Zeb's First Time Experiences

There have been many great 'first times' in my sexual life... this story tells some of my more memorable escapades. My first blowjob, first fuck, first threesome, and first exhibition and voyeur, even an unforgettable first orgy.

I'm Zebulon Whistler Bitterberry... yeah I know what a mouthful. My mother was reading a Gideon bible at the hospital just after I was born and evidently Zebulon was mentioned in a passage she read. Whistler, is Celtic for 'son of the wolf'... I was a loud crier when I arrived. And unfortunately Bitterberry was my mother's family name. Thank goodness everyone has just called me Zeb B for as long as I can remember. I'm presently 28 years old, and I design and build small alternative style houses for a living.

I've always lived a bit of a bohemian lifestyle. I love all the arts and find my creativity expresses itself in my design work and attitudes. I'm not a 'greenie' as such and I aren't adverse to wealth, I just don't spent my time and money it in the ways others might. My mantra is... live on half of my income and give the rest away. I have to admit that over the last few years I have managed to live quite comfortably on my half, so I am able to support a few charities and also travel a bit with a group of other like-minded people helping in third world relief programs. There is also nothing better than spontaneously paying for someone's groceries at the store... I get a real kick out of that.

Let me start by giving you some context as to why I'm the way I am. My mother was 15 when she fell pregnant and her rather loose lifestyle at the time meant she had no idea who my father was. Two years after I was born she decided that kids weren't her thing so she left me with her older sister and never came back. Masie my aunt was a 22 year old lesbian hippy who could never say no to a good cause. She was always taking in stray animals... and people! Most of her friends worked for charities or gave their time and money to them. I guess it rubbed off on me and I can't remember a weekend in my youth when I wasn't out volunteering for some worthy cause. Despite having a degree in political science Masie made her income from painting, in the abstract style. It provided a reasonable income and her work was quite sort after for eye catching colorful designs. Private commissions were her main income and she'd worked for a wide range of people.

We lived in a small two bedroom bungalow which always seemed to have a party on Saturday nights... full on gatherings with a lot of alcohol and drugs involved. My aunt also had a strong sex drive and there was a different woman in her bed almost every night.

Surprisingly, in the midst of all this I grew up fairly normal, attended the local schools and got reasonable grades.

As I said the house was small and my bedroom backed onto Masie's. I would often wake to the sound of orgasmic cries of delight from the various occupants that shared Masie's bed. Nudity wasn't an issue at home either and by the time I was twelve I must have seen more boobs and pussies than most guys do in a lifetime. I knew it wasn't normal to grow up in a household with so much skin on display but I didn't think of it being sexual... at least not until I was eleven... that's when I started having boners at night and would wake up with a stiff little cock in the mornings. It was on one of these mornings that my new physical capability came to Masie's attention. She had come in to wake me up and was surprised to see the tent in the bedsheets... I was embarrassed knowing she had seen it. Masie just smiled and sat on the side of the bed.

"I can see it's time we had a talk about some things," she said with a sigh.

"About what?" I queried while trying to cover my erection.

"In my day they called it the 'birds and the bees' talk, but I'll just call it what it is.. sex."

Masie then spent the next couple of hours explaining the ins and outs of the reproductive system and basic sex. I was amazed and had dozens of questions. We stopped and ate breakfast before continuing with the conversation. I soaked up all the information like a sponge and over the next few weeks Masie told me everything there was to know about sex... and I mean everything.

I remember one of Masie's girlfriends in particular, her name was Celia and she was from Africa, her skin was a dark ebony colour. I was fascinated by the fact that unlike all the other women I had seen this one had no changes of colour in her skin... no tan lines from a bikini or even a darker shade on her legs or face from more exposure to the sun. She was the most beautiful thing I had ever seen.

