A Remembered Evening

“Penny for your thoughts.”

I must have jumped.

“Hey, didn’t mean to startle you.”

I quickly realized where I was. I had been so lost in thought about Dan and our last night.

“Must have been some great thoughts,” Michael continued. I felt my face turn red and grow hot. “Yes, indeed. It must have been some great thought,” he said smiling. “If he only knew, “ I thought, realizing that not only was my face hot, but the tell tale dampness between my legs made me realize other things were hot also.

“Oh, I was just thinking about my boyfriend,” I said. Oh geez, why did I say that?

“Well, he certainly is a lucky man,” Michael replied. We talked some more about how long Dan and I had been together, our hobbies and mutual political interests. He related that he had just gotten out of a long relationship and was not interested in dating any one right now, needing some time for wounds to heal. I told him I could understand that, having been in a couple of situations myself that had not turned out all that well.

I told him I usually had trouble with relationships because I was such a strong, independent woman and men were usually intimidated by me. I didn’t get to the V.P. level of my company by being a softy. He smiled and told me he always liked strong women, they presented a challenge to him. Like a wild horse, he said, they need to be broken and the correct discipline applied to keep them under control.

When he spoke those words, he must have seen my reaction. “Oh, you know of what I speak, don’t you.” More of a statement than a question. I turned my head to look out the window. “You’re no stranger to discipline, are you?” I looked at him and told him that every now and then my boyfriend would take me over his knee and spank me. I couldn’t believe I was telling this total stranger some very private and intimate details of my life but there was something about the way he looked at me; almost as if he had some sort of pull on me. The flight turned bumpy and the pilot flashed the ‘seat belt on’ sign. I was thankful for the distraction and fussed around putting on the seat belt. “How long is your layover in Atlanta?” he asked.

“Almost 4 ½ hours,” I replied.

“Well, by time we get there it will be late afternoon. Would you care to join me for a drink and perhaps a light meal.” Again, I got the feeling this was more a statement than a request and I found myself telling him yes. The rest of the flight was uneventful. We continued our conversation about life in general, his business, my business, family, travel and such. No more was mentioned about discipline.

We landed and headed to a local restaurant in the airport. I wasn’t really that hungry so I had 2 white wines. I still had 2 more hours to kill and felt bad about taking his time so suggested that he go ahead and do whatever it was he had to do and I would sit and wait for my flight. “There’s only one thing I want to do,” he said, “and I want to do it to you.” He continued “I know had you been my girlfriend and had drinks with another man, I would have found that behavior displeasing. You would have been in for a very harsh spanking over my knee. I’m sure your current boyfriend would feel the same.”

I had to admit that Dan would be furious if he knew I had done this and I definitely would have been in for an ass warming over his knee. “Well,” Michael continued, “Dan won’t know, but you and I do and there is only one thing to do. And we both know what it is, don’t we.” Again, more of a statement than a question. I nodded. “Come,” he said. We walked over to the Airport Hotel, located inside the airport and Dan got a room. He took me by the hand and led me to the elevator. Once the doors closed he told me what a bad girl I had been, how he was going to pull up my skirt, pull down my panties and administer a very sound spanking to me. By time we got to the room my pussy was aching and I knew it was wet.

With no ceremony, Michael sat on the edge of the bed and motioned for me to come to him. I stopped in front of him and he lifted my skirt, pulling my panties down, exposing my pussy to him. He turned me around and looked at my ass. “Well, I can see Dan did quite an impressive job,” he said as his hands rubbed over my still sore butt. He took a pillow from the bed and put it on his lap before he pulled me over him. Dan had never used a pillow but I found out by using one, it puts my ass in a more optimal position to receive the blistering is was about to get.

Michael wasted no time in getting to the matter at hand. In no time he had my ass burning more than Dan was ever able to. The man was an expert, delivering each blow almost on top of the previous one to cause to greatest amount of pain, but moving slightly so they only overlapped. He too worked all over my ass and the back of my thighs and back to my ass then back to the thighs, spreading the fire evenly. I put my hand back to cover my ass but Michael easily grabbed it and held in behind my back.

I was squirming and kicking trying to move my ass around so they smacks would come to a place more to my liking but Michael would have none of it. He placed his leg over both of mine holding me so that I could not move and continued to spank me. When I didn’t think I could take any more, he stopped. He didn’t release me, but continued to hold my hand behind my back with his leg pinning mine down. He began rubbing my very heated ass and at first his touch shot more discomfort through me but slowly it began to feel better and I relaxed.

He removed his leg from over mine and released my hand but did not tell me to stand. His hand traveled from my ass to my wet pussy, finding my clit hard and poking out from its usual hiding place. He rubbed the hard nub and inserted two fingers in my drenched hole, finger fucking me to an orgasm. With me still over his knee, he took a well-lubricated finger and inserted it in my anus causing me to jump as I tried to clinch my cheeks together.

“No one been there before.” Again, a statement.

“No,” I said.

“Well, it’s about time to change that, isn’t it.” Not waiting for me to answer he stood me up and began to undress. As his clothes came off I surveyed his body and it was magnificent. This man spent some time in the gym and it showed. Large muscular shoulders and chest, defined arms, a definite six pack and below that, what had to be at least 9 inches of the most beautiful, hard cock I had ever seen.

I snapped back to my senses realizing he wanted, no, was going, to place that large, hard instrument in my never before been entered virgin ass. He turned me around facing the bed and leaned me over with his hand on my lower back. With his other hand he rubbed the head of his cock over my slit and soon it was covered with my juices. I was moaning and begging him to fuck me. He placed the head of his cock at my opening and slowly entered me. I gasped as he stretched me further than any man had before. He stroked in and out slowly bringing me to the brink of orgasm. The he pulled out and I could feel him begin working the head towards my anus. He pushed the head against my anus and I involuntarily tightened up.

“Relax,” he said, placing his fingers on my clit, rubbing it until I was moaning loudly, climaxing. Again he pushed the head of his large cock at my anus but this time I tried to stay relaxed to allow him access. Using a little more force he was able to get the head in. The pain was like no other I had felt but I knew it would be useless to refuse this man and I was in no position to do anything about it anyway. He pulled back just a little bit and shoved forward more. Slowly he filled my ass with his large cock until I could feel his balls hitting my pussy.

He grabbed my hips and began moving in and out. “So very tight I’m not going to last long.” He pace increased and his fingers dug into my hips. Very quickly he was pounding me hard and fast, sliding in and out of my ass.

With a cry of “I’m coming” he did and shot his hot cum deep in me. As he softened some, I expected him to pull out but he didn’t. He stayed inside me, stroking me and I could feel him growing again. He pulled out and in one quick stroke entered my pussy filling me and hitting bottom. He started fucking me with an intensity that almost knocked me over. I exploded with another orgasm as he rammed his shaft in me for all he was worth.

“What a treat,” he said, “a tight virgin ass and a tight pussy. Dan is indeed a lucky man.” A few more hard drives and I could feel his cock spasm as he filled my pussy with his cum. He pulled out and we both showered and cleaned up. I had to rush to catch my connecting flight.

I hated the thought of about 3 more hours on an airplane. I smiled and closed my eyes. Between the spanking from Dan last night and the spanking from Michael today, not to mention the de-flowering of my ass, it had gotten quite a work out. “Excuse me,” I heard him say. “I think you are in my seat.” I opened my eyes to look into the deepest blue eyes as he showed me his ticket. “Oh I’m sorry, you are correct. Here let me move over a seat.” The second part of this flight might not be bad after all.