Girlfriend Agrees to go Topless (First Cuckolding Book 11)

by Matt Coolomon

  Lisa’s blush fires up. “Um…. Okay then,” she utters. “With my arms up like this?”

  “Fuck yeah,” Evan groans. “Just like that.”

  Trent smiles and carefully positions his phone under the front of Lisa’s nightie. It clicks and flashes. He checks the pic while Evan opens his laptop on the counter. Trent shows Lisa a high resolution picture of her pussy and little bush. “Can I show everyone?”

  Lisa nods. “Go on then….”

  “Email it to me,” Evan says to Trent, and after a couple of clicks the file appears in his inbox.

  The men gather around but George invites Lisa close beside him. Evan opens the file to full screen, making the image close to life-size. “Fucking awesome,” Evan groans. “That’s a smooth slit…. I thought it was from that other pic.” He scrolls the mouse and zooms in. “Yeah – just slightly open and pink inside,” he says, grinning back at Lisa.

  Lisa is holding the hem of her nightie down and blushing fully. George has an arm around her, his hand upon her waist, his thumb stroking.

  “You can keep that one if you want,” Lisa says.

  “Forward me a copy, please?” George asks.

  “I’ll send you one so I have your email,” Trent replies, and George tells him the address.

  “That’s a beautiful picture,” George tells Lisa. “That’s a pretty little landing strip and your opening looks – well – inviting, if I can put it that way.”

  Evan chuckles. “Definitely inviting!”

  “Can see the underside of your tits too, Lisa.” Trent is working the picture on Evan’s laptop screen. The others look at what he’s showing them. “See – that’s right up in between them and the bottom of them both.”

  “Another sneak preview of tomorrow?” Evan tries playfully.

  “Yes – you have to wait for the rest,” Lisa says, giggling. She sips more coffee. George’s hand lowers from her hip and touches her bottom. Lisa meets her boyfriend’s glance. George squeezes softly and strokes down her thigh and back up under her nightie. Evan and Trent are still expanding and examining her pic, with Alan watching on beside them. George spreads his hand over one side of Lisa’s bottom and squeezes her bare. He then caresses across the other side and squeezes again. “Have you ever been spanked, love?” he whispers to her. “Just by hand…?”

  Lisa shakes her head and meets his eyes.

  “This little nightie would be perfect for it.”

  “Perfect for what?” Evan asks, grinning over.

  George chuckles and gives Lisa’s bottom another, more overt, squeeze. “Spanking…. I bet our pretty girl’s pussy would look amazing from behind if she was bent over a lap.”

  Lisa turns away from his grip and takes her cup to the sink. “Hmm – sounds a bit kinky to me, thanks very much.”

  “No – spanking’s all in good fun if done right,” George defends.

  “Yeah – by hand and not too much,” Evan argues. “I don’t see anything sexy in BDSM. Most of that looks way over the top to me.”

  “I agree. It’s just about a tiny bit of sting to get the lady nice and wet. Then bent over your lap is the perfect position to use fingers.”

  “Oh my god! Shut up you old perverts!” Lisa cries in mock indignation. “I’m going to bed before you get any more silly ideas.”

  The two older men laugh. Evan claims Lisa as she’s walking past. He hugs her from behind, his arms crossing and his hands covering her breasts. “Okay – no need to get up too early I guess….”

  “No – not too early,” Lisa echoes, lightly holding his arms as he feels her, massaging firmly and making her nipples hard again. She squirms from his bear hug giggling and suddenly there’s a smack on her bottom, making her spin and cover her bum with her hands while glaring at George.

  George is grinning. Lisa smiles. “See – feels good, doesn’t it?” he teases.

  “Hmm – maybe….” Lisa replies confusedly. It did actually feel strangely interesting. She’s blushing fully again. “Is that what you meant – just like that?”

  “Or a tiny bit firmer,” George explains mildly. “Lots of women enjoy it once they try it.”

  “Yeah, but how hard is a little bit firmer exactly?”

  “Would you like me to demonstrate, love?”

  Lisa peers around at everyone. “Um…. Can it be a really small demonstration?”

