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ClaireBearAly
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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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olddenverguy
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01 Dec 2017 1:01PM
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With the house all to myself from Thursday through Sunday night, I suggested to Robby (our gang bang guru) that it would be great for him to arrange a fuck session where we could take advantage of an empty house for a change, rather than renting a hotel room for our activities. He came through within the first couple of hours, which just shows what an amazing track record he has of snagging seriously fuckable women.

He'd connected with Jamie via a Craigslist ad. She's 30, 5-5 120, with blonde-highlighted light brown hair and 32B tits. The photo posted here is the one she sent along with her request to meet. Because it was midday Thursday, Robby was only able to arrange a threesome, since the rest of the guys in our over-50 GB group couldn't make it on such short notice. Jamie was apparently OK with that, though, since this was to be her first multi-guy sex encounter and she wasn't too sure how overwhelmed she might be with more participants. And if her claims could be believed, it would prove the first time in more than a month that she'd had any kind of sex at all.

While waiting for them to show up, I gave Robby some shit via text because, after picking Jamie up from her place in North Denver, he had trouble finding my house on the southeast side. He claimed his GPS was all fucked up, but I was more certain it was operator error. Also on the way over, he "warned" me that Jamie was a bit on the skanky side, but I replied that, given our plans for the afternoon, that was a benefit rather than a flaw.

They showed up at my place just before 1:00 p.m., around 20 minutes late. I'd prepared our guest room in advance by stripping the queen-size bed and putting on a new bottom sheet plus clean pillow cases, setting out a brand-new tube of lube, and adjusting the shades so the room wouldn't be quite so bright. Meeting them at the front door, I saw that Jamie was dressed in a pleasantly slutty outfit: Short green cloth jacket over a black lace sleeveless top with a purple bra showing underneath, a denim micro-mini skirt that barely covered her ass, and over-the-knee high-heeled leather boots. She had her hair tied back in a ponytail and spun around after coming through the door so I could apply the green silk scarf I was using as a blindfold. She'd asked for this as one of the conditions of the afternoon's activities, and I was happy to oblige.

Given the lateness of their arrival and the fact Robby had to leave in an hour to pick up his kids from school, we immediately headed upstairs and got down to business. I helped Jamie off with her jacket and unzipped her skirt so she could slip it off. She quickly removed her lacy top and I unhooked her bra. We all agreed she could leave her boots on for the duration. Meanwhile, Robby was stripping down to bare skin, tossing his clothes haphazardly onto the floor in his haste to start in on Jamie. She asked us to leave her undershorts on -- they were leopard-print boy-shorts -- which was fine because they'd been altered by having two carefully placed holes cut out of the crotch. One showed off her smoothly shaved pussy while the other exposed her tight little asshole. I ran my hand down over her buttocks and slipped my middle finger into her tight, wet pussy while removing my clothes at a pace considerably slower than Robby had achieved. He put his hands on her small, firm tits and began to suck on her nipples, which stood up nicely to the attention. She used one of her hands to tug on his fully erect cock - it was hard even before he took off his trousers -- and meanwhile I disengaged so I could remove the rest of my clothes as well.

Robby suggested she lie on her back, which she did, and he stuck his face in between her thighs to taste some of that sweet, sweet pussy. I thought he might be down there a while, but after only about a minute of some serious licking he stood up, pulled her hips closer to the edge of the mattress, and jammed his seven-inch dick into her wet slit. She had her legs up in the air with Robby pressing his hands against the backs of her thighs to keep them there as he pounded her hard. I'd stroked myself from a semi-hard to a fully erect state and climbed onto the bed so she could take my dick in her mouth. By changing my angle of approach, I was able to slide my entire member into her mouth. Of course I'm less than six inches, so it's not a huge challenge, but I could still sense the tip of my cock hit the back of her throat with every downward thrust, which was a great feeling.

