I knock on Carol’s door, and swallow, nervously. My wife, Jackie, had decided that she wanted to spend the evening with her girlfriend Kim, and arranged for me to have a date with her boss at work. Carol was an older woman, in her late forties, and though I had never met her, I’d seen pictures. She is an attractive woman, easily what one might describe as a cougar. The door opened, and Carol smiled, inviting me in. She looked pretty much like the picture Jackie had shown me, if not even a little hotter. Shorter than I, she stood about about 5’4”, a wrap around dress showing off both the curve of her hips and her C cup bosom. The heels she wore not only accentuated her ass as I followed her in, but also showed off her stunning legs. Thick, firm thighs, strong calves, down to the “DTF” anklet she wore on her right leg, I could tell that this was a woman that took care of herself. As we sat down to the dinner she had prepared, I could feel the confidence and strength in her, both in how she carried herself, and in how she led the conversation.
“That was fantastic, Carol. Thank you for dinner,” I said, looking over at her across the table. “You’re welcome,” she smiled. “I’m enjoying your company for the evening, as well. Why don’t you clear the table.” This was said not so much as a request or a suggestion, but as a statement. She lit a cigarette as I stood up. “Ahem,” she cleared her throat, eyeing the near-empty wine glass. I poured her a second glass of red, and began to clear the plates. As I picked up the last plate, she reached over, caressing my thigh through my jeans. “I don’t know what Jackie is up to this evening, but it was very generous of her to, um, share you with me tonight.” She exhaled her last drag, crushing the cigarette out on the plate I was holding as she stood. From where she was standing, I could clearly see her cleavage, which was firm and full.
“Like the view, do you?” she said, turning. “Why don’t you meet me in the living room when you’re done with this,” she said, walking to the living room. I hurried to finish collecting and cleaning the plates and pans. Carol was a fantastic cook, but she left her kitchen in a bit of disarray. As I finished wiping down the last of the kitchen counter, I looked over absently into the living room, seeing only her legs through the door jamb. They were crossed, and her shoe dangled off her foot. As I turned to leave the kitchen, my erection brushed against the counter. I paused to adjust myself, hoping she didn’t noticed how aroused I was.
As I walked into the living room, I noticed how high her dress had ridden up her lap. In fact, it wasn’t until I saw her sitting there that I realized just how revealing her dress was. Her breasts, her nipples, her thigh all were very much exposed to me, and in fact, I realized, if I were to look closely enough, I could likely get a peek underneath. Hopefully, I’ll get a full look at everything soon enough, if Jackie gave Carol approval, that is.
To be frank, in fact, I’m not sure what’s in store for us this evening. I know that Jackie set this date up so she could spend some time alone at home with Kim, but I don’t know if she intends for me to spend the night, or how far she told Carol we could go. Certainly, Jackie didn’t tell me anything. I don’t have a change of clothes, but this wouldn’t be the first time she’s sent me out for the evening without a bag. In fact, she was quite explicit that not only would she not be giving me an orgasm before I left, but that I wasn’t to get myself off either. “I want you to be ready for Carol,” she’d said, drawing her nude body in close to me. As she slid my hands down across her ample ass, she looked up and practically purred at me. “I hope you’re excited about this date, and you’re able to relax and enjoy it. I know Carol will like spending time with you.”
“I see you like my body,” Carol smiled at me. “It’s OK if you want to look; I don’t mind.” I let myself take her in as much as I felt would be appropriate, drinking in her buxom bosom and full hips and thighs. She patted the seat next to her on the sofa. “Why don’t you come have a seat,” she suggested. I settled in next to her, and she began stroking my thigh, leaning forward toward me. I notice on her wall she has a series of paintings of what appear to be nude boys in various artistic poses. While at first glance they appear to be simply art, there’s something erotic about the way that they’re presented. I feel the plush carpet through my socks with my feet.
