After she drove off, my phone buzzed. Jackpot! A new counselor at the high school I taught at had finally agreed to have a drink with me. We set a date for Friday night. I had asked her out a few times already this semester, but she always gave me a “We’ll see.” I guess I wore her down. She was a bit older than I and a recent divorcee. She had just moved back in with some extended family. Her name was Claudia, and was very pretty, smart, and quick witted. She had wonderful chestnut-colored hair and a petite frame with a nice size set of tits. Honestly, she looked like a more mature version of my sister, although I couldn’t make the connection at the time.
Friday arrived in a hurry and I was just out of the shower, putting on my best slacks when my front door burst open. “Chase, it’s me,” my sister’s voice rang out. Fuck. Why tonight? I walked out to the den shirtless again, and again, she smirked at me. “I came over for some help like you said,” she said, showing me her textbook. I explained I had a date tonight. She pouted but seemed to understand. “I never thought about you going out with anyone.” I told her it was with the new counselor from school and she smiled.
“You mean you aren’t dating old Mr. Barron?” She joked. I promised to help her out any other time, just not tonight. She said she’d come back about noon tomorrow. “As long as that’s enough time for your guest to leave,” and gave me a wicked grin as she left.
The date went well. Claudia and I talked and laughed together over dinner. Afterwards, we went for a walk in the park. It was a bit chilly out, so she snuggled up against my arm as we made our way around. We made out a little in the car before I took her home. She rubbed my chest and toyed with the waistband of my slacks. I felt her tits through her top. They were nice and round, and much firmer than I expected. She said she’d like to invite me inside, but her family was home. I was a little worked up, but I understood. I told her it was fine. And, really, it was. We had a great first date. Hopefully, it would not be the last. I really wanted to see her again.
I awoke the next morning with a massive case of morning wood. Figuring I had plenty of time until Heather came over, I threw back the blanket and started to rub my cock, thinking about Claudia and how I wanted to go so much further with her the next date. My dick had reached its maximum size and was throbbing hard. I was gently rubbing up and down the shaft and thinking about Claudia when suddenly the face in my thoughts became Heather’s. We were making out. I was reaching up her shirt to feel those perfect tits. She was the one fiddling with my belt, reaching for my dick. I couldn’t stop myself.
The knocking at the door interrupted my thoughts. Fuck! I was hard and throbbing and about to get to some serious jerking off. Heather was here. I threw on just a pair shorts and opened the front door to find Heather, Lisa and Mandy all standing there.
“Damn Chase, do you ever wear a shirt?” Heather quipped, smiling at me.
“Not that we’re complaining,” Lisa grinned.
Mandy gave me a wink and Lisa and Heather shared a laugh as they came inside and made themselves comfortable.
Apparently, the dorms were being exterminated, and the girls didn’t care for the chemical smell after the rooms were sprayed. Heather told them I wouldn’t mind if they came over to hang out while we worked on her history class. Of course, I didn’t mind. They were my sister’s best friends. And having three sexy beings in my apartment was never a bad thing.
“You guys are welcome here any time,” I said. And I meant it.
Lisa chided me, “We aren’t guys, dude” and grabbed her small boobs and gave them a heft. I blushed, and they all had another laugh at my expense. Oh well, worse things could happen to me in front of a couple of good-looking women. I gave the girls my Wi-Fi password, then Heather and I made our way to the kitchen table to work. We spent a good ninety minutes going over the build up to the American Revolution and straightening out the dates and names she had problems with. She called for a break and I watched her ass sway as she walked over to the fridge for a bottle of water. I felt eyes on me and looked around to see Mandy standing there, staring at me with a sly grin. Dammit. I was busted. I felt myself blush again. Mandy turned wordlessly and went into the kitchen as well. I joined Lisa in the den, who was scrolling through my Netflix account looking for something to watch.
“Damn Chase, you watch a lot of documentaries and titty movies,” Lisa quipped.
“Ooh, speaking of titties, how did the date go last night?” Heather asked, appearing behind me. I said it went well, then gave them the general summary. Mandy asked if I came home blue balled which made all the girls giggle. I admitted I did a little bit, but it wasn’t terrible. “I’m sure he, uh, handled things himself later on,” Heather joked, and I think I blushed again. She chided me for being embarrassed. Lisa smiled, and Mandy looked away. I assured them I’d be just fine, and hopefully I’d get to see Claudia again very soon. Lisa spoke up and said she hoped I’d get to at least round third base on the next date, which drew another round of laughter at my expense. Then Heather, out of the blue, spoke up, “If not, I’m sure you can call Mandy up. Many a lucky guy in high school got to experience a ‘Handy from Mandy’ you know.”
