As we entered our hotel suite from the elevator, Jack yanked at my dress as if to remove it but he either had yanked hard enough or the dress was well made enough, it didn't give at all.
"I want you out of that dress!" He ordered. "I have been driven crazy by that thing all night."
Still a little wobbly from my alcohol consumption, I started to get a little unbalanced as I reach to pull the dress over my head. Jack rushed in and announced that he didn't need me falling, he would do it. Pulling me in to lean against him, he lifted the dress over my head. Dropping it behind me, he kissed me deeply.
"I think you have a punishment waiting. I believe it is time to administer it." With that he led me to our bedroom. Reaching around me, he unclasped my bra and let it drop to the floor. He then had me turn around and he unclasped my garter belt.
"Remove it completely now!" He commanded.
Using the bed for support, I bent over and slid the hose down my legs and over my ankles. In that bent over position, I felt a cr a c kkkk across my ass. I jumped, not having anticipated the smack or the sting that came with it. I started to stand in response. I felt his hand on my back.
"No, don't move. Finish removing your stockings and then stay in position."
Another smack; this one I was more prepared for. I finished removing my hose and held my position, expecting another one any minute. Instead, I felt Jack lifting my head and attaching a blindfold to my eyes. He drew it in tight so that no that no light was visible. Then I felt the next crack on my ass checks. The one side was starting to sting and I whimpered quietly.
"No noise or I find a gag. I didn't bring one but I can make one."
He proceeded to use his hand to smack my ass another 10 or 12 times, I lost count. When it was red, warm and stinging, he stopped. I felt him push up against me, still in his clothes but with a rock hard cock. He leaned over me and grabbed my tits as they were hanging down, squeezing hard, he dry humped me from behind and announced that he couldn't make that happen soon enough but he had other plans first. I was so hot; I wished he would have just taken me then and there. In fact, my juices were starting to leak out of me and dribble down my thigh.
With the blindfold on, I used my other senses to try to figure out what was going on. I remained with my forearms on the bed and my backside in the air. My nipples just barely touched the fabric of the bedspread which has a roughness that I wouldn't have suspected. It kept my nipples aroused. I could hear Jack moving around in the room. I was pretty sure he was undressing but I wasn't certain. I could hear zippers opening and shutting and occasionally the sound of a lid popping off or fabric rustling. Without realizing it, I moaned.
Crack! Went Jack's hand on my ass. "I told you no noise!"
"I am sorry, sir." I quietly responded.
"I'll bet you are," He replied. I felt his hand gently massage my ass check. I then felt the other hand rub the other check and then ply them apart for a good look at my bung hole. I felt his lips as he sweetly pressed a kiss to each side of my ass. I heard some more rustling and then felt the cold jelly of lubricant being applied to my anal entry.
I stiffened. I had told Jack that everything was in play but anal penetration. Was he going to far, right from the start? I didn't want to panic but the panic was welling up inside of me. He must have felt the tension as he said,
"Relax, I didn't forget you limits. But you told me fingers and small diameter plugs were okay. Now just trust me!"
I felt hard plastic being inserted into my hole. It didn't stretch me and it wasn't really uncomfortable. He just kept pushing and pushing β how long was this thing? I was afraid to talk because I didn't want to displease him. He finally stopped pushing and slowly began to withdraw it. I could feel a pop as it slid out. After a couple of pops, he pushed them back in again. It was a slow, gentle but definite ass fucking. I had never had this kind of penetration and frankly, I wondered why not. It felt fabulous! As he felt me become more relaxed and he could tell I had accepted his toy, he moved them in and out a little faster. I felt so full but no pain, all pleasure. I whimpered.
"Are you okay, sweetie?" He asked gently.
"Yes, sir, more than okay, it feels wonderful."
"Well, then," he laughed, "I guess I need to stop. Not ready yet for you to cum."