High School Harem Pt. 02

When it got to around dinner time, I still hadn't heard from any of the girls. Sure, I could've texted them, but I've never been the type to take the initiative to text someone, and with Molly escpecially I never had to worry about it because she would always be the one to text me first. I decided to just head down to the cafeteria. When I got to the cafeteria, there was Amanda and Erin, but no Molly or Katie. That's strange, I thought. I grabbed some food then joined Amanda and Erin at their table, figuring I'd just ask them.

"Hey you two." I said, sitting down.

"Hey Alan." Amanda said, meanwhile Erin offered a simple nod as her greeting.

"So where's Molly and Katie?" I asked.

"Not sure, I haven't seen them since class let out." Amanda said.

Now, that really is strange, not even Amanda, one of their best friends knew where they were. I tried not to worry about it and just focus on eating. As we ate, we made small talk, but nothing of note, it actually made me realize that Molly really was the heart of out little group. Without her, we just didn't seem to have much to say. When we all finished eating, we parted ways to head to our respective rooms. As I walked to my room, my phone suddenly vibrated in my pocket, it was a text from Molly.

Molly: Sorry I missed dinner, but can you come meet me at the gym?

Me: Sure? I guess.

Molly: Great! I'll be waiting our front.

Me: Alright, I'll head that way.

I hadn't heard from Molly since lunch and now she wants me to meet her at the gym? What gives? Then I remembered what happened the last time I was in that gym, my spirits immediately lifted, I knew what this meant. Sure, before I was disappointed that we didn't have dinner together, but the gym was a much better place to spend time. I quickly made my way to the gym, and sure enough there was Molly waiting near the door.

"Hey Molly, what's up?" I greeted her.

"Hey Alan, just follow me." she said.

Straight to business, I thought. Not that I minded, I'd been looking forward to having another go with her ever since our first. I followed her into the dark gym.

"Look, I know what you're probably thinking, but I didn't invite you here for that. I need to talk to you." she said as we walked across through the darkness.

What? I thought. Then what are we doing here? I wondered. I was more than a little disappointed.

"ummm.. can't we talk elsewhere? Why get my hopes up by bringing me here?" I asked, wondering why the gym.

"Look, I know you're disappointed, trust me, I wanna have another night like our last one just as much as you. But there's a reason I brought you here, just let me explain." she said.

"Okay, go ahead." I said, curious at what she had to say that couldn't be said elsewhere.

"It's about Katie, the reason I missed dinner is because I was talking to her. You Katie was really upset when she found out that me, Amanda, and now Erin have been with you. She feels really left out. And I told her that you'd have sex with her too, if she wanted. So that's why I brought you here, I've got Katie waiting in the locker room."

So that's why, I thought. My heart began to race with anticipation and I quickened my walking pace slightly. It seems I wouldn't have to try and hatch some plan after all, apparently Molly and Katie had done that.

"Now, hold on, not so fast. I'm not done. Look, there's something you need to know. Katie is a virgin, and I told her that you could be her first, she was nervous and took a little convincing. But I assured her, you would be gentlemanly. She only asked that I stay with her the whole time, to help talk her through it." Molly explained.

I almost gasped, Katie's a virgin? I know, that shouldn't be that big of a surprise, but it kind of was. I mean these days, most people have lost their virginities before 18. What's more is she wants me to be her first, or Molly does, to be more accurate. And to be perfectly honest I didn't know how to feel about being a girl's first. The last and only time I was a girl's first was when that same girl was also my first. But then again the idea was rather enticing, Katie was quite the little hottie afterall. Yet that alone didn't alleviate my hesitation, I was kind of worried that it would be like taking advatage of her, plus with Molly there the whole time, I feared it would be kind of awkward. I've never had sex with someone watching before, it seemed strange to me.

"You don't have to if you don't want to. I just feel like this is the only way to make Katie feel better." Molly said.

I continued to mull it over. I was hesitant to be sure, but if Katie was so upset and doing this really would help, how could I refuse? Plus Molly seemed to want this too, and I wasn't sure I could refuse anything coming from her.

"It's understandible to have misgivings about being someone's first. But I really want to help her out an you're the only way I know to do that. So please, do this for me." Molly said, her eyes pleading in the darkness.