After a few minutes of fucking her while standing alongside the bed, Robby suggested it was my turn to squeeze my dick into that pussy. We helped flip her over -- her equilibrium was compromised somewhat by the blindfold -- and I entered her from behind, doggie-style. It had been a couple of months since I'd had sex, so this was a welcome opportunity and I made the most of it, thrusting enthusiastically as Jamie reached down with her right hand and rubbed it briskly across her clit. Meanwhile, Robby had opened up the small bottle of Astroglide he'd brought with him and suggested we DP the girl. She was definitely on board with that idea, so we maneuvered ourselves into position with me on my back and her on top, facing me. She reached down and re-inserted my cock into her pussy and leaned forward so I could suck on her tantalizingly erect nipples. I moved my legs together and Jamie did the same with hers, which allowed Robby to climb aboard and straddle the two of us. He squirted some lube onto his index finger and worked it into Jamie's rear hole, removed it quickly, and leaned forward while pressing his cock's head against her anus. She balanced on one hand above me while reaching back with her other hand and pulling her butt cheek aside to provide him greater access. A deep grunt from her, plus added pressure on my dick inside her pussy, told me he was in her ass. I lay still with my hands on Jamie's hips while Robby did all the work. He pounded her ass with enthusiasm and some deep penetration while she ground my pussy against my lower body. I saw Jamie's chest flushing red and moved my hands from her hips to her tits, tugging insistently on her nipples to match the rhythm the two of them were playing out above me. After a couple of minutes, Jamie let out a big groan and announced she was cumming.

By this point Robby was starting to run out of gas, so he pulled out of her ass and stepped across the hall into the bathroom so he could find a towel for wiping off his dick. Jamie rolled off me and onto her back, but she was clearly far from done. Neither was I -- so I climbed off at the foot of the bed and pulled Jamie toward the edge, pushed her legs up into the air and told her to hold them there (which she did by looping her arms around the backs of her knees), and then I sank my cock into her ass. It was the first time I'd done anal in probably 20 years, and it felt terrific. I was soon pounding her with balls-deep thrusts, and she let go of one leg so she could reach down and mash her fingers against her clit in a rapid-fire manner. Meanwhile, Robby crouched next to her face and stuck his newly cleaned-off dick into her mouth. She sucked him enthusiastically while I fucked her ass; then her butt muscles clenched and she was suddenly in the midst of her second orgasm.

Once it passed I withdrew, especially since my legs were shaky from all the thrusting that I was hardly used to anymore. Robby decided he wanted some more of Jamie's asshole, so we switched positions and he stood at the foot of the bed with his dick inserted all the way into her poop-chute. After about eight or ten thrusts he announced he was ready to cum, so he pulled out and shot a nice thick glob of white goo all over her pussy lips, with some coming to rest on her shorts. I was positioned behind her, with her head cradled in my lap, so I reached down and used two of my fingers to scoop up some of Robby's ejaculate. Then I popped my fingers into Jamie's mouth and she sucked them dry.

By now it was time for Robby to split, but I wasn't quite ready to call it quits and Jamie agreed to let me take her home. As Robby dug around on the floor for his discarded clothes and started to put them on, I finally pulled off Jamie's blindfold -- it was simply too much in the way after all this time -- and convinced her to get on top of me, 69-style. Robby said a quick goodbye, to which Jamie was only able to reply with a muffled grunt, since at that moment she had my entire cock in her mouth. I licked her pussy, sucked on her clit and slipped a finger into her ass, hoping to induce a third orgasm, but she came off my cock long enough to explain we'd made her pretty sore down there, so instead I pulled my face and hands away from her crotch and simply let her do her work. About three minutes into this latest activity I said, "OK, finish me off." Jamie took that as a cue to get me to cum, so she wrapped her hand around the base of my cock, sucked harder on the head, and shortly thereafter I was pumping my jizz down her throat.

She wanted to smoke a cigarette (Marlboro!), so she slipped on her black lace top and I led her toward the deck that's just outside our back door. She also wanted something alcoholic to drink, so I unscrewed the top off a tiny bottle of Barefoot Moscato and poured it into a juice glass. Classy presentation, eh? By now it was nearly 2:30, so rather than begin another fuck session -- we were both pretty sore at this point -- I suggested I drive her home. We got dressed and hit the road. On the way there, we enjoyed an interesting conversation about local politics, the police -- she was on probation for her 2nd DUI, thus a suspended drivers' license and the inability to drive -- and other non-sexual elements. As she exited my car she stuck her head back inside and gave me a warm kiss on the lips. "Tell Robby I'll be in touch again soon, OK? And next time, a couple additional guys would be all right." She'd obviously enjoyed herself!

