The late teenage years and early twenties are a difficult time in a lot of young people’s lives. While the relief of leaving school and the seemingly endless party possibilities end and begin at similar times, it often seems as if young people have it easy. However, this is also a time where young people move away from home – for study, work or other purposes. Where they lose friends and gain new ones, where they begin their journey through “real life” but most importantly, it’s where they start to ask themselves those questions….. Who am I? Where do I fit in, in all of this?
For me, this was a difficult question to answer. I always just felt like one of the numbers at high school. I wasn’t necessarily popular, but I wasn’t unpopular. There was a lot of people I was friendly with, but I didn’t have a lot of people I would call close friends. I wasn’t really invited to high school parties, though I did enjoy going when an invite came up. As I finished high school I was unsure of the direction that I wanted to take in my life. College appealed to me as it did to my parents, who encouraged me that getting a degree would make my life easier and more enjoyable in the long term. Of course, this isn’t the case for everyone, however for me it was an option that worked. I studied away from home, only coming back when on holidays, which provided me with some valuable life experiences such as living with other people, getting used to working, cooking and providing for myself and many other things.
At 22, I now had my life out in front of me after graduating with a degree in accounting. I had always been good with numbers so this was quite a logical step forward. I had impressed the partners with my attitude, willingness to learn and work ethic during an internship at a highly prestigious firm, and they had offered me a job soon afterwards. All of a sudden I was being paid a reasonable amount more than the average living wage in a new city.
While my life was going quite smoothly from the outside, there were still things that were changing. Of the few friends I kept in touch with from high school, it was a rarity that I was able to see them at all. I had met some new people at college and work who were fun to be around but I struggled to find a group of people that I really fit in with. I didn’t have the most outgoing personality which wouldn’t have helped my cause. Lastly, and most importantly I thought…. While I had successfully landed myself a job and was living comfortably by myself I was still a virgin. At 22, I was yet to even kiss a girl, let alone have sex with one. This was difficult for me, and even while at college this played on my mind. I was shy, but I had always taken an interest in the girls at school and college. When in high school I thought I might get lucky somewhere with someone. When I left I thought I’d have plenty of opportunities at college, and now I didn’t know where and how I might lose my virginity.
I had considered many times booking high end escorts to ease my frustration, but I wrestled with this idea a lot. Did I really want to pay someone to take my virginity? I decided that I probably didn’t. As a shy, skinny, white guy standing just short of 5’9, I also struggled with the confidence factor. I knew I wasn’t going to be most girls first, second or even third choice, and that in itself did little for my confidence. Unfortunately I was also a virgin with a less than average sized dick in my early twenties who had known, heard and overheard so many stories about average guys being laughed at and ridiculed for their dick size, and I was even smaller.
As the months ticked by and I settled well into my new job, I was becoming more and more respected within the company. I had been commended many times on my reliability and was enjoying working at a business who’s employees and management actually got along and appreciated each other. However, the only relationship I had had up until this point was with my right hand.
One Friday I walked out of the office in my button up shirt and long pants with a smile on my face. While I enjoyed working at the company, the weeks were still long and I loved my time to rest on the weekends. I stopped by my favourite café on the walk to my car. I ordered my food and decided to sit outside. I enjoyed soaking up the early spring sun, not yet hot enough to cause a sweat. I watched the people walk past, more often than not looking relieved to have finished their work week. I kept my eyes on a group of hot early twenties girls who sat inside the café, however ten minutes later they had up and left.
A short time later I had finished my small meal and was preparing myself to leave, but looking at my phone when I suddenly heard a feminine voice from in front of me.
“Jack Price?” Shocked I looked up, that indeed was my name. I was more shocked when I saw who was on the other side of the table. It was a girl I didn’t recognise, but not because she had unrecognisable features. No, this girl had the biggest tits I had ever seen by some distance, a small, tight waist and as far as I could tell, a massive ass that I could see from the front. She had long blonde hair, blue eyes and thick eyelashes. Her lips were incredibly thick, a result of what I imagined must have been cosmetically done. She was tall, probably about 6 feet, and her long legs stretched into a pair of heels, making her another 3 or 4 inches in height. She was wearing a tight, black dress, her massive cleavage almost popping out the top.
