Connor

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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. Itwas 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 willhurt..." 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.