My fine new life, I guess! [MFM]

This account is well over-due. I’m posting only because /u/rosevillegirl has kept asking me to. This is for you!
However, disclaimer, it is not going to be an overtly pornographic post, sorry. I write professionally, but graphic romance has never been my niche.

So I’d been posting regularly on Reddit (the only reason I’m on here, really) since getting out of a five-year relationship. I’m dead-set on exploring for awhile before settling in again. So in my search for FWBs, or hookups, I’ve also expanded into group play. Now, I’ve been involved in threesomes since high school, and pretty regularly until that serious relationship. Since then, I’ve been meeting couples and arranging group play with some friends of mine.

So I want to share two experiences here: a great one, and a not-so-good (because even my fine new life isn’t all sunshine all the time). First, that not-so-good one.

My “friends” as I’ll refer to them – although we met through CL through a shared interest in group play, and basically formed the “wingmen” (heh) – were not available when I got the message from Emily. She was a 29 year-old who really wanted to experience a foursome. We went back and forth for a couple of nights, emailing and then texting, as both her and I made sure she was serious about this. Sometimes fantasies don’t always want to be realized, you know?

She was extremely nervous, but really warmed up to me and to the idea. Since my friends were out of town or unavailable on the night she wanted to do this, I found a guy to join us (we’d agreed to start with a threesome, since she was still pretty nervous). He seemed very chill, respectful, and open to whatever did or didn’t happen.
So the night came. Now, I couldn’t host because of my rowdy artist roommates. And this guy couldn’t, I assume because he didn’t want to invite strangers over. I got a hotel room for us. And I offered to bring the condoms. He and I arrived first, and about thirty minutes later Emily did.

Unfortunately, I made some bad calls here. First, I’d already agreed to see my family that night around 10pm. They live in Ohio, and I only see them a few times a year. They were visiting and leaving the next day, but catching a show at the Orpheum that night, and I said I’d meet them after. When Emily got to the hotel, it was already 7:30. I didn’t worry much, because usually threesomes (the first time, in my experience) are not marathon affairs. And if she decided to back out, no harm done anyway.

Well, she was more nervous than I thought. Like, I don’t know how she brought herself to drive there. About an hour and a half in, we’d finally all gotten on the same bed and started making out. The other guy went down on her first, and then I did while she gave him head. It was hot at first, especially as she’d confessed to me that she was sometimes a squirter, and about five minutes into eating her out, my face and arm were soaked. She was cumming in waves.

She’d wanted to try DP as well. A bold move for the first time, but we were in. The other guy began fucking her pussy while I lubed up her ass and began working it with my fingers to get her ready.

And now I must confess why this night was doomed to fail. And alas. Through our conversation before things finally started, I realized that I really was not attracted to her. Physically she was fine; cute, curvy, very nice legs, a winning smile. But I’m as much drawn to personality as anything else. When the hookup is sexually charged and escalates quickly, I’ll admit that physical attraction beats all. But this was two hours of talking first, working through her nerves, getting to know each other. And honestly, she just wasn’t someone I wanted to really have sex with. And guys, you’ll know that’s a bummer. Girls, you’ll know it too.

Regardless, I went against my feelings (remember, I had to be out of there within 45 minutes now anyway) and when the other guy took a break, I began fucking her. And this was when I realized she was still too nervous to be doing this. When we’d first all began making out, she kind of just let us kiss her, barely parting her lips in response. And she kept her eyes closed a lot. She did nothing with her hands. Now that I could see her face below me, this hadn’t changed. Lips pursed, eyes closed, arms (there’s no better way to explain this, and I’m sorry) held like a T-Rex’s in front of her. So, worried about what she was thinking, and not into it myself, I stopped. We laid on either side of her, trying to gauge how she was feeling. She said she was fine. We made out again. I fingered her ass. She jerked us off. I came on her ass (it was an awesome handjob, and I’d been saving a load as she had said she wanted us to cum multiple times for her). And then it was 10 pm. I feigned regret as I prepared to leave. And they asked if I minded that they stay. Honestly, I didn’t. She was obviously uncomfortable with the group dynamic, and I figured they should at least enjoy some 1-on-1 time if she was feeling it. I even left the condoms for them.

