My Real Life Bad Boy

by Shygirl2019

What’s your gender? Woman
How old are you? 28
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Toronto
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Single
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual

My Real Life Bad Boy

How long ago did this hookup happen? Over the weekend

What was your relationship status at the time? Same as current status

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For more than 3 years

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? I met “Rob” when were were in high school. He was tall (over 6 feet), always had a decent build, with brown hair. He was kind of popular, and he was a bit of a trouble maker. I was 5’6″, skinny, brown hair, shy and had a small group of friend. He wasn’t part of my group of friends, but he was always nice to me in classes and would always make me laugh. We couldn’t be more different, I was a good student and had a future ahead of me. Him, not so much, but I had a bit of a crush on him though I always kept it to myself. Besides, my parents would have killed me for dating a guy like him.

After high school, I never heard or saw him. I had no idea what happened to him. A few years later he sent me a friend request on facebook. We chatted a few times and then he disappeared again. His account was still there, but there was nothing out of him. It seemed he had a bit of a troubled past with the law, and had been arrested for robbery and was in jail. When I heard this, I did some checking into him and found out there were no violent crimes.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The day he got out of jail, he posted something on Facebook. I replied congratulating him. He thanked me and I sent him a private message and we started talking. He had opened up to me about his past and about how he wanted to make changes. So I was encouraging him, etc. We started talking about various things, the past and all that. Me being shy was one thing that came up. I eventually asked him what it was like to be in jail, and he talked about that. His girlfriend dumped him while he was in. I said sorry to hear that and said it really sucked. He said it did; it had been 3 years without sex and he had no one waiting for him, which he quickly apologized for saying. I laughed it off and told him it was okay. Then I told him I had a crush on him in school, which he was surprised to hear. He told me I should have said something. I told him my parents wouldn’t have been pleased with me dating a guy like him, to which he laughed.

We kept talking about things and I got up the courage to ask him if he wanted to go have a coffee (he doesn’t drink alcohol), and he said sure. We got together and talked for a while. He mentioned how he was surprised I’d want to be seen with him. I was like why not? You’ve always been decent to me, and you’re attractive. He smiled and we kept chatting, but things were a little flirty at times. Occasionally I would get quiet, which he would tease me about. At one point I got the courage and leaned towards him and said, “I’m not being shy. It’s been almost 2 years since my last boyfriend, and the high school girl left in me is wondering what I missed.” He replied back to me saying, “let me show you baby.” I sat back, giggled, and said I’m not normally this spontaneous. He said no pressure, and that if I didn’t want to that was cool. I quickly said, no I want to, let’s go to my place, and we quickly left.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We got to my apartment. He asked me again if I was sure, and I reassured him I was. First, we sat down and just started with some innocent kissing. He was stroking my hair and I could feel my heart racing. I couldn’t believe my lips and his were connected. I stood up and smiled at him then went to turn on the radio. I can’t remember what song was on, but I started dancing towards him. As I got near him, he reached out to grab my hand, but I pulled back. He looked confused at first, but while I was dancing my shirt slid up a bit to show my belly and the bottom part of my bra. I dropped it back down. He smiled. I kept dancing a little closer to him. Finally, I pulled my shirt right off. I had a lacy white bra on. I moved in and kissed him, and I felt his hand on my left breast above the bra. I had my hair tied back and I reached up and pulled it out. It flopped down into our faces. I pulled back and started dancing a little more, then undid my bra and turned around as I took it off. As I turned back around, I put one arm across my breasts to cover them and tossed the bra to him. He called me a tease and sniffed my bra. I moved in towards him. As I got really close, I moved my arm, with my breasts almost in his face. He reached up and grabbed a hold, squeezing and rubbing both of them both. He said to me, “you have awesome tits”, as he started sucking my nipples. I’m not a big girl, only a 32b. He was playing with them for a little bit and it was driving me crazy.

I pulled back and got him to stand up. I took his shirt off. He was in decent shape with some tattoos. I was rubbing his chest and got my hands near the belt of his jeans. I undid the belt and button of my pants showing my panties. He grabbed a hold of me and pushed me down on the bed. He pulled both my pants and panties right off. I smiled and spread my legs; he went right in. I know a few songs played while he was down there. I didn’t mind though. Then he stood up and took his pants off. I sat up and started giving him a bit of head. It didn’t last as long as him being down on me. He stopped me saying that he didn’t want to blow his load that way. I moved back on the bed as he put the condom on. Seconds later, my head was thrusting back as I felt him going into me. He started slow but picked up the pace quickly. I’m not usually too vocal in bed, but this time I was into it. He didn’t last too long, but when he came it felt like a jackhammer. The condom was full. He appologized for the quickness and said if I gave him a few minutes he’d do better. Excitingly I said yes. As we were lying there, I started playing with his dick. He started to get hard again and I decided it was time to 69. As I was getting on top, he commented that I was a little bit kinkier than he thought. This went on for a few minutes, he put a finger or two up my butt. As he was fully up then, I grabbed a condom and put it on. Then I got on top and started to ride him. With my boobs in his hands, as I was going up and down and looking at him, the realization started coming to me of who I was having sex with. I started moaning louder. Then I got off and got on my knees. He helped bend me over, slapped my ass, and went in doggy. Seriously, the best position so far. After a while, he moved me back onto my back and we finished that way. He couldn’t stay though, so he got dressed and I wrapped the sheet around him. Then we kissed good night and he left.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? It’s only been 2 days. He messaged me to ask how I was doing. I still like him, but I’m not interested in a relationship and I don’t think he is either. He took my cell phone at one point and took a naked selfie of himself (from the head down), and another one with the two of us. I’ll admit I keep looking at them. Lol. When we were kissing goodnight, I was saying to him how amazing this was, and I said he didn’t have to ask me twice if I wanted to fuck again because I wanted to. He said “good” and that he was hoping I would. So I figure another hookup will happen soon.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? My neighbor. She’s a single mom, about my age. She heard us at one point and asked me that evening if I had a new boyfriend. I was so embarrassed at first, but she brought up how she’s sure I’ve heard her at times, which was true, she’s always has a new bf over. lol. So I told her about him. She told me it’s always great to have fun like that.

How would you best summarize people’s reactions about this hookup? Neutral

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I got to find out what I had always wondered when I was younger. I ended my sexless drought also.

What was the WORST thing about this hookup? Okay, I’ll admit, he probably wasn’t the best person to be hooking up with. Lol

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really. If I wasn’t so shy at times, I probably would meet up with more guys.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

What do you think about the Casual Sex Project? Neat. Glad I found it to share my story.

You have a hookup story to share? Submit it here!