Opening the Backdoor

I loved foreplay and sex but one of my greatest fears was getting pregnant. I was not on birth control yet so I was riding the line between risk and reward.

I was seeing this great guy named Tommy at the time. Tommy was very physical. He loved getting into my pants in any shape or form that he could. I was always trying to battle being horny and being smart.

Tommy and I were hanging out with a group of friends when one told this joke about three guys trapped in a jungle. There were each told to pickup a numbered stone or a stone with an "x" on it. The first two men picked a numbered stone up and the third guy picked the "x" stone up. The first two men were told they would be fucked in the ass as many times as their number was. The third man was told because he picked the "x" stone he would be fucked in the ass until dead.

Now everyone was laughing at the joke but it honestly gave me an idea. What if I let Tommy fuck my ass? I knew it was a thing but I had never really considered it. It was always kind of a taboo act that was for jokes more than anything else. If I did let Tommy have my ass though, we could have sex and I could avoid pregnancy. The wheels in my head began to turn.

Unfortunately no one I knew did anal sex or at least they were not admitting it. Also how do you go up to your friends and bring up the subject of letting someone fuck your ass? I did not know any gay men so that route was out as well. I could only imagine what an Internet search would bring up. The process was simple enough but I wanted to see if it was something even enjoyable.

It was about a week later I found advice where I had not expected to. I was at a party and sitting on a couch watching a game of beer pong when Audra sat next to me. Audra was the big booty blonde currently dating my friend Ben. Audra had gained a reputation making her way through most of the males in our social circle as well as some others. Audra was also know because she did have a large booty attached to a frame it did not fit.

In all fairness Audra was a nice woman. Her and I did not start talking about sex but it went there when she announced she was a little sore. She then offered up the information that Ben had been really horny as of late and been going through a butt phase. I put two and two together from that, swallowed the lump in my throat and asked if she had any tips for other women who were dating guys into booty stuff.

Audra simply looked at me and smiled. My pulse was racing as I had never really opened up to someone about sex before let alone the fact I was considering anal sex. Lucky for me Audra did not pry and gave me quite a few helpful tips in order to enjoy myself. With advice in hand it was time to get to work.

The first tip was a simple one, lube. It was a simple and logical tip. I had some lube at home that I used with toys but I did not want to pull out my half used bottle of lube and open up that question. I went to the store and got some good unscented lube. I did like a green apple one they had but I was not sure if Tommy wanted his dick to smell like apples during and after.

The second tip was to keep things calm and relaxed. This was going to be my first time so there was going to be some pain and discomfort at first. Audra suggested a few drinks before the experience. I went a little further and visited my friend Big Daddy and acquired one of his custom cigarettes.

Tip number three was the mental battle. Audra said that often women looked at anal sex as all pleasure for the men and discomfort for the woman. She said she knew some women that hated it, some that said it just felt like something shoved in them, and others that loved it. I needed to at least be open to it being an enjoyable experience and that I might like it.

Audra also recommended practicing with toys first to see what it was going to feel like before the actual event. I made a trip to the adult store downtown and was amazed at the number of toys they made to go inside someone's butt. They had vibrators a little bigger than a pen and went all the way up to fists sized dildos. I could not even imagine someone buy the fist and getting that up there. In the end I decided to skip the toy and let Tommy be the first thing inside my ass.

The timing worked for my plan really well. I was going out of town for a few days so I had asked Tommy to keep an eye on my apartment. He informed me he would so long as I paid him prior to leaving. I told him of course and invited him over the night before leaving.

The day of the event I cleaned my place and made it smell amazing for two reasons. One to be a good home owner and two good smells relaxed me. About an hour before Tommy coming over I had my special cigarette out on the deck. When Tommy got there I was nice and relaxed and ready or as much as possible.

Starting things has always been the most awkward part for me. Both Tommy and I knew he was there because we were horny and we wanted to play. So it was goofy as he came in and we were just sitting on my couch pretending to make small talk.

I decided to make the first move and told Tommy to lean back. As he did so I unzipped his jeans and reached inside his boxers finding his cock. I took it out of his pants and began stroking it. I loved watching his cock go from limp to hard in my hands. The size increase was always amazing to me.

