5 comments/ 89397 views/ 7 favorites My First Anal! By: MrJimJim Once I had finished giving my first blowjob, I knew it wouldn't be my last. In fact, I stopped counting! One of the guys I sucked on often was nice. Latin, firm, long slender cock just perfect for being naughty with. We had been together enough times we were comfortable in each others homes. We would fool around at his house or outside in the rain. I would always swallow his cum. We were that comfortable. One night after wine coolers we decided to videotape ourselves. I told him it was OK as long as I could see his cock go all the way down my throat. "Deepthroat?" Anthony asked. "Deepthroat." I replied confidently. "Are you really ready for that, Jim?" He asked. "Do you want your cock in my throat or not?" I answered sternly. With the camcorder whirring, I suddenly found myself getting the back of my throat and below impaled at a slow pace. As time went on, it got faster and faster, until eventually I knew what he wanted to do. He groaned and lurched his hips forward, then jerked back quickly. I felt 1 spurt across my tongue and I was as hard as a rock. The next 5 or 6 strong spurts lept from his cock he had popped out of my mouth and went streaming across my face. That made me send my own spurts shooting down my legs and soaking my pantyhose. When I was done, I licked it up like a greedy dog. After we both were soft we collapsed on the couch next to us, satisfied. Getting a facial had always made me cum so hard. Before he left to get more wine coolers, he leaned over and whispered "I want to do that to your ass. I'll bet my cum will feel twice as good inside you." That caught me off guard. I had never considered myself gay, just very easy and open-minded with my mouth. I was somewhat reeling, the words making me stiff again. Before I knew it I was jacking off and cumming again! He got back with the coolers as I was slurping up my load. "I see you like the idea" Anthony said wryly. "No" I replied bashfully, and hurried to bed. Over the next 6 weeks Anthony would drop little hints to me. "I bought some lube today" or "I wish I could fuck a tight honey" were among his favorites. But I was scared and confused. I didn't know what to think. Someone tell me what to do! A week later Anthony got a promotion, and we were all celebrating. We all drank way too much and eventually we all fell asleep. I'll never forget when I awoke... I was laying face down, half in and half out of sleep. I felt Anthony kiss my back and shoulders, which only meant one thing... Anthony was horny. From the feel of his hard member that touched me some, I would've said VERY horny! He'd never been that solid before, I always had to suck start him. I felt a pair of hands on my shoulder, but something wasn't right. They were backwards! I tried to turn over to get a better look, but those strong hands held me firm. Next I felt warm oil being poured all over my body. Along my shoulders, down my back, down the crack of my ass, and along each leg. Then panic. I felt Anthony's cock pressing against my virgin rosebud! "STOP!" I yelled. But it was too late. I felt the head of his cock press against my hole harder. I tried to hold tight, but the more I tried, the harder he pushed. I couldn't even make a noise. I felt the head of his hard slender cock force itself into me, and there was a flash of heat around my hole. I almost blacked out. It hurt! I managed to whimper "It hurts. Oh it hurts". My only reply was "Shhhh" in my ear. Without warning he heaved his slender latin hips forward, and my hole engulfed his entire rod in one swift shove! My cock twitched to life and got firm, then rigid, then hard. What?! That can't be from this! He slid his cock almost all the way out, so very slowly, stopping just before the head peeked out. It made my cock quiver, and I was getting used to this stiff intruder. The hands let go of my shoulders, and I turned to see a look of sheer ecstasy on Anthony's face. "Fuck me" I managed to get out clumsily. His eyes opened and centered on me quickly, as I pulled him from his ecstasy for a moment. "Fuck me!" I got out louder, and his look of surprise turned to something naughty and devilish. He pushed back into me, then out again. Slow at first then building up to a full-out ramming. I was moaning as this stud ravaged me like he had never fucked before. And I heard it. His tell. He was about to cum... So many thought raced in my mind. Is he going to cum inside me like he said? Is he going to cum all over my pantyhosed ass? Would he pull me up and shoot streams of thick cum across my face. He came. The feeling of his spunk flowing out of his cock into me was more incredible than anything I can describe! He came long, and he came hard. I could feel his cum spurting into me, then cooling. It was amazing! After two or three spurts, I became light-headed. The room started to spin. And... I felt myself unleash a load of cum harder than I have ever cum before. EVER! The room went dark. The air got cooler. When I woke, Anthony was just out of the shower, and calling cabs for guys who started waking up. He came over to me and said "You sure changed your mind in a hurry. Did you like getting fucked and spunked?" "I don't remember" I said as his face showed his puzzlement. "You will have to refresh my memory after everyone leaves" I said with a smile. To this day, I cum instantly when someone cums inside me! My First Anal You and I are both at the mall, after just having blown each other's cocks in the deserted parking lot. Even after that hot session, you can tell I want more, we are just walking aimlessly around, you looking for a bathroom to fuck in, when we come across a Victoria's secret, a hot blonde with big boobs almost bursting out of her chest working at the register. I drag you into the store, and tell her me and my boyfriend (that's you), want some new panties and things to spice up our sex life. After giving us an odd look, she helps us pick out garter belts, pantyhose, bras and thongs that match. After we have quite a selection, we find a large changing room to try it all on in together. We each undress ourselves, staring at each other's bodies. As we try on different items, bumping into each other on "accident," helping each other out putting on the pantyhose as an excuse to feel the other person's legs, we both develop obvious erections. You help me put on my bra, only to kiss my back. "Mmm, do you really want to fuck in here? We might get caught," I say as I feel your breath on my neck. In answer, you push your thong, clad hard-on into my ass, causing me to moan softly. Your hands explore my body fully, feeling me up and rubbing my cock. I turn around and press my body into yours, pushing you against the wall, shoving my tongue into your mouth. My hands explore your ass, massaging it some, you moan into my mouth. I feel one of your hands squeeze my cock, rubbing it through the material, making me moan into your mouth in turn. We both rub and caress each other, assaulting each other's mouths with our tongues, both giving out soft moans, both of us obviously horny. You push me off and drag me to the small seat in the booth, throwing off all the clothes we had piled up onto it. You push me onto the seat and start sucking on my cock through my panties, it throbs and pulses, I'm obviously very close to orgasm. My hip moves forward in a thrusting motion, I'm barely able to contain my moans, turning them into slight squeals of joy. You pull my thong off, causing my cock to twitch again, but you instead move to my asshole, giving it a workout. You shove your tongue into my ass without warning, I groan very loudly that time, but stop my self from moaning again, barely. My head tilted back, I enjoy my first rim-job, my eyes closed as your tongue licks and probes my ass. I know what you want next as you stand, your cock at full attention as I move my hand to it and rub it through the silky material. I pull the thong away, but not off, and whip your full hard-on out, smiling at being able to sample it again. My tongue rubs along the shaft, you moan loudly too, your head tilts back with your eyes closed. I slowly stick all 7'' in my mouth, sucking it in as far as I can, only able to get 5'' of it my first go. I bob my head up and down on your cock, getting it nice and wet for my first anal fucking. I slurp and suck and lick all along the shaft, its thick girth spewing out precum. I greedily lap up the cum, your hips thrusting into my face, and you love every minute of it. You pull out and I look at you with a question on my face, but I realize what you want as you drag me up and moving me so that my back is turned to you, my hands on the small seat. I feel your cock touch my asshole and feel it involuntarily tighten. "Go easy, this is my first time." I look back and grin widely, and turn back around. You slowly push your saliva covered cock into my ass and I groan loudly, not caring if we are heard by anyone anymore. You shove it all the way up my ass, its so tight, I try muffle my screams of pain and joy as you slowly push all the way in. At about halfway, you pull out and slowly push back in. It hurts, but at the same time, sends waves of pleasure all throughout my body, I feel myself pushing back. You finally get it all the way in and just wait there, letting my ass adjust to your hot cock. I feel your hand at my cock, and moan again as you start to jerk me off slowly. As you slide your hand up my cock, I feel your cock pull out of my ass. You squeeze my cock and tug down as you slowly shove it back in. "Fuck my ass, please," I mumble this, barely able to breath in between all my moans. Your cock feels so good while it is inside me, my moan grows slowly higher as you thrust your cock, burying it into my ass. "OH, fuck me, your ass is so tight" You say as you thrust into me, you groan and moan as well, thrusting steadily faster, your hand keeping up the pace. "I'm gonna cum soon, your cock feels so good in my ass, fuck me harder, please!" I feel you move at a very quick pace as you shove your cock in and out of my ass. "OH FUCK! I'M CUMMING!" You cry out as you spurt load after hot load into my ass, my cheeks clench down, trying to keep all of the cum up in my ass. "OH FUCK, ME TOO!" I shout as well as I see my cum shoot up into the air, hitting my face, chest and some even lands back onto my cock. We moan and groan very loudly as our cum shoots out of