Other Matt… again
Last night, a friend of mine, also named Matt (but different from the one in my last post) visited me from Boston and spent the night with me.
When I was 18, I lost my virginity to Matt - on my parents’ bed. It was a senior summer party, my parents were gone for the week. I never had feelings for him, but always thought he was cute. We wound up drunk, in bed together, and he started talking about how hard he was. I decided to feel for myself. I sucked him off and fucked him - he got on top of me and started riding my dick. Before long, I came while inside him. It was pretty short, it wasn’t very romantic, and we never really talked about it after.
Matt actually spent New Year’s Eve with me this year - I was pretty convinced something would happen, especially since when we got in bed we were watching porn together, but nothing ended up happening. This time, not so much.
He’s a pretty sexual person by nature. He’s my age, half-black, maybe 5’9”, cute, fit, and very outspoken (this last one is a new development). My roommate was in bed with her beau when Matt and I decided it was bedtime. We started it by talking - for quite a while, and about a lot of things. He and his “boyfriend” “broke up” hours before - they’re in an open relationship (and have known eachother for about a month), and his boyfriend called drunk to tell Matt he was pursuing someone else earlier in the evening. He was kind of upset about it, but still a little indifferent in some regards. I think maybe more embarrassed and helpless than anything else.
All the while, his leg would rest against mine. Occasionally, he’d push it. We were talking about sex a lot. He bit my arm at some point. He scratched my back for a second. “Want to give me a massage?” “I mean, if you want one.” I lay on my stomach, and he straddled my ass to give me a massage. He was teasing me. “What are you thinking about” “Nothing.” “Hmm…” I felt his hard dick on the small of my back. “What are you thinking about?” I took a minute as he pushed his thumbs into my shoulder. “I’m thinking about what’s going on down by my ass.” After a while, he got off. He asked me for his massage. I got on top of him and worked my magic hands. Unlike him, I wasn’t afraid to go for the ass. Let’s face it - whether it’s by some creepy old masseuse or your boyfriend, getting your ass rubbed down is one of the more pleasurable aspects of a massage.
After I finished, I laid back down next to him. We were wrestling a bit. I could tell he wanted it, and then he confirmed it. “I’m writing a book about how I hate being the guy to make the first move. Do you think you’d read it?”
I gave it a minute. His body was facing away from me. I moved my hips to his ass and grinded my dick, hard under my shorts, against his ass. He pushed back. I repeated. I started rubbing my hand across his stomach, going a little lower each time. Eventually, the back of my hand rubbed against his dick. It’s pretty long, girthy, and quite hard at this point. Yum. Eventually, I slowly ran my pointer finger up and down the length of it. He moaned.
I grabbed his dick through his shorts and slowly jerked up and down. His groans got louder, and I slipped my hand underneath his boxers while kissing his neck and gently pulling at his hair. He liked that a lot and moaned - probably too loud. I have thin walls, and Matt has little awareness of how loud he can be.
I pulled his hair so that he’d crane his neck, bringing his lips closer to mine. We kissed deeply as I continued rubbing his seriously hard cock. After some time, I got up on my knees and licked the head of his dick, him moaning all the while. I took his head inside my mouth, and slowly worked my way down his shaft. When my mouth sufficiently lubed him up, I tried to deep throat him, but couldn’t quite get it all down my throat. He grabbed my pillow and shoved it into his mouth so he didn’t outright scream. I continued to suck and jerk him off for ten minutes or so until he said he was going to cum. He told me to stop, he didn’t want to cum.
I was confused. I didn’t really get why. I teased him, and went back to his cock, gently licking in circles around the head, but he again told me to stop. It seemed like it pained him to say that, but I think he was feeling guilty.
Later when we were laying down, talking again, he sort of brought it up. He said he felt trashy, cumming in my mouth. Not that it was a trashy thing to do, but that it was embarrassing for me. I guess he felt it was immasculating to swallow another guy’s essence. I asked him why he thought I would judge him, and he tried to verbally work his way out of that.
It was a pretty bizarre night. He didn’t get me off - besides grinding his ass into my pelvis a thousand time, whether from in front of me, while mounting me, or asking me to fuck him. I told him I wouldn’t - that I didn’t want to top him, and he’s too girthy for me to bottom. Both of which are true - he is, and I didn’t. When he fell asleep, I went into the bathroom and jerked myself off. We didn’t talk about it in the morning.
Another one of those awkward nights, I guess. I don’t know, maybe I’m weird - I don’t think the friends-with-benefits thing is so weird. It’s not like I felt embarrassed in the morning knowing that we’d fooled around the night before, and it’s not like I was thinking about how disgusting we are or aren’t for being friends fucking around. I don’t mind it - clearly it’s not something he’s so comfortable with.
I also felt - almost guilty, but not really guilty. I had such a good time with the other Matt the night before, and was even telling this Matt about him in the evening before any of this happened. Today after I bid this Matt adieu, I sent the other one a text asking when he was free. When he replied, I suggested that maybe we should go on a legitimate date at some point, and he thought that was a good idea. Then Brian texted me and asked me to come over. I told him I was busy. He said he was out getting dog food. …I had to ask. I live in NYC, I fucking miss having a dog, okay? He’s trying to bribe me to go over to see his dog. I think he made some sugar daddy implications at some point. I have too much of a headache for this.
I don’t think I’ll be able to see Matt this week - I have a pretty hectic schedule for the next several days and then am leaving the city for a school function over the weekend. Maybe late next week, which is a bummer. I was thinking about him a lot today. I’m not kind of obsessively thinking over him, but just keep wondering if I have a crush on him or not. I guess it’s too early to tell.