Heres my confession....
Ive always had this thing for anal sex...Freudian psychology and his bullshit may play a roll but I was never touched or done wrong as a child, anyway...

The first time I had anal sex was with a girl in College...she really didnt like giving head but she loved sex..so one night in a drunkin talk I told her I wanted to stick her in the ass, she would be my first...she replied "its been a long time!" lol yeah right bitch you in college fucking everybody lolol... She agreed and I grabbed some "baby oil" lol...I was still using comdoms at the time so I gently proceeded to put myself inside of her...she moaned low and deep until it was all the way in :-) I started to stoke her gently as she told me to not go to fast. Soon after about 5 mins her asshole was open enough to pound!!! I absolutely loved it!!! Of course I came and that was it :-):-):-)

Alight so the next time we linked I told her I wanted to do it again she agreed but this time half way thru the anal session the condom broke. I felt it immediately but I couldn't stop myself...I kept going and it felt so so so so so so good. And actually before this point in my sexual history I had never raw sex..only protected so this sensation was very new :-):-):-):-):-):-):-)

Okay now here is my true confession....A few years later, I had sex with a chick and she was used to anal sex. I trusted her so I proceeded in her raw...about 15min later I looked down at my dick and it was becoming brown...at first I wanted to stop because I started to smell the odor but then I found myself not able to control myself...I LOVE DIRTY ANAL SEX!!!! ITS JUST SOO RAW and NASTY. I LUV I LUV I LUV....I begin to fuck her harder and harder harder and busted a big ass nut in her ass. She then bent over and pushed it all out...I almost fainted from excitment!

My Confession!!!

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.”

I am a 32 year old male, married for 5 years. My wife is a solid 9, blonde, slim and beautifull. I had my share of girls before I got married, and I never had trouble finding one, but since I got married, I never cheated on my wife.

Instead, I got hooked on porn, and ML, and that got me through those years, because my libido is very high. I cant bitch about my wife, sexually, she is ok, never did anal, but I am no big fan of anal, so it just got boring.

But, as it usually gets, I got attracted by this woman I frequently see in the gym. She is my age, blonde, slim (you notice the patern), with a wonderfull, round ass. For months, I was obssesing with her. I used to spend my entire training gawking at her ass in yoga pants, and wanking after the training, while thinking about her. I started asking questions, found out she is married, a milf, and that even got me fired up more and more.

At this point, I started flirting with her. Hottie like her is used to get hit on, but on the other hand, I am not that bad of a material, and as I said, girls used to like me, so, rusty as I am, I started making my move.

She was flattered, but obviously reluctant to do anything more than casual flirt, so I backed off for a while, but after that, I noticed, that she started seeking my attention, right after my withdrawal. I got her out for coffee, and she pretended that she sees a friend in me, and got thankfull, because in me, she got someone who can listen to her. She told me about her problems in marriage, mediocre husband, no closeness between them. I started making up stories about non existant problems in my marriage, so, one thing led to another, and we got close.

At this point, I was in this for more than 4 months, and I started feeling sick of myself, both because of this girl, and my wife, so I just wanted to back off, but, last week, she asked me out to dinner, so I said yes.

Entire night, she was tensed, we almost didnt talk, and I told her, that I feel bad because of our friendship, that I feel like I am getting more from her emotionally, than I should, if I am faithfull to my wife, so, it got awkward, and we ended it early, and I offered myself to ride her home.

On the way home, she asked me to park in a lot besides the road, so I did. She started kissing me, and grabbed my cock through my pants. That was it, ten seconds later, she was sucking my cock and moaning. I told her I wanna fuck her, but she just kept on going, and pushed her head between my legs, and started sucking my balls. And that was it, I blasted all over her hair, and almost got blacked out, because of all that sexual energy I was collecting for months.

I drove her home, and we didnt say anything to each other.

Yesterday I was back in the gym. She cancelled her membership.

I guess her hubby isnt that bad after all.

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!

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

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

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

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

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

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

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

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

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

I'm really confused right now because I don't think I can fulfill my sexual fantasy... I've been in a relationship with my bf for 2 years now, and I think he will ask me to marry him soon.
I'm kind of a freak and I admit I'm a slut, or a slut wanna be.. I'm in a sorority and seeing all the girls go out and come back in the morning in a mess really turn me on, but I can't. I don't want to cheat on my bf.
My biggest fantasy is to have sex with a big fat biker guy, just some dirty dirty sex. My bf can't grow facial hair so it's hard to play it out with him, and he'd think I'm a freak if I tell him my fantasy. I just find it out hot to get picked up by one of those scary fat biker guy and taken to a motel or his trailer and get fucked in all holes... I haven't done anal but I would be willing to do it.
I'm pretty small and the idea of a big scary man overcome me and fuck me turn me on so much.. Im wet just writing about it.
Any guys out there fit this type? Any idea how I can make it come true?

