0 comments/ 262867 views/ 6 favorites Sometimes Size Does Matter By: biglouis This is a story in which the male in the leading role does not possess a 7 to 11 inch long penis as big around as a beer can. Rather, this man is of average or even slightly below average size. Personally, this author is rather tired of reading about how all men have oversized penises. Yes, I suppose I am jealous because I’m on the short side of normal, and yes I realize that these erotic stories are fantasy. However, I wanted to write this story for us more normal size guys. I met Bob at the athletic club and we hit it off right away. It just so happened that we were on the same workout time schedule, what with work responsibilities, etc. We became buddies and met several times for a beer. One day, after several months of male bonding, we were sitting in a bar having a beer and Bob said that he had a confession to make and a proposition to present to me. The first thing that I thought of was, OH NO HE’S GAY! I told Bob that I didn’t go that way and he started laughing. “No-No he said, I’m not gay. Although after what I’m about to tell you, you may start to wonder.” “You know we have showered together at the club and there have been several times that I’ve seen your penis as you have probably seen mine.” Now, I have to admit that I did glimpse at his penis and in a flaccid state it appeared to be 7 or 8 inches long and quite thick, whereas mine, when fully erect, stands at a proud uncut 5 inches and normal thickness. Bob went on to say that his erect penis extends to about 10 inches and is very thick. “Ok, so you’ve got a big fat cock and I don’t. What’s the deal? Is this where you point and laugh?” “Hear me out before you get all pissed off! I think you’ll like this proposition.” “My wife is a petite woman and a complete anal freak. You see she loves to be ass fucked but she can’t take my oversized cock. We’ve tried many times and used all the lubricants and all the tools like butt plugs, and all the fucking positions to allow her ass to accept my cock, but as much as we’ve tried it’s too painful for her. I’ve hardly been able to get the head of my cock in her sweet ass. Her pussy can stretch to accommodate my cock (just like it stretches when giving birth) but she really misses having a cock in her ass. I love my wife and I want her to be happy, so I’m wondering if you would fuck my wife in her ass. I’m sure she’ll be able to take your size cock.” “Wait, you want me to have anal sex with your wife, and it’s ok with you and her?” “Yes, but there is one condition. I have to be there to watch. You see, since I can’t pleasure my wife anally I want to be able to at least share her pleasure by watching her getting the thing she loves.” “I’ve never fucked another man’s wife in her ass, especially with him watching. I don’t know, I’ll have to think about it. Ok, I’ve thought about it and I’ll do it.” “Good, I know you won’t be disappointed. I’ll call you in a day or two with the time and place.” Bob called me several days later and asked me to come over to his house on Saturday night about 8 PM. When I arrived he met me at the door and invited me in. His wife was sitting on their couch and when she got up to greet me I thought I was going to cum in my pants. She was a gorgeous, petite blonde with the most perfectly shaped ass I’ve ever seen on a woman. Small tits but a great ass! When she took my hand as Bob introduced us, her name was Roxanne, I could feel my cock start to harden and stand at attention. “Oh, look Bob, it seems that our guest can’t wait to get started!” I was a little embarrassed and could feel the blood rushing to my face as well as my dick. “Well, I suppose I can’t really blame him my dear after all you do have the most perfect and sexiest ass any man would lust after. How about I fix us some drinks while you put our guest at ease.” Roxanne put on some music and took my hand. The first song began, and we embraced for the dance. It started innocently enough, but Roxanne began to dance a little more suggestively. She brushed her breasts across my chest several times, and then moved closer to grind against my crotch. Her dancing continued to get more suggestive. At one point she turned her back to me and started grinding her butt against my crotch. She placed my hands on her hips and led them up and down. When my hands drifted to her thighs, she led them back up under her skirt. My hands were rubbing her hips and squeezing her ass. Roxanne parted her legs slightly farther and bent a little at the waist. Her eyes slowly closed and her mouth parted like it was making an “ooohhhh” sound. My swollen cock was really hurting trapped in my jeans. Roxanne turned around unbuttoned my jeans and pulled them and my boxers down freeing my straining cock. Bob had returned with the drinks and had been watching his wife and I dancing. “Ooh, look” Roxanne cooed, staring at my uncircumcised throbbing erection. “He’s got a really nice