Chapter 4

I spent most of the next day in school looking at the girls around me, thinking about what Tess had said. Her encouraging me to try girls my own age bothered me more than I thought she realized. I just couldn’t help but develop serious feelings for her. After all the disdain and ridicule I had experienced from the girls surrounding me in that school and even at home, she was the first who accepted and wanted me. So, when she told me to get a girl my own age just to prove how she, an experienced woman, was better than them ... I didn’t know if I should feel sad about her not taking our relationship as seriously as I did, or just accept it as something kinky.

I realized quickly that it was not going to happen anyway, though. Sure, the girls looked at me differently ever since my makeover, or at least with less obvious contempt, but I was still absolutely clueless about how to even approach a female of my species after years of bullying. After hooking up with Tess so many times, I had regained some self respect and confidence. I was, however, still eating alone in the cafeteria, sitting alone in the library, and was still picked last when teams in PE were formed. There was no way I could just walk up to a girl I didn’t even know and ask her for a date, providing new ammunition to make fun of me with if she blew me off. And I didn’t expect any one of them to just walk up to me and do it herself, despite me looking better now, since I still wasn’t welcome at parties and gathering spots.

The only one I kept making some progress with was my English teacher, Mrs Jenkins. She knew exactly how I was looking at her, and she made no secret of it anymore. While she didn’t openly embrace it, she did seem to give me an increasing number of opportunities to appreciate her assets. When she was checking someone’s work, she would normally lean over the student’s shoulder. But for me, every so often, she would lean down in front of me, with the top three buttons of her blouse opened, allowing me to explore her ample cleavage in great detail. Whenever she noticed my involuntary reactions to that sight, a small smile of satisfaction would curl her lips.

As it turned out, however, I didn’t even need to look for girls at school. The next Friday was Ava’s birthday and, just as announced during the Thanksgiving dinner, she had friends over for a sleepover, with the parents at Uncle John’s. It was one of the first days I had to wear my new suit to work, because part of my new job was to plan and oversee the installation of surveillance equipment and software. So, Bill decided that I should be part of the initial meetings with the clients requiring such installations in their estates.

Despite what happened at Thanksgiving, I set out to look for something special I could get her. Ava was the only one who hadn’t gotten a reminder of our familial bonds yet. Well, except for Logan, but as I already said, he can eat a bag of dicks for all I cared. Although I had told myself that I didn’t want to buy their affection with gifts after the Nest Egg Necklace for Claire didn’t have the desired effect, it at least did have some effect. She did try to initiate a conversation multiple times, even if she bailed out every time for some reason. Maybe, whatever had stopped Claire from going through with it wouldn’t be such a problem for Ava.

I had overheard her talk on and on about wanting a new purse from someone she called “Kate Spade”, because she envied one of her friends who had one. Sadly, I still had absolutely no clue about fashion. Since Tess did a good job with my new outfits, and was a woman, I talked her into helping me choose a purse. Actually holding it in my hands, I couldn’t figure out why anybody would ever want one of these things. They were so small I could barely fit my fist inside, so they were utterly useless as a bag. It was called the “Essential” model, so I guess they didn’t exactly intend people to use them for camping, but then again, why did such a small thing cost $198 dollars!? I just resigned myself to giving it a try, and had the clerk put it in a gift bag. In addition, I talked Tess out of a champagne bottle and decorated it with some ribbons.

When I came back from work at around Eight PM, Ava and her friends were apparently taking a break from enjoying the hot tub, because they were all wearing swimsuits. While Ava was in the kitchen, her three friends were spending time on the sofa with Logan. I knew two of the three girls. One of them was Mia, Ava’s oldest friend since they were little. She was also Jack’s little sister. Since I publicly knocked her big brother out, she usually regarded me with disdain. I only knew the second girl from looks, since I had seen her often at school hanging around Ava and Mia, where she was pretty much indifferent to me. The third girl was vaguely familiar, but I couldn’t really place her.

So, when I stepped into the living room, all eyes were on me, and the contrast was hilarious.

