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!!!

so i've been chatting on ml on-and-off for years. well over five, maybe up to ten. i don't know exactly.

it's addictive and liberating to be so open about my kinks and interests. i usually bury them deep inside of me unless i'm with a partner who i completely trust and know will react positively to them.

but, anyway, i've had plenty of offers to hook up for some fun on ml and i always bat them away. i decline the offers without ever giving them a serious consideration. i guess i do it because i worry about my safety and i guess because i only see ml as a bit of extra fun while wanking.

that was until about three weeks ago. i started chatting to a guy on ml who really put me at ease. we just seemed to click instantly and, even better, he was only about an hour by train from me. in the height of arousal one night, we agreed to meet. we both thought i'd chicken out but i didn't. i don't know why him but this time i went through with it.

after a quick coffee and a very awkward public chat, we went back to his place. i was so nervous. so nervous i could barely speak. he said he'd never met anyone off ml before either. his place was pretty small, a little untidy, nothing too grim though. the blinds were all down and the place stunk of aftershave.

he suggested we watch some porn to break the ice. so we sat on his sofa, with a drink and just went through his favourites on his big tv. i've never seen porn on such a large screen! i'm usually on my phone or laptop at best. i don't know how long we sat watching porn. probably an hour? maybe it was the wine, maybe it was the porn but i eventually got comfortable enough to go further.

as we watched, he got his cock out. i snuggled in a little and let him grope me while he wanked to the porn. as he watched, he went inside my clothes and then i took them off for him. i felt a little lost tbh, i didn't really know what to do but i just tried to follow his lead. eventually i felt brave enough to go even further and go on my knees in front of the sofa. i sucked and i sucked him for ages. he didn't really give much feedback but i sucked him until my jaw ached and had to slow down. he wasn't even particularly hard, which was a bit disheartening. he kind of pushed me off eventually and jerked in my face. it took some super vigorous stroking but eventually he came and dribbled a little bit of cum into my mouth.

we then just kind of cuddled on the sofa for a bit. i thought he'd want more but the body language wasn't good. so i just awkwardly pulled my knickers back up, said goodbye and left him to watch porn.

he messaged me the next day. sort of apologised, said he was in a weird mood. asked to see me again. i'm not sure tho. i know he's not a crazed axe murderer now but we didn't even kiss, let alone fuck.

sorry about the wall of text. i had to get this out of my system.