I don’t know what happened after that. I know they both left sometime in the night because I came back in the early morning to check the room out. By then I was a little annoyed, to be truthful, that I had paid for the room and the condoms (the remainder of which I threw out, because they’d been out of my sight all night) while the other guy contributed nothing. I hope she had some fun. I understand how nerves can be that first time, and I wish I hadn’t set a deadline for myself that night. But of course, that wouldn’t have helped the lack of attraction. The squirting was a big win though.

And now I’ve written a short novel without intending to. Regardless, I’m going to include the more positive threesome I had after that. At the request of some hookups who are interested, but not yet committed to trying it!

About a week after this, I’d gotten another message, from Jordan. She too wanted to fulfill her group fantasy, but asked that we start with a threesome. Smart move. I would always encourage this.

My friend Dan was available for the night we decided. Jordan was a lot more into it, from the beginning. She knew she wanted this, and that it was going to be fun. This is the mindset you need to approach the first time with. Jordan is 24, 5’6 and 125 lbs (if I remember what she said), and stunningly beautiful. I do love women my age and older quite a bit, but sometimes there’s a natural submissiveness with younger women, which when mixed with their eagerness and confidence, is a killer combo. Jordan was like that.

This time my roommates were not going to be around for the night. Jordan came over first, and after a couple drinks we began to kiss (over the clothes handsy stuff included, but we promised to wait for Dan before clothes came off). Dan got there and took a shot with us. Then we brought Jordan to the bed and began to strip her. She was a beach girl for sure, who hadn’t lost her tan over the winter. We must have kissed and licked every part of her body by the time she was naked and laid down. I teased my tongue up her inner thigh while Dan massaged her (size B? they were perfect) breasts and passionately kissed her neck, nipples, stomach. She wasn’t entirely smooth, but trimmed very short, which I thought was perfect. She was soaking wet already, and I loved tasting her before even parting her pussy with my tongue.

I went down on her for a long time, I think. Dan tapped me out and I moved to her mouth while he took a turn. We were naked at that point, and she took me in her mouth and moaned while muffled by my cock as Dan fingered her pretty aggressively. I took that as my cue, and gently held her head while guiding my cock myself. She responded well, and we proceeded to all-out face-fucking. I took a break and Dan got his turn while I felt Jordan’s body up and fingered her. She was more than ready to fuck at this point, and I was up first.

She was still very tight. I have a nice package, but I’m not hung. I do have girth, so feeling the snugness as I slid into her, and having her buck her hips in response and moan over Dan’s dick – I almost came right then. We fucked missionary for a while, until I turned her onto her knees and did her doggy. At this point we were spit-roasting her, and she was loving it. After she came, she needed a little break. Bummer for Dan, who hadn’t gotten to fuck her yet. But we talked for a bit, laughed, did another round of shots. Got back into it.

She climbed over Dan and lowered herself onto him (ladies, he’s got more length, while I have the girth: we make a great team) and was almost instantly cumming again. I stood and proceeded to face-fuck her again. She came, and I blew my first load in her mouth. On a hilarious note, she couldn’t hold it all in, and some dribbled down her chin, onto her breasts, and consequently onto Dan’s stomach. He laughed. That’s a good wingman.
He had to pull her off so that he could cum. She got down as quick as she could and tried to catch it on her breasts. For the most part it worked. And then we all lay there and caught our breath, cum-covered. Partly why you should only do this if you don’t have any hangups about bodily fluids.

After a while, we tried for our second (third?) round. She decided she was too tired to try anal this time, so we each fucked her while she blew the other. Her jaw and pussy was so sore though (what a champ!) that ultimately we finished by jerking off onto her breasts. This turned into kind of a facial, as we’re both heavy cummers and poor aimers. She was okay with that. What a sweetheart.

And that was one of the positive times I’ve had. They usually are positive, which is why I encourage women and even men who are nervous about exploring, to go ahead and try it. Just make sure you have the right people, few hangups, a positive attitude, and plenty of patience. I can promise that while parts of it will feel like a great porno, the overall experience is goofy, odd, sexy, wet, hilarious, breathtaking, and unforgettable.

I’m happy to share that brief foray into my new existence. Will very likely share more stories of past adventures and those to come!
Hope you enjoyed!

Source: reddit.com/r/gonewildstories/comments/6en5gy/my_fine_new_life_i_guess_mfm