Thursday's Session
I met my new friend for another session Thursday evening. I arrived at her place with the wine and the new horse cock dildo she wanted (still in the box as she had instructed). I had done my best to stretch out my hole by wearing a large plug Wednesday evening, and most of the day on Thursday. Still, physically I wasn't prepared for what was to come.
Upon arrival I poured her a glass of wine and gave her the gift. I should note that dildos I have ordered in the past were relatively light, but this cock has to weigh every bit of ten pounds. It's nine inches which is intimidating enough, but the width and girth of it was far more than anything I have experienced before. I've been fucked by a Doc Johnson dildo before which is nearly 8 inches and 1.75 wide. That felt like a truck going through me. This thing is bigger...much bigger.
She unboxed it and it was clear by the look on her face that she loved it. I think it also aroused her that there was genuine fear in my face as I told her I wasn't confident in being able to take that much. I begged her not to hurt me and suggested we go back to using the smaller dildo that we used last Sunday. She told me this was going to be her dildo of choice from now on and I had better get used to it.
As she drank the wine (I abstained), she shared a lot about what turned her on about wielding a cock of that size. To her, it was like I was a virgin and she was going to take my cherry (as you will find out was a very prophetic statement). It was going to hurt, but in the end I would come back to it and want more. In fact, she said eventually I would be begging her for it.
I wish I shared her confidence. It's true that I have a lot of experience with anal sex, but this cock was like going from the amateurs to the pros. You might see some porn dude taking a strapon this size, but those so-called "professional subs" have been stretching themselves for years to take dildos of that magnitude. The fantasy is much different from the reality. For me at least, anal sex is pleasurable with smaller dildos. The larger the cock, the more it hurts.
So here's what happened. She had trouble in the beginning because the size of the dildo didn't really fit the size of the harness. The first challenge was getting the cock through the metal O-ring on her dildo harness. She wound up having to grease the ring and harness and after about five minutes of twisting it back and forth, it finally made it through the ring. The cock tapers off just a bit as you get closer to the base. Once you get it through the ring a few inches it gets easier, and then the last four inches or so it slide right in place.
She stripped and told me to do the same. She saw that my chastity device was still in place and examined the lock to make sure it was the same number as Sunday's. Of course, it was. She asked me if I was horny, and I nodded back at her. "Good", was all she said.
She felt the weight of the dildo, and I also had to help her tighten the harness so as to have better control of the cock. She lifted the dildo up, and while she was holding it she told me to pull the harness straps as tightly as they would go. Then she dropped the cock and it hung from her waist swinging back and forth like a pendulum. There was a part of me that wanted to run for the hills at that point.
She pushed me to my knees and told me to suck it. I stretched my mouth as wide but I could only get an inch or two deep. She thrusted my face like she did on Sunday but the dildo didn't make it any further. I could tell that frustrated her. She told me that my mouth would have to be trained as well as my ass.
After a while she gave up trying to fuck my face and force the thing down my throat. It was time to see if she would have better results in my ass. She told me to get on the bed ass up, face down, and holding my ass cheeks apart. She lubed me good and did the 1 finger, two fingers, three fingers, four fingers exercises. She also used the dildo that was used on Sunday to stretch things deeper inside me. To her credit, she knows what she's doing when it comes to ass play and taking the time to stretch me out was critical to the success of her mission.
After about thirty minutes of this she had me stretched enough to nearly fist me, which by the way would have also been a first for me. I was enjoying what she was doing, and my locked cock was dripping precum. Psychologically I was more receptive now for what was about to come. Physically I was more relaxed than when I had first watched her unbox the monstrous phallus.
She wanted to see the expression on my face, so she told me flip over on my back and she lifted my legs and rested them on her shoulders. She put the head of the cock directly on my hole and pushed....and pushed....and pushed some more, but hole wasn't cooperating, so she came up with a new plan.
She kicked me off the bed and told her lie on my back on the floor with my legs raised. She was utilizing the jackhammer position so that her weight would come down on me and add extra power to her thrusts. She had a look of determination as I stared at her from below. I knew this was the moment of truth.
With my asshole pointed skyward she guided the cock down and when perfectly positioned allowed her weight to come down on it. I have experienced all kind of pain in the BDSM world but I can honestly say this hurt more than anything previously. The hole opened just enough to allow an inch or two and it felt like I was being split in half. I let out a scream, and begged her to stop.
She left the dildo inside me and told me to relax. She didn't push it in any farther, but neither did she remove it. She left it there while I struggled to accommodate it. I tried to embrace the pain, and thoughts of masochism were running through my head. She was giving me exactly what I needed and deserved, so take it like a man....or take it like a bitch if you prefer.
It was several minutes before I stopped shaking, but once I did she announced that she was going to push it an inch deeper. She allowed her weight to come down on me a bit more, and I felt the same pain return. I was biting my lower lip and was in a full sweat. In all my pain I open my eyes and looked at her standing above me like a Goddess. She would probably be considered an average looking middle aged woman to many men, but at that moment she was the most beautiful woman in the world to me. Her strength, her power, her determination, her kinkiness, her sadism, her will....all made me desire her like no other.
