Courtney woke me up with a kiss the next morning.
“Did you get your brooding out last night?” She asked as she cuddled up to me, still naked since we slept that way.
“I wasn’t brooding, I was thinking.” I told my lovely girlfriend.
She laughed, “No, you think all the time. Most of the time when you think, you’re still doing things. You were brooding so you could do nothing but think. And that’s okay, I guess I kinda hit you with some big and hard things. But Tina wants to join the harem in style today and I want you in top form.”
I laughed.
“Oh, before I forget, we haven’t bought tickets to fly to my parents’ place for Thanksgiving. That’s coming up.” I told Courtney.
She looked at me confused, “Is there a reason not to use my family’s jet?”
“You have a… of course you have a jet.” I muttered.
“Oh, you didn’t know?” Courtney asked.
I laughed, pulling her close. “Let’s just assume that I don’t know of any of your family assets, of any kind, in the future. What’s a private jet like?”
“Kinda boring.” She admitted. “Unless we are taking a big group and we take the Boeing. Then there are servants and drinks and food… But we’ll probably take the Cessna. So it’ll just be us and the pilots. We could have one of the butlers serve as a flight attendant, but we usually only do that for overseas flights. They’ll be up in the cockpit and we’ll be in the main cabin. The fridge will probably be stocked, and there’s the TV and there’s a bathroom, but not a whole lot to do during the flight.”
“Unless we want to join the ‘Mile High Club’.” I joked.
Courtney perked up. “What’s that? Daddy loves his country club. Is it like that?”
I looked at her, bewildered. “Have you really never heard of the ‘Mile High Club’?”
Courtney shook her head, “What is it?”
I laughed, “The ‘Mile High Club’ is the term for the group of people who have managed to have sex in an airplane at cruising altitude, hence a ‘mile’ above ground. They say that the low atmospheric pressure and lower oxygen content can lead to amazing sex. Most people try to sneak into the bathroom together on a commercial flight… but if it’s just us and the pilots and they don’t come out of the cockpit until we land…” I left it hanging.
It didn’t take Courtney long to piece together what I was saying.
“You’re saying we could have sex basically the entire flight?” Courtney grinned, “I mean, if one of the pilots had to use the bathroom, they could catch us, but… oh… that’s hot. We’re definitely having sex during the flight.”
“The flight is, what, four hours?” I told her, “I’m sure we can find time in there.”
We got dressed and had breakfast and walked to campus for class. About half-way there, who should job across our path, but Tina? Tina ran across an intersection ahead of us, not seeing us and continuing to run. She was still wearing just a sports top with a built-in bra and running shorts. She was without a doubt the fittest girl that would be in my harem.
“You excited to tap that?” Courtney asked, teasingly.
“Of course, I’ve been excited for each of the girls in my harem. Especially you.” I told her and kissed her.
Class dragged on. Courtney and I had already gone over the materials. I had found that interestingly, having to teach Courtney the principles had enhanced my own understanding. I was easily able to answer the questions when called on, and Courtney was just as quick to answer. The arrangement was definitely working out for us, but it did make class a little boring.
We had lunch in the food court. It was strange to me, being financially stable. I could actually buy lunch, instead of preparing one from home, and it wasn’t an issue. I still had over $3000 in my bank account, and I had already bought myself out of my former housing contract. With vastly increased income, and my major expenses removed, I was more financially free than I had ever been.
Courtney and I had one more class after lunch, which turned into a work session with the teacher assisting others. When Mr. Smith learned that Courtney and I had already completed the assignment, he graded us really quick, giving both of us top marks, then invited us to help the rest of the class, since they were struggling. It was so rewarding, seeing Courtney able to explain and teach the complex issue to other class members. I had practiced teaching this to Courtney, so I was ready with answers and together we helped half of the class with their understanding on the subject.
Finally, it was time to go home.
We arrived, and I nervously began hydrating.
At approximately 2:15 pm, there was a knock on the door.
As expected, Tina walked in. She was wearing yoga pants and a sports top, and carried a duffle bag with, I assumed, another set of clothes.
“Abby told me about yesterday.” Tina informed us. “I had decided I wanted in too, but I didn’t have this yet.”
She reached into her bag and pulled out a printed copy of her STD test results. She was clear. With that, the only thing stopping the fit girl from joining my harem.
“Welcome to the harem.” Courtney said, “Are you excited for this?”
