“Makes sense. Problem is, I kinda lack ... what’s it called... ‘fashion sense’. How would...”
“Oh, I can help with that!” she interrupted me with her eyes sparkling. Apparently, that was just what she wanted to hear. “No Sparring today. Let’s go shopping!”
She grabbed my arm and basically dragged me out of the building. For some reason, everyone we walked past gave me a slightly unsettling smile. Tess took me to what she called a ‘haberdasher’. As it turned out, I needed everything! After spending roughly twelve hours each week in the gym for nine full months, while simultaneously radically reducing my junk food intake, I had successfully shed forty pounds of fat off my body, and started to fill out quite nicely with muscles instead. At 5’10’’, and 196 pounds, I wasn’t exactly small anymore either. I wasn’t a big fan of starvation, so my torso would never get even close to that desirable V-shape, though I did get broad shoulders and was even slowly developing abs. Painstakingly slowly, that is.
I didn’t have anyone to impress, though, so I had stopped caring about my appearance quite a while ago. As long as my clothes covered what needed to be covered, I was contented with them. So, I only got new stuff when the old stuff fell apart. I decided then and there to simply let Tess take the reins and do as I was told.
I got a bunch of T-shirts, button-up shirts, a black m-65 jacket, cargo pants, dress pants, two of those belts without holes, socks without holes, underwear without holes, shoes that didn’t talk, and Tess made me model everything for her. Even the underwear, for some reason. Then came the grooming products and toiletries. Hair Gel, specific deodorants and aftershaves, she even insisted on a pricey cologne that I could only describe as a musky cedarwood smell.
In the end, I even had to get a suit. I let Tess choose a plain black, slim fit three piece, with a collection of gray ties, and then we had them adjust it for me. It almost looked like it was tailored for me. Although Bill would later laugh me out of the conference room the first time he saw it, telling me to lose the vest and tie unless I wanted to start a career as a banker and get strangled.
When the clerk asked me the famous “Left or Right” question, I had absolutely no idea what he was asking, and the confusion showed on my face. When Tess answered him by shouting “LEFT!” through the curtain, the confusion was showing on the clerk’s face, and he fixed me with a calculating look before the exact same small smirk spread across his face I had seen on the guys in the firm. He finally explained the meaning to me, and I, for the life of me, couldn’t figure out how the hell Tess knew where I let my balls hang when I didn’t even know myself.
By the time we were done, my bank account was another $2,800 lighter. I was glad this wasn’t something I had to do every month. Luckily, I could afford it all.
I basically had no friends left to go out with, abandoned all hobbies that could require money, and I also never had a girlfriend I could spend on. Basically, I spent my entire time either in school or working, so I really didn’t have time for anything else even if I had friends to go out with. I worked roughly twenty-six hours a week on the firm’s projects alone. At thirty-five dollars an hour, that makes roughly $3,600 a month. Tess had helped me figure out my taxes in January, and I now knew that I netted about $2,800 a month after taxes. My only expenses were the three-hundred dollars per month I paid Aaron in rent, another two-hundred dollars per month I spent for food, and $480 per month I was going to pay in car insurance from then on (which I got cheap thanks to the safety course from Bill!).
So, from my regular income alone, I had made about $1,800 a month that simply went to my bank account and sat there mostly unused. But in addition to that, I still maintained my old projects from home. I had a nice little revenue stream from my Apps, in addition to the side projects I had picked up from Craigslist and fiverr. That was possible because I got lucky by ignoring european data protection laws. I had learned through Bill that a friend of his, who worked security in Germany, needed an app for his bouncers to check vaccination statuses. So, I pulled the specifications for the EU-Vaccination-Certificates, created an app, and published it. About two months later, the EU required all clubs, bars, discos and restaurants to only allow people with booster-shots to enter their establishments, but their own official App couldn’t differentiate between a vaccination and a booster shot. Mine could, because I didn’t hide that information from the bouncers like the official App did, and soon my app was used all across Europe.
All in all, I made maybe $2,600 per month after taxes, rent and food. And, at that point, I had been working for the firm for ten months without having to pay insurance, so my bank account was nicely filled even after I bought the car.
