Doin’ It With Dr. V: The 28-Year-Old Virgin
This week, I got a letter from a lady who has an itch she’s been meaning to get scratched. She just can’t quite seem to reach it.
I have a dilemma and am looking for some advice. I’m 28 years old and still a virgin. It isn’t something that I planned, and I find it a bit embarrassing. I dated the same guy all through college, but at first I just wasn’t ready yet. Even once I personally was ready, I knew that having my first time be with him wasn’t probably the best idea. (We were complicated, angsty, and breaking up/getting back together all the time, and I felt like having sex with him would just complicate things further.) I dated a guy for quite a while after college whom I wanted to sleep with. We had great chemistry, and plus I was really ready by then. He told me he didn’t want to because he “didn’t want to be the jerk who took it from me,” and eventually he cheated on me. It took a little while to recover from that, and I didn’t even date for a while.
I have dated since then, but nothing serious enough to think about sex. Now I’ve just started seeing a guy that I kind of like. It’s still VERY new, but I know we’re going to have sex soon, and I’m not sure what to do. I don’t really want to tell him that it’s my first time, but I’m afraid he’ll figure it out. I should mention that I’ve done everything else, and have had an orgasm, but I’m afraid that I’ll be bad at sex and won’t know what to do. One of my girlfriends who knows about my situation thinks that I should tell him that it’s my first time, but I really don’t want to. I never meant for sex to be a big deal, am kind of wishing that I had just had sex at some point over the last several years with someone I wasn’t serious with, and I’m afraid if I tell him that he’ll turn it into a big deal (like my ex did). It’s not that I want to lie, and I realize that he should be OK with it if he really likes me, I just don’t see a reason to tell him (other than I might be really bad at it). Any thoughts?
Sounds like you’ve been holding onto a lot of things for too long—so frustrating, I know! Hot stuff, sex is about letting go, opening up. Getting down and dirty. Going all the way with someone, no holding back. And honey, if you can’t tell a man what you’re thinking, how are you going to be able to show him, naked? I’m with your gal pal, you gotta tell him, and here’s why.
From your letter, I get the sense that you just want to give your virginity to someone, like a present. How generous! Sure, there’s a chance you’ll freak him out if you tell him you’ve never done it. But then is a guy that is willing to run away that easily the kind of dude you wanna do? No way. I cannot let you go down like that! So, I’m so glad your ex showed his true colors before you got too deep.
All the emotional stuff aside, even if you lost your hymen horseback riding at summer camp or something, sex hurts the first time. He’s going to need to go slow. You’ve gotta give him a heads-up, no pun intended, before your first time is more painful than it needs to be. And you know, stained sheets will give you away anyhow. Honesty is the best policy.
Besides, the idea of a tight virginal vag is, like, every man’s fantasy. Start thinking of it as a plus, not a minus. You hold the cards, er, the V-card. Plus, if you’ve been lovin’ this long on oral sex alone, clearly, you’re giving in the sack. That’s what we’re all looking for. You big giver, now it’s your turn to get your sexual fantasy!
Honestly, if you’ve gotten the foreplay down and orgasmed, well then, sugar dumpling, you’ve made it! You’ve got more than enough experience under your belt to have sex. And frankly, to get the P in the V really requires no skills—you got the hard stuff out of the way first. Now, you just have to sink one in the hole. But I would wait to put sex on the table until you two have just straight-up hooked up. Then, once you get your kinks worked out and both know how to please each other, you can go the distance.
That being said, I want to warn you: Sex doesn’t keep a man. In fact, in my experience, it is not uncommon that after they get what they want, they don’t want it anymore—even if you screw like a hybrid of Dr. Ruth and Angelina Jolie. So, just be prepared. He might bail on you after sex. Or you might hit a bump and break up shortly there after. But then again, nothing in life is certain. We’ve all got to take it where we can get it. And, might I add, get it while the gettin’ is good. Seems like this new man has real cherry-poppin’ potential, if you want to give him the chance to get to know you!
