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Confessions

Time Confessions

Read the best #time confession stories


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  


we were 12-13 and at a sleep over, he and I at another guys house. We had a few beers and we're watching tv. We had been talking about sex all day and how we had felt up girls and fingered them. The host had dozed off in front of the tv and my friend started asking about feeling a girl up. He pit his hand on my thigh and asked if that was how you started, I was wearing briefs. I was under a blanket and he had his hand under there. He rubbed my thigh a little and in a whisper asked if he was doing right. I just said yes that's right. He didn't stop and he was now inches away from my crotch. I was getting hard and didn't know what to do, I just froze as he slid up and began feeling my dick and balls. He immediately remarked that I must like that and all I said was it feels good. Last I remember is him saying it will feel better if I go in your underwear. His hand went down and his touch was driving me crazy, he had gripped my cock and was stroking it. As I really started getting excited our host woke and rolled looking at us asking if we were still watching the show. I'll never forget how it felt answering him while my other friend had a hold of my dick. I said, you can turn it off. As I rolled away from my friend he let go. The next day he asked me up to his room and it all unfolded. I had been thinking all day how good it felt and how wrong it was, the good won out. We quickly had our pants and underwear down and he was playing with mine and I was looking at his. I finally gave in and reached over and played with his. We were up there for more than an hour, we had no idea that we were edging each other, it came natural. We would stop the other when we got to close to coming. He suggested we try and come at the same time. We laid on our sides then face to face and teased away on one another. We were rubbing them together and looking down watching was putting me very close. I told him and he just responded that he he was going to "shoot off" as we said back then. He started shooting on to me and immediately used his semen on me and I started coming. I never felt anything like that before, I had jerked off but this was different. I wanted to stop doing it with him but didn't. We must have done it 30 times that summer, we did it ever time we could be alone. At 15 I had a girlfriend I was fooling around with and I stopped with him until 17-18. We were alone for some reason and drinking, I think another friend was with us and someone drove by and he got in the car with them. We parked in a secluded spot and were drinking beer when his questions about sex with girls started. I knew where he was going and didn't really want to but was a little drunk and horny. His hand came over and went at my crotch and when I didn't stop him he went for my zipper and had my jeans down in a minute. I was so hoping he would suck me. After a while I felt guilty about no touching him so I reached over, he immediately dropped his pants and I could see his cock. It had gotten so much bigger, bigger than mine by two inches and really thick. I couldn't take my eyes off of it. I was very impressed with it and told him so. We held them together and he was noticeably larger and his turned down a little, while mine turned up. I was a little shy of six inches and mine was really skinny back then. He was well into seven inches I would say and so fing thick. The urge to suck him became unbearable after a while, I couldn't believe I wanted to so badly. Once I went down on him I realized I was going to finish him as well. He was surprised and made me stop after about two minutes so he could suck me, which I enjoyed but all I could think about was getting back on him. We were both very turned on and I said something like let me finish you as I went back down. He gave me two warnings but I never slowed, I took all of him and probably kept sucking him for two minutes after he finished. I remember his shaking as sucked and tongued his sensitive head. As we switched positions he asked me what I did with it, I just said its gone. You swallowed it? Yes. As soon as he took, me in his mouth I was coming. I must have let go ten or more ropes and he couldn't take it all. It was all over us. He was so happy after we finished, he was holding on to me and kissing me, that's when I realized he was fully gay. We kept it up till we were 23 and he found a lover. I was never emotionally attached and never will be to a guy. But that was still some of the best sex I've ever had, only two encounters do I remember so well, that one and when my wife and I had a three way with another guy. It's like those moments are on video in my mind thirty plus years later.