Shortly after becoming fully hard Tommy asked me to stand up. I did and he reached up and grabbed the side of my shorts pulling them and my panties down to my ankles. Once down I kicked them off to the side. I sat back down on the couch and spread my legs open. Tommy started feeling around my pussy and rubbing my clit before pushing two fingers inside of me. I took a deep breath as they went in and then started breathing a little heavy as he fingered me.

For the next few minutes we said nothing as we played. Tommy was the first to break the silence. "Your pussy is amazing. I want to fuck you so bad." His hard cock was bouncing up and down as if it were nodding in agreement.

"Do you want to try something?"

"What?" He asked.

"It's a surprise so yes or no?"

He gave me a little smile, "yes."

Tommy removed his fingers and I stood up. I told him to get naked and went to my bedroom. I took the rest of my clothes off and grabbed the bottle of lube from my dresser. I then returned to the living room where Tommy was naked on the couch.

"What is that for," He asked.

Now was the time, no turning back. "I thought we might use this and you could fuck my ass." It was at this point that the world paused. Did I really just ask my boyfriend to fuck my ass? Was he okay with that? Probably should have asked that before being naked holding a bottle of lube. It seemed like minutes passed before he said anything even though I am sure it was only a few seconds.

"Oh fuck yeah!"

Well that went over well. Tommy stood up and came over to me smiling from ear to ear. He began grabbing my ass and spanking it. I laughed and opened the bottle of lube putting some in the palm of my hand. I then took my hand and started rubbing the lube all over his cock. I was making sure to get the whole thing.

I then went to the middle of the living room floor and got down on my hands and knees. Tommy was quickly behind me and started grinding his cock up and down my ass crack. He also took the moment to push on my asshole with his finger.

"Are you ready?"

Quite the question. Was anyone ever truly ready to have a cock shoved up their ass? "Yes." I went with the simple answer.

Tommy guided the lubed head of his cock to my asshole and began pushing. My body naturally began to tighten up but I took a breath and did my best to relax. With this my back door open and in came Tommy. My butthole did scream a bit as it gave way and I had to take another moment to breath and relax.

Tommy sensed the tense up, "are you okay?"

"Yeah. Just taking a moment to get used to it." The pain subsided and I was left with the feeling that something definitely was shoved up my ass. "Okay."

Tommy began moving slowly with his hips going back and forth. I was happy to find that as his movements continued it actually started to feel good. I was starting to feel pleasure in this. Tommy began moving faster as I relaxed more and got more into it. Soon Tommy was going at his full pace and the living room echoed every time our bodies hit each other.

Both of us were breathing hard when my arms and legs could not hold up anymore. I went down flat on the floor. Tommy adjusted his position a little but did not lose any speed or eagerness to keep up pounding my now eager asshole.

I found myself actually approaching an orgasm. It felt different than a normal orgasm but it felt good. I wanted this orgasm and I wanted Tommy to keep fucking me more and harder.

My orgasm came and hit just before Tommy pinned me down on the floor and grunting aloud. It clicked in my head that he was cumming inside of my ass. It was at this point it really kind of clicked he was shooting cum into my ass and when this was done I would have an ass full of cum. That was a huge turn on for me and made my orgasm all the better.

We laid there with Tommy on top of me and I just felt flooded with warmth. It was great just laying there for the next few minutes. We did eventually have to break apart though.

As we stood up Tommy went and sat on the couch. "That was amazing babe. Your ass is amazing."

"That was a lot of fun actually," I replied. I was a little worried about my ass leaking cum so I put my panties back on before sitting down.

Tommy's phone got a messaged and he checked it. "Ben is having a party, want to go?"

"Sure but I will need to get more than this on."

"I think you could pull off that look."

We got dressed and went to the party. There was quite a few people there and we started making our way around to see everyone. That was when I saw Audra over in the kitchen. I made my way over to her and said hello.

"Did you think about my advice?" She asked.

"The fact that my ass is currently full of cum would say yes," I replied.

"You go girl," she said.

We laughed and the chat moved on to other subjects. I will admit the fact that I was standing in middle of a party with cum inside of me felt like a naughty little secret and I loved it. That together with the fact I felt like I was a little naughtier than most for having anal sex was turning me on again. I felt like this was going to be the start of some fun for me.