Q&A: I had sex for the first time and failed. What should I do?

I had sex for the first time and failed. What should I do?

For a bit of background I am clueless when it comes to girls. I’ve never had a girlfriend before. I have never kissed a girl. I have never held a girls hand. I’ve always been very self conscious about my looks and never thought any female would find me attractive so I never really even bothered trying.

I have been hanging out with this girl for the whole summer. She went to my high school and moved before graduation. She is back for the summer and we have been hanging out nearly every day. Just getting food, smoking weed, watching TV. Normal stuff. She invited me up to her room to check out her current living situation etc. I sit on her bed as there really is no where else to sit. She is showing me some new music she downloaded on her computer and after a while she showed me some funny YouTube videos.

The whole time she is inching closer and being very touchy etc. My dumbass did not pick up on any of these signs. Like I said earlier I didn’t think any girl would be attracted to me. Especially not one this pretty. So it’s getting late and she asks me to spend the night, i asked here where i should crash. She said I could just sleep in her bed with her. So i laid down under the blanket and was about to go to sleep when she gets in my face, maybe an inch or two away. She puckers her lips and closes her eyes. I literally and stupidly said, “what are you doing” and she said “what does it look like” and I said “it looks like you are trying to kiss me” she started laughing and that’s when my dumbass realized what was going on. We made out passionately for maybe five minutes. (I got my first kiss hooray!) Then she began taking my pants off and gave me my first ever hand and blow job (hooray again). She said she is usually really good and quick but I was very nervous and lasted a very long time. Her jaw began to hurt and i told her not to sweat it. Not sure why but I could not finish for the life of me.

She is talking extremely dirty and is asking for it, I talk dirty back and tell her I would give it to her etc. Well i got a condom on and she got on her knees into the doggy position. I have never seen a vagina let alone been in one at this point. Keep in mind it is very dark. I couldn’t find the hole to make things simple. She tried to help guide it in etc but it was just continously slipping out. She is very tall so it put me in a very awkward position. I could hardly reach and when I got it in it would come out easily because for one I am not yall and for two she has a rather large butt and my dick really is not very big either. Also I couldn’t manage to get fully erect with the condom on.

I felt super embarrassed and just sorta stopped after a few more attempts etc. I apologized profusely and she said I was fine and that it’s ok. I told her I was sorry I couldn’t satisfy her and she said something along the lines of no problem. I could tell from her tone she was bummed out. She put her clothes on and I suggested maybe I just go.

I’m at home writing this now and I hate myself smh. I dont know what to do. If I should try again, if that would be too awkward, if she doesnt even want to try again or even see me. Worst part is she doesn’t know I’m a virgin. Should I tell her? I really am bummed out, I didnt think sex would be this difficult. At the same time I am pleased to finally have kissed a girl and received oral. Amazing feeling 🙂

Venice’s response to had sex for the first time

For sure tell her that was your first time.   Had she known prior, she may have helped you a little more or not turned around so you would have to penetrate for the first time doggy style.  Not an easy position for a first timer!

Good ole fashion missionary would have been the way to go.  A good way to get her missionary is to go down on her, run your tongue through her vagina…maybe look at it closely and study it so when you try to stick your penis in it later, you know what you are doing!   And then you can add another first, the first time you ate a girl out.  Out of all those first times, that one is the most important in my opinion!  But maybe I’m bias.

Ryan’s response to had sex for the first time

I’m all about being open and honest.  If she talks with you again, let her know that was your first time.  Believe it or not, she won’t judge you in a negatively.  That’s kind of a guy thing.  Guys can be bullies when it comes to virginity.  She will probably find it adorable.  

Congrats on your first kiss, first blow job, first hand job, and the first time having sex.  Even if it was just a little penetration, that’s pretty much a grand slam right there.  It didn’t go as you planned, but that’s pretty much how everyone’s first time goes.  

Q&A: My Mother Opened A Very Large Dildo on Accident that I ordered

My Mother Opened A Very Large Dildo on Accident that I Ordered

I own two vibrators. One, I bought and had it sent to the post office out of fear of this exact thing happening to me. But, recently, I bought another one and thought fuck it, my family has never opened one of my packages before. It won’t kill me to have it sent directly to my address.