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Something I've just always done since college, car has condoms and lube stashed in it. Every time a girlfriend and I went grocery shopping I'd park in the back of the lot. Before we went in I'd finger her to an O. No rush, just tease and let it build until she went. I wouldn't let her tease me, just me kissing, caressing, and fingering her. Usually I teased her through her panties just to get them soaked. She'd go, we'd get dressed, and go shopping. She'd usually stumble a few times, sometimes get a bit jumpy if I put my hand on her back. I'd always suggest she pick out a carrot or cucumber, maybe bananas or if it was the holidays a thick candy cane. We check out, back to the car, more fun. I'd tell her to pull it out of the bag, slip a condom on it, and hand it to me. I'd pour lube on it, start fingering her and then I'd fuck her with it. She already went earlier so it was more challenging to get a 2nd O. She'd want to touch me, and denying her made her even wetter. Finally she'd go, usually really loud depended on the girlfriend. At that point she'd unzip me, "you're getting sucked", and I'd get amazing head until she completely drained me in her mouth, swallowing all of it. We'd clean up and head to her parents house. She'd help prep dinner, always using that carrot or that cucumber (if it was a banana she made banana bread). Sometimes I'd secretly touch her under the table, run my fingers up her leg etc. After dinner we'd put a movie on and fuck, any position I wanted, any toys I wanted. She's already gone twice and can still taste my cum. Everything now is bonus. To this day I still do it to my wife. She thinks she's the only one. She has no idea I opened other eyes to whoredom! Just saying we need to go grocery shopping makes her weak in the knees.

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@requests
08 Jun 2016 5:44PM
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are there any honest, true, hott,horny folks, females, males, cpls, subs, cpls where there are switches, etc. for this dominate Master and my love, slave naan? wild, dirty, kinky, slutty whores, where anything taboo goes who are what they/you ARE/DO WHAT YOUR WORDS SAY? it seems all these posts ask about others, rate my cock, would you fuck my sisters, aunts daughters teacher, well fuck yeah, BUT what about YOU, in the first person? we are also slutty fucking whores as well, hell we gave up meeting anyone face to face, but what about a great texting/pm which harms no one becum really intense and lets go. what is this site about, children who tell stories and string out bullshit for ...... CUM on, really honest, truthful folks with real honest, truthful sexual inner pent up "Wants'n'Needs" to explore as well as those all ready going on, we want the same.
not once has any person no matter what the kink answered a note being serious, it is a fucking shame, i could go to that place "CHUCKY CHEESE" and find more truthful real people for they know pretty much the truth.
my challenge is this, who is as willing as we are to be as honest and open as we are BUT REAL,
i wonder if that is really difficult.
now is a good time...

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03 Jun 2017 2:28PM
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Part 20: Our Adventure [rest of the story on my profile :) ]

So I havent told you my name at all and that has its reasons. I think I'll just assume a pseudonym. I chose Sam (Still Anonymous Motherless - makes sense right? :D) so things will be a bit easier for me and for you as well.

Anyway, after Anna told me about her sex adventures with Beth, I wanted to get better at oral as well. So when Haley was out of house for a week, we met up whenever Jim left the house. First few times we did the basics. She was laying on her back while I went down on her. We had a deal that she would give me precise instructions on what to do and so I learned fast. When first it took her forever to cum (also because she had to concentrate to give instructions all the time) by the end of day 3 and after 10+ sessions. (Of course we also had sex in between, just left that out because its not really relevant).

The next day Anna went on her knees on the bed and lifted her ass up so I could lick her pussy. I had to get used to this new position but at the end of the day I mastered that as well. The last day Haley was away, we practised 69. Now this is a real challenge, I can barely think when I get my cock sucked by such a godess like Anna. Still, at the end of the day I was doing okay. When Haley came back I also told her I wanted to learn how to please her better and we did the same game, only faster since I already knew what I was doing. I just wanted to make sure she would grow suspicious.

There was another reason, why I wanted to practise my oral skills. I wanted to fuck Beth. And the only way I would get to fuck her was, if I was good at pleasing her.

