Date Night with Wife's Friend

Author's Note -- this is a slow build story not a quick jerk, so fair warning.

Special Thanks to Todger65 for your patient editing of this work.

"Is Katie coming over tonight?" My oldest daughter asks.

"Yes, auntie Jen is going to let her stay the night."

"Yay!"

'Auntie' Jen is my wife's best friend; they'd been so since before I'd met either of them. Jen is a single mom of a little girl between the ages of my own daughters and they are close enough we've started calling them 'cousins'.

Jen's 'ex-' is a dirt bag that not only knocked her up while she was practically unconscious, but has made every effort to avoid parental responsibility since. I couldn't understand how he could want nothing to do with the sweet adorable girl that Katie is and so I kinda try to be a father like figure for her as much as I am able.

As many single moms' do, Jen is having a hard time both being a parent and trying to get out and date. So tonight we are babysitting so she can go out with a new guy she's recently met online through one of those dating sites.

I believe this is her fifth date so it seems like it is going pretty good.

I haven't been home long, just getting changed out of my work clothes when I hear the phone ring, and then Lisa's voice carrying up the stairs sounding both sympathetic and reassuring.

"Honey, take a shower and dress to go out."

"Katie not coming? What happened?"

"Jen's date canceled, but she's still dropping Kate off and you're going to take Jen out tonight."

I can't be sure I'm hearing her correctly. "What's that?"

"Jen needs a night out with a nice guy, and since we don't know any single ones, you are going to substitute."

I duck my head back out of the bedroom to look down the stairs to see if she is pulling a joke on me, "are you serious?"

"Yes, now get into that shower." She responds with a look of complete seriousness, softened by a smile.

I didn't hesitate any further and immediately begin getting ready for a date night, the first one not with my wife since I'd been 18.

I feel my heart race, my body flush, and butterflies in my stomach all with a pre-date nervousness that has me confused. I know it is only a dinner out with a friend and yet it feels like I am a teenager about to go on a first date.

I climb downstairs wearing jeans and a turtleneck and Lisa frowns and shakes her head at me in disappointment.

"Go back up there and dress nice, she has reservations at a nice restaurant, not the diner."

I shrug and go back upstairs to dress more appropriately. When I come back down a second time she smiles at me approvingly.

"That's better, now you look sexy. I'm a little jealous of Jen now." She says with a smile.

"Is it too much?" I'd switched to a two piece dark blue suit with a light purple shirt and tie my wife always liked on me though I didn't wear them often.

"I want you dressed to make me a little jealous tonight, this is perfect."

"Do I hear Katie here already? Is Jen waiting?"

"Yes, Katie is here, Jen dropped her off while you were showering and no she isn't waiting, not yet, she's home getting ready."

"So what am I doing tonight?"

"Everything she was going to do with her date, pick her up, dinner, etc... She's already got the reservations, and you are paying."

"Okay but... I haven't been on a date with anyone but you in ages, and before then I didn't have many dates. I'm a little nervous here."

"Sometimes I forget how cute you are. Don't be so nervous, you certainly know her as well as you knew me by our first year of dating, so it's not really a 'first' date. Let her lead the date and be the good guy I know you are."

"Okay," I say, "but I still feel like I'm cheating on you."

"You're not, go out, have a good time, and most importantly make sure she has one. If she tells me you were anything less than exemplary tonight, then you'll hear from me." Again she smiles at me.

"I'll try..."

"You'll be fine, you've gone out to dinner with her before, never without me true, but you don't need me to have a pleasant evening."

"And you are okay with this?"

"Yes, now go or you're gonna be late and Jen will worry that you aren't going to show."

With that final blessing a hug and kiss, I grabbed my keys, and go out the door to my car.

Fortunately the drive to Jen's is a short one, otherwise I may chicken out, as it is I am all twisted up inside again as I pull into her driveway 10 minutes later.

I walk to her front door and ring the bell. A few moments later she answers and I don't have to feign my reaction.

A black dress with a deep plunge draws immediate attention to her cleavage and it is an excellent choice to work with her curves.

"Wow!" Is about all I can say, and she flushes as she smiles at me.

"You're just being nice, but thank-you."

