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  1. #1

    Best anal sex stories

    we all remember our first time like it is burnt into our memories.. I know for me I also remember the time that I up until a few months ago as being the best sex I had.. up until Dan and my mayor hubby came along it was the best most prolific sex I had ever had.. I learned so much about my self that day and was fucked long and harder than ever before.. I had my first two anal orgasms,, learned that the longer and harder I was fucked I became very loud moaning.. I also learned that when fucked really well that I build up a tremendous amount of heat in my body and sweat profusely..
    I met Chris on a warm spring day.. we had chatted for about two weeks before we decided to meet and have sex.. I went to his place.. he lived in a studio apt.. in a renovated two story house.. when I arrived he was sitting on the front steps chatting with two old ladies that were knitting.. when I pulled into the drive he introduced me to them and told them that he was going to fuck me silly.. it embarrassed me to think that he was that open about what we were going to do.. anyway I parked my jeep on the side of the house by his door.. we went inside.. he walks up to me and kissed me then turned and started getting naked.. so i got naked as well.. then he turned to me and kissed me again and reached down and took me by the cock and led me to his bed.. his bed was along the outside wall under a big window.. he reached over and opened the window.. he then lays on the bed on his back and spreads his legs.. i clawed in between his legs and start sucking him.. after about 10 min of sucking he is now very hard and he pulled me off his cock and up to his mouth and we start kissing and making out for just a short time.. then he tells me that he has a medical issue that won?t let him cum.. it also make his cock hard as a rock for hours.. I looked him in the eyes and told him that I wanted to take it until he couldn?t any more!! He smiles an just says ok.. he then directs me to get up and bend over the corner of the bed.. now I should tell you that he was rock hard but only about average in girth and around 7-7.5? long.. he lubes me up inside and out and him self.. then I feel his cock in my ass sliding up and down.. he asks are you ready baby?? I reply yes give it to me I am so horny from sucking I need to be fucked.. he then finds my pussy hole and drives himself balls deep in me., there was no pain or discomfort just pleasure.. I remember thinking this won?t take long and he will explode in me and want to be done.. for the next hour and a half he bangs away in me.. I have gotten quite loud moaning and being vocal about how good my pussy felt with him in me.. I was building heat,, my body was flush and I was sweating.. he continued fucking me.. he ask if I had enough?? I told him not until you cum in me.. he laughs.. he put me on all fours on his bed and continued fucking me.. an other hour goes by.. then he lays me on the bed and we kiss and roll around making out for a bit.. then he lays me on my stomach and crawls back on top and fucks me for another hour or so., by this time I am really sweating and extremely loud.. he climbs off and he says let?s go cool off in the shower.. I figure he is done.. nope again he bends me over in the shower.. then back to his bed.. this time I am on my back!!! After about an hour we go back to the shower.. then back to his bed.,
    For almost 6 hours he fucked me none stop unless we were rolling around his bed making out or going to or from the shower.. he never did cum not in or on me.. only when his cock went soft did we stop.. he fucked me three more times like that.. almost exactly a month to the day that I met him he was killed in an auto accident..
    the funny thing about that first day that he fucked me.. I never realized that the window over his bed that he opened was just around the corner from where the two old ladies were sitting.. they sat there the whole time and heard and listened to everything.. when I got in my jeep to leave I stopped to say goodbye.. they both had smirky grins on their faces.. the lady seated closest to me looked at me kinda funny and said he fucked you really good!!! I almost fell out of my jeep!!!
    That was my best sex ever until Dan and the Mayor came along..
    so there you have it.. let?s hear your best sex ever story.. share it and don?t leave out the details.. ok 1-2-3 go!!!

  2. #2

    Re: Best anal sex stories

    I remember my best buttfucking because it was done by a gay top 8 inchs thick and he fucked me 4 times he left my asshole sore for a week

  3. #3

    Re: Best anal sex stories

    Two times stand out as my favorites,?one was the first time a friend of mine got me with his extremely wide dick, it took lots of lube and patience and was actually quite uncomfortable at first. But he took his time and got me real slowly and my nuts tingled the whole time. He?s about 6 inches but really very thick round fat, wide and gets wider to the base. The other time was a guy I met on an out of state trip in a nice bar. Bi and gay friendly but not really a gay bar. I had not booked a motel yet so he invited me to sleep at his place. It didn?t take long before the pants came off and we traded blow jobs and he seemed kind of surprised when I asked him to fuck me. He got me on my belly on the bed with plenty of lube. His dick wasn?t big but he fucked me slowly and found all kind of places up me. Also, although around 5 inches and slender, the head shape was like a pronounced bullet and felt amazing.
    Last edited by BackyardShaman; Jun 24, 2023 at 8:03 PM.