So I was sitting in my living room, cool as a fucking cucumber, when the doorbell went, and my mom said it was the neighbour with a package they held for us because we were not home when the delivery guy showed up.  I didn’t think anything of it – my package wasn’t due for like another two weeks. Well, I guess Amazon wanted to give me a really nice surprise, lucky me!

Two things my mom should learn is: 1) Wait for a reply after knocking on my door, and, I guess after this 2) READ THE FUCKING NAME ON A PACKAGE! She stood in front of me opening it, stared at the package for a bit and said “That’s not mine”. My heart fell into my fucking vagina as I realised what it was.

Okay, maybe it isn’t as bad as it sounds, because it isn’t immediately obvious what it is. It’s a huge bat shaped box, shaped like I ordered a golf club or something.  Thankfully, there were no pictures on the front, just the name of the brand and the slogan, which was something like ‘created for your happiness’. I mean, that could be anything, right? But me, being a stupid bitch, after fumbling a bit saying I didn’t know what that could be, decided to say, “oh, I think they’ll probably be my coasters”. Don’t even ask, it’s the only thing I had also ordered that I could think of. Coasters. To put your drinks on. Put into a long box labelled ‘created for your happiness’? Who on earth receives happiness from fucking COASTERS?

To make matters worse, I then had to sit there with my mom watching Game of Thrones, holding this huge Louisville Slugger shaped box in my hand.  To leave the room, I had to go past my mom – how do I walk past my mom holding a vibrator whilst trying to act nonchalant? Oh yeah, no big deal, just my coasters… in a box that is shaped like a loaf of bread, don’t mind me.

Thank God my dad didn’t come home.  I would’ve literally rather unboxed it in front of my mom than explain that shit to my dad. In my room, I looked at the side of the box, and there were fucking vibrating settings. I still have no idea if my mom saw that. Wow, I fucking pray to God she didn’t.

Venice’s response to Mother Opened A Very Large Dildo

Well, at least your mother knows if anyone breaks into your house she can run into your room and use your dildo for protection.  Sounds like you could fight off a dang lion with that thing!

Thanks for sharing your story!   Not really a question, but yes, when ordering sex toys and living with others, you may want to get a P.O. Box to insure privacy.  We share our shipping with our daughter, because she is a student (anything for a student discount), so our story would be the exact opposite!   She’d accidentally open our packages!  Oh gosh.

I will make sure I tackle her  at the door when I see her opening a packages shaped like a huge baseball bat!  

Ryan’s response to Mother Opened A Very Large Dildo

Hilarious story!   

It’s crazy how taboo and scary sex is.  If it was a back massager, or anything else used for personal enjoyment, totally fine.  If it is something sexual?  End of the world!  That’s what is so funny about sex and all the different sex experiences you have in your lifetime.  Sometimes the most embarrassing moments will be the memories you laugh at for years.  For Venice and I, one of our worst experiences we’ve had (with another female) is the funniest story we have.  It’s the gift that keeps on giving.  We have inside jokes, a sure fire funny story we can share with people we meet in the lifestyle, and for such a bad experience, it gave us so much more throughout the years than the actual good experiences.   How weird is that?

Not that this helps, but I assume by now, you are over the embarrassment and have moved on.  Time fixes everything.   Enjoy your tennis racket! 

 

Q&A: Broken Promises, Sleep instead of Sex, What Can I Do?

Broken promises, sleep instead of sex, what can I do?

I understand that sometimes she might just not be feeling it, that’s fine. What frustrates me is when she tells me we will do something and then it doesn’t happen. If she hadn’t said anything, I wouldn’t have been expecting anything in the first place. This is something she does at least a couple times a month, I think she thinks it’s something I want to hear. sleep instead of sex

Yesterday I proposed to her and we had an awesome date after. There was a lot of drinking and eating involved, so when we got home we were both maybe not feeling the sexiest, despite the amazing day. I was fine with relaxing for a while and going to sleep, but she turned to me and said “I’m going to take a one hour nap and let me stomach rest, but then you better be ready”. Sure enough a one hour nap turned into sleep, and now it’s morning and she still isn’t up. I need her to stop doing this, because while her intentions might be good, it makes me expect things and fucks with me.

