3 comments/ 180225 views/ 13 favorites Anal Virgin By: DaddysGrl Molly and I sat there waiting for Dennis. He was a friend of hers. Well, more like an acquaintance. He was roommates with her boyfriend, John and her boyfriend had asked her if she knew any young girls…Dennis like young girls. Even though I was in a relationship at the time, she instantly thought of me because she knows I love older men and would never pass up an opportunity to get something different. Now, I was a little nervous and being in a bar, I naturally did one of the things I do when I am nervous…I drank. I had about 4 beers and 2 White Russians. By the time Dennis showed up, I was very relaxed an in the flirtiest of moods. He walked through the door and Molly nudge me and nodded in his direction. He was very nice looking for an older guy. He had a shaved head and a goatee which is a look that I find very attractive on a man. I think I just like the sinister look of it. He was muscular and dressed casually in jeans and a t-shirt. He walked over to Molly and she introduced us. I motioned him over to sit next to me and we started talking. I learned that he was forty-three yrs old, divorced, and worked in construction. The more we talked, the more relaxed I felt. I began touching his knee and leaning into him giving him a look at my cleavage. I never considered myself the “model type” but I thought I looked pretty good at twenty-one with my long dark brown hair and brown eyes. I am about 5’4 and back then was around 120lbs. I even remember what I had on, my favorite black mini skirt and red sweater. He had a few rum and cokes and by midnight, we were both ready to leave the bar and go somewhere more private. He suggested his house. Molly stayed behind. When we got into his car and started driving, he pulled me closer to him. I kissed his neck and started rubbing his crotch. From what I could tell, he was already getting hard and it felt like I was in for a big treat. At the stop light, he reached down and unzipped his pants and ordered me to suck his cock. That was another thing I liked about Dennis. He was very aggressive and loved dominating me. I leaned down and took his cock out, it was about 7” half hard and I was a bit nervous thinking about how big it would be once he was fully erect. I had never taken a cock bigger than 6 or 7 inches before. I slid it into my mouth slowly, sucking it in and out. He put his hand on the back of my head forcing me to take all of his cock in my mouth. It gagged me a little but my throat quickly opened up allowing the full length to go in. With a few more thrusts, he unloaded into my mouth. I felt his thick cum in my mouth and he wouldn’t let go of my head so I was forced to swallow every drop. His was the first cum I ever swallowed. When we arrived at his house, he showed me inside. He asked if I wanted a beer and I said yes and asked if I could use the phone. He said that was fine. I called my boyfriend at the time and told him I wouldn’t be home. That I was staying the night at Molly’s. I was lucky that he was an understanding and trusting boyfriend. He said that was fine and he would see me tomorrow. I felt guilty for what I was about to do but I have gone too far to turn back now. And at this point I wanted Dennis so bad, my pussy was dripping wet. After some more small talk, he leaned in and started kissing me. I felt his hands go up under my sweater and my bra and cup my breasts. He began massaging and caressing my nipples between his fingers. He laid me back on the couch and pulled my skirt up and slid my panties off. He put them behind him on the couch and then started fingering my pussy. I closed my eyes and threw my hands over my head and just relaxed. Feeling his fingers go in and out while his thumb massaged my clit. He commented on how wet I was and what a nice smooth baby girl pussy I had. He then began licking my clit and sucking it between his lips. I was in heaven. He pushed my legs up and apart exposing my clit even more. As he continued licking me, he slid a finger up my ass. I was surprised as I have never had this done before. It felt so good and he comment on how tight I was. Dennis suggested that we go upstairs because he thought his roommate might come home and he wanted a little more privacy. He took me by the hand and picked up my panties. I pulled my skirt down and followed behind him as he led me upstairs. We walked down the hall to his bedroom. His room was light blue. There was a black light over the bed and an American flag on the wall. On his closet door was a mirror. His bed was lengthwise along the closet door, if you were lying in bed, you could see yourself in the mirror. He went to his stereo and put on The Doors. He then shut the bedroom door and lay down on the bed and unzipped his pants and looked at me. I walked over and sat on the side of his bed and started stroking his cock with my hand. He ordered me to undress him. I walked down to the edge of the bed and took his shoes and socks off and then grabbed the legs of his jeans and pulled them off as well along with his underwear. He then sat up so I could take his shirt off. His cock was rock hard and huge. He told me to get my clothes off. This was an easy task because by this time, I was only wearing my skirt and sweater. Dennis pulled me on top of him and my pussy was so wet already that his cock easily slid in. I began riding his cock. Fucking him hard, being filled with his cock. He reached up and rubbed my breasts using them for leverage as he bounced me up and down on him. He demanded that I cum now or wouldn’t be allowed to cum later. I looked down at him and began rocking back and forth, up and down like I was riding a horse. My pussy walls began to contract and release and then my hot juices were all over him. We changed positions and he made it so we were facing the mirror. I was on all fours on the bed and he was standing behind me. That’s when I felt it, the tip of his cock poised at the entrance of my asshole. I backed away instinctively and laid flat on the bed. I told him that I didn’t want to do that, I have never had anal sex before. He leaned down almost laying on top of me. I could feel his breath against my neck and he whispered in my ear to get my ass up in the air. Then he grabbed me by my hair and pulled me up. He took the palm of his hand and began spanking my ass. Each cheek 10 times. The Doors, Love me two times was playing on the stereo. I begged him to stop. I have never had a man treat me like this before. I was scared and ashamed but at the same time very much turned on. I think that is were my shame came from. He was dominating me and treating me like a whore and I loved it. After he made my ass red, he poised the head of his cock at my entrance again. This time, I didn’t move. I was on my elbows and buried my head into the mattress. I felt him pushing his way into me, slowly. The head of his cock was in my ass. He ran his hand up my back and put his other hand on my hip. With one thrust, he was entirely in me. I was full of his cock, his balls resting against my pussy. I didn’t move nor did he for several moments. I remember feeling sick to my stomach and somewhat shocked that I had a cock up my ass. He was somewhat encouraging, saying things like relax baby girl and it would be over soon and start feeling good. I just laid there whimpering. He began pumping his cock in and out of my ass slowly. It hurt like hell. I never felt anything like this in my entire young