I was always so horny as a teenager. I wanted to be railed all the time. Needless to say, my neighbor was hot, but he was interested in someone else. One night I didn’t care. I was so horny it was driving me crazy. So I walked down my neighborhood 6 houses down to his house. He wasn’t home… but his dad was. He knew what he wanted and didn’t care, he invited me in. We were talking about his son funny enough, but an awkward silence ensued… he started looking me up and down. It wasn’t his fault I had on a skimpy dress, my tits we’re hanging out of it. I wear a triple D. He started caressing my thighs and slowly worked his way up to my vagina. So we started making out. He started grabbing me everywhere. I was so turned on. After about 5 minutes of that I lead him to his living room and pushed him down on his couch and strattled him. His dick was pressed against me, it made me want him even more. He started taking my dress straps off and then my tits were out for the world to see. He started grabbing them while still making out with me and then we stopped making out and he moved down to my tits, he started sucking and biting all over them. Then we made our way to his bedroom… I was grinding on him and then he took my dress off the rest of the way and I unbuckled his belt and unzipped his zipper of his jeans and pulled his pants off leaving him in his boxers, but I didn’t take his dick out, I teased him… I bounced up and down a little and started grinding up and down on him. Then I got off of him and walked out of his room. He came chasing after me, I’m guessing because I gave him blue balls. I was regretting my decision to not wait for his son, and doing it with him… but I said to hell with it, if his son and I ever happened I didn’t want it to be my first time. So I walked back to his bedroom and sat on the side of the bed until he came in, he walked up to me and grabbed my arms and pushed me down onto my back, he towered over me and started with a kiss on my mouth worked his way to my nipples, down my stomach and to my clit, he knew exactly what to do down there, 3 ex wives… I’d hope so. He made me completely unfold on his mouth. What can I say. I wasn’t going to be selfish. I stood up from the bed and pushed him onto it, the I climbed on top or him making out with him and grinding on him until I made sure he was rock hard again, and I got off the bed and pulled his boxers off. I teased him a little and started kissing his thigh, I could tell he wanted to force my mouth on him. But I kept teasing him, until he begged me to put it in my mouth. I did just that, and it was amazing. I finished him off twice. I didn’t think I’d be that good at it considering it was my first time. But it was almost like I knew exactly what to do. But I wanted more. I assume he did too, because after all of that he pulled me on top of him strattling him again and started kissing my neck. But I was thinking of something else… I lifted myself off of him just enough to slide his dick in me. Then we went crazy. I didn’t realize I could bend that way. Figured out the positions that I love and the ones I didn’t enjoy so much because they were uncomfortable. After we finished I put in my skimpy dress and walked back to my house.


#sex   #lust   #fun   #firsttime  


I am 15 yrs male. I masturbate all the time and it feels really good. I love doing it and sometimes in strange places. A man I know (40yrs) caught me doing it in his basement when I was cleaning. He didn't care, he came over and did it for me and put my cock in his mouth and sucked it all down when I shot off. Then he told me to take off my clothes, got me upstairs to his bed and he had sex with me. He was slow and gentle and used a lot of lubrication. After I got used to the feeling it wasn't too bad. I still want to have sex with a pussy but I want to have sex with him too. I let him have sex with me as often as I can, and afterward he sometimes takes me in his mouth. He bought some makeup, lipstick, stockings, bra, panties that I wear for him and I really enjoy it. He said that he knows of a woman who is older than him and not great looking but she would let me have sex with her. I can't wait. I've really come to like having sex with him. He says I'm better than any girl he's ever been with. The woman sent some pictures of herself naked with him, and she's coming over tomorrow. She says first he and I have sex, then she will let me have sex with her.


