12 comments/ 149183 views/ 20 favorites Connor By: bitsieblue Positive voting responses will lead to sequels! My name is Wren O'Malley, and I want to tell you about the first time I got fucked. I had just turned eighteen years old, and I'd been such a tomboy for so long that sex had pretty much escaped my attention until, near the end of my senior year, one of my best friends broke confidence and told everyone in school I'd never had sex. Furthermore, I'd only ever kissed a guy once, and I'd been caught by my parents doing it. I was furious. It had always seemed to me that the when and the how and such should be my choice, not subject to anyone else's opinion, but now every guy in school was making obscene suggestions and every girl was smirking. I had a couple of true friends, who tried to reassure me that it was no big deal, that the girls were just jealous because I valued myself more than they did, and the boys just wanted to fuck a virgin. That, I just couldn't understand. I'm only 5 foot 1 and 95 pounds. I knew my long red hair was something special, but my eyes are brown. Unimpressive. I decided that my friends, albeit good friends, were also virgins and trying to make themselves feel better about their choices by supporting mine. So a couple of weeks before we were graduated, Mom and Dad had decided to go on a cruise. But since they'd caught me necking with Jordan, they were a little anxious about leaving their little girl alone. So they decided they'd have Connie check in on me every day. I didn't really mind. I liked Connie, and I knew there was nothing to hide. Now, Connie is a man. His real name is Connor, but we've always called him Connie. He's about their age, late thirties, and one of Dad's best friends. He's 5 foot 7 and muscular. He's got shoulder-length brown hair, thick and full, which I loved. His eyes are a piercing blue, and very expressive. He wore a goatee, which I also loved. He always came with us on family outings, to the ball games, picnics, and fishing trips we took. Sometimes he'd bring a girlfriend, which I hated. They were always tiny and petite, like me, which I figured was because Connie's not too tall himself. I kind of had a crush on Connie. I thought he was incredibly good looking! I'd been very careful not to tell anyone at all at school that my parents were leaving town. I could see them starting a big party out of my control, or, worse, trying to set some guy up to fuck me. So I was all alone that first night they left. I enjoyed the peace of the house. I made my own dinner and got into Dad's beer a little bit, drinking two. I was feeling a little buzzed and decided it was bedtime. I went upstairs and took a long bath in my parent's bathroom. They have a jacuzzi tub, and I loved the feel of the jets on my skin. I turned one of them onto my pussy for a while and was panting when I got out of the tub. I went to my room and put on a sheer little nightie, pink, and climbed into bed, ready to play with myself and cum till I fell asleep. That's when the doorbell rang. I held my breath and looked at the clock. Nine PM. I peeked out the window to see who would be visiting at this hour and saw Connie's car in the driveway. I smiled at this unexpected surprise and bounded downstairs, yanking the door open. "Hi!" I grinned at him. "I kinda thought you'd call stead of just coming by... want to, um... come in..?" Connie grinned wickedly at me, his eyes roaming that pink nightgown. Oh, hell, I thought, realizing I'd forgotten a robe. But I was enjoying his eyes. Very much. He hesitated, as if he were making a decision. "Yeah, I'd love to come in for a bit, kitten," he chuckled, making me feel like a little girl again. "Gotta make sure you don't have any boys stashed away in here." I flushed with pleasure and giggled as I stepped back to make room for his wide shoulders to come through the door. "Boys? Me? As if! Check the house if you want to." Connie laughed and stepped inside, wrapping his arms around me and hugging tightly. I hugged him back, as we did. I closed the door behind him and crossed my arms over my chest to hide my tightening nipples. "You mean you don't have a boyfriend?" he teased. " I find that hard to believe." I shrugged and grinned. "Well... no... I don't. As you know. There's no one I'm interested in. Have something to drink." Connie turned towards the kitchen. "Yeah, I'd love something to drink. What do you have?" he asked, looking me over again. I blushed a little, probably not noticeable in the dim light. "I think there's some beer and whiskey in the kitchen... or cokes." I started padding across the carpet