Our Big Coc Threesome: the Deed

About three months had passed since Jess and I agreed we wanted to have a threesome with another guy who had a big cock. Over the last few months, the idea consumed us, and it had literally been all we talked about from sunup until sundown. We joined an adult dating site and looked for some strangers that might fit the bill. This was actually quite entertaining, and we had a great time browsing profiles, creating our profiles, taking pictures for our profile, etc. During the day, we would send each other emails of people we had found in searches or who had reached out. We even started several conversations with guys we thought were a good fit. Still, we never actually found anyone that was either serious or who had the right demeanor.

Our fantasy talks in the bedroom revolved around threesomes with either someone we found online, a stranger we met on vacation, or my friend John. John was the real catalyst to all this threesome talk. Several months ago, we had gone naked hot-tubbing with John and his girlfriend. That night ignited the desire already brewing in my and Jess's relationship. You see, John has an incredibly large thick cock. The most impressive thing about his cock is the huge thick head on it. During our night in the hot tub, Jess and I had over an hour of unobstructed view of his manhood, and she was entranced by it. The entire time we were in the hot tub, his cock was in a semihard state, elongated and heavy looking. Jess described his cock later as having an "angry look" because it was flushed from having been in the heat of the hot tub. It also had a large vein that ran along the side of the base, wrapping to the top of his cock.

As I said, John was on our minds a lot. We fantasized and talked a lot about him fucking Jess with his fat cock. What it would feel like spreading her tight pussy. What I would do while he was fucking her. How difficult would it be to get his big head into her tight pussy. What would his mouth feel like on her pussy. Would she be able to suck his cock due to its girth. We covered every angle of what could happen in our emails, texting, and our bedroom dirty talk. We came up with all these scenarios of how to make it happen, but we always got stuck on finding a way to actually make it work. I wasn't comfortable in just calling him up to tell him my girlfriend wanted to fuck his big cock. So, we agreed that it would just have to happen naturally - we didn't want to try to force an arrangement. Then, finally, the opportunity presented itself.

A friend of mine from high school was getting married, and Jess and I planned to attend. Fatefully, a few weeks before the wedding, I received a call from John telling me he had just received a late invite to Brad's wedding and was planning on coming into town for it. It was obvious by the tone of the call that John was looking for an invite to stay at our house again. Which, of course, I was happy to offer. He had some work conflicts and said he would only be able to fly in late the Friday before the wedding, and he had to leave Sunday early afternoon to be back for work on Monday. It was going to be a really fast trip.

When I hung up the phone, I had this nervous feeling in my stomach. I knew that this trip meant there was a possibility we could end up in a threesome or maybe even a foursome with him and Chrissy. At the very least, I knew it was going to be another fun night of naked hot-tubbing, and perhaps we could begin the flirtations that set up a future threesome. My mind was a mess, and I was nervous to tell Jess that John was coming into town for the wedding. I don't know why, but I guess it was because it suddenly got very real going from fantasy to "Do we really want to make this real?"

I waited until that evening after we had dinner to tell Jess. It was a beautiful evening and we decided to have wine outside after dinner. Jess had on her favorite pair of loose burgundy running shorts she always lounged around in. I loved them because they have large loose legs, and she never wore panties with them. I was always treated to peeks of her beautiful smooth pussy when she wore those shorts. This night, she had on a light tank top with no bra. Jess's nipples are always at least semierect. They are never soft, and her hard nipples pushed against the fabric. She knows how much I love her nipples poking through her tops, and she made sure she allowed them to poke through her clothes just about as much as Jennifer Anniston does.

We had just sat down when I casually said, "John is coming to town for Brad and Emily's wedding next weekend."

Jess literally choked a little on her sip of wine and coughed. "Yeah, right. Seriously?"

"I'm serious. He called today. I told him that he and Chrissy could stay with us. He said they're flying in late Friday and will have to leave early Sunday evening to get back for work on Monday. So it will be a very quick trip," I told her.

"That was it? That is all you talked about?" she asked. She looked a little pale and very nervous.

"No, I asked him if he wanted to fuck your tight pussy with his big fat cock and he said 'sure'!" I replied nonchalantly and took a sip of wine.

