ANSWERS: 1
  • Hmm thought I already answered this question. They are both great but I can't help feeling that had I learned to enjoy anal when I was younger I could have developed so I liked that better. Vaginal is more natural, the other requires more preparation so is only for certain situations or with certain people who know what they are doing.
    • dorat
      You did. When I was just starting with this site I assumed that putting something under its subcategory placed it under its general category. When I found that was not the case, I posted a couple of questions twice in order to get a larger number of responses. (Which didn't happen anyhow.) Thanks for answering.
    • WorldOpenSkies2222
      Hi, dorat. Just to let you know, this message is NOT related to the question above. Lol I apologize I have not been online recently, it's just that my life's been very busy lately, especially with Jasmine. :) To update you, she and I have been getting extremely close and we both spent an afternoon together a few days ago and we admitted our (deeper) feelings towards each other, and she actually asked me if we could have sex soon. (Which I find kinda unusual, as it is usually guys who do that, or am I mistaken?) Anyway I told her that I would think about it and she said she will, too. (She was blushing heavily the whole time.) We have done many things together, such as hanging out on a small bridge by a creek, sitting underneath a tree in the middle of a field and sharing stories and secrets with each other, and we've been to a few movies and a few "short" dates. (About an hour or so.) I've got a super big crush on her and she said she does to (towards me). :) As for me, I'm really enjoying the masturbating and I'm having no more concerns or issues or worries anymore. I've set up a regular "schedule" for when I do it: once when I wake up, once in the afternoon if I can get some time alone, and once before bed; plus I do it for about 40 minutes each (either in my bed or in the shower), and I've had some incredible orgasms... and sometimes I've been able to do multiples! So, yeah, I've grown to love my body a lot, and, sorry to tell you this if it "weirds you out", but I'm masturbating at the moment (well, I'm taking a break), and I've been able to have 2 orgasms so far (plus I've cummed lots). It's incredible... I'm probably going to start rubbing my dick in a second.... Anyway, hope you and your girlfriend are doing well, and I can't wait for a reply!
    • dorat
      Congrats pal. I am really glad to hear it. I had a feeling that when you had dropped off the radar that maybe your life was getting a bit busier. It is really great news. Oh, and yes, Jasmine certainly sounds like she knows what she wants. If it helps, when I first met my gf I had been through a rough patch and she was more interested in having sex than I was. She told me later she started to wonder if we were ever going to have sex. I will say this, though, when we did it was one of the most moving experiences I had ever had. I am going to sound like an oldster - which I am - here, but I want throw in just one thing. You one time wrote that you didn't want to have sex unless it was with someone special - that casual sex is not your thing. That's great. I won't kid you - I was 16 (almost 17) when I had sex for the first time. I got lucky in the sense that it was at a time and place where we had lots of time and there was little chance that it would be interrupted. Just so you know, for most people, first time sex is awkward and rushed and a little disappointing, in part because of inexperience and in part because it is rushed and there is a worry of being interrupted. So if you do decide to have sex, make sure that you have time and privacy and just take your time. Your every instinct is going to tell you to rush because when you masturbate you are rubbing fast because you are after an orgasm. (This is where masturbation is not helping you. You are learning what makes you feel good - and are getting the wrong impression of what makes a woman feel good.) Women are built different - as you may have noticed - and so speed is what you DON'T want. The other thing - it almost goes without saying - is make sure you use a condom. With my gf, we had not planned to have sex and so we had no protection. For a couple of days after we were sure we were in love - we dated for two more years and then it fell apart - and I was sure that I was the studliest high school guy in history. Then it hit us - hey, what if I got her pregnant? Duh! Then we spent the next few weeks with me asking my gf every day whether or not she had her period yet. Luckily she didn't get pregnant, but as you can imagine, that strained our relationship for a while. I was 16 almost 17, you are 14 almost 15. Sorry, again, I don't want to sound like an old man, but just be sure that this is what you want. (How will you feel afterward, too? I had one friend who was raised in a fairly religious family and he felt hugely guilty afterward. Kind of spoiled the mood.) Anyhow, enough of the advice column. One thing I will tell you, if you guys are getting serious, the feeling you will have of her laying next to you naked will be like nothing you have ever felt. You enjoy masturbating? Once you've had sex with someone you care about, masturbating will seem like a second best. (By the way, it does not weird me out to hear that you are masturbating - I was 15 once too - but I sure don't see how you can masturbate and type at the same