Lady Barber

As I expected, she was waiting for me when I signed on. I ignored her for 5 minutes while I checked mail and answered those that required it. Finally, I acknowledged her.

“How do your breasts feel today?”

“Erotically painful Sir. I have been wet all day thinking about last night.”

“So a repeat performance would be welcomed?”

“Oh yes Sir, I find myself squeezing my breasts to rekindle the pain.”

“Another time perhaps, I remember you requesting a spanking. Do you think that will be a sufficient amount of pain, or are you game for a more intense pain?”

There was silence as she let the words sink in. I knew she was flowing in anticipation.

“After the zipper, a spanking would be child’s play. The pain on my breasts merely triggered a want that I never knew I had. The thought of you inflicting pain has me aroused and eager to meet you again. If you so choose to use me again, I would be most grateful.”

“Be ready at 6 tomorrow evening.”

I signed off before she could reply.

I had discovered a web site that sold hand made canes of various sizes and had ordered one that was recommended for novices. I had never used one before, but had a friend who had been caned many times and she explained to me the proper procedure as well as the need for caution. I was anxious to try it out, but certainly didn’t wish to draw blood.

I spent the next day in the shop making the accessory that I had previously thought of to enhance a spanking or strapping. Since I had decided to use a cane, I doubted that it would be necessary; however, the arousal I enjoyed from bringing my idea to reality demanded that I make it anyway.

The accessory was custom made according to my measurements from the first session. It resembled a butt plug, but was much larger. The diameter was 2 inches and the length 6 inches from the tapered tip to the groove that would allow her sphincter to grasp it. Someday it might get pushed into her anus, but that would take a lot of preparation and training. For now, her vagina would take the brunt of it. I wanted it of sufficient length to press against her cervix so that any blow to the labia would be transmitted directly to the womb.

I pulled into her driveway at 6:30. I had thought of making her wait until 7 but I was aroused myself and anxious to get started. The door was open and I walked in, closing it behind me. As before, she had dropped the robe she was wearing and was standing nude waiting for me. Either her natural submissive nature or discovery through reading had resulted in her legs being spread in preparedness for me. I grabbed her hair and kissed her. My tongue pushed into her mouth and was met by her own, intertwining in passion. Her arms tentatively went around me; I pinched her nipple in approval, which resulted in her melting against me. Increased pinching and twisting produced what sounded like a purr from her throat.

I broke the kiss and reached down between her legs. As I expected, she was moist, not dripping, but definitely aroused. I pushed two fingers into her and gathered as much fluid as I could; then with my wet fingers, I coated her upper lip and nostrils.

“Do not wipe or lick that off, I want you to smell your sex, I want you to benefit from your arousal as I do.”

I went over to the couch and removed my clothes, then sat down and motioned her over. She knelt down between my open legs and took my cock in her mouth, knowing exactly what I wanted from her. I was somewhat aroused but it didn’t take her long to bring me to complete hardness. Now she couldn’t get all of my cock in her mouth. I let her work on it, coating it with her saliva and my pre-cum, preparing it for what I wanted next. When I felt the juice that ran down from her mouth to the base of my cock, I knew that it was time. When she had pulled back until just the head was in her mouth, I pushed on the back of her head with my finger. She knew exactly what I wanted. Hesitantly she pushed down until the head hit the back of her mouth and the opening to her throat. She gagged and pulled back, looking at me with pleading eyes because of her failure. I placed my hands on her cheeks to indicate my love and indicate that it was not a big deal.

She again tried to take me, gagging again but getting part of the head in her throat. She pulled back again in frustration. I cupped her face and said, “Try yawning or saying Ah, which will open your throat and make it easier.”

With my reassurance, she bent down again and I could feel her throat open as the head slipped. She gagged for a second, swallowed several times, which were awesome to me, but kept it in. I stroked her cheeks to show my pleasure, satisfied with the progress made. Her breathing was rapid because of being forced to breathe through her nose. What she didn’t know was that even her nasal passages would be blocked when full penetration was accomplished. I didn’t want her to become frightened, so I pulled her back off my cock.

