First Times: Nine Tales of Innocence Lost

by Natalie Deschain

  I was just lying there in my sleeping clothes. He came in with a little bag from the drug store and dropped it on the bed. Then he sat down next to me. I sat up and waited.

  “So,” I said.

  He took the hem of my shirt and pulled it up. I lifted up my arms and let him slide it away, and then my arms fell to my sides. I watched him as he slid my bra straps down and reached around me, hugging me to his chest as he did it. I started unbuttoning his shirt, and then his pants.

  He shifted onto the bed and pushed me down, and finished undressing me. He slid my shorts down, and then my underwear. I kept my legs pressed tightly together out of instinct. He caressed the spot just above my pussy with his finger while he leaned down and took my nipple in his mouth. He sucked hard, and tugged on my breast with his mouth.

  My nipples went hard in an instant, and I let out a little moan. He was down to his boxers now. I reached in and pulled out his cock, feeling it in my hand as it hardened, getting bigger and bigger. I felt a twinge, a kind of itch in my butt, as I thought about what I’d agreed to.

  “Do you want to put it in now?”

  “Not yet,” he said.

  “Should I suck you?”

  “No, I want a turn. Spread your legs.”

  I didn’t realize what he meant until my calves slid across the sheets and I was exposed to him. He shifted over on the bed and laid down between my legs, and I felt his breath on my skin. A shiver ran up my spine. I’d never been exposed like this to anyone before.

  Then I felt his tongue.

  The touch was quick, hot and wet. I squeaked and jerked and my legs closed around him. His hands slid under my butt, and I folded my arms across my chest, hugging myself as I felt his tongue again. He traced slowly all around my pussy before working his way between my folds, then up over my clit, then back down again.

  I let out a soft sound. I was used to playing with myself in silence, keeping quiet so no one would hear my cries of pleasure. It made me strain and bit my lip as he lightly grazed my clit with his tongue, then worked it at my entrance, pressing it into my pussy. With his face buried in my sex, he looked up at me over my stomach and met my eyes.

  My head fell back and he tongued me softly, working me up, then moved faster and faster, the tip of his tongue darting everywhere before he dragged the whole hard, wet thing over my clit and I jerked and squealed through my fingers.

  “Like that, huh?”

  “Yeah,” I said, breathless. “It’s good. You wanna do it now?”

  “Do what?” he said, smirking.

  “Put in my butt.”

  He lifted up, moving over me. I looked down at his cock and my heart hammered in my chest. He was big. Very big. A little scary big.

  “You’re a grown woman. You can say it.”

  “Are you gonna fuck my ass, or not?”

  “Turn over.”

  I rolled over. His cock brushed my hip as I did. I flopped on my stomach and he pressed my legs together, sat down beside me, and grabbed his bag. He unpacked a little bottle of clear liquid and smoothed some onto his finger, and worked it between my butt cheeks.

  “Ooch!” I yelped. “It’s cold.”

  “It’ll warm up.”

  He worked the slippery liquid all around my asshole before dipping his finger in. The feeling if his fingertip sliding easily into me was strange, and I liked it.

  “What are you doing?”

  “I need to lube you up,” he said, softly. “It can hurt if we don’t do it right.”

  My stomach fluttered as I looked at his big cock. I thought about that.

  “I’m going to work my fingers in a little deeper.”

  “O-okay,” I said, breathless.

  I could feel his finger moving inside me. He used more of the lube, and slid in another. He moved them together, pumping into my asshole before spreading, moving them around, tickling the inside of my ass.

  “Play with yourself,” he said, softly.

  My hand slipped under my body and I played with my pussy while he worked my ass. I let out a shocked sound as he put a third finger in. It felt so slipper, and I felt stretched. Shivers went down my legs and I started to sweat. It felt so weird.

  “We’ll go slow, okay. Turn on your side.”

  He turned his hand away and I rolled over. facing away from him. I looked over my shoulder and watched as he squirted a lot of the lube on his cock and slopped it up, stroking until there was a thick shiny coat of the stuff all over his shaft. He put his hand under my thigh and pushed up my leg, turning me a little.

