Hi, my name is Emily. This is the story of, you guessed it, my very first time. Not just my first time having anal though, it is the story of my first time with a cock inside me, so enjoy. A couple things have been altered to make the story a little more interesting.

At the time my boyfriend and I had been dating for about three months, give or take a week. We were both very shy; neither of us was brave enough to make the first move. We had had some very heavy make-out sessions, after which I could tell Nick was aroused, but they never led to anything more.

We had gotten into a nice little routine. During the week we would text and video chat when we could and during the weekend we would alternate between staying at my place and his place.

We were at my place on this particular weekend and, after an especially hot mouth-to-mouth session, I knew I couldn’t take it for much longer, but I was a little too shy to start stripping him on the couch. I decided that someone had to make the first move and that it was going to be me, tonight. So after we “recovered” from our lip battle, we started our pre-bedtime ritual.

It was simple but it made us feel like we were playing house in a way. We would basically brush our teeth and change, the latter done in separate rooms. At this point in our relationship we were still super shy so changing in front of each other was not a thing yet.

When we got into bed he wrapped his arms around me, pulled me into my position as his “little spoon,” and nuzzled the back off my next. I giggled and arched my back slightly, making sure my ass grinded lightly against his crotch. I could feel his breath get warmer against my neck and his arm muscles tense up ever so slightly.

It didn’t take long for me to feel his stiff member against my ass, but I continued pretending to innocently rub against for what seemed like forever. I remember what felt like the beginnings of a cramp start to creep up in my lower back.

Finally I felt him shift slightly as he moved to pull down his pajama pants. My heart beat quickened as he struggled to free himself from his cotton drawers.

I quickly learned that he went commando while he slept when I felt something intensely warm press against my back.

By this point my breathing was heavy and I was getting very nervous. It was as if Nick could sense that because he began to kiss and gently bite my neck as his hand ran over my body and brushed against my now hard nipples. His hand quickly ventured down to the waistband of my shorts and began to pull at them.

I was getting worked up at this point and frantically helped him get them, and my panties, out of the way. When they finally were, I felt his warmth settle perfectly between my butt-cheeks.

His hips started to move, making his cock slide between my cheeks. It rubbed against my little rose bud, causing me to shiver and bite my lip. Responding to my body, Nick began to rub circles around it with the tip of his dick, spreading the juices that he had leaked in excitement all around it.

Even these small movements were driving me crazy. I reached down and spread my ass a little more so that he had better access to it.

All shyness had left my body, and also my boyfriends.

I bit my lip as he continued to pleasure my ass. A thought ran through my mind. ‘Will this hurt?’ I knew he was going to fuck me in the ass tonight. It was the only option since I knew I didn’t have any protection and wasn’t sure if he did either, but I was a little nervous.

All my thoughts and cares flew out the window though, and as soon as I felt the entire tip pass my threshold I let out a gasp. Letting me relax and get used to the new feeling, Nick sucked and nibbled at my neck. He was propped up on his right elbow at the point; I was facing away from him still and his other hand kept his cock from slipping out from inside me.

To show him I was ready for more I again pushed my ass towards him, causing more of him to slide inside of me.

He continued to bury more and more of his cock inside me, until finally he was fully sheathed.

Sweat dripped off of us as we lay there connected in this new and exciting way. Nick returned his hand to my chest and began to explore one of my erect nipples with his thumb and index finger. I was enjoying the feeling.

Acting under the influence of a reflex I didn’t know I had I leaned forward a little, bending at the waist, and then began moving my ass away from and back towards my boyfriend. He quickly got the idea of what I was doing and started to slowly fuck me.

As his cock slide in and out of my ass, my own fingers snaked down to where there was a throbbing ache, between my legs. My pussy was slick from all of the excitement; I had never been so wet before.

Seeing where my hand was going, Nick lifted my leg up so that I had better access to my pleasure center.

With every thrust my finger traced a circle around my clit, causing an intense bolt of pleasure to run through my body. Each bolt also caused me to tighten around my boyfriend’s cock.

Nick’s thrust became deeper and deeper; I could sense that we were both close.
My fingers kicked into over drive, rubbing faster and tighter circles against my aching clit. Within a few seconds I could feel my orgasm coming, and with a gasp it took over my body. I tensed up my lower half, my boyfriend still pumping his cock in and out of me.

He could hear and feel my orgasm, which caused what little control he had left to get tossed out the window.

Mere moments after my own orgasm, Nick buried his cock deep inside me one last time and released his seed. I felt the warm sticky liquid coat the inside of my ass as he let out his final moan.

We laid there for a minute or so. No sound except for our panting.

He slowly slid out of me, kissing my neck before going to clean himself off. As he cleaned up I re-adorned my panties and shorts. He came out of the bathroom and lay back down next to me, once again taking up his position as the big spoon.

We were both exhausted and we fell asleep as soon as we were cuddled up together. I was definitely glad that I decided to make that first move.