“To get to have sex with Tom? Well, Abby gave it quite the ringing recommendation. I just hope he can keep up.” Tina told Courtney, “I usually weed out my men with a brisk job, but Abby pointed out that Tom has kept up with having sex with multiple girls, so I am willing to skip that on him, but I really hope I am as impressed as Abby was with him.”
“Do you want to try it now?” Courtney offered.
“I have been so horny all day just thinking about it, of course I want to try it now. I can only do so many three mile jogs before I start cramping up, and I’ve already done two today.” Tina admitted.
“Are you on the pill? Or does Tom need a condom.?” Courtney asked.
“On the pill. I got on it two years ago when I got here.” Tina informed us, “I was sure I’d be having sex with a bunch of studly fit men, but have been seriously disappointed. And before you ask, yes, I’d love to do the post sex photo… but could we do some before and after photos? I want to see how sex changes my vagina.”
“I’d be thrilled to.” Courtney assured her.
Tina grabbed our hands and practically ran to the bedroom.
Her top came off, and there was no bra underneath. Then her yoga pants were off, and all she had on was a g-string she practically ripped off.
“Alright, time for some before photos.” She sighed happily, flopping on her bed. She spread her legs and Courtney snapped the first picture.
“Let me show you the goods.” Tina proclaimed and she gently spread the lips of her vagina showing the hymen inside. After half a dozen pictures, Tina was satisfied.
“Now get over here and show me how you blew Abby’s mind away.” Tina directed me.
I had stripped while her ‘before’ pictures were being taken.
“Now, how much did Abby tell you?” I asked, as I climbed into bed with my newest virgin.
“She said that you took it slow and it seemed to last forever. Other than that, she was a little giddy to try and get specifics out of her.” Tina confessed.
“So, when it comes to actual penis in vagina sex, that is actually generally a smaller part of the whole event.” I started. “We will kiss, and I will touch your body, a lot. I will make sure you are highly aroused, and hopefully give you multiple orgasms before my penis ever touches your vagina. That’s because unless your body doesn’t feel good, the natural process causes a man to reach climax quickly, then he will lose his erection regardless of how aroused he is. It can take me five to fifteen minutes to be able to get my erection back, and usually by that time the sex has wrapped up.”
“But we could just keep making out for that time, get you erect again, and keep going?” Tina asked.
“Probably, but this time, odds are, once I pull out, your vagina is going to get really, really sore.” I told her.
“Fair, we’ll see how it goes and we’ll try that next time.” Tina told me.
“I will take my time and try to make you feel as good as I can. It has taken me an hour to give most of the others the experience I want for them for their first time. I want it to be special.” I told her.
“You really know how to sweet talk a girl, don’t you?” Tina chuckled, “Most of my friends say their sex takes like five or ten minutes. Most of them say they don’t orgasm during it either. I mean, Debbie looked like she was having a good time, but you really think you can give me orgasms before we really have sex?”
“Let’s see, can we?” I told her, and kissed her. I held her head as I kissed her gently, but passionately.
Tina hadn’t been lying when she had said she’d been worked up all day. She responded quickly to my touch, and my kiss. She melted in my hands, allowing me to kiss her and she simply kissed me back. Before long our tongues were caressing each other’s and exploring each other’s mouths. For several minutes, we simply enjoyed
I began to stroke down her neck and caress her breasts. Tina’s breasts were apparently highly sensitive, because as I began squeezing them, Tina’s hand shot out and claimed one of Courtney’s and she gripped Courtney’s hand hard as she adjusted to the stimulation. I was gentle with her breasts because I didn’t want to push her too far, too quickly. Tina slowly relaxed as I continued to massage her b-cup breasts, and I moved to gently pinching her nipples. This caused her to twitch and moan.
I released her mouth, to allow her to breathe and I began kissing her neck, which elicited more shuddering and moaning. I realized if I moved things up, a little clitoris stimulation I could probably get her first orgasm pretty fast. So I kept my left hand on her breast, but dragged my right hand down her body, teasing her with its obvious destination, before I caressed her folds and gently swirled on her clitoris.
Tina’s reaction was extreme, like a tightly wound spring that just broke loose. Her limbs shot straight out, her back arching, as she let out a breathy rasping moan. Then she pulled in her limbs, and began twitching.
“God, Tom!” She gasped, “Don’t stop that!”
I moved my thumb to rub back and forth on her clitoris as my fingers were then free to massage the rest of her slit. My left hand continued to gently squeeze and roll her breasts, and pinch her nipples, switching between them as I continued to kiss her neck.