  “Pull your leg up. Good. Now, relax.”

  He shifted behind me and his chest pressed into my back. He took his cock in his hand and nestled the thick head against my asscheeks. Feeling it press against the tight puckered hole made my heart pound in my chest and my throat went dry. Just the feeling of it touching me made me shiver and I felt fear and anticipation all at the same time.

  “You ready, baby?”

  “Y-yeah,” I nodded.

  He gave a slow, gentle push, gradually building the pressure. It wasn’t like a finger at all. He was so much thicker, and his cockhead pushed and pushed and I felt a little twinge of pain in my ass before I let out a low, long breath and my body just opened. His head popped inside, eased by the lube, and I let out a low moan.

  “Oh. Oh shit it’s big,” I said.

  He slid his arms around me. “Shhh,” he said. “I won’t hurt you. Real slow, okay? Here.”

  He took his other hand and moved it between my legs. Gently, he slipped a single finger inside me and palmed my clit, moving his hand slowly, teasingly as he upped the pressure and more of his shaft slid inside me. I let out a low groan as I lay there, taking his cock in my ass.

  The feeling was so strange. It packed so many sensations together I couldn’t sort them all out. It didn’t hurt, but I felt a kind of pain. Good pain, pain that I liked. I felt his cockhead pushing deeper, opening me up as it slid further inside my body. I felt my walls stretch around him and quiver and pulse as they gripped his shaft. When he was finally all the way in and pressed tight against me, I was so opened up, so used, that I just laid there and whimpered.

  “You okay, baby? You want to stop?”

  I shook my head. “I like it.”

  He fingered me and slowly rolled his hips. Barely moving, his cock pulsed inside me, sending waves of heat spreading through my body. He lightly kissed the curve of my jaw, my throat, and whispered in my ear.

  “I’m going to cum in your tight little ass. You want that?”

  “Yeah,” I groaned, “Please.”

  “Tell me how you want it?”

  “Harder.”

  He moved a little faster, drawing back a little more. I could feel every inch sliding inside me, feel every movement, so intense it made my toes curl. Nothing I’d ever felt was like this. I wanted it to go on forever.

  Slowly, I lowered my leg back down. It tightened my body, gripping his throbbing cock. He kissed my shoulder and slowly worked his finger inside me and rubbed my clit. I hugged myself and shook from the intensity of the stimulation. I felt so full.

  Very gently, he worked me onto my belly and pressed down on my back, spreading his legs so his knees were on the bed, and rested one hand on the back of my neck and the other on the bed. I fingered myself as he fucked me harder, moving his whole body. He drew back slowly, about halfway out, then thrust in quickly, then drew it again.

  Every time he went to thrust my body tightened in anticipation, gripping him hard as his thick shaft slid through the tight walls of my body. He went faster and faster until he was grunting, and lowered himself down on top of me again. I felt his cock throbbing, going so hard I couldn’t believe it, so hard I could barely stand to have something so thick and rigid inside my body.

  He rolled and I cried out as he pulled me with him. I lifted and fell on his cock, impaled, my back arched and a silent cry escaping my throat. He slid back up the bed, pushing with his heels, until
he could sit up on the pillows. He pulled me against him and closed his legs against mine and held me. My ass throbbed from the huge hard rod inside it.

  Again he cupped my breast, kissed my neck softly, and slid his finger inside me. My arms fell to my sides and I started to ride him, moving in slow motions, shuddering as I made myself keep moving despite the intensity of the sensations trying to make me freeze up. The feeling of his cock in my ass met and folded together with the sensation of his fingers and his hand working me.

  I finally began to slow. He slid down a little and started pumping me from below as I lay on him, working his cock in my ass in rhythm with his hand. My legs lifted as my body tightened and he grunted with every thrust. Something in him made him draw back further, move faster, push harder, driving me down an ecstatic edge. I rolled through a thin space that was between pleasure and pain and both. My cunt throbbed, heat tore through me and the fullness spread through my body until I could feel it under my skin.