time. You are more talented than I am, that's for sure.) In the meantime, it sounds like you two are having a great time. (Now at the risk of sounding like your mother, though, make sure you are getting your schoolwork done. I joke a little - but if this is real between you two, you are going to want to be a better man, not the guy who drops everything else in your life. Trust me, she is going to want to see that you are an achiever and - if it comes to that way down the road - a good provider. Show her that you can walk and chew gum at the same time.) On my side, my gf and I are doing great. She has been a stay at home mommy since our first son was born, but she got a freelance project from her old employer that she will - starting next week - be able to work on from home. However, for the first few weeks she had to go into the office every day, so I have been playing Mr. Mom and taking a little extra time off
    • dorat
      However, given that I work in Congress and that things are starting to get busy - as you may have noticed if you watch the news at all - I think my Boss is probably ready to have his full time staffer back full time. Suffice to say that the work put a little crimp in our sex life, but this Saturday night we made up for lost time. It was great. We got the kids to bed and then mommy and daddy got to be gf and bf for a while. (One thing my gf does that drives me crazy is lick my balls. I love it - and after not having had it for a week it almost paralyzed me. All I could do is lay there and moan.) Anyhow, suffice to say, I had a good weekend. Soon Valentine's Day is coming up - make sure you do something special for Jasmine - which is also our "anniversary." So we leave the kids with grandma and grandpa and have an extended grown-up weekend (which includes sex if you were wondering) either in the city - we live in the burbs - or on the Chesapeake Bay. So that's the next big thing for us. Anyhow, pal, I better take off. I was only up now because I thought I heard one of the kids so I got up to check on them. (Dads do that, you may recall from your own boyhood.) All are asleep, but honestly, all this sex talk has given me a hard on. I could wake up the gf for some fun, but as she has to go to work in the morning I think it better to let her sleep. Soooooo... I am going to take a page from your book and go masturbate. (See? Who said I can't learn a few things from you?) Great to hear from you pal. Feel free to keep me posted but as this is your personal business, don't feel obligated either. Have to admit, these letters by public website are different - but always great to hear from you. Best of luck.
    • WorldOpenSkies2222
      Thank you very much for your advice. :) Well, we did it... I... I don't know how to describe it. It was... incredible, to say the least. My parents were out for the night (leaving my cousin in charge, who left shortly after anyway... we're not very close), and I invited Jasmine over so she could sleep the night. She seemed more than enthusiastic over the idea, and before long she was at the front door. I felt my heart flutter and I wanted her so badly, but I restrained myself... for the time being. She and I sat down on my bed in my room and shared secrets and stories, like we do every so often. Somewhere in the conversation she asked if I had ever had sex, and I admitted that I had not. She then admitted that she had once had sex with another girl, and she asked me not to judge her for her being bisexual. Of course I told her the truth and reassured her that I don't judge, and that I actually find it kinda hot. She then blushed heavily and kissed me on my lips, and after we kissed I kissed her again, and she climbed on top of me and began kissing me. My eyes were open for only a second, but I got a brief glance of her breasts as she bent down and climbed on top of me. (She was wearing a light blue shirt - with no bra, and pj bottoms.) We continued kissing each other for a while, and she then said it was getting hot in [my room] and she asked if I could help her take off her shirt... and of course, I did. Omg her breasts are so hot... They're a C-cup, and they are perfectly shaped, and they were super soft, omg... She let me feel them, and later on she even let me suck on them... Turns out she can lick and suck on her own boobs too, which is really hot. Anyway we did many things to each other, such as her rubbing and stroking my penis, fondling with each other's butts and her breasts (we both did this), and I later on got on my condom and we had sexual intercourse (we were snuggling up side-by-side at this point)... We continued to make love for over an hour after that before we fell asleep... Honest to God, it was the most memorable experience of my life... and her body is so beautiful... Also, she was apparently breastfed until she was 12, which was longer than I was! What are the chances? Plus... she knows a friend's cousin who, well, regularly breastfeeds her (and has been doing so for a few months), and she said she could introduce me to her and we both could enjoy the experience together... Of course I, um... said yes. Why wouldn't I? And you're right, by the way. Masturbating is second best. Like, I'm masturbating right now (I'm actually edging, so when I'm about to orgasm I take my hands off my dick and, well, now I'm typing, obviously), and it doesn't compare to having sex with Jasmine... It's still amazing, but not the same. Anyway, I have to go, I'm about to orgasm, but thank you so much!