to the kitchen and turned on another dim light over the kitchen sink. Connie said "Whatever's cool with me." He seemed to hesitate for a second before following me into the kitchen. When I turned, he snatched his eyes up from my little ass. I just caught Connie looking at my ass. I was in a bit of shock. I'd never expected that of Connie. I squirmed as the refrigerator light showed through my nightie and pulled out two beers quickly, opening them with the opener on the door of the fridge. I handed him one and grinned as I clinked my bottle against his. "Don't tell Mom and Dad, okay?" Connie laughed as he took a drink of the beer. "It'll be our little secret... Now where do you hide those boys? In your bedroom?" His eyes gleamed with mischief. I laughed, too. "No. But you can still check." Connie arched an eyebrow. "Well, even though you say no, I still think I should check it out. That way when your parents ask, I can be honest. There were no boys, Mr. O'Malley!" Connie said this last as he pulled to attention, clicking his heels and saluting like a military man. I giggled. "Okay, c'mon." I drank most of the beer in quick gulps as I led him through the dim house to my pink bedroom with the big canopy bed in virginal white. Connie chuckled as he walked into my bedroom. "Damn. This is awfully adorable... It's entirely too cute, my dear," he smirked, knowing me for a tomboy. I shrugged. "Mom on a perfect-girl's-room decorating spree. What could I say?" I flopped back on the bed and finished the beer. Connie watched me throw myself down on the bed, his eyes gleaming still. He winked at me as he took a swig of beer. "And are you? Are you the perfect girl?" I gave a short laugh. "Hardly. You know why Mom and Dad have you checking on me?" Connie was still grinning wickedly, shifting from one leg to the other. "No," he replied, pretending innocence. "What did you do?" I made a face. "They caught me and some guy once... nothing was happening, we were just necking. But you know mom." I had to crane my neck to look up at him. He'd come closer to the bed. I realized I'd left him standing. "Hey, sit down." I scooched over on the bed. Connie laughed with glee, rubbing his hands together and kicking off his shoes as he sat on the bed next to me and leaned against the headboard. "Making out with a boyfriend," he teased me. "Such a naughty girl, so you are." I watched him sitting in my bed, and I felt suddenly very hot. I had to be imagining that Connie's eyes were all over me again. I made another face, this one with an accompanying obscene gesture. Connie laughed. "Oooohhh! Did I touch a nerve? Tell me, baby Wren, adult to adult, just how many men have you had sex with?" My eyes went wide and I blushed furiously. I couldn't believe he asked me that. I shrugged and didn't say anything. Connie didn't let up, he patted his hand on my thigh. "Come on, tell me." I mumbled something, but he pushed me again, so I told him. "None, okay? None." Connie's smile became a little more tender, less mischievous. "That bothers you, doesn't it?" I shrugged, still blushing. "I just haven't been with anyone. I haven't found anyone worth my time yet, so..." I trailed off and shrugged again. "But all my friends say I'm a freak." Connie gave a small smile. "What sort of man is worth your time, kitten? I'm curious." I thought about that for a minute. "I don't know. I mean, guys my age are still little boys, you know?" Connie laughed softly. "True. Guys your age can be pretty bad. I used to be one of them," he said, winking at me again. I was on a roll, though. "I want someone I can really talk to. I mean, you can't fuck all the time, right?" Connie's laugh was a bit surprised at the use of the vulgarity. "True, very true. You can't fuck all the time. It's good to be with someone you can talk to when you're not fucking. I hesitated as I suddenly saw Connie in a different light. In the light of possibility. He was in my bed, and we were talking. His eyes had been doing a lot of talking, too. It made me shy, the possibility of fucking Connie. I laughed. Connie was looking at me gently, speculatively. "Tell me what you're thinking." I shook my head and blushed, hiding my face on the covers between our heads. Connie chuckled a little and stroked my thigh. I shivered, skin goosebumping as his fingers made the flesh come to life. "You're embarrassed, aren't you? Remember, we're friends. Tell me what you're thinking." I peeked up at his reassuring smile for a moment, my eyes still shaded by my long hair in my face. "I was thinking it would have to be someone like you." Connie smiled sweetly, looking a little