I knew about my son`s cuckold relationship thanks to acquaintances. We all belong to the BDSM community. I was having none of it. Although I had always been very dominant with him, I expected he would behave like a man with his wife, not to let her step over him like he did. That´s why I always spanked my daughter in law, to get her to know her place.The worst part was the identity of the “bull”: a SWITCH (ie, someone who can be both a dominant AND a submissive, depending on the circunstances, therefore, NOT A REAL DOMINANT) whom I have dominated several times at BDSM meetups, without sex. Imagine my frustration when I realized this poor excuse for a man, whom I have had literally kissing my feet, was topping both my son and daughter in law, pretending to be an “alpha male”. So I tried to talk him out of the picture in the next meetup. First, I tried to reason with him, to no avail. Then I used my daughter in law as a whipping girl, but this just turned him on even more. So I appealed to his submissive side just by ordering him to end that relationship, to which he said this wasn´t my business. I threatened to reveal to both of them who he really was. He didn´t respond, so I backed him against a wall, slapped him across the face and had him opening his mouth so I could spit inside. After he swallowed, I touched his boner and commented how aroused he was getting with my mistreatment, as a reminder of his true role. He looked at me a bit scared but didn´t cave in. My frustration grew even stronger when my son told me he was planning to get my daughter in law pregnant from their “bull”. I knew they wouldn´t believe me he was a switch, so I arranged a meetup with the four of us, so they could see it by their own eyes. Upon arrival, I told him I was going to spank him and ordered him to strip naked. After a moment of hesitation and looking to the three of us, he obliged. They couldn´t believe their eyes. Then I did the same to my DIL. Then I took the two of them, broken and naked, to my bedroom and told my son to wait outside. Once inside, I sat on the bed and told my DIL to sit in a chair, kiss my feet and take off my heels. While she did, I fondled her body (I´ve always had a bi streak) and taunted her about how I had “her bull” wrapped around my finger now. Then I took off my dress and underwear and told her to lie on the bed. She looked at my naked body with a mix of jealousy and fear and shook her head. She knew what was coming. For a moment I thaught about ordering the “bull” to restrain her for me, but I didn´t want any more physical contact between those two, so, instead, I said to him “Don´t intervene, and don´t masturbate, just sit there and enjoy, this is between she and me, did you get it?”. My DIL couldn´t believe when he just answered with a very submissive “Yes, Ma ´am”.Despite being younger, she is a petite woman, so it was easy for me to push her to the bed and climb over her. She tried to resist and, to her credit, gave quite a good fight, but she was no match for me. I managed to pin her wrists against the headboard, plant a kiss on her and trib her to orgasm. Then I threw her, had her lying flat on her back and sat on her face. I ordered her to lick me to orgasm, which she did. Meanwhile, I taunted her about how much she enjoyed the tribbing and how much “her bull” was enjoying the show. When I came, I told her to sat on the chair and watch how submissive was “her bull” on bed. I had him handcuffed to the bed and told him he couldn´t cum without my permission, to which he only responded “Yes, Ma ´am”. I straddled, scratched, slapped, spat, smother and had him begging to be allowed an orgasm. He obliged like the good submissive he actually is. When he cum, I had my DIL clean up the creampie from my cunt, something she did with my son as part of their cuckolding practices. When she was done, I told her to spit the cum on “her bull”`s face. She did it without hesitation and with a lot of rage. I was having the time of my life, so I told her to feel free to take out her frustration with him, just like I did. She straddled him and spent a good while slapping his face, body and balls and calling him a wimp and a fraud. As you can imagine, I encouraged her to continue. Not only she ended that fake relationship, I ended up turning him into the cuckold he actually is in the following months, having him watching me with other men while he only watched, and performing degrading acts just like he did to my son. And then I dumped him, too. These days, either he performs as a submissive or switches with other fake dominants like him. No one has taken him seriously as a dominant since that day. 

I confess I really want a younger chubby sissy male with tits as a wife to do with as I please.

* Keep feeding you to have that nice plump ass and tits.
* Train you to obey like a good wife.

I'd literally fuck you until you love me, daily. Work from home more just to cream inside your boycunt. Teach you to suck my dick like it's the best thing you've ever done and then fuck that throat until I cum deep down inside you. No, you don't get to pull my dick out of your little throat, I decide when you get to breathe. Have you hold my cock whenever I pee and then suck it clean. Mmm.. we could do so much.

It's my little secret fantasy ;)

last night after a friend fucked my pussy good went straight in one motion into my ass, God that felt good but....after he came in me he stayed as he softened and then a warm feeling started as my insides began to swell....he was peeing in my ass...as piss enema. Now I felt so hot and horny, am I weired, slut or just normal. I want it done again.

When I was 20 I got drunk at a party. Older lady was hitting on me all night(she was 44), so we went out back of the building and I give her some dong. And went back inside and had a couple more drinks with my buddy. He was not feeling good so went to crash in his car and I said I would wake him before I left. So I hung with his #girlfriend who happened to be the daughter of the mom I just humped. She wanted to leave so I said I would take her home, I just left my buddy sleeping. After we got to her house we somehow ended up naked and I did her too. I'm proud of that night. Only way it could have been better was if the mom and daughter were at the same time.

