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Confessions

First Confessions

Read the best #first confession stories


I'm a 21 year old guy, decided I'd try it with a guy for the first time so I hit up Craigslist. I ended up making some plans with a 30 y.o. at his place that night. I went over and we met outside and we walked up. It was my first time so I was kind of nervous and didn't know what to do. After talking for like 5 min on his couch he just started groping me and trying to talk sexy but that part I wasn't into. He eventually got me hard and pulled my shorts down. He got on his knees and started sucking my cock which was nice. Eventually after a few min he got up and pulled his sweats down jumped on top of me again and put his dick in my mouth. I hadn't done it before and his dick wasnt as nice looking as mine but I just started sucking and seeing how much I could take. We started to sixty-nine with me on top and I was pretty into sucking his sick and balls while I fucked his mouth. We got up and he strattled me so I could fuck his ass but we didn't have lube and my dick was to big so we went back to sixty-nine but with him on top which was still pretty hot. I sucked him and gagged on his cock a bit which I realized I wasn't very good because his dick wasnt that big and I couldn't take it all. He then quickly flipped over and lifted my legs like he was going to fuck my ass and I just let him go for it. He jerked me while trying to get it in after he put a condom on but his dick was kinda small and it wasn't working out without lube. He sucked me some more and asked me to cum for him but I was loosing it and he wasn't sucking me good enough to make me finish nor would he let me cum in his mouth which I was bummed about. He eventually came just checking me out while I posed for him naked and let him touch my ass which he was super into because I work out and have very little hair. Then he felt bad because he got something and I didn't but I didn't really care because I kind of realized I'm not into guys at all really, I wasn't even into him making out with me really the hottest thing was 69ing. I'm more into dominating the fuck out of a woman and maybe I'll try with a guy again if I actually get to fuck him but I like the juiciness of a vagina more tbh. Maybe a bi threesome where I fuck both of them who knows but I'm not into it enough to pursue it again over women. Anyway hope you like the story!


#gay   #first  


I am 18 and have been fucking an older married woman for 2 years. She lives in my neighborhood. She is really very pretty, has a little belly and wider hips because she had three kids. She is 38 years old, blonde on top and brunette on her pussy. It all started because a neighbor of hers, a really hard body brunette of 35 was giving me BJ's and she thought it was crazy that the woman wouldn't fuck me, but the woman didn't want to cheat on her husband. So the blonde said she would let me fuck her and being 16 and a guy, I took her up on it. I would play with the neighbors tits, ass and pussy, as she'd usually get totally naked when she blew me, but this time I got to actually fuck someone. She got very excited that she got to take my cherry and told her neighbor that she did it. So the neighbor stopped blowing me because my cock has been inside another woman.

So knowing I wouldn't have any source for sex my new blondy became my lover. She has taught be how to fuck, how to make women cum, and do everything to please a woman. About 8 months into our fucking she got pregnant, she really didn't know if it was mine or her husbands, but since they still fuck a decent amount she says it's his. He and I sort of look alike anyway. I got to fuck a pregnant woman, and more importantly got to suck her big, bulging tits. Mary is only a B cup normally but she grew to a really big C. I liked squeezing her tits and making the colostrum come out while pumping her pregnant pussy, but afterward I really loved the milk. After the baby stopped nursing I got her to keep her milk flowing for me for almost 4 more months. Then her husband was asking about it too much so she had to let it dry up. It's been great having a steady lover. Her husband leaves at 6am everyday and doesn't return until about 7pm so we get plenty of time together in between my work and classes. She's taught me everything, even letting me fuck her butthole. That has become my absolute favorite. I didn't realize it but she has been talking to Carrie her neighbor, the one who used to give me BJ's. So now Carrie let's me fuck her in her butt (her husband has never done that to her) and she feels she isn't cheating because he doesn't do that to her, and I don't stick my cock in her pussy, though I really want to do that. I'd love to know what that smooth shaved pussy feels like. I do eat her out though, and she totally screams when she cums, and loves what Mary has taught me. Carrie actually cums from getting fucked in her butthole. Mary likes that her stuck up neighbor is a bit of a slut too.

