[JerseyGirl12]

So I am in dire need of some feedback about an encounter I had last night. I’m pretty sure the whole thing was a disaster, but looking back, it was HILARIOUS. You can’t not laugh at how ridiculous the whole situation was, I told my friends about it this morning and we laughed for two hours.

Last night we threw a party at my house for my younger sisters birthday. (I’m a recent grad, and I had to move back home after graduation) Her friends from college and high school, as well as some of my friends came to the party and it was really fun. All the kids slept over because drinking and driving is strictly prohibited.

Her one friend—let’s call him Matt—he’s my little sister’s good friend and We’ve always gotten along really well whenever he was hanging out with all the other kids at my house. He’s the nicest kid. He’s 20 and I’m almost 23. He’s a flirty kid and we’ve always had a flirty banter going, he facebook chatted me a couple months ago saying that “we never get to talk or hang out enough”

Let me preface this with saying that I was raised in a rather conservative household. I wouldn’t consider myself a goody two shoes—or prude. I am inexperienced but this is from a lack of opportunity. I am a tad overweight and rather self-conscious about my body. I’m not saying I have zero self confidence--pretty is not the problem, I know I’m a pretty girl. I’m also 5’8 with blonde hair, blue eyes, but just a bunch of extra weight that’s holding me back—hence the hesitation to have had other experiences.

So come 2 am when people are starting to go to sleep Matt texts me saying “text me maybe” a play on the song “call me maybe” which, I think is hilarious. The dialogue is as follows:
Him: text me maybe
Me: whatttt?
Him: do you want to hang out with me after everyone bums out?
Me: Shhhhhhh (sidenote, this is a hilarious response. I was being ambiguous because I didn’t want to say yes or no directly, but rather let him interpret it as he wanted.)
Him: I can be discreet. You wanna hang?
Me: What do you have in mind?
Matt: Whatever you want…should I come upstairs?
Me: Do you, bro. (another vague and ridiculous response.)

Ten minutes later, there’s a knock on my door and he comes in my room. We chat for a few minutes, and then we start making out. Remember aside from making out, I have no freakin idea what I’m doing. Virgin, never blew anyone before, you know.

I will spare gory details, but give a quick overview of what happened—so I can give a clear picture of what went down.

Next thing, we are fooling around, and out of nowhere, I’m giving him a bj, (Which, thanks to previous highly detailed girl talk sessions and instinct, I semi know what I’m doing.) There were no problems on his part, but I didn’t finish him off because then the atmosphere shifted. Next thing I know a condom is coming out, I stop him there, straight up inform him that I haven’t ever done this before. But this doesn’t seem to stop him, and I do not object. I figure why not? I’m almost 23 never done this before, feel like it’s time. I am in a situation with someone I know—we’re safe so, we proceed.

Then after a few minutes of flopping/poking around, there was some penetration. I’d say for like 2 minutes. Then I guess it fell out and he couldn’t get it back in? I can’t really be sure, but all he said was “your ****’s too tight” Very romantic--I know. There was another few minutes of him trying to get it back in and I did everything I could think of to assist. Then he asked if I wanted to get on top.

Since I literally had no idea what the f I was doing, why the f would I want to get on top? At this point is was 4 AM and since sex was backfiring, I kind of just wanted to finish this up. So, I went back downtown to finish the job. Now, if the rest of it wasn’t awkward enough this is where it really got weird. I don’t know if the alcohol played a factor but this kid couldn’t finish. It took like 15 minutes. I kept saying things like “tell me what you like” and “what do you want me to do?” because THAT felt appropriate. Hilarity. He kept saying “I don’t know…its like 5 am I don’t know…I don’t know.” Eventually it became a team effort and the deed was done. Then we awkwardly half-snuggled for a few minutes before he left. And per my request that this be kept a secret, before he left, he said “this didn’t happen---well it did but, it didn’t” he kissed me and left.

Now, here are my questions: Is it normal that during a girls first time that he can’t get it in? He’s fairly well endowed. He is 6’2 and lanky. He had no problem keeping it up, but getting it in and keeping it in was a failure.

Also, why did it take so long for him to finish? Was it me? Was I doing it wrong? Was it a case of whiskey ****? Was he not into it? He didn’t really say anything.

He’s 20 years old, he’s been with other girls but I doubt he’s a seasoned professional. I wouldn’t imagine it would take him very long.

We couldn’t tell ANYONE about what happened (I of course, told my friends) but my sister would be so upset so I made him swear that he wouldn’t tell anyone that we hooked up. Is it normal for these things to be awkward?

Now the girl in me is questioning his intentions. Did he have his eyes set on getting some and I was the only available option, or was this pre-meditated and he actually wanted to hook up with me? If so, WHY is he interested in me? OR my biggest fear is that he did it for the story. Hooking up with his friend’s older sister and BONUS having it be her first time? I’m not an expert, but that sounds like a trophy to tell his friends about.

Most importantly, what do I do next time I see him. Should I expect him to text me? There are a few parties coming up at my house in the next few weeks. (We do an annual beer Olympics and my birthday is coming up) So is he gonna expect this to happen again? Was it really as awkward as I think—or is this weird stuff normal? Have I embarrassed myself to the point that he’s telling his friends and they’re making fun of me?

I’m so confused and sorry for the excessive information and questions but any feedback (please respond!!) you could give me would be MUCH appreciated.

Thanks in advance.

[jns]

Let me go after some of the easy questions first.