I had this girl in hs, my first ever. She wasnt a beauty, but was cute, had big tits, and at that time, we had the most amazing sex I could imagine. Of course, after gaining some experience, I realized sex was shit, since we both were virgins, but it worked for us back then.

More than 20 years have passed, and we kept in touch through social media. She was married (I never was), and when I saw that she is alone now (she wasnt announcing it, I just figured by her online behavior), I started messaging her (a few months after I realized it), and we eventually met, like old friends.

It didnt take long to get back where we left off. I started cumming in her right away, she didnt object. I will marry this woman, just like that, after years of solitude. And the sex...

Oh man, I never knew a woman can be so experienced, yet so eager to please. She even proposed anal (I have never done it before), and we perform it once or twice a month.

I am in heaven.

So, chin up boys, good days might be just around the corner.

I am a 50 yo guy in massachusetts. I have a 7 inch cock and I am looking for younger girls to have sex with. I have been married for over twenty years and we have great sex but I need a younger girl to fulfill my sexual appetite. Love brunettes and redheads and into anal and oral big time. I will definetely mqke it worth your while!

I confess my wife went away for 4 days and I didn't do nothing. So pissed I missed out, I've been looking forward to her going away for 2 months to get some strange pussy and ass decorating my dick but just couldn't make it happen.

Some back ground my wifes hot, a good lay but she lacks tits (deflated A cups), skinny, only does anal 1/10 times when really pressured, absolutely hates to be submissive in any way (even really mild stuff, ass slap etc). Sometimes I just wanted a chubbier girl with god dam big dangly jugs, to pound her shitter and fuck her face with no drama.

Wife picked the most shitty busy dates to go on, I only got Friday 9 till 5 alone no kids and a few hours here and there the other days that where jam packed. Had she had left 2 days later I'd of had the whole weekened to myself and a few days after to clean up. Bonus one of the kids had a cold which I got it too.

I realise there wasn't going to be enough time to find a hooker I liked, that did the things I wanted and still have enough time to cover my tracks. On top of that felt kind blah with the cold. I'd need at least a day or two to look around find any hairs, lube stains, fuck stains to clean and dry out, condom wrappers, glasses etc that are easily over looked.

Last time I had one by the time I'd changed the sheets, tidy up etc found a girl that was free and returned my call took 5hours (most hookers don't start till noon). I had to settle on the looks, she lacked the big tits, but she did the things I wanted. She was a good fuck, for 4 hours took everything including 2 rounds of painal like a champ didn't even complain/sulk. However even with 2 days to clean up there were still clues left.

I washed the sheets that were on the bed wife noticed - what I should of done is take those sheets off left them in laundry basket for the wife to check, put fresh ones on for the hooker and washed those then the wife would of though I'd just put on fresh sheets. I also had to wash towels, glasses all took much longer than imagined the next day.

I gave the hooker a lift back and she left her phone case in the car (a cloth bag). Didn't notice till I got in the car with the wife and saw in on the seat. lucky it was back and the wife never noticed.

The other time I went to the girls place and it stank of cigarettes. Which meant I stank of them and then the fucking car did. Had to air out everything for 2days.

So today I stalked someone for sex. I know how that sounds, but read on.

I was sitting on the bus back to my place from uni, I don't have a license you see, plus there's always a few chicks you can check out as you ride. Now we stop at a shopping centre and a few folks get on, and one of them caught my eye. She wasn't pretty by any means, she was middle aged, wearing clothes for a woman about half her age, with some reddish dye streaked through her frazzled blonde hair. She looked sort of haggard. The best way I could think of to describe it would be someone who used to be addicted to crack and has recovered, but the damage is slow in reversing. Anyway, she got on the bus and cracked open a can of bourbon and coke when she sat down near me.

Now I'm no great looker, my features are average but given my shaved head and my goatee and my rather large build, I look like a biker. Still I don't have too much trouble getting girls, some of them like that dangerous look. But anyway, it'd been a while since I'd gotten laid, and with this haggard lady, no wedding ring, drinking bourbon at 2 in the afternoon? I figured I knew where she would be heading once she got off the bus, and I could practically smell the opportunity to get some pussy.

