13 comments/ 25511 views/ 1 favorites One-Night Stand Hates Foreskin By: DS299 NOTE: Thousands of people read these stories, VERY few comment or send feedback. This has a direct impact on the author's motivation to write further stories. I'd love to hear from anyone the story resonates with for any reason. It was reading break, and I was visiting my friend Meghan in Florida. We were friends from improv team but, now that she'd moved away, we only saw each other a couple times a year. She had a dorm room to herself and she let me sleep on her floor. I was there all week. On the fourth night, we went drinking with a few of her friends. Eventually, some friends of her friends joined our group. This group had a mix of older people. I've always had a thing for older women, never acted on (I'd only ever had one girlfriend, in highschool), and one was exactly my type. Susan had large breasts, dark hair, and was really sarcastic and funny. She had a low cut top and her boobs looked amazing. She looked about 40. Meghan said that Susan was a nurse, but sometimes did improv with the group, which is how everyone knew each other. I was too shy to say too much, but couldn't believe my luck... Susan struck up a conversation with me, kept it going through my occasional awkward silences, and soon we were having a nice conversation. She knew exactly how to get me talking. I offered to buy her a drink and she suggested I get a pitcher for the two of us. I went up to the bathroom, and then the bar, and Meghan stopped me on the way – she was smirking. "So, you and Susan, huh? Cougar hunting?" I smiled, "just easy to talk to." She said, "yeah right. Well, just so you know, if you are interested she'd probably go for it. She has a thing for younger guys. She's been sleeping with another guy on the team for a while now." My heart caught in my chest for a second. I'd been enjoying this as a fantasy, masturbation fodder for later. The possibility of "doing" something never occurred to me. "Would that be weird?" I laughed. I trusted Meghan's opinion. "Not at all," she said. "It's totally okay for younger men and older women to sleep together. I think that'd be awesome. Here, I'll go back to the table and work my magic." "Dude... don't embarrass me." "Don't worry, she won't know I'm doing it. Trust! We're going to get you laid!" I did another lap around the bar, and talked to one of Meghan's guy friends. In the back of my mind I reflected that one reason why I didn't plan on trying to do anything was because I'm uncircumcised. To some people (especially those living in Europe) that might sound weird, but where I live, most guys are circumcised. I've quietly listened for years while people have made fun of uncut dicks, and my first girlfriend reacted pretty weirdly to it. I calmed myself by thinking that if she was a nurse, she'd probably seen her fair share, and that as an older woman, she was probably more experienced and cool. I returned to the table to interrupt Meghan and Susan, now conversing by themselves at the end of the table. We continued to drink and talk, and then Meghan excused herself. I was brainstorming how to take things to the next step and generally feeling very anxious when, to my relief, Susan took the next step: "Hey, want to get out of here? It's so loud. We could hang out at my place for a bit if you want." "Yeah, that'd be awesome." In the parking lot she called a cab and we made small talk. I was a bit nervous about what would happen – I'd never had a one-night stand before. We got in the cab and, again, after some silence, Susan took the lead. "I really want to kiss you right now, is that okay?" "Yes." She kissed me, and I felt her nipples hard on my chest. She seemed really into it, pushing her tongue into my mouth. After a few minutes of intense make-out I gently pushed her away, and we both caught our breath. "You're so fucking cute" she said, then, "I really want to have sex with you... what do you think about that?" "God yes." "Okay, I thought so." She was rubbing my arm. We got to her place and went up the stairs. She let me in. It was nice, modern and tasteful. Grey carpeting and clean. I sat on a black leather couch, while she hung up her jacket. She sat beside me on the couch and continued to kiss me. She pulled away and said: "I don't use condoms, but I guarantee you I'm clean. Meghan says I don't have to worry about anything with you, right?" "Yeah, I'm definitely clean." "I'm on the pill, also," she added. The implication was clear; the expectation was that this beautiful sexy older woman wanted me to come in her vagina. She pointed down the hall to the bedroom and whispered, playfully, "you're going to sleep in mama's bed tonight, aren't you?" It was playful, a joke, but for some reason, I found this incredibly hot. She took off her socks, and shirt. She had a lacy black bra and I could see that her nipples were brown, large, and quite thick. I kiss and sucked her nipples through her bra, leaving wet spots on the fabric, which she caused her to moan. "That feels amazing... I want you