Our Second Threesome with John

If you are not interested in how this event came about or the activities of the night leading up to our second threesome with John and just want to get to the hard-core stuff, skip down until you see the **********Good Stuff********** separator. This is where the real threesome sexual stuff begins. If you like the back story or the details leading up to the night, then here we go...

If you have followed any of the Jess stories, then you know that these are the recounting of events from our relationship that happened over 17 years. They are true stories based on real events, and sometimes I can find old emails where we discussed the events in detail. Most of this story is from recollection, so there might be an overlap in some of our conversations. I did find some emails from around when this happened but not enough to include in the story. Still, at the same time, they are great reference points to remind me of the mood and detail of the events.

Jess and I have a few primary proclivities or fetishes, if you will, and they are the impetus for most of our sexual adventures; large cocks/cock size fetish and exhibitionism. Our cock size obsession revolves around her strong desire for large cocks and the simple fact that I don't have one. Don't get me wrong, I'm not small, exactly. Pretty much average in length and probably slightly larger in girth than average, but overall, a very average, sized dick. Like most guys who are average, I consider my dick to be on the smaller size, especially since I am such a large guy at 6'5" and 230 pounds. I have never had a problem satisfying a woman, and I am an exceptional lover who is very giving. Still, I have noticed that women I have slept with are a bit surprised when they find out what I am not packing down there. It's not the large cock they assumed I had. Jess is one of those women who was surprised and had a preconceived notion that I would be large.

Jess and I have magnificent sex; we experiment and explore all the time. Dirty talk, fantasy talk or even just exploring our fetishes together by asking questions is one of our biggest turn-ons. This is how I discovered just how obsessed Jess is with large cocks. It took some time, but Jess admitted that my dick was on the smaller side. Before me, she had been with 3 other guys. One of them was really small, like the size of her thumb. The other 2 were quite a bit larger than me, with her ex-Mike, whom she was dating right before me, being the largest. Even though Jess does think I have a small dick, she loves me. She knows I enjoy this aspect of our relationship, so the light, no degrading SPH we engage in is never meant to be cruel. It's more about us accepting her desire for large cocks and accepting that I don't have one, which is ok. Because we are at that point, we can both enjoy her desire for large cocks and not be threatened by it.

Jess is 5'6" tall, has long blond hair, dark eyes, full firm C-Cup breasts that sit high, a nice long torso, flat, tight stomach, long legs, perfect ass, a gorgeous tight small bald pussy with beautiful little lips and a killer almost innocent smile to top it off. However, it was not until our first Cancun vacation that I realized how beautiful she really was. Jess was standing by herself, drinking a glass of wine, waiting for me. I was about 50 feet away, talking to someone we had met earlier in the day, when the guy paused, looked at Jess, then said to me, "she is the most beautiful woman here." I looked over at Jess, and it was then that I really took in just how beautiful she really was. I turned to the man and said, "you know the best part of it is? She does not even realize how beautiful she really is and is just as beautiful on the inside." I meant it too. She knew she was hot and sexy but not in a conceded way and did not realize how intense her beauty really was at that point in time.

Jess also has a small hoop piercing in her clitoral hood. I have always had a thing for a girl with her pussy pierced. Preferably through the hood; I like a small hoop instead of a bar. Don't get me wrong, it is all hot, but my preference is a thin hoop through the hood where the tension ball will hang down in front of or over the clit. Jess has what is called a tulip-style pussy (Google it). It's named for how the labia minora resemble a tulip about to bloom. With the tulip shape, her labia minora is slightly visible between the labia majora and all the way down her slit. Still, her labia minora are small and do not hang as in a curtain-shaped pussy. The point is, I always thought that if she had a hoop through her hood, it would be on display so nicely because of how her pussy is shaped. Her clitoris is small but barely hidden by her hood, and when she gets excited, her clit peeks out from her hood. That is why I knew the hoop ring's tension ball would stimulate her clit with that type of piercing.

