Theres just nothing about matching with a 19yo single mother with huge milkers on tinder and having a date set up after just a few messages back and forth. The cherry on the top is when shes immediately telling you that shes gonna drop off her child at her parents house that evening so you just immediately know shes gonna spread her legs wide open for you. Definetly gonna leave condoms at home
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So my mother-in-law decided she wanted to visit us on Mother's Day. I come up with a plan and offer to drop her and the wife off at the nail salon. They're all excited, nails done, hair done, I get an hour and a half to go find something to do. That something turned out to be a strip club where 2 25 year old Latinas pampered me. I thought about dances from one, then I thought about dances from the other. I asked if they did a doubles and they did. I have a weakness for Latina's, and they both had huge racks, so there ya go I'm doing a doubles.
They take me in back, clothes come off, fun was had by all. LOTS of oral. Never had 2 women sucking on me before which was fucking awesome. They completely drained the life out of me. I've never blown a load that hard before (wrapped so I'm good). Pounded both because it was offered, had a 2nd pop in the other one's mouth (again wrapped). In and out in an hour. I hit up a local store for a soda and head back to the hair/nail place.
Wife looks stunning (she's a pale redhead), mother in law is all smiles. We do a late lunch, I'm 100% relaxed. Mother-in-Law is dropped off at home. I'm so relaxed I ask the wife about movie and dinner (reversed it since we just had a late lunch). She picks the movie, some rom/com thing in empty theater. I spend the first 20 minutes fingering her past a couple O's... just because. She's now horny as fuck. We tease back and forth rest of the movie. In the parking lot she tries to suck me off like a woman half her age. It's fun, I enjoyed it, but the strippers left me empty and she doesn't know that. I eventually finger her to another O, my cock still in her mouth, and claim victory with that and we go to dinner.
Nice dinner, lots of candle light and some teasing (we were in a booth). Took her out dancing after just because. She came home with new nails, new hair, freshly fucked face and a smile ear to ear. I came home totally relaxed. More fun in the bedroom, multiple positions. When I get her doggy I've got the oil out and I thought "why not?" I started gentle with a finger. She wasn't sure at first. It's been years since I tried... but she was willing and relaxed and yeah I ass fucked her hard. Balls deep in her tight ass.
That's what it took. The woman has no clue. Her and her mom got their hair and nails done. I got sucked off by 2 amazing latinas with beautiful long nails. They drained my balls twice. I was so empty my wife couldn't even suck me off as a thank you and now here I am balls deep in her ass.... it was a fucking explosion. I saw stars as my head rushed and whatever was left pumped out of me and down her crack. Talk about "Happy Mother's Day" good thing I'm fixed so who cares if it drips in her pussy or not.
I lost my virginity in college. Prior to that, I only had messed around with two women, but didn't have actual sex with. First one was my first gf - I got a few hand jobs, and a single, awkward bj, before we broke up.
Now, the second one was something different.
It was the summer before college, and I was spending it at my grand parents house. They lived in a small house, on the Mediterranean, and I would always spend my summers there. Now, this might sound like a confession of a super rich man, to a non European, but my mom originated from this little place, and my grand parents lived there all of their lives. So, not being rich, every summer, I would do kind of a house and yard work, on neighboring houses that are usually rented weekly, you know the drill.
In one of the small, stone houses, there was a woman, with her husband, but he traveled back and forth to the city, being there mostly on the weekends, and she stayed almost all through July and August.
Now, when you are 19, you imagine a 50 year old woman, as this old, wrinkled up granny. No, she was all the opposite of that, slim, petite, beautiful blonde, and she was so obviously a big city woman, you could see it, by the way she dressed, acted, her accent, and peculiar choice of wine she would drink, all day, every day. I thought about her a lot, since, she would sunbathe topless, when I am around, not caring about my gazes. I remember finding that strange, but on the second thought, she was sunbathing on this stone patio, that got out straight to the sea, so people swimming or passing by in their boats, could see her as well. Her tits were very small, but still firm, and I thought about them, as soon as I would go home, and was by myself.
She was giving me attention, only I would think that I was imagining it. She would suddenly have something to do in the house, while I was cleaning, sometimes in a dress, usually just in a bikini bottom. Now, in retrospect, I was a perfect target for a summer fling, I was young, I looked good, from all the work I put on, tanned from exposure to the sun.
I kissed her one afternoon, when she had to go into the cupboard, at the time I was in it, and it was obvious she just wanted to initiate something. We were in the bed, and when I got down on her (only sexual thing I did before and felt comfortable doing, wanting to show that I am not some schmuck, but a seasoned lover), I saw that she had nothing under her dress. Her pussy was bald and perfect, and she came really, really fast.
As I took my shorts down, ready for more, I guess she came to her senses, and asked me to stop. She said she is sorry, but that I have to go.
You can imagine the blue balls I had that day.
Tomorrow, she acted if nothing has ever happened.
The day after, her husband came back.
And that was it. I thought about that woman, for solid five years, at first, every night, then once a week, than monthly. This morning, I remembered her again, and decided to write this.
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