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.

Gotta love the skinny, tiny-titted MILF! Am I the only one who gets off on them?

take skinny milf for a ride?

Snapped this pic after a good fuck session with this divorced Milf. Very skinny thing flat chest little waist but check out the plump white butt. She told me her ex was into couples swapping and every guy would worship her ass and beg for it.

Skinny milf Nicole

Reluctantly, I have decided to share my mother on this site! What you think? Milf isn't she? In return I'd love a fake so I can visualise her nude, she keeps her body in good shape but isn't too skinny if you know what I mean?
Please fake!:D.

Amatuer skinny milf is ready to fuck with any guy that wants her.

I am a swm and I wanna share some good luck I recently had. About 4 years ago I was casual ling seeing this super hot younger milf. I was in my early 30, she was in her early 20's. She was single, going through a divorce and didn't want a commitment. Sounds good to me. We would get together about once a week or so and have AMAZING sex. It was always epic. She was very submissive by nature and love taking it in the ass. She wasn't skinny but had the perfect set of DD's and the curves to match. It was great. Well after a year or so she met someone she really liked. She decided to end what we had. No bid deal. Fast forward 4 years. She's married to the guy now and we have remained strictly friends. So the other day I get a text from her. She wanted to ask me something. I say ask away. She wants to know if I'd be willing to get together from time to time and fuck the way we used to. She is not unhappy in her marriage but she would like to have the kind of sex we used to have from time to time. Of course I said I'd be a fool to turn that down and that I understand we need to keep it discreet. So now I can't wait to fuck her again. It's been a long time and the memories are faded. But new ones and possible vids will be made.

I confess that I was "raped" but I liked it.

Last Friday nobody was going to be home for a couple of hours so I started to surf craigslist and saw one that stated he wanted a young smooth fem to face fuck. I quickly responded to the ad and began to regret it fast. Within 20 minutes there was a man at my door about 5'9' with a big belly (about 290 lbs.). He then forced me down to my knees and told me to worship his cock through his jeans. After about five minutes of rubbing my face all over his covered cock he told me to get up and get completely naked. He then began to grope me (especially) my ass and then noticed I had a pool. He then suggested we go skinny dipping which is when he started to grope more and began to stick his cock in between my ass cheeks and dry hump me. I just wanted to give him the oral sex but he then stuck the tip of his cock in my ass so i tried to swim away from him but on my way to the stairs he grabbed me from behind by the throat aand pulled me tight and began to fuck me. I whimpered but I secretly loved the pounding he was giving me. He wasn't big, about five inches but he was soon balls deep in my boy pussy. After about four minutes of rough sex he pulled his cock out of my ass and pulled and held my head down while he came in my mouth and made me swallow it all. About fifteen minutes later we were both inside (and ordered to wear my mother's thong and yoga pants (my mom is super hot milf material)). I finally stopped shaking and said "i thought you were just gonna face fuck me" to which he replied, "yeah, i called my friend up. he'll be here in a minute to fix that problem while i reintroduce my cock to your ass"

Skinny British milf to breed. Who wants in?

need serious advice about my lustful mother
We live in canada and I was brought up in a catholic religious family.
she pretends to be religious goes to church on holidays and attends religious family events
but dresses like a slut
goes dancing at older clubs with out her husband and instead with her brother who is a salsa dancer, and close family members who she was mingling with when she was younger to these older style disco clubs.
dad doesn't care/gullible/acts like he trusts her
she also hangs out with her nieces who are 30-38? single, go to clubs, and yearly come by our pool and tan looking sexy as fuck. One year I saw my mom wearing an ankle bracelet and in pictures taken by her nieces at our pool she was showing the ankle bracelet off in every pose and viewed in you can see it has a heart shape in some cube type squares that are part of the brace, I couldn't see the other squares but I was trying to find the ''q'' or a spade to see if that means she is into BBC. she was a bit thicker and had a bit more muscle that year.
I have gone through her drawers and for years known about some pretty ''non religious types of sex clothes'' if you can call it that, beautiful thongs and intricate things like pink straps for her pink lingire costume ,she has in black too, amazing red/black provocative shit that makes me wonder. She has a beautiful ass and is a total MILF at 51 she looks 25, Ive been cumming all over her stuff stealing her stuff with no idea if she knows anyways continuing listen to this I've said I've wanted to fuck you in personal arguements because I don't really have a filter towards her because I've tried to psychologically shame her for this and make her different and she has fought the whole thing and now this is what I think if she is that way truly and is not going to change maybe I'm approaching her the wrong way during these arguments because I've said I want to fuck you because of the way you dress and she takes it as I'm crazy at the time because I am not approaching her correctly?? I say vulgar things like that during arguements to get her to shut up and stuff because she nags me about alot of things. I guess I have no filter. About me; I'm her biggest son. She knows I have the biggest dick in my family. I'm 8 inch non cut. I walk around in underwear all the time whenever I masturbate and shes near the door upstairs I make sure she hears me fapping and my desk shaking I've even told her when shes asked me a few times what I was doing that I was jacking off. I pretty much treat her like shit but I think she wants to be treated with ''respect'' but at the same time to be lusted upon the way I have been Because: recently got really close with her after two - three months of being extremely respectful you can say.

so this is the question and the thing I want to know

Today she asked me if I want to go to I ?taly? with her just me and her wtf? for three weeks alone just me and her

and it is very very wierd.

she said she would pay for the entire thing and she really tried to convince me to go get my passport with her in the next few days so she could sign us up.

I do see her lusting on me but she acts like shes grossed out by my body because I'm an athlete, I workout and pretty much take alot of drugs for competitions. my other brothers are skinny. I also have different skin as them I just look completely different and she knows that I've had bad experiences with women but I've also been the only person in my family to be open to her about women. I've told her I've hurt girls with my penis and shes just like wondered and not said anything I don't know how to explain it. so she asked about that trip and I want to know if theres any way to fuck her on it. My older brother doesn't live here and my younger brother is in college.

that psychological stuff I've been talking about has been going on for about 3+ years. my dad has not cared at all. my dad is like an old man, looks older then his age white hair now and my mom is absolutely fucking beautiful.

I've said absolutely vulgar things to her like

suck my 8 inch juicy cock

I want to eat your asshole

I've seen your slutty clothes

I want to eat your pussy

do you guys think the psychological stuff has been working and now that she asked me that question its because of the constant love Ive been giving her for months, treating her very softly, talking with a very calm voice. she knows me usually as an aggressive person towards her and other people.