our hard cocks, and we slowly calm down. As we finish, we hear a woman shout in the booth next to us, "OH FUCK, I'M CUMMING TOO!" My First Anal I wanted to share my first time having Anal Sex and the first time writing so be kind! It is also a true story so if anyone has any feedback or wants to hear more, please let me know. ------------------------------------------------------------- I'm not sure where my obsessions with anal sex came from but it had increasingly begun to monopolise my fantasies. At 21 I was mocha skinned, 5ft 9" I was pretty lean but relatively muscular, cocky and easy going. But after my first serious relationship I had rebounded into what seemed like a shallow but frisky relationship with Nicole. She was pale skinned, thin but a well stacked fiery redhead. In retrospect she reminded me of a cross between Faye Reagan and Nicole Scott. Most nights out ended in drunken, blazing rows or dirty sex but in the light of day we never seemed to get on. However repeated attempts to end it never seemed to work. My latest attempt to politely end it in a bar initially seemed to go well until the end of the night when she successfully goaded me into a bar fight by making out with the nearest available man. I had stormed out furious but hopeful that the embarrassment of the evening's public rawkus might lend some finality to my decision. Nicole had other ideas. She arrived at my tiny flat that very evening. She was adept at causing a scene and I thought I owed her closure so I let her in to talk. As my flat was tiny we had to talk on the bed and I tried to explain how ill-suited we were and why a break was for the best. Despite all my best intentions Nicole stilled seemed adamant that she wouldn't take no as an answer. What she did next was pretty surprising, even for her. As I protested the finality of it all, and after her desperate apologies and pleas for forgiveness she started to undo my jeans and pull out my cock. I almost laughed at the ludicrousness of the situation but she started to stroke my turgid penis slowly with some aggression. As I pleaded to her, "no," to stop, she took my cock in her mouth, and swirled it around her tongue. As it grew firmer, it buzzed with anticipation overriding most of the good intentions in my head. I managed to push her head away slightly but she forced back enveloping my lengthening cock entirely in her mouth. I paused for a moment taking in the sensation of her deep throating my entire penis. This was a battle I was rapidly losing. Nicole took my momentary weakness and stood up on the bed. Her light green, summery dress clinged to her pert breasts with her pink nipples just lightly protruding from beneath it. The soft, thin straps holding the small dress up, revealed a pale slim chest of porcelain white which she suddenly revealed in full as she dropped them either side of her shoulders. The dress gracefully slid over her nipples across her flat stomach and over her slight hips to reveal a wild strip of ginger red pubes brightly sat above her pink pussy lips. She kicked the dress aside with her glossy black high heels and dipped her fingers into her mouth coating them quickly and thoroughly with as much saliva as she could and spread them over her clitoris and down her parted lips. She then turned round and crouched back down almost as quickly as she had gotten up. Taking my twitching cock from behind her crouching legs she rubbed it along her moist pussy lips and before I could protest further she placed the weight of her pert, white arse down on my cock, sliding it into her pussy with some resistance. Nicole could become very wet but usually required a fair amount of foreplay so the eagerness to take me inside her so quickly seemed an indication of her desperate determination. Whilst my body was enjoying the guilty sensations of it all, my mind was still objecting to her sexual manipulation. I cupped my hands around the underside of her pale arse and tried lifting her off exclaiming a conflicted, but firm "no!" But she refused to listen, raping me rhythmically, with her arse riding my cock up and down like a pneumatic pornstar. She grabbed one of her 34C tits seductively then used my hand to squeeze it firmly until she squealed. Her hand slid down between her bouncing breasts and to her engorged clit, rubbing it furiously before spreading her fingers around the cock she was fucking and then bringing them back up to her mouth to taste her own cunt juices. Sensing my waning resistance Nicole groaned, "Ughnn... finger me!" I really wasn't sure what she meant seeing as her pussy seemed pretty full up with my engorged knob so I asked where and she replied, "Finger my arse!" As instantly as the penny dropped, so did my resolve. Because of my previously resisted attempts to circle her arsehole with my finger, Nicole knew full well my fetishized weakness. And had seemingly planned her backwards facing rape to expose her twitching arse to my filthy mind. Unsure of when I would have this chance at depravity again I relented. Sitting slightly more upright I began stroking the curves of her round arse, a movement that usually turned her on. Signalling this, she began to rock back and forth grinding her clit into the base of my groin and exposing her arsehole further. Grabbing her butt firmly I helped her rock furiously and then stretched her cheeks apart so I could see right into her crevice. My fingers crept gradually inward until they circled the edges of her anus. Pulling the cheeks even further at this point exposed more of her wrinkled sphincter, a tantalising glimpse into her forbidden fruit. I nudged a finger over the surface and we both twitched in pleasure. I began massaging in gentle motions over her tight anus but it was still shyly closed tight. Changing tact I moved my finger to the meeting point of my cock and the base of her pussy lips. Running my finger over the hot, mess of juices lubricating us, I returned it to hover over her arsehole before plunging it in. She gave me little entrance but contracted in surprise. I returned to circling my finger over her anus, gathering a few millimetres of lubricated progress at a time. With just over half of the tip of my finger tightly gripped by her hungry arsehole, she silently squirmed. She could sense that she was reeling me back in, but her arse wasn't quite ready to be entered yet so she made moves to assume my favourite position; 69 with her on top. Nicole's virtues were questionable however one thing she seemed proud of was her ability to give incredible head. So sliding her arse off my cock, she shuffled her body backwards and she took my throbbing penis that was fully drenched in her own pussy juice... and licked it clean. Her filthiness never failed to turn me on. She then went about her business deep throating my cock as expertly as ever whilst presenting her moistening crotch to my face. Her pussy and ass were now very much in close-up above my head. My tongue went to work on her pussy. One of the delights of fucking a redhead is their unique fiery crotch. I equated the colour to a raw, animalised passion, so the fact that she had let the wiry mound on her pussy grow somewhat unkempt was a disgusting turn on. The fact that her pussy was engorged by alcohol fuelled sex and a sordid tinge of sweat and wee was a disgusting turn on. And the fact that her now close-up puckered arsehole was lightly surrounded by a few small, wiry, ginger pubes was also a disgusting turn on. Nicole couldn't usually climax through penetration alone so long bouts of oral sex was usually a necessity but not in the way it was about to go down. Working her pussy with my tongue was already having an effect on her as I could hear the moans escape from her cock filled mouth. Grabbing her pale arse cheeks I gently rocked her pussy up and down on my tongue, dipping both index fingers into her sloppy pussy as she ground her juice into my face. However this close I could see more of her arsehole than ever. I spread her ass cheeks widely inching each fingertip closer and closer inwards. Eventually my middle finger tips bristled past the few pubes around her arsehole and her body began to flinch. Getting braver and more adventurous I moved my tongue further south from her hungry clitoris, along her pink lips and then deep into her pussy, fingering her with my tongue whilst savouring her salty, musky juices and eventually further back around to her untouched perineum. Nicole could sense what might be coming but didn't flinch until my tongue reached her puckered arsehole. It danced around the ridges on her surface before quickly pushing inside her constricted muscles a few millimetres, but her reaction was instant and uncomfortable, "Not with your tongue." So I relented and using my hands I kept her bottom close to my face and inched my fingers inwards to the edges of her wrinkled anus. To see every inch of hidden detail so close-up was scintillating! My fingertips once again tugged gently at the edges of her sphincter, spreading her asshole slightly more open. I returned my fingertips to the horizon of her arsehole gently massaging the surface again. When her body resisted, my hands pinned her closer to my body whilst my tongue distracted her back into sexual oblivion. Dipping my finger through the tight opening proved difficult, I only managed to depress it inwards slightly so I awkwardly removed my wet fingers from her pussy and brought them back up to her opening. With the slightest of dirty lubrication the tips of my fingers were already making progress, pushing their way into her tight arse. The sensation was alien and familiar at the same time, reminding me of the newness of feeling your dick in a warm pussy for the first time. Nicole's body rocked at the foreign intrusion into her butthole, but my grip held fast and my tongue worked harder on her clit to continue to distract her. Not only did the anal grip on my moist fingertip tighten, but her mouth's grip on the length of my penis also tightened. The feeling of my fingertip in her ass for the first time was both driving us to the edge of climax. I worked the digital rhythmic movements in her ass harder in time with the licks to her pussy and felt the wave of orgasm start to rock her body. It was then a magical thing occurred. As her body arched, her asshole momentarily opened up, fully relaxed and dilated I slid my finger quickly in, past the first knuckle, and then her anal muscles tightened again. As the second wave of orgasm broke against her body, she arched her body again, and her asshole flowered open and sucked my finger into the second knuckle. I gently pulsed my finger in and out, eager to soak up the sensation of movement and suction. As the third and final wave of her orgasm washed over her I made one last push, inching my finger almost midway past the second knuckle, once again pulsing and arching my finger to feel the darkest parts of her body that I had never touched before. With my finger nearly entirely swallowed up by her asshole, my face covered in the juice from her pussy overflowing in pleasure and my cock buried deep in her throat, I finally exploded a powerful stream of cum into her throat. Shooting multiple spurts until my cock was left twitching in her paralysed mouth. Was that possibly the best 69 ever?   