"Yeah right. You better not have. Seriously, is he coming next weekend for real or are you just messing with me?"

"He seriously is going to come and stay here. We didn't talk long. It was a very brief conversation. I think he was fishing for an invite to stay."

"Ok. I am sure it will be fun to go to the wedding with them. Let's get a car for the night. I know you wanted to take the boat, but I don't want to deal with the wind after I get my hair done, and it's getting chilly at night now. That way you don't have to worry about drinking either," she said.

Jess was acting nonchalant but also seemed tense or nervous. I am a call out the elephant in the room kind of guy, so I said, "Do you really want to have that threesome with John? This could be our chance."

"No. He is going to have Chrissy with him, and I don't want to make it weird with her," she deflected. "I knew you were going to ask that."

"Why don't I just hint to him before he comes and see what he says?" I asked. "Maybe they would both be down for something fun. You love making out with girls. Maybe they could both pleasure you while I watch," I offered. This was another one of our fantasies we talk about quite often."

"I don't think she's like that," Jess replied. "She was fun, but she also seemed very jealous and competitive. I don't want it to be weird with them. I know we talk about it, but talk is different. Besides, you said yourself it needs to happen naturally if it's with someone we know. We can't force it, and this feels like we would have to set it up. It's not like it's a stranger, and it feels weird trying to set something up beforehand with someone we know," she said.

"Yes, I did say that. But I was kidding more than anything. Maybe we can do some naked hot-tubbing again and get you all horny. That turned out to be a lot of fun last time," I said jokingly.

"You wish!" she said.

I dropped it, but we both knew she would enjoy that just as much as I would.

John was going to be there in 11 days, and each time we had sex before he got there, we didn't talk about him at all. We didn't even talk about threesomes. I think our plans made it weird and too real for her, and I did not want to risk turning her off to the idea, so we stayed away from the topic the week leading up to the wedding.

That Friday before the wedding, with John and Chrissy due to arrive late, Jess and I went out to dinner and had some wine. We both were very tired when we got home. Jess just crashed out and I stayed up to wait for our guests to arrive. About 11:00 PM I got a text from John saying they had landed and would be there in an hour. I told him I was going to go to bed but gave him the door code to let themselves in. They should help themselves to anything in the fridge, bar, etc., and use the same bedroom they stayed in last time. Then I went off to bed.

I usually work out on Saturday mornings, and I got up at 6 and had some coffee, checked my email, etc., then left around 7 to go work out. I finished my workout then headed to the market to get some fresh croissants, bagels, fruit, etc. for breakfast. By the time I got back to the house it was almost 9 AM. I came in and sat the stuff down in the kitchen. It seemed like nobody was up yet, so I went to our room to look for Jess.

Jess was not in bed or in the bathroom. I walked back out to the kitchen and quietly called her name, not knowing if John and Chrissy were up yet. I didn't get an answer, and the house was really quiet, so I figured she was out back having coffee. I poured myself a cup and headed towards the back patio.

When I stepped out onto the patio, I found Jess and John sitting at the table drinking coffee and chatting. "Hey baby," Jess said as she saw me come out of the house. John had his back to me, but stood as I approached and turned to give me a man hug.

"What's up brother? Good to see you," he said.

"Just went and worked out. I know you guys haven't eaten yet. I brought some stuff back from Mario's. It's in the kitchen," I told them.

"No, we haven't eaten," Jess told me as I sat down beside her. "I just got up 15 minutes ago and found John out here. I haven't even finished my first cup of coffee yet."

Jess was wearing a shirt I knew very well. It is actually a long-sleeved baby blue nightshirt. Made of a very thin fabric, and you can easily make out the darkness of her areoles through the material. Her nipples poke through the fabric like it is not even there. The fabric of this shirt seems to just cling to her breasts like a second skin. It literally doesn't leave anything to the imagination. It is also quite short, down just past her ass.

Jess was sitting on the couch with her legs folded under her to the side. Her pussy and ass were not exposed to John at all, but it showed her entire leg and hip. She had actually taken a pillow and had placed it on her lap and was leaning against it. I don't know if this was for modesty or comfort's sake but knowing Jess, it was probably the latter.