life. I remember thinking that I wish it would be over soon. I started thinking about anything else other than what was happening to me and the pain I felt. Then, it happened. I realized that the pain that I once was feeling was slipping away and now I was feeling wave after wave of pleasure. His cock was sliding in and out easier now and I raised up onto my hands and looked in the mirror for the first time and saw Dennis behind me looking at me as well, with his hands on my hips driving his cock inside of me. I started meeting each one of his thrusts trying to drive him deeper into me. It was ecstasy now. I put my fingers in my mouth and licked them then began rubbing my clit. I heard him say that’s it baby girl. I knew you would be into this. He closed his eyes and released his load deep into my bowels. I spanked my pussy and began to cum as well, it was a hard cum and I ended up shooting all over my hand. I had no idea I could cum like that. It was amazing. He collapsed on the bed beside me. And I lay on my stomach. My ass was still stretched wide open from the recent activities. I looked at him and he kissed me on my forehead and rubbed my back. And so it began… Anal Virgin This is a romantic story of how I helped an ex-lover fulfill her desire to have anal sex. I am a businessman who in the 12 years since graduating from college has started and built and very successful business. Part of my success comes from my willingness to travel over 50% of the time. This schedule allows me to stay in touch with friends and old acquaintances. This story is about one of those trips and how I helped an old college lover lose her virginity a second time. The trip was taking me to Memphis a city that I had never visited. As I normally do I check to see if there is anyone in the city with whom I might want to get in touch. It turned out my college lover Jill lived there. When I discovered this it brought back a flood of memories and a question about why I hadn't stuck with her. She was smart, sexy and willing to try just about anything in bed. My drive for business success was the down fall to the relationship. Well I thought, she's a perfect candidate for at least a dinner. I called Jill and after the shock wore off she agreed to dinner. As is usual I travel first class and only dine in the finest restaurants, so when I told where to meet she was impressed. I arrived prior to the appointed time and was seated at a table. I wondered if Jill might look much different 12 years after we last saw each other. My seat had me facing the entrance so I was watching each patron as they arrived. Than Jill entered. Wow, she wore a black slip dress that ended a couple of inches above her knees and spike high heels, Watching her walk to the table with that air of confidence that older women have, made her look better than I remember. I stood and gave her a kiss taking in the smell of her exotic perfume. Time had only improved Jill. Her 5'5" frame was in great shape evidenced by the slinky fit of the dress. She didn't seem to have a bra on yet her 34C breasts stood firm. I exclaimed to Jill how she looked better than I remembered her. She thanked me and kindly expressed the same sentiment of me. We got into our dinner and the catch-up on our lives. She had two children from a marriage which ended in divorce and was now working as an office manager. The dinner went on with good food and wine putting us both at ease. Eventually our discussion turned to our "good old" college days and the good times we had. We started to reminisce about our sexual adventures. At one point Jill said the only thing we hadn't done in college was have anal sex. "Why was that?" I asked "I didn't think it was right then." Jill replied "So have you had anal sex yet?" "Nope, still haven't done it" "Still don't want to do it?" "Oh I want to do it, but my ex-husband didn't think it was right and I haven't had the opportunity since we split." "You don't know what you're missing." I exclaimed. "You've done it than?" Jill asked. "Multiple times and twice helped friends give up their virginity." "How did you do that?" "Have anal sex?" I jokingly asked. "No help them give up their virginity." "Oh, I went out of my way to make it special and to insure that she was very relaxed." "Describe what you did." "No I never do that, I only demonstrate." Smiling and looking into her eyes. Jill paused for a moment and than said 'Would you demonstrate for me?" "On you?" "Yes, I want to experience anal sex and you were a great lover." "I am only in town tonight." "I'm free tonight," Jill smiled. "Well that settles it. Would you like to come to my room?" "When do we leave?" said Jill as she ran her hand up my thigh. Raising my hand, I waved toward the waiter, "Check please". We stood and I placed my hand around Jill's waist pulling her close to me, taking in her intoxicating aroma. In the cab to my hotel I told Jill she must follow my instructions otherwise it wouldn't work. Jill smiled, "OK," and she gave me a deep kiss. Opening the door to my hotel room I told Jill to stand in front of the floor to ceiling mirror which covered one wall. "Step out of your shoes." She did as instructed. Than I came up behind her and wrapped my hands around her waist, leaned my head down to her neck softly beginning to kiss her. "Its nice to have you back in my arms," I whispered. I slid my hands up over her breasts and Jill moaned. Than continued moving my hands to the shoulders and pushed the spaghetti straps over her shoulders. Slowly moving my hands down I pushed the dress off her breast revealing her large brown nipples. We were both watching this in the mirror. Fondling a tit I reached behind her and unzipped the dress, watching it go loose. She smiled into the mirror as I pushed the dress down until it fell to the floor in a pool of fabric. Looking at Jill in the mirror it was just as if we were still in college. "Mmmmm," I moaned. Kissing her neck. Jill pressed back against me in pleasure and smiled into the mirror. Looking over her shoulder I started to slide my hands down to her thong panties. Reaching the waist band I pushed them off the hips down her legs until gravity took over dropping them to the floor. Now that's a change I thought looking at her shaved pussy. Stroking her slit I murmured "no hair, that' new." "For my bikini and it feels good," as she moved her hand down and pressed mine deeper into her slit. We both watched intently as I slid a finger into her cunt. Jill moaned. Kissing her neck as I slid my finger out, I said "come with me". Taking her hand I led her to the bathroom and said "stay warm," while placing a soft hotel bathrobe around her. Turning and kissing her, I said, "I want you to relax". Than I went to the bathtub and turned the water on. 