But the deviancy hadn't ended there. As we lay in a post coital embrace, our bodies entwined more deeply than ever, Nicole asked, "How many fingers do you have up there?" I replied with, "Just the one," and she seemed surprised. The sensation was so unfamiliar to her she couldn't tell what was in her ass or how far it had gone. This may be the reason for her braveness, however it would turn out there had been ulterior motives. With my finger still static in her ass, she turned round to me and said something I thought only porn stars say in my dreams, "Fuck me in my ass." My brain couldn't' quite believe the fantasy that seemed to be coming true so I stumbled and she once again begged, "Please fuck my ass?" Did Cosmo teach her this pornified theatrical dialogue? I didn't stop to contemplate it any further. Sliding my body and still erect penis out from under her, I kept my finger inside her arse, gently massaging it and feeling the inside walls of her. She reached down the side of the bed for her small tub of Vaseline. I wasn't sure if it was still the recommended lube for anal sex but I wasn't going to quibble. Taking a lump of the lumpy moist Vaseline she reached behind her to spread it generously on my still hard cock. It throbbed at her oily grip. Her hand glided over my balls, which seemed a strange thing to lube until I realised where she was going. She stretched back to try and slide a finger up my crevice and into my arse. She partly nudged her oil finger easily in which sent a shuddering sensation of anticipation through my body but the position was too awkward for her to maintain. So I took the tub of Vaseline, smoothing out parts on my penis with my left hand. I then returned my left hand to her arse cheek, spreading it widely and inching a glistening finger back to where the other was still comfortably embedded. I spread the Vaseline around parts of her bum and coated my right finger as much as I could before trying to prize a second finger in. Her arsehole was still tightly gripping one so as I pushed the second finger in I slid the second out. She quickly opened and closed back on the single digit. I applied Vaseline to the other finger, still warm from its cosy time in her arse, before struggling to squeeze it back in. Eventually I had to stretch her arse cheeks with both hands whilst trying to fit both in at the same time. Nicole seemed impatient or eager to have me inside her so she turned back and said, "Just put it in. Fuck my arse now, please!" So whilst keeping both fingers partially inside, and stretching her arsehole as wide as possible, I pushed my rock hard cock into her opening. The fingers were still getting in the way so I had to quickly let go and push the head of my cock in with some force and speed. Nicole's face seemed to wince but not complain. My head was still only partially in so I tried gripping the base of my cock and pushing it through the opening but with little give. So I then tried spreading her cheeks apart, sitting a little higher and pushing downward. I was slowly gaining a few millimetres in traction. Eventually I moved to the best combination. I pushed her back down and grabbed both of her hands commanding her to spread her arse cheeks wide, whilst I grabbed the base of my cock to keep it firm and steady. With one hand on the base of her back, I slowly but forcefully pushed downward. Gradually my penis inched closer inwards, pushing globs of vaseline out of her opening. Unrelenting, I pushed harder and deeper until finally with a satisfying grip, her anal muscles swallowed the head of my cock and gripped it like a vice. She gave a groan of pain, satisfaction and pleasure. I pulled my foreskin a little further back to full appreciate how much she was enveloping my head. From here each movement was slow, deliberate and precise, all with the intention of inching my penis further and further insider her anal canal. Watching my long brown cock disappear into her pale round ass was enough to make me want to blow my load right then but I was starting to gain traction. With each slow rhythmic motion inside her, Nicole was wincing, whilst I was barely trying to hide my ecstasy. As finally half of my penis had disappeared inside her tight arse, I started pounding her heavier and more deeply. I could see the pain on her face as she was also getting lost in the pleasure. The temptation to fuck her arse as aggressively as I might her pussy was too much so I started pounding it with light aggression slowly gaining further depths inside her. Each time I did this Nicole would plead, "Not too hard." And I would momentarily ease up before pounding her a little harder, a little faster and and a little angrier. Soon her groans of pleasure and pain were growing louder and more guttural whilst her hands soon dropped from spreading her cheeks. Each time I punctuated a rhythmic fuck with a deeper entrance she would grip the sheets and wince a little harder. Sensing that she was either losing herself to the moment or reaching a limit of pleasure and pain, I grabbed her arms back by both wrists in one hand and her long ginger hair in the other hand, pounding her arse as deeply and aggressively as I could, watching her tear up whilst a secret part of me became even more aroused at what sexual pain she was enduring for my pleasure. As my long, hard, brown cock disappeared in and out of her pale round arse I finally released her arms and hair, angrily grabbing both cheeks before digging my cock right up to the hilt whilst ejaculating gloriously into her deepest, darkest recesses coating her dark walls with my white warm cum. As my cock twitched inside her dribbling the last spurts of sperm into her arse, I basked in the glow of what may have been the greatest fuck of my life before looking down at Nicole, who despite looking bedraggled with tear stained mascara running down her face, returned a look of pleased satisfaction at what she had achieved. At that point, I realised who had really been fucked. My First Anal Adventure My first year of college I jumped quickly into a long-term relationship. Sarah was her name, at 5'11" 125 lbs. With creamy white skin beautiful 34c breasts and the longest legs I have ever seen thus far, she needed to do little more than smile seductively to turn me on. Of course being an 18-year-old male probably didn't hurt either. We had a healthy and very active sex life during our time together and like most couples I'd imagine we had things that we would joke or tease each other with. One of those things for us was anal sex. We had never tried it and at the time when we first discussed it neither of us was terribly interested. It seemed like a lot of work for what we thought would be little gain. Boy were we wrong. Sometimes when we were fooling around I would gently push the tip of my penis to her ass hole and make some pithy remark about my fucking her ass. Or occasionally she would mock plead with me to take her ass cherry. But of course, this would never result in anything ever happening it was simply a joke. And for a time it remained just that, then I started to realize that all of this teasing had actually piqued my interest. I really wanted to fuck her in the ass. Shortly after I made this realization I went to the store and picked up some lubricant. That night I was a man driven, I had built the experience up in my mind and I needed to act on it. That night we were in bed she was lying on her back one hand playing with her breasts and the other with a death grip on my hair as I lapped furiously at her clit. "Oh god, Oh god yes yes!!" She screamed as I brought her to climax. When the orgasm had faded a bit I pulled away from her wet pussy my face still damp with her dew. I pulled her legs up and rolled her over onto her stomach. She turned her head and looked at me wondering what I was up to now. I showed her by licking up from her throbbing clit, over her swollen lips and hairless taint. I finally came swirl my tongue around her tight pink ass hole. I began to slowly flick my tongue around the edges avoiding the hole at first. She laughed lightly and looked as if she was waiting for the punch line. But I could see in her eyes too that this did feel good. I decided to take things a bit further my tongue spiraled down to the puckered hole. She gasped slightly when I pushed though with my tongue. At the same time I took my finger and pushed it into her pussy. Her body jolted from the pleasures she felt all at once. I kept doing this for a little bit until I felt that she seemed really comfortable. Then I removed my forefinger from her snatch and inserted the well-lubricated digit in to her ass. She let out an audible groan and then turned and asked me what I was doing. I assured her that everything was fine and that she should just relax and enjoy it. With one last skeptical look she turned back around. I then proceeded to slowly push my finger in and out. The sounds Sarah was emitting told me everything was going well. So I decided to up the bet, I removed my finger wiped it off with a near by tissue and then inserted two fingers back into her cunt. They slid in very easily, I thought to myself. I realized then that she was really very wet, more than usual it seemed. I smiled to myself as I moved those two fingers from her sopping pussy and slowly pushed them into her puckered hole. This time the groans were a bit louder and hips were moving slightly in rhythm with my thrusting. With my free hand I reached for the lubricant I had bought. I opened it up and began to rub generous amounts