Squashing Session with an SSBBW
A couple weeks ago, I booked a squashing session with one of my favorite SSBBWs. The session finally happened this last weekend.
As part of the deal, I booked a room at a hotel from a list she gave me. Even though the session was only scheduled for three hours (although I guess that’s a lot going by what she said in her emails), I got the room for the whole night. I don’t know if I actually expected her to stay the night or if I just didn’t feel like asking if I could book a room for a few hours, but regardless I still had the room for a night.
I wound up getting to the hotel about an hour early. I must have paced around the place about a dozen times, I was so nervous. She arrived exactly on time. She had a guy friend with her for safety, like she said she would, and he was pretty cool. He definitely gave her some side-eye when I showed her my ID, but he didn’t object. The three of us chatted for a bit to get comfortable, and after a while he asked if she felt okay with me and she said yes, so he left.
After her friend left, she asked me if I wanted to take anything off to start with, and if I wanted her to start fully clothed or not. She was fine with both of us starting in just our underwear, so that’s what we stripped down to. She had me lie down on the bed and looked me up and down. Before she sat down on me, she paused and asked, “How old are you really?”
I gulped and answered, “Fifteen.”
She had a quick “oh shit” look on her face, then shrugged, laughed, and said, “Well, I’m going to hell anyway.”
She sat down on me, starting with my chest and stomach. I forget how much she weighs according to her latest weigh-in video, but it’s got to be over 450 pounds. I had no idea just how HEAVY that would feel, how completely overwhelming the pressure on my body, my ribs, and my lungs would be. Her whole ass spread out over me and I couldn’t see my arms; it was like her ass had completely devoured me.
I tapped out after no time at all, and she got up, waited until I’d almost caught my breath, and sat down on me again. She teased me about being a “baby cushion” the whole time and said I needed to learn how to hold me breath. She kept me just a little out of breath for almost half an hour, readjusting herself to squash my torso, then my chest, then finally my face.
Before she got up to sit on my face, she looked down at my crotch. I’d been hard since she took off her dress, and it took every ounce of control to not blow my load immediately. She looked down at me, gestured to her panties, and asked, “You want these to come off?” I nodded and she laughed, then peeled her panties off and climbed onto my face.
Her ass smelled of sweat, farts, and a hint of perfume. Her cheeks spilled out on either side of my face, completely engulfing me. She scooter and squirmed until her asshole was directly over my mouth, then she rubbed my face in her ass until I’d tapped out twice. As I gasped for air, she told me to kiss her ass or she’d squash me immediately. Even as I started kissing her ass—left cheek, right cheek, left, right, left, right, faster and faster—she lowered herself back down. “Now lick” was the last thing I heard before she was on me again.
Her asshole tasted like, well, exactly what you’d expect an asshole to taste like. I coughed. I gagged. I winced. But I licked, and I kept licking. I could tell she was putting a little less weight on me so I could rim her more easily. She moaned and purred with pleasure, and leaned forward and put her hand on the tent I was pitching in my boxer-briefs. She caressed my dick and balls through the fabric while telling me to tongue her ass faster. My tongue slipped into her asshole and she moaned even louder and slammed her ass completely down on my face and ground into me while her whole body shook.
She got off of me after a little while, looking very happy. “There’s mouthwash in my bag,” she said. “Rinse yourself out and get back here.” I did, and now she was on her back, legs spread and belly lifted to put her pussy on full display. “Lick,” she commanded. I got between her legs and started licking, and soon her legs closed around me, trapping and engulfing me between her huge fat thighs. I didn’t quite know what I was doing, but she seemed to like it. I settled into a breathing-and-licking rhythm, although the pressure from her legs didn’t make things any easier. From time to time she slapped her belly on top of my head and laughed even as she started to twitch in pleasure (I hope).
She came loud and hard after I’d been licking her for I don’t know how long. She pulled me on top of her and hugged and kissed me. My boner was straining against my underwear at this point, and it practically hurt. As she kissed me, she slid my underwear down and kids-sorta shoved me until my dick was in line with her pussy, and then I slid myself in. No condom, no nothing, just me fucking one of my favorite SSBBWs in a hotel room. Just me feeling her whole body jiggle beneath me as I thrust into her. Just me cumming inside her, resting a couple minutes without taking myself out or off of her, and cumming inside her again.
I rolled off her after I came the second time, and we cuddled and spooned while we both recovered from how intense it was. After a while, she turned on the TV and had me order some pizzas. We spent the night together in that hotel room, fucking, watching movies, me feeding her pizza, her making me put my dick on a slice of pizza while she ate around it (you know, normal sex-pizza stuff, lol), and her sitting and lying on me until we both went to sleep.
In the morning, we showered together, checked out, and went our separate ways. I’ll definitely book with her again when I get my birthday money.