  4. #4

    Re: Best anal sex stories

    My first experience as a bottom was both surreal and intensely pleasurable. He was much older and obviously much more sexually experienced. The previous day, I had the pleasure of sucking his cock to completion (which had been a first for me). And as much as I enjoyed that act, it only fueled my desire to have him take me anally.

    It was a hot July day. His wife and son (who happened to be one of my best friends) were out of the state on an extended vacation. Anxious to pick up where we had left off less than 24 hours earlier, I arrived at their place around 11 a.m. Fortunately, they had a large fence surrounding their backyard and pool area, so privacy wasn't really an issue. He greeted me at the door wearing only a pair of boxers and a tee shirt, and like the day before, I was there in my bathing suit, tennis shoes and tank top.

    He could sense that I was nervous, so he invited me to sit with him on the couch and he broke the ice with a little small talk. It wasn't long, however, that he steered the conversation to the previous day's events by telling me how much he had enjoyed our time together and how much he was looking forward to picking up where we had left off. As he stood up in front of me, I couldn't help but notice the growing bulge in his boxers. That was clearly my clue. I immediately sat up, pulled out his penis, and leaned in for what would be my second taste of his hard cock. I was once again lost in lust as he slowly began feeding me more and more of his 8 inch dick. I continued to suck and stroke him for several minutes. I might have been just as happy to let him cum in my mouth again, except he had other ideas.

    "Why don't you come with me," he said, tapping me on the shoulder. "Let's try something different."

    I followed him through the dining room and into the kitchen. He had placed a couple of towels and a tube of lube on the butcher block that also served as an island. "Are you ready?" he asked. All I could do was nod and I unzipped my trunks and let them drop to the floor. He casually reached for the lube and told me to turn around and get comfortable.

    With a small amount of lube in his hand, he reached between my legs, and for the first time, he began stroking my cock in a downward fashion. Until that moment, no one else had ever touched my cock. The pleasure was intense, and it was all I could do to not cum right there. Sensing my orgasm was approaching, he stopped stroking me and slowly began working his hand up along my crack and between my butt cheeks. Applying more lube as he went, I felt his fingertips massaging my virgin hole. Ever so gently, he slipped his index finger into me. Once I began to relax, he worked another finger in. As I stood there bent over the counter, I could feel his hard cock pulsing against the back of my thigh.

    "Okay," he said. "I think we're ready."

    After placing a generous bead of lube along my crack, and another along the shaft of his cock, I felt him positioning the head of his cock at my hole. This was it. The point of no return. His his left hand on my shoulder and his right wrapped tightly around his cock, he gently began increasing the pressure until my sphincter relented, allowing the head of his cock to penetrate me. He felt enormous - certainly much bigger in my ass than in my mouth.

    Surprisingly, there was no pain. Just an intense feeling of fullness. He paused for several seconds to allow my ass (and my brain) to adjust. "How does that feel?" he asked. I again nodded and gave him a thumbs-up. With that, he began to push in deeper and fuck me in slow, shallow strokes.

    "Wow, you are so tight," he said. "I'm not sure how long I'm going to be able to last."

    He continued to fuck me in that position for a few minutes before pulling completely out. "Let's go back to the living room," he said.

    Once there, he told me to kneel on the floor against couch. Within seconds, he was again behind me pushing into my now stretched hole. Kneeling on his left knee, he placed his right foot on the couch next to my shoulder. This position afforded him better leverage and allowed him to fully penetrate me with long deep strokes.

    I glanced up at the large mirror that hung over their fireplace. There I was, bent over my best friend's living room sofa, watching his stepdad fuck me into oblivion. The physical and emotional sensations were overwhelming, and I began to find myself pushing back and grinding my ass against his crotch with every down stroke.

