WTF?

Lightweight Makes A Huge Mistake

Lightweight Makes A Huge Mistake

19-years-old and RUINED

19-years-old and RUINED

Reverse Road Head

Reverse Road Head

Sexually Inexperienced And Terrified

Sexually Inexperienced And Terrified

Ass to Mouth with Consequences

Ass to Mouth with Consequences

Huge Water Bottle Insertion

Huge Water Bottle Insertion

Board Posts

7
Anonymous
@confessions
17 Oct 2022 12:14PM
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I jerk off into the stepdaughter's panties ( 18+ of course :). They have an extra layer on the crotch that's just sewed at one end, so it makes a perfect pocket to slip over my cock. I love that she wears my cum.

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jldet
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@random
08 Dec 2016 12:37PM
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A few years ago I worked with this delicious slut in a medium sized office. About 75 people worked there, 10 or 12 in the attached warehouse, the rest desk jobs in the office area up front. She sat in a cubicle across and beyond the wall from mine. Blonde, tan, about 5 foot 3, 120 pounds maybe. Big, perky fake tits and a tight little ass. She knew it too. Always wore outfits a bit too tight or revealing. The kind of girl who spent her time on boats and at the beach, always in the sun, always flirting. She was such a tease.

I liked having time to myself in the office, to get things done without others around to interrupt, so I would normally come in very early, get there 530 or 6 AM. That would allow me at least an hour, nobody else in the office came in before 7. A few warehouse guys, but they stayed in the back. One morning I'm at my desk about 615 and I hear this incredibly loud sound coming from one of the cubicles across the wall. Startling and LOUD. I walked over to investigate, and my little office fantasy, let's call her Julie (not her real name), had left her cell phone on her desk, and the alarm was going off. I managed to turn it off, shaking my head at the noise. I was about to put it back on her desk when I thought, I wonder what kind of pics she might have....

Her phone had no secure lock screen, so it wasn't hard to explore. I found her galleries, checking over my shoulder that nobody else was coming in. Mostly boring shots of her dog, some flowers, pinterest type crap. Scrolling down, scrolling, and then - bingo.

A series of selfies that were clearly meant for someone she wanted to fuck. licking her lips, pouty smiles with her hard nipples through a thin shirt, on her stomach with her beautiful ass in the air, and more. They progressively got more revealing. Her ass in boy shorts, then her bare ass. Wearing just a bra, then full exposed tits. they were amazing. playing with her nipples, then her in front of a mirror in only panties, then no panties covering her pussy with her hand, then legs open and her finger tracing her slit. I was rock fucking hard. I checked again to make sure I was still alone, then pulled my cock out and did what any guy would do, stroked myself off to her pics right there in her cubicle.

When it came time to cum I shot my load right on her chair. She never came in before 9, it would dry before then, and I could spend all day getting hard knowing she would be sitting on it.

I wanted to send myself the pics, but she would know I did. So I hooked up a USB and transferred a ton to my hard drive. She had so many more. Then just in time, I put her phone back and returned to my desk just before a co-worker came in.

Fast forward to the next morning, alone in the office, my cock out, stroking to her slutty pics. I printed a few, full color on the office printer, and shot ropes all over her. I must have done this every day for a week. I would throw the photos away after, buried beneath other trash. So i thought at least.

After about a week of this, I came in one morning to find one of my cum stained printed pics of her on my desk. No note, nobody there, just the pic. I was freaked out. I was caught, and going to get fired. I picked up the photo to destroy it and found underneath, another photo of her, one I hadn't seen before. Tight sweater, tight pants, fuck me smile. Written underneath the photo was "do this one next".

I wasn't sure if she had found it and it turned her on, or a creepy coworker found it and took a pic from her facebook or something, but it was exhilarating. I made sure I was alone, grabbed my cock and pumped a huge load all over her slut face. Then I put it in the trash the exact same way as the day before. Neither she nor anyone else said a word about it that day. I was extra sensitive, trying to figure out who did it, nothing.

The next morning when I arrived at 530 my heart was pounding. I walked to my cubicle, almost couldn't breathe. When I turned the corner there was no picture, just a post it note. "check my top drawer - J". It was her. My cock was RAGING before I even got to her desk. When I opened her top drawer there was an 8 x 10 photo of her, spread eagle, sucking a cock while using a vibrator on her pussy. Below it said "when you're done leave it where you found it, xo"

I could not believe this was happening. What a filthy slut! What an amazing place to work! I edged and stroked for about 20 minutes, and pumped a fat load all over her. Then I left the cum covered photo in her drawer. A few hours later she arrived at work. Our area was pretty quiet overall. She walked by my desk, which she didn't have to do, and said good morning, in a very flirtatious tone. A moment later I heard her sit down, put her bag away and open her desk drawer. Then clear as day I heard her moan just a little, and close the drawer. I was immediately hard again.

We did not speak about it. Not at all. There was this understood secrecy about what we were doing, not a hint of it during the work day, no communication. But each morning that week I would check her drawer and find a new photo, and cum all over it. Thursday there was no photo, but a pair of panties.

I sniffed them as I stroked, her delicious pussy all over them. Then I stroked with them, and decorated her panties with my spunk, and put them back in her drawer. That morning, when she got in, she called over the wall to me, "can you come here for a second?". I was so nervous, and so aroused.

Her cubicle was situated with the opening facing a corner, so you couldn't see into it unless you were standing right at the entrance. I walked over, not even trying to hide my erection. There were two other people in the room at that point, about 15 feet away. As I reached the opening and said good morning, she turned in her chair and said good morning back. She was wearing a pencil skirt, which she hiked up just a bit, and opened her legs. She then slid off her panties, and handed them to me, and said "I think these are yours". Then she retrieved the cum soaked panties from her desk, and put them on right in front of me. She then turned around and began working. I almost lost my mind.

I put her panties in my pocket, and walked back to my desk. I pretended to work, but all I could do was replay that exchange over and over in my head. After an hour or so of that I couldn't take it anymore. I went to the bathroom, sat in the stall and began stroking with her panties. I decided to take a short video, about 5 seconds, and text it to her. My heart was pounding as I pressed send. I continued stroking there in the stall until about 3 minutes later she texted back, a 5 second video of her rubbing her pussy at her desk. I watched it on a loop until I blew, right into her panties.

The rest of the day was somewhat normal, we didn't talk, but we both it seemed continued to fantasize about what happened. Then came Friday morning. I arrived about 545. It was routine now, get my coffee, go check her desk for today's stroking material, and bust a huge nut before getting to work. Except that day there was no photo, no panties. Nothing. I walked back to my desk disappointed, and then I saw the post it note on my monitor. "You should check the conference room".

The conference room in our building was big, with a floor to ceiling glass wall that faced an open field. About a dozen chairs, screen, large oval table, standard stuff. It was at the far end of the building. The lights in the main area were still off, nobody was in yet. The conference room door was closed, which was odd. I was so nervous as I reached for the handle. I turned and opened the door, it was dark. As I flipped the first light switch, which activated a soft , low light in the center of the room, I could see her at the head of the table. She was wearing another skirt, hiked up. Her legs were open, and she was playing with her amazing pussy. I entered the room, shut and locked the door behind me, and walked towards her.

"I want you to watch" she said. So I sat down in the chair next to her, and watched as she made herself cum right in front of me. She was a total exhibitionist. Really put on a show. After she came, I got down on my knees, touched her legs for the first time, held them open and ate her pussy like a maniac.

She was pulling me into her, grabbing handfuls of hair, moaning and saying filthy fucking things as I tongued her deep and thorough. She must have came 3 times before I stood up. I was barely upright before she was tugging and pulling at my belt and zipper with both hands, staring up at me the whole time. She lowered my pants, peeled down my boxers and my erect cock bounced up, almost hitting her face. She took it in both hands, stroking it slowly, and proceeded to give me an incredible blow job. One of the 5 best in my life.

She did everything - slapped her tongue and lips with it, rubbed it on her cheeks, kissed, licked, sucked, cheeks caving in, moaning, saying dirty, dirty things to me as she inhaled my engorged cock. I was so close to cumming. She had taken her top off while sucking me, so her gorgeous tits were out for me to enjoy.

She then stood up, bent over completely at the waist, and laid her naked upper body on the conference room table. She reached out with her hands, laying the palms flat on the table, and pointed her incredible ass towards me.

"Do whatever you want" was all she said to me. And I did.

