Cindy’s Stepsister Visits the Office

As I paced the office, I couldn’t help but feel a mix of excitement and nervousness. I had been waiting for what felt like an eternity for Cindy to arrive, and finally, I saw her bike pull up outside. I quickly ran down to let her in, ushering her inside and out of sight from the busy street.

“Quick, come inside,” I whispered, trying to composed myself as I gazed at her in her school uniform. “We don’t want anyone seeing you here.” I picked up her bike and carried it into the small storeroom downstairs, my eyes unable to help but linger on her beautiful bare legs and little bubble butt.

As I led her to the bottom of the stairs, I couldn’t help but feel a surge of blood rush to my dick. “Come on, I’ll show you my office,” I said, trying to sound suave despite my growing arousal.

Cindy smiled up at me as she climbed the stairs, and I strained to look up her skirt, my eyes drinking in the sight of her white panties. “You said you liked it,” she said, noticing my gaze. “I want to look good for you.”

“I would be following you on that bike for miles, just in hopes that you might flash me,” I replied, trying to keep my tone light despite my growing desire for her.

Cindy giggled and lifted her skirt, revealing her panties to me. “Like this?” she asked, her eyes sparkling with mischief.

“Oh my god, you need to be careful,” I said, trying to sound stern despite my growing arousal. “You are every man’s fantasy. Seriously, you can’t imagine how many men, besides me, would want to have their way with you, especially in that outfit.”

Cindy smiled and leaned in close to me, her voice barely above a whisper. “Have their way with me? You mean like the other night? I think I might enjoy that, at least with you. That was amazing.”

“That was more than amazing,” I replied, my voice shaking with desire. “But I would never hurt you. I would never do anything that you didn’t want me to do. There are other men who aren’t so nice… who might hurt you. Please be careful.”

Cindy’s smile widened, and she reached out to touch my crotch. “I trust you,” she said, her voice full of conviction. “I like that I don’t have to be careful with you. And I like that I have this effect on you.”

I looked down, my arousal evident, and felt a wave of shame wash over me. “I’m sorry,” I said, trying to sound contrite despite my growing desire for her.

Cindy’s smile softened, and she leaned in close to me, her voice barely above a whisper. “Don’t be sorry,” she said, her breath hot against my ear. “I love it. I take it as a compliment. No one has ever made me feel as attractive, desirable, like you do.”

“You are extremely attractive, and I have never desired anyone as much as I want you,” I replied, my voice shaking with desire. “That night was truly the best, most erotic sex I have ever had. It was unbelievable.”

Cindy’s eyes sparkled with mischief, and she leaned in close to me, her voice barely above a whisper. “How did you learn to do that with your mouth… your tongue? That was amazing.”

“That is sweet of you to say,” I replied, my voice shaking with desire. “I’ve read a bunch on techniques, but I think practice is the best way. There were some articles I read that taught me some tricks to hit your G-Spot, but you are too tight for my fingers to reach that, at least from the front.”

Cindy’s eyes widened, and she leaned in close to me, her voice barely above a whisper. “What do you mean ‘from the front’… do you mean you could reach it… um… from my… from the back?”

Cindy’s eyes sparkled with excitement as she leaned in, her voice barely above a whisper. “I would love to try. It’s something I read about. Not sure if it would work, or if you would enjoy it… but I know I would.” My dick stirred, betraying my attempt to maintain a neutral tone.

“I’ve never been able to talk to anyone so openly like this. Communication is everything when it comes to sex. You have to tell your partner what you like, and what you don’t like.” Cindy’s gaze drifted off, her brow furrowed in thought.

“I would love to experiment,” I said, my voice low and husky. “Did Chloe like it when you… um… you licked my… um…” I trailed off, allowing Cindy to fill in the blank.

Cindy’s eyes snapped back to mine, a hint of a smile playing on her lips. “That was the first time I ever did that. I never really wanted to before.” I could sense her curiosity, her desire to explore the unknown.

“There is nothing about you that grosses me out,” I said, my voice filled with conviction. “I am very oral, and I loved doing that with you. That was about as intimate as I could get with you. You are beautiful… sexy as hell, top to bottom.” Cindy’s cheeks flushed, and she giggled, her eyes sparkling with mirth.

“Do you want to see my tan line?” she asked, her voice teasing. She lifted her skirt again, and pulled the front of her panties down, exposing her pale panty line and a hint of her sparse bush.

I felt a jolt of desire, my dick straining against my pants. “Dammit, Cindy… you are going to kill me. Or at least ruin my pants.” Cindy laughed, her eyes glinting with mischief.

“Am I in trouble?” she asked, her voice husky. “I’m sorry… I didn’t mean to make you so uncomfortable. Are you going to punish me? Do I need a spanking?” She bent over, her plaid skirt hiking up so I could almost see her panties.

