Category: anal sex

Three Way Date

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One night I decided that I was going to have a threesome with Tony and Kevin as soon as I possibly could. Having sex outside of our marriage was an idea I would never have thought of myself, but my husband had suggested opening up our marriage and since I knew he’d waste no time getting a woman, I wasted no time getting two men.

I work with a guy named Tony who’s a real ladies’ man and has probably banged half the girls in our office. We’ve been good friends and he’s never hit on me—I let him know I wasn’t on the market at our first lunch together—but we always talk candidly about sex and the sexual experiences we’ve had. At a recent lunch he told me that he and his friend Justin took one of Justin’s girlfriends out one night. He explained that it all started innocently enough with a poker game that turned into a strip poker game that turned into a three-way. He and Justin apparently turned her every way but loose, from double blowjobs to a double entry. They kept it going until they were all drained.

Although I feigned some good-natured disgust, the story set my imagination racing. The idea of being with two guys made me warm all over. I imagined two guys making me do nasty things like giving them each blowjobs then fucking them both at once without my husband there for the first time. At any rate, I told him about my husband and I deciding to fuck other people. Tony was enthusiastic and suggested that since we were good friends and didn’t have to worry about becoming romantically involved, he would be a natural to start with.

I said, “I don’t think an office affair would work, but if I change my mind, I’ll let you know.”

A week later, he asked me out for a drink after work and I accepted. I asked him if it would be just us or if I should bring a deck of cards, hoping he’d get the hint.

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The Boys Locker Room

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Sierra hung back in the locker room, watching as her fellow dancers finished getting dressed and left. No one said a word to her-not that she expected they would, since none of them liked her at all. They hated her for being beautiful, with long jet black hair and big icy blue eyes, C-cup breasts and a tiny waist, long legs that went on for forever and a devilishly charming smile. They hated her for being the favorite, the one who brought all the guys to the games, the one who got all the attention.

Quite simply, they hated that she was so obvious about being a slut, while they had to sneak around and pretend they weren’t fucking whoever took them to the movies. She would have with them being in college now, they’d be a little more open with their sexuality.

She let her lips curl into a slow smile as the last one swished past her with her nose in the air. “Bitch,” Sierra muttered under her breath. She despised the trust-fund snobs as much as they despised her, but the dance squad gig was a sweet deal. Not that she really needed an excuse to find her way into the football players’ locker room after dance practice, but it helped.

She waited a minute to make sure no one was going to come back and surprise her, then moved quickly across the hall and slowly pushed open the door to the boys’ locker room. She heard the laughter and the sounds of running water and felt the steam roll out to her. The heat hit her and instantly made her wet.

“Hey boys!” she called out, grinning slyly as she stepped back into the inner sanctum.

There were only five of the guys still there, and they all looked up in anticipation when they heard her voice.

“Hey, Sierra,” Brett drawled. The tall brunette’s eyes sparkled as he shifted his hips, the towel that was loosely knotted around them dropping to the floor. Sierra licked her lips as she eagerly eyed his cock. It was still soft, but that was changing rapidly. “I was beginning to wonder if you weren’t coming today.”

Sierra laughed. “I plan on cumming quite a bit today,” she said with a wink. She walked closer to him and slid her hand down his chest and stomach, wrapping her fingers around his cock and stroking it slowly. He groaned and arched into her hand as his cock hardened.

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Bachelor Party Fuck Up

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Ever think you have the perfect ideal to take care of a problem. You know one of those ideals that makes perfect sense in you head, but when you go through with it falls apart or worst it fucks everything up. Boy did I have one of those. Here is how it all went down.

It was the weekend before Rob, my cousin’s bachelor party, Katie the bride to be and my best friend, found out about the plans by read an email detailing the plans and came to me.

The email talked about how my brother Tim was going get some his buddies and Rob’s buddies together and take Rob out for happy hour and hit a few bars to get Rob drunk, then to go to a strip club before heading back to Tim’s apartment where another stripper would show up.

Katie thought it was strange that they would hire a stripper to go to Tim’s apartment after coming from a strip club. Not understanding that she came to me asking me, why not just stay there?

That’s when I told her that knowing Tim, he had hired the stripper to fuck Rob and taking him to the strip club is just to get him drunk and horny. My brother is a big jerk. He thinks life is too short to be tied to only one piece of ass. So I was sure Tim wanted to give our cousin Rob one last taste of another woman before he was tied to Katie.

Katie got so angry and scared at that thought and wanted to tell Rob he couldn’t go. I told her that would only cause problems and problems like that were not the why to start a marriage.

