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Describe your first time anal

Thx man, I am so paranoid if I go for drinks now. Walk around with my thumb sick inside my beer bottle if it's not being consumed, refuse to set it down for any reason and if I absolutely have to... I toss it and just buy another. I developed PTSD from the event. But I refuse to take xanax , I never want to be out of control of my functions again. I did go on a 2 yr binge drinking, but I cane through it. Now if I have 3-5 beers once a month that is alot. Definitely scarred me tho.
 
Thx man, I am so paranoid if I go for drinks now. Walk around with my thumb sick inside my beer bottle if it's not being consumed, refuse to set it down for any reason and if I absolutely have to... I toss it and just buy another. I developed PTSD from the event. But I refuse to take xanax , I never want to be out of control of my functions again. I did go on a 2 yr binge drinking, but I cane through it. Now if I have 3-5 beers once a month that is alot. Definitely scarred me tho.

Well I respect you so much for sharing with us man. This world is fucked up and all we can do is keep our guard up. Appreciate that paranoia...it is saving you from trusting people who may do you harm. One time I got high with a coworker and he was smoking weed for the first time. He got really really high to the point where he thought he was going to die. Afterwards he thanked me for not raping him and I never understood why he said, thought or even mentioned something like that....but now I do. Maybe he was raped before or something but regardless don't trust people.
 
Shit sorry. Consent was given in my case. Also it was 11 years ago and I'm not quite the same. Also I've been locked up alot already soooooo

Ah man is that my far out far side????

We ain't talked in so so so so so long!!!:eek:

Both B9 and I miss your crazy speak.....I say crazy speak yet me and hubby understands what you say thus we must also be crazy!!=D

Anyways I really do hope you're keeping well and continuing being the loon we love xxxxxxxxxx<3 So long as you're happy pet lambee !!

 
Well I respect you so much for sharing with us man. This world is fucked up and all we can do is keep our guard up. Appreciate that paranoia...it is saving you from trusting people who may do you harm. One time I got high with a coworker and he was smoking weed for the first time. He got really really high to the point where he thought he was going to die. Afterwards he thanked me for not raping him and I never understood why he said, thought or even mentioned something like that....but now I do. Maybe he was raped before or something but regardless don't trust people.

I would say something had gone down before, what an awkward position...like what do you say..." you're welcome?"
 
I was with that black girl and she asked me to do it.I had a very hard time puting the cock in there and the condom broke. Never did it again.
 
I just tried anal for the first time last night. My parter and I have been together 3 years and are very comfortable being intimate together. I'd heard good and bad experiences from some of my female friends, I was curious about it... so I started just rubbing and stimulating the outside while mastubating which made me climax pretty quickly. Then I tried putting a finger in there not knowing I would need lube... that kind of hurt but not enough to be discouraging. I brought it up to my parter and we both got excited. We got drunk on rum and coke, grabbed some coconut oil and I started masturbating in front of him, stimulating my clit with one hand and rubbing my anus rim with the other, then he joined in and rubbed the rim and slowly worked a finger in with my guidance. Then he rubbed the tip of his penis over my anus which felt really good while I was still rubbing my clit. We did that for a while gradually poking the tip in and out adding more and more coconut oil until we eased him in very slowly, when it started to hurt I would have him stop and wait for my muscles to adjust. As I let him go deeper I did feel a sensation like I needed to poop but that subsided as I relaxed more... it was really pleasurable once I was able to relax enough. I liked the full feeling of him inside me and that we really didn't need to do a lot of thrusting, I had three orgasms on the first try! I was to shy to let him cum inside but I think I want him to next time. It definitely put our intimacy on a whole new level of closeness and love, it was really hot. All in all I was nervous at first about the mess and about pain, but taking it at my own pace made it really nice and the mess was very minimal. Baby wipes are a good idea just in case and it just make you feel better about the whole idea. I am kinda sore after but am already eager to do it again... the orgasm from anal sex is different from vaginal sex but in a good way, there is super pleasurable kind of G spot in there, I felt a really sexy kind of all over chills/ loss of control straight into orgasm when that G spot was found.
I never thought I would try anal but It felt way better than I expected!
It's all about working up to it and having total trust with your parter.
 