Plus with all I've learned and the confidence I have around girls, I fuck plenty of them my age now. I guess it's the confidence of my knowing what I'm doing in bed, and the fact that I don't care because I know I can cum in any of two very good looking, older women.


#married   #affair   #virgin   #anal   #oral   #nursing  


A few years ago, when I was 15, there was a very nice but very big girl working at the same store. She and I always had a good rapport but she was about 5ft. 5in and weight about 260lbs. She had huge breasts, but the big size never did anything for me. She was 19 and had a 4 year old son by her 21 year old husband. He knocked her up at 14, married her and at 15 she had the baby. He beat her when he would drink which was several times a week. We worked several evening shifts together and many times were the only ones in the store. She knew I was a virgin, and would make sure every now and then that I could see her tits or even her hairy pussy. Then one time when we had the store locked and were cleaning up, she came into the storeroom and kissed me full on the lips. Not just a peck but a heated, passionate kiss. She said she'd wanted to do that for a long time, and I thanked her and returned her kiss with another. She backed off, and started taking off her dress, then her slip, bra and huge granny panties. She stood before me totally naked, huge tits with pink aureola and thick nipples that stood out about 1/2 inch. Her meaty pussy lips were half hidden under her belly but she lifted her belly for me to enjoy the full view of her black pussy hair, and there was plenty of that hair.
"I won't fuck you, I won't do that to my husband, but I want you to be the only other person who's seen me naked like this" she said
I moved over to her and kissing her again, placed my hand on her pussy, took my mouth to her left nipple, and whispered, then just let me feel what it's like. She let me finger her, and told me to put three fingers into her pussy while I sucked her massive tits, my teeth rolling around those big, rubbery nipples. She moaned and pulled my pants down, I took off my shirt and I knew I was getting my first piece of pussy. I didn't care that it was a fat married girl my cock was hard and wanted pussy.
"I won't let you fuck me" she said again
"Then what are we doing?" I asked
She said she'd suck me and started. I then laid her on the carpeted floor and lain next to her. She was grabbing at my cock and I at her tits and pussy.
"Let me just put it in to feel what one feels like, and to feel what your husband feels. I won't fuck you, only push in and just hold it" I asked
She said that was OK and laid back and spread her legs and closed her eyes. I got on top of her and pushed my 7 inches into her married, fat cunt. "Just hold it there, don't move it around" she told me.
I did just hold it there, telling her how wonderful she felt and that I was glad that she let me have my first feel of a pussy on my cock. She wanted to fuck but held back and made me pull out. As she was rolling over I saw that pink rosebud of her asshole.
"What about back her" I asked as I touched her asshole. "Does he do it to you back here"
"No, no one has ever done that to me" she commented
"What if we do it then? If he doesn't fuck you there, then it's not like you're taking something away from him, and it'll be a sort of mutual thing, two virgins fucking"
"No it will hurt" she said

Having had a cock up my ass once when very young and very unprepared, I vowed to never hurt anyone like that, and I told her I'd be gentle. She stood up and walked to the office totally naked, and got out a jar of Vaseline and rubbed some up into her asshole, and put some all over my cock. She then rolled over on her stomach and reached back and spread her butt cheeks exposing my target. I told her to roll on her back and she did pulling her legs up to give me a full view of her big tits, luscious mouth, hairy pussy, and that tight looking sphincter.
I leaned in kissing her and pushed my cock into her and inch at a time. Once it I gave her time to get used to it and she was through squeezing her ass muscles (which almost made me cum), I began slowly and gently pumping my cock into her ass.
"Is it like you thought? Do you like it this way?" she asked
"yeah, it's great. I liked your pussy too" I whispered back
"That's for my husband but my mouth is for both of you, and this. . . my ass, is only for you"

I kissed her and tweaked both her nipples between my thumbs and forefingers and she started bucking and heaving, breathing heavily, and was actually cumming. That made me shoot off and I couldn't help it I found I was ramming my cock in and out of her to the hilt everytime, and going very fast but she was cumming. I shot rope after rope up into her. As I was doing that and kissing her with our tongues going crazy, I kept remember the man who fucked me, this was the way he was acting, this was what he was feeling, only I had a woman with a pussy behind me.