I dominated her. Fucked her slow and deep as I held her neck, pressed my chest onto her back. I whispered incredibly erotic things into her ear as I pumped her full of my pulsing dick. She gushed on me. The edge of the table was soaked. I flipped her around and fucked her that way for a minute, then pulled her onto my lap in a chair, then put her up against the glass wall, then bent her over the table again and pummeled her cunt until I blew, a gigantic load of cum, right inside her.

After a moment of us both gasping for breath, we began to get dressed. We straightened up the room, wiped the table down, made sure we both looked presentable, and walked out into the main office area. Not 5 minutes later a couple of people arrived at work, and before long it was a normal day again.

That was the first time we fucked each other senseless at work, a tradition that went on for about 6 months, at least twice each week. But that first time, and the erotica that lead up to it, still the most amazing, dirty experience I've ever had.

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Anonymous
@confessions
01 Oct 2024 2:20AM
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I fucked my wife's friend.

She is, actually my SIL's friend, but my wife knows her, as well. She is a very beautiful brunette, I think she is 39, slim, with big tits, and all in all great figure. I am married for a long time, and my wife and her sister are very close, so I heard a few things about her friend - she was unhappy in marriage, cheating frequently, and all this was said in the tone of "she is acting like a slut".

And she was always super flirty with everyone, even me, but I guessed that is just how she is, never gave any extra thought to it, until she started going to my gym.

Talked to her a few times, she was giggly, flirty, like always. I must admit, I did position myself to get as much eye candy while she worked out, what can one do, I am a man after all. Soon enough she started asking me for advice, on how to do certain exercises, and I gladly helped, and, we started working out together, where we would even text back and forth, and schedule our next sessions.

I told this to my wife, didn't want her to find out any other way, and she didn't mind. Well, that was a mistake.

This woman wanted me, and she didn't hesitate to make that clear to me. I was in doubt, with a clear head, I would never do it, but our sexual desires are hard to control, especially when we have someone just offering themselves to us.

So, one evening, after our work out, I asked her to come over for coffee. She asked if my wife is busy, will we be bothering her, and when I responded that her and the kids are away for the weekend, she said yes.

We both knew what was gonna happen, and as soon as we got in, started kissing. I couldn't hold myself, I bent her over on the sofa, and pulled her leggings down. I wanted to eat her sweat soaked pussy and ass, but when I ran my hand over her lips, she was wet as a fountain. So, no time for that, and I just stuck my cock in her.

I fucked her hard, fast, with full thrusts in and out, while slapping her ass. Oh, how hard she moaned. In the end, I pulled out, and came all over her ass, making sure to cover both of her cheeks. She smiled, pulled her leggings up, without even wiping, kissed me, and said she has to go, her husband is waiting for her.

At that point, I didn't care what will happen. I figured, this is a start of something, that I will fuck her many times, even started going through scenarios of what I might do next, got hard again, and even jerked off, the same night.

Well, tomorrow morning, she texted me that she is changing gyms, and that she wanted to thank me for all the help I gave her in her work out routine.

I think she got cold feet, being afraid that if this comes out, she will lose all of her friends, and that is true.

And I am left here, thinking of all the things I could do to her, that night, that I missed out on. Still, can't complain, had sex with a hot woman, what more can one ask.

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12
Anonymous
@confessions
19 Sep 2016 11:36AM
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When I was 19 years old and in college in Florida, I got really heavy into drugs. Mainly party drugs like coke and ecstasy, and of course plenty of weed, but on occasion other drugs as well. I was out of control and living one big party life on my parent's dime while they struggled mightily to pay for me to have the opportunity they never had and go to college. Looking back I feel like a total asshole about it now as they wanted nothing more than for me to be successful and not have to struggle...sorry, I digressed.

Anyway, since I had no money and wanted to keep up my partying lifestyle and since I was always very athletic, in shape and considered "good-looking", through one of the people I met in the party scene I ended up doing some modeling to make some extra money. Pretty low rent stuff, nothing glamorous, but a couple hundred bucks a week.

This quickly evolved into the opportunity to do some "videos". It started with just masturbation videos of me lying in bed, or on a couch or in the shower jerking off. I figured I was going to do it anyway so why not get paid for it and I was getting paid $100-200 per day that I did a shoot. I could sometimes do 3 or 4 scenes in a day. The guy running the operation said he was impressed by my "re-load" ability and also that I had just the right cock for it...I'm about 8 inches, decently thick and my dick looks perfectly formed from shaft to head and can blow pretty big loads even after only a little break in between. I knew that these were primarily for gay guys to watch but I didn't care. If someone gets off from seeing me, so fucking what. I did these for a while and then he asked one day if I'd want to do some full sex movies and photo shoots and showed me some of his portfolio and all things considered the chicks looked pretty hot and we were now talking more like $300-500 per day so I jumped right at the chance.

It was a crazy scene and pretty much everything you wanted was at your fingertips. Women and drugs galore. Parties every night after shooting. We were all in the 18-22 age bracket so it was just a no responsibility show. But as quickly as I made money it went back out the door on drugs and partying. Then one night when we were partying at the main house this director used for shooting videos, him and a couple of the other "big wigs" in their operation asked me if I would be willing to do some more hardcore shit. At first I was thinking they meant bondage, s&m type stuff, but they quickly made it clear they were talking gay action. I immediately said not a chance, I was straight and no way I could do it. They pushed the matter (and a coffee table with a big pile of blow on it) and said that all the actors in their gay shoots are straight guys because that is the look they wanted in their videos, strong masculine men, not femboys. The guys just do "gay for pay" and they also said I could make up to a $1000 per shoot depending on the circumstances. At that point my eyes lit up and I think they knew they had me. I asked them more questions and they said I could be strictly a top and receive blow jobs, that I didn't have to get fucked or suck or kiss anyone if I didn't want to. I could also do bi scenes where a female actress or two would be involved. I said, what the fuck, let's give it a try.

The next week they had scheduled me in for my first scene. I was shaking like a leaf prior to which was totally not like me. In the other stuff I had already done I was totally calm and had no issues getting naked, getting hard and fucking in front of other people. It was a one on one scene with me and another guy. I was going to be swimming naked in the pool and then get out and immediately go to the lounge chair next to the pool when the "pool guy" was going to show up to service the pool and eventually me who was masturbating while watching him clean the pool. I actually was having a difficult time getting hard which was totally not the norm for me, but he came over and began blowing me for a while and soon enough I did get fully hard. I had sunglasses on and just kept my eyes closed and picturing hot women. I put on a condom and ended up fucking him in a few different positions and then to my surprise he end up blowing his load on my chest as he was riding me, then slid off my cock, dropped back down and sucked me to completion taking my load all over his face.

I said afterward that it wasn't that bad, but I didn't think I wanted to do it again...until I got my next offer and more cash. It went on like this for a while and me just doing the fucking and getting sucked. I still was primarily doing straight shoots though. Then the director came to me with a proposal for a scene. It would be me and this girl I had done some straight scenes with and we would be a "married" couple and then another guy who was coming to our house to do some repairs. But he wanted it to be a scene where me and her completely serviced this guy. We all were going to suck and fuck each other, no holds barred type stuff. I was extremely hesitant but he offered up my biggest payday yet and it was a good chunk of money for 4-5 hours of total "work". I was so far gone into the scene at that time that I agreed and said let's do this.

The day came and again I was nervous. I did all my usual prep on my "manscaping" and where I normally do everything I can to keep myself fresh down below, this time I added the step of the diet one of the other male actors recommended and his full enema routine to completely clean me out. The worst thing on a porn set when anal is involved is having a shit accident. It came time for the scene and we were in the bedroom on a king size bed where I was fucking the girl for a while then the "repair" man came in, he joined in with me "thinking" he was just going to play jointly with my wife but then he starts licking my balls and ass and pulling out my cock from the wife's pussy and sucking on it. We go through some more motions and she is sucking him then she tells me she wants to see me suck him and this is it, the moment I took a cock in my mouth. I did what I had to do and then after he fucks her it was my turn to take his cock. I was laying on my back as she sat on my face and then he started fucking my ass. Hurt like hell but I had to put up a good front. He even made a comment that got into the video about how tight my ass was. Anyway, we finished the scene after everyone had been fucked and sucked and I went out that night with some of the other people from set and we got destroyed on drugs and booze. I was fucked up beyond belief and when I got home that night I said that was it, I was done. Absolutely no more of all of it. The drugs the porn, nothing. The next day I called up the director and said to pull me from the stuff he had me scheduled for the next week. He tried to convince me and told me what a fucking amazing job I had done the day before, but I told him I had to get out. I couldn't handle the life and really was regretting all of it. I pulled the plug that day and never looked back.