Kewkewi actually made me think I could "possibly" try it *with consent* in the future. Obviously with someone I fully trust and want to experience it with.

That description detail makes me think I would enjoy it. Im a very sexual person, overly even. I cum super hard, 80% of the time squirtting, if the guy has the slightest clue what he is doing. I'm pretty vocal though, I would want to be in a nice hotel or at home with noone else around. Who knows how loud I would be, with my windows n doors closed I've had neighbors hear me just from straight sex. The old man next door is actually a pretty funny dude.
 


Ah man is that my far out far side????

We ain't talked in so so so so so long!!!:eek:

Both B9 and I miss your crazy speak.....I say crazy speak yet me and hubby understands what you say thus we must also be crazy!!=D

Anyways I really do hope you're keeping well and continuing being the loon we love xxxxxxxxxx<3 So long as you're happy pet lambee !!


aye baybay! Whats good????? MnM its been soooooo long! Are you still active on here?
 
The first time I performed anal on my wife she was hesitant but we took our time and she loved it. Now she loves having a butt plug in during vaginal sex or if I use a dildo on her vaginally while I take her anally. A few years ago she surprised me with a finger in my bum during a bj and it was great. In the past year she used a srapon on me and I have not gotten completely comfortable with it but she has since learned what does feel good for me and it is a great experience. I am always nervous that it may become messy but so far we have not experienced any mess.
 
The first time I performed anal on my wife she was hesitant but we took our time and she loved it. Now she loves having a butt plug in during vaginal sex or if I use a dildo on her vaginally while I take her anally. A few years ago she surprised me with a finger in my bum during a bj and it was great. In the past year she used a srapon on me and I have not gotten completely comfortable with it but she has since learned what does feel good for me and it is a great experience. I am always nervous that it may become messy but so far we have not experienced any mess.

Nice first post. :p

First time: Met a girl on Craigslist "strictly platonic" (this was over a decade ago, when CL personals was a fucking gold mine and not a scam/porn/rape fest) who was just looking for someone who has also been in a bad breakup to commiserate with. Come to think about it, I don't even know if she was interested in meeting up. I, having also just been through a breakup, was all about it. Was chatted for a while, exchanged pics, and it turns out she is DROP DEAD GORGEOUS...no..I mean...seriously my first reaction was HOLY SHIT what are you doing here!??! Half black, half Irish, 100% perfect 10 all around. I was floored. Yeah, I wouldn't believe me either, but read on if you give half a shit. She gave the whole "Oh, you're cute!" deal, and it wasn't long until she suggested we meet for a drink. I drive the ~hour to her neck of the woods and meet her. This is the point where I think "I'm going to get robbed or ass raped aren't I..." but nope, there she was. She's 1000x hotter in person, is taller than me, and a few years older. She also had a kid. So, we get into drinking and playing pool and talking about our exes. Then, at a certain point, she asks "Can I kiss you?". Obviously my response was "Eww no get away from me horse face!!". So we make out for a while, and then says "Lets get out of here and go to my car". We go out, start making passionate love in the car, feeling her up, and then when I go for her pants, she stops me and says "Do you want to go to my house?". Again, I start to think "Am I being lured into a trap of some kind here?" but man, was I ready to take the risk. We go back to her house, where she reveals to me that her favorite thing in the universe, after her daughter, is anal. I, never having done anal (and was honest with her about it too, which I think was exciting for her), was pinching myself at this point because there was no way this was all happening like this!! How!?!? Craigslist!!! Well, we had sex all fucking night, literally watching TV waiting for me to recharge so we could go again, and again. She called a few times again after that, had similar experiences, sent me webcam videos of herself stripping while I was at work, I still just could not believe how fucking hot this chick was. And cool as hell too, into good music, seemed pretty drama free, ONLY issue was she had a kid with a crazy ex, and I was barely 22 so I wasn't interested in getting involved with that at the time. Eventually we lost touch and that was that.

Now that I am all sorts of hot and bothered at work...
 
