My Sexual Life Ch 01 Cynthia

Chapter 1 - Cynthia

Prologue:

If you're reading this what you're about to read is pretty much 99% the truth. I'm writing this in order to quantify my sexual life in a more complete and expressive way than just the usual highlights reel men have in their minds. Sex is something too precious to be taken for granted and allowed to turn stale, wither and die. At least it is for me. In the many, many chapters to follow I'm going to do my best to lay out my entire sexual history in a way that not only helps me to remember all of it but to put it in perspective. In the last year or so I discovered this website and after reading many of the stories, seeing how well some of them are written has had an emotional effect on me. It's made me reflect on not just what sex is but it's potential is. I hope it's not only entertaining but in some way instructive, helpful and even a warning.

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NOTE: If you're looking for non stop sex this won't be for you. But I do promise that I will cover a very, VERY wide range of sexual arcs and there will be many long sex scenes and it'll be explicit, hot, unnerving and all very real. Every chapter will contain at least one explicit sexual scene. I'm not making any of this stuff up. Do enjoy. (Before I begin please note that all of this started 24 years ago. I'm only including direct conversation of the parts I absolutely recall. It might not be 100% but it's close enough)

A little about myself to this point. I was a shy, sheltered child growing up. The youngest of all my siblings with the nearest being eight years older than myself. I'd survived a traumatic surgery as a child so I was white gloved constantly my entire childhood. My graduating class at my high school was all of about 85 people. Ninety percent of us grew up together from kindergarten through high school. There was no dating anyone there because they were all like family. Plus any new students that joined our class during high school were picked clean in the first couple of weeks by either the jocks or the sluts. I was an intensely competitive tennis player who focused 100% on practice anyways. Everyone else was going to prom while I was on the road trying to qualify for the pro events. Basically I was a shy virgin who didn't care to waste my time on frivolous pussy chasing. I always had my hand to keep me company anyways.

ANYWAYS, it was the night of my church's youth group graduate dinner. Every year the church would host all of the graduating seniors from the church at a local place to congratulate them for getting through high school. I wasn't really into church so much as I was into spending time with the youth group there. They were really good kids who were all focused on their studies or their sport or volunteering, etc. It wasn't like high school full of cliques and bullshit.

The dinner was at a local, popular seafood restaurant. I have to admit that I'd been absent for the last couple of months due to state championships, finals, graduating, etc etc. Most of the people in my group were from different schools in the city and I was very happy to be seeing all of my friends who'd made it through graduation.

When I got to the restaurant I was greeted to a long table in a private room with about half the people there already. My old friend Mike was there and a few others. A group with everyone else showed up about 15 minutes later. Among them was a new member to our church. She sat down directly across from me. We introduced ourselves. I remember it almost exactly.

"Hi I'm Byron." as I reached out my hand to shake hers.

"Hi I'm Cynthia." she smiled as she reached out and took my hand. "But you can call me Cyn."

"Cyn?" I quizzed her with wrinkled brow.

"Cyn." she smiled.

"Cyn As in SIN... sin?" I said with a smile.

"Same word, different spelling." she beamed.

"Nice to meet you Cyn." I said very properly. We gazed for only a second and I turned my attention back to my friend Mike. I didn't want to stare too long and make anything uncomfortable. I was very, VERY shy when it came to women. I had no practice, had no idea what I was doing and had absolutely NO direction from my dad, brothers, friends, etc. I treated women with the utmost respect. That behavior overtime apparently lead many women to question the direction of my sexuality (which you'll see many times in my chapters).

We all made small talk and dined on platters of hush puppies, fried catfish, etc. The minister of our church eventually came into the room. He's eating with some of the church elders in another room and was coming over to give his official, 'nice job graduating. You're now ready to go out and face the world, yada yada yada, blah blah, woof woof' speech. While making the speech he made an effort to point out our newest member. Cyn's father come to find out was a high up in the church and had just been assigned to our state. Not being shy AT ALL she smiled and gave a little wave like she was the queen. Before leaving the minister reminded us that even though at the time the drinking age at the time was only 18 that none of us were to order alcohol or drink it at the dinner. It was an official church function and that wasn't' allowed. We all gave the obligatory, low volumned drummed hum and boo noises to which the minister of course laughed.