    The intense physical pleasure, coupled with the sheer visual eroticism, triggered my first hands-free orgasm. With a loud grunt, I spilled my load onto the side of the couch and carpet below. My orgasm was quickly followed by his. Pushing into me hard, I watched as he collapsed on top of me, emptying his entire nut deep into my stomach.

    I've had many other experiences since then, both as bottom and top, and with men and women. But that was by far the most intense.

  5. #5

    Re: Best anal sex stories

    The best anal sex for me was a couple yrs back during a blizzard in Northern MN. All flights were cancelled and I rented a rental car to get to Duluth. Upon getting the keys to the last of the rentals this nicely dressed gentleman asked where I was going, Duluth I said, mind I hitch a ride? I told him the road were really bad and we would have to get a room at one of the local Hotels. He smiled and said if you drive I will buy the hotel. After a few hours of trying to find a room we finally found one 10 miles away. That 10 miles took us 45 minutes so as we arrived as promised he paid for the room.

    once in the room we decided to get something to eat, but being a seasoned traveler I always have Bourbon with me. I offered him a drink and we headed out next door to the cafe that was still open. Upon returning to the room we had some more beverages and the conversation turned to sexual fantasies, when he got up up from the sofa he dropped his pants and said let’s shower. As we were both wer rubbing our cocks from our stories. I undressed and reviewed my 8 inch half hard cock and he did as well. Just then his phone rang, it was his wife, he of course answered it and pretended everything was normal. As he talked to her he was rubbing his now rock hard cock as I rubbed mine. His cock was awesome, 7.5 inches and a huge ball sack. Before he hung up I was sucking his cock, he had precum leaking which I licked up eagerly. When he hung up he called me an asshole for putting him through that while talking to his wife.

    Once in the shower he whispered I want you to fuck me! He licked and sucked my cock like a deprived slut, he and I lathered each other up and he wanted to feel my hard dick between his butt cheeks. After a few minutes he reached down and guided my cock into his man hole. He didn’t even flinch when I went balls deep. After 10 minutes I blew my load in him. He casually cleaned his ass and my cock and we retired to the bed. Once in bed he started stroking me again saying he needed more. Now that his ass was stretched I went in like a bandit. I fuck him rough and hard and he never complained, I blew my 2nd load in him as he collapsed on the bed. The morning came late as the storm still raged and he was bent over once again wanting cock. That people was the the sex I ever had.

  6. #6

    Re: Best anal sex stories

    The best for me was being fucked by a guy whose dick measure 13" - and I measured him twice because I couldn't believe he was that long. But he was and I was... worried about it and to the point where I was about to chicken out for the first time in my life. I was sure he wasn't going to be able to get in me but he slid right in... and all the way in and I had never been fucked so good before in my life; if I didn't know how much dick he had, I would have sworn that he was really only five or six inches. He took his time, assured me that he wasn't going to hurt me in any way and, well, he just didn't and feeling him sliding in and out of me was seriously dreamy and quite orgasmic and when he came, wow. Just wow.

    Whole different story when I went to fuck him but, yeah the best fucking I'd ever had both then and now

  7. #7

    Re: Best anal sex stories

    KDaddy: I had a guy a few times some years back that was 13 well just a smidge over 13” long.. he wasn’t thick about average in girth but all of 13” long!! I too wondered how the hell or should I say where the hell all that was going to go.. he was also very incredibly hard..and he got hard very quickly.. i dough I ever sucked I’m more than5 min to get him hard.. I did once get it all the way down my throat.. but the first time he fucked me I was nervous.. he told me no one had ever take it all.. I told him I would!!! Ski was on a mission.. I was a bit scared!! When he entered me I was relaxed and ready.. like I said he wasn’t thick at all so when he entered me he slid right in.. I had him pull out and squirt lube a lot of lube inside me.. the next time he entered me he slid in balls deep.. his belly was agents my ass and he was grinding away at my ass.. I had 13”of cock up my pussy.. he reached in and touched me where no man had gone before or since.. it was amazing feeling him that far inside me.. he stirred my insides up for a little over an hour.. the he gave me a huge thick load of cum so deep in me that it never leaked out of me.. he fucked me twice that night.. he fucked me about 2 dozen more times over 2-3 months.. always the same no pain no stretching just going deep very deep!! It was amazing

  8. #8

    Re: Best anal sex stories

    @Tight, yeah this guy was stupid long... but was "lacking" in the girth department and I would think that being so skinny was what made it easy for him to get it all in me and it wasn't all that uncomfortable for me. I did deep throat him and, well, let's say that I'll never do that again, not because it was bad but because I like breathing - but it was a challenge I couldn't refuse and I was 2200% sure that I could do it. It impressed him and it had made me feel rather nice to hear that no one had ever done that to him before, let alone tried to.

