My Best Friend Meets My New Husband

"I thought I did, but now I find out your making out with my hot husband and I can see this conversation is making you excited!" I said, pointing towards the tent forming in the sheets near his crotch.

He said, "It's just a morning hard-on, I just woke up, remember?"

"Are you sure it's not because you're visualizing making out with Trent again?" I asked. "What's the real reason you never made a move on me? Come on, we've known each other for over 20 years, tell me!"

His face was starting to turn red and he was stuttering again, "I...I...I..."

I reached over and started rubbing his dick through the sheet. Then my hand wrapped around it and he gasped. I said, "Oh Nicky Baby, this is no morning wood, you are rock hard. This conversation is getting to you. Come on, tell me, tell your Beautiful Jessica why you never hit on her."

Still stuttering he said, "I...I...I...I don't know."

I lifted the sheet, lowered his boxers. With my other hand I took his left hand and placed it on my right breast which was just about to fall out of my babydoll. "Tell me baby, tell me why you don't want me? I can feel how hard you are and I'm sure you can feel how hard my nipple is? You call be Beautiful all the time. Do you really think I'm beautiful?"

I stroked him up and down, jerking him off as he started to breathe heavily. He responded by rubbing my nipple in between his thumb and pointer finger. He said, "Of course I think you're beautiful, you're one of the hottest women I've ever seen!"

"Aw, thank you Baby," I said, jerking him even harder. "But that doesn't explain why you never tried to do something with me. Was Trent right? Are you secretly gay?"

"Noooo," he screamed as I could feel his orgasm approaching.

"Wait, I think I figured it out. You never wanted to be WITH ME, because you want to BE ME! Is that what you want? Do you want to look beautiful like me? Wear sexy lingerie like me and get fucked by a hot guy like me? Do you want to scream his name as he cums deep inside of you?"

"YES! YES! YES!" He screamed as he came all over my hand and onto the sheets. I wiped my hand and he stopped rubbing my breast as he tried to catch his breath.

I leaned down to give him a peck on the lips and said, "I can't believe Trent was right!"

"What do you mean?" He said. "Right about what?"

"I just asked you if you wanted to look beautiful, wear lingerie, and get fucked," I said, "And I'm quoting you here, you said Yes!, Yes!, Yes!"

"That was me responding to my impending orgasm," He said.

"Then answer my question, did you like kissing my hot husband?" I asked.

He took a deep breath and said, "It was nice. Like you said he's a good kisser."

"Did you like it because it was my husband or because it was a guy?" I asked.

"I don't know," I said, "I haven't really thought about it. I've kissed plenty of girls before and who doesn't like a hot kiss."

"Oh, so now it was hot?" I said, "Before you said it was nice. Which is it?"

"I don't know Jess," he said, "Stop nitpicking every word I say."

"Well I bet Trent would consider it hot, because right after you made out with him he came into our bedroom and fucked me in the ass for the first time!" I said.

"Oh my, Jess!" He said surprised.

"It was amazing," I said, "Have you ever had anything in your ass?"

"What?" he said, "No! Hold on, actually one time a girl stuck her finger up there while she was blowing me. Wait, why am I telling you this?"

"Because I'm your best friend," I said, "Did you like it"? Did you like it when she fingered you?"

"I did cum very hard," he said, "But maybe she was just good at giving blowjobs."

"Do you wish I stuck my finger in while I was jerking you off just now? I asked.

"I don't know," he said, "Maybe, all this ass play talk is making me wonder."

"Have you thought about how good it would feel and how hard you would cum with something bigger inside of you?" I asked.

"Not really," he said.

"Trent is a very tender lover," I said, "He was very gentle with me last night and made sure I was comfortable."

"What are you trying to say?" He asked.

"That maybe you want to try it." I said.

"You want your husband to fuck me in the ass???" He asked.

"Only if you want to," I said, "I would be ok with me. You certainly liked kissing him."

"Jess," he said, "Kissing and fucking are two totally different things!"

"Yeah," I said, "Fucking feels one hundred times better!"

"I don't know Jess," he said, "You're kinda messing with my mind right now."

"Just promise me you'll consider it," I said.

"Ok," he said, "I'll think about it, but don't get your hopes up."

"You know what, I'll even sweeten the deal. If you let him fuck you I'll let you do whatever you want to me. Think about it. I'm going to take a shower. Looks like you should too. Oh, and do me a favor and strip the sheets so I can throw them in the wash. I don't think you want to sleep on those again tonight, or maybe you do," I said winking.