For some reason, I don't know why, but I decided that I wanted this used up woman. Something about her, maybe the hint of good looks that she'd obviously had in the past but lost, drew me in.

So I sat on the bus and stared, the bus stopped in an area I know pretty well and she hopped off, I jumped off and followed her, forgoing the trip home. As I suspected, she made her was to a bar. I followed her in and ordered a beer and watched as she proceeded to get steadily more wasted as the afternoon dragged on.

I made my move around 5ish and offered to buy her a drink. She was flattered, some young guy paying attention to her? Which shows how shit faced she was, since I look hella intimidating even if I am in my twenties.

We get to talking, by which I mean she talks and rants at me while I pour more booze into her and listen. She tells me her name is Lyn, and she's obviously into me since she finds almost any excuse to touch me, so I lean and whisper into her ear, "I'm going to take you home and fuck you till you can't stand." Not the best line obviously, it's a gamble whether it works or not, I find chicks who are really desperate for it will go for it, and tonight luck was on my side. We leave the bar, although I buy a bottle of some whiskey for the road, and we begin walking back to her place. She lives nearby, but it takes a good twenty minutes to walk there since she's stumbling all over the place, while I continued drinking and making her drink.

We get to her house and Lyn tells me to be quiet because her kids are probably asleep. I'm not a parent, but if she has kids that go to sleep at 8pm then they must be the wussiest bunch of brats to ever walk the earth.

We creep into her room, or rather I creep, Lyn clomps, and fall onto the bed. I become like an animal, I tear off her jacket and shirt and start sucking and biting her nipples while she tells me to stop and close the door, but I don't care. I pull down her skirt and leggins and her pussy is hairy as fuck. If I wasn't so damn horny I would've walked away right then, but I don't care. I bury my mouth into and go to down on her.

She lies there moaning like crazy and keeps trying to shove my head away while telling me to close the door, finally I stand up and position her so that she can't see the door, while I can, she asks if it's closed, and I say yes. Then I unzip and pull of my pants, I'm hard as a rock and ready to go. She stares up at me all bleary eyed and asks if I have a condom, which I don't. I tell her its on and shove in. She gasps and stops asking me stupid questions and focuses on trying to thrust up at me.

I begin thrusting, hard. I'm strong, really strong. So the bed starts squeaking and making noise while I ram away in her and she starts moaning and telling me to stop being so rough but I don't care at this point. I'm so horny that I've gone mad. I keep thrusting away, shaking the bed when I hear something. I look up and in the doorway are her kids. She had a daughter about who looked about twelvish and a son who was younger. They stood there watching as this stranger was screwing their mother. It made me even hornier. I bent down, keeping my eyes on the kids and start biting their mum's nipples and sucking on her tits. They just stare at me going to town on their mother, before finally I can feel my balls a ragin'. I'd thought I was banging her hard before, but for the last two minutes I begin slamming into her so hard the bed moves around the floor, she begins crying out as she orgasms and a few moments after she finishes, I cum inside her. The kids are still standing there and even though I just came, I'm still hard as shit, still in case she sees, I stand up and walk over to the door, my cock clearly visible, the daughter couldn't take her eyes off me while the son just looked away. I smiled down at the daughter and batted my wet, slimy cock against her cheek and over her lips before closing the door. That was pretty weird for me, not into the sort of shit personally. She was very cute though.

Then I returned to the bed and grabbed Lyn and flipped her over, I pull her ass up and shove my dick in her again. I start banging her away why she starts moaning into the bed. Or maybe she's crying, it was hard to tell. I just keep fucking her. I take forever to finish this time around, it begins to make my cock hurt with how long it takes for me to come, finally I do and her butt collapses onto the bed as soon as I let go of her waist. She lies there, breathing heavily like shes run a marathon, I'm not in much better shape, but I haven't finished yet. I start jerking off trying to get hard again, but its not easy. I think about what I did to her daughter and suddenly I start to harden, once again I found that odd since I generally go for women my own age.

I walk up to my cock sleeve, who's still lying there like she's dying. I pull her ass up again and this time, I spit on her ass crack. I grab my dick and rub the spit up and down her butt. I spit two more times before my mouth feels a little too dry for more, all the while rubbing the spit against her hole. I'm not big on anal without a condom, it can lead to urinary tact infections and all sorts of shit. But tonight, I just don't care. I grab my dick and begin pushing in. She's tight. Really tight. Maybe even an anal virgin, but probably not. She begins squealing, or at least as best she can, before finally I'm in and she gives this little scream of pain before just shutting up and taking it. I begin sawing in and out of her, she's so tight it feels like the blood can't get to my dick, it actually sort of hurts, which was rough as my dick was pretty tender by that point.

