4 comments/ 43119 views/ 11 favorites How It Started By: Chris62 This is the first time that written about my love of anal sex. Thinking about it, it can be traced back to my first anal encounter. With this in mind it is a true story, though the names have been changed. Please send me your comments and encouragement so I can improve my writing. ***** I think of myself as a normal 20 year old male. My name is Chris and my girlfriend is Leanne. I am 5'11" tanned and lean. She is a 5'7" natural blond with spectacular breasts and great curves and a great sense of humor. I am 20 and she is 18 - both in our first year of university. ... Our first encounter. We have been dating for a few weeks now and are still discovering each other. I had been rehearsing with my electro-rock band up at a mutual friends house and Leanne, like the other girlfriends, had hung out with us to watch, listen and talk girl stuff when they got bored with our musical musings. The cheap wine had been flowing so Leanne offered to drive me home in her car. We stop a little up the street from my house sitting together in the dark. I lean over a give Leanne a kiss. Her mouth opens, hungry. I send out my tongue and taste the sweetness of youth. Her tongue joins mine - they swirl together - I search her mouth and then she does mine. We are heating up. I reach up and touch her breast through her T-shirt - she breathes out. I slip my hand up and under, gently caressing her pearly white skin, cupping the fullness of her tit. "God!" I can't believe how ripe her breasts are - different from the other teens I have been dating. I struggle to get my hand under her bra so Leanne reaches back and releases her bouncing puppies with a beautiful smile I can see in the street light. "Touch me," she exhales. My right hand is drawn to her full globe, and my mouth back to hers. Leanne's nipple is hard against the palm of my hand. I cup and squeeze her the fullness of her breast. Leanne's mouth sucks harder on mine, her tongue harder in mine. My thumb and middle finger finds her hard nipple, growing even larger in response. I start to work it hard spurred on by Leanne's soft moans. She is getting seriously turned on. My cock is so hard the neatly circumcised head is almost poking out the top of my tight jeans. I take my wet mouth off hers and start to kiss then teasingly trail the very tip of my tongue slowly down her neck. I pause to sometimes kiss her hard on the neck before heading to her ample fullness. "Suck on it!" Leanne whispers. It would be rude to refuse. I put her rock hard nipple and surrounds in my mouth gripping her breast with my right hand. There is more there to handle than I can manage with one hand and bring up my left hand, first teasing the other breast , then gloriously squeezing, mashing, both breasts together, pushing both nipples as close together as I can. I work my tongue and mouth back and forth from one nipple to the other. "Damn!" I just can't get both nipples in my mouth at the same time. I have lost myself in her beautiful mounds. She brings me back to reality by undoing the tight belt on my jeans. "What's happening down here?" She hums as I continue to whip her nips with the tip of my tongue. Soon my cock is out and in her hands; she starts to roughly stroke up and down my shaft. "Easy, slower," I urge. We get into a shared rhythm. I start to travel south - tickling her oh so soft belly with the tip of my tongue. I reach the for the top of her jeans and quickly unbutton and unzip them with my teeth. I reach under her bum pulling them down and off revealing a her plain white cotton panties. I rub her crotch with my thumb - it's moist and fragrant with her passion. Excited I lean into her V - inhaling deeply. "Like what you see?" Leanne asks lazily. I respond by pulling the gusset of her white panties over so I can gently part her outer folds. I start rubbing her clit through its hood; I can see moisture growing on her inner folders. First one finger, then two snake into her love canal. "Hmmm." I move them in and out. I am transfixed by the beauty of her woman-ness folding itself around my hand. Leanne's clit has swelled, popping out of its hood, begging for attention. This is the first time I have gone down on Leanne and I can't wait to taste her. First I lick her clit then try to suck the whole thing in my mouth while continuing to pump my fingers in and out of her sweet pussy. She pushes her hips up in appreciation grinding her sex into my face. Leanne's breathing is now coming is quick gasps. My fingertips, deep inside her, curve up rubbing the rough skin of her G spot. "Arghhhhh!" Sweaty, moist sex grinds in orgasm