'Relax, I'll be right back," as I left the bathroom. I returned to bathroom naked, after undressing. Jill smiled "now you look much more comfortable" as she reached out and stroked my erect cock. "Get into the bath tub Jill before I lose control!" "Okay," as she stepped into the tub. "Mmmmm comfy warm," she said. "Relax" as I took a natural sponge and began to stroke her shoulders. "Mmmmm," moaned Jill as she leaned back closing her eyes. I worked my way down her body with the sponge paying particular attention to her breast and clit. This elicited further moaning and purring from Jill. My finger also stroked lower between her legs until I felt her anus. I circled her anus and brought another moan out of Jill. Than I pushed the tip of my finger into Jill. She moved her hips around clearly savoring the feeling. Leaning over and kissing Jill, I pushed my finger deeper. "Soon you will have the real thing," I whispered, "but now its time to dry off". Jill let out a sigh as I slid my finger out of her ass. Lifting her out of the tub I once again wrapped her in the robe. Than guided her out to the bedroom. Standing behind her I slid the robe off and instructed her to lie on the bed. Jill was on her back with her legs slightly spread. I was ready to jump on her right than, but instead I pulled a sheet up over her breast. "Just relax Jill. Close your eyes." When she did I climbed onto the bed and started to kiss her head with short soft kisses. I was going to kiss every square inch of her body in my efforts to relax Jill. I gently sucked on her ear lobes, down over her eyes and softly probed her mouth with my tongue. Moving down her chin I covered her neck in kisses. Going from there, I covered each arm in kisses and finished by sensually sucking on each finger. Returning to her neck the direction took me towards her breasts. I climbed the slope of one breast until I reached the peak and took her nipple into my mouth. A strong moan accompanied an upward thrust of her body. Clearly Jill was enjoying this. Covering her stomach with kisses Jill began to squirm in anticipation, but I bypassed her pubic area and worked myself down the outside of one leg and up the inside. Jill spread her legs as I approached the junction between her legs. As I got close enough to smell her juices I jumped to the outside of the other leg working my way down to her toes. I spent time sucking each toe individually. Jill was moving around. I worked my way up the inside of her leg and this time went right to Jill's pussy slit and kissed the length of it to her clit. It was like an electric shock hit Jill by the way she arched her pelvis. I backed away as Jill moaned in frustration. "Turn over," I quietly whispered in her ear. She rolled languidly over and once again spread her legs apart. Moving to her head I began to kiss down her neck and over her shoulders. I covered each arm with moist kisses and gently sucked each finger into my mouth. There was an occasional moan from Jill. I worked my way down her back and focused on the small of her back going as low as the beginning of her crack. I skipped over her ass and went up and down each leg. As I got to the top of her legs I could see her cunt dripping juices. Kissing up one cheek of her ass I reached the top of her crack. Gently spreading her cheeks apart I softly kissed my way down to her anus. Sticking my tongue out I circled her anus. Jill let out a huge moan and I thought she was going to cum than. Kneeling between her legs and positioning myself I slid my cock under Jill until it touched her clit, eliciting another loud moan and thrust of her hips. Then slowly kneeling up my cock dragged over her slit up over her anus. Jill was moaning continuously now. I slid my cock up and down several times until there was a sheen of moisture over Jill's anus. Leaning over I whispered in her ear, "kneel up". She did so quickly. I kissed her back several times and than knelt up. Then taking my cock in hand I gently pressed it against Jill's ass hole. As might be expected of a virgin she instinctively tightened up. Leaning over her back again I gently caressed her breasts while kissing her and telling her to relax. I felt her anus relax and began to press inwards. Jill moaned as she felt her ass being spread open. Slowly the head of my cock went passed her spincter and I paused. I asked Jill, "are you all right?" She responded in a moan, "I'm wonderful!" Pressing deeper I began to feel Jill pushing back. Finally, I was all the way in Jill's ass with my ball's resting on her clit. Pausing I let my cock throb for a moment in Jill's ass. Than I drew about half way out and pushed back in. Jill moaned. I started to pump in and out. I pulled all the way out and briefly admired the gapping anus before shoving myself all the way in. Jill screamed in pleasure. I grabbed her hips and started to pound her ass while leaning over and instructing her to stroke her clit. She did and this caused her to begin pushing back on my cock. I was beginning to moan and my cock was throbbing in Jill's ass. Tightening my grip on her hips I screamed as my cock exploded in a hot stream deep into her ass. The moment Jill felt this hot pressure she came in a massive orgasm. Pushing her ass hard against my cock she sucked rivers of cum out of me. It went on for what seemed like forever until we collapsed on each other. My cock slowly softened and finally slid out of her causing Jill to moan again. Reaching down I stroked her ass covering my finger in my cum. "Here," I said "a taste of your lost virginity." Jill opened her mouth, sucking my fingers in and licked them clean. "Mmmmmmmm," was her response. "Well, was it worth the wait?" I asked. Smiling Jill said "Absolutely... shall we do it again?" Anal Virgin Have you ever walked past an open door and not turned your head and looked in? Of course not. And that's exactly what happened last night. I was going to my room to go to bed when I walked past your room. We haven't started sleeping together, although we have discussed it. A couple of months ago we decided that we would give each other space to do our own thing until we were sure. And seeing you lying there – I knew that the time had come. The light from the hallway illuminated your bed. You were lying there sound asleep. Curled in a semi-fetal position facing away from me with the beautiful globes of your butt - oh so tempting. I hurried to my room; undressed and returned to slide in behind you. Easing into a spooning position, I positioned my rapidly hardening cock between the globes of your butt and pulled you closer. God! You felt so hot. I began to move my cock between your ass cheeks, slowly (so as not to wake you) and my cock began getting harder and harder. You moaned and started to spread out on your stomach, my cock slipping from the grasp of your butt. Moving with you, I took the "ties" that were attached to the head of the bed and began to slip them on your hands. Within minutes, I had your hands and feet tied in a spread-eagled position and, placing several pillows beneath your pussy, had your butt up in the air – just waiting for me. You had been sexually active at college but no one had taken your anal cherry. Your virgin ass was just waiting to be fucked. I found the pear scented love lotion we used occasionally and began applying it to your ass, gently rubbing around the puckered ring. Easing a fingertip in until you began to moan and wiggle your butt. Applying more lotion, I eased my finger in and out until I finally had it in to the last knuckle. Moving it around. Stretching your butt until I could finger-fuck you with ease. Still you haven't awakened although now, you were more vocal and your butt was responding to my ministrations. I applied more lotion and began working a second finger in with the first. Soon – I was able to bury it to the hilt along with its brother. Your ass is so hot and tight! Do I dare try a third finger? I think so. I must be able to stretch your ass more so that it will accommodate my huge cock. I worked the two fingers in and out while putting more lotion on your ass and starting to insert the third finger along with the other two. Your moaning increased. Are you awake? I can't tell. But