My Best Friend Meets My New Husband

Author's Note: I'm trying something different here since I'm having a brain block coming up with more adventures for the original My Best Friend and Her Husband series. This story involves the same characters from that series. Jessica is the narrator and it is about what happens if situations were reversed. I've never written a story from Woman's point of view before, so hopefully I can pull it off. Enjoy!

It all started two years ago when I was sitting at a bar alone in one of my little black dresses looking for some attention. The bartender put a drink in front of me and pointed to the guy that sent it. Wow, he was the hottest guy I've ever seen! Never being shy I took the drink and walked over to thank him. He introduced himself as Trent and we started to talk. He was watching the end a basketball game so his eyes were on the TV a little bit. He apologized and said the Lakers were his favorite team and wanted to watch the last 2 minutes. The game was about to come back from a timeout and I said "I bet they miss the next shot!"

He said, "No way, they'll make it!"

"What do you want to bet?" I asked.

"Loser buys the next round?" He offered.

"Done," I said.

The Lakers missed the next shot and not only was he upset they were still losing, he had lost the bet. "Double or nothing on the next shot, I say they make it this time," he said.

"Ok," I said. They missed again. "Now you owe me two drinks!"

"Double or nothing one more time," he suggested.

"Easy there pal, I don't think I can handle four more drinks," I said.

"Ok," he said, "Let's change the stakes."

That's how our relationship started, by making bets with each other. We made a couple more bets on the outcome of plays in the game, but then it ended and we started betting on things in the bar. I suggested we bet $1 on each since we were just having fun and I was enjoying the flirting. We were betting on things like if a guy would make a shot at the pool table or the dart board. Then it progressed to us betting on people trying to pick up others in the bar. Like if a guy approached a girl, we would bet if she would talk to him or totally blow him off.

It was getting late and I was getting tired. After a whole bunch of bets I was up $10. He looked like he was getting tired too, so he took his shot and said, "Ok, last bet, double the $10...so if you win you get $20, but if I win I owe you nothing and I get a kiss!"

"Deal," I said, "But I get to pick the bet." He nodded and I pointed to a nerdy looking guy walking towards a hot blonde in a tiny dress at the bar. "I bet she doesn't even acknowledge him."

"Jessica," he said, "That's not fair, I have no chance to win that bet."

"Better get your $20 ready then," I said.

Of course I won! I actually felt bad for the poor guy. He walked over and she glanced at him out of the corner of her eye and started looking at her phone. She didn't even look up as he tried to talk to her. Trent was upset and as he went to hand me the $20 I leaned in and kissed him on the lips anyway.

"What was that for?" he asked. "Not that I'm complaining."

"I lost the bet," I said and gave him a big wink.

He asked me for my phone so he could put his number in and he saw a text come in.

"Who's Nick?" He asked. "You could've told me you had a boyfriend."

"No, No, No," I said, "He's my best friend, not my boyfriend."

"Oh good," he said, "I had a really fun time tonight. Is it ok if I text you tomorrow?"

"Of course," I said and kissed him goodnight.

He did text the next day and we started dating. Our silly little bets continued throughout our relationship and he even incorporated them into some serious things. After about a year of dating, there was one night where the first big bet happened. We were sitting on his couch watching another basketball game.

"I say he makes the next shot," he said.

"I say he misses," I replied, "Stakes?"

"If you win I'll clean your apartment once a week for a month, and if I win you move in with me!"

"What?" I said surprised, and before he could say anything the ball swished through the net.

"Well, will you?" He asked.

"I'd love to," I said, "I pretty much live here already anyway!"

Living together was nice. He had a big house with a pool, and I was happy. We were as much friends as we were a couple and our bets kept everything interesting. The stakes had evolved into intimate things, like a blowjob while he was driving or in a restaurant bathroom if he won, and if I won I would get an hour long massage followed by him licking my clit until I screamed.

After almost a year of living together he offered me the second huge bet while watching another basketball game.

"I say he makes the next shot," he said.

"I say he misses," I replied, "Stakes?"

"If you win I'll clean the house once a week for a year, and if I win you'll marry me!"

"Whoa!" I said surprised again, and before I could say anything else, the ball swished through the net and he was holding a huge diamond engagement ring.

"Jessica," he said, "I love you so much, Will You Marry Me?"

"Yes! Of course I'll marry you!" I said.

