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Baby Sitter

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Post videos of the babysitter doing strange or naughty things.

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1
Anonymous
@confessions
02 Sep 2013 5:57PM
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When I had my son I never put much thought into his sexuality. After I got divorce it was hard raising him alone because I worked job that had shifts and so he would be alone sometimes. He was in the upper single digits when I got divorce so it was hard on him.

Due to my job sometimes he would be home alone and that means him having friends over. I was searching for something on my computer one day and I found porn from I site I never visited. I did not know what to say so I said nothing. One day I came home to him and the kid down the hall on my computer and I could tell they were up to no good as they had a guilty look on their face. That night I went in my browser history and their is was again porn from a site that I do not visit. What struck me most was it was straight, bi and gay porn which slept me speechless.

I tried to be open and so I had the sex talk with him and told him I was ok if he was gay. He said he did not know and that he felt funny down their when he saw the videos. The kid that came by was 2 years old than him. It is hard to keep them apart as we lived in an apartment then and so sometimes I had no baby sitter and had to go to work.

He had a birthday coming up and I invited all the kids in the building for a cake, pizza and ice cream party and he had a ball. The next day he called and asked if the friend could come by and I was so guilty for having to leave him I said yes. This time I came home unexpectedly and caught them touching themselves. By this time I noticed he was always hard and he had this habit of rubbing on me. I was so surprised I ended up moving away thinking that would help.

I moved into a house and I had a guy who shared the house with me. He would sometimes let my son come by and play with his games. One day he called to let me know my son could not come by because he caught him watching porn on his tv. I was so embarrassed but thankfully not long after he moved away.

I then started dating this guy as I was single for 3 years now and it was time I had some fun. I would always go to the guys place and sometimes I would take him with me. The guy also had a son who was older and once we were having set in his room and when I came out I saw him and the guys son sucking each other in the kids room. I was so shocked I brought him home right away. When we were going home I asked about the experience and he said he liked it and want to be friends with him. I forbid him because not that I was mad at him being gay but that he was young and I felt it was my fault now a few years later he is secluded he no friends and I wonder if its my fault.

I am ok with him being gay its the age and experiment that scared me. I did experiment at a young age myself and felt that I wanted him to be innocent as long as possible not like myself now I feel I was a hypocrite. Was I wrong? I welcome all comments and suggestions.

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Anonymous
@confessions
16 Dec 2013 11:23PM
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i confess i fucked my wife in the ass for the first time tonight.

it started with her giving me head, sprawled out beside me. slapped her ass a few times and she moaned. she's a pretty conservative girl and hadn't had sex before we got married. over the years i've introduced more and more adventure into our sex life. i was quite the male slut in college.

so with my wife, after getting married and popping that cherry we started with blowjobs, then different positions, sex in public places, in the car in the garage while the baby sitter was inside (don't think i wasnt dreaming of pounding that little freshman in college while balls deep in my wife), rough doggy style, etc.

the last few times she's blown me i've run my hand down her back through her ass cheeks and down to her pussy, making sure to brush my fingers over her little balloon knot and also her taint. tonight, after slapping her ass a few times and spreading her pussy, i got my finger nice and wet and then lightly pushed it in her ass. she yelped a tiny bit but shoved my cock deeper down her throat. did it a few more times and asked if she liked it...

"its... different"
"but it doesnt feel bad?"
"no, not really."

and proceeds to keep polishing my knob. i keep fingering her and teasing her asshole. i keep playing with her clit and she is basically trying to devour my cock. the only thing that stopped me from blowing my load down her throat was getting up the nerve to say this...

