Grown Up Experiences

I should introduce myself. My name is Sam and I am 21 years old and I am a loser. Well, at least I used to be. This story is about how I turned things around. I have always had a negative image of myself. It's something I am constantly working on but it's hard. I guess it started off with parents who never really used positive reinforcement at home. Nothing I did was good enough and when I excelled it was expected. If I didn't excel then I was a failure. This is what I grew up with. My self-esteem wasn't exactly sky-high. I was always a good kid who worked hard in school but that wasn't good enough for my parents because they expected perfection. Nothing short of medical school was acceptable. I realized that science just didn't do it for me though. I really enjoyed all my non-science classes and excelled in them. My science classes were a whole different story. I would bust my ass and get 75 to 80% grades which of course isn't terrible but I may as well have failed.

The sad part of all this was that because I was basically a good kid who worked hard, I was seen as a geek at school by my classmates. I was tall, well built, and played sports but I was quiet, shy, and awkward. I didn't have much success with girls. Let's be honest, even if I did, it's not like I could have brought them home. My parents would have lost their minds that I was wasting time on girls instead of school work.

So high school was mostly a lonely and frustrating affair. I graduated and went into university for a science-related field (not my choice) and bashed my head against the wall for 2 years before I woke up and put my foot down. I knew it wasn't for me. I dropped out and moved out of my parents' house all within a month of my decision. I had a job lined up in another city in a completely unrelated field.

You may ask how I was able to do this. Well, instead of making friends and going out with girls in school, I taught myself how to program. Other than that, I ran and worked out. Those were my only saving graces that kept my mental health intact all those years. Even though I hated pure sciences like Chemistry and Biology, I really enjoyed coding and I used all the resources I could and became a pretty good programmer. I even started to do some work online to sharpen and showcase my skills. I was fluent in several languages soon but most importantly I could problem solve and automate boring tasks with the best of them.

I think it was my nature to find the smartest solution that would mean the least amount of work. I wrote a program that would automatically track all the TV shows I liked and download them to my computer all separated by seasons and episodes and would keep track as I watched them. I shared this program with some of my friends online who loved it. It was one of these friends who told me of a job opportunity. There was a job opening at a company his wife worked at. They needed someone to work nights to do overall maintenance of their systems and input results from the day or something along those lines. It was decent pay because no one really wanted to do it but my buddy figured it would be a fresh start for me. My friend told me that his wife would put in a good word for me and would at least get me an interview. This was perfect timing as the realization had hit me that I was never going to go to Med school and that I needed to get away from my parents.

I told my parents my plans and they, of course, lost their shit on me. Of course, by now I was an adult so they couldn't actually do much. I told them I was leaving and that they could contact me if they wanted but I won't put up with the abuse anymore. I had already packed a bag with some essentials and I walked out. I felt relief, fear, and pride at the same time. I took public transport to the Greyhound station and bought a one-way ticket to my new home.

My buddy John was nice enough to let me crash at his place while I did the interviewing process. He lived in a small bungalow with his very pretty wife Amanda and their 2 dogs. I don't know how he landed her but I was happy for him. She was very attractive but also a sweetheart. It made me feel even sadder knowing I'd probably never have anyone like that.

I decided I needed to make a great impression at the interview because failure was not an option. I couldn't go back to my parents with my tail between my legs. I'd rather be homeless. With that determination, I went in for the interview and met the owner of the company. He was a nice older man and he told me about the job. I knew from doing some research that they produced a very niche product for larger companies. The business was doing quite well and they were looking to expand into a larger space. I explained to the boss about my experience and gave examples of my problem-solving skills. I, of course, had no real job experience as I was a student till a month ago. I used some white lies and real-life examples of my coding skills to sell myself. It turns out that I presented myself quite well and he offered me the job on the spot. I was ecstatic!

We discussed salary and benefits. I was being offered a fairly decent salary for someone with no experience but the job was not exactly exciting and quite frankly not a lot of people were applying. It was also the night shift that deterred a lot of people. These things were not an issue for me at all so I jumped at the opportunity. I was more than okay with this because I was a night owl anyway and enjoyed working at night.