Those were the magic words. I was sold. This was something Molly really wanted, and for whatever reason, I can't bring myself to disappoint her.

"Okay, I'll do it." I finally said.

"Really? You will? Oh thank you so much Alan." Molly said excitedly, immediately wrapping me in and embrace.

All I did was nod a simple "yes." I could tell this really meant a lot to her. She was like me, in a way. Molly couldn't bring herself to disappoint Katie, and I couldn't bring myself to disappoint Molly.

"Great, now just follow me." Molly said, leading me into the locker room.

We entered the locker room, but Katie wasn't in sight.

"She's in the back, before you got here we laid out some mats so she could be more comfortable." Molly explained, seeing my initial confusion.

We continued walking past the lockers and changing area, past the showers, and stopped when we got to the equipment storage area. And there was Katie, sitting nervously on some mats they'd laid out on the floor.

"h..hey Alan." Katie greeted me shyly, as she stared at the floor.

It was a bit off putting to see Katie acting so shy and nervous, she was usually so bubbly and outgoing. I really felt for her, after all I'd been nervous like that before my first time as well. And though I was nervous now, I realized I couldn't show it or it would just make Katie even more nervous. I needed to act confident and comfortable, to show her that she's in good hands. But I also needed to be gentle and reassuring so she wouldn't be freaked out or anything, which it did help that she'd have Molly her best friend there for moral support.

I slowly took a seat next to Katie on the mats, so that I wasn't standing over her. Molly followed suit and sat down a couple of feet from us.

"It's alright Katie, no need to be so nervous. Just follow Alan's lead, I promise he'd never do anything hurt you or make you feel uncomfortable." Molly said in a gentle tone.

"Okay." Katie said, looking up at me for the first time since I entered the room.

I looked directly into her beautiful hazel eyes, then with a few fingers I slowly reached out and gently wiped a few stray strands of her dirty-blonde hair out of her face and her mouth creased into a slight smile. I took this as a good sign and slowly leaned in again until my lips met her's in a soft kiss. It was just a short peck kiss, before I pulled back to gauge her response. I didn't think to ask Molly just how experienced Katie was, so I didn't know if she'd ever even kissed a guy before. To my slight surprise Katie then leaned in towards me and initiated another kiss, this one longer and with more movement in our lips. She then parted her lips and I parted mine, allowing our tongues to meet in the middle, our tongues wrestled for a bit whilst entering each others mouths. We continued making out like that for a minute or so before we the broke apart to catch our breath. Obviously, she had some experience with kissing.

Katie was visibly excited after the short make out session, she was breathing harder and her chest moving more rapidly with her heart beat. The same could be said for myself, with my increased heart rate, I could feel a stirring in my loins. Taking her reaction to kissing as another good sign, I decided to move forward. So I slowly pulled my t-shirt off and laid it beside us, my semi-muscular torso now exposed to Katie for the first time. Luckily, Katie still looked to be comfortable, even biting her bottom lip as she slowly reached her hand out and began lightly running a few fingers over my abdomen and along my chest. Taking this as yet another good sign, I leaned in again and we began making out once more, whislt making out I began to slowly unbotton her school blazer and she didn't stop me, so when I had it unbottoned I broke our kiss and helped her slipped out of it. We set her blazer aside then recommenced with the kissing. What came next would make or break this whole thing, as our tongues explored each others mouths I slowly reached out and undid the top button on her blouse, then waited to see if she was going to stop me. She made no effort to stop me so I unbuttoned the next one, then another, and soon enough her blouse was completely unbuttoned and she hadn't stopped me, so far so good. We broke our kiss once again while I helped her out of her blouse, revealing a pale pink bra that hid her petite a-cup breasts.

Katie looked nervous once again as she used her arms to cover her chest, this was clearly the least amount of clothing she'd ever had on around a guy. I then wrapped her in a comforting embrace, to try and reassure her. It was then that I felt how much her body was shaking, she was really nervous about all this. Luckily Molly took this as her cue and she quickly joined the embrace, wrapping her arms around us as she pressed softly against Katie's trembling back.

"It's alright sweetie, you're doing so well, just relax." Molly whispered words of encouragement into Katie's ear.

"..okay.." Katie replied in a whisper.

"Just remember, I'm right here if you need me." Molly said, breaking her embrace.

