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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.

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Can some one ai strip this hot milf??  Work your magic please.  Need to see her titties 

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My mom sat on my lap as we posed for the camera, this went perfect with the shot of her big round ass in her mini skirt. We had some pics of her spread eagle in a g-string on the hotel bed and one of her grinding on my dick from my pov. The online ad was almost complete and I got ready to fill in the description. The description read: Mom and son looking for straight dick to give mommy her first mmf fucking! Call us for hotel room number and be prepared to sand which this petite, thicc, white, brunette, 38-year-old milf; with her 21 year old son. I was trembling and my heart raced as I entered the ad, mom was going to be a true slut after this.

The guy knocked on the door, I greeted him as we waited for my mom. Mom came out of the restroom in a robe and wasted no time stripping for us. Mom loved the attention especially when we started to grope her up and down. Mom got on her knees and undid our pants, before you knew it two dicks were at her face. Mom sucked us up with so much passion, her curly jet black hair was already smeared with saliva and old-cum. Mom ate us up sloppy and wet, she was so cock hungry, this was her biggest fantasy.

Mom got on the bed and spread her pussy out for us, we started to suck on each of her nipples and fingering her pussy and asshole. Mom got on her knees in the spit roast position with me behind her and her head buried in the strangers crotch. Mom became our fuck toy as we took turns on her ends, feeling mother's raw pussy as her mouth moaned on dick was mind blowing. Mom got fucked by her son and a stranger in a mmf threesome for about 2 hours. I will try to get her to go for about 6 hours when I take her to have a train ran on her.

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I’d like to start off by saying that this is my first attempt at writing so please bear with me.

There was nothing out of the norm about my family or childhood. My dad worked hard at the company he started and would be out of town quite often. His office was that our house and my mom did the secretarial work. This allowed her to be home with my brother, sister, and myself. As we got older she would only be home for one or two days when he was out of town and then she would go to wherever he was. And a lot of ways we were your typical upper middle class family from the Midwest.

There were some differences, though. The type of differences that go unnoticed. My mom wasn’t modest at all. There was nothing uncommon about seeing her in various states of dress. Or even completely nude. It was never anything sexual and being short and overweight, she isn’t what most would consider a milf. So seen her nude, even as a teenager, never led to hidden desires or fantasies. Then, in an instant, all of that changed.

Dad had been called out on a job the day prior. As usual, mom would stay home for a day or two so she could do the banking and such. Those are the night’s that she would either clean everything in the house or just lay in bed reading until the sun came up. Had this been any other night none of this would have occurred. There were three rooms upstairs. My bedroom, my bathroom, and a bonus room where my friends and I would hang out. This meant neither of my parents came upstairs. Ever. Needless to say, I was shocked and confused when the light in the stairway turned on. The door was open but the room was dark and I couldn’t be seen. As mom topped the stairs I noticed she was wearing a hot pink satin chemise that ended about 4 inches below her huge round ass. Something I’ve never seen her wear nor did I know she even owned it. Even though I had seen her in less, I couldn’t take my eyes off of her. I never got out of the recliner after watching a movie, so mom would have never expected me to be in the bonus room. Especially since my bedroom door was closed. Where I was sitting was completely dark but provided me with an unobstructed view of the entire well lighted hall and bathroom.

With a rapidly growing cock, I watched as she entered the bathroom and started cleaning. The way her huge tits swayed inside the smooth silky material was unlike anything I had ever seen. Her large nipples sticking out like the erasers. I couldn’t believe what I was seeing. Even more, I couldn’t believe the thoughts and the reaction my body was having. There I was, sitting in the dark, softly squeezing and rubbing my cock, trying to not make any movements or sound, having my first voyeur experience. Unbeknownst to my own mother. Pulling the shower curtain back and reaching to take down the shower head, she stretched as far as she could, rising on the tips of her toes. Providing me with the most amazing view of under bun. When I thought my cock couldn’t get any harder, my body proved me wrong. With the showerhead in hand I watched as she bent over to remove everything from the tub and turned the water on. For the first time in my life I was looking at my own mother’s pussy. Most people would say that they would be grossed out. I used to be one of the people. But after seeing her plump and smooth pussy peeking between her thick thighs, I knew all of my fantasies were about to change. I continued watching her and to shoot finish cleaning the entire bathroom. Part of me was so disappointed as she started walking down the steps. Another’s part of me was relieved because it meant I could finally give my cock some relief. As soon as the hall light was off my shorts were down and my cock was in my hand. I don’t know if I have ever had so much old-cum even to this day. I also think I set a personal record that night for fastest orgasm.