One morning I had made a rudimentary breakfast for Masie and Celia... coffee and slightly burnt toast with copious amounts of honey spread on top. I put everything on a tray and slowly walked down the hallway to the bedroom. The door was closed so I put the tray down and opened the door. To my amazement Masie and Celia were having sex in what I had been told was a 'tribbing' position. Masie was lying on the bed and Celia was kneeling on top while their legs rubbed each other's pussies. It was a warm summer morning and there were beads of sweat all over the dark girls skin making it seem like she was covered in translucent glass... like an alien from an x rated Star Trek movie. Her breasts rose and fell slightly as she moved, her head was arched and her long hair flowed out down her back. Both women were breathing deeply and it wasn't long before they started to grunt and shake as orgasm's overtook their bodies. I knew that this uncontrollable shaking was the equivalent of my feelings when I ejaculated from my penis so I guessed they were both really happy at the time. I hadn't been noticed standing in the doorway and was about to leave when Celia suddenly pulled away and started to leak a milky liquid over Masie and the bed. I was spell bound as a small stream of warm liquid shot out from her pussy as she continued to shake and quiver. I thought Masie would be disgusted at being covered in the sticky looking goo but she obviously found it to be enjoyable and grabbed Celia pulling her down kissing her while laughing. I found the whole picture so overwhelmingly hot that I couldn't get it out of my mind for weeks.

Now my best friend lived next door... a skinny red haired freckled girl called Ginny. We were the same age and spent a lot of time together. Being my best friend I naturally shared all my new-found sexual knowledge with her. We felt so grown up with our little secret.

Ginny was bullied at school because of her looks... and the fact she was super smart. I mean genius smart, especially in mathematics. I had become her protector over the years and often had to stop kids bullying her with my fists. However the undue taunting stopped abruptly when we were 13 years old. Ginny was in a car crash with her family... she was so severely injured her legs had to be amputated. I was devastated for her and was a constant visitor at the hospital while she recovered. I also helped her with rehab and we became even closer friends. After five months she finally made it back to school and things changed... the bullying stopped, a small silver lining in her big black cloud. The bullies at school had always called her 'Ginger Ginny'... I know, not very original but they were small minded buffoons. For years I had tried to make her feel better by shortening it to Ginz and making it a positive nick name. I was pleased that after the accident my nick name finally caught on and so Ginger Ginny became Ginz and she loved it. Slowly she adapted to her new world of wheel-chairs and limited mobility, it took a long time and I helped as best I could. We even set up a gym in her garage for rehab exercises and worked out daily together.

Three years later things changed at home for me. Masie finally found the love of her life... Wendy, a solo mother with two children aged four and six. When it was announced that they wanted to move in together it seemed as though we would have to shift to a bigger house. That was not what I wanted... my best friend lived next door and our school was close by.

I hatched a plan. My hobby was to design houses using a copy of a computer architect program I had obtained from one of Masie's friends. I was quite proficient at using it and spent hours developing weird and wonderful houses and cabins for my own pleasure. I spent a week on my new plan and presented it to Masie when it was finished. My idea was we build a small cabin on our existing property that I could move in to... the new kids could have my old room. I presented my idea with the design plan and an estimated budget. I knew Masie loved the house we lived in and didn't really want to move so my idea was accepted. I did a lot of the building work myself putting in long days during vacation time, and with a little help from some of Masie's friends we managed to complete the place in less than two months... I ended up with a studio style room with a bed, study area and a couch. A small bathroom was also included.

When Ginny came over to see the finished product she was so impressed.

"Oh Zeb, this is amazing!" she exclaimed in delight. "You even made the door wide enough for my wheels."

"Of course! Now I have my own place I wasn't going to hang out here and watch movies by myself."

"You really are my best friend." Ginny teared up and I felt a little awkward standing there.

"You OK Ginz."

"I need a hug."

I bent down and we hugged for a long time. When we finally parted she kissed me on the mouth. It wasn't a sexual kind of kiss, it was just a nice friendly kiss. I had never thought about Ginz in a sexual way before, you don't do that with your best friend do you. But as I looked down on her I realised how pretty she had become. Her long reddish brown hair and lightly freckled face were now assets and not a reason for distain, her slightly bucked teeth had been fixed with braces and her smile and big brown eyes made her quite beautiful.