After he'd given his schpeal he left to return to the elders room. I was curious about being the child of a traveling minister and wanted to ask Cyn about it. Of course my shyness wouldn't allow me to spark up any conversation unprovoked with a girl. Thankfully someone else at the table did it for me. She told us about having to move every few years and the different places she'd lived. I listened intently without trying to physically LOOK like I was listening intently of course. I noticed though that while rotating her head around the room while telling everyone her story that she's kind of smile with her eyes whenever she'd get to looking in my direction.

When she was asked if it were a dull life having to move and constantly and always being under the watchful eye of a member of the church she just smiled, "Nah, I'm a P.K."

"P.K.?" I said quizzically. Why was I opening my mouth and having sounds coming out? You don't talk to girls I thought to myself. Please don't embarrass yourself!!

"Preacher's kid" she said with sexy eyes and a shit-eating grin straight at me. She held the smile and slowly turned her attention back to her friend to her left.

I still remember every detail of how she looked that night. She had on large, pink-framed eyeglasses. She had fair skin and a large amount of dark strawberry blonde hair done up into a bun. She was wearing a kind of loose, henley style blouse with no collar and a white draw straight tie at the top. She radiates happiness and was without a doubt one of the most extroverted people I'd ever met. She wasn't annoying about it or anything but she just loved to talk to everyone and it just seemed to make everyone happy.

We were all discussing the colleges we were going to go to, what we were planning to do for the summer, etc. I was feeling very relaxed around our new churchmate. I don't remember what everyone else was talking about but at some point I found myself lucky enough to be the focus of Cyn's attention. She started up a conversation with me and I tried my absolute hardest to not sound too eager to talk to her. The exact contents of our conversation I don't remember. All I remember was being lost with every word that came out of her mouth.

We'd gotten back around to the subject of being a 'P.K'. Again being the naive young man that I was I had no idea what that meant. Apparently preacher's kids are wilder than regular people's children. It was a way to rebel against their parents who are usually a little more puritanical about their behavior.

"OH?" I said with my eyebrows raised.

"Yeah... " she said. She put both of her arms under the table along her side, leaned in just enough so that her baggie-ish blouse caught the edge of the table and tightened it underneath her breasts which were now almost resting on the top of the table.

"I'm not always nice... but I'm always good." she said.

'Oh shit' I thought. Did...did anyone else hear that or was that me?! Is... is this girl... is she FLIRTING with me? I couldn't really tell. She's laughing and talking with everyone. At the time I didn't know this was what everyone else in the universe called, 'flirting'. To this day I still don't know when I'm doing it. My wife now actually finds it to be cute. My naivety didn't allow me to know if a woman was interested in me or not. Though every other person in that room knew. The waiters knew, the fish mounted on the wall knew. Hell, the fish being served on the table knew.

After a while someone at the table handed me a pen and asked me to draw. One of the things that I've been blessed with is the natural ability to draw. I used my gift to draw cartoons. I was an award winning political cartoonist by the age of 18 already. The table we were sitting at was covered with a long piece of white paper to help absorb the mess of fried food grease and any spilling tartar sauce or drinks.

I commenced to doing the usual quick funny sketches of things like cartoon dogs humping, a caricature of then new president Bill Clinton, etc. Soon though people were daring me to be a little bold. It was a church function and I always liked pushing boundaries with my cartoons. Editorial and political cartoons are funny in one way because the cartoon while not inherently funny in and of itself will be funny because you know that another group of people you don't agree with will be offended by it. Santa threatening to move his workshop to Mexico because of cheaper labor, drawing the governor of the state going out with his new girlfriend who isn't old enough to get into a bar yet. Those kinds of things.

