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Lost virginity to coworker MILF

Tldr: I lost my virginity to a MILF and now I'm head over heels for her.

I graduated high school last year, but have been taking a break for a bit before I go to college later this fall. I got a job in the interim at a local deli. It's a small place with eight employees and it's kinda like a family. The people are cool. The owner/boss Jim is great as his his wife Britney, who sometimes helps out. They are somewhat neo-hippie types who also dig music, sports, and partying.

My boss Jim invited me over to his house to watch the NFL games with a few of the other employees. I said sure. I got over there and it was me, Jim, Britney, and a few other employees as well as some of Jim's friends. Other than Britney, the only other woman there was our coworker Donna. She's 49, divorced, and is a nice lady. I work a shift that overlaps with hers, but I've enjoyed working with her. She's got a nice body for a lady her age. Great legs and ass. Her face is pretty, although she has spent too much time in the sun over the years. She's a bit of a mother figure to me, and sometimes we'll smoke cigarettes together out back on breaks. I've had a bit of a crush on her, as I like blondes and she is a nice person. She treats me like an equal.

Most of us were hanging out drinking, smoking a little weed, and enjoying the game, but I could tell that Donna and Britney were very flirty with each other. I didn't know they were that friendly. They were laughing, joking, and eventually started making out. Donna took off her jeans and hopped up on a table, and Britney went down on her. I had never seen real pussy in person ever, so seeing Donna's was awesome. The rest of the guys in the room loved the show too.

Donna was still getting warmed up by Britney when she said, "If any of you guys wanna fuck, I could use some cock." Two guys had their dicks out right away. I got mine out too, although I was really nervous. I was a virgin and the thought of losing my virginity in a room full of people that I knew had my heart beating through my chest.

One of our coworkers went over to Donna, got between her legs, and went first. She enjoyed his cock, although it was only evident from her subtle facial expressions and her breathing. After a few minutes, our coworker pulled out and came on her abdomen, and she wiped off with a tissue. She looked over at me and said, "Wanna go next?" I said okay and went over to her.

As I fumbled around and slipped it in, she reached over and lit a cigarette and said, "I don't ever fuck people your age, but we're friends. Just don't tell your parents, okay?" She knew I still lived at home with them. I was already in a haze from being inside my first pussy that I don't remember what I replied. She leaned back a bit to enjoy my cock drilling her, with her eyes closed and occasionally taking deep drags off of her cigarette. She was definitely a girl who likes to fuck.

I'd like to say that I was a stud, but damn, getting my first pussy made me lose it quickly. I had to slow down a couple of times, because I was getting to the edge too soon. I pulled out and came on her pussy, as I didn't want to make her too much of a mess inside. I think I lasted three minutes, but it was the best three minutes of my life. (It was like, "So that is why people like pussy!")

Donna fucked one more guy after me and she had gotten off enough that she was done and just hung out with us to watch the game. I was in a surreal state mentally with endorphins and shit swirling in my brain. I could feel a connection with her, but I could tell that she didn't really feel it with me. I was just a cock to fuck, nothing more, nothing less. She was still nice and friendly afterwards.

We've worked together a couple of times since then, but she has never brought that day up. I have a crush on her even bigger than before, but I know I'm wasting my time thinking about it. But having her be my first pussy makes me really love her. It's insane, I know.

Jan 28

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      • You'll get over her

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