Pegging My Boyfriend Was On My Mind From The Start Of Our Relationship

During my second year of college, I dated an incredible guy named Steven. Steven was tall and muscular, with a short dark beard and a sexy English accent. He was relatively vanilla and definitely an anal virgin. I wasn’t sure he’d ever let me fulfill my dream of pegging my boyfriend. Overall, he was not as sexually open-minded as I was—yet. Due to my past experiences, I was exceptionally kinky and open-minded for my age.

Despite his vanilla tendencies, I loved how he fucked me and licked my pussy. Therefore, I tried taking things slow. I did not want to lose him. However, I wanted to teach him so many new and delicious things in the bedroom. I wanted a man who was sexually flexible and liked to push boundaries. I was especially excited to show him the wonders of pegging. Pegging my boyfriend was a dream, and I wanted him on board. I even daydreamed about pegging him while we were fucking, and I got even wetter.

I couldn’t stop thinking about pegging my boyfriend’s tight, puckered asshole.

Luckily, Steven started experimenting with new things more often in bed. He started to trust me. Obviously, I waited to tell Steven about how much I wanted to peg his ass with a strap-on. I was afraid that he would reject the idea and turn me away. Eventually, I told Steven about my long-term desire to peg him.

“I’ve always had a fantasy about pegging my boyfriend.”

Steven turned bright red. The thought of it turned him on, as he loved light humiliation and being dominated. Furthermore, I wanted him to experience being taken and fucked from the back. I knew he would enjoy the delicious prostate stimulation that came with having a strap-on in his sweet ass. Selfishly, I loved how the base of a strap pressed against my clit. I wanted us to orgasm together, with me in control when I pegged him.

Over time, I got closer to pegging my boyfriend.

Eventually, Steven became progressively more open-minded. He tried anal penetration with other toys. First, I introduced him to smaller anal toys, like plugs and small dildos. Steven used them while masturbating, and he really enjoyed them. Second, I showed him how to stimulate his prostate while we fucked. I loved to help.

Obviously, I wanted him to have a much longer and hotter orgasm. I began to put my thumb up his ass during blowjobs. Afterward, I followed with multiple fingers. I could tell he liked it, but he always acted shy. He did not want to feel less manly. I assured him it was incredibly manly because he was doing it with me. I dreamed of pegging my boyfriend, and thankfully we were getting there. Men who are not confined by societal norms are the sexiest men in the world. I found Steven hotter as he began to experiment more in the bedroom.

I loved our nights of orgasmic pleasure.

One day, I bought the perfect 6-inch strap and a lot of numbing lube. It was important for Steven to be comfortable when I finally pegged my boyfriend. I was so turned on while getting the strap all lubed up for him. I loved standing behind him with the strap-on, so close to living out my fantasy. Clearly, Steven felt similarly.

Lubing up his tight little hole was so sexy. With Steven on his knees, I started slowly sliding the tip of the strap in. The tip of it was wider than the shaft. Therefore, Steven winced at the quick moment of pain. Once I  got the tip in, the rest was easier for his little hole to take. He grabbed the sheets, and immediately he started moaning. Steven loved it, and he came so hard. He loved every second of being pegged, and I continued pegging my boyfriend often, making him spew cum everywhere. 

If you are interested in pegging, anal, or any naughty delicious fun, give Valerie a call.