Hannah and I were driving home from her parents’ house one cool evening, and I didn’t know it yet, but the most amazing night of my life was ahead of me. Hannah’s parents’ lived kind of out in the country, while as college students both Hannah and I lived in the city, so we had a bit of a drive ahead of us. Hannah was always very quiet and soft spoken but on this ride she was especially silent. I thought something might be up but she assured me nothing was amiss.
Finally, after squirming and seeming a little antsy, she spoke up. “I’m not really tired, so, want to hang out at your place for a while?”
“Sure,” I replied. Thoughts of potential sexual exploits entered my mind briefly, but Hannah and I hadn’t even come close to making love yet, so I honestly didn’t expect too much action tonight.
Hannah and I had been dating for a few months now, and believe me, I’ve taken a bit of abuse from my friends for not having gotten anything more than a few deep, soft kisses. Especially as young, hormone-filled college students, dating someone for months without any action seemed seriously out of place. It’s not like I didn’t make advances, running my hand across her shirt and caressing while we kissed, but Hannah was reluctant. She said she had only had sex with one guy and it “got really screwed up” and so she wanted to take it slow. I didn’t want to pry and I figured she’d come around soon, she said she want me too, but it was torture to wait. But I really liked Hannah, in such a serious and kindred way, that I didn’t let our lack of sexual activity stop me from enjoying the relationship. Perhaps another reason I was so patient was that she was so incredibly beautiful, and just painfully sexy, that I always thought today might be the day I actually got with such an amazing woman. This evening, when I briefly thought this while driving, I was right.
Hannah was only five feet tall, to my six, with hypnotically dark hair and passionately green eyes. She was as white and American as myself but I often wondered if her family history didn’t trace back to some Mediterranean ancestors. She had a naturally tan complexion and a gentle grace that drove men, or at least drove me, absolutely wild. She was by no means heavy or out of shape, but she carried just a little extra weight for her frame in all the places that made me drool. She had gorgeous (from what I could tell with clothes on) breasts that were immaculately round and full. They weren’t obscenely large, but like I said, they were one place she had a little extra weight so that they were incredibly full and large for her size. Tonight she wore a black button up blouse to dinner with white trim and white buttons. She had left it tastefully buttoned so as to only hint at the beauty that lay beneath. Hannah also carried that smidgeon of extra weight in her round and perfectly shaped ass. Admittedly, just about every second that Hannah hasn’t spent facing me I’ve spent admiring her ass. Again, it can only be described as just slightly larger than you would expect for someone her size, which makes it just stand out and cry for attention.
Hannah hadn’t been too clear about what she wanted to do this evening. “Just watch a movie or something,” she said, but I was happy to be spending time with her. When we made it to my apartment complex we had six flights of stairs to climb. Hannah didn’t like to take the elevator, she said it was good exercise, and as long as I was behind her, I liked taking the stairs more too. She had to know I was basically eye-fucking her ass as we ascended, but she acted cool. When we entered my apartment and closed the door she pulled my close and locked my in a deep kiss. Her tongue tickled mine and I felt her body press into me before she released.
“Why don’t you pick out a movie and I’ll be right back,” she whispered. My cock had sprung to attention during our kiss, and even though I wasn’t surprised that all we would do was watch a movie, apparently my member was hoping tonight was the night for more. She smiled and headed down the hall and I heard a door close. I figured she had just gone to the bathroom. I made my way into the kitchen to start some popcorn, then I plopped down in front of the DVD rack to find us a nice romantic comedy. I was hoping to find a movie that we wouldn’t mind missing any parts of if we found ourselves in another sweet embrace.
Before I settled on a film I heard a shout from down the hall. When I got up to examine I found that the bathroom was unoccupied but that my bedroom door was closed. As I neared I heard Hannah call, “Shane (that’s me).”
“Yeah,” I called through the door, “what’s up?”
“Can you do exactly as I say?” This was getting strange. Not only the whole talking through a closed door thing, but Hannah wasn’t the type to give orders either.