The next time Anna and Beth met, Anna told Beth she had a surprise for her. While they were away drinking, I waited in my car in front of Beths appartment complex. When I saw them coming, I followed them to the door and got in with them, without Beth noticing. I went to the stairs, Beths flat was on the third floor. When I came there, the door was already closed. I could hear moans, so they had to be very close to the door. So I waited patiently. The moans subsided. I looked around, getting impatient. What if someone saw me? But then the door opened slowly and Anna waved me in. She had a blindfold in her hand and went to the bedroom. I slowly undressed, waited a minute then went to the bedroom door. It wasnt closed completely and I could hear Anna say:"Do you see anything? No? very good. Now let me get the second part of the surprise."
With that I entered the room, silently. There she was. Beth was laying on her bed, legs spread, pussy waiting to get licked. I went down on her while Anna watched me. She was fingering herself, I could hear her wet pussy. I stopped for a bit and Anna, holding her head near mine said "you like that?"
Beth answered "It feels a bit different than usual but I like it." So I kept going and soon Beth's pussy was super wet.
Beth:"Oh damn... when do I get to pleasure you Anna?"
I moved away slowly and Anna started stroking Beth.
A:"Soon enough... But wouldnt you love to get fucked right now? I mean, how long since you had a real dick?"
B:"Way too fucking long..."
Anna(touching Beths pussy):"If we just had a man here... would you let him fuck you? No matter what he looks like or who he is?"
B: "I would take any dick right about now..."
I put on my plain white mask. Anna pulled Beths hips to the edge of the bed, then kissed her on the mouth.
A:"Just imagine my dildo was a dick okay?"
B:"Okay..."
A:"And keep your hand where they are, otherwise you will destroy the illusion."
Beth nodded. I silently got in position, put my tip against her pussy.
A:"I will go slow..."
I pushed in the tip.
B:"That feels so... real... ughh"
I went back and forth, penetrating her deeper every time. When I was half way in Beth said
B:"Damn I wanna be fucked by a real man now." (Anna encouraged her to say more)
B:"I want my wet pussy slammed, and filled with hot cum. I want to be fucked hard and rough. uhhhgghh"
A:"You really what that?"
B:"Yessss.."
A:"Remove the blindfold then."
Beth did as she was told. She stared at me, or rather the mask.
B:"Who are you..?"
She didnt seem afraid, just surprised.
A:"Do you want to know who he is or do you wanna get fucked?"
B:"I want to get fucked."
So I started ramming her. Her tight pussy felt amazing. She moaned like a freak until Anna sat on her face. Anna faced me and pressed her hands against my chest. I couldnt take her hands because I was holding Beths legs up. I felt Beth's pussy contracting with her orgasm. We changed positions. Beth turned 180° so her head was on the edge of the bed, Anna in doggystyle position over her. Beth was eating out Anna while I was lubing up Anna's asshole and my dick. I slowly started penetrating her ass. Anna's moans were loud as never before. I fucked her ass slowly and after only 3 min or so Anna screamed, cumming so hard she gushed all over Beths face and my legs. Then she squirted again. And again. I pulled out and she collapsed next to Beth, twitching in an ongoing orgasm. I started fucking Beths head, since it was in a perfect position for that. When Anna recovered, Beth and her both got on their knees and they finished me off together. Anna was way better at head so I came in her mouth, filling it with my hot cum. She swallowed like a good girl.
B:"I wanted some of that cum as well.."
A:"Sorry sweety... maybe next time..."
B(looking up to me):"So there will be a next time?"
I nodded.

Anna and Beth would meet 2 or 3 times before my next chance with Beth. Beth was getting impatient. She wanted dick again, but only mine, since I knew how to please a girl. She wouldnt directly tell Anna that she wanted to fuck me, just say things like "I REALLY need a dick right now." And so on, but Anna made her wait (as I had suggested). So after three weeks or so, Anna told Beth:"If you want dick, tell me when you're home. Then some day, first you'll hear my voice and then see him."
B:"What does that mean?"
A:"You'll see..."

