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.”