So I came up with an idea to ruin their plans and told her not to worry I fix my brother and his friends. Or so I thought.

Since the email had the name of the stripper and her number, I call the day of the party and canceled the party with her. Then I called my brother disguised my voice and left a message on his answering machine telling him Maria was sick but Amber would be there to take care of the groom.

My plan was to go to the party and start to strip and when I got down to my black lace bra and panties. I would get down on my knees in front of Rob and then tell him I wanted to give him a blowjob. Then I pretend to get sick and run into the bathroom, then after making sound like I was throwing up I would leave. After the guys left I’d go back and bust my brother then I’d give him hell.

The night of Rob’s bachelor party I showed up to Tim’s apartment in disguise. Neither my brother nor my cousin had seen me since I had dyed my hair platinum blond, so blond it was almost white. Plus I never hung out with Tim or his friends so I felt pretty safe. I also wore a lot of make-up, much more than usual and put in colored contacts. I though, there was no way that they recognize could me.

Plus I knew the guys were not there to look at my face but at my body. So I knew that the black velvet push up bra and match thong panties, plus garter belt and fish net stocks would have their attention as soon as I slip off the skin tight dress.

It was 11:30 when I arrived and as my brother, Tim let me in. he looked at me funny and asked me to turn around. Then he squeezed me ass as he commented how hot I was and the other guys quickly made similar comments. My cousin, Rob was sitting on a chair and looked so wasted. They were so drunk I now felt more comfortable that they wouldn’t recognize me. The guys were all horny and drunk and were eager for me to start stripping right away.

I started to dance for them as soon as they turned on the music. Want to get this over with. I danced as sexy as I could, grinding my hips, shaking my ass, touching and squeezing my breasts, as I slowly removed my dress. As I did I found I was actually getting wet and I was becoming very turned on stripping in front this guys , even though my own brother, and my cousin were there.

Feeling brave I turned around and wiggled my ass in front of guys. Then one of the guys made a comment about the butterfly tattoo on my ass check. I spun around quickly and looked at my brother, remembering he had once seen my tattoo, fearful he had recognized me. But he didn’t have a look on his face like my butterfly had registered with him. Then I thought there had to be a lot on strippers with butterfly tattoos on the asses or lower back or other place.
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Anal Virgin Gets Ass Fucked

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Lauren examined her body carefully in the mirror. Tonight was special and she had to look perfect. She ran her hands gently over her round breasts, pausing to linger on her hard nipples. She continued moving her hand south across her flat stomach and into her soft and smooth pussy searching for her clit. It was easy to find because it was already swollen from the excitement of the events planned for tonight. A soft moan escaped her lips as she brushed a finger across it. She turned and looked at her round ass. She reached around and grabbed her cheeks and spread them so she could get a good look at her asshole. A warm rush filled her body. This is what was making tonight special. She was going to let Brandon fuck her ass. It is something she had never done, but Brandon loved it and had been begging her for months to let his cock invade her ass. Finally, she had agreed. She couldn’t resist him any longer. While keeping her left hand on her ass to keep it spread, she ran her right hand up between her legs. She paused to slip a finger in her wet pussy and then she began to play with her asshole. She explored the soft skin around it first. God, it felt so good! She softly pushed one shy fingertip into her ass. Her excitement reached a new high as she watched her asshole swallow her finger. She couldn’t wait to feel Brandon’s cock slide into her like she her finger had.

Oh God! Brandon! He would be there any second! Lauren grabbed the sheer black nightgown she had purchased for tonight and threw it over her head. She took one last look in the mirror to admire the way her breasts pressed against the fabric and how inviting her cream colored thighs looked. She straightened her hair and ran to the kitchen. She pulled the bottle of wine from the ice bucket and opened it. As she was reaching for the glasses, she heard the front door open. Brandon had arrived. He walked into the kitchen as she was pouring the wine. A hungry smile crept across his face as he looked her over.

Lauren gave him her most seductive smile as she handed him his glass. “How was your day”, she asked as nonchalantly as she could.

The hungry smile became a full grin as lust filled Brandon’s eyes. “It just got a lot better”, he answered in his deep voice.
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Cheating Girlfriend

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The time this story takes place is several months back, about 4 to be precise. Me and MIchelle had been dating for nearly a year and a half now. We’d been sexually active with each other for just over a year and had always used protection of some sort because we both agreed it was best.