So, somehow through all of this I didn't flunk out of school. I ended up completing my degree and living out a pretty mundane, boring college life and working a bullshit part-time job in one of the offices on campus answering phones and shit. Really nobody in my "normal" life had any clue about what I had done. My parents were none the wiser about anything I did partying or whatever and were proud as could be the day they saw me get my degree. I started a job with a top consulting firm and in the decade plus since, have worked hard and progressed so much in my career that I look at the "crazy" money I was making from porn and laugh at how little it is compared to now. I am engaged to a very attractive and smart girl who is an attorney and makes plenty of money herself, but also has no clue about my prior life.

I guess my biggest fear is that one day I am going to come on here and see one of my videos front and center. I know they are out there in various places on the web, but they obviously weren't under my real name and the look I had back then was very different than it is now where I am clean cut hair, have a beard, and even back then in a bunch of the scenes I had bleached blonde hair for a while and a deep Floridian tan. I guess my real name and SSN is on file with the porn company somewhere so that could somehow get out, but generally speaking I got away free and clear without any repercussions. Crazy the journey our lives take.

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Anonymous
@confessions
07 Sep 2012 5:32PM
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I guess the TLDR of this is, I fucked a young fatty.

I'm 28, engaged to be married and working as an general IT monkey for a small firm. We have a trial contract for a call centre, and I got talking to the manager, who offered me extra cash to come out and sort his router out and build a pc from parts he bought but pussied out from putting together.

I got there on the weekend, and get to putting the PC together, largely being left to it, before sorting out the networking issues, he was paranoid about wireless signals so it was all LAN only, and I needed to fuck around with every PC connected, I do so on each machine in turn before there is one upstairs. I ask the guy, and he says it's his daughters room, that she is out but to ignore the mess and sort the issue out otherwise he would never hear the end of it.

I venture in, and its a fucking mess. I clear enough room to work, and fix the problem quick. My mind starts wondering what the daughter is like, and I start getting half a mind to do something like investigate her laundry for some nice knickers to steal before the paranoia seeps in that that getting busted could really fuck up my job. I settle for attempting to find shit on her computer (no luck, pretty much a fresh install) and poking around her room in the few minutes I figured I had. Opened the top bedside drawer and among the normal junk staring me in the face is a cheap gold vibrator. I look over my shoulder at a closed door before picking it up. I can smell that it doesn't get cleaned much, and my cock is suddenly raging. I hear footsteps coming up the stairs, so I replace it and bail out of the room, to run into the guy, who is happy I did such a quick job.

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Anonymous
@confessions
05 Jun 2020 5:50PM
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I really like being dominated if you couldn't tell from previous posts, but one of my favourite things to do is to be taken control of even while they are not here, I had a task recently and i thought I'd share it with you.
So, i left my flat, both dildos in hand, they're the lifelike 10 inch dildos you can get and they're amazing beyond words, naked as the day i was born, stuck them to the ground and lay down, positioning them perfectly so i could lean across on my side and suck one off and pick up the other and plunge it into myself.
I knocked the door of the flat with two guys and showed them the message saying i was going to show by invitation only, phones to be left behind in their flat, they jumped at the chance and came outside, i knocked the door of the door opposite mine and told him too, showing the message and he looked at me, the dildos and the two guys stood watching and came out too. It was 23:15, I didn’t want to waste anytime, my pussy already wet but i thought i could use some help so i lubed up one of the dildos while on my knees, ass facing them and wiggling about some, them standing and giving me encouragement as if i was jerking someone off.
I lay on my side on the cold floor, nipples hard, i looked up at them as i took the dildo into my mouth, licking the tip and up and down beforehand of course, sucking the head of it lovingly, closing my eyes and enjoying the experience. I massaged my clit as i did this, playing away with it and then reached for the dildo and spread my legs open and introduced the incredibly large thick thing back to my pussy where it was earlier, slowly pushing it in all the way, them watching keenly, a front row seat to it all and seeing it disappear inside me, the dildo in my mouth disappearing too as if it were a magic trick, i held myself all the way down and gagged on it, saliva dripping from my lips and down to the balls of the dildo that were only centimetres away, i pushed myself back down and my chin touched the balls, i held myself down there for a thirty count, pushing the dildo into my pussy as hard as i could, not wanting to let it out, wanting it to become a part of me almost.
I lay there deepthroating the dildo, lifting my head up and down, never letting my lips leave it, only the tip was the furthest I’d be willing to go, my pussy savouring every stroke in and out of it, the dildo spreading it so wide and the veins rippling inside me, pleasuring every point it past on its journey in and out. My body was loving every second of it, tingling all over, i knew what’s was coming, i looked up and they were stood watching, not far apart, wanking away, I lay on my back and pulled the dildo off the floor and sucked on it as I fucked my mouth and pussy, I lay there on the cold ground in ecstasy, my pussy ready to release, I pulled the dildo out of my mouth and left it on my stomach and focused lower and fucked myself into an orgasm, continuing on for the extra bit to spray some of myself around, and luckily it came.
​I gushed out some of myself and it hit the dildo as I pulled it out and it hit my legs and dropped down.
I lay there, panting, trying to catch my breath and looking up at the light before me, it could’ve easily been the end, and if it was, what a way to go, but my eyes caught the world around me in that small space, and I saw smiles on the faces of my admirers so I messaged my tits and pussy for them, pushing three fingers into myself, dildos cast aside for the night, if had my fun with them for the night, half an hour like that was plenty, I kept letting my hands roam around and find every last part they could reach, then one by one they said they were ready to cum, I leaned up as they got to their knees and I kept my mouth open for them, playing with my nipples the whole time, taking their lovely warm white seed in my mouth, every drop a gift that I gladly accepted, not touching their cocks at all, it was against my orders given to me.
I leaned back and showed them my mouth, then closed it and swished it around for a couple of seconds and then swallowed it, showing it to them.
I rolled over onto my stomach, I could’ve slept there I was so comfortable, my body had heated the tile floor beneath me, I pushed my ass up into the air, my hands finding it and I smacked it hard, massaging it better and then smacking it again, my hands working their way around my thighs, rubbing in what my body forced out in excitement and ecstasy, feeling the wetness in the floor as the back of my hands touched the floor briefly.
I climbed to my knees, my hands roaming over my body, dildos laying on the ground and the men smiling at me, the show was over for now, but I knew i would be here again someday, and soon I had hoped.
I was so in the moment and then had to leave it, felt like a movie director ready to shout cut at even that time of night.
I got up and grabbed my phone, keys, toys and lube and walked away with a smile and leaving a quickly drying specs of me on the floor, I left more of a mark on their memory than i ever could on that floor.

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Sarasera
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@confessions
14 Jul 2020 1:04AM
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Thankfully I’m a bit OCD and had prepared most of the appetizers and sides Friday and burger and dogs are well....burgers and dogs. I set up pretty quickly and with about an hour until the start time I was making my signature Sangria. Nectar of the gods with a sneaky kick if you’re not ready for it. Anyway, Ben’s number shows up in my phone and I’m excited and terrified at the same time. He coming...he’s canceling....worse. He asked if he could bring a friend. A chaperone..a buffer. I’m crushed and screaming in frustration inside but manage to use my big gurl words and cheerily say “of course!”

My friends begin to arrive at the appointed time. If anyone cares, I was wearing denim overall shorts that I think do amazing things for my butt with a plain white tank top. Music, talking, laughing...etc then a knock at the door followed by Ben coming in with his friend. Flashback.....Ben is an adorable twink maybe an inch or two over my 5’6” with a hint of musculature but quite defined. I know from lastnight that his short black hair and eyebrows are the only hair he possesses. Oh, and he has a wonderful 6 inch cock that is perfect for sucking and fucking. Lol. He introduced his friend as Randy. He was similar in build to Ben but with shoulder length blondish hair in a ponytail and sweet looking brown eyes with eyelashes I’d kill for. He was a total cutie. Shy but charming at the same time.

