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.