Still I don't stop. I keep fucking, trying to bust a nut in this lady's ass. She starts moaning again, which makes me even hornier. I keep fucking away and she begins to grind her ass against me, the slut likes it! The first fuck had probably taken ten minutes, the second one maybe forty. The third one, I have no clue. It feels like it took hours though. I was screwing her for so long, I lost count of her orgasms after three, and still I couldn't finish. I reached around and began playing with her slightly saggy tits. About C-cups, there was enough of them for some fun. I begin pinching her nipples and tugging on them really hard while I whisper in her ear what a dirty bitch she was. How she'd probably fuck her son just to get off, and she begins crying that no, she's not like that, and I tell her of course she is, she's a filthy whore.

And still I couldn't get off. My dick hurts not, my abs ache and my back feels like I've slipped a disc. I still fuck her, but it's not nearly as fast or as hard as the earlier ones. I spit on her, I degrade her as much as possible without going into scat or pissing on her, because that shit grosses me out. Finally I wrap my hands around her neck (which wasn't easy from behind with her face down on the bed, but my hands are just big enough to make it work) and choke her a little, which makes her tighten up even more, but for some reason it gets me going a little bit. I start choking her in earnest and she starts fighting back against me, I start fucking harder, the pain in my muscles burns and my dick feels like its going to drop off, but still I fuck. I plow her and scream obscenities in her ear while choking the shit out of her and finally I cum.

I blow my load deep in her ass, and I have no idea why but it was far larger than the previous two I'd left in her pussy. It was possibly the most incredible ejaculation of my life, and it was with this used up broad whose pussy was covered in hair, and a disgusting ass and slightly saggy tits.

I pull out, and my dicks got a bit of brown on it, luckily she has a small en suite which I use to clean myself off, when I come back out she's lying there face down on the bed, not even moving beyond panting like a bitch in heat. I spit on her again and put my pants back on. I was done here. I open the door, her kids are still there, although the son had fallen asleep. The girl gave me a frightened look and I just smiled back. Then I left their home, went back to the bar, called up a mate and got a lift home.

And that's my story, anyone else ever done something like this? As in gone home with some middle aged chick who's past her hotness date and just fucked the shit out of her?

I shall title this confession post:

When Your Hooker Has A Surprise For You (And It's Not a Penis)

I have made a post or two about a blonde MILF hooker (escort, technically) I've been seeing on occasion by the name of Savannah.

The last confession about her that I posted was after going to a strip club. I was drunk, horny and had her roleplay as a stripper that takes me into the vip. That night we sucked, we fucked and in the heat of the roleplay when I wanted to fill her up... she sank into her roll and told me that she wasn't on birth control and that if I wanted to cum in her I would have to fuck her in her ass (she's actually fixed).

She ended up riding me reverse cowgirl with my dick buried deep in her ass. I took in every moment, slowly climbing to a huge orgasm, filling her shitter with my seed. I didn't think I could cum as much as I did. I will never forget the feeling as I erupted deep in her, I wish I could properly describe it.

Tonight was my 8th time going to see her (I believe). I wanted to cum in her ass again, so I told her I wanted that same roleplay.

After seeing her many times I've come to accept that she is always "running late". She leaves me sitting in the driveway while she is preparing for our time. She actually cares about what I want and I have no problem waiting for her to put on outfits, makeup... whatever. I've come to expect the wait.

Same thing this time, no surprise. As per usual she told me that she was getting ready and it was worth the wait.

Then she tells me that she was ready and I went to her door.

I walk in to find her and another, younger hooker dressed up like strippers with a chair in her living room for me to sit in. I'm in shock as I realize that she was setting me up with this girl as well. I didn't bring enough to pay both, but then I gathered that they expecting nothing additional in return. I was in awe of this young, skinny, sexy brunette who keeps starring at me up and down. She seems excited, but I was the one in heaven.

They gave me a hot double lapdance and made out with each other. The young hooker started kissing on me. As things heated up Savannah, taking to her character, says we need to go in vip if we want to keep the fun going because they will get in trouble on the floor. Before long they both have me by a hand and are dragging me into the vip (bedroom). They undress me before Savannah gets down and sucks my cock while the younger girl made out with me and rubbed my balls. After while she joined Savannah and they took turns sucking me taking little breaks to make out.

