Sex With Friends

I don’t have sex with my friends. Friends of friends, yes. Friends of friends of friends, yes. Friends of strangers, yes. Strangers, yes. Guys who wear multiple pairs of pants, yes. But never my friends. Except that one time. And then almost this time that I’m about to tell you about.

We aren’t super close friends, but we chat (flirt) once in awhile, and recently he’s been really, really flirty. One night recently, we went for supper and had a pretty good time. The conversation flowed easily, there were a lot of jokes, and we discussed a lot of topics. One of them was music. He is a fan of bands from the 90’s and 2000’s, including Seven Mary Three (this is important for later). We were out late, and had a little too much to drink. I should mention that I’ve been chatting with another guy that I’ve been feeling pretty into, but he lives out of town and we haven’t gotten to see each other much. But even so, my attention has been focused in that direction. Due to this, I had decided before I even went out that if he made a move, I was going to turn him down. But, the whiskey had other ideas. So when he asked me if I wanted to go back to his place, I said yes. I mean, he’s pretty hot and he makes me laugh. What’s a girl to do? I’m not made of stone!

We get to his place and crack a couple of beer. I have just a couple sips out of mine before he kisses me. Oh, that’s where this is going? (I said innocently) And before I knew it, we were making out on his bed. He kissed me gently and slowly ran his hands over my body. I pulled away and told him that there was someone else I was interested in, and I shouldn’t be doing this, and should go home. He told me I shouldn’t do anything that felt wrong. So I pulled him towards me and kissed him long and deep, because being bad feels so much better than being good. He told me I could spend the night if I wanted to, and that we could just sleep. I went to the bathroom to think about it. When I came out, he was under the covers. I asked him how naked he was under there, and he told me he still had his underwear on. I said ok then, pulled my dress up over my head, handed him a straw, and let him drink it in.

I crawled into bed with him, kissed him, said good night, and rolled over. He spooned up behind me and kissed my shoulder while his fingers trailed over the curves of my body, barely touching me, grazing over the peaks and valleys, sending shivers to all the right spots. I turned towards him and met his lips with mine. He put his hand in my hair and pulled my head back. I moaned and he kissed his way down my neck and up again, licking and nibbling on my ear. I could feel how hard his dick was. I begrudgingly told him to stop.

We went back to cuddling and talking. It got real comfortable, real fast. This back and forth went on for a couple of hours. We’d talk and laugh and cuddle, and then we’d make out, going a little bit farther each time. And then he said, maybe I should put on a condom, you know, just in case. I laaauuughed! And said no. We finally called it a draw and went to sleep.

The next morning, he had to get up early for work, so he showered and got ready and then realized he still had a half hour before he even had to leave. Remember how I said I wasn’t going to hook up with this man? Well, there I was, naked except for a piece of lace covering my kitty, lying in his bed looking up at him, saying, “Well, what are you going to do with all that spare time?” He jumped back into bed pretty quickly and kissed me. Close-mouthed because it’s the morning and we’re not animals. Then he got back out of bed. “These jeans are too tight,” he says. Smooooth. And since his jeans were coming off, well, his sweater might as well come off too! He crawled up between my legs and asked if we could have sex. I told him if he couldn’t get me to agree the night before when I was drunk, the chances of me saying yes while I was hungover were not good. He told me he was going to make me wet and leave then. I suppose that seems only fair. Plus, I could just go home and pull out my vibrator after he did all the legwork 😉

Now he figures he had better get dressed and be on his way. He tells me I can stay as long as I want and sleep. So I don’t move too fast. He grabs his phone and heads to the bathroom. The bathroom is located right by the bedroom, and the entire time we were together, he was a gentleman and always turned the faucet on so I wouldn’t have to listen to him pee. This time was no exception. Except that it was the exception. I hear the faucet turn on, and then I hear, “Oh Jesus, I’m sorry. Amy, I’m so sorry,” followed by the sounds of….his ass exploding. Followed by….Seven Mary Three. Followed by more ass exploding, and his desperate apologies. “I’m sorry Amy, I’m so fucking classy. Jesus.” I am DYING laughing at this point! When he finally emerges from the bathroom, he apologizes again and tears are streaming down my face at how funny this morning turned out to be.