one, honey. Isn’t it a beauty? It looks like it’s just the right size to fit in my ass without tearing and hurting me. Bob, you were right, it’s just perfect.” "Look, guys," she said, "We all know why we're here, so how about we get something going? Bob," she looked directly at her husband, "I'd love to suck his cock and taste his cum!” “Go for it babe, I brought him home for your pleasure and the pleasure I’ll get seeing you enjoying yourself. Just remember one thing”, my friend said to me, “you can do anything you and my wife want, but her pussy is mine and mine alone!” Roxanne dropped to her knees in front of me and started sucking my cock. I looked over at Bob, who had stripped naked and was idly stroking his monster cock as he watched his wife hungrily suck on my cock. Roxanne was every bit the expert cocksucker I’d imagined her to be. Sexy slurping sounds came from deep in her throat as she slobbered over my hard organ. Her husband was offering words of encouragement to urge her on; at one point telling her to show me how well she could swallow a cock. Roxanne responded immediately, and the next thing I knew my whole cock was disappearing down her beautiful throat. The sight alone was enough to start me coming, but Roxanne didn’t flinch as my semen streamed down her throat. She simply swallowed it all and then licked me clean. Watching his wife suck my cock and swallow my cum was too much for Bob. He started moaning as he continued stroking his big dick. Roxanne licked her lips and immediately fell to her knees in front of her husband. Her long slender fingers wrapped seductively around his hard shaft as she began to play with his cock and balls. Bob sighed deeply as she began to work his foreskin up and over his large bulbous cock head and then slide all the way down again to the base. Tickling his balls briefly and grasping the shaft, she parted her lusciously painted lips and, forming an "O", she took the mushroom shaped head into her hot, wet mouth as she began to suck hungrily on his dick. She was sucking on Bob's cock for all she was worth. She was kneeling in front of him with her ass in the air. The sight was too much for me and I quickly joined her on the floor, kneeling at her swaying bottom. Bob was moaning and groaning deeply as I lifted Roxanne’s skirt and flipped it onto her back. She wore a pair of sexy, lace thongs that revealed the smooth, creamy flesh of her buttocks. I pulled the single string that ran between her cheeks to one side and started to lick and kiss her gorgeous ass. The more I licked at her brown hole, the deeper she swallowed Bob’s big cock. I wanted to see what was happening and, looking over her back, I was just in time to see Bob’s penis disappear right down to the balls in Roxanne's throat. She gagged slightly as Bob began to cum, but then adjusted the angle of her head slightly and allowed his emission to pour into her sweet, hot mouth. Bob had his eyes tight shut as he climaxed, but I could clearly see the obscene outline of his huge organ as it spasmed inside of his wife's mouth. As Roxanne slid back to allow his still hard cock to drop from her lips, her lipstick glistened with his seed and I could see some of the residue drip onto her chin. We moved into the bedroom where we took off all our clothes and minutes later I was seated on the edge of the bed while Bob was stretched out on the bed with Roxanne sitting on his face. His wife was gasping and moaning with erotic delight as he licked and sucked on her swollen pussy. She let out a scream and shuddered as her climax overtook her. I lost myself in watching that most erotic scene and my cock was beginning to stir. Roxanne’s magical mouth had me hard again in no time, and when I was set to go she climbed onto the bed and wagged her inviting behind at me. “Go to it” Bob said excitedly. “How can you resist that beautiful ass?” I couldn’t, so after putting on a condom and greasing her tight ass hole with K-Y and finger fucking it for a minute or so. I placed my lubricated penis against her well-lubed anal opening. Then slowly I pressed harder with my cock. Little by little I worked my erect cock deeper into her as she clenched with some small amount of pain. When my cock was completely inside her ass I remained completely still. We lay there for several minutes as I kissed the back of her neck, letting her anal opening adjust to my cock. When she became comfortable, we started towards her anal climax. Slowly I started pumping my cock in and out of her tight opening, increasing the pace and stroke depth as she became more relaxed with my cock in her ass. After only a short time Roxanne started responding and reached a shattering anal orgasm. "God, this is great, I can feel you moving all through my insides,” she gasped. “Oh, Bob, look what he’s doing to me,” Roxanne cried out. “He’s fucking my tight little ass, baby. He’s really filling my asshole with his just right sized cock and it doesn’t hurt, it feels