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Started Anal Training [26M AR]
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ShhNobodyHasToKnow is in Arkansas
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Disclaimer: Iā€™ve never been in a non traditional relationship. Iā€™m not currently looking for any relationship. Just sharing my first legitimate training session.

Day One __In between relationships I get so bored of just taking care of myself. My partners always have a hard time finishing me off. No lack of talents and surely not lack of sheer effort but Iā€™m a hard nut to crack I guess. I wondered if there was something wrong with me for a while but decided maybe Iā€™m not guiding them right. So Iā€™m starting this little experiment on myself to see if I just need another form of stimulation to finish or am I actually defective. Thatā€™s the excuse anyways.šŸ™„ __Once the coast is clear I set the mood for myself. Background noise, lighting, and toy prep. A small plug and two dildos. After a bit of prep work I mounted the 6in to the platform Iā€™d scrounged up. I sat back on my heels and sized it up. Itā€™s realistically sized, nothing too intimidating. Next comes the lube. I pour a generous amount for what Iā€™m working with and start with some self care. Iā€™m already dripping excitement but weā€™re try to stay focused. I need to warm up. I peak myself slowly and while my cock is trembling I slip a finger inside. Still trembling I stroke myself a few times until thereā€™s no resistance. I take a small break, mentally building myself up for the real start of the experiment. More lube. Time for the plug. It stretches me more than I anticipated. Itā€™s the smallest in the set for fuck sake. With a few attempts it finally enters, my cock twitches and drools at the feeling. Once itā€™s fully seated I focus on whatā€™s in front of me and get comfortable with whatā€™s behind. I enjoy the build up as I work both myself and the object. Once everything is slippery to satisfaction I begin.šŸ˜®ā€šŸ’Ø __Eyeing the makeshift platform, I try to think of the best angle of approach. Ultimately deciding that regardless of the start, pleasure should take over and the path of least resistance will slowly become obvious. I make my decent and all is welcomed. I slowly fall until the sensation was too much and caused me to tense with ecstasy. That was the starting point. I lifted myself back up, readjusted, and went again. The stretching wasnā€™t nearly as troublesome as the depth. I needed deeper. I pressed past the previous point and continued to work down. More. Fuck more. More, more, cold. My ass had made contact with the base? It sends a small shock through my body but this time there was no discomfort. The tensing passes and I felt Iā€™d earned a reward so I took some time to feel myself. With every twitch from my dick there was a bolt of pleasure running inside me. I stay down and keep going. At this point Iā€™d found a comfy position where I could sit on my soles. Iā€™d started bouncing without any intention. I rock myself back and thrust down and in. Thatā€™s the spot. I barely felt it but it was there. Something new and intoxicating. I reward myself more and place my other hand on the ground for support. The rocking is rough at first but, as predicted, the correct approach was found. I find a rhythm but as soon as itā€™s found it disappears. The pleasure drives me over the edge and I ruin the rhythm with my own desperation. I keep trying, not knowing how much time had passed. Every stroke was electrifying, powering the next. The finish was on track to be but fading. I needed more.šŸ˜« __I realized the only other option. Massive. Unreal. Pringles can size? Fuck, I was desperate. More lube. Stay seated until the replacement is fully prepared. Grind. Drip. Breathe. Fuck I was gasping. I take my hand off of the new comer. The lube sparkles against the light before dripping to the platform. A quick timeout, changed the star, and here we go. If I can take the tip I can at least stretch myself for the next time. It pushes past with a bit of effort. Itā€™s fucking huge, my legs are trembling. My cock is dripping from tip to platform. Lower. Thereā€™s discomfort again. I try to lift myself up but the sheer length doesnā€™t allow for much relief. I need to readjust. I try putting strength into one leg but it collapses against my will. The other following suit quickly after. Fuck. Iā€™m struck and losing strength to keep myself up. Iā€™m slipping. It slowly pulls me down, finding its way deep into my belly. The pain fades as soon as itā€™s filled me. Iā€™m not even halfway down. I take a moment to regain composure from my much quicker than anticipated way down. Thereā€™s a puddle now formed on the platform. Much more precum than my normal. I canā€™t resist and again reward myself with attention, self care. šŸ’… __Immediately my body is delighted and offers more room within. I let it climb deeper until thereā€™s no more. Iā€™m over halfway now. My body wants to rock and grind but my legs are of no use now. All I can do is pleasure myself and tense on this fucking monster taking me under. Itā€™s not enough. I finally gain enough strength and confidence to move. I manage to take a knee and get one foot planted. Then the other. Then lean back in a squat position. I grab the bed for support. I try bouncing and the tensing suddenly becomes more of a gentle squeeze as the object starts escaping. I drop my ass with the same down and in motion. My whole body trembles. This would work. Faster. Itā€™s getting easier to take. I let more escape only to chase it back down quicker each time. I lose strength again. I fight desperately to stay up high but Iā€™m trembling and losing ground. As another inch slips I try to make a game plan. Iā€™m panicking, thereā€™s nothing to cling to with enough support to keep me from falling. Another inch. Thereā€™s no pain but the pressure of this beast filling me up in becoming too much. Another inch. My ass is on my heels. I managed to support my lower back on the bed frame as not to fall backwards. The intruder filled me up entirely. Still stroking, I let my body go limp and accept my fate. I barely get to touch myself before I squirt all over my legs. šŸ¤¤

Day Two tonightšŸ™Œ

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4 months ago