live4thebj
Literotica Guru
- Joined
- Dec 24, 2012
- Posts
- 4,002
First time doing anal. Tell us about it. Did you plan it? Did you fantasize about it? Spur of the moment thing? Forced? Surprised? Etc. Details!
First time receiving anal
- Thread starter live4thebj
- Start date
kccasey
apprentice
- Joined
- Sep 27, 2015
- Posts
- 370
First time anal was with phallic items I could find around the house. Handle of tools, glass vials, etc. Then I got a dildo, wow, what fun I had.
But you want to know about first time another person fucked me, don't you? Well, the first time was when I was 21, I heard about a bar downtown which was showing porn movies in the bar. Had to check that out ya know. Long story made a little shorter, I met a TS girl there. She turned out to be a prostitute, but I was so horny I went for it. I sucked her cock, and she fucked my ass. She had a nice cock, about 8" and slender, did not Strech me uncomfortably. Anyway, I took her cock and loved it. The feeling of another person fucking me, sliding in and out, pushing deep, the sounds our bodies made, god, it was such a turn on.
I was so turned on it frightened me. Oh no I though, I must be gay. This was around mid 70's, so society was still frowning on homosexuality. I denied my urges for years. Did not have anal sex for long time, except with dildo's. married, but no kids. Could not orgasm with with women most of the time.
Now I am a sexless marriage and looking for a FWB with a big cock.I have worked up to large dildo's.
But you want to know about first time another person fucked me, don't you? Well, the first time was when I was 21, I heard about a bar downtown which was showing porn movies in the bar. Had to check that out ya know. Long story made a little shorter, I met a TS girl there. She turned out to be a prostitute, but I was so horny I went for it. I sucked her cock, and she fucked my ass. She had a nice cock, about 8" and slender, did not Strech me uncomfortably. Anyway, I took her cock and loved it. The feeling of another person fucking me, sliding in and out, pushing deep, the sounds our bodies made, god, it was such a turn on.
I was so turned on it frightened me. Oh no I though, I must be gay. This was around mid 70's, so society was still frowning on homosexuality. I denied my urges for years. Did not have anal sex for long time, except with dildo's. married, but no kids. Could not orgasm with with women most of the time.
Now I am a sexless marriage and looking for a FWB with a big cock.I have worked up to large dildo's.
Last edited:
SweetCuriousDarling
Exploring
- Joined
- May 15, 2015
- Posts
- 33
This is actually one of my most arousing experiences. I was with the only man I've ever truly trusted, sexually. We have amazing sexual chemistry. He knew I was very nervous about trying anal, and had some hang-ups about it due to some bad past experiences. He understood that the only way to make it happen was to ensure that I had no choice but to completely let go.
We started our encounter as we had many before. He dressed me up in some lingerie, so I would feel properly sensual. It's a nice, kind of foreplay ritual that begins to get me into the correct headspace. Then, while kissing and caressing me, he began to bind me to the bed. We'd played with bondage before, so I wasn't surprised by this. This was another ritual that served to adjust my headspace, and turn me on.
Once lightly bound on my back on the bed, a spreader bar between my ankles and my wrists above my head, he went down on me. He's exceptionally good at this, and it wasn't long before I had an explosive orgasm.
Thoroughly lost, now, in the pleasure of the sensations within my body, not thinking and kind of coherent thoughts, I was only dimly aware as he turned me over and fixed my wrists to my ankles. I was completely immobile at that point, my face buried in a pillow, my ass up in the air.
First, he fucked my pussy for a few strokes, knowing how delicious it feels for me to be fucked directly after an orgasm. But then, he began to penetrate my ass. It was shocking, and I know I tensed a bit, but he rested his hands on my ass and held me fast. While he wasn't rough, he also didn't go slow. He'd made sure everything was well-lubed, and before I had time to get back into my head enough to form any objection, he had his cock buried inside me. Then he just held himself there.
He asked me if I was okay. I don't know if I really knew, but I did know I wanted him to keep going, so I just made a motion for him to hold my hand. He did, and then he kept going. Bent over me, he fucked my ass for the first time, grunting softly in my ear, telling me what a good girl I was, until eventually, he pulled out and came all over my cheeks.
I was crying a bit as he came around to cradle my face and kiss me, emotionally overwhelmed. But it was a beautiful experience. Still a masturbatory go-to for me.
We started our encounter as we had many before. He dressed me up in some lingerie, so I would feel properly sensual. It's a nice, kind of foreplay ritual that begins to get me into the correct headspace. Then, while kissing and caressing me, he began to bind me to the bed. We'd played with bondage before, so I wasn't surprised by this. This was another ritual that served to adjust my headspace, and turn me on.
Once lightly bound on my back on the bed, a spreader bar between my ankles and my wrists above my head, he went down on me. He's exceptionally good at this, and it wasn't long before I had an explosive orgasm.
Thoroughly lost, now, in the pleasure of the sensations within my body, not thinking and kind of coherent thoughts, I was only dimly aware as he turned me over and fixed my wrists to my ankles. I was completely immobile at that point, my face buried in a pillow, my ass up in the air.
First, he fucked my pussy for a few strokes, knowing how delicious it feels for me to be fucked directly after an orgasm. But then, he began to penetrate my ass. It was shocking, and I know I tensed a bit, but he rested his hands on my ass and held me fast. While he wasn't rough, he also didn't go slow. He'd made sure everything was well-lubed, and before I had time to get back into my head enough to form any objection, he had his cock buried inside me. Then he just held himself there.
He asked me if I was okay. I don't know if I really knew, but I did know I wanted him to keep going, so I just made a motion for him to hold my hand. He did, and then he kept going. Bent over me, he fucked my ass for the first time, grunting softly in my ear, telling me what a good girl I was, until eventually, he pulled out and came all over my cheeks.
I was crying a bit as he came around to cradle my face and kiss me, emotionally overwhelmed. But it was a beautiful experience. Still a masturbatory go-to for me.
lily_wall_
Literotica Guru
- Joined
- Feb 8, 2024
- Posts
- 1,128
First time was my finger because my friends and I had a conversation about anal earlier that day. Didn't really care for it. I tried a few more times, just one finger, but couldn't get my juices flowing and never understood how people orgasmed with just anal. But I didn't hate it either
Fast forward, tried a small toy with a friend guiding me. She eased it slow and opened me. Apart from the initial pain, nothing exceptional. But once I started taking the toy deeper... *Chef's kiss*
Similar threads
