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Classy Transgender

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For the cute and classy shemale. The kind that makes a straight guy sweat. If your video looks like Howard Stern in a bad dress...DON'T POST IT! No videos of Uncle Carl clomping around the kitchen in his nasty boxers on heels and hose. Trust me..no one has ever, since the beginng of time wanted to SEE that!! lol

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21
Anonymous
@confessions
16 Dec 2016 5:17PM
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I was out of town on business and called my sister who lived in the city I was going to, to see if I can stay at her place rather than get a hotel. She told me, no problem, I could stay in the spare room, but she would not be home until late. (She works odd hours as a nurse)

I got to her place about 7PM after my appointments, put my suitcase and crap in the spare room and then went out for some food and drinks, came back by 10, and basically just went to bed.

I was woken at about 2am to what I thought was the noise of people having sex in the living room. However, after I quietly left the room and peaked around the corner into the living room, there was my sister, buck-ass naked on the floor, watching a porn while fucking the hell out of her self with 2 different dildos.

At first I thought she was stuffing them both in her pussy, but as my eyes focused, I could see she had 1 in her pussy and one in her ass and she was slamming away and moaning and grinding and watching the TV.

The porn she was watching was a lesbian orgy with toys and strap-ons.

Now, my sister is 27, long brown hair, nice body, and DD breasts. Always been a tad overweight, but can still pull off a bikini because of those tits. But she's always been kind of, well....homely. She'd never doll herself up and attempt to look good for anyone. She could use one of those makeover shows. None of my friends ever showed any interest in her. It could be because we're about 10 years apart, but mainly for all the reasons above.

In any event, at that moment, she was fucking hot as the sun.

I watched with my rock hard cock in my hand under my boxers until she came and started to quiet down. So I quietly went back to the room to attempt to go to sleep. (which I was able to, only after wacking off to the thought of my cock up her ass)

Morning comes and I get up, shower....and she comes in the bathroom asking if it's me behind the shower curtain! haha, I said, Yeah. She asked if I just got here. I said, No I got in last night. She's quiet for too long so I added, "I was so tired from work, I hope my snorring didn't keep you up, I was out like a light until I woke up 20 minutes ago!" she laughs and just says, no, but she thought I was coming tonight, and leaves the room. (I'm sure she was freaking, thinking I heard her!)

I get out, get dressed and meet her in the kitchen, say HI, hug, etc

That's basically it. Spend 1 more night...we went out that night with a few of her nurse friends, whom one I believe she might be screwing around with. (girl) They were just way too play flirty.

But that's all there is to tell.

I have no desire to fuck my sister. (sorry creeps)....but when I close my eyes and picture her fucking her holes like that, it still gets me hot!

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Anonymous
@confessions
13 Jan 2017 1:47PM
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Cute Asian Teen Who Works At Subway

I asked out a cute 19-year-old Asian girl from Subway who is out of my league but she surprisingly said yes. We saw a movie then walked around the mall and had some coffee and a pastry. Turns out she only lives about 6 blocks from me so I dropped my car off then I walked her home in the dark as the night was cool but nice.

It was arranged she would come over to my place Wednesday night and after some video games, netflix and some softcore porn she was getting frisky. She said she had only had sex twice before and was interested in messing around but not fucking. I was totally down with that.

She had cute perky B-cup boobs with long, very erect nips which I enjoyed sucking while she rubbed my dick through my jeans. I started moving down her body and she liked when I licked her belly button and kissed her right above her waistline.

I undid the button and zipper on her skinny jeans and pulled them down to reveal super cute blue and pink thong panties with a little white and black checkered bow positioned about at her clit. I could smell her through her panties and it was incredible. I kissed her plump mound for about a minute before she told me to take them off and kiss her.

She had a neatly trimmed triangle of hair above her clit and very thick inner pussy lips. The site and sweet scent of her wet meaty teen pussy had my dick literally throbbing. I pulled her jeans and panties all the way off, admiring her beautiful pedicure and cute little feet.