The cock wasn't even half inside me, but she had enough to work with to start fucking me. In the jackhammer position, it's a lot of knee bending and so it was as she was in an exercise class. As she was doing this the cock was gradually making it's way deeper. Make no mistake, it still hurt like hell but there was also an element of relief as she would withdraw before coming down on me again.
She was happy now that she had something to work and so she put me back in the missionary position so she could watch my face again. This time yielded better results. She was able to remove the cock completely and then shove it in back it about half way. Though the pain was still there, it wasn't as bad. I can't say that I really enjoyed it at any point, but I was able to reach sub space and embrace being fucked and used.
We went on this way for a while, and then she suddenly stopped. "Oh shit, you're bleeding."
She took the cock out of me and sure enough there was a little bit of red on it. The part about "popping my cherry" became reality. Just like that, the session ended. She didn't want to hurt me further, that was a good indicator that it was time to quit.
She broke character and apologized profusely. I told her that I was okay, and this was to be expected. She suggested I see a doctor, but I've experienced blood before when toys have been increased in size. It's normal and goes away. I told her the same thing was going to happen until the hole is permanently stretched to accommodate larger sizes.
So I went to the bathroom and cleaned myself up, and we talked for a while on the bed about what happened. She said she loved taking me that way, but didn't want me to wind up in a hospital. I told her that if she gave me the dildo for a week or two, and I was able to practice on myself it probably wouldn't happen again. I told her that I was disappointed in myself for only taking about half of it. I wanted to feel her skin slapping against mine.
Then I told her that I felt closer to her from the experience and her eyes lit up. Once I said that, she immediately snapped back into Domme mode. She let the bedroom and returned with a pair of scissors and cut the plastic lock off my chastity device. She roughly removed it from my penis and I let out a yelp as my cock felt it's newfound freedom. In five seconds I was hard as a rock with her so much as a touch.
She grabbed me by the base of the cock and started masturbating me. I was ashamed after about three strokes I was spurting all over my chest and stomach. I had no endurance whatsoever. She continued squeezing the last few drops out and stopped. She took two fingers and scooped up my cum with them and fed them to me. I sucked on her fingers until they were clean, and swallowed my own cum on her command.
She told me she had to be up early and it was time for me to leave. She said I needed to take the big dildo (still in the harness) with me and practice, and she got a new plastic lock for the chastity device and locked up my cock again. She walked me to the door and gave me another one of those dominant kisses I alluded to in my last blog post. God I love those things.
She said she'd call me and let me know when she needs me again. So in the meantime practice, practice, practice.
Upon arrival I poured her a glass of wine and gave her the gift. I should note that dildos I have ordered in the past were relatively light, but this cock has to weigh every bit of ten pounds. It's nine inches which is intimidating enough, but the width and girth of it was far more than anything I have experienced before. I've been fucked by a Doc Johnson dildo before which is nearly 8 inches and 1.75 wide. That felt like a truck going through me. This thing is bigger...much bigger.
She unboxed it and it was clear by the look on her face that she loved it. I think it also aroused her that there was genuine fear in my face as I told her I wasn't confident in being able to take that much. I begged her not to hurt me and suggested we go back to using the smaller dildo that we used last Sunday. She told me this was going to be her dildo of choice from now on and I had better get used to it.
As she drank the wine (I abstained), she shared a lot about what turned her on about wielding a cock of that size. To her, it was like I was a virgin and she was going to take my cherry (as you will find out was a very prophetic statement). It was going to hurt, but in the end I would come back to it and want more. In fact, she said eventually I would be begging her for it.
I wish I shared her confidence. It's true that I have a lot of experience with anal sex, but this cock was like going from the amateurs to the pros. You might see some porn dude taking a strapon this size, but those so-called "professional subs" have been stretching themselves for years to take dildos of that magnitude. The fantasy is much different from the reality. For me at least, anal sex is pleasurable with smaller dildos. The larger the cock, the more it hurts.
So here's what happened. She had trouble in the beginning because the size of the dildo didn't really fit the size of the harness. The first challenge was getting the cock through the metal O-ring on her dildo harness. She wound up having to grease the ring and harness and after about five minutes of twisting it back and forth, it finally made it through the ring. The cock tapers off just a bit as you get closer to the base. Once you get it through the ring a few inches it gets easier, and then the last four inches or so it slide right in place.
She stripped and told me to do the same. She saw that my chastity device was still in place and examined the lock to make sure it was the same number as Sunday's. Of course, it was. She asked me if I was horny, and I nodded back at her. "Good", was all she said.
She felt the weight of the dildo, and I also had to help her tighten the harness so as to have better control of the cock. She lifted the dildo up, and while she was holding it she told me to pull the harness straps as tightly as they would go. Then she dropped the cock and it hung from her waist swinging back and forth like a pendulum. There was a part of me that wanted to run for the hills at that point.