“Will you please hand me my cigarettes?” Carol asks, nodding toward the coffee table. I reach over for the pack and the lighter, and notice an art book, Women in History, as I pick them. “Would you mind?” she asks, indicating that I should get her a cigarette. I take it out and place it between her lips, and light it for her. As she inhales, I notice that her breasts are all but hanging out of her dress. “They’re quite full, and large, aren’t they? You can set the pack down on the table, if you’d like.” I lean forward to put them back. “Next to the book that you noticed,” she smiles at me. “Curious? It’s one of my favorites to flip through. Why don’t you bring it over here and I’ll show it to you.” I pick up the book and set it on my lap, hopefully covering my now rock hard erection so that she doesn’t noticed how arousing I find her body. She snuggles up next to me and starts flipping slowly through the pages as she tells me about the artists and their work. After a series of photographs by a West Coast artist featuring extremely attractive women in traditionally men’s roles – CEO, construction worker, auto mechanic – we get to a page featuring a series of paintings of buxom women with nude boys. Their not explicitly sexual, but in some of the paintings the boys have erections and the women seem to always be in some sort of situation where their giving the boys guidance or leading something. Teacher, neighbor, councilor. Carol tells me these are by one of her favorite artists, and she takes the book out of my lap to take a closer look. As she does, she notices that I am hard, and can see the bulge in my jeans. She leans forward and crushes out her cigarette. “I see you’re aroused. It’s my breasts, isn’t it? You’re turned on looking at them. Am I right?” I feel myself blushing. “It’s OK if you are,” she says, almost understandingly. “Many men feel that way when they see the breasts of an attractive woman. You do find me attractive, don’t you?” She slides her hands up her torso and cups her breasts. I nod. She leans in toward me, still cupping her breasts. “Do you? Tell me you do,” she whispers. “I do,” I say, nervous and a little embarrassed. “You do what?” she asks, more forcefully this time. “I do find you attractive.” Carol slips the front of her dress down a bit, popping her breasts out, baring them for me. “Do you like to look?” she asks, sliding her hand up my thigh. “Yes.” I whisper, blushing, looking down at her boobs, her hard, pink nipples. “Say it,” she says to me, in a way that is direct. “I like looking at your breasts,” I say. She squeezes my cock, and then stands up in front of me. “You should see my pussy. I had it completely waxed this afternoon!” She says this with a smile. She slips her hands under her dress and slides her black lace panties down around her ankles, stepping out of them, and then sitting back down next to me. Her knees are apart. “Well, would you like to see mine?” She smiles at me. I feel my face blush, deep red. “Don’t be shy,” she says, patting my knee. “I’d be offended if you didn’t,” she slides her hand up my thigh. “I mean, you obviously find me attractive, right?” I look up at her and nod, embarrassed. “Well then, do you want to see my freshly waxed pussy?” I look back down at her thighs. “Yes. Yes I do,” I whisper. She starts to slide the hem of her dress up, stopping only part of the way. “I think you should slide down closer to take a look,” she says, leaning back. I slouch down on the sofa. “No, silly,” she says, putting her hand on my head and guiding me to the floor. “Lower.” She giggles. I look up and can just see the outline of the labia minora. “Would you like to get a real good look?” I nod, yes, looking up at her. She slides her dress higher, spreading her thighs even wider. I can clearly see her pussy now, pink and hairless, nearly glistening in the living room’s light. Carol shifts her hips, sliding her dress up just over her hips, and spreading her legs open a little further. “Jackie says you’re really good at eating pussy. Why don’t we find out!” She looks at me, smiling, a cocky look on her face. I take a deep breath. She runs a manicured finger across her mound, and spreads her lips slightly with two cherry red fingernails. I can see her clit, surrounded by wet, pink folds. I lean in slightly, slide my hands under her thighs and slip my tongue into her pussy. It’s wet alright, and warm, and I can smell a mixture of her scent and her soap