“You did wonderful, I am proud of you. I know you want to take the next step, but I want to warn you. When you manage, and I say when, not if, you will find that you may not be able to breathe when my cock is all the way in your throat. At any time you feel the need to pull back and get your breath, you have my permission to do so, this is something for both our pleasure.”

She looked at me with those doe-like eyes, and then plunged down on my cock. This time further progress was made. The head went a little deeper before she stopped to make a partial gag. This time she rested and looked up at me in adoration for being patient. Little did she know that I was overwhelmed with her progress, I had envisioned many sessions to get to this point. I felt her throat open and she pushed down, taking all of me. When her nose touched my pubic hairs, I felt such pride. I knew right then that she would do anything I wanted, no matter what.

The effect was as expected. When she felt the whole cock in her throat, she panicked and pulled out until only the head was in her mouth. I showed her my pleasure with her accomplishments. After all this, my cock was sopping wet with saliva and pre-cum, as well as my pubic hair and scrotum. With another loving look, she closed her eyes and took all of me in her mouth. My hands went automatically to her head to show her my pleasure. Her nose this time was buried deep against me, pressing against my pubic bone, trying desperately to take even more of me. My fingers lovingly felt around her lips that were encasing my cock. The realization of the situation caused me to jerk my hips forward in preparation of an ejaculation. I grabbed her face and forced her head back until only the head was in her mouth, then erupted in a gigantic explosion. Each spurt resulted in a swallow, which easily took all I had to give. When the orgasm dwindled to nothing, she sucked hard and drew out the remaining cum in the vein all the way to my prostate.

When she had finished, she crawled up until her head was on my chest. I cupped her cheek in affection, she responded by sucking my nipple. It was an act of love, not sexual since I was spent. I stroked her cheek as she suckled, then pulled her up to my lips. Her nipples rubbed my own as our lips met and opened, tongues caressing each other. I cradled her and whispered, “You have pleasured me, now it is time for you to be pleasured.” “Sir, I have been pleasured, my pleasure is pleasuring you.” I hugged her and told her that her orgasm would pleasure me. We got up and went into the kitchen.

She lay back on the table as before. I secured her wrists, pulled them over her head and restrained them to the table legs. This time I pulled her knees back until they were beside her chest. The effect was her ass was raised high over the table. Velvet ropes under her knees and tied to the same legs as her hands resulted in a raised offering that was splayed open for my access.

I teased her labia open, which only required a touch. She was already aroused and swollen. Because of her raised position, any accumulation of fluid in her cunt would remain there until it was completely full. This was beneficial for what I had in mind. I spread her lips farther apart and placed the tip of the new plug in her wet orifice. Her muscles flexed in anticipation as I prepared to push the device into her. I always enjoyed watching an orifice expand to allow something foreign inside.

The tissue gripped the tip and then spread to accommodate it. The skin around the orifice stretched becoming smooth and glossy, then hugged the shaft of the dildo as it slowly entered her. When it was halfway in, I pulled it out to allow more lubricant to coat the restrictive orifice. The opening remained partly open, allowing me to gaze partially into her passage.

The walls were flooded with her lubricant; any contraction would surely force some out to drip down to her anus. Placing the tip once again at the opening, I pushed it into her. This time it slid in easily, the sphincter was scraping off the coating on the dildo, which constantly aided in lubricating the orifice.

I felt the tip hit her cervix stopping the progress momentarily, then a gentle push, which pushed against the cervix and her womb. This allowed her sphincter to clamp down on the groove, trapping the shaft in her. Nestling it between her labia, I held it in place and folded the soft lips over the flange. It was working out better than I had hoped.

I placed my hand against her cunt lips and pushed in. A gasp spilled from her mouth as she felt the tip push against her cervix. This would work excellently when I brought the belt down across her sex.

Now that I was ready, I brought out the implements I would be using. I made sure she could see them as I laid them out. The 1 and one half-inch wide belt that was doubled over triggered a moan. She had an inkling how it might feel, but I doubted that she knew how awesome the sound of the doubled leather would be.