The party went as they usually do. I flirted with Ben as I had yesterday but being a good hostess I didn’t have the chance to corner him like I did yesterday. The shocker was Randy. He managed to cop several feels on me as I was carrying trays or other items. I would put an extra swish in my walk to let him know I appreciated it. My sangria was a hit and most left feeling no pain leaving me alone with Ben and Randy and a tremendous amount of sexual tension in the air. The second time Randy had goosed me I knew I was getting fucked by someone that night so I slipped into my room and inserted one of my smaller plugs to keep me stretched just enough...

“Boys” I said, “one or both of you need to take me to my room and fuck me. Preferably both of you”. So that’s how I found myself naked in the middle of my bed with two sexy bois sucking, licking, and nibbling on my tender nipples while getting lube fingered into my ass and slowly stroked off at the same time. Ben rolls me over and slides into me slowly (thankfully because I’m still a bit sore from lastnight and this morning. COVID it’s been a while) Randy slid around and sat in front of me and I happily went to work in his dick. A bit bigger than Ben and barely within my ability to deep throat comfortably. A few minutes in that position and he switched to 69 me. Heaven! Ben is giving me long smooth strokes and rubbing my back. Randy’s mouth and tongue are everywhere. On my cock, my balls and inner thigh. Ben is speeding up and thrusting deeper I know he’s ready to cum. His cock pulsates inside me and his fingers dig deep into my hips I’m getting my third load in 2 days! A few moments later Randy succeeds in bringing me off and wanton cum whore I was that night I dove into his mouth with my tongue to share my cum. I decided to ride Randy’s cock and end up pulling it out of Bens mouth so I could sink it into my dripping hole. Dialated by My recent fuck and slick with cum and lube he slid right in consummating my first threesome. Ben put one more load of cum into my ass and I got to fuck Randy too before they had to leave.

Neither are relationship material but I’d love to have them over anytime. Sara.

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I waited a couple of years after graduation to attend college, working to save enough money to give myself a good foot up. I lived with my parents and worked for a farmer.

Occasionally, my folks would go out of town for the weekend and I’d stay home. “No parties!” they’d insist and most of the time I lived up to that. It was a small town in Kansas and the neighbors would have ratted me out so if I had people over, it had to be kept small.

This was in the eighties, when there was still no internet or streaming and not everyone had cable. My folks did. So around Memorial Day, when I knew I’d have an extra day or two off and my folks would be out of town for a week, I stocked up on some groceries and beers and put out a few invitations.

Back then I was sort of seeing, more fucking than seeing, a woman named Mandy. She was older than me by a little bit, wasn’t fat but was definitely chubby, cute but not pretty. But she was very adventurous sexually, had a great set of tits, and a wicked sense of humor. She was a lot of fun and my Mom hated her, another reason I was interested.

Mandy was, by the way, several of my firsts. She was the first woman I’d been with who was on the pill. I could cum inside of her all I liked. She was the first to ever ask me to fuck her ass. And she ate ass. She was also the first person I ever tit-fucked. To completion. And she was my first threesome. This is the story of that threesome.

While everyone else was downstairs watching HBO, something that was still pretty new in our area back then, we snuck off to my room and proceeded to get naked and get busy. My younger brother and my best friend were both there among the eight or nine folks who were over so I wasn’t worried about it getting out of control.

We had enjoyed our foreplay and I had her on her back, spread wide, and I had just gotten balls deep when there was a light knock on the door. I grabbed a blanket and covered us up, staying inside of her.

“Hello? You in here? Mandy?”

It was Carla, a friend of my best friend’s new girlfriend. I didn’t know her well, having only met her a couple of times. I held my finger up to my lips, not wanting to be interrupted. “Shhhhhhh.”

Mandy laughed and said, “Yeah, we’re here.”

The door opened and closed and in the light that came through the open curtains from the streetlight on the corner, I saw her cross to the bed and felt her sit on the edge.

“We?”

“Yeah. Val and me. Who’d you think would be here?”

“Val?”

“Yeah. Hi.”

“Oh shit! Are you two . . .”

“Yeah.”

“Oh, I’m sorry! I just wanted to talk to Mandy for a minute.”

“Whatcha need, Sweeite?”

“I just needed to get away from Matt (Matt was my best friend).”

“Why?”

“I went to the kitchen to grab a beer and he followed me. He tried to kiss me.”

“Isn’t Hillary here (Hillary was Matt’s girlfriend.)”

“Yeah. She’s asleep on the couch.”

Carla had come to the party alone, the only single one there. Everyone else was paired up. Carla didn’t have a boyfriend and Matt, who fancied himself a cocksman, had brought his future ex-wife, Hillary, who had worked all day and had fallen asleep almost immediately. Matt, seeing an opportunity, had made a move on the single girl, who wanted nothing to do with him.

“Would you like to stay here with us? That’d be okay, wouldn’t it, Val?”

“uhhhhhh, sure.”

I started to pull out so I could lay face up and talk to both of them.

“What are you doing?”

“Well, I thought . . . “

“No, no. You don’t mind if we finish, do you, Carla?”

“Um. Finish? OH! Uh, I could find another room or wake up Hillary or something. I don’t want to interrupt you.”

Point of fact, she already had interrupted and I was losing my hard. But, I knew Matt for who and what he was and if he was thinking about getting into this girl’s pants, he wouldn’t stop at one try.

“No. It’s okay. We can stop. We have all night.” I was nothing if not a gentleman.

Mandy set that straight. “No we can’t. As long as Sweetie here doesn’t mind, let’s make this one a quickie and we’ll get something going again later. You don’t mind, do you, Hun?”

“Uh, no. I don’t mind. It’s just sex, right?” There was more than a hint of doubt in her voice.

“In fact, if you want, you can crawl in here with us, if you want.”

I expected a refusal and that she’d leave to go back to the party. Maybe wake Hillary up.. But Mandy reached up and stroked her face with a fingertip, “We won’t bite you, you know,” and then, after a pause, I felt the blanket lift up and a pair of jeans brush against my hip.

Then Mandy’s voice, “What are you doing?”

“Getting in with you.”

“Not like that.”

“Huh?”

“Aw, c’mon, you don’t get to watch us dressed like that.”

Carla stood back up beside the bed. There in the glow of the streetlight, she was lovely to see. First the jeans. Down her lean boyish hips and then stepped out of. She made a gesture as if to ask if that was enough. “C’mon, Sweetie. You’ll be seeing all of us, won’t you?”

She wasn’t wearing a bra so when her t-shirt came off over her head it was to expose lovely B-cups with areolas as small and dark as pennies.

“Everything?”. There was no panic in her voice but you could hear the shyness.

“You can leave those on if you want.”

She crawled back in next to us and I could feel a real thrill as her bare skin brushed against me again. I knew Mandy could feel me stiffen inside of her.

“Now, sir. Where were we?”

I swiveled my hips to let her know that I was listening and leaned in for a kiss. Then Carla’s voice came quietly out of the dark.

“Can I see? I’d like to see.”

I felt Mandy reach over my back and tossed the blanket down to my hips. Carla tugged it off and let it fall beside the bed. Her hand brushing across my bare ass was like electricity.

Slowly I began to stroke and I could feel how much wetter Mandy was now. She was excited, too. Carla leaned down behind us and in the moonlight could see me sliding into and out of a very tight and wet cunt. Then she crawled back up and laid down beside us, her head on a level with my own while she rested on an elbow.

I looked to see if I could catch her glance but she and Mandy had already locked eyes and I was not included in the exchange. Carla’s hand came up and her fingertips began to massage her nipple as I saw Mandy’s right hand sneak across the slight space between us and begin to rub the crotch of Carla’s panties.

Carla’s eyes closed and her head tipped back as the touch of the fingers at her groin had their effect on her. Then her eyes opened and she leaned in between Mandy and I and although I couldn’t see it happen, I knew that they were kissing. At this point, although I was inside of one of them, I was merely an observer.

Mandy’s fingers now sought the elastic of Carla’s panties and began to attempt to reach inside. The angle was awkward and I could see her fingers bending back. Carla extracted herself from the kiss and stood beside the bed. Hooking her thumbs in the waistband at either side, she leaned forward and pushed them down to her knees, and then stepped out of them.

She had just the smallest puff of hair at the juncture of her thighs and it was dark and lovely. Mandy reached out as Carla stepped closer again to the bed and stroked it with her fingertips, pressing between her thighs and parting them. I could myself growing closer to an orgasm, and didn’t want to be.

“Val, scootch down!” Mandy whispered.