  “Of course. What about one firm spank on each side – and we’ll do it standing, not bent over?”

  “Hmm – can I, Alan? Just to try it?” Lisa asks her boyfriend.

  “Alright – just to try it,” Alan agrees, looking to George. “And not too hard.”

  “Firm but not to hurt the lady…. Let me show you, son. You might enjoy trying it yourselves sometime.”

  Lisa peers back at the older man as he approaches. “How should I stand?”

  “Just forward slightly and lean on the counter, love…. Yes – like that – perfect.”

  The others all watch expectantly. Lisa bites a lip and waits, still peering back over her shoulder at the older man. He gathers the bottom of her nightie and inches it up a bit, pressing lightly on her lower back with his left hand. He then smacks her right buttock with an open palm. There’s a resounding slap and a surge of tingles swarm through Lisa’s belly.

  “Okay?” George asks softly, just holding her stinging cheek now. His hand is warm and feels nice.

  “I’m okay,” Lisa tells him. “I’m fine.”

  He smiles and suddenly spanks her left cheek.

  “Uh..hhh,” Lisa moans involuntarily, the tingles surging again, and the hand upon her bottom grips and massages firmly.

  “Can you take another picture, son?” George asks Trent. “Just stay like that, love?”

  “Okay,” Lisa utters. “Mmm – that was incredible.”

  “Yes – good girl,” George goes on warmly, and he just holds her bottom lightly while Trent kneels and snaps a photo. The phone clicks again, then George grips firmly and massages again. Lisa rests forward across the counter. She peers back over her shoulder and sees them all staring. George’s thick fingers press into her inner thigh and spreads her a little as the phone clicks again.

  “Alright that’s enough now,” Alan says. “I think that’s enough tonight.”

  “Yeah – that’s beautiful…. You’re truly beautiful, love.”

  “Thank you,” Lisa says, smoothing her nightie down in back as she faces the men.

  They’re gawking at Trent’s phone. George joins them. “Yes – perfect,” he says.

  “Man, that’s pretty full on,” Alan groans. “That shows A LOT.”

  Lisa peers over her boyfriend’s shoulder and is instantly filled with a mixture of excitement and embarrassment at a picture of her pussy lips being held open.

  “Can even see you’re wet in this one,” Evan says. “Can see the juice inside you.”

  “Uh huh….” Lisa utters. “I think I’ve been wet down there all day.”

  The men chuckle. They send the pics to Evan’s laptop and have them on that screen instantly. They settle on the last one, where Lisa’s opening is actually peeled open. Evan zooms in, enlarging the image so her pussy fills the screen.

  “I think I might leave you dirty men with your pictures,” Lisa says.

  “Okay, baby…. Goodnight,” Evan says, taking her hand and drawing her into a hug with one arm.

  “So, you enjoyed that sample spanking?” George checks with her, taking a hug too.

  “Yes, I enjoyed it….”

  “So, we’ll try again another night while you’re here?”

  Lisa glances back from the door with her boyfriend leading her away. “Maybe….” she teases. “I’m not saying no.”

  5

  Lisa has left Alan at the bathroom door and is gripping the top of the shower screen, holding on there while her orgasm pulses through her belly. The hot water is running over her head and down her tingling body. She’s holding her pussy, seeing it peeled open on
the computer screen, her fingers still between her slick folds.

  She calms herself and finishes showering. Alan is waiting in bed for her afterwards. “I think we need to talk, Lisa. This is really crazy. We’re going to be a married couple.”

  Lisa slips beneath the sheet and kisses Alan’s chest. “We can talk in a minute, okay? After I taste you….” She’s squeezing his cock as she speaks. She then kisses her way down, and her boyfriend strokes her hair and keeps his hand on her head.

  “Are you going to – like that?”

  “Uh huh. I want to taste you, Alan. I want you to cum in my mouth.” The cock in her hand is instantly hard, and she takes the head in and sucks it. She strokes with her hand and allows it to surge in and out of her mouth. After only a minute or two Alan’s body is stiff and pulses of semen are gushing up against the roof of Lisa’s mouth and seeping into her throat. “Mmm – yummy,” she moans as she swallows, and she kisses her way back up to her boyfriend’s chest and settles cuddled up there.

