This Happened the First Time I Had Strap-on Sex with My Girlfriend

Loving Pegging

My girlfriend, Sarah, and I were sitting in bed one night when she started to talk about her friend, Cheryl. We both work long hours at the office, and even though we work in the same building, most of our conversations happen in bed. You know, we ask each other about our days, how horrible our bosses were, everyday couple talk. But I never thought we’d talk about strapon dating.


“Cheryl had strap-on sex last weekend with some guy she met online!” she said with bewilderment.

“Oh yeah?” I replied, my eyes glued to Antman playing on the tv. Man, if I could shrink like that, the first place I’m going is Area 51.

Sarah’s body turned towards mine, demanding my attention. “Yeah, she said it was a little weird at first because she never had to thrust like that before, but it’s apparently a really fun experience.”

I knew where she was going with this. Sure, Cheryl had a good time, but my butt is a no-go zone. What straight guy would allow their ass to get penetrated by a giant dildo?


“Are you sure the guy was straight?” I asked.

“Of course, he was straight. Strap-on sex doesn’t mean you’re gay,” she replied offensively.

I took a deep breath, “is this something you want to try?” I paused in silence, waiting for her answer.

“Well,” she said nervously, “I am really curious about it. I thought we could try something new – it sounds like a lot of fun.”

“Why this? Out of all the things we could try, why this?”

“Why? Why not. We’ve never done it before, I would love to try role reversal, and the male G-spot is in the anus.”

Really? I didn’t want to look curious, so I told her I’d think about it. That night while she was asleep, I did a little research. What sparked my curiosity is the male G-spot; I didn’t know it was in the anus. Does this mean it’s going to feel good? Are my orgasms going to be even better?


Sarah had the day off the next morning, so I wrote her a note and left it on my pillow, “To do list: go get a strap-on.” A couple of hours later, she sent me a photo of the kit, with the message, “can’t wait to see you!” To be honest, I was really excited. The minute I got off work, I basically ran home.


When I got home, Sarah was on the bed, waiting for me. I climbed on top of her, kissing her passionately. She sucked her finger and then slide it into my ass, massaging it slowly. I could feel my body loosen up; I was excited to give this a try. After a couple of minutes, I got off the bed, grabbed the kit, and handed it to her.


Sarah came out of the bathroom with the strap harnessed around her waist. It wasn’t so scary as I imagined. “Listen, I’ve been doing a lot of research about it today, so I think I have a pretty good understanding of it. The most important thing is you tell me if it’s uncomfortable or painful. Don’t try to “take it like a man,” got it? Use the safeword red if you want to stop.” I nodded in agreement, “got it.”


She lathered the dildo up with lube and laid on her back. “Wait,” I said, “aren’t we doing it in doggy style?”

“No,” she shook her head, “that’s for more advanced people. I read that doing it cowgirl is the best for beginners.” I climbed on top of her and straddled her with my legs, we both giggled. “I’ve never seen you from this angle before,” she said.


I took a deep breath and slowly slid the dildo inside of me. Was there pain? No, but it definitely didn’t feel comfortable at first. Sure, she did everything right and used lots of lube, but nothing can explain the initial feeling of something going up your ass. I didn’t move for the first couple of seconds; I was adjusting to the new feeling. Then slowly, I slid up and down the dildo; not too deep, just enough to ease into it. Sarah had her hands on my thighs, lightly pressing into me.


I picked up momentum; a tingling feeling ran through my body. So, I started to go deeper and faster, the sensations streaming up my body; I couldn’t stop, I was jumping like a yo-yo. I knew I was about to orgasm, and that’s something I didn’t want to miss out on. “I want you to come for me,” I heard Sarah say, and that was all I needed to hear. I expected a usual orgasm, but this one was different. It exploded throughout my whole body, paralyzing me for a moment. I had reached pure bliss, something that’s never happened to me before.


Sarah looked at me, and I looked at her in silence. I didn’t know what to say; I couldn’t think of words at that moment; I was emotional. “So, how was it?” she asked. I removed the dildo from me and laid next to her on the bed, “Amazing.”


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