When I was 18 I ventured to the seedy section of Boston called the Combat Zone. I heard all the sordid stories of prostitutes and strippers as well as the crime and how rough it was. I was curious to what really went on down there so one night I skipped out on my friends and headed into Boston to check it out. I was 5'11 long blonde hair and weighed 135lbs. I had on jeans and a t-shirt and definitely peeked the interest of a few men as I walked down the street. I was new to sex with girls and had never had sex with a guy. I knew I wasn't gay or anything like that. I walked by a few strip bars and some adult book stores and came to one that looked interesting. I didn't see anyone in the store so I went in.

As I walked in I was stopped at the counter by the clerk who asked me for my ID. I gave him my drivers license and he laughed and said sure kid have fun. I was very young looking. I was 18 but I looked closer to 14 or 15. I walked up and down the aisles looking at the huge collection of porn magazines and sex toys. When I came to the back of the store I saw another section called Peep Booths. I asked the guy who was sitting at the desk what it was. He asked if I had ever been to a peep show before. I told him no I hadn't he said well its a bunch of booths inside where a person can go and watch some porn videos. I asked how much it was and he said $3 minimum. I gave him a $5 dollar bill and he gave me my tokens. He said go inside and find a booth and enjoy. I took my tokens and walked inside. It was so dark I could hardly see my own hand in front of me. As I walked along I felt hands grabbing my cock and ass. I kept moving not stopping. I walked up and down through this maze of booths and came to one that I thought I would try. I went inside and locked the door behind me and put a token in the machine and the video started playing. As the video played I could see in the booth and noticed a hole on one side of the booth. I looked down and saw a man in the other booth obviously jerking off. I sat up on the chair and watched my video. When the time expired I put another token in.
I then heard a knock on the door and a man said open the door please. I thought it was the man from upfront but when I unlocked the door a black guy pushed his way inside and told me to be quiet. I was very scared. He asked why I was there and I said I was just watching a video. He asked me if I sucked cock and I told him no I was straight. He laughed and said that doesn't mean anything. Lots of straight guys suck dick. I then noticed that he had his cock out. It was very big. Much bigger than my 5.5 inch cock. He told me to suck his cock. I told him I didn't want to. That's when he took out a bottle and said here sniff this it will make you feel better. I didn't know what they were. I asked and he said they were called poppers. I took a sniff and all of a sudden I felt so lightheaded like I was high. I had no control and I went to me knees. The guy then took my head and shoved his cock into my mouth. Suck it he said. I didn't know what to do my head was spinning. I began sucking his cock and I could taste his salty precum. He was holding my head shoving his black cock deep into my throat making me gag. First time my ass he said. You're a natural. I was starting to get my head straight when he stuck the bottle under my nose and told me to sniff it again. I did and it all started again. My head was spinning. I felt helpless and was doing what he told me to do. Then I heard him unlock the door. I saw out of the corner of my eye the door open and could see 2 or 3 guys standing there watching as I sucked my first cock. About 5 mins later I felt him pull my head closer and he shot his load into my mouth and told me to swallow it. I was choking and trying to swallow but it was too much. I spit some out and it landed on my shirt. He let go of my head and I sat there on the floor looking up. Then he got out and another guy got in. He took his cock out and told me to suck him. Feed him some poppers I heard a voice say and the bottle was placed at my nose for me to inhale. I knew what to do at this point and inhaled. Then opened my mouth to take this new guys cock. He was also black and very fat. I sucked his cock and he came rather quickly. Another guy came in and said he wanted my hole. I was pleading for him to not do it. But he pulled my pants down and spun me around and told me to bend over. I did and he again fed me some poppers. He said this will make it better and I felt his cock press against my virgin asshole. I wanted to scream but my head was still spinning and I felt him enter me. I couldn't believe all of this was happening to me. I felt his cock open my tight hole and slide in and out. His balls were slapping my balls as he thrust in and out. That's it baby take that dick. You like it don't you he said and I said no. Then another person held the poppers under my nose again. They were controlling me with these poppers. He fucked my ass and shot his load deep in me. When he pulled out I felt his cum run down my legs. He was then replaced by another and then another. In all I took 4 cocks up my ass and sucked off 4. They all left me there when they were done using me and I sat in the booth crying my eyes out. I was so ashamed and didn't want to leave. After about 30 mins I gathered myself up and walked out. Not making eye contact with anyone. When I got outside there were 3 or 4 guys standing outside and I walked past them. As I walked by they said good night sweet cheeks and all laughed. I felt like shit. I kept walking even when a prostitute asked me if I wanted a date. I kept that story to myself until just now. I now know this was my reason for becoming bi later in life.