She asked if I wanted to eat her pussy. I almost laughed out loud at the way she pronounced it: "poo-see"

I kissed and licked up and down her tasty lips and had no trouble finding her very erect clit which was sticking out from under her meaty hood. Her lips were creamy and flavorful. As she adjusted a little, I noticed her anus. It was big and brown and looked very exotic. I told her she has a juicy little ass and that I wanted to taste it.

I'm not sure she knew exactly what I meant because she shivered and moaned when I touched her pucker with my wet tongue and nose. I pulled her closer and really starting lapping her. She tasted so sexy. I licked, kissed, sucked and grinded my nose on her tight beautiful butthole for about five minutes and she was loving it!

"You love it so much there!" she kept saying and moaning.

I returned my attention to her sweet big clit and after only about 30 seconds of flicking it with my tongue she was spasming in my face and her pussy was creaming down all over her butthole. She asked me for a towel to clean up.

After getting my pants and boxers off and laying on my bed, It took her like two minutes to finish me off with a handjob and blowjob. I wanted to cum on her thick little ass but I didn't get the chance. She used the towel to clean up the cum on my shaft and groin. I played with her toes and sucked her tits a bit.

She asked if I wanted to walk her home because she doesn't like walking that far in the dark, but I drove her home instead because it was raining a little.

Her name is Mydee. I will see her again Saturday night when her shift ends.

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Anonymous
@confessions
20 Dec 2012 12:06AM
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The other night I went out drinking with a friend of mine. We came back to my place to smoke and afterwards he said he was too drunk to drive home so I offered him the couch. I waited about 10-15 minutes after he passed out and I started to feel around his shorts. He was snoring pretty loud at this point so I got a little more bold, I unzipped him and tried to feel around for the hole at the front of his boxers. Finally after what felt like 5 minutes I pulled out his limp but thick cock. After another loud snore assured me he was still asleep I lowered my head onto his dick. After a minute or two he started to get hard and I was really starting to get into it, but also terrified at the same time if he woke up because I would, at best, get my ass kicked. Suddenly he stopped snoring so I backed off for a couple minutes, leaving his dick out in the open air. I came back a couple minutes later when the snoring resumed, sucked him for a couple more minutes then stopped altogether and just took some pictures.

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Anonymous
@confessions
17 Nov 2016 3:01PM
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I confess I'm sitting on my couch, boxers at my ankles, stroking my semihard cock, tracing my finger along the tip, feeling the precum starting to ooze out.

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Anonymous
@confessions
04 Apr 2013 3:30AM
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I confess that my first sexual encounter was with another dude. We were 12 or 13 i think. It was at a beach vacation and it started all weird. We slept in the same bed which is normal at that age. We were horsing around and I ended up touching his dick which had fallen out of his boxers. I remember it being soft. We both got all quite and he said "Do you want to" and i quickly replied in a jokingly manner "Yea if you suck my dick first" and he said ok.
He sucked on my dick for a few min, which was very nice as it was my first blow job ever. I then sucked on his dick as I assumed it was the only right thing to do. It was salty. After that he let me fuck him in his ass for a little while which actually wasn't that great as we had no idea what we were doing. He then asked to fuck me, which i said was ok because once again i assumed it was only fair. He never penetrated me though as I lied and said it was in when it wasnt. the whole thing was over pretty quickly and i remember feeling weird after.
We went on to fuck a lot more for a couple of years until we just stopped one day. I think in the end he only ever penetrated me once or twice as i usually lied and said it was in when it wasn't.
I never felt gay for doing it either, i never questioned if it was right or wrong. I have never done anything else with a guy since then either and have had nothing but girls since. We never kissed or held each other, it was always just blowjobs and fucking.
I have a few more times i remember, but not a lot, none of them were that memorable I guess. I just wanted to see if anyone else ever did this as a kid and if it ever lead to anything else or if it was just "boys being boys"

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ClaireBearAly
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@random
15 Oct 2019 2:18PM
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The following is not real. Some of you know have known me will recognize some of the people, but this is not how this actually happened. People suggested I try writing something else so here you go.