I gave him a quick opened mouth kiss and left the room.

KITCHEN- MORNING

I took my shower and got dressed. I filled Trent in on the progress I had made with Nick this morning, including the handjob and the nipple fondling. He looked a little jealous, but then he realized it was all part of the plan. I sent him out for bagels and muffins so I wouldn't have to make breakfast. He had just walked in the door and the coffee was ready as Nick walked into the kitchen.

"Good morning," Trent said, "How did you sleep?"

"Great," Nick said, "For a guestroom you guys certainly picked a top of the line mattress."

"Anything for my BFF!" I said.

"Yeah," Trent said, "She remembered you had a little trouble sleeping so we went out and bought that special for you."

I punched him lightly in the shoulder and said, "Babe, you weren't supposed to tell him that!"

"Why not?" Trent said. "Aren't we all friends here? There's no secrets between friends. You guys have been best friends forever and I feel like Nick and I are headed that way too."

"That's nice of you to say Trent," Nick said, "I was telling Jess this morning that I really like you too."

We ate our breakfast and talked about our plans for the rest of Nick's visit. Nothing came up about last night or this morning.

"Oh shoot look at the time," I said, "I have an appointment at the salon so I can make myself beautiful for my two guys."

"I don't think my wife could be anymore beautiful!" Trent said.

"Yeah Jess, you know you're gorgeous," Nick said.

"Aw," I said, "You guys are sweet, but I'm gonna go anyway if that's ok."

"Of course," Trent said, "Nick and I will hang out by the pool and drink some beers. Sound good, pal?"

"Sure!" Nick said.

"Cool. Have fun and behave yourselves...or don't." I said giggling.

I spent a few hours at the beauty parlor getting my hair done, a facial, and a massage. I wanted the boys to have plenty of time to bond. When I got home Nick was taking a nap and Trent told me everything that happened while I was out:

TRENT'S STORY AS TOLD TO JESSICA

Trent:

After you left we got changed and jumped in the pool. We swam a little bit and played some H-O-R-S-E on the pool basketball hoop. When we got hungry I barbecued some burgers and dogs.

Jessica:

Would you get to the good stuff?

Trent:

Do you want to hear the story or not?

We were talking while we were having lunch and you came up. He told me more about you guys as kids. I told him how I was a little jealous because I didn't have any close friends from childhood. He said he was happy that you and I found each other and he had a feeling the three of us would be great friends.

Jessica:

Babe, you're killing me. Did you make a move or were you scared? I just about had him ready to go for you this morning.

Trent:

I'm getting there, just listen please.

We didn't want to jump back in the pool so fast after eating so we got in the hot tub. I'll do my best to recreate the conversation for you:

T: Thanks again for coming out. It's been fun and I know Jess has been thrilled to see you.

N: Of course. I needed a vacation and when Jess told me she was married, I wanted to meet you. Thanks again for getting that mattress. I slept like a baby!

T: No problem. Anything to make our guest comfortable. Speaking of being comfortable, should we discuss the elephant in the room?

N: What's that?

T: About what happened last night. Jess told me she told you about our bet.

N: Oh. You mean how you kissed me?

T: I remember you kissing me back.

N: Force of habit, I guess.

T: Come on, it was more than that. I could tell you were into it. Then you told Jess it was nice and then later you said it was hot. Which was it?

N: I don't know, both I guess. What made you want to kiss me anyway when you are married to a beautiful woman?

T: More importantly, how come you really never tried to hookup with that beautiful woman?

N: That seems to be a common question around here. The answer is I don't really know. She's been my friend for so long. We grew up together, spent a ton of time together, had sleepovers, told each other secrets, and then one day she became this beautiful bombshell and I only thought of her as my best friend.

T: Was it just her that you didn't try with or were there other girls?

N: Oh, I've been with a handful of girls, they just never went anywhere?

T: What about guys?

N: Like I told Jess, I'm not gay.

T: So I was your first?

N: Yes, I mean no, I mean Yes you were my first kiss, but there hasn't been a first anything."

T: Not yet.

N: What do you mean by that?

T: Jess told me a little more about your conversation this morning. I'm trying to remember her exact words, but she said you were going to think about putting on sexy lingerie and getting fucked in the ass.