When i had my first girlfrien i had her stay over once when my parents were out of town. She told her parents she was going to a friends house and she came over and we had sex for the first time.
The morning after i woke up and my girlfriend was already up. I heard her in the shower so i thought i would go join her.
I went in the bathroom and pulled the shower curtain back. she was washing her hair so i got in behind her. Her head was down and she was scrubbing away and i put my hard dick between her legs and pushed it up to her pussy from behing her. I reached around and put my hand on her tit and pulled her agaisnt me and said ready for more? She kinda laughed and bent forward and put one hamd agaiant the wall to hold herself up and the other went down between her legs and grabbed my dick. She put it agaisnt her pussy and pushed back agaisnt me until i was deep inside her. We started fucking until someone knocked. My girlfriend said say your in here so they go away. I assumedit was my sister so I stuck my head out through the shower curtain so i could hear her. I felt my dick come out of my girlfriend then felt it go in her mouth. I yelled out to my sister asking what she needed. She said my name and i said ya what. Then the door openned and she said just making sure it was you and she walked in. Only it wasnt my sister that walked in. It was my girlfriend. She started to undress and said il join you. I just stared at her in confusion for a while then thinking wtf i put my head back in the shower.
I looked down and saw my sister sucking my dick. A million different things were going through my head at this point i had no idea what to do. I stuck my head back out the curtain to talk to my girlfriend and pulled my dick away from my suster so she would stop sucking it. My girlfriend was already almost undressed. I felt my sister grab my dick again and she put it back to her pussy and started fucking me again. My girlfriend took her panties off and was about to get in. I said wait im almost done. Then i heard my sister saiy its ok you can cum in me. My girlfriend said wtf was that? And pulled back the curtain. My sister looked up at her and said wtf? And jumped up to cover herself then she looked at me and said omg what the hell are you doing? My girlfriend said i can ask you the same. Arent you his sister? I just stood there not saying anything. My sister said i need to go and ran out. My girlfriend said ya me too dont ever talk to me and she got her clothes and started getting dressed. I finally said sorry i thought she was you i just got in with her i didnt know it was my sister. My girlfriend said yea right like i believe that perv.
I got out of tue shower and said really i was trying to suprse you but it was her i didnt know until you came in just now. She just grabbed the rest of her clothes and walked out. She left my house pretty fast. I havnt heard crom her since. Its a good thing she went to a different school then me. That would have been kinda awkward lol.
Later on i found out my sister had some guy over that night too and thought i was him in the shower. And i gave her my explanation too.
Things are kinda wierd between us niw but i think in a good way. And we always joke about what happened. Also i have seen my sister naked a couple times since then. She doesnt really care what i see. The first time i saw her naked after what happened she was changing in front of me and i said you know im here right? And she just said ya its not like you havnt been with me naked before and laughed.
I think i might try to fuck her again. Iv never been attracted to my sister and it was so wierd knowing i fucked her but i have to admit she is kinda hot and i kinda like the wierdness that comes from knowing i fucked her.
I probably wont try to do anything but if the opportunity is there i will dedinitally do something.

So, we go out to dinner. Nothing too exciting, but we do pick up her birthday present, a Bluetooth mouse for her tablet. She gave me mine yesterday, a paid trip to a local gaming convention, hotel and everything included. Also, one book of my choice, since when she went to go look, the ones I wanted were sold out.