So, Im going to be straight up for a second. I think about fucking everyone I meet. I think about how they would feel under my hands. Or how I could make them cum. I think about what kinky stuff they might be into. Is the fat old charge nurse into anal? What would that paramedic do if I asked him to piss on me? Would the clerk that checked me out at the store rim me if I went down on him?
All of these and more race through my mind. Normally I push them out of the way. Sometimes I dwell on them, and try to find out. And that’s how it was with my father in law.
From the moment I saw him, I wanted to fuck him. Joe and I had just started dating and we had gone to his parents house. My future father in law (lets call him Frank) was a runner. Not just recreationally. He liked to do marathons and shit like that. As such, he was in amazing shape. Athletic and slim. His muscles were well defined under his skin, and he had the sharp facial figures like a sculpture. His hair was still black, aside from the gray that had begun to appear at his temples.
To be fair, I was in shape then too. More than one, actually. They were just circles of various sizes.
From that day forward, I wanted to fuck him. I wouldn’t say I was obsessed, but I did think about it often. I was still occasionally fucking Joe’s brother, so I would find myself comparing their cocks. Joe’s wasn’t small, necessarily, but it lacked his brother’s girth. I began to wonder what it would take to get Frank to fuck around on his wife. He had raised one son to have an intense moral direction. Joe doesn’t like anything I like in the bedroom, mostly because he finds it degrading to me.
On the other hand, his other son was a complete dirtbag. He was the one that came on to me first. To be fair, I kept it going after the wedding, but he could have said no. What kind of a guy fucks his brothers wife the day they leave for their honeymoon?
So what kind of guy was Frank? One of his sons was an outlier, but which one? And then what kind of woman would not only entice him to cheat, but to fuck his sons wife as well. It was the kind of challenge I rose to. I had to find out. It would be quite the accomplishment, fucking all the men in a family. Well, aside from mine, I guess.
It would be a process. A long one. Find out if he would cheat. Find out if he would cheat with a fat girl. Find out if he would cheat with a fat daughter in law. Finally find out if he wanted a whore or an angel. I could do either, but angel was temporary. I would see him pretty regularly, once week or so, more often during the summer. He had a pool, you see, and Joe loved to swim.
So I got to work. First step was to see if he was even interested. I waited until the next time we went swimming. That would be a few weeks away, so I contented myself through masturbation that mostly involved him and my dad tag teaming me. By the time we were actually going, not even these clit sessions could tide me over.
I had thought about doing a two piece, but I couldn’t bring myself to do it. So I settled on my one piece. It would be sufficient for this. The changing room was their bedroom, and it had a sliding glass door that led to the pool. There was a curtain to pull to cover it. I thought about leaving the curtain open, but there was never a time when he was the only one in line of sight. Disappointed, I headed to the pool to join the others.
It was while swimming that I saw my first opportunity. The pool itself was a saltwater pool, and at one end was a hot tub fixture that overflowed in a waterfall into the pool itself. Frank was standing by the waterfall, talking to Joe, who was in the tub. I dove under the water, and while I swam to the waterfall, I adjusted by suit so that I had a nipple peaking out. I wasn’t able to be sure, and I didn’t want too much to show, but it was a gamble.
I rose out of the water next to Frank, my left nipple exposed. I slid up next to him and asked what they were up to. Joe couldn’t see my tits from his position, No one else would be in line of sight if I turned towards Frank. Slowly, with the waterfall falling on me, I turned towards him and asked him what he was drinking.
He looked to me and opened his mouth to answer, but his eyes went right to my tit. I held my breath. Would he say something? Would he freak out? Would he just stare?
The latter. As he responded to me, I slowly exhaled the breath I had been holding. His eyes were flicking between Joe, me, and my nipple. I was looking him over too. His chest had a small v shaped patch of graying hair, his nipples sat flush against his body. His neck was ridged by firm tendons and muscles. Fucking hell he was sooo hot. Joe began moving toward the stairs so I dipped down and fixed my suit.