“Yeah, is everything okay?” I was getting a little worried
“Yeah, fine, just promise you’ll do exactly as I say,” she returned. I was almost certain everything was not okay, but I promised.
“Okay,” she said, “now open the door but don’t turn the light on.”
I complied. I opened the door and stared into darkness. She had shut all the blinds and my bedroom was pitch dark. A column of dull light coming from the door where I stood split the darkness, but it fell on my dresser and didn’t give away anything about what was going on.
“Shane,” she started, “we’ve been together for a while now and you know as well as I that we haven’t… done anything.” I knew that, and I started to get a little excited. Then I considered all the mystery, the darkness, maybe there was something she was ashamed of and wanted to hide. Did she have some deformity or problem that would be a major show stopper?
“Uh-huh,” was all I managed to voice.
“Well, I want you. And I know you want me.”
“Uh-huh,” I grunted again.
“Do you want to fuck me?”
I was momentarily speechless. A bulge grew in my jeans, ready to answer for me. “Yes,” I finally said, “so bad.”
“Mmmm,” she cooed. “I want you to fuck me too. I’m crazy about you, I’ve never felt like this before. We haven’t had sex yet because I didn’t want to just have sex, I wanted to make your fantasies come true.” This was more than I think I’d ever heard her say at once, but I was loving listening. “Do you have fantasies about me?”
“Oh my God,” I said, “so many. I’ve been dreaming about being with you ever since you first giggled at my stupid jokes in that bar.”
She giggled a little here, remembering how we met. “When I tell you to turn on the lights, I want you to explore your fantasies. Whatever you want from me, absolutely anything you’ve been dreaming of, I want you to have it.”
My mind raced, there were so many things I’d thought about, stroked off to, that I didn’t even know where to begin. I felt a little light headed, probably made worse by that fact that my cock was engorged and straining hard against my zipper.
“You… are you serious?” I stammered.
“Mmm, deadly. I want you to indulge in me. That’s been my fantasy ever since we’ve met. Making your fantasies come true, that’s what I dream about. When I tell you to turn on the lights, that’s when I stop telling you what to do. Once you hit the lights, it’s your show.”
I was overcome with desire and speechless. I had so much lust that I didn’t know where to begin. It was such a wild and amazing situation so I wanted to really purge all my naughtiest desires, but it was also our first time, so I thought maybe I should keep it within reason, hold off on the kinky stuff, and just make passionate love. My mind was swimming.
“Turn the lights on,” she order. I hit the switch and immediately I knew exactly what I would do.
With the room illuminated my gaze fell upon Hannah as I’d never seen her before. A little pile of feminine clothes on the floor told me what I already knew. She was on my bed, completely naked, positioned on her knees and elbows. Her head was cradled in my sheets, a sea of dark hair flowing around her beautiful face, and her feet and ankles hung just off the corner of the bed. Her eyes were closed but her lips moved slowly, pulsing with anticipation. She knew exactly what I wanted, it was clear. She obviously noticed all the times that I had stared at her ass and thought she wasn’t noticing. She held her unbelievable ass high in the air, a view I’d dreamed about countless times. I could see the moist folds of her pussy between her legs, highlighted by a halo of dark velvety hair. Her pussy looked inviting, waiting, warm and delicious. In her position she pushed her hips up and pointed her ass as high as she could, and while the beauty of her creamy legs, her soft hair, her angelic face, and her glistening pussy was truly a sight to behold, I was completely transfixed by something else. My eyes followed a trail from the top of her ass down, between two full and amazing cheeks, to her magnificent asshole. The tiny hole looked tight and beautiful, slightly darker than the skin around, the same color as her large areolas, I noticed. Most of my fantasies involved that tight asshole. Hannah was so shy that I assumed she wasn’t sexually adventurous, and one of my greatest fears was that she would never be comfortable exploring anal sex. As I stared longingly at her, I knew tonight I would find out.