you are moving your butt back against my fingers as though it's something you really need. The third finger is finally in. Working them back and forth, twisting them as I go, your ass begins to loosen until I think that my cock will finally fit. Positioning my cock near your sphincter, I begin to ease the huge mushroom shaped crown in. Soon it slides in past the ring and, with no effort at all, goes in to the hilt. All 8 inches of it buried deep within your ass. My God daughter, you are so hot! I begin slowly thrusting in and out of your ass, not knowing how long I can hold out without cumming. Each thrust brings another moan from you. As I increase my pace, you begin telling me to "Fuck me Harder – Fuck me Harder – Harder – Harder –" Now I know you are awake. I lean forward and place a kiss on the nap of your neck, sucking gently until you begin to whimper and thrash about. I bite gently and then harder. Your ass tightens on my cock and I think I'm about ready to cum. That's when you start quivering and thrashing your butt back and forth, milking my cock. I begin to cum. Spurt after spurt of red hot cum deep within your bowels. Then you clamp your ass down as hard as can be and I stop cumming. I withdraw my cock from your butt and go the bathroom where I clean my cock. Then I get a washcloth. From the kitchen, I get a small kettle and fill it with warm water. Returning to the bedroom, I begin to slowly clean you up – rubbing the washcloth gently so as to not hurt your already sore and painful ass. The washing has an effect on you. You begin moving your hips as though you are getting further excited. The pillows beneath your pussy are soaked. I kneel on the bed and reach my tongue toward your pussy lips. Red and swollen, your sex is so beautiful. Your large clit is poking out from its little hood. I can't resist. I begin licking your pussy – working slowly from your clit all the way up to and around your recently fucked ass hole. You are constantly moaning and thrashing. I can hardly hold you still even though you are still tied to the bed. Then you begin to orgasm. Your body is one quivering, shaking mass of jelly. I insert a finger in your pussy and find your G spot. Massaging it gently as you continue to shake and orgasm. Finally – with one massive shudder, you collapse. Out like a light. I untie you and turn you over. Removing most of the pillows from the bed, I hold and cuddle you. You are mine, baby girl. All mine. And I love you very much. Anal Virgin Lauren examined her body carefully in the mirror. Tonight was special and she had to look perfect. She ran her hands gently over her round breasts, pausing to linger on her hard nipples. She continued moving her hand south across her flat stomach and into her soft and smooth pussy searching for her clit. It was easy to find because it was already swollen from the excitement of the events planned for tonight. A soft moan escaped her lips as she brushed a finger across it. She turned and looked at her round ass. She reached around and grabbed her cheeks and spread them so she could get a good look at her asshole. A warm rush filled her body. This is what was making tonight special. She was going to let Brandon fuck her ass. It is something she had never done, but Brandon loved it and had been begging her for months to let his cock invade her ass. Finally, she had agreed. She couldn't resist him any longer. While keeping her left hand on her ass to keep it spread, she ran her right hand up between her legs. She paused to slip a finger in her wet pussy and then she began to play with her asshole. She explored the soft skin around it first. God, it felt so good! She softly pushed one shy fingertip into her ass. Her excitement reached a new high as she watched her asshole swallow her finger. She couldn't wait to feel Brandon's cock slide into her like she her finger had. Oh God! Brandon! He would be there any second! Lauren grabbed the sheer black nightgown she had purchased for tonight and threw it over her head. She took one last look in the mirror to admire the way her breasts pressed against the fabric and how inviting her cream colored thighs looked. She straightened her hair and ran to the kitchen. She pulled the bottle of wine from the ice bucket and opened it. As she was reaching for the glasses, she heard the front door open. Brandon had arrived. He walked into the kitchen as she was pouring the wine. A hungry smile crept across his face as he looked her over. Lauren gave him her most seductive smile as she handed him his glass. "How was your day", she asked as nonchalantly as she could. The hungry smile became a full grin as lust filled Brandon's eyes. "It just got a lot better", he answered in his deep voice. Lauren felt his strong arms reaching around her and she fell into his hard chest. His hands began to move up and down her back and she could feel his hard on through his slacks. She lifted her head and his lips met hers in an explosion of passion. His lips covered hers and his tongue traveled across her lips and into her mouth. She slowly massaged his tongue as she reached down and unzipped his pants. She pulled away so she could reach inside and feel his cock. It was so huge! Lauren couldn't wait any longer. She dropped to her knees and pulled his cock out. She stared at it in wonder. Brandon had the perfect cock. It was long and thick. And perfectly symmetrical, with a big fat smooth head. Lauren licked her lips and began to tease his cock with the tip of her tongue. She started at his head, slowly kissing and licking the tip of his dick. When she looked up, she saw the look of delight on his face so she continued to move down his cock. She licked and kissed every inch of his cock as she worked her way down to his balls. Brandon's balls were big and hard, just like the rest of him. Lauren slide one into her mouth as she continued to stroke his slippery cock with her hands. She let his ball slide across her tongue and she moaned as it filled her mouth. The vibrations made Brandon moan and he reached down and ran his fingers through her hair. Lauren released his ball so she could wet the other one. She kissed her way over to the other side and ran her tongue underneath his sack as she pulled his ball into her mouth with her tongue. Another moan from Brandon let Lauren know she was giving him exactly what he needed. She let go of his ball and began to slide her tongue back up to the top of Brandon's cock, but he had other ideas. "You can have more of that later", he said. In one smooth motion, he pulled her up off the floor and into his arms. He lifted her off of her feet and carried her into the bedroom where he laid her on the bed. Lauren lay trembling as Brandon undressed. She loved watching him. He was the sexiest man she had ever seen as he pulled his pants off and ripped his shirt over his head. His long hair flowed down his back and Lauren's heart rate increased. Brandon then crawled up between Lauren's legs. She could feel his hair tickling her inner thighs and his hot breath on her pussy. "Look at those lips", he said, "How can anyone look at those lips and not want to make out with them?" An electric whimper escaped Lauren's mouth as Brandon's tongue parted her pussy lips. He sucked each lip into his mouth and softly nibbled on each one until they were as hot and swollen as her clit. Brandon loved feeling her lips swell under his teeth and tongue, but Lauren couldn't take anymore. "Please Baby", she said, "Please suck on