5- My High School Sweetheart’s Little Sister- pt. 5 (The Office)

NOTE: This chapter includes anal-play and analingus, which isn’t everyone’s cup of tea. This is a fairly long read, so if this offends please skip this chapter

————-Part 5: ■ THE OFFICE (Chloe comes home) ■ ————-

Chloe said she would be back home on the 5th. We had been in pretty close contact while she was out of state, but this would be the first time I had seen her in about six-months.

It was almost three-weeks since I had played ‘Truth or Dare’ with Cindy, and I hadn’t seen or spoken with her since then because I was scared of calling her house, and I was feeling pretty guilty about taking advantage of her innocence. However, this didn’t stop me from fantasizing about her constantly… I was actually looking more forward to seeing Cindy than her older sister.

I was working when her plane was to arrive, so I ran up to her house as soon as I got off work. It looked like no one was home, but Cindy answered the door when I knocked. She flashed a big smile and stepped in for a hug- I stepped back a little and asked “Where is everybody?”

“They went out to pick up Chloe at the airport. They should be back soon.” she replied, looking a bit disappointed.

“So, no one else is here?” I asked, stepping inside.

“Nope, just you and me and the dog.” she said, looking at me strangely… trying to size me up.

I closed the door behind me, and stepped forward and grabbed her in my arms. Cindy hugged me tightly and looked up to me, with those beautiful innocent eyes, “You haven’t called… I missed you.”

“I have been kinda scared to call. I think your dad is suspicious of… I think he might know… something. But don’t think you haven’t been on my mind… like constantly”. I was still hugging her, and thinking back on that night triggered an erection. My hands fell to her little butt, and I pulled her closer so she could feel my dick growing. She smiled and reached up to my shoulders, and stepping on her tiptoes she opened her mouth for a kiss.

We heard the garage door opening. They were home. We broke apart immediately, and jumped to separate corners of the entry. Cindy looked down at the bulge in my pants. “You might want to hide that thing”, she said with a nervous laugh.

I ran into the bathroom before they came in from the garage. I could hear them in the hallway, laughing and celebrating Chloe’s arrival. “Is Jeff here? I saw his car outside”, I could hear Chloe say.

“Yeah, he’s in the bathroom,” Cindy said, “It’s so nice to have you home! I’ve missed you!”

I flushed the toilet and washed my hands, just for cover. When I came out, Chloe gave me a big hug and a kiss, but she let go faster than I expected. I hadn’t seen her in six-months and she hugged me like I we had just seen each other earlier that day. Her mom gave me a hug too, and her dad gave me an enthusiastic handshake, but his grip was tighter and the smile on his face was more stern than usual.

I snuck a glance at Cindy, and she noticed it too. She turned and looked blankly down the hall.

Everyone sat down around the breakfast nook, Chloe to my right, Cindy on my left, with their mom and dad across the table. Chloe told us all about her college life, her friends, her classes, and how much fun she was having. She jumped up and ran to answer the phone, and her mom and dad asked how I was doing. The conversation dragged on at the table as Chloe talked on the phone, laughing and sometimes whispering. It was only a few minutes after she returned that the phone rang again, and Chloe jumped up again to answer.

Same thing… It was awkward, and everyone felt it. Cindy put her hand on my leg, more as a comforting gesture as compared to flirting. Her mom commented, “She has a lot of friends she hasn’t seen in a long time”, trying to be reassuring, but the fact that she hasn’t seen me either hung in the air.

I excused myself from the table, “I need to get back. I’ve got a pretty strict deadline to meet at work.”

Cindy walked me to the front door. She was visibly angry, “She can be such a… “, shaking her head as her words drifted off. She gave me a hug and whispered, “I miss you. I was hoping we could all cuddle on the couch tonight”, but we both knew those days were over.

I whispered, “Call me when you get a chance.”; my number was in the family’s phone book. She smiled and nodded as I walked out the door.

A car pulled up as I was walking out to my car. A friend from high school got out, and looked a bit startled as he saw me. “Hey Jeff! I came over to see Chloe… are you still seeing her?”

“Not really… have fun”, is all I could manage to say as I walked past him.

Chloe called me later that night but I didn’t answer.