At that moment, the slim fit suit was working its magic by perfectly showing off the fruits of my daily training, and those three girls ogled me without even trying to hide it. The unknown girl wasn’t just ogling me, she was watching me with borderline hunger. Logan, on the other hand, seemed pleasantly unhappy about the attention I was receiving from these girls, who seemed to have momentarily forgotten about him even being there.

I turned to the kitchen and walked towards Ava, who, for some reason, seemed uncomfortable upon seeing me. She came out of the kitchen and met me halfway.

“Happy Birthday.” I said in a casual tone, handing her the bag, as she had just opened her mouth to say something.

“You got me a gift!?” she asked, incredulously. Somehow, she looked even more uncomfortable now.

“And he brought some sparkly wine as well!” commented one of the unknown girls in a happy shout. That made me remember the bottle, so I walked past Ava and placed it in the freezer. When I came back out, Ava was still standing there holding the gift bag in both hands, looking like a lost puppy.

“Go on, look inside. If I got the wrong thing just tell me. I still got the slip, so you can return it.”

She looked at me with some uncertainty for a second, before slowly pulling the piles of useless wax paper out of the bag. When she finally saw what was underneath, she paused. Then, she tentatively pulled out the purse, showed it to her friends, and they started this high-pitched screaming exercise I only knew from teenage girls in movies until then. It looked like Tess got it right again.

“How did you know I wanted one of these?” Ava asked, still breathing heavily from running around.

“You kept mentioning that brand the other day, and I figured the others would have your presents probably already set.” I answered, matter of fact.

After saying that, Ava’s three guests looked at me in silent approval. I noticed Logan eyeing the whole scene, but especially the purse, with disbelief from the sofa. Then he looked at the coffee table with embarrassment. When I followed his eyes, I saw a cheap no-name Bluetooth speaker Ava hadn’t even taken out of the box to check it out. Whether it was being attentive or being able to fulfill a wish, I had just proven myself more reliable than Logan. That alone was worth spending two-hundred bucks on an utterly useless bag.

Then Ava did something that shocked me. She stepped into me, wrapped her arms around my torso and gave me a tight squeeze.

“I’m sorry we forgot your Birthday!” she whispered into my ear.

The shock from the hug faded. At least enough for parts of my brain to start working again, and I remembered that, even though she was too occupied at the time to participate, Ava was there when Granny had that talk with Claire at Thanksgiving. And the way she now reacted confirmed my fear of having to buy her affection. After they all had that talk with Granny, none of them mentioned anything about it to me, or tried anything in the days since then to introduce me to their fun. They didn’t even attempt to close the gap that had formed between us. There was still no consideration for me whatsoever.

But the moment Ava got expensive shit from me, she was suddenly sorry for forgetting my birthday. I had hoped for this present to serve as some kind of reminder of my existence, that would cause her to slowly come around and rethink her opinion of me. This reaction, however, seemed too sudden and extreme to have a lasting effect.

“Why did you even get me something like this after what we did?” she asked, just as quietly as before.

“Maybe I’m just a better person than you four.” I reproachfully whispered back, unwilling to forget, and immediately disproving my own statement without even noticing. “Or, maybe, I just wasn’t eager for your parents to shit on me again, like last year when I didn’t have something for you.”

Ava immediately let go of me and took a step back, looking almost sad. I mentally scolded myself as I saw Logan’s relieved look, but I just couldn’t resist pointing out the double standard. Maybe I should have embraced Ava, just to piss him off further. Coincidentally, one of Ava’s friends helped me out with that.

“Hey, we were just about to watch a movie. Why don’t you join us?” the vaguely familiar girl asked.

She had stepped in close to me when Ava had stepped back, and was brushing one hand over my biceps as her other hand was pulling a strain of shoulder-long ash-brown hair behind her ear. She looked remarkably cute. Her head tilted slightly to the ground with an almost sheepish expression, looking up at me with doe-like big brown eyes and a shy smile. It didn’t help that she was barely five feet tall, with a slender frame supporting maybe an A-Cup chest. I just wanted to cuddle her to death.

