See here for part 1

She was soaking wet, still recovering from her first orgasm of the night. Her tight body was writhing on my bed. I raised my head up and surveyed the results of my handiwork. Her eyes were closed, mouth open, breathing hard. Her porcelain skin was flushed where exposed, an irresistable pink, interrupted by freckles. She still had her tight black dress on, hiked up around her waist. I couldn't wait any longer. I stood up and, at the edge of the bed, grabbed my cock and tapped her clit gently with its head. She inhaled sharply and twitched, opening her eyes in sudden awareness and surprise. A huge smile spread across her face as she made eye contact with me. She nodded, and (I should have gotten better verbal consent, and a condom for that matter, but as I said, this was a long time ago lol) I took this as my queue. I pushed the head of my cock up against her threshhold, meeting with some resistance. She let out a low moan and it spurred me on. I pressed harder and slid in down to the thickest part of my cock, stretching her open and causing her to gasp, then laugh at herself. Now I smiled and started slowly thrusting just at this depth, eyes locked with hers. "Yes, foxtrotalphapapa," she whispered, smile fading, nodding while keping eye contact. Her slippery cunt felt even better than her mouth and I grunted with satisfaction and desire for more as I gradually built speed. I suddenly wanted to kiss her so I bent down, slid my arm under her, picked her up and moved her back, while getting on my knees on the bed. She smiled and purred at being manhandled. I put my elbow down next to her and kissed her, picking up the rythm again. She started to move to meet me, matching my rythm, taking me even deeper.

"Fuck, you feel so good" I whispered into her ear, trying to focus so as to keep up the pace without cumming. I decided to take a break and sat up, still on my knees, with her legs spread, over mine. I grabbed her ass with both hands, lifted her up a bit, and started to thrust like this, slow but hard. "Ah!" She vocalized, mouth and eyes wide with pleasure. Once I neared orgasm again, I dropped her ass back on the mattress, and started peeling her dress up over her head. She wasn't wearing a bra, so now her full body was exposed to me, the only scrap of clothing left, her small gold crucifix. I licked my thumb, put my hand on her mound, thumb on her clit, and rubbed slowly while thrusting at the same pace. "Mmmf yes," she said, eyes closing and chest flushing again. Not much more of this and I felt like she was getting very close, so I slowly eased myself in as deep as I could in this position, kept rubbing her clit, and started nudging her deeply, never really pulling out. Her perky tits were bouncing slightly and she arched her back, letting out a grunt, rolling her eyes, and came again, hard.

Seeing her lose control was so sexy I almost lost it myself, but I somehow managed to pull through. I decided that I wasn't fucking around any longer though, soon I was going to pound her hard until I came. First I gave her some time to recover. I laid back down and nibbled her ear, kissed her neck, sucked her nipples until they were both erect, all the while gliding my cock in and out with long, slow strokes. Some women have trouble taking my full length, but she was very well warmed up at this point, and handling it perfectly. I figured I should let her know how well she was doing, so I whispered in her ear, "I love how you're taking my cock so deep. Your pussy is amazing". I picked up the pace, still giving her long, deep strokes."Oh my god, yes fuck me" she proclaimed as I continued to rail her, faster now. I got up on my knees again, grabbed her waist and started really fucking her, pulling her body down onto my cock and letting the recoil bounce me back out again. She was slender but I had everything on her body capable of it jiggling. "Fuck yes!" she cried, my rock hard cock ramming into her deepest part. I held on like this for what seemed like forever (but was probably considerably more brief in all honesty), then said "I'm gonna cum, where do you want it?!"

"Cum all over me!" she replied breathlessly, which I took to mean "not inside". It was a good thing she responded quickly as I had just enough time to pull out and shoot rope after rope across her writhing form. She glistened with my seed in the dim light of my bedside lamp and I collapsed next to her, spent. After a few moments, I got up and got her a warm damp washcloth, we had some pillow talk, and soon enough I was fast asleep with her beside me.

Believe it or not there's more to this one. I guess I'll do 3 parts.

Note:

This is the first story in a series of stories that are meant to be cathartic for me and hopefully enjoyable for you. Throughout my life I have been insecure sexually to varying degrees despite having a big dick. As I look back, I realize I have many regrets: times I wish I would have been more assertive, less reserved, more confident, more dominant, etc. Each of these stories starts out completely true, although I may change some minor details to protect identities, or fill in things I've forgotten, obviously. Then at the point where my regret begins, they diverge into fantasy. They will be mostly true and embellishments will not have anything to do with my penis size or my patners' reactions to it, nor any other aspect of my or my partners' bodies for that matter. Feel free to guess where the divergence takes place or just enjoy the story. I hope I'm not breaking the 4th wall too much for the rules of the sub by admitting part of the story is false.