and perfume and I start to slowly swirl the tip of my tongue around her clit in slow, looping motions. I glance up at her, and her see her watching me, intently, over her nipples. I close my eyes and focus on bringing her to a slow orgasm, like Jackie’s taught me to do. Twenty minutes later and my knees and jaw are sore, and my chin and cheeks are soaked and Carol is moaning, breathing steadily and heavily, on the verge of orgasm. I see her belly begin to tighten as climax approaches, and her thighs close around me. I feel her cum in my mouth, and she reaches down with her right hand, running her fingers through my hair as she sighs deeply. “I need a cigarette,” she says, looking down at me. I reach over and shake out a fresh one, lighting it on her lips. She exhales. “Well, your wife wasn’t kidding. You are fantastic at cunnilingus.” She drags off her cigarette, and adjusts her dress. I stay on the floor, between her legs, looking up. I can feel the precum on the head of my cock, in my boxers. Carol finishes her cigarette and looks down at me. “Well,” she says slyly. “Maybe we should take this upstairs to the bedroom? Do you think Jackie would approve?” She stands up slowly, over me, and slips out of her dress. She’s completely nude, save for the heels, and takes my hand and helps me up. She presses against me. “I don’t think she’ll mind. And I think you’ll enjoy it better upstairs, too.” I follow her naked body upstairs to a large and well-appointed bedroom. “Oh my,” she exclaimed, turning around to face me. “I haven’t cum that hard in weeks! I hope there’s more where that came from.” She smiles at me, and leans forward. “Oh, and Jackie gave me permission to have penetrative sex with you tonight.” She completely enunciates the word “penetrative” while looking me in the eye. “Is that something that you’d enjoy?” I nod, looking away shyly. “Don’t be shy – I’m sure it will feel very good for you. But please, if that’s something that you’d like, you need to tell me now.” She places her hands on her hips, waiting. “I like it when boys tell me what their needs and desires are. And I enjoy fulfilling those needs and desires, provided my wants and desires are being met as well.”
“I – I.” I clear my throat, and try again, still a little stunned that I am standing in the bedroom of such an attractive woman, who is nude, and that my wife set this up. That I am going to have sex with her tonight. “I would like to have sex tonight.” “You’re going to have to be more specific than that, silly.” “I – I… I would like to have sex with you tonight.” I stammer this out. “I’m sure – many men would. But what would you like?” She says this as I stare at her titties. I screw up the courage to tell her what she wants to hear. My cock is so hard, I am so nearly ready, that I can say just about anything she wants to hear. “I would like to have sex with you tonight. Sex that includes penetration. Please.” “Mmmhmm. That sounds very nice. I think that’s something that I would enjoy. Why don’t you bring me a cigarette?” She heads toward the bed and snaps on the lamp on the nightstand. “I like to fuck with the lights on. I hope that’s OK with you – I find that it’s much more enjoyable if I can see everything.” She lays back on the bed and I light her cigarette. “Well, you should probably remove your clothes. Besides, I’d like to see what we’re working with tonight.” I pull my shirt up over my head and unbuckle my belt, sliding my jeans off. I hook my thumbs under the waistband of my boxers and slide them down, freeing my erection, and stepping out of my clothes as they bunch around my ankles. Carol is laying on the bed, smoking, stroking her clitoris and eyeing my hard on. “Why don’t you bring that mouth of yours back over here, big boy? I loved what you did last time.” After I finish eating her pussy for a second time, I slide up her body, and press my cock against her abdomen. “Oh my you’re hard, aren’t you? I’ll bet you’re ready for something more, aren’t you” she says, slipping her hand down around my cock. I close my eyes and press against her, excited, aroused, thinking about Jackie and how great she is to set this up for me. Thinking about Carol’s pussy and how wet she gets, and how much I want to slide into her. She wraps her legs around my waist, holding me close with her thighs. She reaches down between us, running the head of my cock against her pussy lips, getting me wet and slippery, and looks into my eyes as she