Some days later, I was at Beths appartment complex again. I rang her bell. When she answered over the coms, I held my phone to the mic and played a audio file I had from Anna. On it she said "Hey its me Anna, do you mind if I come up?"
So Beth opened the door for me and I went up. On the third floor I put on my mask. Beths door was open and I went in and shut it.
B(from another room):"Hey Anna, make yourself comfortable.."
When she didnt hear anything back she came to me. She wore panties and a crop top, no underwear. When she first saw me, she jumped.
B:"Woah there, you scared me! I thought you were Anna!... Well I guess thats what she meant when she said I'll hear her voice and then see you..."
I didnt answer and just slipped out of my shoes. She went up to me and touched the mask.
B:"You know I had hoped we could get rid of this mask..."
I shook my head.
B:"I want to see the man behind that mask... I want to know your name, your age... "
I softly pushed her away and pulled down my pants.
B:"Right to work huh? Well I got to admit... the mystery surrounding you kinda turns me on..."
She lifted one of her legs and started rubbing herself while I undressed.
When I was done she was already getting wet. I went to her, lifted her up and carried her to the bed. Now it was her turn to undress. It was done quickly and my erection was coming quickly as well.
B:"So... how is this going to work... if you dont speak... can I command you what to do?"
I thought about it for a second. Shrugged.
B:"I'll just tell you what I like and we'll go from there okay? Would you go down on me please....But wait, you cant with that mask on!"
She looked like she solved the puzzle and came forth victorious. But I went to her, softly took her hands and covered her eyes with them.
B:"You want me to cover my eyes? Arent you afraid I will cheat?"
I signaled her "you peek - I leave". She nodded.
I went down and watched her cover her eyes, moved the mask upwards and started licking her clit. I used all I learned with Anna, started fingering her after a while...
B:"Dont stop please... go on ohh ugghhguh. yeah oh... make me cum please... yeees."
Soon she came, her pussy dripping with her juice. I put the mask back on and removed her hands from her eyes. I showed her a small peace of paper which I had prepared in advance. On it: "Hard or Slow?"
B:"Can you fuck me slow, please? I'm sensitive right now..."
So we went missionary. My masked face right over hers. I just pushed in my tip.
B:"Fucking a total stranger in a mask is so fucking hot..." she kissed the masks mouth. I put my hand behind her neck and pushed the mask onto her mouth, while she made out with it. after a few seconds I had to move my head away, because I couldnt breath enough.

I pushed in inch by inch, feeling every single bit slipping in. Beth's moans got louder with every inch as well. When I was all in, I waited a few seconds before slowly pulling out again. I pushed in slowly again, a bit faster than the first time. I continued like this till I reached an acceptable speed. I started playing with her tits, but she grabbed my hands and said "go more slow here as well... please..."
So I gave her two fingers to suck on and when they were wet I used them on her tits, circling her nipples. Her second orgasm of the night came soon, her pussy contracting around my huge dick. Slowly fucking like this, I could go on forever so after an hour, Beth had had 4 orgasms total and I had none. But I didnt care, her pussy, her body, all felt great. After said hour, Beth finally got on her knees and sucked me dry. I had a huge cumshot coming, since we had been fucking for so long. Nevertheless, she swallowed it all.
B:"Holy shit I never had such a big cumshot..."
I left a few minutes after without ever saying a word.

A few weeks later, Beth was craving for cock again. I hadnt been at her appartment for all that time.

So once again I came to her, this time with a different audio file so she wouldnt expect me once again.
But when I came to her door, she was already standing in it. She smiled when she saw who her visitor was and went inside with me. We went to her bedroom right away and she laid down and spread her legs. I went down on her as soon as she had her eyes covered. Her first orgasm came just as fast as last time and when it did she immediately said "now fuck me hard. Push your dick in right away. and then fuck me hard."
I forced her into doggystyle. I forced myself into her and she squeaked. I grabbed her hips and fucked her as hard as I could. She took the pounding like a boss and when I was panting heavily under my mask we switched positions to cowgirl and she rode my dick like a champ.
B:"Grab my titties... grab em hard..."
I grabbed them and squeezed them, Beth squeaked again and came on my dick. I filled her pussy with my cum. she collapsed onto me. She then slipped off me and cuddled to my side.
B:"You know... all I really what now is to kiss you... I promise, I will keep my eyes closed..."
After thinking for a few moments I nodded. She closed her eyes and I pulled up the mask. I started kissing her lightly but soon enough we were making out really hard. We were making out so much that I god hard again. Her hand found my dick and soon she was sucking me off again. I covered my face again. After I shot my load down her throat I was getting ready to leave when Beth said:"You know whats strange? I feel like I'm falling in love with you..."