I swam away eagerly awaiting my next chance. I was optimistic about this thing for the first time. Pushing the envelope and taking chances were such a turn on for me that I was spent the rest of the swim time rubbing my clit hidden by the water.
We caught eyes a few times after that, but he didn’t really betray anything else. A plan took form. I would be the last to get out. I would go into the room to change, and somehow entice him in there once I had stripped out of my suit and covered myself. Then, a quick flash, or something. I wasn’t sure yet.
As luck would have it, Frank and I were the last two. Improvising, I got out and piddled around outside until Joe had finished changing. I went in, and began to look around the room for something to give me an excuse to get him in here. I had to hurry, and act while he was alone in the pool area. If anyone else was there, they might come instead.
It didn’t take long. There was a hamper in the bathroom for towels, but Joe had been Joe and just piled them on top of it. Under the pile of wet towels, it might be missed. I stripped out of my suit, and wrapped myself in a dry towel. I rushed to the door and looked out. He was still alone, but he was out of the pool.
I slid the door open. “Hey Frank. Where do I put my towels?”
He looked at me in the towel, and flipped his head to the main doors into the house, possibly to see were everyone was, then back to me. “I-In the bathroom, Claire.” He said.
“I looked I don’t see it. Can you show me?” I asked. Deliberately I looked down. His wet trunks clung to his body. It wasn’t hard to see the outline of his cock, hanging flaccid, along his body. It was hard to gage, but he looked bigger than either of his sons. I let my eyes linger, then went back to his face. I bit my lower lip.
Wordlessly he started towards me. “Thanks, Frank.” I said, retreating back into the room before he got there. Now what? I thought to myself. Just dropping the towel would be a high risk high reward situation. If he reacts poorly, it might be impossible to say it was just an accident. Instead, I sat on his bed, facing the bathroom. I spread my legs, leaving the towel on, but parted just enough.
He came in and stopped. My breath caught again. For what seemed like an eternity he stared at me. He smiled slightly, but it was gone as quick as it came. He moved to the bathroom.
“Oh.” He said as he rounded the corner. “Fuckin’ Joe.” He said. He leaned down to begin picking the towels up. He turned his head to me. His eyes right between my legs. I know he could see my pussy. “Does he at least put thigs away at home?”
I just shook my head, looking at him. He looked away and stood. “Well, there’s the hamper. You can put the towel in there.”
I stood, bent over to grab the wet one I had used, and walked into the bathroom, passing him in the door way. I turned sideways, ass to him, as I slipped through. I stuck my ass out, and brushed it across his groin, feeling his bulge as I did so. I dropped the towel in the hamper.
I turned to Frank. He was staring at me. “Can you hand me my clothes? They are on the bed.” His face was red as he turned and proceeded into the room. As soon as his back was turned, I went for it. I dropped the towel. He returned and stopped as soon as he saw me. “Thanks.” I said. And I took the clothes. He stared at me. At my tits. My pussy.
“Claire, I-“ he began. I closed the door.
Fuck. I needed to cum. I heard the door slide open and then close. I thought about his cock, I thought about him pinning me in the doorway and forcing it into me. I wondered if he would try to fuck my ass. My fingers went to my clit. It didn’t take long before I was cumming.
After, I took stock of where I was. I had gone for broke. It hadn’t blown up in my face. And I felt like I knew he would cheat. I felt like he liked big tits, and I felt that he wanted me to be slutty. Maybe this would be easy.
I was wrong. The next few swim days he was noticeably absent. His wife had said that he was running errands or something like that. She never seemed bothered. I fucked myself after one day imaging he had told her and we were going to have a threesome.
The next chance would be an unexpected one.
It was Labor Day. I remember because I was off and Joe worked, taking the double time that he would get. Joe was already gone when I woke, and knowing that I would have 7 hours in the house alone had me wet thinking about who I was going to have over to fuck. I had begun to flip through my contacts when the phone rang, the caller ID showing it was Joes cell. My heart sank. He had to be telling me that he was coming home early.
“Hey, babe.” I answered, forcing a yawn.
“You just getting up?”
“Yeah. Whats up?”
“I need you to do me a favor. I need you to go into the garage and grab a tool and bring it to my dad.” He said.
I sat straight up. “Yeah I can do that.”