on my face and I lick up her juice. Leanne grabs my hair and pulls my head up to kiss and taste her own orgasm on my lips. "Like yourself?" I ask. "Your turn," she answers. In one move Leanne lowers my jeans, grabbing my proud cock at the base of the shaft, and wraps her smiling lips around the glans. "Oh yeah!" I grab the back Leanne's head and push my manhood deeper into her sweet, soft, warm mouth. Pre-cum is running out the end of my dick mixing with her saliva making a slurping noise. I push my cock further in - to the back of her mouth - the top of her throat. "Ahhh!" My cock is in cool free air as Leanne comes up for air, her hand still firmly owning my maleness. "I want you in me." I know Leanne isn't on the pill or using any other kind of birth control. I'm 20 and can't plan ahead any further than my next gig so I don't have any condoms with me; our making out hasn't gone any further than playing stinky finger. I'll have to control myself and pull out before I blow. We're still in the front seat of the car and it's pretty tight. If we are getting down to business we will need a bit more room. I jump into the back and pull her over with me, arranging her beneath me. This will be our first fuck. Leanne is two years younger than me and I don't know if she has done it before. "Have you gone all the way before?" I ask. "Umm, kind of..." "You kind of either have or either haven't." "Steve put it a little bit it in, not all the way. I think I'm still a virgin..." was her cute reply. Steve was a past boyfriend. Thinking about this I wonder if she will want to remember her first time being a quick root in the back of a car. I would want something a bit more special to remember. "I don't have any condoms and don't want to take the risk of you getting pregnant... but I want you." I say this with my throbbing cock firmly lined up her sopping slit, the head hard against her clit. We need an option. "Just the tip!" I think to myself. "Why don't we save your cherry for somewhere more special?" I tell her "Hmmp! I need something..." She replies. "I've got an idea." I smile. Looking at Leanne beneath me, her legs spread, knees high by her side, beautifully framing her full breasts, nipples still keenly sharp, I lower my pulsing cock to her moist folds. My length running from the tip against her clit, along her buttery folds, the root on her puckered anus and my balls sitting between her ripe ass cheeks. "What to do?" I think. I am burning to plunge my cock balls deep into her pussy but we have decided to save that pleasure. I'm also sure I would fill her full of seed after two or three thrusts if I did that I am so turned on. I start to rock my length back and forth where it is. I take Leanne's hand and place it on my cock. "Push down so it rubs your clitty as I go," I whisper. The purple head is slick with her juices, grinding all the way from her ass to her hard nubbin. Time to get my groove on. After a bit of this action I start to concentrate on the beginning and end of my slippery path, working those tender places, just short of piercing her ass and pussy. "Oh yeah!" we say together. I rub her rock hard nipple and suck her open mouth. We are rocking! On the back stroke I circle her soft rear entrance, probing, teasing open the outer ass ring, stopping just short of popping the head all the way in. Ohhhh!" she moans and I move my cock up to work on her clit. "Mmmmm." I move my cock back a little just entering her soft folds and rock my hips, quickly stabbing in and out of her wetness. "MMMMMM!" Her moans growing. Sensing her orgasm is near I reach around her smooth white buns to find the opening of her anus slippery and wet with my work. In time with my front probing I slip a finger in and out of her ass. "Oh yeah!" we cry together! I am soooo close to cuming, I feel an animal growl growing in my throat. Leanne senses that I am close, holds my cock and rubs its head on her clit and labia in a circular motion. I AM CUMING NOW. Leanne squeezes my cock harder, moaning loud and low. I jam my finger all the way up her ass. Her moans turn up in pitch. I SHOOT BUCKETS OF JIZZ over her natural blond pubes. I rock my hips spraying her hand and up onto her baby smooth belly. She milks the last of my cum - her hand cum lubricated, mine mixing with hers. She releases my softening cock and massages our love juice onto her breasts, gently inhaling to savor our pungent sex-scents, tweaking her own nipples. I slowly take my finger out from deep in her ass. "Taste it," I urge her. Leanne lifts up her white breast and starts to lick our cum off her skin. I watch intently as her tongue tip cleans up all traces of