———————— Cindy’s call ————————

I was briefly home in the afternoon, between classes and work, when Cindy called. “Jeff! Finally… I wanted to call earlier but either my parents were here, or Chloe was.” She was alone, but was still speaking quietly, “Is this a good time? Can you talk?”

I was overjoyed to hear her, “Yes… now is a perfect time. I’m not headed to work for another hour.”

“I’m really sorry about the other night. She was so rude to you. I was hoping we could hang out for a while.”

Just hearing her voice got my heart racing. She was so sweet, and she actually cared about my feelings. “How are you doing? I miss you. Did you just get home from school? So, are you still wearing your school uniform?”

Cindy attended a Catholic girls school that required she wear a uniform; white blouse, plaid skirt, the whole deal. This prompted constant teasing from her older sister who went to a public high school, like me.

“Yeah, I just got home. I haven’t changed yet. I hate having to wear this”, she replied.

Doesn’t she realize how hot she looks in that outfit? “You look so sexy in that uniform… you have no idea.”

“I think I look like a dork in it… you really like it?”

“I love it. I may like your nightshirt a little more, but that uniform is a close second.”

Cindy laughed at my flirting, “I want to see you”, she said in a sad tone.

“I want to see you too, but I certainly can’t come up to your house. Did you see the look your dad gave me? And I really don’t want to run into Chloe.”

Cindy was still talking quietly, “Maybe you could pick me up from school some time? Or I could ride my bike over to your house, or your office?”

The office… I’m allowed to work evenings there while I’m attending the university, and no one is there after 5:00. “The office would be great, if that’s not too far for you.”

She laughed, “You forgot I rode over 300-miles last year on the school bike trip.”

I heard her gasp, “Someone’s home! I gotta go!”

I was able to spit out, “Call my office number anytime after 5:30. The number’s in the book”, before she hung up.

I worked every night that week, but it wasn’t until Friday that the phone rang.

“Hi Stace! Are you around tonight? …Great! …is it okay if I ride over? …No, I can’t stay the night tonight…”

I laughed at her plotting, “Stace? …Yes! …Are you sure you can’t spend the night?”

Cindy laughed, “Okay… I’ll be over in a bit”, and she hung up.

I could feel my heart beating faster as I checked everything around the office. I had been thinking about this non-stop since she called earlier in the week. I had brought a few things down to work, a blanket, a pillow, lube, and some condoms, although I couldn’t imagine how I could ever get my 8″ cock inside her tiny pussy… condom or not.

Okay… I could definitely imagine it… in fact, I had been beating my dick raw over the past week imagining exactly that. I was going mad thinking about working my thick cock into her tiny body.

After the way Chloe treated me, my lust for her little sister became even stronger. However, it wasn’t revenge sex I wanted. I truly loved Cindy and I didn’t want to steal her innocence from her. I desperately wanted to fuck her, but I didn’t want to be the one who took her sweet virginity. She was too young, I couldn’t even take her on any respectable dates, or court her in any fashion… but I found her irresistible. I was going slightly mad over it.

———————— The Office ————————

I paced the office and watched the street for her, and the moment I saw her bike I ran down to let her in, “Quick, come inside. This is a pretty busy street… we don’t want anyone seeing you here.”

I picked up her bike and carried it into the small storeroom downstairs. “Come on, I’ll show you my office”, and led her to the bottom of the stairs. I let her go first… she was wearing her school uniform, and I strained to look up her skirt as she climbed the stairs. Watching her beautiful bare legs and her little bubble butt in that skirt immediately sent a surge of blood to my dick. I led her into my office, a large room with a number of desks and tables. I knew she could be seen by the cars driving by, so I guided her to the back of the room, out of sight. I walked over to the window to look down to the parking lot to make sure nobody else was there. Other than my car, the lot was empty.

I turned around, “It looks like we are alone.” I looked her up and down, “You wore your school uniform! I can’t imagine riding your bike in that can be easy, and I thought you hated it.”

“You said you liked it. I want to look good for you”, she replied with a smile. “I ride to school sometimes like this, so I just tuck the front of the skirt between my legs to prevent me from flashing everyone.”