The first time is likely to be tight if the girl has not been masturbating with several penetrating fingers or inserted toys. And it is likely not just the first time, but the first several times (maybe up to a dozen or more). Guys also don't always know where things go all of the time in darkness or low light. It would have been best if you guided him in. On top of that, with you being so tight, he needed to use a lot of lubrication. I was with a girl one time who was so tight it took 15 minutes to penetrate and then when I was done, she was so tight I could not get out for about the same amount of time. She was moaning and breathing heavy for that last period, but to me it was somewhat excruciating because I was so sensitive.

Guys take a differing amount of time to orgasm from a bj. Some do not altogether. Add on top of that the desensitizing from the failed attempts at penetration, the alcohol, being tired and someone who doesn't know a lot of "tricks" and things could take some time. The fact that he orgasmed probably meant that he was into it. And into you.

Awkwardness would be normal given the circumstances.

If he is honorable, he won't tell others. If he is smart, he will keep the whole situation to himself unless you two decide to pursue something more. If that happens, he should only release the bare minimum of you two talking after the party.

If you two don't communicate earlier, get together privately at a future party and hash things out.

[PinkySweet]

I'm also on the chunky side but my husband has helped my self esteem a lot but that never been bad enough to hold me back from sexual exploration.

My first time was AWFUL! The guy wasn't a virgin and it was just awful and awkward.

The thing is everyone I had sex with it was awkward the first time, I cant really get into sex unless I'm use to the person. The first time I had sex with my husband is was pretty awful lol. He couldn't get it in either, and slipped out a few times. I think everything will be okay for you

[DreamP346]

First times are always akward. Nothing to feel ashamed about. We have all been there. You say he is experienced, but has he really had intercourse and if so, how many times. It sounds like both of you were inexperienced. It just takes time to figure it out. Don't believe those romance novels that describe the first experience as this amazing experience. It takes time and experience to get there.

What you should be thinking about is what you want to do next? Do you want to pursue a relationship or was it just a one nighter. Either way, you should talked to him, face-to-face, not text and be very clear about what you want. You could put it playfully and say "hey, last night didn't quite work out, want to give it another try?" or maybe "I know last night we got a little carried away, but I'm not looking for a relationship right now. Hope that is OK with you?"

[SweetPeaches]

My first time was really awkward too. My boyfriend at that time didn't even know what to do and couldn't get in. It was rather frustrating and both of us didn't enjoy it . But then the second time we did some foreplay first then we finally got the hang of it. Just keep doing it you will eventually become a master on it.

Ehh honestly, I would let him come to you. You don't want to become too needy.

[avvie_88]

Is it normal that during a girls first time that he can’t get it in?:
It can happen any time. Depending upon position, especially. Your arousal level can also be a factor (not aroused enough, or super aroused--super slippery, super tight...).

Also, why did it take so long for him to finish?:
Could have been anything you said. It could also just be how he is. I had a boyfriend who took FOREVERRRRRRRRRRRRR (that many "r"s were necessary, I promise). Years later, I'm still friends with him, and volunterialy one conversation, he offered up that I was the most fun/best he's had to date. Yet he still took a **** long time. It's just how he is. I feel bad for the other girls he's been with :-\ haha! I was 19, he was 22.

We couldn’t tell ANYONE about what happened (I of course, told my friends) but my sister would be so upset so I made him swear that he wouldn’t tell anyone that we hooked up. Is it normal for these things to be awkward?:
I would imagine hooking up within a friend circle (that involves family with the same friends) would be weird. My younger brother has a handful of friends who are contantly on him about getting my number and such...and we both think it's weird. And that's not even sexual.

Now the girl in me is questioning his intentions. Did he have his eyes set on getting some and I was the only available option, or was this pre-meditated and he actually wanted to hook up with me? If so, WHY is he interested in me? OR my biggest fear is that he did it for the story. Hooking up with his friend’s older sister and BONUS having it be her first time? I’m not an expert, but that sounds like a trophy to tell his friends about.:
You know if better than any of us. Don't get too worked up over it. Why did YOU hook up with him? To just do it with someone you felt pretty comfortable with? Forcus on that. If that was your intention and that's what you got (as awkward as it may have been), then wahtever! If I were you, I would approach the subject as non-chalantly and carefree (I guess you could say) as possible...which leads to the next question...

Most importantly, what do I do next time I see him. Should I expect him to text me? There are a few parties coming up at my house in the next few weeks. (We do an annual beer Olympics and my birthday is coming up) So is he gonna expect this to happen again? Was it really as awkward as I think—or is this weird stuff normal? Have I embarrassed myself to the point that he’s telling his friends and they’re making fun of me?:
Don't expect much, you can't be disappointed. Maybe just surprised. If you see him again, act like nothing ever happened. See how he acts. Joke as you normally would, speak to him as you normally would... If you find humor in the situation, it won't matter what other people think. They'll laugh and so will you--**** HAPPENS! haha
If you really wanna break down what happened with him, again, approach it in a carefree but curious way. Don't make it weird and like, "so...we hooked up...what does this mean?" Laugh about it, be light about it (ie: "wtf did we do?! ha ha ha")!

[JerseyGirl12]

Thanks so much for your advice, it has been really helpful!

[I_Am_A_Man]

It sounds like a typical first time scenario to me. Sounds like he wasn't too experienced either. A lot of girls, not just virgins, are tight and it takes some work to get inside. Or, if you want to skip the hassle, you could always just use lube. I wouldn't stress much over your situation. This kind of thing happens all the time and it's really not a weird or unique scenario at all. IF you like him, try again with him later.

[alex0_0]

wow that guy sounded like a douche, why would you get with him? much less why would you let him be your first? sometimes you girls horrify me.