#mm   #masturbation   #mf   #mmf   #anal   #oral   #virgin  


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  


I haven't told this to anyone, but when I was 15 my first sex was homosexual anal. I fucked my boy cousins ass one night while staying at his house overnight, he was 15 also. The next day we went to the basement behind some shelves. He had his pants down and bent over the back of an old couch, with Vaseline on his butt and a jar of it in my hand I was going to lube up my cock and them use my receptive cum bucket again. He was wanting it as bad as I wanted to give it. We got so involved we didn't hear his sister (14) come down stairs with some laundry. She came back and asked what we were doing, and he stood bolt upright pulled up his tidy whiteys then his jeans and walked out. I was there with a jar of Vaseline in my hand and a hard 7" thin cock sticking straight out.
Oh, were you guys doing what we all used to do when we were little? she asked. I replied yes. From the time we were about 9 till 11 all three of us, plus one neighbor girl formed a club and used to get naked and play with each other. My cousin used to do strips for me and her brother in her bedroom if no one was around. She would let us rub our little cocks against her butt, even trying to insert them, I fingered her pussy and it got real wet before she chickened out and left me hanging, but once she started developing tits and pussy hair she stopped it all. We tried and tried to get her to at least show us her tits and hairy pussy but she wouldn't.
Don't tell my brother how much hair I have or anything, and you can only stick it in my butt, don't you dare stick it in me in my front, she insisted. Then she bent down and told me to rub some of the Vaseline on her butt. I did, then put some on my cock and fucked her up her ass.
My first and second fuck, were my cousins, a brother and sister, both anal. I continued to fuck them both for about 3 years. Her, only anal and eventually oral and her brother only anal. I did manage to suck his cock to completion about 5 times during that time though. Finally; one time when I took her on a date, we went to our normal motel, and I held her down while I ate her pussy, she loved it. About a month later I was eating her, and spread her legs, pinched her D cup tits and holding her down stuck my cock into her pussy. I finally got my first piece of pussy. Dark, hairy pussy that bled a lot. I always heard it only bled a little when breaking her hymen, but from eating her out the hymen was pretty thick. It bled for about 3 days actually, didn't stop until I fucked her a few more times. She hated that I forced her to fuck and stopped seeing me for a while. Then came back and I had a nice steady piece of pussy, ass, and mouth, plus her brothers ass.


#bi   #anal   #cousins  


18m here. I took a girls cherry, she was my first virgin pussy. I had one virgin ass with a girl but never a pussy. I knew Connie was a virgin, she told me as we were talking in class one day. She is pretty fat, not really good looking, and I'm not into big tits which she has in abundance. But I dated her just to say I had a virgin. She said she'd never blown a guy before either but I think she did, she was too good and swallowed it all, everytime she sucked me off. I want to pop her butt cherry. After that, I don't know. I don't really like going out with her, she's sort of dumb actually, and I've always dated really hot girls with incredible bodies. I keep thinking of the blood on the sheet and on my cock after I popped her pussy though. It was hot. I wiped some of it and my cum up with her panties and I still have them.