I smiled, “I would be following you on that bike for miles, just in hopes that you might flash me.”

“Like this?” and she lifted her skirt so I could see her white panties.

“Oh My God… you need to be careful. 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.”

She smiled, “Have their way with me? You mean like the other night? I think I might enjoy that, at least with you. That was amazing.”

I laughed, “That was more than amazing… I have not been able to get it out of my head. 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.”

“I trust you. I like that I don’t have to be careful with you. And I like that I have this effect on you”, pointing to my crotch.

I looked down and my arousal was pretty evident. My swollen dick was hanging down the right leg of my pants and was trying to lift up, and there was a very visible wet spot at the tip. I was wearing lightweight khakis; probably a bad choice.

“I’m sorry. I can’t help it. Especially after that night. You drive me crazy.”

She smiled, “Don’t be sorry. 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. That night was truly the best, most erotic sex I have ever had. It was unbelievable. I’m sorry I was so rough with you… I kinda lost my mind.”

“Stop saying you’re sorry. I loved everything you did… everything. Was that really the best you’ve had? Even with Chloe? I mean… we didn’t even…”

“Yes… absolutely the best. My heart is racing right now just thinking about it”

“How did you learn to do that with your mouth… your tongue? That was amazing”, she repeated.

“That is sweet of you to say… I’m sure I could do better with your guidance. I have 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…”

“I’m sorry I’m so small. I wish… I… I wish I could… I’ve heard about that spot…

What do you mean ‘from the front’… do you mean you could reach it… um… from my… from the back?”

I smiled at her, “Well, I would certainly 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.” I could feel my dick growing just talking about sex with her.

“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 looked like she was in deep thought, “I would love to experiment. Did Chloe like it when you… um… you licked my… um…”

I laughed a little, “That was the first time I ever did that. I never really wanted to before.”

Cindy looked surprised, “Doesn’t that gross you out? I’ve never heard of anyone doing that.”

“There is nothing about you that grosses me out. 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.”

She giggled, and repeated my word, “bottom”.

“I hope it didn’t gross you out, or make you uncomfortable.” She shook her head and smiled, turning a little red.

She looked back down at the bulge in my pants, “Do you want to see my tan line?”. She lifted her skirt again, and pulled the front of her panties down, exposing her pale panty line and a little bit of her sparse bush.

My dick jumped seeing this, and I felt a large drop of precum come out the end.

“Dammit, Cindy… you are going to kill me. Or at least ruin my pants.”

She laughed and pointed at my pants again. My dick was straining at the material, and the wet spot at the head was huge, and was starting to run down the leg.

“Am I in trouble? I’m sorry… I didn’t mean to make you so uncomfortable. Are you going to punish me? Do I need a spanking?”

She turned around and bent over, her plaid skirt hiking up so I could almost see her panties. She looked back and watched me adjust my dick.

“God Dammit… you are doing this on purpose. I think you just might deserve some punishment…”

She bent further forward, reached back and lifted her skirt up over her waist so her cute little butt and white panties were in full view. She rested her weight on her forearms on the desk against the back wall, and started swinging her ass side to side.

“Oh, please, Mr. Bentsen… please don’t spank me. I’ll be a good girl… I promise.”

She was really enjoying screwing with me. But I was hard as a rock. I had never seen Cindy act this way; she was very confident and totally in control.

I played along, “Well, Cindy, if you do what I say, I might let you off with just a small spanking, and I might not tell your parents.”

She replied, quite dramatically, “I’ll do anything Mr. Bentsen… just don’t tell my parents.”

“Pull those panties down. 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 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, “Gymnastics”.

This was too much, and threw me right over the edge. I walked over and dropped to my knees behind her. I ran my hands 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 separated, and her tiny pussy opened up… dripping wet but still only the size of my pinky finger. Still holding her spread open, 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. Pulling my head back, I took in the sight of her spread open for me, her tiny pussy open for my tongue, her little pink asshole exposed.

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 had played with a number of girls in earlier years, virgins who were younger than Cindy, but I had never touched a pussy so small. I couldn’t reach her hymen with my tongue, but her opening was so small I could still only get the tip of my tongue inside her.

