My First Time(s)

I have a strange, atypical sexual history.  Skipping the sexual experience I gained before I turned 13, which was bizarre by all means, I had my first kiss when I was 14.  First real kiss: tongue, hands, bodies, kissing for only one purpose.  That was followed closely by making out (if there is a difference), and my hands under clothes.  When I was 16, I removed her clothing and put my mouth on her nipples.  Biting came naturally, almost unnaturally available to my mind.  She enjoyed it.

If you remember the last adventure I referenced with Priscilla, then you know the next step in my sexual ladder after the above mentioned teeth and lips on nipples.  After that incredibly porn-like experience, I had to escalate the situation.  We were at my house, my parents were gone for another 3 days, no one was around.  Making out led to an exchange of what should happen next, with both parties agreeing it had to get freaky in a hurry.  She suggested sex, I suggested the shower. We removed clothing, got in, continued the making out, and then sex came back up.  I didn't have any protection, and I did not want to be a moron.  

She agreed that vaginal sex wasn't the answer, and suggested we just have anal sex. 

Whoa.  

Anal sex.

You're 17, have watched a typical amount of porn, are in a shower with a sexy blonde and a pounding reminder begging you to do it.  You don't know anything about what's waiting on the other side of this decision, because it can't be that different than the feeling you get after you jack off, right?

I told her to put her hands on the shower head.  I tried to insert myself as well as I knew how.  It didn't work.  It was tight, the water from the shower had dried out our skin, and exacerbated the problem.  Thanks to the fellas at Old Spice for providing me with body wash, so that I could grab the bottle and apply a copious amount of the blue goo to all the involved parts.  That worked.  I slid myself inside of her.  She whimpered, I groaned.  Then the fucking began.  

My hands faced each other as the pads of my fingers became familiar with her hip bones.  The water ran down her hair, following gravity's path across her skin, falling into the cleft of her ass and dividing its stream over my cock.  I continued my warpath, the ideas of porn in my head as I used my entire being to go as hard and fast as I could.   She came.  Her ass squeezed my cock with consistent force, and she got weak in the knees.  I began to pull out to stop, when she implored me to continue.  

Now, up to this point, I was having an okay time.  "OKAY? You were 17, doing something that most men fantasize about, and some men have to beg or pay to do!!!! What is wrong with you?"

The emotions I had been warned about began to affect me.  I was feeling guilty, shameful, unfortunate, and like I wanted to go.  Also the heat and steam in the air, mixed with the smell of the body wash, mixed with the smell of something else that I should have been prepared for, but didn't, all were beginning to make me a little nauseous.

Needless to say, I fucked her some more.  I reached around and rubbed her clit, I pulled her hair, I really did the picturesque job I had aspired to.  I didn't orgasm, didn't come close, and at the end trying very hard to stay hard.  I think it's really difficult for me to cum standing up, as I have since tried with a variety of stimuli, none of which works.  I may not be able to let go enough, since I am fairly certain if I were to cum while standing up, I would finish on the floor after my legs gave out.  

We got out of the shower and dried off.  We both sat in my living room.  That image, along with the picture of her looking back at me during the act, grabs me.  I haven't forgiven myself for it.  I spent the next week showering and washing my hands with alarming frequency, I couldn't make the smell go away.  It was everywhere, and everyone who looked at me knew what I had done.  It's haunting when I see her to this day. 

I had gone from making out to anal sex.  No warm-up, no progression, no romance, no feelings of attachment.  I wasn't equipped with the ability to see the consequences of that, to see what would happen as a result.  I can't imagine, or would rather not to, what she must have felt like.  What a terrible decision, a decision I still can't get past.   

I had sex for the first time with a girl I didn't know very well.  I had vaginal sex for the first time with a girlfriend of 22 months who had just cheated on me 12 hours previous, and told me That sexual experience consisted of me sliding maybe 3 inches into her, and being halted as she couldn't take anymore. So, with a condom on, and the least amount of my cock inside her, I couldn't feel anything. She subsequently cheated again.  

The first time I had an orgasm while I had sex was with a woman who I can't even remember her name, but I do remember that the guilt and shame I felt.  I had problems staying hard, because of it.  

