Helping Out 12

For spring break, Claire and take a trip to visit some of her friends in the Kansas City area. Aside from Carmen, who is our friend now. Claire has three other good friends: Lindsey, Taylor, and Kelsey. Lindsey and Taylor are both married, but Kelsey is not. Taylor and Kelsey both live in KC while Lindsey lives a few hours away but still closer than Claire and I do. I don't normally go on trips with her to see her friends. I'm alright with their husbands but we're not exactly friends. However, I go along this time because on the way back we're going to stop for a few days to visit my parents. So, I'm along for the ride.

As soon as we get to Taylor's house, they're all chattering away already. They've been friends since high school, so even though they haven't gotten together in months, they fall right back into old habits. I find Drew, Taylor's husband, in another room and hide there. We don't talk much but just sit around watching TV. We watch some old UFC fights and then later

Batman vs. Superman

which was as bad as it sounded. We all go out to eat at some hamburger place that's trying to be trendy. Everything is served on what looks like cutting boards to me. The girls start drinking there, but I'm relieved when Drew doesn't. I do not want to drive a car full of drunken people home in Kansas City traffic. That would be a literal nightmare for me.

When we get back to the house, Drew says he's going out with some friends and asks if I want to go along. I politely decline figuring I can hide here and the girls will ignore me which is preferable to awkward social contact. I return to the living room and watch nothing on TV for a few hours while Claire and her friends drink more wine, talk loudly, and laugh louder. Then suddenly they're all in the TV room with me. Taylor sits right next to me and then the rest of them squeeze on the couch.

"What are you watching?" Taylor asks me and rests her head on my shoulder.

"Nothing," I say. She's always been a little more touchy, so I don't say anything about it.

"Sounds fun," she says jokingly.

"What are you all doing?" I ask trying to be polite.

"Well," Claire says. "We were talking about the videos we've made."

"We knew like years ago when you first made videos. Claire tells us everything," Lindsey says.

"I watched some of your videos online," Taylor blurts out clearly more drunk than the rest of them.

"We know. You won't stop talking about it," Kelsey says.

"That's awkward," I say.

"You know Kelsey's never had sex," Taylor continues. "She'll be 30 soon and that is just too long to not be getting some."

I lose track of the conversation as they all start talking at once. I get the feeling that they've already talked about this many times before. Kelsey gets up and leaves the room and Lindsey follows her. They say they're getting more wine, but I know something is up. Claire gets up to but just scoots me and Taylor over so she can sit on my other side.

"We want you to take Kelsey's virginity," Taylor says and stops resting her head on my shoulder finally.

"What?" I say, completely taken aback. I knew it had something to do with sex, but I figured they'd just talk about the videos or try to embarrass me somehow. "Claire, what is this?"

"I agree," Claire says and looks at me. Her face is serious as she nods.

"You're like the nicest, sweetest guy ever. We'd rather her lose her virginity to someone who is going to take care of her than some asshole," Taylor says and her face is serious too.

"What does she have to say about it?"

"Well, it wasn't her idea," Claire says. "But she wants to. She's just nervous. That's why she left the room when we asked."

"Even if you are okay with it," I say standing up and walking a ways from the couch. "I can't do it. You guys are all drunk."

"See. This is exactly what I'm talking about. You're perfect for it. We're practically throwing a hot piece of ass at you and you won't take advantage of her because we're drunk," Taylor says.

"Look. Maybe. Maybe I would if you weren't all drunk."

"I haven't really drunk anything," Kelsey says and I look over as she and Lindsey return to the room.

"You had a glass of wine at dinner," I say.

"That's all she's had," Lindsey says. "Claire knew you wouldn't agree if she was drunk."

"But she's not," Taylor chimes in. "So get to it. We can have her walk a line if you want."

"Are you sure?" I ask the room.

Claire assures me she's okay with it and I'm inclined to believe her with everything else we've done together. Taylor is obviously overeager. Lindsey has been trying to coach Kelsey up apparently. Kelsey just looks at me and nods. Taylor practically jumps up from the couch and grabs my hand. She leads me to her and Drew's bedroom rather than the guest room. She says the bed is bigger. She lights a few candles and tells me that they're going to help Kelsey get ready. I consider stripping, but decide against it. If she really wants to do this, I need to go slow. Walking into a room with a naked man but be too much for her and end it right there. I do take my shoes, socks, and belt off though and arrange them neatly by the side of the bed. Then I sit down on the edge of the bed.