"No, seriously, you look hot." I respond, "some handsome guy is probably gonna steal you off my arm the moment we get to the restaurant."

"I doubt anyone would be interested, and you are pretty damn good looking yourself. Besides, tonight you are my date."

"Yes I am! Where to?"

"Tony's."

"Nice choice!" I say with a smile and I hold out my hand to escort her to the car.

She was wearing heels, and the walkway is a bit uneven which makes me concerned she might turn an ankle without the support. I open the door and help her into her seat before closing the door and going around to my side and climbing in.

In the car we talk about everyday things, the same stuff we've always talked about to each other, our girls, their schools, our jobs.

Once we are at the restaurant our conversation starts on what we were thinking of ordering, including deciding we'd share an appetizer.

After placing our orders though our conversation seems to stumble to a halt as we run out of the everyday things to talk about. I am only thankful that Jen seems as nervous as I feel.

"Guess it had to get weird at some point." I say with a small smile.

"Yeah, no kidding. What is your wife thinking?" Jen responds with her own smile.

"Don't ask me, she's your best friend, and you've known her longer."

"Okay so what do we do now?"

"I haven't been on a 'date' in nearly 20 years. What would you normally be doing if I were any other guy?"

"Since I'm a bit hard-up, we'd probably be making out." Jen says with a self depreciating smile and a raised eyebrow.

My eyes nearly pop out of my head, "lucky guys!"

"They must not think so." And now her voice takes an even more dejected tone.

"Their loss," I say as I slide my chair around to her side of the table, I hold her chin up in the crook of my right index finger, bringing her eyes to meet mine, "you are a beautiful and sexy woman, and any guy should count himself lucky to be graced by your presence for even a moment. Any guy too dumb to realize that doesn't deserve the privilege."

I bend down to kiss her, in what I intend to be no more than a friendly supportive kiss, but as our lips meet, she seems to melt into me. Her soft and delicate lips part, and my tongue automatically takes that as invitation, and goes in to tickle her tongue for several long delicious moments before we both come back-up for air, both turning a little red and feeling more than a bit self-conscious.

"Um, yeah, sorry about that." I mumble.

"No, I'm sorry; I shouldn't have kissed you like that..."

"I thought I kissed you..." I respond with a smile.

"This is getting more than a little confusing." Jen says softly, "do you mind if I go give your wife a call?"

"No, of course not." I answer immediately.

"Thanks, excuse me." Jen says as she slips out of her chair and takes her phone outside.

I sip on my glass of wine, as I take slow bites from the bread placed on the table.

After several minutes and about the time I am becoming concerned Jen is on her way back to the table with a bemused smile on her face. I feel my phone vibrate, and I check to see a text from Lisa.

'Just remember what I told you. Love you.'

"Everything ok?"

"Yeah, great; first of all I have to say your wife is the most generous and amazing best friend any woman could have."

"She is awesome." I agree with a smile.

"Do you trust me?" Jen asks her eyes open and honest.

"Implicitly."

"Good! Because if you'll just follow my lead I can guarantee you will be within the rules your wife set for our date, and I'll have the best date I've had in months if not years."

"Sounds good to me, so what are the rules?"

"That's the trick, you just have to follow my lead and trust that I won't lead you out of them."

"That sounds like fun already," I say with a smile.

"Glad you agree, now come slide in next to me instead of sitting across from me."

I move around the table and Jen slides in as close to me as she can.

"Make out with me John." She says softly, nearly pleading.

Having already said I was willing to take her word for the night's rules I lift her chin, tilting her head up as I bend down her lips are parted expectantly.

Our lips meet and it is again, pure electricity. There was an excitement of a first or at least early kiss that I vaguely recalled from when my wife and I had first dated. It wasn't that the spark had left us, because I know she still starts a fire in me, but there is something special about the unknown, the previously untouched.

Time stops. The restaurant, the people, the murmur of other voices, they all completely disappear as Jen and I just enjoy each other and the moment. I'm not sure how much time passes before we separate, but our meals are already on the table.

"My god, you are a good kisser." Jen whispers.

"So are you." I reply back with a self conscious smile.

