The Good
As a sex surrogate and sexplorer, I have a philosophy when it comes to people, places and things: Leave them better than you found them. That is always my goal. When I’m in bed with someone, I want them to feel amazing and very special. Despite my best intentions, however, it doesn’t always work out that way.
Virgin #1 was a 38-year-old man with a dismal track record in the bedroom. He went to bars to “pick up chicks,” but would shut down as soon as he got them home. He’d give them oral sex, all the while sweating bullets as he feared letting them down, which in his mind, he did. He counted on alcohol to cloud the evening, mumbling about “whiskey dick” as he sheepishly showed them the door. Finally, he decided enough was enough, and he sought professional help.
I spent a couple hours talking with him about his issues, which was one key to solving them. Having it all out in the open was a relief to him—it was good to be on the same page instead of hiding his insecurities like porn under the mattress.
We then spent a couple hours in a very open and honest setting—he felt safe and understood by me, which was such a contrast to his past experiences. He was getting to the point where he was feeling like women were adversaries, to be feared.
He had successful intercourse with me for the very first time. He was amazed—it felt so right and spectacular. “I can’t believe I’m doing it!” he kept muttering incredulously in my ear as he pushed awkwardly in and out of me.
The sessions he had with me were a breakthrough with him. He found that women are not scary creatures, and went out into the dating world with newfound confidence.
Virgin #2 was a charming 25-year-old with a perfectly charismatic personality. He was pursuing a career in politics, and wanted to be sure the time he spent with me remained under wraps, as he was very conscious of the potential for future scandals.
#2 had never kissed a girl. I was his first on all fronts—first kiss, first oral, first everything. He was so sweet, I asked him how this came to be, and he told me it was due to lack of opportunity, but that he had his eye on a special girl, and wanted to make sure he would be prepared for courtship.
It’s a good thing he went this route, as he was a terrible kisser. I patiently showed him how to relax his mouth and take his time. He went down on me and remarked, “I’ve always heard a woman tastes like fish, but that’s not true at all! You taste wonderful!” He completely freaked when I put my mouth on his penis, saying, “Okay, I’ve always heard a blowjob feels incredible, and that is absolutely true!” The cutest moment was when he got on top of me and started having sex with me.
“I had NO IDEA how much work sex is!” he huffed and puffed. He used pelvic muscles he never realized he had! It felt so great, TOO great; it took him forever to orgasm. He finally resorted to a more familiar method—masturbation as I quietly lay next to him.
Luckily, he started dating the girl of his dreams a month after our session, and he couldn’t thank me enough for giving him a great head start.
Virgin #1 was a 38-year-old man with a dismal track record in the bedroom. He went to bars to “pick up chicks,” but would shut down as soon as he got them home. He’d give them oral sex, all the while sweating bullets as he feared letting them down, which in his mind, he did. He counted on alcohol to cloud the evening, mumbling about “whiskey dick” as he sheepishly showed them the door. Finally, he decided enough was enough, and he sought professional help.
I spent a couple hours talking with him about his issues, which was one key to solving them. Having it all out in the open was a relief to him—it was good to be on the same page instead of hiding his insecurities like porn under the mattress.
We then spent a couple hours in a very open and honest setting—he felt safe and understood by me, which was such a contrast to his past experiences. He was getting to the point where he was feeling like women were adversaries, to be feared.
He had successful intercourse with me for the very first time. He was amazed—it felt so right and spectacular. “I can’t believe I’m doing it!” he kept muttering incredulously in my ear as he pushed awkwardly in and out of me.
The sessions he had with me were a breakthrough with him. He found that women are not scary creatures, and went out into the dating world with newfound confidence.
Virgin #2 was a charming 25-year-old with a perfectly charismatic personality. He was pursuing a career in politics, and wanted to be sure the time he spent with me remained under wraps, as he was very conscious of the potential for future scandals.
#2 had never kissed a girl. I was his first on all fronts—first kiss, first oral, first everything. He was so sweet, I asked him how this came to be, and he told me it was due to lack of opportunity, but that he had his eye on a special girl, and wanted to make sure he would be prepared for courtship.
It’s a good thing he went this route, as he was a terrible kisser. I patiently showed him how to relax his mouth and take his time. He went down on me and remarked, “I’ve always heard a woman tastes like fish, but that’s not true at all! You taste wonderful!” He completely freaked when I put my mouth on his penis, saying, “Okay, I’ve always heard a blowjob feels incredible, and that is absolutely true!” The cutest moment was when he got on top of me and started having sex with me.
“I had NO IDEA how much work sex is!” he huffed and puffed. He used pelvic muscles he never realized he had! It felt so great, TOO great; it took him forever to orgasm. He finally resorted to a more familiar method—masturbation as I quietly lay next to him.
