by Jim

Gender: Male
Age: 29
Race/ethnicity: White
Current location: Los Angeles
Highest education received: Some college (currently in college)
Relationship status: Long distance girlfriend
Religious affiliation: Atheist
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 13 or so
How many hookup stories have you here posted before? 0

MILF in Need Is a Fuck Indeed

How long ago did this hookup happen? 1 month

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? One Night Stand

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? She was a curvy Latina Milf. I think she said her age was 45. Nice hips/ass, HUGE breasts. She was in a bar alone up in Northern California. It was night 2 of a road trip that I took with my buddy. So I decided to do some ¨bar hunting¨.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? As I said before, Me and one of my buddies took a road trip up in Northern California to a big city(I won’t say where). It was basically night 2 of our road trip/ bar hopping adventure. There was a dive bar we had recently visited the night before that we liked. So we decided it was best to stay there for the rest of the night. I had noticed a woman sitting at the bar alone drinking most of the night , but was too occupied seeing all of the other potential hook up victims interacting , reading their body language and such. Anyway, I knew the bar would close in about an hour. Most of the people had already left. So I decided to order another drink in the hopes I would encounter some ¨wandering eyes¨ or attention. Sure enough, the lonely lady at the bar stared right at me for just long enough for me to say something and interact. From there I guess I was on ¨drunken auto pilot¨. One thing let to another, then I was French kissing her at the bar. I told her me and my buddy had a decent Hotel room with 2 large beds , she agreed to come back.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? As we left the bar, she had to pick something up or drop something off at her truck(can’t remember). As she had done her business, she turned around and started grabbing me. Felt up my ass. She then said,¨ It’s just right there¨, referring to my cock(we were still on the street up against her truck at this point). I told her, ¨ If it’s just there then grab it¨. So she did, reached in my pants and started stroking my cock a bit. Told me how horny it made her. She then told me she was going through a divorce, her husband hated her. Then somehow I smooth talked her away from the negative husband B.S. She then said, ¨ I need to be FUCKED!¨ . I kindly agreed as I grabbed her into our rent a car. My buddy half way sober, drove us back to the hotel as I started playing with her pussy through her jeans as I kissed her. We arrived at the hotel, my buddy agreed to stay in the car. As soon as we got on the bed I took off my pants(I’m straight to the point). She started jacking me off , then like a hungry wolf went down on  my cock . Like a gentleman I held her hair out of the way. She told me how she LOVES to suck cock. She was quite the pro, had no gag reflexes as she took my cock all the way down and up her throat. After she was done, I went to go grab a condom. By the time I came back to the bed, I needed to get a little harder again (being drunk has that effect). So I decided to play with her pussy a bit in the anticipation I would get fully erect. So I did, licked her clit a bit as I fingered her at the same time. After a few minutes I explained my dilemma, she willingly agreed to help. So I position over her chest as she started to suck my cock again. I then reached down to reveal some HUGE breasts. So I had no problem getting erect. She reminded me that she wanted my cock inside her. So I slipped on the condom, had her on her back, lifted her legs onto my shoulders , then inserted my throbbing hard drunken cock. She made a gasp as I inserted it like its been quite some time since her last lay. Anyway, I began to work it in pretty good going slow at first then a bit faster. Then I decided to change it up and take her doggy style. As I did I grabbed her huge swinging tits for better control/ hotness. She told me to fuck her harder so I kindly did. Fucking her so hard and fast at certain points it was about 2 hip to ass slaps a second. I also slapped her hard on the ass (I turned her on). I couldn’t resist her anymore. So I decided to finish and cum inside her as I couldn’t hold on anymore. So at the point she was starting to orgasm , I fucker her harder and began to cum inside her but with the condom on. Dropped her back off at her truck, said our goodbyes. And that was it. Traveled back home in Southern California.

Did you have an orgasm? Did your partner(s)? We both did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? 2 Condoms were used. The first one broke (maybe an air pocket).

What were your REASONS for having this hookup? Alcohol, her loneliness from the divorce, my willingness to have sex with strangers.

Were alcohol or drugs involved? If so, how much? Yes, Plenty of beer and cocktails.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I felt bad for leaving my friend in the car for almost 2 hours. But I would do the same for him. It was only fun for the night. It could never amount to anything more for obvious reasons.

To me she is not a slut , just a beautiful woman with needs of company that night. Was beneficial for both parties in my opinion.

To whom did you talk about the hookup? How did they react? Only my friend that was on the trip with me. He seemed a little annoyed he had to stay in the car that long. But after spending the day out, his natural good mood and humor resurfaced.

Was this a consensual and/or wanted experience for you? For your partner? Yes, for both is was indeed consensual and wanted by both parties. By the time we sobered up after the hookup, we both agreed it was a great time.

Do you regret this hookup? If so, why? I only regret that I ¨technically¨ cheated. But I have suspicions about my GF telling me the truth about certain things in her past , so I don’t feel as bad. But that night was about two people feeling long needed pleasure.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing had to be that she was a ¨Milf¨ that was very attractive. Nice body, great attitude. It was an experience I know I will not forget. The worst was the cheating part. I have reasons not to feel bad, but feel partially bad due to the technicality of what I did. It changed in the way that I’ve been avoiding casual sex for so long due to believing in ¨LOVE¨. To me, sex is sex. Its about two membranes rubbing together to create pleasure (Thank you Marcus Aurelius). But I now know ¨love¨ is sort of an artificial feeling in your my (in my own opinions). Now it will be welcomed if the opportunity presents itself.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

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