“Oh, yes! Please, join us!” threw one of Ava’s known friends into the round, but she was giving the small girl a conspiratorial grin. I looked at Ava, awaiting her answer. It was her birthday party after all. It was up to her who she wanted to spend time with today. When she nodded her approval, I looked back at the cute one.

“Don’t take this as a cheesy pick-up line, but ... do we know each other somehow? You seem familiar, but I just can’t place it!” I finally caved, and asked.

First, she acted a little insulted that I didn’t remember her, but then she seemed to reach a conclusion and lit up again.

“I’m Jenny. That... “ she pointed at the girl that supported her when asking me to join them “ ... is my big sister, Joan. You helped me out last year, when Jack and his friend wouldn’t leave me alone.”

“That was you! I remember now! But it was more you helping me out than the other way around. I was just there, but you saved me from Coach Jenkins when he wanted me expelled.” I remembered.

“You did bust them up pretty good.” Joan commented, laughing “Not that I’m complaining. They had it coming!”

“Don’t encourage him!” Logan injected by shouting from the other side of the room.

“Well, I’m gonna have to get out of this suit. I’ll join you in a minute.” I said, before making my way to my room to get changed.

For a moment I was thinking about getting into my own swimming trunks, since the people downstairs were all still wearing their swimsuits. And Jenny seemed to appreciate my looks, so sitting there topless would certainly be advantageous. But sitting with three, well four if you count Ava, basically naked hot girls in only my trunks would certainly lead to embarrassing displays on my part. So, I compromised on cargo shorts and a tight T-shirt. I had just put the shorts on, when my door flew open, and Logan stepped into my room.

“The fuck are you thinking, Tiny Tim?” he seethed.

“What do you mean?” I asked, smirking. There were certainly quite a few things coming to my mind he could be pissed about, and I enjoyed how much it seemed to have gotten under his skin.

“Really? Do I need to spell it out for you? Ava doesn’t want you there with her friends. She just feels guilty about your little hurt feelings. Get over it. I put in a lot of effort to make this fun for us. How the hell am I supposed to do this with your sorry ass around?”

“I don’t know. Fuck yourself?” I asked in an aloof voice while pulling my shirt over my head.

I looked at him for a moment with a blank expression. I didn’t know what he would do next. I didn’t expect him to try and attack me, he knew better than to even try. But if he had some other mean move up his sleeve, I’d rather he tried it before we met up with the others. And I hoped he was angry enough to not realize that. Problem was, he just glared at me before he turned and left. So, I had no idea if he was out of options or wanted to put me down in front of an audience again. I resigned myself to whatever my fate would be and got downstairs myself.

The lights in the living room were dimmed and all of the others had already found their seats. Ava and Joan sat to either side of Logan on the sofa. Mia had made herself at ease in the armchair. The only free spot, other than the floor, was right next to Jenny on the loveseat. She had pulled her legs underneath herself, in that impossible way only women could ever find comfortable. She was giving me a huge smile as I spotted the empty seat next to her, so I took that as an invitation and sat with my arm over the backrest while maintaining a respectful distance between our bodies.

I didn’t really know what to expect from this situation. Under normal circumstances, I would have fully expected them to banish me from their festivities again, like Logan had just tried when he came into my room. An invitation from Ava and her friends, who had tormented me in school, would normally have my alarm bells ringing and make me expect some kind of mean prank. But I did indeed help Jenny last year, so maybe she really was interested in getting to know me. And the seemingly genuine display of regret from Ava that I had witnessed when I presented her gift, however short lived it may turn out to be, made me want to risk it and see if this could possibly be the first sign of change. Though, I hadn’t forgotten that the last time I was hoping our relationship would improve, I was suddenly holding a penis pump in my hands while my mother laughed her ass off.

The first thing we watched was some kind of live special from a stand-up comedian. He was good. And each time the room was filled with laughter, Jenny coincidentally scooted a little closer to me. By the end of it, she was leaning against me, my arm still on the backrest. By then it was 9:30 PM, and, as Ava was scrolling through the Netflix library, I remembered that I had placed the champagne in the freezer. I jumped up and got it out, relieved it wasn’t frozen yet. When the others saw me holding the bottle, they assumed I was about to open it, and sent Logan after me to get some glasses.