Luckily, he started dating the girl of his dreams a month after our session, and he couldn’t thank me enough for giving him a great head start.
Taking virginity is a tricky thing, isn't it? I've taken 2 (well, 3, but I didn't find out that the third had been a virgin until 5 years later!). One was great, one was awful. The great one was my first long-term boyfriend, and we were each other's firsts. The second? I was 20, he was 21, and he got way too emotional and attached and it wasn't good.
I find the conversation especially interesting when we talk about taking guys' virginities. People stereotype women as emotional, and as saving it for "someone special," and expect women to get attached. But guys are often stereotyped as just wanted to get laid, when in actuality, sex is emotional for many of them, too. Especially the first time.
I have a friend (27), who is seeing a girl (22) that is a virgin. He doesn't want to get serious with her, but wants to sleep with her. I've tried to explain that, in most cases, there's gonna be an attachment to the person you lose your virginity to. You've never done those things with someone before, so it's going to feel more intimate and create feelings you've never felt. For men AND women, yet we often forget that.
Great comment! I had a tagline to this piece that didn't make the cut:
"I didn't TAKE their virginity. I gifted them with ME."
Very interesting. I myself have never been with unexperienced men. Well in theory, I have not, but in practice, they really needed to learn a few handy skills.
Love the tagline.
I took my husband's virginity and he took mine. We have been married 7 years and have never been with anyone else. Men are just as needy as women even though they deny it.
What a fascinating minefield. So much responsibility.... I don't believe I've ever taken anyone's virginity (and in sorting through the ashes of lovers past, so to speak, I do think I'd have been privy had that been the case), though I have been thanked after the fact for giving two their first "taste" of another high-value sex act, along with proper instruction that I was told served them very well with subsequent partners. Leave them better than you found them, indeed. Really interesting post.
I don't know, TBK, I'd call the ones you file under "bad" experiences good experiences, too. A man who comes to you for these reasons does so because he's got a lot to learn. Learning to separate is one of those lessons. They may sting for awhile, and I'm sure it's hard for you, in its way, to have to hold the line, but if they're open to learning it, it's a great lesson they've just been taught.
I avoid virgins at this point, and being a guy's second is almost as bad (or worse, if his first was an insensitive nymphomaniac bitch) as being his first. I am not quite patient enough (it's a lot of responsibility to be someone's first, regardless of age or sex or gender), and I don't like hurting people, so now when a virgin comes my way, I run in the other direction, for his own good. I will, however, take a non-virgin male's anal virginity any day of the week (I have taken three or four now). Peculiarly, that one is not hard to handle at all. I can spot a guy who will be into it pretty easily, and I know how to ease his worries about the subject, shockingly, without having to let him put anything in my butt in exchange. Every man whose anal virginity I have taken has walked away fundamentally changed for the better, although one seemed to have become addicted, which I suppose could be troublesome.
On the flipside, it can be tricky to be an older virgin who want to lose one's virginity when your potential partners freak out and bail before hand, expecting that you will be clingy afterward. I lost my virginity at age 31 and he freaked out, worried that I would be clingy, and bailed afterward. I had no intention to be clingy. I was pretty grounded in my life at the time and was not looking for some attachment to complete me. I was not in love with him and he did not seem more alluring or interesting afterward. I was looking for someone fun to date and sleep with. Simple. He made it complicated. I was over it quickly and moved on. As Kendra's post shows, there is diversity amongst virgins and how they react. Not all will be too emotional and attached.
Madshnoodles, what signs indicate a guy would enjoy pegging? Inquiring minds want to know.
I'd love for one of you women to have taken my virginity.
I have a fantasy of taking a Christian woman's virginity.
I fantasize about the look on her eyes as she prepares to give her Christian innocence to me.
“I’ll be gentle,” I tell her. “I promise.”
"But... but... I... I'm... I'm a Christian girl. I don't sleep with the guys I date..." she lightly protests. As she tells him this, they kissed even more passionately. She didn't object nor try to stop him as he caressed her breasts and moved his hands down to her panties, where his fingers entered her pussy, which he discovered to be very wet.
"I know you're this strong Christian girl," he tells her. "But, Christian women sleep with the men they date all the time. It won't hurt that much, and I will go in very gently. You can go on being this 'good Christian girl,' even as you give yourself to me throughout the night. I love you and so want you..."
As he said all those sweet things to him, reassuring his Christian girlfriend this would be for the best, the Christian woman trusts him.
What could it hurt?, she thought. She figured she could try it once, sleep with him just this one time. "No one would know."
It wouldn't be that bad. She could still be this "good Christian girl," even as she enjoyed the pleasures of sex with him once in a while (or often).
