I moved away from my hometown right after I graduated and hadn’t been back in a while. I missed my friends there so I took a weekend off from work and decided to go visit. I was excited to see everyone, especially one person in particular. I won’t give a name, nor pretend to make one up, since it would be easier for me to just refer to him in third person.
We dated about two years ago and remained close friends even after breaking up. We flirted constantly even though we both dated other people. My senior year I gave subtle hints that I still had strong feelings for him, though he’d been dating someone for a while now. He caught on, I think, to the hints but it didn’t go anywhere. He wasn’t happy with his girl and was very vocal about it, and I can’t deny that I, slightly ashamed, thought about breaking them up.
Back to the present, he’s still with his girl and still vocal about being unhappy. In fact, I’m pretty sure she knows it. We’ve talked occasionally since I moved, more frequently since I told him I’m going to visit. He’s made several not-so-subtle hints about us hanging out for awhile. So, of course, the smart thing to do is to prepare myself just in case. I take extra care while shaving and pack my best underwear set, ‘cause really, I don’t own a real lingerie set, but I’m working on it.
So I visit my friends and I see him for the first time since I moved. He looks good. He got taller, which compared to me doesn’t say much since I’m 5’2. He looks just as handsome as before, maybe more. We exchange hellos, but then we just hug for a good minute, slightly rocking back and forth, which is what he normally does when he hugs. We don’t get to say much else and I only see him once more that day, but we make plans to hang out the next morning.
First off, I am nervous. We have a basic non-verbal agreement of what will happen. I’m prepared for it. I’ve thought about it a lot before even making real plans to see him. I am mentally and physically prepared for it. I am extremely nervous, though. It doesn’t help that, never having been to his house before, I get lost. I suck at directions, and he gives crappy ones. After twenty minutes, I finally get there. I go inside and we go to his bedroom. I don’t say much and neither does he. He finishes playing a video game for awhile while I tease him about how bad he is. I lay down on my back while he puts on a movie and turns off the lights.
At this point I am beyond nervous. Nothing happens for a little bit. He is lying on his stomach next to me. Then he turns on his side and looks at me. We talk, bantering back and forth, which is what we do most of the time. He leans in and we kiss. It’s a familiar kiss, full of memories and sweetness. He moves slightly on top of me, still kissing, then rolls so I am on top of him. For me, this is awkward. First, he is skinnier than me (not saying I’m fat but I’m no model, and have full curves), second, me being shorter, to get my waist even with is, it makes his face right between my breasts. He says he’s comfortable, but it’s not for me. We kiss for awhile with some grinding, then I roll so he is back on top of me.
More kissing. He sits up and pulls me up so that my legs are wrapped around his waist. Again, more kissing. He takes off my shirt and bra and happily sucks on each nipple. Honestly, this does nothing for me. Yes I’m turned on at the time, but again, it’s just slightly awkward. I kiss his neck as he pulls away and takes off his shirt. I press my bare flesh to his and we grind.
He then leans me back and takes off my pants and underwear. He kisses me as his hand finds my wet pussy. He then fingers me and licks me. Now, he is not a virgin, but he has never eaten someone out before. I guess his previous girlfriends didn’t care for foreplay. It wasn’t bad for his first time and I, only having it done once before, am not in a place to really judge anyway.
He takes off his pants and his boxers. We are both completely naked. This is my first time seeing a dick in person; therefore it is also my first time giving a blow job. I basically just try to do what I’ve seen on porn. It’s not as bad as I thought it would be (although I do end up gagging since he’s pretty big) and he seems to enjoy it. He groans so I take it as a good sign.
When I pull away from him, he lays me on the bed and puts a condom on. To me this is entertaining because he gets shy and tells me not to look. It makes me feel better to know he’s just as nervous as I am. He gets on top of me and asks if I’m sure. Too nervous to speak I nod. He slowly slides his dick into my virgin pussy. I won’t lie, it hurts. I have masturbated with a brush handle a few times before, but that doesn’t prepare me for the real thing. And he’s not even completely in! He gently thrusts in and out a little and I can’t help but whimper. He apologizes and asks if it hurts too much. I say no and he tells me he is going to push all the way in. I feel a hot pain in my pussy.
He gently continues to thrust in and out and the pain dies to discomfort. And then it hits: pleasure. A moan escapes me as his thrusts get harder. He moves my legs so that they wrap around his waist. He groans as he pushes deeper inside of me. I feel like I’m losing my breath and I start to pant as I moan. He stops so he can pull out as he cums. (I asked him to as a precaution.)
He lays on his back and puts me on top of him in the cowgirl position. I immediately don’t like it. To me it’s awkward and his dick isn’t inside me enough. We switch positions again so he is on top and thrusting hard. My hands explore his back, pulling him closer and holding him there.
I alternate between panting and kissing him. His kisses are as deep as his thrusts. It feels so good, so warm. He pulls out again as he cums and I move off of him to lay beside him. It takes awhile to get my breath back. I turn to look at him.
We both just stare at the other for awhile in a comfortable silence. We then lay together and talk for an hour about absolutely nothing.
I enjoyed my first time with him and hope there will be more to come.
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This story is completely true, full of awkward moments and some not always erotic ones. But it is sweet (in my opinion) and hey, not everybody’s first time is a perfect haze of lust right? (As a side note, we were both 18 and 19 at the time.)