N: What? I didn't say that. I mean I guess I did, but I wasn't seriously considering it.

T: You really should. I've been checking out your ass all afternoon and I think it would look smokin' hot in a thong! Did Jess tell you what we did last night after you and I made out?"

N: Yes.

T: Did she tell you how much she enjoyed it and how gentle I was with her?

N: Yes.

T: It would be the same way for you.

N: I don't understand where all of this is coming from. Are you sure you're not the one who's gay? You are married to a gorgeous woman who will do anything for you. Why would you even think about me?

T: I love Jess and she loves you. This all started because I couldn't understand why you never tried to be with her. That made her start to wonder too. Then she had this crazy idea that the reason why you didn't want to be with her was because you wanted to be her.

N: Yeah, she said something like that earlier.

T: Well is it true? Is that the reason you call her beautiful and gorgeous, but never did anything about it? Do you want to be beautiful and gorgeous? Is that why you had a hot make out session with her husband last night? Because you wish you were her?

N: No. I don't know. Maybe. This is so confusing.

T: Ok, now we're getting somewhere. I love Jessica and I would do anything for her too. That includes helping her best friend. If you're confused and need help figuring things out, I'm here for you. No pressure.

N: Thanks. Until you kissed me last night I never had a thought about being with another man. Between my conversation with Jess this morning and this one right now, I don't know what I want to do.

T: Let me see if I can help. It's just us in this hot tub. Jess won't be back for at least another hour. This conversation has given me a rock solid boner and it looks like you're working on one too. You admitted you liked the kiss last night, so why don't we fool around a little more and see what happens.

(Back to Jessica narrating)

"No way!" I said, "He agreed to make out with you in the hot tub?"

"Like a virgin on prom night! Trent said. "This time he kissed me first and shoved his tongue in my mouth."

"Wow, that's so hot!" I said, "Then what?"

"We probably kissed for 10 minutes straight and then I took off my swim trunks," Trent said.

"No way! I don't think we've ever made out for 10 minutes straight. Are we sure my hot husband wasn't enjoying kissing a dude too much?" I said laughing sarcastically.

"You know I'll do anything to win one of our bets! Even though you already paid up, I still want to win. Plus he really is a good kisser, you may have missed out," He laughed sarcastically back at me.

"Ha, so what happened next?" I asked

"While my trunks were off and we were still kissing, I took his hand and put it on my dick to see what he would do. He wrapped his hand around and started stroking!" Trent said.

"Did you jerk him off too?" I asked.

"No, he tried to pull my hand over to his crotch but I put it on the side of his face instead," he replied.

"So long story short, you got a handjob in our jacuzzi while making out with my best friend?" I said.

"Yeah," he said, "Are you jealous?"

I said, "But I'm not sure which one of you I'm more jealous of... Anything else happen?"

"Oh, while he was in the shower I took that pink babydoll and thong you look so hot in and hung it in his closet. I don't know if he's seen it yet," he said

"I guess we'll find out soon enough!" I said.

PATIO- EVENING

Dinner time was approaching. Nick had woken from his nap and we watched some TV. Trent fired up the grill again to make some steaks. Nick helped me in the kitchen making some sides and we all sat down at the table on our patio. The guys had some typical chit chat about sports and I asked some more details about his life in New York. We were having a pleasant meal when I decided it was time to spice things up.

"So Nick, Trent told me you guys had a fun time this afternoon, especially in the hot tub," I said winking.

Nick's cheeks started to get red. He looked at Trent and said, "You told her? I thought we were keeping that between us?"

"Oops," Trent said, "I guess I forgot."

"So my BFF got to do some more kissing and got acquainted with my hot husband's cock? Isn't it spectacular?" I asked

"Yeah," Nick started to say, "I mean I don't know, I've never touched one before."

"From the way you were stroking it, I could tell you liked it!" Trent said.

"Have you thought anymore about what we talked about?" I asked.

Nick's face was getting redder. "Which part?" he asked.

I took his hand and put it on my breast and said, "About why you never came on to me and that maybe you had some other kinds of feelings deep down inside you never realized."

Nick didn't answer, and removed his hand so he could keep eating. We all ate in silence for a minute or two.

"You know it's ok to have feelings," Trent said, "We're here for you no matter what. You've been best friends with Jess forever and I feel like I know you forever already."

"I don't know what I'm feeling," Nick said, "It's all so confusing. I never had any of these thoughts and then I came to visit my Best Friend and new husband and they came out of nowhere."