“Mom has the car and she’s out at my aunts. He told me not to worry about it, but hes been looking forward to this project for a while.”
“Sure!” I jumped out of bed as he talked me through the garage and the location of the tool. Once identified, I let him go, and began to plot my course of action.
He was clearly hesitant. But he couldn’t trust himself around me. He knew what the game was, he knew he would lose, and he was just trying not to play. I needed to be able to get him to the table.
Clothes would be key. It was a little cooler, too cool for shorts, but leggings would work. No panties. The top would be a little trickier. My tits are huge, H Cups. Braless wasn’t an option, but I had an ill fitting balconette that let the tops of my areolas pop out if I positioned it right. A white camisole and light black sweater completed the outfit. I checked myself out in the mirror. A quick tug on the camisole brought a hint of areola into view. Perfect.
I went out to the truck, threw the tool in the back and headed off to my in laws house. The whole ride over there I had the butterflies in my stomach that were my vice. That anticipation of something new and different. The pushing of boundaries, the taboo of the act, the risk of getting caught. All were combining to give me a high that nothing else could touch.
By the time I pulled into the gravel driveway, my pussy was aching. As I rolled to a stop, I realized I hadn’t even thought about what I was going to do. I had been so preoccupied thinking about fucking him, that I hadn’t even bothered to think about how I was going to do it.
As I got out of the truck, Frank came out from the side of the house. He was in jeans and a long-sleeved red shirt. Sawdust clung to it. He stopped when he say me, but then continued on.
“What are you doing here, Claire?” There was a tinge of anger. Good.
“Joe told me you needed this.” I went to the back and pulled out the saw.
“Yeah I told him not to worry about it.”
“Well he worried.” I passed the saw to him.
He looked me up and down. “Tell him thanks.” He said and then turned with the saw and headed back to the house.
Fuck. This wasn’t working. I watched as he turned around back. He was resisting, but I saw it in his eyes. I know that look. Seen it in plenty of men’s eyes. I pulled the black sweater off, threw it in the truck, and headed off in his footsteps.
I rounded the corner and saw him in his workshop. Formerly a detached garage, he had turned it into his hobby room a few years ago. There was a piece of wood on two stands that he was measuring. A few stools and chairs littered the perimeter of the shop. When he saw me, he stopped and sighed.
“What are you working on?” I asked.
“Claire, why are you here?”
“Im bored.” I said, biting my lip. “Joe is at work, and hes not as entertaining as he could be even when he is home.
“W-well I got a lot of stuff to do here, and I’m not going to be entertaining anyway.” He returned to measuring.
“Well, anything is better than being alone at the house.” I found one of the rocking chairs and sat in it. So far, so good, but I was running out of moves. The silences persisted for a few minutes while he measured and marked different pieces of wood. Then it hit me. I had a plan. All I had to do was wat for my opening.
It didn’t take long. After about 5 more minutes of silence, he left to go inside to get something. I took my shot. As soon as he was gone, I jumped up and headed for the pool. Flipping the cover on the control panel, I flipped the tub to on. I raced back to the shop, and I stripped off all my clothes, placing them in the chair I was sitting in. I then raced through the brisk air to the tub, where I slid in.
The water was ice cold. My nipples immediately hardened. The water coming from the jets was warm, but still, my teeth began to chatter. I prayed the water would heat up quickly.
I heard the side door open. He was heading back into the shop. It didn’t take long before he rounded the corner. I waved at him. He slowly walked over.
“Claire. What the hell are you doing?”
“Entertaining myself.” I said. I made a show of pushing my hands down to my pussy. “Since you wont, I have to find something to do.”
“This ain’t right, Claire. Theres something wrong with you.”
I smiled and closed my eyes as my fingers slipped inside me. “Mmmhm.” I moaned in agreement. “Very wrong.” I said.
He watched me finger myself. He didn’t leave. I went all in. I stood and began to walk out of the tub. The chill in the air brought my chattering teeth back. “I’m going to go into the house and Im going to be entertaining myself. If you are bored, you should follow me.” And I headed for the sliding door.
I entered, thought about the couch, but decided against getting it all wet, and went to the floor instead. I got down on all fours, ass in the air, and began to play with my pussy. I rubbed my asshole too.
