#7 Anal Sex (w/ Bonus List Item)

This by far was the most anticipated item on the list. It was something that had been spoken of since I was in my teenage years; something I had seen in many pornographic videos. The fact I was an ass guy had me naturally drawn to the idea of anal. I had read horror stories about it, but that never deterred me from the fact I wanted to one day try it. The other night was that night.


“J” and I always discuss the list before having sex. Some nights we just don’t get around to anything on the list because we get caught up in the moment and prefer to continue doing what we’re doing instead of trying something new. Anal was always brought up, but neither of us had made the move or suggested it during sex. Finally when “J” asked me what I wanted to do because it was my turn to pick, I jokingly said “how about butt stuff?” as we laid naked on the bed after our first round. “J” agreed to my surprise and suddenly I was excited but a bit nervous.


“What position should we attempt it in?” I asked. “Bent over,” she replied. I got off the bed and rolled on a new condom. A small bottle of anal lube that had been used for “J’s” sensual hand jobs was about to be used what it was made for as I grabbed onto it. Standing next to the bed she played and squeezed my testicles, until I asked her if she was ready. Sitting up, “J” positioned herself on all fours on the bed; presenting her ass to me like an animal in heat. I climbed back onto the bed and inched my way behind her only to realize this position probably wouldn’t work for our first time.


I climbed back off the bed and grabbed onto her hips, pulling her back over to the side of her bed until her feet planted down on the hardwood floor. She remained leaning forward with her face buried in the mattress as I took charge of the situation. I drizzled some lube into my hand and stroked my condom wrapped cock; making sure to coat it thoroughly. Spilling more onto my fingers, I applied lubricant between her ass cheeks; over her anus. I rubbed the rim “J’s” ass for a few moments feeling each wrinkle on her new entrance.


“Here I go,” I said. I knew this wasn’t like you seen in pornography, where they guy just jams his cock in a girl’s ass and she moans in pleasure. This was a first for both of us so I eased my way into it. Rubbing the head of my cock against her anus I started to push forward, but unfortunately I slid away. It was tougher than I thought it would be entering her. Again I tried, this time I felt the head of my cock slowly sliding in. I asked her if she was okay and she said she was fine through gritted teeth.


Eventually as her clenching anus relaxed I slide in a little bit more at a time. In fact I slid so slowly inside her that I wasn’t sure if I was moving in deeper at all until I was balls deep in her ass. I looked down at the two arches of her ass and couldn’t believe we had finally accomplished this item on The Fucket List. I moved my hips slowly, feeling the rim of her anus grip onto my shaft and slide up. In and out I went at a very slow pace until I could feel myself fucking her without as much force. I thrust into her harder and faster; her ass cheeks rippling with each pound of my hips.



Now here is where it gets a bit interesting because I didn’t feel much of a difference. I get that the anus is tighter than the vagina, but for me I thought to myself, “what is the big deal?” I think anal was a bit over hyped for me, or I couldn’t feel the difference because I was wearing a condom. I continued to fuck “J” from behind, but soon pulled back and allowed my cock to pop out of her anus. “How was it?” I asked. She explained it stung a bit, but she was fine. “J” had a new found lust emulating from her, she pulled off my condom quickly and pushed me down to her bed on my back. Rummaging through her dresser she found a new condom and immediately rolled it down over my shaft as soon as the packaging was off.


“J” climbed on top of me and I entered her with ease from how wet her cunt was. The two of us managed to find the perfect position like we never had before. I was a bit lower on her body with her breasts nearly bouncing against my face. I clutched onto her thighs as she rode up and down and her breathing got heavier. I put my knees up and planted my feet in her bed and thrust up into “J”. The two of us were now drenched in sweat and as I thrust into her there had been so much cum that the sounds of liquid smacking against skin echoed through the bedroom. I always enjoyed a mess; the messier the better I say and this was the messiest the two of us had ever gotten.


I continued thrusting up into her at the same pace and could feel a tingling sensation in the head of my cock. That feeling gave me the boost I needed to finish “J” off as her breathing stuttered and she lifted herself up far enough so that I could slide my fingers into her until she came. I felt a sense of accomplishment after this session. She lifted herself up and our skin peeled off one another from the intense sweat we created. I had never seen her squirt before but it seemed to have happened this time as the sheets of her bed were literally sprayed with cum. It was a night to remember for more than just the anal.


I laid back down on the bed because “J” was deadest on getting me off. She used some of the lubricant to stroke my cock and I swear this was the closest she came to getting me off. Unfortunately my body hates me and I lost that feeling of close to cumming. She asked me where I wanted to cum on her because then we could cross something else off the list.  I said her breasts with the plan to masturbate until I was close and jump on top of “J” and cum all over her breasts. She had other plans, I got to the point of no return and she lay next to me on the bed and put her breasts right in the line of my orgasm. I came hard and streams of cum coated her breasts; trickling down over her nipples. Like I said, it was a night to remember.


Again I must say that anal for me didn’t live up to the hype and was really not worth the extra effort. Although I would like to try it again someday without a condom to really be able to judge. This experience was in by no means a bad one, it was good but just not great if that makes any sense. “J” wrote her own perspective on this night and if you’d like to read is click here:




Until next time, happy fucking!


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