I walked in slowly, savoring the sight of her. When I reached the bed I saw she was nervous, not quite shivering, but definitely tense. I placed my hands on her bare ass, one for each side, and squeezed. As I did she sighed and the squeezing stretched her ass apart. I watched as her pussy spread gently, wet deep within the folds, and I saw into her beautiful vagina. Her asshole quivered as the skin around it slowly stretched, and I’m certain I surprised her as I dove my face down and buried myself in her tight ass. My tongue plunged past my lips and met stiff resistance at her clenched asshole. I heard Hannah breathe deeply in and I expected the exhalation to be a stern denial of my anal probing. But Hannah just sighed and relaxed some, sinking a little into the sheets. She was still tight and resistant but with each push my tongue burrowed into her tiny asshole. She continued to moan and sigh, sounds that I hoped indicated pleasure but I wasn’t honestly sure, but as long as she didn’t protest I was determined to continue.
As my tongue alternated between licking the rim of her asshole and exploring deep inside, my hands started working the rest of her body. I was sure her audible sounds were from pleasure as I massaged her ass, caressed her smooth legs, and ran my hands up her stomach and back. I briefly reached her breasts, which I hadn’t seen very clearly when I stared at her because of her bent over position, and I found they were overflowing in my hands. Her hands joined mine some as I took her in, her fingers mingling with mine as I felt her hard nipples for the first time. I then brought my hands back toward me and settled on her soaking pussy. She was clearly excited by the whole situation, I hoped the anal tonguing was turning her on, and my fingers were covered in silky moisture before I even inserted them. I gently ran the index finger of my right hand in between her folds and grazed across her clit. This sent shivers through her body and I focused the next few minutes of my attention on playing with her tiny clit. As I did she shook and moaned, rocking gently against my finger, which only improved the depth and quality of my continued ass tonguing. I was absolutely in heaven, the taste of her ass was indescribably divine, and by now I had wiggled my tongue in as deep as I could reach. My tongue slipped and slid within as her sphincter contracted around it and all I could think about was how those contractions would feel around the shaft of my cock.
Moments later I pushed my finger down her pussy and into her tight vagina. Not that I was any kind of expert, but it was pretty obvious she hadn’t had a lot of sex as her tight pussy clamped around my finger. I stood up slightly, reluctantly retreating from her delicious ass. The sight was something to behold: a beautiful girl, who I was crazy about, with her sopping pussy wrapped around my finger and rocking along as I gently probed, with an absolutely soaking wet asshole. With my left hand I began to undo my jeans. My cock was suffocating in there, dying for its turn in these tight holes. I was so overcome with lust that I knew my cock was going to go crazy in her. I hoped I didn’t hurt her. I believe I have at least an above average size cock, thick and strong, and I knew it would be a struggle fitting it in her anywhere.
She knew it was show time when I slid my finger out of her pussy and used both hands to quickly undress. She looked at me and bit her lip but didn’t say a word, still openly waiting to fulfill my fantasies. I hoped beyond hope that my next move didn’t turn her off and stop this whole amazing night in its tracks. It was bold, but I couldn’t help myself, couldn’t even really control it. The taste of her ass still filled my mouth and my cock was determined to fuck that delicious little hole. I got up onto the bed and was squatting above her. She closed her eyes and reached her hand between her legs. I saw that she was sliding her fingers through her pussy, opening it to me, and I prayed that she would not hate me for ignoring it. I told myself that she had invited to me to explore my fantasies, she said absolutely anything would go, and so I went.
I leaned in and the head of my cock pressed against her firm asshole. She gasped and grunted, and her eyes shot wide open. My licking had well lubricated her ass but even still, it was going to be unbelievably tight. My first push barely even breeched her defenses and she screamed, quickly reaching her hand up from between her legs to cover her mouth. I pushed again and still made no progress. I could feel her clenching and holding herself closed. I wanted her ass so bad, uncontrollably, but I was afraid to push her too far.
