them for a while. And I started getting hot again.
Really hot. Like, I have to get the vibrator out right now or I think I’m going to die. I usually don’t make too much noise when I masturbate or do it for too long. This time, everything was different. I flopped down next to all those anal sex toys and humped that vibrator for all I was worth. I grunted and groaned and got really loud. I’m sure the upstairs neighbors would have been surprised to learn my boyfriend wasn’t over.
I made myself come the first time before I even got my pants off. Then I did it again through my underwear. I thought I might stop at that point, but then I glanced over at the toy she’d recommended the most, the one that was squishy and large and shaped sort of like a screw. I imagined her easing that thing into her ass, and I moaned and had to keep going, shoving my panties down to my knees because I couldn’t be bothered to take them all the way off.
I still don’t know what got me so incredibly turned on. Like I said, I didn’t even think I liked anal sex before I talked to that girl. Maybe it’s because she was so pretty, or maybe it’s because she made it sound like so much fun.
Whatever started it, I’d discovered something big. I got all the way naked and turned my vibrator all the way up. I was scared to even touch the toys, but eventually I got turned on enough that I did. First, I picked up that favorite butt plug of hers and just held it. It was brand new, so I felt OK about bringing it up to my face. Pretty soon, I was rubbing it across my cheek while I ran the vibrator up and down my clit.
I’d come so much by then it almost hurt to keep stimulating myself anymore, but I just couldn’t convince myself to take a break. I got an impulse to lick the butt plug, so I did. It didn’t really taste like anything, but I pictured myself behind the girl from the store, licking the butt plug to get it ready for her. Before I knew it, I was sucking the butt plug, runni
ng my tongue over the screw threads and pushing it in and out of my mouth like I was giving it a blowjob.
I switched off the vibrator for a second because I wanted to free up my other hand. I snuck that hand around to my ass and started to feel around. I don’t know what I expected to find – obviously, I touch myself there all the time in the shower to clean myself. Still, I held my breath because I was so nervous about playing with my ass at all, even in private.
I got between the cheeks and found the hole, and was surprised at how soft it was, and how nice it felt to stroke it. After a few minutes of that, I got the lube and spread it around. It felt cold and kind of strange, but not bad. I slipped my fingertip easily into my ass and felt no pain – quite the opposite.
That butt plug was calling to me. The girl from the store probably grinned just before sticking it in. I tried to copy her, then lubed it up and pressed it against my asshole. I did have to push a little to get more than the tip in. She’d talked a lot about going slow, so I took a deep breath and prepared for patience.
That wasn’t what happened at all. I guess I’d gotten so relaxed and aroused from all the orgasms that my ass was more ready than I knew. As soon as I applied a little real pressure, the butt plug popped right in. I yelped out loud, I was so surprised.
I squirmed back and forth on the bed, trying to get used to it. I did feel full inside, like she said she did. I wasn’t used to feeling stuffed there, but empty in my pussy. I wished my boyfriend were there to fix that, and the image of him thrusting into me while her butt plug sat up my ass got me going again.
The first orgasm I had with the butt plug inside me blew my mind. Everything was tenser, tighter, harder, longer-lasting. The plug pushed the walls of my pussy closer together so that when I came, it felt like they caressed each other. Now I really knew what she was talking about, and why she smiled like that.
The Mammoth Book of Urban Erotic Confessions Page 37