I never saw her again.

End of Part 20

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@requests
22 Jul 2023 8:25AM
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Having a Blast! I love a good cum challenge

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06 Mar 2015 4:26PM
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THE GREAT PANTY HUNT

I have a challenge for the Motherless ladies.
Shoot a short video of you masturbating in a pair of panties, then slide them off and put them in a ziplock bag. Cut off the video.

Write something on the panties or pin a note to it, and then hide them somewhere in town. Take a picture of it in it's hidden location to give them a clue.

Post the video, the picture of the panties in the hiding place, and the location for them to look.

Your prize to all if someone finds them is a video of you naked and masturbating, showering nude, or having sex, and the winner get's to keep your cum stained panties from the video.

Anybody brave enough?

And if anybody wants this to happen, keep hitting that up arrow to keep it popular.

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@requests
10 Apr 2013 5:36PM
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I'd like to issue a CHALLENGE to all of you on Motherless.
Print off this pic and use it as a cum target. Tell me they aren't begging for it!

Reply with a pic of your cum on their pretty faces here and lets see how sloppy we can get these sexy little skunks ;)

Amanda is the blonde, Carlee the brunette :)
Enjoy!

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@confessions
19 Aug 2023 8:49AM
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I love and hate way You make me feel like just a toy Your cold nature never lets me forget that. I love and hate how You constantly make me on my toes challenging me to please unique nature of Yours. Your focus makes it more tasty and more willful to suffer and choke in every way for Sadist, every bit of our nature mixing well crossing the lines in every direction where the trust builds and where i was allowed to be submissive daily trying to sense how You feel so I can be good. Not feeling less of a toy. And always loved hated the way i have to work hard to earn Your cum. Loving and hating crazy task we do giggling and contorting in them. And Your mind fuck where You get me so troubled and then lower me down making me feel like a puppet dependent just like I should be.
But it makes me mad when i think You want to ruin all, take away primal lust and playfulness and make it all meaningless and ruin efforts You did and every one You did made me step up my submissiveness more and even when not, and when every tease I would like to gift is refused killing all the fun and suffering. You give You take.
with all the emotions and living in a moment and how much it’s complicated it’s actually a simple when not ruined path one that fits because dynamic is our language. And this is not about Your sadistic closed up nature that’s a tasty thing at times.. just makes me reasonable mad when I think You want to ruin all the tasty things, Devil had fun to with how it was.. all i was begging for was not to change that and keep it light for us and not to drop me all the way, my Master isn’t like that. Either way i am not assuming things

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15 Apr 2017 5:42AM
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Part8:Once a day, keeps the doctor away.

Part1: http://motherless.com/VA8BDBBF
Part2: http://motherless.com/VDA1A9DB
Part3: http://motherless.com/VDF3D844
Part4: http://motherless.com/VF9F9A88
Part5: http://motherless.com/V8538BC7
Part6: http://motherless.com/VA86BDD4
Part7.1: http://motherless.com/V136D601
Part7.2: http://motherless.com/VF285529
Part7.3: http://motherless.com/VBB2A1F7

There was a point in time where me and Anna hadnt had sex for 5 or 6 months (even longer than when I got together with Kelsey). There were multiple reasons as to why: bad timing of illness, vacation, jobs etc. Over that time we exchanged more nudes than ever. I masturbated a lot, Anna fucked Jim a lot and masturbated as well, but still, we craved each others touch. After those 5 or 6 months we made a pact...

I cannot recall every single time we had sex (in that time), but I want to tell you about some special times.