Hi, I’m Dr. V. I’m not a real doctor; I just play one on the internet. What I am is a lady, a lady who is a fool for love! And I love nothing more than sex. My deepest desires have happily led me on many adventures in the sack, but they have also, sadly, made me one of my gyno’s most valuable players. But I’ve lived to tell the tale(s)! So, from time to time, I will dish the dirt on everything from getting freaky to getting freaked-out. And please, if you have a question, email me. You know I love to read your smut too!


















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Ginger
wrote on September 27 2009 @ 01:17 pm: [report]
Dr. V, I think this is one of the best responses you’ve written.
I was a lot younger when I lost my virginity, but I had a similar situation in that I had had guys say they didn’t want to be my first because it was some big responsibility (even though I was just looking for sex) and then when I did have sex, I didn’t tell the guy. And it hurt a lot. Later when he found out he said if he had known he would have taken it a bit slower.
This woman would do right to listen to her friend and to you about this.
draymond
wrote on September 27 2009 @ 01:36 pm: [report]
Spot on response, She should definitly tell him before it happens. Simply put a guy who she trusts enough to lose her virginity to is a guy that she trusts enough to tell him that she is a virgin.
Lone Wolf
wrote on September 27 2009 @ 01:39 pm: [report]
How about a different perspective (if I may)? I was proud for a while to be a virgin much later than 80+ % of my age group. I almost made it to the age of 22 when I lost mine. Granted, it was awkward, even though she was a very well experienced older woman (gotta’ love them Cougars). ;p~~~
To a degree I wish (as the nice lady above stated) that I too, had a couple of experiences early on. But what if that would have changed my WHOLE perspective? Would I have met my wonderful Wife, that I’ve been with for almost 10-years now?
I applaud people that can old onto their V-Card, BUT, because of MY frustration, toward the end I was almost willing to give mine up to any lady. Because of my lost time, I was almost a man-whore, sleeping with anything female that walks. Some just for the sex & some turned out to be totally psychotic, uh, “ladies”.
Look, do what feels right - - protect yourself, make sure you don’t get any of the nasty things that are goin’ around. Protect your heart & mind by telling yourself, if it happens, it happens - - it doesn’t have to be a perfect thing. Do you know BEFORE the sex that this is a guy you’d like to wake up next to in a long-term relationship or does that even matter in your life right now?
Maybe you’re the one that will decide: “o.k. I let this happen, now I want to play the field a while”. Don’t limit yourself if that’s something you would like to do. I’m SO LUCKY that I didn’t get any of the ladies I was with pregnant. That would have messed up our lives, like it does to SOOO many. I agree with BOTH the Good Dr. & Ginger above, be honest, with YOURSELF & your potential first partner. If nothing else, it saves a LOT of confusion & pain in the long run.
Good luck & I hope it all works out for YOU - - he’ll be a lucky guy indeed.
Be SAFE, Be WELL - - PEACE To ALL. . .
-Lone Wolf
theattack
wrote on September 27 2009 @ 02:39 pm: [report]
Dr. V makes a lot of good points here. It’s all contrary to my experience though. I was in a serious relationship with someone I loved, but we never had sex. He was away at college, and I was still in high school. He didn’t want to have sex yet, because he wanted to be able to sleep together afterward (which was something I did not care about). The seriousness of the relationship started to freak me out, so I broke up with him after graduation and slept with the first jackass that came my way a couple of weeks later. He still doesn’t know he was my first. It didn’t hurt, no bleeding, and it was meaningless. It wasn’t a big deal to me, so I didn’t want to tell him and make him assume it was, thus scaring him off.
Ginger
wrote on September 27 2009 @ 02:41 pm: [report]
@theattack A lot of guys seem to think that if a girl sleeps with them first, they must mean something to her romantically. Like, it can never be a ‘you’re cool and I’m sexually attracted to you’ thing or a ‘I want sex, not a relationship’ thing. For most of them it seems to be a ‘I want to marry you and have your children’ thing.