    • dorat
      Well, I guess that settles that! I'm happy for you, pal. (By the way, how do you know she is specifically a "C" cup? Did you ask?) Seems like she knew what she wanted all along - and is a bit more experienced than you to boot. Not bad for your first time. Be happy together, buddy. Just - again at the risk of sounding like your mother - don't get in over your head. Now you are talking threesomes. Not bad for 15 - I was in my 20s before I had my first threesome. However, you were the one who said you only wanted to have sex with someone special. You are 15, you're horny, you just had sex with your gf for the first time. So now you are off to the races and what boy wouldn't want more sex? Don't get mad at me, though, but maybe you should learn to be happy with your gf first. She clearly enjoys sex, so that's good, but she is more experienced and may be more ready to handle all the emotions than you are. I know, I know, I'm a killjoy. I just think that you seem to be going from 0 to 70 in no time and you could get hurt. You are both young, and I would hate to see either of you get hurt. It can be hard to imagine, but from here on your feelings are going to be all over the place - especially seeing that you went from wanting sex with "someone special" to sex with anyone who wants it. Be careful. Anyhow, that's it for my mothering. (Other than to add a "be careful" to keep your condoms handy. I got lucky that I didn't get my gf pregnant at age 16. Truth in advertising. Later in my life - my 30s - I got into a relationship with a woman and got her pregnant. I wanted to keep the baby and at first she agreed and then had an abortion. That baby that I never knew still haunts me to this day. You are 15 and while there will be nothing like the day the girl you love puts a squawking little life into your arms and you'll swell with pride and love - I've done it three times now - you have a long, long way to go before you are ready for that.) Anyhow, enjoy that orgasm buddy. Stay in touch if you like and keep me posted.
    • WorldOpenSkies2222
      Thank you for the warnings, I'll definitely take them into consideration. And I'm sorry about the baby... Also I had a really good orgasm, and I'm now considering masturbating just one more time because I can't sleep and I still have a boner. And I know she has a C-cup because, as you guessed it, she told me. :P Truth be told, I wish I was sucking on them and feeling them right now. :P I wish I was with her... *Begins rubbing my dick*
    • WorldOpenSkies2222
      And yeah, I'm really horny, in case you couldn't tell. Lol :P
    • dorat
      Right there with ya pal. My gf and I had sex tonight. She has been busy with a new freelance job and so we have been doing it a little less than normal. Tonight, though, I just couldn't take it anymore. Luckily my gf is kind of old fashioned, for lack of a better term, and she believes that she should be available for sex when I need it. I love her so I try not to abuse that, but tonight I just could not control myself. We got the munchkins to bed and then I just made my move, so to speak. It felt so good. I love her so much. Anyhow, I confess I am still a bit horny tonight, too, and I have quite the hard on, but she has to go to work in the morning so I'll behave myself. We have a party to go to this weekend, so maybe she and I will come home and extend the party. Anyhow, more sympathetic I could not be. Thanks, also pal, about your kind words. I tell you though, one of the happiest days of my life was the day I came home from work and my gf told me she was expecting our first. (Our first two were unplanned. The third was planned.) By the way, you still have something to look forward to. The first time you can have sex without a condom, you'll KNOW the difference. Believe me. Take care, buddy.
    • dorat
      Quick P.S. Buddy, I hope I was not too much of a buzzkill. Here you are all happy about having sex for the first time with a girl you really like and I come out sounding like a cross between your mother and a Public Service Announcement from the Health Department. Sorry. I just know because I have been there, If you are anything like me, right now all you can do is think about her, and you want to be with her and feeling her naked next to you, and you are walking on clouds and then you masturbate and think about her some more. You think you are in love while part of you is thinking that you can't be because you are so young - and then you think again and decide, what the heck, you ARE in love. Then there is another part of you who has just decided that you finally attained your manhood - finally - and are probably a stud, ready for breeding, to boot. You are no longer a boy. You're a man!!! Been there, done that. Though since you were bright enough to use a condom you are probably not worrying about whether you got Jasmine pregnant, the way I was worrying with my gf. Anyhow, I am really happy for you. I just am a bit protective I guess - I am a dad after all, even if I am not your dad. (Details, details.) She is more experienced than you and this is all new to you. So, no warnings. Just take it slow. Okay?

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