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 ūüôā

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: I’m A Virgin and Depressed, Should I Hire An Escort?!

escortsHey guys, from Australia here. First off, where I am from escorts are totally legal and regulated.  I figured I would at least get that part out of the way to save the legality part of this question.  Okay, now on to my dilemma.

I am in college, a senior and I am still a virgin at 22¬†years old. It’s Ironic too because I dress¬†decent, have a good group of friends, and I work out everyday. ¬† However I have always believed my face is ugly. ¬†My mom has tried to diagnose me with body dysmorphia,¬†but I think that’s what all mothers do. I’ve overheard plenty of girls whispering that I am unattractive. ¬†The few girls I have asked out have responded in what I took as disgust. ¬†I can’t help or fix my face, so I am going to be ugly forever. ¬†I have felt this way for as long as I can remember and as a result I have never achieved any form of confidence in my life.¬†It really sucks walking around campus with people, and you are just thinking the whole time about how you don’t measure up to anyone else in terms of looks and confidence. ¬†I do have a pretty good job for a college student and also play in a band on the side. ¬†I don’t think I am lacking in extra curricular activities or depressed because of anything other than feeling like no girl will ever really want me.

The past few months I have become even more depressed because It seems that I work so hard to feel good but still feel like shit.  I hate not having confidence because of my v card and facial unattractiveness, which then perpetuates the cycle of not being able to get women because I am insecure. I feel like when I am talking with a girl, all I can think about is how I suck and how there are so many better guys out there that she could easily get. This then oozes out of me in minor ways which women sniff out in an instant. Sometimes I do feel confident because my day is going well, but I find most of the time it sucks.

Continue Reading Q & A: I’m A Virgin and Depressed, Should I Hire An Escort?!

Q&A: I have been married 3 years and have never had sex with my wife.

Velvi Dilators for Treating Vaginismus

Sam from California

Hello, I am male,¬†33 years old, and ¬†married my high school sweetheart.¬†¬† We have been married¬†3+ years and still haven’t had sex.¬†¬†¬† Yes, I have never had sex with her.¬†¬† I do get the occasional hand job, and maybe once every few months she will actually put her mouth on my penis, so I guess I would call that a blow job.¬†¬† However, I have never had intercourse with her in any way.¬†
She has tried with other men in the past but it was so painful it made her scream and cry. ¬†Eventually she went to her OB and he diagnosed her with Vaginismus. ¬†She has always been too embarrassed to deal with it.¬† I love her with all my heart and do not want to put her through any¬†unnecessary shame either. ¬† I would like a child so I have suggested we adopt a child¬†to keep her as stress free as possible.¬†¬† At times though, I get weak and feel like I am really missing something from this relationship, but I don’t want to blame her.¬† Am I wrong to feel a bit resentful?¬†¬†

