Foreskin Anxiety

They'd met on Bumble. It was their fourth date. Covid had changed the dynamics of dating, everyone felt a bit uneasy meeting with strangers. It was as though there was a whole extra layer of social protocol to navigate before anyone felt comfortable. They'd gone for a walk on the beach, then drinks in the park, then on their third date they'd gone to the art gallery, and then out for wonton soup and beers. On the second date, they hugged goodbye, and on the third he'd kissed her on the cheek. For the fourth date, she'd come over to his apartment, he cooked her dinner, and then they watched a movie and shared a low-dosage weed gummy. They made out. All the extra build-up made the intimacy, when it came, that much more intense. With so much more time interacting with people through screens, he'd forgotten the basic power of looking into someone's eyes directly, feeling their skin on yours.

He hadn't expected things to progress so quickly. He had been thinking they would just make out. But he'd let his hand find her breast through her sweater, with its hard little nipples, and she'd palmed her hand on the crotch of his jeans, finding his erection, and they made out vigorously, with her tongue occasionally forcing its way into his mouth. When they first pulled away, she admitted how horny she'd been for months. She asked him if he wanted to go to his bed, and he agreed.

He stripped down to a t-shirt and underwear, and she took off her sweater, tight blue jeans, and little black socks, and he caught a glimpse of her matching lacy black bra and panties before she slipped under the covers. The weed was starting to hit and they continued to make out side by side in bed, before he fumbled behind her back with the claps of her bra, before releasing it and lifted it off her chest. Her breasts were on the larger side, with brown areolas, nipples standing erect. She moaned when he grazed them with his fingers.

"I'm so wet," she said.

He kissed down past her breasts, to her toned navel, and then to her inner thighs. He kissed the crotch of her panties, and could feel their dampness, and her fragrance, almost like sweet rum full of rich and deep flavours.

"Oh god," she said, and hurriedly lifted her bum and slipped her panties off, before he could tease her further.

Her vulva looked freshly shaved, and she had pink, medium-length labia, which opened up like a flower. She had a perfect vagina - neither too plump, nor too long, without any bumps or blemishes, or even any sign that she'd ever had pubic hair. It pouted, and unfolded, with labia just textured enough for him to feel against his fingertips.

He had one ex-girlfriend who was self-conscious about her vagina. She'd had especially long labia, and an ex of hers had made fun of it once. He was sure his current date had never had this problem, and that her vagina brought all of her partners total pleasure.

He kissed it first, and took in her smell, before giving her several long flat licks with his tongue. She trembled with pleasure. He continued, before circling her clit, and then finding a rhythm with two fingers sliding in and out of her vagina. He sensed that she was enjoying it, but he felt her hands on his arms, drawing him up. She told him it felt really good, and that she wanted to go down on him too.

He felt a surge of anxiety, but tamped it down.

"Um... I don't really like receiving oral sex, if that's okay."

Reading her confusion, he tried to clarify. "I just find it really intimate."

She analyzed him for a moment then said, "I totally get that, what if I just went really slow?"

His mind was racing, but he decided to resist his anxiety, knowing it to be irrational. "Okay, let's try it for a bit."

She began to kiss down his chest, until he added,

"By the way, I'm uncircumcised, just so you know."

She didn't seem to react, but kept kissing down, until she arrived at his boxer-briefs, and squeezed at his bulge through them, before sliding them off.

She kissed at the base of the shaft, and then the tip of the penis. He was still half soft - small, and very wrinkled against her lips - but felt himself growing harder. She used a soft grip on his penis, and began to slowly draw back his foreskin, paying attention to his reaction. She was tentative, not quite sure how to touch him or if she was hurting him. Jeff closed his eyes and tried to focus on the sensation. He could feel that she had to push back quite a lot of skin to finally expose the head of his penis. He had a particularly long and thick foreskin, so that even the few women who'd had uncircumcised partners before him were sometimes briefly startled. The foreskin tapered off at the tip, into a sort of nozzle.

The THC he'd consumed helped him sink into the sensations. His long foreskin being repeatedly pushed back out of the way, sliding down over the glans, while his date's warm mouth slid up and down his erection.