"You're staring, and it's freaking me out." Ginny looked at me frowning.

"You are beautiful, you know that right?" I replied.

" Zeb B, it was only a kiss, it didn't mean anything."

"I know, and it's not the kiss. It's just I don't think I've ever told you how good you look." I said smiling.

"Thank you, but can you stop staring now." Her skin was flushed.

"No... I don't think so. I like looking at beautiful things." I responded enjoying her embarrassment.

"Freaking heck Zeb, keep this up and I'm leaving!" her voice was raised in frustration.

"Okay... Okay. Don't throw your shoes in a hissy fit." I answered back smiling. I knew the shoe joke would make amends for my actions. It had always been a stupid thing I said when she got upset to release tension. Black humor, she loved it.

"Yeah well you keep you pecker down." Her classic retort. One she had started when I told her about my embarrassing erections seeing Masie's girlfriends naked.

We both laughed. I grabbed her under the arms and pulled her out of her wheelchair and unceremoniously dumped her on the couch.

"Movie time!" I sat beside her and switched on the TV.

My arm went around her shoulder as we huddled together to watch a movie. Neither of us had had a real boyfriend or girlfriend. I suppose we spent so much time together and enjoyed each-others company that it wasn't a big issue.

A week later we were sitting in her house watching a documentary on the science channel... way out of my league but I enjoyed the experiments they showed. Ginny was of course taking notes in her own version of shorthand... she had books of facts and figures in her room that she'd made over the years. We were suddenly disturbed by her younger sister and friends making a huge lot of noise.

"Shut up!" Ginny yelled a number of times. Unfortunately the rebuke only seemed to succeed in increasing their volume. "I wish I had a room like yours." She moaned to me in frustration.

We ended up leaving the girls to it and went outside.

"Could you build me a room like yours? Ginny queried as I pushed her chair out into the sunshine.

"Yeah I suppose I could. I know how to do it now." I replied sitting on an upturned wheel-barrow.

"How much would it cost, remembering I'd need to pay an electrician and a plumber whereas you didn't."

"I guess about five grand for the materials and two grand for the sparky and plumber."

"Okay, I'll get the money. You supply the blood, sweat and tears."

"Are you serious?" I asked in reply. "Where are you going to get that sort of money anyway?"

"I'm going to win it." Ginny replied with a grin.

"Yeah right." I laughed back.

"Give me two months and I'll have it."

She had that look in her eye that I knew only too well. It was her 'I've got a plan' look.

A month Ginny handed me a thousand dollars on the way home from school.

"Fuck Ginz! Where did you get this from?"

"I've been working on a system to predict winners of horse races. I place bets on outsiders that have the best statistical chance of winning. It's based on a whole lot of data and math."

"And it works?"

"I just gave you two weeks winnings," she smiled up at me and spun her chair in a circle for added effect. "I tested the theory for two weeks and refined my parameters and calculations before placing any real bets."

"But how did you even place the bets, you can't do that at seventeen?"

"I got my Mum to open up a phone betting account, I tell her what bets to place and she does it."

"Your Mum went along with it?"

"I showed her how my predictions went in the two week non betting trial and she was on board. As long as my Dad doesn't find out then all good."

Ginny's parents were divorced but her father was still around and he was a cop. Even though they weren't breaking any laws he probably wouldn't be impressed at Ginny's scheme.

"So how much do you bet?" I was getting really interested in this, especially as I still had the results in my hot little hand.

"I get Mum to put $100.00 on each horse for the win, and $100.00 for a place. We doubled our money each weekend. The goal is to increase the bets to $200.00 each time."

"And you double your money!"

"Yeah it's not a good as I had hoped so I'm still refining the data."

"Shit Ginz, that's unreal... you little genius. How long does all this take to work out each week?"

"About five hours of crunching the numbers... I need to know track conditions and log those into the system as well on race day."

"What happens when you get to the seven grand you need?"

"I dunno, maybe some university money, a new chair, some clothes for me and Mum. I might even consider a present for my best friend." She giggled and wheeled herself off down the sidewalk.