onto my hard cock. When I felt that her sphincters had loosened. I removed my fingers again only this time I replaced it with my dick. Though my penis is considerably larger than two fingers, I was getting anxious. I wanted to take her ass cherry and I wanted it now. I pushed the tip of my head gently into her hole. She turned around suddenly as if realizing what was happened. She looked as if she was going to say something, but then she just smiled and turned away. Smiling wide I proceeded with the task at hand. It took me some time to finally get my whole head into her ass. I had to push in and out and in and out each time getting only a slight bit further in. I decided to let her ass get used to what little of my cock was already in her. I waited for a bit then pulled out completely. I applied more lubricant to my cock and this time I put some right in her hole. Then I pushed my head back in her tight pink hole. This time I faced much less resistance. So I pushed forward, I managed to get half of my cock in her ass before pulling out and re-applying lubricant. Then I gripped her hips and plunged my whole seven inched into her. She let out a muffled gasp. I kept myself still insider her, wanting to cause her as little discomfort as possible. Her sphincters adjusted to accommodate my penis as she relaxed her body. I took this as a cue to begin. In and out of her ass I started piston building up momentum. Sarah was moaning loudly now. One of her hands gripped a bedpost as the other traveled down to her crotch she began masturbating furiously. Her moaning started to build in intensity until they were full-fledged screams. Her usually porcelain white face was now flushed a deep red and her eyes were tightly shut. I could feel the bed starting to soak with her juices. It was more than I could handle I began to cum right there in her ass. I kept pumping until I started to go limp. Then I pulled out, a trail of cum oozed down her crack. I laid down next to her. She was still breathing heavily, but she reached up and pulled my face to hers roughly and kissed me, teeth biting down on my lips hard enough to draw blood. "My god that was wonderful. I never thought it would feel like that. I've never cum so many times in my life. I don't even know how many I had." Sarah said to me as she caught her breath. "I'm glad you liked it, I really did too. We'll have to do it again sometime." I replied. "We certainly will!" My First Anal Experience This is my 2nd submission of my true experiences. My first story is how I experienced my first Contact with men, giving and receiving blowjobs through a gloryhole. Months had passed since my first experience but that first experience had a great effect on me. I started going every Friday night for some quick action before I headed home from the clubs. I also like going to different bookstores because not knowing the layout and exploring the whole place was exciting. On one particular night I did try a new bookstore and quickly found a booth with a GH. When I heard someone enter the other booth and saw the fingers through the whole I went into action. I put on my condom and stuck my dick through the hole but nothing happened. I heard a lot of movement and then the sound of his belt being undone and his pants going down. It was normal noise you hear all the time so I thought nothing of it. All of the sudden I feel pressure against my dick. This was not a warm mouth taking me in so I was confused as to what was going on when it hit me. He kept moving in and out and I realized he was trying to get fucked. All of the sudden my juices started to flow really hard. I finally felt my head enter him and slowly little by little my dick was inside him. I did nothing but let him do all the work and about three minutes of this I came. To this day I do not know how I entered him without lube. When I left all I could think about was how it would feel if I had someone do me. After three weeks of attempting to do this then chicken out at the last minute, I went for it. There was this one bookstore that had some really good holes and action. It was late Saturday morning; I bought some lube and several condoms then headed to the bookstore. The place was packed with guys. My regular booth was being used so I started to walk around. I walk into the movie theater area and while watching the movie I noticed a tall guy in his late 30’s, long blond hair checking me out. After a while you know what certain looks mean and I knew he was looking for action. I decided to go back to the booth area and wait. As I settled against the wall in front of my favorite booth and wait for it to be free when the tall blond came by and settled himself in front of a booth which happened to be next to me. I could see in the corner of my eye the guy looking at me. Finally! The door opens and I enter the booth, at the same time the guy in the other booth leaves so I know the Blond hair guy is now in the booth next to me. I begin to flip channels until I find a video I like. Looking at the hole I see the guy looking through the hole waiting for some action. Feeling brave all of the sudden I put my fingers through the hole and invite him to put his dick through. When I saw his dick I was shocked. It was big! Too big for me to have him fuck me, this was going to hurt. I start off giving him a blowjob, at the same time I finger myself to try and loosen myself up. I’m ready, so I take the lube and put some on the condom and some in and on my asshole. The guy begins to insert his dick and I feel pain so I pull away and wait for it to go away. Again he tries but he is slow about it as if he knows he hurt me the first time. Once he is fully in he begins to thrust in and out real slow. Man, I started to enjoy it. This was one of the best feelings I have experienced. I could not believe how good this felt! I kept adding more lube and he kept pumping faster and faster. Looking down I noticed I was cumming! Not once did I touch my self and there was cum dripping from my dick. My whole body was relaxed and enjoying the experience. The guy started to thrust as fast as he could and then he came. He was in me for another 15 – 20 seconds before he pulled out. I did not hang around for the next guy or clean myself up. I left the bookstore and went straight home to shower. As I was cleaning up I realized I was still horny. Even though I was cumming during the fuck I never really got myself off. As I masturbated I imagined the blond guy fucking me. Three fingers were in my ass as I played with myself. I came very hard and my whole body felt like it was cumming. To this day I wish I had hung around to talk with the blond hair man. I would have loved to been his fuck buddy. I never saw him again but what he did to me that day left me wanting more. And I did get more but that is another story for another day. I hope you enjoyed my story. Please contact me and let me know what you thought. I love to hear from everyone. My First Anal Experience I would like to tell you about the first time my old girlfriend and I had anal sex… We hadn’t been going out for very long and it was still in the beginning glow of sex all the time. Our day had been good and we were on number 3 sex session for the day. This was still in the time of the do it and do it all and do it right now at the beginning of a relationship. She was great in bed regardless but that added the extra spice. The first time that day was after we woke up in the morning and I went down on her to get ride of my morning breath. Naturally she returned the favor by engulfing my cock in her mouth, she couldn’t deep throat me, but she still gave very good head. She was always ready to suck my dick and loved doing it. She would lick all around the head, very gently. One of my favorite things to do was walk in on her in the bathroom and whip my dick out and have her suck me when she was on the toilet. She wouldn’t complain, she would just smile and then lick and suck me for a minute or two to tease me and then finish her business and we would go on with what we were doing. If you were wondering I have a moderately sized dick, about 7 1/2 inches long, and quite thick, it was as thick as her wrist, now that I think about it. The first time we ever did actually have sex, the first time I put it in her, she grunted kind of oddly. We were doing it missionary and she had of course already seen me and played with it a good bit, sucked on it etcetera but apparently it didn’t really strike home until I was deep in her pussy. I pulled back and stopped moving to ask her “Honey, what’s wrong? Are you all right?” She looked back up at me with this lustful expression as she said, “No, I’m okay, it’s just that you’re much bigger than I am used too.” Talk about an ego building moment! “Do you want to stop, does it hurt?” I asked. “No! Don’t stop, it feels fuckin’ great!” she exclaimed. And too prove her point, she pulled my hips back down into her again. But I digress. She always tasted oh so sweet. I had shaved her pussy about 3 days ago, it was the first time for her, and we both really liked it. She said that there was better sensation, and I liked it because I didn’t have any hair in my mouth, and wow did it look awesome. Her name was Irene and man what a lady. She didn’t have really big boobs or a great ass, but it was a nice ass, and good firm small titties. This is a true story, not a fantasy. But she had wonderfully sensitive nipples and would gasp and moan every time I would suck on them or play with them. Sorry, back to the story. As I was licking on her clit, and she was sucking my dick, I could tell she was getting close to cumming, she was starting to move her hips around in a circular motion, and she was moaning around my dick also she was pushing up with her pussy into my mouth, especially when I would lick her clit with the underside of my tongue, the smoother side so to speak. To make her cum just a little sooner and a little better, I put two fingers inside her pussy and started to rub around the top wall towards my chin, I could feel her g-spot after a moment or two of searching. It was an awkward position for my arm, but the way she moaned made it was totally worth it… She started almost humming on my cock as she got closer and closer to cumming with my dick in her mouth. Quicker than I thought, she came, spitting out my cock and pulling my head down on her pussy. She had a very nice little