Anyway, when we get back, as soon as the door is closed she’s stripping, like a good little Slut. She then gets up on the bed on all fours, presenting her ass for her spanking. New rule implemented starting this weekend, and one she loves. So, I take care of a couple things while she’s waiting, and then get onto the bed behind her and start administering her spanking, light slaps, nothing hard, but they do come fairly fast. It takes a couple minutes before her ass is red, but it does happen. As I’m doing this, I look over and see her hairbrush nearby. I reach over and grab it and slide it into her wet cunt (you can smell it, from her excitement about being spanked) and resume my spanking. She moans like a good little Slut.

I give her a few more spankings, then reach down and start manipulating the brush in her cunt, sliding it in and out, turning it, wiggling it side to side and up and down, just driving her crazy. Soon she’s begging to cum. I let her, with her countdown starting at 15. As she’s counting down, my hands are wiggling that brush side to side, and you can see her jiggling, and hear the trouble she’s already having with numbers.  My hand needs a couple seconds break, and she rushes through as many numbers as she can. Probably wouldn’t have made it if I didn’t need a break. Seems those hours of popping a counter 3 times a second helped out. ;)

After she cums I have her roll over onto her back, leaving the brush inside. She spreads her legs for me, and I continue with fucking her cunt. I keep up the same things, eliciting a different feel due to the position change. Pretty soon she’s asking to cum again, and without hesitation I tell her to go. She has a good orgasm. As she’s coming down off of it, I slide her brush out and tell her to clean it. The little hole in the handle is filled with her goo, nice, white, and creamy. She opens her mouth and in it goes. I leave her there as I go to the toy drawer, thinking about what I want to use.

I come back and first cuff her hands, and then secure them above her head (while putting on the cuffs, some of the cold metal touches her skin, and she gives a little shiver. Delicious to watch). Next comes the blindfold. I make sure it’s in place correctly, and then go to get the rest. I put a couple more cuffs around her ankles, and then tie a couple of short ropes around the runners on the top of the bed. Next I snag her little red vibrator, turning it on and slide it into her still wet hole. She moans in satisfaction as two of her three holes are now filled. I then thread the rope through the rings on her ankle cuffs, and secure them in place, pulling her legs up and out. With both like that, her cunt is nice and exposed.

I point this out to her just as the little leather strands from her flogger find her cunt and clit. The reaction is sublime, as she tries to shy away, but with her legs as they are, she isn’t very effective. I’m using the small end, which is thinner and has more strands, and faster. She squirms as I continue the assault, the vibrator going about half speed. I continue this for a couple minutes, varying the tempo and placement of the strikes to keep her guessing.

As I ease up with the flogger I reach down and start work with that vibrator, which has her going all over again in no time, begging to cum. Tonight I’m in an obliging mood. She only has to count down from five this time. With a vibrator in her cunt and a brush in her mouth. It takes longer than normal, but she holds out until she’s allowed to cum, and then watching that back arch and that body spasm is great. I smile to myself as I catch it on video.

I toy with her feet a bit, watching her jump away from my hands as they slide along the soles, unable to go too far, being held in place by the ropes. Then, I turn her vibrator off (it shouldn’t be on for more than 15 minutes, and it’s been about that long since I broke it out) and pull it our of her, with an audible pop. Reaching up, I remove her brush, which she gladly relinquishes, leaving her mouth open, her tongue seeking for what’s coming next. The vibe goes in, and her mouth closes around it hungrily, tongue already working on licking those juices off. Not wanting to leave the brush alone, I pop it against her clit a couple times, getting a good jump from her, and then slide the handle back inside of her.