The first time I licked my wife's butt for about an hour and then slid my cock in. It felt great. I had previously been finger fiucked by other women and have a history of stocking toys up my butt. I guess I'm pretty anal
 
Taking it up the ass:

I am a closet transgender MTF, the revelation has come to me during junior high when I saw my first image of a transsexual MTF in a magazine. I remember she had a very sad face. Since I come from a semi-rural town and I have a religious upbringing, my early anal experiments were a form of skittish single-player with a huge feeling of guilt afterwards. I had to improvise the dildo and the lube, and it always felt *right* if I also used elements of a female disguise. I used to go "female" as often as possible and would dream of a "magic pill" that may turn me into a female. I have prayed to God for this transformation as well. I have always worked extra-hard at covering my tracks, and I didn't get very far with experimentation before college. At some non-distinct point I discovered that concomitant anal and penile stimulation yields mindblowing orgasms that leave you limp in the legs and fucking happy as hell, no drugs required.
Sadly, in my 32 years of life I have never been fucked by another person in the ass. It's easy to find someone, but I have always been afraid of disease.
Nowadays and for many years now I have not been religious at all (yay!) but I am too implicated in a day-to-day routine to transition to full female and I have found many reasons not to do it. Though I have no pussy, I am still a "pussy" when it comes to social interaction and disease.

Giving it up the ass:

I have patiently tried to show all my female partners the pleasures of anal sex. I have repeatedly failed because some refused outright and others just tried "for my sake" but were not fully into it.
The best experience I had was with my female martial arts instructor that actually seduced me into her bed. To this day I believe that the sex was so good because there was a lot of teasing and hopeful expectation for both of us before we actually did it. In our chats she also explained that she was OK with anal sex and that anal sex brought her a lot of pleasure, actually she stated that anal brings her MORE pleasure than vaginal sex.
I remember that she casually retired to the bathroom beforehand and then the whole experience was very clean, though a bit underwhelming. The first time I vaguely recall wearing a condom and of course using lube but she relaxed and it was very easy for me to penetrate her. I do not recall her orgasm, I recall my orgasm and this thought "How nice it must be for a woman to find a gentle partner to share this feeling with..." I clearly recall my enthusiasm afterwards, I may or may not have suggested that I want her to peg me, but surely I chatted a lot because I was happy with my new experience. She wanted to have her nap because it was 3AM by the time we finished our fucking but she patiently satisfied my girlish need for conversation up until the point I cuddled to her breast and slept. At least one of us snored and to this day she says it was me.
The second time was also clean and fun, but even more underwhelming, perhaps the room was too hot or... perhaps the realization that I need role reversal as far as anal goes dawned on me at that point. I "came bareback in her ass with a grunt and felt her constrictive muscles milking my shaft" just like you read in the stories, but I knew I needed something else. Should you, dear reader, wish to call it so - you have my sincere approval to call it jealousy for indeed it was what it was.
I am sad to report that I broke her heart afterwards, but she holds a spot in my heart somewhere along my fondest memories.
 
Had a lot of fun reading some of these stories! I had to take a moment and post my appreciation for them. First time post... will be back again I am sure. As I have a strong fascination with anal.

