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.