Firsts are so much fun! I wanted to share some of my firsts with ya’ll.

My First Kiss:
I remember my first kiss very clearly. It was such a funny situation. Jordin and I were sitting on the porch of our friend Jon’s house with Jon and his girlfriend Elizabeth. (Elizabeth and I are the best of friends now, and that was how we met – our high school boyfriends were best friends, and that first summer, we spent an insane amount of time together….watching them play video games.) We were all cozy and cuddly, not talking, when Jon went inside to set up the N64 at Elizabeth’s suggestion – a smart girl, that one. She knew I wanted to be alone with Jordin, and that Jon wouldn’t think to do so.

We were finally alone, sitting curled up under the porch light. I turned to face him, and tilted my head up. He leaned down, and we kissed. It was sweet, and to my teenage brain, magical. Right then, Jon came bursting out the door.

‘Are you guys gonna play N64 or what?!’ I could see Elizabeth trying to pull him back into the house. But that’s Jon, sweet and oblivious. We went in, and Elizabeth and I watched them play.

My First Blowjob:
It was later that year, late December, that Jordin and I were parked just up the block from Jon’s house where he way staying, sitting in my car. It was almost 11, my curfew time.

By this time, we had discovered the wonders of making out, and did so at every opportunity, to the embarrassment of our friends. Since he was visiting from Florida, and my parents would practically follow us around our house, we didn’t get much time alone. But in the car…well, I know I’m not the only one who has fond memories of my first car for that reason. God I miss that car.

I slid across the bench seat in my old Buick Regal, closer to Jordin. Goddamn, did I love that car. It was so good for teenage makeouts. We made out frantically , with the sort of passion you only really have when you’re a teenager, in love, and just figuring out this sort of thing. It was messy, imperfect, and left me absolutely breathless, but that was mostly because he was eating my face. (Sorry Jordin. But you did improve with age!) When we finally came up for air, still groping, I finally asked to do something I’d been fiending to do for ages.

“Um…can I suck your dick?” His pants were off so fucking fast it was funny. I didn’t even hear the zipper go or anything. But nothing is faster than a teenage boy. Heh.

I slid down to the floor of the car, wedged between his legs and the dashboard, with one knee on the hump, and went for the prize. I was so excited! I was finally getting to try all those tips I read on the Internet. (I studied.)

It was fun! This was so much better than dry humping.

I also felt an amazing sense of power. Even though I was the one on my knees with his dick in my mouth, I was the one totally in control of the situation. I was the one making him squirm. And squirm he did. He had a death grip on the side of the seat and on the seat belt.

When he came, which due to our age and already excited state was fairly soon, he came in my mouth, and I swallowed. Jordin was the only boy who I allowed to come in my mouth, and even that was only if we were in the car. Swallowing is easier clean up, you see. Even that stopped after a while. I kept a nice stock of napkins in my car from then on. I’ve never been able to tolerate the taste of come. (I only have three hard and fast rules about sex. 1. Don’t come in my mouth 2. When fingering me, keep your thumb where I can see it and 3. Don’t use a gag on me, unless you want things to turn ugly. Most other things are negotiable.)

“That was awesome! Can I do it again?!” I exclaimed, scooting back up on the seat and wiping my mouth.

“What, now!?”

“Well, yeah, why not?”

“Wendy, I can’t get it back up again that fast. And its almost time for you to be home, and I don’t want your dad to kill me in the face.” (I’m Italian. My dad is a big scary dude, especially to a 16 year old boy)

Unfortunately, he did have a point. We said our good byes until the next day, and I drove home.

But that night…Ah, that night, a cocksucker was born!

My first Chubby Chaser:
And, the first boy I saw jerk off via the Internet.

I walked into the computer room at my friend Cindy’s house.

“Hey hon, whats up?” I sat down next to her.

“Ooh, lots! I just had a great idea. I’m just talking to my friend Pete. I’m going to set you two up. He’s perfect for you! He’s really cute, sweet, bisexual, and he loves big girls! I’m talking to him right now, and he’s interested.”

“Holy shit, really?” My jaw dropped. I had spent most of my adult life assuming that boys liked me *despite* my size, not because of it. That it was something they found distasteful, but put up with to get me to blow them. (I was already known as one who gave good head by then, and it was rather easy to get it.) The thought that someone might actually want me because I was a big girl floored me. I don’t know why it never occurred to me before, but I was ready to run with it.

I leaned over, to see what they were saying. He seemed very interested, especially after she told him I worked at the Avenue (A plus sized clothing store) Right away, he asked if I also shopped there. Sweet!

She gave him my screen name, and the next night, we chatted online, trading pictures and such.
My god, he was gorgeous, and even better, just as racy as me. He sent me a very lovely video of himself jerking off. I sent back some photos of me in lingerie and such. We made a date for coffee in three days time.

Pete didn’t drive, so we agreed to meet at the Cup, a coffee shop right across the street from a train station on Long Island. I agreed to drive him home afterwards, hoping that after we met, things would go well, and that I wouldn’t want to stab him in the face. It was a fairly long drive home.

