Part 2: [M]y Actual [F]irst | 2016

Part 1 Part 3

So if you read the first part I just posted, and weren't totally bored, you'll know where I left off: Dejected and depressed and not feeling studly at all.

Quite a bit of time passed like this. I almost gave up on ever having sex or putting any effort into it.

I mentioned in the first post that after my first failed attempts, and losing boners while my dick was in a girl's mouth, I started to think maybe my masturbation habits and porn viewing needed to change. So I cut back a lot. I came to these conclusions on my own.

Eventually I came across http://yourbrainonporn.com/ and /r/nofap. Say what you will -- it seems everyone has their opinions. Some of the people on there are highly religious moral crusaders, some are dogmatic -- but a lot of the guys on there are average guys who have no medical reason for experiencing sexual dysfunctions who are trying to better themselves. This was me.

I'm not going to really go into that much, because this isn't about that. I approached it as a interesting personal experiment, and a way to possibly make myself a "better man" in my own eyes. I wasn't looking for a magic cure. Just trying something new.

Well, if you're like most guys in their mid-20s, if you don't jack off for a month, your hormones start to take over. Add being a virgin into the mix, and it's an interesting cocktail. At about a month and a half my confidence was sky high and I was ready to just fuck until I couldn't fuck anymore. I wasn't going to do it myself, so I needed to find someone who would do it for me.

Enter OKCupid. Trolling around, looking for the ones most likely to fuck me, and figuring out how to best approach them. I really don't remember getting too sleazy or sending out too many messages in this span. The one who responded basically got a "Hey, you seem open to fucking. Want to fuck?" in her inbox. And she replied in the affirmative.

Cari was kind of having a period of weird sexual discovery of her own. She was feeling very, very sexual, and in her own words, "slutty." She was 19 and had had sex with two guys before me. Sex with both of them was fairly vanilla and in her mind, boring. She wanted adventurous. She wanted dirty. She wanted to be a bad girl. And being the horny virgin with six weeks of jizz backed up in his balls, I wanted to make her my adventurous, dirty, bad girl.

She had almost no reservations, and was in from the beginning. We talked online quite a bit and I found out that she was indeed a dirty girl. She was already telling me that she wanted me to fuck her in the ass. I expressed my interest in squirting, and even though she didn't like the idea of it at first, she came around to it, and hard. I sent her DickPix™, and she sent me pictures of her tits. Very large. A little less "perky" than ideal, but pretty nice. I like big boobs, and these were that. She told me I had "the perfect penis" -- I tried not to let it go to my head.

I guess we did what you could call "cybering," and somehow, some way, she told me I got her to cum when she wasn't even touching herself while in the middle of her living room with her family when she was at her computer. I felt like a God.

We met on a Saturday night. She lived with her parents and her house wasn't an option. I lived 45 minutes away and, honestly, didn't want to drive all the way back home and drive her all the way back in one night. So we found an option that would work.

Granted, this sounds super shady, but it really wasn't. We were both wanting to make this happen really bad, and I guess we were willing to make some compromises in order to do it.

So what did we settle on? An abandoned house across from her grandmother's old house that she used to go into with her friends and cousins. We would be able to get in, she was sure. I brought a futon pad and many blankets (it was winter), as well as some lights.

Sounds super shady, but really wasn't. Call it "adventurous."

She was really nervous when I picked her up, so much so that she wasn't even looking at me at first. We didn't say much on the short drive, but I did try my best to ease her mind. When we got there, I unloaded all of the stuff, she grabbed a flashlight, and we made our way into this place. Pretty run down, but here we were, breaking in and getting ready to fuck on a cold Saturday night. We made something resembling a bed. I took a couple shots of whiskey to ease my own nerves -- I wasn't particularly nervous, just wanted to be loose. She didn't. We took off our jackets and boots and put them aside, and just got under the covers together. We started to warm up, but we just laid there kind of awkwardly.

"Are you still nervous?"

"Yeah, kind of. But I'm here. You're not weirding me out or anything, it's just me. I'm being weird."