I was hired on a Friday and I was told I would start work Monday night. My shifts would be 9 pm to 7 am 4 days a week. I would work Monday to Thursday one week and then Tuesday to Friday the next week. This was, of course, amazing as I would always have long weekends. I couldn't wait to tell John and Amanda. I bought a nice bottle of wine and steaks for dinner. John and I handled the grill while Amanda made some side dishes. I think I was happy for the first time in my life. I didn't feel like a huge failure. We had a very pleasant weekend with me thanking them both profusely.

Amanda told me she had a friend who was a real estate agent and could help me find a place now that I was employed. I made an appointment to meet with her to discuss what I could get. Amanda's friend Robin asked me to meet me at a vacant apartment so we wouldn't waste time. I liked her already. We met at the location and I was in awe of her. She was gorgeous. I picked my jaw off the ground and introduced myself. We started the tour of the place. It was a second-floor loft on top of a yoga studio in an up and coming part of town. I think it's a polite way of saying it's a shitty part of town but it's getting better. To me, it was perfect! I was able to haggle a bit and get the rent to a reasonable number and I jumped in with both feet and signed the lease. The loft was fantastic. The building must have been an old industrial factory of some sort. The loft had 2 levels with a bedroom and bathroom on the top floor that overlooked the living room on the main level. It wasn't overly big but it was perfect for me.

I called Amanda to let her know that I had met Robin and that I had signed the lease. Amanda laughed and told me that she had heard from Robin just before me. Amanda said that Robin thought I was very cute and friendly. I must have not said anything for a bit because Amanda laughed and asked me if I was still there. I laughed and said, "There's no way she said that. You're just messing with me."

Amanda assured me that she wasn't and that Robin liked me.

If you recall, I had quite a low self-esteem and Robin was gorgeous. She was in her late 20s with a fit body you only get from working out. She was 5'6 120 lbs brown hair, hazel eyes, and had amazing tits. I mean they looked fake, that's how big and perky they looked on her small frame. At least that's what I remember. I had to try and keep her eye contact and not stare at her magnificent tits. Apparently I was so excited about the place that I didn't realize Robin had been checking me out and flirting with me. I was quite oblivious.

I still didn't really believe Amanda though and in my idiot brain I thought it was some kind of mean prank where I show interest in Robin only to have her laugh at me. So I put that aside and went in for my first night of work. The owner had waited up for me which was very nice of him. He showed me my office, which was awesome. It had the computer setup obviously but also a couch, and lots of open space. He told me it used to be for project meetings but they got a better location for it so this was sitting empty. He also showed me the lunchroom and gym. I couldn't believe how nice everything was. I was just happy to have a job but this was getting cushy. I asked if anyone else worked nights and was told that unfortunately no I would be working alone. Mr. Young said this as if he was expecting me to be upset about it but I just smiled and told him it was no problem.

I got my list of tasks to be completed from him and he went off to go home. I really wanted to make a good impression so I got right to work. I started to see what needed to be done and right away my lazy but creative brain started to pop out ideas. Within 3 hours I had figured out that I could do 90% of the work by automating it. The rest could be done in less than an hour. This was unbelievable. I spent about 2 hours hammering out a program that did exactly what I needed and ran the script. Boom! It was just like old times. My entire task sheet was completed and I couldn't stop grinning.

I got up from the desk finally and decided to look around. It was kind of eerie how quiet it was but I enjoyed solitude and this was perfect. I went to the lunchroom where I had stowed my lunch. Amanda had been nice enough to pack me some food. "Ugh, she is so amazing," I thought to myself. I made a mental note to get John and Amanda a nice gift. I was moving into the loft next weekend so I was still crashing at their place. I had to get all the furniture still as I had barely anything with me. John and Amanda had insisted on giving me some of their things that they were looking to upgrade. This was such a huge help I honestly felt I could cry. I basically had a bed, a dresser, kitchen table, and a sofa. I would work on buying a TV and other electronics once I was moved in.