#virgin   #bbw  


It all started when I was 9 years old . My family needed to travel for a few weeks and hired a sitter for me, As I had to be at school without a long absence if I was to move up to the next grade without Summer School ! Bob was young, athletic and good natured so we were a better fit than I understood at that time. Over the first few hours, we got closer and closer. Bob was very attentive to me and my whims. He would look deeply into my eyes it was as if He was reaching my soul. This drew me even closer to him. soon there was a bit of brushing my hair out of my eyes & soon there was gentile furtive brushing my hair back or out of my eyes, light pats, touches or rubs and this made me feel pleasantly different than usual. After several hours of talk and play I was beginning to feel very relaxed and strangely attracted to by all the attention.. Then, He looked very deep into my eyes for a long time which started to arouse me and he pulled me very close up to him. I could feel his heat and became aware of his musky scent which gave me a tingling in my crotch. Now he clasped my head in his hands and and firmly planted a very sensuous French Kiss on my stunned lips. His tongue pushed into my mouth and started a fire to smolder that I never knew was possible. We Kissed again and again ,each time with more heat and a rising passion that I could not yet understand. We ground into each other as his hands ran all over me. he gave me hot kisses on my earlobes and the sides of my neck as he worked my shirt open. soon he was tweaking and kissing my nipples and this was making me burn with lust and desire for things I did not as yet understand. Then he let his hands slipped down on my globes in a very warm and sensuous way as he squeezed and massaged. Somehow he managed to drop my pants and undershorts to the floor and step me clear of them. Bob kissed my shoulders and chest as he removed my shirt and I was now very aroused and could not think what to do about it. gentily Bob's fingers moved from my globes towards my crevice and went lightly exploring as he moved inward. I felt a light electric fluttering as the finger tips brushed my rear entrance, but soon the touch was more intense and pulsation on that small rosebud. Out of nowhere some Crisco appeared on his fingers and it was soon spreading around my entrance with a pulsing and thrusting motion. I started to thrill to this new intense sensation and he slipped a finger slowly in and out ever so slowly with a twisting and circular motion. This got a follow up of a second finger and a more vigorous stretching and expanding motion. I noticed that my small tool was now very hard and then I felt a third finger join the stretching party. By now I was loosening up and becoming very relaxed, so I started to thrust back on his fingers as he pushed in and after some time He was all in up to the third knuckles and now rotating too ! Bob withdrew slowly from me while giving me a very hot and deep French Kiss that seemed to reach way down into me. At this point he took my hand and lead me easily down the hall to the Bedroom ! Once there, he places his hands on my shoulders and gently pushed me down on my knees as he moved in with his fully erect Cock which he rubbed on my lips as he massaged the nap of my neck. As his cock brushed back and forth on my lips, it was as if I was mesmerized and my mouth opened as he slid in. I closed my lips around his head and got to work with my tongue and soon he was thrusting in and out, all the time going a bit deeper. After a while he was all the way down my throat with his 8 in. tool and I was loving it ! Then he stopped and let me, up so he could take me onto the Queen sized bed. He whispered in my ear hotly that he needed me and wanted to make me his ! He asked if he could have an orgasm deep inside of me because he wanted and needed me badly. We French Kissed for a bit and I said YES that I needed that too ! After a time he moved into the missionary position and prepared to open my carnal love canal up, wide ! I was so besides myself with Heat, Passion & Raw Lust, that I would have done absolutely anything he asked of me ! Many very enjoyable hours had past to get me to this point and now I wanted to give it up completely to become his cock slut and pussy-boi ! Bob took firm but gentile charge and mounted me to make me his Bottom as I spread my legs open to give him all the access he wanted. Bob kissed my little head just a short bit, then scooped my legs under the knees and raised them to my chest as he slid a hard pillow under my buns which gave him perfect alignment to enter me. i placed my arms and shoulders over my calfs, thus locking my position up to give Bob all the action room he wanted. We continued to French Kiss and feel each other all over. I felt a tapping on my rosebud and it sent thrills through out my entire body. this continues for sometime and got stronger and stronger which sent me over the edge with craziness as I was now so hot that I was mumbling incoherently and begging Bob to ram me hard and deep, as I tried to thrust to meet his teasing thrusts ! Now Bob moved forward a bit at a time with each thrust going in slowly and deeper. After some time when he was well in, he met with some resistance that had him pause. Then he told me that he now needed to break my anal cherry and there would be some pain, but if I could bear with it the feeling afterwards would be beyond anything I could even imagine as it spread throughout my mind and body ! I told him I wanted to be his and he should go ahead with it ! Bob braces himself and quickly placed a French Kiss lip lock on my mouth that completely covered any possibility of sound coming out and strongly thrusted forward into my deep as I yelped as the pain consumed me. Now he paused to let me get my balance and let the pain subside. Soon he was thrusting in and almost out slowly again and now was starting to feel like I was being elevated to paradise on a cloud ! The feeling was very electric & thrilled every cell in my Body to the point of disorienting me far away from reality ! My Lover soon picked up the pace of his thrusting until he was hitting into me hard fast and strong and I was thrusting to meet him with all my strength ! I never dreamed Life could get this joyous & Good and juice was flowing freely ! After some time I felt a charge in my crotch & Bob filed my deep up with a massive breathtaking Orgasm that shook us both from end to end ! Now,I was marked as His & a wide open Happy Bottom ! This was just the first 24 hours of a month long Sitting Job and I was an eager student that was willing to learn to do it all. We were at it every day, as often as our strength would allow ! After that, I went to his place on the down low almost ever day to practice what we shared together freely but privately ! Then he bought other Men Friends around to try me out and I just loved the variety that some of these hot sessions brought ! Most of these men loved my Carnal Skills and use them as often as they can even now !


