If you've read any of my stories, you know who I am and what I'm pretty much all about sexually. I stayed single until I was damn near forty and lived my sexual life to the fullest. There are many stories, some may seem to many like fantasy, but I've lived every one of them and written them down as well as I can recall.
Holidays are always special. For example, there are thousands, (maybe tens of thousands) of stories, told and untold, about wives and lovers allowing their sex partner to sample anal sex as a special birthday, anniversary, or even Christmas or Hanukkah gift. Anal sex still seems to have enough mystique about it for both sexes, to merit a special place in the intimacy scoresheet of both men and women.
The first time I had anal sex was with my very first sexual partner and it happened on Christmas Eve. She was a beautiful girl I'd been hot for quite a long time and ended up dating as my first serious romance. That winter night in her family's living room, after everyone else had gone to bed, and were hopefully fast asleep. we were screwing in front of the slowly dying fire in the big brick fireplace. The lights on the Christmas tree gave off a warm romantic glow. It was close to two in the morning and we were sure nobody would come downstairs. Even if someone had to use the bathroom, the main facility was on the second floor, and for as many times as we'd done our late-night exploits nobody had ever come down.
At that young adult age, we were both in the experimental stages of our sexuality and somebody, probably me, mentioned that was too bad I always had to pull out of her tight little pussy and either cum on her belly, breasts, or back depending on the situation. Often, with enough warning, I'd cum in her mouth. She either enjoyed or didn't mind swallowing my cum or having to clean up her body each time, but I'm not sure which as I was young and stupid and never thought to ask.
Anyway, this time, we agreed that no harm would come from squirting my load in her butt. It would eliminate any clean-up or getting jizz on her mom's carpet, so hey...win/win.
She had a perfectly shaped, round, firm butt that I always liked to walk behind, and maybe once or twice had entertained thoughts of fucking. Truthfully, neither of us had any experience using the alternate orifice as a point of entry, as our mutual encounters were the only ones either of us had ever had. The more we thought and whispered about it that night, the more we wanted to try it.
While we were discussing an anal finish we were having a slow, gentle fuck as we always did when her family was sleeping upstairs. Anticipation and youth made my cock incredibly hard, and she was dripping a river of pussy juice on the folded towel we'd learned to put under her ass while we fucked. When I felt my orgasm coming, I whispered to her "I'm coming."
As I withdrew from her soaking pussy, she raised her legs and put her feet over her head positioning her tight little pink butthole at the perfect angle. She reached down and guided my slippery cock to the chosen opening, and pushed upward against its glistening head. Without drama or hesitation, the head of my cock was suddenly in the tightest place it had ever been. Only the very head, but the full head, of my cock was inside her butt, and it felt like it was in a fire. It immediately began to pulsate as stream after stream of cum made the voyage into her virgin ass.