She greeted me with a warm smile, however, even though she new my name, and even though she was indistinguishable from anyone I had ever met, I had no idea who this woman was. She looked to be in her late 20s, or maybe even early 30s I thought. She had the definition of a trophy wife look, which meant I couldn’t really be sure. She really did have the perfect bimbo look. What I was sure of however, was that with a body built as insanely as hers, there was no way this girl was under 27. To that end, I had no idea who I was talking to. Confused, I reached out my hand and shook hers. I took the opportunity to motion for her to sit, and she joined me on the other side of the table. She immediately started talking, saying things like “It’s been such a long time since I’ve seen you.” Unfortunately for me, nothing she was saying rung a bell.
After letting her speak for a minute or two and not gathering much more helpful information, I had to ask. “Hey, I’m really sorry, and I don’t mean this to be rude in any way….. but I’m honestly not sure who you are.” I said as delicately as I could. I looked into her eyes, they were familiar but I had no idea where from. “Oh my god Jack I’m so sorry,” She said. “I’m Kenzie….. Kenzie Walsh from high school…. We used to sit next to each other sometimes in Math.” It took me a while to realise what she had said, and for my brain to process this information, but when I had, I did finally realise that this indeed was Kenzie Walsh, and there was a reason that those eyes were familiar. I had an enormous crush on Kenzie in high school. She had big tits, a skinny waist and a shapely ass back then, but nothing compared to what she had now.
“Oh my god Kenzie, I’m so sorry I didn’t recognise you,” I said shyly as I continued to process that this goddess was actually not in fact in her late twenties, but the same age as me – 22.
“It’s ok Jack… I’ve changed a bit,” she said with a smile and a half laugh.
It was true that Kenzie and I used to sit next to each other in class, but not necessarily because we were best friends. Sometimes the only seat left in the room was the one next to me, and while I’m sure she would have much preferred to sit with her friends, she would show interest in my life and talk to me about hers. Of the few parties I attended during high school, she was always there. She would always have a small chat, even it was just a quick “hello” in passing. She always had a boyfriend however, and more often than not it was some older guy and/or much bigger guy. Like most teenage girls she went through her share of breakups and even admitted to me a few times that she had a poor choice in guys, though I knew I never had a chance. I hadn’t kept in touch with her, even with social media, as she had seemingly dropped off the face of the earth less than a year out of high school.
“Did you ever end up asking out Lindsay?” she asked me with a smile as she finished telling me about how busy she had been – she was working in marketing somewhere nearby. Lindsay was the girl I told Kenzie I had a crush on, when in fact it was Kenzie that I was crushing on the whole time. Lindsay was a short, petite blonde, with large tits, similar sized to Kenzie’s at the time, a small waist and a nice round ass. We had talked about how to approach her a few times in class, though she too was way out of my league. She actually happened to run in similar groups to Kenzie.
“Um… no,” I said with an awkward smile. Before I could add anything else Kenzie responded; “That’s alright, I think you two would have been cute together in high school anyways,” she smiled. “It was fun chatting about it in class with you,” she said with a wink.
We talked for another half an hour or so, as we both caught each other up on what we were doing and how we had got to some city a fair distance away from where we had gone to high school with each other. The time ticked over to 5pm, when Kenzie looked at her phone. “Ok Jack, I’ve got to get going but it was really nice to catch up with you, it was a great surprise,” she grinned as she pulled her chair out and stood up. I joined her, feeling dwarfed standing next to her giantess like frame. “Hey, are you doing anything tomorrow night?” she asked as I stood beside her.
“Um…. no, I don’t think so…. Why is that?” I asked.
“Well there’s an amazing rooftop bar not too far away from here if you’d be interested in checking it out. I kind of do the marketing for the place so me and my guests get free entry,” she smiled.
“Oh…. um…. yeah, I’d love to come,” I said nervously, as I looked back up at her.
“Great!” she smiled warmly. “I’ll be happy to add you to my guest list, just come up any time between 7 and 8pm,” she explained which I nodded and thanked her.
“Oh and Jack, what’s your phone number? I’ll text you the name of the place and the address,” she added. I quickly pulled my phone out of my pocket and we exchanged numbers.