"I have never enjoyed making out with anyone so much." Jen says with her eyes practically sparkling.

"Actually just sitting and making out, Lisa and I haven't done in years. Didn't realize how much I missed it."

Dinner passes, with conversation and eyes meeting for long moments. There is a palpable charge in the air, a sense of suspended expectation.

When the server asked about coffee and desert I turn to Jen with a raised brow.

"No thank-you," as the server walks away Jen continues, "I have other desert plans."

As the bill arrives Jen starts reaching for her wallet I clear my throat and she looks up surprised.

"I was instructed to pay, so don't you dare."

"You can't! That's too much."

"My wife's rules, if you have to obey the ones she gave you, I have to obey the ones she gave me."

"God, your wife is a bossy bitch isn't she?" Jen says with a smile and a laugh as she relents.

"That's why we love her."

We leave the restaurant and again holding the door for her I admire her as she steps into the car.

As I start the car I ask, "Where to now?"

"Desert." Jen answers with an enigmatic smile. "Just follow my directions."

My curiosity pique I follow her directions as we drive out of our town into a little larger one 25 minutes away and finally she has me turning to the parking lot for a relatively new hotel that boasts "spacious suites".

Jen looks over at me expectantly and I suspect nervously, I smile reassuringly.

"We both keep our promises," I say simply. "Under your last name I presume?"

"Yes," she says with a nod.

After getting the room paid for I return to the car with a surprise and a smile.

"You got upgraded." I say as I climb in to move the car closer to the room.

"What do you mean?"

"They had someone ask for several of the business suites connected to each other and so they had to give up your original room. Tonight we'll be in the honeymoon villa suite."

"Seriously? No way."

"You're good luck, I never get upgrades."

"So it's my doing?"

"Of course." I say matter-of-factly and with a smile.

I pull the car around to the 'villa' which is a little cottage like set-up set apart from the rest of the establishment. The two of us walk up to the door and I flash the key card at it before the unlock light flashes green and then I push the door open. With a grin I turn to Jen, and pick her up making her gasp a bit in surprise.

"It is a 'Honeymoon' suite, seems appropriate to carry you across the threshold."

Jen laughs, "if you say so, should I be calling you 'hubby'?"

"Tonight it is whatever makes you happy." I say with a smile.

Jen seems to mull it over a moment, "I think not. I don't think I could be comfortable with that, I am only borrowing you after all."

I carry her over to a sofa set in front of a fireplace before gently setting her down. "A fair point and it is as you wish, beautiful." I say with a smile, "I see we have a fireplace, a bar, according to the front desk the drinks are included with the room, and a hot tub."

"Hmmm the hot tub sounds tempting, but maybe later right now maybe you can get that fireplace going and then slide onto the couch with me."

I smiled back at her and quickly had the fireplace going and then I was on the couch wrapping my arm behind her, for a moment she just snuggled in closer to me, and sighed contentedly as we both watched the fire chirp merrily.

After several long moments I felt her hand sliding over my chest in a way that made me know she wanted me to turn back towards her. I turned and her lips were already parted for a kiss.

Our lips met again and as I pulled her closer to me I felt her entire body just melt into the kiss. My tongue darted out to tease her lips and she moaned as she let her tongue come out and slide along mine. Both of us were beginning to breathe heavier as I sucked her lower lip between mine and gave it a nibble that made her moan once again.

I felt her hand slip inside my shirt and was a little surprised as I had not noticed my shirt being unbuttoned, but the feel of her fingers sliding over my chest quickly had my heart racing even more. I was hesitant to allow my hands to roam too far as I was not entirely sure what the actual boundaries for the night was and what Jen's comfort zone was. She seemed pleased with the kissing and just being held so that is what I stuck to and allowed her to let her hands roam beneath my shirt to her heart's content.

She broke the kiss first and smiled at me her eyes still half closed; "yes, best date in a very long time." She said softly almost just to herself.

"I am glad you are pleased, be sure you tell my wife that I haven't disappointed you." I said with my own smile, "I feel like the luckiest guy in the world sitting here with you, and knowing that I still have my amazing wife at home. Only thing better is if both of you were here."