    As you said, no stretching but every time he buried all of that dick in me, wow. Can't begin to say how it felt; not that "full" feeling you can get with most guys but you just know there's a lot of dick in your ass and very deep inside of you and, yeah, touching me in places I'd never been touched before (until my first colonoscopy) and, again, wow.

  9. #9

    Re: Best anal sex stories

    KDaddy: I agree there was no full feeling.. no stretching.. just deep very deep feeling.. it felt amazing to feel him that deep in me.. his thrusting was mind blowing,, he would almost pull out then back in balls deep.. his cum was very thick.. I don’t rennet ever having gotten cum that thick and all at once.. it was almost like pudding.. it stuck to the inside of my pussy,, well more like the inside of my lower back.. it was wild..

  10. #10

    Re: Best anal sex stories

    hmm (:

    Objectifying other bisexual men based on dick size is somewhat juvenile and shallow. Anus is not "pussy" in the real world. You do little to advance bisexuality in society.
    Last edited by tenni; Jul 2, 2023 at 12:49 AM.

  11. #11

    Re: Best anal sex stories

    I'm still waiting for the best anal I have ever had. While I have bottomed more than a few times, I cant say I have experienced what I think is possible. I've enjoyed them all (well, except the first one which I mentally enjoyed, but physically, yikes!). They were erotic and fun and felt good. But I've not yet been with a guy that was experienced enough, could stay hard with condoms, or franky well endowed enough for what I believe the possibilities are. I wrote in another thread (time for bareback?) that I think Ihave the right guy (we have great sex), but those condoms kill his hardon almost immediately. That and I think he has performance anxiety. Dildos are fun sometimes, but for me it's the person to person interaction that makes it worthwhile

    So! Still looking for what I think is possible!

  12. #12

    Re: Best anal sex stories

    Tenni said, "Objectifying other bisexual men based on dick size is somewhat juvenile and shallow."

    Yet men and women engage in this objectification and as a matter of course; it shouldn't matter but for many, it sure as hell does. Somewhere along the line, someone instituted that bigger dicks are better and, very likely, because larger dicks were great at achieving conception and it just... stuck. Without offense to Tight or other guys, it cracks me up to hear them refer to their anus as a pussy but, okay, I get it and while I find it funny, it always comes down to the individual and how he's thinking about things and I respect that.

    And as far as cock size goes, it's personal preference, isn't it? Don't a lot of us objectify each other at early ages by comparing our dicks? Mine's bigger than yours? Don't a lot of us who aren't so well-endowed suffer moments of penis envy over the guys who are well-endowed? A lot of people are superficial because they eat with their eyes first - nothing new about this - and, yes, it makes them shallow but... that's them. You'd think that over all this time and how enlightened we're supposed to be that these... traits would have gone by the wayside - but they haven't.