Jen
 
Well. I'm actually a very "good" girl...as far as my friends and family know. But my first boyfriend knew me better than that. We started dating shortly after I joined college..all the freedom I suddenly had made me go a bit crazy. Not that it was apparent from the outside - I just knew myself that things were changing for me. So anyway, there was this boy in math. I wasn't really into boys at school but all of a sudden this boy called Scott caught my eye. He had a cheeky grin and I caught him looking at me on several occasions...you know..checking me out. I was intrigued at first because this was all new to me. Over the summer I had matured quite quickly and my flat chest had developed nicely which made me noticeable (I was quite slim and petite). Anyway, Scott...we flirted for a few weeks, before he finally asked me out. I couldn't say no, but I had to keep it a secret. I needed to keep up my good girl look. He took me to the cinema and I have to be honest, nothing naughty was on my mind. I obviously knew about sex and stuff as my friends were always talking about it, but I had never had the urge before. So anyway, the cinema, we watched the lego movie and it was hilarious. Afterwards he asked me back to his for dinner to which I agreed (he said his mum was cooking spaghetti bolognaise) - how could I resist! I told my parents I was at a friends...they weren't too keen on my seeing guys, even now I was in college. When we got to his house I walked in and said hi to his mum and dad, they were lovely and so welcoming. Scott said he had never brought a girl back before so it was new for both of us really. He was so kind and such a gentleman, he would open doors for me and was constantly asking me if I was okay. While we were waiting for dinner he showed me upstairs and gave me a tour of his room. It was a nice house and his room was a typical lads room, a few posters on the wall...a calendar with some girls on. I pointed at one and made a comment about how little clothes she was wearing. He laughed. While he went downstairs to check on the dinner I had a look through his cupboard (I was being nosey, I wanted to find out more about him). At this point he seemed too nice to be true! After a while of rummaging about I came across a small white leotard and was just inspecting it when Scott came back into the room. The look on his face was pure embarrassment. I didn't even need to ask him what he was doing with it as he immediately said "oh that's my sisters". I laughed and said I thought it was cute. What he said next threw me off guard. "Try it on if you like". I was sceptical, what if he saw too much and got the wrong idea? No. It would be fine. He's a really nice boy, he would never make a move or anything like that. So I went into the bathroom and took my clothes off. I made sure the door was locked - nothing would have been worse if I had been walked in on! Once I had slipped it on I had a look in the mirror. It really was tight. I knew my breasts had grown a fair bit over the summer but this really made them look disproportionately large compared with me slender figure. I thought I looked a bit slutty but there was no turning back now, I didn't want to disappoint Scott. I would quickly show him and then get back changed in time for dinner. It wasn't like me to do something like this, but what the hell. I was in college now so screw it, I can live a little if I want. As I walked towards the door I looked back in the mirror and noticed how peachy my bum looked, I had never really realised before - but I had a decent sized bum for a small white girl. As I walked it jumped up and down a little. I opened the bathroom door and whispered "Josh". He appeared around the corner and couldn't hide his grin. He quickly snuck inside and closed the door behind him. He looked me up and down and said "boy" "wow". I couldn't help but blush. No one had ever really complimented me before. I always wore sensible clothes, none of this modern day attire which shows your every curve. I was purely in it for the comfort...until now. I stood there waiting to him to say something other than "wow"...eventually he said "so I guess it's my turn". I laughed, how are you going to get in this I said?! He bet me anything in his room that he could get into the leotard I was wearing. No way I said. Impossible. Scott was quite slim like me, but at least a foot taller. He had some muscle, but was mostly toned. For a brief moment I imagined what he looked like shirtless. He was quite tanned for an English guy and had no facial hair, quite young looking really. I imagined he had a nice body. Did I want to see it? I wasn't sure. But I know one thing, I wanted to see him struggle getting into this tiny girls outfit. I shook his hand and said "deal". I forced him to stand facing the wall while I took it off, I covered myself with a towel and handed it over to him and said "your turn". He took it, turned around to face the wall and pulled down his shorts. I quickly looked away. I wasn't sure if I wanted to see, but I certainly didn't want him to see me looking. As he continued getting changed I caught the mirror in the corner of my eye. I found myself staring right at his bum. I didn't realise boys could have such a nice smooth bottom. I'd seen my dads before and it was disgustingly hairy. But not this one. Scott's was slightly paler than the rest of his body, and peachy. It looked so smooth. Not a hair in sight. I realised I had been looking too long so diverted my eyes back to the wall. After a few seconds he said "I win". I turned around and there he was, squeezed into this tiny leotard. It didn't leave much to the imagination. I tried not to look below his belly button but I couldn't help but catch a glimpse of his ...area. He certainly looked well ...er...equipped down there. I felt a strange tingling and a warm fuzzy feeling go through my body. I worked my way back up to his face and said "well done". At that moment I was so unsure what my body was doing. I was frozen. I wanted to kiss him, I wanted to say something. But I couldn't move. He slowly started walking over to me. I could feel myself getting warmer, and fuzzier. He came within a foot of me and put his hand up to my face, and stroked my cheek. I wanted him so bad. But I still couldn't move and didn't know what I would do even if I could move. He walked around behind me and slowly began to remove the towel which was covering my naked body. It felt wrong, but it also felt right. All of a sudden I was stood there, completely naked. In front of a boy I had met just 3 weeks ago. I