I look up and see her toybox sitting open, and notice the nipple suction cups we’ve hardly used since buying. I grab them and apply to first one nipple, and then the other, and her voice goes up an octave. The little Slut likes this. Then it’s back to fucking her with her brush, which she actively participates in, fucking it back like a bitch in heat. I pull out all the way out a couple times, and once it slaps against the coverlet, leaving a gooey mess. Guess I’ll have to wash the bedding after this. Oh well, worth it, I think. It doesn’t take long before she’s begging to cum again, this time on video, unbeknownst to her. I let her, and give her a few seconds to recover before I tell her to cum again. She spasms even harder than the previous one as the orgasm racks her body. Such an obedient little Slut. I do love her trick of being able to cum on command. For fun I have her do it a third time, and that one must have been pretty intense for her, and she writhes around on the bed, lifting her ass into the air and pulling those legs every which way. I had to make sure the ropes were holding and the knots weren’t slipping, but everything was fine. She didn’t pull the bed down around our ears, not for lack of trying though.

I ease her brush out one more time, and it goes into her mouth, her vibrator being set off to the side. She’s recovering, but I can’t just leave her there, can I? I reach down, two fingers parting her folds while a third finds her clit. She goes wild as soon as I do, and within a minute is ready for another go. She starts at 10, as told, and does have some trouble getting there. She manages, and cums, legs clasping around my hand as much as they can. It’s a nice long orgasm. Must have enjoyed that one. :)

She is spent, so it’s time to get her released. The ropes and cuffs come off, the nipple cups go back into their box, and the brush and vibe are set off to the side for cleaning (she’ll take care of that and put away the ropes when she’s recovered enough). I get her a glass of water, which she accepts, before going back and just laying there for the next five minutes, unable to really think or move. I cuddle a bit, and she rolls onto her side, molding against me.

While we lay there, I lightly stroke her side and squeeze her shoulder. She’s still horny, the little Slut. You can hear it in her moans and see it in her movements. Yes, well trained. As soon as I tell her to get a hand busy on her cunt it‘s there, working that pussy. I concentrate on her shoulder, one of her weak spots, and let my other hand idly play with her nipples as she undulates against her hand. The action on her shoulder is what really gets her going, the nipple play is just a bonus. As I increase the pressure, she is asking to cum. I let her, and it’s a nice and easy one, she’s had time to cool down.

I stroke up and down her exposed side as her hand continues it’s ministrations (she hasn’t been told she can stop yet). I then stroke lower, over her ass and then into her wet pussy from behind. She moans louder as I begin to lightly pump in and out of her, every few strokes taking time to just rub up and down on those lips of hers. It’s constant attention, though, and with her hand still going she doesn’t last long. She cums, hard, with me inside her. I do love her doing as she’s told.

Then, to end the session like it began, I slide out and land a slap to that ass. The sounds she lets out is exquisite, and I continue, the slaps becoming harder and faster, but only on the one cheek that is not covered by me. She doesn’t seem to notice that only one side is getting the attention, or doesn’t care. She’s bucking against her hand in no time. And her request for permission to cum takes her 30 seconds to say, the words won’t come to her pleasure addled brain. I love that, too. Can’t even concentrate enough to say “Sir, may I cum?” She doesn’t get to cum until she’s finished her words. It’s difficult for her, but she perseveres and lets out one final orgasm for the night, before collapsing, as I tell her she can stop.

We cuddle for a few more minutes. As I get up to leave, I lean down and kiss her ear, whispering “Happy Birthday”. I’ll take the grunt that elicits from her to mean “Very happy indeed”. After I leave, it’s another 20 minutes before she can get up and move again without falling down. She does clean her toys and tries to put away the ropes. But she can’t remember how to wrap them just yet, so I show her one, and she does the other. Brain foggy and all that.

Anyway, that’s how our night went. Hope you enjoyed. :)

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.”

Confessing to something that happened around 20 years ago. No pics, just my recollection of what transpired. There was a Gus Macker tournament about 30 minutes from my sister in laws house, which would have saved my buddy and I a 3 hour trip in the morning. Our third lived downtown near the tourney and being married and having kids didnt have the room for us to spend the night. My wife asked her sister if me and my buddy could stay at her house and she was good with that.

Sister in law was divorced at the time and not dating. This is where it got funny. I told my buddy he should hook up with my sister in law. I described her and he said he wanted to see her first. Unknown to us, my wife and her sister were talking on the phone and my wife said you might like the other guy staying with you. (My wife told me this after the tourney). I'm 6'3 my buddy is 6'4 btw. When we got to her house she made a great dinner for us and bought a bunch of beer, like more than we could drink.