With my third push she yielded, sighing, relaxing, and opening. The head of my cock was now being strangled by her clenching asshole and I had never been happier. As I pushed she continued to scream and moan, but as she did she opened further and began to swallow my cock in her ass. The sensation of anal sex was better than I imagined in my fantasies. The tightness didn’t stop at Hannah’s asshole; the inside of her ass was that tight the whole way in. As her asshole gripped and squeezed my shaft so did the rest of her ass so that my cock was enveloped in flesh tighter and warmer than it ever had before.
I pushed further and finally hit bottom. The hairs along Hannah’s pussy mingled with those on my balls and my cock was fully entrenched in her magnificent ass. Hannah let out one long moan, most certainly experiencing pain but I hoped pleasure too. I could feel miniscule muscle twitches deep inside, each one serving to massage my cock. Tight winces of her asshole absolutely rocked my entire body and I knew I was building to a fantastic orgasm. As much as I wanted this feeling to last forever, I knew we were probably nearing Hannah’s breaking point too. I lurched back, sliding about halfway out, eliciting a shocked moan from Hannah. At that point I forced back in, slowly but steadily, feeling her tightening ass fight the invasion of my cock. I reached the deep again and almost came, matching Hannah in grunts and moans, though mine were completely from pleasure.
My fantasies were truly coming to life, and this wild adventure had made me confident that I could take it as far as I wanted. This woman, with whom I had never even been close to intimate, was welcoming my assault on her virgin asshole during our first time together. If that wasn’t proof that she would do everything I wanted, I don’t know what is. And I wanted to make her eat my cum.
After a few more thrusts I was boiling and losing control. I didn’t think Hannah could take much more and I knew that I certainly couldn’t.
“Hannah,” I whispered, “do you still want to make my dreams come true.”
“Ye… ahhhhhh… yeah….. baby,” she managed to grunt.
I pulled out slowly and carefully, savoring every millimeter of clenching ass along the way. Pulling out was driving Hannah crazy and both her hands had shot up and were squeezing her ass together, both holding me in and expelling me simultaneously. When I exited I held my cock in my right hand and made my way around in front of her. Hannah slouched onto the bed and was still holding her ass with both hands.
“Then open you mouth,” I commanded, enjoying being a little dominant. Hannah lifted her head and looked dazed. Her eyes met mine and her chin dropped. Every time Hannah and I were together, whether it was eating a meal or chewing on a pencil or nibbling on her finger, I had always imagined my cock being pleasured by those beautiful lips. I reached my left hand out and held her chin, angling her head up to face me. Her mouth was open wide and her soft tongue sat on her bottom teeth, inviting my cock to slide in. She stared directly at me with wide eyes but clearly held no malice or disapproval. I think she was as lost and unsure as I was for most of this, but her gaping mouth told me that she was willing.
I guided my cock onto her tongue and felt her lips gently wrap around my shaft. She looked so beautiful with her mouth around my cock, and assuming this wasn’t going to be the end of our sex together, I vowed to see her like this every chance I could. Her tongue moved back and along my shaft until it reached the underside of my head and with a few strokes of my hand at the base I felt my cum rushing to climax. I pushed a little deeper, careful not to choke or gag her, though in truth those were some fantasies of mine as well. I threw my head back as the first wave of cum blast across the precipice and fired against the back of Hannah’s throat. My orgasms always produce a lot of cum but I knew this was going to be gallons. I looked back down to see Hannah’s eyes close and her throat begin to swallow. I pumped again, gushing another load down into her throat. Hannah swallowed hard but couldn’t keep up. I quaked with pleasure as the full quantity of my cum began flooding her mouth in repeated and powerful bursts. Hannah’s cheeks filled and cum began to seep out the corners of her mouth. Still holding her chin in place I took my right hand off my cock and gripped the hair behind her head. I held Hannah still to ensure that every last drop of cum would flood her sweet mouth. The bursts subsided, giving way to the final ecstatic throes of climax where the last and thickest cum from deepest within my balls doesn’t burst but rather oozes down my shaft and into Hannah’s crowded mouth. Hannah was still overwhelmed and full of cum. I started thrusting gently, using my spent but still swollen cock as a plunger to push cum down her throat. My plunging pushed cum out of her mouth on all sides and down her chin, but Hannah swallowed and sucked my load down her throat.