  13. #13

    Re: Best anal sex stories

    i can give the best year i ever had and it was 2021. i tried for a couple of years got close in 2019 and covid hit and kill everything in 2020 but 2021 i did it. there is 365 days in a year and i wanted 365 different dicks to fill my ass with cum in one year. not one per day but 365 different cocks up my ass. i have this one friend i have known for years. told me she was going to help me. and for new years we always have a party and there is lots of sex. so right after midnight she called me to the kitchen and told me to bend over the table and she tied my hands to the legs and pulled off my pants and cleaned my ass with a cold rag and i mean COLD. then she called everyone into the kitchen and the men 11 of them used me as a cum dump. that night. not counting the repeats. it took about 2 weeks and tessa my daughter brought home two guys and watched them use me. over the next month we would hit the beach or the creek and guys would use me. and i was already 112 different loads dumped in me then i had a dry spell i couldn't get a dick no matter what i tried. in april 2021 me and my friend went to the nude beach. and we found trucks parked like a wagon train. she told me to park she told me to stay there and put on my G string. and she walked about 100 feet to the trucks and talked to someone then she text me get over here now and get naked before you get here. so i did and when i got there they had 19 guys there and had a sling hung up between two trucks. when i walked in everyone just pointed to the sling. and all 19 dumped their load in me and when they was done the told me to get my old ass out of there and thanks for the fuck. over the nest few months i would add a few here and there and buy Dec 15 i was up to 301. i didn't think i was going to make it then my friend came over and told me and tessa we was going to Austin and Dallas. when we got to Austin my ass was used 43 times all weekend. not counting the repeats. repeats don't count. ok now i was close. and and Christmas day i was one away. i knew i was going to make it but we still had to go to Dallas everything was already set up and she already had it planed so i was going anyways. and from the 29th to the 31th i didn't only get my 365 different loads. i passed it by 24.

  14. #14

    Re: Best anal sex stories

    sounds like there is a bigger story here about your daughter tessa. i would love to here all about it.

  15. #15

    Re: Best anal sex stories

    This one is a very memorable one.

    This couple who booty calls us all the time, popped over about 8 pm recently. They knew our kids were all gone for the weekend. They were dressed to kill getting out of their car in our neighborhood in the sexiest clothing. Well she wasn’t in much. They texted us to watch in the drive way, hopped out once they knew we were watching, came to the front door (no one ever comes to our front door), her boobs and ass were hanging out, his cock dangling but at least only from a front view. We let them in quickly. Before we could get the door shut they dropped to their knees pulling out my husband’s cock sucking together right there. I saw two dog walkers coming. Oh MY GOSH! I was up to the top of the stairs bent over ass offered as fast as I could go. The wife moved up licking me crevice to crevice. Her husband joined. My husband closed the door, wheeeeewww!

    I had the giant cock of her husband in my hand with the head prying open my mouth as he now knelt in front of me, his wife tonguing my ass, my husband fingering the tiny little blonde’s pussy. Okay to the short version, after playing for quite a while some variety in sex play, fucking, and sucking we wound up with my husband on his back in the long ottoman with me straddling his waist trying to help get that over 9 incher cock in his ass of John’s. It took forever but worth the entire adventure. His wife was grinding on my husband’s face while playing with my pussy and ass. She loves fingering me for some reason. John was able to get enough of the head of his massive cock in to slowly fuck in and out of my husband. I was humping on him grinding along with the fingers working in and out of me. I now had a hand from the wife around me pinching a nipple I also had her husband’s hand on the other doing the same, kneading and pinching. The wife had fingers inside both my holes from the first hand. I was ready to cum and I did. I told her I wanted to slide back on my husband’s face which I did as she slid off soaking him with her pussy.

    About an inch and a half of the biggest dick to ever invade my husband’s ass was pumping in and out. I heard muffled sounds of pleasure from my man. Leaning forward to suck on him, the wife stuck her tongue up my ass again. I squealed egging her on all the more. Between my husband sucking on my pussy below and her tongue darting in and out of my anal hole, I orgasmed many more times. 2 inches – oh my goodness “FFFFUUUUCCKKKKK My Man’s HOLE. Tear IT UP!” I screamed in my head. I was riding, bucking, fucking the tongue and soaking my husband. I came hard so hard I sucked off my husband pleading for her to finger fuck me. She did, two fingers right in. I yelped with pleasure. My husband sucking my clit. I orgasm.

    3 and a half inches of 7.5 girth meaty cock fucking in and out stretching my husband’s man pussy beyond and back. I was so fixated I didn’t realize my hips were being grabbed and I was being thrust into my anal hole, big, wide, deep. UUUHHHHH. I was being fucked in the ass. The wife had manage to get on a strap on during my mind blank stare at the 4 inches of bull cock in my husband’s ass fucking him right in front of my face. Oh MY I had a large load of cum in my mouth. My husband filled me up. I swallowed but still some ran out all over him. I continued swallowing trying to catch up to his unloading his cum in my mouth. Oh mmmmmyyyyyyyyy inches and going in further. I felt the spasms from underneath me as my man’s body rocked with orgasms from his cock and ass. He was having an enormous group of orgasms. I love it when he has these. Yuuummmmm!