“Okay cool, see you tomorrow night,” Kenzie said, wrapping her arms around my neck and pulling me in for a hug. She didn’t bother to duck down, instead opting to just pull my head into her enormous cleavage. I’d be lying if I said that I was calm. At this point I had almost just cum in my pants. With that, she turned and walked away – and my god her ass was enormous. The first time I had seen it in four years, and it had blown up to a monumental size. I watched it jiggle and sway as she walked in the opposite direction to which I needed to go.
I returned home and later had what I would describe as the wank of my life. My dick, even only maxing out at 4 inches was hard as a rock and throbbing uncontrollably as I took it out. It was all of 30 seconds before I shot my load just thinking about what had happened not even an hour earlier. I cleaned myself up, had a nice, lengthy, warm shower before deciding to order some takeaway over the phone and watch a movie. My phone, still on silent mode had a few notifications. I had received 2 messages from Kenzie surrounding details for tomorrow night. There was a bunch of random app notifications, and a notification of a follower request on Instagram. I had a look, expecting it to be another of many scam accounts but was even more pleasantly surprised to find that Kenzie had requested to follow me. She had created a new account to use, which is why I hadn’t seen anything since we had finished high school. Impressively, it was a public account with over 20K followers. I rapidly accepted her request and followed her back, becoming only the 300th person she followed. I looked through her following list quickly and it was something. Most of the accounts she followed were female Instagram models. She followed a few businesses, mostly in line with fashion and jewellery and about 100 other accounts. Of most were girls, some being girls we had gone to school with. I was surprised to see Lindsay had found herself there. One thing I didn’t see many of, was male accounts. I was almost certain she would have a boyfriend, but none of her posts suggested that this would be true.
The next day went quite slowly as I waited nervously for the time to come for me to leave. I jerked again, with a similar result to the previous night before I decided to go for a run. I showered before heading to the shops to top up my food supplies. While time was going slowly, I was doing my best to keep myself busy. The clock finally ticked over and I dressed myself as nicely as a single 22 year old guy could. A button up top with the sleeves rolled up, a pair of long pants and some boots. Nervously I left my apartment, quickly got into an Uber and arrived outside the rooftop bar at about 7 15pm. I made my way up the top of the building via the elevator, and was met immediately with amazing city views. I was quickly accompanied by security for an ID check. I then spoke to a beautiful girl who would have been in her early twenties. I remembered what Kenzie had said about the list, and when I was asked to pay an entry fee I brought it up. The girl looked at me confused, before looking at a piece of paper in front of her. “What’s your name?” she asked to which I quickly replied. She scanned the list before shaking her head. “Are you sure you’re on Kenzie’s guest list?” She asked as another gorgeous blonde girl walked around the corner. “Yeah…. I’m pretty sure,” I said as my confidence waned from me and I immediately started to think of the worst. “I’m sorry I can’t find you on her list,” she said as she shook her head again. The other girl quickly spoke up. “Are you Jack Price by any chance?” she asked. Relieved I nodded my head. The second girl turned to the girl with the list and told her that I had been a late addition and I was quickly let through.
I walked out onto the terrace and took in the incredible view of the lights that I had only partly seen from the inside. I looked around a relatively busy rooftop and noticed a few things immediately. Every single waitress was stunning, just as the two employees inside were. The other thing I noticed was a big gap in female to male ratio. Surprisingly, there was a much higher number of females. Not seeing Kenzie I walked over towards the bar. I saw movement to my right as someone got up from a seat. I turned slightly and saw a giantess approaching me. Kenzie was rocking a pair of enormous heels, about 6 inches in height. She was wearing an incredibly tight white dress that left little to the imagination as her plunging neckline showed maximal cleavage. The dress was as tight around her huge and waist as it was around her tits, and a high thigh slit made her look even sexier. I walked slowly towards her and she again hugged me by pulling me in to her enormous cleavage. She held me between her massive tits for a while before slowly pulling away. My dick throbbed away in my pants, and I contracted all the muscles in my body to stop me from cumming then and there.
“It’s great to see you again Jack,” she said as she touched my upper arm. “I hope that you don’t mind that I’m wearing a pair high stiletto’s,” she said with a smile. “I just love how long they make my legs look.”
