Tell us about the naughtiest mom

I've actually seen someone who's a trans mommy in Literotica chat, but she doesn't seem easy to talk to. Oh well, no one said you can't try multiple times.
 
In my friend group back in the day there was a girl named Hannah. Her mom was a total drunk. I remember when we would stay the night at her house she was always plastered and trying to get the guys to give her a massage. Eventually a boyfriend of one of her daughters friends Jess, ended up fucking her. The whole thing lasted awhile. I heard she sucked a couple guys dicks one night at the same time all shitfaced drunk and her and Hannah got in a huge fight about it. The woman was a hot mess express!
I've been soooo tempted to do a drunk mommy story. I find the idea very sexy.
 
Tell us about the naughtiest mom you had relations with. What made her the naughtiest?

I’ll start. Her name started with a M.

Our first time meeting each other wasn’t so much a date but us sitting down and talking which lasted two hours. As she was about to leave to get her son I had to kiss her before she left. That turned into a make out session that lasted about 2 minutes because as soon as she saw my cock she sucked that thing like her life depended on it. That blowjob was one for the record books. I don’t think I lasted 30 seconds. Probably due to me not having an orgasm for 5 days prior.

From there it was non-stop sex. And I had full access to all 3 holes. Total submissive. I would tell her to do my dishes, and as she was doing them I would get behind her, bend her over, hold her down and yank down her yoga pants and fuck her in the ass. When done I would leave her there with cum dripping out and she would whisper: Thank You.

[redacted]

She was sexually open enough that I was able to tell her my fetish for incest. Because of that she would randomly suddenly go into mom character and did it so well I actually felt like I was her son.

She gave me blowjobs whenever I wanted as well as whenever she wanted and that was very often. Sometimes several times in one day.

[redacted]

I even set her up on a gang-bang and she loved it.

She was totally into bondage and wanted to be in one of those movies inflicting pain and forced orgasms. if we knew someone that did it we would have totally set that up. [redacted]

We constantly DP with me and a dildo playing the second cock.

I didn’t meet her in the right time of my life otherwise we may have been together still.

it was some of the best sex of my life for 2 plus years.

Your turn.
 
Tell us about the naughtiest mom you had relations with. What made her the naughtiest?

I’ll start. Her name started with a M.

Our first time meeting each other wasn’t so much a date but us sitting down and talking which lasted two hours. As she was about to leave to get her son I had to kiss her before she left. That turned into a make out session that lasted about 2 minutes because as soon as she saw my cock she sucked that thing like her life depended on it. That blowjob was one for the record books. I don’t think I lasted 30 seconds. Probably due to me not having an orgasm for 5 days prior.

From there it was non-stop sex. And I had full access to all 3 holes. Total submissive. I would tell her to do my dishes, and as she was doing them I would get behind her, bend her over, hold her down and yank down her yoga pants and fuck her in the ass. When done I would leave her there with cum dripping out and she would whisper: Thank You.

[redacted]

She was sexually open enough that I was able to tell her my fetish for incest. Because of that she would randomly suddenly go into mom character and did it so well I actually felt like I was her son.

She gave me blowjobs whenever I wanted as well as whenever she wanted and that was very often. Sometimes several times in one day.

[redacted]

I even set her up on a gang-bang and she loved it.

She was totally into bondage and wanted to be in one of those movies inflicting pain and forced orgasms. if we knew someone that did it we would have totally set that up. [redacted]

We constantly DP with me and a dildo playing the second cock.

I didn’t meet her in the right time of my life otherwise we may have been together still.

it was some of the best sex of my life for 2 plus years.

Your turn.
Wow....!!! its all just WOW..... !!!!
You are hell pf a lucky guy dude.
Bh the way how old was she and how old were you when it all started ?
And are you still in contact with her ?
Whats the status now a days ?
And have you ever been into real life incest stuff ?
 
I used to meet a naughty married Mother two or three times a month.

Sex with her husband was not enough, so after attending to her kids and on the way to the office in her city she would drop off at my hotel for a fuck. Usually between 6 and 8am and sometimes after work.

We seen each other for years, purely sex, and nobody ever knew until I just told you lot 😂 maybe her husband is reading this now.
 
Tell us about the naughtiest mom you had relations with. What made her the naughtiest?

I’ll start. Her name started with a M.