What she didn't expect was how good it would feel. After she gave him her Christian virginity, letting HIM -- this nonChristian man she was seeing instead of the Christian man she may later marry -- be her first, she would long for him and want him to make love with her even more.
Many a morning after their dates, she would wake up alongside him, holding him, kissing him, caressing his godless nonChristian cock which she craved in him. She'd even climb on top of him and guide his manhood into her. She wanted to feel his passionate thrusts deep into her good Christian girl pussy before work. Those impromptu times, she wouldn't make him wear a condom. As a Christian girl, there was nothing to protect her pussy from his potent sperm-laden cum, which she loved conquering her. She always loved the feeling of his cum splashing against her pussy walls, almost as much as she loved sucking it from him and swallowing.
In those intimate moments in the early morning light, as they kissed and caressed each other, she, the Christian girl, wouldn't think about her God, her faith or moral convictions, which she so easily put aside to enjoy the moments of pleasure he would give her. He lasted very long and wouldn't cum quickly, another manly trait about him which she loved. Her Christian girlfriends often told her how their dates would often cum quickly once inside them. She knew what she wanted and was thankful he knew a lot about sex and was willing to be "taught" by him.
It's true that when she felt his penis spasming and knew he was about to explode his cum deep into her pussy, she did, on occasion, think about her faith and her devotion to God. These thoughts enter the minds of many Christian women in such intimate moments where they become emotionally closer to their men, the closest they've ever been to anyone. As they enjoy the feelings of their men's penises pushing in and out of them and fucking their pussies hard, showing them what real life is about, such heavenly thoughts don't linger for long. The Christian women will hold their men even more tightly and kiss them even more passionately as they take-in their men's impressive cocks, which sink even more deeply into their good-girl pussies, which so want to be fucked.
"Oh... oh.... go deeper... deeper.... Yes... ummmm... that's the spot you always go to... I love you..." the Christian woman will tell her man. As she climbs on top of him and takes his mighty penis in her hand, guiding it into her "innocent" pussy, as she moves her body up and down on it, shaking it wildly to the wonderful sensations his manhood provides her, she has no thoughts of her Christian stance, her wanting to "wait" until marriage or her moral convictions. All she wants is to be fucked over and over throughout the night. After he cums, his Christian girlfriend will go down on him and suck him until she brings him back, so they can make love even more. "God, I want you..." she tells him as she brings his flaccid penis back to life. "Don't wear a condom. I want to feel ALL OF YOU in me..."
I would love to try this. i have never been with a woman, as i am very socially awkward. Any time I've gotten close, I've chickened out mostly due to fear of the unknown, and the fear that she will hate it. Anytime I've tried to push past this, i find myself making excuses and backing out. Every sing time. I just want to find someone that can help me over this hump and help me get over my fears. someone to teach me and show me what it's like so i am no longer afraid.
@coltonthevirgin, I wouldn't get too worried about it. Next time you're in an intimate situation with a woman, say you're holding and kissing each other (with you clothes on) on the couch, as you kiss her, start approaching her sexually slowly. Begin to (lightly) caress her breasts from outside her shirt. Take things slow, not too fast, so as to not scare her. Try to be subtle. This is especially important if she's a virgin or hasn't had much sexual experience.
Then move onto to deeper things, by unbuttoning her top (she may help you remove her shirt), to gain access to her breasts, which you can caress, feel-up and kiss and suck on. After a period of pleasing her via her breasts, as you continue kissing her nipples and lips, move your hand to her pants, moving your fingers into her pants and into her panties. Start by caressing her vagina from the outside of her panties, feel her folds and form. If no resistance, move your fingers into her panties and begin caressing her that way. You can judge her excitement (and interest) by how wet she feels. Perhaps she's fantasizing about you entering her with your manhood.
As you kiss and finger her, she may help you remove her panties, exposing her womanhood in all its beauty to you. She may notice the bulge in your pants, so unbutton your jeans and let her caress you.
Tell her you've never met a girl like her and how you want her. As a woman, her instinct may be to please you, so she may be accommodating and "expect" you to take the lead, be the man and seduce her.
Climb onto her and position your manhood in front of her opening. Go in gently but be resolute and deliberate.
You may wish to put on a condom, to protect her innocence from conceiving a child and to protect each of you from the long-term consequences of your actions made during the heights of passion. If she's on birth control pills, it may be okay to enter her without protection. The feelings and sensations for both of you will be better sans rubber.
I, too, was once shy and not purposeful in my interactions with women. I would be happy to give you more advice, if interested.
Forgot to add... if during your advances, she tells you "maybe next time" when you prepare to penetrate her, don't be upset. You will have time on your next date. Try not to rush things, as rushing never helps matters and puts pressure on the other.