Welcome to another fictional journal entry from "The Cougar Chronicles". This chapter was inspired by a discussion thead on fetlife that I read this morning. Hope you enjoy it!
Years ago, long before I had any concept at all of D/s, kink, etc. I found myself in a situation of being asked by my partner of the time to consider a sexual activity that had considerable baggage attached to it from my childhood. What had happened to me as a child was never explained to me before or after. It happened at the hands of trusted adults in a clinical setting, but was a significant violation of my young body and a real test of my trust for the people involved. It was uncomfortable to the point of being painful. I lost control of my bodily functions as a result and was extremely embarrassed afterwards. The response of both adults afterwards was no different than if I had just had my weight checked. What had actually occurred was a doctor with very large hands had stuck two of his very large fingers in my ass in order to conduct an internal examination of my lower bowel and abdomen. Remember, these were the days before CT scans and MRIs. I hadn’t reached puberty and my anal cherry had been popped.
Getting back to the request my young partner had made of me. He didn’t rush me and I gave it much thought. I was not at all coerced and I cared deeply for him so I agreed to try. We were both under 20 and fairly inexperienced so it was not very pleasant for me. In truth it was fairly painful, but I endured and at the end, seemed to have horrified him when he realized I had cried silently through most of it. He held me and comforted me, and then thanked me profusely as he began to understand what had happened and why I didn't ask him to stop. Through the spontaneous aftercare and discussion that followed, I came to feel very different than I had during my first anal experience. This time instead of being embarrassed, I felt his gratitude and love and heard pride in his voice when he talked about what I had been willing to do for him. What a very different experience this was.
Even without the internet, I was able to find some “naughty” books (actually several geared towards gay men) that actually had some practical information about anal sex. I quickly understood that body position, a good lubricant and patience go a long way to ensuring a positive experience for the receiver. Armed with new information and a tube of KY Jelly from the local drug store, I planned a surprise for my then-boyfriend.
It was a Friday night and I had dropped over to his place to hang out with him and his room-mate. The usual routine was that we would hang out together for a while, maybe watch a movie and then his room-mate would go on and do his own thing, often leaving the apartment for the evening. When we were finally alone, I cuddled close and asked him if he remembered our first attempt at anal sex. He smiled and then looked at me with a question in his eyes. I silently smiled and nodded back, pulling the lubricant out at the same time. He had to reach down and rearrange himself in his jeans he was getting hard so quickly! I told him what I had learned since last time. He made me promise to tell him if it hurt too much, so I did. We then agreed we would take our time, use lots of lubricant then headed off to his room, pulling our clothes off as we went.
Soon we were tangled in each other’s arms, lying on his bed, our mouths greedily searching each other’s bodies. I could feel his cock jutting up between us, as hard as stone, and I rubbed my stomach against it causing him to moan and grind back. He reached down between my legs and rubbed his thick fingers against my flesh. Assured of my arousal, he wrapped his hand around his swollen rod and slipped it between my thighs. I gasped as he slid the head of his prick inside me. And as usual it was as much a gasp of trepidation as it was lust.
My boyfriend had an intimidating penis. It was about seven and a half inches long and was much thicker than average. We were about the same size and build, so you would think we would have been a good match everywhere, so to speak, but this was not the case. We quickly learned that even when I was fully aroused, he had to take his time with me otherwise he could tear my sensitive parts. He used to tell me I was good for his self-control! I would retort that he just liked my very tight pussy and he always answered “True on both counts.”
I liked straddling his body like this. I had more control over the depth of penetration, which always helped me to relax, and I enjoyed rubbing my breasts against his chest hair. Because he had pretty good endurance, we fucked for a while in different positions. We often started with me on top, but invariably moved to positions where he was more dominant. His favourite position for climax was up behind me, doggy style, so it was little surprise to me when he flipped me over, grabbed my hips and started pumping.
I let him go for a few minutes and then, begging for patience, I pulled several pillows under my abdomen to provide support, allowing me to relax. As I leaned forward and slid off his rod, I suggested he lube up a finger and start getting my ass ready for what we both knew was ahead. He grinned wickedly as he slicked up his middle finger.