After that we had oral sex (she taught me how to eat pussy well) and anal sex. Every once in a while she'd let me stick my cock inside her pussy. She got to where she would sometimes get a bit demanding and would make me eat her pussy after her husband had fucked her. She liked getting rid of his sperm and liked making me eat it I think. Then I could always fuck her ass, hard and fast. Finally one of the times I was inside her pussy, I started pumping and she tried to make me stop. I held her arms down and fucked that fat cunt and came buckets into her. It was my first piece of pussy. Unfortunately I guess I raped her to get it. She stopped letting me fuck her for about a month, then we started in again, right as I was about to slip my cock into her asshole she reached down and put it in her pussy.
"Fuck me baby, fuck me like I'm your woman"
I did and after I shot another big load up her cunt, she told me she was pregnant and that he husband had been out of town during the time she could have been fertile, which means the baby was mine. I had gotten her pregnant while I was raping her pussy.

She stayed with her husband, which was good as I had lots of college plans, moving plans, and had plans of laying girls who weren't so damn fat in my future. During her pregnancy I got to nurse on her (and after as well) fuck her in the pussy or ass or mouth as my choosing, then about 3 months after the baby she quit. I went on to a great job, traveling internationally, have several svelte girlfriends, and never looked back. Though I can say that any woman who has not been a one night stand, has had to take it up the ass as well as the other two holes. I guess I'm an anal addict now, after all that was my first way of getting laid.


#anal   #nc   #pregnancy   #cheating  


The first time I performed oral sex on a girl it was in 1975 and I was 14 years old and the girl was 15. I was just reaching puberty and she was there. I wanted put my dick in her so bad but she was soo tight, so the only thing I could think of doing to get lubrication down there was to lick her pussy. She was very skinny and tight, I licked and sucked, not having a clue of what I was doing, but then I again tried to get my dick in her, she lifted her leg wide and I still could not get it in her and gave up. We walked back to my house and she asked if I wanted to try again and said if I spent more time down there she thought it might make it go in, I think she just wanted me to lick her pussy more. Never did get it in her. Dammit!


#sex   #oral  


My first time having sex was with a woman much older, I was early teens. She was married and her husband watched her with other guys. He set up many gangbangs for her usually all men their age (mid 30's). They let me come in at the end of one of her gangbangs, in a motel room, after everyone had left and it was just the two of them, I guess because of my being underaged. She hadn't cleaned up at all as he liked her to get all messy during and didn't even permit her 1 clean up during her gangbangs. She was lying there on the bed with a pool of cum beneath her ass and pussy. She had a very hairy pussy and much of it was matted with cum too, cum splashed on her belly, her face, her tits. Her legs were open, I sucked her C cup tits and make her nipples perk up. He told me I didn't have to be nice because she was a whore and you just piled on and fucked whores. Then I got between her legs, and stuck my cock into her loose cunt and felt the pool of cum on the bed on my balls. I fucked her loose, cum filled cunt and added mine to the mix. He made her stay there while I recouped, even made her suck me and I got hard again, and once again filled her with my sperm. While I was doing that she sucked her husband and he came in her mouth. She kissed me while I was fucking her and squeezing her boobs, and I could taste his cum as she pushed some into my mouth with her tongue. It was not only my first fuck, she was also my first kiss, with her husbands cum in her mouth.

He said I could come by there house and fuck her sometime there, without all the gangbang mess. I can't wait.


#mf   #gangbang  


I was waiting for a friend to. visit from out of town. He didn't have a car so he was traveling Greyhound. It was getting late and then the Dispatcher announced a two hour delay for mechanical reasons. Stuck in a bus terminal late at night with mothers with young kids,, assorted lowlifes, and the homeless.

Visiting the restroom, I found it cleaner than I expected but all the toilet stalls had holes in sidewalls. Being only 18, I was inexperienced and had never heard of a glory hole. The toilet seemed a more private option than the urinals. Someone followed me into an adjacent toilet and immediately I saw the biggest black dick in the world. Well, maybe the biggest in my world.