Michelle was really stoked about the next several days because her parents were leaving on vacation to Mexico and were leaving her alone to watch over the house while they were gone. Like most teenagers she immediately began planning for a party by calling and telling everybody she could. She was especially wanting me to go because she said she was gonna be wearing my favorite outfit just for me, which was a tight miniskirt and spaghetti strap tank top. When she said this I sensed a bit of tease and eroticness in her voice so naturally that got me stoked for the party as well. Naturally I had to help with getting the party going. My job was to find a way to get as much alcohol as I could and bring it to her house. The day of the party I got up about 11, showered, and by noon had called my friend Steven (who was 22) to run to the liquor store and pick up about $100 worth of alcohol for the party. I lived across town from the store so it took Steven around an hour and half to run the errand for me. I finally made it to Michelle’s house around 2 in the afternoon only to discover she wasn’t home. There was a note on the door saying that she’d gone out to run errands and would be home around 5. She’d left the door unlocked for me so I could go inside and store all the drinks till tonight. Well I still hadn’t done my laundry and it was piled quite high so I left her a note saying I had laundry and would be by around 8, possibly 8:30 and went on my way to accomplish my task.

I finally finished my laundry about 7:45, showered, and was ready for the party by 8:10. I hurried out to my truck and began driving to Michelle’s. She lived across town so it was gonna take me about 20 minutes to get there, which wasn’t so bad considering my laundry had already made me almost 2 hours late for the party. I arrived around 8:30 so I was still in the clear for being in time of my prediction in the note from earlier that day. I arrived only to notice the driveway full of cars and several cars lining the street, so I was forced to park several houses down. I decided to go thru the front door since it was closer and so I started to walk across the front yard at an upward angle heading for the front door. Michelle’s bedroom window was located by the front door so I had to walk right past it to get to the door. As I walked by I heard a guy’s voice say “Would you be offended if we told you that we thought you looked really hot and that outfit is turning us on?” I looked in the window expecting to see a couple people fooling around in Michelle’s room. When I looked in I saw two guys I didn’t know and to my shock, Michelle sitting between them.
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You Want to Fuck Me Where

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When I was 20 years old I had been living with my boy friend for 2 years and relitively speaking still inexperenced in the pleasures that sex had to offer me. Jack was very tall and well built, being an ex-high school football player he has continued to keep himself in pretty good shape. Looking back now I can understand why we eventually went our own way, you see, his cock was rather small, less than 6″ from head to base. But because I had only been with 2 other men up to this time I really had no idea that cocks could be larger and so much more fun.

Jack was always getting rather kinky, like the time I was in the tub bathing and he came in to pee. Yep, you guessed it, he turned from the toilet and sprayed my face with his pee. And he was always trying to talk me into letting him fuck me in the ass. I had no idea what his fasination with my ass was, but every time we made love and would get into the 69 position, he would always lick my ass and put a finger into my ass as he licked my clit. Of coarse this would always get him rock hard, and I did come to enjoy his probings and licking my ass. So it really was no suprise when one day I told him he could fuck me in the ass. It actually felt pretty good, feeling his cock stretching my virgin ass hole open. He really pounded my ass hard and fast and came right inside of my ass. Being the first ass fucking I had experenced I hadn’t douched my ass out first, and his cock was covered with my shit.

Well, about 3 weeks later Jack had 5 of his buddies from work over for pizza and beer while they watched a football game on the TV. I was left to do what ever since I never really got into the football thing. So while they watched the game and drank beer, I was in the bathroom douching my ass really good, I just kept putting the nozzle from the enema bag into my ass and squirting the shitty water out. I must have done this at least a dozzed times, untill I was satisfied that I was nice and clean inside my ass. And just to make sure, as a little test, I fucked a vibrater into my ass for 4 or 5 minutes, then sucked on it to see if there was going to be a shitt taste. To my suprise there wasn’t, infact it tasted clean and fresh. So now I bathed and dressed in a pair of old cut off jeans, really cut high so as to leave nothing to the imagination. I toped this off with a tank-top that showed my titties really nicely.
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Dancing Girls

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I moved out of my parents’ house when I was nineteen. My best friend Carl and I got a two-bedroom apartment together and agreed to share expenses. Up until, and right after we moved we talked endlessly, fantasizing about all of the adventures we would have at our new pad. We talked about swapping women, sharing women, orgies and everything else that can be imagined by horny, nineteen year-old guys.

About two months after getting settled in, we both became anxious to experience at least one of the escapades we had foreseen. We paced back and forth in the apartment plotting and complaining. We finally decided that purchasing new fuck flicks would at least settle us down for a little while. We found a good movie store and carefully picked out one movie each. When we got home we immediately put in one of the movies, Carl’s choice, I think. After a few minutes Carl asked me to leave the room so he could masturbate. I definitely understood his need to stroke after watching some of the movie he had picked out, so I exited the living room and went to my room. I picked up a book and began reading when the phone rang. Carl talked for at least thirty minutes. I finally came out of my bedroom when Carl hung up the phone. He had a devious look on his face. I knew he was going to tell me something good. All I could think of was group sex. Carl smiled at me and said, “Melina wants to practice her new dance routine at our apartment and get our opinion.”