“Uhhh…. n-no it’s okay,” I said, stuttering. Kenzie quickly turned around and walked next to me, placing an arm around my shoulder and motioning for me to place my arm up around her waist as we walked. While this was an uncomfortable position due to our height difference, I was hell-bent on making it work. Kenzie lead us to a small private area, with a booth. Already seated at the booth were 10 girls, all looking to be about 25 or 26, and all 11/10s. Tight dresses and big tits seemed to be a common theme, even though 4 of the girls were flatter chested (though still had big enough breasts).
“This is Jack everyone,” Kenzie announced walking over to the booth. “He’s an old friend from high school. I was welcomed and quickly introduced to all the girls, later finding out that Bri, the oldest of the group was only 24, and Lilly the youngest had only just turned 21. Kenzie lead me to a free spot and sat down almost on my lap, her arm still around my shoulder and mine still around her tight waist. I made conversation with everyone when I had something to add, which turned out to be quite a lot as I fielded a lot of questions about myself which I handled reasonably well.
As the night went on, and a few drinks went by, we were all talking like good friends, and when the bar closed at 11pm we were all surprised the time had gone so fast. Often it seemed that the hottest girls didn’t have personalities, but these ones certainly did. We finished our last round of drinks before heading down towards the road-side. Shortly afterwards we split up into small groups. Kenzie lived with two of the other girls – Gabby, a 5’10 blonde with big tits, and Mikaylah, a 5’5 blonde with big tits and a massive ass. They were both the same age as us, but looked at least 3 years older.
“Hey Jack, would you like to come back to our apartment?” Kenzie asked as I was about to book an Uber for myself. “We can play a few games, watch a movie, catch up some more, whatever you feel like really,” she added. I jumped at the opportunity. I had been nervous all night, but they really hit me at that moment. I had been rock hard all night but somehow my dick got harder.
The Uber didn’t take long to arrive and the much shorter Mikaylah decided it would be funny if she called shotgun. Luckily the car was big enough for the two taller girls to fit into the back with me in the middle. Fortunately for me, it wasn’t a long care ride to their apartment. Kenzie had decided to press her enormous tits into my arm and rest a hand on my leg. Gabby had also decided that she would sit as close as she possibly could to me, and rested her hand on my other leg for most of the car ride. All of this contact was almost too much for me to handle.
Upon entering the apartment, Mikaylah came up with an idea. “Why don’t we go for a swim?” she asked. “Yes!” Gabby and Kenzie said almost in unison. Mikaylah and Gabby went off to get changed while Kenzie stayed with me. Bending down for once, she kissed me passionately, her tongue dominating mine. “Are you coming for a swim Jack?” she asked as she placed her hand on my chest.
“Um…. I don’t have any swimmers,” I barely managed to get out.
“That’s ok, just go in your underwear,” Kenzie replied. “I’ve got to go get changed, promise you’ll wait for me,” she said as she looked down into my eyes. I nodded and she turned to walk into her room.
A short time later the other two girls came back together. Both Gabby and Mikaylah were wearing tiny bikinis, much too small for their massive tits. Their bikini bottoms also left little to the imagination. “Do you like our bikini’s Jack?” Gabby asked teasingly, as both girls leaned forward slightly to show an even bigger overflow of cleavage. I moaned under my breath and barely managed to stammer out a positive response as Kenzie emerged from her room.
Kenzie walked out towards me in a small white bikini. The top, while bigger than the other girls tops, was smaller comparatively to her enormous tits. She walked over to me and passed me a towel. Her thong bikini bottom clearly outlined a pair of fat pussy lips, and her monstrous ass easily ate the thin strip of material. We walked outside, towards the elevator, and ended up at a pool within the building complex.
Gabby and Mikaylah both set their things down before using the steps to slowly lower themselves into the heated pool. Kenzie set her things down and looked at me as I slowly pulled my shirt over my head. “Mmmm nice,” she purred as she ran her hand over my skinny chest. I looked up her desperately and she giggled. “I look forward to seeing you in there,” she said as she turned. I watched her long legs and her massive ass sway away from me and slowly down the pool steps. I quickly unbuckled my belt and removed my long pants before quickly jumping into the pool myself.