Staring at it didn't do any good. After a minute Dickman said well stick yours through. Still not bold enough. Fortunately a man came into the stall on the other side of Dickman. When I could tell the other two had gotten going, I stood on the toilet seat and watched the action. Dickman got off first than the short white guy I couldn't see very well.

I waited outside the stall after things wound down. Dickman told me that's how it's done, Kid, Don't hang around here if you don't want to play. It took a while, but eventually I took my turn with a different guy. Lucky for my friend I was so turned on when he finally got in he got the first BJ of his life and I gave the first BJ of mine.


#bj  


Weird dream I somewhat remember me eating out another woman when my husband walked in on us. And that is all I remember, but I keep thinking about it. And when I do, I end up getting wet and horny. If I am alone, I end up masturbating. I am twenty one, married, and never even thought of another girl. So weird and wrong. What is going on. I cannot make sense of it. A love / hate thing.


#firsttime   #weird   #lesbianaction   #husband   #sex   #horny   #wet   #wrong   #eatingout   #masturbation  


When I was 17 a stranger in a bathroom asked if he could give me a blowjob. I was always curious so I let him and I came right away and he swallowed it all. Since then I’ve played with men and enjoy putting my cock in their mouth.


#firsttimegay   #firstblowjob   #bi   #gay  


I had sex for the first time and didn't tell the guy it was my first. Blamed the bleeding on his big dick. He believed me


#sex  


My husband convinced me to have a threesome. He won't admit it, but he has the hots for this sexy neighbor. And I won't tell him I was curious. It was my first experience with another female. I expected one and done. Wow, she was/is awesome. Now just the two of us go at it when we can. If my husband only knew what he started. Girls, just try it once, you might be surprised. With that being said, I am now open to mmf, just once?


#threesome   #ffm   #mmf   #husband   #neighbor   #sexy   #orgasm   #curious  


it was a hit and run kind of thing, and the friend group i was with liked the idea of me being their sacrifical dirty lamb sexually as a virgin so ugly and it was drunk and drugged rape the first night and mulling abusive relationship same guy the next time months apart and we never loved each other. we agreed to just never see each other again as he had many wife's and kids and i didn't find it good loving experience. I guess I am just really ugly and boring, and I don't care anymore. I was so ugly I was a virgin til 30. no n liked me.

i have never been a hot guys first choice.


#want   #to   #be   #a   #first   #choice  


Back when I was a little girl (5 yr old) I was at church and me and my friend lucy were at the back of the church where no one was and we played house and we pretended to be cats but then we started playing as husband and wife I was the husband and she was the wife and we kissed just a peck and we heard someone coming so we hid under a table and we giggled and this is where it got sexual we looked at eachother and we slowley moved in to kiss eachother and we kissed there and we kissed roughly and we used tongue too she now goes to my school and we never mention this to anyone I get uncomfortable and awkward around her but I have a boyfriend now


#regret   #lucy  


I had my first hookup last Friday night. I usually party with my friends every Friday or Saturday night. It's our only outlet for the stressful work week. First time I got completely drunk, off myself and went home with someone. I feel completely horrible about right after.


#hookup  


When I was young my parents divorced , was was mad at my mom for treating him badly , I stayed with him as much as I could but he met and arrived another women who was really jello us of me .
They moved away , my mom had turned I to this huge slug and had guy after guy visit.
I stayed with my auntie a few times but she ended up coming on to me, she went down on me a few times but I just didn't like it as I'm not a lesion.
I went back to my mom's and tried to get used to shit, more than a few times I witnessed her giving blow jobs, she would come out of her bedroom cum dripping out the side of her mouth, .
There was one guy that came by a lot, he had a very pretty pens , it was lovely , I would master ate thinking of him.
I was in the bathroom peeing and he came in , he looked down saw my bald pussy I could see him start to grow as he was wearing boxers, I finished up but didn't get off toilet, he came over or me pulled his shorts down and I did what I saw my mom do.
I was so turned on I grabbed his ass as he pumped my mouth, he started to breath heavy and felt his dick get harder, I pulled back so just my lips were at his hole as I felt him pulse into my mouth, I loved the feeling , enjoyed the taste of sperm .
He finished I got up off the toilet, and went outside right into my mom, she yelled at me and slipped me on the face , unfortunately I still had cum in my mouth and when she slapped me it left my mouth and was all over my face.
She yelled at the guy told him to get out and take this slutime with him.
We left together him holding his pants me in a long tee shirt and drove away in silence . After about a hour he asked me what I wanted to do , I said I was cold and hungry so we went to his place he made me some breakfast and gave me some of his daughters clothes .
I tried to go back to my mom's house , but she was Pisces, I we think back to his place and asked him if I could stay there , he was a bit nervous about it as I was younger than his daughter (she visited on weekends) and how he could explain me being there , I went up to him took his dick out and gave him a blow job looked up at him with my mouth full of cum and said I can be your girlfriend .
He smiled and asked me if I had ever had sex before I said yes 2 times I gave a blow job , we laughed.
I've been with him since


