My first anal sex was with a girlfriend when I was a teenager, didn't know what we were doing and it was painful for her but I loved it. Well never got to do it with her again but wanted to ass fuck every girlfriend after that. Once I learned to use lots of lube and go slow at first I got to fuck a lot of ass.
I didn't discover my bi side until I was 40, then I started fucking younger guys. I love to watch my cock slide in a small smooth ass so I seek and find young twinks who like older men.
I too was a teenager but was seduced by an older guy although he didn?t fuck me he did use several fingers on me which led to me enjoying anal both ways and with both men and women
My first anal sex was with a much older guy. Fortunately, he knew his way and I didn't have hardly any pain at all. In fact, it was a highly pleasurable experience in that he gave me my first hands-free orgasm.Originally Posted by chongster
Since, I've been with other guys and women who've wanted anal sex. There is a definite skill to employing pleasure through the act. I was lucky and had a great teacher.
I have posted here quite a few times that I consider myself to be very lucky as I feel like I have 3 different first times.. all different and original..
#1 I was 12-13 older cousin and his 3 friends each fucked me that summer 1-2 a day..
#2 my football coach when I was a junior in high school bent me over in the shower one night.. then fucked me every day during school till I graduated..
#3 18 years old an adult.. I started my journey as a trans female dressing and full on having sex with men because I wanted it..
My first time was with an ex girlfriend in the woods when we were 16. she pulled her skirt up and her thong down and leaned against a tree, i put a condom on and unfortunately not enough lube. We did quite a bit of anal over the years that followed
I was in my late teens. I'd done women and knew I liked it but I had questions about men as well so one evening I went to the adult theater in an old grand style movie house from the 20s. Instead of going to the main theater I went upstairs to the gay films. I wasn't up there five minutes when a guy sat down beside me and the next thing I knew he was feeling me up. I told him I'd never been with a man. He said he understood. We left and I followed him back to his place. He was a great teacher. Well hung. He was very patient with me. He would do something like rim my ass then let me do it to him. Eventually he fucked me and came then let me fuck him to orgasm. We lounged around in bed until we could both get it up and did it all over again. I love anal, male or female, top or bottom in large part it was thanks to that guy's skillful teaching of me.
first anal sex i was 14 and fucked a girl in the ass who lived next door to me
My first experience was in university days pleasuring a girlfriend who discovered she enjoyed. First time with a guy was in my mid-30s, the first time I played with a male. We took turns sucking, had a long session of 69 and then ended up fucking each other. I recall it being briefly uncomfortable and then quickly into the pleasurable zone. I still remember the feeling of his cum shooting onto the small of my back, something I found quite erotic.
My first time I was 13 or so, me and a guy friend my age decided to practice on each other to get ready for girls, which I had jokingly suggested we do and he replied sure, but we both get to do it (the penetrating). He bent over first and I couldn’t get my dick in him (no lube), so when he stood up he reminded me it was his turn. My butt was bigger, his dick was erect but smaller than mine. So after some pushing and wiggling around he got it up me. I let him do it until it got sore, i didn’t hate it but I thought it felt weird.
I believe I was about 16 the first time I fucked a girls asshole, and omg I was hooked. That little stinker hole felt so much better than pussy. The way it grips my cock is totally different. Since my first time with her, I have tried it with everyone else, and 99% of the time I got in there. Still love pussy, but that asshole is King in my book, male or female.
19, in the back of my van in a bar parking lot with an older man. I had wanted it so badly for a while. Was a bit scared at first, but after he got it all into me and I relaxed, soon after he started thrusting I came all over the floor of my truck. First time with a girl was the same year, with my high school/college girlfriend. She had an orgasm too.
My first anal sex experience was with a girlfriend, Paula. Although she was 13 years my junior, and a 23-year-old virgin when we met, she was sexually inquisitive – and unapologetically so.
At first, sex with Paula was pretty conventional, but eventually came to include exploration of different sexual positions, oral sex, vibrators, sex toys, and some fairly unconventional sex acts. She would bring me off orally then kiss me deeply, passing my ejaculate between us. She would insert a lubricated finger into my backside whilst administering a hand job with the other, or ask me to cum on her tits, then lick them clean. She seemed to be a regular dynamo with a bottomless sexual bucket list.
One night she climbed into my bed and assumed the butt-up, head-down position. I assumed she wanted me to stand at bedside and fuck her from behind, something she enjoyed because it provided the deepest possible penetration. As I went to enter her, she pushed my cock away from her opening “Uh-uh,” she said, “Tonight I want you to feel you in my butt . . . you know, anal sex.”
To that moment, I’d never actually thought of fucking Paula’s backside, but she clearly wanted this, and I wasn’t about to pass on the opportunity. To my surprise, she’d already prepped herself, and with a little bit of lubricant, and a couple of gentle thrusts, I slid right in, right to the hilt. I was afraid of hurting her and asked how it felt. She said it felt like having a baseball bat shoved up her ass, but urged me to fuck her vigorously, which I did.
Paula’s anus was tighter and had a somewhat rougher texture than her vagina, but I enjoyed the difference and fucked her backdoor enthusiastically. Sadly, I didn’t last very long before I found myself being rocked by a massive orgasm. I stayed inside her until my erection began to subside, and when I pulled out, I was shocked to discover that my condom had broken and had pumped a full load into Paula’s anus. I thought she’d be upset, but she said she actually preferred having my cum inside her.
I thought anal sex might become a regular part of our sex play, but oddly, we never did it again. Interestingly, about a year and a half ago, I received a text message from Paula who lives now in North Carolina. She said she was lying naked in bed, masturbating and fantasizing about having anal sex with me again. Hope springs eternal.
I was about 17, had a girl naked on the bed, first time together, climbed in between her legs ,she reached down and grabbed my dick and rubbed it on her ass and told me to push. Didn't take me long to cum. Never put it in her pussy. I liked it!
My first time was as a teenager a friend of mine and I were experimenting when he said he wanted to rub his cock up and down my ass crack well I let him and after a few rubs he began pushing and next thing I know he’s inside my ass and starting to fuck me I was shocked at first but realized how good it felt especially when he shot his load in me ! It oozed out for a long time lol !
My very 1st experience with anal sex was with a man. In 09 after my wife and I separated, I had spent the evening nursing rum and cokes and feeling extremely frisky. I set out online to get my virginity taken. After some small chat And a few shots, I set out with condoms and lube to meet a man that lived in my neighborhood. I don't know if it was a combination of alcohol and years of toy experience but when I bent over my tailgate and he roughly shoved his cock in me, it really didn't hurt.
It was low 50s, in the middle of the nearby desert and I had my pants down around my ankles, sweatshirt around my neck, my pale white ass glowing under the full moon, getting fucked at 3 am like there was no tomorrow. While nothing like I had fantasized about, it was good enough to try a 2nd time a month later.
1st woman I ever fucked in the ass was a couple years after that, didn't think it was anywhereclose to as good as pussy. When it comes to anal, I'd rather be on the receiving end
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