to suck my tits when we get to bed, okay?" "Fuck yes." She took off my shirt, licked my chest, then asked me to take off my socks and jeans. I was just in my boxer-briefs. She eased out of her pants, and I could see her thick pubic hair through her thin cotton panties. She pressed me into the couch and we continued to kiss. I know she could feel my erection on her belly. She tugged at the waistband of my underwear. Moment of truth. She perched at the end of the couch, her legs slightly spread with tufts of pubic hair showing off both sides of her panties, tight against her pussy lips, watching as I slid my underwear down. I took them off my legs and tossed them to the floor. I had an erection, about 6", and the glans of my penis was poking out of the foreskin. I waited for her response. She took a deep breath. "Oh honey," she said. "Why didn't you tell me you aren't circumcised?" My heart sank. My erection began to falter. "I'm sorry," she said, "I don't sleep with uncircumcised guys. I've had too many problems. I'm just very careful about what goes into my vagina. Foreskin holds bacteria. It increases the chance of cervical cancer in women." My indignation had a mild flare, and I sputtered a defense. She stopped me: "I'm a nurse, sweetheart. I know, really. All boys should be circumcised." "It's okay," she said, "you're still going to have an orgasm tonight, it's just not going to be inside me. I'm not going to let you put your foreskin inside of my vagina, or in my mouth. Sorry." "Besides, it wouldn't feel good for me. That's another thing. Uncut guys thrust too quickly. There's not enough friction against my vaginal walls. It's like they're just masturbating in their own foreskin, and it makes it very hard for the woman to achieve orgasm. And I usually come really easily." "In my mouth, the texture of foreskin is really gross, and it gets slimy from pre-cum. Just... not good." She looked as if she was about to wretch. I apologized for not saying something earlier. In hindsight, it seemed obvious. It's a basic courtesy to give potential partners a heads-up. "It's okay. I bet you're hating your mom right now, though." "Kind of." "Well, it's your responsibility. You're an adult. You should go get it done, it's not a big deal. Women prefer circumcised penises by far, and it's way, way, healthier. Just get it over with. You'll feel more confident." "Now," she said, "if you can get hard, you can masturbate onto my breasts." "Okay." She took off her bra, and her heavy tits hung free, with the indentations of the tight bra still visible on her skin. I asked if we could go to her bedroom but she said that she'd prefer to stay in the living room. She got on her knees, and held my ass while I stroked my cock up to erection. "For the record, if you were circumcised, you were going to have the best sex of your life. It's nothing personal." "I know." She kissed my stomach as I masturbated. At one point she put her hand on my penis and stroked me. I could feel the soft callouses on her hand, it felt incredible. She pulled my foreskin back tightly and said, "this is how a normal penis looks. Isn't it neat and sexy?" "You'd masturbate like this," sliding her other hand up and down the shaft, bumping against my sensitive pink glans. "It feels just as good, just different." She let my foreskin loose, and had me continue. I began to stroke myself again, and imagined how incredible it would've felt to suck her fat brown nipples. Then, to slide my penis past the lips of her hairy pussy, feeling myself press entirely inside her, her tongue in my mouth, her hands on my thighs showing me the pace at which she wanted to be fucked, her heels on my buttocks, so I wouldn't dare dream of pulling out of mommy until inevitably spraying her cervix with my semen. She'd hold me through my orgasm, wind me down by having me suck at her breasts, and we'd sleep together all night. My orgasm hit and I shot a few spurts of cum onto her breasts. "There you go, get it out, shoot your cum out, good boy." She took a few drops of cum from her breast, and put it to my lips. "Taste." She put on her bra and I got dressed. She called me a cab, and gave me a peck on the cheek. She looked me straight in the eyes and said, "get it done! Seriously!" One hesitates to generalize, but this is my experience. Older women are very open to sex with young men. But they hate uncircumcised penises. The foreskin has to go. I got back to Meghan's place and she said she was surprised to see me so soon. I explained what happened, not bothering to censor myself. Meghan said, "I'm so sorry..." I thought she meant for what had happened – my humiliation – but she followed up with, "I can't believe your mom didn't get that done when you were a baby. That must be really hard for you." It's been a few years, but this night does sum up my experience as an uncircumcised man living in the US. My next girlfriend tolerated it, but didn't like it, and now I'm probably going to get in done. Not all women will admit it, but in general they much prefer their guys circumcised.