by Nate

Gender: Male
Age: 22
Race/ethnicity: White
Current location: Georgia
Highest education received: High school diploma
Occupation: Restaurant Crew Leader
Relationship status: Single
Religious affiliation: Christian
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 13
How many hookup stories have you here posted before? 0

Doubt She Planned That

How long ago did this hookup happen? Last 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…)? Booty call

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’s probably in her late thirties. I never have bothered to ask. For her sake I will just call her Amber. Amber has 2 children and no husband. She also is my next door neighbor, and pretty hot. Her skin has that perfect tan, and goes with her black hair in a sexy way. Nice breasts, but the ass is just amazing. She has glasses which actually do give her that sexy Secretary look. Its her mouth though that really draws me in. I don’t even know how to describe it, but she has a beautiful mouth.
Anyway we met a year or so ago and honestly we didn’t talk for several months. I could see she liked her privacy. We certainly never hooked up before the time I’m talking about. I was always attracted to her though. I guess that’s why I wasn’t opposed to it when she made the first move.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Well she certainly instigated it. One day on a walk down the street she decided to walk with me. She brought her damn little dog with her to. He’s a cool dog, but pretty stupid honestly. I discovered quick that this chick likes to talk. Even more than me, and that’s saying something. She told me about the troubles of being a single mother, and about how she meant to introduce herself to me yet never did. She seemed like a breath of fresh air considering some of my ex’s. I didn’t think at the time that she had the hots for me, mainly due to our age gap. Then things started to get actually pretty cool and teasing though. She walked with me more often sometimes a few times a week, and eventually decided to leave the dog at home. I loved her company, but she is pretty hot and I mean hormones get tired of  coming close without going all the way. Then one day she invited me to have lunch with her after the walk. I may have let the excitement slip when I said HELL YEAH, but I could care less at the time. Her kids were there so she could scarcely give me a moments attention, but she still watched television with me for about thirty minutes. She kept touching me when we sat together. I would feel her fingers caress along my shoulder and my thighs, and I loved it. She had lowered her voice to almost a whisper on that couch and I could feel my body practically begging to fuck her. Yet her kids came back in the room and we decided on a rain check and I went home with another disappointed boner.
Then it happened. On a random ass day when I had been working out on the lawn she gave me a call on my cell. She asked if I could come watch this show, Penny Dreadful with her. Okay show (Josh Hartnett is still alive and acting, which is awesome), but kinda random. I said yes in a heartbeat. SOOO Glad I did. And yes I am pretty damn sure she planned this.

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? The kids were gone. She didn’t answer the door when I knocked. She just yelled that it was open. So I went in and all the lights were off except for the kitchen. I headed toward the living room and found the tv on, but she wasn’t in the room. I found out later that the show on was Penny Dreadful. I called out to find her and she yelled back from the bedroom. She told me to come in, and when I did…. it was instant boner. She had on panties and bra and that was it. They were yellow which actually looked fucking great on her. She said and I quote: “Wanna watch the show, or Fuck my brains out?” It was mindblowing. I wrapped my arms around her and lifted her by the ass to the bed. She felt so light and smooth in my hands. We kissed for only a moment before I started down on her. I sucked and tasted and kissed every inch of her body from her bottom lip to her waist line. I didn’t stop for long on her nipples, but I damn sure thought about it. I wanted to taste her Pussy. Wait… rephrase that… I had to taste that pussy. After I ran the tip of my tongue along her slit I kissed gently on her clit. The moaning was driving my cock to a whole new level of an erection. I used my thumb and middle finger to spread her open just a little and then found her g-spot with my index finger. I stroked it and sucked her lips at the same time going faster at points and in circles at points. She came three times that way, and she is definitely a squirter. She would arch her back and clench up then just do some sort of a gasp/scream at the same time. It was sexy as hell.
After that she returned the favor. I stood beside the bed while she laid along the end sucking my dick with my pants around my knees. I admit to fucking her throat… its a habit when they use their tongue so effectively. She sucked my balls and the tip of my shaft and I marveled at her expertise. I wanted her bad. She turned her eyes to look up into mine as she sucked on me. I watched her head go in motion with my thrusts. Her hair covered a lot of her face but not her eyes. It was so incredibly hot. We continued like that for a bit, but I wanted to fuck her. And we did it like animals. She would moan my name and beg me to cum inside her. I was so turned on that it was hard to keep my vision clear at some points. When she rode me she did it with her ass always stroking my balls at the end of each grind on my cock. I had never experienced that before and it did the trick. I grabbed her by the shoulders and pushed her down on my cock as I thrust into her viciously. I came inside of her and I said probably at least 5 different 4 letter words. It felt like I was nutting in her for over ten seconds. Then she laid on top of me and we kissed and held each other for a couple of hours. I had to leave because her kids were coming home, but I damn sure didn’t want to. It was the greatest sex of my life.

Did you have an orgasm? Did your partner(s)? I had one HUGE one. She had three when I gave her oral and at least two during the sex.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Um very little but we both are clean and both have been checked out

What were your REASONS for having this hookup? I wanted to experience this AMAZING Milf in every way possible.

Were alcohol or drugs involved? If so, how much? None. She could have drank before I came over, but I doubt it.

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? We still walk together every few days and that gives me hope for several more encounters. Phone calls are a big no no. I think it would feel awkward to us at this point. Plus she doesn’t want her kids knowing our sexual activities and who can blame her. But I can honestly say she is now officially the sexiest woman in my book. I would love to feel my tongue around her vagina at least once more.

To whom did you talk about the hookup? How did they react? Not a soul. Its a small town.

Was this a consensual and/or wanted experience for you? For your partner? Oh yeah it was consensual

Do you regret this hookup? If so, why? FUCK NO

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? Honestly she was the best part. That woman is amazing, and I was damn lucky to have her even for just a few hours. Only thing I feel different about is its hard to compare my exs to her now. They are so far behind that woman.

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

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

Anything else you want to add about this hookup or anything else? Sorry if I’m not too good at writing these sex stories… Never thought I ever would write one.

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