I pulled out as she pushed with her hands against the headboard and shoved her body farther down the bed, making room around her head.

She gestured and Carla climbed up, with her back to me.

“No, no, no. Turn around..”

Carla adjusted herself and parked her knees on either side of Mandy’s head. Then, with a sigh, she settled that taut body and I could see her relax as her pussy made contact with Mandy’s mouth, as if Mandy was sucking all of the energy out of her.

Her thumbs and forefingers began again to pleasure her sharp, little nipples as Mandy pulled her knees up, spreading herself for me to re-enter. Which I did. In one stroke, grinding at the end.

I tried to hold out. I did. And I got maybe a minute of stroking into and out of that plump, tight, slippery pussy, but watching Carla ride and writhe on Mandy’s mouth was too much for me and I could feel myself about to finish.

“I’m . . . I’m gonna cum.” I began to bottom out into her, knowing I could put it in as deep as I wanted.

“Please,” Carla’s whisper was gruff, “I want to see it. I want to see it! I want to see it cum!”

l pulled out and didn’t even need to touch myself. Streams of cum shot from me, the first couple of which were hard and thick enough that they splashed against Carla’s crotch where it rested on Mandy’s chin. The rest decreased until the last one bubbled against the thick mat between Mandy’s legs.

Carla fell forward and before I was fully aware, she had my cock in her mouth, sucking the last of my cum from me. It was a nearly painfully exquisite sensation. I knew she couldn’t have been extremely experienced but she knew enough to make me nearly faint from the pleasure.

As my cock deflated, she shook it from her mouth and as I watched, she began to lick the cum from Mandy’s body. First mine from just above her pussy, then Mandy’s from her open cunt.

As I watched and stroked my once-again stiffening cock, remember, I was a young man, they brought each other to shivering climaxes. Not simultaneously, but close enough for them to exhaust each other. As they rolled apart, and Carla crawled up to lay beside us, I saw the shine of my cum, which had been pressed between them, on both of their bodies. Mandy’s fingers traced patterns in it and she leaned down to lick it from between Carla’s tan-lined breasts.

“Fuck,” Many whispered. “Fuck. I could stand to do that again. Where’d you learn to eat pussy like that, Sweetie?”

“I didn’t.”

“You mean that was your first time?”

“Yeah.”

“Well don’t stop on my account. You’re good. So you’ve only ever been with guys?”

“No,” this whisper was shy and I could almost hear her blush.

“You mean?”

“I’m a virgin? Yeah.”

“Shit. I’m sorry! I didn’t know!” This from me. I wouldn’t have guessed.

“No. It’s okay. I had to have a first time with someone. This was fun.”

“But we didn’t? It wasn’t really a first time.”

“No. And I don’t want to do . . . that. But what else can we do? I’ve read the letters in the magazines in the bathroom cupboard at home. I know there’s other . . . stuff. Can we do some of that?”

If I hadn’t already been hard again, that would have done it.

Mandy reached over and pulled her down for another kiss which I leaned in to join. “We sure can, Hun.”

There was a loud knock on the door and then Matt’s voice. “Val? I’m going to take Hillary home. She’s tired. But I’ll be back. I can’t find Carla so I think she snuck out early. I was thinking about getting on that. She looks like she might know what’s going on. Val? You in there?”

We all three snuggled quietly, not answering.

“Val? You in there?”

“Yeah.”

“Can I come in?”

“No. Probably shouldn’t.”

“Hi Mandy!”

“Hey, Matt.”

“I’ll be back a little later if I can’t get Hillary to wake up. If you see Carla, tell her I’m looking for her.”

“Yeah.”

His footsteps retreated down the hall and then down the stairs

“So,” Mandy asked, “what other things are you thinking?”

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@confessions
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When I was younger and chatrooms were still popular, I spent some time on Yahoo in local, state chatrooms. I chatted with a few women over the years, but had never worked up the courage to actually meet one in person. The internet still had a stigma attached to it back then and I guess I was just afraid of the potential consequences.

When I was 22, I began having a conversation with a 40 year old, married mom whom lived about an hour and a half from me. Her children were older so they were rarely home and her husband was deployed to Afghanistan. She told me that their relationship had been slowly deteriorating for months. She said the few times that she would get to talk to him, it often ended in an argument and that they were most likely headed for divorce once he returned home permanently.

She was a beautiful woman. She told me that before her husband had left, she was a bit heavier, but had worked her tail off to lose the extra weight. By the time we began chatting, she was down to I’d guess around 130 pounds—perfect for her five foot, seven inch frame.

We chatted for several weeks and would occasionally use the webcam. Webcam technology was still pretty new and the image was always laggy and blurry with no sound. As our conversations became more intimate, I would ask for her to show me different things. She was hesitant to show me her breasts. She explained how the weight loss had taken its toll on them. Reluctantly, she showed me. While I thought she was gorgeous either way, she was right. The radical change to her body had done wonders in other places, but the opposite was true in others.

One day, after having been absent from Yahoo Messenger for a few days, she hopped on and said that she was sorry that she had been away. She said that she had had some surgery and wanted to show me something. She turned on her webcam and proceeded to take off her shirt and bra to show me that she had gotten breast implants. Like I said, I thought she was beautiful before, but now every inch of her body was perfect. She would definitely be causing heads to turn everywhere she went.

She told me that I was the first to see them and that she hoped I would see them in person someday. We exchanged phone numbers and within a day or two she texted me to tell me that she was in town to pick up her husband from the airport. His plane would not be coming in until the next day. She had gotten a hotel room downtown and had nothing to do so she wanted to know if I would want to meet to have coffee or something. I agreed to the meeting, despite being nervous as hell.

We had planned to meet at Starbuck’s. It was my hope to get their first simply so she would have to come up to me as I was scared to death to have to come up to her. When I arrived, I was too late. I could see her standing at the counter waiting for her order, but I could really only see her from the side. As I approached the counter from behind her, I heard the kid working the register tell her how beautiful she looked. She said thank you and turned around to see me standing there nervously. My jaw nearly hit the floor. She was stunning! She wore a tight tank tope that amplified her already amazing cleavage. She was also wearing those sexy, cat-eye glasses that I absolutely love on girls.

We awkwardly hugged and I placed my order before joining her out on the patio. We made small talk for well over an hour. It was getting later in the afternoon—early evening. I asked if she wanted to go somewhere and get some dinner. She agreed so we walked a few blocks to a nice Italian restaurant where we had a nice dinner and a few drinks. We continued to make small talk for another good while before I finally paid the check and waited to see where things went next.

I nearly jumped for joy when she asked if I would like to go back to her hotel room and order a movie or something. We walked to her hotel and as we were going up the elevator, yet another guy commented on how beautiful she was. He looked at me jealously as if he knew what was going through my mind.

We entered the room and we both made ourselves comfortable on the bed. She turned on the TV and began searching the pay-per-view titles for a movie to watch. She could’ve turned on anything at that point—I didn’t care. She picked a movie and we began to watch. While I do remember the name of the movie, I couldn’t tell you anything about it as my mind was racing a hundred miles an hour.

We lay there for about forty-five minutes to an hour in silence—except for me getting up to go to the bathroom every ten minutes because I was so damn nervous. Finally, I figured it was now or never so I gently began to caress her cheek with the back of my hand before leaning over and kissing her. This lead to a very passionate make out session before I asked if I could finally see the work that she done.

She lifted her shirt over her head and I wrapped my arms around her back to unclasp her bra. I threw it to the floor, exposing the biggest, most perfect pair of breasts that I had ever been this close to. I asked if I could touch them or if they still hurt too much for them to be handled. She said that she had taken some painkillers as soon as we returned to the room so it would be fine. I gently placed my hands on them being very careful not to be too rough. However, she insisted that she was fine and such delicate care was not required. I continued to fondle her as we kissed, our tongues swirling in and out of each other’s mouths. I lowered my head and carefully licked her breasts, churning my tongue around her nipples.

She told me to lie back and relax. She removed her shorts leaving on the lacey, pink panties that she wore. She undid my belt, unbuttoned my jeans and slowly slid down my zipper. She was somewhat surprised by the fact that I wasn’t wearing underwear, but this only slowed her a second as she took my cock in to her hand. She stroked it gently before lowering her head to give it a lick. She slid her tongue down the length of it stopping at the base to take my balls in to her mouth. She slid back up and whirled her tongue around the head before finally taking the whole thing in to her mouth.