“God Dammit… you are doing this on purpose. I think you just might deserve some punishment…” I growled, my eyes locked on the tantalizing sight before me.

Cindy looked back at me, her eyes sparkling with defiance. “I’ll be a good girl… I promise. Please don’t spank me, Mr. Bentsen.” She was playing with fire, and I was more than happy to oblige.

“Pull those panties down,” I commanded, my voice low and husky. “I want to see that cute little butt.” Cindy reached back with both hands and slowly pulled her panties down over her little bubble butt, and down to her knees.

“Like this, Mr. Bentsen?” she asked, her voice husky. She then slowly bent over further and pulled them completely off, over her shoes. She stayed bent in half like this, holding onto her ankles and looked back and smiled at my shocked expression.

This was too much, and I threw caution to the wind. I walked over and dropped to my knees behind her, my hands running up the backside of her legs, feeling the smooth skin of her thighs, and up over her pale ass. I grabbed both sides of her butt and spread her cheeks apart, her lips separating, and her tiny pussy opening up… dripping wet but still only the size of my pinky finger.

I brought my face close to her and licked the drip of her lube that was running down her lips. She flinched when my tongue hit her little button, then she moved her feet apart and arched her back so I had better access. I pushed my face into her box, my nose pressing into her ass, and my tongue pushing into her tiny little pussy… actually, too tiny to get my tongue in very far.

I pulled away and looked up at Cindy, my eyes locked on hers. “My God, you are so fucking hot.” I picked her up and laid her on her back on the desk, pulled her legs up and asked her to hold them there. She was incredible – innocent and obscene at the same time… holding her knees up close to her shoulders, her plaid skirt flipped up so her tiny pussy and ass were exposed, shoes and socks still on.

I pulled over the desk chair and sat down, placed my hands on her thighs, and started running my tongue up and down her open lips and little button, “Tell me if I do something you like, or don’t like.” Cindy’s eyes fluttered closed, her body relaxing into my touch.

“That feels pretty good so far…,” she said, her voice husky. I tried sliding my tongue further inside her again, with little success, so I concentrated on her little button, and her body shook at the contact. I slid my index finger inside her… but it came to a halt before my second knuckle.

I went back to her clit, working my tongue around and sucking her button. “Maybe you could try that thing with my G-Spot… you were talking about… from the back?” Cindy’s eyes snapped open, a look of surprise on her face.

I moved my hands down and spread her cheeks apart and gently licked around her ass with the flat part of my tongue, to soften and unclench her. Once I felt her ass relax I licked over the center and pressed harder with my tongue… I could feel her little butthole open up, and I slid the tip of my tongue inside. It tightened at first, then started to relax again as I slid my tongue in and out.

I pulled my head back and looked up at Cindy, my eyes locked on hers. “I am just trying to relax you. Does it hurt?” Cindy’s eyes fluttered closed, her body relaxing into my touch.

“No… I just… I wasn’t expecting that. It feels weird… I think I like it, but I… I’m kinda self conscious.” I looked back at her ass, still gaping open, about twice as large as her tiny pussy.

“Don’t be self conscious,” I said, my voice low and husky. “I am absolutely loving this… you are so fucking sexy. And I love your ass. I love the way it reacts… the way it opens and closes on my tongue.” With this she closed her eyes and laid her head back.

Sliding my tongue into her ass again, it tightened a little, then quickly relaxed and opened up further. I grabbed the lube and poured some on the fingers of my right hand, and some into her open ass. It clenched a little from the cold, but still gaped open. I slid my right index finger slowly into her ass, and went back to licking her clit… her body jerked and her ass tightened down on my finger.

“Is that okay?” I asked, my voice husky. Cindy jerked a little more, then her anus relaxed on my probing finger, “Uh… I… uhh… yeah… that feels good.” I rotated my hand and started stroking the top side of her canal, curling my finger back in a ‘come hither’ motion.

Cindy’s eyes fluttered closed, her body relaxing into my touch. I increased the pressure with my finger, wiggled it side to side, and slid it in and out of her ass, while I licked her pussy. Her clit was engorged, and my face was getting soaked from the lube leaking from her little slit.

I pulled my index finger out slightly, then added my middle finger, gently sliding both into her asshole. “Does that hurt?” Cindy said nothing, but shook her head quickly… her eyes still closed, her rapid breathing increasing.

I stroked her ass with my fingers, curling them alternately against the upper wall, like my fingers were trying to walk further into her. Her older sister loved this when I went down on her, except this time I was stroking deep in Cindy’s asshole.

“Whoa… that feels… oh my god…,” Cindy grabbed my head and pulled my mouth in harder against her. “Oh My God… That feels Good… Keep doing that! You’re gonna make me Cum! Ohhh… God… Jeff…”. Her body started shaking and her ass dilated further as she started to climax.