Antiquity
wrote on September 27 2009 @ 03:49 pm: [report]
I totally am with the Dr. on this one! I lost my v-car to a great guy but I never told him before hand that I was a virgin. It hurt so bad and I bled allot- he figured it out. Just be honest. If I had a do over- I would have told him. The guy I was with also said he would have been more gentle and done something a little more special. (Although I didn’t want special. I was like the chick that wrote, I just wanted to be rid of it.)
develange
wrote on September 27 2009 @ 03:54 pm: [report]
the first time doesn’t have to hurt. The guy can go slow and use shallow penetration. If you’re freaked out about pain, you can practice with penetration on your own, using a sex toy or some other clean/safe phallic object.
Telling the guy is probably a better idea, so he won’t #&@$% the #&@$% out of you and end up just hurting you and having you associate sex with something negative.
But first time didn’t hurt, but it still sucked. I wished I had waited for another person.
mutam
wrote on September 27 2009 @ 04:16 pm: [report]
I agree that you should tell him! I lost my virginity 10 months ago, one month after my 23 birthday. My boyfriend was 27 and had prior experience. I knew we were getting close to having sex, so one night when things were getting a bit hot and heavy, I told him. Unfortunately he did freak out a little bit. He had a previous girlfriend who said that and it wasn’t true. But I explained the situation, and then he was very nice about it. Yes my first time hurt a bit, we had some trouble actually getting it in, but once we did, things were golden! And the best part was we laughed our way through it! It made it fun and not a serious and stressful thing!!
Just be honest and have fun!
Knitter79
wrote on September 27 2009 @ 07:31 pm: [report]
Great advice! Especially about what may happen after they have sex. My first was a virgin as well, we’d been together for about a year, but had been friends for a few years prior to getting together. I was losing interest in the relationship and we weren’t getting along the way we used to. But I was 23 and out of college and had no idea how to date outside of a school environment. So one night we had sex (or tried since we didn’t know what we were doing). And afterwards it was like ‘I waited all this time for that?’ I know your first time is supposed to be a big deal, but as a friend once described it to me, ‘it’s kind of like poke poke poke and then it’s over’. I didn’t bleed (athletic as a kid so hymen was long gone) and he was small so it didn’t hurt all that much either. We kept at it but after a few months it was obvious the chemistry wasn’t there so I ended things. I certainly don’t regret what happened, and looking back I wonder why I waited so long.
My new guy has only slept with one other woman-his HS/college girlfriend (he’s now 31). When I found out (after we had sex for the first time) I felt a little weird. It made it seem way more meaningful. Not that my list is long by any stretch of the imagination, but I had a couple casual flings. At the time I didn’t know what we were to each other or how things would change. It’s working out great, but I definitely panicked a little about what I perceived to be his lack of experience. He has taught me, though, that the number is no indication of experience level. I’m glad I didn’t know before we slept together, though. Not because we wouldn’t have done it, but I would have taken control instead of letting him run the show.
But I agree she should tell the guy before hand. If he freaks and bolts because he doesn’t want to ‘deflower’ her, then he’s not worth it.
drebella
wrote on September 27 2009 @ 07:59 pm: [report]
ahah. I was 17 and in a relationship for 8 months before we had sex, It really wasn’t a big deal to either of us, it didn’t hurt alot even though he was really big and I didn’t bleed at all. It was however not even good and I don’t think he even finished cause someone walked in on us or something.I was more freaked out to give head for the first time, which strangely enough was the same night…anyways what Im saying is it isn’t a big deal if you dont make it a big deal…but you should definitely tell him!
snap
wrote on September 27 2009 @ 09:30 pm: [report]
i HIGHLY DOUBT that first-time sex will hurt for a 28-year-old. just saying.
txstar
wrote on September 27 2009 @ 09:37 pm: [report]
i’m 23 and still a virgin. i’m not dating anyone and i’m not even close to losing my virginity at the moment, but i have no problem with that. i’m not waiting for marriage or for the perfect time, i’m just waiting for a moment that feels right for me. it could be next month or next year. just as long as i’m 100% positive it’s what i want. i agree with some of the other ladies that it’s only as serious as you make it. tell him. and if he’s weird about it, then he’s not the one, and you can move on. i think being a 20-something virgin these days is also about having a positive attitude. just be honest and open, and things will fall into place.