While drawing two certain cartoon dogs (who will remain nameless as I like avoiding lawsuits) humping I had my head down, concentrating on getting it right. In the top of my eyeline I see a pen enter my field of vision and someone writing funny dialog bubbles of each character. I peer up to see Cyn with a pen leaned over the table to add her own lil contributions to my scribblings. Her non writing arm back under the table and now her breasts were firmly planted on the table. Her shirt wasn't low cut in anyway but that didn't stop me from basically having my brain go into a schism. After a few seconds I see her look up from her glasses that had slid a little down her nose over her glasses and flash me a smile.

I thought, 'wow this chick is REALLY cool'. Yeah... I know. WOW did I not see it. Seriously, NO clue.

The minister made another appearance and I scrambled to cover up the cartoon I drew of Jesus on the cross asking for a ham sandwich, It was next to the one of Noah's wife after being wrong about the flood having to do anal because she lost the bet with her husband. He thanked us for coming out and reiterated how nice it is to have such a large and devoted youth segment to the church, etc etc. We all meandered outside into the car park and were saying our goodbyes. Cyn asked if anyone wanted to go get coffee and beignets just down the street from where we were. I of course was too shy to immediately say yes. Anything, ANYTHING that looked like being interested in a woman was always shut off from my mind. A couple of other people agreed to go and then Cyn put her hand on my arm.

"Come on you should join us" she says, smiling flashing a mile wide.

"Oh okay fine!" I smile back, shrug my shoulders and tilt my head.

For the next hour we sip coffee, have beignets and chat about all kinds of fascinating yet purely useless topics. I say that because I don't remember a word of it. I was trying to keep myself as non threatening as I could.

After an hour the two people, the boy and girl who'd come along left. I was having a good time so I stayed. For the next THREE hours Cyn and I talked and talked. We discussed everything we could think of. Looking back now it was like a delicate dance of weaving between subjects and measuring each other's responses. Laughs, feigned outrages, you name it.

Finally it was really late and both Cyn and I were wiped. I could have talked to her for hours more but all I wanted was my bed and some sleep. We walked out to where our cars were and even though we both wanted to go home we spent another 30 minutes talking. I'd just happened to have my art folder in the back of my car so we stood there while I showed her a bunch of my art. I'd taken AP art in high school at the art teacher's request. Ironically my art abilities didn't blossom until my senior year. The teach said she just knew I was an artist and recommended me for the class.

Before we parted I found a little piece I'd done in ballpoint pen of a dragon breathing fire and gave it to her. To me this was all very, very innocent. I'm just having a nice time with a wonderful new person who I could see becoming a good friend. What happened next all happened in slow motion. She looks at her piece of art, smiles at it, reaches into her pocket, pulls out a pen, grabs my hand and writes her number on my hand.

"I had a great time. Call me and let's hang out." and she kissed me on the cheek.

The naive side of me realized exactly what was going on!

'FUuuuuuuuuuuu...' I thought. I'm in trouble. Trou-BLE! T-R-O-U-B-L-E!

I don't remember how I got home. For all I know I picked my car up with my hands, lifted it over my head and floated home.

I got home. Mom and dad were already asleep. I don't remember whether or not they heard me come in or if I even talked to them. I simply headed up to my room.

It was like 3am at that point. I furiously found a pen and paper on my desk and wrote her number down so that I wouldn't lose it. When that was done I laid in bed and no matter what I thought of it was her. Her face, her voice, the way she laughed. Then I thought about how she looked leaning over the table at me. Her breasts pushing against her shirt, her collar bones looked like ribs I wanted to chew on. Her neck was like something I still can't describe.

My cock pushed against my pants HARD. What the hell WAS I waiting for?! I unzipped my slacks, shoved them and my boxers down and took hold of him. Now I'm not ashamed to admit that I have a pretty decent cock. Its seven inches long but doesn't look very long because it's also over two and a half inches wide and circumcised. My hands are medium sized so it looks even larger when I hold him. :D

I started stroking myself slowly thinking about her. Not about her touching me, or kissing me or doing anything sexual to me. I was just thinking of her. I'd always masturbated to the thoughts of sexual activities with magazine models. I'd seen some softcore porn on cable as well. I didn't really own a huge porn collection. Hell let's be honest. I was 18. If the wind blew from the wrong direction I'd be hard and with a hair trigger at that!