"Is Chrissy still sleeping?" I asked John.

"She didn't come," John told me. "We got into a huge fight Thursday, and we broke up. I tried to patch it up with her and have her come along, but it's been one of those things that have been coming so I just let it be. I was just telling Jess that Chrissy was fun, but we weren't going anywhere and we both knew it. We've broken up 3 times in the last 6 weeks. It's just too much drama and I am getting too old for that shit. If I wanted drama I would have stayed with Tonya," he said with a shrug. Tonya was his ex-wife he divorced a little more than a year ago.

"Well, that sucks. Sorry man, but it sounds like it's for the better. I guess you'll be the swinging single guy at the wedding, catching the garter and banging a bridesmaid," I told him.

"Yep. That's the plan. Brad's sister is standing up, and I heard she is separated and going to the wedding single. We used to hook up after high school," he said with a shit eating grin.

"Oh, now it makes sense. You have a convenient fight with Chrissy, and Ryan (Brad's sister) just happens to be single. Just a little bit of a coincidence there," I said, kidding with him.

"Well, I didn't plan it that way, but when Chrissy said she wasn't coming, I didn't try really hard to convince her to. I would love another chance at Ryan. She still looks amazing," he said.

Jess broke in. "You guys are all the same. Either way, we are going to have fun. For now, though, I have to get ready to leave soon. My appointment is at 10:30 to get all done up."

As Jess got up from the couch, her shirt was pulled up a little and John and I got the very briefest flash of her bare hip and side of her ass. I didn't see her pussy, and I don't think John did either, but we both sure tried. As she walked away, we both watched the bottom of her ass when she stepped into the house. She is such a fucking exhibitionist tease!

Jess showered, then put on some shorts and a tank top. Still no bra, with her nipples poking at us, but the top wasn't transparent and was made of a much thicker material than the one she had on earlier. It was sexy, and her nipples were alluring, but it was an outfit she could wear in public. It was normal for Jess on Saturdays to wear no bra with her nipples poking through a tight shirt. She loved teasing people and having them stare while she acted completely nonchalant about what she was wearing. She was leaving to get a mani/petti, get her hair done, and then she was having her makeup professionally done. She said she was going to be gone until about 2:00 PM.

I had convinced Jess that we should take the boat to the wedding and we would make it a nice slow leisurely ride so the wind wouldn't mess up her hair. The 3 of us would sit in the cockpit area to keep her out of the wind, and we would enjoy some drinks and snacks on the way over. That being the plan, we were set to leave at 3PM and take a nice, slow, one-hour ride to the marina where the wedding was being held.

After Jess left, John and I had time to kill. John needed a haircut and wanted to get a new shirt to wear. I was all set, so I decided to tag along with him. While we were out, I kept my ears open for an opportunity to feel John out regarding a threesome or his interest in Jess. I really didn't know how to bring it up, but as luck would have it, John opened the door to slip in some inuendoes.

"How long have you and Jess been together now?" he asked.

"Almost a year and a half. I am actually surprised it has been that long. Seems like we just started dating a few months ago," I said.

"She is one hot woman, and the way she dresses all the time is so sexy. Do you get much grief over it from your buddy's wives or from other women when you go out?" he asked.

"Yeah, she really pushes boundaries, that's for sure. We've had a few incidents where her appearance or antics didn't go over well at all. She and I have actually talked about it. We've gotten pretty good at discussing who we are going to be around and what she shouldn't wear in certain circumstances. Like tonight, it's a wedding, so we talked about making sure that whatever she wore wouldn't be so sexy that it became a spectacle that takes attention away from the bride. She got a very sexy black dress that should do the trick. It's sexy enough to keep Jess happy but shouldn't be too much to cause an issue," I told him.

"Sounds about right. She is too hot for most women to handle their men being around her. That's what Chrissy and I got in a fight over. She didn't want to stay here because she says that all I do is stare and flirt with Jess. She's really intimidated by her." he said.