Claire comes in first and tells me again that she's okay with it. She tells me to go slow and gentle. I promise I'll stop at any time. She gives me a condom but also tells me that Kelsey is on birth control if things go that direction. I stare blankly at her for a moment. I wonder what my high school self would think of this situation. I probably fantasized about it before. Claire leaves and Lindsey and Taylor guide Kelsey into the room. She has on a satin bath robe. Taylor looks at me disappointed, and I get the feeling she was hoping to see me naked already. They close the door behind them. Kelsey stands just inside the room quietly looking everywhere around the room except at me.

"It is totally okay if you change your mind," I reassure.

"You don't find me attractive?" she asks, and the look on her face is as if she's made some sort of horrible mistake.

"No, not at all," I say. "What I mean is that isn't it all. I was just trying to reassure you. Your long hair is sexy, and I remember how good you looked in your prom dress in high school. I'm sure you're an even sexier woman now."

"Thanks," she says and takes a few steps toward the bed. "I've never done anything like this before."

"I know. We can stop at any time."

She walks the rest of the way toward me and sits on the edge of the bed next to me. She fidgets with the hem of the robe. I decide that I have to start things otherwise nothing will happen. If I start, at least she has the opportunity to change her mind then and know she tried. I put my hand on her leg just above the knee. I put my other hand on the side of her head and pull her face towards mine. She closes her eyes, and I kiss her softly on the lips. After a few seconds, I break the kiss to give her time. Then she leans in again and kisses me. Her lips part and we explore each other's mouths. It's like a first kiss all over again. We fall to our sides on the bed and continue to make out. I stop and take her hand. We climb fully onto the bed and lay side by side kissing. She begins to run her hands down my chest and then up under my shirt. I keep my hands only caressing her back and avoid venturing too far too fast. She begins to pull the shirt off me, so I sit up and pull it all the way off.

"Will you take it all off for me?" she asks. "Please."

Her timidity is endearing and cute. I kiss her gently again and then get out of bed. I pull down my jeans and take them off. I stand there for a moment in my boxer briefs letting her look me over or protest. When she doesn't, I pull those down too and reveal my hardening cock.

"It's so big," she says and her eyes open wider.

In porn that reaction is always faked, but I get the feeling that Kelsey's reaction is genuine. I get back into the bed and lay down allowing her to decide what she wants to do next. She sits up and runs her hands across my chest some more. Her hands go lower and lower until they're hovering over my cock with has continued to swell. She looks at me then quickly turns back to my cock. She grabs it with both hands and lets out a little breath of air.

"It's so hard, yet soft," she says, and strokes it a little bit. "Like that?"

"Perfect."

I let her explore my naked body with her eyes and then her hands. She caresses my thighs and massages my balls. I roll onto my side and she squeezes my ass while still firmly gripping my cock. She kisses me on the lips with the most force yet and then kisses her way down my chest. She kisses my thighs and then hesitates. Then she kisses the tip of my cock and kisses up and down it. She gives it a tentative lick and puts just the head in her mouth. I moan a little and she stops and looks at me concerned.

"That's a good noise," I tell her.

She continues to kiss and lick and suck my cock just a little bit. Then she stops abruptly saying that she can't do it. She gets up, and in a flash she's out of the room. I wait a moment to see if she'll come back, but after a few minutes when she doesn't, I get up to get dressed. It's then that I notice she didn't close the door all the way. I walk over to it and am startled when I see both Taylor and Lindsey peaking at me. Seeing as they'd already seen my cock online and just now when peeping, I fling the door open and they step back looking embarrassed.

"May I help you?" I ask pretending that I'm not naked and that my cock isn't twitching in the air just a foot away from two of my wife's best friends.

"Yes you can," Taylor says and grabs Lindsey by the hand. She pushes passed me into the room. "We wanted to see your cock for real. Those vides you and Claire have been uploading are so hot. I wanted to see what you look like naked in person."