    OOOOHHHHH my ass was getting thumped harder. I orgasmed. 6 inches. I had suck my guy dry, reaching around I attempted to spread his hole wider for more cock. 7 inches and out, back in and out. I felt the uuuuuuuggghhhhhs and uuuhhhhhhhs, and oooooooooooohhhhhs, from my husband’s mouth against my pussy. Holy smokes John was full on fucking my man’s pussy hole, it was glorious! I orgasmed again. The dildo she was using was rather large I noticed. I felt so full, much like my man’s hole. Together we shook, shivered, shimmied, and orgasmed repeatedly.

    Legs over john’s arms, held up, spread as wide as possible. Now this was an ass fucking. Oh MY it was Marvelous! I was still getting mine as well. When John came in my husband’s ass it was so powerful it blew out the sides of his penis somewhat. Cum oozed out from the sides of his giant cock. Dang but that thing looked like a moose’s dick. I was orgasming again leaning over in the pool of cum on my man’s cock. I licked and sucked it up and his cock. It came to life. When my fucking stopped I sat up, climbed off, moved around to watch John continue to fuck my husband in his ass. Dang it was a fabulous sight. His wife came around to watch as well purring at the sight telling how much she loved seeing her man’s cock burying into an ass hole. I love it too. John loves fucking my husband, he takes it the best of us all.

    John’s wife pushed me over spreading my ass telling her husband, “Her ass is next. It’s all fucked and ready for your cock.” John smiled, “A two for one special tonight, glad we popped by.” When we pulled out we all four went, “AAAAHHHHHHHH!” seeing the aftermath of what John does is orgasmic in itself.

    He got up, took a shower to clean up. His wife climbed on board my husband’s cock working it until was able to ride it. And yes she took it right up her ass. It apparently was an anal night. She rode him until he came in her ass. John was walking out as they two of them finished their last orgasm. He clapped. Then told me to lean over my husband because he was about to fuck me until I couldn’t walk. And he did. My husband sat up after the wife got off. He spread me to help John as did his wife. Everyone worked together to get his cock inside my anal hole. It took longer that my husband’s but when it did. I hit the roof with orgasms.

    Before we all retired to the bedroom I was able to take 6 inches and take two loads of this beast of a cock’s cum. It fucked my husband twice as well cumming two times in him. I say it, because it has a mind of its own – lol. We offered to have them stay. After cleaning up we all fell asleep on the large bed. I awoke to the sounds of his wife in a 69 with my husband and her’s with his whale cock in my guy’s man hole once again. Big John never gets enough. They all fucked and sucked to many more orgasms. What the heck. After they finished I are the wife out like crazy screaming wild woman good. She sleep hard after that.

    I woke 7 hours later to John pressing his horse cock head into my anus. Oh my goodness this guy! We fucked, I came, and came, and came. He flooded my ass with cum. I came even more. My husband fucked his wife missionary but in her ass again. We had so much cum leaking, we had to change the sheets and lining. Showered off, cleaned up, fixed breakfast and decided it was pussy and cock time. Couples sucked cock together, drank cum together, kissed a ton, took a break, then fucked our spouses side by side swapping back and forth. We’d never done that. All pussy swapping. Neither me or the other wife can take her husband vaginally but we have a way to make it fun and pleasurable. My man usually winds up taking his load orally which we love. Me and the other wife three way kiss with him and the cum. LOVE love love that. Never thought I’d love French kissing with another woman but Grrrrrrrrrr this is the way to do it. My husband enjoys it as well.

    We spent the entire weekend with the couple. They are a lot of fun for certain. And yes my husband and I both got fucked in our asses several more times and while our faces were buried in his wife.

  16. #16

    Re: Best anal sex stories

    Very hot,lucky guy!