I roughly fucked her ass with my two fingers and sucked greedily on her pussy… she bucked against my mouth and fingers and arched her back, “OH MY GOD!… OH… fuck… ohh… JEFF!!…”. Her body convulsed violently for 15 or 20 seconds as she rode wave after wave of her orgasm.

Cindy’s body finally stopped shaking and fell back onto the desk, her hands fell from my head, her chest heaving with deep breaths. I gently slid my fingers out of her ass, and her body flinched as I pulled my mouth from her swollen pussy, like she was getting small electric shocks.

“Oh my God, Jeff… that was wild. I’ve never had an orgasm like that. That was crazy… amazing… it felt deeper and stronger than I ever… was that a G-Spot thing?” Cindy’s face was flushed, her eyes sparkling with excitement.

“I would think so… I was certainly trying to reach that. I hope I didn’t hurt you.” I said, my voice filled with concern.

“No… not at all. It was weird at first… you know, when you started playing with my… my bum… but then… wow.” Cindy’s face flipped to a look of concern. “Once again you didn’t get to enjoy yourself.”

I laughed, my voice husky. “Um, I was definitely enjoying myself. That was sexy as hell. I don’t always have to cum.” Cindy’s eyes sparkled with amusement, and she leaned in, her voice barely above a whisper.

“Well, maybe I could help you cum. I feel really bad I’m so small we can’t make love. Maybe you could teach me how to give a blowjob? Or… maybe anal?” I was stunned, my jaw dropping at her suggestion.

“Anal? Are you serious? I thought you never heard of that.” Cindy’s eyes sparkled with mischief, and she leaned in closer, her voice husky.

“No… I said I never heard of anyone licking down there. My friend said anal was a great way of having sex without losing your virginity, and you can’t get pregnant either. I thought it was nasty when I first heard about it, but I don’t anymore… especially after what we just did. What you just did… That was amazing…”. I was taken aback by her words, my heart racing with excitement.

The sound of the door slamming downstairs shot adrenaline and fear into us both. I threw myself to my feet and literally picked Cindy up and threw her and the pillow under a desk, and pushed a chair up to hide her. I could hear footsteps coming up the stairs. I ran over and sat down at my desk, inching up close to hide my erection and wet pants.

“Hey, Jeff, working late again?” Ken’s voice echoed from downstairs, and I froze, my heart pounding in my chest.

“Hi Ken, yeah.. I gotta get the materials for the GE job on order first thing tomorrow. Can’t be late on that one.” I said, my voice steady, but my heart racing with fear.

I looked over to the desk where Cindy was hiding, and you couldn’t see much. But my heart stopped when I saw her panties on the floor a couple of feet away. The lube was still on the top of the desk, top open.

Ken, the top salesman, walked out of the room with a confident stride, his words dripping with an air of importance. “I need to grab some files for a huge proposal I’m working on.”

“Everything is always huge with Ken,” I muttered to myself, trying to maintain a composed expression as my heart pounded in my chest.

As I focused on the papers on my desk, sweat beaded on my forehead. I took a deep breath, attempting to calm myself down.

Ken headed back downstairs, his voice carrying through the floor. “Don’t work too late… you should be out having fun with some young, beautiful girl, instead of working here at night…”

I bit back a groan as a giggle escaped from under my desk, and my face grew hotter.

After Ken’s car left the lot, I let out a sigh of relief and peeked under the desk. Cindy grinned up at me, her eyes sparkling with mischief.

“Oh my God, did he see those?” she whispered, her voice trembling as she spotted her panties on the floor.

“I don’t think so… Don’t worry about Ken, he’s cool,” I said, trying to reassure her and calm my racing heart.

“Oh, geese… I told dad I’d be home before dark. He doesn’t like me riding my bike at night. I’m sorry…” Cindy’s voice trailed off, and I wrapped my arms around her, pulling her close.

“There’s nothing to apologize for. Tonight was… unforgettable. I’ve never felt anything like that before.”

Cindy’s lips met mine in a soft, tender kiss. For a moment, I forgot about the danger and the consequences of our actions.

“I’ll follow you home in my car to make sure you’re safe,” I said, helping her get ready to leave.

As I watched her ride away, my mind replayed the events of the night, and my body responded in kind. My dick hardened in my pants, and I couldn’t help but feel a sense of possessiveness over this innocent girl who had awakened a part of me I never knew existed.

But as I drove back to the office, I knew I had to be careful. I couldn’t risk losing everything I had worked for, not for the sake of a fleeting pleasure.

Yet, as I sat at my desk, my mind kept wandering back to Cindy, her open sexuality, her body, the sound of her voice when she climaxes… and the danger that lurked beneath our forbidden relationship.

I knew I had to stay away from her. This was self-destructive. I was making her grow up too fast, and I was an asshole for corrupting this sweet girl.

But my conscience seemed to be losing the battle, and my body was screaming for more. I was trapped in a web of my own desires, and I didn’t know how to escape.