I grabbed my sandwich and ate it on the couch in my office all the while thinking about what I should do next. I didn't want to shoot the golden goose by talking myself out of a sweet job by telling the boss about my automation tricks. I was going to keep that quiet and just turn in my completed tasks done professionally. I opened up a word document and started a to-do list.

Get in shape, use the office gym every day.

Meet new people. Sign up for online dating.

Stop being so awkward.

Try the yoga place under my loft.

Maximize this job.

I realized that I could get into work, do about an hour or so of work, get a good workout in, let the automation do its thing and then get some solid sleep on the couch. I would wake up nice and refreshed and ready to go for the day. I could spend all day doing whatever I wanted instead of sleeping. It was like having a superpower.

The next night when I came in there was no one there to greet me but by now I had all the access codes and keys. The place was secured pretty tight so I wasn't worried. Besides, if anyone entered the main door, a chime rang near my office so I'd know someone was coming. I decided to actually implement my new plan. I came in and did a very detailed read-through of the tasks and realized that again the automation would take care of most of it. I did some things that needed to be done by hand and then hit the execute button and leaned back. I was sipping the non-stimulating pre-workout drink I had read about. I wanted to get a good workout but also be able to sleep after. I changed in the men's room and went to the gym. I had my phone on me in case anyone was to call and the desk phone was forwarded to my cell. I was extra paranoid because I really liked this job and didn't want to get in trouble.

I blasted some good tunes on the sound system and had a very good weight lifting session. I had spent quite a few hours reading up on workout plans for getting jacked. I had an excellent workout and I spent a good 30 minutes in the shower after just relaxing and stretching. It was an amazing experience really. I was all alone and the whole place was my playground.

I had made sure to pack everything I'd need for my overnights. I had towels, my toiletry kit, and lots of change of clothes and workout clothes that I'd leave in the office. I came back to the office, made sure my tasks were completed, and made myself comfortable on the couch. I had brought in a blanket and the couch was quite comfortable. I was out like a light and didn't wake up till my alarm went off half an hour before my shift ended. I got up and freshened up before doing one final check on my tasks and shutting down for the day. I locked up my office that no one else had access to and left for the day.

I ran into Amanda in the kitchen of their house as she was cooking breakfast. John was still sleeping. Amanda smiled and asked if I wanted breakfast. I said sure and sat down. We chatted and ate breakfast for a bit before she asked me about Robin. I must have looked confused because I didn't know what she was asking exactly.

"Have you asked her out on a date yet?" she asked me in a patient manner.

"Wait, what? Why would I? A girl like that would never go for someone like me!" I said with some sharpness in my voice.

Amanda's eyes flashed and I could tell she was angry.

"Sam, you are a smart, good looking guy! My friend Robin told me she liked you. I told you about it but you for some reason don't believe me. Are you calling me a liar? What is your problem?" she yelled.

I was quite taken aback and grinned slowly. I walked around the kitchen table and picked her up in my arms and gave her a huge bear hug. "You're my favorite," I said as I felt my eyes get a little wet. I had never really had someone who looked out for me and saw me as anything but a failure. As cute as she was, she was like a protective older sister to me now and I felt ashamed at having had some impure thoughts about her.

I was still holding her in a bear hug and she was tapping out because she probably couldn't breathe when John walked down the stairs. The look on his face was hilarious as I almost dropped his wife and started stammering an apology. They both burst out laughing and I joined them. I asked John what he thought about me asking Robin out. He was fully supportive and said I should go for it.

Amanda and John left for work shortly after and I decided to call. I called Robin but it went to voicemail. "Ugh, of course", I thought to myself. "She is definitely screening my calls."

I put my phone away and flipped on the TV. Within 5 minutes my phone rang and caller ID said it was Robin. "Oh shit!" I thought. "I am in for it now".

"Hello", I answered. How original!

"Hey Sam, sorry I was in the shower when you called and I wasn't able to answer."

I told her it was no problem and that I was wondering if she wanted to go out for dinner Friday night. There was a pause and my heart stopped.