exquisite.” The words excited her husband to the point where he could barely speak. He just stood there as if nailed to the spot, with his face flushed and his eyes riveted to his wife’s upturned ass and my hard cock repeatedly spearing those creamy smooth cheeks. I was close to coming when Roxanne reached around and cupped my swaying balls. After several more of her orgasms my cock erupted its sperm filled load into her bowels. Roxanne screamed out with her strongest and final orgasm, and then Bob, jumping onto the bed next to his wife, clutched a handful of her hair and positioned her head so he could treat her to a semen facial. She was sucking the remaining cum from his cock as I staggered backward and fell into a chair, thoroughly and happily sated. And that, as it turned out, was enough for Roxanne and Bob as well. All we wanted to do now was curl up and get some sleep. “But tomorrow’s another day,” Bob said as he walked me to the door. “No, not tomorrow,” I said. “I need to rest.” Bob chuckled. “Next Saturday night then.” He paused briefly. “We have another fantasy you might want to help us with, but we can discuss that later.” I told Bob I would be up for what ever it was and that I’d definitely be there. Sometimes Size Does Matter It was the smallest penis I had ever seen. I fought back my laughter, hoping he didn't notice. If he did he let it go. I didn't know what to do; I was frozen in place shocked at something so small when the rest of him was so big. His entire body was muscular, bronze and extremely nice to look at. I was immediately attracted to him and could hardly wait to get him naked where I could run my hands down his chest, and devour his rippling flesh for hours. It was all I could do to wait for the third date before making my move. But now I sat there speechless looking at his tiny penis. Maybe it wasn't hard yet? But I didn't think that was possible because he had previously been kissing me and fondling my breasts under my shirt before pulling it off me and removing my bra. He had to be hard after sucking my nipples and licking every inch of my breasts. I guess this was all he had. I've heard of guys with tiny dicks but I never thought it was true. Girls that talked about a guy they know with a pinky sized cock; I thought they were kidding but I was wrong. I was face to face with one now and still not moving. I was so eager to get his shorts of and see what he had. I was looking forward to sucking a healthy cock, to feel the throbbing vein lined shaft and large bulbous head in my mouth. Wet with anticipation, wondering if I would be able to swallow most of him, but now seeing it, I could swallow him without a second thought. "Something wrong?" he asked since I still hadn't moved to touch him. "No, nothing," I quickly lied. In my head I was freaking out, "Wrong! Yes there is something wrong. You're dick is tiny. What the hell?" I knew I couldn't just sit there and stare so I moved my hand forward and cupped his small testicles, which matched his small penis. It was so strange his little boner sticking straight up only two inches if that and I swear smaller in diameter than my ring finger! I put my thumb and index finger on the small shaft. It felt like a little play thing instead of a man's cock. Stroking it up and down almost made me laugh again but it was covered up with his moan. I couldn't believe I was using a thumb and finger to stroke him off when I'm normally using two hands or at least all my fingers and thumb. He continued to moan and enjoy what I was doing. He acted just like a normal guy, and I wondered if he even knew how small he was compared to average men. I kept up the ruse, acting like nothing was wrong and never let on how small I thought he was. I went so far as to drop my head and take him into my mouth with ease. I completely let go with my hand, gripping his narrow shaft between my lips and sucking up and down the entire length like sucking my pinky off after eating ribs. It was pathetic but what else could I do? He really liked my sucking and swallowing his dick, actually putting his hands on my head and helping me move a whole two inches. Since it was so easy and never started to make my mouth sore I had him on the verge of climax very rapidly. Unfortunately he stopped me before he ejaculated. I guess he wanted to have sex. I was wondering if it was even possible with something so small, and especially wondering if I would actually feel anything. When he laid down on me after removing the rest of my clothes I knew I was going to have to fake everything. Not only an orgasm but any kind of pleasure for that matter. I was used to five to eight inch cocks, and wide ones. Cocks that filled me up and took my breath away when they entered the first time. Cocks that pounded deep and spread me wide. I could hardly feel anything. There was no depth of penetration, no feeling of fullness or my lips spreading open and clinging to the hot shaft. I got more pleasure