First time, first boyfriend (m/f) “So at 21 years of age with...

First time, first boyfriend (m/f)

“So at 21 years of age with no experience in any aspects of relationships, I was beginning to think maybe I wasn’t cut out for them at all. None of the guys I fancied (or girls, for that matter) were ever into me, and those who were into me, I did not like at all. I was okay with that, if a bit lonely… and then he came along.

We met in a college class and from the get-go he was funny, smart, and geeky like me, so we hit it off just fine. I wasn’t interested in him as anything more than a friend at first, but he asked me out on several fun dates and slowly but surely made his way to my heart. We became official, and he was very patient with me learning how not to be all by myself.

Now he’s a bit older than me so he has more experience, whereas I was still a virgin when I met him. Also, with barely a month of relationship, I thought maybe we ought to take things slow. But he’s so open and honest and kind that he earned my trust, and we started talking about sex themes, what we liked and didn’t like and all that. And we’d been progressing from hand-holding and pecks on the lips to deeper kisses to making out in his car before he took me home from college. He was always very nice about it, asking for permission before doing anything and asking me if I was comfortable and okay with things.

One day, we’d gotten particularly hot and heavy, which led to him rubbing me out through my jeans and me giving him a handjob in his car, but we kept getting interrupted by nosy neighbors, so we were both left wanting much, much more.

So next day, he asks me if I want to go to his house (his mom and sister were both away on a trip so we had the place to ourselves) and keep going where we’d left off. I said yes, and we went up to his room. We got on the bed and made out for a while, him touching my boobs over my shirt and me palming him over his jeans. He asked if he could undo my bra, and I wanted to surprise him (and also I needed to feel his hands on me) so I went one up and took off both shirt and bra. He was surprised, to say the least, but in the good way, and we kept making out, with the added bonus that he could now lick and tease my nipples. I’ve never been much of a boob girl but gosh is his mouth talented!

He then asked if he could take off my jeans, and I said yes as long as he took off his jeans too. He took off jeans and shirt and even his boxers. So there we were, naked, making out and just touching everywhere. Then his hand hovers near my pussy, and he asks “May I?“

I’m breathless by this point so I just nod and he starts caressing me ever so gently. I’d never been touched there before by any hands that weren’t mine, and it felt really, really good. He takes off my panties to keep caressing me, this time with nothing between his hand and my pussy. He keeps at it for some time, then his finger hovers above my entrance, and he once again asks if I’m ok with it. I nod, and he slowly slid in his finger. He has very thick, strong hands, but he’s also used to handling delicate objects because of his work, so needless to say he has a magic touch. He starts fucking me with his finger, slow and deliberate, and it felt wonderful. I’ve also never been much for penetration while masturbating, but it felt very different having someone else do it.

Then he gets this look in his eye, and he pulls out a packet of condoms. We’d talked before about safe oral sex, so I had a pretty good idea of what he wanted to do, and I was so on board for it because I’d always wondered what it felt to have someone go down on me. He preps the condom and asks me to hold it, and then he goes to town.

Boy, is he talented! I think probably all his neighbors heard me, because he told me not to hold back on the sounds, and I am, I’ve discovered, quite the noisy girl when it comes to sex. And he’s there, kissing the inside of my legs and licking my pussy and tongue-fucking me; even through the condom, it was intensely pleasurable and I must’ve come several times (not that I was counting!).

Not to be left behind, after he takes a breather, I ask him to put a condom on himself because I want to go down on him. He does and, well, even with no practice, I had a bit of theoretical knowledge on blowjobs (bless this site and porn and also fanfic), so I just tried to make it good for him. I could hear him above me, breathing heavily and grunting as I licked and sucked. I found out that he really likes having his balls suckled, and when I pull the skin down as far as it will go. So again, I work on him and even through the latex of the condom I could feel his warmth. He pulls me up for kisses, and I begin to have a feeling, a need of something more.

“What are you thinking?” he asks me, his voice a harsh whisper.

“I want us to do it,” I answer, and I am feeling a bit nervous but I’m also so certain that this is what I want. “Just please be gentle and go slow?”

“Tell you what,” he says. “You go on top, and that way you can control it, yes?”

He changes the condom and lies back, and I feel a bit awkward as I kneel on top of him. He helps me guide his cock into my entrance, and I lower myself slowly.

It didn’t quite hurt, even if he is a bit thicker than average, but it was a peculiar sensation. He asks me if I’m okay (“I am, just gets a bit of getting used to”) and then he starts moving. And that’s when I go wild, because I never imagined something could feel so good. He keeps it slow at first but then changes the pace to something faster, and I try to match his thrusts while I ride him. Again, I think his neighbors probably heard us, hehe. Then I lean forward to kiss him, and he starts making his thrusts deep and hard, and he smiles when I moan into his mouth. After a while, I get another idea.

“Could we maybe…” I start. “I’ve always been turned on by the doggy style position…”

He nods and we change positions, and I’m feeling surprised at myself because I’m wiggling my ass at him as I get into place, ass in the air, elbows on the bed. He enters me again and it feels good. Then, his hand is on my back.

“Curve your back downwards,” he tells me. I do, and holy moly have I found my favorite position! I was in ecstasy, moaning like crazy as he hit my G-spot over and over again. He keeps changing the pace, from fast and pumping to deep hard thrusts that I really, really loved. But by then I’m getting a bit tired, and he notices, so he asks if I need a break.

We lie down, he takes off the condom and touches me again, and I start jerking him off. Thing is, and lucky me, he has wonderful stamina and very good control over when he wants to come. So he asks me “want me to finish myself off?”

I nod and he takes himself in hand, me watching and lying next to him, and when he does come, it is all over my hip and the side of my abdomen. We lay there, spent and content, and then we get up to clean ourselves up in his shower. My legs were so shaky I could barely walk!

The great thing was, as we showered together, I could feel that we hadn’t just had sex, we’d made love and were still doing it. He was very caring of me afterwards, kept telling me how good it had been and asking me if I was ok or if I needed anything.

I’m really really happy that my first time really was something so special and that it was with someone I can trust, someone I love so much. Only problem was, now I can’t get enough!”