The weekend passed far too quickly as all weekends do. I decided to start shaving my man parts. I wanted to have Courtney swallow my dick at some point, and didn’t want my hairs getting stuck in her teeth. That had happened once with my high school girlfriend and it wasn’t fun for anyone.
Monday, after class and before I had to head to my job doing tech support for one of the departments on campus, I was sitting at one of the tables in the student center working on three latest assessments for my Operating Systems class, when Courtney sat down across from me. I tried not to panic, and managed to react normally, at least normally enough. I did take some satisfaction in noting that the days after I fucked her ass, she still sat a little gingerly.
“Hello, it’s Tom, right?” Courtney asked.
“Yeah, and you’re Courtney, right? We’ve had a lot of classes together but never really talked, have we?” I replied.
“No, and that is my fault. Sorry about that.” She replied and I relaxed. If she’d figured out I was the one blackmailing her, she wouldn’t be apologizing right now. So this was something else. “Listen, I’m struggling with the 2nd problem on our OS homework. Would you be willing to come by my place this evening and help me with it?”
I was a touch surprised, but replied, “Sure! I’d be happy to.” Then realizing I was not supposed to know where she lived, I asked, “Which dorm do you live in?”
“I’m actually in my own place,” she replied, “Here’s the address and my phone number.” And she handed me a paper with the promised address and number.
“Great!” I said, the address was indeed where she lived. “I get off work at 5, I could probably be at your place at 5:30, how does that sound?”
“Perfect!” She said, “See you then!” With that she quickly got up and walked away, going around the nearby corner.
I was torn. There was no reason for me to not go, unless she knew I was her mysterious blackmail. There was no way I would have passed this up two weeks ago. It would be far too suspicious if I didn’t go. My heart beat fast and I had a hard time concentrating the rest of the day.
After work, I knocked on her door and was surprised to see Courtney in a nice blouse and skirt. “Come on in!” She invited.
Her place looked about the same as when I’d been here the week before, except there were some of our class textbooks open on the table. “Well, shall we get started?” I asked.
I knew she had cheated to get where she was, but her understanding of software, and electronic systems was worse than I feared. It took a half hour to answer the first part of question 2, and there were 6 parts.
Courrney broke. “I’m sorry,” she confessed, “I didn’t bring you here to help me with homework. I’ve already submitted this assignment, I need your help with something else.”
I was genuinely confused, “What did you mean?”
She squirmed a bit, “Well, you see… I kinda…” she sighed, “I lost a bet, and in two weeks I’ve got to have sex with the guy I lost to. No, I don’t want to talk about the bet.” She replied to my opening mouth, “And no, backing out isn’t an option.”
She sighed, “Would you have sex with me first? I don’t want to have that loser be the one to take my virginity.”
I was trying not to gape. “Of course! I’d be happy to!” My mind struggling to catch up to with what was happening.
“Great!” She exalted, “I was trying to be seductive, but I guess haven’t ever tried to seduce a guy before, I’m usually busier trying to chase then off or to run away.”
I felt like an idiot. She’d sat next to me on a rectangular table, leaned way too close and kept rubbing her leg up against mine and grazing me with her tits wherever she could. I’d ignored it because it’d been around way too many sluts and teases, but I knew she had to find a guy to fuck fast.
Courtney shyly led me to the bedroom and I noted her pink sheets were gone and instead white sheets covered her bed. Her blankets were folded at the bottom.
Courtney stood awkwardly once we were both in the room. “Have you ever…. you’ve had sex before, right?” She asked peering at me inquisitively.
“Yes, but not in a while,” I admitted, “I had a girlfriend in high school and we regularly had sex, but since we broke up, I haven’t done anything sexual, except now I guess with you.” (And your ass on Friday) I thought, but kept it to myself.
“How does this usually go?” She asked, shyly, “I am sorry I am bad at this, I just….” She made a sort of shrugging gesture, “Could you help me?”
I chucked, “Well, my girlfriend liked to strip me naked, then kinda do a sexy strip for me and laugh as my erection twitched. But sometimes she’d just strip, climb in bed and tell me to make her feel good. My buddy said his girl liked to make him undress her. So however you want to do it is probably fairly normal.”
