My eyes went wide when she brought out some small C-clamps. She tightened one on my left nipple causing me to groan in pain. After my groan she tightened another quarter turn, causing me real pain and agony. Next was my right nipple where she followed the same procedure. My nipples burned and throbbed from the pain. Then she brought out several dozen clothes pins which she placed onto my chest, abdomen, and penis and scrotum. When they were all attached she told me, “Now for the fun part. I’m going to knock them all off you with this crop. Lie still or I might hit you instead of the clothes pins.”
Victoria’s aim wasn’t very good—either that or she was deliberately missing so she could hurt me during “our fun.” As much as the clothes pins hurt when they were attached, the pain of removal was much worse. She started with my chest, moving down toward my cock and balls, each of which had at least eight pins gouging into my skin. I was in agony, but I was pretty sure it was going to get worse. When they were knocked off the pins left small circular red welts. My torso was covered in them. Hopefully they wouldn’t turn black and blue. It was a full five minutes before she began striking the first she had stuck to my sensitive abdomen. She swatted wildly, striking my penis several times, either missing the clothes pin entirely or on the follow through. My poor cock was turning purple from the lack of circulation. That’s how tightly she had tied me. I was still rock hard, maybe even harder than I had been when all this had started.
When I looked up at Victoria I could see that she was ecstatic. She had somehow removed her dress and was kneeling on the bed in her thigh high stockings and black silk panties. There was a huge wet spot between her legs. I was glad that one of us was having a good time—I certainly wasn’t. So far I’d been hurt and told I couldn’t even jerk off any more—what could be worse? I was afraid to even think.
I knew now why she had insisted on the gag. I was screaming into it almost non-stop as she moved to the clothes pins on my hard cock. The pain was more than intense and it was made all the worse when several pins refused to come off. She hit one of them at least eight times, striking my hard penis every time before it finally came loose. Suddenly, Victoria stopped. There were four pins still on my cock and another eight on my scrotum. “Oh, Mortimer, you’re being so good for me. Just look at my panties—see how wet I’ve become. I’ve already cum once. Just wait ‘til I get down to those lovely balls of yours. I’m getting a drink. Would you like one? Oh, silly me—how are you supposed to drink anything with that gag in your mouth?” She patted my head and left.
Five minutes later she reappeared with a tall drink. “Gin and tonic, Mortimer, I bet you’d love one right about now, wouldn’t you? Maybe later—we’ll see. I have to tell you…alcohol makes my aim worse. I’ll probably hurt you even more now. It’s a good thing you’re gagged. OK, back to the fun.” She picked up the crop and resumed swinging; I resumed screaming. It was some fifteen minutes later that she finally removed the final clothes pin. She must have struck me forty times to remove those dozen pins. My cock ached; my balls were swollen and blue. I was in extreme agony. Beads of sweat formed on my face.
“Wow, Mortimer, you gave me more orgasms than anyone I’ve ever done this to. Now we’re going to do something else. I think you’ll like this; I know I love it.” She removed the restraints from my wrists and recuffed me, this time in front of my body. She helped me up and fastened my wrists to a chain hanging from the ceiling; she locked the cuffs to the chain. Once again I was stretched and helpless, but this time I was vertical. I didn’t know if that was good or bad—time would tell.
Victoria brought out a chain that she attached to my nipple clamps. When she added a weight my agony began anew. Every movement caused the weight to sway and pull on one nipple or the other. When she added a second I was afraid she would pull my nipples off. I stood as still as I could on the springy bed. Unfortunately, standing perfectly still was impossible. While I was concentrating on my poor aching nipples Victoria cut the bindings on my balls and cock. The restored flow of blood was reassuring, but the pain was terrible. She rubbed my testicles in what I mistakenly thought was an act of caring. But that idea was quickly wiped from my brain. She hung a large weight from the loop she had placed under my helmet. My cock, already as hard and long as it had been in years, stretched another two inches. Then she attached a circular weight to my scrotum. When she had screwed the pieces together she added two eye bolts and hung additional weights to my ball sac. “What else could go wrong?” I soon found out. She applied some gel to my asshole and pushed in a large butt plug. I could see a cord running from the end—a vibrator—oh, wonderful! It made me shimmy and shake causing the weights to move and sway. When Victoria saw how much I was struggling she added additional weights to each area. My knees buckled and I was hanging by my wrists. She turned out the lights and left me, closing the door and leaving me in total darkness.
