So I have a friend with benefits that I will hook up with every couple of months or so. His name is Jack.
We live several hours apart but I had to visit his city for work reasons and so I hit him up to let him know I would be about.
“Great. But if you’re coming over I’m finally getting to fuck that asshole. Be ready.” He said.
Now Jack is incredible in bed, but so aggressive and dominating. He’s 6ft 4 and well built, to my 5ft and the size difference makes me feel so naturally submissive to him and is a huuge turn on. He also has a fetish for making me squirt with his fingers and will do this many, many times a session. He’s expressed many times how badly he wants us to do anal but I really didn’t know if I could handle our sex being any more intense that it already is, so have always said “not yet.”
But as I’d been instructed to prepare I spent the next 1-2 weeks using my plug to masterbate and fingers to get myself ready.
So I went out for dinner and drinks with my co-workers, finished an entire bottle of wine to calm my nerves and then went over to his apartment as we agreed.
He invited me in and made me some tea and we got caught up, cuddling on the sofa. It wasn’t long until we were kissing and he stripped my clothes off. Underneath, I wore low denier tights, with a black lace underwear set. He broke away from our kiss to pick me up over his shoulder and carry me into his bedroom.
He sat down on the bed and had me grind into his lap, he taken the bra off and was tweaking my nipples, while kissing my neck. It felt amazing, I couldn’t stop my hips bucking because I just wanted to feel him inside me.
His hands moved down to stroke my clit through the tights, and he suddenly ripped the crotch open so he could pull my thong to the side.
I was soaked, and I knew what his fingers could do so I warned him.
“ Do you want to take your trousers off before I squirt all over them?”
He covered my mouth and pushed two fingers deep in.
“ I don’t care. I don’t care if you leak all over my bed, but you will come for me.”
I was weak then and my first orgasm and huge release of squirt hit me.
Jack then told me to lie down on all fours and he took a rope and tied it around my neck, then wrapped it behind and bound my arms together all the way down. Next he said, “I’m going to have gag you because you don’t know how to shut the fuck up.” He put a silk tie into my mouth and really tightened it. I could still make noise but couldn’t speak and it had me drooling a little.
Tied up he left me on all fours and took some photos of me bound.
“You look so good right now, you’re little asshole looks so cute.” Needing to remind me what was coming I guess.
He used his fingers on my clit and gspot to pleasure me more, after 2 more orgasms I heard him open a condom.
He kicked my legs apart wide with his knees and pushed his big cock into me, and reached round again to play with my clit. not being able to use my hands to control the depth or say anything was overwhelming but felt amazing at the same time. I couldn’t think about anything else but the cock inside me and the orgasms that were being forced out.
Once I squirted again, Jack rubbed the mess all over my pussy and asshole, then added more and more lube. He slipped his fingers in and I was so turned on it felt amazing. Still bound with my hands behind me jack pulled me by my legs down the bed so I was completely flat on my stomach. Then he eased his cock into my ass. It felt so tight but the friction was amazing.
“Are you going to be a good girl and let me fill this little asshole with cum?” He asked.
I could only nod and droll while he stared to fuck me harder, knowing his orgasm was building. He grabbed my chin and turned my head to look at him, and slipped the gag out of my mouth . we were both so messy and sweaty. I started to get goosebumps on my body and the anal was getting uncomfortable.
“Don’t stop looking at me. I want to see your face while I fuck this ass”
“Yes daddy.” I was able to reply and that finished him off. He came grunting and collapsing into me.
~aftercare~
After I was shaking and still covered in goosebumps. I found it really hard to speak and my head was cloudy from cumming so hard. My arms and shoulders were sore from holding the same position.
Jack carried me into his bathroom and he ran me bath. He left me to have a soak and I came back into the bedroom. He gave me cozy sweats and a big glass of water.
I slept so soundly, after getting spooned and being called a good girl.
?
Source: reddit.com/r/gonewildstories/comments/krztxw/surrendering_my_asshole_to_my_fuck_buddy_fm
Goodness me.
I love that you included the aftercare. Thank you!