#sitter   #anal  


I had been bi-curious for years. Since my early teens I would jack off while bent over the bed imagining someone fucking me from behind. I always had a girlfriend and back then the internet was new so it wasn't easy to contact others feeling the same way.
I was divorced by the age of 31 and decided it was time to check out my bi-side so I placed an add on CL.
I got many responses but one was from a younger guy near me and we clicked a bit as we traded messages.
I gave him my address and he came over on a Sunday night.
We talked for about 10 mins and had a cocktail and then I said, well, lets do this.
We traded off sucking each other going back and forth and then we started to 69. It was SO HOT!!
It was all I could do to keep from cumming too early.
Then he tried to top me but I was too tight. He said he was used to being a bottom and I could get behind him if I wanted so I put on a condom and climbed in behind him for as long as I could before having the most intense orgasm I think I had ever had!! He was about 5ft6 and 150 pounds, totally smooth perfect ass.
This went on for about a year as we would get together on Sunday nights at my house.
It was SO HOT and Im bi but mostly attracted to women.
I will never forget how much fun that was. Wish I knew where he was nowadays.


#bi   #hot  


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  


Can't believe I am posting this.....Fml
so I had been seeing this guy for a few years and I figured hey I wonder what he would think if I wanted to have a 3way. I was so so nervous to ask him about it so I waited until the weekend when we were going out with some friends. we got pretty faded and ended up at home just he and I. we started fooling around and I started sucking his Dick and he was hella horny so I figured it would be perfect to ask him. he said sure and so I got on this app for gay guys called grinder and posted a pic and immediately got a shot load of responses, even weird guys that sent gross body pics lol. well me being drunk and horny made me message back a few hot guys. I made a mistake of chatting with a guy and sending him my location and he never responded back so I figured he had crashed out or something. so I start chatting with a different guy.[hope in not going to fast this is all in the same night. ] this other guy was hot too I had never been ducked by a white guy and always wanted to take it so I gave the guy my number and my bf n I started texting him back and forth meanwhile I was still on the grinder app and starting talking to a another guy who right away caught me with the game he threw at me. I asked him if he wanted to come over and he said yeah. We had never done a 3way before and I was kinda scared to Elbe honest. well the 3rd guy I had talked to showed up and dam he was fine as fuck like his pic. I was afraid he was going to catfish me ha. we started getting naked and in my bed and sucking eachothers clocks when our doorbell rings and I am like wtf who the hell could that be....so I answer it and its the black guy I had talked to earlier. I didnt know what to say so I let him in and just like that he picked me up and literally pulled his cock out and wow! seriously black guys are hung. well now instead of a 3way it was a 4way and so my bf n I agreed I wouldn't let them bareback me so we used condoms. I have never been fucked so hard in my life all 3 of them pretty much ran a train on me and then I wanted to get double penetrated like in a born I had seen so I tried and the black guy was too big so my bf n the white guy fucked me hard while I pretty much choked on black Dick. well then we hear a knock on the door and my bf had given the other guy we were talking to on grinder our address and he showed up and he was alright looking but he had a nice body and like the perfect nicest Dick. I let him in and omg my 3 way was a 5way. yeah I took 4 dicks that night and seriously scared me because we didn't have enough condoms and I took the guys word that they were clean and thank god they were I let all of them unload in me. I kinda felt gross afterwards and after I came I asked them to leave even though they wanted to cuddle. yeah that happebed.


#3way   #sex   #5way   #black  


So my whole story starts with one of my favorite shows as a kid. What might this be? Little Nicky, none the less. So what got me curious? Well, anyone who has seen this distinctly knows of the scene where Hitler's punishment in hell ( spoilers for those who have never seen it) is to pick a pineapple from a cupboard and have it rimmed into his ass while he wears a maid outfit. As a kid, I got curious from this and began inserting fingers into my ass quite often and loved the feeling of it. I kept looking for what other things I could ram up there and get away with. Anything from the neck of bottles, to toys, to whatever I could get my hands on.

So skip ahead a couple years of doing this regularly. I now am finding shampoo bottles to lodge up there for the length of my shower, or to keep in there until I felt like I should get it out, then getting to where I do those plus some fingers or, hell, even another bottle ( by these I mean the ones like what you would get from a hotel)

Skip ahead a bit more and I am finding larger bottles of shampoo ( like, 12 Oz bottles with circular bottoms) to ram in there and keep in there as I finish my shower, and then rub one off after words when I am all loose and can put some fingers in there and move em around too.