I gulped, I tried not to let it show. Mandy hid her face in embarrassment, ostensibly from the comment and not the fact she had in fact jerked me off the last time they were over. The girls laughed and laughed at my expense, Lisa throwing her head back and arching her back, making her small breasts press against her shirt. Her nipples were clearly on display. Did she ever wear a bra I wondered? Heather smirked at me and announced it was time to get back to work. I agreed.
We continued working on her assignments, including starting a research paper, for another hour. I showed her notes on similar research I had done last year for a class, and she was really excited about using it as a source. We wrapped up and the girls mentioned not wanting to leave right away. Lisa and Mandy were binging a new series on Netflix and they wanted to finish. I didn’t mind the company and said they could stay for as long as they liked.
“You think we could all have a beer?” Heather asked.
I consented and sat in the recliner. Heather brought out four longnecks and passed them around. She then joined the other two on the couch. I texted Claudia to see what she had planned for the evening. She did not give me a quick response. Damn. I was hoping to make another date with her. Heather noticed my face buried in my phone, “Hey, no sexting while we’re here.”
“No such luck,” I told her. One of them asked Claudia’s name and what she looked like and while I described her, Lisa had already gone and found her IG account.
“Ooooh, she’s a hottie Chase,” she cooed.
She showed the other two the pictures and Mandy spoke up, “She looks a lot like Heather, you know. The same color hair and eyes, with plenty of boobs as well.”
The girls all giggled, and I tried to hide the fact my dick was getting harder. Heather’s phone went off, and suddenly they were all talking about some event on campus that they were going to the next day. Thank God. The girls finished their beers and then headed out the door, each giving me a long hug and kiss on the cheek. I pressed a little harder than normal into each hug, feeling Mandy and Heather’s breasts against me, as well as Lisa’s perky nipples. Damn I was hard. I wondered if they could feel it.
Heather texted me later that night, saying she hoped I was OK with them talking about my date with Claudia and all of that. I replied that it was fine, it had just caught me off guard having a sexually themed chat with my sister and her friends. I did reiterate they were welcome to come by any time they wanted, and that I had enjoyed the company.
Another few weeks went by. I saw Claudia a few more times. And after a few dates, we did start to sleep together. The sex was great, her tits were amazing, her ass begged to be spanked, her pussy surprisingly tight and tasted heavenly, and she gave great head. But… and there’s always a but, eventually, there was a problem. And a big one.
One Friday night, Claudia and I were at her place having sex on her couch. She had her face on the cushion and ass pointed up at me as I fucked her from behind, everything according to plan. She was pinching her hard nipples and we both were moaning and calling out little things to each other. Suddenly, without thinking, I said, “Mmmm Heather, this feels so good.” Yeah. That was the end of that. Call a girl you’re dating the wrong name during sex and see how fast it all screeches to a halt. She got understandably mad. I apologized profusely. I tried to tell her Heather was someone I was no longer involved with. Now, I’m a terrible liar, and she seemed to sense that. She said if even if I wasn’t cheating on her, I clearly had feelings for this Heather woman and that she refused to share or play games. I grabbed my clothes and left in a hurry, full of shame.
I don’t blame her at all. If I was fucking a girl and she called out another guy’s name, I’d be upset too. I came home to an unlocked door. I eased inside and found Mandy and Lisa sitting on my couch staring at the TV. I had given Heather a spare key by this point, but where was she tonight? On a date of her own I soon discovered. “Why are you two here and not out also?” I asked. Apparently, my Wi-Fi was better and the common room at the dorms was too cold. All of which made sense. Not that I cared much at that point.
I plopped down in the recliner and unbuttoned my shirt for comfort. Lisa cooed, “Ooh, are you going to give us a show?” I didn’t reply. My bad mood was obvious. Mandy pried further, and I tried to shoot her down. Then Lisa joined in and I eventually relented, telling them part of, but not all, the story of my disastrous night. They both expressed their sympathies, then Lisa perked up, “Well, if you’re a bit blue-balled, we could always arrange a ‘Handy from Mandy’ for you.” She laughed, Mandy giggled, and I managed a weak smile.