orgasm from that manipulation of her pussy and pushed me over on my side, off of her. Then she turned over, got on all fours, and made here decision very clear. “Fuck me.” She moaned in a soft voice. I could still see the ripples on her thighs as she continued to have small contractions from her orgasm. Quickly I got a squirt of Wet, (a wonderful lubricant if you need some!) rubbing it all over my very hard dick and then smeared the rest on and in her already wet pussy. I moved in behind her and aimed as best I could without being able to see very well at her little slice of heaven. Of course, I missed, and hit right between her pussy and backdoor, pushing down to the right spot she pushed back as she felt me on her opening. In I went and both of us stared to grunt and moan and strain as we fucked faster and faster. I first I was just holding her hips, and then pulling on her hips, then unable to get enough leverage I moved one hand to her shoulders and then both to pull her back even faster and harder onto my cock. “Faster, more, more, harder! Yes, here I cum,” she cried, I could feel her pussy pulsating around me and soon I exploded deep inside her. Later that day… at about 12 or so, we had been watching tv and just relaxing on the couch for a while. Neither of us was wearing very much at all and she was leaning up against me. This was some great cuddle time and after not too much longer it started to have an effect on my second head. Up it rose, like a submarine periscope. I wasn’t really doing anything about it other than enjoying my hand on her tit as we sat there, but soon she noticed my member at attention. I was in sweats so it was pretty noticeable I guess, she reached down to the waistband and pushed it back behind my balls. Gently she leaned over and licked the head, slowly while looking sideways up at me. It was so erotic, she even did the porn star hair flip so that I could watch as she bobbed up and down on my cock. Licking and sucking gently, using her lips a lot, and going even farther down to suck my balls occasionally. After she had really got my dick nice and wet she stood up and took her shorts and t-shirt off. “I wanna try a position that I saw in porno movie one time.” She had the most devilish grin. “Sure, what do we need to do?” I asked, very interested as you can imagine. Porno positions?? What’s next with her? “Okay, I am going to lie on the floor with my legs in the air and my back against the couch, I want you to put your cock in me from above, while I have my legs out to the sides.” Having said that, she promptly moved into that position. It took some doing, and a little acrobatics to get into this contortion, I think its called the “pile driver” and it seemed okay, but neither of us liked it too much. It hurt a little to have my dick pointing straight down and she said that all the blood had rushed to her head, so she wasn’t getting as much sensation out of it. We even tried turning around so that I was facing towards her butt, and doing it that way, it was easier to get into that position, and a little easier on my cock, but didn’t do too much for her or I. After about 5 more minutes of that we stopped. I sat back on the couch, and she got up to sit in my lap with me now back where I belonged inside her tight puss. I could also suck on her tits from this position and was quite able to get both nipples in my mouth at the same time. She felt so nice and it was much less energetic and painful. But still very friendly, fairly quickly she rode me to a great orgasm for both of us. Have you ever had a simultaneous orgasm? When you can just feel her contracting and pulsating around you, sometimes you can feel her juices just flowing out and around your cock, as you feel like you’re about to blow the top of her head off from your own eruption? Its one of the best feelings in the world. But the reason that I started this story was to tell you about the first time I ever had anal sex. After our lunchtime fun, I had gone to run some errands and do some things at my house. She had had to go out and about as well and we agreed to meet at her place at about 8:00 that night to go out and have a good time with some friends. Well when I got to her apartment, she was there, but in a foul mood. I don’t remember exactly why, maybe it was traffic; maybe she just couldn’t get her errands done. Either way, after I was there for a little while, I noticed that she was being really bitchy. Never one to be yelled at for nothing, and still horny from earlier that day, I tried to talk with her for a while about what was wrong. To listen, not to fix a problem, just too listen. That seemed to take some of the wind out of her sails. Maybe a better way to say that is that it seemed to help her to be able to just vent about it. Then I just decided that I didn’t want to wait until after dinner and some time out to get laid again. She was also getting dressed at the time and was only wearing a bra and thong. That might have had something to do with turning me on. I love a good thong, where you know its disappeared into the crack of her ass, and you can just barely see it in between her cheeks as she walked around the room. I moved in for the kill. As I started to approach Irene, I had stopped talking with her. She looked over her shoulder at my silent approach and smiled slightly, and moved farther down her closet from me. Not much, but I knew and why and so did she. The farther I moved forward, the farther down the wall/closet she moved. It was a full wall 3-door closet. Mostly full too. As she got to the end, she turned and put her finger up in my face. “Doug!” she exclaimed. But she also had this devilish smile on her face at the time. “Yeah? What? You tell me to stop I will. Just say NO, but until then I am going to get you naked and the fuck the hell out of you, maybe it will put you in a better mood. Telling me No is the only way I will stop.” I said. I was actually getting kind of irritated at her for the way she had been acting. On the other hand if she was willing to put out, well it would make her feel better and me too. As I grabbed her arms and pulled her close, she struggled just a bit, but only playfully. I had given her the out, if she said no, I was really going to stop. I pulled her too me and started to nibble on her neck, slowly moving up to her ear, nipping the lobe and gently biting the skin. Not hard, but softly. I held her arms down on her sides, so she couldn’t reach all the way around me as I reached behind her for her bra clasp. After that was undone and I was holding her tight too me, I reached down to her ass and pulled her tight against my thighs. She is 5’4” I am 5’ 11” and about 70 lbs heavier than her at 195 or so. It wasn’t so much of a contest of strength, just of wriggling until her bra was gone. By this point she was starting to kiss me back and run her hands up my back and to pull me closer to her. Looking her right in the eye, “Get naked and on the bed, right now!” I growled softly in her ear. She looked at me, smiled and quickly backed away from me, pulled off her thong and got on the bed, lying on her side to watch as I undressed. That took about 45 seconds at the most, and I quickly got on the bed with her. But not exactly like she was expecting. I kneeled on the bed and as I moved towards her, I moved right too her head, my cock was stiff as could be and standing at its normal 65 degree angle. I moved right too her face and pushed it into her mouth. She smiled around my cock as she started to suck and lick at the head. She wasn’t moving really deep on it as she was licking, but it still felt like a warm bath, as she breathed out and on my dick. I was really enjoying her lips and suction as she slowly continued the blowjob. Playing with her tits as she sucked me was quite nice as well, but I really wanted to fuck her and fuck her now. Besides it was more about making her feel good and not me at this point. So after letting go of her head I shifted my body around so that I could get at licking her sweet pussy. She moved to her back and kept up her good work on the head of my cock. After about 10 more minutes of eating her pussy and another orgasm, I decided that it was time to fuck what I was eating. So I sat up, pulled my dick out of her mouth, along with her murmured protest, and moved in between her legs. As I slipped the head up and down her slit to tease her, she started to pout and tried to pull me inside by grabbing my hips. “Ha! Not a chance babe” I smirked down at her Slowly I teased her pussy for about 30 seconds or so, moving up and down, pushing hard on her clit, rubbing back and forth, all the way down to her ass and pushing a little on that and then back up, I even pushed along her clit and almost up to her belly button… She really liked that and it tickled me as well. Finally though I wanted to be in her tight heat and slipped in her. She closed her eyes as I slowly pushed all the way into the very bottom. I could feel the string from her diaphragm and so could she. We looked into each other’s eyes as I started to piston my hips up and down. She was moaning and thrashing on the bed very soon after that and reached up to run her nails across my lower back. Unfortunately she had really sharp nails. I probably still have scars to prove it. On the other hand it got me even deeper inside of her, which was what she wanted. I wasn’t about to complain other than about the red nearly bleeding streaks in the skin of my back. It was at this point that I realized I really wanted her to be on top. She usually didn’t like that, said she felt fat in that position. It’s a silly complaint, especially when I am as deep inside her as I can get at the time, I certainly didn’t feel she was fat, and she didn’t look that way to me, even more important, I have less stimulation if she’s on top and can last almost indefinitely from that position. Ah well. On the other hand, I didn’t give her a choice. I simply pulled her left leg in tight to me and rolled that way. It squishes her leg for moment, but that’s about it. Like I said, I didn’t give her the choice and as she was on top, I pulled her down so I could kiss her and suck her nipples and I started to fuck up into her pussy. Reaching around I started to finger her asshole, it was always one of my big fantasies to do a girl in the ass, and little did I suspect! As I reached, and started to finger gently around her asshole, I