Tag Archives: CHERRY

TABOOTY – PART 3

By now, at the tender age of 33, anal play had become quite a staple in my world of sex. The first time I had a finger in my ass I was still in high school. My boyfriend and I were making out under the stairs in his house and our bodies were pinned against each other. I was in jeans and he slid his hands inside my pants. As his middle finger began to tease my booty-hole, I got extremely wet. When he finally stuck his finger in my ass I was totally under his control. With every flick of his finger I writhed with pleasure; until his grandmother came downstairs and we ran back to the couch. It would be years before I dabbled into full-on anal sex; but ever since that day, I loved fingers in my ass. 

The first time I tried anal sex, it was an ill attempt to maintain my “virginity”. He tried to stick it in my ass, but the pressure was too much, so Pop! Went my cherry! The first time I actually had anal sex was with my Dominican Bae. We were in his room and I was completely naked on his couch. He took his time to play with and lick at my pussy, to get me ready. When he finally went to enter my ass (being quite endowed); he took his time. He waited for my body to adjust to his length and girth; he waited for me to give him permission to keep going, and finally, only once my body was ready, he slowly thrusted in and out. As he fucked my ass so tenderly, I rubbed at my clit until I reached my orgasm. That was the pleasurable first experience of anal sex I was glad I had. However, the few that followed were not so good. 

I have a love-hate relationship with porn. I love watching porn for the sake of enjoyment. But I hate the fact that society has become so jaded on what sex looks like and/or is, because porn is such a fucking lie. No female squirts across a room. Not every woman wants to be abused and/or man-handled. And for crying out loud, my ass (and the average woman’s ass) is not a vagina. A vagina is a self-lubricating orifice that can stretch to accommodate penetration and child birth. No ass-hole self-lubricates and the average human’s poop is no bigger than 1” diameter (It’s been proven- I think!). The muscles that keep my shit from free-flowing, will always resist an attack; so, if desiring entry, one must take it slow.  

I tried anal sex twice; both in the missionary position, which is supposed to be easier, and it was painful almost the entire time. Only having one experience to go off of and the exaggerated porn, I allowed my partners to find their pleasure, and disregarded my discomfort. It would take years before I would agree to anal sex ever again.  

By now, I was well versed in anal play. I loved and yearned for fingers, tongue and on occasion, the filling sensation of a butt-plug; but I was still hesitant to allow my partners to enter my ass. I had set up a rule for myself.  The next partner to enter my ass had to be able to demonstrate an extreme amount of restraint. Men would enter with patience, but one inside they would go ham; and I was not having my ass abused like that.  

The weekend I finally revisited anal-sex, I just so happened to be on my period. My partner had previously mentioned that he “didn’t run red lights” so, I was prepared for a weekend of cuddles and delivering him oral. Eventually that position was tossed out the window when I got out the shower with my diva cup in and started to give him oral. As I sucked at his dick, he positioned my vagina to rest on his chin and he licked at my clit. It got to the point where he wanted to have sex and he suggested anal. With a very stern voice, I made it abundantly clear that he had to take his time and if he hurt me, I would punch him.  

I bent over on my bed and he positioned himself behind me. He lubed up my ass and slid in his fingers, one then two. After playing for a bit he got a condom and applied lube to his penis and slowly entered me. With my womanizer vibrator on my clit; coupled with the sensation of him entering my ass, it felt amazing. Once he was fully inside of me, I turned up the setting and I gave him permission to “fuck my ass”. As his thrusts grew more powerful the sensation on my clit intensified. What started as moans, grew to screams, and peaked at a howl as I had my orgasm. With my clit numb and the orgasmic bliss radiating all over my body, I fell into the mattress as he continued thrusting until he had his orgasm; then he collapsed on top of me.  

It took a few days for my poops to feel normal again (I wonder if that’s a thing after anal sex? I still haven’t gotten an answer from Reddit). It was quite possibly the best sexual experience I had in years. For the days following, I found myself stopping and reminiscing. I was happy I found a way to enjoy anal sex again, and I was even more happy with my partner. Originally, I had promised my ass to another partner, but since time kept us apart; I’m glad my experience was with someone I now love.  

In the future, anal sex will become the seasonal item on the menu. I have no desire to have anal sex everyday but, I’m delighted to know that it’s there.