I thought it was fun that he incorporated the proposal into one of our bets since they had become such a big part of our relationship. We eloped in Vegas and on our wedding night he admitted he rigged both of the big bets, because both of the games were pre-recorded. I didn't care and it made me love him even more.

About six months into our marriage he noticed me texting Nick again. "You know," he said, "For your supposed best friend, you rarely talk about him and I've never met him."

"He lives in New York," I said, "I've known him since I was 5. We've lost touch a bit over the years, but we're still best friends. If you want to meet him, I'll invite him to come out. I've been thinking about it anyway, I miss him."

"That's the most you ever told me about him," he said. "So you guys must have hooked up, right? That's why you've been hiding him from me?"

"No," I said, "We're just friends."

"You're telling me he's been your friend since childhood and he never made a move?" He said.

"I'm telling you Trent, we're best friends, that's all," I said.

"Oh, I get it he's gay," he said, "You're gorgeous. There's no way he wouldn't be all over you if he was straight."

I smiled at his compliment and said "He not gay, you'll see."

"Ok," he said, "I'll prove it to you...let me think...I bet your hot husband can seduce your 'straight' best friend."

"No way," I said, "We can't bet that! Plus I'm guaranteed to win. Why would you even want to bet that?"

"If you're guaranteed to win, why not make the bet?" He asked with a grin on his face.

"What's your definition of seduce?" I asked.

"I haven't really thought about it...how about I get him to kiss me?" he said.

"No way, that's not seducing," I said, "Plus how would I know if you didn't initiate the kiss to win the bet?"

"Blowjob?" He asked.

"Not good enough," I said.

"Are you saying that for me to win the bet, he would have to agree to let me fuck him?" He said.

"Yeah," I said, "You're the one that brought up seducing my best friend to prove to me that he's gay. If he's gay like you say he is, it should be easy to convince him to let you fuck him. If you want, you can even tell him I'm ok with it."

"This certainly went off the rails, quickly," he said chuckling.

"Aren't you glad these crazy bets are part of our relationship?" I said laughing, "C'mon what are the stakes?"

"Um..." he began, "How about if he gives me his ass, you finally give me yours!"

"What?" I said. "You know I don't do that!"

"Once again", he said, "If you're guaranteed to win, what are you afraid of?"

"Ok fine," I said, "If you can convince my straight best friend to let you fuck him then you're welcome to fuck my virgin ass, but if I win you put on my lingerie and I get to fuck your ass with a strap-on!"

"Holy Shit, Jess," he said, "Where did that come from?"

"All of this ass fucking talk got me thinking," I said, "You've been bugging me to let you do that forever so I figure you should know what it feels like!"

"Are we really doing this?" He asked.

"Once again," I started, using the same line as him earlier, "You brought it up. If you're so confident in your seducing abilities, you stand to have a ton of fun and fuck two virgin asses!"

"Ok," he said, "It's a bet!"

"One last addendum," I said, "If he actually agrees to let you fuck him, I get to watch!"

"Deal!" He said.

ONE WEEK LATER- NICK ARRIVES

After our bet I made the call. Nick was thrilled to hear from me since we just about only texted. I told him I missed him and wanted to introduce him to my new husband. I said there was plenty of room and he should come out and visit. He said he could fly out Friday morning and stay until Sunday.

I picked Nick up at the airport and brought him to the house. He clicked with Trent right away and it was like we were three best friends. I started to question if Trent would even try to win the bet. We had lunch and Nick went to the guestroom to unpack and get settled.

"Babe," Trent said, "Why didn't you tell me he was so cool?"

"I tried to tell you," I said, "He's been my best friend forever. I knew you'd like him too."

"I think we should call off the bet," he said, "I can see we're all gonna be good friends and I don't want to make it awkward."

"No way Jose," I said, "If you want to forfeit you can go pick out your favorite set of lingerie and get ready for your pegging!"

"Come on Jess!" he said.

"Nope!" I said. "This was your idea. Take your shot and if it gets awkward I'll explain to him that it was a silly bet. He'll be fine with it. You see how cool he is!"

"So you still want me to try to seduce him?" he asked.

"I don't want you to do anything you don't want to do," I said, "We made a bet and if you lose, you know where I keep my lingerie."

Nick walked back into the kitchen and told us he had forgotten to pack his toothbrush and razor and asked if we could go to the store.

