Too Good To Be True Ch. 02

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.

My tongue touched her right nipple, as my fingers found her soaking slit. Her eyes popped open as the combined stimulation hit her brain. I started suckling on her tit and exploring her slit for spots that gave a good reaction. I found her clit fairly easily and started making little circle motions on it, duplicating the action with my tongue on her nipple. I sucked and switched my weight onto my elbow, freeing my other hand to start playing with her other boob.

It only took a moment before her legs started thrashing and she grabbed handfuls of her sheets as she moaned and gasped. Her first orgasm of the night. I was only further motivated and redoubled my efforts, increasing the speed and pressure on her clit, though being careful not to mash her pleasure button. Moments after her thrashing ended a second wave hit her.

I eased off on playing with her sensitive virgin cunt and let her breathing stabilize for a moment.

I let her tit slip from my mouth, and kissed up her neck to whisper in her ear. "Have you ever had anything inside your pussy before?"

She shook her head, "Not really." She admitted breathily. "I tried tampons once, but I didn't like them."

"You won't be able to say that anymore." I told her a little smugly, and renewed my rubbing up and down her slit. "I am going to put my finger in you, and once you get a chance to get used to it, I'll add a second. I am going to see if I can find your G-spot without breaking your hymen, then after I make you cum again, I'll get in position and we'll make love."

She moaned, and I took that as permission to continue.

Her pussy was so tight as my index finger dipped into the sopping sauna of her sex. Courtney pushed with her legs driving her back into the bed as she moaned again. It only took a moment to feel the barrier of her hymen preventing my finger from going deeper. I could try to work around it, but I really didn't want to risk damaging it with my fingers. I took a moment to look down at her sex as I played with it. I used my fingers to spread her pussy so I could see her hymen. And was pleased to realize I had dozens of pictures of her spreading her pussy such that her hymen was visible. Those had been some of my favorite pictures to make her take since she always hated taking them, and now they were the only pictures I couldn't get more of.

I let her pussy close normally and began feeling around inside her with two fingers, while my thumb massaged her clitoris. Her hymen didn't let me in too far, and I wasn't sure I could reach her g-spot this way. I was disappointed, I knew roughly where her g-spot would be from my previous girlfriend, but breaking my ex-girlfriend's hymen had been one of the first things we did so I didn't realize Courtney's hymen would block her g-spot.

Luckily, Courtney's body didn't seem to care and she started thrashing in another orgasm.

I didn't waste any time, and while she was thrashing I got myself between her legs lined myself up and presented the head of my dick at her opening, I knew that breaking her hymen would hurt and hoped that by couching it in an orgasm, it would lessen the pain for her. My left hand grabbed her hip and my right thumb started working her clit.

Courtney gasped, "My god..." her eyes fluttering and she seemed almost delirious.

I figured this was the best chance I'd get and started pressing forward.

Her pussy separated to let my clock's head in, and with just the tip in, I felt her hymen draw tight. I leaned in, and said, "Breathe."

Courtney looked up at me a sex haze evident in her muddled expression as she just said, "Huh?"

I couldn't wait any longer to be in her.

Maybe it was the fact that I'd been putting off my satisfaction, maybe she moved with me, and maybe it had just been long enough I'd forgotten the amount of force needed to break a hymen, but one moment just my tip was in her, and the next I was bottomed out. The small popping sensation of her hymen being obliterated was almost lost in the sensation of her vagina being split for the first time. Only because I was consciously paying attention did I feel and savor it. But it was gone in a moment as my balls slapped her ass after her hymen broke and my dick slammed into her depths.

Courtney let out a pained squeal and latched onto me, pulling me down on top of her, and possibly deeper into her. Her legs instinctively wrapped around me and clamped down.

"I'm sorry Courtney, I didn't mean to be rough..." I started.

"I'm fine." She breathed, "I must need a second." And a tremor went through her body.

I had an epiphany at that moment. Here I was, balls deep in a former virgin with no condom, and glancing over at her bedside table, her birth control wasn't visible.

"Um, just realized, I don't have any condoms on me..." I started lamely.

"I'm on the pill, so don't worry about that, just don't move for a second." Courtney shushed me.

The sensation of her pulsating hot pussy on my dick was more then enough to keep me hard, even without her erect nipples pressing into my chest. And a moment later her body began to relax a bit.

