Lost a bet, had sex with a fat girl, LOVED it!
My sister has a friend who is way overweight. For years now her friend has had a crush on me but I’ve never been interested because, well, she’s fat. Recently my sister became friends with a smoking hot chick that I’d like to get to know better. I don’t need her help getting myself set up with her, but when I mentioned I was interested sister got a little pissed at me.
“What about Melissa?” She asked. “I’ve been trying to put you together with Melissa since we were kids!” (We’re all early 20s now.) Melissa is a very nice girl, she’s smart, talented, and so on. But she’s so...fat!
Well...unbeknownst to me, my sister’s new friend, the one I was interested in, likes watching people fuck. Melissa, upon hearing this, admitted it would be fun to have someone watch her fuck. My sister, being a devious cunt, started conjuring up a way she could get me in bed with Melissa and she and Aura could watch.
So she presented me with a proposition. We’d play a game of chess and if I won she’d agree to set me up with Aura. If I lost, I had to let Melissa ride me with she and Aura watching. I consider myself pretty solid at chess and most of the time we played I beat my sister. I don’t know if I felt pressured or what but after a good start to the game where it looked like it would be a route my momentum slowed and to make a long story short my sister check mates me after a war of attrition.
I begged her not to make me fuck Melissa. But not only did she tell Melissa she told her I was excited about it and told me I’d better tow the line. So I’m getting texts from Melissa telling me how much she’s looking forward to “our night” and I’m dying inside.
Then came the big night. We all met at Melissa’s apartment. I was nervous I’d even be able to get hard because I genuinely didn’t want to go through with it. But I also pretended I was excited because I did consider Melissa a nice person and a friend and dreading what was about to happen to me as I was, there was something endearing about her excitement.
I’m not going to get into the details of what it was like. I’ll say this: stripping naked with my sister watching was a little weird. But no sooner was my penis out of my pants than it was in Melissa’s mouth. She ate it up like it was a slice of cheesecake! Any fears I had of being able to get hard were gone within seconds. I felt she was going to slurp me down whole and alive! Then she forced me back onto the bed and mounted me.
And I said I wasn’t going to share details, so I’ll stop there. At first it was anguish looking across the room at seeing Aura, the woman I wanted to be fucking, watching me get devoured alive by Melissa. Also seeing Melissa’s fat reflection in the mirror as she rode me, it was embarrassing to me. But as we continued to fuck I started to like it more and more.
After we finished my sister and Aura went into the living room for a drink. I lay there breathing heavy and with Melissa resting her head on my shoulder. She kept kissing me gently and whispering how good it felt to have me after so long.
After a few minutes my sister came back in and asked if we wanted a drink. I said no and squeezed Melissa. My sister gave me a look that said, “I knew you’d like it!” And left us alone.
Melissa and I are now in a committed relationship, going on about 2 weeks now. For years my sister insisted we’d be perfect for each other and even though (if I’m honest with myself) deep down inside I agreed, her weight kept me away. Now I don’t give a damn, I think I have the most amazing girlfriend I could find. And the sex is amazing.
Oh and it turns out that even had I won that chess game I’d have lost. Aura likes girls and my sister is going through a bit of a “bi-curious” phase I guess. Melissa and I want to watch them fuck next.