"It was her idea," Lindsey says looking more embarrassed than Taylor.

"You wouldn't stop talking about it either," Taylor says. "You know. Ever since high school I've wanted to see your cock. I knew you were with Claire, and she's my friend so I never ever said anything about it. I just knew you'd be good at taking care of a girl's needs. It was my idea for you to pop Kelsey's cherry."

"How is she?" I ask pretending like the confession didn't cause my heart to skip and my cock to twitch with the excitement of being wanted and desired.

"She'll be back," Lindsey says. "She just needs a little more time."

"I figured we could help pass the time," Taylor says and pulls her shirt over her head revealing she has no bra on. Her tits swing free, and I stare just like she stared at me. "I knew you'd like them. Your turn," she says and nudges Lindsey.

Lindsey takes her shirt off too and reveals a plain black bra that is still sexy. She reaches behind her and unclasps it.

"Now we promised Claire we'd only watch," Taylor says. "She said you'd get off for us though. She said you'd last longer with Kelsey that way."

"I see," I say.

I turn to close the door, and I see Claire standing in the doorway. She winks at me and closes the door as she heads back down the hallway. I walk closer to the two friends and slowly begin to stroke my cock. Lindsey looks away for a moment and then can't resist the urge and looks back. Taylor watches hungrily. I cup my balls and play with them. I continue to stroke my cock and stop just out of reach of my wife's friends. Just then, Taylor gets up and walks in front of me. She walks as close to me as she possibly can without actually touching me. She rummages through a dresser drawer then returns along the same close orbit. She hands me a bottle of lube before she sits down. She immediately puts her hands in her pants, and I know she's playing with herself.

I open the cap and pour some lube up and down the top of my cock. I slowly work it over my shaft until I'm gleaming in the candlelight. I hold my cock in my hand and begin to thrust my hips just like if I was fucking Claire from behind. Taylor's breathing quickens. Lindsey's mouth hangs open. I continue to stroke and thrust until I begin to approach my climax. I slow down and look at Taylor again. Her cheeks are flushed and her legs shaking. She moans softly as I watch her come quietly to me stroking her cock. I begin to look around for something to come on when Taylor throws Lindsey's bra at me.

"Come for us," she tells me.

I hold the bra so that one of the cups is under my cock ready to catch my load. I begin to combine strokes with thrusts. Again I work toward climax. I groan loudly and begin to come for them. I see the first rope of cum plaster the soft cup of the bra. Then I look toward the two women. Lindsey looks mesmerized as I fill her bra with my hot cum. I catch Taylor's eyes and lock them with my own. I look deep into her eyes as I continue to thrust and stroke and spurt every last drop of cum out of my hard cock. I want her to feel like I'm coming just for her. This is the one chance she'll ever have to even approach her high school fantasy. With one last groan I finish coming and look down at my softening cock. The cup of the bra is filled with a huge load that is soaking into the fabric. I use the other cop to wipe off my cock of lube and cum. Then on a whim, I hand the used bra to Taylor and head toward the master bathroom to clean myself off better. When I come out of the bathroom, Taylor, Lindsey, and the bra are all gone. All that is left of the encounter is a slight wet spot on the sheet where Taylor was sitting.

"Not that I was watching though a crack in the door, but that was really hot, Jake," Claire says as she walks in the room. "You made Taylor so happy."

"That wasn't weird for you?"

"Not at all. I love knowing other people want my sexy man," she says and comes over to hug me. "Who better to share him with than people I trust?"

I nod and hug her back.

"How's Kelsey?" I ask a little worried about her.

"Oh she'll be back in just as soon as I leave."

"What are you going to do?"

"Taylor and Lindsey haven't seen the video we made with Carmen last month, and I think they're really going to like it after just watching you," Claire says and kisses me before leaving the room.

Immediately after she leaves, Kelsey walks back into the bedroom. She closes the door and makes sure it latches. Then she opens her robe and lets it fall in one quick motion. She's got on a pair of white lace panties and a matching bra. After a moment, I recognize it as the bachelorette party gift that Claire got Taylor when she got married. She walks toward me and kisses me more passionately than before. She breaks off the kiss and then leads me to the bed.