had never even kissed a boy, let alone..done anything else. He came closer behind me. I could feel him up against me. I reached my hand behind me and ran it up his leg. I felt it. I might not have touched one before but I knew what I was touching. He still had the leotard on. I massage it for a few seconds. He then touched my left thigh, and ran his hand around to my left buttock. He squeezed it. I could hear him sigh. I looked down and noticed my nipples, which were usually fairly small - were now hard and pointy. I had never seen them like that. Scott moved his other hand up my right side and on to my boob. He squeezed that too. There I was. Standing naked in front of a guy who I hardly knew, having my bare buttock and bare breast squeezed. I stood there for a moment completely overwhelmed. Time seemed to stand still. I had no idea where I was. I went for his willy again. By now he had removed the leotard and was standing behind me, as nude as I was. I grabbed it, and ran my hand down it, trying to gauge the size. It was huge. I could feel the veins as my fingers went from one end all the way towards his body. He started slowly rubbing the tip of it on my back. I could feel something wet on my back as he started to prod with more force. He ushered me towards the sink where I learnt over more, my face almost touching the side. I wasn't sure what I wanted. But I knew I didn't want it to stop. Without warning he slipped it inside me. It was smooth, but it was painful. It wasn't like how I imagined. I thought it would feel good - not that I thought about it much in the past. He slipped it back out. And I gasped for air. SLAP. "Ahh" I shouted. I couldn't even control it. He slammed it back inside me with such force, that his balls slapped against my bum so hard I could feel where they made contact. He whispered "shh". Despite being in pain, it was good pain, you know? Like the pain after a workout. It hurts, but you sort of don't mind at the same time. He did it again. And again. SLAP. SLAP. I could hear him panting. I reached behind me, to give myself some time to recover. I grabbed his cock and just rubbed my hand up and down it. It was so wet and juicy. I thought to myself "is that all mine?". I felt my vagina and yep...it was all me. I hardly had to touch it before my fingers were soaked. I went back to his cock, still facing the sink and squeezed it hard. he sighed loudly. I ran my fingers back up again and over his bell end. It felt like a monster cock. I still had seen it properly. I didn't want to ruin the moment so stayed wher I was and moved my hand back to the front. He put both his hands on my bottom and slipped the monster back inside me. In. Out. In. Out. SLAP. SLAP. SLAP. I could hear the squelching as his juicy cock entered and exited my wet, ever expanding vagina. I caught a glimpse of my hand and noticed something red on it. Weird, must be some ink or something from college. SLAP. SLAP. Squelch. AAAAAH. "Shit!!!" My pain level, which was just beginning to lower suddenly hit the roof. He'd accidentally put it in my arse. It felt like someone had poured chilli powder inside me. I stood there, bent over, for a few seconds. Trying to come to terms with what had just happened. Before I had managed to gather my thoughts it was back in. But this time slowly, and softer. Surprisingly it didn't hurt too much. The initial whack must have killed all my pain receptors! He kept going. In and out of my arse, it felt different to before. Before it felt painful and a little bit pleasureable. Now it just felt weird. I felt like I needed to poo. Not a nice feeling. And I certainly didn't want him to see that...I let him continue and just concentrated on not reliving myself. He started picking up the pace. SLAP SLAP SLAP. His balls slamming into my thighs. My arse feeling like it was being torn in two. My breasts were also starting to ache, after having spent the past 10 minutes being thrown backwards and forwards. With one mighty sigh he stopped. His huge penis had penetrated my arse as far as it could go. I could feel it throbbing. His pelvis was touching my cheeks. His entire monster was inside my arse. I felt constipated. More than I ever had felt in my life. I could still feel it throbbing inside me. Until he finally pulled it out. I felt like I had just done the biggest number 2 of my life. I slumped a little. My back has started to ache and my legs were getting tired. I spent a few seconds catching my breath before turning around. I wasn't exactly sure what I expected to see. The first thing I saw was his monster cock. Staring at me. It was still throbbing a little bit, as if it was catching its own breath. It was dripping. It's veins were sticking out. I couldn't believe that it had just spent the last 5 minutes in my arse. I looked down, there was a fair bit of blood, mixed with what I assumed was semen. I knew virgins sometimes bled so I wasn't alarmed. I slowly stood up and made eye contact with him for the first time in what seemed like for ever. He was sweaty. But sexy. I took a step towards and kiss him on the lips. Then on his nipple. Then I made my way down to penis. I spent a few seconds inspecting it. It was honestly the biggest one I had ever seen. I had seen a few, my mates often sent pictures to our group chat. I didn't take much interest but I knew this one was special. It was still semi hard from being inside me. I grabbed it with my right hand, lifted it up and licked all the way from his ball sack to the tip. Salty. I then put it in my mouth. He groaned. It got about half way in before I knew I had run out of space. I sucked it hard. Wow. It was so hard, yet so soft. The taste of what I presume was semen was making its way around my mouth. Then he said "its its my turn to clean up". He turned my around to the same position I had just been in, but this tim for he got on his knees. He starting licking all around the area he had just been fucking. He didn't hold back either. The noises were incredible and it felt even better. I could feel him all over my vagina and around my anus. After he had spent a good five minutes cleaning up we both stood up and took a long deep breath. His penis had finally reduced in size and was red raw. Either from ththe blood or the friction of my tight arse. My vagina felt damaged and my arse...well. It certainly felt violated. We put our clothes back and went downstairs for dinner. We didn't talk much. I left straight after and went to home to bed. We didn't talk again, when we saw each other we gave a knowing look, as if to say this is our little secret.
 
