My First Anal Sex Experience

My posts about anal sex have always been among my most popular with readers, especially my post 10 Steps to Great First-Time Anal Sex. However, my own first-time anal sex wasn’t planned (at least by me) and didn’t follow the ten steps.

My first anal experience happened during my senior year of high school. My mother was out of town on a business trip, so my boyfriend came over that afternoon after school. We drank my mother’s vodka while we watched a movie. It didn’t take long for both of us us to get pretty drunk (which helped a lot for what was about to come). Soon, we had forgotten about the movie and were in my bedroom, stripped down to our underwear, making out.

It wasn’t long before my bra was off and then my panties. Almost as soon as my panties came off,  my boyfriend started going down on me. Back then, being eaten out was my absolute favorite thing, so I just lay back, enjoying the wave of endorphins washing over me. Suddenly, I felt a sensation I hadn’t felt before. My boyfriend was running his tongue along my perineum and getting closer to my anus with every lick. There was a part of me that wanted him to stop, but there was another part of me (the drunk part) that was telling me to relax and enjoy the sensations.

I had to admit that it felt good. My boyfriend did the trick where you blow on all the wet spots, and it was driving me crazy! He pushed my legs back even farther and dove right in, I’d never felt a tongue on that part of body – ever – but it felt incredible! He pushed his finger into my butt, and because it was so wet back there, it slid in easily.

When my boyfriend finally came up for air, I was afraid that he was going to try to kiss me. Instead he rolled me over on to my stomach so that I was lying flat on the bed. He pulled off his boxers, and then he climbed on top of me. I was really nervous about what he was going to do next (though I had a pretty good idea). Without saying a word, he pressed the head of his penis against my anus, and I remember whispering to myself, “Oh, my god. Oh, my god.” He was really going to put it in my butt, but I wasn’t as scared as I though I should be. After being licked and fingered back there, I actually wanted it.

He used his legs to spread my legs wider. I felt him press harder against me, and then the head was in. He started very slowly, but after a few strokes, he pushed all the way in.

It felt very tight inside, and I thought he was going to rip me at first, but I took deep, deep breaths and did my best to relax. Fortunately, my boyfriend wasn’t that big. If he had been any bigger, I don’t think I would have been able to take it.

Although it still hurt, with every stroke  it also began to feel good. It felt so good that I even put one hand underneath me and got myself off. (I’d never touched myself during partner sex before, so that was another first.) It was a very intense orgasm because of the amazing sensation of feeling him so deep inside me as my muscles contracted. My boyfriend came inside me right after I came .

Afterward, when I asked him how he knew I wouldn’t make him stop, my boyfriend smirked and said, “When have you ever stopped me from doing something?” I didn’t like his answer very much, but I had to admit he was right. Not long after, though, his cockiness caused him to go too far. To read about what happened, click here.

What was your first anal sex experience like? Was it great, awful, or somewhere in between? Tell me about it in the comments.

Tags: Anal Sex, first anal experience, first-time anal, personal sex experiences

2 Responses to “My First Anal Sex Experience”

  1. digvijay Says:

    it sounds good but it must be taking enough of the time as you both were drunked so you can’t feel any pain or you might had felt after reply

  2. natasha allex Says:

    anal sex is initailly painful but i get enjoyement after initial 5 min. I am regular anal sex lover. My hubby drill my anus these days as i am pregnant. Best way is apply some lube then finger ur self and in last take the tool.

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About Me
I came to the U.S. at age of 12 with my mother. We settled in sunny Florida, which was quite a contrast to Minsk. I have always been fascinated by sex and relationships. My sexual history and preferences are detailed in my post 100 Things about Me Sexually. Sex Secrets is where I share sex advice, experiences, news, and sometimes a little humor.
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