Carl had known Melina since high school when they used to date off and on. She was kind of sleazy, she had a low self-esteem, she was a titty dancer. I told Carl I was most definitely game as my cock partially hardened. The rest of the day expired, night fell, and late finally came. I was tired of waiting for Melina to show up and I knew it was too good to be true anyway so I went to bed. Before I knew it Carl was waking me up saying “she’s here…and she brought a friend”. I sprung out of bed and immediately looked in the mirror to make sure I didn’t look too asleep. I combed my fingers through my hair, threw on that day’s clothes, from the floor, and went into the living room. Carl had one of our new movies playing with the sound muted and Melina’s dance routine music playing.

Melina’s friend, who’s name, I don’t think I was ever told (we’ll call her “Naughty”), was hot. She was not beautiful, she was kind of dirty, sexy. She had a great body and a sexy face, but she was kind of stinky looking, which really made me want to fuck her dirty. She said “hi, you’re Darren right, I came to watch too”. Melina instructed us to all sit on the couch. When she got her tape to the right song she began her routine. She did the typical titty dance routine, pushing her ass out, rubbing her breasts, and looking at us with permissive eyes. After she gave her routine one go around and she received our approval she began giving us lap dances one by one. I was first. Melina stood over me, her nipples erect, and let her hair drape over my face and chest. I felt her soft tendrils against my skin and stared at her breasts and navel. My cock was bulging and she didn’t hesitate to make sure I knew she saw the tent that was forming on my pants. She moved to Carl then, giving him the same treatment. When everyone was paying attention to Melina’s lap dance for Carl, I began rubbing my cock through my pants. Melina lingered at Carl for a while really giving him the deluxe version.
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Annas First Time

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I have a girl that works for me in my law office every Saturday. Her name is Anna. She’s such a delight, a sweet innocent young girl. Saturday is the day I’m always there alone catching up from the week while Anna does all my filing for me. Anna is really quite a cute little girl; at least that’s the way I see her. She’s about 5′ 7″ tall and very, very slender. I figure she only weighs about 100 pounds. Anna just turned eighteen a few weeks ago, but you’d never guess that. She looks like she’s only 14 or 15 years old. Maybe that’s what makes her so exciting to me. She’s got a great body with small breasts maybe only a 30 or 32 inch chest. Her waist is very thin perhaps 22 inches if that, and hips matching her attractive figure. But then there’s Anna’s rear end. Yes, her ass. Her ass is what always catches my attention. Many Saturday afternoons I’ve stared at her while she was filing and just gazed at her well-proportioned bottom.

I always loved those days when Anna would wear a blouse and a short skirt, especially her pleated skirt. When she wears that, she looks like she’s ready for cheerleading practice. Needless to say I have a hard time concentrating on my work those days. I would spend most of my time watching Anna and those smooth slender legs. Every time she bent down and her skirt rode up higher, I’d catch a glimpse of her soft supple thighs.

“My God,” I would think. “Look at those gorgeous legs.” You talk about driving a man nuts; well this is what was happening to me. Sometimes when she sat at the table next to my desk her legs would be apart a bit and I would get a peek up underneath her skirt. One day she inadvertently had her legs spread allot and I could see everything. “Pink panties,’ I said to myself. “What a fucking cute kid.” It took allot of willpower to keep from grabbing her and feeling her up.

Anna is a very proper young lady always being quite polite and appreciative of having a job and working for me. Although I’ve daydreamed many times of having a go at her petite gorgeous body, I never really thought anything more of it or that anything could happen because she always acted so professional. She did her work, went home and that was that.

Well this one Saturday everything was normal. Anna was filing some papers bending down to the bottom drawer and I was staring at her cute ass as I usually did. And she had on that pleated skirt. I must have been daydreaming more than usual looking up her dress, because the next thing I realized was Anna staring right back at me. At first I was a little embarrassed for being caught staring at her, but she just smiled and looked back at me. However, what started out as a simple glance at each other soon became a long inviting stare. I was wondering what she was thinking and I was convinced she was thinking about my nasty thoughts.

So there we were just looking and looking at each other. She was only a few feet from me, so to break the moment I stood up and moved right in front of her. “Sorry, Anna. I didn’t mean to stare.” Well, that was a lie, but I didn’t know what else to say.

“You think I’m pretty?” She asked.
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