Wow, Molly really is like a big sister to her, I thought to myself. Feeling nostalgiac once again as I briefly reminisced about how my own older sister and I used to be, and that sense of nostalgia was soon replaced with a feeling of melancholy. I was quickly brought back to reality as I realized I sill had a half-naked girl in front of me.

With Katie still in my arms, I began planting soft kisses along her neck, in my experience that was always a sure fire way to turn a girl on, and to my delight Katie was no different. She let out a subtle moan as I kissed her flawless neck. Taking that as the good sign that it was, I used my hands which were still wrapped around her to unclasp her bra. I broke our embrace as she nervously let the straps fall from her shoulders and the cups fall from her breasts. I sat back and admired her bare chest. Her breasts were no more than an a-cup, in fact I'd seen on her bra that the size was 32a to be exact. While, not very big, they actually fit her small frame quite well. And the two petite lumps of flesh were topped with a pair of perky little pink nipples that stuck straight out.

"You're beautiful, you know that?" I said, as she stared at the ground nervously.

"You really mean that?" she asked shyly.

"Of course I mean it." I replied, offering a reassuring smile.

"So you don't think my boobs are too small?" she asked, finally looking up at me.

"No, they're perfect." I answered truthfully.

I was being honest, from what I've seen, bust size is relative to the particular person's body type. Basically, with her petite body type, her a-cups were actually a perfect fit for her, if her breasts were much bigger then they'd look weird and disproportionate on her small frame.

"Thank you, Alan." she said with a smile, clearly no longer feeling so self-conscious about her breast size.

With that boost in her self esteem, I leaned towards her and planted deep kiss on her lips. I then parted my lips from her's and began planting kisses down her neck once again, to which she responded with another subtle moan. I slowly planted a trail kisses from her neck down to her chest. Once I reach the two soft mounds of flesh on her chest, I moved to one and planted kisses upon it until I reached the little pink nub that was her nipple. She let out another moan as I flicked my tongue across her stiff nipple, before taking it in my mouth and suckling on it. When I finished with one, I gave the same treatment to the other, eliciting the same moan in response from Katie.

Before taking things any further, I glanced up to see Molly, who was sitting behind Katie. Molly had her skirt hiked up and her panties pushed aside as she rubbed her pussy with one hand whilst groping her chest with the other. Obviously she'd gotten pretty turned on while watching the events with Katie and I slowly unfold. And I couldn't blame her, as my cock had been rock hard since I got Katie's shirt off.

I lifted my mouth from Katie's chest and began kissing down her smooth lean stomach until I stopped at the waistband of her skirt. I looked up at Katie questioningly, as if to ask permission to remove her skirt, she slowly nodded in the affirmative. I hooked my fingers into the waistband of her skirt, careful not to grab her panties as well, and began pulling. As I slowly slid her skirt down, she lifted her butt off the mat slightly, to allow me to slide the skirt down past her hips. I removed her skirt, revealing a pair of simple white cotton panties with a small pink floral pattern on them.

Now with Katie in only her little pair of panties, I pulled back, figuring it best that I even the playing field. So I removed my own pants as Katie watched intently, exposing my plain boxers with the large tent my erection was creating in the crotch of them. Katie just stared curiously at the large bulge in my boxers.

"Do you wanna see it?" I asked her.

"I've never seen one before, not in real life." she said innocently.

In response I slowly pulled my boxers down, letting my stiff 9 inches spring free. Katie's mouth was agape and her eyes wide.

"wow, it's so big. Are they all this big?" she innocently asked in surprise.

"Nah, he's certainly above average." Molly chimed in from behind her, licking her lips as she too stared at my member.

"wow" Katie uttered.

"Just wait till you feel that thing inside you." Molly said, biting her lip.

"Are you sure it'll fit?" Katie asked, suddenly looking a little worried.

"Don't worry sweetie, he'll be gentle and slow. All you have to do is relax." Molly said, in a reassuring tone.

"Ok" Katie replied.

Katie and I then met for another kiss. After breaking the kiss and feeling that she was ready to move forward, I began making my way down her lean body to her panties. I hooked my fingers in the small elastic waistband and began peeling them off slowly, Katie lifted her butt so I pull them past her hips. With her little cotton panties removed, she was now completely naked, like me. And her bald pussy was exposed, but not for long as she quickly moved her hands to cover it up. Still at eye level with her pussy, I looked up at her face, she looked a little nervous and scared.