my clit. Oh please make me cum. I need to cum!" Brandon swiftly found her clit and pulled it between his lips. He could feel Lauren's excitement rising and reached up to grab her hips. Lauren's moans grew loader and more intense. Her legs started shaking and Brandon prepared for her orgasm. He held her clit with his teeth and attacked it with the tip of his tongue until Lauren's hips bucked and every muscle in her abdomen began to convulse, but Brandon wasn't done. He ran his tongue down between her lips and down more until he had found her ass. Lauren gasped in pleasure as she felt his tongue circle the sensitive skin she had been fingering a short time before. Her finger felt good, but his tongue was amazing! She could feel her pussy getting hotter as his tongue dug deeper and deeper into her ass. She couldn't stop the orgasm when she felt his soft tongue push into her ass. He held her onto his tongue so she could feel her asshole squeezing his tongue as she came. Before Lauren could recover, Brandon had her clit back between his teeth. He slid a finger into her saturated pussy and once it was good and wet he moved that finger to her ass. Lauren could feel her ass stretch as Brandon forced his finger inside. Lauren began to fuck Brandon's finger with her ass. She couldn't get enough of his finger. "Want to try it with two fingers", Brandon asked. Lauren could only respond with a moan, but Brandon knew she wanted it. He moved anther finger into her pussy and then he slipped it in her ass with the other finger. Lauren's moans were uncontrollable. Brandon kept his tongue on her clit while he slowly fucked her ass with his index and middle fingers. Lauren could not keep still. She pushed her ass down onto his fingers and rolled her hips until she was shaken by another violent orgasm. "Your cock", Lauren gasped, "I need your cock inside me right now!" Brandon quickly climbed on top of Lauren. The desire in her eyes burned into him as he shoved his huge cock into her throbbing pussy. Her muscles grabbed him and pulled him deeper and deeper inside of him as her hips rocked with his in perfect unison. He watched the orgasm build on her face. He reached down and pulled her right leg up over his shoulder so he could reach even deeper inside her. Lauren's breath came out in fast gasps and he could see her heart pounding through her beautiful breast. Brandon fucked her harder to force the orgasm out of her. Lauren's back arched as she cried out and came all over his massive cock. Lauren could feel her cum dripping down her ass. She was shaking as she looked Brandon in the eye and said, "Please Baby, please fuck my ass." Brandon leaned down and kissed her gently on the lips as he pulled he cock out of her drenched pussy and positioned it on her asshole. Lauren moaned as she felt the smooth head of his cock push against her slippery ass. "Be gentle," she pleaded. Brandon nodded as he held her leg over his shoulder and slowly pushed his cock into Lauren's ass. He watched Lauren's eyes grow wide as his girth forced its way into her virgin asshole, pausing every few seconds to let her adjust to his size. Lauren reached down and started fingering her pussy as Brandon began to fuck her ass with a slow and steady rhythm. She couldn't believe how full she felt. It was thrilling to feel his cock in her ass. She could see his pleasure on his face and it only turned her on more. She could feel her own orgasm building as Brandon watched his cock slide in and out of Lauren's ass. She wondered how her ass looked with Brandon's cock stuffed in it. She was sure it looked amazing. Her orgasm tore through her body with a vengeance. Every muscle flexed and twitched as her pussy overflowed with cum. Brandon's breath was hot on her ear. "Where do you want me to cum," he asked. "My mouth. Come in my mouth so I can swallow every last drop of you", Lauren answered eagerly. Brandon pulled his cock out of her ass and into Lauren's waiting mouth. She swallowed his head and began to run her tongue around his cock. Back and forth and circling the head of his cock. She used one hand to stroke his thick shaft while she tickled his balls with the other. She moaned loudly on his dick as he fucked her face. Brandon's moans got loader as his orgasm got closer. A masculine growl ripped out of his lungs as he came. He thrust forward and his cock slide down the back of Lauren's mouth where he shot a huge load down her throat. Brandon climbed off of Lauren and pulled her into his arms as he lay beside her. "Maybe next time we should tie you up," he said with a grin. "Anything you want," Lauren answered with a matching grin. Anal Virgin Molly and I sat there waiting for Dennis. He was a friend of hers. Well, more like an acquaintance. He was roommates with her boyfriend, John and her boyfriend had asked her if she knew any young girls...Dennis like young girls. Even though I was in a relationship at the time, she instantly thought of me because she knows I love older men and would never pass up an opportunity to get something different. Now, I was a little nervous and being in a bar, I naturally did one of the things I do when I am nervous...I drank. I had about 4 beers and 2 White Russians. By the time Dennis showed up, I was very relaxed an in the flirtiest of moods. He walked through the door and Molly nudge me and nodded in his direction. He was very nice looking for an older guy. He had a shaved head and a goatee which is a look that I find very attractive on a man. I think I just like the sinister look of it. He was muscular and dressed casually in jeans and a t-shirt. He walked over to Molly and she introduced us. I motioned him over to sit next to me and we started talking. I learned that he was forty-three yrs old, divorced, and worked in construction. The more we talked, the more relaxed I felt. I began touching his knee and leaning into him giving him a look at my cleavage. I never considered myself the "model type" but I thought I looked pretty good at twenty-one with my long dark brown hair and brown eyes. I am about 5'4 and back then was around 120lbs. I even remember what I had on, my favorite black mini skirt and red sweater. He had a few rum and cokes and by midnight, we were both ready to leave the bar and go somewhere more private. He suggested his house. Molly stayed behind. When we got into his car and started driving, he pulled me closer to him. I kissed his neck and started rubbing his crotch. From what I could tell, he was already getting hard and it felt like I was in for a big treat. At the stop light, he reached down and unzipped his pants and ordered me to suck his cock. That was another thing I liked about Dennis. He was very aggressive and loved dominating me. I leaned down and took his cock out, it was about 7" half hard and I was a bit nervous thinking about how big it would be once he was fully erect. I had never taken a cock bigger than 6 or 7 inches before. I slid it into my mouth slowly, sucking it in and out. He put his hand on the back of my head forcing me to take all of his cock in my mouth. It gagged me a little but my throat quickly opened up allowing the full length to go in. With a few more thrusts, he unloaded into my mouth. I felt his thick cum in my mouth and he wouldn't let go of my head so I was forced to swallow every drop. His was the first cum I ever swallowed. When we arrived at his house, he showed me inside. He asked if I wanted a beer and I said yes and asked if I could use the phone. He