I pulled away and took a long lustful look at her while holding her cheeks spread apart, “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.”

“That feels pretty good so far…”, she said with a giggle and a small gasp. 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 started sliding it in and out of her, hoping her little opening would relax, but she pushed my hand away after only a few strokes.

“I’m sorry… I really like what you’re doing, but that kinda hurts a little.”

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?”

…holy shit. I never expected her to be okay with that suggestion

“Really? I would love to… just let me know if it hurts, or if you don’t like it.”

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. After several strokes with my tongue, her ass relaxed and opened more. I drove my tongue into her as far as it would reach… pulled it out a bit, and back in deep… her asshole expanding with each thrust, again and again until it stayed open even when I pulled my tongue out.

I pulled my head back and looked up at Cindy. She was staring at me wide-eyed… a look of shock on her face.

“I am just trying to relax you. Does it hurt?”

“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 and it was still gaping open, about twice as large as her tiny pussy.

“Don’t be self conscious. 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. The warmth and feeling of the smooth sides of the inner part of her canal was incredible.

“Is that okay?”

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. I was hoping the pressure would reach her G-Spot through the thin membrane between her vagina and rectum… by her reaction it was working.

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. The more I played with her asshole, the more it relaxed and opened up to my probing. I pulled my index finger out slightly, then added my middle finger, gently sliding both into her asshole.

“Does that hurt?”

She 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. The more I played with and probed her ass, the more it relaxed and opened, until I was pretty sure I could get more than just my fingers inside of her.

“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.

She was out of breath, “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?”

“I would think so… I was certainly trying to reach that. I hope I didn’t hurt you.”

“No… not at all. It was weird at first… you know, when you started playing with my… my bum… but then… wow.”

Her face flipped to a look of concern. “Once again you didn’t get to enjoy yourself.”

I laughed, “Um, I was definitely enjoying myself. That was sexy as hell. I don’t always have to cum.”

“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?”

My jaw dropped when she said this, “Anal? Are you serious? I thought you never heard of that.”

“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 stunned. I couldn’t imagine my sweet Cindy suggesting such a thing… but my heart was suddenly beating out of my chest and my dick was

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.

Ken came around the corner, “Hey, Jeff, working late again?” My heart was pounding, but I was able to spit out, “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 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 was the top salesman there, and sharp as hell. We got along well, but I didn’t want him to know anything he could hold against me.

He turned and walked towards his office, “I need to grab some files for a huge proposal I’m working on.”

Everything was always “huge” with Ken.

I focused on the papers on my desk, my heart beating through my chest, sweat breaking across my face. Keep cool, Jeff…

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

I heard a giggle under the desk.

I waited until Ken’s car left the lot before I moved. “Holy shit… that was too fucking close.”

Cindy scooted out from under the desk, laughing until she saw her panties on the floor. She gasped, “Oh My God, did he see those?”

“I don’t think so… Don’t worry about Ken… he’s cool”, I said, trying to convince myself and slow my heartbeat.

“Oh, Geese.. It’s almost dark! I told dad I would be home before dark. He doesn’t like me riding my bike at night. I’m sorry… I’ll make it up to you later, I promise.”

“Don’t say you’re sorry. Tonight was unbelievable. There is absolutely nothing better on this earth than watching you climax like that.”

I kissed her and helped her get ready. I wondered if she was grossed out kissing me after my tongue was in her ass.

“I’ll follow you home in my car to make sure you’re safe.”

I let her get a block away before I pulled out of the lot. It was a fairly long ride to her house, and I watched her the entire time. I couldn’t believe what just occurred, and with Cindy no less… that innocent little virgin girl I had known for so long. Chloe never even let me play with her ass, and here was her little sister… my dick was hard in my pants as I watched her ride her bike in front of me.

It was dark before she turned down her block. I went past her street, then drove back to the office. I worked late, but got little done. My mind was stuck on Cindy, her open sexuality, her body, the sound and movements she makes when she climaxes… and the danger of our relationship.

I should stay away from her. This is self destructive. I’m making her grow up too fast. I’m an asshole for corrupting this sweet girl.

Regardless, my dick was rock hard thinking of her, and it can overpower my conscience and good intentions every time.

---