"It's alright, I would never do anything to hurt you, Katie." I said truthfully.

Molly who'd stopped rubbing herself, wrapped Katie in her arms from behind.

"Just relax, sweetie. No rush. Why don't you just let him eat you out for a bit? I promise you'll love it, and I'm sure he wouldn't mind." Molly said in her sisterly kind of tone.

"Okay" Katie relented, both her and Molly looked down at me questioningly.

"I wouldn't mind at all." I said, smiling a reassuring smile at her.

Now, I didn't have a whole lot of experience with eating pussy, having only done it a couple times before. So I wasn't an expert or anything, but I did generally know my way around.

Katie moved her hands away and I planted a kiss just above her slit. I stopped for a moment just to take in the sweet musky scent of her pussy. She then let out a moan as I dragged my tongue along her outer lips, getting my first taste of the juices that had begun to leak from her pussy. I then gently parted her lips slightly with my fingers and began running my tongue along the inner folds near the entrance of her snatch. I continued lapping up the sweet juices that began to almost pour from her, and she continued to let out audible moans, she was getting very turned on. She was as ready as she'll ever be.

I moved back up her body and looked her in the eye.

"Are you ready?" I asked.

"Yeah." she said, biting her lip now.

"Now just to warn you, it may hurt for a bit in the beginning. But don't worry, that's only natural. Just relax and go with it. But if it gets to be too painful, then just tell me to stop and I will." I said.

She nodded an "ok" and I began to position myself over her. I spread her legs so that I was knealing between her thighs, my cock just inches from her pussy. Molly then grabbed Katie's hand and kept a hold of it, whispering in her ear words of encouragement.

"Okay, here goes." I said, then leaned down to kiss her again as I inched my cock forward.

She moaned into my mouth as the tip of my cock spread her lips apart and began to push into her tight wet hole. She broke our kiss and let out a little yelp as her pussy stretched around the first couple of inches of my member.

"Are you okay? Want me to stop?" I asked, concerned.

"No, just go slow." she said, biting her lip.

She was extremely tight, which was to be expected, but I kept slowly gently pushing, feeling her tightness stretch ever so slightly around my thick cock. Then suddenly I came to a dead stop just a couple of inches inside her, I'd reached her hymen. This would be the real painful part.

"Okay, now Katie, I need you to brace yourself. I'm gonna need to push a little harder to get past your hymen." I said.

"Yeah, and it will hurt. Hopefully not too much, but just relax and prepare yourself, you're about to be a woman." Molly told her, rubbing her hand and kissing her forehead.

Katie nodded in response, her nervousness showing in her eyes.

I then resumed pushing, this time harder, feeling her hymen began to give way.

"mmmm" Katie moaned through clenched teeth, while she held Molly's hand in a death grip.

I kept steadily pushing, until finally with a vocal yelp from Katie, her hymen had broken and my cock burrowed deeper into her hole. Katie's eyes began to water up as she gasped for air and her tight pussy clamped down on my shaft, I stopped moving immediately.

"It's okay sweetie, you did so well." Molly said, stroking Katie's head.

"But it hurts, Molly." Katie said, tears now running down her cheeks.

"I know, baby. It'll stop soon, I promise. But guess what? You're now officially no longer a virgin. You're a woman now." Molly said, trying to cheer her up.

I just watched silently as Molly continued talking to Katie, trying to comfort her. I still had my member buried in her tight hole and was careful not to move a single inch as she was still in pain and moving even a little bit would only hurt her more.

Finally after several minutes, Katie had calmed down and the muscles in her pussy that had me in a vice-grip seemed to relax.

"Are you ready to continue?" Molly asked Katie, seeing that she was more relaxed.

"Yeah, I think so." Katie replied, looking at Molly, then to me.

I nodded and began slowly pushing once again. Katie winced a bit in pain, but told me to keep going. She was still really tight, but her pussy had finally begun to get used to my thickness. A couple of more inches and I had finally bottomed out in her tight wet hole. I began to pull out a little bit, before pushing back in. I repeated that numerous times, keeping a slow pace, and Katie started to moan again in pleasure.