Approaching the loss of my v-card

[luckyman]

Background

I've spent the last few years casting out religion and superstition from my life. Previously, I was a sheep of the Catholic faith. This caused an issue for me: I've known since I was a young boy that I do not want kids, but the Catholic Church requires the faithful to 1) save sex for marriage, and 2) always keep sex open to the possibility of procreation (i.e., never use contraception). So, as a good Catholic, I believed for over twenty years that I could never get married nor have sex (this was God's will, after all).

Fast forward to today, where I've semi-publicly gone godless (I've told a handful of friends and acquaintances, but am still scared silly about telling my immediate family). Because I grew up thinking I'd never get married, I put almost zero effort into pursuing intimate relationships with women. As a result, I feel like I'm awkward and blind in situations involving women (though my friends have given me conflicting assessments of my "game", and I'm in the "friend-zone" with quite a few women). In any case, I'm looking to improve the area of my life involving romantic relationships, but I have some hang-ups I haven't yet been able to shake.

One of these hang-ups is the mental roadblock I've placed on myself for still being a virgin in my late twenties. Intellectually, I know that being a virgin is not - and should not - be a big deal. I know that having sex for the first time won't change my life. Afterwards, I'm still going to be inexperienced, after all. However, my self-talk often goes along the lines of, "well, that cute girl deserves someone with experience in bed... since I have zero experience, I won't bother showing any romantic interest in her," which clearly isn't very empowering. Besides, Steve mentioned that losing your virginity is one of many examples of measurable personal growth, so I'd like to do it .


My Questions

The "problem" of my virginity was recently relayed by my close friend, whom we'll call Friend A, to her good friend (an acquaintance of mine), whom we'll call Friend B. Over the course of the conversation, Friend B told Friend A that she would like to "help me out" by having sex with me.

I'm definitely physically attracted to Friend B, and neither of us wants a long-term relationship with each other, which suits me quite well. I presume this is a desire by two adults to help each other out. And I do think it will help me - again, not in an earth-shattering way, but I think it could push me "over the hump," and I'll have one less hang-up. My best friend, in fact, called this my "ultimate slump-buster."

What issues should I consider as I'm deciding whether I should sleep with Friend B? If I do decide that I'd like to sleep with her, how should I approach her about it? Should I just play cool and make a move the next time I see her, never mentioning my virginity when we're alone and things escalate? (I don't have a problem discussing it or any other issue, I just don't want to make it awkward for her or ruin the mood). Friend A has apparently told a bunch of our mutual friends about the situation... would this change the way I would approach it?

What issues might crop up after the deed that I should be cognizant of? If she's patient and a good teacher, would it be inadvisable for me to pursue a friends-with-benefits relationship? (I'd like to be good in bed, after all).

Am I over-thinking and over-analyzing?

Thanks!
luckyman

[Rose of Cairo]

Originally Posted by luckyman

Am I over-thinking and over-analyzing?

Yes

Everything seems to be pretty clear about the situation, I don't see what there is to think about.

Why would you hide your virginity to her, given that she already knows about it and wants to help you out exactly for this reason?

Why don't you ask her if it's true that she wants to teach you a few things? This way things will be clear very fast.

As for what will happen afterwards, you can think about it when it happens. Stay in the now.

[funchy]

Hi Luckyman. I spent most of my childhood at a Catholic school, so I've heard all those rules before.

I'm going to disagree with you. You've put a lot of thought into your sexuality and beliefs. But it doesn't seem very meaningful to give up one of your most special and intimate moments with a "friend" who wants no relationship with you besides sex... basically not liking you for you but for your erection. This reduces sex to just some casual act, and you're missing the whole point that makes it special: to do it with someone who cares about you.

It sounds like you're a caring person. Is it going to be helpful to your personal development to be used for sex? Is it going to remain and empty act forever? What of the possibility one of you will develop feelings even know the other clearly doesn't want a relationship with the other? Are you going to be ok to be rejected after you lose your virginity to this experienced girl and start bonding to her? Or the flip side is she starts to bond to you, and now you've got to deal with drama.

Is it possible that, although she's experienced, she may not be that good? Could she teach you bad habits or transfer some of her emotional baggage to you? Just because someone has sex doesn't mean they're any good at it.

There is also the value of the existing friendship. Are you ok possibly losing her as a friend? Are you ok with mutual friends eventually finding something out and someone has to tell them "Noooo.... FriendB isn't dating LuckyMan, she's just getting a booty call" ?

What are your thoughts when the experienced and sexually-open FriendB finds others to sleep with, too? Are you ok sharing her around? Knowing she's the only one you're sleeping with but she may be sleeping with anyone throws the balance-of-power out of whack in a relationship.