Tess made me wear the suit when we left the store and loaded the bags into my Jeep. Then she announced there was only one thing left to do, before she dragged me further to a barber shop for a haircut. I got, what they called, a ‘Long Crew Cut’. A style basically every guy in the firm seemed to prefer, but then they put a little gel to style what was left of my hair. Cut, styled and dressed, Tess and the woman who cut my hair took an appraising look at me. They gave each other approving nods, and then we finally left. But as soon as we were in the car, Tess startled me.
“So, now that we finally got you presentable, you have to take me out for a drink as a thanks for the hard work I put in.”
I didn’t rightly know how to respond to that. It was almost Eight PM by then and I’d have loved to take her out, but I just turned sixteen and it was a Thursday, a school night. It would be hard for me to get into a bar. Tess didn’t seem to believe so and directed me to a little club she apparently visited on a regular basis.
We got a table and ordered our drinks. We sipped them as we talked, and I tried to not appear too hopeful or desperate. But the way her tight business attire framed her body was quite distracting. I mentally scolded myself whenever my eyes got stuck on her breasts, and wondered just how much of a pervert I would have been, had I been drinking something more fun than a diet coke. After a while, she asked me to dance, and with that I got visibly nervous. Like, a lot. I had no fucking clue how to fucking dance! Tess took one look at my demeanor and chuckled. I immediately thought this date was over, but then she just grabbed me by the hand.
“So you’re one of those guys who don’t dance. Too bad, I demand entertainment!” she announced and pulled me onto the dance floor.
I looked around, trying to figure out how to move and basically copying whatever I saw other guys doing. Within seconds, I was simply captivated by Tess and the way she looked at me with that big smile on her face. I had absolutely no idea why, but she seemed to genuinely enjoy being there with me. I forgot about the others around us and just moved with her, when she turned around and started to rub her butt into my groin while her hand was moving behind my head. Then she leaned her head back and pulled mine down, so she could whisper in my ear.
“You remember how I told you I’m from Virginia?”
I nodded my head, yes.
“You turned sixteen today. That means back home...” she paused, getting even closer, her lips momentarily brushing my neck and her hot breath in my ear “ ... you’re legal now.”
My cock was somewhat stiffening since I started to relax, but now it got rock hard in record time. Before I could react in any other way, Tess had pressed her butt into it with determination. To my immense surprise she suddenly turned around and looked at me with big sparkling eyes. Slowly, a big grin spread across her face. She put her arms around my neck, pressed her breasts into my chest, and brought her face close to mine with a sultry look.
“Baby, is that thing as hard as it feels? Is it for me?” she whispered directly into my ear before biting my earlobe.
I involuntarily swallowed and asked, “Want to check and find out?”, surprised at my own boldness.
Tess grabbed my hand again and, like she did the entire day already, dragged me after her towards the ladies’ bathroom. In there, she pushed me into one of the stalls by pressing her whole body into me, while giving me the most passionate of kisses I could imagine. Her tongue explored my mouth before wrapping itself around my own. All the while stroking my dick through my new pants. As fast as it started, it stopped. Suddenly she was on her knees in front of me, fiddling with my pants. By now, the outline of my cock was clearly visible. Once she had pulled my pants down, my cock sprang up and hit her in the chin. I was so fucking hard, but also so fucking nervous, I thought I would pass out any moment.
Seeing the pole of hard meat pointing at her, her eyes glimmered with lust while glancing up at me. She tried to wrap her hand around it, but it seemed to be just a tiny bit too thick for her hand to reach all the way around. Something she noted with approval before she started stroking it. Then she leaned forward and let the thing rest on her face for a second, grinning madly while looking into my eyes. Slowly she stuck her tongue out, dragged it over my balls, and then licked the underside of my shaft all the way from the bottom to the top.
I shivered. This was so much better than my hand! This was so much better than anything I had ever experienced before. Her warm, spongy tongue gliding over the sensitive skin on the underside of my dick caused my entire body to tense up. When it reached my frenulum and she let the tip of her tongue flick over it, I even involuntarily bent forward and quietly gasped.
My reaction caused her to chuckle. She liked to see the effect she had on me. I never felt anything comparable to this level of lust, and would have been ready to explode the moment my cock hit her face. The thing holding me back at that moment, however, was the almost overwhelming fear of someone coming in and catching us in the act. The fucking stall door was still wide open and blocked by Tess kneeling next to it! A fear Tess herself didn’t seem to share, though, when she wrapped her lips around my tip and started to suck on it.
