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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.

My 21 year old girl and I were on a rafting trip, we took a break on a secluded river bank, we got to fucking, sue rode my cock, I pounded her doggy, then she finished my off for 5 mins with a blowjob in doggy position. As she took my load in her mouth, we looked over and people were just floating by us, her ass clearly on display for them so see, my hand on her head, she saw me look and asked if someone was there, I said: No. Just then a girl on the raft yelled, Nice ass!!!, her head popped up, she drooled the cum out of her mouth,, down her chin, face, neck, all over, she looked over and was So embarrassed 😳 😔. The guy yelled did she swallow, I yelled No she saw yall and drooled it out!,  she slapped my leg. We had just drove 20 mins in a van with those people 30tr oldish an hr before.   Funny experience. This young shy girl was so red it the face!   I told her BFF later how she got caught sucking cock while cum drooled down her chin  and her face flared up again. Said it was the most Embarrassing thing to ever happen to her, we had just drove I.

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.

My sister in law caught her husband (my wife's brother) in the act. The whole family found out and she was ready to split. In-laws talked to her. My wife talked to her. Didn't matter, my brother-in-law was so fucking screwed. I figured the last thing she'd want was another guy saying something to her but my wife pleaded with me. So I called, did the whole "meet at a bar" routine. We meet up and she's what I expected, one seriously pissed off woman. She asks if I'm gonna try to talk her out of it? "No, I just wanted a blowjob." It made her do a double take. At first she wasn't sure if it was a joke so I dead panned it, poker face. Then she laughs, slightly embarrassed, slightly nervous. We down a couple beers and talk through it. She wants him but doesn't want to go back etc. Usual bullshit. He can promise but he won't change. I let her vent, no intention of stepping into that one. 2 beers in she asks about my wife. I tell her the whole family was on her side. My wife was embarrassed her little brother fucked around like that. She has another beer and I settle for a coke, have to drive her home and all. Once she's done we head to the car. I pop the passenger door and she sits but leaves her legs out. She looks up and replies "how about that blowjob?" She deadpanned this one and I'm waiting for a smile or a laugh. Instead I feel my zipper slide down. I could fight it. I could resist. But he fucked up and she wanted revenge. Right there, in the parking lot, she got it. At some point I slipped her top down. She went from sucking to getting her tits fucked, and back to sucking. Sometimes it was deep. Sometimes it was a tongue lashing. She was clearly enjoying herself. We'd parked pretty far from the door, lots of cars, so I wanted to see if I could push this. I got her up. I got her in back of the car. I got her turned around. I got her bent the fuck over the trunk. Clearly she'd enjoyed the blowjob as much as I had. Fucking her out in the open like that was just for the fun of it. As I went deeper I realized she may talk. I needed an insurance policy. So I licked a finger and started teasing her asshole. She didn't fight it so I went with it. Fingering her tight ass, fucking her from behind. I grabbed her hands and made her hold her own asscheeks open. She stood there like a stupid whore, holding her cheeks wide while I finger fucked her ass and pounded her from behind. When I slipped the finger out she cringed a bit. I think she could tell what was next. Nothing quite compares to that feeling of total dominance when you shove your cock up a woman's ass. That feeling doubles when you look down and the stupid whore is holding her own ass cheeks open. I didn't hold back. I pounded away. Between moans I hear her say her husband isn't allowed to fuck her ass. That's what I wanted to hear. I slammed her even harder and blew a huge load.

Now prior to that there was a risk of her saying she sucked me off in a bar parking lot. But what woman will admit she held her cheeks open, took it up the ass, and let me blow a load in it? I don't think she'll do doggy now. LMAO.

Fucked her. She loves doggy and blowjobs. Hot or not?

Last night I was over a good friends house. I wouldnt say he is my best friend but he is up there in people I trust. We were unashamefully watching porn when a girl was getting fucked in the ass. He started talking about how it feels better for guys and the he once read an article or interview from he believed was Asa Akira and how she wished she could be a man because she loves anal and it feel better for men. After a few drinks and talking we both said fuck it and we would try it on each other as neither of us had. So we both went and emptied out what we could that was in us. 

We flipped a coin to see who got fucked first.  I luckily won not getting fucked first, which was good because I could see how he was with it. We agreed only anal, no blowjobs or anything else. So he breaks out the coconut oil, gets doggy and I try and start. It was tight and i had to get the angle right (also my first time fucking an ass, none of my exs would let me). When I did get it in though, it felt good.  I was slow put it all in.  (Now I'm no pornstar but I have had women tell me I'm over average, and my friend while not as big was not small by any means) 

So you know sex is sex, nothing really specials, it gets easier for him,  i speed up,  go deeper etc. I shoot my load in him (the first creampie i have ever given by the way) and damn did it ever feel good.  I pull put ,he says he needs as sec. I ask him how it was and he said it was weird, not the worst, and interesting.

