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When I was 19, I was dating a girl named Anna. I had moved out of state for school but her family lived 40 minutes from campus. Anna was still living in a dorm but for her 21st birthday we were going to go have dinner with her family, then later that night go out drinking.

Now in her defense, she did warn me that her family had some weird tests to make sure I was fit to date her. And she even mentioned that they might make me prove myself sexually. Obviously, I wondered she was joking. Apparently, she wasn’t.

When we got there everyone was really nice. Anna introduced me to everyone, her mom Helen, her dad Tom, her sister Quinn, her aunt Tavi and her other aunt Martha. Tavi and Martha’s husbands had decided to stay home. I’d later realize why. At first they just seemed like they were flattering me. They’d say things like “oh you’re even more handsome then Anna described!” I smiled and said nice things back, trying to be a courteous boyfriend and get her family to like me. Then the first weird thing happened.

“Anna’s told us all about how fit you are! Let’s see your abs.” I laughed with Quinn but then her mom chimed in. “Oh yes, take off your shirt.” Before I could even process what she said, her and Martha were unbuttoning my shirt. I looked at Anna but she just had the same passive smile. So I just kept smiling as they pulled off my shirt and Tavi started spreading massage oil on me.

I felt like a zoo animal as they all just sort of gawked at me. At one point I looked at Tom and he seemed just as into it as the women. I stood there waiting for a sign that I could put my shirt back on and go eat dinner. But after a few moments of staring and the occasional grabbing, Helen moved for my pants.

“Oh uh, I’m good. No thanks.” I stepped back and put my hands over my belt but then Tom cleared his throat. So I let her pull out my belt. And then my pants, and Quinn was quick onto my underwear. And as soon as I was naked Tavi was back on me with the massage oil. I kept looking to Anna but her expression never changed.

Helen was an Italian immigrant in her late 40’s. I’ve seen a few pictures of her when she was young, pictures of her in bikinis on the beach in her 20’s, she was cute. She was twig thin with little B cup breasts and a round little ass. She had a cute round face, big eyes, button nose, etc. But in her late 40’s, she was still gorgeous, but she had definitely aged. She was a little chubby, her cute perky tits were now sagging D cups, and her tight core was now a bit of a belly. Tom didn’t believe in body augmentation so all she had was makeup.

That night when I first met Helen she was wearing a tight sleeveless black dress with mesh down the sides and a zipper in the back. Through the mesh I could see the sides of her black bra and the straps of her matching lace panties which were decorated with white butterflies made of ribbon. She wore shiny black heels bringing her up to a whopping 5’6. She had on a pearl necklace, silver hoop earrings and of course her wedding ring which felt weird when she was giving me a handjob. Her rich brown hair cascaded down her left side over her breast. She had purple eye shadow and bright pink lipstick that stained whatever it touched.

“Now I’m sure Anna told you what comes next.” She stepped close to me. “Yeah.” I hesitantly put my hands on her hips, she nodded. I leaned in and kissed her. I had my eyes closed fully expecting to be decked by her husband, but when I pulled back, they were all just watching. She was a good kisser, much more experienced than Anna, and knew a lot of really fun tricks, but her mouth tasted like an ash tray. Nonetheless I kissed her again, her lipstick making a sticky film on my lips, I slid one hand on to her ass. I pulled her closer to me until I felt my dick touch her dress then slid my other hand up her body on the mesh and on to her chin, guiding her kiss.

At this point I started to get a bit more comfortable and my dick started to harden. It was sort of thrilling to be watched. I pulled her body until it was fully touching mine. The control she had over my tongue was incredible. I pulled back slightly, leaning my forehead onto hers so that we could lock eyes for a second before pulling back fully. I looked around again, they seemed to be enjoying the show. I looked back at her. “Do you want help with your dress?”

NSFW: yes

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