First Time

Allow me to introduce us. I'm Oscar (obviously not my real name). I'm male; bisexual; mid twenties; a recent graduate in an engineering field. The buxom young woman to my right is Estrella (also not her real name). She's two years younger than me, straight, and hasn't quite graduated from school. We've been together for several years. We're to be married in a couple of weeks.

For the time being, I'd like to get this history down in print before I forget the details. I'll post my reflections and thoughts soon. Estrella says that she's interested in writing here as well, so you may well get her version of things as well.

We'd talked about swinging for a long time, mostly in the abstract. I've never found monogamy to have any inherent value, although I've towed the line of expectations and remained faithful to every lover I've had. Estrella seemed to understand my argument that a lifetime was a very long time to spend having sex with just one person. She also expressed a great deal of interest in seeing me get fucked. Like I suspect many girls do, she wanted to be doubly penetrated. She seems to have other fantasies that involve multiple partners, as well. But, I'll not put more words in her mouth, and let her discuss her fantasies herself.

On Friday, at work, I sent Estrella a text message asking if we could look for a man (or a couple) on craigslist to come over and play that weekend. To my surprise, she was downright enthusiastic about the prospect. After we got home, we trawled craigslist for a little while, responding to a few folks. We then decided to post our own.

Almost immediately, we started to receive a flood of messages. I've posted on casual encounters before, but it surprised me how much more of a response you get when you're offering sex with a woman. The response was even more immediate and heavy than if I'd posted in m4m. I found the thought of other men wanting my fiancee, in and of itself, very arousing.

Friday night didn't pan out, although we did have some really good sex while discussing what we wanted out of a frimp scene. On Saturday morning, however, we received an email from a very cute young man not named Roger. Roger had a cute face, a nice body, and a beautiful cock just the right size for my anus--that is, not monstrous. We exchanged photos, phone numbers, and a rough intention to meet, then went about our days' business.

At around 6pm, I called Roger on the phone. This was probably the most psychologically difficult part of the process. Neither Estrella nor I especially like talking to strangers on the phone. I'm sure I sounded nervous. Despite the nerve, however, I managed to make arrangements to meet at a gay bar for a couple of drinks at eight. The plan was to arrange for a hotel to retire to after the drinks.

Half an hour on the phone convinced us that there were no hotel rooms to be had downtown for any reasonable price. We decided to meet Roger and, if we decided he wasn't too creepy, just bring him back to our place.

We spent the rest of our time primping and preparing. I took a shower and shaved my face and balls. Estrella dressed, allowing me to make her decisions. I found it surprisingly exciting to help her look her slutty best for somebody else.

We beat Roger to the bar by about ten minutes. This was plenty of time for a drink and a bit of last minute encouragement. By the time Roger was there, I was starting to loosen up.

Roger arrived, and turned out to be even cuter than in his photos. He also turned out to be relatively articulate and educated. He seemed decidedly non-creepy. So, we took him home.

After getting him home, we sat around and talked for a few minutes. We discussed boundaries (there were no hard boundaries), and condoms (there were plenty of those, and we used them for all non-oral contact). Then, anxious to proceed, I informed Roger that I had no nudity taboos, and peeled. Estrella and Roger immediately followed suit. After getting naked, I smoked while Estrella fulfilled Roger's request to wear a pair of heels. She doesn't wear them often, but Estrella looks absolutely gorgeous in heels--her calves and ass round out just perfectly when she's stretched up on her toes a bit.

While Estrella finished shoeing herself, I made my introductions to Roger's cock. It's a wonderful instrument: six inches long or so, as thick as two thumbs, and with a giant mushroom tip easily twice the diameter of the shaft. I stroked it lightly while Roger touched mine and commented that he'd never had an uncut cock before.

I led Roger to the couch, pushed him down on it, and sat beside him. I'd just started sucking his cock when Estrella joined us. Roger's cock was delicious; the first I'd had in over two years. One thing that made him so fun to suck was that he seemed to constantly bubble with precum. Every bob of my head rewarded me with a new droplet.

Estrella and I took turns sucking Roger's cock for a few minutes before she made a move for mine. I slid up on the couch so that she could blow Roger and me at the same time. She rather seemed to like licking two dicks at once. This didn't last long before Roger announced he wanted to fuck us, and it was time to get our holes opened up.