"so are you going to make me cum before i put in in your ass?"

she stops looks up and says "this won't end well"
"well, in that case it will be pretty short and you can get back to blowing me." what the hell, might as well give it a shot.

i tell her to run get the ky. she comes back and i get behind her and push her down on the bed, legs still on the floor - i spread her ass cheeks and put more than a few drops on my hand and wipe it all over her asshole and up into her pussy and clit (gotta keep her horny before this seems like a bad idea). put a few drops on my cock and get ready for the plunge.

i did this one with college girlfriend but she was one of the tiniest little cheerleader girls at our school and the moment i got the head of my cock in her ass she basically started crying. i'm not huge - just average to slightly above average. so, i didn't think it'd last long for the wife...

well, got the head in and she was not enjoying it - so i reach my hand around and played with her clit and started fingering here. magic! now the fun began.

so... the confession is this - it wasn't that great. i think it's the buildup and the slightly taboo nature of it. honestly id rather her deepthroat me all day than do that again, and a pussy is at least able to contract and i can feel her tighten when she cums. that ass got fucked hard tonight and it really didn't feel any better than anything else we've done. i eventually pulled out and came on her face/tits. kissed her and told her thanks and that she doesn't have to worry about doing that again as long as the blowjobs stay regular.

some men complain about never getting a blowjob in marriage - me? i get them frequently and never been happier. now i think they'll be even more frequent if she thinks it'll get her outta ever having to offer up the ass again.

is this odd? any of you other guys prefer vag and mouth over the ass? is it one of those things that guys have to do once or multiple times just to show dominance or something? for me it was hot knowing my every movement - big or small - could make her moan in pain or pleasure. what made her scream my name the loudest was finding the right balance between pain and speed of me fucking her ass and making her feel pleasure by fingering her and teasing her clit.

no pics, sorry.

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7
Anonymous
@confessions
31 May 2016 12:24PM
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[ − ] thread [ 1 reply ]

