First Time Anal Experiences

First anal sex…not quite sure… did it to please my new lover and put on a brave face even though it stung. Painful yes, because he spit in my asshole instead of using lube and fucked too fast

Not giving my anus time to stretch…Now I enjoy anal at certain times…like in a steamy shower. — BooBabe 28

First time was with my fiancé. He was humping my pussy & wanted to fuck my ass. I was really into the guy, so I let him. His dick felt gigantic when it first shoved in– hurt like crazy! Better when I relaxed… Wish I knew about lube back then…lol!–Fluffy 19

An older guy, when I was 18. Roger had me on my back, pushing my knees up to expose my butt-hole. He stuck a finger in, stretching my anus. A second finger went in, slow and gentle. Asked me if I was ready. I wasn’t but I nodded. Roger pushed his cock, fucking my ass slow the whole time. Felt like I had to poop, I was proud for taking it. The next time Roger fucked my ass faster and harder.– Kim 21

Making out with this chick. Got her panties off and she whined that she wasn’t on the pill. “Butt fuck me.” So I did and it was great….very tight and very willing to take it up her ass.–Fat Stax 25

We undressed. I wasn’t ashamed to be naked in front of Kim. He had a huge (I thought it was huge) ‘thing’. How did it fit in his pants? Kim turned me over, to show me the safest way to not get pregnant. He stuck his cock in my butt. No luck. We lubed his cock, it went in. He fucked my ass and squirted his sperm… First anal didn’t hurt too bad. Kim did my butt daily. On my belly was how I fell in love. Now I wanted baby. Kim fucked my pussy–THAT FELT GOOD!! Moving to US we learned all about sex. For years we thought that the only safe sex was anally.–Pasha 32

Very painful….I cried… Max was hung like a porn star… used tons of lube, it was still awful. But it got better. He got some anal toys which helped me stretch out. Now I can take Max’s cock up my ass without crying… — Isha 28

That day my ex wanted something different. Sucking my tits, his finger poked my anus. He lifted me on top and I eased my butthole onto his pole which was covered in KY. My ex had a very wide girth and really reamed me out. I rode on his cock slowly and it seemed okay. Tried it a couple days later and it hurt so bad I cried! Now I won’t do anal unless the guy has a small dick. Lol. — Minx 29

My fuck-friend bent me over and slipped it up my ass during a college threesome. First anal. I cried while sucking his friend’s cock. It hurt bad, but I took it up my ass, wearing nothing but my heels… After they finished I put on a robe. Mascara ran down my face, I looked like a racoon…a butt fucked raccoon. — Bandita 21

First time was a surprise. Doing it doggie-style. On my hands and knees, Bruce pulled my hair as we screwed. I was into it. Then I felt his knob between my butt cheeks. Didn’t know what Bruce was doing until his horse-dick shoved up my anus. I yelled as Bruce pushed all the way in and pounded my asshole. When he finally finished I collapsed, feeling like I’d been reamed out by a baseball bat.– Ouchie18

Started letting guys fuck my ass when I was 18yo in high school. Didn’t like giving blowjobs because I threw up. Guys need to get their rocks off. With anal I could fuck without worrying about dropping babies. So I spent a lot of time face-down and butt-up, with a horny prick riding my asshole. — Filly 27

First anal was with my stepbrother. My ass hurt and I felt like such a perv.–Ann 19

Painfully weird… having a hard cock shoved up my butt. After a few more ass fuckings all that went away, and I tried to enjoy it. Just had to get used to anal like I did when I learned to how give blowjobs and swallow gobs of jizz. — Sweet 18

New girlfriend was pregnant by another guy. Her doctor said no vaginal sex. We were hot & horny as fuck that night. She handed me some lube and lifted her ass. Sodomized her daily until the baby popped out.–Roger 27

Ran into my old chemistry teacher. Myles checked out my boobs and made a pass, “We have this sexual chemistry…” Drinks at his place, Myles got my clothes off and we fucked. Later he talked me into anal…Awful/amazing pain. I wanted him to stop and keep going at the same time. It felt weird having something hard pumping in and out of my asshole. That night we fucked for hours.– Nola 20

Me and my brother messing around with the neighborhood nympho. She wanted both holes filled. Her took her twat, I took her asshole. Very enjoyable.–Arlo 31

First time. My ex was determined to do it, fucked my butt too hard and too fast …Hurt like hell. I freaked out, said I’d never do that thing again! Married a dude a few years later. He was dying to ride my ass. Better this time, slow screw, plenty of lube…Now I get ass-fucked all the time. — Seraphina 31