After I was in pure heaven for half a minute, she did something I did not expect. Without taking my rock hard member out of her mouth, without even moving her head at all, she took my right hand and placed it on the back of her head, glancing up at me with an expectant look. I couldn’t hold back anymore, I needed that heavenly feeling of her mouth and tongue to come back, so I just pushed her head down on my cock, but she again just remained still with my cock now deeper in her mouth. So, I grabbed her ponytail and pulled her head back again. Realizing she wouldn’t do it herself and wanted me to do it for her, I fucked her mouth. A few times even sending my dick just past her uvula without intending to. I simply didn’t have enough control over my body anymore.
Luckily, Tess didn’t seem to mind it that much. In fact, the first time it happened, I was so overwhelmed by the sudden extra stimulation, I momentarily forgot to pull her head back. Instead of complaining or moving on her own again, she simply stuck her tongue out like she was trying to reach my balls. I just kept going and, an embarrassingly short minute later, her eyes went wide as my cum flooded into her mouth. She loudly swallowed most of it while moaning her appreciation.
I had never imagined just how overwhelmingly sexy it would really be to see a woman swallow my cum while moaning in approval. It felt like she had just ultimately accepted everything about me, and nothing about me could disgust or repulse her. I immediately knew that I had no reason to be ashamed about my lust when I was with this woman. And, even more importantly, I immediately knew that she would not reject me like my family had. So, when she thought I was done, I really wasn’t. The whole ordeal was just so stimulating that I wouldn’t grow soft. Much to Tess’ pleasure, because she also wanted more.
“I need you to fuck me! Now!” she said, finally closing and locking the damn stall door.
She pulled her skirt up to her hips, leaned forwards against the door with one hand, and pulled her panties to the side with the other. I didn’t waste a second. Not having any experience, and being unable to control myself any longer, I just grabbed her by her hips and rammed my entire length into her wet pussy in one quick thrust. Just as I felt the tip of my dick pass through what felt like an extra tightness inside her channel, Tess let out a mixture of a scream and a moan.
“Fuck MEEEE! YES! Stretch me out! Take me HARD, Baby!”
Since I just came in her mouth, I could now last longer. Encouraged by her loud moaning, I just kept doing hard strokes. Pulling my dick halfway out of her, then hardly ramming it back in. She leaned back into me and I wanted to explore her body while fucking her, although I did notice that, since she leaned back, I couldn’t reach that wonderfully tight part inside her anymore. I reached around her with my left arm to grab her right breast, while my right hand reached down to rub the skin above her clitoris in a circular motion. After just a few short minutes, I felt her spasm on my cock, and she leaned forward again to hold on to the door.
Like a piston I went back to hard strokes, as more and more of her juices flowed out of her. My thighs and balls were now drenched in her fluids, she started to lose her hold on the door and slid ever so slightly down with every stroke I gave her. This was even better than the blowjob! The way her walls wrapped around me, stimulating my entire lengths all at once, had me almost abandon all reason and forget about where we were. The only thing that existed for me at that moment was the pleasure of being buried inside this wonderful woman.
Consequently, I felt my balls tighten very soon. I knew I had to warn her, but she could barely speak.
“Yes ... come ... safe...”
So that’s what I did, recklessly abandoning all precautions I was taught about. She had slid down the door so far, the angle was perfect again. As my own orgasm came crashing onto me, I forced as much of my cock into her as I could, finally penetrating her innermost parts once more and pumped her quivering womb full of my seed, sending Tess over the edge of a final and powerful orgasm. Once I was able to open my eyes, I pulled out and let go of her. Tess just slumped down onto the floor, catching her breath while bathing in the aftermath of her orgasm, while my cum slowly leaked out of her.
“
After another minute, we both had mostly recovered and were standing, albeit on somewhat wobbly legs. Tess gave me another kiss.
“Tim, Baby? We SO have to do this again sometime.” she said, causing me to start laughing.
All the tension in my body was completely gone, and I felt better than I had ever before. Especially better than I had felt in the last three years. I wasn’t too happy about her choice of a pet name, since “Baby” put such an emphasis on me being so much younger than her, but a gorgeous woman calling me by a pet name was simply too good to complain about it.