"It's okay if you don't, I am sorry for wasting your time." I blurted out before she said anything and hung up.

Within a few minutes, I had already made up my mind that I would die alone and was moping when my phone beeped again. This time it was a text and it was from Robin.

"Hi Sam, you didn't let me finish. I'd be delighted to go to dinner with you on Friday. How about 7? I know a place in town that is excellent. I will make reservations for us. Why don't you pick me up at 630 at my place? ;)"

To say I was stunned would be an understatement. I read the text over and over and couldn't believe it. I knew I had to stop acting like an idiot and for once in my life, be cool. I responded to her text with a short apology about hanging up on her and said I would see her soon. Apparently I was better over text than talking. Who knew?

The rest of the week flew by as I settled into a nice routine of making sure my work was done perfectly and getting after it in the gym and sleeping. My days were filled with researching the area and looking for deals to buy the things I would need.

I had nervously asked Amanda earlier in the week if she would go clothes shopping with me since I was hopeless. I wore comfortable jeans and T-shirts or workout clothes. I had really nothing else. Amanda was overjoyed and wouldn't stop talking about it. She was so excited that I think we went a little overboard. I got a whole new wardrobe and I sure hope I didn't lose my job because my credit card was still smoking after we had finished. I specifically wanted one outfit that she thought would be good for my date with Robin. Amanda just smiled and helped me pick out the whole outfit. We even bought new underwear because she said no one liked old boxers. When we got home she wanted a fashion show of sorts which I wasn't sure about but I couldn't say no.

I paraded out in all the new outfits to her whistles and hoots with a totally red face. She then asked me to show her the new boxers. I turned an even darker shade of red and stammered something like, "Oh no! I can't do that."

She stared at me with a mock stern expression and said, "Oh yes you can! You are a confident and sexy man! Start acting like it. I want you ready to go for the date with Robin and I am going to make sure that you are ready."

"Did she just call me sexy?" I thought as I stared at her and asked, "So um, you want me to pull my pants off to show you my boxers?"

"Duh, how else can you do it? Now come on! Let's see what Robin is going to see on Friday!" she said with a laugh.

I decided to stop being so damn nervous and overly cautious and dropped my pants down and stepped out. The new underwear I had gotten was quite form-fitting with the pouch in the front that nicely accentuated the package. To be honest, it felt quite nice. Much nicer than the old stuff I had. So there I was standing in front of my buddy's wife in my boxers and she was saying how good I looked when I felt my cock twitch. I had never been in a situation like this where I was almost naked and an attractive girl was happy about it. Before I could even think I had a full-blown hardon. I clamped my hands over my cock and fell back on the couch and started to apologize to Amanda.

"Oh my god, I am so sorry! I don't know what's wrong with me." I said desperately.

"Well, well well", she teased. "I see Robin is in for a fun time with you. It's nice to know that you're big all over!"

I had no real reference for how big I was since I was still very much so a virgin. I mean I wasn't as big as the pornstars I had seen in porn but I was above average. I asked her if she was done making fun of me and if I could get dressed now. Amanda winked at me and said, "I am done for now, but I hold the right to demand another fashion show whenever I want."

I wasn't sure what to say to that so I quickly pulled up my pants and pushed down my finally softening cock back in. What a confusing experience. Obviously, Amanda was gorgeous but she was like family. Was she flirting with me? Or was it just teasing? She would never do anything with me obviously so it must have just been teasing. I thought all this as I put my clothes away and got ready for work. I was getting a little backed up though since I hadn't masturbated since arriving at their place. I needed relief and it came at work that night when I was taking a long hot shower after my workout. I just grabbed some lotion as I had the hot water beat on my back and shoulders and started to stroke. Usually, I fantasized about the pornstars or some hot classmates but this time both Amanda and Robin flashed in my fantasies and before I knew it I was blowing a massive load on the shower floor. I felt weak as I stood there watching my cum swirl down the drain. It was a huge relief though because I felt much lighter and more relaxed.