It took only eight more weeks before I had the rest of the money to start the build. Two months later we had a grand opening and Ginny was the proud owner of her own place. Our two cabins were backed onto each other on either side of our adjoining fence. We were separated by only an arm's length and I took this into account when I did the build. I put a window into the back of Ginny's place facing the fence and before moving her cabin into its final position I cut a hole in the fence and put a matching window it my place. We now had the ability to both slide back our glass and talk to one another through the short space between the cabins. I even put a nice piece of polished wood under the windows so we could use it as a table. It was like living in one apartment.

During our last year at high school the race winnings were still coming in and since we had we had both turned eighteen we had opened our own betting accounts, always careful not to bet too much so the little system remained a secret. Both of us had amassed enough money to see us through the first few years of post-high school study... not that Ginz needed it as she was almost assured of a major scholarship to study science at a good university. I was planning to attend a technical college to study design and architectural draughting. I did use some of my cash to buy a small van with a sliding back door that made it easier for Ginny to get in and out of. I removed the back seats so she could roll up a short ramp I'd made while in her chair and then swap out and get into the front passenger seat. Her dad was impressed that I'd bought something with Ginny in mind and offered to pay for the special front swivel seat I'd installed. Being more mobile we went out a lot more and had fun.

Now well into our senior year neither of us had had a serious relationship and we were both still virgins. Ginny had been trying to set me up with one of her girlfriends and a month before graduation I finally relented and said okay. The girls name was Erin. She was the bubbly kind of person who sometimes got on your nerves but I thought one date would shut Ginz up.

I took Erin to the movies and then we got something to eat at a local burger joint. She had made an effort to impress me with her low cut top revealing a fair amount of cleavage and her mini dress also revealed a lot of leg. I was surprised at how much she was flirting as we really didn't know each other that well. After our meal I drove her home. Again I was surprised when she leaned in for a kiss, one that involved a fair amount of tongue. We kissed for a couple of minutes before Erin suggested we park a little down the road. It was a semi-rural area and there were no houses close by.

"Let's take a walk." Erin immediately suggested as soon as I turned off the engine.

"Ahh. Okay." I was more than a little a little confused and disappointed by this development. The night wasn't the warmest outside and I had thought we were going to get back to some physical stuff.

"Don't look so glum, I've got a surprise for you." Erin smiled enthusiastically and grabbed my hand pulling me back down the road towards her house.

We entered her front yard and then detoured to the side down a driveway. Parked behind the garage was a camper van. Erin opened the door and pulled me inside... seconds later her lips crashed into mine in a passionate kiss. Things were happening fast and our hands were roaming over each other's bodies. I wasn't really used to this sort of thing and felt a little unsure of what to do next. How far do you go on a first date? Erin solved that question by taking a step back as she removed her blouse, then she reached behind her back and unclipped her bra letting it fall between us on the floor. The camper was only lit by the moonlight coming through a large skylight in the roof but it was more than enough for me to see two very nice breasts only inches in front of me.

"You can feel them if you want." Erin arched her back slightly so the twin globes of flesh stuck out proudly.

I didn't need to be told twice and my hands reached out and touched their first pair of breasts. I squeezed them gently and rolled the nipples between my fingers before lowering my head and taking one of the little nubs of flesh in my mouth. I sucked on it greedily!

"Oh yeah." Erin sighed and placed her hands on the back of my head.

I nibbled on each nipple until they stood out like little raspberries. Erin was now trying to get my shirt off by undoing the buttons with limited success as my head was in the way.

"Fucking buttons!" she exclaimed in frustration.

I stood and lifted the shirt over my head and dropped it on the floor. We kissed again while stumbling backwards and fell onto the bed at the back of the camper.

It wasn't long before her skirt and my jeans were also strewn across the floor and our roaming hands had more to skin to explore. Our making out became more intense and our breathing came in gasps as we tried to get air between kisses.

My hand had slowly descended to the front of Erin's panties and my fingers slightly lifted the elastic.