Vaginismus, sometimes anglicized vaginism, is the German name for a condition that affects a woman’s ability to engage in any form of vaginal penetration, includingsexual intercourse, insertion of tampons¬†and/or menstrual cups, and the penetration involved in gynecological examinations. This is the result of a reflex of the pubococcygeus muscle, which is sometimes referred to as the “PC muscle”. The reflex causes the muscles in the vagina to tense suddenly, which makes any kind of vaginal penetration‚ÄĒincluding sexual intercourse‚ÄĒpainful or impossible.
Venice Bloggs response: 
It’s disappointing to hear that you guys have been married for so long and have not been successful at achieving a sex life that includes active sex. To be honest, I’ve had to do some researching on what exactly was vagismus was. The consensus seems to echo several key ideas: vaginal pain during intercourse, vagismus can stem from physical trauma to the vagina, psychological factors, and/or history of discomfort during sex. Fortunately, this is a real medical condition that can be rectified with treatment. Ignoring the problem (and, yes, this is a real problem for you both) or believing adoption of a child will make everything better are two of the worst things you can do. That’s like taking Tylenol for pain caused by kidney stones, when really, you need to take out the dang kidney stones. Treating the symptoms and ignoring the disease will end up disastrous.
By not addressing this problem, you are preventing each other from fully enjoying each other in ways every married couple, in my opinion, should. That may sound a little shallow and maybe it is, but I know I need to have physical, sexual contact with Ryan to feel like I am fully connecting with him. Which is why it’s not the same if I perform oral sex on him until he cums when I’m on my period. I can’t imagine living my marriage like I was menstruating 24-hours a day. People need to connect, mesh, get dirty, plain ol’ fuck, to complete the relationship stage. It’s as if you were both stuck in your 17-year-old mind states: ignoring the problem, appeasing your partner by not taking a stand to do what will help you both, and finding ways to mask the dilemma with an equally problematic solution.
Though your wife’s problem is not uncommon, all the information suggests the same: it’s treatable. Talk to your wife and let her know that it will help you grow and strengthen your marriage. Overcoming her condition will open other doors as far as marital or other problems, as well as break down barriers in and out of the bedroom.
Ryan Bloggs response:
Oh man, I could probably type an essay answering this one.  First, if she is too embarrassed to deal with it, how does she even know she has Vaginismus?  My first suggestion is for her to see an OB/GYN and actually get some sort of confirmation she has this ailment.   If she has already done this, how many times have you yourself actually tried to have intercourse with her?   Did she have a boyfriend before you that she tried with and it hurt too bad?  I am sorry I am answering your question with my questions, but it seems like too much is missing here.
As a man, which is the purpose of me and Venice both answering questions, I’d suggest you have a serious discussion with your wife about the importance of sex in your relationship.¬† I understand this may stress her out, but she needs to decide which stressor is more serious¬†to her¬†.¬† The stress of an unhappy husband and marriage or the stress of seeing a doctor regarding her condition.¬†¬†Vaginismus¬†is very treatable, and although it may take¬†a while for her to gradually get used to¬† the size of your penis, had she started 3 years ago, you both would have been sexually active at this point.
You’ve even suggested adopting a child to ignore the issue altogether.¬† Is it your plan to be married and raise a family with a woman you’ve never had sex with?¬†¬† I will never understand this behavior or reasoning.¬† The foundation to a strong marriage is a great sex life.¬† If everything is going wrong in your life, the bills aren’t being paid and you are working long hours, the one thing you can control and depend on, is your sex life.¬†¬† As long as you are both on the same page.¬† Two people in a marriage can’t control the economy, random stressors, or outside elements that effect a marriage, but they can definitely control their intimacy.¬† When I am being intimate with Venice, the whole world shuts off around me.¬† My bubble consists of me and her, her body and mine, our words, our kisses,¬†our bodies melting into each other, ¬†no matter what is around me.¬† I feel the following statement has became a bit cliche, but women want an Alpha male.¬†¬† Everything in¬† your post suggests that you do not mind being her good little boy, even if her condition is serious.¬†¬† I say that carefully, because I do not want to mock women that suffer from Vaginismus, but I do know that your wife doesn’t suffer from Mouthismus.¬† Your comment regarding her putting her mouth on your penis every few months tells me that you really are bitter deep down inside and you are taking whatever it is you can get from her sexually.¬† If your wife wanted to be intimate with you, she would have went to the doctor’s office 3 years ago.¬†¬† If she was so embarrassed but wanted to please you, she’d satisfy you orally much more than just every few months.¬† That is absolutely ridiculous.¬†¬† There are also other¬†options, such as¬†having anal sex, which we have posted about on this blog numerous times.¬†¬†I am sure her anus functions properly, so she is capable of pleasing you this way if she wanted.¬† Gay men also have Vaginismus, it’s called a penis hole, but they still seem to have great sex lives. ¬†There are other holes besides the vagina that feel amazing. ¬†I really doubt the lack of sex after 3 years has anything to do with Vaginismus.
Man up.  If her condition is serious, get her to her OB/GYN so she can work her way into at least trying intercourse with you.   Do not suggest adopting kids, as this behavior suggests that you are okay with never have sex with her.  Are you okay with that?
Also, you both need to see a marriage counselor and a sex therapist, this one is way beyond my capacity.  3 years is habit forming.  She possibly has ruled out sex in her life forever.   Not good.