  “You’re so tight,” he whispered.

  I couldn’t stand it. I thrashed, and when my peak hit it was an explosion, a blast that rolled through my body and sent waves of shivering heat and cold through me, sent shocks down my limbs, curled my toes and balled my hands into fists, clenched my teeth and made it feel like my hair was standing on end, like waves and waves of fingers were rolling over my scalp, and all though it that hot rod was there, throbbing, urgent, using me, filling me.

  He bucked up under me and lifted me up and I could feel it. I could feel the throbbing pulse as he spent himself inside me, as his motions became hotter, faster, slicker as he pumped the cum and slipped his cock all through it inside me.

  I sprawled out on top of him. He slid his arms around my waist and worked his hips slowly as he finished, and I slid off of him and landed on the bed with a little grunt. As his cock left my ass I felt the first real pain. Pulling out hurt more than putting it in, for some reason. I yelped a little and he turned around to hold me in his arms while I shuddered and whimpered from the aftershocks of the most intense orgasm I’d ever felt.

  My ass throbbed. It wasn’t sore, really, it just felt so weird. Like I’d been spread open.

  “Hey,” he said, after a while. “Lilly will be home soon. You should get cleaned up.”

  I nodded. “Was it good? Did I do good?”

  “You did great. Especially for your first time.”

  As he left and I went to clean myself up I felt strange. I sat in the tub for a long time, soaking in the heat from the bath, but I didn’t feel clean. I fucked my sister’s husband. Two parts of me warred. I couldn’t let this happen again, but it felt so good. If she found out…

  ***

  He gave me little gifts, touched my shoulders, but as the second semester wore on it happened less and less. In the summer, Lilly gave birth to a baby girl. By then the arguments had stopped and Todd slowly stopped showing me attention. We never had sex again after that. I thought about it, and I know he thought about it, but I refused.

  It was a terrible thing I did, a betrayal, but it could have been worse. He needed release and I needed to be that release. They have two kids now, they’re still together, and I’m going to marry my boyfriend when I finish grad school.

  His name is Jason. He always says he’s lucky to have found a girl that loves it in the ass.

  If he only knew how I acquired that taste.

  Taylor

  “We can work something out. We’ll make this work, I promise.”

  Dr. Carrington had been pressuring me on this for months. The head of the history department had something of a reputation as the ‘party professor’ around campus. People said her ‘gatherings’ could get pretty wild, and there were some pretty intense stories about the Christmas party she threw every year for her top students, but invitation only. I always found her a little intimidating. The idea of a female history professor conjures images of a beeteley woman in shapeless pantsuits with thick glasses and chalk dust in her hair, but Carrington was everything but. Taller than most men, she was a bombshell and it was said that freshmen and education majors and others that had to take cross-curricular classes in history would fight over spots in her courses, which always filled up fast. To take all her classes you had to be a history major and she had to pull strings to get you in. I ended up with her for my intro course by chance and she took a liking to me right away.

  Sitting in her office made me feel a little uncomfortable. It shouldn’t have, I mean we were two women. As nervous as she made me, I adored her. She was everything I wanted to be and never was. Besides her height she was buxom, shapely, and graceful. She had actually done some modeling in her youth and there were some borderline lewd pinup pictures of herself on her wall in a place of prominence along with her diplomas and awards. Her flawless skin was always just tanned enough to be a lovely golden color and freckles dusted her cheeks and chin, and her hair was a lovely honey brown that was almost dirty blonde, and she made it shine. She usually wore it loose, spilling down around her shoulders. As we had the argument again, she played with it, twirling heavy soft locks of hair around her fingers as she scribbled on a pad with a fountain pen clutched between her delicate fingers. Her big blue eyes had a kind of force, pinning me down in the chair.