BUCKLE UP FOR THIS GUYS! I think I can make just about any one of you laugh with this story. And yes, I swear to god this all happened exactly as I am typing this!

So, the day I first performed anal... My gf and I had ate some sea food, afterwards we went to my place. The food did NOT settle with me in the least bit but she insisted on kissing etc. She started to give me a bj (this parts for shits and giggles...) And I felt my stomach start to turn...I then got really stiff and she kind of gave me an odd look but I didn't say anything, I felt like if I moved I was going to shit everywhere... I was mad at her (we were arguing, she was pretty bitchy and bossy and we were in an extreme rough patch in our relationship) Well while she was still down there I ended up letting out a huge fart in her face...lmao. She was very pissed at me! (Which I don't blame her, and I did tell her my stomach hurt before hand...) Well it got pretty awkward after that, didn't help I laughed my ass off. Later we tried again, all was well, and I told her I wanted to try anal. After some convincing she let me do it. (I had just watched south park before this) I REALLY wanted to do something at this moment and hesitated. I loved the feeling a lot but she hated it, and wanted me to stop so I started laughing a bit, and started singing "what what in the butt, I said what what in the butt butt!" Butter's reference from South Park. All of this was happening WHILE I WAS PERFORMING anal...she was mad, she yelled at me and told me to bring her home. There was not one word spoken on the ride home, and 2 weeks later we were both single. Lmfao.
 
You have to work the anus with fingers/tongue/butplug, and the lube always ends up everywhere. And of course, the room will get spiced up by a weak smell of poop, as well as fingers, dick etc.

Not entirely true. I've warmed myself up plenty of times with my fingers and have been so horny, that as soon as I lubed up I was able to insert it with ease. There was no smell at all. With enough lube and proper prep (cleaning the canal out beforehand) there won't be a smell on your fingers or the 'toy' of choice.
 
It happened naturally. I was extremely turned on and open to anything. I was also buzzed which helped a lot. Also, his cock was the perfect size, not too big. We were having sex and I turned around and he gently eased his cock in my ass. It hurt at first and I told him to get plenty of lube. He lubed everything up really good, slowly entered me from behind, got it all the way in and it felt incredible. I was lying on my stomach and he was able to start pounding me hard. I never thought I would enjoy anal so much. Kinda felt like a porn star when he was fucking me hard in my ass. hehe

Oh and he told me in the past, he had a messy experience with a girl. Luckily, everything went smoothly, no mess. I didn't plan on anal, but I guess I happened to be cleaned out pretty well. lol
 
The first time I had anal sex was 2 years ago at age 33. It was completely spontaneous. My now husband talked me into trying it (he really didnt have to try all that hard to talk me into it, I had been curious about it for awhile). He was patient and slow and did everything right. It was the most intense orgasm I had ever had. I couldn't form a complete sentence for about 10 min afterwards and kinda just laid there and twitched for a little bit less than that. We now do it once a month sometimes once every 2 months and I'm normally the one begging for it and it's still just as amazing as it was the first time.
 
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