Friday, June 11, 2010

My first time

No. This isn’t about my first time venturing off into sexual relationships. Nothing went wrong for me, so it wouldn’t make for interesting reading.

No, no. This is about his first time.

How the hell could this happen to me?!

Trevor and I met up for our second date earlier this week at a pub for trivia night. We had a good time, conversing about simple subjects and whatnot. He opened up a little more about his past and went on to say that he hadn’t dated for the last six years that he was in college.  The only girlfriends he'd had had been in high school.  We later went on to a pizza parlor to have dinner and then brought me back to where I had parked my car.  It was a bit awkward for me considering I wasn’t ready to call it a night at 10pm yet, so I huffed silently to myself, gave him a hug and walked back to my car a bit upset.


The next day while at work, I text him “I feel it was a bit awkward last night, and I’m wondering if we’re compatible. However, I’d like to suggest we hang out in a more casual setting, say to watch a movie. What do you think?”

He agreed, and invited me back to his place after work, but not before asking “awkward how?”

I told him we could talk about it later and that I’d stop by around 8 that night.

I tried to work myself up for that night and get excited. I mean, it was another date….. behind closed doors….. you know what I mean?

I showed up to his place; he gave me a tour of the house and I later picked out the movie: Quantum of Solace. We sat down next to each other on the couch until halfway through the movie when he finally moved closer to put his arm around me.  Slowly but surely I started inching my way over until I finally just lay on his chest for the duration of the movie.

 Awww, how cute.


 When the movie ended, he started talking again about his shyness and lack of dating experience in the past.  I was starting to get tired of the same song- having heard it twice previously.  I somehow managed to ask him about his experience.

A few silent moments pass until he opens up and says "Yeah um.... I’m still a virgin”


I try to comprise myself and add “Yeah, I kinda had a feeling you might be.”

”I might as well tell you now, you were going to find out anyway” he said.


A few more silent moments pass, my mind starts to wonder and I ask “Were you waiting for something? Like, that special person, or do you just want to get it over with?”

He pauses, thinks and says “It’s not that I was waiting. It just….. never happened for me. I never got the chance. I never dated while I was in college. I was too focused on school. And now that I have a job and am stable, I’m looking to start dating.”

My mind was beginning to wander even further.

“I’m not sure if I should be here right now. My hormones are a little off, and I could easily just pounce on you right now” I told him, at which he laughed. Nervously.

“I mean, would it be wrong to say that I want to right now? Would you be up for it?” I asked.


“Uh, I don’t know how good I’d be. I’d probably be really nervous and I wouldn’t last long” he said.

In the back of my head I’m thinking- if he’s a virgin, he’s bound to be really excited right? At least, my first time with my virgin boyfriend was pretty great. Meh, might as well give it a shot.

After nearly 15 minutes of mulling it over, I asked him if he had condoms to which he answered “Yeah, they’re old, but I don’t think they’re expired.”

Hey, at least he’s prepared.

 I moved back up to his face and slowly put my mouth on his.

 W.T.F?! Where the hell is his tongue??

Imagine a pucker fish. Got it? Good. He kissed with his mouth wide open. While trembling.

 Oh my god- he doesn’t know how to kiss.  Shit, how will the sex be?

 After about 15 minutes trying to fight with his mouth and telling him “give me your tongue” I suggested we go into his bedroom.

He goes into his bathroom and produces a brand new box of Trojans, Non-Lubricated condoms and a tiny bottle of lube.

Oh man, this is going to hurt.

We go on his bedside and both start undressing ourselves. No- not each other, but one selves. I get on his bed and notice him grabbing a condom and try to put it on. I see he still has his boxers on, and tell him to take them off.

That’s when I notice it. And gasp internally.

 What the hell is he doing??

I calmly tell him “You’re not hard- You’re not going to be able to get the condom on.”

He looks down confused and continues trying.

Does he seriously not know there’s no way in hell he can get a condom on without an erection?

I look at him and notice he’s smiling nervously. “You’re going to have to help me” he says.

Yeah, I can see that.

Once hard enough, I manage to pull the condom all the way down and he gets on top of me, at which I grab to guide him through.


What the hell? How can- what the hell??

I tell him to slowly start thrusting while I try to get him to go in, with the hopes he’ll become erect again.

Nothing. Nowhere close. He’s just not hard!

I tell him “It’s not going to work. You’re not hard” as he moves to the side and I take off the condom.

I look at his penis and decide to head south, thinking maybe he needs foreplay. It works, for a while, but as soon as I fight to put on the condom, it deflates. Somehow though, I sense he’s still excited.

Is it possible to be turned on but not have an erection?

I try again, and as soon as I sense enough hardening, I get a third condom out and put it on for him.  As soon as it is on again, he loses the erection.

“I think I’m just really nervous” he says.

I’m trying to be really patient, but I’m getting frustrated. I’m sorry.

He comes over to my side and looks a little lost as well, but not quite disappointed. Seeing as to how he’s still willing to continue, I guide his hand to my nether region.  Hell, if I can’t get it the regular way, might as well go in the easiest way.

 He moves his hand every which way, not knowing what to do.

“Put your fingers here, like this” I say as I guide him.

He fumbles but finally manages to get them in right. Deep enough to actually hit my G-spot.  I actually squealed. At least he got that right. Right enough to give me three orgasms. I’m not making this up.

After that’s done, I try to work on him again to see if maybe we can salvage something.

He actually says to me “Maybe I should lie down, that would help me relax.”


“Yeah, sure” I tell him.

As I’m working on him, I notice he doesn’t become fully erect but manages to wince and gasp nervously. It’s as if he is enjoying it, but is too nervous to become fully erect.

 Or maybe he just can’t get erect at all?


By midnight, I decide to call it a night and wind things down. I got mine, but he didn’t get his, considering he never came. I got dressed and got my stuff to head out. He walks me to door, hugs me and misses my lips by a mile.

I do the walk of shame back to my car, all the while cussing myself out for assuming he’d be a “reasonable participant.”

Today, while at work, I text my guy friend to break in the news to which he responds with a text full of “hahahaahahhhahaahahahahaha”

I tell him I feel guilty and obligated to continue trying until he finally completes the deed, at which he tells me to be patient, work with him and give him some alcohol, but not get him drunk. “Hey, at least you can teach him to your satisfaction!” he adds.

What do you think? Should I keep trying to get him ready for the next person? Or just save my dignity and walk away?


  1. Save your dignity and walk away. You're no charity worker. Seriously, when it was my first time, I put myself out there for my partner, and tried my best to make it feel as hot and natural as I possibly could for him. (Yes, it's a him. I could probably have a long conversation with you about that kind of sex.)

    After the sex, I felt great, just because I knew I had given him no reason to worry about the same things you're worrying about in this situation with Trevor. I told him afterwards I was a virgin before it, and he said to me, "Wow, I had no idea. It felt like you had done it many, many times before."

    He's not right for you, sweetie. (I'm bisexual, and not completely homosexual - is 'sweetie' too much?) ... sigh. Leave him be and find another?

  2. He is way too nervous to get hard. I think there is more to this than meets the eye as well. I mean, he is what, 22? and he doesn't even know that you have to be hard to get a condom on?! Sounds a bit...Weird.

    Anyway, I don't think you should take this any further. As much as you want to help him, you're far too experienced, the best thing to do is leave it. He is trying to put himself out there on dating sites after all.

    Although, if you really feel you have to help him out, try and get him laid by another virgin the lack of experience they have may be a little easier for Trev.