embarrassed himself. "That's very sweet of you to say." I smiled slowly. He hadn't told me what an idiot I was. "You're a very sweet girl," he continued. "It's good to see that you're trying to find the right opportunity before you do it." I sighed, still smiling. "Still, I guess I should get it out of the way, huh?" Connie's hand was still on my thigh as he conceded the point. "Sometimes that's best, so it doesn't take over your life or become a big scary thing." My heart was pounding. My thigh seemed on fire at the light touch of his fingers. "Can I ask you something, Connie?" "Sure." "Do you want to fuck me?" Connie's wicked grin spread across his face as his eyes roamed my slender frame. "I'll be honest, kitten. The thought has crossed my mind. More than once." My breath caught in my throat. I smiled, eyes crinkling at him. "Can I ask you something else?" My hips moved against his hand. "Sure," he agreed, eyes still on my body. I noticed the lump in his trousers growing. I felt attractive, powerful. It was heady. "Would you fuck me right now?" Connie's grin got even more wicked. "Are you sure about that, kitten?" I nodded, my face still mostly hidden by my mane of hair and my arm. Connie's eyes found mine under all that hair. "You know, kitten, I should warn you that I'm rather large. I couldn't see much of his bulge now. His body had moved closer to mine. His hand stroked up my thigh to the curve of my hip. I tossed my hair out of my face so I could see him well. "Good," I said boldly. "That way there'll be no doubt, will there?" Connie chuckled. "I always knew you were a naughty girl," he murmured moving closer still. His eyes were still surprised when I moved towards him, my mouth boldly meeting his. Connie moaned softly, pressing my slight frame to his thick chest, meeting my eager kiss as our mouths opened and our tongues met, hard. I gasped, sensation shooting through my body. This was what had been missing. I wrapped my arms around his neck, pulling him mostly on top of me, legs entwining like our tongues. Connie pressed down on me, carefully resting his weight just a bit on his forearms so as not to crush me, but definitely enough so that I felt aware of his presence. He continue to kiss me, his tongue exploring my mouth. I wrapped slender legs wrapped around his waist and rubbed my tiny mound against him, back arching to push harder, sucking at his lips and tongue. He ground into me, letting me feel his bulge. It was huge. I broke the kiss, breathless "Oh god," I breathed, "You weren't kidding were you? I want to see." Connie grinned wickedly. "Take it out for me, kitten." He sat up on his knees between my legs, pulling his shirt off and exposing that chest corded with muscle. I fumbled inexpertly with the buttons on his fly, pushing his jeans down as far as my hands would reach. He watched me intently, obviously wanting to see my reaction to his cock. I pulled my feet up on his hips, pushing the jeans down with them as I hooked my fingers in his boxer briefs, pulling them out and over his cock and down. My eyes were wide as saucers, I'm sure. It was huge. "Oh my... how big is it, exactly?" Connie's cock was jutting free, pulsing, pointed at me menacingly. It was bigger than my arm. "It's about 8 inches long and about 6½ inches around." He smiled gently, hands rubbing comfortingly on my belly. "Have you ever seen a man's cock before, kitten?" I slowly shook my head no. He watched me staring at his cock, fingers still on his briefs. "What are you thinking, kitten" I shook my head slowly. "It's too big. It won't fit. It will hurt..." I said. Connie smiled softly at me. "It will fit, kitten. It'll just take a bit of time. We'll have to go slow." I bit my lip, suddenly feeling raw and hungry. "But I don't want to go slow." Connie laughed softly. "We can build up to that, kitten," he said so softly as one of his hands slid down to my naked crotch and cupped my whole mound. My eyes closed, and my mouth opened in a gasp. "Oh god," I groaned, pulling at the low neck of my nightie, pulling my tits out the top. Connie continued teasing my sex, lightly playing with my clit after moistening his fingers with my juices. "Take off your nightie, kitten." I scooted up the bed enough that I could pull it over my head, letting my legs splay obscenely wide, enjoying catching him staring at my tiny slit with eyes glazed with lust. He continued rubbing his fingers against me, alternating between my pussy and my clit, stroking it all in one large motion. I groaned and my hands went to my breasts, squeezing. Connie pushed my hands away and started licking at the