The first time I received a handjob was from my former stepmother, who, when I wasn't even 13 years old, told me to take a shower with her so that she could help me wash off.  Interesting I returned to the shower to take part in my first explicit sexual experience since.  Of course, I didn't orgasm, but it was a handjob nonetheless.

I don't believe I am the only person who has ever been a victim of traumatic experiences, sexually.  People have suffered far worse things, and my past would pale in comparison.  That being said, I know my progression has not been something people would consider average.  Taking into account the room of variation, I don't believe the crazy shit I have been a part of would qualify as standard.  

Hmm. 

Lame car/sex reference story time: Can you handle a stick

Everybody that has had a good time with someone in a Biblical sense has probably had to navigate steering wheel and center console.  Broad, sweeping generalizations in mind, Ms. Inconspicuous  inspired me to recall my most indulgent car ride.  I was a junior in high school, involved in a few extracurricular activities that I shared with Priscilla.  She was dating another member of these activities, a young closet case gay guy.  Everyone knew he was gay, he just hadn't revealed his fondness for playing catch yet.  Priscilla was in need of some sticky loving, and I suggested in semi-jest that she buy a dildo.  Her response was warm, and I thought it would be fun to push her to see how far it would go.  Eventually I figured out she wasn't joking, and she wanted to go get one.  Not wanting her to embark on such an adult journey alone, and seeing as how I was so experienced myself,  I promised to accompany her to the nearest retailer. 

The day came, we went to the store, and I was amazed at what I saw when I went in.  Sex shops are wild, especially for a Midwestern kid who had spent the first 14 years of his life baptized in the beautiful sexual honesty of a Protestant church.  A whole wall of cocks and knobbers, hehe sounds like cops and robbers, along with the shelves of clothing and videos assailed my eyes as I took all of the debauchery in!  I think the best part were the condoms and penis-shaped gag gifts.  Something penis shaped used as a gag gift?  I love that shit. 

It took Priscilla about 30 minutes to pick out the one she wanted, while I spent the rest of the time giggling like a high school boy at the hilarity of a penis pump demonstration video being played.  She called me over to ask my input on which one I thought was best.  If anyone else realizes the issue with this, I'm glad I'm not alone.  She made her purchase, and took her military-grade-plastic encased phallus, along with a 76 inch toy, back to her car. 

The sexual flirting that had taken place up to the point of getting back in the car was playful, cute, silly even.  Door shut, music down, it's biznass time.  Palpable tension in the air, and that awkward we-just-came-out-of-a-sex-shop silence enveloped us.  We've all been there-- two high school kids in the car trying to decide who the hell is going to put the included Double A duracells in the toy.  It's a pretty common thing. What isn't common is, after removing the Joe Cocker from his wrapping and providing it with current, my sudden notice of how savvy she had been.  "She's wearing a skirt," my mind recognized.  As she started to drive, her hands found their way to my trousers.  "Her nails have been Frenched up", my mind recognized.  At the nearest stoplight, her mouth met mine.  "She's wearing a fair amount of lip gloss and smells damn good," my mind recognized.  I have since figured out that these things are buying yes's.  I was naive, that's my only excuse.  

"Priscilla, why don't you take your panties off?"

"Okay," her sheepish voice responded.  For a girl who had gone a long way to make sure things were conducive to the act about to take place, she sure sounded tentative.  

As she and I made the trip back to our meeting place, I was impressed at her ability to focus on driving.  Despite the stop-and-go traffic, despite the men in utility trucks looking into the window at the girl with one foot in the seat and one hand on my hair, and despite the humming sound hokey-pokeying its way in and out, she was able to safely navigate the roads back to my car.  I remember the visual of her hand on mine between her legs as she grasped my hair with extra zest.  Thankfully, she waited until we came to a full and complete stop before she washed my hand with her orgasm.

After exchanging pleasantries, drying off some skin, and making jokes I got out of the car and went home.  I couldn't believe I had done that, and I still have problems understanding how everything had escalated so quickly. 

The extracurricular activities we shared at school? We were both in a musical.  

I played her father.