"It's ok sweetie," I said, rubbing his hand, "Take as much time as you need."

"Let me see if I can help," Trent said, "I'm gonna ask you some rapid fire questions and you answer Yes or No as fast as you can. Then the three of us will have a discussion. Sound good?"

"Ok," Nick said hesitantly.

T: Did you like it when we kissed?

N: Yes.

T: Did you like it when Jess kissed you?

N: Yes.

T: Did you like rubbing Jess' breast and nipples?

N: Yes.

T: Did you like it when she jerked you off?

N: Yes.

T: Did you like it when you jerked me off?

N: Yes.

"Ok," Trent said, "I don't know if you realized it but you said Yes to every one of my questions. So it's safe to say you've enjoyed your time with us."

"Yes," Nick said, "I've had a great time so far."

"I have one last question with a couple of follow-ups," Trent said, "Did Jess tell you what we did last night after our make out session?

"Yes," Nick said.

"What did she tell you?" Trent asked.

"That she let you fuck her in the ass for the first time," Nick said.

"What else did she say?" Trent asked.

"That you were very gentle and she loved it," Nick replied.

"Do you think it would be any different for you?' Trent asked.

"I don't know," Nick said.

"You know that men have that little button inside their ass that women don't have, right? I bet I can make you cum like a fire hose and scream my name!"

Nick didn't respond and now his face was bright red and he was sipping his drink nervously. I started rubbing his hand and said, "It''s ok, Handsome."

"Yeah, it's ok," Trent said, "We're just trying to help bring out those feelings, assuming they're even in there. Just say the word and we'll drop it. We'll go back on our path to becoming three best friends and the make outs and handjobs will be things we joke about in 20 years...Or maybe you want to try it? You might love getting fucked? You might love being Jessica's twin? You might hate it and never want to do it again, but you won't know if you don't try."

Trent had really laid it on thick. I was starting to wonder if he was just trying to win the bet or if he really wanted to fuck my best friend. Either way my panties were starting to get a little damp. Still rubbing Nick's hand I said, "Take you're time and think about it. Remember afterwards you can do whatever you want to me."

"After we eat, Jess made Chocolate Lava Cakes that are so good they may make you orgasm just from eating them! Maybe they'll help you decide," Trent said laughing.

We finished dinner and I put the Lava Cakes in the oven. Trent went to get a tray for some after dinner drinks and Nick got some glasses with ice. We were enjoying dessert and everyone was acting like the previous conversation never happened.

Suddenly Nick said, "I think I'd like to try."

Knowing full well what he meant I started to rub his leg and said, "Try what?"

"You know, the thing we were talking about. I want to know what it feels like." Nick said.

I started slowly moving my hand up his thigh until I reached his crotch. I felt his dick start to stir and I said, "We need you to say it so there's no misunderstanding."

I was really rubbing him now and he yelled out, "I want to put on the sexy lingerie that's hanging in my closet so your hot husband can fuck me!"

"And wear my makeup and a wig? I asked, egging him on.

"And wear your makeup and a wig!" He replied.

"So you can be my twin?" I kept going, rubbing his dick harder.

"Yes! So we can be twins!" He said.

"You really want to be me don't you?" I asked.

"Yes!" he screamed.

"What should we call you?" I asked, knowing this would be the final piece.

"Nicole!" He screamed again.

I stopped rubbing him and put my hand back on the table leaving him with a raging hard on. I gave Trent a look and smiled as our plan had worked. "I'm so proud of you," I said to Nick, "You're really going to enjoy this, I promise."

MASTER BEDROOM- EVENING

We finished dessert and cleaned up the dishes. Nick said he needed to use the restroom so I told him to grab the lingerie set from his closet and meet me in my room so we could get dressed. Trent went into the family room to watch TV and we told him we would call him when we were ready. As I was walking to my room I felt a little guilt creep up. Had I corrupted my best friend of over 20 years because of a bet? Did we talk him into something he didn't want to do? I know I am very persuasive and have a somewhat dominant side, but I would never want to hurt someone I love. He did kiss Trent back and admitted he liked it, but he also liked touching me and kissing me.

I was reassured when he walked into the room, the pink babydoll and thong in his hands and a big smile on his face and said, "So how do we do this?" He was clearly into it and I was gonna make sure he had the night of his life before he leaves to go home tomorrow.