Written by Leesa (the blogger for this site)
When I walked into the restaurant and was led to the table of my blind date, I was a bit surprised. He was supposed to be 49 years old, which would make him 5 years my senior. During the first few minutes, I don't know exactly what we talked about because I was trying to figure out how old he was. But then we started talking about books, about traveling, about all sorts of things, and I enjoyed myself.
The gentleman was well-known at the restaurant, so I thought he probably eats out a lot. And it was such a nice place . . . I was sure he had money. That, plus him being well-read, and I knew he was intellectually my equal. The only strange thing was that people at the restaurant called him Henry, and he introduced himself as Hank. I was not sure why at the time. I assumed it was to make him seem younger, and I was wrong.
During the evening, he said he had a rare book by Kafka,"Die Verwandlung", or in English, "The Metamorphosis". He was impressed that I did not site the first lines incorrectly - most people think the protagonist wakes up as a cockroach. It was actually an unidentified vermin.
By the end of the evening, I suggested that I would very much like to see this near 100-year-old book of his. I knew he had others, and other older books, but this is one of the most important works of the 20th century, and it is in its original German.
I normally don't go in dates homes the first date, but I guess it seemed less like a date than a meal with a friend. When we got inside, he showed me immediately to the library, and as I was admiring his large collection of books, he brought two tumblers of a dark liquor. It was oaky and strong, and I drank it in small sips.
I kissed him after handling "Die Verwandlung"; I guess I just appreciated the book so much, and it was better than an awkward kiss while by my car door later that evening.
After appreciating several rare books including the one I asked to see, I pardoned myself to use the restroom. The downstairs restroom was immaculate, but it definitely had a man's touch in the design. After washing my hands and looking in the mirror to ensure that I didn't need to touch up my makeup, I particularly liked the way my hair was framing my face. And then, on a whim, I stepped out of my dress, took off my shoes, paused for a moment, then removed my panties and bra.
I exited the bathroom completely in the buff and found Hank in the library. His jaw dropped, but he had the biggest smile on his face. I started kissing him, and he had his hands on my bottom as he returned my kisses. With almost no words, he led me upstairs into his bedroom, again pristinely clean. I could smell the faint scent of cigar smoke . . . I am particularly sensitive . . . but it had to have been smoked on a previous day. The light scent hung in the dark drapes.
He pardoned himself for a moment, and he entered his own restroom while I was on the large bed. He came out of the restroom, having taken a pill and was smiling. He asked if he could tie me up slowly, and I agreed, partly because I assumed he was stalling to allow his pharmaceutical helper to catch up to his desires.
He placed leather wrist and ankles restraints on me, and just the thought of being helpless excited me. I wanted to have this older man inside of me so bad. He placed restraints on the bed frame, telling me how sexy I looked, and then using hardware to clip me to the restraints. I tugged on them, and I could tell I was held tightly in place. I was not going anywhere.
He kissed my breasts tenderly, but I could feel the scratching of his whiskers. The stubble may have been fresh, but it was rougher then my ex's stubble ever got. He then did something curious. He plugged in what I thought would have been a vibrator, but it looked more like a back massager that you would get from the mall. He then took the massager, which had a rather large, almost garlic shaped attachment, and placed it on my pelvic bone.
Deftly, he turned on the massager, and I thought to myself that this stimulation would never get me to orgasm. I started planning on whether I would fake it, and then he grabbed an edge of the massage head with one hand, and with that same hand, inserted his index finger inside of me. Well, the massager was moving his finger inside of me, and in short order, I was cumming. I arched my back as I got close, and with his strength, he pushed me into the bed again, making my orgasms come fast and hard.
Inside of ten minutes, I must have had nearly a dozen orgasms, and I could feel tears leak out of the corners of my eyes. "Yes," I was practically screaming, "you can do anything to me, Hank!"
After another minute, and another two orgasms, he turned off the massager, and I was almost glad of it. I was weak, vulnerable, and I started wondering if I looked a mess.
He left me, tied, for a moment, and he returned with a towel and some oil, wipes and some condoms. He placed the towel under me - me assisting by lifting my butt - and then he wiped my vagina, moving his hand down towards cleaning the anus, like I might do if I were on the toilet. I recoiled a little, but he cleaned me off. He then put a liberal amount of oil where I could feel it on my pelvic area, him ensuring it kept me wet. He then slipped on a condom, and he asked if he could "fuck my ass."
I said, "Fuck yes!" And he asked me to repeat myself, which I did. Then he started kneading some of the lube into my asshole, and I realized he thought I meant anal sex. I had assumed he wanted to cum inside of me.
"Hank," I said, a bit of fear in my voice, "I am not that experienced in such matters." He said he would be right back, and he had a syringe. He unscrewed the cap of the bottle of lube, stuck the syringe in, and filled it full of oil, which he placed inside of my asshole. I was embarrassed and excited.
He placed the head of his hard cock inside my butt, but only the head. And then I started squeezing his cock with my ass. As I squeezed, he seemed to squeeze as well, his cock's head getting bigger inside of me. But he did not push his cock deeper; he let me squeeze him.
"You are squeezing your anal sphincter and your pelvic floor at the same time. Try squeezing your sphincter only."
I tried but could not really control one without the other. His cock, however, was getting squeezed and he was getting near. He began pushing into me more and more, and then when I felt my anus open slightly, he pushed his pelvis, thrusting his cock deeper inside of me.
"Deeper," I asked, and his reply was shocking: "I am all the way in."
He did not move in and out immediately. He stayed in, and I continued doing my exercises. And when he got closer, he started moving slowly in and out of my asshole, not coming all of the way out. When he came, I really wanted him to be inside of my pussy. I could feel him erupt, and it made me feel good. Complete. I held him on my chest for a few minutes afterwards. I was spent, and so was he.
He untied me and I cleaned myself away from his prying eyes. Although the anal sex did not hurt at all, the first time it didn't, I wanted to dress quickly. I was embarrassed.
The next day, my ass hurt during my first two bowel movements. I looked for blood, but there was none. And the pain I felt in my ass made me think of that evening. I loved everything about the experience, how I was the aggressor early on, how Hank took over, how it was a new experience that turned out to be positive, and how I enjoyed him being older than me. I still smile about this.
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