"I'm ready now," she says and lies on her back on the bed. "Please."

I join her in the bed and lay on top of her. I start by more kissing and this time she responds by running her hands down my back and squeezing my ass. She grinds upwards against me, and I know she's really resolved now. I decide that she deserves something more than just sex, so I begin to kiss my way down her neck. I stop for a while at her tits and lick and kiss them. Then I kiss down her stomach. I veer away from her mound and kiss my way down her thigh and then calf ending by kissing the top of her foot. I move to the other foot and kiss my way back up. I follow the trail back up her stomach, and as I reach her breasts, I pull the bra down a little so that her small nipples come free. I gently suck them and pinch them and bite them. With each movement she squirms more and her breathing quickens. I kiss my way back up her neck and then our tongues join again. But, I soon depart again and kiss my way back down through her cleave and across her stomach. I end by nuzzling my face in her bush. It hasn't been completely shaven, but it appears that it has been trimmed a little.

She moans as my hot breath reaches her pussy. I give her pussy a quick kiss before I part the lips and place my tongue on her clit. She moans loudly and arches her back at this newfound pleasure. Then her hands are in my hair begging for more. I twirl my tongue around her clit and lap at it. I trail my tongue around and up and down her pouty pussy lips. I spread them wide and gently drink deep of her excitement. She tastes different than Claire but just as desirable. After I've tasted my fill, I return to her clit and work my tongue over it faster and faster. She moans louder and louder. She gets so loud that I'm sure that the others can hear her and then she's quiet as if she's lost all her breath. She begins to shudder and shake with an orgasm that has been withheld for years. She squeezes my head with her thighs involuntarily as she shudders with pleasure. I lick her pussy a little longer but stop more quickly than I do with Claire not wanting to overwhelm her.

I lay down beside her as she pants for air still twitching every now and then. I put my arm around her and hold her close as she sifts through the emotions of her first real orgasm. After a while, she dries her silent tears on her arm and sits up. She looks me up and down and her eyes come to a rest on my cock which is thick and hard and ready to go again. She holds it in her hands and squeezes it. She retrieves the condom sitting on the bed and unwraps it on my cock. Then she lies back down on her back. She tugs on my arm, and I roll on top of her. She grabs my cock and pulls it to the entrance of her pussy. She pauses a moment, and then with one hand on my ass and the other holding my cock, she pushes me deep into her. She moans again as I penetrate her.

She shudders as I fill her with my length and girth. I push all the way in and remain like that a moment, letting her feel her pussy completely filled. Then I slowly pull out and thrust back in. I start extremely slow at first and she sighs with each gentle thrust. As she gets used to it, her hands begin to clutch at my back and she brings her face to mine to kiss me. She pulls me in close and my hips grind into her as I start to pick up speed.

"You feel so good," she whispers into my ear between heavy breaths. "Please don't stop. I need it. I need more."

I take her invitation to fuck her harder. I slow down again but this time start thrusting harder. The bed creaks with each thrust and she moans louder each time. Then I switch to fast shallow thrusts and her fingernails scrape against me as she is filled with pleasure. Finally, I begin both hard and fast strokes and soon I'm near the edge. I keep fucking her virgin pussy until I can't take it anymore. I groan loudly as I begin to come. I slow down with each passing wave of orgasm until I'm finally done. I pull out and then lay down next to her.

"Thank you, Jake," she says and kisses me. "That was perfect." Then she gets up and puts on her robe and leaves the room.

Later that night as Claire and I lay in bed, she thanks me for making her friends happy. She tells me that Kelsey is fine and was blown away by how good it felt. Claire says eating her out was a good choice. In the end, she's glad I helped out. Although, I feel like helping out is a bit of an understatement, and I can't help but wonder how this will change her relationship with her friends and how they'll view me from now on. As I wonder, she rolls over on top of me and straddles me.

"You're still mine though," she says. "And I think you owe me."

She presses her lips against mine, and I begin to feel my cock swell. She begins to kiss her way down my chest, and I look over at the door. I can't be sure but it seems like it might be cracked open just a little. I turn back to Claire and give her my full attention.