sensitive flesh. I squealed and my body arched under him again. He teased all around the tip with his tongue before sucking the hard nub in with teeth and lips. I groaned again, hips working against his hand. My fingers tangled in his long brown hair, pulling. Connie's mouth pulled extra hard at my nipple, and it popped free. I groaned. Connie attacked the other one the same way, tongue and teeth and lips, fervent, sucking hard. I pulled harder on his hair. I started to gasp as his mouth made fire shoot through my limbs, body jerking electrically under him. "Ooh... oh God, Connie, please lick me there," I groaned. Connie leaned down, glancing once at my face before moving his tongue across my pussy. My hips were rolling desperately. He stroked back and forth for a moment before moving to my clit and lightly sucking on it. My pink puss felt hot and wet and swollen. My fingers were on his shoulders, in his hair, pulling, as I watched him, panting, tense. I just got more and more excited, pushing my cunt harder against his face as he continued the light teasing of his tongue tip. As I pushed up, though, he licked harder, and gently slid a finger just inside my pussy. I moaned, long and low, back arching, my pussy clutching at his finger. He twisted his fingertip back and forth as his teeth ran over my clit and I squealed, frantic. "Connie, please!" I begged hoarsely. He pushed his face against my pussy so that when he talked, it rumbled through me. "Please what, kitten?" "Please! I don't know, do something! I need more," I implored. Connie rubbed his goatee all over my pussy, finger pushing deeper and deeper, slowly, until his finger filled my little cunt. I squirmed and mewled, fingers on my tits, crushing them, pulling and twisting at my nipples harshly. Connie sucked in his breath, watching carefully as he drove me insane. Finally he cupped his mouth over my clit, sucking softly, tongue dancing over the throbbing nub. I screamed. Connie sucked harder, tongue flicking harder, finger twisting again, and I screamed louder, nails digging into my tits. Connie moaned against my little mound and started fucking me with his finger, faster, harder, sucking my clit hard, and I went nuts, thrashing and screaming and finally cumming on his face. It seemed like I came forever, in waves, the sensation receding only to be pushed over again by Connie's tongue, softly caressing as I peaked, then attacking when I tried to rest. Finally he stopped. I panted, exhausted on the bed, looking down at his glistening face as he crawled up from between my legs. I was shaking. "Jesus Christ." I said, eyes wide. Connie grinned, and it was different now. A knowing grin. He passionately, languidly sucked at a nipple. I groaned. He kissed my mouth hard, tongue thrusting into my mouth and I tasted my cum in his mouth. I sucked greedily at it. Connie's hands were on my tits and belly, squeezing, passionate but slow, pulling at my nipples. "Lick your juice off my face, kitten," he demanded. I complied, arms around his neck, holding his face to mine as I sucked at his goatee, licked at his mouth and nose, hungry for my taste on his skin. Connie began rubbing his thick shaft between my legs, making me whimper as I cleaned his face. When I opened my eyes, his were on me, full of lust. "I want you to suck me, kitten," he said, and I nodded as he stood, pulling his clothes the rest of the way off, then yanking me roughly to the side of the bed. My eyes burned. I would do anything he said. He hung my head off the side of the bed and stood, cock near my face, fingers caressing my lips. I opened them as he nudged with his cockhead, and he pushed the tip in, stretching my little lips. I groaned. His hands slid down to my tits, rubbing, kneading, pulling at the nipples as he fucked just the head of his dick into my mouth. His eyelids fluttered and his head rocked back as I sucked, flicking my tongue the way he'd done my clit. I groaned and rubbed my belly, my thighs, rubbing the sticky juice over my skin. Connie's fingers moved farther down my body, too, our hands meeting and twining before breaking apart to explore my body. More and more of his thick cock entered my mouth until he bumped the back of my throat. His hand cupped my wet bush, kneading so the lips spread and were pushed together. He pulled up, pulling my little slit wide, and tapped my clit with the fingers of his other hand. I groaned deeply on his cock, making him groan and thrust in my mouth. He tapped his fingers harder, then harder, till he was spanking my clit with them. I shuddered and yelled around his thick meat. Then Connie leaned down