I was incredibly horny, throbbing against my underwear and harder than I had ever been as Kenzie walked over towards me, her massive tits spilling out of her small bikini top. She put her arms around my neck before pulling me in for another deep kiss. “Catch me,” she said as she pulled away, before jumping up into my arms and wrapping her toned legs around my small waist. My full erection slammed against her incredible body, and seeing her in that bikini was too much for me to take. My muscles contracted fiercely as I exploded with cum. I moaned quietly and closed my eyes, as my hands supported Kenzie’s huge ass. My body eventually relaxed from one of the most intense orgasms I had ever experienced, and thankfully it seemed that none of the girls had noticed.
A while passed and we moved from the pool to the smaller hot tub off to the side. In this company, It hadn’t taken me long to recover from my first orgasm, and by the time we were changing from the pool to the hot tub, I was once again rock hard. There was room for four people in the hot tub, probably more, but as Kenzie was the last to get in, she immediately sat down onto my lap, pressing my small, hard dick into my stomach. Whether she knew exactly what she was doing to me, I didn’t quite know. It seemed as if she knew she was teasing me, but it took all of 20 seconds for me to be exploding again. Her body language didn’t change, and she didn’t say anything, she just kept sitting there for a little while longer.
Eventually we all ended up back in our room. Now, well past midnight, the other girls showered and called it a night. Kenzie had asked me whether I would like to shower and I took her up on the offer. Once I was done she had told me to meet her in her room which is where I presumed I would be sleeping. I slowly opened her door, turning the main apartment lights off in doing so. I looked up to see Kenzie, laying naked on the bed. Her tits were enormous, much more than a handful each, and I had the experience not long prior to know her ass was even bigger.
For the third time that night, in the space of about half an hour, I returned to my fully erect state. “Come here baby,” she said as she motioned for me to join her on her bed. I slowly ventured into her room and shut the door, this was now unchartered territory for me. I had never seen a girl naked before. I climbed onto her bed and she immediately and skilfully unbuttoned my shirt that I had put back on, before she ripped off the pair of her spare shorts she had given me to sleep in.
I took a deep breath as my small, fully erect dick was released into the room. Kenzie giggled lightly upon seeing it. “Awwww it’s so cute Jack!” was the first thing she said. She immediately crawled towards me and took it in her hand, dwarfing my member in comparison. “Oh my god you’re so hard for me!” she giggled to which I nodded breathlessly. “How big is it?” she asked inquisitively.
“4 inches,” I replied quickly as I closed my eyes, her feminine fingers still holding my dick.
“Awwwww is that it Jack?” She asked teasingly. “I’ve never seen one so small!” she giggled again. She used her big thick lips to plant a gentle kiss on it’s head. “Fuuuckk” I could only moan. It was again too much for me to handle. I spurted a few small, weak shots of cum onto her face and juicy bimbo lips.
“Awww you poor thing,” Kenzie said teasingly as she grinned up at me, my cum dribbling down her face and lips. She quickly stuck out her tongue and used her fingers to clean it up, and proceeded to swallow it all. Even after 3 cum shots this extra act made my dick jump.
Kenzie slid back onto the bed, bending her knees up and showing off her perfect, glistening pussy. She played with herself for a few minutes as I watched, getting hornier and hornier once more, before she ordered me to eat it. I went in with no idea what to do or how to do it, but tried to listen out for her moans. After almost half an hour of work (and a very tired jaw) Kenzie pushed me away. My dick was rock hard once again. “Fuck me Jack,” she encouraged as she pulled me on top of her. I rested my body on her huge tits as she slowly helped guide my underdeveloped dick into her wet pussy. As I entered her, the warmth, wetness and tightness enveloped me in a feeling I have never come close to before. I closed my eyes in an attempt to regather but I knew what was coming. I felt the cum building in my balls rapidly once again. “Fuck me Jack!” Kenzie ordered this time. I thrust roughly into her warm, wet hole, bringing me to the brink. The feeling of all of this, for the first time around my small dick, was way too much to handle, and that’s not even considering her long legs gently wrapped around me, her huge tits underneath me and her gentle moans and giggles. I came almost immediately. I would like to say it was shot after shot and that I didn’t stop cumming for 5 minutes. However, that’s not the case. It was intense, but 3 or 4 small shots was what I had. I moaned quietly as I released and sunk into Kenzie’s soft body.
