I didn't have many "firsts" that I could give my ex-husband, but I did save my anal cherry for him.
It wasn't a conscious thing -- I had been horny and open to most anything since college, and seemed to have an amazing ability to get myself in sexual trouble ("sexual sin," my evangelical sister, Amber, would put it). Early on, men loved fucking me from behind -- my ass was a magnet for guys, and they would tell me how sexy it looked to fuck me from behind, seeing my long back spread into my hips, and back then I also had longer red hair flopping around. I let a few men finger me in the ass and it felt good, especially the friction along the sensitive skin of my perineum. But I was a little tight girl, and I was afraid to let them fuck me there. If they tried, I would pull forward and change the position. A couple begged, but I was afraid of the pain.
My first husband was if nothing else a gentleman and a gentle, caring lover. He also had a nice, average cock -- nothing monstrous or scary. That definitely helped his cause here. For whatever reason, after I turned 30, I began to think more and more about anal sex. One long Sunday afternoon was spent in bed, fucking, sucking and him giving me exquisite cunnilingus. After a brief nap, we were at it again. Did I tell you I was wearing a white garter belt and sheer white stockings? He was fucking me missionary style and I looked up at him.
"I want you to fuck me in the ass," I said.
His face was like that of a man who had just won the lottery, but I could see he was trying to be cool about it. He got the KY out of the bedside table drawer and I got on my hands and knees. I felt his cock push back in my pussy, and my mini-orgasm contractions began almost immediately. He fucked me awhile this way, gently, rhythmically, then breaking into a hard, fast fucking ("Don't come yet," I gasped) before slowing down again.
I heard the plastic pop on the KY and felt the cool gel around the sensitive edge of my ass. He fucked me slowly and slipped a finger inside my anus. It felt good, as usual. I was very aroused, but also apprehensive. The next feeling was fuller: he has put two fingers inside and was finger-fucking my virgin ass. It felt very odd and arousing to process the sensation of his cock in my pussy and this thickness in my anus. My pussy flooded with new lubrication, mixing with the sperm I already had inside me. He pushed my shoulders down and I put my head on the sheets, my hands in front of me to steady myself.
"Does that hurt?" he asked.
His fingers went away and he pulled out. A few seconds later, the head of his cock was rubbing against my perineum. It felt great and he didn't give me time to change my mind. He pushed into my well-lubed anus. This was new. Different from the feeling of cock-in-pussy. It wasn't quite as intense physically, except for the feeling of being very filled up. Now he felt huge and even though he was fucking me slowly and the rubbing against my perineum was very, very nice...this sharp pain overtook me.
"Hurting," I managed as he pushed me forward and pulled me back with his strokes and his hands steady on my hips. But I knew he was a gentleman, so I added, "Don't stop." I had no pain when I lost my pussy cherry -- I was an athletic girl -- so this was new and I had nothing to compare it.
I tilted my pelvis and it hurt less. I thought about what a taboo I was breaking considering my repressed upbringing and almost came from the mental turn-on alone. Pain and pleasure. "Fuck me in the ass," I half groaned, half screamed. And he did, until he screamed and ejaculated inside me.
How long did he last? To me it was about twenty minutes -- he claimed it was about five. I hurt for days afterward. But we were back at it soon (pun intended), and I learned how to angle myself to handle it. He grew to love it, not only because he loved my ass, but because he got into the taboo turn-on thing, as well. And he was always good never to try to fuck my pussy after he had been inside my ass. Anal sex was never my favorite, but I do love it in its special way, especially when it brings out my inner submissive. I've had big guys try to fuck me in the ass, but they can rarely get far inside. My ex -- he could do deep and it got to where it felt great, and I loved feeling semen leak out of my ass. So forbidden. Linda Sue, you bad bad bad girl.