with my fingers than his small cock was giving me. His thrusts were tiny and all I could feel was his body hitting mine and a slight annoyance, like an itch in my pussy. I wondered if he was getting any kind of friction from it, or was I just too wide and worn in for him to have pleasure. I guess he was because he moaned and exclaimed how good it felt while fondling my breasts, which was the only pleasure I was getting from it. I figured I'd put in a few moans, urge him on and act like I was cumming when he was. Girls can fake much easier than guys. We don't have to actually ejaculate or anything. Problem was, he decided he wanted to try all sorts of different positions, from doggy style to me on top and then modified missionary when my legs up over my head. Nothing felt any better, especially with me on top. I kept going to high and he'd fall out and I wouldn't be able to tell until he said something or tried to get it back in. I finally feigned being tired so he would change again even though I was far from tired. I usually love riding a large cock, bending it where I want it and driving down hard over and over. This one wasn't worth the time. It was hard to stay in the moment, my mind kept wandering away from sex, going as far as thinking about work tomorrow or what was on TV at home. I was bored, his penis was doing nothing for me and there is only so much breast play a girl can take before it becomes lame. Finally after doggy and me on top he bent me over on my back and stood over me, driving his tiny penis in as deep as it would go. I almost suggested he stick it in my ass so I could actually feel something but I held my tongue. He was working hard, and normally if a guy was thrusting as hard as he was with a normal dick it would have been heaven, making me cum at least two times by now but I wasn't even close. Sweat was dripping from his forehead and his incredible body was shiny with a sheen of perspiration. That was the only good thing about this, watching his muscular body work and looking at his handsome face in the pangs of pleasure. He was damn hot and that was why this was such a disappointment. I urged him on, going as far as telling him to fuck me harder and faster to get him to cum already. Seeing he was getting close I figured I'd get some pleasure out of it and began to play with my clitoris, hoping to have a small orgasm so this wasn't a complete waste of time. I guess seeing me playing with myself pushed him over the limit because he said he was going to cum seconds later. I felt his load ooze into my pussy, dripping deeper than his penis ever did. He cursed and shook, holding his small penis inside me while it convulsed. I pretended I was cumming, screaming and shaking with him until he backed away. He had a little semen dripping down his narrow shaft. The odd difference between the rest of him and that small penis was something I knew I could never get used to. That and the lack of stimulation for me was the deal breaker. He offered for me to stay the night but I told him I had to go 'cause of work in the morning and quickly dressed, driving back to my apartment. The first thing I did was replaced the weaker batteries in my Rabbit and got naked. I needed something real, something deep and wide. I fucked myself for two hours since I was so frustrated with what he gave me, cumming several times before falling asleep with my toy next to me. At least I had it. ***** He called me three days later but I told him it wasn't going to work out between us and never saw him again. Sometimes size does matter. Sometimes Size Does Matter Ch. 02 I would like to thank all of the people who e-mailed and encouraged me to continue writing. I also would like to dedicate this to my friend Chad who is as much an ass man as I am. This is a continuation of my original story, in which the male in the leading role does not possess a 7 to 11 inch long penis as big around as a beer can. You may need to read my original submission to pick up the thread of the story which is about the husband (Bob) who has an extremely large penis and his wife (Roxanne) who loves anal sex but can't take Bob's big cock in her ass. Enter the friend (me) with the slightly smaller than average cock, just right for Roxanne's ass. * * * * * When I left Bob and his wife last week they invited me to come back again this Saturday night for a continuation of some fantasies they wanted me to help them out with. When I arrived and knocked on their door, Roxanne met me and gave me a big hug and kiss. She looked just as sexy as the first time I met her. Only this time she was wearing a short spaghetti strap dress that showed off her tan legs and perfect body. She took my hand and led me into the living room where her husband Bob was mixing drinks. Bob greeted me with a drink in hand and told me to sit down. We enjoyed a relaxing time drinking and talking. After awhile Roxanne suggested we play a game of strip poker --normal rules: the loser