She pushed me to my knees and told me to suck it. I stretched my mouth as wide but I could only get an inch or two deep. She thrusted my face like she did on Sunday but the dildo didn't make it any further. I could tell that frustrated her. She told me that my mouth would have to be trained as well as my ass.
After a while she gave up trying to fuck my face and force the thing down my throat. It was time to see if she would have better results in my ass. She told me to get on the bed ass up, face down, and holding my ass cheeks apart. She lubed me good and did the 1 finger, two fingers, three fingers, four fingers exercises. She also used the dildo that was used on Sunday to stretch things deeper inside me. To her credit, she knows what she's doing when it comes to ass play and taking the time to stretch me out was critical to the success of her mission.
After about thirty minutes of this she had me stretched enough to nearly fist me, which by the way would have also been a first for me. I was enjoying what she was doing, and my locked cock was dripping precum. Psychologically I was more receptive now for what was about to come. Physically I was more relaxed than when I had first watched her unbox the monstrous phallus.
She wanted to see the expression on my face, so she told me flip over on my back and she lifted my legs and rested them on her shoulders. She put the head of the cock directly on my hole and pushed....and pushed....and pushed some more, but hole wasn't cooperating, so she came up with a new plan.
She kicked me off the bed and told her lie on my back on the floor with my legs raised. She was utilizing the jackhammer position so that her weight would come down on me and add extra power to her thrusts. She had a look of determination as I stared at her from below. I knew this was the moment of truth.
With my asshole pointed skyward she guided the cock down and when perfectly positioned allowed her weight to come down on it. I have experienced all kind of pain in the BDSM world but I can honestly say this hurt more than anything previously. The hole opened just enough to allow an inch or two and it felt like I was being split in half. I let out a scream, and begged her to stop.
She left the dildo inside me and told me to relax. She didn't push it in any farther, but neither did she remove it. She left it there while I struggled to accommodate it. I tried to embrace the pain, and thoughts of masochism were running through my head. She was giving me exactly what I needed and deserved, so take it like a man....or take it like a bitch if you prefer.
It was several minutes before I stopped shaking, but once I did she announced that she was going to push it an inch deeper. She allowed her weight to come down on me a bit more, and I felt the same pain return. I was biting my lower lip and was in a full sweat. In all my pain I open my eyes and looked at her standing above me like a Goddess. She would probably be considered an average looking middle aged woman to many men, but at that moment she was the most beautiful woman in the world to me. Her strength, her power, her determination, her kinkiness, her sadism, her will....all made me desire her like no other.
The cock wasn't even half inside me, but she had enough to work with to start fucking me. In the jackhammer position, it's a lot of knee bending and so it was as she was in an exercise class. As she was doing this the cock was gradually making it's way deeper. Make no mistake, it still hurt like hell but there was also an element of relief as she would withdraw before coming down on me again.
She was happy now that she had something to work and so she put me back in the missionary position so she could watch my face again. This time yielded better results. She was able to remove the cock completely and then shove it in back it about half way. Though the pain was still there, it wasn't as bad. I can't say that I really enjoyed it at any point, but I was able to reach sub space and embrace being fucked and used.
We went on this way for a while, and then she suddenly stopped. "Oh shit, you're bleeding."
She took the cock out of me and sure enough there was a little bit of red on it. The part about "popping my cherry" became reality. Just like that, the session ended. She didn't want to hurt me further, that was a good indicator that it was time to quit.
She broke character and apologized profusely. I told her that I was okay, and this was to be expected. She suggested I see a doctor, but I've experienced blood before when toys have been increased in size. It's normal and goes away. I told her the same thing was going to happen until the hole is permanently stretched to accommodate larger sizes.
So I went to the bathroom and cleaned myself up, and we talked for a while on the bed about what happened. She said she loved taking me that way, but didn't want me to wind up in a hospital. I told her that if she gave me the dildo for a week or two, and I was able to practice on myself it probably wouldn't happen again. I told her that I was disappointed in myself for only taking about half of it. I wanted to feel her skin slapping against mine.
Then I told her that I felt closer to her from the experience and her eyes lit up. Once I said that, she immediately snapped back into Domme mode. She let the bedroom and returned with a pair of scissors and cut the plastic lock off my chastity device. She roughly removed it from my penis and I let out a yelp as my cock felt it's newfound freedom. In five seconds I was hard as a rock with her so much as a touch.
She grabbed me by the base of the cock and started masturbating me. I was ashamed after about three strokes I was spurting all over my chest and stomach. I had no endurance whatsoever. She continued squeezing the last few drops out and stopped. She took two fingers and scooped up my cum with them and fed them to me. I sucked on her fingers until they were clean, and swallowed my own cum on her command.
She told me she had to be up early and it was time for me to leave. She said I needed to take the big dildo (still in the harness) with me and practice, and she got a new plastic lock for the chastity device and locked up my cock again. She walked me to the door and gave me another one of those dominant kisses I alluded to in my last blog post. God I love those things.
She said she'd call me and let me know when she needs me again. So in the meantime practice, practice, practice.
8年前