“Well, I don’t know how to strip ‘sexily’ so I’ll strip, and you strip… then can I touch your thing? I’ve never seen a real one before.” She asked.
“Sure,” I told her, “having a sexy girl play with your dick usually feels pretty good.” I told her, shedding my shirt and offing my pants.
I stripped much faster than her, and so I got to watch her remove her bra and panties as I sat on her bed. She was blushing profusely and half-heartedly covering her breasts and was keeping her legs tight together, but I assured her, “You look fabulous.”
“Thanks.” She said, sitting beside me. Relaxing a little bit, but still obviously uncomfortable.
I laid back, causing my dick to stand almost straight up. I wasn’t fully erect, but I wasn’t limp either. I was probably a good five inches at this point and from the look on Courtney’s face, this was the most experience she’d ever had with a penis. Her wide eyed innocence was such a turn on that as she reached for my dick it went from partial to fully erect, drawing a gasp from Courtney.
“It’s so big…” She breathed, a mixture of fear and excitement in her voice as she touched the tip with her finger.
I jumped a little, and she looked at me concerned, “Did that hurt?”
I laughed, “It doesn’t hurt but it is really sensitive, especially when it is erect like this. If you do too much to the top like that, I’ll probably cum on your hand and then we’ll have to wait for me to get hard again before we can do anything.”
She lowered her fingers to touch my shaft, “I can’t believe I’m doing this…” She breathed.
I was so horny it hurt, and was starting to get nervous that she was going to back out. “Here,” I said shifting so the center of the bed was all hers, “Let me show you how good this can be.” and I patted the spot I’d just been warming on her bed.
Relieved that she didn’t have to take the lead anymore she laid down.
“Just to be sure, is there anything you don’t want me to do?” I asked her.
She rolled her eyes, “Well, the guy I lost the bet to isn’t going to give me that option…” She muttered and subconsciously rubbed her butt, “Just be gentle and explain what you are doing…. Okay?”
I smiled, lay down beside her, supporting myself with my left hand and got really close to her, “So the first thing I am going to do is I am going to kiss you, and I will probably do that a lot.” I told her lightly, taking her chin in my hand. “Then I am going to start touching you, starting with your neck,” I let my hand drift down toward her neck, “then your breasts, your stomach, your legs, and finally, your vagina.” She was starting to tremble, a mixture of excitement and nervous energy. “I will then start to lick and suck on your beautiful breasts and nipples, and see about finding what parts of your vagina really feels good for you, and hopefully around then, you’ll get your first orgasm, assuming I do this right.”
Her breathing was starting to get heavy, and the musky odor of her vaginal fluids started to fill the room.
“Then, I’ll keep going, I like giving a couple of orgasms to my girl before actually making love to her,” I told her, bringing my face close, “Because once we start making love, it will only be a few minutes tops, and I want you to remember this.”
“Fuck.” She breathed, “I guess I got lucky.” She chuckled.
Our lips met. And she immediately responded to my tongue and opened her mouth, and we were almost immediately making out. Courtney tried to mimic what I did as our tongues met in the dance of sensations.
Her body began to respond, and her back began to arch. As I told her, my hand began to caress her, my hand wandering down her neck to her breasts. The firm but supple flesh molding to my hand, eliciting a moan through our kiss. Part of me wanted both of my hands on her heavenly tits, but one hand supported me as I rolled and squeezed her boob in my hand. Courtney didn’t seem to care, as she was just in bliss as she surrendered her body to me.
I rolled her nipple in my hand, causing her to sink back to the bed and moan again. I began alternating between her wondrous breasts, mauling and teasing the sensitive flesh. Her tongue periodically became inactive as she lost track of everything in her pleasure.
After a few minutes of playing with her tits and smelling her sopping sex, I decided I couldn’t wait any longer and I leaned more toward her waist, and my hand began rubbing down her stomach, drawing a shiver from her. My hand caressed down her stomach, over her pelvis, tantalizingly close to her yearning sex, and down her left leg, massaging the inside of her thigh. Courtney instictively spread her legs to allow the pleasing hand to do what it needed to. Her higher brain functions had clearly stopped at this point, and I withdrew my mouth from hers, letting her breathe deeply as my hand switched from caressing down her left leg to feeling up her right leg.