_jsw_
wrote on September 27 2009 @ 10:20 pm: [report]
Note: jab705 has been reported.
SamL
wrote on September 28 2009 @ 02:41 am: [report]
@amanda2m You sad, sad little man!
Rose
wrote on September 28 2009 @ 03:36 am: [report]
amanda2m has just been reported
majicksand
wrote on September 28 2009 @ 09:33 am: [report]
You really need to tell him. Losing your virginity should be a big deal. It is a gift, a unique gift that you can only give once. I completely wasted mine, and I wish I hadn’t. It did hurt, it wasn’t really fun, and I also thought, much like knitter79, “I waited for this?” I believe the experience would have been a much better one had I been with someone I really cared about, so the emotional end could have compensated for the lack of physical enjoyment.
In good news, it does get better. If you’re with someone you love, it gets MUCH better.
lawyrgrl
wrote on September 28 2009 @ 10:18 am: [report]
**MY APOLOGIES FOR POSTING OFF TOPIC**
Thank you _jsw_ and Rose for reporting the spammers on this thread. The trolls are definitely getting out of hand. May I just take a quick moment to say how much I like this site and thank ALL of you for the wonderful postings? You brighten my day!
MediaExecutive
wrote on September 28 2009 @ 02:15 pm: [report]
Deflowering virgins is the best feeling. He’s a lucky bastard.
C.Munro
wrote on September 28 2009 @ 02:17 pm: [report]
The good doc has got it right on this one. I agree on all points.
When I was about to turn 29, I ended up dating a 20-year-old virgin. We’d started out as friends, and I could tell she was attracted, but like many other guys I was a little intimidated by the v-card. But as we spent more time together, I realized that no matter how innocent her virginity made her appear in my eyes, she didn’t want to be seen as a little sister; she wanted to be seen as a woman. One night, she put the moves on me and we went to bed together.
It wasn’t what would typically be considered “great sex.” Neither of us got off. But never before or since have I experienced such an intensity of affection during sex. Her eagerness, my trepidation, neither of us wanting to hurt or disappoint the other ... it was all very sweet. Even though there weren’t any mind-blowing orgasms involved, it is both one of my favorite sexual encounters and one of my most treasured memories.
It’s true that sex doesn’t keep a relationship together. We broke up about six weeks after our first time. I wasn’t particularly invested in the relationship, partly because I was freaked out by the age difference and partly because she started the relationship by telling me she didn’t want to get too serious. I didn’t realize how great she really was until a couple of days before she dumped me.
We’re still friends, and we keep in touch. I know we have places in our hearts for each other. But I don’t think she knows that I look back at her as the one who got away.
Enough sentimentality. The point I want to get across is that the letter-writer should be honest about her virginity. I shudder to think at how badly things would have turned out in my own late encounter with a virgin had she not told me. Don’t worry about being bad at sex. There are many kinds of good sex, and if you’re into it it’ll be one of them.
Loves2Spooge
wrote on September 28 2009 @ 02:41 pm: [report]
Just know that you ARE going to freak him out. At age 28, he’s going to wonder why it took you this long to take the plunge. Whether you legitimately were waiting for Mr. Right or the stars just never aligned, odds are he is going to be skeptical of your reasoning and feel a modest burden.
That’s just the way it goes senorita, lo siento.
niftynymph
wrote on September 29 2009 @ 12:07 am: [report]
I lost my virginity at 25 to some guy in the back of my car after a party. Romantic, eh? The guy didn’t know it was my first time. I think the fear of telling him and having him freak out kept me silent. I didn’t care for him and by that time in my life, I just wanted to get rid of it. Had circumstances been different—like if I had feelings for him or if we were dating—I would have told him.