I picked up the cane first, lightly swishing it through the air, so she could identify the sound. Her moans were already prominent and we hadn’t even started. Fearing that her screams might alert the neighbors, I decided to give her some support in that matter.

A quick rummaging through the kitchen drawers yielded a wooded spoon. I pulled open her mouth and pushed the handle between her lips so her rear molars could clamp down on it. When she had clamped down on it, I explained that it would help endure the pain, but would also be a safety. If at any time she wished me to stop, all she had to do was allow the spoon to drop out of her mouth. Her eyes were wide in anticipation, but also aroused. She acknowledged understanding the act by nodding her head.

The time had come. I picked up the cane and drawing my arm back, brought the cane down across her buttocks. There was a swish as it cut the air and then a sound all it’s own as it buried itself in the flesh. As instructed, I left it there until the initial sting went away, then pulled it away quickly and watched the welt form. The blood rushing to the surface was more intense than the strike; at least that was what I was told. Her grunt seemed to support that.

While she was accepting the pain, I picked up the belt, folded it half and brought it down on her sex. The effect was exactly as I intended. Not only did the leather crush her labia, it pushed against the dildo jamming her cervix. There was a groaning scream this time.

I knelt down, spread her lips with my fingers and licked her clitoris. The huge dildo inside her pushed her clit up and made it more accessible. It didn’t take long, soon she was grunting and ready to climax. I moved away leaving her very near an orgasm, but not quite.

She was so close to cumming she didn’t see me pick up the cane, but she felt the slash as it landed just below the welt from the first hit. I watched as she now concentrated on the pain, and then pulled the cane away from the flesh. It was fascinating to watch the welt form, from red to blue as she squirmed.

This time I made sure she saw me pick up the belt. Knowledge is sometimes difficult to have. She knew how much it would hurt, yet she craved it anyway, her eyes told me that. The strike on her sex made her flinch; yet she moaned in passion also. I didn’t have to spread her lips this time, the swollen nubbin was just below the crease and found easily by my tongue. After only three strokes she was panting and close to cumming. I quit and picked up the cane.

Even though she was restrained to be immobile, I could see her trying to push her ass out to accept the blow. She not only craved it, she was helping me, trying to present a better target. This time I put my whole body into the blow. The sound was deafening. I was afraid to pull the rod away from the flesh; afraid I had split the cane, or split the flesh. Yanking it away I looked apprehensively. As the rod left the flesh, the area was white, no color at all. Then a transformation as the color came back as a red stripe, then slowly faded to a deep purple. It continued to swell into a furrow of a nasty bruise. Her anus was clenching in passion, there was no doubt the blow from the belt would push her over the edge.

I brought the belt down across her stuffed cunt and watched as she groaned and sought release. All the muscles in her crotch were working feverishly to gain the last little climb to the pinnacle. Her anus was clenching and opening, seeking penetration of anything. The overflow of juices from her vagina had coated it. I placed my finger there and felt it being drawn inside. Pressing towards her vagina, I could feel the dildo in her cunt, the membrane not much of a barrier. I tried to press the rod but my finger wasn’t long enough. I needed something that would go deep.

I remembered the ad for the cane, “Handle smoothed carefully, multiple coats of urethane, insertable”. I grabbed the K-Y and liberally coated the handle, then placed the end on her anus. The very end was small and slipped inside easily and then tapered to the bulk of the handle. The flesh stretched in an effort to allow entrance, but it was perhaps larger than she could take. Maintaining pressure, I twisted the cane as I pushed. Slowly it strained the sphincter until it slipped in as far as the widest part. The progress was slow but steady as it disappeared inside her.

Once the receding taper reached the entrance, the handle was almost sucked in by the contracting anus. I kept pushing until I decided it was as deep as the end of the dildo in her cunt. It was time for her reward. I pumped the cane back and forth in her colon at an angle so it would rub against the other rod in her cunt, then bent down and stroked my tongue up over her clitoris. I felt a warm spray on my neck and chest as the contractions in her vagina pushed the fluid past the dildo buried in her.