of each hand of poker has to remove an article of clothing. Soon we were all pretty much into the game. Roxanne was down to her bra and panties, Bob in his pants only, and I was in my boxers (I'm a terrible poker player). After Roxanne lost the next two hands in a row, she was out of her clothes, much to Bob's and my delight. When she lost the next hand, Bob told her that since she was the loser she had to submit to whatever the guest asked. I told her that I wanted to eat her pussy. She looked at her husband and all he said was, "Let the Guest do what he wants!" His wife got up and walked over to the table on my side. She sat on the table in front of me and spread her legs wide. I could see her pussy already dripping from her excitement as I leaned in to bury my face into it. His wife turned and watched her husband's expression as I noisily lapped at her wet pussy. He could see that she was enjoying my attention to her pussy as he began stroking his hard cock. His wife hitched her legs up around my shoulders, her back arching as she approached climax. She cried out as she climaxed, grabbing my head and holding it hard into her pussy. She looked at both of us and then smiled as she said it was time to make some fantasies come true. She told her husband to lie down on the rug, which he immediately did. She straddled him and, as he began playing with her tits, slowly lowered herself onto his huge cock. She began pumping Bob at a furious pace as he lay back squeezing and fondling her bouncing breasts. Then she leaned forward on all fours, and with Bob's cock still deep in her pussy, she reached around with both hands and spread her ass cheeks as far as she could and told me to told me to fuck her in the ass. She said, "I want to feel your just right cock fucking my backdoor hole." I moved in between them, positioning myself to enter Roxanne from behind. Her ass and pussy were soaking wet; I could see her moisture dripping down Bob's cock. I lubricated my cock with some Astro Glide that I had spotted on the table while we were having drinks. As I pressed my dick against her ass, she began pushing back against me slowly easing my lubricated cock into her ass. Man was she tight. It was the first time we had ever done a double penetration and she was moaning at both the discomfort and the pleasure it was causing her. After a moment I was all the way in and could feel Bob's cock moving inside her as he began thrusting. Slowly at first then with increasing tempo I began thrusting with a tempo matching his thrusting while Roxanne screamed out in pleasure. She was bucking against us, tits slapping against Bob's chest as we double fucked her. I felt my balls slapping against Bob's as we both fucked wildly. At one point I imagined the neighbors calling the cops because of Roxanne's cries but soon forgot about it as I approached orgasm. By the spasms of Roxanne's body I could tell she was already there. I felt Bob pull his wife onto his cock and hold her as he released deep inside of her beautiful cunt. I let go, filling her ass with my cum. I pulled out gushing cum all over her ass and onto Bob. As soon as I pulled out she collapsed on to her husband, kissing him deeply as I went towards the bathroom to clean off. When I came back she was between her husband's legs sucking on his slowing reviving cock. I sat down on a chair where I had a good view of her beautiful mouth sucking his huge cock. Roxanne removed her husbands cock from her mouth and turned her head just enough so that she could see me. She then started running her tongue across the tip, tasting his cum soaked cock and then took him deep into her mouth and began sucking on him intently. "Oh, baby," Bob moaned, "You really know how to suck my cock to make it hard again." Roxanne than began pounding his throbbing cock deep into her throat with her fist. The sight of Roxanne eagerly slurping up her husband's creamy load brought my cock back to life. Just then their doorbell rang. Roxanne jumped up and skipped to the door like an excited little girl squealing "They're here"! I turned to Bob with a "What in the hell is going on" look. As Roxanne returned with a guy and girl following her, Bob introduced them as Ray and Ann. They explained that they were their close friends with the same problem they have. That is, Ray has a large cock (9 1/2 inches) and Ann loves anal sex. They apparently told Ray and Ann about my smaller than average cock (5 inches) that Roxanne loves in her ass. Therefore, they wanted to join the party and have me fuck Ann in the ass so she could satisfy her need for anal sex without extreme pain. Ray moved over to the lounge chair and began undressing. Ann moved over to her husband and slowly pulled down his underwear. His cock sprang out and began to rise to meet Ann's mouth. She grabbed the base of Ray's cock and slowly started to stroke it. Her small hand couldn't reach around Ray's huge cock. She slowly jacked his cock and rubbed her