But I agree with the others and say she should tell him. Hopefully he doesn’t freak out and leave. But if he sticks around and they get it on, the best thing about getting this weight off her chest is that she won’t be distracted by worrying whether he’ll figure out she’s a virgin.
Faith
wrote on September 29 2009 @ 12:10 am: [report]
My first time was with a guy I didn’t know all that well but was very attracted to. We had a few classes together and hung out with a few of the same people, so we weren’t total strangers or anything. He invited me over one night and we did it…but I told him beforehand I had never before. I don’t regret it one bit; I am definitely the type of person to become attached to someone easily, so I wanted my first time to be with someone I liked as a person, but wasn’t necessarily in love with. But that’s not for everyone. He was a lot more gentle because I told him beforehand; it’s always good to let people know what’s going on. I always thought guys were stoked to get to de-flower virgins. Myth?
adamjs
wrote on September 29 2009 @ 05:25 am: [report]
@ Faith: not entirely a myth - it’s just that the type of guys who would be stoked to de-flower are the same ones who keep notches on their bed posts for bragging rights. I would say that the rest of us would be more cautious about it than anything….
C.Munro
wrote on September 29 2009 @ 12:32 pm: [report]
@Faith: There are a lot of reasons why guys are hesitant to deflower a virgin, some of them sweet, some of them selfish, and some just plain stupid. It could be the protective instinct kicking in, and the resultant feelings of guilt when thinking of her in a sexual context. Or it could be fear of a bad performance, either on his part or hers, combined with a certainty that it will be remembered. A lot of us also have this irrational idea that a virgin will fall hopelessly in love with her first (which may be somewhat true when you’re high-school-age, but rapidly becomes less so the older you get).
I wanted to (and did) lose my own virginity to a fellow virgin, but that was the only time I specifically wanted to have sex with a virgin. I thought it would be nice if my partner and I took each others’ v-cards. But subsequent sexual encounters happened because I wanted to sleep with a girl for who she was, not what she was.
pragmatryst
wrote on September 29 2009 @ 02:54 pm: [report]
I should mention that I’ve done everything else, and have had an orgasm, but I’m afraid that I’ll be bad at sex and won’t know what to do.
I’m sure “everything else” is open to interpretation, but if that includes at the very least kissing, groping, hand jobs, fingering, blow jobs, and oral sex where you’ve had an orgasm then you may be a “virgin” in the technical sense, but you are hardly some naive shrinking violet who has been locked in a castle tower for the last 28 years. I would go as far as to say you actually do know what to do, you just haven’t done it yet. I won’t underplay the whole hymen/pain issue because that could be no big deal or it could be a hot bloody mess, but don’t let that stop you. As other commenters have mentioned, there are ways to reduce that problem on your own before the big night. I was involved in an “everything else” relationship for several months with the girl I eventually “lost” my virginity to and honestly it was a much bigger deal in my mind than it turned out to be in reality, and although I didn’t recognize it at the time, all the extra practice I had in the art of foreplay has been paying dividends ever since.
Saartje
wrote on September 30 2009 @ 10:46 am: [report]
I lost my virginity two months ago, a week after my 24th birthday. I’d met the guy four weeks prior, but went on holiday for two of those weeks. That gave me plenty of time to think about it, and when I got back, I knew I was ready for it. I had been for a long long time, but just didn’t find the right guy to go all the way with. He knew I didn’t have a steady relationship before, but I only told him about being a virgin on the night itself. My first kiss was horrible and he never knew he was the first guy I kissed, so I wanted this first time to be special, with a guy that knew about it. He wasn’t a virgin, but he wasn’t exactly experienced. He reacted surprised but very sweet, that he’d be gentle and he put me at ease. That night, we didn’t succeed because I was too tense, but when we tried again, it went okay. Awkward, it took forever, the condom ripped, it hurt, I had the same ‘I waited for this?!’ feeling, and he had to get up at six the morning after, but we had fun, we laughed about it and now we share an unique story. (IT was playing in the background..) It continued to hurt for a couple of times after as well, but now I really enjoy it and it all feels very natural.