Over the weekend the wife and I went to a bar with another married couple. I noticed a really attractive brunette that had long legs, perky tits (no bra) and a short skirt eyeing us. I thought nothing of it; maybe she knew my wife or something – didn’t care. Around 11:30pm the other couple said they had to leave because of their baby sitter having to leave at 11:30pm. I asked the wife if she wanted to have another drink, she said yes. Three more beers later I had to piss like a race horse and told the wife that I needed to use the washroom. Usually, there is no line for the men’s wash room but this time it was out the damn door so I stood in line, the urge to piss was beyond measure but I held it. I could see my wife across the bar, and the woman that was looking at us before approached my wife. So, I thought nothing of it, it’s just a co-worker or whatever. After a good 5 minutes of waiting I was able to piss, washed my hands and came out of the washroom to see both my wife and this woman chatting up a storm, laughing and getting along great!
“Hi,” I said I as I approached them.
The brunette woman gave this sexy evil grin – it is the only way I can describe it – sexy as fuck, like her lustful intent was showing right through whatever she was talking about with my wife.
“This is Maria, we used to work together,” my wife said, a little tipsy from drinking.
“Oh, we had the biggest crush on each other, but you chose him over me” Maria winked at me.
My wife looked down at the ground, embarrassed. Tears started to stream out of her eyes (she cries very easily).
“He… he doesn’t know,” my wife said her face flush.
Maria was taken aback a bit, “I - I’m sorry,” she stammered.
Confused by this transaction between this super-hot woman I asked, “Know about what?”
“I’m bisexual,” my wife said, “I like women too.”
She looked at me with sorry eyes, pleading with me – but me being the pervert that I am, looked back at her and said, “kiss her.”
“No, we’re married and I don’t want that,” my wife said shaking her head, seemingly offended.
“I want that, kiss her.” My wife didn’t have time to react as Maria stepped towards her without hesitation and bit her lip.
“I want you both to have fun,” I told them, feeling excited and nervous. I could feel the blood flowing to my cock; it was so beautiful to see this gorgeous brunette kissing my wife. Yeah, I wanted that pussy too – I was guessing it was nice and tight.
Heads were beginning to turn, and an audience was forming. I could tell my wife was really getting horny.
“Hey, you can come back to our place if you want,” I interrupted their bliss.
“um, it’s okay honey… I-“ my wife started speaking, pulling away from Maria.
“I want you to,” I said looking at my wife in the eyes.
Maria walked over to me, “I’m really not into men, but you are good for her. I’m glad she met you,” I felt her hand graze my erect cock, “seems he does want this,” she said smiling and pointing to my erection.
My wife smirked, “he can watch,” she said shyly.
I was kind of embarrassed and a little pissed off, this would have been my first threesome and she was ruining it. Yeah, I guess I was being selfish but I needed this.
We went back to our house, Maria took her car and we drove our own car. On the drive to back to our place my wife was starting to have second thoughts.
“I’m going to tell Maria no, we can’t do this because I don’t want it to ruin our marriage. I love you very much and I don’t want to lose you. I just want you all to myself and I don’t think you watching me with another woman will do that, I don’t think you can handle it.”
I reached over across the seat and felt the wetness between her legs.
“Yeah, bullshit – you’re doing this.”
Images of my wife getting fingered, licked and sucked by this gorgeous woman were racing through my mind. I couldn’t wait to get them inside, even if all I was able to do was watch.
Once we got inside, Maria and my wife were giggling – it seemed the mood was getting ruined so I had to get it back on track.
“You’re both sexy as hell.” I said.
Maria let her dress slide to the ground revealing that she didn’t have any panties on. Her pussy was shaved clean. She took her top off revealing nice “B” cups, perky small round pointy erect nipples. My wife’s tits are bigger, 38C but not as perky and bigger areolas. Maria walked over to my wife, “Let’s give him a show.”
As they made out in the living room, Maria stripped my wife’s clothes off her – fondling her breasts, grazing her pussy lightly. My wife moaned. I was so hard. They both collapsed down on the sofa, and I sat down in a chair across from them – watching. Maria was so beautiful, and I wanted to feel what she felt like but knew I couldn’t interfere or I would ruin my chances.
I was pretty buzzed and horny as all hell – while they had their fun, I unzipped my pants and slid my erection out of my pants and started to jerk off. I watched Maria work her way down to my wife’s pussy, which wasn’t shaved but had a nice racing stripe down the middle. My wife’s legs were spread and Maria knelt down, her ass arched up in the air as if it was inviting me to enter it. Maria’s ass was so soft and round, I watched her slim waist snaking back and forth – tempting me. I stroked my cock as they both moaned.