thumb across the mushroom shaped head. A small drop of pre-cum appeared and Ann's small tongue flicked the head of Ray's cock and took it in. It was obvious that Ann was a natural-born cocksucker. She opened her mouth and began to take Ray's cock down her throat. She worked her lips and tongue around his cock and it slowly sank out of sight into her mouth. Ray let out a moan and said "Yeah, baby suck my cock good!" Ann began to work the cock in and out of her mouth-teasing the head with her tongue. Ray grabbed the side of Ann's head and slowly started to fuck her mouth. He pulled his cock out until only the head was touching Ann's lips and then slowly pushed it back down her throat. Ann's saliva mixed with pre-cum covered Ray's cock and was dripping from the corners of Ann's mouth. Roxanne crawled over beside me and leaned against my chest. She reached down and took my cock in her hand and slowly started to jack me. She watched Ray fuck Ann's mouth and started encouraging Ray with comments. "Fuck her mouth Ray-fuck her good! Give her a big load of cum." "That's it baby, suck that big cock. Make it cum, baby!" As Roxanne continued to jack my cock, I slowly started to get a hard-on. Roxanne whispered in my ear, "Ann has always wanted to be fucked by two guys. Now we can make her fantasy come true!" Roxanne turned to Ray and said, "Ray, why don't both of you fuck Ann." Ray slowly pulled his cock from Ann's mouth and said, "That's what we're here for!" Roxanne grabbed one of the cushions from a lounge chair and laid it down on the floor. Ray lay down with his ass on the cushion and Ann straddled her husband's hips. She grabbed the base of his cock and slowly guided it into her wet cunt. She worked his cock into her cunt slowly and then started to ride up and down on it. Ann's eyes rolled back and she really began to get into a good fucking motion. As she moved up and down on the hard cock, she began letting out moans of pleasure and ecstasy. Roxanne jumped up and said, "Wait just one second." She grabbed the bottle of Astro Glide lubricant that I used on her ass. She then moved over by Ann and Ray and told Ann to lean forward. Ann leaned forward exposing her ass to Roxanne. As Ann continued fucking Ray, Roxanne slowly dropped lubricant on Ann's puckered asshole. She then poured a small amount on her fingers and began to work one finger and then two fingers into Ann's ass. Ann continued to let out moans as Ray's cock worked in and out of her cunt and Roxanne's fingers moved in and out of her ass. I grabbed my cock and started jacking it. What a sight to behold. I couldn't wait to get my cock into that tight ass. Roxanne motioned for me to come closer. As I moved over behind Ann, Roxanne leaned forward and took my cock into her mouth. She gave me a couple of good sucks and then poured some lubricant on my hard cock. She guided my cock to Ann's ass. Ray stopped fucking Ann long enough for me to begin working my cock into her ass. I slowly pushed my cock against Ann's asshole and told her to push back. Roxanne whispered in my ear "This is only her second time to be fucked in the ass-so be gentle with her." That got me even more excited. It was a tight fit-the tightest I had ever felt. I slowly worked my cock into Ann's ass. I could feel Ray's cock on the other side of the membrane separating Ann's two fuck holes. Roxanne talked to Ann and offered her encouragement. "That's it baby-almost there. You are so hot with two cocks in you. Baby, if you could only see the look of ecstasy on your face." I finally worked my cock all the way into Ann's ass. I stopped for a few seconds and let her ass adjust to my cock and then I slowly began a fucking motion. I wanted to get her used to my cock before we both started fucking her in earnest. Ray obliged by just lying still for a while as I fucked her ass. After a few strokes, Ann let out a low moan and said "Oh yeah, fuck me, both of you, fuck me!" That was all the encouragement we needed. Ray and I set up a fucking motion like a machine. Both of us began to plunge our cocks in and out of Ann's cunt and ass. Roxanne began to shout. "Fuck her, fuck her hard. Pound her ass! Fuck that ass and cunt. Make her cum, make her cum!" Ann offered up encouragement of her own. "Fuck me! Fuck me harder! Both of you cum in me. Oh, yeah-cum in my ass and cunt. Fuck meeeee!" This was too much for Roxanne; she had to get in on the action. She got on her hands and knees and started lapping my balls from behind as I fucked Ann in the ass. At this point Bob was fully erect again and moved behind his wife and started fucking her doggie style. None of us guys could last long with two wild women fucking and lapping like that. I rammed my cock deeper into Ann's ass and Ray did the same thing to her cunt. Ann collapsed on Ray's chest as we both shot our loads deep into her ass and cunt. I could feel Ray's cock pulsing in Ann's cunt. I'm sure he could feel mine doing the same. At almost the same time, Bob