Move forward 5 or 10 years. Lets say you do finally meet the woman so wonderful you want to spend you life with. Even know you've renounced Catholicism as an adult, the thought will cross your mind about virgins and wedding night. Will you ever regret throwing away this moment with someone who doesn't care for you?

Perhaps the problem isn't the virginity but rather your difficulty in starting and developing romantic relationships with others? Putting your --> in some woman's (.) doesn't make you a better person, a good lover, or more confident.

And this could go badly. She is a friend but not close. If she's disappointed in your first time, what's to stop her from saying "forget this" or even worse accidentally saying something hurtful. That could set you back. This is all the more reason to save it for someone who loves you, not loves the f----ing.

Overall I see there being too many bad outcomes and too little chance it will really help you achieve your goals.

[eskimo]

Seems like you're already leaning toward having sex with Friend B and you just want to make sure you're prepared for everything so you're not disappointed with the ramifications. I wonder if that's the right way to approach something as important as this.

Ultimately it's your decision, luckyman, but I'll tell you my story with the hope it will help you make a more aware one.

I was kinda in your situation - a late-bloomer and a virgin in my early twenties. Some of my friends had already had sex while in high school and I kept hearing stories about some of the other kids in school already having done it multiple times, not to mention all the experimentation that goes on in college for someone my age.

In my case, instead of enrolling straight into college after high school, I joined the army for four years and had great experiences traveling and working throughout various parts of the world, but lo and behold I still hadn't gotten laid by the time I finished my first two tours of duty.

My last tour was in Korea and that's when I met this girl. She taught English at a high school right next to my military base. I was lonely, concerned about my virginism, and if you know anything about enlisted military (especially those stationed overseas in hardship tours) you know it seems they have sex on any given night with any warm body - so the pressure kept building for me.

So this girl and I got close and I had sex with her in my barracks one night. It wasn't a bad experience (like I hear from some people who relay nightmares about their first encounters) but it wasn't great either. It was just sex - no love, no passion, no mindblowing orgasm.

So this girl and I kept seeing each other for the next few months and my tour in Korea was coming to an end and I had to make a decision on what to do with the relationship - do I break it off and return to the States or do I marry her and make her an honest woman since I took her virginity as well. I decided to do the latter because I felt some responsibility for her losing her virginity to me and so we married right before my tour ended and I returned back home while she had to wait a year for immigration processing before she could join me.

I didn't know it at the time but looking back on it now I was not ready for an intimate relationship with a woman and I definitely wasn't ready for marriage. I was never in love with my wife, didn't have much in common with her (except for a common ethnic heritage), and I wasn't truly happy being married, but we started having children from the third year of our marriage and so as a dutiful husband and father, I persevered and tried my best.

Unfortunately in life, when you're not being true to yourself and you're not pursuing those things you desire in your heart, things oftentimes don't seem to go well. Everything in my life suffered - my relationships, my career, my personal development, my happiness.

So last year, after 13 years of building a "relationship" on a false foundation, the pressure kept building and I couldn't put up with the charade anymore. So I finally had the courage to file for divorce and push through with it for good this time, but not before taking myself so far off my true path to fulfilling my life purpose.

I feel great now and free for the first time in a long time. After my divorce became final, it seemed like I was starting things back over again, picking everything back up from right before I got married. God is accelerating my development now and things are moving quick, but sometimes I think back on all the years I wasted because I made the decision to marry a girl I didn't love, which was greatly influenced by a selfish and fear-based desire to have sex before I was ready.

I'm at a point now where I believe I'm ready for a serious intimate relationship and I feel I'm close to being ready to get married again - this time though with the right woman. The beautiful thing now is that, in the various worlds I inhabit, I'm experiencing incredibly strong heart connections with a few different girls and I know that maybe one or some of these girls may be the right one for me to develop something serious with. And I know when I do, this time it'll be beautiful and based on the right foundation of unconditional love and service. And the sex will be the ultimate expression of this connection - something powerful, stirring, and mindblowing.

Well luckyman, many of the specifics in my story probably don't apply in your case, but you never really know the full extent of the ramifications of any major decision you make. Who knows, you may end up getting this girl pregnant or it becomes an embarrassing fiasco that scars you and sets you back even more, or you may find it an incredibly passionate and moving experience and find that this girl may be someone you can truly love and develop something with.

I don't know the answer to this but I can tell you from experience that when you're ready for this type of relationship and you find the right girl, you'll experience a passion and a desire for her that will be unmistakable - you'll just know with every fiber of your being. You just gotta keep developing yourself to prepare for such a stage.

Good luck!

Steve