It wasn’t much. With six people to share, maybe two glasses per person, so I didn’t really feel guilty about underaged drinking. As we took our seats again, Jenny immediately cuddled into me. By the time Ava had found the rom-com she wanted to watch, Jenny had taken my arm from the backrest and wrapped it around herself instead. Ava looked around the room, took a sip from her glass, and threw me a big happy smile. She seemed to like it.

The champagne combined with the cheesy movie apparently had a certain effect on Jenny. She soon placed her hand on my arm she had wrapped around herself, and was absentmindedly stroking it as she sipped away. Now, I wasn’t used to drinking either, and I had to admit that Jenny wasn’t the only one affected by it. The furniture and seating arrangements had the benefit that Jenny was sitting at the far outside, with my body hiding hers from the others. The main effect the champagne had on me was my lowered guard. I liked being so close to a girl. As long as I didn’t try anything they could use against me, maybe it wasn’t so bad if I allowed myself to simply enjoy it.

I started by softly scraping my fingernails over the inside of her forearm for a few minutes, just to test how she would react, and she snuggled deeper into me. Then I let my fingers wander from her arm, over the top of her thigh, to the middle of her belly. Since the swimsuit she was wearing was a two-piece, her entire midsection was exposed skin, so I carefully caressed her bellybutton. This coaxed a cute little moan of approval from her lips, and she nested her face into my chest. Without letting up my light caresses, I raised the hand holding my own glass, moved a few strands of hair from her forehead, and placed a light kiss on it. Now she was purring like a kitten. She looked up into my eyes, then at my mouth, and tilted her head a little.

I contemplated if I should risk it. The gesture seemed unambiguous, but I was still held back by the possibility of this being some kind of set-up. Soon, though, the champagne did its work and I decided that, even if it was a set-up, I had nothing to lose with my school life and reputation already being as bad as they were. I placed a small kiss on her lips, and she rewarded me with a content sigh, before nesting her face back into my chest. This girl barely knew me, never had a real conversation with me, but she thoroughly enjoyed acting like intimate lovers. It was almost ridiculous to even consider this, but ... maybe she had a crush on me since I saved her?

Then she surprised me. I had only planned to slowly familiarize myself with her body, while making sure not to push too far, but she seemed to have a different idea. Her breathing had become a little shallow, as she slowly grabbed the hand caressing her navel and started pulling it down to the bottom piece of her swimsuit. As my fingertips were resting just at the edge of her waistband, she placed both her hands on top of mine, pressed it into her lower belly, and she gave me a quiet but sensual kiss.

My mind rattled by her boldness and overwhelmed with the desire for what this could possibly lead to, my hand moved down without me thinking about it, as she spread her legs as much as her sitting position allowed. The entire way down she pressed it into her body with both of her own hands, silently encouraging me. I didn’t go underneath her swimsuit, yet, as I seriously didn’t want to risk overstepping. Not in front of Logan, who was undoubtedly engaged in his own fun with at least Ava, if not Joan as well, at the time. Golden Boy wouldn’t be pushed away, since I already knew how close he and Ava really were. If I was rejected in front of an audience, none of them would ever let me live that down. If I was to have any chance with this girl, I had to remember every single lesson I received from Tess, and make this as enjoyable for Jenny as possible while I still could.

I gently massaged the skin just above where I surmised her clitoris to be in a circular motion. Slowly increasing the pressure as her breathing increased in intensity. Then I pushed my hand further down, splitting my fingers, so two of them would scrape over each of her outer lips, and worked those for a while. Finally, I moved my hand up enough so my index and middle finger could directly massage her clit. She was now grabbing onto my arm with desperation, pressing her small breasts into my upper arm and her face into my shoulder, trying to stifle the cute mouselike squeaking noises escaping her. Suddenly, her entire body tensed up, her legs clamped shut, and her fingernails dug painfully into the skin of my arm. She stayed like this, not breathing, for maybe ten seconds, before finally relaxing and melting into me.

