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Thread: First anal sex?

  1. #1

    First anal sex?

    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.

  2. #2

    Re: First anal sex?

    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

  3. #3

    Re: First anal sex?

    Quote Originally Posted by chongster View Post

    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.
    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.

    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.

  4. #4

    Re: First anal sex?

    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..

  5. #5

    Re: First anal sex?

    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

  6. #6

    Re: First anal sex?

    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.

  7. #7

    Re: First anal sex?

    first anal sex i was 14 and fucked a girl in the ass who lived next door to me

  8. #8

    Re: First anal sex?

    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.

  9. #9

    Re: First anal sex?

    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.

  10. #10

    Re: First anal sex?

    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.

  11. #11

    Re: First anal sex?

    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.

  12. #12

    Re: First anal sex?

    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.

  13. #13

    Re: First anal sex?

    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!

  14. #14

    Re: First anal sex?

    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 !

  15. #15

    Re: First anal sex?

    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

  16. #16

    Re: First anal sex?

    My first time receiving anal sex was just over six years ago.

    I?d connected online with Dave, a retired dentist who lives about 45 minutes west of me. Dave shared my avid interest in social nudism and, since separating from his wife, had begun wrestling with an emergent interest in guy-on-guy forms of play. While very much a bi newbie, Dave had a large bucket list of things he wanted to explore and shared many of my sexual interests. Explicit emails and nude picture exchanges led to some very uninhibited camming sessions, and around Memorial Day, Dave invited me out to his secluded home on the shores of Lake Nemahbin for a nude hike around his secluded 20-acre woods followed by a leisurely soak in his big Jacuzzi. Although sex pay wasn?t specifically mentioned, it seemed more-or-less a certainly, given what we?d already shared online.

    In what would become sort of a weekly ritual that summer, Dave and I took a sensuous nude stroll punctuated by occasional stops for intimate touching in the woods, then jumped into the hot tub where we sipped cocktails and jerked one another to orgasm without the slightest hesitation. As the summer wore on, Dave became often mentioned wanting ?the whole bisexual experience.? To that point, we?d never progressed beyond mutual masturbation, cock-to-cock play and when the mood was exactly right, to my giving him oral sex. I had no particular interest in doing more.

    One warm August evening, Dave and I got pretty looped doing tequila shots in the Jacuzzi. He suggested we take a break to sober up a bit before resuming our play. We clamored out of the hot tub onto Dave?s big redwood deck where Dave sat at the patio table and I reclined in a chaise a few feet away, keeping my legs parted sensuously for Dave?s benefit. Inhibitions were down that night and after an uncomfortable pause Dave asked point blank, ?Would you ever consider letting me fuck you??

    The directness of Dave?s question surprised me, but not nearly as much as my answer. Maybe it was the tequila talking. Maybe I didn?t want to seem prudish or disappoint my horned-up host.
    ?Sure!? I said. ?I?d love to let you fuck me!?

    ?Let?s go!? said Dave.

    The next thing I knew the two of us were bouncing bare-assed up the stairs that led to Dave's bedroom. Still wondering what was about to happen, I got on my knees and took up the head down, ass high doggy position while Dave lubed his cock, and then my bottom with a bottle of Astrolube.

    He got on the bed behind me, pressed firmly against my opening, and after a few moments, I felt his cockhead go maybe two inches inside me! He began thrusting, trying to penetrate me more deeply, but it just wouldn?t go ? and it sort of hurt when he tried. So we tried a different position; with me standing at the bedside with my forearms on the mattress, Dave standing behind me, gripping my hips and trying drive his penis home. Again, he never got more than a couple of inches inside me before it began to hurt. Then we tried lying on our sides, and in the so-called gay missionary position; me on my back with my legs splayed over Dave?s shoulders. We tried for probably 40 minutes in a half dozen positions to get Dave?s cock inside me, but without much success. We ended bringing one another off in the usual way, and as I concession I granted Dave?s request to cum on my stubborn butthole.

    The following week, I found myself frustrated and disappointed at what had happened. It?s not that I particularly wanted to be butt fucked, but I knew Dave wanted the experience of fucking me, and I hadn?t been able to accommodate him. Ultimately, I wound up confiding in TJ, a gay friend whom experienced in such matters. After he got over the shock of learning I was bisexual, he went on to explain that there?s a whole protocol that needs to be followed in advance of anal penetration.