I heard the door open and smiled. I had won.
I rolled over and lay on my back. He stood over me. He began to undo his jeans and I moved to my knees. “You are going to love this, Frank.” I told him.
I was eager to finally see this cock. As his jeans fell I reached up and took his boxers in my hands, I pulled them down.
It was wonderful. Bigger than either of his sons. A good 6 or 7 inches, if I have to guess, but thick. His balls hung in a sack covered in gray pubic hairs. I opened my mouth, and licked the length of his shaft, my eyes locked with his. From the tip to the base, and then back again. He began to grow. I took him into my mouth and began to suck. Using my mouth, suction, tongue, suction, tongue. He grew to an impressive level of fullness in my mouth. I pulled it out.
“Gag me, daddy.” I said before plunging down on it again. This time I felt him hit the back of my throat and the first gag began. I felt his hand on the back of my head as he held me there. Oh yes. He wanted a whore. I’d give him that.
He let me up and I pulled back, rubbing the slime covered cock on my face. “You are so much bigger than Joe.” I said.
“Shut the fuck up.” He said and he forced it back in my mouth. Another round of gaging began. When he let me up from it, I went back to his balls, letting the cock lay across my face. I licked and gently sucked each ball, and then I moved lower. He moved back. He looked at me confused. “What are you doing?”
Poor bastard. He’d never been rimmed. I smiled. I stood and undid his shirt. Once off I sucked and nibbled at his nipples as I walked him back to his chair. He fell down into it. I returned to my knees and the blow job. Building up a good supply of saliva, I worked down to his balls again, and then to under them.
It was clear he had been working, but it turned me on even more. Lower and further I pushed, my tongue searching for his ass. I could hear him moaning. I reached up and grabbed his cock. Mainly to keep him from jerking it and cumming too quick. I finally found it. I thought about how wanton and whoreish I was being. On my knees, with my tongue on my husbands fathers ass.
“Fucking hell, Claire.” He moaned. I pulled out.
“Betty doesn’t to that, does she?” I smiled.
He shook his head and stood up. It was his turn to take control. He turned me around and began kissing my neck and rubbing my tits. I felt his cock pressing into my back. He reached down and inserted a finger into my pussy. I felt him pushing me down and over. I resumed my position on my knees, my shoulders and head on the carpet.
“Fuck me daddy.” I said.
“Where?” he asked
“Anywhere you want.”
“Does he do anal?” I shook my head no, preparing for the possibility that I was about to take a pretty big cock in my ass. “Just my pussy.”
I felt the head at my ass. I reached back and spread for him. “Yessss, daddy.” He began to push in. I gasped when he first popped in. We had no lube, aside from my spit, and he was bigger than any I had been buttfucked with in a while. I let my cheeks go. The pain was reaching my threshold. I took my other hand and went to my clit, hoping to off set it.
That seemed to work. The searing pain became more bearable. “Im a whore. Im a whore. Im a whore.” I began to repeat to myself reminding myself that I wanted this. He began to slid in and out.
“Do you fuck Bettys ass, Frank?”
“Call me daddy.”
“Do you fuck Bettys ass, Daddy?”
“Not in a while.” It turned me on even more that Betty used to take dicks in her ass.
“Pull my hair daddy.” He obliged as he began to pick up speed. He had the stamina I expected from a runner, as well as the endurance.
He was pounding my ass now. My own fingers had brought me to the point of climax. I screamed as the cum took me, clinching my ass around his thick invading cock. I fully expected him to cum. But he slowed down. Not wanting to hurt me as my ass was clenching, he slowed, delaying his own satisfaction.
As soon as I subsided, we resumed the fucking. His relentless assault on my body. I couldn’t wait to have him fucking my pussy like this. “Im gonna cum, Claire.” He exclaimed.
“Do it daddy. Cum inside me.”
With a shudder he did. With each pump he moaned and shook. I couldn’t feel him cumming, but I knew it was a lot. I only felt it as he fell out of my ass. He fell next to me, catching his breath. I moved to my side and snuggled up next to him. “Good?” he asked me.
“Better than both your sons.” I smiled.
He looked at me shocked for a moment. Before he began to smile, letting his head fall back to the floor. “Wow. You are a whore. But you are an amazing fuck.”
I smiled and looked down at his cock. The cum coated it, but it didnt look bad. I leaned over and took it into my mouth. He looked at me with a mixture of lust and confusion. I felt his cock twitch a little in my mouth.
I pulled off it. “I want you to fuck my pussy next.”