I kissed her again, and began massaging one of her breasts, and was rewarded with her returning the kiss. After a moment, I began to feel the moisture returning to her vagina. I reached my left hand down and awkwardly began rubbing her clit with my hand sandwiched between our bodies and she once again moaned. I had salvaged to erotic energy of our sex. She released me and lay back, enjoying the sensations.

I sat up, enabling me to work her clit more effectively, and began a gentle rocking movement in and out of her.

"Oh, god...." she moaned, putting one hand on her head, her other hand stretching out to grab her sheets again.

I could see her virginal blood on my dick as it gently moved in and out of her. The thought of just having taken her maidenhood caused my dick to throb and I stated to pick up the pace.

"Oh, fuck..."she moaned, both hands moving to my knees as her vagina enjoyed my onslaught.

I slowly increased in speed, recieving positive responses from my inexperienced lover. "Oh, do that more, and faster..." She begged. Before long I was pounding her pussy like a jackhammer and she was moaning and gasping.

I must have hit an especially good spot, because she stifled a scream and her pussy clenched around my throbbing dick, pushing me over the edge and I rammed my dick as deep as I could and squirted my sperm deep inside her.

Obviously, fucking a virgin was s fucking turn on because I must have had six or seven squirts before my balls were done emptying themselves into her wet deflowered cunt. I sat back content as Courtney's breast heaved with the lingering tingles of her orgasm.

Suddenly, her head popped up. "Fuck, I almost forgot..." and she grabbed her phone of the nightstand and opened her camera. "I need you to take pictures of.... this." Courtney instructed, gesturing to her cunt. And when I looked at her confused, she mumbled, "Part of the bet..."

I had completely forgotten my demand for pictures of her deflowered body, but trying not to be too happy about it I asked how she wanted me to go about it.

"I don't know... honestly, he asked for at least a dozen post sex pictures... I have no idea what he really wants. What kind of pictures would you want?"

I couldn't believe my luck. First I had her pull her knees back to her shoulders and got a shot of the sperm and virginal blood leaking from her pussy and dripping down her ass. Then I had her lay back and cup her breasts to emphasize them. Then started taking pictures of her spreading her pussy with sperm everywhere. I grinned, getting to be creative and now, instead of trying to give what resistance she could to her blackmailer, she happily posed for me.

As I took the pictures a question started to bother me, "Courtney, why are you on birth control? I mean, you don't seem like the type of girl who would just be on it."

Courtney rolled her eyes as she posed with her cum-covered ass in the air, "It was my mother's idea. She thinks just because she is a slut that all girls are sluts, so I needed to be on birth control as soon as I had my first period. I stayed on them because it means I only have the cramps and bleeding once every six months."

I snapped another picture. "You don't like your mom then?"

Courtney shook her head, "She just wants my dad for his money, and I was always just a problem for her. If my dad didn't have a prenup she'd be spreading her legs for any guy she could get between them." And she left it at that. I like to think I'm smart enough to read the room and let it drop.

"You know," Courtney laughed, "I've had to take lots of nudes... because of the bet I lost, and I much prefer you taking them of me. Especially while I can watch that react." Courtney informed me, smiling at my twitching cock. I was pretty sure I had my dozen photos pretty quickly, but Courtney didn't seem to mind me continuing to tell her sexy poses for more photos.

After well over two dozen photos, Courtney got a wicked smile, "If you wanted a girl all to yourself, what photo would bother you the most to get her doing with another man... though, only one man, I'm not doing multiple guys. I wanted to save myself for my husband, but..." she gestured to her deflowered pussy, "obviously, that's not happening. I was told to find someone acceptable and deal with the fact that I'd end up fucking whoever I chose, the asshole I lost the bet to and my future husband. I don't want any more people on that list. However, the asshole that gets to fuck me in two weeks has let it slip that he loves how 'pure' I am. He was seriously ticked when I talked him into letting me pick who gets my cherry. But I'd love to have some more pictures of you doing things that'll piss him off."

I thought for a moment. I had to be careful. If I let slip something I shouldn't know, this entire situation could blow up in my face and it'd be my future toast, not hers. "I get that you don't want to talk about your bet," I started, "but what were the conditions? Because pissing off a guy intentionally before he fucks you sounds like a bad idea. I mean, he could get pretty mean and rough..."