Even so, his anxious thoughts would sometimes creep back in. He was very self-conscious about being uncircumcised, he always had been. Physically, his foreskin always felt very "extra". It made him feel awkward and vulnerable to be laying back with his wide legs open, and a beautiful woman's mouth sucking his penis. Even though he was a good size, above average, the thought of his cumbersome foreskin in her mouth made him uncomfortable and uneasy. It was hard not to think about it. He briefly worried that he might not have cleaned adequately after going pee earlier. On some level, vaguely, receiving oral sex grossed him out.

Something felt very strange about the fact that because his own mother had neglected to have him circumcised as a baby, this beautiful woman was forced to deal with extra skin in her mouth during sex. He felt awkward for the both of them.

She pushed his foreskin all the way back, and held it there, while sucking his bare head. That felt a bit easier and more comfortable and natural.

She came up after not too long. He thanked her, and told her that it felt good. She kissed him, and they cuddled for a while, and then she got up to leave.

They continued to date. He could look at her face for hours. She had pretty eyes and perfect teeth. (She had had braces as a teen, and still diligently wore her retainer through her twenties when she went to bed.) She was intelligent. Warm. Playful. Talking with her was fun. She was charmingly self-deprecating at times, make him feel at ease. And, she had a very high sex drive. He was perfectly willing to initiate, but she would always beat him to it.

She'd become comfortable with his discomfort around receiving oral sex. She would occasionally go down on him very briefly, but in general their routine was for him to suck her breasts, give her one orgasm with his mouth, before they would have intercourse, usually in missionary.

While he didn't like the sensation of his foreskin sliding up and down during intercourse, he felt less self-conscious about it than he did during oral. He'd also heard from a friend that women's vaginas aren't sensitive enough to feel the difference, so he figured it didn't matter to her.

But one time, they got high before sex. She had more than he did. Her head was rolling while he fucked her. At one point she said, "take the condom off". He said, "I'm not wearing a condom". She looked confused, reached down, felt at his foreskin, before realizing her mistake. He pulled it back and began to thrust, and asked, "does this feel better?" She moaned and it was clear that it did. But after a few seconds the foreskin rucked back over the head.

As the continued to date, it was becoming increasingly clear that my foreskin was an issue. At first we could chalk the awkwardness up to general social anxiety, or just getting comfortable with someone new. But it was starting to feel like something was fundamentally in the way.

We both felt clumsy during sex, as though we could never quite get comfortable. No position was quite right, we could never quite let go. We wanted to be more in love, but our sex wasn't quite right.

"Do you know why your mom didn't get your circumcised?" She asked one night.

"I asked her once. Apparently she was right about to. My doctor had already given me an injection of anaesthetic. But at the last minute my aunt talked her into thinking it over for night, and then I just never ended up being done. But it was like, a really close call."

"It sounds like you might rather have just been circumcised then."

"Yeah. It's so much easier at that age."

"I can imagine. Have you ever thought about getting circumcised now, like as an adult?" She asked.

"Is that possible?"

"As far as I know, it's not that big of a deal. My cousin had to get circumcised when he was a teenager."

"Do you think I should?"

"It seems like you're not really into having foreskin. Maybe you'd just feel more comfortable being circumcised?"

The truth was he hated not being circumcised.

"Do you think it would make our sex better?"

She took a moment to consider her answer. "Yes, I do."

"How so?"

She paused, gathering her words. "Oral sex, I think, would be a lot... easier, maybe a better texture or sensation for both of us. Penetration will feel more direct, just cleaner, in a way. In general, I just think things will just be less in the way."

"Having surgery on my penis sounds really intense, as an adult."

"But would you rather live your whole life not feeling great about your penis? Within a couple months you could be circumcised and healed."

Something about the prospect of finally getting circumcised invigorated him. It had never been within his real range of possibilities.

He mounted her. He was erect, but his loose frilly foreskin still crowned his glans, as he began to push into her welcoming vagina.

They were both hyper-conscious of his thick foreskin sliding in and out of her vagina, only allowing his glans to be fully exposed during the maximum extension of his thrust. But this time, they were able to gaze into one another's eyes and feel the sensation anew, focusing not only on how it felt, but how it would to be gone.

"If you were a guy, would you want to be circumcised?"

"Yes," she answered immediately.

"If we had a son, would you want to get him circumcised?"

"Yeah."

"Do you prefer guys who are circumcised?"

"Yes, I do."

She kissed him, fucked him back, had an idea, talked to him.

"Pretend I'm your mom. What would you say to me?"

"You should...-"

"Let it out. You can be loud."

She wrapped her legs around him.

He spoke, loudly: "You should have had me circumcised!"