#curiosity   #parents   #confession  


I am a 16 year old highschool boy, and I finally fucked someone. My best friend who is 15 lived on the same street as me for about 8 or 9 years with his divorced mom. We've always hung out, explored together, and as puberty happened to us we would strip around each other, even jack off together. I even tasted some of his sperm and he tasted some of mine. I have a sister who is 15 also, and when possible and no one was home we would go through her dirty clothes and pull out her used panties and smell them, even jack off into them. Then we started doing the same to my moms hamper. In her pants we would see more, even some of what I assume was my dads sperm in them, and they always smelled more of her sex than my sisters panties. We would do the same with his mom's dirty undies and bras.

His mom left us alone for this past weekend, staying at his house, my parents just down the street she didn't think anything of it. On Saturday morning we both got naked and were in his moms room going through her things. We found some pretty wet panties and we sniffed them, rubbed our cocks in them. Both our moms are pretty hot still, in their early 40's but really nice bodies. My mom actually has a better body than my sister does. Going into a drawer in her walk-in closet he brought out a huge vibrating dildo. I mean this things was bigger than any cock. It was like two soda cans stacked on top of each other. We couldn't believe she stuck that thing inside her. I turned it on and rubbed it against his cock and balls and he got instantly hard. He did the same to me. In her nightstand I found some KY jelly.
"You know what this is for?" I asked
"What?"
I explained that it's for anal sex mostly and it lets things slip in really easy. He took some on his finger and pushed his finger inside his ass while I watched. I put some on my finger and pulled his out, and stuck my finger in his ass and moved it back and forth, penetrating him fully the entire length of my middle finger.
"Goes in nice and smooth huh?" I said
"Really smooth" he muttered through his grunts and moans.
He laid down on the bed face down spreading his cheeks, and told me to put some on his butt. I did, pushing it in and around his hole.
"Now put some more on you, get it all over it" he said
I started putting more on my finger and he said no, that he meant to put it on my cock. I rubbed it all over my cock and took up his invitation, laying on top of him on his mother bed. I slowly but steadily pushed my thick 7 inches into his baby smooth butthole. I was in and stopped. He was moving his bottom around and asked if I was all the way in. I had about an inch left and he grunted as I pushed it all the way. He started rocking his ass in fucking motions and I asked if that was what he wanted me to move like. The reply was almost a pleading for me to do it. I started fucking him. It felt so good to be inside someone I didn't care that it wasn't a girl. I always dreamt of fucking a girls but his ass felt so good, so tight along my shaft. I could feel his warmth all the way with every stroke. Added to the great feeling, I was sniffing his moms panties and could smell her pussy. I couldn't hold out more and after about 4 or 5 minutes I started moaning and thrusting really fast and really hard.
"Do it, do it, fuck me, fuck me real hard" he kept saying over and over as I was shooting my sperm inside his butt.