After dinner we were sitting outside on her deck chilling and the 2 of them were getting to know each other and she got up to use the bathroom and I asked him what he thought of her. He told me he'd let her suck his dick, so I was figuring I'd be watching movies later while they fucked. By 10pm we had drank more beer than I realized and headed inside. She put some music on and we were drinking and talking about basketball etc.

Dont remember what song came on but my buddy was dancing around the living room and acting like an idiot. He got me to join in and we tried to get her to get up and dance but she wouldn't. A slower song came on and he finally got her to dance, they weren't close but they were on their way. I got up to take a piss and grab another beer and when I came back with 3 beers, they were making out. I walked over and was like hey hey enough of that and laughing.

I came up behind her and put my long arms around her and my buddy and I was joking around and said group hug. They just kept on kissing and I started pressing against her ass. I could see his hands squeezing her boobs outside of her sweater, so I started squeezing her ass. She didnt do anything so I tried moving my hands up to her boobs but his we're still there. When he felt my hands he moved his and I was able to get 2 handfuls of her boobs. Checked her bra later and she was a 34C.
The fact she was letting us both play around with her made me a little bolder, so I moved my hands up and under her sweater and unhooked her bra. Felt both of my sister in law boobs for the first time and couldn't believe this was happening. I started lifting her sweater and told my buddy check these out.When I got the sweater to her shoulders she put her arms up and let me lift it over her head. My buddy was looking at me like dude this is your sister in law and I looked back and nodded.

After her top was off he started sucking her boobs and I remember she had her head tilted back and I was kissing her neck. I told my buddy to switch and he got behind her and my sister in law was like I cant believe I'm doing this with you. I started sucking her boobs and I think he had his hand between her legs because she was moaning a little. He reached around and unzipped her shorts and she was like I shouldn't be doing this with both of you at the same time and then she looked at me and said especially you. He slid her shorts and panties down her legs and she stepped out and they resumed kissing. I wasnt sure how far this go but wanted to make sure at least he got something out of the deal. I was just happy I sucked her boobs and felt her ass.

I think I remember telling him to show her his cock and when he pulled his shorts down they said something to each other and she got on her knees and started sucking him. So while she was sucking him we're looking at each other and trying not to laugh. I stepped to the side of them so I could watch and jerk off and I was impressed on how much cock she could swallow. After a minute she looked over and saw me jerking off and went back to sucking, but would glance over once in awhile to check. I was trying to hold off but it was kinda hard and my buddy goes why dont you take care of him as well. She stopped sucking and wiped her mouth and said he's my brother in law and something about it getting weird. He coaxed her into just taking the head and she did but then she started taking all of me just like she did with him. We were high 5 ing and she was like dont do that so we stopped. I thought he would let me cum in her mouth but her grabbed her arm and they started walking to the bedroom.

I followed them and she said something to him and I did hear him say, just this once. In bed she started off sucking him so I licked her pussy and ass from behind. After a few minutes we switched and I laid back and let her mouth go to work. He got behind her and started fucking her and I was thinking to myself, this is the kinda shit I jerk off to. She was loving having 2 guys at the same time. She would stop sucking me for a sec and either moan or tell us she couldn't believe she was getting 2 big cocks at the same time. I wasnt sure if she would let me fuck her but she did. For the next hour we took turns letting her ride one of us while she sucked the other or spitroast her. He even let me have her a couple of minutes alone. Eventually I came in her which was a fucking rush and she swallowed his load right after.
She slept between us in her bed that night and we were so tired from messing around we slept until the alarm went off. Next morning I woke up and she was sucking him so I got behind her and started licking and fingering her asshole. We won the 30-34 age that day and went back to her house to celebrate. As a reward she let us DP her. Kinda long but had to give all the details.