It was pure ecstasy! I had never felt anything like this—the things she could do with her tongue! I desperately tried to recite baseball statistics in my head to keep from cumming too soon so that I could enjoy this for as long as possible. I gave the best effort that I could before finally exploding in to her mouth. It was the most intense orgasm I had ever had. She swallowed it all and smiled as she came up and rested her head on my chest. She must have been able to feel how fast my heart was racing.

We laid there for a few minutes. The entire time she was gently playing with my now soft cock in her hand. After a few minutes, I was hard again and she began stroking me harder. I tried to slide my hand into the front of her panties, but she cut me off and resisted my advance. I told her how bad I wanted to fuck her. She said that she wanted me too, but unfortunately, it was just not a convenient time of the month to do so. So she continued to just stroke my cock for a few minutes.

I was as hard as a rock; throbbing in her hand when suddenly, she stopped and excused herself to the bathroom. I hedged my bets and assumed this was simply and excuse to make preparations as she wanted to fuck as badly as I did. I reached down and took my wallet from my pants that were still lying on the end of the bed. I removed one of the condoms that I had bought on my way to meet her in hopes that something like this would happen. I had been so nervous about what this encounter would be like that I bought those condoms with the desensitizing lubricant to help ensure that you can last longer. I took one and placed it on the corner of the nightstand.

A moment later she returned from the bathroom, having removed the pair of panties that had blocked me from getting to her pussy earlier. She was ready, and so was I. She noticed the condom that I had placed on the nightstand. Standing next to the bed, she took the condom and unrolled it down my penis before climbing on top of me and guiding me in to her pussy.

We fucked forever—in every position imaginable. If it hadn’t been for the extended pleasure condom; I know I only would have lasted a couple of minutes, if not a few seconds. I eventually reached the point where I desperately wanted to cum, but the condom was working all too well. I knew that if I kept it on, I was never going to climax.

Remembering one of our more intimate conversations from Yahoo, I knew that doggy style was her favorite position so I asked if we could do that next. She happily climbed up on all fours and I took my position behind her, discreetly removing the condom in the process. We were facing the mirror so I could see the look on her face as I slid my now naked cock inside of her. She could tell right away what I had done, but didn’t seem inclined to care. I began thrusting harder and harder and told her that I was going to cum. In the slightest whimper, she said, “I want you to cum inside me, baby.”

That was the moment of no return as I thrust my cock one last time and pulled her as close I could by her ass. I unloaded inside of her before we both finally collapsed on the bed. We continued to lie there, now in the dark; kissing and fondling each other before finally falling asleep in each other’s arms.

We spent the entire next day texting back and forth about the encounter and how incredible it had been for both of us. Later that week, she told me that she was going to be coming back to the city to return her husband to the airport. She asked if she could stay with me once she was rid of him. At this point in time I had just returned home from college and was still living with my parents. I was too embarrassed to tell her, so I essentially just dodged the question and explained that I would be busy. Our messages became fewer and fewer over the next couple of days before just finally ending altogether.

To this day, I still think about this night and recreate it in my mind. About a year ago, right before my own wedding, I decided to see if I could find her. All I had to go on was a first name, an old cell phone number that was no longer in service, and the screen name she had used on Yahoo Messenger.

After some creative Googling, I managed to find her Facebook profile. I discovered that she was now living in another state as her husband had been reassigned. They were still married; apparently living much happier than she was at the time of our meeting. I sent her a friend request, but she never responded. I took this to mean that it was best to leave well enough alone. I still check in on her Facebook page from time to time. I have since learned that her son is right around my age and that her daughter, only a couple of years younger than me, is as gorgeous as her mother.

I wish that I could simply tell her how much that night meant to me, but I wouldn’t want to risk jeopardizing her marriage or my own. I am left with the lasting memory in the back of my mind and very few days pass that I do not recall that evening and wish that I would have met her again the following week like she wanted to.

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@confessions
11 Sep 2012 10:51PM
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So, I have a confession. More of an admission I guess.

I'm not homosexual, maybe I'm bisexual. It's hard to tell, because I've never been with a man. I've always loved women, and I'll never stop wanting them. But lately, I've been thinking about experimenting with being a "bottom".

I guess I should start from the beginning here. The last girl I was with, I guess it was a year or so ago, was the love of my life. I had finally found the girl I wanted to marry, to be with until one of us died. I was happy, and she was EXTREMELY adventurous sexually. Our first night together before we were a couple involved a threesome with her friend. It was actually initiated by her friend actually. That's another tale though.

SO, after we started really dating, things clicked quick, and we fell in love. Love isn't something that I throw around without meaning, she's actually the first of any of the girls I was with that I truly felt it for.

Sex was fantastic. We fucked like rabbits, we fucked in public, in my car, just, wherever, whenever. I STILL to this day dream about the sex. Well, while she would be blowing me, she would always massage around with her other hand, and one day, she went low and started pushing her finger against my asshole.

I never really got into the idea of having my ass fondled, but she was the kind of girl who would convince me to jump off of a cliff. I mean, this girl was heavenly, with a mix of the devil. Natural beauty, un-dyed Raven hair, tits that were out of this world, hell I doubt I'll ever do better.

Anyway, so she starts working around it, and I'm not so much in a panic, but just wondering what I should do. Damn if she didn't figure it out for me, a quick deep throat made me release whatever pucker I had as I felt the ecstasy of her pleasuring, and she worked her finger right in.

She looked at me, and just held her finger in as she stroked my cock with her other hand, and smiled. I smiled too, because, I loved her, in my head I was worried that if I enjoyed it, she might think I was weird.

Well, more and more times during sex, she would work her finger in during a blow job right to the point where she started working her finger in and out. I didn't stop her, because she enjoyed it, and honestly I did too now. It was an extra pleasuring to my already fantastic fucking.

I decided to pay her back with some ass play of my own one day, and I turned her on her belly as I massaged her, working down along the hump of her bottom, spreading her cheeks and working my tongue in. She moaned in joy as I tongued her ass and fingered her clit at the same time. I had never eaten a girl's ass before, but if there was a girl to try it on, it was her. I had fun, she was very clean, as am I, so I wasn't worried about anything "gross". Who am I kidding, I freaked out at first, but in the moment, you just go all in. You know it.

Well, the next night, she decided to PAY me back for her pleasure. She told me to lay on my back, because she wanted to give me a massage. I told her it wasn't a big deal, because massages didnt do it for me. They still really dont. I don't find them too erotic unless I get a bj at the end. Which I never did haha.

She playfully tells me to just do it, so I abide. She starts massaging me, and after a few moments, I realize she started working a lotion around my bottom. Now, I've been told that if I posted a picture of my ass, and hid the fact that I was a dude, I could have men jerking off to it. I've often considered doing it as a joke. Then revealing that the ass belonged to good ol' me. Anyway, back to the story..

She starts rubbing lotion on me, and beckons for me to get up on my knees and elbows. She starts to use the lotion to stroke my dick and balls, and it feels fucking fantastic. I'm wondering to myself, "My god, how can it get any more awesome??!!" When all of a sudden, I feel a warm moistness start to tickle around my cheeks. I tensed up when I felt her breath roll over my ass, a little warm air against my bottom.

Suddenly, she begins licking and rolling her lips around my ass hole as she strokes. I tried my best to not cum, but it was probably the best feeling I've ever had in my entire life. I came BUCKETS. I'm pretty sure I applauded her.

So, some time passes, and one day after lunch on a weekend, she tells me she wants to start using toys. Again, I've never used toys. Never really figured much for them, as I have the perfect toy for a girl right between the legs.

I tell her to get whatever she wants, and we'll try them out. So, a few days later a package from Amazon shows up at our door (we lived together for a bit in a nice rental house) and low and behold, she ordered a vibrating dildo.

I joked with her and said I was sad that she didn't think my dick was up to par anymore and she laughed and said that they were the same size, she just wanted to try a few things. So the night the dildo came, I was eager to see what she had in mind.

She asked me if I'd fuck her in her ass. I'd never had anal sex with a girl before. Don't get me wrong, I tried. My ex some time before her flew off the bed in pain because I was too big. And since then, its never really been anything I thought of doing. The vagina and mouth work just as well.

I said hell yeah, and after careful careful careful amounts of effort, we got it in, and the fuck began. At first it was slow, incredibly slow. Almost to the point where I was just wanting to take it out and fuck her normal. But, as she always did, she surprised me. She started fucking speeding up to the point where it was like I was railing away at her like normal. I still was careful, I'd read too many horror stories.