said that was fine. I called my boyfriend at the time and told him I wouldn't be home. That I was staying the night at Molly's. I was lucky that he was an understanding and trusting boyfriend. He said that was fine and he would see me tomorrow. I felt guilty for what I was about to do but I have gone too far to turn back now. And at this point I wanted Dennis so bad, my pussy was dripping wet. After some more small talk, he leaned in and started kissing me. I felt his hands go up under my sweater and my bra and cup my breasts. He began massaging and caressing my nipples between his fingers. He laid me back on the couch and pulled my skirt up and slid my panties off. He put them behind him on the couch and then started fingering my pussy. I closed my eyes and threw my hands over my head and just relaxed. Feeling his fingers go in and out while his thumb massaged my clit. He commented on how wet I was and what a nice smooth baby girl pussy I had. He then began licking my clit and sucking it between his lips. I was in heaven. He pushed my legs up and apart exposing my clit even more. As he continued licking me, he slid a finger up my ass. I was surprised as I have never had this done before. It felt so good and he comment on how tight I was. Dennis suggested that we go upstairs because he thought his roommate might come home and he wanted a little more privacy. He took me by the hand and picked up my panties. I pulled my skirt down and followed behind him as he led me upstairs. We walked down the hall to his bedroom. His room was light blue. There was a black light over the bed and an American flag on the wall. On his closet door was a mirror. His bed was lengthwise along the closet door, if you were lying in bed, you could see yourself in the mirror. He went to his stereo and put on The Doors. He then shut the bedroom door and lay down on the bed and unzipped his pants and looked at me I walked over and sat on the side of his bed and started stroking his cock with my hand. He ordered me to undress him. I walked down to the edge of the bed and took his shoes and socks off and then grabbed the legs of his jeans and pulled them off as well along with his underwear. He then sat up so I could take his shirt off. His cock was rock hard and huge. He told me to get my clothes off. This was an easy task because by this time, I was only wearing my skirt and sweater. Dennis pulled me on top of him and my pussy was so wet already that his cock easily slid in. I began riding his cock. Fucking him hard, being filled with his cock. He reached up and rubbed my breasts using them for leverage as he bounced me up and down on him. He demanded that I cum now or wouldn't be allowed to cum later. I looked down at him and began rocking back and forth, up and down like I was riding a horse. My pussy walls began to contract and release and then my hot juices were all over him. We changed positions and he made it so we were facing the mirror. I was on all fours on the bed and he was standing behind me. That's when I felt it, the tip of his cock poised at the entrance of my asshole. I backed away instinctively and laid flat on the bed. I told him that I didn't want to do that, I have never had anal sex before. He leaned down almost laying on top of me. I could feel his breath against my neck and he whispered in my ear to get my ass up in the air. Then he grabbed me by my hair and pulled me up. He took the palm of his hand and began spanking my ass. Each cheek 10 times. The Doors, Love me two times was playing on the stereo. I begged him to stop. I have never had a man treat me like this before. I was scared and ashamed but at the same time very much turned on. I think that is were my shame came from. He was dominating me and treating me like a whore and I loved it. After he made my ass red, he poised the head of his cock at my entrance again. This time, I didn't move. I was on my elbows and buried my head into the mattress. I felt him pushing his way into me, slowly. The head of his cock was in my ass. He ran his hand up my back and put his other hand on my hip. With one thrust, he was entirely in me. I was full of his cock, his balls resting against my pussy. I didn't move nor did he for several moments. I remember feeling sick to my stomach and somewhat shocked that I had a cock up my ass. He was somewhat encouraging, saying things like relax baby girl and it would be over soon and start feeling good. I just laid there whimpering. He began pumping his cock in and out of my ass slowly. It hurt like hell. I never felt anything like this in my entire young life. I remember thinking that I wish it would be over soon. I started thinking about anything else other than what was happening to me and the pain I felt. Then, it happened. I realized that the pain that I once was feeling was slipping away and now I was feeling wave after wave of pleasure. His cock was sliding in and out easier now and I raised up onto my hands and looked in the mirror for the first time and saw Dennis behind me looking at me as well, with his hands on my hips driving his cock inside of me. I started meeting each one of his thrusts trying to drive him deeper into me. It was ecstasy now. I put my fingers in my mouth and licked them then began rubbing my clit. I heard him say that's it baby girl. I knew you would be into this. He closed his eyes and released his load deep into my bowels. I spanked my pussy and began to cum as well, it was a hard cum and I ended up shooting all over my hand. I had no idea I could cum like that. It was amazing. He collapsed on the bed beside me. And I lay on my stomach. My ass was still stretched wide open from the recent activities. I looked at him and he kissed me on my forehead and rubbed my back. And so it began... Anal Virginity "It would hurt so bad." Vanessa told me. " I mean that's an out hole not an in!" "I guess." I said "But… she likes it." I finished pointing at a picture online of a blonde girl with her ass in the air and a large vibrator inside of it. "That picture probably isn't even real." She said, "You know all the shit they can do with pictures on the Internet." "I dunno it looks real." Starring at the picture I couldn't help but think what was going through the girls mind… what would it feel like do guys like it better in there then in a pussy? "Its not real silly girl… I have to get to work." She said "Are we hooking up tonight at the club?" "Sure." I said absentmindedly clicking to the next picture this time a blond girl with a huge black cock in her ass making a painful face. "Ok don't stare at that thing to long. I'll see you at 11." She said closing the door behind her. I bit my lip and clicked the next picture an up close shot of cum drooling out of an asshole. Licking my lips I glanced up at the clock 4pm. I shut down the computer and went into my bedroom taking off my clothing I stared in the mirror. "Not bad." I thought to myself noting how short I was. Just barely 5 feet tall I thought cupping my large full breasts letting my soft fingertips run against my big round hard nipples. Turning slowly I stared at my ass round full nice wide hips. Bending over and spreading my legs I looked into the mirror again bent fully at the waist my ass was high in the air I could see my bare shaven pussy my lips were puffy and drenched with wetness. I stroked a finger up my cunt. It looked hot, like the pictures on the computer. I pressed my tiny finger into my pussy UHHH Moaning softly. In and out I pumped my