Skip ahead a little bit farther, now basically in the future. Have had a steady relationship with my girlfriend for years, and finally after 2 during a night of exploring, I got her to try putting a finger in my ass as she jacked me off. She was surprised I liked it as she doesn't like anal at all. Then I told her I knew I did previously, and she got curious so she wanted to know what I could take. About 20 minutes later she ended up getting her fist inside my ass and now all I ever want is size. I can never get enough. She now on the other hand wants to peg me and keeps looking to get a strap on because she gets furiously turned on by taking control and putting anything in my ass she can find. Every now and then I wonder what it would be like to be manhandled and fucked in the ass by a guy, but I am not attracted to them, nor do I want to ruin my relationship with this wonderful woman. Maybe next time she tries to put things in my ass I ask for two hands, not just one :D


#curiosity   #straight   #destroyed   #lust  


I had been out of town for a month and getting desperate. I was in New Orleans, and walked past a tiny little bar and decided to go have a beer. As I sipped my beer I noticed a small, rather shy looking girl at a table all alone next to the dance floor. I kept watching her, she had a yellow sun dress on, and small boobs which I like, and very nice, shapely legs which I LOVE. I didn't see her butt, though all in all, she was looking pretty good. I saw some guys come out of a door at the back of the place, then a couple of what could only be crossdressers. Oh well, New Orleans, and live and let live. Then I noticed a butch patron and the bartender were a guy in drag, and a super butch lesbian. I figured it was a safe bet that the object of my immediate lust was a CD. I bought her a drink, sent it over, and then asked if I could join her and she said yes. She was definitely a He. Not being gay, but very desperate to have someone to have sex with other than my hand or a paid masseuse, and her being actually very pretty with a very feminine petite body, I started talking. She didn't want to talk much as her voice gave her away, but she was still pretty femmie sounding. After several hours, and a burger each for us, I made her stand up and start slow dancing. She was shorter than me, about 5ft. 8in, with a very thin body. I put both arms around her waist and as we danced, I went towards the corner and with her back to the corner and no one seeing, I pulled up her dress in the back and stuck my hands in her panties. She protested, and I wouldn't stop. Finally she said "Back Room" , I didn't know what that meant, but she advanced to that door at the back showing everyone my hands were on her bare ass. It was a totally dark room. "We can do whatever we want here" he/she said. So I pulled up the dress and pulled off the panties and started groping her ass. Kissing and licking, and rubbing, she asked if I wanted to do it there. I said no, I wanted her in my hotel room. Instead she said to go to her apartment which was only a block away. So I put the panties in my pocket and saw her moving what must be her cock between her legs, and we walked out, paid the tab and left, with the patrons wishing us a very sexy and good night.
At her place in subdued light I could imagine myself with a girl not a guy. I like buttfucking girls, so this should be no different. I got the dress off, kept her bra on, and with no panties saw her little cock a little bigger than my thumb, that was all. . . and it was fully hard. I pushed her down on her knees and she began sucking my cock, I told her to suck my cum so I could last longer when I fucked her. She was excellent and I was cumming in about 10 minutes. She the laid me down, got some oil and gave me a great massage for about 20 minutes ending up with her using the oil and getting my cock hard again. I pushed her on her back and got between her legs and kissing her, stuck my cock in her cumhole. It was very loose with all that oil, and I'm sure because she'd been fucked by a LOT of cocks in her time. I fucked her for about 30 minutes very rough and hard it felt like I was fucking a pussy, not at all like the girls butts I'd fucked. I rammed my cock up into this little cum bucket and flooded her with my cum. Adding to my 8inches I'm guessing I shot hard enough that it went over a foot up her poop chute. Exhausted I rolled off her and lain next to her. She moved my hand to her little cock which we called a clit and asked me to suck her. I told her I didn't suck, actually had never done it with a guy. She gave me the oil and told me to use my hand and help her out, and in her most feminine manner said "A good lover makes sure the girl cums too!". So I did. I actually gave a cock a hand job. When she was shooting I had moved my face close to watch, I did lick just a couple of drops off my hand. With that done I stuck around and fucked her ass one more time this time her on her belly and I left.
We met a few times in the next couple of weeks, and she finally got me sucking her little thumb sized clit, till she'd cum in my mouth. I don't mind so much. Last night we went out as two guys, and I fucked her all night at her place, stayed over and woke up to a smooth, girl in lingerie for my morning fuck. Then she rolled me over on my belly and got on top of me.
It's amazing what being desperate can do for what I used to think was the straightest guy on the planet.