The doorball rang. I looked at my watch. It was around 4 pm. At that time, there usually is no package delivery or mail. Anna (and also Jim) was still at work. Who else would be there? jehovas witnesses? I went to the door and was pushed back into my house immediately. I stumbled, the door closed and "someone" jumped into my arms. Only out of reflex I held her up. I looked down right into her bright smiling eyes. I put her back on the ground, Anna looked amazing in her working outfit. Dark blue blazer, dark blue skirt and white blouse. The skirt was a tight fit. Her ass looked amazing in it. Her blouse was low cut, revealing a lot of her cleavage. I knew she was professional at her job, she once told me her tactic was: get their looks first, then convince with your cunning. I do believe that works. A:"I was so horny at work, I thought about masturbating... again... and then I thought: why not finish early today and get something better..." She winked at me. I grabbed her ass "well now thats a nice surprise..." I pulled up her skirt and revealed her g-string. Me:"Thats not a lot you are wearing under that skirt, but I would prefer even less..." She grinned and got rid of the string. We went into the bedroom, she laid down on the bed and pulled up her skirt a little. She looked so freaking sexy. A:"What kind of contract do you want, Sir?" she said in her innocent voice. Me:"One that says I can fuck you every single day from now on." She giggled and said "That I can do.." and wanted to start undressing, but I stopped her and said "I want to fuck you like this..." so she turned over, presenting her ass to me. I got rid of my pants and started licking her. She was soaking within seconds. A:"Jim never does that to me.." she moaned. When I stopped, her juice was dripping out of her pussy. My dick was already rock hard, so I started fucking her pussy right away. Every pound was followed by a short moan. Her tight pussy welcomed me with warmth. I started fingering her asshole. Her moans deepened. I couldnt hold on for long so I told her "I'm going to cum..." so she turned around and sucked me off till I shot my hot load in her mouth. She collapsed on the bed. A:"I missed the taste of your cum so much..." I laid besides her. Me:"I missed the taste of your pussy as well. By the way about that contract..." she looked at me in astonishment, me: "We should really fuck every single day from now on. There was to be a way." She nodded and said:"Deal. We will have to take risks though" I nodded in agreement.
Before she left, I picked up her panties. She reached out for them but I said "ah-ah-ah! No panties for you. Not today and not tomorrow. I already have an idea for tomorrow." A:"What is it?" Me:"Can you get me a appointment with you tomorrow?" She looked scared, but I said "We have to take some risks. Can you do it?" She nodded, kissed me goodbye and went home. Later I got a text telling me to come to her office around 2 pm the next day.

Since some of her colleagues saw me before (also there was Kelsey), I wore a cap to hide my face a little and looked away whenever I could. When I got to her office, she still had another client. When he left, she came out to greet me and invite me into her office. She wore the same outfit as yesterday with a different blouse. She looked nervous. A:"We only have 30 min till my next client is up." Me:"Why are you so nervous?" Anna lifted her skirt a little and I got to see her bare pussy. A:"Because, I did what you told me, no panties. And closer out appointment came, the more I was aroused. I got close to her and felt her pussy. It was wet, her lips already swollen. I pulled up her skirt a little more and lifted her on her desk. A:" Fuck me right now, else I'm going to explode." I was happy to oblige. I dropped my pants, already half erect. A few strokes from her hand did the rest. Her legs closed around me and pulled me closer. I had a hard time getting in, because she was tighter than usual. I looked at her as if to ask her why she was so tight. A:"If I cant relax its more tight..." I forced my dick into her, accompanied by her moans. She pressed her mouth against me to muffle the moans. She moaned even harder than usual and after just 15 min of slow fucking I was ready to climax. I pulled out and she got on her knees. She sucked me dry. No drop wasted. When she got up I asked:"Did you cum?" She shook her head. A:"But its okay.." I signaled her to turn around and bend over. She did and I started licking her soaking pussy. I started using fingers as well. After some time there was a knock on the door. She came instantly. Her juice spraying on my face and even a bit on the floor. She then yelled:"Just 5 more minutes. I have a client right now." We cleaned ourselfs up in a rush and she opened the window to let the stink of sex out. The spots on the floor remained. I kissed her goodbye and left. I didnt knew the guy waiting outside, but as I left I spotted Kelsey. I'm not sure if she saw me, but she had her head turned away from me.