Since our first threesome with my friend John, we have talked endlessly about that night and what we enjoyed. It filled our sex talk with fantasies of having another threesome with a large cock. As this story unfolds, you will see that she thinks a lot about fucking a big cock again and admits that she misses that full and deep feeling you can only get from a big cock. We use a large dildo regularly, but she still gets to the point where she can only think about the real thing, and the desire in her grows beyond her control. Because she is so open about this, with constant encouragement from me, I have told her that I want her to find a big cock and go fuck it. As this was early on in our relationship, that did not seem realistic, and also, I wanted to be there to watch that fat cock spread her tight pussy wide and make her cum. These are all the reasons we ended up having a second threesome with my friend John.

We were lying in bed one night, fooling around. Sometimes we would have a longer foreplay session where we would play with each other or even self-masturbate and tease ourselves. At the same time, we talked or fantasized about sexual things that turned us on. This particular night I was laying on my side and lightly rubbing her pussy while I looked at her amazing tits and beautiful face while we talked. She had my hard dick in her hand and lightly stroked me while we talked about the upcoming weekend.

It had been about 3 months since our threesome with John. John lives out of state, so we don't see him often unless he is in town visiting. However, Thanksgiving was coming up, and our friends have an annual "Friendsgiving" on the Saturday after Thanksgiving every year. John was usually at that party, but because of our threesome event, I had not reached out to him to see if he was actually coming. I assumed he would be, though. Regardless, his being there was the topic of our conversation/foreplay this night.

"I think it is going to be weird Saturday. We have not talked to him since then," Jess said.

"It might be weird for a minute, but then it will be fine. I think it could be fun to invite him over after and see what happens," I said. I really wanted to see her take his big monster again.

"You might not feel weird, but I am going to. I wonder if he will say anything about it or act differently?"

"I bet he doesn't unless you do. If he was smart, he would not bring it up unless we did. Either way, you can flirt with him. You have been really craving a big cock lately," I told her.

"I know, but now it's getting real, and I am getting nervous."

"Baby, we talk about it all the time, and we have done it once; if it happens, it will be fun. You told me last night that you can't stop thinking about fucking a big cock again. You said it's all you think about."

"It is. I want it, but it freaks me out a little."

"Baby, I want you to have a big cock. I love the idea of you fucking a big cock, and I totally want to see that," I reassured her.

"I know you do. I love that about you that we can be so open. I am so glad I don't have to hide this side of me," she said, leaning in and kissing me. Then she climbed on top of me and slid my hard dick into her wet pussy.

"Your pussy is so wet. Talking about a big cock fucking you turns you on. You can't hide it," I teased her.

"You were playing with my pussy, too. That is why I am so wet."

"Yes, but don't you wish you had a big hard cock instead of mine," I teased as I lifted up and ground my hard dick into her wet pussy.

"I wouldn't mind it if your dick was bigger if that is what you mean," she said. Moaning a little.

"Tell me why you want my dick to be bigger," I urged her on.

"I miss that full feeling," she said.

"My dick doesn't feel like that, does it?"

"No. It feels good but does not give me that full feeling."

"Why is that? Describe it to me. Tell me again what you like better about a big cock and why you crave it so much. I love hearing you describe it," I urged. I loved when she described things. Over time she has gotten incredibly good at it.

"You know I love how you feel and fuck me, but you also know it's smaller than what I like. I like the feeling of resistance as a large cock pushes into my pussy and the pop feeling when it first pushes through. It hurts, but it feels so good too."

"Can you feel my head at all?"

"A little bit, but not really. Your head is not much larger than your shaft. So I feel like I can feel your shaft better than your head. But when you fuck me, you know exactly how to get your head to my good spot, which I love," she said.

"That is hot baby. Keep fucking me. Tell me what else you miss," I told her.

"I like how deep it goes and when it bottoms out. I like when he can't put it in any further because he is too long. I like to teach down and feel him buried in my pussy, but at the same time, he is too long to go all the way in, so I can feel the part of his cock that won't fit. Then, I like to stroke the base that is still outside my pussy while I grind on it."