So it was my turn. He used the coconut oil and made his way in me.  Let me tell you guys , last night was the night that I found out I do not like a dick in my ass. Now it didn't hurt or anything bad, and he did go slow and well did speed up eventually and go harder.  But the whole time it felt like I needed to shit, which yeah isn't the best.  Now, he let me fuck his ass so I put up with it, eventually he came in me and pulled out.  So i now have a wet feeling ass due to oil and cum I'm guessing. I strait to the bathroom where I tried so shit but I only felt like I pushed out a little liquid. 

We talked after about it,  I confessed I didn't like it and he felt bad, i told him it wasn't him and made a joke that I hope he had a good time in there.  He said he didn't mind it but he still preferred to be the one doing the fucking.  Which is a take I definitely agree with. I don't think this changed our friendship but we will see I guess. 

Prior to Covid, I would often travel on the overnight ferries that run between the UK and Ireland. Most of the passengers are those with cars, people who don’t like flying, or truck drivers taking goods between Britain and Ireland.

These are large car ferries with an enormous hold underneath for trucks and smaller vehicles. On the upper decks, there’s a cinema, bar, restaurants, and a lounge. It’s a bit like an airport in a way, only they have hotel-room-like cabins for travellers to sleep in.

To while away the hours, I would use hookup apps to have sex in my cabin with various passengers. I must admit that truckers were my favourite type of hookup. All of that pent up sexual frustration from too long on the road often resulted in some intense sex. But I’m a girl of many tastes, and sometimes the ferries would provide opportunities in many forms.

Whilst swiping through a hookup app during a weeknight crossing from Liverpool to Belfast, I noticed a large number of 18 to 21-year-olds online. I would later find out that they were part of a university trip to Belfast to study The Troubles conflict.

The history of The Troubles is horrendous. So I decided to make it my mission to provide at least some of these students a happy boat sex memory or two to take home from the trip. From 22:00 until after 03:00, I spent the night hitting up the university students I was attracted to and inviting them to visit me in my cabin. As wild as students can be, they can also be sexually nervous.

A few were too nervous to take me up on my offer and whilst I would have loved two or more to take me at the same time, it wasn’t to be. Over the course of the night, I ended up sleeping with five of them.

Two were full of bravado but came within seconds as soon as I began talking dirty. As I’ve found many times in my sex life, it was the quiet and nervous types who turned into animals in bed. One, in particular, a shy-looking 19 year old from the North East of England, was a perfect example.

As I answered his polite knock on my cabin door dressed in stockings and lingerie, he choked on his greeting when he walked in. Once the door closed, his eyes were transfixed on my puffy slit that had been fucked by one of his fellow students about twenty minutes before.

After making small talk on the bed for a few minutes, we started talking about our sex lives. He claimed to have only slept with three girls and seemed to have a slight obsession with anal, what it feels like, and if girls enjoy it, etc.

We started to kiss deeply and his shaking hands explored my body. I grinned as his hand caressed my left tit that still had dried cum that one of the previous students had sprayed me with.

Pawing at his pants, I felt his girthy cock bursting out of them. Dropping to my knees, I gave him a sloppy blowjob and left his shaft dripping with spit and old-cum. Bending over, I gasped as he pushed himself into me inch by inch in the doggy style.

”Not too fast, love. Pace yourself”, I warned him. But he ignored me and began pounding into me ferociously. I genuinely thought he would cum like the other students, but his stamina was incredible. As his balls slapped on my aching clit, his anal obsession began to shine through once again.

As he fucked me, his hands gripped my ass cheeks and pulled them apart to reveal my asshole. ”You really are fascinated by anal aren’t you?” I joked. Inside, I knew this naive student wasn’t leaving this cabin without his fantasy fulfilled.

After a few minutes of intense fucking, I slid off his cock and went to my bag and pulled out a bottle of lube. The look in his eyes was like a deer in the headlights with a layer of ecstasy. He looked in disbelief that he was finally about to fuck a woman in the ass.

As I was about to lube up for this anal boat sex, I stopped in my tracks and passed him the bottle. I’ve lubed myself up countless times, I wanted this to be part of his experience. He slathered his throbbing cock in the clear jelly before I instructed him to coat his index finger with it and insert it inside me.

As the cold embrace of the lube hit my asshole, he gasped at the feeling of my sphincter gripping his finger. Feeling his naive fingers exploring my slutty hole was turning me immensely. When he was satisfied, his thick cock head soon replaced his finger.

As his cock slid into my ass, I gasped as my hole stretched to accommodate him. He’d lubed both of us perfectly and, after getting comfortable, he built up to an aggressive rhythm and began slamming into my asshole as I encouraged him.