  The upcoming trip was a big deal. Twice a year, Carrington put together class trips, one overseas and one within the United States, and spots on the trip were reserved for people taking the associated course. Now here I was, being talked into a trip I couldn’t afford. The course was covered by tuition, but the fee for the trip was more than I made in six months at my part-time job working at the record store in the mall. Yet I sat there and let Carrington write the course in on my schedule for next semester with the expectation that I would cover the costs. The trip was two weeks in Italy. Carrington had been planning this one for two years, which was, incidentally, why I had two courses in Italian as electives. The woman would not take no for an answer. We chatted about a few more things and she listened to my plans for graduate school, grinning her vulpine grin. It was settled. I was going to Italy.

  With her.

  The big day finally came. Carrington made a deal with me. If I kept an A average in her class, she’d cover half my costs and all my meals. That made it more manageable, but I was a few hundred short when the time came to put in my fee, and she told me not to worry about it. I ended up pacing my dorm room that night. We had to leave at three in the morning to catch the flight, so I paced and paced until two, then put on my backpack and grabbed my suitcases and trundled down the stairs, much to the relief of my sleepy roommate. From there it was half a block to the College Center and the vans. Carrington had her hair pulled into a severe ponytail and was dressed in sweats. Seeing her that was a shock compared to her usual designer suits and heels. Even without added heigh from her shoes, she was still imposing and of a height with most of the boys going on the trip.

  “Taylor!” she called as I drew near. “Here, put your bags in this compartment.”

  There were three big white vans with the college livery painted on the side. Of course, I was going to be putting my bags in the first one in line, and Carrington was probably driving. There were two other professors going, and two alumni, chaperones in all but name. The rest were the students in the class, fifteen of us in all. Carrington helped me heft my bags into the back of the van and took my arm. Her soft fingers gripped my wrist tightly, her thumb moving lazily over the side of my hand. She grinned at me and almost shoved me into the front seat, giving me pride-of-place. I would be riding to the airport next to her. She must have already down half of the absurdly tall coffee cup sitting next to her seat, and she gulped down even more after she slid in to place. She turned around to face the rest of the students.

  “Buckle up,” she chirped, grinning.

  She turned to me and lowered her voice as she tugged the gearshift down. “This is going to be so much fun. You’ll see. You have your passport, right?”

  I
yawned, and nodded.

  “You can sleep on the way to the airport, if you want. Once we get on the plane everybody should get a few hours of rest.”

  I didn’t need to be told. I nodded in agreement and then nodded off.

  When I woke up, My head was resting on her shoulder. I pulled away like I’d set my cheek on a hot stove and she smirked and gave me the side-eye.

  “Are we close?” I yawned.

  “We’ll be at the airport in ten.”

  We were leaving from Philadelphia. I did my best to perk myself up a bit as our little wagon train pulled off I-95 and flowed up the big, sweeping ramp that headed around towards the airport garage.

  “Here,” she said, pulling her coffee from the cup. “Red Alert double-mocha. I saved you a couple of swigs.”

  I took it and winced at the bitterness of the cold coffee.

  “Thanks,” I choked, slipping the now empty cup back.

  We pulled into the long-term garage and Carrington led the little procession to the next-to-top, mostly empty floor. From there we all saddled up. Carrington had the most luggage of all of us, and her million watt smile put most of it into the hands of the young men joining us on the trip. As did one of mine. I ended up with only my backpack and rolling suitcase. From there to baggage check, and then to cheek in. They had those spinny backscatter machines, and to my surprise, when it was Carrington’s turn, she looked right at the bored TSA official.

  “You’re going to feel me up anyway. I’m not getting in that thing.”

  She was waved through, and glanced back at me and winked as one of the agents ran the backs of her hands over Carrington’s ample chest. By then I was already through the backscatter machine and scrambling to get my shoes on. Carrington slipped into a pair of Crocs and walked over, patting my shoulder.

  “It’s too bad there wasn’t a spider in the irradiator machine. You’d get superpowers.”

  I gave her a look as I stood up, and wilted. I hated looking at her too hard. She was so perfect, so graceful and beautiful and the little hints of crows feet around her eyes and the single thin strip of silver amid the gold of her hair only made her look regal and wise. I rubbed my arms and grabbed my carry-on.