over me, cock pushing hard on the back of my throat as he licked my cunt again. This time, he held my cuntlips wide and sucked, licked, and bit my clit hungrily, hard. His cockhead kept pushing at my throat, and I swallowed, trying to take the huge thing. It just wouldn't go into my throat, but I groaned, mewled as he worked at my pussy again. I came quickly, screams muffled by the thick shaft pumping slowly at my mouth, and then Connie bit my clit. I came again, thrashing, seeing stars as he licked the little nub gently. Connie stood, hauling his cock from my mouth, pulling with some effort. If I'd thought it was big before, now it was mammoth, pulsing as he stared down at me with lust. He turned me around on my white bed, pushing his jeans under my hips. Then he climbed between my legs, eyes locked on mine, both burning, as he licked his way up my legs, across my pussy lightly, up my belly to my tits. There he stopped briefly, tugging on my nipples with his teeth and lips, his tongue flicking hard over the distended tips. I groaned, body rocking up to his. His thighs were between mine, pushing mine farther and farther open. "Wren. I'm going to fuck you now," he told me, and sat back on his knees. My eyes strayed from his to that monster cock as he rubbed it all over my pussy, teasing my clit and my hole. Connor I am director of sales for a hotel. Most times I am tucked away in my office while my sales team handles the booking of the banquet rooms and group blocks. Both sales agents were busy when a potential customer came in to the lobby asking for information. The front desk clerk buzzed back to my office and asked me if I was free to come out and give some assistance with booking a banquet room. I was pleasantly surprised when I came out to the lobby. There he was around 6'2", dark hair and a neatly trimmed goatee. A neatly pressed button up and snug fitting jeans. Shaking his hand I introduced myself and showed him down the hall towards our banquet rooms. Stepping into our larger room with the small dance floor, I began to ask my basic sales questions. "What type of even was he having?" "A birthday party." "How many guests would be attending?" "Possibly 100 people." "Would there be music and or food?" "Yes, both food and a DJ." "We could provide both tables and chairs, setting up the room to your specifications." He said, "I won't need 100 chairs. Maybe just 50 scattered through out the room and some high rise tables if possible and also two larger tables for the food and gifts." After walking around the room I told him "This room should be the perfect size for your event." His eyes locked onto mine. He just stood there quietly. I responded with a shy smile as I nervously straightened my skirt. He smiled then walked toward the door. "Could I get back with you on the dates and other specifics?" "Ofcourse," then I asked "Would you like a quote on the price of the room?" He smiled and said "No, money is no object. I am VERY pleased with what I have seen so far", emphasizing the word very. I nervously cleared my throat as I opened the door. "If you will please follow me back to my office I will get you one of my business cards." He quickly replied, "Gladly." He stopped in my office door way. As I leaned down to get one of my cards I heard him clear his throat. I smiled as I momentarily held my pose. I turned around to a very sexy smile. I was speechless. I have been in this business for a good while now. No one has ever had this effect on me. After taking my card from me he shook my hand again. Slowly releasing my hand he said "I look forward to seeing you again." As he turned to walk away I remembered he never gave me his name. So to his back I loudly asked "Could please get your name sir?" He looked back over his shoulder with a grin, "Connor." I practically fell into my chair after he left. I took a deep breath and shook my head as if to clear the cobwebs. Connor had set my body on fire with just his eyes. How would I survive another meeting? A week later Conner calls to set up a meeting to finalize things. He also mentioned his was interested in blocking off a group of rooms for guests who want to stay over night at our hotel. On the day of our meeting I left word for the front desk clerk to just show him to my office when he arrived. The date he wanted for the party was open. So we completed the contract for the banquet room and he paid the deposit. We agreed that the balance for the room rental would be paid in full by the night of the party. It was when we were diagramming out how to set up the tables and chairs that I got my surprise. He asked for