Tell the guy, it will make the experience better and more relaxed for you, because you don’t need to pretend you’re experienced, and you can make something special of it together. No candlelight-and-rosepetals-kind of special, but just something memorable.
agm007
wrote on October 8 2009 @ 10:04 pm: [report]
i’m actually still a virgin and i’m 20. i pretty much had the same concerns as the writer does, except that my boyfriend knows i’m a virgin. and actually, he’s the one that answered alot of my questions about losing it. due to school distance, we have had to wait.. i mean, i’ve already orgasmed on my own, so i’m not too worried about being a bumbling idiot in bed my first time.
but i really think that waiting until you are a bit more mature (as opposed to some people that pop their cherries at 14) will help mentally, and that should help make the experience better physically. because after all my solo experience, i’m no longer scared or nervous to actually lose my v-card anymore.
but to the writer, i think that telling him is the best scenario. my boyfriend was not freaked out at all. if anything, he is supportive of me still being a card carrying member of the V club
TheUnusualSuspect
wrote on October 9 2009 @ 01:21 am: [report]
The doctor is wise. Tell him. Talk about it. Share your insecurities. Find out what he thinks. If you can’t be honest, what’s the point in being in a relationship? Then have fun with it. Work up to it as slowly as you need. Have foreplay for a whole week or six months if that’s what it takes to feel ready. If he’s worth being with, he’ll enjoy the journey!
Fyndy
wrote on October 18 2009 @ 07:36 am: [report]
So true. Or, they’ll use you for a little bit and discard you like a piece of garbage.
I was 20 when I lost my virginity to a much older man that I had met online. We met, the first day he wanted to take me back to his place, but I refused. After a few more meet-ups, I spent most of the night at his place. We had been fooling around, and when he found out I was a virgin, he was surprised and, it seemed, a little disappointed. *shrugs* It wasn’t anything really special, he made me feel like a piece of meat.
The “realationship” ended 6 months later, with me feeling stupid of being used for just sex, but I had learned my lesson.
Tell the truth, and don’t ever apologize for being a virgin. If he’s worth it, he’ll wait for you to be ready!
AL1124
wrote on October 20 2009 @ 11:28 am: [report]
I lost my virginity at 27 to a guy I’d been dating for about 3 months. Like other posters said, I hadn’t been waiting for anything or anyone in particular, it just had never happened. I felt I had waited too long, and I just wanted to do it with someone and move on.
So, I decided to have sex with that guy, and not say anything to him about it being my first time. I just told him that it’d been awhile since I’d dated anyone (true), so I’d need him to go slow. There was some pain, but nothing major. That part was actually fine.
At first, I didn’t feel bad about keeping my virginity a secret, because I honestly didn’t think we would end up in a real relationship. I figured it didn’t matter if he knew or not. Now, we’ve been together for over a year, and I still haven’t found a way to tell him. Maybe he has guessed, based on my questions about sexual positions, etc, but if he has, he hasn’t said anything to me. It feels strange to have this big secret from him but I don’t know how to tell him without doing serious damage to our relationship.
So I guess I agree with Dr.V, but for different reasons. If you want to just “get it over with,” you can have a one-night stand with a guy and your virginity doesn’t have to come up. But with a guy you’re dating and even ‘kind of like’, you should tell the truth. You could end up in a real relationship, and then be forced to have a secret you’d rather not have to keep.
TheUnusualSuspect
wrote on October 20 2009 @ 09:22 pm: [report]
@AL1124
Do you really think it would damage the relationship? Why is that? I think if I were in his shoes, I would be able to laugh about it with my girlfriend, especially after being together for over a year.