Kenzie had just been lying there, fully expectant of what was going to happen. She giggled as I released and sunk into her limply. “Awwww,” she said as she patted the back of my head. “I think I might be just way too much for that little dick of yours to handle,” she said teasingly, with another light giggle. I began to breathlessly apologise, feeling guilty about my size and lack of stamina. “It’s ok Jack, guys with twice your size and much more experience often struggle to fuck me for more than 5 minutes at a time. When I saw your little guy I knew you’d have no chance,” she said as she rubbed the back of my head.
Still horny she asked me to move aside and I did as asked, as she removed a thick 10 inch dildo from her bedside drawer. “Now this…. this is what I’m talking about,” she said as she showed me her toy up close before gently pushing its length into her entrance. She moaned and sighed as she fucked herself with the massive plastic toy, slowly increasing the pace. She watched me carefully as I looked on in shock, disappointment and a sense of longing, wishing I would be able to do something like that. Her moans and cries increased in volume as she continued to fuck herself. For minutes this repeated, at least 10, possibly 15 minutes went by as she bucked her hips against the enormity of the toy, outsizing me by 6 inches in length, until she finally managed to bring herself to satisfaction.
Kenzie released a big sigh as she finally removed the big dildo from between her fat pussy lips before opening her eyes and looking at me. “Can you go again Jack?” she asked, maintaining eye contact. Shocked, and practically unable to speak I shook my head, before a few seconds later responding with an “I don’t think so.”
“Two cumshots is all that little dick can handle I guess,” Kenzie laughed, not knowing about my earlier experiences.
“Actually….. um” I decided to speak up after a few moments of silence. “That was the fourth one,” I confessed, leading to a perplexed look from Kenzie.
“And when were the first two then baby?” she asked teasingly. I took a long breath to regather myself again before answering. “Um… In the pool,” I responded quietly. This response caused an immediate, though short bout of laughter from Kenzie.
“Really? You came twice in the pool?” she asked, quizzing me on my experience now.
“Um… Yes,” I responded.
“Well… When?” she grinned as she asked.
“Ummmm, well when I first got in the pool I was extremely hard and then you wrapped your legs around my waist and pushed your tits into my chest, and told me to grab your ass and that was too much for me,” I slowly explained.
“And the other time?” she asked expectantly, with a further grin on her face.
“Um.. That was when we moved to the hot tub and you sat on my lap,” I explained. Kenzie laughed again. “See Jack, just what I said before. That poor little dick had no chance of handling my massive ass and big tits, even me just sitting on your lap was too much for you to handle,” she laughed before excusing herself to clean up. She had a quick shower, walking back into the room in a sexy pair of pyjamas before offering me the opportunity to clean up. In the short space of time I had alone, when she had cleaned herself up, and when I was cleaning up after myself, I had not been able to stop my head from spinning. I could not believe what had just happened, and had no idea about how to feel given what I had just witnessed.
I walked back into Kenzie’s bedroom in a pair of her shorts, further cementing the embarrassment I had felt. She made a quick joke about the pink shorts being cute, and that they suited me. She motioned for me to come over to her bed, and I climbed in next to her.
“You know…..” she started. “I always liked you in high school Jack. You were always sweet to me, always kind. I talked to you so much about other boys, and I even knew what effect that might have on you, but you were always nice to me,” She continued. “I was a bit of a slut in high school, and I’ll be honest, I still am now – I have fucked a lot of guys, but talking to you about things always used to make me feel a bit better, even if it was only a short conversation, and even if we didn’t have them all that often.”
I didn’t really know what to say in response as she rolled over and wrapped her arms around me, pulling me towards her with her legs. I knew she was expecting a response, but my head was still spinning from everything that had happened. I finally committed to a response as I did my best to regather myself.
“Um, I always liked you in high school too Kenzie,” I started, which caused her to squeeze me tighter. “I actually had a massive crush on you for the longest time,” I admitted.
“Awwwww that’s so cute,” she said, as her massive breasts heaved against my skinny chest as she breathed.
We talked for a short while longer before Kenzie expressed how tired she was. I rolled over, turned off the light and immediately returned to Kenzie’s side at her request. She quickly fell asleep, while I laid awake, still trying to process what had happened, and a few questions kept rolling around in my head: Does this mean I’ve lost my virginity? Does one pump inside a pussy really count?