After finally pulling my spent cock from her mouth I collapsed backward and onto my bed. I laid in ecstasy, beaming, paralyzed with pleasure. I heard Hannah suck in her first post-cum breath and gag a little my load still coated her throat. I expected she might just collapse down there, or get up and wobble to the bathroom, but to my surprise I felt Hannah’s small hand slide up my leg until it reached my cock and balls. I was even further surprised to feel the unmistakable warmth of Hannah’s tongue massaging my softening cock. I could hear little slurps as she pulled globs of cum that had proven too much for her back into her mouth. She nibbled and snacked on me for a few moments, cleaning cum and fluids from my entire package, before she slid up next to me and put her head on my chest. Neither of us said a word and we fell fast asleep.
I awoke later that night, around midnight, with Hannah still sleeping and breathing gently on my chest. We had gotten back to my place about 8 pm, so it was early for bed even after our exercise. I was wide awake and, not surprisingly considering the beauty that was draped across me, so was my cock.
I gave Hannah a kiss on her forehead and my right hand began caressing her soft back. She slowly roused to consciousness and gave me a few sweet kisses on my chest and neck. Noticing my cock, standing tall, Hannah reached down slowly and began gently stroking my shaft. The silence was interrupted by Hannah’s one of a kind cute giggle.
“I can’t believe you fucked my ass,” she exclaimed, wiggling against me as if she’d just said something really gross.
“I was pretty surprised you let me,” I admitted sheepishly. “What did you think?”
“Well, it hurt,” she said, and she looked up at me with a very serious expression. I thought she might be telling me that it was a one time thing because she didn’t like it but instead she said, “but it was so fucking hot.”
“Wow, yeah, it was, for me,” I tripped over my words. I hoped that meant we’d do it again because it was going to take a lot more than once to satisfy all my lustful fantasies.
“I love you,” Hannah said, looking up at me and just melting me with her gorgeous eyes.
“I love you,” I replied and we shared a soft kiss. That was the first time we’d ever said that, and I was sure it wasn’t just a hormone-fueled lie. Hannah had become so vulnerable to me, and I to her by exposing my fantasies at the risk of turning her away, and we had come out of it closer.
Hannah continued to stroke my cock, with a little more vigor now, and I think she was planning on starting again.
“Why don’t we take a shower,” I suggested, and Hannah nodded. As she got up I took in how beautiful she was once again, admiring her body from each new angle I saw. Her breasts were full and looked heavy and I found myself aching to explore them. Her stomach was neither athletically flat nor flabby, but had a softness that somehow seemed inviting. Being only five feet tall she had generally short legs, which of course finished in a perfect ass, but as she climbed out of bed and she led me to the bathroom I noticed how strong and sexy her legs were. We pinched and tickled as we got the shower ready, enjoying experiencing each other’s bodies for the first time.
Our bodies caressed one another for the entire shower. We lathered up and slid against each other, cleaning and feeling and groping all at the same time. My cock remained hard throughout and Hannah teased me with her soft hands and the wash cloths. Finally, when most of the suds had been rinsed away, our lips met and locked together. Our tongues twisted around one another and we would stay locked in a passionate kiss for most of the rest of the shower. As our tongues teased our hands squeezed and groped aggressively. I tugged at Hannah’s hair, cupped and squeezed her ass, and rubbed her back. She explored my skin as well, roughly squeezing my arms and back. When she pulled away slightly to access my cock, my hands swept to her front and cupped her fantastic tits. They were in fact heavy, substantial, and I kneaded them hard. Hannah moan her approval and started pumping my cock. She gripped it tight and I was sure I would cum in her hands if she kept up for long. Grabbing her ass with both hands I lifted her off her feet and pushed her up against the back wall of the shower. With all the suds and water all of this was very slippery and dangerous, but I managed to hold my balance and line my cock up with her pussy.