That night we had great sex, and I used the big guy on her telling her it was John fucking her with his big cock. I came up with a sexy scenario where John cornered her in the bathroom alone, bent her over the sink, and fucked her hard with his massive cock. She came in record time. Then she played with my dick and told me how she wished it filled her hands like John's big cock. She was very dirty, telling me how much John gets off knowing his cock is so much bigger than mine and how it turns him on to make her cum repeatedly while she tells him how much she loves his big cock. Needless to say, I didn't last long either.

When the night got there, we were all set to go. Jess looked amazing, of course. This party is a bit more formal, and people usually dress up more than usual. I wore a sports coat and dress pants, and Jess was in a very nice dress that came to just above her knees. The dress was made of a tight fabric that clung to her every curve. It had a deep neckline providing a ton of cleavage and accentuated her flat-fit tummy and natural curves. Because of the group of people at this party, she did wear nipple covers to tone her nipples down. Also, because of the thin fabric and tight fit of the dress, she did not wear any panties because no matter how skimpy they were, they showed through the dress, and she did not like that. So, to everyone's benefit, commando it was!

We got to the party, and quite a few people were already there. There were going to probably be about 40 people at this party. 25-30 were already there when we arrived, including John. Everyone's eyes turned to us when we came in, partly because I am a bit loud at times, but mainly they turned to look to see what Jess was wearing. The men want to drool, and the women want to critique. What is great about Jess, though, is she has this carefree, non-confrontational way of laughing people off. She also has a self-deprecating sense of humor and sometimes makes fun of her outfits. It typically puts most people at ease, and she pulls it off somehow.

As we said our hellos and made our way through the room, I went to the bar, made a drink for myself, and got Jess a glass of wine. Jess had stopped in the kitchen and was talking to Joanne (hostess) and some of the other women. So I went in there and gave her the glass of wine, then I went back to the great room to chat with people. The first-person being John.

"What's up, buddy. I was wondering if you would be here," I told him as I shook his hand and gave him a bro hug.

"Yeah, I got in Wednesday and went to my parents for Thanksgiving," he said.

"You should have given us a call and come and hung out," I immediately wanted the elephant in the room called out, and this seemed like the best time to do it before Jess came around.

"I thought about it, but since I had not heard from you guys since I was here last, I thought maybe I shouldn't?" He said kind of sheepishly.

"No, man. We're good. We had a great time then. We have no regrets, and hopefully, you don't either. It's only going to be weird if we make it weird," I told him, reassuring him and taking the driver's seat.

"Hell no! I don't have any regrets at all. That was one amazing night. I still can't believe it happened," he said, shaking his head and taking a sip of his beer.

"Yeah, it was wild. We talk about it quite a bit, to be honest. We had a good time, but Jess worries seeing you here tonight will be weird. I reassured her it would be cool and wanted to ensure you didn't act weird around her. Just be yourself, ok? Say hi, and hug her when you see her, just like you always do. Just be yourself, you know. Sound good?"

"Ok yeah, for sure. Thanks, man. Honestly, I was really nervous and didn't know how to act. I probably would have acted totally weird and different. But, if you guys are cool, then so am I, and I won't act weird at all," he said.

"Good, because she is headed this way now, so say hi to her first right when she gets her and goes in for a big hug. That will put her at ease," I told him.

Just as Jess got to us, he did just that. John gave her a big hug and a kiss on the cheek. Basically, what he always did before our threesome. I could see in her eyes that she was immediately put at ease. We stood there talking for a little bit catching up on John's life since we saw him last. He was single but had just started to date someone new, but it was too new to bring her to town to meet the family. We chatted some more, and I noticed we all needed a refill, so I offered to get them and left those two to talk as I went to the bar.

I got distracted at the bar talking to someone and was gone for a solid 10-15 minutes. I kept stealing glances over to John and Jess, and they were getting along great... actually, they looked like they were flirting. I immediately got that exciting feeling in my stomach, and my dick got chubby. Yes, they were most definitely flirting or at least Jess was. She kept laughing and touching his arm and, one time, his chest. I was very curious about what they were talking about.