  17. #17

    Re: Best anal sex stories

    i went to the nude beach back in the late 80's. the beach was in really good shape. you could have went down it in any car. for about 5 miles then he became a nightmare. so i stopped i didn't want to take a chance of getting stuck and not have anyone large enough to pull me out. there was alot of nude people out nothing really going on but people walking around nude. and i was laying in the bed up my truck relaxing. when 2 sexy little girls showed up and ask me if i could come pull them out they was about 2 miles down. they had bikini's on but they was tiny just the way i like my girls. anyways as we was driving they said they had no money but would pay me something anyways and she leaned over and started sucking me off. after a few minutes the girls traded places. then we got to their truck. i told them they needed to be nude out here and they said they was until the got stuck. and they was naked in less than a minute. i hooked up the rope and pulled them out. and we hung out and fucked until about a hour before dark then they headed back home. i told this if they get stuck again i will be here. and they left. then 3 more trucks showed up they ask if it was ok if the parked here for the night. and i said sure water wont get here even when the tide comes in and they said they know thats why they wanted to park their. 3 trucks about 15 people 8 guys and 7 girls and the let me join in on their fun. no sex. YET. then one girl came up to me and said do you have a problem if we start fucking i said hell no i don't. then she said does gays upset you. i said nope. then she turned around and told some guy to suck his dick and he did. when she saw i was starting to get hard she set on the tailgate with me. and she ask do you want one to suck you. i told her sure. but she can also if she wants to. she said no tonight its only the guys and we going to watch. after about a hour i said what the fuck so i joined in and i fucked every guy there that night. and every guy fucked me and each other. it was such a turn on having girls. i say girls because i was young myself back then. watching all us guys fuck. that was one fun night. i have more stories about that beach before they started busting every one. i will tell as i figure out site.

  18. #18

    Re: Best anal sex stories

    Super hot wifekinky! If I'd met a woman like you, no letting go!

  19. #19

    Re: Best anal sex stories

    First time topping anal with a female was with my older sister (if you're not into incest related stories, please read on). She was only a year older than me, but very petit. We were both sunburned from being in my friend's pool all day, so when we got home, we decided to trade sunburn lotion massages. After we both showered, I was to be the first patient. She climbed onto my back and started rubbing in aloe lotion.

    Dressed only with a towel around my waist, the feel of her warm body on top of me got me so hard I thought I was going to pop. After making some adjustments, I positioned my cock so that it was sticking straight down between my legs and I was leaking pre-cum like a faucet. I don't know how she knew, but she reached around behind her and grabbed my cock and started to stroke me, all the while grinding her pussy into the small of my back (later she told me that was when she had for first orgasm). She continued to rub my shoulders and back with her free hand and made sure to let her hair fall onto me. Then, just as I was about to cum, she slapped me on the back and said it was her turn. We exchanged places, I tried to adjust my towel as much as I could, but there was no denying I was harder than a rock and it showed, and she had a visible wet spot on her bikini bottom.

    Being the trooper that she was, she took her place on her tummy under me. Because I was much larger and heavier, I placed my weight onto her thighs and began with a fairly light massage. Before long, she told me to press harder, but as I did, my cock was clearly trying to penetrate the sheer piece of fabric that separated her steaming pussy from my prying cock.

    "Ok, let's do this," she said, as she slid her bikini bottom down to her ankles. In the process, she made a point to grab my cock and give me a couple of strokes. Within seconds I was again massaging her back with my cock pointed down and sliding between her butt cheeks. The smell of sex was everywhere. After a couple of minutes, she reached back and took my cock in her hand and placed it against her. "Push it in... I want to feel you inside me."

    As told, I did. The funny part was while I was fucking her, even though she was so tight, I thought I was fucking her pussy the whole time.

    Later that night she snuck into my room and we cuddled like we had done when we were kids. I told her thank you, but expressed my concern over her getting pregnant. That's when she told me that I had cum in her butt, and to not be worried. But that she had cum several times that afternoon.

    Parents were never the wiser. To this day, I am the only man she has ever slept with, although she's gone through several same sex relationships.
    Last edited by jjourneyman; Dec 6, 2023 at 1:55 PM.

  20. #20

    Re: Best anal sex stories

    Quote Originally Posted by i'm uncut View Post
    she said no tonight its only the guys and we going to watch. after about a hour i said what the fuck so i joined in and i fucked every guy there that night. and every guy fucked me and each other. it was such a turn on having girls. i say girls because i was young myself back then. watching all us guys fuck. that was one fun night. i have more stories about that beach before they started busting every one. i will tell as i figure out site.
    YUUUMMMMMM I would be there with lights on staring up close. LOVE watching the men get it on.




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