I was in the throes of pleasure gazing out onto the Irish Sea as this anal sex session sent bolts of pleasure through my body. I demanded he not stop as I felt an orgasm building and, right on cue, I gushed down his thighs and all over the floor of the cabin.

A few seconds after, this formerly shy student let out a roar of pleasure as he came hard into my ass before pulling out with a pop and collapsing on the bed. With my ass gaping, we carried on with some more small talk, had a little kissing session and I sucked him off once again before he went on his way.

i confess i fucked my brothers wife to get back at my wife! lets start from the begining. so for a long time now my brothers partner and i would sometimes do stuff she would suck my cock, quite nicely might i add ;), she knows how to deep throat and swirl her tongue around a cock. but we only had sex once a long LONG time ago. here recently i found out my partner of 5 and half years has been lying to me about a lot of things. so the other day my brothers wife and i were sitting alone talking about what was going on and starting talking about some other stuff. about how shes sucked my cock so nicely before and how she loved when i would finger her or pull her hair or choke her. she enjoys it all. so one thing led to another and at this point i was so fucking hard because i had walked up to her and was messing with her pulling her hair choking her started kissing her playing with her nipples giving them a nice little pinch. so i told her i wanted some pics of her she said no because she was scared either my brother or my partner would find them. so i asked her to suck my cock again. and it felt soo fucking good just sitting here typign this thinking about it already makes me wanna cum again. so i kept playing with her hair pulling it and shoving my cock down her throat. i reached down and started tugging at her nipples again and went to play with her pussy, she pushed me away and said no. but i said come on lets fuck and she just looked at me for a moment and said ok. so she bent over and pulled her panties down (all she had on was a t-shirt and panties) i was in shorts and my boxers. so she was in doggy position leaning on the coffee table. i could BARELY fit my cock in side her. it took a minute to get it in but when i did i pounded her pussy hard and fast i almost came instantly but i was able to hold out for a little while but not to long, maybe 10-15 minutes. but she came almost instantly as well i could feel her pussy tense up around my cock and explode on me. so after this we hung out for a bit more (was kinda awkward now. i mean we dont look at each other in a romantic way just physical enjoyment at times..like a toy ;) ). then i went home and woke my wife up. my cock was still wet with her pussy juices on it. and i asked her for a blowjob she said yes with no hesitation and sucked my sister in laws pussy juices clean off. it was probably the best blowjob ever at that moment.

My new years resolution was to have more sex, even if it meant lowering my standards considerably. I met a few women off Tinder in 2025 but it wasn't a great year for sex for me.

Someone recommended Facebook Dating if your standards are low and, yeah, wow. They weren't wrong. I got chatting to this women and we exchanged some flirty messages. She's a single mom, 30s, teenage sons and very selective with the angles she takes selfies from! I guess that was a bit of a red flag but I persisted.

We meet in a local pub. She turned out to be a big girl and slightly unkempt. I thought about bolting at this stage but I was determined to stick to my new year's resolution. We have a few drinks, we chat, I actually have fun talking to her. The conversation isn't exactly intellectually stimulating but we share a lot of the same favourite TV shows and films. After the third drink, she asks if I fancy going back to hers as her sons are with their dad. Jackpot.

We get back to hers and start kissing as soon as we're in the front door. The place is a mess but I'm far too horny to care. We kiss and explore each other's bodies. Her body felt so soft in my hands and I was super aroused. My new years resolution was paying off. She leads me to her bedroom and the real action begins.

We get in there and she takes down my jeans and boxers with a bit of help and gives me an amazing sloppy blowjob. She showed real enthusiasm and I was loving it. After about five minutes, I was ready to shoot so decided to slow things down a bit. We kissed and then I pulled her jeans and panties down so I could return the favour.

What greeted me completely ruined my boner though. Yes, she was wet but the state of her pussy was grim in ways far beyond a bit of pussy juice. It smelt... I don't know... like stale beer? The amount of hair she had down there certainly didn't help. She was like a gorilla down there. At this point, I wanted to flee but she was a nice girl and I didn't want to hurt her feelings. I kinda hesitated for a bit, kissing her inner thighs, trying to steel myself for what was about to happen.

But eventually I caved. It would have been too awkward to make a run for it. I gave it a lick and it tasted sour - somewhere between sour milk and licking a battery. I licked and licked, pushed a finger inside and just hoped she'd cum quickly. She really got into it and was giving me lots of feedback and grabbing my hair. I was completely limp by this point and just pushed on as best I could. To be fair to her, she didn't take an eternity to orgasm and we kissed again as she came down. I eventually did get hard again, fucked her doggy style and then made my excuses to leave.

I really don't know if I made the right decision to stay though.

So my question for Motherless... have you ever pulled a girl's panties off and noped out? Or are you like me and too polite to stop?