started to gently tease her pucker, ever outside, but mainly to just let her know of what I was thinking about and test out her reaction. The reaction was good, she gasped straight in my ear as I put in my middle finger to the second knuckle and started to wiggle it around inside her butt. God it felt soooo good in there, There we were on the bed, doing it with her on top and she suddenly pressed down on my cock sat up straight, put her hands on my chest and looked down into my eyes. “I wanna switch to doggy style on the floor next to the bed.” Now I am a gentleman and always willing to please a lady, so I let go of her hips and she got off of me. It was at this point that I told her to “assume the position” it was our favorite position, and that was the code words for doing it doggy. I scooted up behind her and slipped into her wonderfully tight pussy. Like I said it was the 3rd time that day, so I was able to last quite a while, even in though doggy gives me the most stimulation. I started to really pound into her pussy from behind. Holding tightly on to her hips so that she couldn’t get too far forward and I certainly didn’t want to slip out. We were both so sweaty at this point it probably would have been dangerous. Besides, I already knew that she loved to have her hips held tightly as we did it doggy style, she said it felt even better than normal that way. Its her hips, who am I too argue?? That was when she really threw me for a loop, we were going at it hammer and tongs, and she knew that I was a curious about putting my cock in her ass from prior conversations, aside from just having my finger in there. She looked back after she had come like two more times and I was starting to get close… and said “Doug do you want to fuck my ass?” Such wonderful words! “Oh god! Honey do you mean it?!?” I gasped back to her, my eyes very wide. She grinned and nodded. Now remember that this was my first time… and I pretty much fucked it up. I pulled out, got up grabbed the bottle of Wet and put some on my cock and her ass, some in her ass as well. She jumped when I put it on, and so did I. Dang that stuff was cold!!! I might have been too rough with putting some in her ass as well, know that I think about it. So after getting the lube on both of us, and without any of the better preparation that I would do these days, you know, fingers, toys, possibly my tongue, or my tongue on her clit as I played with her pussy and put a toy or fingers into her ass, but oh no, not me, I put the head to her ass and pushed too hard. She yelped and jumped forward to get off my cock then she looked back and said, “Hold still so that I can get used to your cock up my ass!” What a wonderful thing to say! I can still see her face as she pushed back on to my throbbingly hard cock. “Line it up again, and I will do the work.” Of course I readily complied with that command! She slowly pushed back on to me, it felt like my whole body was on fire as my cock entered her ass, I swear it was about 150 degrees in the room at that point, even though it was snowing out at the time. So gently, slowly, lovingly she pushed more than the head into herself. It was at this point that my cock twitched and she jumped again. It wasn’t on purpose, but the reaction to how good it felt almost made me cum. When I twitched later on after I was all the way in, just let out a soft cry and moaned, “yes, do it again!” And then she pressed even farther back until I was all the way in to the hilt, buried in her colon. Have you ever felt a woman’s ass-cheeks pressed against your groin when you are as deep as you can get inside her ass? I was in heaven! Holy shit it was great! I can still feel her hips and everything pressed back to me. I could even lightly feel my balls pressed against her pussy and her fingers manipulating away on her clit, I leaned forward and played with her nice little titties, she was so close to orgasm at that point that she went over the top with the extra stimulation of my tongue in her ear, and my hands on her boobs, along with playing with her clit and my dick up her ass. I can still imagine her as I look down from behind her and can feel the contractions in her ass and pussy as she came really nice and hard. Even more so as I lay on her back playing with her boobs. After she was more used to me, she said to start fucking her ass, which I did, a bit too hard and then as I was really getting into it she tightened up, a lot, and not in a good way. Unfortunately I didn’t realize this at first, and was getting really close my self. I was pulling hard on her hips and had gotten back up off of her back as I fucked into her ass at high normal pussy speeds. Like when you’re both close and really want to come hard and fast. It was my fault for not noticing, she groaned and then cried out in a very different tone of voice and she had to reach back to stop me, she pushed on my lower stomach to stop me from still pummeling her asshole. As she did I understood that there was a problem. She grimaced a bit and said, “I tightened up and to hold still for a while so that I can calm down and relax.” “Is that normal?” “No but it happens,” she replied I asked, I was in a state of aroused and frozen shock, I didn’t want to hurt her at all of course, and here I had gone and hurt her anyway. I don’t know when exactly she tightened up as I was too caught up in the moment, but there were probably three full strokes that I did before I knew that there was a problem. I felt terrible about that and still do. We waited about a minute or so and then after she felt better she told me to hold still and she put her head down and started moving her hips on my cock. I was back in heaven. I could feel the tightening and loosening as her sphincter worked to eject me from her tunnel, it wasn’t having any luck, but it felt so damn good. Then she reached down to her pussy again and after tickling my balls she pressed two fingers inside herself and up against the back wall of her pussy. I could feel her fingers right against the bottom of my cock, but inside her pussy and through the walls of flesh, she was so amazing! Suddenly I couldn’t take it any more and grabbed her hips and pushed as hard as I could up her ass and she leaned back against me. We could both feel this molten blast coming out of my cock up into her rectum, I usually have a pretty good load but that one was out of this world. She came right at about the same time, God it was wonderful! She usually wasn’t very loud, but that time she made the most wonderful sounds. And they were loud sounds! Things like “fuck my ass faster, a little harder, oooh more more, right there, Yes YES! My First Anal Experience The bad part of the whole experience was that she was sore in her backdoor for about 5 days or so after that. I felt really bad, but she never was mad at me, she just said it was a heat of the moment thing. Then she turned me on again so hard that I basically wanted to tear her clothes off in the kitchen and couldn’t was when she told me this, “Actually even though it was a heat of the moment, I don’t mind that, but I think of how good it was every time I have to use the bathroom, it turns me on all over again! Now that I think about it, we did it that way again about 10 days later. Fortunately without the tightening u though, so she wasn’t sore at all the next day. In fact we had simultaneous orgasms the next time I was in her ass, she came just before I did, which caused me to cum and the she came again from the flood of my load going up her canal. Anal was never the main ingredient but it sure did add some spice sometimes. And it could give some of the best orgasms for both of us. There are times that I still miss her. Please let me know what you think! My First Anal Fuck Carrying on the subject of "firsts" - this is a good one! I was having a fling with a guy I worked with - It had been going on for about 6 months and we were fucking in offices And store cupboards and all sorts - we even snuck into an Empty house that he still had the key for a fucked there! When I moved into my own flat it became easier - we would Sneak off after work and spend hours fucking each other! No-one knew about the two of us as he had a girlfriend (ok Don't judge me!!) On his last day of work we all sat around In the bar getting very drunk and saying goodbye to him. Our boss had given us the keys and said for us to lock up When we were done but to make sure that we were out by Midnight! So we all got very drunk and then suggested that we went Back to mine for some late night drinking - we were all in The living room and my friend and another guy we worked With were snuggled on one sofa - me and my "friend" were Sat together on another and there were 5 or 6 people on the Floor. We were all drinking and Becky started to Go down on Wayne in front of all of us! Everyone was Laughing and giggling about it and Wayne sat there with his Eyes closed enjoying the experience. With this going on right in front of us it was making me And my friend very hot and he was fingering me under the Duvet we had over us. Eventually I couldn't stand it anymore And I announced that I was going to bed - with a quick Squeeze of his cock which I knew he would interpret as an Invite I left the room. I hadn't even got all my clothes off Before he was there hands down my pants and pulling my bra Off of me and letting my 36G boobs out. I undid his trousers and pulled out his huge cock! He was a Black man and his cock was so thick and juicy! I pushed him back onto my bed and climbed on top of him - I Was so wet from the performance that we had just received in The living room I was already wanting him to fuck me - we Were kissing each other passionately as I slipped his Enormous cock into my soaking pussy. I sat up on top of him And rode his hard cock feeling it push in and out of me - The bed was banging against the wall and I was moaning Loudly as I could feel my orgasm building up inside of me - We knew that we had a house full of people that weren't Supposed to know about us but that didn't matter we were Going for it. Just as I could sense him getting ready to cum I pulled off of him and shuffled up so he could eat my pussy. We swapped Positions on the bed as I like it when I am underneath and Sucking cock in 69 positions. I came really hard while his tongue was in my cunt and I Was ready for him to fuck me again so I could feel his hot Cum inside