To avoid acting awkward, I left the house shortly after waking up and getting dressed. Mom called like she normally did as she was leaving town. I almost laughed out loud when she said that she wished she would have been able to see more of me before she left. I apologized and blamed it on having to help a friend move. Before she would let me get off of the phone, she made me promise that we would hang out when she got back. She had no idea how much I meant it when I said that I can’t wait to see her again. I headed home me only after hanging up the phone. My cock throbbing the entire drive there. The moment the store was shut behind me I began stripping off my clothes. Walking down the hall to my parents’ room, I knew what I was about to do was wrong. I had never snooped through my parents belongings. But I had to find that chemise. I had to find out if she had any other sexy items. It didn’t take long to find her drawer of bras and learn that those huge tits I had just became a fan of were 44DDDs. There were some sexy bras I had never seen buried in the back. But something told me that there was more than a couple bras and a chemise. I have always enjoyed seeing a woman in a pair of panties. So it goes without saying that my cock twitched the moment I opened her panty drawer. In the front were the typical mom panties I had seen her in countless of times. Pulling the drawer out further I began seeing bright colors and silky material. I knew I’d found just what I was looking for. Once again, I received another surprise.

Taking a mental picture of the everything’s location, I began to gently remove everything. After removing the first couple pair of sexy underwear is when I noticed a medium sized envelope. Leaving it in its place I continued removing her panties. When I picked up the last three pair is when I first chain laid my eyes on a dildo. It looked to be about 8 inches long, flesh colored, and covered in thick veins. Placing it on her bed beside all of her panties I removed the envelope in laid in the center of my parents’ bed. Completely naked with a hard cock I was surrounded by all of my mom’s silky and lacy under garments. Gripping the fleshy feeling fake cock, I’d twisted the bottom making it start to vibrate. Putting it to my nose I inhaled deeply to try and get my mother’s scent. I have no idea what came over me but it went directly from my nose into my mouth. I had never had any gay or bisexual thoughts. All I knew it is if I had to put a cock in my mouth in older to taste my mom, then I would have let 20 hung studs fuck my face until I had a sore throat and was covered in cum. Fucking my mouth with my mother’s dildo with one hand I opened the envelope with the other. Gently dumping the contents on the bed I couldn’t believe what I saw. At least two dozen pictures of my mom fell out of the envelope in front of me. Immediately dropping her fuck toy out of my mouth, I carefully studied every picture. Putting them all back in the in the exact order that they were, I ran to the computer room and scanned all of them. Making sure I sent them to two separate e-mail accounts and cleared the history I ran back to the room to put everything back. Knowing she wouldn’t be home for couple of days I decided to take her toy cock and a few of her sexiest panties back to my room.

I’d be lying if I said I didn’t feel guilty the moment I shot the biggest load of my life into the crotch of her slutty lace cheeky panties as I had the thick cock as deep in my throat as I could. But that feeling quickly went away when I realized that my cock was still hard 15 minutes later. After releasing a few more loads of hot cum I decided to finish looking in the rest of her drawers. I didn’t find anything out of the ordinary and was about to return to my room to spend the rest of the night looking at pictures of my mom stuffing dad’s cock in her mouth and pussy. Deciding to take a quick look in her closet I soon found her stash of magazines containing erotic stories. These weren’t your regular penthouse letters. Every one of them were incest themed. To be continued…

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The new milf in our office likes wearing cowboy boots. Maybe i should teach this cowgirl what a tight hogtie in my office feels like. After shes stripped naked ill leave her there as our own rape whore