I dressed up for him - I haven't done that for anyone in years. His specific request was for stockings and heels so I made sure to have them, along with a bra that I was spilling out of, a waist cincher and black panties with red cherries on them and a floor length red robe tied just under my tits.
I was nervous waiting for him, not exactly sure what I gotten myself into. I was afraid of disappointing him, as I felt I had the last time we were together. I had waited for this for so long, I really didn't want to mess it up.
He said he was impressed with what I came up with, despite my telling him I'm not one much for lingerie. I was in awe that he was in my house, in my bedroom, and could only imagine the fun we were about to have. We kissed, then I sat down on the bed to show off the stockings he requested. He seemed to enjoy them.
He was really there to be fucked, so just the robe came off of me but we got him completely naked. I relished the sight of him as he laid down on my bed sideways, spread eagle. I never in a million years would have thought this would happen, him eager and willing to let me have my way with his ass.
I got down on my knees, and placed a pillow under him so he was at the proper angle. My nails were too long to warrant fingering him so I started with beads, nothing too large, to serve as a warm-up.
We talked through it, to make sure he was ready for the next bead and that I wasn't hurting him. I had a whole host of toys and wanted every last one to make it inside of him.
I loved watching his face, the pain that evolved into pleasure as each bead disappeared into his willing ass. I slid his cock into my mouth once most of them were in, and his eyes nearly rolled back into his
head. I enjoyed giving him this unique pleasure.
He became a bit uncomfortable once they were all in, so I slowly withdrew them. Up next was a vibrating plug, one of my favorites. It was too large to get all the way in at first but he definitely enjoyed the vibrating sensations. I wish I could have recorded just the looks on his face. "Let's make that the end game, I could totally cum just from that."
From there we moved on to a dildo...while small in diameter it has a interesting curve to it. I slid it in as far as I believed that special spot to be and then rolled it in a circular motion.
At this point, he was eager to see me with a cock of my own. We chose the double ended one, and struggled a bit with the straps as it had been a while since I had last used it. Of his own accord, he got own on his knees and sucked my big purple cock. I gently guided his head as he worked it, enjoying the gentle sensations inside of me from the other end. "I've seen this done in porn and it never really did anything for me, but in person, it's really hot...mmm..."
"Let's try that last toy and if it slides in easily than I'll let you fuck me with this." Considering how unsuccessful my last attempt to fuck a boy in the ass was, I wasn't going to hold my breath. But the opportunity to take him like that, it was almost too much to imagine.
I got out the next toy, my favorite one. "My friend calls this my David Bowie dildo because it's silver and sparkly." This toy has a slight curve, but mainly just gets slightly larger as you move toward the base. I used lots of lube this time, wanting to make sure I didn't hurt him. I slid it in ever so slowly...he barely moved at all and so I just kept going. He asked at one point why I hadn't put it in very far and I told him it was about 2/3 in...he reached down to feel it because he didn't believe me. Holding the toy inside him, I stood up and leaned over to kiss him. I began to fuck him gently as I kissed down his body. "You're ready for my cock, aren't you?" He nodded.
I had invested in some under the bed restraints months prior to this occasion, but had never gotten the opportunity to use them. I was glad I had saved them for him. I really thought he would use them on me but he turned around on the bed and actually started to put himself in them. I tightened the straps, and leaned back. This is something I never expected to see - KH in my bed at all was shocking enough. But in restraints, it was too delicious.
I grabbed the lube, pushed his knees to his chest, and prepared for entry. It was difficult to get the correct angle at first, but it was so worth it. I loved feeling the pressure on my clit and inside me as I pressed into him. The restraints weren't working as well as either of us had hoped as they are designed to have all four extremities in them at once, so I pinned his hands over his head and kept on fucking. I kept watching his face to catch any glimmer of him being uncomfortable but I didn't see anything but pleasure. My cunt was dripping at this point,the entire thing was so intense.
I soon realized that being the one doing the fucking was exhausting! I sat down for a moment, and then had an idea. I pushed my cock down and attempted the lotus position. It seemed to work at first, but after a while I could tell it wasn't the proper angle for him. I had every intention of flipping him over and fucking him from behind but he had other ideas.
"Is there way to leave that strapped on but pull it out so you can sit on my face?" He was totally topping from the bottom, but how I could resist his tongue exploring my cunt? I'm always a little nervous about sitting on anyone's face, I don't want to smother anyone...but sometimes I think this is the point. The strap on got in the way so I took it off and let him have his way with my cunt. I must have covered his face in my cum I was so wet.
After I came we took a break for a bit. I thought he would want me to fuck him some more, but he had much more intense ideas. I had mentioned something earlier in the evening about needing a spanking. Somehow, I had forgotten that this wasn't going to be an open hand spanking where I get to touch myself and cum whenever I want to. I was about to get the most intense beating of my life.