blew his load into his wife's pussy and Roxanne shuddered in climax. "That was great," shrieked Ann, "I've never cum so hard in all my life." "That was great for me too," Ray said as he gave his wife a hug and a kiss. After Ray and I had finished cumming we both drew our cocks out. Ann rolled onto her back exhausted. Cum started seeping out of Ann's cunt and ass. Roxanne crawled over between her friend's legs and began to suck the cum from her cunt. I thought to myself-"Sometimes a smaller dick does matter." Sometimes Size Does Matter Ch. 02 It was huge, way bigger than I expected. All I could do was stare at it, too shocked to move or say anything. "What's wrong?" he asked. "Umm, well, I wasn't expecting you to be that big. It makes me nervous," I finally said. "It's not that big," he said, moving closer to me. I looked back down at his erect penis. Who was he kidding; the thing looked like a horse cock, way to big to go inside of me. I moved away from him, which caused him to stop with a worried look on his face. "Yes it is! You're not putting that thing in me." "Are you serious? I thought women liked them big." "Not that big. You'll hurt me for sure. I should go." "Go... You're not going anywhere. We had a deal." "Deals off, no one told me anything about that monster," I said, standing up to leave. "That's the price you pay and the luck of the pick, girl. Big small, you never know what you're going to get in your line of work. I already paid, you're going to deliver," he said blocking the door. "You'll be refunded, now let me out." He didn't move. His enormous cock remained hard and throbbing between his legs, angled directly at me and slightly moving up and down with each heartbeat. "How about a handjob or blow?" I asked, getting a little scared. "No go, I paid for anal and I want anal. Hell, a slut like you should be able to handle it." "Oh, real nice, asshole, nice way to relax a girl. Look, I'll suck you good, for a long time. You'll love it, trust me." "You can suck all you want but I'm still getting what I paid for. If you want to throw a blowjob in for free, be my guest but you're not leaving until I fuck your ass." Again I looked at his raging cock, wondering if I could really take him, because it was looking like I didn't have a choice. I'm not a big girl only five four and now 105lbs since I got my new boobs so you can picture how tiny I really am. If he managed to get that thing in my ass all the way I'd be choking on it practically. Pre-cum was beginning to bead-up on the slit and the veins on the sides were standing off the shaft. I swallowed, trying to think of what to do. Maybe if I could get him to cum by sucking him he'd let me go after the climax. It was worth a shot. "Okay, you win," I said falling to my knees on the hotel carpet and reaching up to grab hold of his cock. Good hell it was amazing, I've never felt anything like it before or since. His balls were heavy his shaft so wide my hand had two or three inches of space between my thumb and fingers when I tried to touch them together. He was hard, more ridged then I expected for something so large. I began to stroke him and fondle his nuts, moving he skin up and down his shaft in long motions due to the sheer size of the thing. When I tried to put his head in my mouth I had to open as wide as I could and even then it stretched my lips further. He grabbed my head and thrust forward, forcing more of his cock in my mouth. I suddenly couldn't breathe he was blocking my mouth completely and I panicked, pulling away from him and gasping for air. He laughed and mocked me, saying I wasn't much of a whore if I can't suck better than that. I shut him up by grabbing him again and stoking hard and fast. I got up the courage to put him in my mouth again, remembering to breathe through my nose this time. He thrust forward, just like before but this time I opened wide and let him pound his cock against the back of my throat. It was so big it didn't go very far and I managed. Keeping up the stroking as much as I could, I notice his heavy balls were beginning to rise. My goal was his orgasm and I worked very hard to accomplish the task. Problem was, just as I was getting close he pulled away from me, like I thought he might. "Oh no, slut, you're not getting me off that easy. I'm fucking your ass for sure tonight. Now, get on the bed. It's time you earn your money." I thought about going for the door, or my phone in my purse. I didn't think he would allow either and decided against both. I stood up and he grabbed my breasts pulling my bra away from them before pinching my nipples and turning me around roughly. He pushed me forward onto the bed and finished taking off my bra. My panties came next. My heart was pounding in my chest. I hadn't been this nervous about sex since my first time. He spread my ass with his hands and suddenly I felt his warm wet tongue slather my tight hole with saliva. With his finger he began to explore, penetrating