jizz and then suckles on her own nipple. My cock, now half hard, rests in a mess of jizz on her pudenda and pubes, softy squelching amongst it all. "Want to taste it too?" She asks. How It Started My girlfriend-sharing fantasies started when I was in college. The girl I was seeing at the time was going to a university that was about a 6-hour drive away- she was an extremely pretty redhead who had played soccer in high school and she had a kinky streak, which suited me just fine. She was five-foot-five, roughly, and curvy in a really athletic way. She had red hair and a dazzling smile, and a thick ass and thighs that I worshiped almost daily. Needless to say when we parted ways for school in the fall, I was left wanting. Wanting her, mostly. The college life seemed to be treating her just fine when she and I talked. I knew she liked to drink, and she liked to go out with her friends and dance, and I knew she loved sex. Our sex life had always been very active, starting in high school, and we fucked in her car to a Kings of Leon CD so many times that, like one of Pavlov's dogs, I feel a rush of blood to my groin whenever I hear those songs on the radio. She still keeps that album in her car to the best of my knowledge. So back to this story and when it took place – the fall of my sophomore year of college, not long after she started her freshman year at a bigger school, she quit talking to me for several days. I was mad that she had chosen to attend a big football game instead of meeting up with me back in our hometown for a weekend together. Turns out, as she explained over the phone when I finally called, she had been hooking up with other guys at parties and having a good time. No actual sex yet but lots of kissing, groping, even a few blowjobs, if I was going to take her word for it. It wasn't a stretch to believe. So as much as she would love to see me, she said, she wanted to just have fun this weekend. She promised we would schedule a few days soon when we could both come home and meet up. I hung up the phone, nearly in tears, not knowing what in the hell I should do. For a few days and nights this new knowledge about her activities destroyed me. I was in a fever dream; I didn't eat, I barely slept, and I didn't even think about going to class. But one morning I woke up at dawn and, her admissions not being at the forefront of my mind, I grabbed some granola bars and headed out for a lengthy bike ride. I needed the fresh air. I was doing battle with stupid Midwest headwinds, typical for where I'd chosen to become a road cyclist, and thinking deep thoughts. Did this girl love me any less? No. She had said she was torn between sexual gratification and being in a relationship with me, and sex had never been a problem. I'm well-endowed and very fit, and our chemistry in bed was amazing. She just wanted to get some of that when I couldn't give it to her. I mulled over the thought of her getting fucked by other guys and giving head at parties, and as much as my stomach clenched, I realized that on some primal level... I was getting turned on. Despite the blood volume circulating through my legs, I started to get hard in my spandex bike shorts. I calmed myself down, because it got uncomfortable really fast, and turned around and headed home. I can tell you, I was grateful to have the wind at my back as I pedaled back to my dorm room. I just wanted to get the hell off my bike and ponder these new thoughts in a private setting. Under a blanket, maybe. I carried my bike up the flight of stairs in my dorm, unlocked my room (my roommate, mercifully, had a block of classes that kept him gone for most of the day) and stripped off my sweaty bike clothes. I had made a decision – I was going to make the best of what was racing around my brain. I was going to get off on it, instead of letting it kill me. I went into the bathroom and shut the door. I was rock hard before the shower even got up to temperature. I stepped into the stall, drawing the curtain behind me, and stroked myself as I let the jets of water pelt my head and shoulders. I summoned up memories of Anna, drunk and tasting of booze, putting her tongue in my mouth and kissing me sloppily, the way I loved it best for some reason. I thought of her coming home late and whispering in my ear that she'd been naughty, and taking my hand... and sliding it inside the waistband of her leggings. She loved wearing leggings when she went out, showing off that beautiful ass of hers. She would be so wet, her sticky sex covering my fingers and her voice in my ear, moaning her approval. "Please don't be mad," she would say, giving me the best cute-pouty look