Pleasing my partner has always been top priority for me when it comes to bedroom time. When we first started seeing each other, we started off with very basic positions and activities, but it wasn’t long before it felt like we were always doing the same things. I never wanted him to feel like sex was boring, so I brought up the idea of sex toys. I had only used a few prior to us being together, and I didn’t really enjoy them (if you can believe that!) but I thought if we found some to use together, it would really enhance our playtime. We started looking at toys together, and after seeing toys geared toward anal pleasure, I finally got the courage to mention how much I thought he would enjoy anal play. Now, we had already engaged in anal sex (with me being on the receiving end) but the idea of his ass being penetrated was not only a brand new thought to him, it was a scary one.
He laughed at me, not thinking I was serious about wanting to try it, and the first words out of his mouth were, “I’m not gay!”. I shook my head, having a feeling that this would be his reaction, and explained that I didn’t and wouldn’t think that at all. After a pretty extensive conversation, he agreed that someday we could try it out. We decided to start off with fingers, since they were small and non-intimidating, and decided to use a glove since he was concerned about making a mess and I truly didn’t know what to expect. I left the conversation at that, expecting to wait awhile before it was brought up again.
I was pregnant at the time, and had a check-up later that week. Once we were alone in the room, I saw my husband grab a couple gloves and stuff them in his pocket. At first I was upset, I’ve always had such a conscience about doing the wrong thing, but once I was able to separate myself from what he had done, it made me realize that he was actually interested in trying it as well.
He had to work that night, and on the way home he picked up a tube of KY Jelly at the local drug store (can you tell we were totally new to this stuff?). He was so cute talking with me on his cell phone while he was picking it up, wanting to make sure he got the right thing. When he arrived home, it was obvious he was excited to try it out. It amazed me how quickly he went from so unsure, to wanting it right away. We showered, went back to our room, and got started.
We started off laying naked together, kissing and touching. We were both pretty turned on when he told me he was ready. I put the glove on, slathered it with the lube, and started rubbing him externally while I pleasured him orally. It was evident he was already enjoying it, I kept tasting his pre-cum and he kept telling me to stop so he could hold back his orgasm. After a little more rubbing, I could tell he was relaxed. I made sure he was ready, and slipped my finger inside of him.
The look on his face gave away his feelings; he was experiencing his first taste of anal pleasure, loving every second of it! I went back to pleasuring his cock with my mouth while trying to rhythmically stroke the right areas inside. Truth is, I had no clue what I was doing, but I just kept paying close attention to how he was reacting and kept asking him if what I was doing was okay.
When he finally stopped telling me to slow up or stop, I knew it was time for the big finish. His breathing changed, his body started shaking, and I could tell he was cumming for a while before he actually ejaculated in my mouth. Up to that point, it was the strongest orgasm he had ever experienced! My mouth was insanely full, he was in a state of ecstasy, and I felt like we had connected on a totally different level. It was a beautiful, powerful, and amazing bonding experience!
My husband is a straight man who enjoys anal pleasure, and there’s nothing wrong with that!
Our experience with this type of play proves an amazing point. When you eliminate your fears (emotional and physical) you’re opening yourself up to amazing possibilities. Will you love everything you try? Not necessarily. But you’ll never learn to experience maximum pleasure if you let fears get in the way of potential pleasure!
-Side Note-
My first knowledge of anal play being pleasurable to a man was discovered in a very unconventional way (I’m assuming). I was watching the movie Road Trip with my sister and there’s a scene where they’re trying to make a little money and decide to donate their sperm. One of the characters decided he need a little help from the nurse and they go into one of the rooms together, where he thinks he’s going to get some action. Here’s the clip to show what happens:
Now, while I didn’t expect it to be exactly like this movie, it certainly remained in my mind for years after, assuming there must be some truth in the pleasure experience. Don’t expect your experience to be just like the movies, and keep in mind that it takes time to learn what you like. Start slowly and let go of any expectations, it will be a much more enjoyable experience that way!
GREAT article! Thanks for sharing your experiences.
Well told. Thanks for the good story, and I’m happy for you both!
I go in modes where I like anal more. Anal was something it took time and patience to get use to. Thanks for sharing your experience.
Very well written – and hotasallhell!
This is a great post. I love hearing about first times, especially when they’re as full of love and pleasure as this one. Good for you for asking, and good for him for being brave!
Great article. Definitely something I would like to try