“Why did you start playing Seven Mary Three?! That didn’t help at all!”

“I just wanted something else to help cover up the sound and that was the first song that played on my phone. I’m so embarrassed, I thought I could make it to work, and then it hit! Oh god, now every time you hear that song, you’re going to think of this moment!”

Oh man, we laughed. So. Hard. I probably won’t be able to resist him again.

The City Worker

I’ll call him “Ron”.

I met Ron through Tinder. We had a decent conversation and I gave him my number. We texted for a few days and everything was cool. He’s 41 and works for the city. We had some decent conversations, but of course he would eventually lead it towards sex. I don’t mind talking about sex, but there’s limits. He told me a lot of things he likes, and that he’s pretty kinky. I told him that I didn’t want to keep talking about sex or things that I like and don’t like because then if we end up sleeping together, there’s weird expectations and limited surprises. Plus, I just didn’t want to only talk about sex and told him he could get to know me. He agreed, and we had some more good conversations. Then Thursday came along, and I went out. He told me ahead of time that if I needed a ride, I could call him. We hadn’t met in person yet, so I said I didn’t think that was a good idea and I didn’t want to wake him up since he starts work at 6. He said he didn’t mind. What I really meant was that I would be drunk and prone to bad decisions. He didn’t mind that either.

Well, at the end of the night, after finding and wearing a random hat and dancing on some sort of table at Q nightclub, Drunk Amy remembered that there was someone who would drive us home and we didn’t need to pay for a cab. Obviously my friend thought this was a great idea, especially since I never introduce her to anyone that I’m interested in, or sleeping with. To be fair, I don’t usually introduce any of my friends to anyone. And for good reason, as you’ll find out. So I call Ron, and he says yep, he’ll come get us.

Ron shows up and we get into his truck and head to the north end to drop my friend off. The entire way there, she makes jokes about me, asks him inappropriate questions, and shares waayyyy too much about my life. The next day she tells me she now understands why I never introduce her to anyone that I’m interested in.

After we drop her off, we head back downtown to my house. When we get there, he parks and comments on how he has a very nice down-blouse view. I may have had a slightly tasteless amount of buttons undone on my shirt. He leans over and kisses me. He’s a very good kisser. I kiss him back, hard. And then pull away and say, Thanks for the ride! And hop out of the truck. Goddamn prick tease.

He texts me the next day to tell me how much he enjoyed making out with me, and wants to see me again. But my schedule doesn’t work for the next few days for going out, so I say we’ll have to plan for the next week. Well, the next evening I have free happens to be Thursday again. And I’m going out. Again, he tells me to call him if I need a ride. Obviously I call him. Drunk Amy already made a hypocrite out of Sober Amy, so why the hell wouldn’t I? And once again, he drives all the way to the north end to drop my friend off, and then back downtown to drop me off. This time, I have my hand on his thigh when we make out in his truck. And by thigh, I mean upper thigh. And by upper thigh, I mean his dick. He seemed to like that. I’m sure he would have liked it even more if I hadn’t gotten out and gone inside my house alone again.

We keep trying to make plans, but again, my schedule is not always conducive to making dates. I make some time for him before one of my night shifts and stop by his house on my way to work. Well, his apartment. It’s weird how a simple thing like taking your shirt off leads to having a dick in your mouth, but who am I to stop the natural progression of things? He already had a cock ring over his dick and balls. And what he really wanted to do was jerk off while looking at me, so that was easy enough, plus I like watching guys jerk off. I told him he could cum on me if he wanted, and that then he should lick it off after. He didn’t like that idea. And he calls himself kinky! I laughed, I thought it was a great idea! He came on himself.

So then I left because I didn’t have time to hang around and do anything that would get me off. But I was relatively turned on by the experience. Not enough to see him again though. After hanging out with him soberly, I wasn’t that interested. Plus, he was 41 and still renting. The older I get, the more I realize the things that are really important in a man: Real Estate and RRSP’s.

We didn’t talk much after that. He texted a couple of times and I didn’t respond. And then a couple weeks after that, he found me on Pof AND Tinder again and messaged me on both. He told me he lost his phone or some bullshit like that and to text him and left his number. I didn’t text.