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Anonymous
@confessions
26 Jun 2014 11:20AM
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So I had this wonderfull girlfriend, she was 18 when I met her and I was 19.
Still a virgin she asked for me to be patient, to give her some time before all the action started to happen.

At first she gave me a handjob, and i made her cum using my hands.
When the first blowjob came it was awesome, and after a few times she suprised me by not stopping to suck my dick when i told her i was cumming.
She sucked it gently while i filled her mouth with my hot cum and before i could say 'you dont have to swallow it' it was allready gone.
As a proud slutty girl she raised her head and opened her empty mouth.

After a few months it went bad.. I didn't got the attention i wanted to have, the sex was almost none and above all the blowjobs with happy ending were also gone.


So.. I found this other girl on a chat website by pure luck.
She was having a bad time at home.. Probably a bit physical problematic there..
And we decided to date, on one condition that she would listen to me and do as i say.

At the first date we weren't planning a lot to do but just talk.
At the end i wanted to bring her home, but she wasn't in a hurry so i decided to test her willingness.

I took her to a forest, and when we were in the middle of nowhere i asked her to undress herself.
Without hesitation her clothes came of untill she stood in her underwear.
I waited and crossed my arms, to let her see i wasnt satisfied.
She understood it and undressed further untill she was naked.
She was 18, and stood there.. Slim figure but with nice tits and a cute ass.
Hard nipples because it was a bit breezy.

I walked up to her, touched her thighs and then her pussy.
She was practically on fire at that moment as my hand touched her hot and wet pussy.
I told her to get on her knees and let her open my belt and pull my pants down.
With my hard cock still in my boxers i told her to kiss it, and she gently and passionatly kissed the cotton surrounding my dick..
Then i took it out, and forced her mouth open.

She pulled her toungue out, trying to lick it.
Gently i pushed it in, and let her head out of my hands.
She started to suck it, first gently then a bit rougher.
Following my directions if to take it as deep as possible, or just lick it.
Her saliva mixed with my precum ran down her chin onto her chest, forming a stream over her body.

I instucted her that when i was to come, she wouldn't stop and let me cum in her mouth, with her lips sealed around it sucking everything out.
It was the best blowjob i'd ever had, wich resulted in masses of cum on wich she gagged a bit when i shot it against her troath.
She couldn't keep it in completely and let some cum down her chin, and chest towards her pussy.

When i pulled out she showed her full mouth to me, even i was amazed by the load i shot.
She then swallowed it at once and licked my dick clean.

After that i told her to dress up again and brought her to her home and said goodbye.

During my relationship i'd met her about 100 times over 2 years.. practically every week we had sex.
I tought her how to suck the best way so every guy would like it.
I deflowerd her pussy and ass, and now she would be every mans dream.

Then i got caugt in the act.. It changed everything.
Now i have a new girlfriend, and i still meet my little cumslut now and then.
But without the sex.

Were still pretty close and talking about it though, and everytime we meet when her friend is away, my dick is always eager to come out of my pants.
And her eyes, are always on my bulge.

We think the same things, the things we did.
But keeping it safe at the moment.

Do i regret it? not by a mile!

(the legal age in the netherlands to have sex is 18)

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@confessions
19 Oct 2011 3:00PM
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I was working in my sister in laws house today. Her hubby and the mother in law went out shopping and while they were out the sister in law mad e lunge for my cock while i was up a pair of steps, telling me her hubby never fucked her so what could i do i had to oblige especially when her hand was down my shorts, would be rude to say no. Anyway after that MIL and hubby came back. 3 hrs later im in the garden shed checking out the electrics and MIL comes out and grabbed me from behind saying she hadnt seen my cock for ages....fucking hell i thought so i pulled down my shorts and boxers and she gave it a right old tugging made me cum again and she loved it. Asked me to go round her house to check out her electrics now ...she smiled and said i can have a bit more attention next time....role on Friday.

