"You've come to the right place."
"Wanna make this happen tonight?"
I made him bring cider and we sat and chatted for a bit so I could get a sense of what he really wanted. From his response of "I just wanna get fucked", I could tell he was a newbie to D/s things so I was nice about the experience - at first.
Made him strip down to his boxer briefs and teased him with my touch and fingernails for a while up and down his body, watching him grow hard in his shorts. I removed them and was treated to the sight of a decently thick cock.
"I might have use for this later, but that's not what you came here for."
I made him get on all fours and I put on a glove and grabbed the lube. He was rather hairy so it was difficult to find his pucker which proved to be a hassle for most of the evening, but I persevered. He was so tight I had no idea how I was going to get a cock in him at all.
Before that night, he'd said he'd only had fingers and plugs inside him before, but never a cock, and he'd been fantasizing about a girl fucking his ass for over a year. I told him to relax and eventually squeezed two fingers inside him, massaging his prostate gently and watched his cock grow hard beneath him. I made sure to put a towel down in case his cock leaked from the anal attention.
I started with my vibrating plug to get him to open up a bit more. He was concerned about the feeling of needing to shit so he got up 3 or 4 times during the evening to run to the bathroom which was a bit of a mood killer but I wanted him to be comfortable so I texted a friend while he was out of the room.
I never got the plug fully inside him as the base of it is rather wide. I had him turn onto his back at some point so I could see his face and better be able to judge his reactions since he was pretty quiet.
Eventually I turned on the vibration of the plug and he enjoyed that...and started rubbing his thick cock. He wasn't super hard but I think he wanted some other stimulation on top of what was happening in his ass.
He really wanted to be fucked so I got out my smallest dildo and began using that on him with my hands. He really liked that one and wanted me to put it in the strap on but I knew it would be too small to fit with the cock ring I currently had on my harness. He seemed disappointed as he turned back over on all fours. I pressed my body against his ass as I pushed the cock in with my hand and ran my nails down his back to mimic the idea of me fucking him.
After doing that for a while, he consented to me using a larger toy in the harness even though he didn't think it would fit. He was always asking for more lube, to the point where I told him if he were to come back, he'd owe me some.
It took me a minute to get myself in the right position to be able to control my cock inside him, to get the right angle. I had one knee up and was doing lunges into him. Eventually he was completely face down on the bed, his cock rubbing against the towel, his face pressed into the bed right against the wall, my full body weight on his as I thrusted inside.
My animal instincts came out and I began to bite his neck and back and growled in his ear about how much of a slut he was for traveling over an hour to get his tight ass fucked by someone he just met.
He moaned loudly at each thrust and kept saying "thank you for fucking me" and begged me to slap his ass. I tried to get him to call me Mistress at one point but I think he was too lost in sensation to think clearly enough about that so I let it go.
At one point I had my hand over his mouth and I was fucking him pretty deep and he was loving it but eventually I could tell it was getting to be a bit much for him. I asked if he wanted to flip onto his back so he did - sideways on the bed so I could stand on the floor and fuck him. As much as I liked being dominant over him face down and pressing him into the mattress, I also enjoyed the zen look on his face as I pumped in and out of his tight ass.
We took a break when I got a text from a friend that was dropping by to pay back some money he owed me. I removed the harness but told him to hold the cock in his ass and brought him some water. I was gone probably ten minutes and came back to him in the exact same position, on his back with his legs in the air, cock held firmly in his ass.
I started to fuck him again with it but I could tell his ass was pretty worn out so I stopped. He then asked for an OTK spanking. His cock was hard against my leg as I slapped his ass and rubbed it intermittently. telling him all the while how naughty a boy he was. I drew my nails along his back when I was done and he sat up.
Earlier, I had told him how wet fucking him was making me, so he asked if I was still wet.
"Uh, yeah, where is it gonna go?" I laughed.
He asked if I wanted to fuck and after all that I definitely wanted a cock inside me. I sucked him a bit and relished at how he grew hard in my mouth. I handed him a condom and asked how he wanted me and he said from behind so I got on all fours on the bed.
He saw how wet I truly was and slid all the way in immediately and started fucking me hard with no pretense which was exactly what I needed. He was hitting bottom in a great way and I didn't even rub my clit...his cock filled me up perfectly and I just kept cumming. He eventually had me face down on the bed and I crossed my legs to make my pussy tighter and was screaming into the mattress.
We shifted positions a bit and his cock punched my cervix hard and it hurt! I almost wanted to stop but I repositioned myself to be able to take more and told him to use my pussy to cum so hard, and he did. He was done soon after and I was dizzy from getting railed like that. It was awesome.
I knew he was grateful because he texted me the next day:
"Thank you for taking my ass."
Maybe next time he can take the double ended toy. ;)