I wanted my ass plugged first, so enthusiastically hopped off the couch to start stretching out with a buttplug. As I wandered off to the bathroom to finish that up, I head Estrella say, "So, while he's gone, do you want to have sex with me?" I just about came right there. My fiancee offering herself to some other dude, on my couch, while I was in the bathroom.

I came back to find Roger buried balls deep in Estrella's cunt. I sat down and had a smoke while I watched them fuck. I'd never seen Estrella from this angle. I've never seen her more desirable, sexy, alluring, beautiful, or attractive than while she had her neck arched, her blond hair spread around her head, her mouth slightly open and her eyes closed. Since I wasn't directly involved, I had the opportunity to really savor the sounds she makes when she's fucking: tiny high-pitched grunts, and little squeaks.

After a few minutes of that, I decided I needed some dick. I expressed that desire to the company, and Roger pulled out of Estrella while I got into position. I hadn't been fucked with a real dick in a long time, and so I went for a nice and easy position. I got on my knees and elbows, with my ass wagging in the air. Roger didn't waste much time before he pressed his cock into me.

He fucked me gently for a little while until I began meeting his thrusts with my own. At that point, he picked up the pace. He fucked me for a few minutes before I decided my ass needed a break. He pulled out and we sat around chatting for a few minutes.

After my butt had relaxed, I told Roger that I'd like some more. I don't remember who it was, but somebody suggested that I fuck Estrella while Roger had me. Since this is my Number One Fantasy, I immediately agreed.

I put Estrella on her back, and then climbed between her legs. After I was in her puss, Roger got in position and slid into me. Immediately it felt awesome, having the smooth, wet grip of Estrella's cunt around my cock, and a big, warm dick plugging away at my prostrate. The rhythm was difficult to get right, and I think will require rather more practice. This time around, Roger set the rhythm, essentially fucking Estrella through me. I would have preferred a rhythm that had my cock sliding out of Estrella at the same time Roger slid out of me. But, the sensation was too excellent to interrupt with discussion. After only a few minutes of that treatment, I came inside Estrella.

Roger and I got cleaned up, and Estrella mopped a big glob of cum out of her snatch. We talked and smoked for a few minutes before we decided that it was about time to double fuck Estrella. I continued smoking while Roger and Estrella went back to the couch.

They started with Estrella blowing Roger. But, that only lasted a couple of minutes before Roger swung her ass around and went down on her. I only realized it the day after, but he ate my cum out of her. They sixty-nined for a few more minutes before Roger decided he'd like to fuck her. He initially went for her pussy, but found that wet and open already. He changed his mind and, after checking with me for consent, slid into her ass. He fucked her ass for a while before I decided it was time for me to get involved.

Since they were already fucking doggy style, I simply slid under Estrella to get my cock in. I managed to accomplish this without Roger and Estrella disengaging. As I pressed into her, she gasped. I was surprised to find that I could actually feel Roger's cock through Estrella's partition; it wasn't just a porn-story conceit. Almost immediately after I'd gotten inside, Roger resumed his fucking.

I have absolutely no idea how long we fucked Estrella. I saw and felt her cum at least three times; she claims five. But, eventually, she got tired and asked us to stop.

We took another break, after which Estrella and I decided it was time to take care of Roger. Estrella demanded that I choose who and how Roger fucked. I told him to take her pussy.

He put her on her side, and entered her from behind. Meanwhile, I stuffed my dick in her mouth. I eventually decided that I was more entertained by paying attention to her fucking than to getting head, so I pulled out of her mouth and devoted my attention to absorbing the scene and running my hands along her body.

After a while, Roger pulled out of Estrella's cunt, whipped off the condom, and jerked off. He sprayed cum all over Estrella, and I rubbed it in to her tits. I didn't expect to have such a strong, positive reaction to somebody cumming on her. But, that was nearly as hot as any of it.

We let Roger get cleaned up, and then asked him to leave. I wanted him to stay and play a little while longer, but Estrella was completely fucked out and just wanted to collapse. After he left, we talked about what had happened and attempted to process it. When she told me what it was like during the DP, I found myself masturbating furiously. I came all over myself just as she was telling me how thin and delicate the partition was between her ass and cunt.

Next post will be my analysis and reflections on this incident. They're mostly formed already, but I want them textually separated from the history of the event itself.