In all this, I'd forgotten about the dildo. The purple, ugly, veiny didlo. The damn thing sat next to her as I fucked her ass sideways.

Now, I've watched a lot of pornos. And they've been the best education a man could ever need. I grabbed the damn thing, I never held one before, so it was like holding another man's penis. Odd. I decided I was going to double penetrate my girlfriend. I slowed down enough to work it in, and with the satisfactory moan from her, I did my best to maintain a rhythm. Eventually, I handed the rains of ol' Veiny to her and it was epic. She came a lot, I came a lot, and it was a fantastic night.

A few nights later, because I was out of town, I came home to her in a sexy little number and the ol Veiny on the bed. I figured we'd be repeating the night we had earlier in the week, and I was excited. The way she could work a dick, damn I hate the guy who she's with now...

So, we set about it, and she gets the lube out and starts applying it all over the dildo. I kind of had an idea what she was up to. I'm not a moron, and I'm horny like 99% of the time. The other percent I'm sleeping. She asks if she can use it on me.

I stared at her for a while wondering if there was a wrong answer here. I didn't know if it'd be like Indiana Jones and The Last Crusade, where I had to "Choose Wisely", or not. I decided, since she and I had been having wild nights, what the hell. We only live once.

Well, haha, it didn't work out. I did not have the anal space for anything like that, and honestly, I was terrified. I could tell she was disappointed, but not completely downtrodden about it. She told me that we'd have to work up to it. I agreed, if only to appease her.

So over the next couple of months, she would use two fingers instead of one, increasing slowly to three, to the point where it almost hurt when she was working her hand in and out.

Well, things didn't work out between us, and we ended up breaking up before ol' Veiny ended up anywhere near my ass. This is where I'm at now, and I can't figure out what's going on in my head.

I've had thoughts about having a dick jammed into my ass, and it subsequently railing it. I mean, not just any dick, a fit, young fellow like myself. Not a beary old dude. I dunno, there's just something about it that turns me on. I dunno if its because I still am drawn back to the passion with my ex, and kind of "finishing" what we set out to do, or what. I mean if that was the case, I'd just stick a dildo up there and call it a day. I think there's more to it than that.

I have what some may say is a sexy penis. Its not ugly or funny looking, its just exactly what its supposed to be. And I think thats the kind of penis I'd hope for haha. I see some of them in porn, and its kind of a turn off. So, I know its not the penis that draws me.

I've thought, maybe just a girl with a strap on? But I dunno, I feel like if I were to go that far, why not have it be a real, pulsing, throbbing cock?

These are questions I ask myself all the time. I know I love women, but maybe I'm not opposed to the idea of an attractive man. Only sexually though. I couldn't have a "relationship", per se. I mean, don't get me wrong, I'm a supporter of equal rights, politically, sexually, you name it. I'm just not gay in that way. If at all. I think its a sort of bicurious attraction that I'll never fullfill. I dunno. I just had to get it out I suppose. I don't really talk to anyone about my sexual habits, so I figure a sex message board might be the place to do it.

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04 Jun 2014 8:05PM
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I'm nearly 60 and have enjoyed 30 years of paid sex with some really memorable occasions. Unlike many other guys who have satisfying sex lives with partners or girlfriends I have had to pay, but I have used the opportunity to have sex with attractive young women that I would never have been able to enjoy any other way. I'm always after the elusive girlfriend experience, however but treat girls well and have often been very pleased with the outcome.

A bit of history: Back in 2010 I used the Adultwork website to meet up with a beautiful 19yo photographic model model (we'll call her Clare) who also liked to offer extras. After a very successful sexual encounter I told her I enjoyed gangbangs. "What's a gangbang?" she asked! Well I didn't just tell her, I felt obliged to educate her properly and organised one with myself and 3 other middle aged guys. She and we loved it and she held several with other organisers before at Christmas 2011 I suggested another new experience, a visit to a well known naturist/swinging club. Let's call it Oreos.

All organised, several guys and her met at a pub before going the club. At reception, however she was turned away. We hadn't realised they had a 21yo age limit and she was 4 days short of her birthday. Fortunately one of the guys had a hotel room so we were still able to party but this was always the special event that didn't happen.

Soon after that Clare started a relationship and stopped working. She became pregnant and had three children. She left a lot of punters bereft, we wished her well but she had been one of the most enthusiastic and lovely amateur hookers, with a genuine fondness for older men and a strong exhibitionist streak and sense of fun.

I could never get over the missed event however and kept trying to arrange it with other girls. In the end I advertised a reverse booking on Adultwork and my very cheap offer of £100 for 'at least two hours' at the club was accepted by a girl calling herself Lush Companion. She was delightful, half Philipino, petite and sweet. We stayed the whole evening and I had a great time. We treated two guys to joining us in a private room although they only got to watch us and be wanked off by her.

Earlier this year, I heard rumours that Clare was working again and established email contact. In a racy chat session she let on that she felt occasionally stifled by motherhood and craved the attention she used to command from guys. She also wanted to prove she was as tight and passionate as before she delivered her babies vaginally. She was proud that her figure was almost as slim and firm as before.

We arranged to do the Oreos visit nearly five years after the first time. She would travel from home in Birmingham to Bristol, I would pay her travel expenses, plus £60/hour for two hours and would try and arrange a couple of other guys to increase her income and make up more of a party.

I advertised on Craiglist for single guys to "share an 25yo slim amateur hooker at Oreos" and when I had a disappointing response, advertised for couples as well. I did have about 2 guys and 2 couples expressing an intention to attend and participate. As it turned out nobody from Craigslist or any of my usual gangbang circulation list turned up (Losers) but we had a ball anyway.

When Clare's train arrived I was delighted to discover she was just as pretty and slim as I remembered and just as friendly and up for it. She looked stunning in the nude at Oreo's and I enjoyed a shower with her as she experienced some initial embarrassment.

Clare was only shy for about ten minutes and then realised that there were worse fates than being fancied by 20-30 blokes. She really entered into the swinging spirit. We fooled around in the Jacuzzi, were joined by a black couple who were very naughty with each other underwater. The woman, Kate, said she wanted to lick Clare out so we went to the largest of the private rooms. I could tell that Clare was really getting off on the very polite but obvious attention from guy in particular one and feeling magnanimous to both Clare and the guy said Puss could do whatever she wanted and she asked the very 'buff' and extremely nice guy, John, if he wanted to join us to 'help use up a bottle of baby oil'.

In the private room I french kissed Clare and slathered her slim torso and pussy with oil while Clare wanked John. She then sucked him while the Kate licked Clare out and fingered Clare's pale pink pussy with her brown fingers and crimson nails whilst declaring that "Oh my god you have most gorgeous pussy (True) and you taste so good". While she did that her partner fucked her in doggy with his stereotypically large cock.

Then I said it was Ok, so John found himself fucking Clare but forbidden to cum. He and I took her in turns and in several position before he came on her smooth belly. As the client, I reckoned I would finish the session by coming inside her. OMG that was lovely. Winston was fiddling with her anus and my balls which I quite enjoyed but Clare didn't appreciate!

Winston was pissed because Clare wouldn't let him fuck her "You'd split me open" she said, which seemed unlikely seeing as she had delivered several babies, but she was still very tight and I gather she had had a bad experience with a BBC in the past. Absolutely her call, after all, I was the only one paying!

After the joint session in the private room John had to leave. He had a huge grin and still couldn't believe his luck having had Clare choose him and me telling him he couldn't come until I said so!

With only 45 minutes until we had to catch the train, I had a second wind and having asked Clare just for a cuddle, we had a very sweet spoons and cowgirl quickie session in a clean private room, by ourselves (I'm afraid we left the other one with soggy towels and pools of oil and worse. Disgraceful!).

Well, after two and half hours in total at the club we ran out laughing into the street and hailed a taxi, getting her to the station just 5 minutes before her train. I don't know how many times she came over the evening. I managed more than I thought I was capable of and the subsequent Viagra headache was just mild enough for me to bask in the afterglow.

I won't forget this amazing experience for a long time. It hugely exceeded already high expectations, mostly because of a wonderful girl and a very good vibe at the club.