Going by her breathing, she was taking a nap. At that moment, I was damn glad I opted for the cargo shorts. Otherwise I would be pitching an obscene tent right in front of everyone. I looked around and realized with horror that we were being watched by Joan. She knew exactly what I had just done to her little sister, and in the darkness of the room, I could see a sinister looking smile on her face. I thought I was done for, as I realized this must have been their plan all along. After Logan had watched in glee as I was beaten, I wouldn’t put it past them to accuse me of taking advantage of a drunk, innocent girl. And I was even the one providing the alcohol!

Just as my anxiety was reaching dangerous levels, however, the TV illuminated the room more effectively, and I realized that Joan’s smile was anything but sinister. It was actually a quite warm smile she was displaying. She seemed to be happy for her little sister.

I lightly shook my head, trying to get my assumptions under control and push my expectations for being played out of my thoughts. Jenny stayed asleep until the movie was over, and I gently nudged her awake. She looked around, then at me, her eyes focused, and then she blushed with a coy smile on her lips. Again, I could just cuddle the girl to death.

My erection was gone by then, and while the others had spent the entire afternoon after school relaxing in the hot tub, I was at work. That, combined with the effect of the two glasses I had during the movie, started to have an effect on me, so I excused myself to make my way to my room and get some shut eye myself.

I had just stepped out of my shorts after a trip to the bathroom, when I heard a soft knock at my door. When I opened it, Jenny was standing there in an oversized shirt and panties. Without saying a word, she placed her hands on the back of my neck, went on her toes, and pulled me down for a passionate kiss while pushing me backwards into my room. Then she turned around and closed the door.

“Can we ... continue?” she asked meekly.

I just wrapped her into my arms and kissed her again. That was when things started to get less enjoyable. But not yet in the way I had feared for most part of the evening.

As we kissed, I opened my mouth and let my tongue glide along her lips, coercing her to open her mouth. She soon did, but as I tried to massage her tongue with my own, I realized her tongue was wildly thrashing around inside her mouth. What the hell was she trying to do? Swat flies? Don’t try to tell me she never kissed a boy, she just had me finger her to an orgasm in the middle of a packed room, not even five feet away from her own sister. There was no way this girl was innocent.

So, I switched gears. My hands ran down her spine and cupped her sweet little ass, pulling her onto her toes and further into me. As this motion spread her cheeks apart, she let out another moan into my mouth. Then my hands moved back up, but under her shirt. I grabbed the seams and pulled it over her head. As soon as it had passed her arms, she used them to cover her breasts and looked at me in an insecure way. I just smiled at her, gently took her hands into mine, and pulled them aside. Her nipples were hard knobs that just begged to be kissed, licked and sucked, so that is what I did. She soon had overcome her insecurity and her breathing, once again, became ragged. As she placed her hands on the back of my head, she spoke.

“They’re not too small?” she asked, clearly hoping for my approval.

“Jenny, men are simple creatures. We like all kinds of boobs!” I said, before circling her other nipple with my tongue and lightly scraping my teeth over it.

I placed kisses on her breasts, along her sternum to her belly, over her navel, and finally further down. After I went to my knees, I took hold of the sides of her panties and started tugging, but she stopped me.

“I don’t ... Can we do something else first? I owe you after what you did before!” she said, and I complied.

I got back up on my feet and pulled my shirt over my head. Her eyes grew wide as she appreciated what she saw. She stretched out her hand and caressed my abs, before going to her knees herself and tugging on my underwear. My dick was rock hard again and tenting my shorts considerably. When the waistband finally passed my tip, she halted and just stared at it.

A serious look of doubt mixed itself into her features. She let the shorts fall to the ground, and my dick jumped a little as I stepped out of them, but mainly stayed pointed directly at her face. Finally she grabbed it with both hands, causing me to groan in anticipation. Her hands were so small, she couldn’t reach all the way around it. She pumped my shaft a few times, took a deep breath as if to steady herself, and I could hear her mumble to herself.

“Just like a lollipop.”