I laid down on the bed and my [new] favorite hooker jumped straight to sucking me off. She gave a much better blowjob than Savannah. A lot more tasteful use of suction and tongue.

As she did so, Savannah played with and nibbled on my nipples before looking me in the eye and told me that I need to pick one of them to fuck from behind.

I thought about it and had to clarify... pick one to fuck "first". I was correct, they both wanted to fuck. I was getting ready to fuck Savannah when she stops me me. "One thing different this time..." she reached for a condom and told me we were going to be using rubbers.

Savannah and I had not used a condom since our second time together. By the third meet I was exploding deep in any hole I wanted... down her throat, in her pussy, and in her ass. I wasn't excited about using one but I agreed.

Two naked whores in front of you, you don't complain.

The brunette put the condom on with her mouth and I was staring down Savannah who knew I wanted her. Before I could fuck Savannah the younger one was already telling me that she wanted to go first. She hadn't got the vibe that I was ready to fuck savannah first, but I liked that she was eager to fuck me. I looked at savannah as the brunette took position bent over with her ass in the air, face in Savannah's pussy. She liked to keep her legs together for doggy style, so I slid between her skinny thighs and started fucking her pussy from behind.

It was a beautiful sight, as I'm sure you're imagining right now.

But the rubber was having negative consequences. After a little while I was having a bit of difficulty staying fully erect due to not being able to feel her pussy around my cock. Savannah knows this is not normal and she looks up at me saying "your dick just doesn't like condoms, does it?".

No, no it doesn't.

Savannah tells me that I can take it off and she would fuck me. Apparently the condoms were just for the younger girl.

I get ready to pull it off when I hear the younger one talking to Savannah saying that it was okay and that she wanted to take it too. I could see Savannah giving her a serious look as she says "are you sure...? I guess if you want to, you're the one who knows your cycle." I hear this and before I even have confirmed that was fucking her raw also I had the rubber off, was at full erection and positioning to fuck her, completely ready and go.

This sexy skinny brunette with a beautiful tight ass looks back at me as I line up to enter her bareback. With the look of approval, I slide in and feel everything. She was way tighter than Savannah and I truly loved the way her pussy gripped my hard cock as it began to get more and more wet.

After while I had her pushed down flat on her stomach as I pounded away, making her squirm under me as she came. Her pussy overflowed , contracting in all different ways. I pushed myself to the edge a few times. I began pulling out to where just my head rested inside of her opening, in order to control my orgasm.

There were definitely a few times that cum was leaking out of my overe-stimulated dick into her pussy. After pulling out to my head a few times I remark at how badly her pussy makes me want to cum. Savannah tells me to make sure that I don't and tells me to save it for her.

She obviously didn't want her younger hooker friend to get knocked up.

I fucked her for another 5 or 10 minutes before telling Savannah that I wanted her to ride my dick.

I slid out from behind her young friend who was panting, covered in sweat (both her own and sweat i was dripping down onto her) and laid down on the bed. Savannah took position and slid onto me. I began thrusting upwards, pulling her down as I pounded up into her. I made her squirt on me and her friend remarks at how hot this was to watch. I fucked her into three squinting orgasms, completely soaking me. Her friend assumed position at some point during this to lick my balls. Next thing I know I feel my orgasm building... I smack her ass as I grow closer and closer, finally throwing my arms around her back, digging my nails in and flood her pussy with my jizz. I lay there with my pulsating dick buried in her as her friend cleans the leaking mess, remarking at how she was content and that was "the biggest dick she had all day". It being just before midnight, this gave me a nice boost. After 5 minutes or so Savannah climbs off.

We began to talk as I tried to get dressed. It turns out that she asked her friend to join us for two reasons: she loved my dick and told her friend how much she appreciated me for being cool, and having a dick that was "something special". I first heard those words come out of her mouth the first time we met and I made her cum over and over, nearly to the point of her passing out. Also, it wasn't a good day for her when it came to anal and she thought this might make up for it.

It did.

Savannah mentioned one thing that caught me off guard but really turned me on.

The first time we fucked bareback I tried to get her roleplay mom/son with me. She wasn't comfortable with it, but agreed to stepmom/stepson. After we got together for it, I didn't think she was that into it... but on this night she mentioned how much it turned her on and that she didn't expect it to.

I think it might be worth trying to convince her to do mom/son. Maybe mom/son/daughter, if that sexy young thing can get kinky with us.

What I do know is that I will at least definitely be filling my stepmom's ass with a nice big load very soon here. I really want to see if I can push her boundaries even more and go full mom/son.