Jen smiled even bigger, "You are a one of kind guy; you make me feel beautiful and loved even while it is clear you do not love your wife any less."

"You are beautiful, absolutely gorgeous in fact. And the honest truth is I do love you, not the same way as I do my wife, but there is no other woman I care for more. You and Katie are part of my family as far as I am concerned; you will both always have secure and safe homes in my heart."

Jen's eyes glistened and I was worried I had spoken too much, but truthfully I had always loved her much like a sister and at the very least Katie felt like a close niece or even step daughter.

Jen wrapped her arms around my neck and swung herself into my lap her eyes met mine. "I love you, I love your kids, and I absolutely adore your wife. I have always admired what a wonderful friend you've been to me, and what a kind and caring husband and boyfriend you were to my best friend. The way you are such a great father to your little girls and it has never escaped my notice the way you include Katie and care for her like your daughters."

Jen just sat on my lap looking me in the eyes, seeming to consider something. There was no hiding I was excited, she was sitting directly on my barely restrained manhood. She reached behind herself and unzipped the back of her dress. She slowly, sensually pulled it up. Revealing her black lace panties first, then her stomach, which I could not resist letting my hands slide over, my finger tips gliding over her skin made her moan.

She continued pulling the dress, revealing more of her stomach and her ribs, which my fingers also traced making goose bumps spring up on her skin and making her squirm a bit in my lap, grinding herself against me.

As she lifted the dress higher her bra is revealed, matching her panties it was also black and lace, and accented well against the creaminess of her skin tone, so much lighter than my wife's rich olive. I leaned in and kissed between her breasts in the cleavage making her gasp a bit, my fingers still gently tracing patterns over her skin, sliding to her back and making her moan still more.

She lifts her dress still higher and my lips move from kissing her breasts to nibble first at her collar bone and then working up to her neck causing her to pause and moan, grinding herself against me even harder.

I reach for the dress and resume pulling it off of her, revealing her lips which I kiss, leaving her blind as our lips meet again. Then I finish pulling her dress over her head and lay it aside on the couch, she looks at me expectantly, maybe even nervously, for the first time I am seeing my wife's best friend in just her under wear, and while no more revealing than a bikini that I had seen her in plenty of times there is definitely something more to it. I let her see me drink in the vision of her, and then my eyes meet hers again.

"You are absolutely beautiful." I said simply, her response was a smile with her eyes shining brightly at me, which just served to make her even more beautiful to me.

She put her hands under my shirt and pushed it off of my shoulders fully revealing my chest she runs her fingers behind my neck and then up the back of my head thru my hair before leaning back in to have our lips meet again in a kiss. A kiss that turns hungrier by the moment as our excitement raises higher with every nerve we trigger as our fingers explore each other's skin.

Jen unclasped her bra and as she revealed her breasts to me my eyes drank them in and he skin flushed a bit with I assumed pleasure in seeing my honest reaction of want and desire. I ran my fingers over her breasts and my fingers traced over her nipples that poked out screaming for attention.

I lean in close and suck and nibble first her left breast giving her engorged nipple a gentle bite that causes her to moan and then I moved to her right breast giving it similar attention, Jen's hands pulling my head close to her as she grinds herself against me, I can hear her heart pounding in her chest with her continuously rising excitement.

She pulls away just enough that she can pull my pants open. Freeing my hard cock she wraps her fingers around it stroking me making it my turn to moan my own pleasure.

"Fuck Lisa was right; you really are a surprise down there. A deliciously wonderful surprise, she is such a lucky girl!"

Jen climbed out of my lap just long enough pull her panties down and off then she was back in my lap, she began sliding herself along the length of my shaft her body giving a shiver every time the head of my dick brushed against her clit.

I let her ride me, bringing herself pleasure with my dick, not sure exactly how far she was going to take things but willing to let her use me for her gratification knowing that if my wife had given her this kind of leeway it must be something she really needed. I stayed content running my fingers over her skin which seemed to be working to enhance her pleasure and as I gave her nipples little pinches she'd gasp with increased excitement.

This belief seemed confirmed as she threw back her head and screamed she ground herself even harder against me as she continued riding me right thru her orgasm.

"Fuck that was good!"