of me. I hooked my legs over his shoulders and could feel him Pushing against my hard clit. "Down a bit......." He asked me what I meant "Down a bit - I want you to fuck my ass - I wanna feel you Cum inside my tight ass hole" I don't think he could believe His ears - we had never discussed this - it wasn't even Something I'd said I wanted to do but at that point in time I was so turned on I wanted nothing more than to feel him Rip into me. He positioned the head of his cock over the entrance to my Ass and pushed gently - I rocked my hips up to ease him in And took a deep breath - he went slow at first but once his Pre cum started flowing we were rocking together hard and Fast - I put my arms up and held onto the headboard as he Pulled on my hips and pushed into me hard and rough. "You like this = you like me fucking your ass - god you are So tight!" "Yeah that's good - yeah do it - harder - fuck me harder - I Love your cock in me!" The sensation was amazing - it felt dirty and naughty but Unbelievable at the same time, when his thumb found my clit I felt the orgasm rock through my body and he grunted Loudly and shuddered as he filled my ass with his cum! When we had finished we were all too aware of the sound of The TV from the living room but the absence of voices - we Both fell back onto the bed and led there together for ages Not saying anything - I was sore but still so horny - after About twenty minutes I climbed on top of him again and moved My hips back and forth - feeling his cock getting harder With every movement -when he was fully erect I slipped him Into me and rode him slowly he massaged my boobs as I rode Him and rubbed my clit - I could hear the voices now right Outside my door and the fact that people could hear us was Really getting us off and we got louder and louder - Eventually he flipped me over and was fucking me doggy Style with my hands up against the headboard - the whole Bed was rocking back and forth and smashing against the Wall - I screamed out as he made me cum and he pulled me up So my back was pressed against his body as he squirted his Cum into my pussy. It was about 6am before I put him in a taxi home and from That night on it was quite difficult to deny our Relationship to the rest of my colleagues! My First Anal Sex 4pm... One of the things I want to experience the most is anal sex. Haha, I've just admitted to myself that I want anal sex. Now it is just a matter of bringing it up to my husband. He isn't the most adventurous man. I met him at a high school reunion. I hadn't known him at all in high school but he did admit to seeing me around. "I remember you having long brown hair and glasses, "he told me over our third glass of wine. We went to bed that night and have been inseparable ever since. Two kids and a home later, we are still entertaining each other's failing bodies. The brown hair is graying and the perky high school cheerleader breasts have lost some elasticity. My ass however, is the same tight rear end that used to poke out beneath my tiny cheerleading bottoms. So, tonight I'm going to give in to one of the nagging desires at the base of my brain. Tonight I'm going to get my husband to fuck my ass. 7pm... Hubby is home and hugging him my nipples instantly go hard. He cups my rear end and thoughts go to the butt plug waiting for us upstairs. His kisses are gentle but long. I lean into him and he can tell from the look in my eye that I want it bad. 10pm... The kids are in bed. Our oldest is out on a date. She is able to take care of herself, so I don't worry too much. She is a lot like me in different ways. I slide into a bath. I read online that you have to prepare for anal sex. The bubbles play along my skin as I spread my ass cheeks apart with my right hand. I begin to finger the outside of the hole. My nipples are rock hard. A gasp escapes me as I slide my ring finger into my tight pink hole. I adjust a little so I am as open as I can be. I can hear the TV going in the other room. Biting my lip I use my other hand to flick lightly across my left breast. I nudge my finger in and out of the tight hole which seems to be loosening with a mixture of arousal and force. The wet feeling between my legs calls to my hand. I remove the left from my breast and ease my clit in tiny circles. My hair is soaking across my shoulders as I lean my head back. I use to fingers now to play with the virgin hole. I feel myself so tight and wet both holes giving in to my deep desires and needs. Another moan escapes my lips. The door opens startling me, but I keep my hands where they are. "Sorry had to go pee," hubby says closing the door behind him. Situating himself over the toilet he looks back to see me. He sees my missing hand and just as he flushes, his cock springs to life. "Lay back", he says coming to me. His hand goes between my legs. He runs them up and down my thigh as I continue to fuck my own pussy and ass. A thicker masculine finger slips under the water probing at the innocent opening I've begun to create. Moans start in hurried fashion as he pushes his ring finger inside me. I can barely stand it. "I think you can take more," he says with a smile, "we need lube". He leaves the room and returns with the butt plug I had hidden in the dresser. I guess it really is hard to hide things from your spouse. I blush but he doesn't react. Instead he helps me from the bath and dries me off. Each touch sparks a pulsating sensation between my legs. He spreads the towel on the toilet seat and instructs me to straddle it away from him. I move into position. Cool liquid squirts across my athletic derrière. Then the same liquid is sprayed on the butt plug. He starts by working a finger and then another into my firm ass. My leg begins to shake as my fingers find a familiar button to circle and tease. When he finally places the butt plug against the outside of my ass, my whole is open from lust. A hungry whole waits as he quickly thrusts inwards. My head bows back as I push down on my thick clit. In and out he moves the plug almost in a clumsy fashion but the feeling is intense. "Take a breath," he says as he removes the plug, "I think you are now ready for something bigger." I brace myself as his cock now tries to enter my taunt hole. My hands go to the bowl as he pushes himself in. I can barely keep from coming. "I'm going to cum soon, "my husband says in a thick gutted growl. I am holding back as well. We both let go in a stream of pure sex. His dick explodes into my ass like a rocket launcher. I can barely breathe. "When did you get into anal sex?" He asks helping me clean up from the most cum I've had in me in years. "When did you?" I ask. We both just stare at each other and laugh. My First Anal Sex - Receiving I was nervous. I was horny, but sober. But I admit I was really nervous. I had wanted to have a cock up my ass just to try it, but as I got my nerve up, the first couple of encounters were so large that I stayed with giving them a long blow job and bringing them off in my throat. I liked it and they seemed satisfied. But now I had been on travel and away for a week and I was horny and felt a little adventurous.. I decided that I needed to stretch my virgin ass, so I got a soft fake cock and some lube. And I practiced, and practiced, and stretched and came and practiced. I posted on a site that I wanted to play in the next 12 hours and received a couple of offers. The first did not show so I tried another. I did not promise anything specific, just sex. I could chicken out again. When I opened to the man who knocked on the door, a slightly younger (30-40s) Asian man walked in and smiled. He bowed nicely, and I kissed him. He kissed back, hard. He was buff, I mean he was tight; I am not. He made me out to be the sissy I am. And he took over. I tried to undress him and he pushed me back gently and opened the hotel bathrobe. He pushed me onto the bed and spread my legs. He felt up each leg and massaged my balls and my cock, letting spit drop down and then stroked me. I do not always get that nard anymore, but this did it. I started to stiffen hard. He dropped onto my cock and took me into his mouth. It was wonderful. Then he stopped and gave my thigh a slap, gentle, but a good slap. He stood up and I sat up unbuttoning his shirt, then unbuckling his belt, unzipped him, and pulled off his pants. He was almost hairless on his chest, and his stiff cock was sticking out from his shorts with sprays of dark stiff hair. His nipples were at my mouth level and I began to suck and bite him and he grasped the back of my head and pulled me hard until I thought my teeth might make marks. I nervously pulled back, but he smiled and shook his head "no." So I applied pressure and he pushed in until I knew I would leave marks. And he moaned. I suddenly thought I would not be able to go home for a week after this guy. But I was wrong. He wanted me to mark him only. Then he took over again. Funny, but he made sudden changes in tempo and who was leading. I was confused, but very excited. Long story shorter...His cock was just what I was looking for. Hard, long and not too thick. It hit the back of my throat again and again, and then he looked at me. I got up on my knees after opening the drawer and bringing out the lube and condoms. I was hoping for tenderness, but either our language barrier or his lust and dominant attitude took over and he rammed me hard. He was thick enough! I almost buckled as I winced. He slide in and out a couple of times, roughly opening me up, and then he stopped. He turned gentle and pulled out, got some lube and then gently came back in a little at a time, letting me open more comfortably as he rocked in and out, just a little. I felt his hairy groin hit my ass. Then he waited, gently moving just a little until I squeezed his cock in my ass. And he began the smoothest fuck, increasing the lengths of his strokes and keeping a very sexy rhythm while he stroked my back and waist. So this was anal sex from the receiving end. I actually remembered one Korean woman who had loved it when I fucked her ass and smiled thinking that I hoped she had enjoyed it this much. Suddenly, he slapped my ass hard several times, grabbed my shoulders and rammed in hard. I thought he must be getting ready to cum, and I was sort of happy. Then he pulled out, spanked me harder, several times and laid down on the bed. I was ready to fuck him now and he shook his head. I had me sit on