Small Dick Virgin

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.