Still deeply lost in each other’s mouths, I pressed my hips forward and my cock penetrated her pussy for the first time. The feeling was fantastic. Hannah’s pussy was tight, not restrictively so like her virgin asshole, but instead like it was a perfectly snug fit for my cock. Hannah squealed as I entered and our kiss finally broke. She looked at me with more lust in her eyes than I’d ever seen before. Her pussy was beyond warm, literally hot, and I could feel her desire coursing through her as I slowly buried myself inside.
I started slowly thrusting, barely moving in or out and more simply rocking in her pussy. Hannah gyrated on my cock and licked her lips in the same clockwise rotation as her gyration. Taking this opportunity, I bent my head down and buried my face in her fabulous tits. Because my hands were stuck on her ass holding her up, not a bad place for them though, Hannah took her tits in her hands and guided each nipple into my mouth. Hannah clearly enjoyed nipple play, so I spent a good deal of time licking and sucking, even gently biting, the whole time letting her enjoy the sensation of my cock buried as far inside her as I could muster. As I continued to suck I heard Hannah’s breath and moans change noticeably. She was building to climax, and after experiencing the best orgasm of my life a few hours ago, I wanted Hannah to cum her fucking brains out. I stood rigid and pressed my cock in as deep as I could, letting her dictate the pace and motion. Soon, Hannah found a particular spot inside that sent shivers through her body each time it brushed against the tip of my cock.
Hannah focused her bouncing and rocking on this spot and, as I increased the intensity of my tit sucking, began to quake and shutter. Her moans turned into a solid cry and she bit into my shoulder to stifle the scream. Her body shook and she gave one hard hip thrust, planting herself as deep on my cock as she could, and she came. Her pussy clenched and released repeatedly and she moaned expletives into my ear. Finally she slacked and relaxed, still impaled on my cock, and we met for another long kiss.
We weren’t finished, however. I was still rock hard and Hannah still seemed horny and willing. I lifted my right leg up and braced it on the bathtub ledge. In doing so I removed one hand from holding Hannah’s ass and used it to further spread her legs. At this point she was pinned up against the shower’s back wall with her right leg wrapped tight around my waist and her left leg held out wide by my right hand. My left hand wrapped over her leg and held her by the bottom, supporting her, and it truly was a miracle that we were able to balance and stay up this precariously.
This new angle offered me unprecedented access to her pussy; Hannah was spread wider than ever. Slowly I pulled my cock out to the tip and sunk it back in. Hannah moaned and swore with lust. Never before this evening had I heard her use this many swear words. After a few slow insertions to ensure that this angle would work, I began increasing the tempo and strength of my attack. Soon my thrusts were hard and violent, pounding my cock deep into Hannah’s pussy. She shut her eyes and opened her mouth, silently shouting as my cock punished her pussy. I fucked as hard as I knew how, slamming into Hannah and nearly cumming with each thrust. Hannah was relaxed and open, letting me violate her, and still her pussy was agonizingly tight. Soon my balls ached and I stared deep into Hannah’s eyes. My final thrust was the strongest, forcing a pained yelp from Hannah as I impaled her with my cock. I removed my left hand from her ass and squeezed her hip tight. Now neither of my hands were under her, she was literally pinned to wall by my cock. My cum burst out of my cock and soaked her pussy. She moaned with delight as I filled her. Cum began sliding out of her pussy and I imagined no hole on her body could hold all my cum. I pumped the last of my load into her with a long sigh before leaning into her and slumping from exhaustion.
Once again we let the shower clean us, and after drying off and many long kisses, we retreated to my bed. The sex had been exhilarating but also exhausting, and this time we fell asleep and slept the rest of the night through.