The Eighth Wonder of Reddit [MF]

This post is about Caitlin, the eighth Redditor I’ve hooked up with. It also details three encounters we’ve had, so you fine folks get a three-for-one. That’s the kinda guy I am.

**About me**

You can skip if you’ve read my other posts. If not, here’s a verbal snapshot of myself: 28 yo 6-ft, 195 lbs. Gym-goer, but average shape. I’ve lost 12 pounds since March though (woot woot!) Brown hair, (usually) green eyes. I’m hit on quite a bit, which is flattering. Though I do keep my slutty side private, and most friends would have no idea the sort of debauchery I’ve gotten into. Since college I’ve gone from one long relationship to the next. The most recent was an engagement that ended and finally found me embracing the bachelor life. I’ve always had an extremely high sex drive, but being antisocial found myself on Reddit as opposed to a hookup app, or at a bar.

I’ve recently been referred to (I choose to believe lovingly) as a fuckboy. I’m not a fan of the term, but there’s a point where you have to accept it. So sure: I am. I don’t like the word “bull” either, but I love fucking other fellas’ SO’s. So I guess I’m that too.

I’ve met eight women on here in the last four months, a couple of them with their hubbies. I guess my post history covers quite a bit of that. I’ve been messaged by a number of guys asking how I get responses. To put it simply, I communicate. I’m genuinely interested in her; I write in complete sentences; I can talk about more than sex; I’m kinky as hell and willing to try just about anything she’s been fantasizing. I also have a friend who’s extremely reliable, also attractive, and willing to join me in threesomes. And that undoubtedly helps my odds. But honestly, it’s about communication, and making an effort.

**Caitlin**

Caitlin responded to my post seeking a girl for a threesome. That threesome hasn’t happened yet (but it will soon) and I had to look back at our first messages to confirm that that was indeed what she was initially looking for. Her PM to me stated that she was warily interested in my post, she liked the idea, but it made her nervous. She offered her kik right away along with a description of herself: 26, 5’2, 140, works out often, is in good shape. Long, dark brown hair. I’m awful at translating stats into a mental image, but what I was picturing (cute as it was) was nothing compared to what Cailtin is in person.

We swapped photos via kik after she admitted that she was very picky about guys she slept with. Attraction would be important. I wasn’t too worried, but I sent my pic with bated breath. She liked it enough that I’d earned a drink with her. Boom! And her pic, needless to see, impressed the hell out of me. I was excited. We set a date.

We agreed on a bar in Uptown late Saturday night. I had to work late, and headed straight there without stopping to shower and change (it’s somewhat of an office job, so I didn’t look bad). I knew that no matter how the night went though, I would not be able to let her do anything to me. I’m a hygiene freak. To a ridiculous extent. I’m also obsessive-compulsive, and showering has become a thrice-a-day ritual. So this was a big step for me.

I got there first. It was quiet for a Saturday night at 10:30. I got a little table and messaged her. She walked over a couple minutes later. And I was blown away. The smile on this girl! Not to mention her body. She wore a sexy leather (?) jacket and looked just like you hope every blind date will. Her smile was that nervous, yet confident one you see worn by girls who have life by the balls, but are trying a new juggling act. The waitress (whom I kept commenting on; I swear I went to school with her) brought us our first round. We liked each other’s beer better and switched. I felt immediately at ease with her (yes, we fuckboys (shudder) get nervous too). And we got to chatting.

Quite a bit about our careers, lives, past relationship drama. The perils of searching for hookups on Reddit, my odd success with CL, and my disdain for Fetlife. And of course, why she responded to my ad. She said she has a FWB already. But she was intrigued because, while she never intended on responding to a Reddit post (she looks at the personals for fun), she could tell from my post history that I might be someone she could have fun with. And I was eloquent, educated, respectful. These things mattered to her, and they matter greatly to me. So I felt more at ease.

Throughout this, by the way, she was being eyed by a dude sitting behind me, who was with his own girl. Yes, she was the kind of girl you stared through your GF to look at. Again, boom.

Three hours went by. Somehow. Still can’t believe we hung out that long. I don’t do that at bars. But being able to hold a conversation with someone is important to me, and clearly I hadn’t bored her too much. One thing I made very clear was that I did not expect this to go any further than us having a drink. She’d reiterated how attraction was important to her. And I know how some guys feel entitled to something more on “dates” like this. So we decided it was late and we should head out.