By the time we were both presentable again, it was half past Ten at night. We were in the Bathroom for almost twenty minutes. Thank God that club had so few customers, or we would certainly have had an audience. As we made our way out of the bathroom, I caught the looks of some of the patrons and immediately realized that we indeed did have an audience. With every step we took towards the door, my face grew hotter, and, by the time we stepped outside, I was sure It must’ve been glowing red. Tess, however, seemed to be absolutely indifferent towards it.
I drove us back to the company parking lot so she could get her own car, and we parted with her giving me yet another toe-curling kiss, pressing her full body hard into mine. Then she spoke.
“How about we finally exchange phone numbers? I was serious when I asked to do this again.”
I eagerly pulled out my phone but, when she looked at it, she started laughing.
“What is that? I haven’t seen one of those in years! Aren’t you our IT-Guy? Don’t you need a smartphone?”
“Oh, I have one for work. But privately I use feature-phones. They were stolen too many times in school.”
“Well, whenever you wear the suit, you should switch to the smartphone. That foldable brick causes some unhealthy-looking bulges.”
“Okay, I have to ask! Today, you chose what clothes I’m to buy, what hairstyle I’m to wear, how I’m supposed to smell, and now you complain about how my phone looks. Not that I’m complaining, since I have no idea about any of that, but what’s this all about?”
Before she answered, she closed the distance between us again and put her arms around my neck.
“Maybe I’m just trying to make you look as mature as you’re behaving, so less people will accuse me of cradle robbing.” she lightly laughed.
She probably meant that as a joke, but her calling me mature was actually a problem for me. I was behaving maturely because I had to. I had to work a job because Aaron refused to pay for my textbooks. I had to do my own laundry because the family couldn’t be bothered to. I had to learn how to cook because Claire would simply forget about me when grocery shopping, in favor of whatever her two other children wanted to eat. And it didn’t help that I had barely any people my own age left to interact with. I was spending all my leisure time with the adults from work.
Again, I had no illusions this could ever lead to a relationship. I had nothing to offer this woman, never had a romantic relationship before, and, until a few minutes ago, was an insecure virgin. Well, I was still insecure, which is why I kept asking myself what she would even want with me. Especially if she learned about all of my baggage. But, if I were to address that now, there wouldn’t even be the chance for casual sex left, so I just opted to not go into details at that moment.
“I could live with that.” I answered, before giving her a light peck.
“In all seriousness, Tim. What we did in there ... Please understand, I grew up where sex at sixteen was perfectly fine. And you do have your charms. I’d really like to continue, but we can’t let people know until you’re seventeen. Can you promise me that?”
“I can. Though, I’m pretty sure the guys at work know already. Going by the looks they gave me when we left, at least. I don’t think that many people would have a problem with it. But I will not run around and advertise the whole thing.”
We exchanged numbers and got on our way. When I finally made it back to the house, I grabbed the five bags with my new clothes from the Jeep, fumbled with my keys, and finally got inside. As I stepped into the living room, I didn’t notice how every seat in there was packed, since I was trying to get my keys out of the door with only one hand.
When I turned my head, I saw the entire family, except the grandparents, huddled on the sofa and loveseat. All of them regarded me with big eyes. Ava actually looked like she just froze mid-movement, as a spoon full of chocolate ice cream was poised halfway between the bucket in her lap and her mouth.
“Huh.” Meggie remarked, looking at me appraisingly.
“What?” I asked, clear irritation in my voice.
“Wha ... wh ... how...” came Claire’s and Aaron’s mixed stammer.
“What - THE FUCK - happened to you!?” Ava burst out.
“Told ya!” came Aunt Danielle’s triumphant voice while pointing at Ava, before turning her attention to me. “Haircut is new, though. Looks nice!”
“Thanks?” I replied, uncertainty in my voice.
I wasn’t sure if she actually meant it or was building up to something. It was then I finally understood what was happening. For everyone other than John and Danielle, right up until this moment, I was still “Tiny Tim the fat geek”. This was the very first time they got a good look at me in over a year. I lost fat and replaced it with muscle, filled out my stature and fixed my posture, but normally that was all concealed under baggy and worn-out clothes. Now was the first time I wore anything form fitting, and it was a suit of all things, adding a little extra effect. That must have been quite the shock for them.