I was confused and blurted out, “What?”

“It’s just ... I haven’t done this very often. And I thought you’d be...”

Instead of finishing her statement, she shook her head, opened her mouth wide and placed her lips just underneath my crown. And then she simply stayed like this. Completely unmoving, while suckling on it like it was a lollipop! Or a pacifier, was more like it. Occasionally, I could feel her tongue glide along the underside of it, but that was as far as she would go. After a few moments, she at least started stroking me with her hands again, but this wasn’t fun. It didn’t feel good. This was the exact opposite of what I experienced with Tess.

“Could you ... maybe ... take more of it into your mouth?” I carefully asked.

She looked at me without taking it out of her mouth, but seemed to think it over. Then she tried, took an entire additional half inch into her mouth, and stopped again. That wasn’t enough for a blowjob, especially if she wouldn’t move her head. While I didn’t comment about it in any way, she probably sensed me slightly deflating, because she tried to take more on her own. She had to immediately back up again to ease her gag reflex. This wasn’t going to happen, and I had absolutely no intention in just forcing it down her throat or making her feel bad about it.

“Let me do it for you now.” I demanded, picked her up into my arms, and sat her on my bed.

I went down on my knees in front of her, grabbed her legs, and pulled her towards me until her hips were on the edge of the mattress. But she wouldn’t let go of her panties, so I asked her what was wrong.

“I normally don’t let someone put his face there, until I really trust him.” she said, and I had to admit, it made sense to me. I was accustomed to feeling insecure about my own body after being teased about it for years.

“Jenny, we can just stop if you’re not sure. No hard feelings. But I can assure you, I like going down on girls.” I proposed.

She thought about it for a moment, and then relaxed at least somewhat. I gently pulled her underwear off, opened her legs, and kissed my way up her legs. From her knees, along her inner thighs, right up to her center. She was already glistening wet. She smelled different than Tess, less intense, and certainly nothing she would need to be shy or embarrassed about.

I gave her everything I learned from Tess. Gently nibbling her clit, testing out what strength she preferred, massaging its hood with my tongue, while slowly penetrating her with my fingers. I was right, this girl was not innocent, but she certainly wasn’t awfully experienced either. I had eaten her to a small orgasm within two minutes but didn’t let up.

One thing I noticed was that I had a rough time finding that special spot inside her, as she wasn’t nearly as vocal as Tess was in bed. Tess knew exactly what she wanted and how she wanted it, and she had no trouble communicating it. Jenny was holding herself back the entire time, as if she was afraid of making sounds or expressing pleasure in any way. After another five minutes, however, she was building up to an orgasm even she couldn’t hold in. By the time it hit her, she was lifting her hips off the mattress, pressing her sex into my face, while simultaneously pulling my head into her by my hair. She was throwing her head from side to side as it built and finally screamed so loud I was sure the entire house heard it.

I was totally fine with that, to be honest. Let them all know that I had just given that girl a massive orgasm. Even better, scream out what I did to achieve it! From what I had seen on the videos on Golden Boy’s phone, the men of the family weren’t big on oral, unless it was about receiving it themselves. Though, I could somehow understand that, given how much they traded partners. Maybe they were not exactly eager to taste dick residue or something.

When Jenny was done convulsing, I grabbed her ankles, placed her legs over my shoulders, and my dick along her slit. Then I started humping, dragging the underside of my shaft over her slit with my crown hitting her clit, lubricating it with her juices while waiting for her to finally come back from her orgasm. When her eyes were focused again, I leaned in to kiss her, which she eagerly responded to. But when I leaned back, she looked down, and the look of satisfied bliss vanished instantly.

Following her gaze, I looked down at myself to see what could be bothering her. As I had moved up to kiss her, my dick had slid upwards as well. Now only my balls were resting in front of her entrance, while my fully erect cock lay across her belly, looking quite impressive against her tiny body. It reached all the way from her clitoris, along her lower abdomen, with the tip reaching her belly button. As I just developed a slight grin while imagining how this would feel for me once I entered her, Jenny’s stern voice pulled me back to reality.