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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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@confessions
08 Jun 2012 2:36AM
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I confess im layin next to my friend in bed (were both guys) and i have my cock hangong out of my boxers and im horny as fuck and i just wana experiment but hes not gay what do i do?

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@confessions
16 Nov 2013 8:05AM
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Need Advice pls.
Have been seeing my gf a couple of years and our sex life is healthy but her teen daughter kinda flirts with me. She sometimes comes into the bedroom when I'm changing and stares at my crotch, commenting on how many buttons I have on the fly or says "look at your sausage sticking out" when she can see the outline through my shorts.
She like having a back and shoulder massage as well as running my fingers down the back of her arms as it tickles her and gives her goosebumps. She pretty much likes gentle "tickles"/strokes anywhere on her shoulders, collar bone, back of her legs etc. So over the months theres been a few incidents. She's had on short sleeping shorts and one weekend morning we sat on sofa together, she was curled up with her bum facing towards me and I spent ages stroking the back of her legs, right up the top of her thighs and even across the bottom of her exposed bum cheeks. She liked it but never says much other than "it tickles" and she squirms and giggles. Also she doesn't wear a bra in bed, the other day I came home from work and she'd been home all day ill. When I sat with her, she put pillow on my lap and laid back on it playing on her iPad, knees bent up and I was stroking her head, tickling her arms and also just above the hip bone where its sensitive. Pretty much all round her exposed midriff, running my hands along and up her rib cage and I was literally about an inch from the base of her breasts!! My heart was pounding, I could see her breathing was increased but she just lay calmly lapping up the attention. When I ran my fingers along the waistband of her pyjama bottoms, due to her slightly curled position and being long-legged but short body and having her knees bent right up, her crotch was only about 6 inches from my fingers. I didn't know whether she was just waiting to see what happened or what. Another weekend morning we did a similar thing but she lay on one side with her face inches from my cock! Back in summer she put her hand almost right in my lap so I could tickle the back of her arm and she kept twisting it about so I could tickle all of it but the base of her thumb kept touching my cock which then got harder. Next thing I know, rather than putting her head in my lap with a cushion as normal, she just plonked her head down right on my growing erection!! I didn't know what to do or say and her mum was in the house this time so stayed quiet.
Another time she asked for a proper back massage so got her to lay on my bed, again on a weekend morning, small vest and shorts, no bra and I spent ages doing the same, running my hands over this tall slim, pretty blonde girl with a bubble butt!
One night in bed she got in to give her mum a rare cuddle (shes too old for all that really), I got in behind her and she shoved her bum right back in my lap and I know she could feel all my package! I only had thin boxers on and my cock started to grow so I twisted away slightly cos she's cheeky I thought she might call out "whats your sausage doing pressing against me" or similar cos she thinks saying things like that in front of her mum is funny. After I twisted my cock away, she moved her bum about, not sure if she was trying to find it!! Me and her mum are pretty open and they both know I'm comfortable with nudity so her mum trusts me around her, luckily.
On another occasion I'd been in the shower and was stood in the bath still drying off and her mum called up to me from downstairs so I opened the bathroom door to shout back, the step daughter was in her room and knew I'd just been in the shower and without asking or knocking on the open door just walked into the bathroom! My towel I think was just covering my cock but I don't know. We all just laughed it off. Unfortunately the hand in lap or looking at my crotch while I'm changing hasn't happened for a while.
Really don't know what to do, she's gorgeous and its a massive thrill stroking her body and being inches from her bare breasts while she lays happily on my lap. How would you guys take it from here? On one hand she prob wants something to happen but its seriously taboo, on the other, she may just enjoy the attention.

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@confessions
31 Jul 2012 10:27AM
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I confess i want to expose myself to my mom. but i'm not sure how. I was thinking of
two things. either walk out into the hallway where she is with a hardon in the morning, or play with myself and lay my boner to the side in my boxers so she can see it through them wwhile pretending to sleep.
what do you guys think i should do?
ps: sorry for bad English, it's a secound language

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