#cd   #crossdresser  


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  


Although our time was brief, I know that I really liked you and I still wish that it could have worked out between us.
What hurts the most is not anything that you did but all that didn't happen.
I believed I would never find love in this life and that this was enough.
Meeting you has taught me that I want to love.
It was so easy to like you and easy to imagine and desire more.
However, in our time together it was inescapably evident to me that I am not the person you would love. Not now, not as I am now.
Would there have been a chance for us if this was another time in our lives?


#longing   #wistful   #heartache   #alone  


I am a happily married man. I never thought my self as gay or bisexual. However, one night while attending a party with friends, a male friend asked if I could give him a ride home. It is well known he is gay. I told him I would. It was obvious he had a little too much to drink. On the way to his place, he said that he would "show me his if I showed him mine." I laughed it off.

We we arrived at his place, I had to piss really bad. I asked him if I could use his bathroom. We went into his place. I quickly went to the bathroom. I almost pissed myself. I was so rushed that I didn't close the bathroom door.

When I was finishing up I heard my friend say, "Don't put it away. I want to see it." For some reason I didn't. He complicated me on my cock. Then he unzipped his pants and pulled his cock out. Not sure why but I instantly reached out and grabbed it. It felt so good in my hand. I started to stroke it. I was instantly rock hard. He took my rock hard cock in his hand and slowly started stroking. He leaned forward and gave me a long deep passionate kiss.

We got hot and heavy quickly. Before I knew it, we were both naked. Hands exploring each other. I wanted to suck his big beautiful cock. I did. It felt so good to feel the head slide over my tongue. I softly fondled his balls in my one hand and tickled his anus with the other.

He reached down a brought me to my feet. He led me to his bedroom. We laid down on his bed and sucked each other in a 69 position. It was so exciting. I came first and he swallowed all of my cum. I stopped sucking his cock. I leaned up and whispered in his ear, "I want you inside me."

He positioned me face down on the bed and got lube from his bedside table. He lubed my willing hole gently. I felt one finger go in. Then after a while, I felt a second. He then pulled me back on the bed so my legs were hanging off the bed.

I felt his hard cock rub against my butt cheeks and gently spread them apart until he was right against my welcoming anus. He slowly slid his cock inside me. I felt wonderful. I wanted him deep inside me. I backed up to him. His cock filled my ass. I asked him to go faster. He obliged. It felt soooooo good.

He said I was a naughty boy. I nodded. He said he spanks naughty boys. I nodded again. Then SMACK! His hand landed hard on my butt cheek. Then he thrusted hard inside me. I moaned with delight. He did it again.

I could tell he was getting close as he repeated thrusting and spanking me. With a grunt, he pushed deep inside me and held my hips tight to mine. I felt him cumming in my virgin ass. It felt awesome.

He laid down on top of me with his cock still deep in my ass and let out a sigh of relief.

He suggested we take a shower to clean up. We washed each other. Dried each other and laid on his bed naked. We caressed each other all over for a while until I left.

I still see him and yearn to do it again. Maybe one day.


#gay   #straight  


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  


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  


I come from a very religious family and I have always been told that I MUST remain a virgin until I get married. Listening to all my friends talking about how great sex is and how much they want to have sex with this guy or that guy was just to much for me. I placed an ad on Craigslist and met this guy is and had sex for the first time in my life. No one knows what I did over the weekend and everyone thinks I'm still a good little girl and virgin. I live in Guatemala City and I would love to have sex again without anyone knowing about it. Oh by the way I was 42 when I lost my virginity


#virgin   #sex   #unaware  


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  



Pray and roll the dice for #time

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