The next days we managed to fuck at my house, after work. The more we had sex, the longer I lasted. The next exciting fuck followed on friday. Anna and Jim planned to stay at home and watch a movie (without me, just as a couple). I was worried we would break our pact before even the first week was over, but then at 11 pm, Anna messaged me.
A: "Can you come over? Jim is going to take a shower any minute now. Hurry. Come in through the door in the garden."
I jumped to my feet and rushed to their house. From the garden I could already hear the shower. Anna awaited me, signaled me to be silent and led me to the other bathroom. It was just a guests bathroom so relatively small. She wore a tanktop and pajama shorts. She almost ripped off my pants and started sucking me, while I sat on the toilet. As soon as I was hard enough (didnt take long) she stripped naked. I got up and behind her, pressing her face against the door. As I pushed inside her, I notice how tight she was again. I fucked her so hard that the door made squeaking noises. After 20 min or so we heard the shower stop. I pulled her back a little and put my hand on her throat. J:"Anna? Where are you?" I stopped fucking her for a second, but she signaled me to continue. A:"I'm using the bathroom right now honey, I'll be right with you." As she talked with him, her pussy contracted around my dick and she came hard. I was ready as well so she got on her knees to swallow my load. I instantly blew it in her mouth. J: "Are you alright?" His voice was just outside the door. I got dressed but she stayed naked and signaled me to go behind the door. Just as I did she opened the door and said "Yes... do you like what you see?" She turned off the light in the bathroom and got out. I heard their steps leaving. I waited for 5 more min until I left the bathroom. I could hear them fucking in their bedroom, the door was half open. I sneaked to the door and peeked in. He was fucking her missionary, his face turned away from the door. She moaned but I heard that it were fake moans. She was looking at him all the time, but he was just staring at her tits. Her eyes went to the ceiling for a moment. I shifted my weight a little. Her eyes must have caught the movement and she looked directly at me for a split second. She looked at Jim in fear but he was caught up in the moment. She then kept staring at me, moaning harder and harder. Real moans this time. She even urged Jim to fuck her harder. He was still doing a bad job as far as I could tell, but Anna kept staring at me and soon she came, and Jim as well. I knew I had to leave immediately. I sneaked to the garden door as fast as I could. Jim never saw me.
Later that night Anna texted me: "That was crazy. And dangerous. But it was also the first time I came with Jim in years. So... cant complain I guess..."
Me: "Glad you liked it. Was fun for me too."

The weekend and the following week was easy again. Jim was away for that time and only returned the weekend after on saturday. I invited them over that night. Jim was so tired that he left early so again an easy fuck. But on Sunday, Anna had invited me to their house for dinner. Another challenge. But Anna had a plan. She has sleeping pills for when she's on her period. So after dinner she put one of the pills contents in his glass. He got sleepy about 30 min after drinking that. He went to bed and left me and Anna behind. Me: "Is he knocked out for good?" A: "In combination with alcohol I sleep like a rock when I take those." She started teasing me. I sat on the couched and she did a little lapdance in her light blue skin tight dress. When we were naked and ready to go, I took her hand and lead her to the bedroom. She peeked in. Jim was sleeping tight. A:"You sure about this?" I just pushed her in and she slowly walked towards the bed and laid down besides Jim. I started fucking her missionary. She clawed into my chest and arms. I then told her to turn over. Doggystyle, her head just over Jim's. While fucking her I said "kiss him" she hesitated but did as she was told. The first kiss was light, the second one longer. Then she came. And I did as well. I filled her pussy with my load. She collapsed besides Jim. I let her suck off my cum. Then I kissed her goodbye. She smiled and cuddled with Jim. I left and went my way.

We went on with this for another week until we stopped. It just took too long to make me cum in the end.


End of Part 8

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01 Mar 2022 5:27AM
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Anyone up for a challenge? Cum tribute and try to cum more than I do in this clip!

Go hard or go home.
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@requests
11 Jun 2012 7:42AM
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I'm putting out an open challenge to Dublindare or anyone who makes similar vids:

Let me first say that I like the idea of your vids, I am a perv like you! But I feel that 90% of the time it seems like a waste. The chicks most of the time don't see your cock, know they are touching it, and you don't even masturbate or cum. It just seems like a wasted opportunity, since you go as far as rubbing yourself on her, why not make her aware or at least spunk one out?

Get to it fellow pervs, the future of our great society is depending on you!

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