  It takes Alan a few minutes to say anything. He’s stroking Lisa’s hair. “It just seems like things have gotten out of hand a bit, baby. They’re really touching you a lot now.”

  “I know, but it feels different to me,” Lisa answers softly. “It’s not like what we do together. It feels really exciting.”

  “Exciting? So, what we do isn’t exciting?”

  “It hasn’t been lately, Alan. But right now it is. Sucking you off is exciting.”

  “Yeah, but that’s got nothing to do with them.”

  “Yes it has. Everything that has happened today has made me want to do it. Ever since I was talking to the woman at the resort pool, I’ve been feeling naughty and curious about stuff.”

  “The woman at the pool? What about her?” Alan asks.

  Lisa lifts to her elbows to meet her boyfriend’s eyes. “Well, she told me all about when she was young and her boyfriend let another man have sex with her…. She said it has made her sex life with her boyfriend amazing ever since…. She said it made her boyfriend start to be more forceful with her and start taking what he wanted instead of asking.”

  “Taking what he wanted from her, you mean? Like – sex?”

  “Yes – sex – taking her!”

  “Huh? What does that even mean? A husband can’t force his wife to do anything.”

  “No – not force exactly, Alan. If a woman doesn’t want to, then that’s the end of the matter. But if you wanted me to suck you off and you insisted – well, there’s every chance I’d give in and do it.”

  “If I insisted? Like if I told you to do it instead of asking?”

  “Well yeah…. Or if a guy held my head with a small amount of force and pressed his cock against my lips…. Which would be different to just saying that I have to do it, because I’d feel how strong he is and would only have to open my mouth to change my mind.” Lisa bites a grin. “That might not work every time, but it would work quite often with me.”

  “Shit – really?”

  “Uh huh…. Or if you just started feeling me up like these other men are doing…. If you did that instead of saying you want sex, I’d find it a lot harder to say no.”

  “Oh okay…. I didn’t know that,” Alan says ponderingly.

  “But does it make sense to you? Do you understand what I mean?” Lisa asks softly. “It’s not about being forced unwillingly. It’s just about a man feeling strong and determined…. That’s a huge turn-on for a girl.”

  “Yeah, I get that now, baby…. It makes sense the way you explain it.”

  “Well, everything that’s been happening today has been like that for me, Alan. Evan and George are exactly like that, and they’ve been making what that woman told me make perfect sense.”

  “Oh…. And that’s why you wanted to suck me off? I don’t really get that bit.”

  Lisa giggles. “I was pretending you were insisting that I do it, Alan…. I was imagining it’s something my boyfriend expects to have done for him, and that my only choice is whether I do it or he finds another girl to do it for him.”

  Alan smiles huge. “Yeah, but there’s no way I’d want to find another girl, baby.”

  “Well, that’s too bad then…. I’d definitely do what I needed to do to keep my boyfriend from looking elsewhere…. If you expect certain things with sex and insist on getting them, I won’t be too quick to say no.”

  Lisa rests her head upon Alan’s chest again. He strokes her hair for a while. She’s dozing off when he speaks.

  “But what about from now on, baby? What about tomorrow with these old dudes – it all makes sense now, so there’s no need to do anything with them anymore, is there?”

  Lisa’s skin tingles all over. She’s instantly awake. “Um…. I’m not so sure about that actually.” She lifts to her elbows again. “I also like the thought of pushing boundaries a bit, since we’ve been together since we were kids and never experienced anything else…. Or ANYONE else, I should say.”

  “ANYONE else?” Alan echoes weakly.

  “Yeah….” Lisa utters. “I guess it might be different for a guy, but as a female it’s all about things happening inside me – like in my mouth or in me down there – like with how excited everyone was to look at my pussy in that pic and see it a little bit open. The way they said it looks inviting.” Lisa shrugs a little. “I really like the thought of some other men having sex with me, Alan…. Just the thought of being penetrated by some other man’s cock – and also about you knowing that he’s been in me…. I just find the thought of that so exciting!”