FAMILY ROOM- EVENING

We took Nick to buy some toiletries and we stopped at the grocery store so I could buy something for dinner. We ate and caught up while my two guys bonded some more. After dinner we went into the family room to watch TV. I was tired and the guys stayed up to watch a basketball game. They were both sitting on the same couch and Trent decided he would at least try to win the bet, even though he didn't think he had a chance.

"Jess hasn't even told me how you guys met," Trent said.

"We were next door neighbors when we were five. Our moms were friends and we were over each other's houses playing together all the time," Nick said.

Trent started to inch closer on the couch and asked, "And after all this time you never hooked up?"

"Nope," Nick said.

"But you're a handsome guy," Trent said, "And we both know how hot my Jessica is..."

"That's nice of you to say," Nick said, "I guess there were times I thought about it and I'm sure there were times she thought about it, but I guess we were such good friends that we didn't want to ruin it."

Trent put his hand on Nick's leg and asked, "Do you think I'm handsome?"

Nick was totally caught off guard and started to stutter, "I...I...I..."

Trent took advantage of Nick's open mouth and before Nick could get a word out Trent kissed him, slipping his tongue into his mouth. Totally surprised by what was happening to him, instinct took over and Nick returned the kiss and they made out.

"What the hell was that?" Nick said, "I'm not..., You're not...,You're married to my best friend!"

"I thought it was nice," Trent said, "It seemed like you enjoyed it too by the way you kissed back!"

"It was a force of habit!" Nick said, "Plus I don't think we should be doing this with you're wife sleeping in the next room!"

"Are you saying it would be ok if she wasn't sleeping in the next room?" Trent asked.

"You know what I mean!" Nick said, "I'm tired, I'm gonna go to bed."

"Ok," Trent said, "Goodnight!"

MASTER BEDROOM- EVENING

Nick went to his room and Trent got into bed with me.

"That was fast!" I said.

"What do you mean?" Trent asked.

"You seduced him and fucked him on the couch, right, Mr. Big Shot?" I said sarcastically.

"No, my dear," he said, "It's gonna take some time."

"How far did you get?" I asked.

"I...uh...I rubbed his leg and kissed him," he said.

"What?" I said. "You kissed him? You're supposed to get him to put out for you. You're not supposed to initiating anything!"

"But he kissed me back!" He said.

"Interesting," I said, "Then what happened?"

"He got flustered and went to bed," he said.

"I can't believe he kissed you back!" I said, "Like with tongue?"

"Yeah, I stuck my tongue in his mouth and he stuck his tongue in mine. We actually made out for about thirty seconds, I could tell he was really getting into it," he replied.

"That little slut!" I said, "If my best friend was a girl and she made out with my husband I would kill her."

"And since he's a guy?" He asked.

"You know what?" I said, "This changes things. Now I want you to win the bet!"

"Really?" He said.

"Yeah," I said, "I'll even help you. Since you say he enjoyed kissing you so much, I'll get him to put on my lingerie and you can fuck him in the ass!"

"But what about your end of the bet?" He asked, "Isn't this like you forfeiting?"

"I was gonna let you fuck my ass anyway," I said, "You can do it right now if you want. We just have to be quiet so we don't wake him."

"I'm not gonna say no to that!" He said.

He pulled the sheet off me and in a split second we were both naked and kissing.

"So who's a better kisser?" I asked jokingly.

"What do you think?" he said sternly, "You're gonna pay for that!"

He kissed my neck and down my body, pausing to take each nipple in his mouth and sucking on them for a little while. I was doing my best to keep quiet, but when he reached my clit and gave it a long lick, I screamed out and he said "Shhhh." He started to lick my pussy and I had to put my hand over my mouth. Then he took my feet and put them on the bed, bending my knees. He put his hands under my waist and lifted me up a little bit. I wasn't sure what he was doing, but then I felt his tongue against my asshole. As he started to lick me I wanted to scream again, so I put a pillow over my face and screamed into it! My body was thrashing up and down as he bathed my asshole with his tongue. I was moaning into my pillow until he stuck a finger inside me and I yelled out "Holy Shit!" He added a second and a third while continuing to lick the edges of my hole. I felt silly holding a pillow over my face, but I think the tingling sensation I was feeling all over my body was heightened by the fact that I couldn't see anything.

