There is something so beautiful and eye-opening about a man with his guard down, his legs spread, and a dildo inside of his sweetest spot, bringing him pleasure that not every man experiences.
It’s a downright sin that some men won’t ever experience anal pleasure and my boyfriend, luckily, isn’t one of those men because he just loves me poking his prostate and bringing him over the edge into an orgasmic world unknown by his friends.
My boyfriend introduced me to pegging, we had been together for a few months, and one day, whilst relaxing in bed, a new indie tune playing from the radio in the next room, he told me he wanted to tell me something. Part of me thought he was going to admit to something like cheating on me from the look on his face but as I got to my elbows and listened to his confession, he poured his heart out, telling me we didn’t have to do anything, I could be repulsed if I wanted too but he enjoyed pegging and anal play in general.
At first, I didn’t know what to say, this had come out of nowhere but it wasn’t because I was shocked it was because I was turned on.
I had never pegged a man before but I had always, always wanted to try and my boyfriend didn’t believe me when I jumped up with glee, excited at getting to finally try out something I had begged past boyfriends to try.
“You’re serious? you’re really okay with it?”, he said, dumbfounded.
I told him all about my fantasies, my desire to peg men, and how I had always kept it a secret from him because I didn’t want to weird him out. He showered me in kisses and in that loved-up bubble we had sex, it was passionate and exciting, full of new things to come and as he filled me with his seed and sucked on my breasts, I yearned for him on all fours, begging for release and I couldn’t wait to give it to him.
It all seemed to happen quite quickly, we went from talking about it to actually doing it and one Friday evening as the sunset and the mood kicked in, my boyfriend presented me with a gift box. Inside was a strap-on with a modest dildo beside it. My eyes were wide as I began exploring it, feeling its power and its possibilities. The harness was easily slipped around my waist and the dildo fell into place easily, I paraded around the room giggling and my boyfriend joined in, smiling at my silliness and enjoying my excitement.
Sitting back down, I turned to him with a serious tone to my voice, “Are you ready?”, I asked him, my eyes looking for a flutter of doubt to shimmer across his face.
He looked at me and nodded, trusting me with such an intimate procedure but there was no doubt on his face and before I knew it we were in the bedroom and it was time for me to finally feel what it was like to peg a man.
“Look if you want to stop at all…”, my boyfriend trailed off as we quickly got undressed. He was telling me again and again how I didn’t have to do this to make him happy and how he wouldn’t mind if I didn’t like the idea. I shushed him with my finger, telling him to be quiet and guide me that I wanted this more than anything and was ready to give him something he loved. He smiled at that and we kissed, before falling into bed together and getting lost in the moment.
The air was filled with apprehension as he sucked on my clit, my mind raced with not being good enough, not knowing how it all worked but I wanted this and I wanted my boyfriend to feel satisfied. He sucked on me ravenously, making me wriggle and moan, making me forget the anxiety in my head, and making me cum furiously all over his face.
I was on cloud 9, elated and ready to make him feel as good as he had just made me.
“Your turn”, I whispered into his ear as he kissed my neck. His body tensed on top of me, his cock was hard against my bare leg. He turned onto his back and I was on top of him now, planting kisses on his body, unsure of my next move. I slipped the harness on and secured the dildo, it was easier than I had anticipated. I continued kissing my boyfriend as I jerked his cock before slowly pressing a finger against his ass.
I had already put lube all over his asshole and my finger slid inside of him with ease, making him wince and moan at the same time. I fingered his ass for some time, sliding another of my fingers into his tight hole, I was breathing heavily, it was turning me on so much pleasuring my boyfriend like that, and I knew the best was yet to come.
Gently and slowly I pressed the tip of my dildo against his hole where my fingers were and inch by inch I eased my fingers out and swapped them for the dildo. I pressed slowly, easing the tip of the dildo inside of my boyfriend, I had no idea what I was doing but his eyes were closed and his mouth open, giving me the signs that this felt good for him.
I bit my lip as I eased more and more of the dildo inside of him before I felt I could begin thrusting, something I had never done before yet felt surprisingly natural to do.
He let out a loud groan as I thrust into him, again and again, keeping my rhythm as best as I could. I felt his body hot and aroused beneath me, he kissed my neck as I lay on top of him thrusting as deep as I could, I felt a cramp in my butt but I continued going, I didn’t want anything to ruin this moment.
My boyfriend’s cock was hard and twitching beneath me, I instinctively reached down and began jerking him off as he moaned louder, I thrust into him and rubbed his cock simultaneously. It was magical, I felt his cock pulsating in my hand as my dildo buried itself deep inside of him. Pre-cum spilled from the tip, coating my hand in his glistening sperm.
I panted and groaned as I fucked his ass, my boyfriend had squeezed his eyes tightly shut and was gripping the sheets beside him, I knew he was still a little apprehensive and so I whispered into his ear seductively and said: “Just let go”. He let out a loud sigh when I said then, his eyes still closed but not squeezed so tightly, his jaw untensed and he began making louder noises.
“Does that feel okay?”, I said, breathlessly.
He nodded quickly, he was riding the wave of pleasure that I knew so well and I wanted this to never end, pegging was going to become my favorite pass time, I just knew it. I thrust a little quicker into him now, I felt inflamed with arousal and his ass was un-tensing, letting me push it further to its limits.
Suddenly, my boyfriend tried to say something but the words wouldn’t come out, he was too lost in the moment, the pleasure consuming him. I knew he was trying to tell me he was going to cum but I pretended to be oblivious I wanted this moment to blow his mind. I continued thrusting, my cramp getting worse but then he began to blow, his body tensed, his jaw tensed harshly, his breathing all but stopped as he took harsh, deep breaths. His cock dribbled with cum and he let out a huge moan as he experienced a full-body orgasm.
I had never seen my boyfriend like this, he made noises I had never heard him back before and he practically went unconscious a few moments later. I slowly pulled my dildo from his ass and kissed his forehead, laying down next to him to snuggle as he fell into a post-orgasm, deep slumber.
“That was the best thing I have ever experienced”, I whispered to him a few minutes later. He remained silent but he squeezed my hand and I knew he thought it too.
I lay there for some time, listening to his gentle snoring and I realized that to be the best girlfriend you have to peg your man.