    He recommended having Dave administer an enema first, then oceans of lubrication inside and out, followed by stretching with fingers, and then a dildo or a butt plug, all before trying to admit Dave?s cock. He also said the best position for anal newbies like me was for me to be on top straddling Dave?s penis. He said that would give me complete control of the speed and depth of penetration, allowing me to be more relaxed.
    The following weekend, armed with TJ?s advice, the recommended supplies and a new bottle of Jose? Cuervo, I offered Dave another shot at my anal virginity. He jumped at the chance, as I knew he would, and patiently followed the protocol to the letter; warm, soapy enema, Astroglide applied liberally inside and out, then one lubed finger then two. That felt pretty nice, so I asked him to insert the pink, life-sized, anatomically correct pink dildo I?d picked up at the local sex shop.
    I felt silly at first, but as Dave worked the thing in and out, I became more than a little aroused knowing his gorgeous cock would soon follow.
    I asked Dave to put on a condom ? another TJ suggestion -- but he said he?d prefer to go bareback, and since I knew he?s never been with another guy, I relented, thinking that perhaps having Dave cum inside me might actually be kind of sexy.
    Bravely, I mounded Dave, straddled his hips, and reached behind me to position his cock at the right angle, Then I pushed back against it. As before, his cock went in a couple of inches, but this time I held my breath, bore down again and to my amazement Dave?s cock slid in almost to the hilt with minimal resistance. I was actually being fucked by another man, and I was actually kind of proud of the accomplishment

    Now, from my perspective, being anal sex wasn?t all that pleasant, just a lot of pressure and a sense of fullness, but as I bobbed up and down, David was in ecstasy, moaning slightly, eyes half closed, savoring every nuance of the act. I took some satisfaction from seeing the joy I was giving him reflected in his face. After maybe three of four minutes, Dave began bucking his hips, his breathing grew ragged and his moaning became louder. When I reached behind and found his ball sac drawn up tight, I knew he was about to cum.

    ?I?m really close? he said. ?Are you sure it?s okay if I cum inside you??

    I never got to reply because in that instant I felt my friend?s penis grow super-rigid, then twitch and throb as he pumped his seed inside me. ?Oh, God,? he gasped. ?I?m cumming! I?m cumming! I so needed this! Thank you!?

    Even as his orgasm subsided, I continued bouncing up and down on Dave?s cock. Finally, he begged me to stop, and I collapsed in a sweaty heap onto his chest. We remained joined like that until his erection subsided and fell out. When it did, a trickle of fresh semen trickled out of my opening and ran down onto my ball sac ? proof positive that I?d actually let another man cum inside me.
    Last edited by Ken Hadashi; Jun 3, 2024 at 6:40 PM.

  17. #17

    Re: First anal sex?

    My first time receiving was also my first time giving. I was about 14 and in juvie. A friend and I had been playing together for a bit mostly blow jobs when we could be alone, but he would only suck for a bit, and didn’t want me to cum in his mouth. I always took and swallowed his load though. One evening we managed to get some alone time and he asked me if we could do anal. I brought some Vaseline for the occasion and agreed to try. It was my first but not his I guess. He started to push in (well lubed) and it hurt pretty bad, but he got it in past the ring and held still and told me to relax. The cramp will subside, but you have to relax. He held still as I got adjusted. It took a couple of mins then he slowly started to push in and pull most of the way out. Long strong strokes then he told me he was cumming. He held inside for a moment or two enjoying his orgasm then pulled out. I went to the bathroom and cleaned up and felt like I had to poo, but didn’t. Then after a bit he said it was my turn and had me fuck him. I did the same thing he did, but didn’t last very long and quickly came inside him. It was a great experience and I wish we had more opportunities to repeat it, but back to me blowing him and jerking myself off. I got released soon after and lost touch with him.
    Several years later and I got a chance to get fucked again by a guy a little older than me. He fucked me while I was sitting slumped on his couch legs up and he knelt in front of the couch and started into me. Same thing enter, pause to relax, then pump. He hit my prostate just right as he pumped me, that he came and so did I hands free! It was incredible and secured my desire to be topped ever since.

  18. #18

    Re: First anal sex?

    I wear a butt plug everyday. Helps when I ride larger cocks




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