two corners of the room to be left open. I agreed that we would set things up to his specifics. He said that they would set up a spanking bench in one and a Saint Andrews Cross. I stopped writing and looked up at him like a deer in the headlights. He just gave me that sexy smile. He assured that all of his guests will be legal consenting adults. I tried to breathe slowly and continue my paperwork. Breaking the silence he asked, "Could look at your guest rooms now?" I nervously started stacking my papers as I stuttered, "Yes, ofcourse." I quickly grabbed my keys and walked toward my door. Connor just laughed. Stopping by the front desk I asked for an available room to see. I asked her not to rent the room until we come back from viewing it. Unlocking the door I walked in first. I stood quietly while he looked over the room. He sat on the bed rubbing his hand over the area beside him. "This is a nice soft bed." He was staring at me. I coughed a little and turned toward the tv. I was hoping maybe to take his attention off the bed by talking about the features of our tv. "We have expanded cable with 3 movie channels on a 32" HD tv." He was still staring so I walked over to the bathroom. "In here there is an over sized shower and tub with Jacuzzi jets." As I turned to walk out of the bathroom Conner quickly appeared behind me. He asked, "Could you repeat that please?" I turned to go back over the features and he gently pushed me face first toward the counter. "These counters seemed to be just the right height." Connor said. I met his eyes in the mirror. He moved my hair to one side exposing my neck. Quietly I added, "The mirror gives a great view as well." In between the kisses he was putting down the side of my neck he gave a growl. I began to unbutton my blouse as he slid his hands under my skirt pushing it up around my waist. I instinctively began to rub my ass against him. His hand went into the side of my panties quickly, dipping one finger then two between my pussy lips. I started to moan. I was so close. I felt a sharp nibble on my neck as he removed his fingers. "Not yet" he commanded as he removed his hand from my panties. We both were watching in the mirror as he took off my blouse and bra. He began to twist on my hard nipples, palming my tits as he squeezed them together. He turned me around and sat me on the counter. He began to suck my tits pulling on my hard nipples with his teeth. I began to play with my tits, squeezing them as I offered them up to him. This time Connor moaned. "Play with you pussy while I unzipped my pants. I need to see if you are wet enough for a good fucking." Pulling my panties to the side I slowly began to finger myself. He stood back watching me as he stroked his thick cock. Hoping to drive him as wild as he has me I began to suck on my wet fingers, tasting myself. He gave a big growl as he pulled me off the counter and pulled of my panties. "Let me see that sweet ass" as he bent me over the counter. He commanded, "Spread those cheeks." I watched in the mirror him pulling a square foil package from his pocket. I started to stand back up "No, not my ass." "No sweetie, I want your pussy today. That tight ass will be mine the next time. " He slid into me with one slow push. His thick hard cock stretched me, filling me up. With a fist full of my hair he had me look into the mirror. "Tell me what you want," he demanded. I could hardly speak. He pulled out of me a little then putting his hands on my shoulders he pulled me down onto him. He stopped balls deep inside me. "I won't move until you tell me." Then he pushed forward adding pressure to my g spot. "Oh please Connor Fuck me. Fuck me now", I begged. Sliding his hands down my arms he pulled them behind me. Pulling me back to him he began to fuck me harder and faster with each stroke. Quickly he drove me over the edge, shortly after I felt him give his final push as he orgasmed. Quickly we both cleaned up. Quietly, I was thinking about his statement about the next time. Just before we left the room he pushed me against the door. He kissed me passionately. "Yes, I meant what I said about the next time." I just smiled! Back in the lobby he extended his hand for a handshake. He smiled. "Thank you for all your help. I look forward to seeing you again." I felt like I was walking on a cloud back to my office. After sitting down and catching my breath I called up to the front desk. I had he put that room on the housekeeping list for cleaning tomorrow. Not once have I ever shown a guest room and had such an experience. There is just something about Connor. I cannot wait to see him again!!