I had a shared 'first time' for two experiences. It was the first time I had anal sex and then had my partner eat my pussy. I underestimated how painful anal sex would be; I knew nothing of how to make it better or how to prepare myself for it. My partner was equally unprepared, although he seemed to enjoy himself.
I remember all the care he took in making me comfortable, easing my head down to the bed, as he gently massaged my pussy. I remember getting wet for him, but not caring. I used to think it was an embarrassing thing to be so wet and disgusting. I remember him rubbing his hard cock between my legs and getting it drenched in all my juices. Feeling his cock against my clit made me so excited for what was to come.
He eased the tip of his cock into my ass and I remember being surprised at how good it felt. He wasn't very far in and he just left his tip and moved it with his hand. It felt surprisingly good to have his cock massaging the rim of my asshole. He put his hand on my back, as if assuring me it was going to be okay (liar!). He moved his cock a little deeper into my ass, hardly a centimeter, but I felt everything. It felt like a thin little wall in me was breaking; he might as well have slammed his cock all the way inside! I let off an embarrassing moan and he asked me if I was okay. I whimpered 'yes', but he hesitated to continue. We were so scared. It's kind of funny now.
He moved his cock inside me some more. He was doing his best to ease his cock inside my ass without trying to hurt me. He didn't understand that it hurt no matter what and that I just wanted him to cum and get this over! Every time his cock pressed into my ass it felt like my insides were tearing. We used no lubrication; I never thought I'd be doing this! There was no bracing against the pain. Even with him being gentle, the pain of his cock forcing its way inside me left me crying into my fluffy pink pillow. I remember pleading and whimpering into the pillow for this to end soon. I didn't think I could do this much longer, but I didn't want to be a bad partner. He was a little older and, as stupid as this sounds now, I wanted him to like me. I felt like stopping would make him hate me.
It hurt so bad to feel him pressing against my insides, but when he was almost completely in he jammed that last centimeter of his cock in so fast I couldn't help but offer an ineffectual squeak into the bed sheets. He asked if I was okay and I nodded, without removing my head from the bed. I felt so impotent. I felt like a doll meant for abuse. It turns me on now to think of, though in the moment I couldn't think passed the pain. He moved faster inside me and I couldn't help but sob. I tried to make sure he couldn't hear me, so he would finish and we could forget ever doing this again. He never stopped. He moved faster and faster; I remember his hips slamming against my backside, as his pace continued to pick up.
His cock invaded my tight virgin asshole. My body was so tense. All I could feel was his cock invading my ass! I bit down hard on my lip to take away from the pain, but nothing could distract me. I felt so awkward and ashamed, embarrassed and humiliated, but I didn't want him to stop. I thought this was sex; this is what it's about. I thought I needed to serve my partner however he wanted, to answer to the demands of his body. He moved his cock faster and faster inside my raw asshole. The pain was constant and seemed to shoot deeper inside me each time he jammed his cock a little further. I drooled over my blankets. I was such a mess, as I made these embarrassing whimpering noises. I couldn't help myself and I know by then that he must be ignoring my cries.
He would force it all the way inside me and hold it there, even with my body pushing against him. I couldn't deny his power; my body succumb to every inch, until he finally came and I felt his cum dripping inside me. I felt his cock seize inside my sore asshole and the last shock of pain came when he finally pulled it out. For a long, uncomfortable few seconds, he left his flaccid cock in my ass and hold me to him, enjoying every bit of our moment together. He held me in place and no matter how I wanted this to end I couldn't, I didn't possess the power to end it. He did.
I remember feeling his cum dripping into my ass and feeling so disgusted by it, as it oozed inside me. I remember panicking and thinking it would be with me forever or like slip down into my pussy and I'd get pregnant, so I stayed there longer so it would disappear inside me. I hated the feeling of being full of his cum, especially inside my ass, but I had no say in the matter. When he finally pulled out of me it came as an amazing relief. I was so sore, but I couldn't move. I just sit there with my throbbing ass in the air, breathing hot air against the bed and making my face sweaty and red. I tried to wipe away the tears and couldn't. He saw them and said nothing.
He lay me down on my back and without a word lowered his head between my legs. I felt his tongue sliding inside me. It took a while of him tasting me for the pleasure to overwhelm the pain, but when it did it hit me so hard. It mixed with the pain. I could feel my body still so sore from before, but now the pleasure was rising over it. His tongue rolled over my clit and deep inside me. He'd never done this before and it was awkward, but every time he hit my clit it was like a pulse of pleasure shocking me out of the pain.
I felt the pain throbbing inside my body and the pleasure went with it. It felt good to have him between my legs, making it all better, taking care of me after he'd caused me so much pain. He moved his tongue all along my dripping pussy and when I finally came my body rocked out of control; he pulled me into him and tasted every bit of me. He seemed to love it and I loved when he kissed me and I could taste myself. I wasn't thinking of how disgusting it was to taste my own pussy on his lips. I just wanted a kiss. I needed to kiss him to show him how good he'd made me feel; how there was nothing that could get in the way of me making him feel good. I'd given to him and him to me and for a while that was all we needed.
Source: reddit.com/r/gonewildstories/comments/3pl8we/two_first_times_pleasure_and_pain
Incredible writing. Have you done anal since then? And if so, how does it feel?
Thank you! Yes, I have done it again, but it still does not feel… comfortable. It’s never been as bad as this experience and sometimes it can feel good, though I’ve never had an orgasm from it!
You’re incredibly lucky your anal walls didn’t tear….always always use lube for anal, especially if you’re still new to it!!!!
I know now and during how stupid I was, and oh god am I glad that didn’t happen!