Oh. My. God. He was, in person, even better looking than I’d thought. He was the first guy who was *exactly* my ‘type’ that I met in person. He was very tall, about 6′3, and very very scrawny, pale and pretty. He had gorgeous curly hair, and a pageboy cap that he almost never took off. Long legs, tight jeans, and a fitted tshirt completed the picture. (He’s starting to sound oddly familiar *cough*Sebastian*cough*)

I couldn’t take my eyes off him. Whats more, he couldn’t take his eyes off me! It was really awesome, knowing for a fact that he was looking at me and thinking about how good I looked, and not thinking ‘Ick. She’s fat!’ but rather ‘Mmm..’

We had the entire half out are of the Cup to ourselves, which was nice, and we spent a lovely evening talking and such. When they started to close, we figured that would be a good time to get going. I knew the general area where he lived, so I didn’t have to worry about getting directions for quite a while. First we drove around randomly, while he flipped through my CD’s and picked one to play. (That’s what we did on Long Island. Sometimes, half a date is driving around randomly while talking and groping, ok? There isn’t much to do.)

As I normally kept the cd’s between my seat and the passenger seat, this also gave him an excellent opportunity to put the cd case on the floor and slide closer to me while I drove.
He was very tactile, touching any bit of bare skin he could reach. I of course, didn’t dissuade him. I was having entirely too much fun reveling in the fact that this beautiful man was attracted to me! When you’ve spent most of your life thinking your unattractive, its a heady feeling to have someone telling you, with words and touches, how hot they think you are.

When we got to his house, we wasted no time after parking before we dove into the backseat, half naked and panting, and fogging up the windows on that rainy summers night. It was another hour before we were able to stop, and by then the rain had stopped.

When I got home, I found an email from him, to set up another date.

We only got together a few more times, before he decided he was in love with his ex girlfriend and couldn’t be with anyone else, (That fat bitch! I bet my fat ass was much more awesome than hers!) But we had a quite a good time before them. And I was at least memorable enough for him to email me again a few years later, when he saw my photos on RedClouds.com, and I was able to walk away with a much better body image of myself.

My First Coitus:
I was one of the last of my friends to lose my virginity, but it wasn’t through lack of trying. I desperately wanted to get laid, but for some reason, I couldn’t make it happen. (Funny, considering now I have no trouble making sex happen.) I was a month shy of my 20th birthday when I finally did have sex, with my college boyfriend.

The boy I lost my virginity to was a total geek. I loved it. He took the statistics from my birth control, and mathematically calculated, based on my age and weight, the chances of my getting knocked up using the birth control alone. I think it was a 1 in 7oo some odd chance, and we decided to take it. It was oddly clinical, but then again everything about Brian was like that. He was severely mentally ill, to the point where he didn’t even recognize it. He had terrible OCD, terrible anxiety and depression, and there was an entire year of his childhood he can’t remember, due to a tragic incident. When we rented hotel rooms, we always got one with two full sized beds. One that we would sit on to eat, hang out, watch TV, and play on, and the other to sleep in, because he couldn’t do all that in one bed. He was an extraordinarily picky eater.

But my god, at times, the OCD tendencies were great. He was absolutely fantastic at rope work. (I was never once able to wiggle or squirm out of his knots) He also gave amazingly long lasting girl head. He played the euphonium, and had very well developed mouth and tongue muscles, and must have known some sort of awesome breathing technique, because he would eat me out for ages. I think the record, the one time I could see the clock, was a solid 45 minutes. I assumed that this stamina and attention to detail would carry over to sex as well, but I was sorely disappointed.

We had tried previously, and just hadn’t been able to make it work. (he was not a virgin, but hadn’t had much sex before me either.) We figured it was the condom, so that was when he did the mathematics to see what the chances of insemination were. Since we had both been tested recently, and hadn’t been with anyone else, we decided to not use the condoms. We had put a towel down on my bed spread, because he didn’t want to get it messy. We of course opted for the missionary position, because he probably would have had a panic attack at the thought of anything more than that. He sort of kneeled over me, and slowly slid in. It didn’t hurt, but it wasn’t particularly spectacular either. I felt nicely full, but that was it. We didn’t kiss. He wasn’t big on kissing, which made it seem very impersonal. He thrust a few more times, but it was all over very quickly. He immediately got up and got dressed. He couldn’t tolerate being naked for very long.

I was kind of disappointed.

I knew better than to expect fireworks and bells ringing or a choir singing the ‘Ode to Joy’, or anything silly like that. I was a virgin, not an idiot. I didn’t have high expectations for my first time, but I thought that there would be more too it than that.

I ran into Brian a few months ago, at school, and it was an odd experience. I had just left Jefferson’s, and was rushing to get to my Anthropology midterm, all satiated and thoroughly fucked, when I saw him coming out of a classroom.

‘Brian! Brian Pancettia, from Bethpage! Hey! Its Wendy! Remember me?’

‘Yeah, that’s me…do I know you?’ He looked at me blankly.

‘We dated, remember? I was a Mortuary Science student…’ I threw out other details, things that would have reminded him, shit I only would have known if we actually knew each other. It was him. I know it was him. And he…denied it. Said it must have been some other Brian from Bethpage. Yeah, right.
Most people, I think tend to remember when they have dated someone who touched dead people. And besides, how can you forget me?! I’m freaking awesome. I cooked for him! I gave him the best head he’d ever got! Ah well. I suppose some boys are just dumb.

To this day, whenever I hear ‘Angry Young man” by Billy Joel, I think of Brian.

Ah, I like this trip down memory lane. I think I’ll be doing another post of firsts soon.