finger pressing another in now two hot fingers probing in and out of my hot pussy the blood rushing to my head from bending this way it felt hot I felt so dizzy cuming hard it drooled down my thighs. Pulling my fingers out again I tickled my asshole with my index finger twitching slightly I pressed it into the first knuckle pressing back and forth a little bit then more. Pushing my whole finger in now and wiggling it around twitching again then moaning out. I got down on my knees ass still in the air face pressed to the floor now I wiggled my finger in my ass more. Now my other hand up to my pussy pushing two fingers into it pumping my hot pussy with my fingers and fucking my asshole with my finger. UHH SHIT. I screamed loud so loud I'm sure the whole apartment complex heard my body falling to the floor and shaking uncontrollably. "UHHHHHHHH FUCK MY Asshole BABY UHHHH!" After a few moments I pulled my fingers out of my cunt and licked them clean then walked to the bathroom and washed my hands. That was the most intense orgasm I have ever felt…. I HAVE TO HAVE MORE. I thought! I took a shower and got dressed. Low slung pants so low that it was good that I shave because my pubes would have been obviously view able. My shirt was just to the waist of my pants. That way if I wanted to I could raise my arms above my head while dancing and bare my abdomen. My breasts were full and firm pressed together even tighter in my red lace bra. I wore a black shirt that was cut in a V formation showing the lace at the edge of my bra fully exposing the thick cleavage the bra had formed. I got into my car. And old Chevrolet and drove to the club. Checking my watch… 9:30. Sighing slightly I found a parking place and touched up my makeup one final time glossfying my lips and adding a dab of mascara. I try to keep my makeup light when I am at a club since you get so sweaty on the dance floor it all ends up on someone's clothing if you get to heavy with it. I walked to the bouncer and handed him my ID. I'm sure he barely glanced at the id because his eyes were focused on my tits. He moved out of the way and opened the door for me handing my ID back. I giggled inside because he forgot to stamp my hand with the UNDER 21 stamp. Although maybe he just can't add because I will be 21 this year. The loud music hit my ears as I stepped into the club. Squinting my eyes I saw the dancers on the floor. I wandered out and began dancing with a few of my friends. I didn't know all of them by name but we were the regulars. Pumping my ass against the man behind my I felt his cock getting hard with each wiggle against him I felt his prick get harder and harder for me. I loved to tease men and make them horny with my body. "Hey Samantha you better watch it." He said It looked like he was watching me plenty for the both of us so I just shrugged. I turned around pressing my tittys against him for a few moments then taking a step back and raising my arms above my head rocking my pelvis forward and back in a pumping fashion. My pubic area visible now his hands swept across my belly then lower to my shaven area and back up to my navel our bodies touched while I rocked my pelvis forward then back humping against his pants his bulge now completely firm. Thankfully for him he was wearing baggy dark blue jeans that hid his package and a tight white "wife beater" with a short sleeved black button down shirt unbuttoned over it. He was hot how could I not press against him. He towered over my and had a strong build green eyes black short hair nice cologne. His hands touched my hips and I turned around again pressing my ass up and brushing it against his cock again bending at the waist like I was in the mirror I put my hands on the floor and popped my ass up against him to the beat. He took my hips and pulled my ass against him harder again. Again. Again. To the beat. He pulled me up so I was standing face to face with him and grabbed my wrist hard. We moved away from the crowd. My heart raced as he pulled me into his car. "Where we going Ben?" I asked giggling inside. He didn't say anything just rubbed the bulge in his pants awkwardly trying to move it to a more comfortable position. I turned on the radio to the local channel that broadcasts the club live every Friday night and the music pumped in his car. It felt like forever but I'm sure it was only a few minutes before he pulled into a parking lot and slid out of the car. Moving around to my side he opened the door and took me by my hand again shutting the car his alarm blooped a few times. Practically dragging my now we moved up to a doorway and he opened it pushing me inside he slammed the door behind us and deadbolted it. "Need to change your boxers?" I Joked. He grabbed me and lifted me up in to a cradle position like a groom carrying his bride he walked into the bedroom and plopped me onto his bed on top of me in seconds he was biting my flesh kissing my mouth. His tongue darted into my mouth and I twirled mine back against his. His hands in my pants rubbing my hot pussy it was wet SOO wet I'm sure my jeans were soaking as well. He plunged two fingers in pumping them against my g-spot he bite my neck again. He slid his hand out of my pussy and licked his fingers then pulled my shirt off roughly over my head. My breasts were heaving up and down panting with anticipation he pulled my tits out of my bra pushing it down under them he bite my hard nipple with his teeth. Licking at my nipple his other hand slid down and unbuttoned my pants I kicked them off the baggy leg holes making it easy to do so even with my shoes on. He moved down my body licking it then spread my legs apart roughly with his hands his face was pressed against my pussy his tongue pressing into my cunt hole. Lapping my pussy juices his hands kneaded my ass flesh. "UHHHH. EHHHHH MMMMMMAHHHHH." I screamed and moaned. He flipped me over my ass in the air. He spanked me. Hard to It tingled for long after that. I had never been spanked by a man before. It felt nice. He pulled his bulge out of his pants and ran it between my pussy lips like a hot-dog. It felt good probably six and a half inches and average thick. He grabbed my hair and caused me to arch back to him my ass going even higher in the air he plunged his cock into my pussy from behind. Pumping my cunt his hands were on my hips slamming my body against him. HARDER! HARDER! HARDER! "OH YES PLEASE FUCK ME FROM BEHIND FUCK ME BABY FUCK THE SHIT OUT OF MY PUSSY!" I screamed I moaned he fucked me harder and harder. His hands were digging at my back my flesh squeezing my tittys VERY hard. The fleshy tittys escaping through the spaces of his fingers leaving two hand prints on them. He let my breasts go again smacking my ass. "Such a nice ass Samantha A teasing little ass!" he slapped my ass again, then again then 10 more times. "PLEASE IT HURTS NO PLEASE." I begged him to stop but the fucking felt so good it was barely coming out as a plead more like begging him to keep fucking me. He pulled his cock from my cunt and I felt disappointed. He leaned down and smelled my pussy then licked and lapped at my pussy from behind with his mouth. Fucking my pussy with his tongue I screamed and cummed again drenching him. He licked up the skin between my asshole and pussy then he licked my asshole with his tongue. I flinched noticeably. "MMM you like that?" He asked not waiting for an answer before his tongue was pressing hard against my asshole. My asshole clenched around it not wanting to let