I had no idea how long I was hanging there, but my arms and shoulders ached when Victoria finally returned. “Oh, Mortimer I’m so proud of you.” She kissed my cheek as she finally began to remove the weights. It was a great relief when the weight was lifted from my balls, but when she opened the nipple clamps, the circulation again caused me to wince and whine. I was crying with tears running down my cheeks. Eventually, Victoria released me and I sank to the bed. She put my head in her lap and massaged my shoulders, rubbed my nipples, and, finally, moved her attention to my groin. My ball sac was sore to the touch and badly swollen; my penis was bruised—turning black and blue.
“You did marvelously, Mortimer. I came five times while we were playing. Now I’m going to give you another chance to satisfy me. Roll over and eat this pussy,” She spread her legs and twisted my head. I found my face in her wet sweaty cunt. I’d had absolutely no experience doing this just as I had no experience at any kind of sex—at 37 I was still a virgin. Maybe that’s why I had accepted Victoria’s date offer. However, living alone allowed me to watch a ton of porn so I had some idea what to do. I kissed her cunt all over before sticking out my tongue and licking her from asshole to clit. When Victoria moaned in response I knew I was doing something right. I began at the edge of her pussy and moved slowly toward the center. She almost jumped when I licked her slit and again when I pushed my tongue into her tunnel. I fucked that tunnel furiously, almost exhausting my tongue in the process. I moved up to her clit. I used my hand to pull back the hood, exposing the hard red button to my lips and teeth. I sucked hard, pulling it between my teeth. Victoria came hard, flooding my face with her juices. I knew I was done when she pushed my head away. I licked around my face, savoring the taste of her wonderful pussy.
“Mortimer, you certainly are full of surprises. I would have thought you’d be an amateur and now I find you’re an experienced cunt licker.”
“Actually, Victoria, you were right the first time. Yours is the first pussy I’ve ever licked.”
“Come on, Mortimer, next you’ll be telling me you’re a virgin.”
I turned red with humiliation and Victoria saw it. She immediately pulled her hands to her face. “I’m sorry, Mortimer, I didn’t mean to embarrass you.”
“It’s OK,” I replied once I found my voice, “it’s not your fault. I’ve never been very good with women. In fact all my dates have been disasters until tonight.”
“Mortimer, that’s the sweetest thing anyone’s ever said to me. Just for that I’m giving you an extra big reward. Come over here and lie back. I’m going to jerk you off.” I settled back on the pillow as Victoria slowly stroked and caressed my bruised organ. I was surprised when it responded immediately, hardening to her touch. Slowly she began to stroke my cock and twist with her right hand while the left rubbed my tender balls. She increased her pace with every stroke and in my excited state it took no time whatsoever for me to come. My first rope shot more than three feet into the air, landing on my chest and neck. The next two were almost as strong and the final three still shot more than a foot into the air. I had never cum so much in my life. All the pain and humiliation were worth it. What an incredible orgasm!
“Don’t get too comfortable yet, Mortimer, you still have to clean up this mess. I’ll help you. I’ll scoop it up and you can lick it off my fingers.” I looked at her as if she was crazy, but her stern expression told me she was not. Meekly, I complied. Five minutes later I had consumed my entire ejaculation. It wasn’t horrible, but….
“Well, Mortimer, usually I tell my dates to go home now, but I wonder if you’d like to stay the night?”
“That’s a great idea. Which side do you want?”
“Oh, Mortimer you’re such a joker. You can’t stay in my bed. You have to earn that. You can sleep down here.” She got up and led me to the foot of the bed. She whipped off the cover and my mouth dropped at least a foot.
“A dog cage? You expect me to sleep in a dog cage?”
“Of course. You’ll be close by and I’ll know you’ll be safe. See, there’s a nice pad on the floor and I’ll get you a pillow and a blanket. You’re not very tall so there will be plenty of room in there for you, but first I’m going to lock you up.” She went to the closet, retrieved something, and pulled me to the side of the bed. She pulled my balls and cock through a plastic ring, slid my cock into a plastic sleeve and locked it with a padlock. I stood there dumbfounded. She must have seen the expression on my face because she continued, “If we’re going to see each other I need to be sure you’re saving all your sexual energy for me. No masturbation, ever, unless I say so. Of course, you can just go home and we’ll never see each other again. It’s your choice.” Reluctantly I climbed into the dog cage. She gave me a small blanket, a half-size pillow, and a kiss on the forehead. She closed and locked the door behind me. “Good night, sweetie. I can’t wait to play with you some more tomorrow.”
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