"Seriously? I find that surprising. It seemed like she and Jess were best friends last time you were here. Jess said they even made out in the bathroom before they decided to go naked in the hot tub. So it really surprises me that Chrissy was intimidated by her," I told him, and I really was.

"You know how women are, man. They hate the hotter woman. Chrissy constantly brought it up after that weekend and it got very annoying," he said.

"She kept bringing up things about Jess? What did Jess do that made her that jealous?" I asked, completely confused by this.

"Jess didn't do anything other than have a good time and be fun. It was Chrissy's problem, man. She is just a very jealous person. She just kept bringing up that I was staring at Jess, and I was flirting with her. I told her that we were all starting at each other - we were naked, for heaven's sake! Besides, you were there the whole time and I told her she was just being crazy and jealous. She just wouldn't let it go and kept saying that she knew what I was up to. We didn't even fuck that night. She was pissed at me and made me go to the bedroom with her. That is why we just disappeared like that.

"Wow, that is wild. I didn't think you were out of line at all. We were all having fun. You guys were flirting, but I was flirting with Chrissy too. We all were flirting. We all were, but we were naked and drunk in a hot tub. That is what you do. And to be honest, as far as Jess goes, she was very tame that night if you ask me. She was flirty, but she can be over the top at times. But that night she was on par with everyone else. I think Chrissy was just being insecure, it sounds like," I reassured him.

"She brought it up again when I told her we were going to stay with you guys. She started her shit about it again, so I told her she didn't need to come. We had fun with you guys last time and I was looking forward to this trip. I wasn't going to come down here and have a shitty time if she was going to be like that, so I just left her at home."

"Wow, man. This really is surprising to me because I really didn't think you were out of line at all. Shit, she's the one who asked Jess to show us her piercing. If she didn't want you staring at Jess, she shouldn't have asked her to show everyone her pussy ring. That was just asking us all to stare at Jess's pussy," I said with sarcasm.

"Tell me about it, man. That's the problem with her. One minute we're having fun and I think she's cool with things and the next she turns it into something it isn't. It's just too much drama. You're very lucky you have Jess and that she's not like that," he commented.

"What a bummer. We had a lot of fun that night. Jess and I talk about it all the time. To be honest, I was hoping we would all end up in the hot tub again this weekend," I told him, looking for an opening.

"You and me both. That was a lot of fun, and while I didn't think I was staring, I'm happy to see Jess naked in the hot tub anytime. Maybe Ryan will come back with us and be up for some naked hot-tubbing herself," he said with a grin.

"Even if she doesn't, we can still go naked again. I don't think Jess will say no just because Chrissy or Ryan isn't there. Everyone has already seen everyone else naked, and to be honest, Jess looks for any reason to take her clothes off. She loves being nude around people. I'm sure tonight won't be any different, with or without Ryan," I said.

"She is wild, man. I know I keep saying it, but you are a very lucky man. I don't want to be a third wheel, you know, and I don't want you to think I am creeping on your girl," he said.

"Don't be ridiculous, man. Jess loves that kind of stuff. If it were up to her clothing wouldn't be allowed in our hot tub at all. And I know she won't turn down the chance to see your third leg again either," I said jokingly, hoping it didn't come across weird.

"That is funny. Third leg! Well, I've never been a shy guy, so I am up for it if you guys are," he replied enthusiastically.

"And neither are we. Let's just have fun tonight and whatever happens, happens. Sound good?" I said to him.

"Yep, works for me," John replied.

The rest of the afternoon was uneventful. Jess got back around 2 PM. Her hair, nails, and makeup all looked amazing. Not that I expected anything else, but she looked like a runway model. She had chosen a backless, loose flowing dress that was black with glittery stuff in the fabric that made it sheen. She slipped it on, and it came down just past mid-thigh. It wasn't slutty at all. Very elegant, but the open back made it extremely sexy. The open back and neck strap showed the world she wasn't wearing a bra. The material did a good job of hiding her hard nipples, so they were not obnoxious. You could see them poking through if you looked closely but were not obvious. She had slipped on a tiny black silk thong that nestled her little pussy perfectly. She topped it off with 4-inch red-soled heels. She literally looked like she was ready for a red-carpet event.