him in he pressed harder finger fucking my pussy. He pulled his tongue out again then nibbled at my ass with his teeth. Pressing his tongue in pushing his spitty tongue in and out of my ass. I was in heaven screaming yelling and moaning thrashing around against his tongue. He moved his body quickly up mine and slammed his cock into my cunt a few more times drenching it wet. I sighed disappointed that he had not fucked my ass feeling he was going to cum inside of my pussy. "please." I whispered so low I'm sure he didn't hear me. Then I felt it. The most shocking pain I had felt since I lost my virginity two years ago. Ben had slammed all six and a half inches of his hard cock into my asshole. It burned it hurt so bad. My ass tried to expel hos cock from my ass but he held it there resting his chest against my back he rubbed my tittys lovingly. "Relax… unclench breath sweaty it will feel so good in a second just let your asshole get used to my cock… relax baby" he cooed soothing me. I let my body relax my asshole stopped protesting so much it started to feel almost used to his member being there. He begin pumping slowly maybe half an inch at first up and down softly softly…. So gentle he was with my virgin asshole. In and out half an inch then an inch. Slowly moving in and out inch by inch until half was moving in and out at a time. It started to feel UNBELIEVABLY FUCKING GOOD. Not just the cock in my ass but the idea that my ass was making his cock feel so good. That I was being SUCH a naughty dirty little slut getting my ass fucked. He moved faster now more and more friction and heat building and building his finger fiddled with my clitty and I came. I came hard and loud thrashing beneath him screaming and moaning with pleasure. Ben pummeled my ass with his cock faster and faster harder and faster grinding into my body until his cock exploded in a thick cummy orgasm. As he withdrew from my ass there was a slurping noise. My asshole tightened back up and his cum drooled out of my anus. With a soft pat on my ass he stood up and went into the bathroom turning on his shower. My mind was flooded with all the feelings that I felt. My first ass fucking. I knew from that day on I was hooked. Now I can't get enough cock and cum in my ass. After Ben and I showered he took me back to the club. I made sure to let Vanessa know that it did feel good and the pictures weren't faked. Now she can't wait to try it! The End I love a good fuck in the ass don't you? Now vote for my story if ya like it and send those comments! Love ya'll >:) Anal Virginity **Names have been changed... I'll leave it up to my readers to decide whether or not this ever truly happened...ax Cindy moaned softly as Dane slipped two fingers inside of her. She felt the familiar ripples of orgasm overwhelm her senses, body tightening around his digits, juices dripping onto his hand. She stood there, rigid as his fingers worked their magic, rubbing and caressing her secret places. She looked down at him sitting in front of her, arm muscles tensed, and saw the predatory gleam in his eyes, he wanted her... NOW... She whimpered at this, remembering the other times he had made her cum until it felt like her head would explode. He seemed to be holding back now, teasing her, his fingers stroking her g-spot as his thumb rubbed her clit. Suddenly his fingers withdrew, and her pussy clenched, already missing the pleasure he gave her. She whimpered, expecting him to turn her around, drop her shorts and enter her. Instead she felt his finger pressing into her ass, rubbing her juices around the rim to ease his entrance. He slipped inside. Cindy threw her head back, God how his finger in her ass turned her on. Her clit throbbed with anticipation; she needed him inside her so badly. For the next half hour she didn't know what was where, two fingers in her pussy, one in her ass, or two in her ass and one in her pussy, the time passed so swiftly, and before she knew it she was hitting her ninth or tenth orgasm, this one making her teeth clench and her legs tremble. Dane looked up at her, green eyes smiling, "You just came from me finger fucking only your ass, Cindy." Her head spun, did she? "Wow I knew it was possible but I never knew that I could cum from anal." she said softly. "Ok baby, now let me fuck you, I'm so hard it hurts." Dane whispered. Cindy looked around, thinking, her grandma was asleep in the house, they were out on the front porch, where anyone could see or hear. She turned off the porch light and took up a position outside the living room window to keep watch, bending over a tool bench. Her pants dropped to her ankles as she presented her tight tan little ass for his pleasure. He entered her pussy so swiftly she gasped, his thick, hard cock filling her tightness. She moaned in pleasure as he started to move in her, bringing her to orgasm after orgasm. She began to wonder after a few minutes, he seemed to be holding back from his pleasure, purposely not cumming. Since they were pressed for time before one of the kids woke up or her grandma got up, she urged him on, pushing her hips into his, but he still held back. She felt an extra width inside her as he pushed in two fingers alongside his cock. She reveled in the even fuller feeling, being stretched to her limit by the thickness of cock and fingers. After a few minutes he withdrew them, and she felt him sliding them into her ass, keeping rhythm with the thrusting of his hips. Feeling so filled and content Cindy's excitement peaked, throwing her into an orgasm like none before. Suddenly, he withdrew, holding her hips in a vise grip as she looked back at him questioningly, the light from the window lit a strip of his face up, what she could see looked like a mask of control, he was holding back from her. She felt his hands caress her back and buttocks, squeezing her cheeks. His hands parted her and she felt his fingers withdraw from her ass, to be replaced with the head of his cock. Pressing into her, she felt the head slip inside, the pain making her whimper, but it wasn't as bad as the times he'd tried before, his fingers had been stretching her all night. She looked back at him, hunched over her, slowly sliding another inch inside her tight passage, it burned, she whined. Dane stroked her back, encouraging her to loosen up her muscles. He slid in inch by slow inch, her whimpering all the while, the burning pain turning her on yet hurting her. Finally he was fully inside her, she could feel him throbbing, as her tight little ass gripped his cock with everything it had, trying to expel the invader. She felt the heat of his crotch pressed against her buttocks. Her insides felt sore with him in there. Cindy concentrated on the tightness, and soon figured out how to let go of those muscles, so different from the muscles of her pussy. Dane felt the release and gave a sigh of his own, slowly pulling it out of her virgin ass. He gently fucked her for a while; she reveled in the new sensation, as he started moving harder and faster. She felt an orgasm building, and whispered loudly, "Fuck I feel so DIRTY now. Make me your dirty little slut!!" Now he was slamming her ass, balls slapping against her swollen pussy. She dug her fingernails into the bench as she came so hard; her knees went weak with exhaustion. Suddenly his cock seemed to swell even bigger inside her tightest hole as she felt it start to jerk and she came again, knowing he was cumming inside her ass, where no man had ever came before...