Men think we’re stupid, that cocks “accidentally” poke into our assholes. First anal was an “accident.” Doing it doggie style when BF pushed into the wrong hole. I let him do it. Now BF is addicted to anal. Usually I give in… and sometimes it’s almost enjoyable. BF stands for boyfriend, and Butt-Fucker. — Fay 29

Squeezing girlfriend’s tits and twat. No condoms. Gina suggested anal, it shocked me. She lay on her belly, I slid my cock up her anus. It was way tighter than her twat. Gina gasped through her first assfuck. I drilled her butt HARD. We were sweaty by the time I spewed. I’m still impressed how well Gina took it. — Cole 33

First time wasn’t too bad. I was young and stoned. Boyfriend had a skinny cock, so it didn’t hurt too much. I enjoy it more now and can take larger guys. But I still prefer a pussy fucking because I can usually orgasm. The only time I orgasm from anal sex is if the guy, or someone else, tickles my clitty. — Jazzy 29

Bar hopping. Went home with a jock. We kissed and groped naked, and he fingered my anus. The next thing I know I’m bent me over with his cock plowing up my ass. It hurt and felt weird… the dude was so strong and hard that I didn’t try to stop him. I couldn’t. He fucked my ass good. In the morning he fucked my pussy, then rolled me over for butt-fuck 2.0. Now I get FULLY FUCKED! — Simone 30

Bf always fingered my asshole. Never thought I’d like anal, but that night I was drunk and horny, and with a gob of lube, he fucked my ass, deep and hard. Getting reamed out for the first time hurt like blazes. Eventually I got used to backdoor sex, and I’ll give it up whenever boyfriend asks. — Zella 35

I never liked anal, I still don’t, it’s too squicky. One day BF woke up after a dream about assfucking. It gave him a super-boner. So I got nominated to try it. Bf rolled me over and spit in my ass. We did the deed, he shot gobs of jism way up my butt. He enjoyed it a lot more than I did. Later we broke up, but I’d do anal again for the right guy. — Junie 24

First 2 times weren’t good. A couple of guys tried, only got the tip in and it HURT! My real first time was like romantic. Sounds crazy, talking about getting assfucked. I was on my stomach, Bf kissed my lips…trying to distract from the cock ramming my butthole. I cried but didn’t make him stop. Finally took it all the way. I guess I was still an anal virgin. Lol. I do enjoy it more now though.– Patti P 25

Didn’t want PIV sex because I was “saving” myself. But a cute guy talked me into trying anal. My anus was so tight he couldn’t get it in at first. The horny dude kept trying. In the end he got it in my end… and it hurt like hell. But he was happy and now we’re GF/BF. Now I get sodomized all the time. — Deva 24

Date with a skank who got drunk at dinner. Ready to dump her off until her drunk ass wiggled in my lap, asking if I had a rubber. I didn’t. In my car she sucked my cock, got on all fours, and opened her butthole I still remember how tight her ass was and how she squeaked as I fucked it. Squeaking still turn me on. — Stud 21

Eddie kept wanting to do anal, I said no. But after he licked my pussy I finally let him…and cried when Eddie’s big prick invaded my asshole. He fucked deep.. I took it whining. Eddie shot his wad up my ass and collapsed on my back, leaving his huge cock buried all the way in my butt… I felt fully fucked. — Tina 21

Met a “Just friends” girl. She was horny, but had a boyfriend. One night, petting and fingering, the girl got burning hot. I suggested anal sex so she could save her pussy for bf. She reluctantly agreed and got on all fours… Good, tight assfucking– Later I talked into being my gf so I could get pussy. But I still like screwing her ass from time to time (probably more than she likes getting it). –Stew 29

Two days after our first date. We kissed until our lips went numb. He took off my blouse and bra… I agreed to let him take off my panties but no way did I want to get knocked up…He guided his hard-on into my ass-hole and fucked it. –Hella 24

Met a musician at a bar. We drank and watched pornos together. He stuck it up my ass without warning– it was painful. Tried it later with lube and another guy. Better but the dude liked it way more than I did. Never as good as in the pornos. Now I’ll only do it if the dude licks my cunt first. –Lyra Z 20

Fucking girlfriend with her legs over my shoulders. I mid-fuck she wanted to try anal, and guided my cock to her ass. We took it slow but only got a few inches up her butt before she screamed to STOP… The next morning she was more relaxed. My cock gave her a good assfucking. She told me anal sex was so intense it was almost a “spiritual” experience. My eager cock agrees. –Agnew 31

My first anal was like, Ooh Fuck… now I know what my cunt is for! — Ouchy 23