I finally got back over to them and apologized for the wait. As I got there and gave them their drinks, Joanne and her husband, Doug, came over and talked to us. We all chatted, and then it was time to eat. They had a company decorate their very large and very nice garage so everyone could be seated together to eat.

They had tables set up for all 40 of us, and it was so well decorated you felt like you were in a banquet room and not a garage. We all got food and sat down, and enjoyed our meal. After dinner, Jess and I went back to the bar, did a shot with some friends, grabbed a drink and went outside. It was cool in the upper 60's, so I gave her my coat, and we looked out at the water while chatting.

"What were you and John talking about when I went to the bar?" I asked.

"Yeah, that conversation took a turn really fast. I guess the wine hit me because I embarrassed him," she replied.

"Oh boy! I can't wait to hear this," I was internally so excited I couldn't wait to hear what she said.

"It was actually really funny the look on his face. We were catching up, and he told me about this girl he was seeing. I asked the normal questions about how they met, what she was like, was he into her or was it a fling, you know. That kind of stuff. Then he said he wasn't sure she seemed intimidated by him. Then I blurted out without thinking, 'with that monster of yours, I bet she is intimated' I don't know where it came from, but after I said it, I started laughing really hard and hit him on the arm. His face went blank for a second, and then he said, 'dear lord, where are Jim and those drinks?' Then we both just laughed."

"Well, that didn't take long. I can't believe you said that. Where did it go from there?" I asked, excited and anxious to hear more.

Jess replied, "He tried to laugh it off, but I was feeling brave and asked, 'be honest, is that what you meant by intimidated?' he replied, 'not exactly but yes, sometimes that can be a bit of a challenge.' He told me they tried to have sex a few times, but she said it hurt too much and made him stop. So I teased him some more about it and agreed his size was not for the faint of heart."

"What did you say exactly? Don't hold out on me," I said. Actually, a bit annoyed she was holding back.

"Relax. Nothing bad. I am just teasing you some," she said, reaching up and kissing me. "I just joked with him a little after that and said, 'with something that big, I am surprised word hasn't gotten around, and more women aren't wanting to give it a try,'" she told me, then she reached down and grabbed my hard dick. "Someone likes me talking to other guys about their big cocks I see," and she proceeded to stroke me through my dress pants.

"It is very hot that you brought it up. I am still slightly surprised, but it's hot to hear about. Although, if I am being honest, I am a little jealous, too," I confessed.

"In a bad way? I am sorry. I didn't mean to go too far. I was making it a joke," she said with real concern.

"Not in a bad way. In an exciting way. I don't know, I am jealous, but it is turning me on too. I think I am jealous because I wasn't there to hear it but having you tell me is really turning me on," I said.

"I can tell. Your dick is hard as a rock. You never get jealous. That turns me on that this got you so worked up," she said and continued to rub my dick through my pants.

"Do you want to bring him home and fuck him?" I asked.

"I don't know, do you want to watch him fuck me with his huge cock?" she said teasingly, licking my ear and continuing to stroke my dick through my pants, letting her hand slide down and give my balls a squeeze through the thin fabric.

"Only if you want to, but I need you to really want it. Last time I made it all happen, but I want you to really want it and be fully on board," I said.

"I was fully on board last time. You didn't force me," she replied, a little indignant.

"I know I didn't force you, but I orchestrated the whole thing. This time I want you to really want it, and I want you to tell me that you really want this. Lately, you have been talking about how much you miss and are craving a big cock, so I want you to be honest and tell me if you really want it and then go for it," I told her.

"I don't want to take him back and fuck him without you if that is what you mean. I would want you there."

"Oh, I will be there. I am not missing out on this and want to have fun too, but I want you to make it happen, and I love how you tell me how much you desire it. So, you need to seduce him and get him to come back with us," I reassured her.

"Ok. Just so you know, I do want him to come back. My pussy has been wet, and I have been so horny since I said something to him about his cock. I went to the bathroom and wiped myself because I was so wet. I don't have any panties on, and I didn't want a droplet running down my leg," she said, laughing a little while licking my ear as she said it.