“Bill made me an actual employee today, so from now on I might come into contact with clients. That’s why they made me go shopping for new clothes. Mine had holes in them.” I replied and then waited a moment for someone to say something.
Most of them just kept staring in disbelief. Only Uncle John gave me an approving nod, while Danielle had a big smug smile on her face. Did she actually tell them about my transformation and they simply didn’t believe her? Just as I decided to get up to my room and made my way to the stairs, the parents seemed to have found their voices again.
“Wait up, young man! Do you realize how late it is!? It’s a school night!” I heard from Aaron.
“And didn’t you see the chores list I pinned to the fridge, or did you just forget about it? You were to clean the living room after school today. I had to do that myself instead!” Claire added.
I paused for a second, looking at them in disbelief, before engaging in a mock conversation with myself.
“Wow, Tim, did you just say you got properly employed today? I’m so happy for you, I know how hard you’ve been working for this Job. So, you were late because you were celebrating, right? That’s so nice, Tim, you didn’t have a chance to do anything fun in such a long time. I sure hope you enjoyed yourself!”
Finished with my sarcastic rant, I stared at them with clear anger in my eyes. I was fully expecting Claire and Aaron to be angry with me for talking back to them. Instead, both looked kind of uncomfortable, almost awkward. Aunt Danielle and Uncle John seemed to understand as well, since they threw disapproving looks at the parents, though their daughter watched the whole ‘exchange’ with amusement. Ava and Logan also had disapproving looks. Theirs, however, were directed at me. Whether for making a scene or interrupting their fun night, I couldn’t tell. I just continued in a calm, casual, and maybe slightly sarcastic tone.
“I’m SO sorry I didn’t find your note, telling me to pretty up the living room for your little family evening I wasn’t invited to. But, as you should know, Claire, I rarely use your damn kitchen anymore, so that’s a bad place to keep shit you want me to find. Though, I’m starting to think you could just as well delegate those chores to someone who wasn’t asked to pay rent for his room. And since when do any of you even care when I get home?” I asked, incredulously.
“What’s that supposed to mean!? I AM your father and you ARE a fifteen-year-old teenager! Of course I care!” revolted Aaron.
His comment about my age pressed all the wrong buttons and pissed me off big time, which was audible when I continued the discussion and failed to maintain a calm tone.
“The lack of messages and missed calls on my phone doesn’t exactly make it look like you were worried or looking for me. In fact, I’d be willing to bet none of you even knew I wasn’t in the house until I walked through that damn door.” I pointedly looked at Aunt Danielle when I asked, “Did ANY of them mention waiting for or missing me even ONCE during this lovely gathering?”
Aunt Danielle looked uncomfortable at that. This certainly wasn’t the first argument she witnessed between us. It was, however, the first that she was suddenly involved in. When she didn’t answer, I continued.
“I take that as a ‘No’. Didn’t miss me at dinner either, like usual, I guess. Did you give the same damn speech to your Princess and Golden Boy over there? It’s a school night for them too, but, going by that bucket in her lap and the movie with an hour runtime left on the TV, you weren’t planning on sending them to bed anytime soon. So, how about you spare me your fucking ‘parents of the year’ act you’re putting on because others are watching, and in return I won’t disturb your fun any longer.”
Claire was speechless, and I didn’t think it was just because of what I had said, but how I had said it. The clear contempt in my voice, paired with the apparent disdain in my eyes when I looked at them, caused her to keep quiet. I was sure Aaron wasn’t finished with me, but after I just pointed out how they caused most of the major problems we had in that house themselves, he didn’t want to get into it even further while witnesses were present. As a result, neither of them spoke up when I turned to finally get into my room.
“Don’t be such an asshole, Tiny!” Ava suddenly threw in.
“I love you too, Princess.” I replied exhausted, while finally moving up the stairs. Logan had wisely chosen to shut up.
Once in my room, I leaned against the closed door, shut my eyes, and took a few deep breaths to calm down.
“I got my license. Work was awesome. I got a bunch of cool new clothes and a new look. And I just lost my virginity in the fucking of a lifetime with a gorgeous woman.” I quietly told myself. “Who gives a fuck if they didn’t remember it? Still a damn good birthday!”
After another few minutes of assuring myself that I didn’t care about my family not giving a flying fuck about my sweet sixteen, I got out of my suit and emptied the bags onto my bed to fill them with most of the old stuff from my wardrobe instead. Then I put the new stuff into the closet, and placed the bags next to my door. I planned to just dump them at Goodwill, if they even wanted them.