My wife shook with an intense orgasm within five minutes of Maria going down on her. I was speechless, it always took me thirty to forty-five minutes of intense licking.
“It’s my turn,” Maria said as her face glistened with my wife’s pussy juice. Maria sat on the couch, and my wife went down on her. Maria was watching me stroke my cock and licked her lips and mouthed, “Fuck me.”
I stayed in my chair as Maria’s moans erupted into an orgasm – her eyes constantly upon me.
“I missed you,” she told my wife.
My wife didn’t say anything and I kept stroking and I was almost to the point of busting a nut when Maria stood up.
“Your poor hubby, he’s so neglected.”
“He’ll get some, just not right now.”
Maria walked over to me, “you should at least give him a blow job,” she said smiling and pointing to me.
I must have looked pathetic. My wife walked over and knelt before me. She took the tip of me in her mouth, she couldn’t deep throat me but just sucked the top half.
“Looks like you need a little help with that,” Maria said as she started licking my shaft as my wife continued to suck on me. My hand reached out and I groped Maria’s soft tit. I could feel her hot breath and tongue going up and down my cock as my wife continued to suck me.
“I wish I could try that out,” she whispered to my wife.
My wife thought she was talking about sucking my dick, so she stopped and told Maria, “Okay you can.”
Maria mounted me. She spread her legs over me and I felt her hot wet cunt impale itself on my hardness. I’ve never had a woman so tight. She began to move up and down, I felt her clenching every inch of me.
“HEY!” my wife protested, but Maria took her by the hair and buried her face in her asshole. Maria’s soft tits bounced with every thrust as I looked into her beautiful brown eyes. She smile at me, kissed my lips and I could feel my wife’s tongue now licking my dripping wet nuts. I couldn’t hold off, that pussy was so perfect.
“I’m going to cum,” I panted, I felt my wife massaging my testicles with her fingers and licking them.
Maria quickened her pace and clamped down harder.
Pulses of cum shot deep inside Maria, I looked at her in shock. She was letting me cum inside her and my wife was sucking and licking up all the juices flowing out of Maria’s tight pussy.
Maria could feel my erection going down and I slid out of her. She stood up as cum ran down her leg. My wife started licking Maria’s thigh’s and my cum. I wish I would have known about my wife being a freak earlier.
“Are you on birth control,” was the first thing out of my mouth.
“Hell no, I don’t really need it – I usually fuck females,” Maria said with a smile.
Later, my wife was mad because I came inside Maria, and that I had sex with Maria – so I told my wife that she is the one that can’t handle it, and that Maria was only a fuck.
“Yeah, well what if Maria gets pregnant because of what we did.”
So I joked with her, “Well, then Maria can move in with us and I’ll have two wives.”
“I’m your wife, I don’t want to share you. It killed me when she was riding you. That’s MY cum, no one else’s I own that cum.”
I told her, “and I own that pussy, but I let you share it with another woman. Get over your jealousy. Of course you are my wife, and if something happens – it seems you like Maria too, I don’t see why we couldn’t all get along and have nice lives together. You can have as much fun as you want with her, I just wish you would have told me you were bisexual. You don’t have to hide anything from me – I’m very open minded, I love you very much.”
“If she is pregnant, she’ll ruin you, that is how she is, that is why we stopped being friends. She’s a little whore. She cheated on me with a bunch of girls, she’s no good for us – so get whatever warped fantasy out of your head you’re having right now. I wouldn’t want her living with us.”
This Maria woman, she’s super fucking hot – short brown hair, brown eyes, perfect body – yes I was thinking with my dick and I could have pushed her off of me when I came – but it felt so good. Plus, why was my wife licking my cum from her thigh? If my wife was so concerned, why didn’t she push Maria off me and put a stop to the entire thing? I think my wife secretly wants Maria to be part of our family but is afraid that she’ll lose me in the process. Fuck, I want both of them now and it is hard to imagine having sex with just only my wife. I want more threesomes; I want more of Maria satisfying my wife. You could totally tell from their vibe that they’re kind of “soul mates.” Fuck, it almost feels like we’re all soul mates – like we’ve all known each other forever and we are finally all together… weird shit.
In a weird way, I hope Maria is pregnant, and that she does move in with us – because I’d knock my wife up too lol. Am I wrong??? Or am I just being weird about all this? My wife totally could have stopped Maria from having sex with me, but she didn't.