she could manage. "What's... going on? What do you mean?" I'd reply. She would pull back from me for a second, her gaze going to the floor. "I... fucked someone tonight. I was at this party and it just happened." I would be in shock for a second, but I would need her to finish telling me. My brain would lock up, unable to process with all the blood in my body flowing to my dick. A small smile played across her face as I asked her to go on, every bit of my attention focused on what she was saying. "We were dancing, and I just really wanted him, so I took his hand and we went upstairs... and I let him cum inside me. His dick was so big, and it felt amazing... God I just want more..." And then she'd start kissing me like that again, sloppy and lots of tongue, like she needed my dick inside her. Needed it the way you need air. I stroked myself in the shower, thinking of this, and almost came in my hand thinking of how she would kiss me but I slowed down to savor the fantasy for a moment. Maybe see how well my creative brain was functioning. I would grab her and kiss her, wanting nothing but her right then. "It felt like a lot of cum... Want to see?" She would ask, pulling away from the kiss so she could talk. Well, yeah. Yeah, I want to see. I would let her lay back on my bed and kiss down her body, her slightly sweaty body that smelled like coconut rum and her perfume, pulling off her leggings to reveal- Cum, and her sex, smeared everywhere between her legs, panties missing. Cum dripping down to her ass, and smeared in what little hair there was above her clit where she'd shaved a landing strip. Smeared on the insides of her thighs. What was hers and what was his, I couldn't say, but I also wouldn't care, not for a second. I'd dive in. She would moan instantly, her hands going to my head, fingers locking into my blond hair as my tongue, lips, cheeks, nose and chin would be instantly soaked in her sex. My tongue would travel from her thighs to her clit, teasing her little bud as I moved down to her puckered asshole to retrieve cum that had dripped down. The heavy taste would be like heaven, and the slippery feeling on my face that I was imagining almost made me cum again, but like last time I slowed down and held back. This was going to be a monster orgasm when I finally did let loose. My shoulders and chest were blotchy-red from the heat of the shower, and steam obscured the overhead light. I kept stroking myself, imagining her writhing at my tongue's assault on her freshly fucked pussy. "Baby, I want you to fuck me," she'd say through her moans. "I want to feel you where he was. Please." I would move my kisses and licks up her body, stripping off her tank top and unclipping her bra as I went to kiss her hard little nipples. Her left breast would fill my hand as I squeezed it, using my right arm to steady myself as we kiss wildly, tongues thrashing and lips gliding together, and the tip of my dick would feel the hot slick entrance of her pussy. Whenever we had sex we would go down on each other first, for our mutual benefit and to make sure that everything was as lubricated as it could be. But in this fantasy, and likely in the event it happened, she would be so wet that I could enter her smoothly without a worry. Her fingernails would bite into the backs of my arms, and her moan past my ear would sound like a masterpiece sonata's finishing chord. Just the right amount of rasp, full of desire, the way she had sounded when I entered her so many times before. The novelty and excitement of that moment could never wear off. I would feel her, from the inside now, hotter than she had ever felt and slick with cum. The mere thought was enough, but to actually feel it? To be there, and to know for sure? It would send us both into orbit. And finally, it did – standing in the shower, playing this scene behind my eyelids, I came so hard my knees gave out. After I cleaned up and got out of the shower I felt like a new man. I knew that as long as she came back to me at the end of the day (or night, as it were) I could handle this. Hell, I could love this. I wanted my girlfriend to be as sexual and sexually satisfied as she could, and since she showed no signs of holding herself back, I figured my new fantasy was about to be granted. This frame of mind was far and above better than letting myself get derailed by whoever else was fucking my girlfriend. After all I'd be reclaiming her every time I made the trip home, right? And I was left with a lesson, which had been imparted to me before but hadn't stuck the first time: never underestimate the power of some fresh air and time alone to get your head on straight.