My mind lingered on Tess and that incredible evening I had with her, as my eyes fell onto the shelves with fantasy novels on my wall. Tess had told me once that she also enjoyed that genre, and she hadn’t read most of what stood in my shelves yet. Maybe, if this thing between me and Tess was going to continue, these could come in handy.
Chapter 3
The next morning, it took a while before my hair looked at least somewhat like it did at the barber shop, but close enough. I got dressed in my new black cargo pants, paired it with a royal blue button up shirt to stay within the school’s clothing regulations, and tucked it into my pants to show off the new belt. Everything really fit perfectly and showed my new figure off quite nicely. Since it was now mid-November again, I put on my black field jacket, slung my bookbag over my shoulder, and carried the shopping bags with my old clothes to my Jeep.
The change of attitude in the other students towards me was immediately apparent when I got out of my Jeep. Most people looked at me with quite some interest, but then their expressions changed to surprise and moved on to disbelief. The changes in my appearance seemed to be so drastic, most people couldn’t even recognize me at first. That effect even intensified once I was inside and moved around without my jacket.
The best part was, however, the reaction I saw on Mrs. Jenkin’s face when I entered her English class. The wife of Coach Jenkins, the man who wanted to expel me and then refused to let me take driver’s ed at school, seemed to appreciate my looks. When I entered the classroom, she first lifted her head barely enough for a quick glance, but then did a double-take. She stared at me quite intently for a while with one of her eyebrows lifted. I wasn’t sure if it was my new appearance or if she was trying to decide whether my new clothes violated the school’s dress code, but, from then on, she kept throwing me side glances throughout the entire period. A stark contrast to her normally ignoring me as best as she could. And whenever our eyes met, she put her hair behind her ear in a subconscious move.
The woman was in her late thirties and kept herself in remarkable shape. Maybe a result of being the wife of a gym teacher and football coach. Whenever I checked her out and wasn’t as subtle about it as I would have liked, I could’ve sworn she had the faintest little smile on her lips. I didn’t know if I would ever have a chance with her, but if I did, I would take it in a heartbeat. And not just as some kind of payback to Coach Jenkins, even though that would’ve been a nice little added bonus.
After I got out of school, I went to Goodwill for my old clothes. Turns out they accept absolutely everything. Even if they can’t resell my torn and worn stuff, they give it to textile recyclers to keep it out of the landfills. Suits me. Then I was off to work. Upon entering the building, I soon realized that Tess actually had chosen clothes that fit right in at work.
“Nice shirt!” I heard from a guy, who wore the exact same shirt as I did, and two minutes later I heard “Nice pants!” from the guy who wore the exact same pants. When I stepped into my office, though, I wished I hadn’t visited Goodwill before going to work, so I would have something to change into.
They had dumped what seemed like every piece of spare hardware into the room. Dozens of keyboards and mouses, old laptops, monitors, and three big boxes full of mixed cables. To my big surprise, I also found multiple moving boxes full of spare hardware components, like bare graphics cards or discarded mainboards. I had no idea how those had accrued, but my next job was to sort through all this, and it was dusty as hell. At least someone had also placed a few more shelves in the back of the room ... though I had to assemble them first. I put my earplugs in and spent the next hour assembling the metal shelves. Then I took a break, sat down at my desk, and leaned back with closed eyes.
I didn’t even get to listen to a full song through my earplugs before I felt something tugging at my zipper under the desk. I recoiled a bit before I looked down, where I saw Tess’ head sticking out from under the desk, looking up at me with a mischievous smirk on her lips while she refused to let go of my pants. As I took the earplugs out, she pulled my crotch back towards her.
“Don’t you dare move away from me! I always wanted to do this.” she commanded happily.
“You know I can’t lock the door, right?”
That gave her pause for a second. But then she bit her lower lip like she did the evening before, seemed to come to a conclusion, and continued.
“No ... but I want you! Maybe it will be extra fun!” she grinned, as she had just unbuckled my belt and was now working on the pants themselves.
“The way the others looked at me yesterday when we left, they probably already knew anyway. Or suspect, at least.” I reminded her of what I said the evening before, but back then she hadn’t commented on it.