licks her fingers. I slip inside of her, just an inch, and I feel her tighten around me before she pops my cock out of her mound. I feel her hand wrap around my cock as she starts to rub the head slowly, firmly. “I’ll bet you’d like to stick your cock deep inside of my wet cunt, wouldn’t you,” she whispers in my ear as she rubs me. “Here you are, laying on top of me, your cock in my hand, thinking about my smooth, hairless pussy, how wet and pink it is. Wouldn’t you like to know how tight I am? How deep inside of me you could fit?” She licks my ear and sighs, stroking me harder, pulling on my cock, which is wet and slick from the combination of pussy and saliva. I try to shift my weight so I can slip inside of her, but she holds me tight with her thighs. “Wait, hold on,” she says. I feel her breasts press into me. She rubs my cock faster, and I can feel my balls start to tighten up. “But I – “ presses her other hand to my lips. “Shhhhh. Just a moment. Be patient, boy,” she whispers this to me as she rubs the head of my cock. I can feel my orgasm coming, and I want to be inside of her when I cum. I try to hold off, try to stop my climax from happening, but then Carol licks my lips and looks at me and says “wouldn’t you just love to explode in my wet, pink hole? Wouldn’t you love to just fill me up? To fill. Me. Up. With all of your cum?” I feel that familiar tightening in my scrotum as I cum, hard, the hours of tension and teasing all being released into her hand. “Oh my! Oh dear! Did you just pop off in my hand? Oh, well…” she says, pulling her hand away mid-ejaculation. I’m left with my cock still pumping on her belly as we’re pressed together, and she pulling away from me, mid-climax. “Well, I hope that felt good?” She unwraps her thighs and slips out from under me. “Oh my goodness that’s a lot of semen. I need to get cleaned up. Be right back!” she says, slipping into her bathroom. I roll over, laying back on the bed. I take a deep breath. I had hoped that I’d get the chance to slip into her before cumming. And while it’s a little embarrassing, maybe it’s for the best to get that first one out of the way, so that I can focus more on the next session. Focus more on pleasing her, but also on taking my time and enjoying her body. I hope that she’s not disappointed. I hear her close the faucet and the pocket door slides open. She’s wearing a Japanese-inspired silk bathrobe as she steps back into the bedroom. “Well, that was… fun? Right, you liked that? I do love making boys feel good, especially when they fulfill my desires as well. And you’ve done such a good job with that tonight, I wanted to make you feel good.” She sits on the edge of the bed next to me, as I lay there, flaccid, sticky, nude. “Did that make you feel good?” I nod yes. Because it did, even if I didn’t get to actually stick it into her yet. And because I want her to feel nice as well, so that we can keep things up. “That’s good,” she says, stroking my thigh, brushing my cock, caressing my scrotum. “Because I want boys to feel good. And I like to feel good. When I feel good, I want to make boys feel good.” She reaches up and cups my balls, playing with my cock gently. I become semi-erect again. “Well, Jackie did say that we could have penetrative sex tonight. And that’s something you told me you’d like to try, right?” I nod, looking at her. “That’s good, because that’s something that I enjoy doing, too.” She says this in the most understanding way you could imagine. So gentle, so kind. She stands up and unties her bathrobe, revealing her breasts to me, slowly. “I know you like what you see, right?” I nod. “Good, because I have a special surprise for you tonight. Actually, it was Jackie’s idea. You’re very lucky to have such a bold, creative and loving woman in your life.” Carol slips off her bathrobe and it falls to the floor. Between her legs is a six inch rubber cock, held in place with nylon straps. “Don’t worry, I’ll be gentle, of course. I like to make my boys feel good. I know that I have been looking forward to sex with you. And I can hardly wait to penetrate you!” She rubbed her cock like the real thing, and reached toward me. “Go ahead and roll over,baby. We can start nice and slow….”
Did you write this? I thought it was great – and the end made me laugh out loud :)
I did! I write a lot, not all of it erotica. I’m glad you enjoyed it. I’d like to write more about these characters; if you have any ideas, I’d love to hear them.