Our first time meeting each other wasn’t so much a date but us sitting down and talking which lasted two hours. As she was about to leave to get her son I had to kiss her before she left. That turned into a make out session that lasted about 2 minutes because as soon as she saw my cock she sucked that thing like her life depended on it. That blowjob was one for the record books. I don’t think I lasted 30 seconds. Probably due to me not having an orgasm for 5 days prior.

From there it was non-stop sex. And I had full access to all 3 holes. Total submissive. I would tell her to do my dishes, and as she was doing them I would get behind her, bend her over, hold her down and yank down her yoga pants and fuck her in the ass. When done I would leave her there with cum dripping out and she would whisper: Thank You.

[redacted]

She was sexually open enough that I was able to tell her my fetish for incest. Because of that she would randomly suddenly go into mom character and did it so well I actually felt like I was her son.

She gave me blowjobs whenever I wanted as well as whenever she wanted and that was very often. Sometimes several times in one day.

[redacted]

I even set her up on a gang-bang and she loved it.

She was totally into bondage and wanted to be in one of those movies inflicting pain and forced orgasms. if we knew someone that did it we would have totally set that up. [redacted]

We constantly DP with me and a dildo playing the second cock.

I didn’t meet her in the right time of my life otherwise we may have been together still.

it was some of the best sex of my life for 2 plus years.

Your turn.
Well, I met a woman at a gas station and we chatted and she invited me to her house. We kissed briefly and soon she had my cock in her mouth as I stood and she sat on her couched. I heard noise in the hallway and her teenaged daughter asked her something and she kept on sucking me. I stopped and said something about waiting for daughter to go to bed and she said, :"she has watched me before" and continued sucking me until I erupted into her mouth, with daughter watching it all. I left....;
 
Well, I met a woman at a gas station and we chatted and she invited me to her house. We kissed briefly and soon she had my cock in her mouth as I stood and she sat on her couched. I heard noise in the hallway and her teenaged daughter asked her something and she kept on sucking me. I stopped and said something about waiting for daughter to go to bed and she said, :"she has watched me before" and continued sucking me until I erupted into her mouth, with daughter watching it all. I left....;
I would have dated her after that.
 
I've noticed a lot of guys love the whole mom thing, for me its the other way round and i have enough of being a mom in real life! haha rather be the one taken care of! :D
Looking at your pics it seems incredible that nobody takes care of you!
 
When I first read the topic I was thinking of fucking mom's older than me which happened in my late teens and at that time they would have been the naughtiest I had ever had but realizing any woman with a child is a mom I've had more than I can count and impossible to pick one as being the naughtiest.

Then I realize my current wife by far is the naughtiest and that is the reason we married. There is nothing she will not do to please and shock me.
Same here:)
Don't know why but I initially thought of moms that I had sexual relationships with that were older than me.
But Biguy77578's reply made me think.....and yeah, my wife is probably the naughtiest mom I know. Always willing to do whatever it takes to turn me on....and her too;)
 
When I lived in NYC I worked with a sexy Puerto Rican woman who was 35 and had 3 kids (I was 25). We had a good working relationship but one night we were all together for a work night out singing karaoke. Like 25 employees. As it got pretty late she told me I owed her a kiss. She took me into the empty room adjacent and we started fervently making out. Within 5 minutes her pants were down and I was fucking her from behind. She grabbed my cock and slid it up to her ass. As I came one of our coworkers walked in. There was no scrambling for cover. She was bent over with my cock in her ass.

That was the only time we ever did anything before or after. Made for interesting conversations at work. Great memory 🫣
 
I went to a party when I was in my 20s. There was an older woman there who seemed to be a bit "separate" as everyone else was younger. She was mid40s, "well oadded" and very chatty. She got pretty drunk so I took her back to her place and helped her into her bedroom. I was going to leave but she started getting undressed, taking off her dress and fell over wearing just her bra and panties... One thing lead to another and I banged her hard on her back and doggystyle... I came in her pussy and was just laying next to her when her daughter walked in... smiled and just said "come see me when she falls asleep". It was the only time in my life where I did a mother and daughter in the same night!
 
I wouldn't say I was the naughtiest mom, but I would take advantage of situations with my son's friends. All were out of high school and over 19. I loved to tan on our deck and would use 'flex time' to get home to sunbathe in the afternoons. I was caught topless a few times, and then it became a 'game' to see to what extent my son's friend would go to see me.
Beautiful
 
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