Venice’s response to sleep instead of sex:

Let her know how you feel.  Sometimes a woman is horny and gets caught up in the moment.  I have been a bit tipsy to where all I can think about is fucking Ryan.  I grab him, stroke him through his pants, rub his body, and whisper to him how much I want to fuck him.  And then I drink a bit more and all that changes because I get tired as hell.  Communicate with her about her drinking too much, or about not offering you sex if she isn’t going to follow through.  Maybe find a place for a quickie when she is in the perfect mood and all over you.  I can see how her falling asleep would be extremely frustrating.  I think she will understand as well.   

Going to sleep instead of having sex?  Well, have sex in your sleep!

Going to sleep instead of having sex?  Well, have sex in your sleep!  This is why I always sleep nude!  I know we are taught that this is bad and scary, but if its two adults and both find it sexy, try it!  I find it kinky to be taken advantage of, even when I am sleeping.  For us, this works.  I trust Ryan with my life and know he takes care of me at all times.  This comfort and trust allows me to open up to him and enjoy something maybe most women never get to enjoy.  Sometimes Ryan could be rubbing me or moving his penis in and out of me slowly while we lay in a spoon position.  I may fall asleep and wake up with my whole crotch wet and sticky.  This really turns me on.  Chance are, I will either sit on his face and make him clean me up that morning, or fuck his brains out to make up for lost time. 

Ryan’s response to sleep instead of sex:

As always, the answer is communication.  Talk to your girl and let her know that you feel her intentions are good, but when she promises sex and doesn’t make good on her promises, it does more bad than good.  In our relationship, we have an open door policy (pun).  If Venice falls asleep when I am turned on and erect, I can grab some coconut oil and gently slide my dick inside her.  There have been times after a few drinks she doesn’t completely wake up.  It sounds weird, but with two consenting (consent through communication and having relationship rules) adults, this is an amazing experience.  I always move slow as to not startle her.  Sometimes I fall asleep inside her before I finish, and sometimes I finish and we both just lay dripping wet through the night.  I’ve woken up before with my penis “water logged’, shriveled and wrinkled because it rested inside her body all night.  She doesn’t mind, she loves waking up sticky and dripping, and it turns her on to know I enjoyed her body without her having any memory of it.  It’s kind of a sexy mind fuck the following day for her.  This doesn’t happen often, but it does prevent broken promises.   And of course it works both ways.  If she reaches over and feels me sleeping and erect, she can hop on me at any time and use my body for her pleasure.  I don’t think I have ever not woken up from her getting on top of me, but there has been many times when I will jump from a weird tickle feeling or have a dream that I am peeing myself, and when I wake up, Venice’s face in my lap, mouth around my penis, as she lays sideways masturbating herself.   This may be advanced for your situation, but an open door policy is a fun and exciting way to keep from having your night ruined.  If you trust each other, love each other, and know either of you wouldn’t hurt the other, this is a great way to solve falling asleep instead of having sex.  

Q&A: My girlfriend asked me if I wanted to have a threesome in front of the other guy.

My girlfriend asked me if I wanted to have a threesome in front of the other guy.

She’s 21 and I’m 25. We were at a party with her friends from high school and out of no where while I was talking to one the guys she went to school with she came up and asked if we could have a three some. I was caught off guard by this and didn’t say anything at first. The other guy said immediately that he was down. I eventually said no and she didn’t bring it up the rest of the party.

On the way home she asked again and I once again said no. Then she told me how hot it would be for both of us and that it would spice our sex life up (which I though was fine). I’ve always dealt with insecurities sexually and she has helped me overcome some of it, but after this it is coming back. Am I in the wrong here for not wanting one or should we try it?

Venice’s response threesome

Even though I have already had threesomes with Ryan and other girls, even now, if he asked me on the spot in front of the another girl, I would be pissed off.  It’s inconsiderate and all communication about your relationship should be done privately.  Especially a bomb shell like that.  I’d seriously consider finding a new girlfriend.

Ryan’s response threesome

You could do 2 things in my opinion.   Break up with her.  For her to ask you in front of the other guy was just a garbage thing to do.  For her to ask him prior to asking  you, was even more garbage.  Your other option is, if you want to see her fucked by 2 dicks before you leave her, say yes.  Have the threesome and break up with her afterwards. I’ve always said I would only have a mmf threesome if I didn’t really care much about the girl.  It’s not something I’d want to experience with a girl I love.