his cock and start up and down. I pinched nipples and had to climb off to kiss him. He kissed as hard as he fucked and told me to get back on. This time his cock was thicker and even though I was spread, I seemed to feel a tearing. And he started to thrust up as he leaned his head back into the mattress and started to moan. Suddenly I felt myself start to cum all over his stomach and chest and he opened his eyes and smiled and fucked me harder. I took a while until my asshole was healed up, but I had two more guests that week. They felt good, but they never got close to him. But, good sex is good sex. But my first was special, I will admit. My First Anal Treat Hi everyone - my name is Jill - at least after I shed my drab old male clothing and slip into my real clothes. You see, I am genetically a male: caucasian, blond, blue eyes, tall, slender, and very submissive. I love wearing makeup, sheer black nylons and garter, long blond wig, short dresses, and heels. I won't bore you with how I started - but let me tell you, I love it! My encounters with men have been all through this most wonderful of inventions - the PC. Thank you, Bill Gates and Steve Jobs (not necessarily in that order). After hooking up online, I would meet them at local motels and do everything for them but anal. I guess I was afraid. Then, one day, things changed. I hooked up with my first Black man. He was married to a Black woman who had let herself go, refused to give him any oral, did not dress sexy, and generally ignored his sexual needs. Altho he still loved her, he needed more. So he sought out white transvestites - maybe that made him feel less guilty. But I was so glad he preferred those like me! We spoke once over the phone, and his deep baritone voice had me wanting him even more. We agreed to oral only on the first date, and decided to meet at a motel that was mutually convenient to us. I got the room, as I wanted to change for him and get pretty for him before he arrived. The night before, I took a long hot bath, shaved myself silky smooth, and went to bed. The next morning I awoke and shaved again, put my nylons, garter, heels, teddies, long blond wig, and short black dress in my luggage and drove nervously to the motel. I was so nervous. I mean, I had fantasized about Black men, and absolutely loved looking at sexy pics of white women with their Black lovers...but now I was going to experience my fantasy! I got the room and prepared. I knew he liked black stockings, heels, and teddies, so that was how I dressed. I also applied extra makeup, as he said he wife never wore that anymore. I wanted to please him in every single way! There was a knock at the door. I slowly walked to it and looked thru the peephole. It was Richard! We had exchanged pics, and I had been afraid he had sent me one of him as a younger man. But he hadn't. My heart pounded as I opened the door and smiled. "Hi Richard! I'm so glad you could make it." "Hello Jill. I got out of work an hour early. My God, you look fantastic!" "Please come in and sit down. You look wonderful yourself." He was wearing jean shorts and a t-shirt, both of which showed off his dark skin and muscles. I went weak at the knees. "I'm sorry. I'm still hot from work. I'm a foreman at a construction site, and didn't have time to shower or change. I was in such a hurry to get here." His scent had already intoxicated me. His short curly hair had a few beads of sweat and I longed to hold him, sweat and all, close to me. "Oh, sit over here." I pointed to the only chair in the room. I sat opposite him on the bed. We talked for a few minutes. He was such a gentleman! And so handsome and strong and, well, dark! I crossed my legs and my teddie rose up a bit higher, showing him the tops of my stockings and revealing the soft white skin of my thighs. I could wait no longer. I patted the bed and he sat next to me. I licked my lips and my eyes closed halfway. No he took charge. His right arm encircled my shoulder and held me as he leaned in. He said, "I love your red lipstick." Just before I felt his lips on mine, I murmured, "I wore it for you." Our lips met - black on white. I had never been kissed by a Black man before. His lips were soft yet demanding. His tongue entered my mouth and our tongues began a long slow dance together. I moaned as I felt his hand touch my knee. It moved slowly up my thigh and my teddie was soon at my waist. I had tucked myself beforehand so I hoped he felt nothing but my womanly body and tasted my desire for him. Our kisses went on for many minutes and my heart was racing! He lowered me onto my back on the bed and stood next to it. He began to lower his shorts. My God - he wasn't wearing underwear! "I hope you don't mind. I took the liberty of taking them off in my car before I got here." "Mind? I'm flattered." But my eyes were not on his as we spoke. I followed the progress of his shorts dropping to the floor. He kicked his shoes off and removed his socks. Before me stood my first Black man. Yes his cock was larger than any white man I had been with. It was longer and looked both menacing and delicious. But it was not so big that I feared it. "Jill, I want you." "Richard, please hold me." I couldn't think straight anymore. He laid down next to me, and pulled my close, kissing me again. I held his head to mine. I wouldn't let this man go. He gently pushed my legs apart and rolled over on top of me. "I love your long legs and the feel of your stockings. It's been so long since I've had a woman dress like this for me." "Oh darling, you make me feel like such a woman. I'll always dress like this for you. You are the sexiest man I've ever known." I felt his cock get harder as we kissed again. "Richard...may I do something?" "Anything Jill...anything..." I rolled him onto his back and began trailing kisses down his chest, letting my tongue touch both of his nipples. He rewarded me with a groan. His strong dark hands stroked my long blond hair as I moved to the top of his pubic hair. It was short and tightly curled. His sweat added spice to this oral dessert. My hands then touched his manhood. My lips rained kisses on it. My tongue rode up and down his shaft as I looked lovingly up at him. "Oh Jill...you love sucking Black cock, don't you?" I could only mumble hmmm hmmmmm as by now my man's cock was in my mouth and I refused to let it out! I was in heaven and did not want an exit. He got harder as I began pumping his cock in and out of my desperate mouth. My hair was all over his hot Black skin and the contrast drove me to even greater heights of passion and love. My red nails lightly stroked his very large balls and reached gently to his ass. One tiny finger stroked his asshole and he almost came on the spot. I retreated. I wanted this to last a long time - for both him and I. I wanted him to have the greatest pleasure he had ever had. He was a hardworking Black man and he wanted a tall, blond, submissive TV to satisfy him. I would not disappoint. Suddenly I stopped and took his precum covered cock from my mouth. "Jill - what's wrong? I was almost cumming..." "Do you remember earlier that you said you wanted me?" "Yeah, of course. I want you even more now." "Well, I want you too. I want you inside me. I mean really inside me." "But I thought we agreed not to...on the first date." "I know. But a woman has a right to change her mind, doesn't she?" Without a word he pulled me to him and kissed, more passionately than ever. "Straighten your stockings. The seams aren't straight. Then roll over on your stomach. I'm going to make you mine." I obeyed. He was my man. I was his woman. He pulled my panties to the side, and I expected pain. But instead I felt his hot wet tongue running up and down my hole. I shivered and begged him to keep going. "I figured you don't bring any KY on your first date, so I'm applying some of my own natural kind." "God, Richard, I need that hard Black cock so bad, darling. Please..." I felt his get into position to mount me. His strong thighs touched mine. I felt the tip of his manhood against my tight, virginal hole. "Richard, I'm a...a virgin." "I'll go slow." Did I feel his cock get even harder after I told him I was a virgin? Yes...it did. The head opened me and I gasped. It hurt just a little, but my man was keeping his word. He went slow. I felt him lean forward and about two inches entered me. The pain was sharp, but I tried to relax. When I willed myself to relax my anal muscles, four more inches suddenly invaded me. Now the pain was gone, and a feeling of such fullness, lust, and desire filled me that I began to cry. "Am I hurting you?" I had to catch my breath. Richard was both horny and sweet. I wasn't about to let this man get away from me! "No, darling...please...more..." He pushed into me and I felt those delicious black balls slap against my soft white ass. He began to slowly pump in and out, in and out. Our breathing was ragged. His hands reached under me and rubbed my nipples. My nipples are always very sensitive and now they were at their peaks! My small clit was at full attention. He was still moving in and out when I turned my head to him. He kissed me again. What a loving man! Our tongues met and I sucked his saliva into my mouth. He seemed a bit surprised but then locked his open lips on mine and I drank of him like a thirsty whore in the desert. I broke our kiss. "Sweetheart, I need something else..." His total weight was on me and his cock was deep inside me. I felt fulfilled as a woman, but needed just one more thing... "Anything, my Jill..." "Please cum inside me." "You know I'm not wearing a condom." "Two things: I never want you to wear a condom, and remember you never have to masturbate as long as you have me." He kissed me. Again. And again. And did not say a word. His thrusts became harder, and deeper. He was a man possessed. I knew he wanted me as much as I wanted him. Black into white. It felt so right. He was breathing so fast I was concerned for him. He leaned back, gripped my hips and roared out the primal scream of pleasure as he drove to my depths and began spasaming his very essence into me. How many thrusts? How many spurts of black cum were deposited deep inside me, his white submissive girlfriend? I lost count. But when he was done, when I had fulfilled him as a woman should, I asked him not to pull out. He didn't. We slept. He was mine and I was his. The seams on my nylons were in delightful disarray.