During my late teens (19yo), I used to work as a delivery boy. It was in a small town, filled with lovely and well-decorated houses. I worked for the main pizza company in town, so we got a *lot* of customers from all over the place. At the time, I had a boyfriend. We had been together for a couple months already.
Anyways, I used to work the night shift, and during a hot summer night, we got a call from a house I had never delivered to before. It was on the outer side of town, but didn’t feel creepy or dangerous, I didn’t give it much thought. So, I got the pizza, and drove all the way down to this place. It was a very big, white and brown mansion, with a pool and a huge garden. I ringed the bell, and a lady answered, and told me to wait while she looks for the keys. She opened the door, wearing only a bathrobe that outlined the edge of her breasts. She was tall, light brown hair, thick lips with red lipstick on them, and makeup on.
She asked me to come in, and wait for a bit. I was holding the pizza on one hand, standing still. She went to her bedroom, and came back totally naked. She started walking towards me. I wasn’t turned on… not at first. I’m gay, why would that get me horny, right?
“You know, it gets pretty lonely here at night”, she told me seductively while looking at me in the eyes.
“Yeah…” I answered kind of weirded out. “Why don’t you just pay me, so I’ll leave. You’ll have the pizza, I’ll have my money, and that’s it”.
“Oh sweetie, what, you’re gonna tell me you wouldn’t like it if I did…” She started rubbing my crotch “this?”.
I started getting nervous, backed away and told her I was gay. Which seemed to turn her on *even more*.
“Well you’re gay because you have never tried me. Believe me, no hot guy like you would resist me”. She said as she started cornering me against the wall. At that point, I felt trapped.
“I… I have a boyfriend” I told her, with the words just muttering out of my mouth.
“After me… You’ll have a girlfriend” she whispered on my ear.
I tried pushing her off me, but she grabbed my hand, and took me to her bedroom. The bed was huge, and it smelled like roses. I was speechless. I was in the house of a naked MILF, who wanted to have sex with me. She sat me down on the bed, me being shocked and still resisting her. She sat on my lap, her breasts basically on my face and started touching me. I started getting a huge boner. It’s like… I couldn’t control it. My dick was hard, and wanted her. I didn’t, but my dick did. It started twitching since I was wearing tight jeans, and she noticed. She grabbed my bulge, and said with a very sexy voice:
“See? I told you, you couldn’t resist me.” While licking my ear. She then went down my jawline, and started making out with me. Her breasts were rubbing against my chest, which was covered by the pizza place’s T-Shirt. Her tongue was in my mouth, and her lips were brushing against mine, while her ass grinded my dick. Quickly, she got down, and unzipped my pants. I was wearing tight boxers, which let the erection be very easily seeable. She noticed it and started stroking it.
For one last time, I tried resisting my internal urges, saying, while panting with pleasure from her soft hands, “but I’m gay, I- I have a boyfriend, I can’t do this”, while trying to get up. When I did, she jumped onto me, throwing herself and me on the bed.
“Don’t try to escape honey” she said while pulling down my boxers and pushing my head in between her tits.
At that point, I entered a state of pure ecstacy. She noticed I was a virgin, and started rubbing her ass against my bare boner. In the meanwhile, I was licking her nipples and the inside of her boobs. She pulled my head up and started kissing my neck, and finally gave my kiss a mouthful kiss. Then, she got on top of me, inserted my dick into her pussy, and rode me. She rode me so hard I didn’t even notice I hadn’t brought a condom. She bounced up and down, and I was mesmerized by the look of her tits touching each other and coming back at me. She kept on going for 15 minutes while I licked every inch of her beautiful huge breasts. I had felt nothing like that before. I came inside her, and she told me she loved the sensation of a virginal teenage horny boy fucking her.
Once we were done, I grabbed my pants, and my T-shirt, and started walking towards the door. Before I left, she said:
“What’s your name?”
Me, being naive as I was, and totally in shock, answered with my real one:
“B-Blaine, I’m Blaine”.
“Ok, Blaine, I’ll ask for you next time I order food”.
We had other subsequent encounters, but don’t wanna tell them right now
Source: reddit.com/r/sexystories/comments/fb5iwq/how_i_lost_my_virginity_to_a_milf_as_a_gay
That’s hot as fuck