We’d parked near each other. We walked together, and I realized just how significant the difference is between 6-foot and 5’2. And just how petite she really was. We got to her car and I awkwardly (because I am awkward) said something like, “Well, let me know if you want to have a drink with Brian too,” and then, when she kept smiling and wasn’t breaking away, “I don’t usually make the first move.” This isn’t exactly true. I make the first move a lot. But I was nervous about a) was I attractive to her? and b) I had not taken my third shower yet. And she said, “Well, I’d make out with you right now.”

And that was all I needed. I stepped toward her, pulled her in, hand on her chin to turn her lips up towards mine, and kissed her. She was kissing me through that mischievous smile, I could feel it. Her tongue darted past my lips, over my own. Her hands gripped my shirt and she moved in closer. She rubbed up against me, needing to feel how hard I was. A group of college guys walked by and cheered us on. A few minutes later a car drove by and catcalled her. We laughed and continued making out on the sidewalk for fifteen minutes. I nibbled at her neck, her shoulder, daring to squeeze her ass in public. She responded with soft moans, pressing against my erection with her own eager body.

“I’m debating whether to invite you back to my place or not,” she said.

I don’t know what dumb response I gave. But it led her to decide “yes”, and we parted for our cars, and she messaged me her address. It was blessedly nearby.

We met at her house and went in. The roommates were out or in bed. Caitlin warned me we’d have to be quiet. We went to her room, and I got an even better sense of who she was. I liked what I saw. I let her know that tonight would be about her. She didn’t mind that at all. We continued kissing, all the while I felt her up. I love feeling a woman’s body through her clothes, and then exploring again once they’ve been shed. Every moment, you know? When I got her clothes off…fuck. I’d really fallen into something special. Caitlin is fit. And small. I feel like I could throw her pretty far. At least set her up on a pretty high shelf. Her breasts are perfect, fitting in my hands so that I can firmly massage them entirely while pinching and pulling her nipples. Her nipples get extremely hard too, which I go crazy for. She said later her breasts aren’t usually sensitive, they must just like me.

I explored her body with my hands and mouth, returning to her lips often, but biting her shoulder and tenderly kissing along her neck, breasts, stomach. When I couldn’t wait anymore, I kissed her pussy through her panties. She gasped. I licked along her inner thigh, traced my tongue over her panties, finding her clit through the fabric. Once her panties were wet, we took them off.

She’d asked me whether Brian and I preferred shaved or not. We don’t care. We like women confident in their bodies and sexuality. She hadn’t shaven smooth, but her pussy was bare, glistening. Absolutely the perfect look. I probably don’t enjoy anything as much as performing oral sex on my partner. Caitlin is a lot of fun to go down on. Too much fun. She’s very responsive, quick to bring to the brink, communicative in what she likes and wants you to keep doing. Being a tease, and loving to draw out a session, I mixed it up quite a bit. Kissing softly, kissing harder; blowing cool air on her skin when she got hot; teasing her hole with my tongue, running it up and massaging her labia. Quick flicks at her clit, and long, wet strokes. Pressure on her clit, intense, sustained pressure and rhythmic movement. And eventually, introducing my fingers at the same time.

That was what our first night consisted of. In my memory now, I want to say she came twice. But actually, it may have been only once, or several more. When she was exhausted she said, “What about you?” But alas, I couldn’t. The freak in me is not that freaky. I would have needed to shower first. It was so hard to turn her down, after all, would I see her again? She got dressed and walked me down, confirming that she would. I went home, very satisfied.

**Fuckboy**

I don’t like the term, but I like the honesty of the word. I can’t have a relationship at this point in my life. Old wounds haven’t healed yet. I still have feelings for my ex, my own baggage to eventually set aside. Caitlin appreciates the FWB relationship for the same reasons I do. One hot aspect of that relationship is the booty call.

We’d messaged a couple times since that night. But on a night that we were both busy, I found myself especially hoping to hook up with her again. And I’d already taken my third shower, so no outs for me this time. She was busy too, but after messaging for awhile, she gave in. She said I could come over, but I’d probably have to be social with her friends for a bit. Ugh, the things I do for a hot girl.