my pussy and ass with two different fingers. It felt good, but I still couldn't get the thought of how big he was out of my head. Looked like I really was going to earn my money. He continued to lick and finger my holes, adding another to my ass and really working me in. I didn't think the prep was going to really matter much. Nothing he did was going to prepare me for the width and length of his cock. I guess it was nice of him to try and it felt really good, made me cum a little. He must have enjoyed it as well because he did it for quite a while, probably as long as I sucked him. But all good things come to an end. "That should do it. I think you're ready," he said pulling his fingers out. I looked back on my hands and knees, watching him stand on the bed and move toward me. His cock was really hard now. The head was purple and pre-cum was running down the underside of his shaft. "Is this your first time doing anal?" I asked him, trying to delay the inevitable. "What do you think?" "I'm thinking yes because no woman in her right mind would want that in her ass. That's why you had to hire one." "Got that right. So let's do this." I turned my head, not wanting to watch. My heart was pounding again and then I felt him move his giant head into position. It felt like someone's fist against my ass. There was no fucking way it was going to go in, but he started trying anyway. At first I felt pressure; just a large force pushing on me and then my muscles began to be opened. The strain began as he leaned harder and part of his tapered head began to enter. "Oh... fuck... shit... too much... fuck!" I screamed as he put more pressure into it. Suddenly he pulled back, removing his cock. Not much had been in me, not even the head had passed my outer ring. He was just too big. "I think we need more lube. Hold on." He jumped off the bed and started rummaging through a duffle bag he brought with him. My ass throbbed a little and I thought about running again while he was distracted. He was back too quick with a bottle of anal lube. He stood over me again and squirted a very large amount onto my throbbing asshole. Working it in with two fingers, felt pretty good and I was very wet and lubricated. He dropped the bottle on the bed and moved his cock into position again. The lube helped, but not much. He got further inside of me but the strain was incredible, turning my lubed as on fire. "Almost in... almost there," he said, commentating while I panted for air and bit my lip. Suddenly my muscles gave way and he popped in, past my tight sphincter with an audible noise. A flash of pain grabbed me, making my ass throb and spasm. Fuck, I had never felt anything so big before and he only had the tip in. I was breathing so hard I couldn't even swear anymore, just moan and pant. "The heads in, I knew you could handle it." At least he stopped for a minute before trying to move further, giving me a small respite. I started rubbing my clit as fast as I could, hoping the pleasure would take some of the pain away. It helped, right up until he started to move forward again. The burn returned as his ridged shaft slid across my sore opening. He was so hard and so big I could feel every vein and texture on his cock. He was way too big to be fucking my tiny ass. As he eased in the feeling of being really full increased as did the burn. I was going ballistic on my clit and it was the only thing keeping me from screaming and moving away from him. I didn't know how much he had gotten in but it felt like my insides were going to burst and his cock was going to come out of my throat. I never stopped playing with my clit, and I know it's the only thing that got me through. I never felt his balls on my ass so I don't think he ever got all of himself inside. The forward movement finally stopped and he began to withdraw, bringing a totally new sensation. It felt like my insides were moving back into place and falling out of my ass. It was better than being stuffed full but not by much. Then, of course, he slid back in, filling me to the bursting point again before taking it out. Thankfully this was his first time and the excitement of the moment made him cum quickly. If he would have been used to anal I probably would have been killed by his enormous cock from internal rupture or something. Luckily he only thrust in and out about five times before removing it completely and cumming all over my back. His large load fit his huge cock and by the time he finished I was covered and so was the hotel bed. I fell on my face and lay there with my ass throbbing and burning from the stress. "That was worth the money. What the guys said about anal was right on. I'm going to take off, I'm sure you'll let yourself out." Usually it's me that leaves the client but I couldn't move let alone walk. I lay there for about an hour before crawling to the bathroom and running a hot bath. My ass was on fire and was sore for a week afterwards. Sometimes size does matter.