It cost me £140 for her (all I could afford), £15 entrance (special offer for couples on Tuesday), £30 in cabs, £40 for her train fare. This is twice as much as I've ever spent on a punt. Would have got 4 half hour sessions with my hometown regular - but what an experience!

She and I have exchanged texts and emails over the subsequent 24 hours. It is abundantly clear that she really enjoyed it. I'm so glad.

Details have been changed to protect the guilty but this actually happened last night 3rd June. I know - I was there !!!!!!!!!!!!!!!!!!!!!!

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@confessions
27 Aug 2015 12:41AM
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My Son’s Girlfriend at http://readyourporn.tumblr.com

When my family moved, No one knew the layout of the new house. We’d wander the dark halls those first few weeks, stumbling into the linen closet looking for the bathroom or the guest bedroom for the main. It was easy to get lost.

That’s why this story is complicated.

The house was just an hour north and our old house was still on the market. We moved to get closer to my son’s college, and my wife (his mother) and I agreed it’d be cheaper than paying for a dorm, meal plan, and all the others bloated expenses of an already enormous tuition.

But our son was in love.

With this beautiful curvy brunette, Cecily. An Italian-American. She looked it, but I got real confirmation when she wore these green booty shorts that stretched Italia across her ass. She could touch her nose to her knees when she stretched and was happy to show everyone her flexibility. She was a yoga enthusiast, cheerleader, high jumper, guitarist, and Hooters girl. I didn’t know that last part until I went in with a coworker after a hard day and she served us. She acknowledged me like I was any other customer and I made no mention of it to my coworker, who kept her around as much as possible with refills and innocent flirting. She acted happy to stick around and regular customers, like my buddy, knew the unspoken rule of tipping that was $10 for every hour spent there. He tipped $50. I just did the usual 20%. My receipt got a winky face. His didn’t.

“She must’ve mixed us up,” he concluded.

Sometimes she’d call the house and I’d answer and she’d launch into talking about her day because my son and I sounded pretty similar.

Regardless, she was hot. And I didn’t mind her in the backseat of the car as we drove up to the new house. We had hired movers to get the major stuff like dresser drawers, beds, washing machine, etc, but our personal stuff we decided to take ourselves and that meant extra trips. We’d take Cecily home on our next trip for the final boxes. She was going to the community college in the other town, which broke our son’s heart.

His mother and I also knew that by inviting his girlfriend to the new house, they’d christen the bed with their young love. We were okay with pretending that wasn’t happening.

We got to the new house and ordered Chinese for dinner and ate on the floor because the table had broken during the move and we ordered a new one but it wasn’t here yet. We were all on the floor. Cecily’s legs were spread casually and I could see a bit of frilly panties on the inside of her shorts. Since they’d been dating, my wife and I had reunited our passions. For me, I was teased by Cecily’s outfits and body and even face. She was fun enough to listen to as she had a real passion for music, classics that I’d listened to in high school, so I’d have the occasional conversation with her about it. And I couldn’t act on that. She was 18. But it still got me going so I’d go into the bedroom and enjoy my wife, who was definitely an older version of Cecily. Easily tanned, dark hair, a curvy body that sagged a little with age but still attractive but so familiar that it wasn’t still exciting.

I don’t know why my wife was so into it lately.

Maybe she had an attraction to the girl too, wishful thinking surely, but it seemed like she was in the mood most often after catching the kids making out or even fooling around once. I swear I didn’t peek, but Cecily had our son’s cock in her mouth, and we started doing it to drown out the sucking sound Cecily was making.

It was pretty late and storming.

Then the power went out.

We lit candles and it wasn’t a huge deal as it’d been a long day of packing and moving boxes and it was bedtime anyway so we didn’t need a lot of light.

We wandered the upstairs halls in the dark to find our rooms and we each had to stare at the unfurnished, undecorated rooms to make sure they were the right ones. It was hard to tell in the dark. My wife and I went to our room. Cecily went to the guest room. Our son went to his room. We knew that wouldn’t last.

Well my wife was in the mood. Me too. I checked the end table for condoms before starting and…

They were packed away somewhere.

“Fuck,” I said.

I put on my shirt and had on boxers still and hoped the dark would hide the slobbering boner. I think it did because I passed my son on the way to the bathroom and he didn’t say anything.

I checked the downstairs drawers, the boxes, everywhere I could think I might’ve stashed them. But I’d been gone 10 minutes and I couldn’t wait and we’d just be extra careful about pulling out tonight. It’d be fine.

Back upstairs, I couldn’t remember which was my room. I thought I did but all the doors looked the same and it was either the one on the left or the one on the right and I put my ear to the left and heard the moaning of youthful experimentation and pleasure, extreme pleasure actually, “More! Oh yeah. You’re so good tonight,” and so on.

So I went into the dark room on the right. Just a bed and a silhouette lady ripe for the taking, already spreading her legs, moaning softly.

I pulled her to the edge of the bed. I was on my knees, licking her. She had shaved. Normally my wife was a little hairy and there was something about the smooth vag that was especially nice tonight. I’d always heard that food can change the flavor and my wife had been on a fruit diet lately so that must’ve been why it was delicious and I couldn’t stop myself from partaking. Normally it was just warm up. Lubrication (before the real lube). But tonight I only wanted to feast on this pussy till her fingers gripped my hair and pulled me her way. She made me kiss her. Slipped her tongue in. She grabbed my ass. She lined up my cock then moaned into my mouth as I penetrated that wet, warm pussy. It was so tight tonight. Her body felt so good. I fucked her till the pushed me aside then switched up our positions so she was on all fours, doggy style, usually an anniversary treat for us. I fucked her hard. Her tits swung. I reached around to finger her clit, tease her nipples, she sucked my fingers. Told me to pull her hair. Her ass felt so firm and I teased the anus with my thumb till she begged me to stick it in.

She was really into it tonight. More than I think ever before. Like it was the best lay ever. It was for me. In all our time together, she seemed more wild than ever. Ready to please. Try anything. She collapsed to her belly so her large tits smashed into the covers and she only moaned and begged into the pillows.

I’d definitely made her cum already from the fucking, maybe twice as I got so lost in my own pleasure to completely notice her signs, but I was about to cum. I moaned it into her ear and she breathlessly said “Face. Please. I’m yours. Mark me.”

So kinky tonight.

So I pulled out and she got on her knees by the bed and stroked and sucked me. She never sucked her pussy juices off me! But I guess a great fuck deserves a reward. A kinky fantasy. I was about to cum so I grabbed my cock and aimed for the silhouette.

The lights came on.

Cecily has a black sun tattoo outlining her left nipple.

I didn’t know that till that night.

Her eyes were shut so the cum didn’t get into them. And I was right there, right at the edge, couldn’t stop if my mother had walked in, so I just shot thick ropes of cum across her beautiful young face.

She kept her eyes shut, giggling, sucking at my tip.

I grabbed my clothes and left for the downstairs to let my heart settle. How would the shit hit the fan? It wasn’t my fault! I thought I’d been fucking my wife! It was the new house.

I heard a door and I went upstairs. It was my son coming out of the bathroom. With the lights on we could see each other and it was awkward. I was awkward for obvious reasons. Maybe he was awkward from seeing I was still pitching a tent in my boxers after fucking his hot girlfriend. But he didn’t know that. He wasn’t even really looking my way, so we just passed each other wordlessly.

I went into the bedroom, my bedroom, with my lovely wife on the bed, naked, as up as if still waiting. I got into bed with her, not wanting to let on that I’d already been satiated. I’d have to keep fucking and honestly, I thought I could thanks to the fulfilled fantasy of Cecily.

“Oh you want even more?” she said.

And I ignored her as I was lost in my head, in panic.

She was really into it too, moving her ass towards me so there was a loud smack that jiggled those cheeks every time I pressed deep into her. But slowly she realized I wasn’t on top of the game. “You seemed so eager before,” she said. “Don’t worry. Just let me do it this time,” she said and got on top of me and rode me reverse cowgirl so I could see her ass bouncing and I rubbed my thumb against her anus but she said, “Maybe I’ll let you next time.” It’d felt so nice sticking it in Cecily’s…

My wife never found out. Maybe Cecily and my son did because they broke up shortly after. He broke up with her. It made the trip taking her home even worse.

But to fill his time and loneliness, I guess my son needed someone so he got a lot closer to his mom. She laughed about how much of a sweet mama’s boy he was being suddenly but she took it as flattery that she could replace Cecily.

(hopefully you notice the plot twist)

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