As he pushed past the sphincter, he felt me tense involuntarily and paused. I breathed deeply and relaxed my body. Once he felt the tension let up, he pressed in deeper, taking note of the different angle needed. He took his time, giving me a chance to adjust, and showered me with honeyed words about my beautiful bottom. Soon he was working that one finger around pretty good so I asked him for another. He withdrew both, slicked them up and quickly reinserted them. This time I groaned with pleasure, reaching back to spread my ass cheeks for him. His fingers pushed in easily and he started to saucily taunt me.
“So, you like having your ass filled up, do you? Answer me woman. Do you like having your ass filled up.”
“Yes,” I muttered, “Yes, I do.”
“Then tell me what you want,” he said, “Tell me exactly what you want.”
“I want you to fuck my ass,” I said breathlessly as his fingers worked in and out. Minutes past and I couldn't believe how wonderfully full I felt.
“Maybe I don’t want to fuck your ass with my fingers,” he said, withdrawing them in one sudden motion. I whimpered in protest. “Maybe I want to fuck your ass with this.” I could feel the lubed head of his penis rubbing against my hole, causing me to groan.
I spread my ass cheeks and tried to capture his prick inside me, but he pulled back just far enough that I couldn’t reach. “Not so fast,” he said, “If you want it, you have to ask me for it. Ask me really nice baby.”
Face down on the bed, with my ass in the air and hands spreading my ass cheeks wide, I hungrily replied, “I want your hard, thick prick inside me. Please, fuck my ass with your cock” The last words had hardly passed my lips when his hands gripped my hips and the head of his dick slipped inside.
I cried out and pushed back against him, swallowing him up in one motion. I could hear his gasp of surprise and his fingers dug into my flesh. “Hold still,” he whispered. I waited and wallowed in the sensation of fullness.
“Damn, woman, you almost made me cum,” he muttered when he could once again speak. “I want to savour this for a while so when I say stop, I need you to stop moving right away, understand? I nodded, and tried to pull forward. He slapped my ass saying, “I meant it – I really need to do the driving. Man, you are so incredibly tight in here. Doesn’t it hurt you?”
Surprisingly it didn’t hurt at all. Unlike my pussy which seemed very reluctant to stretch even after a good warm up, my ass was more than ready to accommodate his girth. I saucily replied, “Maybe my ass likes your cock better than my pussy, because it isn’t complaining at all,” and swayed my hips in invitation.
I could hear his breathing becoming louder. “So, what are you saying woman? You know if you let this horse out of the barn there will be no going back. You know how he likes to run. Are you sure you want the horse to run?” I knew he was getting very turned on. His fingers dug into my hips and I could feel a slight tremor as he awaited my reply.
I reached down between my legs with one hand and stuck my fingers in my sopping wet pussy, then started to rub my clit before I answered him. “I want you to ram that rod of yours inside me and ride me. I want you to make me cum while fucking my ass and I want my ass to milk you dry.”
“Oh baby,” he replied as he pulled my ass back on his dick and started to fuck me. I could feel the hardness of his quads as they made contact with the backs of my thighs, the hair rubbing against my skin. I spread my legs further apart in an attempt to give him even more access. He used short strokes to ensure we stayed well-connected, thrusting hard with each push, his heavy balls bouncing against my cunt. By now I was in a complete fog, overwhelmed by new sensations and a growing tension between my legs as I fingered myself savagely. I was fighting to hang on. I didn’t want to climax before him as I was afraid I might tighten up too quickly.
Suddenly he let go of my hips, leaned forward catching himself on his hands so he made full contact with my back. He reached down with one hand to grab a hip and groaned into my back, “Come over the edge with me now baby!”
With that I was undone, "Fuck me baby please!" Crushed beneath him, crotch grinding into my hand, dick pummelling my hole, I crashed over the edge. Wave after orgasmic wave rolled over me. I felt his cock swell even larger; then he withdrew his full length before grunting and ramming himself home. I could feel his prick spurting and bucking inside as he held his pubic bone tight to my ass. Finally we both went limp.
Minutes past before either of us could speak. He kissed the back of my neck and propped himself up on his elbows. I worked my hand up from under me and sucked in a large gulp of air. We managed to get onto our sides enabling us to spoon. I gently squeezed his softening dick as it was still inside me. He threw and arm over me and tweaked my nipple. It was a good half hour later before either of us moved again.