They’re actually very cool. It couldn’t have been more obvious that I was a fuck buddy, but they were very chill. So was she. And I. We were all very chill. Then she took me up to her room. We started out similar to the previous encounter; slowly undressing her, making out, exploring her body. Going down on her. She stopped me and started undoing the buttons on my shirt. I admitted I’d sewn on an extra to make it more difficult. When my clothes were off, she got down on her knees beside the bed and took me in her mouth. Fuck, her mouth felt so good. I’d been dreaming of this girl sucking me off. And she gave head like a fucking expert. She’d admitted she had trouble deepthroating, and she didn’t get far with me. “You *are* a mouthful,” she remarked.

“Yeah?”

“Yeah. Thicker than I’m used to.”

As a guy, that’s always a huge turn-on to hear. She continued eagerly blowing me until my erection was absolutely demanding her pussy. I moved her to the bed and positioned myself over her, and proceeded to tease her a bit. Rubbing the length of my cock along her clit and pussy, getting myself wet with her, finally entering just the head of my cock. She looked up at me with wide eyes, an open mouth gasping, that expression that screams “Fuck me”. I slid into her and her body jolted, a full reaction to me inside her. I leaned down to kiss her as we fucked. We fucked missionary for awhile until rolling over, her on top of me. She lowered onto me slowly, taking me in inch by inch while I massaged her breasts and held her throat. When I put my hands around her waist I marveled at how huge they looked on her body. She rode me faster. We switched positions again.

I pulled Caitlin to the end of the bed to fuck her. I get a lot better traction with my feet firmly on the floor. And I love watching my cock move in and out, getting creamed on and soaked. I couldn’t resist pulling out and going down on her, tasting her cum and used pussy. We fucked for awhile like this, me alternating between eating her out and pounding her, until she was too tired. I hadn’t cum yet, but I assured her it wasn’t a big deal; I last awhile, and sometimes I don’t cum at all. This only seemed to make her more excited.

“You’re more fun than my other FWB.” That was probably my favorite comment of the night.

**How my tattoo cock-blocked me**

The most recent night with Caitlin was still hot, but my body did rebel against me. I’d gotten a tattoo the day before, and for whatever reason it was extremely sore the next day, and I’d even gotten a bad headache. So that afternoon I took some painkillers.

Caitlin and I had been messaging about getting together with Brian for a drink, but that night wasn’t working for him, and Caitlin had a lot of work to do. After messaging some more though, she admitted, “I’m not doing anything productive…” I took the hint and said I’d be over shortly.

We went up to her room again and chatted for a bit before I couldn’t resist pulling her in and kissing her. She lost her shirt and bra and I sat on the edge of the bed with her standing in front of me, just adoring her body. Flat stomach with perky breasts. Killer combo.

She took off my pants and went down on me again. She was so eager, it seemed like she’d been dying to get me in her mouth for a week. One of the best blowjobs I’ve ever gotten. I didn’t want to blow early, so I moved her up on the bed and got her undressed, and went down on her in turn. She tasted amazing. I couldn’t resist fucking her, and finally thrust into her. She was so responsive, loving it. Instead of keeping up my momentum though, I decided to alternate eating her out again. And that was when my body failed me. I haven’t had trouble keeping hard before (maybe the occasional time with an ex?) so it was a sore blow to me. I’m positive it was the damn painkillers (sure enough, on my drive home I had to pull over from dizziness). Caitlin was awesome about it though. We made out, took a break and just chilled on her bed. She even went down on me again for awhile (she’d said she had no interest in tasting herself, so the fact that she did this after we fucked meant a lot to me). I did get it up briefly again, but the numbness took over again and I lost feeling. We continued chatting while I kissed her body. We got to talking about her exploring her submissiveness, and that started getting me going again.

While kissing her and playing with her breasts, particularly her hard nipples, I started teasing her with comments about what Brian and I would do to her. We discovered we share some of the same kinks and interest in bondage and rough sex. She also found out I’m able to cum without being fully hard. Or at least, sorta. Ha. I gushed a bit over her pussy and thighs, but never felt an orgasm. So either it was some crazy precum, or I was really that numb. Either way, it felt amazing.

I also learned that she’s okay with us cumming inside her. Boom. That’s a third boom.

We chatted a bit more and joked around as she got dressed. Kissing her goodbye at the door, I promised her the next time would be a bit more…rough.

Can’t wait.

Source: reddit.com/r/gonewildstories/comments/6vwix5/the_eighth_wonder_of_reddit_mf