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9
Anonymous
@confessions
16 Oct 2013 2:17PM
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I confess I'm fucking the woman who molested me as a kid.

When I was 13, my parents were both working night shifts so I required I baby sitter. It was this 20 year old university student. She was fat, but had a cute face and nice big titties.

Anyway, she used to read me stories as a kid to get me to go to sleep. Then when I'd finally nod off, she'd feel my dick, balls and sometimes finger my ass. I didn't know this at first, but I got suspicious one day when I woke up and PJ pants weren't all the way up correctly.

So I decided one day to pretend to be asleep. She said my name 4 times before reaching for my cock. Since I was aware of what was going on I got a rock solid boner. And she caught me peaking. She gasped and about to pull away, but I was close to cumming so I whispered "don't stop". She jerked me and I came. She was a bit awkward and shocked after this because she was caught and said "I wont tell if you wont".

From then on, every time she visited she'd be all over me. She gave me a rimjob/prostate massage for my 14th birthday. Man that was fucking incredible. Sometimes she'd have to come over on weekends, and she'd bring booze, pot and DVD's.

Years on, I'm now 19 years old. She's 27. We're a couple and we have fucking amazing sex. We always do roleplays of her coming in and fucking the bad little boy. We've done mommy roleplays and all sorts of shit.

I love my rapist :)

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Anonymous
@chicks
11 Jul 2023 4:02AM
• 71 views • 1 attachment
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I think the baby sitter knows why I'm a big fan of her.The wife knows too, and I think she's into it 


What would you do to lily? 

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Anonymous
@confessions
10 Aug 2018 10:20PM
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I fucked our 19 year old bbw baby sitter and filled her with my cum. It was amazing. Afterwards she asked if we can do it again and i said yes. Now on to home to fuck my wife and spread our sitters pussy juice in her pussy.

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Anonymous
@confessions
29 Apr 2012 2:45AM
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had a baby sitter tonight so the wife n i could go out. this chick is hot as fuck and has sat for us a few times. she showed up tonight in a light see through flowery skirt and loose shirt. she spent the first 5-10 minutes leaned over playing with the dog while the wife finished gettin ready. her shirt was so loose i could see right down. she has small tits and her bra fits loose, had a clear shot of nip.

we tell her we will be late and head out.

we end up coming back earlier than expected. as we come in the house, i see her at the top of the stairs. she had been watching tv in the loft outside of the kids room. as i look up, i see her skirt is pulled up on one side like the end was caught in her waistband. from the angle, i couldnt tell if she was wearing panties or not. ohh, instant boner just staring up there thinking about it.

she saw that i was looking up, realized how her skirt was and adjusted it then came down. by this time the wife was in from the kitchen with her money thanking her for sitting and apologizing for cutting the evening short.

the sitter walked out and was gone.

within a few minutes, the wife was in bed watching tv and i heard snoring. nothing for me tonight. then i remembered the couch in the loft. i lifted the blanket and found a patch of blonde pubes. they dont belong to anyone in my house. the cusion was still a little moist and i could smell sweet pussy. omg, had to rub one out right there.

we have a few things coming up so hopefuly, the wife lines her up again. now that i know she is playful, i think i may need to set up something to monitor with.

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-1
jihad2bthere
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@chicks
28 Jan 2014 4:39AM
• 746 views • 1 attachment
[ − ] thread [ 2 replies ]

That's right slut, clean up that mess because I have brought home all my Army buddies and we're going to take turns fucking you all day and night on the floor. Thankfully, we got a baby sitter, because you're going to spread your legs and fuck my whole fucking platoon of buddies. We're going to fill those nasty holes full of our cocks and our cum until it oozes all over your body and on the floor.

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Anonymous
@confessions
29 Sep 2011 3:43AM
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I confess that I miss THE THREAD...you know which thread I mean right? Dad, daughter, registered baby sitter? Where has it gone and why?

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Anonymous
@confessions
10 Nov 2011 1:26PM
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I came home from work last night and paid the baby sitter then went and checked on my daughter. she was fast asleep so I went and took a shower and got ready for bed. thats when i went over and pulled my dilo out and it was wet. i thought that was odd so i smelt it. It was not my smell so i fegered it was the girl I have baby set for me. that got me hot so I went and fucked myself crazy with it. I think tonight Im going to talk to her about it and I'm hoping I end up between her legs.

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Anonymous
@hookups
07 Nov 2012 5:07PM
• 6,104 views • 7 attachments
[ − ] thread [ 45 replies ]

Hey there. :) I'm a 19 year old girl from Texas who is very interested in having sex with an older man. I love daddy/daughter, incest, and baby-sitter scenarios. I do have very small breasts, but I am thin and attractive. If anyone in the area is interested please let me know!

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Anonymous
@confessions
27 Apr 2013 1:09PM
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My baby sitter used to play a game where I would get spanked, then sh would have me pank her. Both of us were in just panties most times. Sometimes she would take hers off and bend over my parent table and have me us a wooden spoon over and over. I see looking back she was totally rubbing her clit on the edge as I was spanking. Now I wih I could go back and play! She is still friends with my parents

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