I just thought about her face and her smiling with her perfect breasts and how she wanted to have coffee with me. The orgasm was starting building up before I had even started! I slowly pumped my cock for what seemed like an eternity which in real time was about 30 seconds. The wave was coming. I started to shake. I came and my mind went blank white. Cum splashed up on my chest. I kept stroking until the searing orgasm finally subsided. There's nothing like cumming the first time you meet someone and have butterflies. There's a large percentage of sex that doesn't compare to how that feels and you have to enjoy it while you can because its fleeting!

I cleaned myself off and slept the sleep of the dead. I dreamed about her that night.

...

The next morning I woke up and it was like my brain was stuck. I could only think of her. I needed to go to the tennis courts and practice. I did but it was just her!

'I wonder what she'd look like in a tennis skirt and sweater vest... or no vest. Would she have a good swing? She'd probably have a good swing.' were the thoughts running through my head. Every other thought of course was, 'I have her number... do I call her? NO I don't call her. You don't call women. You're way too shy for that. The embarrassment would kill you on the spot when you called her and she didn't remember who you were. Also, think about what'd happen at the church when you go to call her and she tells everyone in the youth group you called her? They'll all laugh at you.' You guys see what I was working with here?

The oddest part is that I truly started to not remember what she looked like. I'd thought about her so much that all I had in my mind was a vague recollection of a red headed angel with glasses and a great smile. Was this infatuation? Or maybe just lust?

Anyways, I don't remember if I called her or if she called me or if I saw her at church the next week but I'm pretty sure it was me calling her house. Her mom, lovely lady that she was was one of those moms who'd give you the third degree for all of about 30 seconds and if you passed her test she'd love you despite pretending to barely tolerate your existence. Her mom LOVED me btw.

Long story short she invited me over to her house for dinner. I accepted because to decline an offer for dinner would of course be the rudest thing you can do especially to a young lady who seems to not only like me but is very pretty and OMG SHE INVITED ME TO DINNER!! AIIGGGHHH!!

...

I arrived at her house and her mom was home and I was more nervous about meeting her mom than the fact that I was at a girl's house and had absolutely NO idea what I was doing there. Her mom of course loved me. I poured on the southern charm. There was a vague threat about cutting my balls off and dragging me across main st if I hurt her daughter. Honestly I was more afraid of her daughter than I was of the mom.

What was I doing there? From the time I walked into the front door it was like being in a raft on a rapids, tossing the paddles out of the raft and just going downstream in half shock waiting for any moment to see a waterfall in front of you that drops off for about OH a million feet. I knew on the inside that this is what people must do right? You meet people, you get invited to dinner and you feel as though you may vomit at any moment. My non-existent knowledge of women or what to do with them was making its way straight into the forefront. Why was I there anyways? Why was her mom there?

The only thing that broke what I considered the tornado in my head and gigantic lump in my throat was the fact that Cyn had two beautiful miniature collies. One caramel and one black. She told me their names a dozen times but at the time they might as well have been named, 'awkward' and 'virgin'.

Cyn had made chicken with green beans and cornbread. I made small talk with her mom while she was preparing the plates. Just before we were about to eat she told us to enjoy the meal and she left. She was going to out do some kind of church function with her husband. When the door shut I felt alone. I was alone in a house with a beautiful girl who was making me dinner.

'Uuuhhhh... how do I get out without her knowing I've left' rolled through my mind.

We sat down at the dinner table and she had the plates ready with a nice glass of iced tea. She sat down across from me.

She was a vision. Her hair was down tonight. It was long and thick and fell over her shoulders and arms. She was wearing a faded red, white and blue plaid shirt and jeans.

I sat and ate and we talked about church. She'd been showing the piece of art I'd given her to her friends. I think she wanted me to relax so she kept asking questions about me and my art, what I liked to draw, etc. Naturally I was trying to come up with the most profound answers I could to make myself look more interesting to her.