"You're not being weird. It's a weird situation. I just want you to be comfortable." I put my hand on her side and moved it up and down a little. I guess that was my "move."

"So, what should we do?" I asked. Not so much trying to push things along as just keep the conversation going.

She leaned up at this. "I guess I could just do this," she said as she pulled her shirt up and over her head.

"That works for me!"

Cari was of average height and build. Long brown hair, and wore glasses. As I mentioned, she had big ol' boobs, not exactly model quality, but very enjoyable. She wasn't thin, but wasn't very big either. Full figured might be the right description, but not exactly "vulumptuous." I don't know. Average. Not incredibly pretty, but not bad to look at. Big boobs, but not perfect boobs. Decent ass. But dirty. A naughty, dirty, bad girl. And that counts for a lot.

You could tell she put some effort into picking out her underwear, and if I was smoother/in a different mood, I would have taken some time to praise her. It was a cute bra, but I was far more interested in what was underneath it.

It was off in an instant, and my hands went right to work. They were a little cold at first, but the feeling of her warm boobs warmed them up very quickly. It didn't take her long to relax. Having this stranger fondle her breasts seemed to be working for her, as a smile crept across her face. This was the fourth set of tits I'd ever felt, each one D-cup or larger. Feeling them was really fun, but obviously my mouth wanted in on the action as well. Not really knowing the best way to go about sucking nipples, I just kind of toyed around until I found what she liked. I like putting my mouth over the entire areola and circling around the nipples with my tongue, giving a light nibble, and then sucking the whole thing as I pull my head back. She really seemed to enjoy that. So I would do it on first her left nipple, then the right.

I spent a considerable amount of time enjoying those big boobs, running my hands up and down her sides, pulling her hips into me, rubbing my body between her legs, and giving her ass an occasional feel. I was rock hard inside my jeans. Even though my history of losing boners was in the back of my mind, I didn't think I'd have to worry about that that night.

"I want you to suck my dick." I told her. She smiled at me, and just said "OK." I leaned back off of her and started removing my clothes. I'm tall and fit. Not very muscular, and I don't work out for the sake of working out very often, but I stay active. 6'1", 160lbs. Thin, for sure, but fit. Decent definition, and so on. I have long blondish-brown hair, blue eyes, and a full beard.

So my shirt was off, pants were off, and the boxers were last. She saw the pictures, so she knew what to expect, but suddenly, there it was.

She reached her hand out and tentatively grasped at it, a little unsure of herself. To feel her touch was amazing. I had hardly even touched myself for over a month, remember. I was rock hard. She slowly started to wrap her hand around my shaft, and gave me a couple strokes. I laid myself down next to where she lied, and she worked her way down south. I could feel her big tits grazing against my chest, down my stomach, over my cock and balls, and they stayed brushing against my thighs now and then. The feeling of boobs just barely touching my body is one of my favorites.

She told me beforehand that she always liked to give head, but that she didn't know how good she was at it. I'd only had two half-blowjobs before, so I didn't know what to expect.

She took my head into her mouth and rolled her tongue around it before moving down a little deeper. It was clear she was eager to please. She kept looking up at me for reassurance. It felt really good, and I told her to keep going.

She was certainly feeling adventurous. She started to work her way down as deep as she could, and would come back up with a gasp. It felt awesome. She might not have been the most skilled cock-sucker in the world, but she was eager to please and enthusiasm always makes a sex act better.

Not that I had any reason to stop her, but I wanted to fuck her big tits. So I stopped her, pulled her toward me a little, until I could feel them once again around my cock. I looked her in the eyes while I grabbed one large tit in each hand and pressed them around my swollen hard on, still wet with her spit, and started pumping up and down. "How does that feel?" I asked her.

"Really, really good," was her response.

I kept doing this for some time, really just very excited about the newness of everything, the fact that my boner wasn't just sticking around, but as hard as ever -- and just enjoying myself.

But of course before too long I wanted her. "It's your turn."

Continued in the comments.