After I was done I just laid there with my cock still inside him. Eventually it slipped out of him and we both got up and cleaned up. I'd finally fucked someone. Not what I'd imagined but at least I fucked and came inside someone.
We don't talk about it, but we went and bought our own KY so we wouldn't use up his moms. We even found some naked pictures of his mom. That evening we both slept in her bed, I had slept there the night before alone. This time I fucked him on his back. I even sucked his cock after fucking him once, one of the times he jacked off while getting fucked. I don't really want to suck him or to get fucked, I just want to fuck and get sucked. So it's Friday now, we have another weekend without his mom. We've stayed all week together. I fucked him 5 times that Saturday and Sunday and got sucked off once, and sucked him once. This week, we would fuck when we woke up in the morning, or he'd suck my cock and jack off while doing it. We always had some form of sex at least for me, if not him when we got home from school, and at night in bed we fuck like newlyweds.

I really want to fuck a womans pussy but I like this for a nice substitute for now.


#mm   #anal   #oral  


I really like my ex. He was my first boyfriend and I can't stop thinking about how funny, cute, and nice he was to me. He broke up with me because of long distance (We live in the same city, and just go to different schools). It's been 3 months. He's had over 4 other girls. I still like him, but just want to be friends. Any advice.


#firstboyfriend   #ex   #missingex   #crushing   #likemyex   #hopingtobefriends  


When I was 17 I got lost in the woods on the mountain. We were camping with friends, and I walked off to explore and when I looked up I was lost. I yelled but no answer, the sun was coming down and the chill was in the air, my father had said there would be snow flurries that night. I kept walking, and I came upon a camp site with a man. He asked me what I was doing there and I told him I was lost. He told me that it was late and I would have to wait till the next morning.

He gave me something to eat and he said I would have to share his tent, a small one man tent with sleeping bag. He put out the fire and hung his stuff up in a tree and set some bells out around a perimeter, just in case he said. Early warning, he showed me where the bear mace was and he had a gun and showed me where to pee. He stood by me talking while I peed. When I was done he peed into the same puddle and then covered it with dirt. Back at the tent he told me to take off my pants and jacket and he got down to his underwear and put me in the sleeping bag and he got in, adjusting us until we were both trapped inside. It got hot real fast so he took off my top and he felt me up taking off my bra. My panties came off and in less than five minutes after we got in the sleeping bag he had sex with me. Naked he pulled me into a spoon and put his arm under me for me to lay my head on and we went to sleep.

Twice more during the night he had sex with me, once from behind in the spoon position, and the second time he put me under him and we had missionary sex. All three times he completed himself in me. I knew about that, I had the talk and my grandmother was the type of person who was explicit about those things. Nothing was a surprise, except that it was happening. I slept in his arms and when it was light we got up, we peed naked into the dirt again, he stood me up tall so he could get a good look at me and he told me I was a fine young woman, he was proud that I was carrying his sperm inside. We got dressed and I told everything I could about where we were camping and he said he would try to find the campsite if they were still there.

We walked back up the mountain, he went pretty straight and when we topped this ridge he showed me the camp with my parents. He told me how to walk down and to keep to the open country, and he would watch until I got into camp. To remember I was carrying his offspring and he would give me another one next fall.


#first   #time  


When I was 16 I slept at my best friends house and we watched Babestation on his TV in his room. Being horny teenagers we found ourselves, sat next to each other on his bed, wanking.

Being curious about touching another guys dick, I asked if I could touch him. He agreed and for a while we wanked each other, which I quite enjoyed.

Anyway long story short, he finished before me and kinda lost control of where it landed. Since I was sat next to him some landed on my leg and arm which I was pretty surprised about but it was hot. In fact, it actually helped me cum. But that's a secret. As revenge, I came over his bed. He wasn't impressed.

We cleaned up and went to sleep. We joke about it from time to time, but it nothing has happened since.


#gay   #masturbation   #cum   #friends   #wank   #funny  


I had my first kiss with a girl named Britni. It was amazing. Sadly her mom found out and she isn’t allowed to ever see me again.. she was my everything. I lost a piece of me.


#brokenheart   #whyme   #firstkiss  


I had my first kiss a year and one day ago at the age of 17. It was with the girl I had the biggest crush on in 8th grade through highschool. We were just friends but she let me kiss her, and now we don’t even speak. I miss her sometimes even though she just kind of stopped talking to me.


#firstkiss   #relationships   #sad  



Pray and roll the dice for #first

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