  Alan just stares in the dim light. Lisa has been fondling his cock all along. It begins to firm so she squeezes. He strokes her hair once and takes hold of the back of her head. Her skin tingles wildly and she resists a little. He scoots up a bit and pulls her head forward, his hand closing over hers and his cock pressed against her lips. She opens and he sticks it in her mouth. He then starts thrusting – fucking her lips. He works her onto her back and straddles her, holding the bedhead with one hand and a bunch of her hair with his other. He’s staring at her and she’s holding his eyes. He humps slowly and deliberately but soon loses it and surges one final time to hold firm. His first pulse of semen hits the back of Lisa’s throat and gags her. She coughs a little but recovers quickly, the remaining spurts of her boyfriend’s cum flooding the back of her mouth.

  Lisa swallows, grimacing at the taste, then sucks softly. Alan is breathing hard and sweating. She takes his cock from her mouth and kisses it. “Did my boyfriend enjoy that?” she asks sweetly.

  “Felt good,” Alan says.

  Lisa giggles. “I’m pleased to hear it.”

  Alan rolls off and flops on his back. Lisa props herself beside him, smiling. “So…? What about what I said?”

  “About wanting to um…?”

  “Uh huh…. I think Evan and George would be perfect for it…. It’s not like it could ever mean anything or amount to any kind of relationship. It would be purely physical.”

  Alan gulps. “And you want it to be more than just flashing and touching – you want it to be actual sex?”

  “Uh huh…. It would be up to them of course, but yes.” Lisa places her chin on her boyfriend’s chest. “Maybe you could even film them fucking me…?”

  “What? Seriously?” Alan gulps again. “Shit.”

  “I know – but imagine if we had clips like that to keep for us to watch sometimes after we’re married. That would be super sexy, wouldn’t it?”

  “Yeah, except it would be other dudes fucking MY wife.”

  “Uh huh…. Taking me while you have to watch,” Lisa whispers excitedly. “You liked them touching me in front of you today, didn’t you?”

  “Yeah – I guess it was mostly interesting to watch. But it felt too weird sometimes.”

  “Well yes – for me too – but I like that they were kind of the dominant males. They’re older and more experienced than you, so it seems right somehow…. What if you were to just accept it and
let the more mature men have first rights with me while we’re doing this…? Just for this visit as something we’ll always be able to think back on later?”

  Alan swallows, his throat seemingly dry. “I guess it’s true that they do seem sort of dominant to me too. When they touch you it feels kind of natural to me.”

  “Exactly!” Lisa enthuses. “That’s exactly what I mean…. It’s like the natural order for the mature males to be first with the young female…. While we’re all playing this sexy game together, it just makes sense to me that the two mature men should be allowed to touch me and even fuck me if they want to.”

  “Yeah – I guess,” Alan agrees tentatively. “That’s if they try to go that far with you. They haven’t yet, so maybe they won’t even try.”

  Lisa kisses her boyfriend’s chest and rests her head, closing her eyes. “Mmm – I hope they do, Alan…. I’d love for them both to fuck me.”

  6

  The distant hum of a mower wakes Lisa the next morning. She’s alone in bed, the thoughts from yesterday flooding back and filling her with excitement and anticipation. She crawls up to look out the window and sees Trent on the ride-on mower. She also sees Alan getting into Evan’s truck and driving away, and she remembers Evan asking Alan if he would go to the store in the morning.

  Lisa quickly brushes her hair and puts on panties beneath her nightie. She then checks her drawer and decides on a short towelling bathrobe but takes off her nightie before putting it on. She hopes Evan is up but finds his bedroom door closed and the house empty. There’s cereal for breakfast, and she brews coffee. While she’s sitting at the breakfast counter eating, the mower approaches and stops. Trent then comes into the kitchen and greets her with a big smile.

  Lisa blushes at thought of what part he played in the sex games the previous night. “Hi, Trent, there’s fresh coffee,” she says.

  “Hey, Lisa….” He pours a tall glass of juice and sits on the stool beside her with his back to the counter. “You were so fucking hot last night,” he says mildly.

  Lisa smiles through her blush. He leans back and looks at her legs, her robe parting at her waist and open below that, her blue panties on display.