When he thought I was ready, he pulled his fingers out and went into the bathroom to look for some lube. He came back with a tube and I was surprised that we had any. Later he would tell me that he bought it in anticipation of winning our bet.

"Feeling good Babe," he asked.

"Yeah," I said, "I'm only about to explode."

"And we haven't reached the main event yet!" he said. "Do you think you can control your screaming? It would be a shame for you to have your first anal experience with a pillow over your face."

"Well I guess you're gonna have to come up here and make out with your wife as you make love to her asshole for the first time!" I said.

He started to lube me up and slowly put a finger back inside. Then he lubed himself up and put my legs on his shoulders. I raised my ass off the bed a little to give him the right angle as he lowered himself on top of me and started kissing me. He reached down to line up his cock and slowly entered me. "Slowly," I moaned into his mouth. He listened and moved as slow as he possibly could, filling me inch by inch. It took some time, but when I felt him stop pushing I knew he was all the way inside me. I yelled a muffled, "Oh My God!" into his mouth. He didn't move and held himself deep inside of me to let me get used to it. We were still making out like crazy and when I felt ready I said "Fuck my ass!"

He started to pull out slowly until just the tip was in my ass, then he plunged back in to the hilt. I moaned into his mouth again and he repeated fucking me with full strokes. I couldn't believe how big he felt inside my rectum as he was thrusting in and out of me. My whole body was starting to tingle like I was about to have an orgasm. I had no idea women could have an orgasm from anal sex alone, but here we were. I started to cum and I could feel my asshole squeezing his dick. It was his turn to scream in my mouth as he started to shoot and leave a huge load in my ass. He rolled off of me and we were both out of breath.

"That was amazing!" I said. "If I knew it would feel this good I wouldn't have resisted so much!"

"Yeah," he said, "That was awesome! The way you squeezed my dick! Wow! How did you do that?"

"I have no idea," I said, "I think it was involuntary from the orgasm you gave me."

"We're definitely doing that again!" He said.

"Absolutely," I said, "Thank you for being so gentle with me for my first time. I bet Nick is going to enjoy himself even more!"

GUESTROOM- MORNING

Trent and I got a good night's sleep and when I went to check on Nick he was still sleeping. I changed into a short light blue babydoll with my boobs pretty much hanging out. I walked into his room quietly, sat on his bed, and waited for him to wake up. It took only a few minutes until he started to rise and he looked at me.

"Oh, Good Morning Beautiful!" He said. "How long have you been sitting there?"

"Good morning Handsome," I said exchanging out pet names for each other. "Only a few minutes. How did you sleep?"

"Great," he said, "And Whoa! Do you always walk around the house like that?"

"Only for special occasions," I said and giggling. "So I heard you had a nice time with Trent last night."

"Yeah, Beautiful," he said, "He's a really nice guy, you did well for yourself!"

"You know, you always call me Beautiful and I always call you Handsome, but you never made a move on me," I said.

"Oh Jess," he said, "We've been friends forever. I would never want to ruin that."

"Do you think Trent is handsome?" I asked, starting to pry.

"I guess," he said, "It doesn't matter what I think though. You obviously thought he was handsome enough to marry."

"He told me what happened on the couch last night," I said, continuing to push.

"What did he say?" he asked, starting to get nervous.

"That you kissed him!" I said. "That's why I asked if you thought he was handsome."

He was getting extra nervous now to the point of stuttering, "But...Jess...I didn't want to say anything, but he kissed me...first!"

"I heard you stuck your tongue in his mouth and you two made out. I had no idea my best friend and I had the same taste in men!" I said winking.

He was totally stunned now and could barely get the words out, "No...Jess...I don't...I didn't...this is a whole big misunderstanding...I guess we drank too much...but believe me, he started it!"

"Even if he started it, you still kissed him back, right?" I asked with a grin.

"Well, yeah, I guess so." He said.

"Did you like it?" I asked. "He said you were into it."

"I don't know Jess," he said, "I've never kissed a guy before."

"It's ok to like it, Trent is a great kisser," I said.

"Wait," he said, "Why is your husband kissing me in the first place?"

"Because I told him he could," I replied.

"What?!" he said, "Why would you do that?"

"It was one of our bets," I said, "He bet me you were gay and I said no way. Now I'm not so sure."

"I'm not gay, Jess, you know me!" He said.